WO2025059043A1 - A modified maleated natural oil containing a lactam moiety, salts, compositions, and use thereof - Google Patents
A modified maleated natural oil containing a lactam moiety, salts, compositions, and use thereof Download PDFInfo
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- WO2025059043A1 WO2025059043A1 PCT/US2024/045994 US2024045994W WO2025059043A1 WO 2025059043 A1 WO2025059043 A1 WO 2025059043A1 US 2024045994 W US2024045994 W US 2024045994W WO 2025059043 A1 WO2025059043 A1 WO 2025059043A1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Definitions
- the present application relates to a renewable, modified natural oil containing a lactam moiety, salts, and compositions thereof, that exhibit improved physical properties, and more particularly, to a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (C) a base.
- Natural oils such as soybean and linseed oils, are one of the most promising raw materials for the synthesis of renewable compounds, including polymers, plastics, and plasticizers. These natural materials are inexpensive, highly abundant, come from reliable and sustainable sources, and have high potential for modification. Natural oils are generally blends of different triglycerides, the esterification product of fatty acids and glycerol, and contain varying degrees of unsaturation (i.e., double bonds). Oils can be characterized by a hydroxyl value and the fatty acid compositions.
- Modified natural oils are natural oils that have been chemically functionalized by the chemical addition of epoxide (oxirane) and succinic anhydride functional groups. Examples include epoxidized and maleated soybean oil and linseed oil, unsaturated natural oils lend themselves to these chemical functionalizations.
- US Patent 9809538B2 describes a modified natural compound synthesized from epoxidized natural fatty acid, maleated natural fatty acid, epoxidized natural oil, or maleated natural oil; and lactam compound with hydroxyl(s) to form e.g., adhesive or beverage composition.
- a discussion of reaction scheme for the maleinization reaction in the vegetable oil is provided in the article “Maleated soybean oil and its multifunctional properties,” by Gripp, Anna A., Steinberg, David C., published in Cosmetics Exhibition & Conference Proceedings, Barcelona, Mar.22-24, 1994.
- PCT Application 2019113068A1 and 2005071050A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives.
- a discussion of maleic anhydride polymerization and modified plant oils with polyols is provided in the article “Polymerization of Maleic Anhydride–Modified Plant Oils with Polyols,” by Tarik Eren, Selim H. Kusefoglu, Richard Wool published in Journal of Applied Polymer Science, Barcelona, Volume 90, Issue 1, Pages 197-202, 2003.
- EP Patent 2754306A describes an adhesive containing a polycondensate and a dienophile modified fatty acid as a cross-linking agent.
- PCT Application 2005071050A1 describes a metalworking fluid comprising oil in water emulsion from a reaction product of maleic anhydride and a triglyceride oil from a plant or land animal and further reacted with water, Group IA and IIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, poly (alkylene oxide)s, or polyamines or mixtures.
- Group IA and IIA metals ammonium hydroxide
- various amines alkanolamines, polyols, alkoxylated alkanolamines, poly (alkylene oxide)s, or polyamines or mixtures.
- both ESO and maleated soybean oil are insoluble and non-dispersible in water or alcohols.
- these fatty acids and oils may tend to exude or phase-separate from formulated compositions. This feature makes their formulation more difficult, often requiring additional ingredients to facilitate solutions, emulsions, or dispersions.
- Natural and epoxidized/maleated natural oils may not impart the desired property needed in end- uses, such as solubilization capability, glass transition, flexibility, shine, and/or plasticization.
- the present application provides a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure: R wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between th group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl,
- reaction product of (A) maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium.
- the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties.
- composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
- Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between the group and the group;
- Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);
- X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups,
- a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: R wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the O group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl,
- a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between th e group and th e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl
- an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl
- reaction product of (A) a maleated natural oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone.
- the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties.
- a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and th group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, ary
- Yet another aspect of the present application provides a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
- Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the group and th group;
- Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);
- R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
- a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and th e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl,
- an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl
- Another aspect of the present application provides a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and
- reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product has the structure: wherein R 7 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1
- a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th group and th group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl
- a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between th group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl
- branched and unbranched alkyl groups refers to alkyl groups, which may be straight chained or branched. Branched groups include isopropyl, tert-butyl, and the like.
- references herein to “one embodiment” or “another embodiment” or “one aspect” or “another aspect” of the application include one or more such embodiment, or aspect, unless the context clearly dictates otherwise.
- the term “personal care composition” refers to a composition intended for use on or in the human body and may be an oral care composition, a hair care composition, a hair styling composition, a face care composition, a lip care composition, an eye care composition, a foot care composition, a nail care composition, a sun care composition, a deodorant composition, an antiperspirant composition, a cosmetic composition (including color cosmetics), a skin cleaning composition, an insect repellant composition, a shaving composition, a toothpaste, a mouthwash, a tooth whitener, a tooth stain remover, and/or a hygiene composition.
- hair care and hair styling compositions find application in enhancing hair shine, cleansing hair, conditioning hair, repairing split ends, enhancing hair manageability, modulating hair stylability, protecting hair from thermal damage, imparting humidity resistance to hair and hair styles, promoting hair style durability, changing the hair color, straightening and/or relaxing hair, and/or providing protection from UV-A and/or UV-B radiation.
- compositions such as those for skin care and sun care compositions, are useful for protecting from UV-A and/or UV- B radiation, imparting water resistance or water proofness, moisturizing skin, decreasing and/or minimizing the appearance of wrinkles, firming skin, decreasing or minimizing the appearance of skin blemishes (such as lentigo, skin discolorations, pimples, or acne), changing skin color (such as color cosmetics for the face, cheeks, eyelids, or eye lashes).
- Oral care compositions according to the invention may be used as denture adhesives, toothpastes, mouthwashes, tooth whiteners, and/or stain removers.
- Personal care compositions also are used for delivering an active (such as to the skin, hair, or oral cavity).
- polymer refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted or end-capped. Non-limiting examples of polymers include copolymers, terpolymers, tetrapolymers, quaternary polymers, and homologues.
- copolymer refers to a polymer consisting essentially of two or more different types of monomers polymerized to obtain the copolymer.
- reaction product refers to a substance produced from a chemical reaction of one or more reactant substances.
- natural oil refers to compounds comprising triglycerides and may contain varying levels of fatty acids, monoglycerides, diglycerides and triglycerides refer to oil derived from plants or animal sources. Natural oils also include fatty acid glyceryl esters, which are synthesized by reacting glycerol with 1, 2, or 3 molar equivalents of a fatty acid or a mixture of fatty acids. These compounds can be mono, di or triglycerides of a single fatty acid or a mixture of fatty acids.
- maleated natural oil or “natural oil with maleated functionality”, can be used interchangeable without limiting the scope of the present disclosure, and refer to natural oil comprising at least one maleated functionality. Accordingly, the term “maleation” or “maleated” as used hereafter should be understood to mean “functionalization” insofar as the use of functionalizing reagents other than maleic anhydride are contemplated for use in the process of the invention.
- the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule.
- maleated functionality refers to moieties formed by attaching maleic anhydride to unsaturated fatty acyl chains, found in natural oils, by ene reaction. “Maleated functionality” includes but is not limited to the cyclic anhydride form (I), the diacid form (II), the disodium dicarboxylate form (III), other dicarboxylate salt forms, and the half ester form (IV).
- maleated functionality pictured in I, II, III and IV might also be called by one of ordinary skill in the art succinic anhydride, succinic acid, succinate salt or succinate half ester functionality.
- base refers to any substance which can alter the pH of a solution from a neutral pH of 7.0 to a basic pH (i.e., 7.1 to 14).
- a base is a substance of a large class of compounds with one or more of the following properties: bitter taste, slippery feeling in solution, ability to turn litmus blue and to cause other indicators to take on characteristic colors, ability to react with (neutralize) acids to form salts includes both organic base or an inorganic base and combinations thereof.
- inorganic base includes oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
- the term “functionalized” with reference to any moiety refers to the presence of one or more functional groups in the moiety. Various functional groups may be introduced in a moiety by way of one or more functionalization reactions known to a person having ordinary skill in the art.
- Non-limiting examples of functionalization reactions include: alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling, and the like.
- the term “functionalized” with reference to any moiety refers to the presence of one more functional group is selected from the group consisting of alkyl, alkenyl, hydroxyl, carboxyl, halogen, alkoxy, amino, imino, and combinations thereof, in the moiety.
- the term “hydrocarbyl” includes straight-chain and branched-chain alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl groups, and combinations thereof with optional heteroatom(s).
- a hydrocarbyl group may be mono-, di- or polyvalent and have carbon chains containing 2 to 100 carbon atoms.
- alkyl refers to a functionalized or unfunctionalized, monovalent, straight- chain, branched-chain, or cyclic C1-C60 hydrocarbyl group optionally having one or more heteroatoms.
- an alkyl is a C1-C45 hydrocarbyl group.
- an alkyl is a C1-C30 hydrocarbyl group.
- Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n- hexyl, n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n-dodecyl, tert-dodecyl, n- tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
- alkyl also includes groups obtained by combinations of straight-chain, branched-chain and/or cyclic structures.
- aryl refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms.
- the definition of aryl includes carbocyclic and heterocyclic aromatic groups.
- Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenz
- aralkyl refers to an alkyl group comprising one or more aryl substituent(s) wherein "aryl” and “alkyl” are as defined above.
- Non-limiting examples of aralkyl groups include benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.
- alkaryl refers to an aryl group substituted with one or more alkyl groups, such as, for example, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-nonylphenyl, dimethylphenyl, or trimethylphenyl, which may optionally be further substituted on one or more of the carbon atoms of the radical.
- alkaryl refers to an aryl group comprising one or more alkyl substituent(s), wherein “alkyl” and “aryl” are as defined above.
- alkaryl groups include 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-nonylphenyl, and the like.
- alkylene refers to a functionalized or unfunctionalized, divalent, straight- chain, branched-chain, or cyclic C1-C40 hydrocarbyl group optionally having one or more heteroatoms.
- an alkylene is a C1-C30 group.
- an alkylene is a C1-C20 group.
- Non-limiting examples of alkylene groups include: [0059]
- arylene refers to a functionalized or unfunctionalized, divalent, aromatic hydrocarbyl group optionally having one or more heteroatoms.
- the definition of arylene includes carbocyclic and heterocyclic groups.
- Non-limiting examples of arylene groups include phenylene, naphthalene, pyridinylene, and the like.
- heteroatom refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heteroatom(s) may be present as a part of one or more heteroatom-containing functional groups.
- heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups.
- the heteroatom(s) may also be present as a part of a ring such as in heteroaryl and heteroarylene groups.
- the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between the group and th group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl
- the coating composition of the present application is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.
- Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th group and the group;
- Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);
- X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups,
- the personal care composition of the present application comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the pharmaceutical composition of the present application further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to
- Examples of pharmaceutically accepted excipients used in the pharmaceutical composition of the present application include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof.
- Non-limiting examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition of the present application include, foaming agents, mucoadhesive agents, preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof.
- the pharmaceutical composition of the present application is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension.
- an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl
- the agricultural composition of the present application further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 w
- Non-limiting examples of the adjuvants used in the agricultural composition of the present application include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof.
- the agricultural composition of the present application is in the form of an aqueous or a non-aqueous composition
- a capsule suspension an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
- the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and, (B) a lactam moiety having at least one amine functional group, wherein the lactam moiety having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl,
- the reaction component (B) comprising a lactam having at least one amine functional group is selected from the group consisting of: and combinations thereof, wherein: Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
- reaction component (B) comprising a lactam having at least one amine functional group is selected from the group consisting of: , and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH 2 -CH 2 –).
- the reaction component (B) comprising a lactam having at least one amine functional group is 1-(2-aminoethyl)-2-pyrrolidone, having the structure: [00111]
- maleated natural oil used as the reaction component (A) include maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
- reaction component (A) maleated natural oil is a maleated soybean oil.
- Another aspect of the present application discloses a reaction product of (A) maleated natural oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone.
- the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties.
- the reaction product comprises one or more structure(s) selected from:
- R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
- the reaction product disclosed hereinabove is used in end-user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions.
- end-user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions.
- a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between th group and t group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl,
- the coating composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the coating composition further comprises at least one additive in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or
- additives used in the coating composition include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers, or combinations thereof.
- the coating composition is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non- metallic coatings.
- the coating composition is coated on a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
- a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
- a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: R wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between th group and th group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl,
- the personal care composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt
- the personal care composition further comprises at least one personal care active ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt
- Examples of personal care active ingredients used herein include, but are not limited to, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof.
- Non-limiting examples of personal care active ingredient used herein include, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, or combinations thereof.
- Examples of the personal care composition include, but are not limited to, body wash composition, skin lotion composition, sunscreen composition, anti-wrinkle composition, moisturizer composition, facial cleaning composition, lipstick composition, lip-gloss composition, mascara composition, foundation composition, anti-perspirant composition, shaving composition, hair conditioner composition, anti-perspirant composition, deodorant composition, hair rinse composition, hair shampoo composition, hair styling composition, make-up remover composition, or oral care composition.
- the personal care composition is a formulation of an aqueous or a non-aqueous composition in the form of, but are not limited to, sprays, lotions, mousses, fluids, serums, solutions, suspensions, perms, emulsions, gels, mists, vesicles, dispersions, pastes, creams, solid sticks, shampoos, balms, wipes, milks, foams, jellies, or liquids.
- a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl
- the pharmaceutical composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 w
- Examples of pharmaceutically accepted excipients used herein include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof.
- Examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition include, but are not limited to, foaming agents, mucoadhesive agents, preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof.
- the pharmaceutical composition is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension.
- an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: R wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the group and th group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R 1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl,
- the agricultural composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to
- Examples of one or more agriculturally active ingredient used herein include, but not limited to, fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof.
- the additional ingredient used in the agricultural composition further includes an adjuvant or an inert ingredient.
- Non-limiting examples of the adjuvants used herein include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof.
- Non-limiting examples of inert ingredients used herein include, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or mixtures thereof.
- the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition.
- a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifung
- the agricultural composition is in the form of an aqueous or a non-aqueous composition
- a capsule suspension an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
- the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between t e group and t group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl,
- the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of: and combinations thereof, wherein: Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized
- the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of: and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH 2 -CH 2 –); and X is selected from OH, SH and NH 2 .
- the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is 1-(2- hydroxyethyl)-2-pyrrolidone (HEP), having the structure: H .
- maleated natural oil used as reaction component (A) include maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
- the maleated natural oil or natural oil with maleated functionality of the present application can be prepared by the maleation of natural oils.
- one or more of an ⁇ , ⁇ -unsaturated carboxylic acid or anhydride thereof, for example, maleic anhydride reacts with unsaturated fatty acyl chains present in natural oils.
- the maleation of natural oils can occur under heating in three different ways. The first one is known as “Ene” reaction (reaction between an allylic moiety and an enophile in a pericyclic reaction), obtaining a triglyceride structure with anhydride moieties (succinic anhydride).
- the second one is a radical addition, which consumes a double bond in the fatty acid, incorporating the succinic anhydride into the natural oil structure.
- the preparation of maleated natural oils is well known to persons skilled in the art. Accordingly, the maleated natural oils as used for the purpose of the present disclosure can be prepared by methods known in the related arts. In one non-limiting embodiment of the present disclosure, maleic anhydride and at least one natural oil can be reacted together at elevated temperatures.
- the maleation can be carried out at a temperature varying in the range of from about 150 °C to about 250 °C. In another non-limiting embodiment of the present disclosure, the maleation can be carried out at a temperature of from about 200 °C to about 230 °C, or from about 180 °C to about 190 °C. [00150] Further, the maleation can be carried out for a time period varying from about 0.5 hours to about 14 hours. In another non-limiting embodiment of the present disclosure, the reaction time can vary from about 1 hour to about 5 hours, or from about 2 hours to about 6 hours, or from about 6 hours to 10 hours.
- the mole ratio of maleic anhydride to natural can be equal to 1.
- the mole ratio can vary from about 1 to about 2, or from about 1 to about 2.8, or from about 1 to about 3.2 moles of maleic anhydride for each mole of natural oil.
- the mole ratio of maleic anhydride to natural oil in some embodiments is equal to 1, in other embodiments from 1 to 2, in other embodiments from 1 to 2.8 and in still other embodiments from 1 to 3.2 moles of maleic anhydride for each mole of natural oil.
- the reaction component (A) maleated natural oil is a maleated soybean oil.
- the reaction component (C), functionalized or unfunctionalized moiety includes hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety.
- the hydrophobic moiety and/or hydrophilic moiety is selected from those of a hydrocarbyl alcohol, a hydrocarbyl amine, a silicon-based compound, and combinations thereof.
- Hydrocarbyl alcohols are classified as primary, secondary and tertiary alcohols, based on the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. Each classification of alcohol has a general formula.
- the general formula for primary alcohols is the general formula for secondary alcohols is and the general formula for tertiary alcohols is OH wherein R, R′ and R′′ stand for different alkyl, alkylene, aryl, aralkyl, and arylene groups.
- R, R′ and R′′ stand for different alkyl, alkylene, aryl, aralkyl, and arylene groups.
- Examples of the hydrophobic moiety include those of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; silicon-based compounds; and combinations thereof.
- hydrophilic moiety examples include those of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; silanes; and combinations thereof.
- the silane is functionalized with an alcohol, an amine or combinations thereof.
- hydrophobic alcohol examples include hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1- octanol, 2-hexyl-1-decanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, and mixtures thereof.
- hydrophilic alcohol examples include methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof.
- hydrophilic polyol examples include, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.
- hydrophobic amine examples include benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof.
- hydrophilic amine examples include diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, and mixtures thereof.
- hydrophobic polyol examples include 1,6-hexanediol, 1,7-heptanediol, 1,8- octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate), poly(hexamethylene carbonate) and castor oil.
- hydrophobic silicon-based compound examples include aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy) propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane,
- hydrophilic silane examples include, 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof.
- the hydrophobic moiety is that of a hydrocarbyl alcohol that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.
- the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose and mixtures thereof.
- the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof.
- Hydrocarbyl amines are classified as primary, secondary, or tertiary, based on the number of carbon atoms attached to the amine nitrogen atom.
- the general formula for primary amine is the general formula for secondary amine is and the general formula for tertiary amine is wherein R 1 , R 2 and R 3 stand for the same or different alkyl, alkylene, aryl, aralkyl, or arylene groups.
- the hydrophobic moiety is that of a hydrocarbyl amine that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional.
- the silicon-based compound is a compound having the structure wherein R stands for different alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohol, amine or a combination thereof and n has the value of 1 to 10.
- the silicon-based compound is a siloxane, or a silane functionalized with an alcohol, an amine or a combination thereof.
- the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.
- the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxan
- reaction component (D) base is selected from the group consisting of inorganic bases, organic bases, or combinations thereof.
- Non-limiting examples of inorganic bases used as the reaction component (D) include oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
- Examples of the inorganic base used as the reaction component (D) are oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, or combinations thereof.
- Non-limiting examples of the reaction component (D) base of the present application include, alkali metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr); alkaline earth metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra); transition metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium
- Non-limiting examples of organic bases used as the reaction component (D) include, ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, or combinations thereof.
- Another aspect of the present application discloses a reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.
- the reaction product disclosed herein has the structure: wherein R 7 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 ⁇ 2 Mg, 1 ⁇ 2 Ca, 1 ⁇ 2 Co, 1 ⁇ 2 Cu, 1 ⁇ 2 Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
- the reaction product comprises one or more structure(s) selected from:
- R 7 is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl- 1-dodecyl, or mixtures thereof; and wherein R 8 , R 9 and R 10 are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.
- the reaction product disclosed herein is a polymer having the structure: wherein n is greater than 1; R 11 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, 1 ⁇ 2 Mg, 1 ⁇ 2 Ca, 1 ⁇ 2 Co, 1 ⁇ 2 Cu, 1 ⁇ 2 Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
- the reaction product disclosed herein is a polymer having one or more structure(s) selected from:
- reaction product of the present application is used in end- user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions
- a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between th e group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, ary
- the coating composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the coating composition further comprises at least one additive in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or
- additives used in the coating composition include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers, or combinations thereof.
- the coating composition is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non- metallic coatings.
- the coating composition is coated on a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
- a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
- a personal care composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, al
- the personal care composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt
- the personal care composition further comprises at least one personal care active ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt
- Examples of personal care active ingredients used herein include, but are not limited to, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof.
- Non-limiting examples of personal care active ingredient used herein include, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, or combinations thereof.
- Examples of the personal care composition include, but are not limited to, body wash composition, skin lotion composition, sunscreen composition, anti-wrinkle composition, moisturizer composition, facial cleaning composition, lipstick composition, lip-gloss composition, mascara composition, foundation composition, anti-perspirant composition, shaving composition, hair conditioner composition, anti-perspirant composition, deodorant composition, hair rinse composition, hair shampoo composition, hair styling composition, make-up remover composition, or oral care composition.
- the personal care composition is a formulation of an aqueous or a non-aqueous composition in the form of, but are not limited to, sprays, lotions, mousses, fluids, serums, solutions, suspensions, perms, emulsions, gels, mists, vesicles, dispersions, pastes, creams, solid sticks, shampoos, balms, wipes, milks, foams, jellies, or liquids.
- a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and the group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alka
- the pharmaceutical composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 w
- Examples of pharmaceutically accepted excipients used herein include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof.
- Examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition include, but are not limited to, foaming agents, mucoadhesive agents, preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof.
- the pharmaceutical composition is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension.
- an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and th e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR 1 , wherein R 1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl,
- the agricultural composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.
- the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to
- Examples of one or more agriculturally active ingredient used herein include, but not limited to, fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof.
- the additional ingredient used in the agricultural composition further includes an adjuvant or an inert ingredient.
- Non-limiting examples of the adjuvants used herein include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof.
- Non-limiting examples of inert ingredients used herein include, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or mixtures thereof.
- the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition.
- a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifung
- the agricultural composition is in the form of an aqueous or a non-aqueous composition
- a capsule suspension an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
- Example A1 Grafting of maleic anhydride onto soybean oil: [00213] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g of soybean oil and 204 g (3 mole equivalents based on soybean oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 6-8 hours. Completion of the reaction was indicated by NMR, and LC indicated ⁇ 0.5% of residual maleic anhydride.
- Example A2 Grafting of maleic anhydride onto palm oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of palm oil and 23 g (2 mole equivalents based on palm oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ⁇ C and then held at 210 ⁇ C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated ⁇ 1% of residual maleic anhydride. Yield was >96%.
- Example A3 Grafting of maleic anhydride onto canola oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of canola oil and 22.2 g (2 mole equivalents based on canola oil) of maleic anhydride.
- the mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ⁇ C and then held at 210 ⁇ C for 8-10 hours.
- the amber, viscous product was characterized by NMR, and LC indicated ⁇ 1% of residual maleic anhydride. Yield was >96%.
- Example A4 Grafting of maleic anhydride onto sunflower oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of sunflower oil and 22.4 g (2 mole equivalents based on sunflower oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ⁇ C and then held at 210 ⁇ C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated ⁇ 1% of residual maleic anhydride. Yield was >96%.
- Example A5 Grafting of maleic anhydride onto castor oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of castor oil and 21 g (2 mole equivalents based on castor oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ⁇ C and then held at 210 ⁇ C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated ⁇ 1% of residual maleic anhydride. Yield was >96%.
- Example A6 Grafting of maleic anhydride onto chickpea oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of chickpea oil and 38 g (3.4 mole equivalents relative to chickpea oil) of maleic anhydride.
- the mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 10-14 hours.
- the amber, viscous product was characterized by NMR, and LC indicated ⁇ 0.5% of residual maleic anhydride. Yield of maleated chickpea oil was >96%.
- Example A7 Grafting of maleic anhydride onto clary sage oil
- a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of clary sage oil and 51.5 g (3 mole equivalents relative to clary sage oil) of maleic anhydride.
- the mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 8 hours.
- the amber, viscous product was characterized by NMR, and LC indicated ⁇ 0.5% of residual maleic anhydride. Yield of maleated clary sage oil was >96%.
- Example B1 Sodium salt of maleated soybean oil (MSBO) from aqueous sodium hydroxide
- MSBO maleated soybean oil
- Example A1 100 g of maleated soybean oil (MSBO) from Example A1 was heated to 90 °C, and a mixture of 20.20 g (3 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 70 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.
- Example B2 Sodium salt of maleated soybean oil (MSBO) from sodium carbonate
- MSBO maleated soybean oil
- Example A1 100 g was heated to 90 °C, and 27.86 g (3 mole equivalents based on soybean oil) of sodium carbonate dissolved in 85 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 56 weight % solids and was characterized by IR. Yield was >96%.
- Example B3 Sodium salt of maleated soybean oil (MSBO) from aqueous sodium hydroxide
- MSBO maleated soybean oil
- Example A1 In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of MSBO from Example A1 was heated to 90 °C, and a mixture of 9.04 g (2 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 80 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.
- Example C1 Grafting of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) onto maleated soybean oil (MSBO)
- MSBO maleated soybean oil
- 100 g of MSBO from Example A1 and either 0.5, 1, 1.5, 2, 2.5 or 3 mole equivalents, relative to MSBO, of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) were combined, heated to 120 °C and held at 120 °C for 6 hours.
- the amber, viscous product was characterized by NMR and IR, and GC indicated ⁇ 5% of residual HEP. Yield was >96%.
- Example C2 Grafting of 1-(2-aminoethyl)-2-pyrrolidone onto maleated soybean oil (MSBO) [00235] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and 10.0 g (1 mole equivalent, relative to MSBO) of 1-(2-aminoethyl)-2-pyrrolidone are combined, heated to 80 °C and held at 80 °C for 6 hours.
- MSBO maleated soybean oil
- Example D1 Sodium salt of maleated soybean oil (MSBO) reacted with 1-(2- hydroxyethyl)-2-pyrrolidone (HEP) [00237]
- MSBO maleated soybean oil
- HEP 1-(2- hydroxyethyl)-2-pyrrolidone
- 100 g of the product from Example C1 was heated to 85 °C.
- Water and 50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 85 °C for 4 hours.
- the amount of sodium hydroxide added was sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with HEP into the corresponding sodium carboxylate salt.
- Example D2 Lithium salt of maleated soybean oil (MSBO) reacted with 1-(2- hydroxyethyl)-2-pyrrolidone (HEP) [00239] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152.1 g of MSBO made according to Example A1 and 41.8g (2.5 mole equivalents relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours.
- MSBO maleated soybean oil
- HEP 1-(2- hydroxyethyl)-2-pyrrolidone
- the amber, viscous product was cooled to 80 °C, and 9.31 g (3 mole equivalents relative to MSBO) of lithium hydroxide dissolved in 204 g of water was added over 1 hour to create a final solution that was 50 weight % solids. The mixture was heated to 85 °C and held at 85 °C for 2 hours. The amber product was characterized by NMR and IR. Yield was >96%.
- Example E1 Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and 2-octyl-1-dodecanol and crosslinked with glycerol
- MSBO Maleated soybean oil
- HEP 1-(2-hydroxyethyl)-2- pyrrolidone
- 2-octyl-1-dodecanol crosslinked with glycerol
- the mixture was cooled to 85 °C, and 29.8 g (1.3 mole equivalents) of 2-ethyl-1-hexanol was added, and the mixture was held at 85 °C for 6 hours.
- the mixture was heated to 90 °C, 16.2 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours.
- the amber, viscous product was characterized by NMR and IR. Yield was >96%.
- Example E4 Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and 1-naphthalenemethanol and crosslinked with glycerol
- MSBO Maleated soybean oil
- HEP 1-(2-hydroxyethyl)-2- pyrrolidone
- 1-naphthalenemethanol crosslinked with glycerol
- Example E5 Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and lauryl alcohol and crosslinked with glycerol
- MSBO 1-(2-hydroxyethyl)-2- pyrrolidone
- HEP 1-(2-hydroxyethyl)-2- pyrrolidone
- lauryl alcohol crosslinked with glycerol
- 161 g of MSBO made according to Example A1 and 7.34 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 34.4 g (1.3 mole equivalents) of lauryl alcohol was added, and the mixture was held at 85 °C for 6 hours.
- the mixture was cooled to 85 °C, and 59.4 g (1.3 mole equivalents) of behenyl alcohol was added, and the mixture was held at 85 °C for 6 hours.
- the mixture was heated to 90 °C, 12.24 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours.
- the amber, viscous product was characterized by NMR and IR. Yield was >96%.
- Example F1 Nonionic sunscreen emulsion using reaction product of Example E1 or Example E6
- Phase A is prepared by combining 60 parts by weight of water and 2 parts of propylene glycol. Carbomer (0.30 parts) is sprinkled in and mixed until smooth.
- Phase B is prepared by combining 3 parts avobenzone, 5 parts ethylhexyl salicylate, 5 parts octocrylene, 6 parts benzophenone-3, 10 parts homosalate, 4 parts PEG-100 stearate (and) glyceryl stearate, 2 parts of C12-C15 alkyl benzoate, benzyl O- toluate or phenethyl benzoate, and 1 part of the reaction product of Example E1 or Example E6 and heating to 75-80 °C.
- Phase B is added to phase A with homogenization. The homogenized mixture is cooled to 60-65 °C.
- Example F2 Water in silicone mineral (zinc and titanium) emulsion using reaction product of Example E1 or Example E6
- Phase A is prepared by combining 47.5 part by weight of water, 5 parts glycerin, 0.50 part hydroxyethyl cellulose, 0.50 part sodium chloride and 1.50 parts caprylyl glycol, phenoxyethanol, heating with mixing to 40-45 °C, homogenizing until uniform and cooling to 30- 35 °C.
- Phase B is prepared by pulverizing together 8 parts zinc oxide (and) ITT and 8 parts titanium dioxide (and) ITT.
- Phase C is prepared by combining 2.50 parts dimethicone (and) dimethicone/PEG-10/15 crosspolymer, 3 parts lauryl PEG-9 polydimethylsiloxyethyl dimethicone, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 4 parts phenyl trimethicone, 5 parts p, 5 parts octyl palmitate, 2.50 parts stearalkonium hectorite (and) caprylic/capric triglyceride (and) propylene carbonate, 2 parts of the reaction product of Example E1 or Example E6 and 5 parts butyloctyl salicylate and heating to 65 °C with mixing until clear.
- Phase C is cooled to 35-40 °C, and phase B is added with mixing at moderate high speed for about 10 minutes.
- Phase A is then added slowly to the mixture of phases B and C, with mixing at moderate to high speed for about 10 minutes.
- the mixture is cooled to room temperature.
- Example F3 Water in silicone mineral (zinc) emulsion using reaction product of Example E1 or Example E6 [00261] To prepare phase A, 5 parts by weight of dimethicone 1cst and 10 parts of dimethicone 2cst are combined and mixed using a high-lift mixing blade at high speed. Cetyl PEG/PPG-10/1 dimethicone (0.50 part) is added, and mixing at high speed is continued.
- phase C 0.20 part of hydroxyethyl cellulose is added with mixing to 37.82 parts water, and the mixture is heated to 80-85 °C. Once the hydroxyethyl cellulose is dispersed, 2 parts glycerin and 0.50 part 1,2-hexanediol are added and mixing at 85 °C is continued. Once hydroxyethyl cellulose is solubilized, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 1 part phenoxyethanol (and) benzoic acid (and) dehydroacetic acid and dehydroacetic acid and 1 part sodium chloride are added. Once the salt is dissolved, phase C is cooled to room temperature.
- Phase B is prepared by combining 1.50 parts potassium cetyl phosphate, 5 parts ethylhexyl triazone, 3 parts avobenzone, 3 parts bis-ethylhexyloxyphenol methoxyphenyl triazine, 5 parts octisalate, 10 parts homosalate, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 2 parts dimethicone, 1.50 parts behenyl alcohol (and) polyglycerol-10 pentastearate (and) sodium stearoyl lactate and 2 parts of the reaction product of Example E1 or Example E6 and heating to 75-80 °C.
- Phase B is added slowly to phase A, and the mixture is homogenized.
- the homogenized mixture is cooled to 60-65 °C, and 2 parts of 10% sodium hydroxide solution is added slowly with continued homogenization.
- the mixture is sweep mixed with pH adjustment, as needed, until cooled.
- Example F5 HydrosheerTM spray using reaction product of Example E1 or Example E6
- Phase A is prepared by combining 44 parts by weight of ethanol and 2 parts of the reaction product of Example E1 or Example E6 and mixing until fully combined.
- Phase B is prepared by combining 3 parts avobenzone, 5 parts octisalate, 10 parts homosalate, 8 parts octocrylene, 2 parts bemotrizinol, 3 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 5 parts diisopropyl adipate, 5 parts lauryl lactate, 5 parts C12-C15 lactate, 4 parts dicaprylyl carbonate and 3 parts isodecyl salicylate and heating with low heat until solids are fully dissolved. Phase B is then added to phase A and mixed until homogeneous.
- Example F6 Lipstick using reaction product of Example E1 or Example E6 [00267]
- Phase A is prepared by combining 12.97 parts by weight of ozokerite wax, 6.25 parts polyethylene, 6 parts octyldodecyl stearate, 5 parts diisopropyl adipate, 5.5 parts octyldodecyl stearoyl stearate, 3.44 parts pentaerythrityl tetraoctanoate, 4.4 parts C12-C15 alkyl lactate, 3.4 parts myristyl lactate, 3.7 parts hydrogenated polyisobutene, 2 parts of the reaction product of Example E1 or Example E6, 6.52 parts octocrylene, 4.66 parts ethylhexyl salicylate, 5.6 parts avobenzone, 8.36 parts homosalate and 1.2 parts caprylyl glycol (and) phenoxyethanol and heating to 90-95 °C with homogenization
- Phase B is prepared by combining and pulverizing 0.78 part Ricinus communis seed oil (and) CI 15850, 1.54 parts Ricinus communis (castor) seed oil (and) CI 77891 (and) polyhydroxystearic acid, 0.11 part Ricinus communis (castor) seed oil (and) CI 77491 (and) CI 77492(and) polyhydroxystearic acid, 2.99 parts mica (and) iron oxides CI 77491 (and) titanium dioxide, 11.17 parts synthetic fluorphogopite (and) titanium dioxide (and) tin oxide, 3.41 parts CI 77491 (and) CI 77891 (and) synthetic fluorphogopite, and 1 part water (and) butylene glycol (and) hexapeptide-3.
- Example G1 Seed coating using reaction product of Example D1 and polyvinyl alcohol
- a seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 4 parts polyvinyl alcohol, 1 part of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
- Example G2 Seed coating using reaction product of Example D1 and PEG 400
- a seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts PEG 400, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
- Example G3 Seed coating using reaction product of Example D1 and styrene acrylic copolymer
- a seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 2.5 parts styrene acrylic copolymer, 2.5 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
- Example G4 Seed coating using reaction product of Example D1 and vinyl pyrrolidone/vinyl acetate copolymer
- a seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts vinylpyrrolidone/vinyl acetate copolymer, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse.
- Example G5 Seed coating using reaction products of Examples B1 and E1 [00277] Reaction product of Example E1 (2.50 g), 7.50 g of the reaction product of Example B1, 45.56 g of water and 12.00 g of propylene glycol are combined and mixed using an overhead stirrer with a propellor blade at 400 rpm for 10 minutes. Xanthan gum (0.25 g) is added slowly and mixed for 15 minutes or until fully hydrated.
- Example G6 Seed coating using reaction products of Examples B1 and E6 [00279] Reaction product of Example E6 (2.50 g), 7.50 g of the reaction product of Example B1, 45.56 g of water and 12.00 g of propylene glycol are combined and mixed using an overhead stirrer with a propellor blade at 400 rpm for 10 minutes. Xanthan gum (0.25 g) is added slowly and mixed for 15 minutes or until fully hydrated.
- Example G7 Agrochemical oil dispersion of imidacloprid and bifenthrin using reaction products of Examples B1 and E1
- Imidacloprid (270 g) is dispersed in a mixture of soy methyl ester, 26.5 g of the reaction product of Example E1, 79.5 g of the reaction product of Example B1, and 67.0 g of attapulgite. The mixture is milled until the particle size reaches 1 to 5 ⁇ m.
- Example G8 Agrochemical oil dispersion of imidacloprid and bifenthrin using reaction products of Examples B1 and E6
- Imidacloprid (270 g) is dispersed in a mixture of soy methyl ester, 26.5 g of the reaction product of Example E6, 79.5 g of the reaction product of Example B1, and 67.0 g of attapulgite. The mixture is milled until the particle size reaches 1 to 5 ⁇ m.
- compositions and methods of the disclosed and/or claimed inventive concept(s) have been described in terms of particular aspects, it will be apparent to those of ordinary skill in the art that variations may be applied to the compositions and/or methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit and scope of the disclosed and/or claimed inventive concept(s). All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and/or claimed inventive concept(s).
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Abstract
Present application provides a renewable, modified natural oil that exhibits improved physical properties, comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (C) a base; and compositions comprising the reaction product thereof. Present application also relates to a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one amine functional group, and compositions comprising the reaction product thereof. Present application further relates to reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base; and compositions comprising the reaction product thereof.
Description
A MODIFIED MALEATED NATURAL OIL CONTAINING A LACTAM MOIETY, SALTS, COMPOSITIONS, AND USE THEREOF FIELD OF THE INVENTION [0001] The present application relates to a renewable, modified natural oil containing a lactam moiety, salts, and compositions thereof, that exhibit improved physical properties, and more particularly, to a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, and (C) a base. BACKGROUND OF THE INVENTION [0002] Natural oils, such as soybean and linseed oils, are one of the most promising raw materials for the synthesis of renewable compounds, including polymers, plastics, and plasticizers. These natural materials are inexpensive, highly abundant, come from reliable and sustainable sources, and have high potential for modification. Natural oils are generally blends of different triglycerides, the esterification product of fatty acids and glycerol, and contain varying degrees of unsaturation (i.e., double bonds). Oils can be characterized by a hydroxyl value and the fatty acid compositions. Both natural fatty acids and natural oils must be chemically modified to make them sufficiently reactive to allow structural alterations and polymerizations to occur because the olefin functional groups are relatively unreactive. Unsaturated double bonds in these compounds have been converted to epoxide functional groups and succinic anhydride functional groups, allowing the addition of many hydroxyl containing species to be introduced into the natural oils. [0003] Modified natural oils are natural oils that have been chemically functionalized by the chemical addition of epoxide (oxirane) and succinic anhydride functional groups. Examples include epoxidized and maleated soybean oil and linseed oil, unsaturated natural oils lend themselves to these chemical functionalizations. [0004] US Patent 9809538B2 describes a modified natural compound synthesized from epoxidized natural fatty acid, maleated natural fatty acid, epoxidized natural oil, or maleated natural oil; and lactam compound with hydroxyl(s) to form e.g., adhesive or beverage composition. [0005] A discussion of reaction scheme for the maleinization reaction in the vegetable oil is provided in the article “Maleated soybean oil and its multifunctional properties,” by Gripp, Anna
A., Steinberg, David C., published in Cosmetics Exhibition & Conference Proceedings, Barcelona, Mar.22-24, 1994. [0006] A discussion of reaction scheme for the maleation reaction in the vegetable oil is provided in the article “Microwave Assisted Syntheses of Vegetable Oil Based Monomer,” by Rafael T. Alarcon et al., published in Journal of Polymers and the Environment 28:1265–1278, 2020. [0007] A discussion of generalized reaction between maleic anhydride and unsaturated vegetable oils is provided in the Handbook of Maleic Anhydride Based Materials: Syntheses, Properties and Applications by Osama M. Musa in chapter 3 page 166, published in Springer International Publishing Switzerland 2016. [0008] US Patent 2754306A describes a reaction with a soybean oil, maleic anhydride and iso- octyl alcohol to provide an improved plasticizer for nitrocellulose compositions. [0009] PCT Application 2019113068A1 and 2005071050A1 describe a technology related to metalworking fluids comprising maleated soybean oil derivatives. [0010] A discussion of maleic anhydride polymerization and modified plant oils with polyols is provided in the article “Polymerization of Maleic Anhydride–Modified Plant Oils with Polyols,” by Tarik Eren, Selim H. Kusefoglu, Richard Wool published in Journal of Applied Polymer Science, Barcelona, Volume 90, Issue 1, Pages 197-202, 2003. [0011] EP Patent 2754306A describes an adhesive containing a polycondensate and a dienophile modified fatty acid as a cross-linking agent. [0012] PCT Application 2005071050A1 describes a metalworking fluid comprising oil in water emulsion from a reaction product of maleic anhydride and a triglyceride oil from a plant or land animal and further reacted with water, Group IA and IIA metals, ammonium hydroxide, various amines, alkanolamines, polyols, alkoxylated alkanolamines, poly (alkylene oxide)s, or polyamines or mixtures. [0013] Despite the renewability, biodegradability, sustainability, and beneficial functions provided by natural fatty acids, natural oils and their maleated counterparts, they exhibit properties that can limit their application. For example, both ESO and maleated soybean oil are insoluble and non-dispersible in water or alcohols. As a result, these fatty acids and oils may tend to exude or phase-separate from formulated compositions. This feature makes their formulation more difficult, often requiring additional ingredients to facilitate solutions, emulsions, or dispersions. Natural and epoxidized/maleated natural oils may not impart the desired property needed in end-
uses, such as solubilization capability, glass transition, flexibility, shine, and/or plasticization. Consequently, the performance (including, but are not limited to stability, resistance to phase separation, absorption, clean-up, solubility potential, staining potential, lubrication, film formation, uniformity of spreading, comedogenic tendency, ease of removal,) and aesthetic qualities (such as skin-feel, greasiness, shiny appearance) may be less than desired. Finally, although such fatty acids and oils are an important renewable material, they are not always the formulator’s first choice, and, in fact, often are not considered at all. [0014] Accordingly, there is a need for materials that are renewable, natural, and biodegradable having different and controllable chemical, physical, and/or mechanical properties such that the limitations found in natural and maleated natural oils are minimized or eliminated.
SUMMARY OF THE INVENTION [0015] The present application provides a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure: R
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between th
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0016] Another aspect of the present application discloses a reaction product of (A) maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium. Particularly, the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties. [0017] Yet another aspect of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between the
group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0018] Yet another aspect of the present application provides a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure: R
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
O group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic
structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0019] Yet another aspect of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between th
e group and th
e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0020] Yet another aspect of the present application provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group,
wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0021] Another aspect of the present application provides a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least one amine functional group, wherein the lactam moiety having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0022] Another aspect of the present application discloses a reaction product of (A) a maleated natural oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone. Particularly, the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties. [0023] Yet another aspect of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the group and th
group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0024] Yet another aspect of the present application provides a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0025] Yet another aspect of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and th
e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and
unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0026] Yet another aspect of the present application provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0027] Another aspect of the present application provides a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [0028] Another aspect of the present application discloses a reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium, wherein the reaction product has the structure:
wherein R7 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl
moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium. [0029] Yet another aspect of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [0030] Yet another aspect of the present application provides a personal care composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [0031] Yet another aspect of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between th
group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [0032] Yet another aspect of the present application provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the O H
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and
aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. DETAILED DESCRIPTION OF THE INVENTION [0033] Before explaining at least one aspect of the disclosed and/or claimed inventive concept(s) in detail, it is to be understood that the disclosed and/or claimed inventive concept(s) is not limited in its application to the details of construction and the arrangement of the components or steps or methodologies set forth in the following description or illustrated in the drawings. The disclosed and/or claimed inventive concept(s) is capable of other aspects or of being practiced or carried out in various ways. Also, it is to be understood that the phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting. [0034] Unless otherwise defined herein, technical terms used in connection with the disclosed and/or claimed inventive concept(s) shall have the meanings that are commonly understood by those of ordinary skill in the art. Further, unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular. [0035] The singular forms "a," "an," and "the" include plural forms unless the context clearly dictates otherwise specified or clearly implied to the contrary by the context in which the reference is made. The term “Comprising” and “Comprises of” includes the more restrictive claims such as “Consisting essentially of” and “Consisting of.” [0036] For purposes of the following detailed description, other than in any operating examples, or where otherwise indicated, numbers that express, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties to be obtained in carrying out the invention.
[0037] All percentages, parts, proportions, and ratios as used herein, are by weight of the total composition, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore; do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified. [0038] All publications, articles, papers, patents, patent publications, and other references cited herein are hereby incorporated herein in their entirety for all purposes to the extent consistent with the disclosure herein. [0039] As used herein, the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps. [0040] The term "branched and unbranched alkyl groups" refers to alkyl groups, which may be straight chained or branched. Branched groups include isopropyl, tert-butyl, and the like. [0041] References herein to “one embodiment” or “another embodiment” or “one aspect” or “another aspect” of the application include one or more such embodiment, or aspect, unless the context clearly dictates otherwise. [0042] The term “personal care composition” refers to a composition intended for use on or in the human body and may be an oral care composition, a hair care composition, a hair styling composition, a face care composition, a lip care composition, an eye care composition, a foot care composition, a nail care composition, a sun care composition, a deodorant composition, an antiperspirant composition, a cosmetic composition (including color cosmetics), a skin cleaning composition, an insect repellant composition, a shaving composition, a toothpaste, a mouthwash, a tooth whitener, a tooth stain remover, and/or a hygiene composition. Among their many uses, hair care and hair styling compositions find application in enhancing hair shine, cleansing hair, conditioning hair, repairing split ends, enhancing hair manageability, modulating hair stylability, protecting hair from thermal damage, imparting humidity resistance to hair and hair styles, promoting hair style durability, changing the hair color, straightening and/or relaxing hair, and/or providing protection from UV-A and/or UV-B radiation. Other personal care compositions, such as those for skin care and sun care compositions, are useful for protecting from UV-A and/or UV- B radiation, imparting water resistance or water proofness, moisturizing skin, decreasing and/or
minimizing the appearance of wrinkles, firming skin, decreasing or minimizing the appearance of skin blemishes (such as lentigo, skin discolorations, pimples, or acne), changing skin color (such as color cosmetics for the face, cheeks, eyelids, or eye lashes). Oral care compositions according to the invention may be used as denture adhesives, toothpastes, mouthwashes, tooth whiteners, and/or stain removers. Personal care compositions also are used for delivering an active (such as to the skin, hair, or oral cavity). [0043] The term “polymer” refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted or end-capped. Non-limiting examples of polymers include copolymers, terpolymers, tetrapolymers, quaternary polymers, and homologues. The term “copolymer” refers to a polymer consisting essentially of two or more different types of monomers polymerized to obtain the copolymer. [0044] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances. [0045] The term “natural oil” refers to compounds comprising triglycerides and may contain varying levels of fatty acids, monoglycerides, diglycerides and triglycerides refer to oil derived from plants or animal sources. Natural oils also include fatty acid glyceryl esters, which are synthesized by reacting glycerol with 1, 2, or 3 molar equivalents of a fatty acid or a mixture of fatty acids. These compounds can be mono, di or triglycerides of a single fatty acid or a mixture of fatty acids. [0046] As used herein the terms, “maleated natural oil” or “natural oil with maleated functionality”, can be used interchangeable without limiting the scope of the present disclosure, and refer to natural oil comprising at least one maleated functionality. Accordingly, the term "maleation" or "maleated" as used hereafter should be understood to mean "functionalization" insofar as the use of functionalizing reagents other than maleic anhydride are contemplated for use in the process of the invention. [0047] As used herein, the term “moiety” or “moieties” refers to a part or a functional group(s) of a molecule. [0048] The term, “maleated functionality” refers to moieties formed by attaching maleic anhydride to unsaturated fatty acyl chains, found in natural oils, by ene reaction. “Maleated functionality” includes but is not limited to the cyclic anhydride form (I), the diacid form (II), the
disodium dicarboxylate form (III), other dicarboxylate salt forms, and the half ester form (IV). Since the carbon-carbon double bond of maleic anhydride becomes a saturated carbon-carbon single bond during the ene reaction, the “maleated functionality” pictured in I, II, III and IV might also be called by one of ordinary skill in the art succinic anhydride, succinic acid, succinate salt or succinate half ester functionality. O
[0049] The term “base”, as used herein, refers to any substance which can alter the pH of a solution from a neutral pH of 7.0 to a basic pH (i.e., 7.1 to 14). Typically, a base is a substance of a large class of compounds with one or more of the following properties: bitter taste, slippery feeling in solution, ability to turn litmus blue and to cause other indicators to take on characteristic colors, ability to react with (neutralize) acids to form salts includes both organic base or an inorganic base and combinations thereof. [0050] The term “inorganic base”, as used herein, includes oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof. [0051] The term “functionalized” with reference to any moiety refers to the presence of one or more functional groups in the moiety. Various functional groups may be introduced in a moiety by way of one or more functionalization reactions known to a person having ordinary skill in the art. Non-limiting examples of functionalization reactions include: alkylation, epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, amination, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, Claisen condensation, Suzuki coupling, and the like. In one non-limiting embodiment, the term “functionalized” with reference to any moiety refers to the presence of one more functional group is selected from the group
consisting of alkyl, alkenyl, hydroxyl, carboxyl, halogen, alkoxy, amino, imino, and combinations thereof, in the moiety. [0052] The term “hydrocarbyl” includes straight-chain and branched-chain alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl groups, and combinations thereof with optional heteroatom(s). A hydrocarbyl group may be mono-, di- or polyvalent and have carbon chains containing 2 to 100 carbon atoms. [0053] The term “alkyl” refers to a functionalized or unfunctionalized, monovalent, straight- chain, branched-chain, or cyclic C1-C60 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkyl is a C1-C45 hydrocarbyl group. In another non-limiting embodiment, an alkyl is a C1-C30 hydrocarbyl group. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n- hexyl, n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n-dodecyl, tert-dodecyl, n- tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The definition of “alkyl” also includes groups obtained by combinations of straight-chain, branched-chain and/or cyclic structures. [0054] The term “aryl” refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenzofuranyl, benzo[b]thiophenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxyazinyl, pyrazolo[1,5-c]triazinyl, and the like. [0055] The term “aralkyl” refers to an alkyl group comprising one or more aryl substituent(s) wherein "aryl" and "alkyl" are as defined above. Non-limiting examples of aralkyl groups include benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.
[0056] The term “alkaryl” refers to an aryl group substituted with one or more alkyl groups, such as, for example, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-nonylphenyl, dimethylphenyl, or trimethylphenyl, which may optionally be further substituted on one or more of the carbon atoms of the radical. [0057] The term “alkaryl” refers to an aryl group comprising one or more alkyl substituent(s), wherein “alkyl” and “aryl” are as defined above. Non-limiting examples of alkaryl groups include 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-nonylphenyl, and the like. [0058] The term “alkylene” refers to a functionalized or unfunctionalized, divalent, straight- chain, branched-chain, or cyclic C1-C40 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkylene is a C1-C30 group. In another non- limiting embodiment, an alkylene is a C1-C20 group. Non-limiting examples of alkylene groups include:
[0059] The term “arylene” refers to a functionalized or unfunctionalized, divalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of arylene includes carbocyclic and heterocyclic groups. Non-limiting examples of arylene groups include phenylene, naphthalene, pyridinylene, and the like. [0060] The term “heteroatom” refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heteroatom(s) may be present as a part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups. The heteroatom(s) may also be present as a part of a ring such as in heteroaryl and heteroarylene groups. [0061] In a non-limiting embodiment, the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein
H 2 to 4 carbon atoms reside in the lactam ring between the
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base.
[0062] In another embodiment present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein: Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [0063] In another embodiment of the present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2. [0064] In another embodiment of the present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is 1-(2-hydroxyethyl)-2- pyrrolidone (HEP), having the structure:
[0065] Non-limiting examples of maleated natural oil used as reaction component (A) of the present application include maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof. [0066] Further, the maleated natural oil or natural oil with maleated functionality of the present application can be prepared by the maleation of natural oils. During maleation, one or more of an α,β-unsaturated carboxylic acid or anhydride thereof, for example, maleic anhydride reacts with unsaturated fatty acyl chains present in natural oils. The maleation of natural oils can occur under heating in three different ways. The first one is known as “Ene” reaction (reaction between an allylic moiety and an enophile in a pericyclic reaction), obtaining a triglyceride structure with anhydride moieties (succinic anhydride). The second one is a radical addition, which consumes a double bond in the fatty acid, incorporating the succinic anhydride into the natural oil structure. The final reaction is also a radical addition that incorporates the maleic anhydride into the natural oil structure without consuming C=C bonds (fatty acid chain and maleic anhydride); this reaction occurs due to abstraction of hydrogen atoms from two alkenes groups. [0067] The preparation of maleated natural oils is well known to persons skilled in the art. Accordingly, the maleated natural oils as used for the purpose of the present disclosure can be prepared by methods known in the related arts. In one non-limiting embodiment of the present disclosure, maleic anhydride and at least one natural oil can be reacted together at elevated temperatures. In one non-limiting embodiment of the present disclosure, the maleation can be carried out at a temperature varying in the range of from about 150 °C to about 250 °C. In another non-limiting embodiment of the present disclosure, the maleation can be carried out at a temperature of from about 200 °C to about 230 °C, or from about 180 °C to about 190 °C.
[0068] Further, the maleation can be carried out for a time period varying from about 0.5 hours to about 14 hours. In another non-limiting embodiment of the present disclosure, the reaction time can vary from about 1 hour to about 5 hours, or from about 2 hours to about 6 hours, or from about 6 hours to 10 hours. [0069] In one non-limiting embodiment of the present disclosure, the mole ratio of maleic anhydride to natural can be equal to 1. In a still another non-limiting embodiment of the present disclosure, the mole ratio can vary from about 1 to about 2, or from about 1 to about 2.8, or from about 1 to about 3.2 moles of maleic anhydride for each mole of natural oil. During maleation, the mole ratio of maleic anhydride to natural oil in some embodiments is equal to 1, in other embodiments from 1 to 2, in other embodiments from 1 to 2.8 and in still other embodiments from 1 to 3.2 moles of maleic anhydride for each mole of natural oil. [0070] In another embodiment, the reaction component (A) maleated natural oil of the present application is a maleated soybean oil. [0071] In another embodiment of the present application, the reaction component (C) base is selected from the group consisting of inorganic bases, organic bases, or combinations thereof. [0072] Non-limiting examples of inorganic bases used as the reaction component (C) of the present application include, oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof. [0073] Examples of inorganic base used as the reaction component (C) of the present application is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, or combinations thereof. [0074] Non-limiting examples of the reaction component (C) of the present application include, alkali metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr); alkaline earth metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra); transition metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn),
yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), cadmium (Cd), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), mercury (Hg), rutherfordium (Rf), dubnium (Db), seaborgium (Sg), bohrium (Bh), hassium (Hs), meitnerium (Mt), darmstadtium (Ds) and roentgenium (Rg); or combinations thereof. [0075] Non-limiting examples of organic bases used as the reaction component (C) of the present application include, ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, or combinations thereof. [0076] Another aspect of the present application discloses a reaction product of (A) maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium. Particularly, the reaction product is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties. [0077] In a non-limiting embodiment, the reaction product of the present application comprises one or more structure(s) selected from: N
[0078] In another embodiment, the reaction product of the present application is used in end- user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions. [0079] Yet another embodiment of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R H 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0080] In another embodiment, the coating composition of the present application comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [0081] In another embodiment, the coating composition of the present application further comprises at least one additive in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to
about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [0082] Examples of additives used in the coating composition of the present application include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers, or combinations thereof. [0083] In another embodiment, the coating composition of the present application is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings. [0084] In another embodiment, the coating composition of the present application is coated on a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non- woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers. [0085] Yet another embodiment of the present application provides a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between th
group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0086] In another embodiment, the personal care composition of the present application comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [0087] In another embodiment, the personal care composition of the present application further comprises at least one personal care active ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%;
or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [0088] Examples of personal care active ingredient used in the personal care composition of the present application include, but are not limited to, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof. [0089] Non-limiting examples of personal care active ingredient used in the personal care composition of the present application include, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, or combinations thereof. [0090] Examples of the personal care composition of the present application includes, but are not limited to, body wash composition, skin lotion composition, sunscreen composition, anti- wrinkle composition, moisturizer composition, facial cleaning composition, lipstick composition, lip-gloss composition, mascara composition, foundation composition, anti-perspirant composition, shaving composition, hair conditioner composition, anti-perspirant composition, deodorant composition, hair rinse composition, hair shampoo composition, hair styling composition, make- up remover composition, or oral care composition. [0091] In another embodiment, the personal care composition of the present application is a formulation of an aqueous or a non-aqueous composition in the form of, but are not limited to, sprays, lotions, mousses, fluids, serums, solutions, suspensions, perms, emulsions, gels, mists,
vesicles, dispersions, pastes, creams, solid sticks, shampoos, balms, wipes, milks, foams, jellies, or liquids. [0092] Yet another embodiment of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between th
e group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0093] In another embodiment, the pharmaceutical composition of the present application comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from
about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [0094] In another embodiment, the pharmaceutical composition of the present application further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [0095] Examples of pharmaceutically accepted excipients used in the pharmaceutical composition of the present application include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof. [0096] Non-limiting examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition of the present application include, foaming agents, mucoadhesive agents, preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof. [0097] In another embodiment, the pharmaceutical composition of the present application is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions,
liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension. [0098] Yet another embodiment of the present application provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and (C) a base. [0099] In another embodiment, the agricultural composition of the present application comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about
70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00100] In another embodiment, the agricultural composition of the present application further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00101] Examples of one or more agriculturally active ingredient used in the agricultural composition of the present application include, but not limited to, fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof. [00102] In another embodiment, the additional ingredient used in the agricultural composition of the present application further includes an adjuvant or an inert ingredient. [00103] Non-limiting examples of the adjuvants used in the agricultural composition of the present application include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof. [00104] Non-limiting examples of inert ingredients used in the agricultural composition of the present application include, solvents, liquid carriers, solid carriers or fillers, surfactants,
solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or mixtures thereof. [00105] In another non-limiting embodiment, the agricultural composition of the present application is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition. [00106] In another non-limiting embodiment, the agricultural composition of the present application is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder. [00107] In a non-limiting embodiment, the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and, (B) a lactam moiety having at least one amine functional group, wherein the lactam moiety having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the group; Q is
selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00108] In another embodiment present application, the reaction component (B) comprising a lactam having at least one amine functional group is selected from the group consisting of:
and combinations thereof, wherein: Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R1, R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00109] In embodiment of the present application, the reaction component (B) comprising a lactam having at least one amine functional group is selected from the group consisting of:
, and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–). [00110] In another embodiment of the present application, the reaction component (B) comprising a lactam having at least one amine functional group is 1-(2-aminoethyl)-2-pyrrolidone, having the structure:
[00111] Non-limiting examples of maleated natural oil used as the reaction component (A) include maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof. [00112] In another embodiment, the reaction component (A) maleated natural oil is a maleated soybean oil. [00113] Another aspect of the present application discloses a reaction product of (A) maleated natural oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone. Particularly, the reaction product is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties.As used herein, the reaction product comprises one or more structure(s) selected from:
wherein, R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
[00114] In another embodiment, the reaction product disclosed hereinabove is used in end-user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions. [00115] Yet another aspect of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between th
group and t
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00116] In another embodiment, the coating composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%;
or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00117] In another embodiment, the coating composition further comprises at least one additive in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00118] Examples of additives used in the coating composition include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers, or combinations thereof. [00119] In another embodiment, the coating composition is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non- metallic coatings. [00120] In another embodiment, the coating composition is coated on a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air
bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers. [00121] Yet another aspect of the present application provides a personal care comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: R
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between th
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00122] In another embodiment, the personal care composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition.
[00123] In another embodiment, the personal care composition further comprises at least one personal care active ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00124] Examples of personal care active ingredients used herein include, but are not limited to, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof. [00125] Non-limiting examples of personal care active ingredient used herein include, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, or combinations thereof. [00126] Examples of the personal care composition include, but are not limited to, body wash composition, skin lotion composition, sunscreen composition, anti-wrinkle composition, moisturizer composition, facial cleaning composition, lipstick composition, lip-gloss composition, mascara composition, foundation composition, anti-perspirant composition, shaving composition, hair conditioner composition, anti-perspirant composition, deodorant composition, hair rinse composition, hair shampoo composition, hair styling composition, make-up remover composition, or oral care composition.
[00127] In another embodiment, the personal care composition is a formulation of an aqueous or a non-aqueous composition in the form of, but are not limited to, sprays, lotions, mousses, fluids, serums, solutions, suspensions, perms, emulsions, gels, mists, vesicles, dispersions, pastes, creams, solid sticks, shampoos, balms, wipes, milks, foams, jellies, or liquids. [00128] Yet another aspect of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00129] In another embodiment, the pharmaceutical composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80
wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00130] In another embodiment, the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00131] Examples of pharmaceutically accepted excipients used herein include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof. [00132] Examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition include, but are not limited to, foaming agents, mucoadhesive agents, preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof. [00133] In another embodiment, the pharmaceutical composition is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension. [00134] Yet another aspect of the present application provides an agricultural composition
comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) a lactam moiety having at least amine functional group, wherein the lactam having at least one amine functional group has the structure: R
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein R 2 to 4 carbon atoms reside in the lactam ring between the
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00135] In another embodiment, the agricultural composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00136] In another embodiment, the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to
about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00137] Examples of one or more agriculturally active ingredient used herein include, but not limited to, fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof. [00138] In another embodiment, the additional ingredient used in the agricultural composition further includes an adjuvant or an inert ingredient. [00139] Non-limiting examples of the adjuvants used herein include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof. [00140] Non-limiting examples of inert ingredients used herein include, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or mixtures thereof. [00141] In another non-limiting embodiment, the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide,
avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition. [00142] In another non-limiting embodiment, the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder. [00143] In a non-limiting embodiment, the present application discloses a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam moiety having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between t
e group and t
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic
moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00144] In another embodiment present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein: Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms. [00145] In another embodiment of the present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
[00146] In another embodiment of the present application, the reaction component (B) comprising a lactam having at least one hydroxyl, thiol or amine functional group is 1-(2- hydroxyethyl)-2-pyrrolidone (HEP), having the structure: H
. [00147] Non-limiting examples of maleated natural oil used as reaction component (A) include maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof. [00148] Further, the maleated natural oil or natural oil with maleated functionality of the present application can be prepared by the maleation of natural oils. During maleation, one or more of an α,β-unsaturated carboxylic acid or anhydride thereof, for example, maleic anhydride reacts with unsaturated fatty acyl chains present in natural oils. The maleation of natural oils can occur under heating in three different ways. The first one is known as “Ene” reaction (reaction between an allylic moiety and an enophile in a pericyclic reaction), obtaining a triglyceride structure with anhydride moieties (succinic anhydride). The second one is a radical addition, which consumes a double bond in the fatty acid, incorporating the succinic anhydride into the natural oil structure. The final reaction is also a radical addition that incorporates the maleic anhydride into the natural oil structure without consuming C=C bonds (fatty acid chain and maleic anhydride); this reaction occurs due to abstraction of hydrogen atoms from two alkenes groups. [00149] The preparation of maleated natural oils is well known to persons skilled in the art. Accordingly, the maleated natural oils as used for the purpose of the present disclosure can be prepared by methods known in the related arts. In one non-limiting embodiment of the present disclosure, maleic anhydride and at least one natural oil can be reacted together at elevated temperatures. In one non-limiting embodiment of the present disclosure, the maleation can be
carried out at a temperature varying in the range of from about 150 °C to about 250 °C. In another non-limiting embodiment of the present disclosure, the maleation can be carried out at a temperature of from about 200 °C to about 230 °C, or from about 180 °C to about 190 °C. [00150] Further, the maleation can be carried out for a time period varying from about 0.5 hours to about 14 hours. In another non-limiting embodiment of the present disclosure, the reaction time can vary from about 1 hour to about 5 hours, or from about 2 hours to about 6 hours, or from about 6 hours to 10 hours. [00151] In one non-limiting embodiment of the present disclosure, the mole ratio of maleic anhydride to natural can be equal to 1. In a still another non-limiting embodiment of the present disclosure, the mole ratio can vary from about 1 to about 2, or from about 1 to about 2.8, or from about 1 to about 3.2 moles of maleic anhydride for each mole of natural oil. During maleation, the mole ratio of maleic anhydride to natural oil in some embodiments is equal to 1, in other embodiments from 1 to 2, in other embodiments from 1 to 2.8 and in still other embodiments from 1 to 3.2 moles of maleic anhydride for each mole of natural oil. [00152] In another embodiment, the reaction component (A) maleated natural oil is a maleated soybean oil. [00153] In another non-limiting embodiment, the reaction component (C), functionalized or unfunctionalized moiety includes hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety. [00154] In another non-limiting embodiment of the aforementioned invention, the hydrophobic moiety and/or hydrophilic moiety is selected from those of a hydrocarbyl alcohol, a hydrocarbyl amine, a silicon-based compound, and combinations thereof. [00155] Hydrocarbyl alcohols are classified as primary, secondary and tertiary alcohols, based on the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. Each classification of alcohol has a general formula. For example, the general formula for primary alcohols is
the general formula for secondary alcohols is and
the general formula for tertiary alcohols is OH
wherein R, R′ and R″ stand for different alkyl, alkylene, aryl, aralkyl, and arylene groups. [00156] Examples of the hydrophobic moiety include those of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; silicon-based compounds; and combinations thereof. [00157] Examples of the hydrophilic moiety include those of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; silanes; and combinations thereof. [00158] Preferably, the silane is functionalized with an alcohol, an amine or combinations thereof. Examples of the hydrophobic alcohol include hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1- octanol, 2-hexyl-1-decanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, behenyl alcohol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4- methyl-1-pentanol, and mixtures thereof. Examples of the hydrophilic alcohol include methanol, ethanol, propanol, isopropanol, butanol, methoxypolyethylene glycol, and mixtures thereof. Examples of the hydrophilic polyol include, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, and mixtures thereof.
[00159] Examples of hydrophobic amine include benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof. Examples of the hydrophilic amine include diethanolamine, serinol hydrochloride, 2-amino-2-ethyl-1,3-propanediol, dimethylamine, and mixtures thereof. [00160] Examples of the hydrophobic polyol include 1,6-hexanediol, 1,7-heptanediol, 1,8- octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, poly(tetramethylene ether) glycol, poly(tetramethylene carbonate), poly(hexamethylene carbonate) and castor oil. [00161] Examples of the hydrophobic silicon-based compound includes aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy) propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane- hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof. Examples of hydrophilic silane include, 3-aminopropylsilanetriol, N-(2-aminoethyl)-3-aminopropylsilanetriol, and mixtures thereof. [00162] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl alcohol that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional. [00163] In one non-limiting embodiment, the hydrophilic polyol is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose and mixtures thereof. [00164] In one non-limiting embodiment, the amines selected from the group consisting of primary, secondary, and tertiary amines and combinations thereof.
[00165] Hydrocarbyl amines are classified as primary, secondary, or tertiary, based on the number of carbon atoms attached to the amine nitrogen atom. The general formula for primary amine is
the general formula for secondary amine is
and the general formula for tertiary amine is
wherein R1, R2 and R3 stand for the same or different alkyl, alkylene, aryl, aralkyl, or arylene groups. [00166] In one non-limiting embodiment, the hydrophobic moiety is that of a hydrocarbyl amine that contains from about 6 to about 36 carbon atoms and that is linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional. [00167] In one non-limiting embodiment, the silicon-based compound is a compound having the structure
wherein R stands for different alkyl, alkylene, aryl, aralkyl, arylene, hetero groups functionalized with at least one or more alcohol, amine or a combination thereof and n has the value of 1 to 10. [00168] In one non-limiting embodiment, the silicon-based compound is a siloxane, or a silane functionalized with an alcohol, an amine or a combination thereof. [00169] In one non-limiting embodiment, the silicon-based compound is a linear, branched, saturated, unsaturated, aliphatic, aromatic, monofunctional or multifunctional compound.
[00170] In one non-limiting embodiment, the silicon-based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane–dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1-dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]-dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane and mixtures thereof.
aminopropylmethylsiloxane n-ethylaminoisobutyl terminated dimethylsiloxane (amino siloxane) polydimethylsiloxane (amino siloxane)
poly(1,1-dimethylsilazane) telomer aminopropyl terminated polydimethylsiloxane (amino siloxane)
Monoaminopropylterminated (tetramethylpiperidinyloxy)propylmethylsilox polydimethylsiloxane (amino siloxane) ane]-dimethylsiloxane copolymer
Polydimethylsiloxane carbinol (hydroxyl) terminated polydimethylsiloxane
monocarbinol terminated monocarbinol terminated functional polydimethylsiloxane polydimethylsiloxane
[bis(hydroxyethyl)amine]terminated silanol terminated polydimethylsiloxane polydimethylsiloxane
silanol terminated polydiphenylsiloxane dodecylmethylsiloxane- hydroxypolyalkyleneoxypropyl methylsiloxane
[00171] In one non-limiting embodiment, the silicon-based compound is hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol and mixtures thereof.
3-aminopropylsilanetriol (silica-based n-(2-aminoethyl)-3-aminopropylsilanetriol alcohol) [00172] In another embodiment of the present application, the reaction component (D) base is selected from the group consisting of inorganic bases, organic bases, or combinations thereof. [00173] Non-limiting examples of inorganic bases used as the reaction component (D) include oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof. [00174] Examples of the inorganic base used as the reaction component (D) are oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, or combinations thereof. [00175] Non-limiting examples of the reaction component (D) base of the present application include, alkali metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr); alkaline earth metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra); transition metal bases selected from oxides, hydroxides, carbonates, or bicarbonates of scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), cadmium (Cd), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), mercury (Hg), rutherfordium (Rf), dubnium (Db), seaborgium (Sg), bohrium (Bh), hassium (Hs), meitnerium (Mt), darmstadtium (Ds) and roentgenium (Rg); or combinations thereof.
[00176] Non-limiting examples of organic bases used as the reaction component (D) include, ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, or combinations thereof. [00177] Another aspect of the present application discloses a reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00178] In a non-limiting embodiment, the reaction product disclosed herein has the structure:
wherein R7 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium. [00179] In a non-limiting embodiment, the reaction product comprises one or more structure(s) selected from:
wherein R7 is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl- 1-dodecyl, or mixtures thereof; and wherein R8, R9 and R10 are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms. [00180] In another non-limiting embodiment, the reaction product disclosed herein is a polymer having the structure:
wherein n is greater than 1; R11 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium. [00181] In another non-limiting embodiment, the reaction product disclosed herein is a polymer having one or more structure(s) selected from:
wherein 1 < n < 30; wherein R8, R9 and R10 are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and more particularly, R11 is selected from -CH2CH2CH2-,
[00182] In another embodiment, the reaction product of the present application is used in end- user compositions selected from, but not limited to, skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield
compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions. [00183] Yet another aspect of the present application provides a coating composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein H 2 to 4 carbon atoms reside in the lactam ring between th
e group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00184] In another embodiment, the coating composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to
about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00185] In another embodiment, the coating composition further comprises at least one additive in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00186] Examples of additives used in the coating composition include, but are not limited to, film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers, or combinations thereof. [00187] In another embodiment, the coating composition is an aqueous or a non-aqueous composition used for, but are not limited to, lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non- metallic coatings. [00188] In another embodiment, the coating composition is coated on a substrate selected from, but are not limited to, porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass,
polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers. [00189] Yet another aspect of the present application provides a personal care composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00190] In another embodiment, the personal care composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about
35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00191] In another embodiment, the personal care composition further comprises at least one personal care active ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00192] Examples of personal care active ingredients used herein include, but are not limited to, color agents, hair care agents, skin care agents, and sun care agents, or combinations of two or more thereof. [00193] Non-limiting examples of personal care active ingredient used herein include, fragrances, preservatives, solvents, propellants, exfoliants, surfactants, skin cell renewal agents, anti-acne medications, antiperspirant compounds, sunscreens, decomposition products of oils or fats, water- insoluble ingredients, oxidizing agents, conditioning agents, humectants, pH adjusting buffers, waxes, mineral oils, emulsifiers, fatty substances, gelling agents, thickeners, moisturizers, emollients, hydrophilic or lipophilic active agent, antioxidants, sequestering agents, acidifying or basifying agents, fillers, dyestuffs, plant extracts, proteins, peptides, neutralizing agents, solvents, anti-dandruff ingredients, reducing agents, or combinations thereof. [00194] Examples of the personal care composition include, but are not limited to, body wash composition, skin lotion composition, sunscreen composition, anti-wrinkle composition,
moisturizer composition, facial cleaning composition, lipstick composition, lip-gloss composition, mascara composition, foundation composition, anti-perspirant composition, shaving composition, hair conditioner composition, anti-perspirant composition, deodorant composition, hair rinse composition, hair shampoo composition, hair styling composition, make-up remover composition, or oral care composition. [00195] In another embodiment, the personal care composition is a formulation of an aqueous or a non-aqueous composition in the form of, but are not limited to, sprays, lotions, mousses, fluids, serums, solutions, suspensions, perms, emulsions, gels, mists, vesicles, dispersions, pastes, creams, solid sticks, shampoos, balms, wipes, milks, foams, jellies, or liquids. [00196] Yet another aspect of the present application provides a pharmaceutical composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and the
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic
moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00197] In another embodiment, the pharmaceutical composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00198] In another embodiment, the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00199] Examples of pharmaceutically accepted excipients used herein include, but are not limited to, binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti-adherents, surfactants, pH modifiers, coloring agents, diluents, sweeteners, anti-tacking agents, colorants or combinations thereof. [00200] Examples of other pharmaceutically accepted ingredients that can be used in the pharmaceutical composition include, but are not limited to, foaming agents, mucoadhesive agents,
preservatives, stabilizers, moisturizers, buffers, antibacterial agents, antioxidants or absorption enhancers, complexing agents, ionic dispersion modulators, fillers, suspensions, taste-masking agents, dispersants, surfactants, lubricant, diluent, solubilizer, wetting agent, plasticizer, stabilizer, penetration enhancer, disinfectants, foaming agents, antioxidants, or two or more combinations thereof. [00201] In another embodiment, the pharmaceutical composition is in the form of, but are not limited to, solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials or a non-aqueous or aqueous liquid suspension. [00202] Yet another aspect of the present application provides an agricultural composition comprising a reaction product of (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group, wherein the lactam having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and th
e group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; (C) a functionalized or
unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base. [00203] In another embodiment, the agricultural composition disclosed hereinabove comprises the reaction product in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.% based on the total weight of the coating composition. [00204] In another embodiment, the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in a range varied from about 0.1 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.% ; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 95 wt.%; or from about 95 wt.% to about 99.9 wt.% based on the total weight of the coating composition. [00205] Examples of one or more agriculturally active ingredient used herein include, but not limited to, fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti-parasites, antimicrobials, or combinations thereof.
[00206] In another embodiment, the additional ingredient used in the agricultural composition further includes an adjuvant or an inert ingredient. [00207] Non-limiting examples of the adjuvants used herein include acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners, or mixtures thereof. [00208] Non-limiting examples of inert ingredients used herein include, solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, or mixtures thereof. [00209] In another non-limiting embodiment, the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition. [00210] In another non-limiting embodiment, the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder. [00211] Further, certain aspects of the present application are illustrated in detail by way of the following examples. The examples are given herein for illustration of the application and are not intended to be limiting thereof.
EXAMPLES [00212] Example A1: Grafting of maleic anhydride onto soybean oil: [00213] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 600 g of soybean oil and 204 g (3 mole equivalents based on soybean oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 6-8 hours. Completion of the reaction was indicated by NMR, and LC indicated <0.5% of residual maleic anhydride. [00214] Example A2: Grafting of maleic anhydride onto palm oil [00215] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of palm oil and 23 g (2 mole equivalents based on palm oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%. [00216] Example A3: Grafting of maleic anhydride onto canola oil [00217] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of canola oil and 22.2 g (2 mole equivalents based on canola oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%. [00218] Example A4: Grafting of maleic anhydride onto sunflower oil [00219] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of sunflower oil and 22.4 g (2 mole equivalents based on sunflower oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚C and then held at 210 ˚C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%.
[00220] Example A5: Grafting of maleic anhydride onto castor oil [00221] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter, and mechanical stirrer was charged with 100 g of castor oil and 21 g (2 mole equivalents based on castor oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 ˚ C and then held at 210 ˚ C for 8-10 hours. The amber, viscous product was characterized by NMR, and LC indicated <1% of residual maleic anhydride. Yield was >96%. [00222] Example A6: Grafting of maleic anhydride onto chickpea oil [00223] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of chickpea oil and 38 g (3.4 mole equivalents relative to chickpea oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 10-14 hours. The amber, viscous product was characterized by NMR, and LC indicated <0.5% of residual maleic anhydride. Yield of maleated chickpea oil was >96%. [00224] Example A7: Grafting of maleic anhydride onto clary sage oil [00225] A 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen sparge adapter and mechanical stirrer was charged with 100 g of clary sage oil and 51.5 g (3 mole equivalents relative to clary sage oil) of maleic anhydride. The mixture was sparged at room temperature with nitrogen for 15 minutes, heated slowly from room temperature to 210 °C and then held at 210 °C for 8 hours. The amber, viscous product was characterized by NMR, and LC indicated <0.5% of residual maleic anhydride. Yield of maleated clary sage oil was >96%. [00226] Example B1: Sodium salt of maleated soybean oil (MSBO) from aqueous sodium hydroxide [00227] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of maleated soybean oil (MSBO) from Example A1 was heated to 90 °C, and a mixture of 20.20 g (3 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 70 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%.
[00228] Example B2: Sodium salt of maleated soybean oil (MSBO) from sodium carbonate [00229] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 was heated to 90 °C, and 27.86 g (3 mole equivalents based on soybean oil) of sodium carbonate dissolved in 85 g of water was added over 3 hours, controlling the foam formation. The reaction was held at 90 °C for 3 hours. The product contained 56 weight % solids and was characterized by IR. Yield was >96%. [00230] Example B3: Sodium salt of maleated soybean oil (MSBO) from aqueous sodium hydroxide [00231] In a 1-L , 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 123 g of MSBO from Example A1 was heated to 90 °C, and a mixture of 9.04 g (2 mole equivalents based on soybean oil) of 50% aqueous sodium hydroxide and 80 g of water was added over 1 hour, controlling foaming. After completing the addition, the mixture was held at 90 °C for 3 hours. The product contained 70 weight % solids and was characterized by IR and NMR. Yield was >96%. [00232] Example C1: Grafting of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) onto maleated soybean oil (MSBO) [00233] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and either 0.5, 1, 1.5, 2, 2.5 or 3 mole equivalents, relative to MSBO, of 1-(2-hydroxyethyl)-2-pyrrolidone (HEP) were combined, heated to 120 °C and held at 120 °C for 6 hours. The amber, viscous product was characterized by NMR and IR, and GC indicated <5% of residual HEP. Yield was >96%. [00234] Example C2: Grafting of 1-(2-aminoethyl)-2-pyrrolidone onto maleated soybean oil (MSBO) [00235] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 100 g of MSBO from Example A1 and 10.0 g (1 mole equivalent, relative to MSBO) of 1-(2-aminoethyl)-2-pyrrolidone are combined, heated to 80 °C and held at 80 °C for 6 hours. [00236] Example D1: Sodium salt of maleated soybean oil (MSBO) reacted with 1-(2- hydroxyethyl)-2-pyrrolidone (HEP) [00237] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C1 was heated to 85 °C. Water and
50% aqueous sodium hydroxide were added over 60 minutes to create a final solution that was 50 weight % solids, and the mixture was held at 85 °C for 4 hours. The amount of sodium hydroxide added was sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with HEP into the corresponding sodium carboxylate salt. The amber liquid product was characterized by NMR and IR. Yield of MSBO-HEP adduct sodium salt was >98%. [00238] Example D2: Lithium salt of maleated soybean oil (MSBO) reacted with 1-(2- hydroxyethyl)-2-pyrrolidone (HEP) [00239] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter, and mechanical stirrer, 152.1 g of MSBO made according to Example A1 and 41.8g (2.5 mole equivalents relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The amber, viscous product was cooled to 80 °C, and 9.31 g (3 mole equivalents relative to MSBO) of lithium hydroxide dissolved in 204 g of water was added over 1 hour to create a final solution that was 50 weight % solids. The mixture was heated to 85 °C and held at 85 °C for 2 hours. The amber product was characterized by NMR and IR. Yield was >96%. [00240] Example D3: Sodium salt of maleated soybean oil (MSBO) reacted with 1-(2- aminoethyl)-2-pyrrolidone [00241] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen purge adapter and mechanical stirrer, 100 g of the product from Example C2 is heated to 85 °C. Water and 50% aqueous sodium hydroxide are added over 60 minutes to create a final solution that is 50 weight % solids, and the mixture is held at 85 °C for 4 hours. The amount of sodium hydroxide added is sufficient to convert each carboxylic acid group generated by hydrolysis of anhydride or reaction of anhydride with 1-(2-aminoethyl)-2-pyrrolidone into the corresponding sodium carboxylate salt. [00242] Example E1: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and 2-octyl-1-dodecanol and crosslinked with glycerol [00243] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example A1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) was
added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00244] Example E2: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and 2-ethyl-1-hexanol and crosslinked with glycerol [00245] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 200 g of MSBO made according to Example A1 and 9.10 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.8 g (1.3 mole equivalents) of 2-ethyl-1-hexanol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 16.2 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00246] Example E3: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and benzyl alcohol and crosslinked with glycerol [00247] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, 20.0 g (1.3 mole equivalents) of benzyl alcohol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00248] Example E4: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and 1-naphthalenemethanol and crosslinked with glycerol [00249] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 167 g of MSBO made according to Example A1 and 11.0 g (0.6 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 29.2 g (1.3 mole equivalents) of 1-naphthalenemethanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (13.1 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%.
[00250] Example E5: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and lauryl alcohol and crosslinked with glycerol [00251] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 161 g of MSBO made according to Example A1 and 7.34 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 34.4 g (1.3 mole equivalents) of lauryl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 13.1 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00252] Example E6: Maleated soybean oil (MSBO) reacted with 1-(2-hydroxyethyl)-2- pyrrolidone (HEP) and behenyl alcohol and crosslinked with glycerol [00253] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 151 g of MSBO made according to Example A1 and 6.87 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was cooled to 85 °C, and 59.4 g (1.3 mole equivalents) of behenyl alcohol was added, and the mixture was held at 85 °C for 6 hours. The mixture was heated to 90 °C, 12.24 g (1.0 mole equivalent) of glycerol was added, and the mixture was held at 90 °C for 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00254] Example E7: Maleated soybean oil (MSBO) reacted with 1-(2-aminoethyl)-2- pyrrolidone and 2-octyl-1-dodecanol and crosslinked with glycerol [00255] In a 1-L, 4-neck kettle equipped with a thermocouple, condenser, nitrogen adapter, and mechanical stirrer, 211 g of MSBO made according to Example A1 and 9.69 g (0.4 mole equivalent relative to MSBO) of HEP were combined, heated to 125 °C and held at 125 °C for 8 hours. The mixture was adjusted to 85 °C, and 72.8 g (1.3 mole equivalents) of 2-octyl-1-dodecanol was added, and the mixture was held at 85 °C for 8 hours. Glycerol (17.3 g, 1.0 mole equivalent) was added, and the mixture was held at 85 °C for an additional 6 hours. The amber, viscous product was characterized by NMR and IR. Yield was >96%. [00256] Example F1: Nonionic sunscreen emulsion using reaction product of Example E1 or Example E6
[00257] Phase A is prepared by combining 60 parts by weight of water and 2 parts of propylene glycol. Carbomer (0.30 parts) is sprinkled in and mixed until smooth. Methylparaben (1 part by weight) is added and mixed until combined. Phase B is prepared by combining 3 parts avobenzone, 5 parts ethylhexyl salicylate, 5 parts octocrylene, 6 parts benzophenone-3, 10 parts homosalate, 4 parts PEG-100 stearate (and) glyceryl stearate, 2 parts of C12-C15 alkyl benzoate, benzyl O- toluate or phenethyl benzoate, and 1 part of the reaction product of Example E1 or Example E6 and heating to 75-80 °C. Phase B is added to phase A with homogenization. The homogenized mixture is cooled to 60-65 °C. Ten percent sodium hydroxide solution (0.70 part) is added to the homogenized mixture of phases A and B with continued homogenization. The mixture is sweep mixed with pH adjustment, as needed, until cooled. [00258] Example F2: Water in silicone mineral (zinc and titanium) emulsion using reaction product of Example E1 or Example E6 [00259] Phase A is prepared by combining 47.5 part by weight of water, 5 parts glycerin, 0.50 part hydroxyethyl cellulose, 0.50 part sodium chloride and 1.50 parts caprylyl glycol, phenoxyethanol, heating with mixing to 40-45 °C, homogenizing until uniform and cooling to 30- 35 °C. Phase B is prepared by pulverizing together 8 parts zinc oxide (and) ITT and 8 parts titanium dioxide (and) ITT. Phase C is prepared by combining 2.50 parts dimethicone (and) dimethicone/PEG-10/15 crosspolymer, 3 parts lauryl PEG-9 polydimethylsiloxyethyl dimethicone, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 4 parts phenyl trimethicone, 5 parts p, 5 parts octyl palmitate, 2.50 parts stearalkonium hectorite (and) caprylic/capric triglyceride (and) propylene carbonate, 2 parts of the reaction product of Example E1 or Example E6 and 5 parts butyloctyl salicylate and heating to 65 °C with mixing until clear. Phase C is cooled to 35-40 °C, and phase B is added with mixing at moderate high speed for about 10 minutes. Phase A is then added slowly to the mixture of phases B and C, with mixing at moderate to high speed for about 10 minutes. The mixture is cooled to room temperature. [00260] Example F3: Water in silicone mineral (zinc) emulsion using reaction product of Example E1 or Example E6 [00261] To prepare phase A, 5 parts by weight of dimethicone 1cst and 10 parts of dimethicone 2cst are combined and mixed using a high-lift mixing blade at high speed. Cetyl PEG/PPG-10/1 dimethicone (0.50 part) is added, and mixing at high speed is continued. Then, 3 parts polyglyceryl-4 isostearate (and) cetyl PEG/PPG-10/1 dimethicone (and) hexyl laurate is added
with continued mixing. Then, 3.50 parts caprylic/capric triglyceride (and) stearalkonium hectorite (and) propylene carbonate is added. Phase B is prepared by combining 1.50 parts diisopropyl adipate, 5 parts butyloctyl salicylate and 2 parts of the reaction product of Example E1 or Example E6 and mixing until uniform. and mixing until uniform. Phase B is added to phase A with mixing. To prepare phase C, 0.20 part of hydroxyethyl cellulose is added with mixing to 37.82 parts water, and the mixture is heated to 80-85 °C. Once the hydroxyethyl cellulose is dispersed, 2 parts glycerin and 0.50 part 1,2-hexanediol are added and mixing at 85 °C is continued. Once hydroxyethyl cellulose is solubilized, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 1 part phenoxyethanol (and) benzoic acid (and) dehydroacetic acid and dehydroacetic acid and 1 part sodium chloride are added. Once the salt is dissolved, phase C is cooled to room temperature. While the mixture of phases A and B is mixed, phase C is added and mixing continued until uniform. Zinc oxide (and) triethoxycaprylylsilane (21.98 parts) is added to the mixture of phases A, B and C, and prop mixing is continued until the mixture is homogeneous. The mixture is then homogenized for 10 minutes. [00262] Example F4: Anionic emulsion using reaction product of Example E1 or Example E6 [00263] To prepare phase A, 53.30 parts by weight of water and 5 parts glycerin (and) glyceryl acrylate/acrylic acid copolymer (and) PVM/MA are combined and heated to 75-80 °C. Acrylic Acid/VP crosspolymer (0.30 part) is sprinkled in, and the mixture is mixed until smooth. Tetrasodium EDTA (0.10 part), 1 part benzoic acid (and) dehydroacetic acid in phenoxyethanol and 0.30 part methylparaben NF are added and mixed until combined. Phase B is prepared by combining 1.50 parts potassium cetyl phosphate, 5 parts ethylhexyl triazone, 3 parts avobenzone, 3 parts bis-ethylhexyloxyphenol methoxyphenyl triazine, 5 parts octisalate, 10 parts homosalate, 5 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 2 parts dimethicone, 1.50 parts behenyl alcohol (and) polyglycerol-10 pentastearate (and) sodium stearoyl lactate and 2 parts of the reaction product of Example E1 or Example E6 and heating to 75-80 °C. Phase B is added slowly to phase A, and the mixture is homogenized. The homogenized mixture is cooled to 60-65 °C, and 2 parts of 10% sodium hydroxide solution is added slowly with continued homogenization. The mixture is sweep mixed with pH adjustment, as needed, until cooled. [00264] Example F5: Hydrosheer™ spray using reaction product of Example E1 or Example E6
[00265] Phase A is prepared by combining 44 parts by weight of ethanol and 2 parts of the reaction product of Example E1 or Example E6 and mixing until fully combined. Phase B is prepared by combining 3 parts avobenzone, 5 parts octisalate, 10 parts homosalate, 8 parts octocrylene, 2 parts bemotrizinol, 3 parts of C12-C15 alkyl benzoate, benzyl O-toluate or phenethyl benzoate, 5 parts diisopropyl adipate, 5 parts lauryl lactate, 5 parts C12-C15 lactate, 4 parts dicaprylyl carbonate and 3 parts isodecyl salicylate and heating with low heat until solids are fully dissolved. Phase B is then added to phase A and mixed until homogeneous. [00266] Example F6: Lipstick using reaction product of Example E1 or Example E6 [00267] Phase A is prepared by combining 12.97 parts by weight of ozokerite wax, 6.25 parts polyethylene, 6 parts octyldodecyl stearate, 5 parts diisopropyl adipate, 5.5 parts octyldodecyl stearoyl stearate, 3.44 parts pentaerythrityl tetraoctanoate, 4.4 parts C12-C15 alkyl lactate, 3.4 parts myristyl lactate, 3.7 parts hydrogenated polyisobutene, 2 parts of the reaction product of Example E1 or Example E6, 6.52 parts octocrylene, 4.66 parts ethylhexyl salicylate, 5.6 parts avobenzone, 8.36 parts homosalate and 1.2 parts caprylyl glycol (and) phenoxyethanol and heating to 90-95 °C with homogenization until clear. Phase B is prepared by combining and pulverizing 0.78 part Ricinus communis seed oil (and) CI 15850, 1.54 parts Ricinus communis (castor) seed oil (and) CI 77891 (and) polyhydroxystearic acid, 0.11 part Ricinus communis (castor) seed oil (and) CI 77491 (and) CI 77492(and) polyhydroxystearic acid, 2.99 parts mica (and) iron oxides CI 77491 (and) titanium dioxide, 11.17 parts synthetic fluorphogopite (and) titanium dioxide (and) tin oxide, 3.41 parts CI 77491 (and) CI 77891 (and) synthetic fluorphogopite, and 1 part water (and) butylene glycol (and) hexapeptide-3. Phase B is combined with phase A, and mixing is continued until pigment dispersion is confirmed using two glass slides. The mixture is poured into molds at 80 °C and refrigerated for 10 minutes. [00268] Example G1: Seed coating using reaction product of Example D1 and polyvinyl alcohol [00269] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 4 parts polyvinyl alcohol, 1 part of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse. [00270] Example G2: Seed coating using reaction product of Example D1 and PEG 400
[00271] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts PEG 400, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse. [00272] Example G3: Seed coating using reaction product of Example D1 and styrene acrylic copolymer [00273] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 2.5 parts styrene acrylic copolymer, 2.5 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse. [00274] Example G4: Seed coating using reaction product of Example D1 and vinyl pyrrolidone/vinyl acetate copolymer [00275] A seed coating is prepared by combining 10 parts by weight of tebuconazole SC (20%), 1.55 parts composite of PVP and MVE-MAHE, 0.075 parts xanthan gum, 1.75 parts propylene glycol, 0.1 part paraffin oil based with silica agent, 3 parts vinylpyrrolidone/vinyl acetate copolymer, 2 parts of the reaction product of Example D1, 2.5 parts aqueous pigment dispersion (60% solids) and 79.025 parts water and stirring for 1 hour to disperse. [00276] Example G5: Seed coating using reaction products of Examples B1 and E1 [00277] Reaction product of Example E1 (2.50 g), 7.50 g of the reaction product of Example B1, 45.56 g of water and 12.00 g of propylene glycol are combined and mixed using an overhead stirrer with a propellor blade at 400 rpm for 10 minutes. Xanthan gum (0.25 g) is added slowly and mixed for 15 minutes or until fully hydrated. Composite of PVP (polyvinyl pyrrolidone) and MVE- MAHE (methyl vinyl ether/maleic acid half ester, neutralized) copolymer (0.83 g), 0.30 g of silicone defoamer and 0.24 g of 20% aqueous dipropylene glycol solution of 1,2-benzisothiazolin- 3-one are added with mixing. Mixing speed is increased to 600 rpm, and 25 g of zinc oxide, 3.33 g of zinc EDTA, 0.26 g of sodium molybdate and 2.5 g of red pigment are added slowly and mixed for 15 minutes. [00278] Example G6: Seed coating using reaction products of Examples B1 and E6
[00279] Reaction product of Example E6 (2.50 g), 7.50 g of the reaction product of Example B1, 45.56 g of water and 12.00 g of propylene glycol are combined and mixed using an overhead stirrer with a propellor blade at 400 rpm for 10 minutes. Xanthan gum (0.25 g) is added slowly and mixed for 15 minutes or until fully hydrated. Composite of PVP (polyvinyl pyrrolidone) and MVE- MAHE (methyl vinyl ether/maleic acid half ester, neutralized) copolymer (0.83 g), 0.30 g of silicone defoamer and 0.24 g of 20% aqueous dipropylene glycol solution of 1,2-benzisothiazolin- 3-one are added with mixing. Mixing speed is increased to 600 rpm, and 25 g of zinc oxide, 3.33 g of zinc EDTA, 0.26 g of sodium molybdate and 2.5 g of red pigment are added slowly and mixed for 15 minutes. [00280] Example G7: Agrochemical oil dispersion of imidacloprid and bifenthrin using reaction products of Examples B1 and E1 [00281] Imidacloprid (270 g) is dispersed in a mixture of soy methyl ester, 26.5 g of the reaction product of Example E1, 79.5 g of the reaction product of Example B1, and 67.0 g of attapulgite. The mixture is milled until the particle size reaches 1 to 5 μm. Finally, 100 g of bifenthrin, 17.0 g of calcium dodecyl benzene sulfonate, 88.0 g of ethoxylated castor oil, 6.0 g of EO/PO butanol and 6.5 g of hydroxyethyl cellulose are added with mixing, adjusting the volume to 1 L with additional soy methyl ester. [00282] Example G8: Agrochemical oil dispersion of imidacloprid and bifenthrin using reaction products of Examples B1 and E6 [00283] Imidacloprid (270 g) is dispersed in a mixture of soy methyl ester, 26.5 g of the reaction product of Example E6, 79.5 g of the reaction product of Example B1, and 67.0 g of attapulgite. The mixture is milled until the particle size reaches 1 to 5 μm. Finally, 100 g of bifenthrin, 17.0 g of calcium dodecyl benzene sulfonate, 88.0 g of ethoxylated castor oil, 6.0 g of EO/PO butanol and 6.5 g of hydroxyethyl cellulose are added with mixing, adjusting the volume to 1 L with additional soy methyl ester. [00284] While the compositions and methods of the disclosed and/or claimed inventive concept(s) have been described in terms of particular aspects, it will be apparent to those of ordinary skill in the art that variations may be applied to the compositions and/or methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit and scope of the disclosed and/or claimed inventive concept(s). All such similar
substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and/or claimed inventive concept(s).
Claims
What is Claimed is: 1. A reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; and, (C) a base.
2. The reaction product according to claim 1, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 H to 4 carbon atoms reside in the lactam ring between the
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
3. The reaction product according to claim 2, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
4. The reaction product according to claim 2, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
6. The reaction product according to claim 1, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
7. The reaction product according to claim 1, wherein the maleated natural oil is a maleated soybean oil.
8. The reaction product according to claim 1, wherein the base (C) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
9. The reaction product according to claim 8, wherein the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
10. The reaction product according to claim 8, wherein the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
11. The reaction product according to claim 9, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
12. The reaction product according to claim 9, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
13. The reaction product according to claim 9, wherein the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
14. The reaction product according to claim 8, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
15. The reaction product according to claim 1 that is a reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; and (C) a base selected from oxides, hydroxides, carbonates, and bicarbonates of sodium.
16. The reaction product according to claim 15 that is a sodium salt of a maleated soybean oil substituted with one, two or three 1-(2-hydroxyethyl)-2-pyrrolidone moieties.
18. A composition comprising the reaction product of claim 1, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions.
19. A coating composition comprising the reaction product of claim 1.
20. The coating composition according to claim 19, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
21. The coating composition according to claim 19, wherein the coating composition further comprises at least one additive in the range of from about 0.01 wt.% to about 99.9 wt.%.
22. The coating composition according to claim 21, wherein the additive is selected from the group consisting of film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers.
23. The coating composition according to claim 19, wherein the coating composition is an aqueous or a non-aqueous composition used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.
24. The coating composition according to claim 19, wherein the coating composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
25. A personal care composition comprising the reaction product of claim 1.
26. The personal care composition according to claim 25, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
27. The personal care composition according to claim 25, wherein the personal care composition further comprises at least one personal care active ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
28. The personal care composition according to claim 27, wherein the personal care active ingredient is selected from the group consisting of color cosmetic agents, hair care agents, skin care agents, sun care agents, and oral care agents.
29. The personal care composition according to claim 25, wherein the personal care composition is selected from the group comprising body wash compositions, skin lotion compositions, sunscreen compositions, anti-wrinkle compositions, moisturizer compositions, facial cleaning compositions, lipstick compositions, lip-gloss compositions, mascara compositions, foundation compositions, anti-perspirant compositions, shaving compositions, hair conditioner compositions, anti-perspirant compositions, deodorant compositions, hair rinse compositions, hair shampoo compositions, hair styling compositions, make-up remover compositions, and oral care compositions.
30. The personal care composition according to claim 25, wherein the personal care composition is an aqueous or a non-aqueous formulation in the form of a spray, lotion, mousse, fluid, serum, solution, suspension, perm, emulsion, gel, mist, vesicle, dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jelly, or liquid.
31. A pharmaceutical composition comprising the reaction product of claim 1.
32. The pharmaceutical composition according to claim 31, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
33. The pharmaceutical composition according to claim 31, wherein the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in the range of from about 0.01 wt.% to about 99.9 wt.%.
34. The pharmaceutical composition according to claim 33, wherein the pharmaceutically accepted excipient is selected from the group consisting of binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti- adherents, surfactants, pH modifiers and coloring agents, diluents, sweeteners, anti-tacking agents, colorants and mixtures thereof.
35. The pharmaceutical composition according to claim 31, wherein the pharmaceutical composition is of a form selected from the group consisting of solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders,
lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials, and non-aqueous and aqueous liquid suspensions.
36. An agricultural composition comprising the reaction product of claim 1.
37. The agricultural composition according to claim 36, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
38. The agricultural composition according to claim 36, wherein the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
39. The agricultural composition according to claim 38, wherein the agriculturally active ingredient is selected from the group consisting of fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites and antimicrobials.
40. The agricultural composition according to claim 38, wherein the additional ingredient is an adjuvant or an inert ingredient.
41. The agricultural composition according to claim 40, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners and mixtures thereof.
42. The agricultural composition according to claim 40, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
43. The agricultural composition according to claim 36, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant
strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition.
44. The agricultural composition according to claim 36, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
45. A reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; and (B) at least one lactam moiety having at least one amine functional group.
46. The reaction product according to claim 45, wherein the lactam (B) having at least one amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 H to 4 carbon atoms reside in the lactam ring between the
group and the
group;
Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s); and R, and R1 are selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
47. The reaction product according to claim 46, wherein the lactam (B) having at least one amine functional group is selected from the group consisting of:
and combinations thereof, wherein, Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R1, R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
50. The reaction product according to claim 45, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
51. The reaction product according to claim 45, wherein the maleated natural oil is a maleated soybean oil.
52. The reaction product according to claim 45 that is a reaction product of (A) a maleated natural oil; and (B) 1-(2-aminoethyl)-2-pyrrolidone.
53. The reaction product according to claim 52 that is a maleated soybean oil substituted with one, two or three 1-(2-aminoethyl)-2-pyrrolidone moieties.
54. The reaction product according to claim 52, comprising one or more structure(s) selected from:
55. A composition comprising the reaction product of claim 45, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions.
56. A coating composition comprising the reaction product of claim 45.
57. The coating composition according to claim 56, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
58. The coating composition according to claim 56, wherein the coating composition further comprises at least one additive in the range of from about 0.01 wt.% to about 99.9 wt.%.
59. The coating composition according to claim 58, wherein the additive is selected from the group consisting of film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents,
humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers.
60. The coating composition according to claim 56, wherein the coating composition is an aqueous or a non-aqueous composition used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.
61. The coating composition according to claim 56, wherein the coating composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
62. A personal care composition comprising the reaction product of Claim 45.
63. The personal care composition according to claim 62, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
64. The personal care composition according to claim 62, wherein the personal care composition further comprises at least one personal care active ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
65. The personal care composition according to claim 64, wherein the personal care active ingredient is selected from the group consisting of color cosmetic agents, hair care agents, skin care agents, sun care agents, and oral care agents.
66. The personal care composition according to claim 62, wherein the personal care composition is selected from the group comprising body wash compositions, skin lotion compositions, sunscreen compositions, anti-wrinkle compositions, moisturizer compositions, facial cleaning compositions, lipstick compositions, lip-gloss compositions, mascara compositions, foundation compositions, anti-perspirant compositions, shaving compositions, hair conditioner compositions, anti-perspirant compositions, deodorant compositions, hair rinse
compositions, hair shampoo compositions, hair styling compositions, make-up remover compositions, and oral care compositions.
67. The personal care composition according to claim 62, wherein the personal care composition is an aqueous or a non-aqueous formulation in the form of a spray, lotion, mousse, fluid, serum, solution, suspension, perm, emulsion, gel, mist, vesicle, dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jelly, or liquid.
68. A pharmaceutical composition comprising the reaction product of claim 45.
69. The pharmaceutical composition according to claim 68, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
70. The pharmaceutical composition according to claim 68, wherein the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in the range of from about 0.01 wt.% to about 99.9 wt.%.
71. The pharmaceutical composition according to claim 70, wherein the pharmaceutically accepted excipient is selected from the group consisting of binders, carriers, lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti- adherents, surfactants, pH modifiers and coloring agents, diluents, sweeteners, anti-tacking agents, colorants, and mixtures thereof.
72. The pharmaceutical composition according to claim 68, wherein the pharmaceutical composition is of a form selected from the group consisting of solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials, and non-aqueous and aqueous liquid suspensions.
73. An agricultural composition comprising the reaction product of claim 45.
74. The agricultural composition according to claim 73, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
75. The agricultural composition according to claim 73, wherein the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
76. The agricultural composition according to claim 75, wherein the agriculturally active ingredient is selected from the group consisting of fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites and antimicrobials.
77. The agricultural composition according to claim 75, wherein the additional ingredient is an adjuvant or an inert ingredient.
78. The agricultural composition according to claim 77, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners and mixtures thereof.
79. The agricultural composition according to claim 77, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
80. The agricultural composition according to claim 73, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition.
81. The agricultural composition according to claim 73, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule
suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
82. A reaction product of: (A) a maleated natural oil, comprising a natural oil with maleated functionality; (B) a lactam moiety having at least one hydroxyl, thiol or amine functional group; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and, (D) optionally, a base.
83. The reaction product according to claim 82, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group has the structure:
wherein: Y is an alkylene or alkenylene group comprising 2 to 50 carbon atoms, wherein 2 to 4 carbon atoms reside in the lactam ring between the
group and th
group; Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein the aforementioned groups may or may not contain oxygen atom(s);
X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and, R is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
84. The reaction product according to claim 83, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of: ,
and combinations thereof, wherein Q is selected from functionalized and unfunctionalized alkylenes of linear, branched, or cyclic structure, arylenes, and combinations thereof, wherein any of the aforementioned groups may or may not contain oxygen atom(s); and each R2, R3, R4, R5, and R6 is independently selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms; and, X is selected from OH, SH and NHR1, wherein R1 is selected from hydrogen and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups, wherein the alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl groups may or may not contain heteroatoms.
85. The reaction product according to claim 83, wherein the lactam (B) having at least one hydroxyl, thiol or amine functional group is selected from the group consisting of:
and combinations thereof, wherein, Q is a linear alkylene chain having at least two carbon atoms (–CH2-CH2–); and X is selected from OH, SH and NH2.
87. The reaction product according to claim 82, wherein the maleated natural oil is selected from the group consisting of maleated avocado oils, maleated coconut oils, maleated corn oils, maleated cottonseed oils, maleated jojoba oils, maleated linseed oils, maleated nut oils, maleated olive oils, maleated palm oils, maleated raisin oils, maleated rapeseed oils, maleated safflower oils, maleated sesame oils, maleated soybean oils, maleated squash oils, maleated sunflower oils, maleated almond oils, maleated canola oils, maleated flaxseed oils, maleated grapeseed oils, maleated palm kernel oils, maleated peanut oils, maleated walnut oils, maleated chickpea oils, maleated clary sage oils, and mixtures thereof.
88. The reaction product according to claim 82, wherein the maleated natural oil is a maleated soybean oil.
89. The reaction product according to claim 82, wherein the hydrophobic moiety (C) is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 6 to about 36 carbon atoms and may contain additional heteroatoms; unsubstituted or
substituted polyols, with or without additional heteroatoms, containing about 37 to about 60 carbon atoms; silicon-based compounds; and combinations thereof.
90. The reaction product according to claim 82, wherein the hydrophilic moiety (C) is a moiety selected from those of the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, and aryl alcohols and amines, wherein the alcohols and amines contain from about 1 to about 5 carbon atoms and may contain additional heteroatoms; unsubstituted or substituted polyols, wherein the unsubstituted or substituted polyols contain from about 2 to about 36 carbon atoms and may contain additional heteroatoms; poly(ethylene glycol) monomethyl ethers (mPEGs) containing from 5 to 45 carbon atoms; silanes; and combinations thereof.
91. The reaction product according to claim 90, wherein the silane is functionalized with an alcohol, an amine, or combinations thereof.
92. The reaction product according to claim 89, wherein the hydrophobic moiety is that of an alcohol selected from the group consisting of hexanol, heptanol, nonanol, decanol, dodecanol, phenol, ethylbenzyl alcohol, 2-ethyl-1-hexanol, 1-octanol, 2-octanol, 2-butyl-1- octanol, 2-hexyl-1-decanol, 2-octyl-1-dodecyl alcohol, 1-tetradecanol, 2-tetradecanol, 1- hexadecanol, 2-hexadecanol, 3,7-dimethyl-1-octanol, 2-propyl-1-pentanol, 4-methyl-1-pentanol, behenyl alcohol, 1-naphthalenemethanol, benzyl alcohol, and mixtures thereof.
93. The reaction product according to claim 90, wherein the hydrophilic moiety is that of an alcohol selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.
94. The reaction product according to claim 90, wherein the hydrophilic moiety is that of a polyol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, polyethylene glycol, glycerol, polypropylene glycol, hexylene glycol, sorbitol, neopentyl glycol, erythritol, mannitol, xylitol, threitol, pentaerythritol, beta-cyclodextrin, ribose, 2-deoxygalactose, glucosamine, mannosamine, galactosamine, N- methylglucosamine, and mixtures thereof.
95. The reaction product according to claim 89, wherein the hydrophobic moiety is that of an amine selected from the group consisting of benzylamine, cyclohexylamine, hexylamine, methylhexylamine, phenethylamine, octylamine, oleylamine, decylamine, dodecylamine,
hexadecylamine, octadecylamine, undecylamine, pentadecylamine, 2-methylbutylamine, and mixtures thereof.
96. The reaction product according to claim 90, wherein the hydrophilic moiety is that of an amine selected from the group consisting of diethanolamine, serinol, 2-amino-2-ethyl-1,3- propanediol, dimethylamine, 2-methylbutylamine, 3-amino-1-propanol, their hydrochloride salts, their ammonium salts, and mixtures thereof.
97. The reaction product according to claim 89, wherein the silicon based compound is a hydrophobic compound selected from the group consisting of aminopropylmethylsiloxane– dimethylsiloxane, N-ethylaminoisobutyl terminated polydimethylsiloxane, poly(1,1- dimethylsilazane) telomer, aminopropyl terminated polydimethylsiloxane, monoaminopropyl terminated polydimethylsiloxane, (tetramethylpiperidinyloxy)propylmethylsiloxane]- dimethylsiloxane copolymer, polydimethylsiloxane, carbinol (hydroxyl) terminated polydimethylsiloxane, monocarbinol terminated polydimethylsiloxane, monocarbinol terminated functional polydimethylsiloxane, [Bis(hydroxyethyl)amine] terminated polydimethylsiloxane, silanol terminated polydimethylsiloxane, silanol terminated polydiphenylsiloxane, dodecylmethylsiloxane-hydroxypolyalkyleneoxypropyl methylsiloxane, and mixtures thereof.
98. The reaction product according to claim 90, wherein the silane is a hydrophilic compound selected from the group consisting of 3-aminopropylsilanetriol, N-(2-aminoethyl)-3- aminopropylsilanetriol, and mixtures thereof.
99. The reaction product according to claim 82, wherein the base (D) is selected from the group consisting of inorganic bases, organic bases, and mixtures thereof.
100. The reaction product according to claim 99, wherein the inorganic base is selected from the group consisting of oxides of alkali metals and alkaline earth metals, hydroxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, bicarbonates of alkali metals and alkaline earth metals, oxides of transition metals, hydroxides of transition metals, carbonates of transition metals, bicarbonates of transition metals, and combinations thereof.
101. The reaction product according to claim 99, wherein the organic base is selected from the group consisting of ammonia, primary amines, secondary amines, tertiary amines, pyridine, imidazole, benzimidazole, histidine, guanidine, and mixtures thereof.
102. The reaction product according to claim 100, wherein the alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, francium, and mixtures thereof.
103. The reaction product according to claim 100, wherein the alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, radium, and mixtures thereof.
104. The reaction product according to claim 100, wherein the transition metal is selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, yttrium zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, silver, cadmium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, rutherfordium, dubnium, seaborgium, bohrium, hassium, meitnerium, darmstadtium, roentgenium, and mixtures thereof.
105. The reaction product according to claim 99, wherein the inorganic base is selected from the group consisting of oxides, hydroxides, carbonates and bicarbonates of sodium, calcium, and combinations thereof.
106. The reaction product according to claim 82, comprising the reaction product of (A) a maleated natural oil; (B) 1-(2-hydroxyethyl)-2-pyrrolidone; (C) a functionalized or unfunctionalized moiety selected from the group consisting of hydrophobic moieties, hydrophilic moieties, and combinations thereof, wherein the maleated functionality has been partially reacted with the functionalized or unfunctionalized moiety; and (D) optionally, a base.
107. The reaction product according to claim 106, wherein the reaction product has the structure:
wherein R7 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aryl, alkaryl and aralkyl moieties containing from about 1 to about 36 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
108. The reaction product according to claim 107, comprising one or more structure(s) selected from:
wherein R7 is ethyl, butyl, hexyl, octyl, 2-ethyl-1-hexyl, 2-butyl-1-octyl, 2-hexyl-1-decyl, 2-octyl-1-dodecyl, or mixtures thereof; and wherein R8, R9 and R10 are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms.
109. The reaction product according to claim 106, wherein the reaction product is a polymer having the structure:
wherein n is greater than 1; wherein R11 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms; and wherein each Q is independently selected from the group consisting of H, Li, Na, K, Rb, Cs, Fr, ½ Mg, ½ Ca, ½ Co, ½ Cu, ½ Zn, ammonium, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium.
110. The reaction product according to claim 109, wherein the polymer comprises one or more structure(s) selected from:
wherein 1 < n < 30; wherein R8, R9 and R10 are each, independently, hydrogen, methyl, or an unsubstituted or substituted alkyl, aryl, alkaryl or aralkyl group containing 2 to 18 carbon atoms and, optionally, containing heteroatoms; and wherein R11 is one or more hydrophilic or hydrophobic moiety selected from the group consisting of unsubstituted or substituted alkylene, cycloalkylene, and arylene moieties containing from about 2 to about 60 carbon atoms.
112. A composition comprising the reaction product of claim 82, wherein the composition is selected from the group consisting of skin care compositions, hair care compositions, oral care compositions, home care compositions, energy compositions, construction compositions, pharmaceutical compositions, biocide compositions, preservative compositions, nutraceutical compositions, food compositions, agricultural compositions, coating compositions, oilfield compositions, cosmetic compositions, industrial and institutional compositions, textile compositions, laundry compositions, cleaning compositions, ceramic coating compositions, battery compositions, and disinfection compositions.
113. A coating composition comprising the reaction product of claim 82.
114. The coating composition according to claim 113, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
115. The coating composition according to claim 113, wherein the coating composition further comprises at least one additive in the range of from about 0.01 wt.% to about 99.9 wt.%.
116. The coating composition according to claim 115, wherein the additive is selected from the group consisting of film forming polymers, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers.
117. The coating composition according to claim 113, wherein the coating composition is an aqueous or a non-aqueous composition used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.
118. The coating composition according to claim 113, wherein the coating composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, ceramics, yarns, and woven, knitted, natural, synthetic, and regenerated fibers.
119. A personal care composition comprising the reaction product of claim 82.
120. The personal care composition according to claim 119, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
121. The personal care composition according to claim 119, wherein the personal care composition further comprises at least one personal care active ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
122. The personal care composition according to claim 121, wherein the personal care active ingredient is selected from the group consisting of color cosmetic agents, hair care agents, skin care agents, sun care agents, and oral care agents.
123. The personal care composition according to claim 119, wherein the personal care composition is selected from the group comprising body wash compositions, skin lotion compositions, sunscreen compositions, anti-wrinkle compositions, moisturizer compositions, facial cleaning compositions, lipstick compositions, lip-gloss compositions, mascara compositions, foundation compositions, anti-perspirant compositions, shaving compositions, hair conditioner compositions, anti-perspirant compositions, deodorant compositions, hair rinse compositions, hair shampoo compositions, hair styling compositions, make-up remover compositions, and oral care compositions.
124. The personal care composition according to claim 119, wherein the personal care composition is an aqueous or a non-aqueous formulation in the form of a spray, lotion, mousse, fluid, serum, solution, suspension, perm, emulsion, gel, mist, vesicle, dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jelly, or liquid.
125. A pharmaceutical composition comprising the reaction product of claim 82.
126. The pharmaceutical composition according to claim 125, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
127. The pharmaceutical composition according to claim 125, wherein the pharmaceutical composition further comprises at least one pharmaceutically accepted excipient in the range of from about 0.01 wt.% to about 99.9 wt.%.
128. The pharmaceutical composition according to claim 127, wherein the pharmaceutically accepted excipient is selected from the group consisting of binders, carriers,
lubricants, flow agents, adsorbents, crystallization retarders, disintegrants, solubilizers, anti- adherents, surfactants, pH modifiers and coloring agents, diluents, sweeteners, anti-tacking agents, colorants and mixtures thereof.
129. The pharmaceutical composition according to claim 125, wherein pharmaceutical composition is of a form selected from the group consisting of solids, semi-solids, liquids, tablets, powders, granules, lozenges, capsules, patches, caplets, ointments, powders, lotions, gels, creams, suppositories, suspensions, liposomes, aerosols, syrups, elixirs, emulsions, sterile liquids, injections, suppositories, vials, and non-aqueous and aqueous liquid suspensions.
130. An agricultural composition comprising the reaction product of claim 82.
131. The agricultural composition according to claim 130, wherein the reaction product is in the range of from about 0.1 wt.% to about 95.0 wt.% of the composition.
132. The agricultural composition according to claim 130, wherein the agricultural composition further comprises one or more agriculturally active ingredient and one or more additional ingredient in the range of from about 0.01 wt.% to about 99.9 wt.%.
133. The agricultural composition according to claim 132, wherein the agriculturally active ingredient is selected from the group consisting of fertilizers, pesticides, rodenticides, miticides, algicides, molluscicides, acaricides, avicides, insecticides, herbicides, ovicides, fungicides, germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals, anti- parasites and antimicrobials.
134. The agricultural composition according to claim 132, wherein the additional ingredient is an adjuvant or an inert ingredient.
135. The agricultural composition according to claim 134, wherein the adjuvant is selected from the group consisting of acidifying agents, buffering agents, anti-foam agents, defoaming agents, anti-transpirants, dyes and brighteners, compatibility agents, crop oil concentrates, oil surfactants, deposition agents, drift reduction agents, foam markers, feeding stimulants, herbicide safeners, spreaders, extenders, adhesive agents, suspension agents, gelling agents, synergists, wetting agents, emulsifiers, dispersing agents, penetrants, tank and equipment cleaners, adjusters, water absorbents, water softeners and mixtures thereof.
136. The agricultural composition according to claim 134, wherein the inert ingredient is selected from the group consisting of solvents, liquid carriers, solid carriers or fillers, surfactants, solubilizers, protective colloids, thickeners, humectants, repellents, attractants, compatibilizers, bactericides, anti-freezing agents, crystallization inhibitors, colorants, tackifiers, binders, preservatives, pH adjuster, clarifiers, stabilizers, UV stabilizers, and mixtures thereof.
137. The agricultural composition according to claim 130, wherein the agricultural composition is an adjuvant composition, a fertilizer composition, a nutrient composition, a plant strengthener composition, a seed coating composition, a soil conditioner composition, a livestock composition, a granular composition, a controlled release composition, a film coating composition, a pesticide composition selected from ovicide, rodenticide, insecticide, miticide, algicide, molluscicide, acaricide, avicide, fungicide and herbicide compositions, a germicide composition, an antibiotic composition, an antibacterial composition, an antiviral composition, an antifungal composition, an antiprotozoal composition, an anti-parasite composition, a wood preservation composition, an antimicrobial composition, or a yield enhancer composition.
138. The agricultural composition according to claim 130, wherein the agricultural composition is in the form of an aqueous or a non-aqueous composition comprising a capsule suspension, an emulsifiable concentrate, an emulsion for seed treatment, a concentrated aqueous emulsion, a microemulsion, a suspoemulsion, an oil-in-water emulsion, a flowable concentrate for seed treatment, an oil dispersion, a suspension concentrate, a water dispersible granule or a wettable powder.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202363581833P | 2023-09-11 | 2023-09-11 | |
| US63/581,833 | 2023-09-11 |
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| WO2025059043A1 true WO2025059043A1 (en) | 2025-03-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/US2024/045994 Pending WO2025059043A1 (en) | 2023-09-11 | 2024-09-10 | A modified maleated natural oil containing a lactam moiety, salts, compositions, and use thereof |
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| WO (1) | WO2025059043A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090065736A1 (en) * | 2007-07-03 | 2009-03-12 | Georgia-Pacific Chemicals Llc | Chemical modification of maleated fatty acids |
| US20130289284A1 (en) * | 2010-07-26 | 2013-10-31 | Osama M. Musa | Renewable modified natural compounds |
| WO2014145972A2 (en) * | 2013-03-15 | 2014-09-18 | Ethox Chemicals, Llc | Bio-based dispersants |
| US20180070584A1 (en) * | 2015-03-25 | 2018-03-15 | Huntsman Petrochemical Llc | Maleated Natural Oil Derivatives as Agrochemical Inert Ingredients |
-
2024
- 2024-09-10 WO PCT/US2024/045994 patent/WO2025059043A1/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090065736A1 (en) * | 2007-07-03 | 2009-03-12 | Georgia-Pacific Chemicals Llc | Chemical modification of maleated fatty acids |
| US20130289284A1 (en) * | 2010-07-26 | 2013-10-31 | Osama M. Musa | Renewable modified natural compounds |
| WO2014145972A2 (en) * | 2013-03-15 | 2014-09-18 | Ethox Chemicals, Llc | Bio-based dispersants |
| US20180070584A1 (en) * | 2015-03-25 | 2018-03-15 | Huntsman Petrochemical Llc | Maleated Natural Oil Derivatives as Agrochemical Inert Ingredients |
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