FR2845902A1 - Composition for the permanent deformation of hair comprises an alkaline bisulfite combination of acetone, acetaldehyde, propionaldehyde, lactaldehyde or glyceraldehyde, or a salt - Google Patents

Abstract

Reducing composition for the first stage in the process of permanent deformation of hair comprises a bisulfite combination of acetone (A), acetaldehyde (B), propionaldehyde (C), lactaldehyde (D) or glyceraldehyde (E) or their organic or mineral salts, in an acceptable cosmetic medium. The pH of the composition is greater than 7. Reducing composition for the first stage in the process of permanent deformation of hair comprises a bisulfite combination of acetone (A), acetaldehyde (B), propionaldehyde (C), lactaldehyde (D) or glyceraldehyde (E) of the following formulae or their organic or mineral salts, in an acceptable cosmetic medium. The pH of the composition is greater than 7. Independent claims are also included for: (1) the hair treatment process; and (2) a 2-compartment preparation kit for containing the reducing solution and an oxidizing solution.

Description

PERMANENT DEFORMATION COMPOSITION OF HAIR CONTAINING AT LEAST ONE

  BISULFICIAL COMBINATION IN ALKALINE ENVIRONMENT

  The present invention relates to an aqueous reducing composition at alkaline pH, for the permanent deformation of keratinous fibers, containing, as reducing agent, the bisulfite combination of acetone, acetaldehyde, propionaldehyde, lactaldehyde or glyceraldehyde or a cosmetically acceptable salt thereof, as well as processes using this composition.

  By keratinous fibers is meant according to the invention fibers of human or animal origin such as hair, hair, eyelashes, wool, angora, cashmere, fur, etc. Although the invention is not limited to the treatment of particular keratinous fibers, it will nevertheless be more particularly referred to the treatment of hair.

  The most usual technique for obtaining a permanent deformation of the hair consists, firstly, in opening the disulfide bonds of keratin (cystine) using a composition containing a reducing agent and then preferably rinsed the hair, to reconstitute in a second time said disulfide bonds by applying to the hair previously tensioned by hair curlers or others or shaped or smoothed by other means, an oxidizing composition still called fixer to give to the hair the desired form. This technique allows indifferently to achieve either the waving of the hair, or their straightening or curing or smoothing.

  Reducing compositions generally used for the first step of a permanent operation contain sulphites, bisulphites or, preferably, thiols as the reducing agent. Of these, those commonly used are thioglycolic acid, cysteamine, thiolactic acid and cysteine. Thioglycolic acid is particularly effective in reducing the disulfide bonds of keratin at alkaline pH, especially in the form of ammonium thioglycolate, and is the most widely used permanent product. However, it has been found that thioglycolic acid should be used in a sufficiently basic medium (in practice at pH 28.5) if satisfactory crimp in intensity is to be obtained. Besides the inconvenience of giving off an odor

  unpleasant requiring the use of more or less effective perfumes to mask the odors, the combination thiol + alkaline pH leads to degradations of the fiber such as partial hydrolysis of the peptide bonds.

  Sulphites or bisulphites have been used before thiols in general and thioglycolic acid in particular. Unlike thiols, they are used at an acidic pH generally between pH 4 and pH 6. However, they do not allow to obtain degrees of crimping as important as thioglycolic acid, and also have an unpleasant spicy odor typical of sulfur dioxide.

  Sulphites (or bisulphites) and thiols have the further disadvantage of having poor stability in aqueous solution.

  Various studies have been conducted to overcome the disadvantages of these various reducing agents. For this purpose, it has been proposed in patent application GB473641 the use of bisulfitic combinations of acetone and formaldehyde at their spontaneous pH (acidic pH) and in patent application GB468845 the use of bisulfitic combinations of acetone, acetaldehyde, propionaldehyde, lactaldehyde or glyceraldehyde at a pH of between 4.5 and 7.0. These compounds make it possible in part to overcome the drawbacks of odor and stability, but their use at pH 7 as defined in these patents leads to a significant degradation of the state of the fiber.

  After various studies, the Applicant has now discovered, quite surprisingly and unexpectedly, that the use of these compounds at a pH strictly greater than 7, on the one hand, makes it possible to obtain a satisfactory crimp in intensity and withstand and, on the other hand, leads to less significant degradation of the hair, not only with respect to the use of these compounds at an acidic pH, but also with respect to the use of thioglycolic acid under usual alkaline conditions.

  The subject of the present invention is a reducing aqueous composition, for the first time of a permanent hair deformation operation, comprising, in a cosmetically acceptable medium, at least one of the bisulfite combinations chosen from the bisulfite combination of acetone. (A), acetaldehyde (B), propionaldehyde (C), lactaldehyde (D) or glyceraldehyde (E) of the following formulas: OH I

H3C-C-CH3

SO3H OH I

CH3CH: -C - H

SO3H OH I

(A) H3C-C-H

SO3H (B) OH I

(C) CH3-CH (OH) -C-H

SO3H (D) OH I

HO-CH2-CH (OH) -C - H

SO3H (E)

  and their organic and inorganic salts, characterized in that the pH of this composition is strictly greater than 7.

  By the expression "lactaldehyde" and "glyceraldehyde", it is of course to be understood according to the invention as well the stereoisomers of configuration L or D as the racemic (DL).

  Although these compounds are known compounds, an example of preparation will nevertheless be given hereinafter.

  For the purposes of the present invention, the term "alkaline pH" means a pH strictly greater than 7.

  Advantageously, the pH of the compositions according to the invention is between 7.1 and 11, and more advantageously between 7.1 and 9.5.

  In the compositions according to the invention, among the compounds (A), (B), (C), (D) and

  (E), the compounds (A), (B) and (E), and more particularly the compound (A).

  The method according to the invention of permanent hair deformation comprises the application of a reducing composition containing, in a cosmetically acceptable medium, at least one of the bisulfite combinations chosen from the bisulfite combination of acetone.

  (A), acetaldehyde (B), propionaldehyde (C), lactaldehyde (D) or glyceraldehyde (E). The hair is shaped using mechanical means well known to those skilled in the art, such as curlers, the reducing composition being applied before or after the hair shaping means, and a fixing composition being applied. after the reducing composition, with or without an intermediate or subsequent step of rinsing or application of an intermediate composition.

  Preferably, a reducing composition as defined above is applied to wet hair previously wound on rolls having a diameter of 4 to 20 mm, the composition possibly being able to be applied as and when rolled up. hair; the reducing composition is then allowed to act for a period of 5 to 60 minutes, preferably 15 to 45 minutes, followed by extensive rinsing; after which, on the wound hair, an oxidizing composition is applied to reform the disulfide bonds of keratin during a laying time of 2 to 10 minutes. After removing the rollers, the hair is thoroughly rinsed.

  The oxidation or oxidizing composition is of the type currently used and contains, for example, as an oxidizing agent for hydrogen peroxide, an alkaline bromate, a persalt, a polythionate or a mixture of alkaline bromate and persalt. The concentration of hydrogen peroxide can vary from 1 to 20 volumes and preferably from 1 to 10, the alkali bromate concentration from 2 to 12% and that persalt from 0.1 to 15% by weight relative to the total weight of the oxidizing composition. The pH of the oxidizing composition is generally between 2 and 10. This oxidation can be carried out immediately or be delayed.

  The deformation of the hair according to the invention may also consist of a hair straightening or decreping process, in which a composition is applied to the hair.

  reducing agent according to the invention, then the hair is subjected to a mechanical deformation to fix them in their new form, by a smoothing operation of the hair with a comb with large teeth, with the back of a comb or at the hand. After a laying time of 5 to 60 minutes, in particular 15 to 45 minutes, wholly or partly accompanied by a heat treatment as defined above, then a new smoothing is carried out, then rinsed thoroughly and an oxidizing or fixing composition as defined above is applied, which is allowed to act for about 2 to 10 minutes, and then the hair is thoroughly rinsed.

  According to the present invention, the permanent deformation of the hair is preferably, in a first step, to reduce the disulfide bonds of keratin by applying, for about 5 to 60 min, a reducing composition as defined above and then in a second step, to reform said bonds by application of an oxidizing composition or, optionally, by letting the oxygen of the air act.

  According to a preferred step of the methods of the invention, it is possible, after application of the reducing composition, to subject the hair to heat treatment by heating at a temperature of between 30 and 60 ° C, during all or part of the exposure time. In practice, this operation can be carried out by means of a hairdressing helmet, a hair dryer, an infrared ray dispenser and other conventional heaters.

  In the hair deformation compositions according to the invention, the reducing agent of general formula (D) is generally present at a concentration of between 0.05 and 40% and preferably between 0.1 and 30% by weight. relative to the total weight of the reducing composition.

  The pH of the composition is preferably obtained with the aid of an alkaline agent such as, for example, ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, an alkaline carbonate or bicarbonate or ammonium, an organic carbonate such as guanidine carbonate, an alkaline hydroxide or using conventional buffers, such as borate, phosphate, TRIS or other buffers.

  The reducing composition may also contain other known reducing agents, such as, for example, thioglycolic acid or thiolactic acid and their ester and amide derivatives, in particular glycerol monothioglycolate, cysteamine and its C 1 -C 4 acyl derivatives, such as Nacetyl-cysteamine or N-propionyl-cysteamine, cysteine, N-acetyl-cysteine, thiomalic acid, panthetein, 2,3-dimercaptosuccinic acid, sulphites or bisulfites of an alkaline or alkaline-earth metal the N- (mercaptoalkyl) -α-hydroxyalkylamides described in patent application EP-A-354,835, the N-mono- or N, N-dialkylmercapto4-butyramides described in patent application EP-A-368,763, aminomercaptoalkylamides, described in patent application EP-A432 000, derivatives of N- (mercaptoalkyl) succinamic acids and N (mercaptoalkyl) succinimides described in patent application EP-A-465342, the alkylamino mercaptoalkylamides described in application bre EP-A-514 282, the azeotropic mixture of 2-hydroxypropyl thioglycolate and (2-hydroxy-1-methyl) ethyl thioglycolate described in FR-A-2 679 448, the mercaptoalkylamino amides described in US Pat. patent application FR-A-2 692 481, the N-mercaptoalkylalkanediamides described in the patent application EPA-653 202, as well as the formamidine sulfinic acid derivatives described in application PCT / US01 / 43124, filed by the Applicant.

  According to a preferred embodiment, the reducing composition also contains a surfactant of the nonionic, anionic, cationic or amphoteric type, and among these there may be mentioned alkyl sulphates, alkyl benzene sulphates, alkyl ether sulphates, alkyl sulphonates, quaternary ammonium, alkyl betaines, oxyethylenated alkylphenols, fatty acid alkanolamides, oxyethylenated fatty acid esters as well as other nonionic surfactants of the hydroxypropyl ether type.

  When the reducing composition contains at least one surfactant, it is generally present at a maximum concentration of 30% by weight, and preferably between 0.5 and 10% by weight relative to the total weight of the reducing composition. .

  In order to improve the cosmetic properties of the hair or to reduce or prevent its degradation, the reducing composition may also contain a treating agent of cationic, anionic, nonionic or amphoteric nature.

  Among the particularly preferred treating agents include those described in French Patent Nos. 2,598,613 and 2,470,596. It is also possible to use volatile or non-volatile, linear or cyclic silicones and mixtures thereof, polydimethylsiloxanes, quaternized polyorganosiloxanes such as those described in French Patent Application No. 2,535,730, and polyorganosiloxanes containing group-modified aminoalkyl groups. alkoxycarbonylalkyls such as those described in US Pat. No. 4,749,732, polyorganosiloxanes such as polydimethylsiloxane-polyoxyalkyl copolymer of dimethicone copolyol type, polydimethylsiloxane containing stearoxy end groups (stearoxydimethicone), polydimethylsiloxane-dialkylammonium acetate copolymer or polydimethylsiloxane copolymer; polyalkyl betafne described in British Patent No. 2,197,352, organopolysiloxanes modified with mercapto or mercaptoalkyl groups such as those described in French Patent No. 1,530. 369 and in European Patent Application No. 295,780, as well as silanes such as stearoxytrimethylsilane.

  The reducing composition may also contain other treating ingredients such as cationic polymers such as those used in the compositions of French Pat. Nos. 79,320,778 (2,472,382) and 80,26421 (2,495,931), or cationic polymers of the ionene type such as that those used in the compositions of Luxembourg Patent No. 83703, basic amino acids (such as lysine, arginine) or acidic acids (such as glutamic acid, aspartic acid), peptides and their derivatives, hydrolysates of proteins, waxes, swelling and penetration agents or to enhance the effectiveness of the reducing agent, such as SiO 2 / PDMS (polydimethylsiloxane), dimethylisosorbitol, urea and its derivatives, pyrrolidone, N-alkylpyrrolidones, thiamorpholinone, alkylene glycol or dialkylene glycol alkyl ethers such as, for example, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, ethylene glycol monoethyl ether and diethylene glycol monoethyl ether, C3C6 alkanediols such as, for example, 1,2-propanediol and 1,2-butanediol, imidazolidinone-2 and other compounds such as fatty alcohols; , lanolin derivatives, active ingredients such as pantothenic acid, anti-hair loss agents, anti-dandruff agents, thickeners, suspending agents, sequestering agents, opacifying agents, dyes, sunscreens as well as perfumes and preservatives.

  The reducing composition according to the invention is essentially in aqueous form, especially in the form of a thickened lotion or not, a cream or a gel.

  The reducing composition according to the invention may also be of the exothermic type, that is to say causing a certain heating during application to the hair, which gives an approval to the person who undergoes the first time of the permanent or the straightening.

  The reducing composition according to the invention may also contain a solvent such as, for example, ethanol, propanol or isopropanol or glycerol, at a maximum concentration of 20% relative to the total weight of the composition.

  The vehicle of the compositions according to the invention is preferably water or a hydroalcoholic solution of a lower alcohol, such as ethanol, isopropanol or butanol.

  When the compositions are intended for hair straightening or straightening operation, the reducing composition is preferably in the form of a thickened cream so as to keep the hair as stiff as possible. These creams are produced in the form of "heavy" emulsions, for example based on glyceryl stearate, glycol stearate, self-emulsifiable waxes or fatty alcohols.

  It is also possible to use liquids or gels containing thickeners such as carboxyvinyl polymers or copolymers which "stick" the hair and keep it in the smooth position during the exposure time.

  The invention also relates to a kit, in particular, for the permanent deformation of the hair comprising, in a first compartment, as a reducing composition, a composition according to the invention comprising a compound of formula (I), and in a second compartment an oxidizing composition.

  The invention may be better understood with the aid of the nonlimiting examples which follow and which constitute preferred embodiments of the compositions according to the invention.

  Example 1 Preparation of sodium 2-hydroxypropane-2-sulfonate

  To 33.4 cm3 of a 38% aqueous solution of sodium hydrogen sulfite was added with stirring 25 cm3 of water and then dropwise 13 cm3 of acetone cooling slightly with an ice / water bath to maintain the temperature below 50 ° C. The stirring of the medium was maintained for 2 hours while allowing to return to ambient temperature. The solution thus obtained was precipitated by pouring slowly into 80 cm3 of absolute ethanol with stirring, and the suspension was cooled to 0-50C with an ice bath for 1 hour. After wringing on a sintered glass n03 and then washing with 20 cm3 of cooled absolute ethanol, the crystals were dried in vacuo over P2O5 at 30 ° C. Precipitation was again observed in the filtrate. 30 cm3 of absolute ethanol were added to the filtrate and then cooled to 0-50 ° C, drained, washed and dried the crystals as before. The two fractions were united. 20.15 g of sodium 2-hydroxy-propane-2-sulfonate were thus obtained in the form of pearlescent white crystals of melting point above 250 ° C.

  The Hi and C13 NMR spectra in DMSO-d6 are consistent with the expected structure.

Example 2

  A reducing composition for permanent deformation of the hair has been prepared according to the invention by mixing the following ingredients: compound of example 1 ..................... ..............................

  ...... 16.2 g - mixture cocoamidopropylbétaine and glyceryl laurate 30% aqueous solution sold under the name "Tégobétaine HS" ......... DTD: ......... ......................................... I g Monoethanolamine ...... .................................................. .. qsp pH 8.4 - Diethylenetriamine pentaacetic acid, pentasodium salt in 40% aqueous solution ....................... 0.2 g - Oleyl alcohol Oxyethylene Oleth -20 ................................................ ........ DTD: ... 0.8 g - Demineralized water .............................. ............... DTD: ................................. ......................................... D TD: ...... .... qsp 100 g This composition was applied to wet hair previously wound on styling rollers. After having allowed the composition to act for about 15 minutes under a 50 ° C. thermostat, the mixture was rinsed thoroughly with water and then the following oxidizing composition was applied: DTD: - hydrogen peroxide at 200 volumes ......... .....................................

  .................................................. ............... DTD: 4.8 g - hnci e ........................ c ........ t ........ ne ........... 0,05 .................. .g0 0 - o yq ae iupo ..............................

  .......................... 0.3 ............. g, - cocoamidopropyl hydroxysultaine ... .......................................... ....... i g -c of c tiacide ................. c ....... cudgel .................. ..q .......... DTD: .... p ........ s 3p - ad mneaus e ........ d ..... mineralized ............... DTD: ............. qsp .......... 100 ........ qp g0..DTD: The oxidizing composition was allowed to act for 5 minutes then rinsed thoroughly with water, removed the curlers and dried under helmet. We have obtained a beautiful soft curl that allows easier recoiling over time.

Example 3

  According to the invention, a reducing composition for the permanent deformation of the hair has been prepared by mixing the following ingredients: - omecompound 1 .............. of ....... l. ....example......................

  4 g - Cocoaminopropylbetane and glyceryl laurate mixture in 30% aqueous solution sold under the name "Tegobétaifne HS" ........ DTD: ....... ..................... i ...... g - o oh noa inonoé ............... ..DTD: .n ........ a ......... ne ....... qsp .......... pH ...... ..8,5 sp, - Diethylenetriamine pentaacetic acid, pentasodium salt in 40% aqueous solution ............. 0.2 g - Oleth-20.0.8 Oxyethoxylated Ole ... ....... DTD: .................................... 'g - ad mnEaus e ........ demineralized ................................ qsp ...... This composition was applied to wet hair previously wound on styling rollers. After allowing the composition to act for about 30 minutes under a 50 ° C thermostat, it was rinsed thoroughly with water and then the following oxidizing composition was applied.

  - r ma ed s duro ......... ate ........... of ......... sodium ........... ......

.............. g, - a po hotampon ................... phosphate ......... .... DTD: .............. pH ............, .. 5p, - ad mneause ........ demineralized .... DTD: ................................ sp ....... 100 .. ...... qp g0..DTD: The oxidizing composition was allowed to act for 10 minutes and then rinsed abundantly with water, removed the hair curlers and then dried under a helmet and a nice curl was obtained.

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Claims (9)

  1. A reducing aqueous composition, for the first time of a permanent hair deformation operation, comprising, in a cosmetically acceptable medium, at least one of the bisulfite combinations chosen from the bisulfite combination of acetone (A), acetaldehyde (B), propionaldehyde (C), lactaldehyde (D) or glyceraldehyde (E) of the following formulas: OH OH H3C-uC-CH3 (A) H3C-C-H (B) SO3H SO3H OH OH   CH 3 CH 2 --H (C) CH 3 -CH (OH) - C-H (D) SO3H SO3H OH HO-CH2-CH (OH) -Cl-H (E) I SO3H   and their organic and inorganic salts, characterized in that the pH of this composition is strictly greater than 7.   2. Composition according to Claim 1, characterized in that the bisulfite combination is chosen from compounds (A), (B) and (E).   3. Composition according to claim 1, characterized in that the bisulfite combination is the compound (A).   4. Composition according to any one of the preceding claims, characterized in that it comprises, in addition, at least one other reducing agent chosen from thioglycolic acid or thiolactic acid and their ester and amide derivatives, especially the glycerol monothioglycolate, cysteamine and its acyl derivatives C1 C4 such as N-acetyl-cysteamine or N-propionyl-cysteamine, cysteine, N-acetyl-cysteine, thiomalic acid, pantheatin, acid 2 , 3dimercaptosuccinic, sulphites or bisulphites of an alkali or alkaline earth metal, N-   (Mercaptoalkyl) -co-hydroxyalkylamides, N-mono or N, N-dialkylmercapto4-butyramides, aminomercaptoalkylamides, N (mercaptoalkyl) succinamic acid derivatives and N (mercaptoalkyl) succinimides, alkylamino mercaptoalkylamides, azeotropic mixture of thioglycolate 2-hydroxypropyl and (2-hydroxy-1-methyl) ethyl thioglycolate, the mercaptoalkylaminoamides, the N-mercaptoalkylalkanediamides, and the formamidine sulfinic acid derivatives.   5. Composition according to any one of the preceding claims, characterized in that the reducing agent of general formula (1) is present in a concentration of between 0.05 and 40% and preferably between 0.1 and 30% by weight relative to the total weight of the reducing composition.   6. Composition according to any one of the preceding claims, characterized in that it has a pH of between 7.1 and 11, and preferably between 7.1 and 9.5.   7. Composition according to any one of the preceding claims, characterized in that it additionally contains an additive chosen from a surfactant of nonionic, anionic, cationic or amphoteric type, a cationic treating agent, anionic, nonionic or amphoteric, fatty alcohols, lanolin derivatives, active ingredients such as pantothenic acid, anti-hair loss agents, anti-dandruff agents, thickeners, suspending agents, sequestering agents, agents opacifiers, dyes, sunscreens, fragrances and preservatives.   8. A method of permanent deformation of hair, characterized in that it comprises the application of a reducing composition defined in any one of claims 1 to 7, the hair being shaped by mechanical means and the composition reducing agent being applied before or after the means for shaping the hair; a fixing composition being, in addition, applied after the reducing composition.   9. Kit comprising, in a first compartment, as a reducing composition, a composition according to any one of claims 1 to 7, and in a second compartment, an oxidizing composition.