Use of unsaturated fatty acid amidopropyl betaines as thickeners

Abstract

The present invention relates to the use of fatty acid amidopropyl betaines derived from rapeseed oil and / or sunflower oil fatty acids as thickeners to increase the viscosity of personal care compositions, and in particular to amidopropyl betaines derived from rapeseed oil fatty acids and methods for their preparation.

Description

[Technical Field]

[0001] The present invention relates to the use of fatty acid amidopropyl betaines derived from rapeseed oil and / or sunflower oil fatty acids as thickeners for increasing the viscosity of personal care compositions, personal care compositions containing them, amidopropyl betaines derived from rapeseed oil fatty acids and methods for preparing the same. [Background technology]

[0002] Thickeners are widely used in cosmetic personal care compositions to increase their viscosity. For example, if the viscosity is too low, there is a risk of overusing the personal care composition. Thickeners provide consumers with better application on the one hand and protect the environment on the other. In recent years, synthetic polymer compounds containing EO / PO have often been used as thickeners. However, more and more manufacturers and consumers are seeking alternative thickeners that do not contain EO and / or PO units.

[0003] Fatty acid amidopropyl betaines have been suggested as thickeners for cosmetic compositions for several years. International Publication No. 9915610 describes the use of unsaturated fatty acid betaines as thickeners for aqueous surfactant solutions. It has been suggested that oleyl amidopropyl betaine be used to thicken the anionic surfactant sodium glyceryl sulfate, the nonionic surfactant lauroyl-N-methyl-glucamide, or amphoteric surfactants. However, although aqueous formulations of oleyl amidopropyl betaine appear to be highly effective, they are only available in gel form and are difficult to incorporate into personal care formulations.

[0004] U.S. Patent Application Publication No. 2016 / 0221935, corresponding to Evonik's European Patent Application No. 3050946, recommends amidopropyl betaines derived from specialized palm kernel oils with a high oleic acid content of 12-21% as more effective than amidopropyl betaines derived from other triglycerides containing lower percentages of oleic acid, and these amidopropyl betaines exhibit good thickening properties in the context of compositions containing ethoxylated surfactants. Summary of the Invention [Problem to be solved by the invention]

[0005] There is currently a need in the market for thickeners that can increase the viscosity of personal care compositions, particularly those containing surfactants that are substantially free of ethylene oxide (EO) and / or propylene oxide (PO) units and / or sulfate groups.

[0006] EP 121791 discloses that blends of cocoamidopropyl betaine and oleylamidopropyl betaine in a ratio of 1:4 to 3:2 have improved thickening properties compared to pure cocoamidopropyl betaine. According to EP 121791, the blends were used in amounts of 5 to 30 wt %, which is higher than the amounts typically used in synthetic thickeners that use EO / PO groups. However, there is a need to provide thickeners that can be used in lower amounts, in the range of 2 or 3 wt %, because this would allow manufacturers of personal care compositions to avoid changing their entire formulations. Additionally, lower amounts of thickener generally mean lower costs and less environmental impact.

[0007] Furthermore, the thickener should not only increase viscosity, but also determine the flow behavior (e.g., shear thinning) or temperature sensitivity of the viscosity (e.g., a constant viscosity over a wide temperature range is desired).

[0008] Additionally, the thickener should not adversely affect other aspects of the personal care composition, such as appearance or shelf stability. [Means for solving the problem]

[0009] Surprisingly, it has been found that amidopropyl betaines derived from rapeseed oil and / or sunflower oil are excellent thickeners, are very effective in small amounts, and are easier to handle than gel-like oleyl amidopropyl betaines.In addition, it has been surprisingly found that amidopropyl betaines based on rapeseed oil and / or sunflower oil are very effective thickeners for personal care compositions that are difficult to thicken because they contain surfactants that are substantially free of ethylene oxide (EO) units and / or propylene oxide (PO) units and / or sulfate groups. DETAILED DESCRIPTION OF THE INVENTION

[0010] In the context of the present invention, "thickener" means a substance capable of increasing the viscosity of a personal care composition, measured in mPas, for example using a Brookfield viscometer, compared to a personal care composition that does not contain that substance.

[0011] Thickeners that increase the viscosity of a personal care composition by more than 10% as measured in mPas by a Brookfield Viscometer compared to the value measured in mPas by a Brookfield Viscometer under the same conditions without the thickener of the present invention are preferred.

[0012] In the context of the present invention, "quantity" or "amount" in "wt%" means % by weight (= wt%). It may be calculated as active substance (= AM), calculated as the difference between 100% and the sum of the contents of water and by-products.

[0013] In the context of the present invention, "personal care composition" means a composition useful for cleansing or nourishing hair and / or body. The term includes surfactant compositions with and without additional further ingredients. The terms "personal care composition," "personal care formulation," or "personal care formulation" are used interchangeably.

[0014] In the context of the present invention, the characterization of betaines using the terms "derived from" rapeseed oil and / or sunflower oil or "based on" rapeseed oil and / or sunflower oil or "of" rapeseed oil and / or sunflower oil is used synonymously.

[0015] In the context of the present invention, the term "sunflower oil" includes natural sunflower oil or sunflower oil with a high oleic acid content or a mixture of both.

[0016] A first aspect of the present invention provides a compound of formula (I) as a thickening agent for increasing the viscosity of a personal care composition. [ka] wherein n=3 and 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.

[0017] According to the present invention, it is preferred to use fatty acid amidopropyl betaines corresponding to formula (I) derived from natural rapeseed oil and / or sunflower oil, for example, natural sunflower oil and / or sunflower oil with a particularly high oleic acid content, or any mixture thereof.Natural rapeseed oil and / or sunflower oil are natural products, so they may have different amounts of saturated and unsaturated fatty acids.In terms of converted mass, this also applies to sunflower oil with a particularly high oleic acid content.Although it is a breeding product, it is based on natural oil, and therefore is included in the term "natural oil" in the present invention.

[0018] The inventors have found that fatty acid amidopropyl betaines according to the claimed formula (I), characterized in that the RCO is a mixture of acyl groups derived from rapeseed and / or sunflower oil fatty acids, containing more than 80 wt. % and less than 95 wt. % unsaturated acyl groups, based on the acyl groups, are excellent thickeners.

[0019] Preferably, fatty acid amidopropyl betaines corresponding to formula (I) are used in which RCO is a mixture of acyl groups derived from rapeseed oil and / or sunflower oil fatty acids, containing more than 5 wt. % and less than 20 wt. % saturated acyl groups.

[0020] According to one embodiment of the present invention, fatty acid amidopropyl betaines are used, which correspond to formula (I), characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 55% to 65% by weight, in particular 58 to 64% by weight, of oleic acid acyl groups. Furthermore, fatty acid amidopropyl betaines corresponding to formula (I), characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 15% to 25% by weight, in particular 18 to 21% by weight, of linoleic acid acyl groups, are preferred. Furthermore, fatty acid amidopropyl betaines corresponding to formula (I), characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 7.5% to 12.5% ​​by weight, in particular 8 to 10% by weight, of linolenic acid acyl groups, are preferred. It is also preferred to use fatty acid amidopropyl betaines corresponding to formula (I) in which RCO is a mixture of acyl groups derived from rapeseed oil, containing 0.5 wt. % to 6.5 wt. %, in particular 1 wt. % to 5 wt. %, of palmitic acid acyl groups.

[0021] The wt% of acyl groups is always defined as the weight percent based on the weight of the mixture of acyl groups.

[0022] According to this embodiment, the RCO: 55wt% to 65wt% acyl groups of oleic acid (C18:1) 15wt% to 25wt% acyl groups of linoleic acid (C18:2) 7.5wt% to 12.5wt% acyl groups of linolenic acid (C18:3) 0.5wt% to 6.5wt% of palmitic acid (C16:0) acyl groups 0.5wt% to 3.5wt% of stearic acid (C18:0) acyl groups 0.0wt%~0.1wt% acyl group of myristic acid (C14:0) Most preferred fatty acid amidopropyl betaines are used corresponding to formula (I), which is a mixture of acyl groups of natural rapeseed oil consisting of:

[0023] According to another embodiment of the invention, fatty acid amidopropyl betaines corresponding to formula (I) are used, characterized in that RCO is a mixture of acyl groups derived from natural sunflower oil, containing 25% to 40% by weight of oleic acid acyl groups.

[0024] Furthermore, preference is given to fatty acid amidopropyl betaines corresponding to formula (I), characterized in that RCO is a mixture of acyl groups derived from natural sunflower oil, containing 45 wt% to 65 wt% of linoleic acid acyl groups.

[0025] According to this embodiment, the RCO: 25wt%~40wt% acyl groups of oleic acid (C18:1) 50wt%~65wt% acyl groups of linoleic acid (C18:2) 0.0wt% to 0.5wt% acyl groups of linolenic acid (C18:3) 0.5wt% to 6.5wt% of palmitic acid (C16:0) acyl groups 0.5wt% to 5.5wt% acyl groups of stearic acid (C18:0) 0.0wt%~0.1wt% acyl group of myristic acid (C14:0) Most preferred fatty acid amidopropyl betaines according to formula (I) are used, which are a mixture of acyl groups of natural sunflower oil consisting of:

[0026] According to another embodiment of the invention, fatty acid amidopropyl betaines corresponding to formula (I) are used, characterized in that RCO is a mixture of acyl groups derived from sunflower oil with a particularly high content of oleic acid, containing 80% to 90% by weight of oleic acid acyl groups.

[0027] Furthermore, fatty acid amidopropyl betaines corresponding to formula (I) are preferred, characterized in that RCO is a mixture of acyl groups derived from sunflower oil containing 5% to 10% by weight of linoleic acid acyl groups, in particular from sunflower oil with a high content of oleic acid.

[0028] According to this embodiment, the RCO: 80wt%~90wt% acyl groups of oleic acid (C18:1) 5.0wt% to 10wt% of acyl groups of linoleic acid (C18:2) 0.0wt% to 0.5wt% acyl groups of linolenic acid (C18:3) 0.5wt% to 6.5wt% of palmitic acid (C16:0) acyl groups 0.5wt% to 5.5wt% acyl groups of stearic acid (C18:0) 0.0wt%~0.1wt% acyl group of myristic acid (C14:0) Most preferably fatty acid amidopropyl betaines are used corresponding to formula (I), which is a mixture of acyl groups of sunflower oil with a particularly high content of oleic acid consisting of:

[0029] Some fatty acid aminopropyl betaines have been known in the literature since the 1980s.For example, German Patent No. 2926479 describes a method for preparing betaines based on fatty acids having 6 to 18 carbon atoms by quaternization of fatty acid amides with halogen alkyl carboxylic acids in aqueous solution.US Patent Application Publication No. 20160221935 discloses a modification method using fatty acid triglyceride esters.

[0030] According to the present invention, the fatty acid aminopropyl betaines are preferably used in the form of an aqueous solution. The term "aqueous solution" refers to a composition containing water. The aqueous solution according to the present invention comprises fatty acid amidopropyl betaines in an amount of 15% to 55% by weight and at least 40% by weight of water (wt% based on the aqueous solution). Preferably, the aqueous solution according to the present invention comprises fatty acid amidopropyl betaines in an amount of 20% to 40% by weight, water in an amount of 55 to 70% by weight, and 0 to 10% by weight of by-products. The by-products may result from the process for preparing the fatty acid amidopropyl betaines, and in particular, the by-products are selected from the group consisting of glycerol and salts. According to the present invention, the aqueous solution containing fatty acid amidopropyl betaines preferably has a pH range of 8.0 to 12.5.

[0031] According to the present invention, the fatty acid amidopropyl betaines according to the formula (I) described above are used as thickeners for increasing the viscosity of personal care compositions, especially in the form of their aqueous solutions. Generally, it is recommended to use the fatty acid amidopropyl betaines according to the formula (I) in an amount of 0.01 to 5 wt %, especially 0.5 to 3 wt %, based on the personal care composition. When the betaines are used in the form of their aqueous solutions, the amount is calculated as active substance based on the personal care composition.

[0032] The inventors have found that the fatty acid amidopropyl betaines exhibit excellent thickening performance even in small amounts, even in personal care compositions with surfactants that are difficult to thicken. Compared to similar amidopropyl betaines based solely on oleic acid, the betaines of the present invention exhibit significantly higher viscosity, even in personal care compositions containing, for example, sulfosuccinate as an EO / PO-free surfactant.

[0033] Personal care compositions for cleaning and nourishing hair and skin are herein understood to mean all compositions known to those skilled in the art that are intended to be applied exclusively or primarily to the outside of the human body or hair for cleaning, caring for, protecting and maintaining good condition, perfumery, changing or influencing the appearance, etc. Personal care compositions are in particular surfactant-containing personal care compositions, such as foam baths, shower gels, shower baths, shower milks, shower creams, shampoos, hair masks, hair milks, and hair conditioners.

[0034] Another object of the present invention is a personal care composition for cleansing and nourishing hair and / or skin, comprising a thickener for increasing the viscosity of the personal care composition, characterized in that the personal care composition contains fatty acid amidopropyl betaines corresponding to formula (I) corresponding to claim 1 as thickener in an amount of 0.01 to 5 wt %, based on the personal care composition.

[0035] A) 1.0 to 30 wt. %, in particular 5.0 to 25.0 wt. %, of one or more surfactants selected from the group consisting of anionic surfactants, nonionic surfactants, amphoteric and / or zwitterionic surfactants, B) 0.01 to 5 wt. % of fatty acid amidopropyl betaines corresponding to formula (I) as thickeners as claimed in claim 1, C) up to 100 wt% of other components different from A) and / or B). Preferred are personal care compositions comprising:

[0036] A) Anionic surfactants, nonionic surfactants, amphoteric and / or zwitterionic surfactants Anionic surfactants are known surfactants in personal compositions for cleansing and nourishing hair and skin. Examples of anionic surfactants include soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, methyl ester sulfonates, simple and / or double salts of alpha-sulfofatty acids, 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 dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, alkyl glucose carboxylates, acyl isethionates, acyl taurates, acyl glycinates, acyl glutamates, acyl sarcosinates, acyl succinates, alkyl ether carboxylates, fatty alcohol ether phosphates, protein / fatty acid condensation products, and alkyl oligoglucoside sulfates. When the anionic surfactant contains a polyglycol ether chain, the polyglycol ether chain may have a conventional homolog distribution, but preferably has a narrow homolog distribution.

[0037] Alkyl ether sulfates ("ether sulfates") are known anionic surfactants prepared by sulfating polyglycol ethers of fatty alcohols or oxoalcohols with SO or chlorosulfonic acid (CSA), followed by neutralization, e.g., in the form of the sodium and / or magnesium salts of C12 / 14 or C12 / 18 coconut fatty alcohol ether sulfates having 1 to 8 moles of ethylene oxide. A preferred fatty alcohol ether sulfate is disodium laureth sulfate, commercially available as Texapon® N70 from BASF Personal Care Nutrition GmbH.

[0038] Alkyl sulfates are known products produced by sulfation of alcohols, preferably C12-C18 fatty alcohols, more preferably C12 / C14 or C12 / C18 fatty alcohol mixtures, such as sodium lauryl sulfate commercially available as Sulfopon® 1218G or Texapon® K12 from BASF Personal Care Nutrition GmbH.

[0039] The double salts of alpha-sulfofatty acids can be prepared by any method known to those skilled in the art, with a particularly preferred method being by sulfation of the corresponding carboxylic acid with gaseous sulfur trioxide, followed by partial or complete neutralization.

[0040] A preferred double salt of alpha-sulfo fatty acids is a technical grade mixture of double salts of alpha-sulfo fatty acids, which is commercially available as Texapon® SFA from BASF Personal Care Nutrition GmbH.

[0041] According to the present invention, sulfate-free anionic surfactants are preferred. The term "sulfate-free anionic surfactants" as used herein refers to surfactants containing sulfate groups -OSO3, such as those carried by fatty alcohol sulfates. - X + It refers to anionic surfactants that do not carry a

[0042] Preferably, the sulfate-free anionic surfactant is selected from the group consisting of acyl isethionates, acyl taurates, acyl glycinates, acyl glutamates, acyl sarcosinates, acyl sulfosuccinates, mono- and / or double salts of alpha-sulfo fatty acids, alkyl glucose carboxylates, protein / fatty acid condensation products, and mixtures thereof.

[0043] More preferably, 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 particularly 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, mono- and / or double salts of alpha-sulfo fatty acids, protein / fatty acid condensation products, and mixtures thereof.

[0044] Examples of preferred sulfate-free anionic surfactants include sodium lauroyl isethionate, sodium cocoyl isethionate, sodium cocoyl methyl 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.

[0045] Additional useful anionic surfactants in the context of the present invention are selected from the group of alkyl- and / or alkenyl oligoglucoside carboxylates. Alkyl- and / or alkenyl oligoglucoside carboxylates are known products and can be prepared from alkyl- and / or alkenyl oligoglucosides and Ω-halogen carboxylic acids in the presence of alkali metal hydroxides according to WO 02 / 090369. Sodium lauryl glucose carboxylate is particularly preferred.

[0046] Isethionates are known and can be prepared by any method known to those skilled in the art, such as by direct condensation of a salt of isethionic acid with one or more fatty acids, or alternatively by indirect means in which one or more fatty acids are first converted into the fatty acid chloride form, which is then reacted with a salt of isethionic acid.

[0047] Isethionates derived from C12 to C18 fatty acids are preferred, with isethionates derived from mixtures of C12 / C18 fatty acids being more preferred, and isethionates derived from technical C12 fatty acids containing about 70-99 wt% lauric acid and the remainder being higher C14 to C18 fatty acids being especially preferred.

[0048] Further anionic surfactants useful in the context of the present invention are N-acylamino acid salts, such as acylglycinates, acylglutamates, or acylsarcosinates. N-acylamino acid salts are known products and can be prepared in various ways, for example, by using the Schotten-Baumann reaction from the corresponding fatty acyl chloride and amino acid salt, or by preparing a fatty amide from the corresponding fatty acid and amino alcohol, followed by oxidation to obtain the N-acylamino acid salt, or by contacting an aminocarboxylic acid or its metal salt with a lower alkylcarboxylic acid ester in the presence of an alkali metal or alkaline earth metal alcoholate, as described in U.S. Pat. No. 4,380,646, or by reacting a mono-, di-, or triglyceride with an amino acid salt in the presence of a strong base, as described in WO 97 / 03043.

[0049] Preferred N-acylglycinates are selected from the group of sodium cocoyl glycinate, sodium myristyl glycinate, and sodium lauryl glycinate.

[0050] The preferred sarcosinate is N-methylglycinate, selected from the group of sodium cocoyl sarcosinate, sodium myristyl sarcosinate, and sodium lauryl sarcosinate.

[0051] Typical examples of suitable acylglutamates within the meaning of the present invention are anionic surfactants derived from fatty acids having 12 to 18 carbon atoms, such as mixtures of C12 / 14 fatty acids or mixtures of C12 / 18 coconut fatty acids, or from lauric, myristic, palmitic and / or stearic acid. Disodium N-cocoyl L-glutamate and disodium N-stearoyl-L-glutamate are particularly preferred.

[0052] Also suitable as anionic surfactants are protein fatty acid condensates, which can be prepared by any method known to those skilled in the art, for example, by reacting the corresponding fatty acid chloride with hydrolyzed protein in an alkaline medium. Particularly useful are C12-C24 fatty acid condensates of wheat-, soybean- or rice-based protein hydrolysates, and particularly C12-C24 condensates of soybean protein hydrolysates, which are commercially available as Plantapon® Soy from BASF Personal Care Nutrition GmbH.

[0053] Furthermore, the personal care composition may contain amphoteric and / or zwitterionic surfactants in addition to or instead of the anionic surfactant. 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, in which case the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined in formula (I) claim 1.

[0054] Betaines are neutral chemical compounds of a positively charged cationic functional group, such as a quaternary ammonium cation that does not carry a hydrogen atom, and a negatively charged functional group, such as a carboxylate group.

[0055] A preferred group of betaines are the carboxylation products of secondary and / or tertiary amines, preferably carboxylated with halogen carboxylic acids or their salts, more particularly with sodium chloroacetate. Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, dodecylethylmethylamine, C12 / 14 cocoalkyldimethylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearylethylmethylamine, oleyldimethylamine, C16 / 18 tallow alkyldimethylamine and technical mixtures thereof.

[0056] Other suitable betaines are the carboxyalkylation products of amidoamines, which are preferably carboxylated with a halocarboxylic acid or its salt, more particularly with sodium chloroacetate.

[0057] Typical examples are the carboxyalkylation products of fatty acid alkylamidopropyl betaines, which can be prepared from fatty acids containing 6 to 22 carbon atoms, i.e., caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid, and erucic acid, and technical mixtures thereof, with N,N-dimethylaminoethylamine, N,N-dimethylaminopropylamine, N,N-diethylaminoethylamine, and N,N-diethylaminopropylamine. As already mentioned, these fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined by formula (I). Preferred fatty acid alkylamidopropyl betaines are cocodimethylcarboxymethyl betaine, lauryldimethylcarboxymethyl betaine, lauryldimethylalphacarboxyethyl betaine, cetyldimethylcarboxymethyl betaine, laurylbis(2-hydroxypropyl)alphacarboxyethyl betaine, and mixtures thereof.

[0058] Highly preferred within the group of fatty acid alkylamidopropyl betaines is the carboxylation product of C8 / 18 coco fatty acid-N,N-dimethylaminopropylamide with sodium chloroacetate, known under the CTFA name cocamidopropyl betaine and available as Dehyton® PK45 from BASF Personal Care Nutrition GmbH.

[0059] Furthermore, imidazolinium betaines can be used. These substances are known and can be obtained, for example, by cyclocondensation of one or two moles of a fatty acid with a polyfunctional amine, such as aminoethylethanolamine (AEEA) or diethylenetriamine. The corresponding carboxyalkylation products are mixtures of different open-chain betaines. Typical examples are the condensation products of the above-mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or also C12 / 14-coconut fatty acid, which are then betained with sodium chloroacetate.

[0060] Among the amphoteric surfactants, salts of amphoacetates are preferred. Amphoacetates can be obtained by a two-step reaction: in the first step, a long-chain fatty acid or a mixture of fatty acids (e.g., by hydrolysis of coconut, palm, or soybean oil) is reacted with 2-(2-aminoethylamine)ethanol under reduced pressure and elevated temperature to give the corresponding 2-alkyl-1-hydroxyethyl imidazoline. In the second step, the resulting imidazoline is hydrolyzed and carboxymethylated with the sodium salt of monochloroacetic acid.

[0061] A particularly preferred amphoacetate is sodium cocoamphoacetate, commercially available as Dehyton® MC (supplied by BASF Personal Care and Nutrition GmbH).

[0062] When the personal care composition comprises fatty acid alkylamidopropyl betaines as zwitterionic surfactants, it is preferred according to the present invention that the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined as thickeners in formula (I).

[0063] Additionally, the personal care compositions may include nonionic surfactants in addition to or in place of the anionic surfactants and / or in addition to or in place of the amphoteric and / or zwitterionic surfactants.

[0064] Suitable nonionic surfactants are selected from the group consisting of fatty alcohol polyglycol ethers, ethoxylated fatty acid glycerol esters, glycerol mono- and / or di-fatty acid esters, polyglyceryl fatty acid esters, mixed ethers or mixed formals, polysorbates, and sugar-based carbohydrates such as glucamines or alkyl / alkenyl (poly)glycosides, preferably from the group consisting of glycerol mono- and / or di-fatty acid esters, polyglyceryl fatty acid esters, and sugar-based carbohydrates.

[0065] In particular, alkyl / alkenyl (poly)glycosides are preferred as sugar-based carbohydrates.

[0066] Alkyl / alkenyl (poly)glycosides means alkyl and / or alkenyl (poly)glycosides, in particular those of formula (II), R1O-[G]p(II) is a known nonionic surfactant having the formula During the ceremony, R1 is an alkyl / alkenyl group having 6 to 22 carbon atoms, - G is a sugar group having 5 or 6 carbon atoms, and - p is a number between 1 and 10.

[0067] Alkyl and / or alkenyl (poly)glycosides can be obtained by suitable methods of synthetic organic chemistry. Alkyl / alkenyl (poly)glycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably glucose. Therefore, preferred alkyl / alkenyl (poly)glycosides are alkyl / alkenyl (poly)glucosides. The index p in 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. p in a given compound must always be an integer. Here, values ​​of p = 1 to 6 are particularly conceivable, but the value p of a specific alkyl / alkenyl polyglycoside is an analytically determined and calculated parameter, and is most often a fraction. Preferably, alkyl / alkenyl (poly)glucosides with an average degree of polymerization p of 1.1 to 3.0 are used. From the viewpoint of technical application, preference is given to those with a degree of polymerization of less than 1.7, in particular between 1.2 and 1.7.

[0068] The alkyl and / or alkenyl radicals R1 can be derived from primary alcohols having 6 to 22, preferably 6 to 18, carbon atoms. Typical examples are caproic, caprylic, decyl and undecyl alcohols, lauryl, myristyl, cetyl, palmoleyl, stearyl, isostearyl, oleyl, elaidyl, petroselinyl, arachyl, gadoleyl, behenyl, erucyl, brassidyl alcohols, as well as technical grade mixtures thereof.

[0069] Particularly preferred alkyl (poly)glucosides are selected from the group consisting of decyl polyglucosides, lauryl polyglucosides, and C8-C18 polyglucosides (C8-C18 means derived from a mixture of alcohols having 8 to 18 carbon atoms). Preferably, R1 is derived from a saturated primary alcohol mixture, for example, containing 10-50% by weight of C8 / C10 saturated primary alcohols and 50-90% by weight of C12-C18 saturated primary alcohols. Separate preference is given to R1 of formula (II) in which R1 is derived from a saturated primary alcohol mixture, containing 75-95% by weight of saturated primary alcohols having 12-16 carbon atoms.

[0070] Suitable alkyl (poly)glucosides are the products known as Plantacare® 810, Plantacare® 1200, Plantacare® 2000, and Plantacare® 818, all available from BASF Personal Care Nutrition GmbH.

[0071] Alkyl and / or alkenyl glucamides, or "N-alkyl / alkenyl glucamides," are known products derived from glucuronic acid and fatty acids. Preference is given to N-alkyl glucamides derived from lauric acid, myristic acid, palmitic acid, palm oleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, and technical mixtures thereof. Particular preference is given to the use of N-methyl glucamides, especially those based on technical C12-C14 palm fatty acid fractions. Suitable products are Glucopure® Foam or Glucopure® Sense, available from Clariant.

[0072] Other useful nonionic surfactants are glycerol mono- and / or di-fatty acid esters or polyglyceryl fatty acid esters. Examples of polyglycerol esters are esters of polyglycerol with linear and / or branched fatty alcohols, particularly partial esters of polyglycerol with 2 to 6 glycerol adducts. Particularly preferred are partial esters of hydroxy fatty acids having 18 carbon atoms and / or partial esters of branched fatty acids having 18 carbon atoms. For example, polyglyceryl-2-dihydroxystearate, commercially available as Dehymuls® PGPH from BASF Personal Care and Nutrition GmbH, or triglycerol-3 diisostearate, commercially available as Lameform® TGI from BASF Personal Care and Nutrition GmbH.

[0073] Examples of glycerol monoesters are monoglycerol esters of fatty acids, particularly linear and / or branched fatty acids having 12 to 22 carbon atoms and / or linear and / or branched hydroxy fatty acids having 12 to 18 carbon atoms, such as hydroxystearic acid monoglyceride, isostearic acid monoglyceride, oleic acid monoglyceride, ricinoleic acid monoglyceride, linoleic acid monoglyceride, linolenic acid monoglyceride, stearic acid monoglyceride, and / or oleic acid stearate monoglyceride, etc. Glycerol monoesters of linear saturated and / or unsaturated fatty acids, particularly glycerol monostearate and / or glycerol monooleate, are preferred.

[0074] Of these products, technical esters of fatty acid monoglycerides are highly preferred, which may still contain small amounts of glycerol and / or diglyceride esters and / or triglycerides due to the production method. Preferred esters are technical mixtures of fatty acid monoglycerides with a monoglyceride content in the range of 50-95 wt.%, preferably 60-90 wt.%. Particularly preferred are mono-fatty acid esters of (technical) glycerol and a fatty acid mixture containing 90-100 wt.% oleic acid, based on the fatty acid mixture.

[0075] Such technical grade glycerol monooleate is commercially available, for example, as Monomuls® 90 / 18 from BASF personal Care and Nutrition GmbH.

[0076] Examples of fatty alcohol polyglycol ethers, ethoxylated fatty acid glycerol esters are addition products of 2 to 50 moles of ethylene oxide and / or 0 to 20 moles of propylene oxide to linear fatty alcohols having 8 to 40 C atoms, to fatty acids having 12 to 40 C atoms, and to alkylphenols having 8 to 15 C atoms in the alkyl group.

[0077] However, in accordance with the present invention, it is preferred that the personal care composition be substantially free of surfactants comprising ethylene oxide and / or propylene oxide units.

[0078] Additionally, personal care compositions that are substantially free of surfactants containing sulfate groups are preferred.

[0079] B) Thickener of the Present Invention The personal care composition comprises, as component B), 0.01 to 5 wt % of a thickener of the present invention, where wt % is calculated based on the personal care composition as active material.

[0080] The present personal care compositions may additionally contain thickeners as described in other ingredients C).

[0081] C) Other ingredients For end-user applications, the personal care compositions may contain a range of further auxiliaries and additives, including water, such as, for example, additional thickeners, thickeners, viscosity reducers, salts, superfatting agents, stabilizers, polymers, fats, waxes, silicones, lecithin, protein hydrolysates, phospholipids, biologically derived active ingredients, UV sunscreen agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, tyrosinase inhibitors (bleaching agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes, pH adjusting additives, pearlizing agents and / or opacifiers.

[0082] Preferred are personal care compositions comprising, as component C), a cationic polymer. These cationic polymers include cationic guar polymers, cationic non-guar galactomannan polymers, cationic tapioca polymers, cationic copolymers of acrylamide monomers and cationic monomers, synthetic non-crosslinked cationic polymers, cationic cellulose derivatives such as quaternized hydroxyethyl cellulose, cationic starch, copolymers of diallylammonium salts and acrylamide, quaternized vinylpyrrolidone / vinylimidazole polymers such as Luviquat® (BASF), condensation products of polyglycols with amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat® L, Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyl dimethicone, and copolymers of adipic acid and dimethylaminohydroxypropyl dimethicone. The polymers may include at least one of copolymers with ethylenetriamine (Cartaretine®, Sandoz), copolymers of acrylic acid and dimethyldiallylammonium chloride (Merquat® 550, Chemviron), polyaminopolyamides and crosslinked water-soluble polymers thereof, cationic chitin derivatives such as quaternized chitosan, optionally in microcrystalline dispersion, condensation products of dihaloalkyls, such as dibromobutane, with bis-dialkylamines, such as bis-dimethylamino-1,3-propane, cationic guar gums, such as Celanese's Jaguar® CBS, Jaguar® C-17, Jaguar® C-16, and quaternized ammonium salt polymers, such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1, and the like.

[0083] In particular, the personal care compositions may comprise a cationic polymer selected from the group consisting of cationically modified cellulose derivatives, PQ10, PQ67, cationically modified guar derivatives such as Dehyquart® Guar N, guar hydroxypropyltrimonium chloride, acrylamide-based cationic homo- or copolymers, vinylpyrrolidone-based cationic homo- or copolymers, quaternized vinylimidazole-based cationic homo- or copolymers, and methacrylate-based cationic homo- or copolymers.

[0084] In particular, there is present a cationically modified guar derivative, preferably guar hydroxypropyltrimonium chloride.

[0085] The personal care compositions may additionally contain a polyol as an optional ingredient. Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. The polyol may contain other functional groups, more particularly amino groups, or may be nitrogen-modified. Typical examples are glycerol, alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1,000 daltons, technical oligoglycerol mixtures having a degree of self-condensation of 1.5 to 10, such as technical diglycerol mixtures having a diglycerol content of 40 to 50% by weight, methylol compounds such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol, and dipentaerythritol, methyl and butyl glucoside, sugar alcohols such as sorbitol or mannitol, dialcoholamines such as diethanolamine or 2-aminopropane-1,3-diol.

[0086] The personal care compositions may contain an oil component, such as Guerbet alcohols based on fatty alcohols containing 6 to 18, 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 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 palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, The hydroxybenzoates may additionally contain stearyl phosphate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, and erucyl erucate.Esters of linear C6-22 fatty acids with branched alcohols, more particularly 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-22 fatty alcohols, more particularly dioctyl malate, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g. propylene glycol, dimerdiol or trimertriol 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, substituted cyclohexanes, linear or branched C6-22 fatty alcohol carbonate esters, Guerbet alcohol carbonate esters (Guerbet Also suitable are esters of benzoic acid with linear and / or branched C6-22 alcohols (e.g. Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, ring-opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons, such as squalane, squalene or dialkylcyclohexanes.

[0087] The personal care compositions may additionally contain superfatting agents such as lanolin and lecithin, acylated lanolin, lecithin derivatives, polyol fatty acid esters, monoglycerides, and fatty acid alkanolamides.

[0088] The personal care compositions may additionally contain consistency agents, such as fatty alcohols or hydroxy fatty alcohols containing 12 to 22, preferably 16 to 18, carbon atoms, and partial glycerides, fatty acids or hydroxy-fatty acids. Combinations of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates are preferably used.

[0089] The present personal care compositions may additionally contain thickeners, such as those of the Aerosil series (hydrophilic silica), polysaccharides, more particularly xanthan gum, guar-guar, agar, alginates, and tylose, carboxymethylcellulose and hydroxyethylcellulose, relatively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates (e.g., Carbopol® [Goodrich] or Synthalen® [Sigma]), polyacrylamides, polyvinyl alcohols, and polyvinylpyrrolidones, surfactants, such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols, such as pentaerythritol or trimethylolpropane, narrow-range fatty alcohol ethoxylates or alkyl oligoglucosides, and electrolytes, such as sodium chloride and ammonium chloride. According to the present invention, the personal care compositions are substantially free of thickeners containing EO / PO units. Preferably, the personal care compositions may contain only salts as additional thickeners in addition to the thickeners according to the present invention.

[0090] The personal care compositions may additionally contain fats and / or waxes such as candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugarcane wax, ouricle wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), tail fat, ceresin, ozokerite (earth wax), petrolatum, paraffin wax, microcrystalline wax, chemically modified waxes (hard waxes) such as montan ester wax, sazol wax, hydrogenated jojoba wax, and synthetic waxes such as polyalkylene waxes and polyethylene glycol waxes.

[0091] The personal care compositions may additionally contain metal salts of fatty acids, such as magnesium stearate, aluminum stearate, and / or zinc stearate, or magnesium ricinoleate, aluminum ricinoleate, and / or zinc ricinoleate, and the like, which may be used as stabilizers.

[0092] The personal care compositions may additionally contain biogenic agents such as tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts, and vitamin complexes.

[0093] The personal care compositions may additionally contain film-forming agents such as chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymer, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and its salts, and similar compounds.

[0094] The personal care compositions may additionally contain protein hydrolysates, such as those based on keratin, such as the commercially available Nutrilan® Keratin WPP, or those based on wheat and / or soy, such as Gluadin® WLM Benz, Gluadin® WK or Gluadin® WP, Gluadin® Kera-PLM, etc. Small amounts of free amino acids, such as lysine or arginine, can also be added.

[0095] The personal care compositions may additionally contain anti-dandruff agents such as climbazole, octopirox, and zinc pyrithione.

[0096] Additionally, hydrotropes such as ethanol, isopropyl alcohol or polyols may be used to improve flow properties.

[0097] The personal care compositions may additionally contain preservatives such as benzoic acid, salts of benzoic acid, e.g., sodium benzoate, phenoxyethanol, formaldehyde solution, parabens, pentanediol, or sorbic acid, and other classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverordnung ("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.

[0098] The personal care compositions may additionally contain perfume oils, such as natural or synthetic fragrances or mixtures thereof. The personal care compositions may additionally contain dyes, which may be used are materials approved and suitable for cosmetic purposes, such as cochineal red A (CI 16255), patent blue V (CI 42051), indigotin (CI 73015), chlorophyllin (CI 75810), quinoline yellow (CI 47005), titanium dioxide (CI 77891), indanthrene blue RS (CI 69800), and madder lake (CI 58000).

[0099] The personal care composition may additionally contain water.

[0100] These other ingredients C) are preferably used in an amount of up to 100 wt % based on the personal care composition. The personal care composition may have a pH < 6, preferably in the range of pH 4.5 to 5.5.

[0101] The present inventors have discovered that fatty acid amidopropyl betaines themselves are excellent thickeners for personal care compositions that are substantially free of surfactants containing ethylene oxide and / or propylene oxide units and / or substantially free of surfactants containing sulfate groups.

[0102] This is highly advantageous as personal care compositions containing such surfactant systems are difficult to thicken.

[0103] Another object of the present invention is to provide a compound of formula (I') [ka] The present invention relates to fatty acid amidopropyl betaines corresponding to the formula (wherein n=3 and RCO is a mixture of acyl groups), characterized in that RCO is a mixture of acyl groups of rapeseed oil.

[0104] According to this embodiment of the present invention, fatty acid amidopropyl betaines corresponding to formula (I') are preferred, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 55% to 65% by weight, in particular 58 to 64% by weight, of oleic acid acyl groups.Furthermore, fatty acid amidopropyl betaines corresponding to formula (I') are preferred, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 15% to 25% by weight, in particular 18 to 21% by weight, of linoleic acid acyl groups.Furthermore, fatty acid amidopropyl betaines corresponding to formula (I') are preferred, characterized in that RCO is a mixture of acyl groups derived from rapeseed oil containing 7.5% to 12.5% ​​by weight, in particular 8 to 10% by weight, of linolenic acid acyl groups. Also preferred are fatty acid amidopropyl betaines corresponding to formula (I') in which RCO is a mixture of acyl groups derived from rapeseed oil containing 0.5 wt% to 6.5 wt%, in particular 1 wt% to 5 wt%, of palmitic acid acyl groups.

[0105] The wt% of acyl groups is always defined as the weight percent based on the weight of the mixture of acyl groups.

[0106] According to this embodiment, the RCO: 55wt% to 65wt% acyl groups of oleic acid (C18:1) 15wt% to 25wt% acyl groups of linoleic acid (C18:2) 7.5wt% to 12.5wt% acyl groups of linolenic acid (C18:3) 0.5wt% to 6.5wt% of palmitic acid (C16:0) acyl groups 0.5wt% to 3.5wt% of stearic acid (C18:0) acyl groups 0.0wt%~0.1wt% acyl group of myristic acid (C14:0) The most preferred fatty acid amidopropyl betaines correspond to formula (I'), which is a mixture of acyl groups of natural rapeseed oil consisting of:

[0107] Another object of the present invention is a method for preparing an aqueous solution of fatty acid amidopropyl betaines corresponding to formula (I'), comprising in a first step a) reacting rapeseed oil with dimethylaminopropylamine to obtain the corresponding dimethylaminopropylamide, then in step b) reacting said dimethylaminopropylamide with sodium chloroacetate in the presence of water to form an aqueous solution of fatty acid amidopropyl betaines corresponding to formula (I'), then in step c) adjusting the pH of the aqueous solution of fatty acid amidopropyl betaines corresponding to formula (I') to a pH of 8.0-12.5. [Example]

[0108] A) Preparation of base amidopropyl betaines Example A1) Amidopropyl betaines based on rapeseed oil Rapeseed oil containing the following wt% fatty acids was used:

[0109] [Table 1]

[0110] Step a): In a reaction vessel, 739.7 kg of rapeseed oil, 335.9 kg of dimethylaminopropylamine, and 2.0 kg of hypophosphorous acid (H3PO2 50%) were added and heated together under reflux at 170°C for 4 hours. The excess amine was removed by condensation under vacuum at 130°C with 3.59% N titr. Distillation was continued until the temperature reached 3.6% (theoretical: 3.6% N titr. ). %N titr. The values ​​were determined according to the method DGF-H-VI4b, whereby the sample is dissolved in acetic acid and titrated potentiometrically against perchloric acid.

[0111] 1000 kg of rapeseed oil based amidopropylamine was obtained.

[0112] Step b): A second reaction vessel was charged with 59.3 kg of sodium monochloroacetate and 620.4 kg of water. 203.9 kg of the rapeseed oil-based amidopropylamine obtained in step a) was added at 70°C. The betaine reaction was carried out at 90°C under pH control (pH 9.5) for approximately 3-4 hours until a theoretical amine value of titratable residual nitrogen equivalent to Houben-Weyl DGF-C-V2 (4.5 mg NH2 in KOH) was achieved.

[0113] To quench the remaining amount of unreacted Na monochloroacetate, the pH was raised to 12 (measured as a 10 wt % solution in the amidopropylamine mixture). Approximately 16.4 kg of NaOH solution (25 wt %) was used for quenching and pH control.

[0114] After the unreacted sodium monochloroacetate was removed, the pH was adjusted to 10.5 to 11.5 with a citric acid solution.

[0115] An aqueous solution of amidopropyl betaine based on rapeseed oil was obtained containing 40 wt% of the active substance. At pH 12.5, the Brookfield viscosity was 23.745 mPas, measured at room temperature with a spindle S64 at 12 RPM.

[0116] A2) Sunflower oil-based amidopropyl betaines Sunflower oil was used with the following wt% fatty acids:

[0117] [Table 2]

[0118] Betaine was prepared in a two-step process according to Example A1). In step a), 442.7 g of sunflower oil, 189.0 g of dimethylaminopropylamine, and 1.3 g of hypophosphorous acid (H3PO2 50%) were used. In step b), 183.8 g (corresponding to 0.5 mol) of amidopropylamine based on the sunflower oil obtained in step a), 52.3 g (corresponding to 0.45 mol) of sodium monochloroacetate, and 354.0 g of water were used. An aqueous solution of amidopropylbetaine based on natural sunflower oil was obtained, containing 36.9 wt% of the active substance.

[0119] The resulting betaine has a Brookfield viscosity of 6.200 mPas measured with a spindle T93 at 0.3 RPM, at room temperature, and at a pH of 12.5.

[0120] A3) Comparative Examples of Oleic Acid-Based Amidopropyl Betaines Betaine was prepared in a two-step process. In step a), 353.1 g (corresponding to 1.25 mol) of technical oleic acid (98 wt % oleic acid, remainder other fatty acids) was charged to a reactor, 1.0 g of hypophosphorous acid (H3PO2 50%) was added, and the mixture was heated under reflux. At 140 °C, 140.5 g (corresponding to 1.375 mol) of dimethylaminopropylamine was added. The reaction temperature was increased to 200 °C. The resulting water was distilled off using a reflux condenser. Excess amine was distilled off under vacuum at 130 °C until an approximate theoretical %Ntitr was reached.

[0121] Step b) was then carried out according to step b) of Example A1), but using 170.3 g (0.5 mol) of amidopropylamine based on oleic acid obtained in step a), 52.3 g (0.45 mol) of sodium monochloroacetate, and 303.0 g of water. An aqueous solution of amidopropylbetaine based on oleic acid was obtained, which contained 39.1 wt. % of active substance.

[0122] The resulting betaine has a Brookfield viscosity of 837,000 mPas measured at pH 12.1 with spindle S64 at 30 RPM and room temperature.

[0123] Personal care compositions containing amidopropyl betaines according to A1) to A3) Tables 1 and 2 disclose cosmetic compositions containing amidopropyl betaines based on rapeseed oil according to A1), or on sunflower oil according to A2), or on oleic acid according to A3), all compositions containing surfactants that do not contain EO / PO units.

[0124] The amounts / quantities in Tables 1 and 2 below are given in "wt%" meaning weight (wt) % and are calculated as active substance unless otherwise specified. Viscosity was measured at room temperature.

[0125] Ingredients used: Plantapon® PSC: available from BASF Personal Care Nutrition GmbH, surfactant mixture, INCI: Coco-glucoside (and) disodium lauryl sulfosuccinate (and) glycerin, active substance: 45 wt% Dehyton® PK45: available from BASF Personal Care Nutrition GmbH, surfactant, INCI: Cocamidopropyl betaine, active substance: 37 wt% Dehyquart® CC6: available from BASF Personal Care Nutrition GmbH, conditioning agent, INCI: Polyquaternium-6, active substance: 100% Lamesoft® PO65: available from BASF Personal Care Nutrition GmbH, lipid layer enhancer, INCI: Coco-glucoside (and) glyceryl oleate, active substance: 100% Dehyton® SFA: available from BASF Personal Care Nutrition GmbH, surfactant mixture, INCI: cocamidopropyl betaine (and) disodium 2-sulfolaurate, active substance: 45 wt% Plantacare® 818UP: available from BASF Personal Care Nutrition GmbH, non-ionic surfactant, INCI: Coco-glucoside, active substance: 51 wt% Plantasil® Micro: available from BASF Personal Care Nutrition GmbH, conditioning agent, INCI: Dicaprylyl ether (and) decyl glucoside (and) glyceryl oleate, active substances: 50 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 substance 30 wt%

[0126] [Table 3]

[0127] [Table 4]

[0128] Tables 1+2 show that the amidopropyl betaines of the present invention, both based on rapeseed oil or sunflower oil, have very good thickening properties in personal care compositions.

[0129] Table 1 shows that a personal care composition containing a surfactant mixture comprising the nonionic surfactant alkyl (poly)glucoside and the anionic surfactant sulfosuccinate had a viscosity of 5049 mPas (Comparative Example B1), which increased to 8278 mPas (Inventive Example B2) or 7288 mPas (Inventive Example B3) after adding the amidopropyl betaines of the present invention. Comparative Example B7 shows the same personal care composition, but with the oleic acid-based betaine A3, which had a lower viscosity than the inventive composition.

[0130] Table 2 shows that the viscosity of personal care compositions containing different surfactant mixtures was increased by adding inventive amidopropyl betaines A1 or A2 (inventive examples B6+B7).

[0131] [Table 5]

[0132] Table 3 shows that the viscosity of further personal care compositions comprising different surfactant mixtures was increased by adding the inventive amidopropyl betaines A1 or A2 (inventive examples B9+B10) compared to other betaines such as cocamidopropyl betaine (comparative example B8).

Claims

1. as thickeners for increasing the viscosity of personal care compositions; 【Chemistry 1】 1. Use of fatty acid amidopropyl betaines corresponding to the formula: wherein n=3 and 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.

2. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from rapeseed and / or sunflower oil fatty acids, comprising more than 80 wt. % and less than 95 wt. % of unsaturated acyl groups, based on the acyl groups.

3. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from rapeseed and / or sunflower oil fatty acids, containing more than 5 wt. % and less than 20 wt. % saturated acyl groups, based on the acyl groups.

4. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups of fatty acids derived from rapeseed oil, containing 55% to 65% by weight, in particular 58 to 64% by weight, of oleic acid acyl groups.

5. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from rapeseed oil, containing 15 wt. % to 25 wt. %, in particular 18 wt. % to 21 wt. % of linoleic acid acyl groups.

6. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from rapeseed oil, containing 7.5 wt. % to 12.5 wt. %, in particular 8 wt. % to 10 wt. % of linolenic acid acyl groups.

7. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups of fatty acids derived from rapeseed oil, containing 0.5 wt. % to 6.5 wt. %, in particular 1 wt. % to 5 wt. % of acyl groups of palmitic acid.

8. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups of fatty acids derived from natural sunflower oil, containing 25 wt% to 40 wt% of acyl groups of oleic acid.

9. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from natural sunflower oil, containing 45% to 65% by weight of linoleic acid acyl groups.

10. 2. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 1, characterized in that the RCO is a mixture of acyl groups derived from sunflower oil, containing 80% to 90% by weight of oleic acid acyl groups.

11. 11. Use of fatty acid amidopropyl betaines according to formula (I) according to claim 10, characterized in that the RCO is a mixture of acyl groups of fatty acids derived from sunflower oil, containing from 5 wt% to 10 wt% of acyl groups of linoleic acid.

12. 2. Use of fatty acid amidopropyl betaines corresponding to formula (I) according to claim 1, characterized in that the fatty acid amidopropyl betaines are used as thickeners for increasing the viscosity of personal care compositions in an amount of 0.01 to 5 wt % based on the personal care composition.

13. 2. Use of fatty acid amidopropyl betaines corresponding to formula (I) according to claim 1, characterized in that the fatty acid amidopropyl betaines are used as an aqueous solution comprising the fatty acid amidopropyl betaines in an amount of 15% to 55% wt % and at least 40% by weight of water, said wt % being based on the aqueous solution.

14. 1. A personal care composition for cleansing and nourishing hair and / or skin, comprising a thickener for increasing the viscosity of the personal care composition, characterized in that the personal care composition comprises fatty acid amidopropyl betaines corresponding to formula (I) of claim 1 as thickeners in an amount of 0.01 to 5 wt % based on the personal care composition.

15. The personal care composition comprises: A) 1.0 to 30 wt. %, in particular 5.0 to 25.0 wt. %, of one or more surfactants selected from the group consisting of anionic surfactants, nonionic surfactants, amphoteric and / or zwitterionic surfactants, B) 0.01 to 5 wt. % of fatty acid amidopropyl betaines corresponding to formula (I) as thickeners according to claim 1, and C) up to 100 wt. % of other components C) different from A) and / or B).

15. The personal care composition of claim 14, wherein wt% is calculated based on the personal care composition as active material.

16. 16. The personal care composition of claim 15, further comprising a thickener for increasing the viscosity of the personal care composition, wherein the personal care composition comprises an anionic surfactant selected from the group consisting of acyl isethionates, acyl taurates, acyl glycinates, acyl glutamates, acyl sarcosinates, acyl sulfosuccinates, mono- and / or double salts of alpha-sulfo fatty acids, alkyl glucose carboxylates, protein / fatty acid condensation products, and mixtures thereof.

17. 16. The personal care composition of claim 15, further comprising a thickener for increasing the viscosity of the personal care composition, characterized in that the personal care composition comprises a nonionic surfactant selected from the group consisting of fatty alcohol polyglycol ethers, ethoxylated fatty acid glycerol esters, glycerol mono- and / or di-fatty acid esters, polyglyceryl fatty acid esters, mixed ethers or mixed formals, polysorbates, and sugar-based carbohydrates such as glucamines or alkyl / alkenyl (poly)glycosides.

18. 16. The personal care composition of claim 15, further comprising a thickener for increasing the viscosity of the personal care composition, wherein the personal care composition comprises a zwitterionic and / or amphoteric surfactant selected from the group consisting of carboxylation products of secondary and / or tertiary amines, carboxylation products of amidoamines, imidazolinium betaines and / or amphoacetate surfactants, wherein the fatty acid alkylamidopropyl betaines are different from the fatty acid alkylamidopropyl betaines defined in formula (I).

19. 16. The personal care composition of claim 15, comprising a thickener for increasing the viscosity of the personal care composition, wherein the personal care composition is substantially free of surfactants comprising ethylene oxide units and / or propylene oxide units.

20. 16. The personal care composition of claim 15, comprising a thickener for increasing the viscosity of the personal care composition, wherein the personal care composition is substantially free of surfactants containing sulfate groups.

21. Formula (I') 【Chemistry 2】 (wherein n=3 and RCO is a mixture of acyl groups), wherein RCO is a mixture of acyl groups derived from rapeseed oil.

22. A method for preparing an aqueous solution of fatty acid amidopropyl betaines corresponding to formula (I'), comprising: in a first step a), reacting rapeseed oil with dimethylaminopropylamine to obtain the corresponding dimethylaminopropylamide; then in step b), reacting the dimethylaminopropylamide with sodium chloroacetate in the presence of water to form the aqueous solution 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 8.0-12.5.

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