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WO2025226781A1 - Compositions de revêtement comprenant des polyamides fonctionnels - Google Patents

Compositions de revêtement comprenant des polyamides fonctionnels

Info

Publication number
WO2025226781A1
WO2025226781A1 PCT/US2025/025916 US2025025916W WO2025226781A1 WO 2025226781 A1 WO2025226781 A1 WO 2025226781A1 US 2025025916 W US2025025916 W US 2025025916W WO 2025226781 A1 WO2025226781 A1 WO 2025226781A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
functional
polyamide
groups
percent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/025916
Other languages
English (en)
Inventor
Milena Maria GARAY-TOVAR
Chandra Pandey
Gabor Erdodi
Alec KRIENEN
Samantha DETGEN
Emily Robertson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Advanced Materials Inc
Original Assignee
Lubrizol Advanced Materials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lubrizol Advanced Materials Inc filed Critical Lubrizol Advanced Materials Inc
Publication of WO2025226781A1 publication Critical patent/WO2025226781A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/60—Polyamides or polyester-amides
    • C08G18/603—Polyamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/60—Polyamides or polyester-amides
    • C08G18/606—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • Two-component (“2K”) polyurethane coating compositions are subject to constant efforts to improve properties, increase sustainability, and reduce environmental impacts of manufacture and use of these compositions.
  • Solvent-borne 2K polyurethane coating compositions may sometimes present challenges related to volatile organic compounds which may evolve when the compositions dry/cure, and, although the solvent-borne compositions have certain superior properties, there have been efforts to replace certain solvent-borne compositions with water-borne polyurethane compositions. Such efforts are not always successful.
  • the disclosed technology utilizes novel functional polyamides in polyurethane coating compositions, with a focus on solve-borne compositions, to ameliorate at least some of the downsides associated with certain solvent-borne compositions.
  • the disclosed technology provides a composition which may be utilized in clear and pigmented coating compositions, which have good curing characteristics with or without the use of catalysts, and which provides excellent chemical resistance and/or weatherability.
  • compositions including: a polyisocyanate having an average of greater than two isocyanate groups per molecule; a functional polyamide having an average of greater than two reactive groups per molecule which are chemically reactive with an isocyanate group of the polyisocyanate; and a solvent; wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 3 : 1.
  • a composition comprising: (a) a polyisocyanate having an average of greater than two isocyanate groups per molecule; (b) a functional polyamide having an average of greater than two reactive groups per molecule which are chemically reactive with an isocyanate group of the polyisocyanate; and (c) a solvent; wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 3: 1; wherein the functional polyamide comprises monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, polycarboxylic acids, or polyamines, wherein: the monomeric units have an average of greater than two functional groups per monomeric unit; the functional groups of the monomeric units comprise at least one of primary amine groups, secondary amine groups, carboxyl groups, or hydroxyl groups; at least a portion of the functional groups of the monomeric units react together to form linkages between the monomeric units
  • 60 weight percent of the monomeric units of the functional polyamide are derived from monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, polycarboxylic acids, or polyamines, based on the total weight of the functional polyamide.
  • composition of any one of embodiments 1 to 34, wherein at least 55 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 35, wherein at least 60 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 36, wherein at least 65 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 37, wherein at least 70 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 38, wherein at least 75 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 39, wherein at least 80 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 40, wherein at least 85 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 41, wherein at least 90 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • composition of any one of embodiments 1 to 46, wherein the functionality in at least 75 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl-functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 47, wherein the functionality in at least 80 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 48, wherein the functionality in at least 85 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl-functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 49, wherein the functionality in at least 90 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 50, wherein the functionality in at least 95 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl-functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 51, wherein the functionality in at least 96 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 52, wherein the functionality in at least 97 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl-functional, or hydroxyl-functional.
  • composition of any one of embodiments 1 to 53, wherein the functionality in at least 98 mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional .
  • functionality in substantially all molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl-functional, or hydroxyl- functional.
  • composition of any one of embodiments 1 to 56, wherein the functionality in at least 70 mole percent of molecules of the functional polyamide is of the same functional type and is hydroxyl-functional.
  • composition of any one of embodiments 1 to 58, wherein the functionality in at least 80 mole percent of molecules of the functional polyamide is of the same functional type and is hydroxyl -functional.
  • composition of any one of embodiments 1 to 61, wherein the functionality in at least 95 mole percent of molecules of the functional polyamide is of the same functional type and is hydroxyl -functional.
  • composition of any one of embodiments 1 to 66, wherein the functionality in substantially all molecules of the functional polyamide is of the same functional type and is hydroxyl-functional.
  • composition of any one of embodiments 1 to 94, wherein the functional polyamide has a viscosity of less than 10,000 cps measured in methyl amyl ketone solvent at 85% solids at room temperature, as measured by a Brookfield circular disk viscometer with the circular disk spinning at 5 rpm.
  • composition of any one of embodiments 1 to 102, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 3 : 1.
  • composition of any one of embodiments 1 to 103, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 3: 1.
  • composition of any one of embodiments 1 to 104, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 2: 1.
  • composition of any one of embodiments 1 to 105, wherein the stoichiometric ratio of the isocyanate groups of the poly isocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 2: 1.
  • composition of any one of embodiments 1 to 107, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 1.6: 1.
  • composition of any one of embodiments 1 to 108, wherein the stoichiometric ratio of the isocyanate groups of the poly isocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 1.6: 1.
  • composition of any one of embodiments 1 to 109, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 1.6: 1.
  • composition of any one of embodiments 1 to 110, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 1.5: 1.
  • composition of any one of embodiments 1 to 1 11, wherein the stoichiometric ratio of the isocyanate groups of the poly isocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 1.5: 1.
  • composition of any one of embodiments 1 to 112, wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 1.5: 1.
  • composition of any one of embodiments 1 to 114, wherein the amount of the polyisocyanate in the composition is from 10 to 35 weight percent, based on the total weight of the composition.
  • at least one additive selected from at least one rheology modifier, at least one polymeric additive, at least one moisture scavenger, at least one dispersant, at least one pigment, at least one catalyst, at least one matting agent, at least one leveling agent, at least one anti-popping additive, at least one defoamer, at least one antimicrobial agent, at least one surface modifier, or at least one hardener.
  • composition of embodiment 122, wherein the catalyst comprises a tin- based catalyst or a tin-free catalyst.
  • composition of embodiment 123, wherein the tin-based catalyst comprises dibutyltin dilaurate.
  • composition of embodiment 124, wherein the tin-free catalyst comprises a zirconium chelate or an aluminum chelate.
  • AMS Method B
  • a coated substrate comprising the composition of any one of embodiments
  • hydrocarbyl refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group includes at least carbon and hydrogen atoms. If the hydrocarbyl group comprises more than one carbon atom, then those carbons need not necessarily be linked to each other. For example, at least two of the carbons may be linked via a suitable element or group.
  • hydrocarbyl refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group consists of carbon, hydrogen, optionally one or more heteroatoms provided the heteroatoms do not alter the predominantly hydrocarbon nature of the substituent.
  • the heteroatom may link to at least two of the carbons in the hydrocarbyl group, and optionally no more than two non-hydrocarbon substituents.
  • Suitable heteroatoms will be apparent to those skilled in the art and include, for instance, sulphur, nitrogen, oxygen, phosphorus, and silicon.
  • the hydrocarbyl contains heteroatoms, optionally, no more than two heteroatoms will be present for every ten carbon atoms in the hydrocarbyl group.
  • Suitable non-hydrocarbon substituents will also be apparent to those skilled in the art and include, for instance, halo, hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulphoxy.
  • hydrocarbyls within the context of the present technology therefore include: (i) hydrocarbon groups selected from aliphatic (e g. alkyl or alkenyl), alicyclic (e g. cycloalkyl, cycloalkenyl, cycloalkadienyl), and aromatic groups; (ii) substituted hydrocarbon groups, selected from hydrocarbon groups defined in (i) substituted with no more than two non- hydrocarbon substituents and/or one or more hydrocarbon substituents, the non-hydrocarbon substituents being selected from the group consisting of halo, hydroxy, alkoxy, mercapto, alkyl mercapto, nitro, nitroso, and sulphoxy; and/or (iii) hetero-containing hydrocarbon groups, selected from hydrocarbon groups defined in (i) containing one or more heteroatom in the ring or chain, provided that the group has no more than two heteroatoms present for every ten carbon atoms in the group, the heteroatoms being
  • hetero-containing hydrocarbon groups may be substituted with no more than two non-hydrocarbon substituents and/or one or more hydrocarbon substituents.
  • hydrocarbyl refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group consists of carbon and hydrogen atoms.
  • the indefinite article “a”/“an” is intended to mean one or more than one.
  • the phrase “at least one” means one or more than one of the following terms.
  • “a”/“an” and “at least one” may be used interchangeably.
  • “at least one of A, B or C” means that just one of A, B or C may be included, and any mixture of two or more of A, B and C may be included, in alternative embodiments.
  • the transitional term “comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, un-recited elements or method steps.
  • the term also encompass, as alternative embodiments, the phrases “consisting essentially of’ and “consisting of,” where “consisting of’ excludes any element or step not specified and “consisting essentially of’ permits the inclusion of additional un-recited elements or steps that do not materially affect the essential or basic and novel characteristics of the composition or method under consideration.
  • composition including: a polyisocyanate having an average of greater than two isocyanate groups per molecule; a functional polyamide having an average of greater than two reactive groups per molecule which are chemically reactive with an isocyanate group of the polyisocyanate; and a solvent; wherein the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 3 : 1.
  • the functional polyamide comprises monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, polycarboxylic acids, or polyamines, wherein: the monomeric units have an average of greater than two functional groups per monomeric unit; the functional groups of the monomeric units comprise at least one of primary amine groups, secondary amine groups, carboxyl groups, or hydroxyl groups; at least a portion of the functional groups of the monomeric units react together to form linkages between the monomeric units, forming molecules of the functional polyamide; at least 30 percent of the linkages between the monomeric units are amide linkages; at least 50 percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group; and the reactive groups of the functional polyamide provide a theoretical functionality to the functional polyamide of greater than two, wherein the functionality in at least 70 mole percent
  • the composition may be, or may be included in, a 2K polyurethane coating composition.
  • the composition may be included in an unreacted form, such as an unreacted 2K polyurethane coating composition, or may be in reacted form, such as in a reacted coating composition, which may be coated onto a substrate.
  • the composition will form a polyurethane composition once the poly isocyanate and the functional polyamide chemically react with one another (potentially in the presence of other reactants and/or additives which may or may not react into the polyurethane).
  • the term “functional”, in the context of a polyamide or monomeric unit, means a group on a molecule which will react with other groups; in the context of the polyamide, for example, a functional group on the polyamide will be capable of reacting with a group on another oligomer/macromonomer when forming a polymer based on the polyamide; in the context of a monomeric unit, for example, a functional group on a monomeric unit will be capable of reacting with other monomeric units to form the polyamide, and some functional groups on monomeric units may remain to create the functional groups on the polyamide (or the functional groups on the polyamide may result from other groups during reaction of the monomeric groups to form the polyamide).
  • the functional polyamide is described as comprising monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, poly carboxy lie acids, or polyamines.
  • polyamide requires that a monomer with a functional group based on a nitrogen atom reacts with a monomer with a functional group based on an atom other than nitrogen.
  • polyamide that at least two monomeric units be reacted together to form the polyamide (one with a functional group including a nitrogen atom reacting with one with a functional groups including an atom other than nitrogen), and that there be at least two amide groups present in the polyamide.
  • lactams are a somewhat special case, in that they may not be considered to have functional groups until they are ring- opened to be reacted into a polyamide. As such, for purposes of the present disclosure, it is considered that lactams include functional groups based on their structure after they are ring- opened to react with other monomeric units. Those of ordinary skill in the relevant art understand that lactams are used in reactions such as this, and that they ring-open before or during reaction with other monomeric units.
  • Formula 1 includes circled locations where intramolecular hydrogen bonds may form, and Formulas 2 and 3 show equilibrium states of Formula 1 including the intramolecular hydrogen bonds.
  • Formula 4 includes circled locations where intramolecular hydrogen bonds may form, and Formula 5 shows an equilibrium state of Formula 4 including the intramolecular hydrogen bonds.
  • intramolecular hydrogen bonds there are many possibilities of where intramolecular hydrogen bonds could form.
  • a general guideline is that an intramolecular hydrogen bond may form at sites like those shown in Formulae 1 through 5, when the sites are within roughly 5 to 8 atoms of one another; this allows for enough proximity that the intramolecular hydrogen bond will form somewhat readily, and in preference to forming an intermolecular hydrogen bond.
  • a person of ordinary skill in the relevant art would understand how to determine whether intramolecular hydrogen bonds may form in a specific embodiment of the present subject matter.
  • At least 50 (such as at least 55, at least 60, at least 65, at least 70, at least 75, at least 80, at least 85, at least 90, at least 95, at least 96, at least 97, at least 98, or at least 99) weight percent of the monomeric units of the functional polyamide are derived from monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, polycarboxylic acids, or polyamines, based on the total weight of the functional polyamide.
  • substantially all of the monomeric units of the functional polyamide are derived from monomeric units selected from at least one of lactams, aminocarboxylic acids, aminoalcohols, polycarboxylic acids, or polyamines, based on the total weight of the functional polyamide.
  • from 50 to substantially all (such as from 50 to 99, from 50 to 98, from 50 to 97, from 50 to 96, from 50 to 95, from 50 to 90, from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to substantially all, from 55 to 99, from 55 to 98, from 55 to 97, from 55 to 96, from 55 to 95, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to substantially all, from 60 to 99, from 60 to 98, from 60 to 97, from 60 to 96, from 60 to 95, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to substantially all, from 65 to 99, from 65 to 98, from 65 to 97, from 65 to 96, from 65 to 95, from 65 to 90, from 65 to 85, from
  • the monomeric units have an average of greater than two functional groups per monomeric unit. In certain embodiments, the monomeric units have at least three functional groups per monomeric unit. In certain embodiments, the monomeric units have from 2 to 20 (such as from 2 to 19, from 2 to 18, from 2 to 17, from 2 to 16, from 2 to 15, from 2 to 14, from 2 to 13, from 2 to 12, from 2 to 11, from 2 to 10, from 2 to 9, from 2 to 8, from 2 to 7, from 2 to 6, from 2 to 5, from 2 to 4, from 2 to 3, from 3 to 20, from 3 to 19, from 3 to 18, from 3 to 17, from 3 to 16, from 3 to 15, from 3 to 14, from 3 to 13, from 3 to 12, from 3 to 11, from 3 to 10, from 3 to 9, from 3 to 8, from 3 to 7, from 3 to 6, from 3 to 5, from 3 to 4, from 4 to 20, from 4 to 19, from 4 to 18, from 4 to 17, from 4 to 16, from 4 to 15, from 4 to 14, from 4 to 13, from 4 to 12, from 4 to 11, from 4 to 10, from 4 to 15, from 4 to 14, from 4 to 13, from 4 to 12, from 4 to
  • At least 50 (such as at least 55, at least 60, at least 65, at least 70, at least 75, at least 80, at least 85, or at least 90) percent of the functional groups of the monomeric units are selected from at least one of primary amine groups, secondary amine groups, carboxyl groups, or hydroxyl groups.
  • from 50 to 90 (such as from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to 90, from 65 to 85, from 65 to 80, from 65 to 75, from 65 to 70, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 90, from 80 to 85, or from 85 to 90) percent of the functional groups of the monomeric units are selected from at least one of primary amine groups, secondary amine groups, carboxyl groups, or hydroxyl groups.
  • At least 30 (such as at least 35, at least 40, at least 45, at least 50, at least 55, at least 60, at least 65, at least 70, at least 75, at least 80, at least 85, at least 90, or at least 95) percent of the linkages between the monomeric units are amide linkages.
  • from 30 to 95 (such as from 30 to 90, from 30 to 85, from 30 to 80, from 30 to 75, from 30 to 70, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to 45, from 30 to 40, from 30 to 35, from 35 to 95, from 35 to 90, from 35 to 85, from 35 to 80, from 35 to 75, from 35 to 70, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to 50, from 35 to 45, from 35 to 40, from 40 to 95, from 40 to 90, from 40 to 85, from 40 to 80, from 40 to 75, from 40 to 70, from 40 to 65, from 40 to 60, from 40 to 55, from 40 to 50, from 40 to 45, from 45 to 95, from 45 to 90, from 45 to 85, from 45 to 80, from 45 to 75, from 45 to 70, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to 95, from 50 to 90, from 50 to 85, from 50 to 85, from 50
  • At least 50 (such as at least 55, at least 60, at least 65, at least 70, at least 75, at least 80, at least 85, or at least 90) percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • from 50 to 90 (such as from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 75, from 60 to 65, from 65 to 90, from 65 to 85, from 65 to 80, from 65 to 75, from 65 to 70, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 90, from 80 to 85, or from 85 to 90) percent of the amide linkages are: (i) tertiary amide linkages; and/or (ii) secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group.
  • the functional polyamide has a theoretical functionality of greater than two (such as 3 or more, or 4 or more). In certain embodiments, the functional polyamide has a theoretical functionality of from greater than 2 to 30 (such as from greater than 2 to 25, from greater than 2 to 20, from greater than 2 to 15, from greater than 2 to 10, from greater than 2 to 9, from greater than 2 to 8, from greater than 2 to 7, from greater than 2 to 6, from greater than 2 to 5, from 3 to 30, from 3 to 25, from 3 to 20, from 3 to 15, from 3 to 10, from 3 to 9, from 3 to 8, from 3 to 7, from 3 to 6, from 3 to 5, from 4 to 30, from 4 to 25, from 4 to 20, from 4 to 15, from 4 to 10, from 4 to 9, from 4 to 8, from 4 to 7, from 4 to 6, or from 4 to 5).
  • polyamides with just two functionalities may not completely react with other oligomers/macromonomers to form cured polymers.
  • a polyamide with greater than two functionalities may improve curing over polyamides with just two functionalities, and thereby provide better properties to the resulting cured polymer.
  • the functionality in at least 70 (such as at least 75, at least 80, at least 85, at least 90, at least 95, at least 96, at least 97, at least 98, or at least 99, or 100) mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • the functionality in substantially all molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • the functionality in from 70 to 100 (such as from 70 to 99, from 70 to 98, from 70 to 97, from 70 to 96, from 70 to 95, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 100, from 75 to 99, from 75 to 98, from 75 to 97, from 75 to 96, from 75 to 95, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 100, from 80 to 99, from 80 to 98, from 80 to 97, from 80 to 96, from 80 to 95, from 80 to 90, from 80 to 85, from 85 to 100, from 85 to 99, from 85 to 98, from 85 to 97, from 85 to 96, from 85 to 95, from 85 to 90, from 90 to 100, from 90 to 99, from 90 to 98, from 90 to 97, from 90 to 96, from 90 to 95, from 95 to 100, from 90 to 99, from 90 to 98, from 90 to 97, from 90 to 96, from 90 to 95, from
  • the functionality in from 70 (such as from 75, from 80, from 85, from 90, from 95, from 96, from 97, from 98, or from 99) mole percent of molecules, to substantially all molecules, of the functional polyamide is of the same functional type, selected from at least one of aminofunctional, carboxyl-functional, or hydroxyl-functional.
  • the functionality in at least 70 (such as at least 75, at least 80, at least 85, at least 90, at least 95, at least 96, at least 97, at least 98, or at least 99, or 100) mole percent of molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional, carboxyl -functional, or hydroxyl-functional.
  • the functionality in substantially all molecules of the functional polyamide is of the same functional type, selected from at least one of amino-functional or hydroxyl-functional.
  • the functionality in from 70 to 100 (such as from 70 to 99, from 70 to 98, from 70 to 97, from 70 to 96, from 70 to 95, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 100, from 75 to 99, from 75 to 98, from 75 to 97, from 75 to 96, from 75 to 95, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 100, from 80 to 99, from 80 to 98, from 80 to 97, from 80 to 96, from 80 to 95, from 80 to 90, from 80 to 85, from 85 to 100, from 85 to 99, from 85 to 98, from 85 to 97, from 85 to 96, from 85 to 95, from 85 to 90, from 90 to 100, from 90 to 99, from 90 to 98, from 90 to 100, from 90 to 99, from 90 to 98
  • the functionality in from 70 (such as from 75, from 80, from 85, from 90, from 95, from 96, from 97, from 98, or from 99) mole percent of molecules, to substantially all molecules, of the functional polyamide is of the same functional type, selected from at least one of aminofunctional or hydroxyl-functional.
  • the functionality of a molecule of the polyamide is of the same functional type, what is meant that each functional group on the polyamide is of the same type; when stating that a certain mole percentage of molecules have functionality of the same type, what is meant is that each individual molecule includes functionalities which are all the same type, but it is possible that each individual molecule could have a different functionality from another molecule.
  • 70 mole percent of molecules of the functional polyamide would be of the same functional type. That being said, it is also contemplated that the functionality of all molecules of the polyamide would be of the same functional type, for example 70 mole percent could be hydroxyl-functional.
  • the functionality in at least 70 (such as at least 75, at least 80, at least 85, at least 90, at least 95, at least 96, at least 97, at least 98, or at least 99, or 100) mole percent of molecules of the functional polyamide is of the same functional type and is hydroxyl-functional. In certain embodiments, the functionality in substantially all molecules of the functional polyamide is of the same functional type and is hydroxyl-functional.
  • the functionality in from 70 to 100 (such as from 70 to 99, from 70 to 98, from 70 to 97, from 70 to 96, from 70 to 95, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 100, from 75 to 99, from 75 to 98, from 75 to 97, from 75 to 96, from 75 to 95, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 100, from 80 to 99, from 80 to 98, from 80 to 97, from 80 to 96, from 80 to 95, from 80 to 90, from 80 to 85, from 85 to 100, from 85 to 99, from 85 to 98, from 85 to 97, from 85 to 96, from 85 to 95, from 85 to 90, from 90 to 100, from 90 to 99, from 90 to 98, from 90 to 97, from 90 to 96, from 90 to 95, from 95 to 100, from 90 to 99, from 90 to 98, from 90 to 97, from 90 to 96, from 90 to 95, from
  • the functionality in from 70 (such as from 75, from 80, from 85, from 90, from 95, from 96, from 97, from 98, or from 99) mole percent of molecules, to substantially all molecules, of the functional polyamide is of the same functional type and is hydroxyl-functional.
  • the functional polyamide has a number average molecular weight of from 200 (such as from 300, from 400, from 500, from 600, from 700, from 800, from 900, or from 1,000) to 10,000 (such as to 9,000, to 8,000, to 7,000, to 6,000, to 5,000, to 4,000, to 3,000, or to 2,000) g/mole.
  • Number average molecular weights described herein may be measured using gel permeation chromatography (GPC) using a Waters GPC 2000 equipped with a refractive index detector and Waters Empower® data acquisition and analysis software. Samples were run against polystyrene calibration standards.
  • the columns are polystyrene (PLgel, 5 micron, available from Agilent/Polymer Laboratories, Inc.).
  • PLgel polystyrene
  • PTFE filters for the mobile phase, individual samples are dissolved in tetrahydrofuran and fdtered with PTFE filters before they are injected into the GPC port.
  • the functional polyamide has a viscosity of less than 100,000 (such as less than 90,00, less than 80,000, less than 70,000, less than 60,000, less than 50,000, less than 40,000, less than 30,000, less than 20,000, or less than 10,000) cps measured in methyl amyl ketone solvent at 85% solids at room temperature, as measured by a Brookfield circular disk viscometer with the circular disk spinning at 5 rpm.
  • room temperature is considered to be about 20 to about 25 °C, and within that range, it is expected that these viscosity measurements would not significantly vary.
  • room temperature may mean any one temperature within the range of from about 20 to about 25 °C.
  • the functional polyamide has an acid fragment (A) as follows, connected to an amine fragment (B) as follows, which is terminated by an end group fragment (EG) as follows: wherein, independently for each fragment and each instance of each variable in each fragment: R 1 is a 2- to 36-carbon hydrocarbyl group; B is where the (A) fragment or the (EG) fragment connects to the (B) fragment; m is an integer of from 1 to 3; A is where the (A) fragment connects to the (B) fragment; R 2 is a 2- to 36-carbon hydrocarbyl group; R 3 is H, a 1- to 12- carbon hydrocarbyl group, R 5 -O-H, or R 5 -O-(A) (wherein R 5 is a 2- to 36-carbon hydrocarbyl group, and (A) is where an (A) fragment connects to the (B) fragment via the R 5 -0 linkage); n is an integer of from 1 to 4; X is O or NR 3 ; R
  • fragment (A) represents a hydrocarbyl group with from 1 to 3 carboxyl-derived groups as functionalities anywhere on the hydrocarbyl group, as opposed to a hydrocarbyl group with 1 to 3 repeating carboxyl -derived groups.
  • the “X” in fragment (B) could be OH to provide a functional group for the polyamide, rather than joining to another (A) fragment.
  • end group segment (EG) represents a hydroxyl-functional end group for the polyamide. Similar embodiments including other end groups are possible as set forth herein.
  • any permutations are possible which would result in a polyamide as described herein.
  • the hydroxyl number of the resulting polyamide is from 3 to 400 mg KOH/g.
  • the percent of tertiary amide linkages of the total number of amide linkages may be calculated using the following equation: 100 where n is the number of monomers, the index i refers to a certain monomer, w ter tN is the average number nitrogen atoms in a monomer that form or are part of tertiary amide linkages in the polymerizations, (note: end-group forming amines do not form amide groups during the polymerizations and their amounts are excluded from «.v), WtotaiN is the average number nitrogen atoms in a monomer that form or are part of tertiary amide linkages in the polymerizations (note: the end-group forming amines do not form amide groups during the polymerizations and their amounts are excluded from w to taiN), and n, is the number of moles of the monomer with the index i.
  • the percent of amide linkages of the total number of all heteroatom containing linkages (connecting hydrocarbon linkages) may be calculated using the following equation: 100 where Wtotais is the sum of the average number of heteroatom containing linkages (connecting hydrocarbon linkages) in a monomer and the number of heteroatom containing linkages (connecting hydrocarbon linkages) forming from that monomer by the reaction with a carboxylic acid bearing monomer during the polyamide polymerizations.
  • “Hydrocarbon linkages” are just the hydrocarbon portion of each repeat unit formed from continuous carbon to carbon bonds (i.e. without heteroatoms such as nitrogen or oxygen) in a repeat unit.
  • This hydrocarbon portion would be the ethylene or propylene portion of ethylene oxide or propylene oxide; the undecyl group of dodecyllactam, the ethylene group of ethylenediamine, and the (CH2)4 (or butylene) group of adipic acid.
  • Linkage % The percent of secondary amide linkages capable of individually forming an intramolecular hydrogen bond with a carbonyl group or an ether group (“Linkage %”) may be calculated using the following equation: 100 where wintraN.i refers to the weight fraction of an amide group capable of forming intramolecular hydrogen bonds due to the presence of carbonyl, alcohol or amine groups in the vicinity of that amide group.
  • Intramolecular hydrogen bonds can form when the distance of a hydrogen connected to the nitrogen atom of a secondary amide group is 4 to 7, or most optimally 4 to 5 bonds away from an atom carrying lone electron pairs that are capable of forming strong intramolecular hydrogen bonds with the said hydrogen atom due to the stabilizing effect of 5 or 8, or most optimally 5 to 6 membered rings.
  • the atom carrying the lone electron pair is preferably an alcohol or carbonyl type of oxygen or an amine type of nitrogen and the spacer between said hydrogen atom and the atom carrying the lone electron pair is preferably hydrocarbon.
  • the functional polyamide has a hydroxyl content of from 50 to 400 (such as from 75 to 400, from 100 to 400, from 150 to 400, from 200 to 400, from 250 to 400, from 300 to 400, from 350 to 400, from 50 to 350, from 75 to 350, from 100 to 350, from 150 to 350, from 200 to 350, from 250 to 350, from 300 to 350, from 50 to 300, from 75 to 300, from 100 to 300, from 150 to 300, from 200 to 300, from 250 to 300, from 50 to 250, from 75 to 250, from 100 to 250, from 150 to 250, from 200 to 250, from 50 to 200, from 75 to 200, from 100 to 200, from 150 to 200, from 50 to 150, from 75 to 150, from 100 to 150, from 50 to 100, from 75 to 100, or from 50 to 75) mg KOH/g of functional polyamide, based on the total solids content of the functional polyamide.
  • 50 to 400 such as from 75 to 400, from 100 to 400, from 150 to 400, from 200 to 400, from 250 to 400, from 300 to
  • the polyisocyanate has an average of from greater than 2 to 5 isocyanate groups per molecule. In certain embodiments, the polyisocyanate has an average of from greater than 2 to 4 isocyanate groups per molecule. In certain embodiments, the poly isocyanate has an average of from greater than 2 to 3 isocyanate groups per molecule. In certain embodiments, the poly isocyanate has an average of from 2.1 to 5 isocyanate groups per molecule. In certain embodiments, the polyisocyanate has an average of from 2.1 to 4 isocyanate groups per molecule. In certain embodiments, the polyisocyanate has an average of from 2.1 to 3 isocyanate groups per molecule.
  • the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 3 : 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 3:1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the poly isocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 2: 1.
  • the stoichiometric ratio of the isocyanate groups of the poly isocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 2: 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 2: 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 1.6: 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.1: 1 to 1.6: 1.
  • the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 1.6: 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1 : 1 to 1.5 : 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.1 : 1 to 1.5: 1. In certain embodiments, the stoichiometric ratio of the isocyanate groups of the polyisocyanate to the reactive groups of the functional polyamide is from 1.2: 1 to 1.5: 1.
  • the solvent comprises at least one of methyl amyl ketone, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol methyl ether acetate, propyl acetate, dimethyl carbonate, or butyl acetate.
  • the amount of the polyisocyanate in the composition is from 10 to 35 (such as from 15 to 35, from 20 to 35, from 25 to 35, from 30 to 35, from 10 to 30, from 15 to 30, from 20 to 30, from 25 to 30, from 10 to 25, from 15 to 25, from 20 to 25, from 10 to 20, from 15 to 20, or from 10 to 15) weight percent, based on the total weight of the composition.
  • the amount of the functional polyamide in the composition is from 20 to 45 (such as from 25 to 45, from 30 to 45, from 35 to 45, from 40 to 45, from 20 to 40, from 25 to 40, from 30 to 40, from 35 to 40, from 20 to 35, from 25 to 35, from 30 to 35, from 20 to 30, from 25 to 30, or from 20 to 25) weight percent, based on the total weight of the composition.
  • the amount of the solvent in the composition is from 10 to 25 (such as from 15 to 25, from 20 to 25, from 10 to 20, from 15 to 20, or from 10 to 15) weight percent, based on the total weight of the composition.
  • the composition further comprises at least one additive selected from at least one rheology modifier, at least one polymeric additive, at least one moisture scavenger, at least one dispersant, at least one pigment, at least one catalyst, at least one matting agent, at least one leveling agent, at least one anti-popping additive, at least one defoamer, at least one antimicrobial agent, at least one surface modifier, or at least one hardener.
  • the composition comprises at least one catalyst.
  • the catalyst comprises a tin-based catalyst or a tin-free catalyst.
  • the tin-based catalyst comprises dibutyltin dilaurate.
  • the tin-free catalyst comprises a zirconium chelate or an aluminum chelate.
  • the catalyst is present in the composition in an amount as low as 0.0025 percent by weight, based on the total solids content of the functional polyamide and the polyisocyanate.
  • the composition has a biobased content of from 20 to 40 (such as from 25 to 40, from 30 to 40, from 35 to 40, from 20 to 35, from 25 to 35, from 30 to 35, from 20 to 30, from 25 to 30, or from 20 to 25) percent, as measured by ASTM D6866-22, Method B (AMS) TOC.
  • the composition has a volatile organic compounds content of 250 g/L or less, as measured by EPA Method 24.
  • a coated substrate comprising the composition described herein at least partially coated, directly or indirectly, onto a substrate, to form a coating on the substrate.
  • the substrate comprises at least one of metal, fiberglass, composite, plastic, wood, paper, leather, fabric, ceramic, or cementitious material.
  • the substrate is a primed substrate, such that the coating is applied to the primed substrate.
  • the coating is applied to the substrate via air-assisted spraying, airless spraying, brushing, or rolling onto the substrate.
  • the coating has a film thickness of 1 to 20 mils, as measured by an electronic gauge.
  • the coating is applied as a top coat over the substrate and at least one optional intervening coating layer, and wherein no further coating layers are applied over the top coat.
  • the coating has an abrasion resistance of 36 mg of weight loss or less, as measured by ASTM D4060.
  • polyurethane means polymers which contain urethane and/or urea linkages, as is known to those of ordinary skill in the art. Polyurethanes may contain other polymers and/or materials either as physical blends or where the other polymers and/or materials are co-reacted into the polyurethane polymer.
  • compositions and coating compositions described herein may be made according to known methods for making polyurethane compositions and/or coating compositions.
  • Example functional polyamides (Polyamides A through C) were prepared as follows, with amounts of each component (in grams) being shown in Table 1.
  • Polyamide B Hydrogenated dimer acid, N-(2-hydroxyethyl)ethylenediamine, N-methyl ethanol amine and heat stabilizer were charged to a reactor equipped with a column (Vigreux) and a condenser. The reactor was flushed with nitrogen, heated to 150 °C and held for 6 h at atmospheric pressure, then at 500 mbar for 24 h and then reduced to 40 mbar for 1 h. The reactor was filled with nitrogen and cooled to 50 °C. Methyl amyl ketone was charged and mixed for 1 h at 50 °C. The batch was then cooled to room temperature. The product is a clear viscous liquid at room temperature.
  • Polyamide C Hydrogenated dimer acid, diethanolamine and heat stabilizer were charged to a reactor equipped with a column (Vigreux) and a condenser. The reactor was flushed with nitrogen, heated to 130 °C under 50 mbar pressure and held for 20 h. Then the reactor was filled with nitrogen and the batch was cooled to 50 °C. Methyl amyl ketone was charged and mixed for 1 h at 50 °C. The batch was then cooled to room temperature. The product is a clear viscous liquid at room temperature.
  • Examples 1 to 4 and 6 were prepared by the following process, with compositional information being provided in Table 2 (all amounts shown in weight percentage), below:
  • the functional polyamides Polyamide A, Polyamide B, or Polyamide C, as indicated
  • the hyperdispersant was added to the metal container under gentle mixing.
  • the pigment and solvent were mixed in gradually, following the order as listed in Table 2, and the blend was dispersed for 10 minutes under high speed, creating a donut shape vortex.
  • the fineness of dispersion was evaluated by ASTM D1210-05 using a Hegman- type gage.
  • Example 5 was prepared according to a similar process, except that the dispersion stage was not needed due to absence of pigment, and all the materials were gradually added under mixing as in the letdown stage.
  • Part A was individually agitated and then it was mixed with Part B ingredients as shown in Table 2, for 3 minutes.
  • the ready -to- spray blend was applied over ground cold rolled steel and/or blasted steel, previously cleaned with acetone-wet paper towel.
  • the fdm was allowed to cure for 7 days at ambient conditions.
  • the adhesion and QUV data are based off performance over blasted epoxy-primed steel.
  • An 80/20 methyl amyl ketone/methyl ethyl ketone blend was used as reducer depending on the application method.
  • PLD Phenethyl Ethyl Ketone Resistance
  • MEKR Methyl Ethyl Ketone Resistance
  • IRST Impact Resistance
  • AWR Accelerated Weathering Resistance
  • lOOOh QUV-A was tested according to ASTM G154-23, Cycle 1, with dE and Gloss Retention (“GR”) being reported.
  • compositions based on functional polyamides form top coating films capable to reach high glosses but also showing versatility of the chemistry to provide lower glosses without the use of flattening agents to do so.
  • the compositions exhibit good gloss retention and low color change against accelerated weatherability, without the addition of ultraviolet light absorbers and stabilizers, which is a very relevant property for a top coating and a good indicator of the performance of the functional polyamides when used in a top coating.
  • these coatings display very good mechanical and chemical resistance properties, measured through pencil hardness, Methyl Ethyl Ketone spot test, and impact resistance; confirming these functional polyamides are capable of create polyurethane coating films of high performance.

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Abstract

L'invention concerne des compositions comprenant : un polyisocyanate ayant une moyenne supérieure à deux groupes isocyanate par molécule ; un polyamide fonctionnel ayant une moyenne supérieure à deux groupes réactifs par molécule qui sont chimiquement réactifs avec un groupe isocyanate du polyisocyanate ; et un solvant ; le rapport stœchiométrique entre les groupes isocyanate du polyisocyanate et les groupes réactifs du polyamide fonctionnel étant de 1:1 à 3:1. L'invention concerne également des compositions de revêtement et des substrats revêtus utilisant la composition.
PCT/US2025/025916 2024-04-26 2025-04-23 Compositions de revêtement comprenant des polyamides fonctionnels Pending WO2025226781A1 (fr)

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