Use of betaine derivatives as conditioning agents for keratin fibers

Abstract

The present invention relates to a method for conditioning keratinous fibers, comprising the step of topically applying to the keratinous fibers a cosmetic composition in emulsion form, comprising a surfactant composition comprising at least one ester or amide salt of glycine betaine containing from 14 to 24 carbon atoms in a cosmetically acceptable medium. The present invention also relates to the use of the surfactant composition defined above as a conditioning agent for keratinous fibers.

Description

[Technical Field]

[0001] The present invention relates to the use of a surfactant composition comprising at least one glycine betaine ester or amide salt containing 14 to 24 carbon atoms as a keratin fiber conditioning agent. The present invention also relates to a method for conditioning keratin fibers, comprising the step of topically applying a cosmetic composition in the form of an emulsion containing the surfactant composition defined above to the keratin fibers in a cosmetic-acceptable medium. [Background technology]

[0002] It is well known that hair, sensitized to varying degrees, particularly damaged and / or brittle, under the influence of surrounding factors, or mechanical and / or chemical treatments such as dyeing, bleaching, and permanent waves, is often difficult to detangle, unmanageable, and particularly difficult to style and shape. Hair may also lack luster because its surface may be damaged and therefore light reflection may be more uneven.

[0003] To overcome these shortcomings, it is common to use hair treatments that can condition the hair. These hair care compositions may be conditioning shampoos or hair conditioners, and they may be in the form of hair gels or lotions or thick creams containing conditioning agents whose primary purpose is to repair or limit the harmful or undesirable effects caused by various treatments or aggressive factors to which hair fibers are repeatedly exposed to to varying degrees.

[0004] Hair treatment compositions containing cationic polymers and / or cationic surfactants have already been proposed as conditioning agents. These compounds adhere to the hair, enabling improvements in the condition of the fibers and their cosmetic properties.

[0005] However, a certain number of these compounds are not entirely environmentally friendly. Therefore, there is a need for the development of cosmetic compositions that are environmentally toxic or non-environmentally toxic and that enable adequate or superior hair conditioning compared to conventional compositions.

[0006] The applicant hereby discovers, as expected and surprisingly, that certain glycine betaine derivatives can impart favorable conditioning properties to hair. These compositions, in particular, enable improved detangling and smoothness of hair, as well as its suppleness; hair becomes easier to style, and the hair feels very comfortable and fluid. These compounds can also impart similar properties to other keratin fibers, especially beards.

[0007] In the field of cosmetics, glycine betaine esters or amide salts or surfactant compositions containing them have already been described for their use in deodorants (WO2015 / 003968) or in acidic aqueous-based foaming shampoos (WO2005 / 121291). Reference WO2015 / 078890 further discloses a surfactant composition obtained by reacting glycine betaine with an alcohol of formula R1-OH containing 1 to 6 carbon atoms in the first step, and then reacting it with an alcohol of formula R2-OH having a longer chain in the presence of a sugar hemiacetal. This two-step process yields a complex surfactant composition containing, in addition to the long-chain glycine betaine ester salt, the corresponding ester having a shorter chain containing up to 6 carbon atoms, always in a proportion greater than 15% by mass, and also containing a cationized alkyl polyglycoside. The resulting composition can be used in particular for the preparation of hair care products, especially detangle sprays. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] WO2015 / 003968 [Patent Document 2] WO2005 / 121291

Patent Document 3

SUMMARY OF THE INVENTION

PROBLEMS TO BE SOLVED BY THE INVENTION

[0009] However, as far as the applicant knows, the use of long-chain glycine betaine esters or amide salts to facilitate the detangling of hair has not been proposed, nor has the use of these compounds in keratin fiber conditioning products in the form of an emulsion been proposed. [[ID=十六]]

MEANS FOR SOLVING THE PROBLEMS

[0010] One subject of the present invention is the use of a surfactant composition comprising at least one glycine betaine derivative of formula (1): X n- [(CH3)3N + -CH2-COZ-R] n (wherein Z represents an oxygen atom or -NH group, R is a saturated or unsaturated, linear or branched alkyl group containing 14 to 24 carbon atoms, X is an organic or inorganic anion, and n is equal to 1 or 2) as a keratin fiber conditioning agent.

[0011] Another subject of the present invention is a method for conditioning keratin fibers, comprising the step of topically applying a cosmetic composition in the form of an emulsion containing the surfactant composition as defined above in a cosmetically acceptable medium to the keratin fibers, it being understood that the surfactant composition does not contain alkyl polyglycosides.

[0012] The present invention relates to the application of a surfactant composition based on at least one glycine betaine derivative which is a long-chain glycine betaine ester or amide salt for the conditioning of keratin fibers. These two types of glycine betaine derivatives, and their preparation methods, will be described in more detail hereinafter.

[0013] Glycine betaine ester salt The glycine betaine ester salt can be obtained according to a method including the following consecutive steps: (1) A step of reacting glycine betaine or a salt thereof with at least one saturated or unsaturated, linear or branched fatty alcohol containing 14 to 24 carbon atoms in the presence of an organic acid or an inorganic acid, (2) A step of cooling the reaction medium to a temperature of 20°C to 90°C, and (3) A step of recovering the surfactant composition thus obtained The first step of the method is the esterification of glycine betaine or trimethylglycine. Glycine betaine may be of plant origin or synthetic. In view of glycine betaine being in the zwitterionic form (the presence of the carboxylate functionality), prior protonation with an organic acid or an inorganic acid is necessary. The acid may be selected particularly from inorganic acids such as hydrochloric acid, sulfuric acid, perhalogenated hydroacids such as perchloric acid, and mixtures thereof. As a variant, an organic acid such as alkyl sulfuric acid such as decyl sulfuric acid or lauryl sulfuric acid; aryl sulfonic acid such as benzene sulfonic acid, para-toluenesulfonic acid; alkyl sulfonic acid such as triflic acid, methanesulfonic acid, ethanesulfonic acid, decyl sulfonic acid, lauryl sulfonic acid, or camphorsulfonic acid; sulfosuccinic acid; and mixtures thereof may also be selected. Lewis acids can also be used. Preferably, an alkyl sulfonic acid, particularly ethanesulfonic acid or methanesulfonic acid in view of being readily biodegradable.

[0014]

[0015] [[ID=I7]] During esterification, the acidic function of the salted-out betaine is reacted with a fatty alcohol to produce a salt-form glycine betaine ester. The term "fatty alcohol" refers to saturated or unsaturated, linear or branched (preferably linear) alcohols containing 14 to 24 carbon atoms. Examples of such fatty alcohols include the group consisting of myristyl alcohol (C14:0), cetyl alcohol (C16:0), palmitrail alcohol (C16:1), stearyl alcohol (C18:0), oleyl alcohol (C18:1), linoleyl alcohol (C18:2), linolenyl alcohol (C18:3), arachidyl alcohol (C20:0), arachidonyl alcohol (C20:4), behenyl alcohol (C22:0), 2-hexyldecanol, 2-octyldodecanol, 2-decyltetradecanol, and mixtures thereof. A usable fatty alcohol mixture can be produced from one or more vegetable oils, in particular from, for example, soybean oil, olive oil, sunflower oil, corn oil, palm oil, coconut oil, cottonseed oil, linseed oil, wheat germ oil, safflower oil, or rapeseed oil.

[0016] According to the present invention, it is preferable to use one or more alcohols containing 18 to 22 carbon atoms, more preferably a mixture of such fatty alcohols.

[0017] Esterification reactions generally occur in the absence of a solvent. The water produced during the reaction further contributes to the solubilization of glycine betaine in the reaction mixture.

[0018] For carrying out this reaction, for example, 0.8 to 6.0 equivalents, preferably 0.8 to 2 equivalents, for example 0.9 to 1.0 equivalent, or as a variation, 1.1 to 1.8 equivalents, in this case preferably 1.2 to 1.6 equivalents, more preferably 1.3 to 1.5 equivalents of fatty alcohol, or as a second variation, 4.0 to 6.0 equivalents, in this case preferably 4.5 to 5.5 equivalents, more preferably 4.8 to 5.2 equivalents of fatty alcohol may be used.

[0019] Furthermore, advantageously, 1.01 to 3.0 equivalents, preferably 1.5 to 2.0 equivalents, for example 1.5 to 1.9 equivalents, preferably 1.5 to 1.7 molar equivalents of organic or inorganic acid, or as a variation (preferably in the second variation above) 1.02 to 1.08 equivalents, in this case preferably 1.03 to 1.07 equivalents, more preferably 1.04 to 1.06 molar equivalents of organic or inorganic acid per equivalent of glycine betaine, can be used. Esterification is carried out at a temperature in the range of, for example, 120°C to 180°C, preferably 150°C to 180°C. The reaction may be carried out under atmospheric pressure, or preferably under reduced pressure, for example, at a pressure of 10 to 600 mbar. In general, the pressure decreases proportionally as the chain length of the fatty alcohol used increases. The reaction mixture is then cooled to a temperature of 20°C to 90°C.

[0020] Next, the surfactant composition thus obtained is recovered, and the composition is composed of formula X n- [(CH3)3N + -CH2-COO-R] n The formula comprises at least one glycine betaine ester salt of (wherein X is an organic or inorganic anion, R is an alkyl group corresponding to the R-OH fatty alcohol used in the esterification reaction, and n is equal to 1 or 2).

[0021] The X anion is derived from the acid used in the first step of this process and can thus be, in particular, chloride, sulfate, perchlorate, alkyl sulfate ion, especially decyl sulfate or lauryl sulfate, aryl sulfonate ion, especially benzene sulfonate or para-toluenesulfonate, alkyl sulfonate ion, especially triflate, methanesulfonate, ethanesulfonate, decyl sulfonate, lauryl sulfonate, or camphorsulfonate, or sulfosuccinate ion. According to the invention, X is preferably selected from alkyl sulfonates and aryl sulfonates, in particular from methanesulfonate, triflate, para-toluenesulfonate, and camphorsulfonate ions. Advantageously, it is methanesulfonate or ethanesulfonate ion, more preferably ethanesulfonate ion.

[0022] The R group can itself be selected from the following groups: myristyl (C14:0), cetyl (C16:0), palmitoleyl (C16:1), stearyl (C18:0), oleyl (C18:1), linoleyl (C18:2), linolenyl (C18:3), arachidyl (C20:0), arachidonyl (C20:4), behenyl (C22:0), 2-hexyldecyl, 2-octyldodecyl, and 2-decyltetradecyl.

[0023] When several fatty alcohols are used in the esterification reaction, it is clearly understood that the surfactant composition obtained according to the invention will contain several glycine betaine ester salts. Therefore, the expression "glycine betaine ester salt" should be understood in the context of this specification as referring to one or more salts, unless otherwise specified.

[0024] The method described above consists, more precisely, of the following components: (a) of formula (1): X n- [(CH3)3N + -CH2-COO-R] nAt least one glycine betaine ester salt of (wherein R is a saturated or unsaturated linear or branched alkyl group containing 14 to 24 carbon atoms, preferably 18 to 22 carbon atoms), (b) At least one fatty alcohol of formula R-OH, (c) Organic or inorganic acid of formula XH, (d) Formula X n- [(CH3)3N + -CH2-COOH] n Glycine betaine salt, and (e) Any dialkyl ether of formula ROR (wherein X is an organic or inorganic anion and n is equal to 1 or 2) This makes it possible to obtain a surfactant composition containing the above.

[0025] This surfactant composition can be used as is in the present invention. In this case, it generally contains 15 to 85% by mass of a glycine betaine ester salt.

[0026] In the first variation, the surfactant composition, (a) 65-85% by mass, preferably 70-80% by mass of glycine betaine ester salt, (b) 1 to 20% by mass, for example, 1 to 9% by mass or 10 to 20% by mass, fatty alcohols (c) 1 to 20% by mass, for example, 5 to 15% by mass, organic or inorganic acid, (d) 1 to 20% by mass, for example, 2 to 15% by mass of glycine betaine salt, (e) 0 to 15% by mass, for example, 2 to 10% by mass of dialkyl ether Includes.

[0027] In a preferred second variation, the surfactant composition comprises the following: (a) 15% to 45% by weight, preferably 20% to 30% by weight, more preferably 25% to 30% by weight of a glycine betaine ester salt. (b) 55% to 80% by weight of fatty alcohols, for example, 60% to 65% or 65% to 70% or 70% to 80% by weight. (c) 0 to 5% by weight of an organic or inorganic acid, for example, 0 to 1% by weight. (d) 0 to 3% by weight, for example, 0 to 1% by weight of glycine betaine salt (e) 0 to 15% by weight, for example, 2 to 10% by weight of a dialkyl ether.

[0028] This composition can be obtained using the method described above, which uses 4 to 6 equivalents of fatty alcohol and 1.02 to 1.08 equivalents of acid per equivalent of glycine betaine. The resulting composition is rich in alcohol and low in acid, and has several advantages compared to the composition obtained by the first modification using 1.1 to 1.8 equivalents of fatty alcohol and 1.5 to 2.0 equivalents of acid. Specifically, the lower amount of acid present in the composition increases its naturalness and allows for a reduction in the amount of pH corrector to be added during the formulation of the surfactant composition, although this pH corrector can negatively affect the stability of the emulsion and the predetermined properties imparted to the keratin fibers. The performance of the surfactant composition is also improved by increasing the amount of residual alcohol it contains.

[0029] Preferably, the mass ratio of glycine betaine ester salt to fatty alcohol is between 20:80 and 30:70.

[0030] Advantageously, the surfactant composition contains no components other than components (a) to (e) above. As a variation, the method may include an additional step of isolating the glycine betaine ester salt present in the composition, which may be used as is in the present invention. In the latter case, the surfactant composition used in the present invention will contain at least 90% by mass, preferably at least 95% by mass, or at least 99% by mass of the glycine betaine derivative.

[0031] Glycine betaine amide salt These glycine betaine derivatives are produced in the following sequential process: (1) A step of reacting glycine betaine or a salt thereof with saturated or unsaturated linear or branched C4-C8 alcohol in the presence of an organic or inorganic acid, for example, at a temperature in the range of 100°C to 180°C and under reduced pressure. (2) A step of cooling the reaction medium to a temperature of 20°C to 80°C. (3) A step of adding one or more alkylamines containing 14 to 24 carbon atoms, (4) A step to remove residual alcohol, and (5) A step of recovering the surfactant composition thus obtained. It can be prepared according to a method that includes [the following].

[0032] The first step of this method consists of the esterification reaction of glycine betaine, which can be carried out in the same manner as the production of glycine betaine esters, except that one or more linear and / or branched C4-C8 alcohols are used in the presence of an acid which may be selected from those described above. Examples of such alcohols include butanol, pentanol, 3-methylbutan-1-ol (or isoamyl alcohol), fusel alcohols (a mixture of pentanol, 2-methylbutan-1-ol, and 3-methylbutan-1-ol), hexanol, heptanol, octanol, and mixtures thereof. The term "butanol" is understood herein to be equivalent to n-butanol, isobutanol, and sec-butanol. Butanol, more specifically n-butanol, and hexanol are preferred for use in the present invention, with hexanol being particularly preferred. This reaction is generally carried out in the absence of a solvent, and the alcohols used constitute both the reactants and the medium. The water produced during the reaction also contributes to the solubilization of glycine betaine in the reaction mixture. Generally, 1.1 to 20 equivalents, for example 2 to 4 equivalents, of linear or branched C4-C8 alcohol and 1.0 to 1.5 equivalents, for example 1.0 to 1.2 equivalents, preferably 1.1 equivalents, of sulfonic acid can be used per equivalent of glycine betaine. Esterification may be carried out at temperatures of 100°C to 180°C, preferably 100°C to 160°C, more preferably 120°C to 150°C, or 130°C to 160°C, under atmospheric pressure or reduced pressure.

[0033] The product of the esterification reaction may be optionally treated to separate the salt of the formed glycine betaine ester from the reaction medium. For example, the reaction medium can be filtered, which allows the alcohol-soluble chloride ester to be separated from other insoluble components.

[0034] Next, one or more C atoms are added to either the reaction medium or the isolated ester. 14 -C 24These are alkylamines. Examples of such amines include tetradecylamines, hexadecylamines, octadecylamines, docosanylamines, eicosanylamines, and mixtures thereof. According to the present invention, it is preferable to use one or more amines containing 16 to 22 carbon atoms, more preferably a mixture of such amines.

[0035] In this step, the alkylamine is preferably used in a molten state. The amount of alkylamine added may be, for example, 0.9 to 1.5 equivalents, preferably 1.0 to 1.2 equivalents, per equivalent of the glycine betaine initially used. This aminolysis reaction is typically carried out under reduced pressure, for example, 1 to 30 mbar, at a temperature of 50°C to 180°C, preferably 120°C to 140°C. Simultaneously with the aminolysis reaction, the alcohol is removed by distillation under reduced pressure. The aminolysis reaction and distillation are carried out over a period of 1 to 7 hours, particularly 3 to 5 hours. The surfactant composition thus obtained is then recovered.

[0036] This method allows you to: (a) Formula (1):X n- [(CH3)3N + -CH2-CONH-R] n One or more glycine betaine amide salts of (wherein R is a saturated or unsaturated linear or branched alkyl group containing 14 to 24 carbon atoms, preferably 16 to 22 carbon atoms), (b) Formula (2):X n- [NH3 + R] n One or more alkylammonium salts of (wherein R is a saturated or unsaturated linear or branched alkyl group containing 14 to 24 carbon atoms, preferably 16 to 22 carbon atoms), (c) Formula (3):X n- [(CH3)3N + -CH2-COOR'] n One or more glycine betaine ester salts of (wherein R' is a saturated or unsaturated linear or branched alkyl group containing 4 to 8 carbon atoms), and (d) Formula (4): (CH3)3N + -CH2-COO - Glycine betaine (wherein X is an organic or inorganic anion, and n is equal to 1 or 2) A surfactant composition containing the above can be obtained.

[0037] This surfactant composition may be used as is in the present invention. In this case, the composition generally contains 60 to 98% by mass, for example 70 to 80% by mass, of a glycine betaine amide salt. Component (b) may account for 0 to 25% by mass, for example 15 to 20% by mass, component (c) for 0 to 15% by mass, for example 5 to 10% by mass, and component (d) for 0 to 5% by mass, relative to the total mass of the surfactant composition. Advantageously, this surfactant composition does not contain any components other than those described above (a) to (d). As a variation, the above method may include an additional step of isolating the glycine betaine amide salt present in the composition, which may be used as is in the present invention. In the latter case, the surfactant composition used according to the present invention will contain at least 90% by mass, preferably at least 95% by mass, or at least 99% by mass, of a glycine betaine derivative.

[0038] In any case, the surfactant composition containing the glycine betaine ester or amide salt as defined above does not contain cationized or non-cationized alkyl polyglycosides, and / or, in the case of esters (Z=O), further contains formula (1')X n- [(CH3)3N + -CH2-COO-R] n It is preferable that the formula does not contain a glycine betaine derivative of (wherein Re is a saturated or unsaturated linear or branched alkyl group containing 1 to 6 carbon atoms, X is an organic or inorganic anion, and n is equal to 1 or 2).

[0039] In one preferred embodiment, the surfactant composition according to the present invention contains at least 90% by mass, preferably at least 95% by mass, or at least 99% by mass of naturally derived components, calculated according to ISO-16128.

[0040] Cosmetic composition For the implementation of the present invention, a cosmetic composition in the form of an emulsion containing the surfactant composition described above is used. This emulsion may have a liquid or semi-liquid consistency, a soft consistency of the cream or balm type, or a solid consistency of the stick type. It may be oil-in-water (O / W), oil-in-glycerol, water-in-oil (W / O), water-in-glycerol, or multiphase (e.g., W / O / W) type. The emulsion is preferably oil-in-water. It generally contains 1 to 8% by mass, preferably 1 to 4% by mass, of the glycine betaine derivative used according to the present invention.

[0041] This cosmetic composition may be packaged in a tube, pump dispenser bottle, or jar. As a variation, it may be packaged in an aerosol container to ensure application of the composition in its evaporated form. In the latter case, the cosmetic composition preferably includes at least one propellant.

[0042] The cosmetic compositions used in accordance with the present invention include a medium that is acceptable as a cosmetic, namely a medium that is compatible with keratin fibers and skin, particularly hair and scalp, and that does not cause skin or scalp irritation or other undesirable effects after application to keratin fibers.

[0043] This cosmetic composition comprises an aqueous phase containing water, a C1-C4 alcohol such as ethanol, isopropanol, tert-butanol, or n-butanol, a polyol such as glycerol, propylene glycol, and polyethylene glycol, and one or more water-soluble solvents acceptable as cosmetics, selected from mixtures thereof. As a variation, this may include a mixture of water and one or more of the above-mentioned solvents. Preferably, this cosmetic composition has a total water content between 5 and 95% by mass, preferably between 10 and 90% by mass, for example between 40 and 85% by mass, and particularly between 50 and 80% by mass, based on the total mass of the composition. The pH of this composition generally varies from 3 to 9, preferably 3 to 7, preferredly 3.5 to 6, and more preferably 3.5 to 5. The pH may be adjusted within this range using at least one pH adjuster selected from, for example, sodium gluconate or calcium gluconate, sodium lactate, sodium glycinate, sodium citrate, and lactate / sodium lactate, acetate / sodium acetate, and gluconate / sodium gluconate buffer solutions.

[0044] This further comprises at least one fatty phase containing at least one fatty substance to form an emulsion. Preferably, the fatty substance is selected from oils, paste-like fatty substances, waxes, and mixtures thereof. The term "oil" refers to oils at room temperature (25°C) and atmospheric pressure (10°C). 5 The term “paste-like fatty substance” is understood to mean a compound that is liquid at Pa and, when introduced into water at 25°C in a proportion of at least 1% by mass, is either completely insoluble in water or soluble to less than 10% by mass relative to the mass of oil introduced into the water. The term “paste-like fatty substance” is understood to mean a fatty substance that exhibits a reversible solid / liquid state change, has an anisotropic crystalline structure in the solid state, and contains a liquid fraction and a solid fraction at a temperature of 23°C, such as vegetable butter. The term “wax” in the context of this specification means a fatty substance that is solid at 25°C, exhibits a reversible solid / liquid state change, and has a melting point generally from 30°C to 160°C, preferably from 50°C to 90°C, as measured by differential scanning calorimetry (DSC).

[0045] Preferably, the cosmetic composition used in accordance with the present invention contains at least one oil. Examples of oils include, in particular, fatty alcohols, fatty esters, hydrocarbons of plant or mineral origin, triglycerides and vegetable oils containing these, and mixtures thereof. Examples of fatty alcohols include, in particular, branched and / or unsaturated C10-C20 fatty alcohols, such as octyldodecanol and oleyl alcohol. Examples of fatty esters are esters of acids and monoalcohols selected from the following: monoesters and polyesters of C2-C10 (preferably C6-C10) saturated linear acids and C10-C18 (preferably C10-C14) saturated linear monoalcohols, monoesters and polyesters of C10-C20 saturated linear acids and C3-C20 (preferably C3-C10) branched or unsaturated monoalcohols, and monoesters and polyesters of C5-C20 branched or unsaturated acids and C5-C20 branched or unsaturated monoalcohols. Examples of these fatty esters include, in particular, mixtures of cococaprate and caprylate, ethyl macadamiate, ethyl shea butter ester, isostearyl isostearate, isononyl isononanoate, ethylhexyl isononanoate, hexyl neopentanoate, ethylhexyl neopentanoate, isostearyl neopentanoate, isodecyl neopentanoate, isopropyl myristate, octyldodecyl myristate, isopropyl palmitate, ethylhexyl palmitate, hexyl laurate, isoamyl laurate, cetostearyl nonanoate, propylheptyl caprylate, diisopropyl adipate, diethylhexyl adipate, diisopropyl sebacate, and diisoamyl sebacate.

[0046] Examples of hydrocarbons include squalane (C30), particularly plant-derived squalane extracted from olive oil or biosynthesized, and hemisqualane (C15). Examples of triglycerides include triglycerides of C6-C12 fatty acids, such as caprylic and capric acid triglycerides, and triheptanoin. Examples of vegetable oils include, in particular, wheat germ oil, sunflower oil, argan oil, hibiscus oil, coriander oil, grapeseed oil, sesame oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy seed oil, pumpkin oil, sesame oil, mallow oil, blackcurrant oil, evening primrose oil, lavender oil, borage oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, echium oil, camelina oil, or camellia oil.

[0047] Fatty substances may account for 1 to 30% by mass, preferably 5 to 25% by mass, and more preferably 10 to 20% by mass, based on the total mass of the cosmetic composition.

[0048] The cosmetic composition used in accordance with the present invention may also contain at least one standard cosmetic component particularly selected from nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, sunscreens, surfactants, such as vitamins, anti-dandruff agents, anti-seborrheic agents, anti-hair loss agents and / or hair growth promoters, antioxidants, pearlescent agents and / or opacifiers, pigments, fillers, metal ion chelating agents, non-thickening polymers, such as aminosilicones and / or cationic polymers, fragrances, preservatives, and mixtures thereof.

[0049] The organic acid that can be used in this composition has a pKa of 7 or less, preferably 6 or less, particularly in the range of 1 to 6, preferably 2 to 5. According to a preferred embodiment, the organic acid is selected from carboxylic acids, sulfonic acids, and mixtures thereof. In particular, the organic acid is selected from α- and β-hydroxy acids, such as lactic acid, citric acid, glycolic acid, salicylic acid, malic acid, tartaric acid, and mixtures thereof, with citric acid or lactic acid being more preferred.

[0050] Preferably, the anionic surfactant is selected from alkylcarbonyl isethionates, for example, those with the INCI names sodium cocoyl isethionate and sodium cocoyl methyl isethionate, lactylic acid salts, for example sodium lauroyl lactate, N-acyl amino acid salts, for example sodium lauroyl glycinate, sodium lauroyl sarcosinate, sodium lauroyl taurate, and sodium olive oil fatty acid glutamate, anionic sulfate surfactants, especially alkyl sulfates, especially sodium coco sulfate and potassium lauroyl sulfate, C8-C14 alkyl ether sulfate alkyl salts, for example sodium lauryl ether sulfate, soaps in the form of carboxylates, especially sodium olive oil fatty acid and sodium palmitate; and alkyl ether carboxylic acid surfactants, for example lauryl ether carboxylic acid or sodium lauryl ether carboxylic acid.

[0051] Nonionic surfactants used in cosmetic compositions are preferably the following: saturated or unsaturated linear or branched oxyethylene-containing C8-C40 alcohols containing 1 to 100 moles of ethylene oxide, preferably 2 to 50, particularly 2 to 40 moles of ethylene oxide, and preferably containing 1 or 2 fatty chains; saturated or unsaturated oxyethylene-containing vegetable oils containing 1 to 100, preferably 2 to 50 moles of ethylene oxide; (C8-C30) alkyl(poly)glucosides optionally oxyalkylene-containing (0 to 100 EO) and containing 1 to 15 glucose units; The following are selected: sugar esters, such as sucrose stearate and sucrose distearate; monoglycerolated or polyglycerolated C8-C40 alcohols containing 1-50 moles of glycerol, preferably 1-10 moles of glycerol; saturated or unsaturated linear or branched oxyalkylene C8-C30 fatty acid amides; saturated or unsaturated linear or branched C8-C30 acids with polyethylene glycol; preferably saturated or unsaturated linear or branched C8-C30 acids with sorbitol; and mixtures thereof.

[0052] The amphoteric surfactant, preferably a non-silicone surfactant, used in the cosmetic composition used in the present invention is, in particular, an optionally quaternized secondary or tertiary aliphatic amine derivative, wherein the aliphatic group is linear or branched, containing 8 to 22 carbon atoms, and the amine derivative contains at least one anionic group, such as a carboxylate, sulfonate, sulfate, phosphate, or phosphonate group. In particular, (C8-C20) alkylbetaine, (C8-C20) alkylsulfobetaine, (C8-C20) alkylamide (C3-C8) alkylbetaine, and (C8-C20) alkylamide (C6-C8) alkylsulfobetaine are examples.

[0053] In addition to the glycine betaine derivative, the cationic surfactants optionally used may be optionally selected from polyoxyalkylene-modified primary, secondary, or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.

[0054] The thickeners may be selected from cellulose thickeners, such as hydroxyethylcellulose, hydroxypropylcellulose, and carboxymethylcellulose; naturally derived rubbers, such as tara gum (Caesalpinia spinosa gum) and guar gum and their derivatives, such as hydroxypropyl guar and guar hydroxypropyltrimonium chloride; microbially derived rubbers, such as xanthan gum and scleroglucan gum; synthetic thickeners, such as crosslinked homopolymers of acrylic acid or acrylamidepropanesulfonic acid; or nonionic, anionic, cationic, or amphoteric associative polymers. Among the cationic polymers that can be used as thickening polymers, polyamine, poly(aminoamide), and poly(quaternary ammonium) type polymers are particularly noteworthy, especially cationic cellulose, cationic guar gum, and homopolymers or copolymers of dimethyldiallylammonium halide.

[0055] Examples of activators that may be included in the compositions according to the present invention include sodium hyaluronate, tocopherol and its derivatives, such as tocopherol acetate, panthenol, serine, glycerol, arginine, ceramide, such as 2-oleamido-1,3-octadecanediol, hydroxypropyl starch phosphate, and mixtures thereof, and this list is not limiting. Hair conditioning agents, such as silicones, particularly dimethicone and amodimethicone, can also be mentioned.

[0056] Method / Usage The cosmetic compositions used in accordance with the present invention are in the form of care products for keratin fibers, particularly conditioners or hair masks intended for hair treatment. In particular, it is intended for the treatment of weakened and / or damaged hair, for example, hair weakened and / or damaged by chemical or mechanical treatments, especially dyeing, bleaching, permanent wave, or straightening, or by brushing, and is therefore preferably applied to such hair. It can also be used as a treatment cream shampoo, particularly an anti-seborrheic or anti-dandruff shampoo. This composition can constitute a rinse product or a rinse-free product. It generally does not have foaming properties. This composition may also be in the form of a rinse-out product applied before or after dyeing, bleaching, permanent wave, or straightening, or between the two steps of a permanent wave or straightening treatment.

[0057] As a variation, the cosmetic composition according to the present invention may take the form of a beard care product.

[0058] More specifically, the present invention relates to a cosmetic method for conditioning keratin fibers, the method comprising the step of topically applying a cosmetic composition in the form of the emulsion described above to the keratin fibers. The term "keratin fibers" is understood to mean scalp hair and body hair, particularly beards and eyebrows. Hair types to which the compositions according to the present invention may be applied include Caucasians, Africans, and Asians. These may be curly or frizzy to varying degrees. The term "conditioning" in the context herein is understood to mean improvement of at least one property of the keratin fibers, selected from combability, detangling, softness, suppleness, luster, and manageability. Preferably, conditioning of keratin fibers does not involve its cleansing. Therefore, the compositions according to the present invention generally do not constitute shampoo.

[0059] The composition may be applied to dry or wet hair, preferably wet or damp hair, i.e., hair that has been washed and rinsed beforehand. In one embodiment, the method according to the present invention comprises the steps of applying an effective amount of the cosmetic composition to the hair, optionally kneading the hair, optionally leaving the composition on the surface of the hair, and rinsing. The time the composition is left on the surface of the hair may be between a few seconds and 15 minutes, preferably between 30 seconds and 5 minutes. The composition is generally rinsed with water. An optional step of drying the hair may be performed. In another embodiment, the method according to the present invention comprises the steps of applying an effective amount of the cosmetic composition to the hair, optionally kneading the hair, optionally leaving the composition on the surface of the hair, and optionally drying without rinsing. This method is intended to improve the combability and / or softness and / or suppleness and / or manageability and / or luster of keratin fibers, and / or to smooth them, and / or to hydrate them, and / or to reduce their static electricity. It is generally not suitable for, or intended for, cleaning keratin fibers. [Brief explanation of the drawing]

[0060] [Figure 1] Figure 1 shows the combability of hair strands treated with compositions containing water, a reference surfactant, a mixture of the glycine betaine ester salt according to the present invention, and a mixture of the glycine betaine amide salt according to the present invention. [Figure 2] Figure 2 is a graph showing the softness of hair strands treated with compositions containing a reference surfactant, a mixture of glycine betaine ester salts according to the present invention, and a mixture of glycine betaine amide salts according to the present invention, compared to a commercially available hair detangler. [Modes for carrying out the invention]

[0061] The present invention is given purely for illustrative purposes and will be better understood in light of the following embodiments, which are not intended to limit the scope of the invention as defined by the appended claims.

[0062] Example 1: Synthesis of a surfactant composition based on glycine betaine ester salt Synthesis of methanesulfonates Glycine betaine (1.0 equivalent) and a mixture of C18-C22 fatty alcohols (1.4 equivalents) are introduced into the reactor. The set temperature of the mixture is set to 170°C and the pressure is reduced to 60 mbar. Once the set pressure and temperature are reached, a 70% methanesulfonic acid solution (1.6 equivalents) is added to the reaction mixture. As soon as the addition is complete, the set temperature is increased to 150°C and the pressure is maintained at 30 mbar. Five hours after the start of acid introduction, the reaction mixture is cooled to 80°C, then the product is collected and cooled to room temperature, and the following components are obtained: [Table 1] The present invention constitutes a surfactant composition comprising the following:

[0063] Synthesis of ethanesulfonates Glycine betaine (1.0 equivalent) and a mixture of C18-C22 fatty alcohols (5.0 equivalents) are introduced into the reactor. The temperature of the mixture is set to 170°C and the pressure is reduced to 60 mbar. Once the set pressure and temperature are reached, a 70% ethanesulfonic acid solution (1.05 equivalents) is added to the reaction mixture. As soon as the addition is complete, the temperature is raised to 150°C and the pressure is maintained at 30 mbar. Six hours after the start of acid introduction, the reaction mixture is cooled to 80°C, then the product is collected and cooled to room temperature, and the following components are obtained: [Table 2] The present invention constitutes a surfactant composition comprising the following:

[0064] Example 2: Synthesis of a surfactant composition based on glycine betaine amide salt Synthesis of methanesulfonates Glycine betaine (1.0 equivalent), butanol (3.0 equivalents), and a 70% methanesulfonic acid solution (1.1 equivalents) are introduced into a reactor fitted with a condenser. This mixture is heated to 140°C under atmospheric pressure. After reacting for 3 hours, a Dean-Stark trap filled with butanol is attached to the reactor. The mixture is left at atmospheric pressure as the water-butanol azeotrope distillation occurs sufficiently from the beginning. After reacting for another 3 hours, when the distillation rate of the water-butanol azeotrope decreases, the pressure is reduced to 700 mbar to promote the removal of water and allow the equilibrium to shift towards glycine betaine butyl ester. The conversion rate is: 1 It is monitored by 1H NMR analysis.

[0065] In NMR spectroscopy, the sample dissolved in a CDCl3 / CD3OD mixture (1 / 1, v / v) 1 H spectra were obtained, and the methanol signal at 3.31 ppm was used as the reference. Subsequently, the characteristic signals of various compounds were integrated: MsOGBOBu (4.35 ppm, s, 2H), MsOGB (4.28 ppm, s, 2H), butanol (3.53 ppm, t, 2H), methanesulfonate (2.74 ppm, s, 3H), and dibutyl ether (3.40 ppm, t, 4H), where XOGBOBu represents the generated glycine betaine ester sulfonate salt and XOGB represents the generated glycine betaine sulfonate. The characteristic signal of methanesulfonate considers both the methanesulfonic acid present in the medium and methanesulfonate (MsOGBOBu), which is the counterion of glycine betaine and butyl betaine mesylate.

[0066] The conversion rate of the reaction is calculated as follows:

number

[0067] When the conversion rate of the esterification reaction reaches 96%, the reaction mixture is cooled to 60°C. During this cooling stage, the Dean-Stark apparatus is replaced with a distillation apparatus, and the reactor is placed under reduced pressure to remove some of the butanol and trace amounts of residual water from the reaction mixture. When the mixture reaches 60°C, the pre-melted mixture of C16-C22 fatty amines (1.1 equivalents) is added. The reaction mixture is then heated under reduced pressure to 150°C. The pressure is gradually reduced to 10 mbar. After distilling all of the butanol (approximately 4 hours), the reaction mixture is collected and the following components are obtained: [Table 3] The present invention comprises a surfactant composition containing the following:

[0068] Synthesis of ethanesulfonates Glycine betaine (1.0 equivalent) and hexanol (3.0 equivalents) are introduced into a reactor fitted with a Dean-Stark trap filled with hexanol. An isobaric dropping funnel containing 1.1 equivalents of 70% ethanesulfonic acid solution is fixed to the reactor lid. The mixture is stirred and heated to 150°C under reduced pressure of 600 mbar. Once the reaction conditions are met, the 70% ethanesulfonic acid solution is gradually introduced into the reaction mixture. After the addition is complete, the pressure is gradually reduced to 400 mbar to facilitate the removal of water and allow the equilibrium to shift towards the glycine betaine ester side. The conversion rate is: 1 It is monitored by 1H NMR analysis.

[0069] In NMR spectroscopy, the sample dissolved in a CDCl3 / CD3OD mixture (1 / 1, v / v) 1The H spectrum was obtained, and the methanol signal at 3.31 ppm was used as the reference. Subsequently, the characteristic signals of various compounds were integrated: EsOGBOC6 (4.35 ppm, s, 2H), EsOGB (4.28 ppm, s, 2H), hexanol (3.53 ppm, t, 2H), ethanesulfonate (2.82 ppm, q, 3H), and dihexyl ether (3.40 ppm, t, 4H), where XOGBOC6 represents the generated glycine betaine ester sulfonate salt and XOGB represents the generated glycine betaine sulfonate. The characteristic signal of ethanesulfonate takes into account both the ethanesulfonic acid present in the medium and the ethanesulfonate (EsOGBOC6), which is the counterion of glycine betaine and hexyl esylate.

[0070] The conversion rate of the reaction is calculated as follows:

number

[0071] When the conversion rate of the esterification reaction reaches 96%, the reaction mixture is cooled to 80°C. During this cooling stage, the Dean-Stark apparatus is replaced with a distillation apparatus, and the reactor is placed under reduced pressure to remove some of the hexanol and trace amounts of residual water from the reaction mixture. When the mixture reaches 80°C, the pre-melted mixture of C16-C22 fatty amines (1.1 equivalents) is added. The reaction mixture is then heated under reduced pressure to 150°C. The pressure is gradually reduced to 5 mbar. After distilling all of the hexanol (approximately 4 hours), the reaction mixture is collected and the following components are obtained: [Table 4] The present invention comprises a surfactant composition containing the following:

[0072] Example 3: Tangle-untangling test (sensory evaluation) Comparative tests for detangling hair strands were conducted using either a mixture of C18-C22 glycine betaine ester salts or a mixture of C16-C22 glycine betaine amide salts according to the present invention as a conditioning agent, or an aqueous fatty alcohol emulsion containing the conditioning agent, namely behentrimonium chloride (Varisoft® BT85 manufactured by EVONIK).

[0073] The glycine betaine ester and amide salt corresponded to the compositions shown in Table 1 of Example 1 and Table 3 of Example 2, respectively. These emulsions have the following composition: Cetyl alcohol 6.00%~10.00%* Conditioning agent (as active substance) 3.00% Preservative 0.60% A suitable amount of buffer solution to achieve a pH of 4.0-5.0. Desalinated water, an appropriate amount to make it 100.00% He possessed it. *The amount at which the viscosity is between 7,000 and 22,000 mPa.s (LV4, 20 rpm, 20℃) All of these emulsions had the appearance of an opaque, viscous cream. Furthermore, tap water (hardness 30°F, temperature: 37°C) was used as a control.

[0074] Two strands of hair were pre-moistened, squeezed, and then rubbed together 15 times in the palms of the hands to entangle the hair. Then, 1g of each product was applied to one of the two moistened strands of hair, and the product was massaged in 8 times along the entire length of the strand to ensure even distribution. After a 3-minute waiting period, the strands were rinsed with tap water and squeezed by hand. These were then placed on a flat surface, and the number of comb strokes required to obtain a strand that could be combed smoothly without snagging was measured. This procedure was repeated 3 times for each product, using 3 different strands of hair. Only one test was performed with tap water (30°F).

[0075] The results of this test are shown in Figure 1. As is clear from this figure, the glycine betaine ester salt according to the present invention provides performance equivalent to that of the reference surfactant. However, this glycine betaine derivative is more biodegradable than the reference surfactant, is 100% bio-based, and its synthesis method is more environmentally friendly. The glycine betaine amide salt has superior effects compared to the ester salt.

[0076] Next, a sensory analysis of the softness of the resulting hair bundles was performed by a trained panel, in the same manner as described above, but in comparison to hair bundles treated with a commercially available detangler (Elseve® Total Repair Rapid Restore) containing the same amount of cationic conditioning agent (behentrimonium chloride) and having the same pH and substantially the same viscosity as the emulsion described above.

[0077] The evaluation results are shown in Figure 2. As shown in this figure, hair bundles treated with the cosmetic composition according to the present invention, which contains a glycine betaine ester salt, are perceived to be significantly softer than those treated with a composition containing a reference surfactant, and even more so than those treated with commercially available detanglers.

[0078] Additional tests were conducted under the same conditions using the surfactant compositions shown in Table 2 of Example 1. All results are summarized in the table below. [Table 5] The performance of this surfactant composition is significantly superior to that of similar surfactant compositions prepared in the presence of smaller amounts of fatty alcohol and larger amounts of acid.

[0079] Example 4: Tangle-untangling test (mechanical test) Materials and methods Using a Diastron® Fibra One machine equipped with a comb, measure the amount of work (joules) required to comb a strand of hair completely. To do this, five flattened strands of bleached Caucasian hair (3.5g, 28cm) are first washed with 1ml of sodium lauryl ether sulfate solution (28% active substance). The strands are rubbed together 20 times between both hands, and then rinsed in water for 1 minute and 30 seconds. After repeating this washing process twice, excess water is removed by squeezing the strands three times with two fingers. The aforementioned machine is as follows: Starting position: 75mm Comb length: 200mm Speed: 2000mm / min Adjust it like this. Three measurements are taken for each hair strand; that is, one measurement is taken after each rinsing step, and then the average of the three measurements is calculated.

[0080] Next, apply the same conditioner treatment (0.5 ml) to one side of each of the five hair strands, spread the product 10 times with two fingers, then apply (0.5 ml) to the other side of the hair strand and spread it 10 times with two fingers. Then, rinse each hair strand under running water for 16 seconds (changing sides every 8 seconds). Remove excess water by squeezing it three times with equal force between two fingers. Then, test the hair strands again with the Diastron® product described above. Next, rinse twice in a row (run under running water for 10 seconds, then squeeze out excess water three times between two fingers), and send each strand back to the Diastron® product after each rinse. Calculate the average of the three measurements obtained.

[0081] For each strand of hair, the percentage reduction in the force required to untangle the strand is calculated using the following formula: D=(W T -W o ) / 100(in the formula, W T This is the work measured after processing, W o This is determined using the work (which is measured before processing). The average DM (damage reduction) obtained for the five hair strands is calculated.

[0082] The conditioner products tested are as follows: 1) A surfactant composition according to Example 2, containing approximately 1% by mass of glycine betaine ester and 3% by mass of C18-22 alcohol. 2) A comparative surfactant composition containing 1% by mass of a nonionic surfactant (sorbitan stearate) and 3% by mass of a C18-22 alcohol, 3) A comparative surfactant composition containing 1% by mass of behentrimonium chloride and 3% by mass of C18-22 alcohol as cationic surfactants. 4) A comparative surfactant composition containing 1% by mass of cetrimonium chloride and 3% by mass of C18-22 alcohol as cationic surfactants. As stated above, "C18-22 alcohol" here refers to a mixture of fatty alcohols containing 18 to 22 carbon atoms (BASF's Stenol® 1822A).

[0083] result The results of the above-mentioned tests are summarized in Table 6 below. [Table 6]

[0084] As shown in this table, the product according to the present invention (Product 1) provides detangle-free properties to treated hair bundles, which is represented by a reduction in the work required to comb the hair bundles. This reduction is comparable to that obtained using non-biodegradable cationic surfactants (Product 3) conventionally used in detangle products, and higher than that obtained using commercially available cationic surfactants (Product 4) that have lower biodegradability than the product according to the present invention. The performance of the product according to the present invention is even more significantly better than that obtained using nonionic surfactants (Product 2).

[0085] Example 5: Formulation Several products can be prepared using the surfactant composition according to the present invention, based on palmityl (GBE C16:0 or GBA C16:0), stearyl (GBE C18:0 or GBA C18:0), arachidyl (GBE C20:0 or GBA C20:0), or behenyl (GBE C22:0 or GBA C22:0) esters or amide salts or mixtures thereof, more specifically, esters containing at least 55% by mass of fatty alcohol according to a second variation of the present invention. Examples of such products are shown below, with capitalized components identified as their INCI names.

[0086] [Table 7]

[0087] [Table 8]

[0088] [Table 9]

[0089] [Table 10]

[0090] [Table 11]

[0091] [Table 12]

[0092] [Table 13]

[0093] Table 14

Claims

1. A cosmetic method for conditioning keratin fibers, wherein the medium is acceptable as a cosmetic, (a) Formula (1) for 15–45 mass%: X n- [(CH 3 ) 3 N + -CH 2 -COZ-R] n at least one glycine betaine derivative, (b) 55-80% by mass of at least one fatty alcohol of formula R-OH, (c) an organic acid of formula XH in an amount of up to 5% by mass, (d) glycine betaine salt of formula X in an amount of up to 3% by mass, and n- [(CH 3 ) 3 N + -CH 2 -COOH] n ​ (e) at least one dialkyl ether of formula ROR in an amount of up to 15% by mass. surfactant composition containing [In the above formula, Z represents an oxygen atom, R is a saturated or unsaturated linear or branched alkyl group containing 14 to 24 carbon atoms, X is an organic anion, and n is equal to 1 or 2.] A method comprising the step of topically applying a cosmetic composition in emulsion form containing a surfactant to keratin fibers, wherein the surfactant composition does not contain alkyl polyglycosides.

2. The method according to claim 1, characterized in that the R group is selected from the following groups: myristyl (C14:0), cetyl (C16:0), palmitrail (C16:1), stearyl (C18:0), oleyl (C18:1), linoleyl (C18:2), linolenyl (C18:3), arachidyl (C20:0), arachidonyl (C20:4), behenyl (C22:0), 2-hexyldecyl, 2-octyldodecyl, and 2-decyltetradecyl.

3. The method according to claim 1 or 2, characterized in that the X anion is selected from alkyl sulfate ions, aryl sulfonate ions, or sulfosuccinate ions.

4. The method according to claim 3, characterized in that X is a methanesulfonate or ethanesulfonate ion.

5. The method according to any one of claims 1 to 4, characterized in that R is a saturated or unsaturated linear or branched alkyl group containing 18 to 22 carbon atoms.

6. The method according to any one of claims 1 to 5, characterized in that the keratin fibers are selected from hair, beard, and eyebrows.

7. The method according to claim 6, characterized in that the composition is applied to weakened and / or damaged hair.

8. The method according to any one of claims 1 to 7, characterized in that it aims to improve the combability and / or softness and / or suppleness and / or ease of handling and / or gloss of keratin fibers, and / or to smooth them, and / or to hydrate them and / or to reduce their static electricity.

9. The method according to any one of claims 1 to 8, characterized in that the cosmetic composition is applied to hair that has been washed and rinsed beforehand.

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