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WO2024149654A1 - Utilisation d'amidopropyl bétaïnes d'acides gras insaturés comme épaississants - Google Patents

Utilisation d'amidopropyl bétaïnes d'acides gras insaturés comme épaississants Download PDF

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Publication number
WO2024149654A1
WO2024149654A1 PCT/EP2024/050102 EP2024050102W WO2024149654A1 WO 2024149654 A1 WO2024149654 A1 WO 2024149654A1 EP 2024050102 W EP2024050102 W EP 2024050102W WO 2024149654 A1 WO2024149654 A1 WO 2024149654A1
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Prior art keywords
fatty acid
acyl groups
personal care
formula
care compositions
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English (en)
Inventor
Frank Clasen
Christiane Hoeltgen
Monika Barbenheim
Claudia Brunn
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BASF SE
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BASF SE
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Priority to CN202480007373.3A priority Critical patent/CN120500324A/zh
Priority to EP24700675.2A priority patent/EP4648740A1/fr
Priority to KR1020257022984A priority patent/KR20250133893A/ko
Publication of WO2024149654A1 publication Critical patent/WO2024149654A1/fr
Anticipated expiration legal-status Critical
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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system

Definitions

  • This invention relates to the use of fatty acid amidopropyl betaines derived from fatty acids of rapeseed oil and/or sunflower oil as thickeners for increasing the viscosity of personal care compositions, personal care compositions comprising them, amidopropyl betaines derived from fatty acids of rapeseed oil and its preparation process.
  • Thickeners are widely used in cosmetic personal care compositions for increasing their viscosity. For example, there is a risk of overdose personal care compositions if the viscosity is too low. Thickeners give on the one hand a better applicability for the consumer and on the other hand protect the environment. In recent years synthetic polymeric compounds containing EO/PO have often been used as thickeners. However, more and more manufacturers and consumers want alternative thickeners without EO and or PO units.
  • Amidopropyl betaines of fatty acids have been suggested as a thickener for cosmetic compositions years ago.
  • WO9915610 describes the use of unsaturated fatty acid betaines as thickener for aqueous surfactant solutions. It was suggested to use oleyl amidopropyl betaine for thickening the anionic surfactant sodium glyceryl sulfate or the nonionic surfactant lauroyl-N-methyl-glu- camide or an amphoteric surfactant.
  • oleyl amidopropyl betaine seems to be very effective, they are only available in form of a gel, which are difficult to mix in personal care preparations.
  • thickener which are especially able to increase the viscosity of personal care compositions comprising surfactants, which are essentially free of ethylene oxide (EO) and/ or propylene oxide (PO) units and/or sulfate groups.
  • surfactants which are essentially free of ethylene oxide (EO) and/ or propylene oxide (PO) units and/or sulfate groups.
  • EP121791 discloses that blends of coco amidopropyl betaine and oleyl amidopropyl betaine in a ratio of 1 : 4 to 3: 2 have improved thickener properties compared to pure coco amidopropyl betaine. According to EP121791 the blends were used in amounts from 5 - 30 wt%, which is higher than the amounts of the usual thickeners on a synthetic basis with EO/PO groups. However, there is a need to provide thickeners, which can be used in lower quantities in the range of 2 or 3 wt%, because then the manufacturer of personal care compositions does not have to change their entire formulation. Additionally, lower amounts of thickeners mean mostly lower costs and lower environment impact.
  • thickeners should not only increase the viscosity, but also determine the flow-behavior (e.g. shear-thinning) or temperature sensitivity of the viscosity (e.g. constant viscosity over broad temperature range is desired).
  • thickeners should not negatively impact other aspects of the personal care composition (like appearance or storage stability).
  • amidopropyl betaine derived from rapeseed oil and/or sunflower oil are excellent thickeners, which are very effective in small quantities, and which are easier to handle then the gel-like oleylamidopropyl betaine. Additionally, it was surprisingly found that amidopropyl betaine based on rapeseed oil and/or sunflower oil are very effective thickener for personal care compositions which are difficult to thicken because they are comprising surfactants which are essentially free of ethylene oxide (EO) and/ or propylene oxide (PO) units and/or sulfate groups.
  • EO ethylene oxide
  • PO propylene oxide
  • thickener means substances, which are able to increase the viscosity of personal care composition compared to personal care compositions without those substances, for example determined with the Brookfield Viscosimeter in mPas.
  • Thickeners are preferred, which increase the viscosity of the personal care composition more than 10 % of the value determined with the Brookfield Viscosimeter in mPas compared to the value determined with the Brookfield Viscosimeter in mPas under the same condition without the inventive thickener.
  • Personal Care Compositions in the context of the invention means compositions useful for cleaning or nourishing hair and/or body.
  • the term includes surfactant compositions with and without additional further ingredients.
  • the terms ’’personal care compositions”, “personal care preparations” or “personal care formulations” are used synonymously.
  • the characterization of the betaines with the terms “derived from” or “based on “or “of” rapeseed oil/ and/or sunflower oil(s) are used synonymously.
  • sunflower oil(s) includes natural sunflower oil or sunflower oil with a high oleic acid content or mixtures of both.
  • a first aspect of the invention is directed to the use of fatty acid amidopropyl betaines as thickeners for increasing the viscosity of personal care compositions corresponding to formula (I)
  • RCO is a mixture of acyl groups, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil and/or sunflower oil(s).
  • fatty acid amido propyl betaines corresponding to formula (I) derived from natural rapeseed oil and/or derived from sunflower oil, for example natural sunflower oil and/or or sunflower oil with an especially high content of oleic acid, or any mixtures of them.
  • natural rapeseed oil and/or sunflower oil can have different amounts of saturated and unsaturated fatty acids. In a reduced mass, this also applies to the sunflower oil with an especially high content of oleic acid, which is a bred product, but based on a natural oil and is therefore covered by the term “natural oil” within the invention.
  • the claimed fatty acid amidopropyl betaines corresponding to formula (I), characterized in that RCO is a mixture of acyl groups derived from fatty acids of rapeseed oil and/or sunflower oil (s) comprising more than 80 and less than 95 wt% unsaturated acyl groups - based on acyl groups - are excellent thickeners.
  • RCO is a mixture of acyl groups derived from fatty acids of rapeseed oil and/or sunflower oil(s) comprising more than 5 and less than 20 wt% saturated acyl groups.
  • fatty acid amido propyl betaines corresponding to formula (I) are used, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 55 wt% - 65 wt%, especially 58-64 wt%, acyl groups of oleic acid.
  • RCO is a mixture of acyl groups derived from rapeseed oil comprising 15 wt% - 25 wt%, especially 18 wt% - 21 wt%, acyl groups of linoleic acid.
  • fatty acid amido propyl betaines corresponding to formula (I) in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 7.5 wt% - 12.5 wt%, especially 8 wt% -10 wt%, acyl groups of linolenic acid.
  • fatty acid amido propyl betaines corresponding to formula (I) are used in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 0.5 wt% - 6.5 wt%, especially 1 wt% - 5 wt%, acyl groups of palmitic acid.
  • the wt% acyl groups are always defined as weight percentage based on the weight of the mixture of acyl groups.
  • fatty acid amido propyl betaines corresponding to formula (I) are used where RCO is a mixture of acyl groups of natural rapeseed oil consisting of: 55 wt% - 65 wt% acyl group of oleic acid (C18:1) 15 wt% - 25 wt% acyl group of linoleic acid (C18:2)
  • fatty acid amido propyl betaines corresponding to formula (I) are used, characterized in that RCO is a mixture of acyl groups derived from natural sunflower oil comprising 25 wt% - 40 wt%, acyl groups of oleic acid.
  • fatty acid amido propyl betaines corresponding to formula (I) characterized in that RCO is a mixture of acyl groups derived from natural sunflower oil comprising 45 wt% - 65 wt% acyl groups of linoleic acid.
  • RCO is a mixture of acyl groups of natural sunflower oil consisting of: 25 wt% - 40 wt% acyl groups of oleic acid (C18:1) 50 wt% - 65 wt% acyl groups of linoleic acid (C18:2) 0.0 wt% - 0.5 wt% acyl groups of linolenic acid (C18:3) 0.5 wt% - 6.5 wt% acyl groups of palmitic acid (C16:0) 0.5 wt% - 5.5 wt% acyl groups of stearic acid (C18:0) 0.0 wt% - 0.1 wt% acyl groups of myristic acid (C14:0).
  • fatty acid amido propyl betaines corresponding to formula (I) are used, characterized in that RCO is a mixture of acyl groups derived from sunflower oil with an especially high content of oleic acid comprising 80 wt% - 90 wt%, acyl groups of oleic acid.
  • fatty acid amido propyl betaines corresponding to formula (I) characterized in that RCO is a mixture of acyl groups derived from derived from sunflower oil with an especially high content of oleic acid comprising 5 wt% - 10 wt% acyl groups of linoleic acid.
  • RCO is a mixture of acyl groups of sunflower oil with an especially high content of oleic acid consisting of:
  • acyl group of oleic acid (C18:1) 5.0 wt% - 10 wt% acyl group of linoleic acid (C18:2) 0. 0 wt% - 0.5 wt% acyl group of linolenic acid (C18:3) 0.5 wt% - 6.5 wt% acyl group of palmitic acid (C16:0) 0.5 wt% - 5.5 wt% acyl groups of stearic acid (C18:0) 0.0 wt% - 0.1 wt% acyl groups of myristic acid (C14:0).
  • fatty acid amino propyl betaines are known from literature since the 1980s.
  • DE2926479 describes a process for the preparation of betaines based on fatty acids with from 6 to 18 carbon atoms by quaternization of fatty acid amides with halogen alkylcarboxylic acids in aqueous solution.
  • LIS20160221935 discloses a modified process by using the fatty acid triglyceride esters.
  • fatty acid amino propyl betaines are used in form of an aqueous solution.
  • aqueous solutions means compositions with water.
  • the aqueous solutions according to the invention comprising the fatty acid amidopropyl betaines in quantities of 15% to 55% wt% and water of at least 40% by weight, wherein the wt% is based on the aqueous solution.
  • the aqueous solutions according to the invention comprising the fatty acid amidopropyl betaines in quantities of 20% to 40 wt% and water in quantities of 55 to 70 wt% and 0 to 10 wt% by-products.
  • the by-products may result from the process of making the fatty acid amidopropyl betaines, especially the by-products are selected from the group consisting of glycerol and salts.
  • the aqueous solution comprising the fatty acid amido propyl betaines preferably has a pH range between 8.0 to 12.5.
  • fatty acid amido propyl betaines corresponding to formula (I) as described are used as a thickener for increasing the viscosity of personal care compositions.
  • the betaines are used in form of their aqueous solutions the quantities are calculated as active matter and based on personal care composition.
  • this fatty acid amidopropyl betaines show excellent thickening performance, even in personal care compositions with surfactants, which are difficult to be thickened and even in a small quantity.
  • the inventive betaines also show significantly higher viscosities for example in personal care compositions comprising sulfosuccinates as an EO/PO - free surfactant.
  • Personal care compositions for cleansing and nourishing hair and skin are to be understood here as all compositions known to a person skilled in the art which are exclusively or primarily intended to be applied externally to the human body or hair for the cleaning, caring, protection, and maintaining of a good condition, perfuming, changing the appearance or for influencing.
  • Personal care compositions are in particular surfactant comprising personal care compositions, such as, for example, foam baths, shower gels, shower baths, shower milks, shower creams, shampoos, hair masks, hair milks and hair conditioners.
  • compositions for cleansing and nourishing hair and/or skin comprising thickeners for increasing the viscosity of the personal care compositions, characterized in that they are comprising fatty acid amidopropyl betaines corresponding to formula (I) corresponding to claim 1 in quantities of 0.01-5 wt % - based on personal care composition as thickeners.
  • C) up to 100 wt% other components, different from A) and/or B), wt% calculated as active matter and based on personal care composition.
  • Anionic surfactants nonionic surfactants, amphoteric and/or zwitterionic surfactants
  • Anionic surfactants are known surfactants in personal compositions for cleansing and nourishing hair and skin.
  • anionic surfactants are soaps, alkyl benzenesulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, Methyl ester sulfonates, Alpha-sulfo fatty acid mono and/or di salts, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and di alkyl sulfosuccinates, mono- and di alkyl sulfosuccinamates, sulfotriglycerides
  • ether sulfates are known anionic surfactants which are produced by SO3 or chlorosulfonic acid (CSA) sulfation of fatty alcohol or oxoalcohol polyglycol ethers and subsequent neutralization, for example C12/14 or C12/18 coconut fatty alcohol ether sulfates with 1 to 8 mol ethylene oxide in form of their sodium and/or magnesium salts.
  • CSA chlorosulfonic acid
  • Preferred fatty alcohol ether sulfates are Disodium Laureth Sulfate, commercially available as Texapon® N 70 from BASF Personal Care Nutrition GmbH.
  • Alkyl sulfates are known products which are produced by sulfation of alcohols, preferred of C12- C18 fatty alcohols and more preferred of C12/C14 or C12/C18 fatty alcohol mixtures, for example Sodium Lauryl sulfate, commercially available as Sulfopon® 1218G orTexapon® K 12 from BASF Personal Care Nutrition GmbH.
  • Alpha-sulfo fatty acid di salts can be prepared by all methods known appropriately to those skilled in the art. A particularly preferred method of preparation is the sulfation of the corresponding carboxylic acids with gaseous sulfur trioxide, followed by partially or completely neutralization.
  • Preferred alpha-sulfo fatty acid di salts are technical-grade mixtures of the alpha-sulfo fatty acid di salts, which is commercially available as Texapon® SFA from BASF Personal Care Nutrition GmbH.
  • sulfate-free anionic surfactants are preferred.
  • sulfate-free anionic surfactant refers to an anionic surfactant which does not bear the sulfate group -OSO3 X + as the fatty alcohol sulfates do.
  • the sulfate-free anionic surfactant is selected from the group consisting of acyl isethionates, acyl taurates, acyl glycinates, acyl glutamates, acyl sarcosinates, acyl sulfosuccinates, alpha-sulfo fatty acid mono and/or di salts, alkyl glucose carboxylates, protein/fatty acid condensation products, and mixtures thereof.
  • the sulfate-free anionic surfactant is selected from the group consisting of acyl isethionates, acyl taurates, acyl glycinates, acyl glutamates, and mixtures thereof. It is especially preferred that the sulfate-free anionic surfactant is selected from the group consisting of C12-C18 acyl isethionates, C12-C18 acyl taurates, C12-C18 acyl glycinates, C12-C18 acyl glutamates, acyl sulfosuccinates, alpha-sulfo fatty acid mono and/or di salts, protein/fatty acid condensation products and mixtures thereof.
  • sulfate-free anionic surfactants are sodium lauroyl isethionate, sodium co- coyl isethionate, sodium methyl cocoyl taurate, sodium lauroyl glycinate, sodium cocoyl glycinate, disodium salts of alpha-sulfo fatty acids (C12-14), disodium lauryl sulfosuccinate, sodium cocoyl glutamate, or mixtures thereof.
  • Additional useful anionic surfactants within the context of the invention are selected from the group alkyl- and/or alkenyl oligo glucoside carboxylates.
  • Alkyl- and/or alkenyl oligo glucoside carboxylates are known products and can be made according W002/090369 from alkyl- and/or alkenyl oligo glucoside and Q-halogen carboxylic acid in presence of alkali metal hydroxides.
  • Especially preferred is sodium lauryl glucose carboxylate.
  • Isethionate are known and can be prepared by all methods known to those skilled in the art. For example, by the direct condensation of a salt of isethionic acid with one or more fatty acid(s) or alternatively by indirect means in which first one or more fatty acid(s) is converted into the fatty acid chloride form and then brought to the reaction with the salt of isethionic acid.
  • Isethionates derived from C12 to C18 fatty acids are preferred from C12/C18 fatty acid mixtures and especially preferred from technical C12 fatty acids containing about 70-99 wt% lauric acid and residual amounts higher C14-C18 fatty acids.
  • N-acyl amino acid salts like acyl glycinates, acyl glutamates or acyl sarcosinates.
  • N-Acyl amino acid salts are known products and can be made in different ways, for example from the corresponding fatty acyl chlorides and amino acid salts using Schotten-Baumann chemistry or from the corresponding fatty acid and amino alcohol to give a fatty amide, which is then oxidized to give the N-acyl amino acid salt or according US Pat. No.
  • Preferred N-acyl glycinates are selected from the group sodium cocoyl glycinate, sodium myristyl glycinate and sodium lauryl glycinate.
  • acyl glutamate which are considered in the sense of the invention, are anionic surfactants derived from fatty acids having 12 to 18 carbon atoms such as C12/14 fatty acid mixtures or C 12/18 coconut fatty acid mixtures or of lauric acid, myristic acid, palmitic acid and I or stearic acid. Particularly preferred are di-natrium-N-cocoyl and di-sodium-N-stearoyl- L-glutamate.
  • suitable as anionic surfactants are protein fatty acid condensates, which can be prepared by all methods known appropriately to those skilled in the art, for example reaction of the corresponding fatty acid chloride with the hydrolyzed protein in alkaline medium.
  • useful are C12-C24 fatty acid condensation products of protein hydrolysates, especially based on wheat or soja or rice, very specially C12-C24 condensation products of soja protein hydrolysate, which is commercially available as Plantapon® Soy from BASF Personal Care Nutrition GmbH.
  • the personal care compositions may comprise amphoteric and/or zwitterionic surfactants in addition with or instead of the anionic surfactants.
  • Suitable amphoteric and/or zwitterionic surfactants are betaines and/or amphoacetates.
  • Preferred betaines and/or amphoacetates are selected from the group consisting of carboxylation products of secondary and/or tertiary amines, carboxylation products of amidoamines, imidazolinium betaines and/or amphoacetate surfactants, whereby the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined in formula (I) claim 1.
  • Betaines are neutral chemical compounds with a positively charged cationic functional group such as a quaternary ammonium cation which bears no hydrogen atom and with a negatively charged functional group such as a carboxylate group.
  • betaines are carboxylation products of secondary and/or tertiary amines, preferably carboxylated with halogencarboxylic acids or salts thereof, more particularly with sodium chloroacetate.
  • Typical examples are the carboxymethylation products of hexyl methyl amine, hexyl dimethyl amine, octyl dimethyl amine, decyl dimethyl amine, dodecyl methyl amine, dodecyl dimethyl amine, dodecyl ethyl methyl amine, C12/14 cocoalkyl dimethyl amine, myristyl dimethyl amine, cetyl dimethyl amine, stearyl dimethyl amine, stearyl ethyl methyl amine, oleyl dimethyl amine, C16/18 tallow alkyl dimethyl amine and technical mixtures thereof.
  • betaines are carboxyalkylation products of amidoamines preferably carboxylated with halocarboxylic acids or salts thereof, more particularly with sodium chloroacetate.
  • Typical examples are carboxyalkylation products of fatty acid alkylamidopropyl betaines, wherein the fatty acid alkylamidopropyl betaines can be prepared from fatty acids containing 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof, with N,N-dimethyl aminoethyl amine, N,N-dimethyl aminopropyl amine, N,N-diethyl aminoethyl amine and N,N-diethyl aminopropyl amine.
  • the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined in formula (I).
  • Preferred fatty acid alkylamidopropyl betaines are cocodimethylcarbox- ymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethylalphacarboxyethylbetaine, cetyldimethylcarboxymethylbetaine, laurylbis(2-hydroxypropyl)alphacarboxyethylbetaine, and mixtures thereof.
  • fatty acid alkylamidopropyl betaines Very preferred within the group of fatty acid alkylamidopropyl betaines is the carboxylation product of C8/18 coco fatty acid -N,N-dimethyl aminopropyl amide with sodium chloroacetate, which is known under the CTFA name of Cocamidopropyl Betaine, and which is available as Dehyton® PK45 from BASF Personal Care Nutrition GmbH.
  • imidazolinium betaines can be used. These substances are known and can be obtained for example by cyclizing condensation of 1 or 2 mol of fatty acid with polyfunctional amines such as, for example, aminoethylethanolamine (AEEA) or di-ethylenetriamine.
  • polyfunctional amines such as, for example, aminoethylethanolamine (AEEA) or di-ethylenetriamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the abovementioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C12/14-coconut fatty acid which are subsequently betainized with sodium chloroacetate.
  • amphoteric surfactants salts of amphoacetates are preferred.
  • Amphoacetates can be obtained by a 2-stage reaction, wherein the first stage, a long-chain fatty acid or a fatty acid mixture (e.g. by hydrolysis of coconut oil, palm oil or soybean oil) reacts with 2-(2-aminoethyl- amine) ethanol under reduced pressure and high temperatures to the corresponding 2-alkyl-1- hydroxyethylimidazoline.
  • the obtained imidazoline is hydrolyzed and carboxymethylated with a sodium salt of monochloroacetic acid.
  • amphoacetate sodium cocoamphoacetate, commercially available as Dehyton® MC (supplied by BASF Personal Care and Nutrition GmbH).
  • the personal care compositions are comprising fatty acid alkylamidopropyl betaines as zwitterion surfactants
  • the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined as thickeners in formula (I).
  • the personal care compositions may comprise nonionic surfactants in addition with or instead of anionic surfactants and/or in addition with or instead of amphoteric and/or zwitterionic surfactants.
  • Suitable nonionic surfactants are selected from the group consisting of fatty alcohol polyglycol ether, ethoxylated fatty acid glycerol ester, glycerol mono- and/or di fatty acid esters, polyglyceryl fatty acid esters, mixed ethers or mixed formals; polysorbates and sugar-based carbohydrates like glucamines or alk(en)yl (poly)glycosides, preferably consisting of, glycerol mono- and/or di fatty acid esters, polyglyceryl fatty acid esters and sugar-based carbohydrates.
  • alk(en)yl (poly)glycoside are preferred as sugar-based carbohydrate.
  • Alk(en)yl (poly)glycoside means alkyl and/or alkenyl (poly)glycosides and are known nonionic surfactants which have in particular the formula (II), R1O-[G]p (II) in which
  • R1 is an alkyl/alkenyl radical having 6 to 22 carbon atoms
  • G is a sugar radical having five or six carbon atoms and p is a number from 1 to 10.
  • the alkyl/alkenyl (poly)glycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably from glucose.
  • the preferred alk(en)yl (poly)glycosides are therefore alk(en)yl (poly)glucosides.
  • the index number p in the general formula (II) specifies the degree of polymerization (DP), i.e. the distribution of mono- and polyglycosides, and is a number between 1 and 10.
  • the alkyl and/or alkenyl radical R1 can be derived from primary alcohols having 6 to 22, preferably 6 to 18 carbon atoms. Typical examples are caproic alcohol, caprylic alcohol, decyl alcohol and undecyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and also technical grade mixtures thereof.
  • alkyl (poly) glucosides are selected from the group consisting of Decyl polyglucoside, Lauryl polyglucoside, C8-C18 polyglucoside, wherein C8-C18 means is derived from a mixture of alcohols with 8 to 18 carbon atoms.
  • R1 is derived from primary saturated alcohol mixtures e.g. comprising 10 to 50% by weight of C8/C10 primary saturated alcohol and 50 to 90% by weight of C12 to C18 primary saturated alcohols.
  • R1 of the formula (II) is derived from primary saturated alcohol mixtures comprising 75 to 95% by weight primary saturated alcohols with 12 to 16 carbon atoms.
  • Suitable alkyl (poly) glucoside are products known as Plantacare®810, Plantacare® 1200, Plantacare® 2000, and Plantacare® 818, all available by BASF Personal Care Nutrition GmbH.
  • Alkyl and/or alkenyl glucamide or “N-alkyl/alkenyl glucamides” are known products and derived from glucuronic acid and fatty acids.
  • Preferred are N-alkylglucamides derived from lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid and their technical mixtures.
  • Particular preference is given to the use of a N-methyl glucamides and especially on the basis of a technical C12-C14- coconut fatty acid fraction.
  • Suitable products are Glucopure® Foam or Glucopure® Sense obtainable by Clariant.
  • glycerol mono- and/or di fatty acid esters or polyglyceryl fatty acid esters examples are esters of polyglycerol and linear and/or branched fatty alcohols, especially partial esters of polyglycerol having 2-6 glycerol adducts.
  • polyglycerol esters are esters of polyglycerol and linear and/or branched fatty alcohols, especially partial esters of polyglycerol having 2-6 glycerol adducts.
  • polyglyceryl-2-di hydroxy stearate commercially available as Dehymuls® PGPH from BASF Personal Care and Nutrition GmbH or for example triglycerol-3 diisostearate, commercially available as Lameform® TGI from BASF Personal Care and Nutrition GmbH.
  • glycerol mono esters are mono glycerol esters of fatty acids, especially linear and/or branched fatty acids with 12 to 22 carbon atoms and/or linear and/or branched hydroxy fatty acids with 12-18 carbon atoms like hydroxy stearic acid monoglyceride, isostearic acid monoglyceride, oleic acid monoglyceride, ricinoleic acid monoglyceride, linoleic acid monoglyceride, linolenic acid monoglyceride, stearic acid monoglyceride and/or oleic stearic acid mono glyceride.
  • Preferred are glycerol mono esters of linear saturated and/or unsaturated fatty acids, especially of glycerol mono stearate and/ or glycerol mono oleate.
  • esters of fatty acid monoglycerides which may still contain small amounts of glycerol and/or diglyceride esters and/or triglycerides due to the manufacturing process.
  • Preferred esters are technical mixtures of fatty acid mono glycerides which have a monoglyceride content in the range of 50 to 95 wt%, preferably 60 to 90 wt%.
  • Particularly preferred are mono fatty acid esters of (technical) glycerol and a fatty acid mixture which contains 90 to 100% by weight of oleic acid - based on fatty acid mixture.
  • Such a technical glycerol mono oleate is for example commercially available as Monomuls® 90/18 from BASF personal Care and Nutrition GmbH.
  • fatty alcohol polyglycol ether, ethoxylated fatty acid glycerol ester are addition products of from 2 to 50 mol of ethylene oxide and/or 0 to 20 mol of propylene oxide on linear fatty alcohols having 8 to 40 C atoms, on fatty acids having 12 to 40 C atoms and on alkylphenols having 8 to 15 C atoms in the alkyl group.
  • the personal care compositions are essentially free of surfactants comprising ethylene oxide and/or propylene oxide units.
  • the personal care compositions are comprising as component B) 0.01 to 5 wt% of the inventive thickeners, wt% calculated as active matter and based on personal care composition.
  • the personal care compositions may comprise a series of further auxiliaries and additives, such as, for example, additionally thickeners, bodying agents, viscosity reducers, salts, superfatting agents, stabilizers, polymers, fats, waxes, silicones, lecithins, protein hydrolyates, phospholipids, biogenic active ingredients, UV sunscreen factors, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, selftanning agents, tyrosinase inhibitors (depigmenting agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes, additives for pH adjustment, pearlizers and/or opacifiers and the like, including water.
  • auxiliaries and additives such as, for example, additionally thickeners, bodying agents, viscosity reducers, salts, superfatting agents, stabilizers, polymers, fats, waxes, silicones, lecithins,
  • cationic polymers can include at least one of a cationic guar polymer, a cationic non-guar galactomannan polymer, a cationic tapioca polymer, a cationic copolymer of acrylamide monomers and cationic monomers, synthetic, non-crosslinked, cationic polymers, cationic cellulose derivatives such as, for example, the quaternized hydroxyethyl cellulose, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as, for example, Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat® L, Grunau), quaternized wheat polypeptides, poly-ethylene- imine, cationic silicone polymers
  • the personal care composition may comprise cationic polymer selected from the group consisting of cationically modified cellulose derivatives, PQ 10, PQ 67, cationically modified guar derivatives, such as, for example, Dehyquart® Guar N, guar hydroxypropyltrimonium chloride, cationic homo- or copolymers based on acrylamide, cationic homo- or copolymers based on vinyl pyrrolidone, cationic homo- or copolymers based on quaternized vinyl imidazole and cationic homo- or copolymers based on methacrylates.
  • cationic polymer selected from the group consisting of cationically modified cellulose derivatives, PQ 10, PQ 67, cationically modified guar derivatives, such as, for example, Dehyquart® Guar N, guar hydroxypropyltrimonium chloride, cationic homo- or copolymers based on acrylamide, cationic homo- or copolymers
  • cationically modified guar derivates preferably Guar Hydroxypropyltrimonium Chloride, are present.
  • the personal care compositions may additionally contain polyols as an optional component.
  • Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols may contain other functional groups, more especially amino groups, or may be modified with nitrogen.
  • Typical examples are glycerol; alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1.000 dalton; technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10 such as, for example, technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight; methylol compounds such as, in particular, trimethylol ethane, trimethylol propane, trimethylol butane, pentaerythritol and di pentaerythritol; methyl and butyl glucoside; sugar alcohols for example sorbitol or mannitol; dialcoholamines, such as diethanolamine or 2-aminopropane-1 ,3-diol.
  • alkylene glycols such as, for example, ethylene glyco
  • the personal care compositions may additionally contain oil components for example, Guerbet alcohols based on fatty alcohols containing 6 to 18 and preferably 8 to 10 carbon atoms, esters of linear C6-22 fatty acids with linear C6-22 fatty alcohols, esters of branched C6-13 carboxylic acids with linear C6-22 fatty alcohols such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmi-tate, stearyl stearate, stearyl isostearate, stearyl oleate
  • esters of linear C6- 22 fatty acids with branched alcohols are particularly 2-ethyl hexanol, esters of hydroxy carboxylic acids with linear or branched C6-22 fatty alcohols, more especially Dioctyl Malate, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol and/or Guerbet alcohols, triglycerides based on C6-10 fatty acids, liquid mono- /di-/triglyceride mixtures based on C6-18 fatty acids, esters of C6-22 fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of C2-12 dicarboxylic acids with linear or branched alcohols containing 1 to 22 carbon atoms or polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substitute
  • the personal care compositions may additionally contain superfatting agents, for example, lanolin and lecithin, acylated lanolin, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides.
  • superfatting agents for example, lanolin and lecithin, acylated lanolin, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides.
  • the personal care compositions may additionally contain consistency agents like fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxy-fatty acids.
  • a combination of these substances with alkyl oligoglucosides and/or fatty acid N-methyl glucamides of the same chain length and/or polyglycerol poly-12-hydroxystearates is preferably used.
  • the personal care compositions may additionally contain thickeners, for example Aerosil types (hydrophilic silicas), polysaccharides, more especially xanthan gum, guar-guar, agar-agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also relatively high molecular weight polyethylene glycol mono-esters and diesters of fatty acids, polyacrylates (for example Carbopols® [Goodrich] or Synthalens® [Sigma]), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates or alkyl oligoglucosides and electrolytes, such as sodium chloride and ammonium chloride.
  • thickeners for example Aero
  • the personal care compositions may additionally contain fats and/or waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial fat, ceresine, ozocerite (earth wax), petrolatum, paraffin waxes, microwaxes; chemically modified waxes (hard waxes) such as, for example, montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as, for example, polyalkylene waxes and polyethylene glycol waxes.
  • fats and/or waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, gu
  • the personal care compositions may additionally contain metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers.
  • metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers.
  • the personal care compositions may additionally contain biogenic agents, for example tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisab- olol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • biogenic agents for example tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisab- olol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
  • the personal care compositions may additionally contain film formers, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
  • film formers for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
  • the personal care compositions may additionally contain protein hydrolyzates for example based on keratin such as the commercially available Nutrilan® Keratin W PP or based on wheat and/or soya such as Gluadin® WLM Benz, Gluadin® WK or Gluadin® WP, Gluadain® Kera-P LM. It is also possible to add small amounts of free amino acids such as lysine or arginine.
  • the personal care compositions may additionally contain antidandruff agents like climbazol, oc- topirox and zinc pyrithione.
  • hydrotropes for example ethanol, isopropyl alcohol or polyols, may be used to improve flow behavior.
  • the personal care compositions may additionally contain preservatives for example, benzoic acid, salts of benzoic acid like sodium benzoate, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverowski (“Cosmetics Directive”).
  • Suitable insect repellents are N,N-diethyl- m-toluamide, pentane-1 ,2-diol or Ethyl Butylacetylaminopropionate.
  • a suitable self-tanning agent is dihydroxyacetone.
  • the personal care compositions may additionally contain perfume oils like natural or synthetic fragrances or mixtures of them.
  • the personal care compositions may additionally contain dyes which can be used are the substances approved and suitable for cosmetic purposes, as listed, like cochineal red A (C.l. 16255), patent blue V (C.l. 42051), indigotin (C.l. 73015), chlorophyllin (C.l. 75810), quinoline yellow (C.l. 47005), titanium dioxide (C.l. 77891), indanthrene blue RS (C.l. 69800) and madder lake (C.l. 58000).
  • the personal care compositions may additionally contain water.
  • the personal care composition may have a pH ⁇ 6, preferably in the range of pH 4.5-5.5.
  • fatty acid amidopropyl betains itself are excellent thickener for personal care compositions, which are essential free of surfactants comprising ethylene oxide and/or propylene oxide units and /or which are essential free of surfactants comprising sulfate groups.
  • Another object of the invention is relating to fatty acid amidopropyl betaines corresponding to formula (I')
  • Formula (I’) where n 3 and RCO is a mixture of acyl groups, characterized in that RCO is a mixture of acyl groups of rapeseed oil.
  • fatty acid amido propyl betaines corresponding to formula (I') are preferred, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 55 wt% - 65 wt%, especially 58-64 wt%, acyl groups of oleic acid.
  • RCO is a mixture of acyl groups derived from rapeseed oil comprising 15 wt% - 25 wt%, especially 18 wt% - 21 wt%, acyl groups of linoleic acid.
  • fatty acid amido propyl betaines corresponding to formula (I') in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 7.5 wt% - 12.5 wt%, especially 8 wt % - 10 wt%, acyl groups of linolenic acid.
  • fatty acid amido propyl betaines corresponding to formula (I') in that RCO is a mixture of acyl groups derived from rapeseed oil comprising 0.5 wt% - 6.5 wt%, especially 1 wt % - 5 wt%, acyl groups of palmitic acid.
  • the wt% acyl groups are always defined as weight percentage based on the weight of the mixture of acyl groups.
  • fatty acid amido propyl betaines corresponding to formula (I') in that RCO is a mixture of acyl groups of natural rapeseed oil consisting of: 55 wt% - 65 wt% acyl group of oleic acid (C18:1) 15 wt% - 25 wt% acyl group of linoleic acid (C18:2)
  • Another object of the invention is a process for the preparation of the aqueous solutions of fatty acid amidopropyl betaines corresponding to formula (I'), wherein in the first step a) rapeseed oil and Dimethylaminopropylamine are reacting to the corresponding dimethyl aminopropyl amide and then in step b) reacting said dimethyl amino propylamide with sodium chloroacetate in the presence of water to form water solutions of the fatty acid amidopropyl betaines corresponding to formula (I'), and then in step c) adjusting the pH of the aqueous solution of the fatty acid amidopropyl betaines corresponding to formula (I') to pH 8.0 to 12.5.
  • Example A1 Amidopropyl betaines based on rapeseed oil
  • Rapeseed oil comprising the following fatty acids in wt% was used:
  • Step b) a second reactor vessel was filled with 59.3 kg Na-mono chloroacetate and 620.4 kg water. 203.9 kg of the amidopropyl amine based on rapeseed oil obtained in step a) were added at 70°C.
  • the betaine reaction was carried out under pH control (control at pH 9.5) at 90°C for about 3 to 4 h until the theoretical amine value of titratable residual nitrogen was achieved corresponding to Houben-Weyl DGF-C-V2 (NH2-value theoretical 4.5 in mg KOH).
  • Sunflower oil comprising the following fatty acids in wt% was used:
  • the betaine was prepared in a 2-step process.
  • step a) 442.7 g sunflower oil, 189.0 g dimethylaminopropylamine and 1.3 g hypophosphorous acid (H3PO2 50%) was used.
  • step b) 183.8 g (corresponding 0,5 mol) amidopropyl amine based on sunflower oil obtained in step a), 52.3 g (corresponding 0,45 mol) Na-mono chloroacetate and 354.0 g water was used.
  • An aqueous solution of amidopropyl betaine based on natural sunflower oil with 36.9 wt% active matter was obtained.
  • the obtained betaine has a Brookfield viscosity of 6.200 mPas determined with spindle T93, 0.3 RPM room temperature at pH 12.5.
  • the betaine was prepared in a 2-step process.
  • step a 353.1 g (corresponding 1.25 mol) technical oleic acid (98 wt% oleic acid; residual other fatty acids) was filled in a reactor and 1.0 g hypophosphorous acid (H3PO2 50%) was added and heated up under reflux.
  • H3PO2 50% hypophosphorous acid
  • step b 353.1 g (corresponding 1.25 mol) technical oleic acid (98 wt% oleic acid; residual other fatty acids) was filled in a reactor and 1.0 g hypophosphorous acid (H3PO2 50%) was added and heated up under reflux.
  • H3PO2 50% hypophosphorous acid
  • dimethylaminopropylamine was added.
  • the reaction temperature was heated to 200°C.
  • Resulting water was distilled off with a reflux condenser.
  • the excess of the amine was distilled off at 130°C under vacuum until approximately the theoretical value % N titr. was reached.
  • step b) was carried out according to step b) in Example A1), but wherein 170.3 g 0.5 mol) amidopropyl amine based on oleic acid obtained in step a), 52.3 g (0.45 mol) Na-mono chloroacetate and 303.0 g water was used. An aqueous solution of amidopropyl betaine based on oleic acid was obtained with 39.1 wt% active matter.
  • compositions comprising amidopropyl betaines according to A1) to A3)
  • Table 1 and 2 disclose cosmetic compositions comprising amido propyl betaines based on rapeseed oil according A1) or based on sunflower oil according to A2 or based on oleic acid as comparison according A3). All compositions comprising surfactants without EO/PO units.
  • Plantapon® PSC available from BASF Personal Care Nutrition GmbH; surfactant mixture; INCI: Coco-Glucoside (and) Disodium Lauryl Sulfosuccinate (and) Glycerin; Active matter: 45 wt% Dehyton® PK 45 available from BASF Personal Care Nutrition GmbH; surfactant; INCI: Cocami- dopropyl Betaine; Active Matter: 37 wt%
  • Dehyquart® CC6 available from BASF Personal Care Nutrition GmbH; conditioning agent;
  • Dehyton® SFA available from BASF Personal Care Nutrition GmbH; surfactant mixture; INCI: Cocamidopropyl Betaine (and) Disodium 2-Sulfolaurate; Active Matter: 45 wt%
  • Plantapon® SF-N available from BASF Personal Care Nutrition GmbH; surfactant mixture; INCI: Sodium Cocoamphoacetate (and) Glycerin (and) Lauryl Glucoside (and) Sodium Cocoyl Glutamate (and) Sodium Lauryl Glucose Carboxylate Active Matter 30 wt%
  • Table 1 + 2 show that the inventive amidopropyl betaines based on both rapeseed oil or sunflower oil have very good thickening properties in personal care compositions.
  • Table 1 shows that personal care compositions comprising a surfactant mixture comprising the nonionic-surfactant alkyl(poly)glucoside and the anionic surfactant sulfosuccinate has a viscosity of 5049 mPas (Comp. example B1) and increased to 8278 mPas (Inventive example B2) or to 7288 mPas (Inventive example B3) after adding the inventive amido propyl betaines.
  • Compar. example B1 shows the same personal care composition comprising oleic acid-based betaine A3 with lower viscosities than the inventive ones.
  • Table 2 shows that the viscosity of a personal care compositions comprising a different surfactant mixture was increased by adding the inventive amido propyl betaines A1 or A2 (Inventive Example B6 + B7).
  • Table 3 shows that the viscosity of a further personal care compositions comprising a different surfactant mixture was increased by adding the inventive amido propyl betaines A1 or A2 (Inventive Example B9+ B10) compared to other betaines like Cocamidopropyl Betaine (Comparison Example B8)

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Abstract

La présente invention concerne l'utilisation d'amidopropyl bétaïnes d'acides gras dérivées d'acides gras d'huile de colza et/ou d'huile de tournesol en tant qu'épaississants pour augmenter la viscosité de compositions de soins personnels et concerne en particulier des amidopropyl bétaïnes dérivées d'acides gras d'huile de colza et leur procédé de préparation.
PCT/EP2024/050102 2023-01-11 2024-01-03 Utilisation d'amidopropyl bétaïnes d'acides gras insaturés comme épaississants Ceased WO2024149654A1 (fr)

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EP24700675.2A EP4648740A1 (fr) 2023-01-11 2024-01-03 Utilisation d'amidopropyl bétaïnes d'acides gras insaturés comme épaississants
KR1020257022984A KR20250133893A (ko) 2023-01-11 2024-01-03 증점제로서의 불포화 지방산 아미도프로필 베타인의 용도

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Publication number Priority date Publication date Assignee Title
DE2926479B1 (de) 1979-06-30 1980-11-06 Goldschmidt Ag Th Verfahren zur Herstellung von Betainen
US4380646A (en) 1980-02-02 1983-04-19 Dynamit Nobel Aktiengesellschaft Method for the N-acylation of aminocarboxylic acids
EP0121791A2 (fr) 1983-03-14 1984-10-17 Miranol Inc. Compositions cosmétiques à base de bétaines
EP0560114A2 (fr) * 1992-03-09 1993-09-15 Th. Goldschmidt AG Solution aqueuse liquide d'une bétaine avec une teneur en solides d'au moins 40 % en poids
WO1997003043A1 (fr) 1995-07-13 1997-01-30 Basf Aktiengesellschaft Procede de production d'acides n-acylaminocarboxiliques et d'acides n-acylaminosulfoniques et leurs sels de metaux alcalins
WO1999015610A1 (fr) 1997-09-25 1999-04-01 Cognis Deutschland Gmbh Utilisation de tensioactifs betainiques insatures comme epaississsants
WO2002090369A2 (fr) 2001-05-08 2002-11-14 Cognis Deutschland Gmbh & Co. Kg Procede de production de melanges d'agents tensioactifs
EP3050946A1 (fr) 2015-01-30 2016-08-03 Evonik Degussa GmbH Betaïne comprenant une repartition speciale des acides gras

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DE2926479B1 (de) 1979-06-30 1980-11-06 Goldschmidt Ag Th Verfahren zur Herstellung von Betainen
EP0020907A2 (fr) * 1979-06-30 1981-01-07 Th. Goldschmidt AG Procédé de préparation de bétaines
US4380646A (en) 1980-02-02 1983-04-19 Dynamit Nobel Aktiengesellschaft Method for the N-acylation of aminocarboxylic acids
EP0121791A2 (fr) 1983-03-14 1984-10-17 Miranol Inc. Compositions cosmétiques à base de bétaines
EP0560114A2 (fr) * 1992-03-09 1993-09-15 Th. Goldschmidt AG Solution aqueuse liquide d'une bétaine avec une teneur en solides d'au moins 40 % en poids
WO1997003043A1 (fr) 1995-07-13 1997-01-30 Basf Aktiengesellschaft Procede de production d'acides n-acylaminocarboxiliques et d'acides n-acylaminosulfoniques et leurs sels de metaux alcalins
WO1999015610A1 (fr) 1997-09-25 1999-04-01 Cognis Deutschland Gmbh Utilisation de tensioactifs betainiques insatures comme epaississsants
WO2002090369A2 (fr) 2001-05-08 2002-11-14 Cognis Deutschland Gmbh & Co. Kg Procede de production de melanges d'agents tensioactifs
EP3050946A1 (fr) 2015-01-30 2016-08-03 Evonik Degussa GmbH Betaïne comprenant une repartition speciale des acides gras
US20160221935A1 (en) 2015-01-30 2016-08-04 Evonik Degussa Gmbh Betaines with special fatty acid chain distribution

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