FR2657254A1 - Cosmetic reducing composition for the permanent-reshaping of hair, based on N-acetylcysteamine and a cation polymer, and its use in a process for the permanent-reshaping of hair - Google Patents

Abstract

Cosmetic reducing composition containing a combination of a reducing agent and a cationic polymer. The reducing agent is N-acetylcysteamine, and the cationic polymer is a copolymer of 45 to 99.5 mol% of N-vinylpyrrolidone and 55 to 0.5 mol% of unquaternised di(C1-C4 alkyl)amino(C1-C18 alkyl) acrylate or methacrylate. Use of the composition in a cold-state process for the permanent-reshaping of hair.

Description

 The subject of the present invention is a reducing cosmetic composition for perming hair based on N-acetylcysteamine and a cationic polymer and its use in a process for permanent deformation of hair when cold.

 The conventional technique for carrying out permanent deformation of the hair consists in firstly opening the disulphide bridges of the keratin using a composition containing a reducing agent (reduction step), then, after having preferably rinsed the hair, to reconstitute in a second time said disulfide bonds by applying, to the hair under tension, an oxidizing composition, (oxidation step, also called fixing) so as to give the hair the desired final shape. This technique makes it possible to achieve either a waving of the hair or a straightening or decreping.

 Among the reducing agents making it possible to carry out the first stage of a perming operation, mercaptans such as thioglycolic acid, thiolactic acid or a mixture of these acids are generally used, as well as their esters, for example glycerol or glycol monothioglycolate.

 Furthermore, it has also been proposed to use, as reducing agent, 2-amino ethanethiol or cysteamine, following the work of PURI et al (International Journal of Cosmetic Science 1,59-67,1979) .

 These reducing agents having a deteriorating effect on the hair, it has been recommended to combine them with cationic polymers.

However, it has been observed that the use of a certain number of these cationic polymers, associated with cysteamine, gives rise to reducing compositions which are unstable over time. After various studies, it has been found quite unexpectedly and surprisingly that these drawbacks can be resolved by the use of N-acetylcysteamine and of a particular class of cationic copolymers, based on
N-vinylpyrrolidone and dialkyl (C1-C4) aminoalkyl (CI'C18) dialkyl methacrylate or methacrylate, not quaternized. The reducing compositions have been shown to be particularly stable and made it possible to obtain perms of excellent quality having in particular good hold with a crease more durable over time.

 In addition, it has been found that these reducing compositions are free of odor, which is particularly sought after not only for people undergoing a hair permanent operation but also for the people who perform them.

 Finally, the reducing compositions according to the invention make it possible to obtain a better effect treating the ends of the hair.

 The good stability of the reducing compositions according to the invention therefore makes it possible to remedy the drawbacks of the compositions of the prior art which most often had to be produced at the time of use, by mixing the reducing agent on the one hand and the cationic polymer on the other hand, these being packaged separately.

 The present invention therefore relates to a reducing cosmetic composition for carrying out permanent deformation of the hair when cold, containing a combination of a reducing agent and a cationic polymer, the reducing agent being N-acetylcysteamine and the cationic polymer a copolymer from 45 to 99.5 mol% of N-vinylpyrrolidone and from 55 to 0.5 mol Z of dialkyl (C1-C4) aminoalkyl (C1-Cl8) dialkyl acrylate or methacrylate.

 According to the invention, N-acetylcysteamine is used at a concentration of between 0.1 and 15% by weight, preferably between 3 and 8% by weight relative to the total weight of the reducing composition.

 Among the cationic copolymers corresponding to the above definition, it is preferred to use, according to the invention, copolymers of 80 to 99.5 moles Z of N-vinylpyrrolidone and from 0.5 to 20 moles% of dimethylaminoethyl methacrylate.

 Among the latter, those which are particularly preferred are the copolymers sold by the company GAF under the trade names of "Copolymer 845", "Copolymer 937" and "Copolymer 958"; "Copolymer 845" being very particularly preferred.

The characteristics of these cationic copolymers, based on
N-vinylpyrrolidone and dimethylaminoethyl methacrylate, are as follows
"Copolymer 845"
average molecular weight = 106
sold in the form of an aqueous solution at 20% by weight
"Copolymer 937"
6
average molecular weight = 10
sold in the form of an aqueous solution at 20% by weight
"Copolymer 958"
average molecular weight = 105
sold in the form of an alcoholic solution at 50% by weight.

 In the reducing compositions according to the invention, the concentration of cationic copolymer as defined above is generally between 0.1 and 3% by weight and preferably between 0.5 and 2% (expressed as active material) relative to the total weight of the reducing composition.

According to a preferred embodiment of the invention the
N-acetylcysteamine may be associated with cysteine or
N-acetylcysteine and in this case the latter are present in the composition at a concentration of between 0.1 and 10% by weight and preferably between 1.5 and 8% by weight.

 Preferably, the reducing composition also contains at least one surfactant of the nonionic, anionic or amphoteric type but preferably of the nonionic type and more particularly a nonionic poly (hydroxypropylether) surfactant.

Among the polyionic (hydroxypropylether) nonionic surfactants that may be mentioned in particular are the compounds of formulas (I) to (III) below and / or the compounds prepared according to the methods described in paragraphs (3) and (4) below

in which
the divalent motif -C3H5 (0H) O- represents the following structures, taken as a mixture or separately

 R1 represents a radical or mixture of alkyl radicals containing from 10 to 14 carbon atoms and n is a statistical integer or decimal number from 2 to 10 and preferably from 3 to 6.

 The compounds of formulas (I) above which are particularly preferred are those in which either R1 represents the radical C12 H25 and n = 4.2; either R1 represents a mixture of C10 H21 and C12 H25 alkyl radicals and n = 3.75.

These compounds of formula (I) are described in French patent No. 1,477,048.

in which
the divalent unit -C3 H5 (OH) O- has the same meaning as above for formula (I),
R2 represents a radical or a mixture of alkyl and / or alkenyl radicals having from 11 to 17 carbon atoms and m denotes a statistical integer or decimal number from 1 to 5, preferably 1.5 to 4.

Among these compounds of formula (II), the compound having the following formula is particularly preferred.

in which
the divalent unit -C3 H (OH) O- has the same meaning as above for formula (I),
R2 represents a mixture of alkyl and alkenyl radicals chosen from the radicals C11 H23 or C13 H27 and the radicals derived from the fatty acids of coconut and of olelic acid.

These compounds of formula (II) are more particularly described in French patent No. 76-31975 (2,328,763).

in which
the divalent unit -C3 H5 (OH) O- has the same meaning as above for formula (I),
R3 denotes an aliphatic, cycloaliphatic, arylaliphatic radical, preferably having from 7 to 21 carbon atoms and their mixtures, the aliphatic chains representing in particular alkyl chains having from 1 to 6 ether, thioether and / or hydroxymethylene groups and p is a statistical number between 1 and 10 inclusive.

 These compounds are prepared by condensation in alkaline catalysis, from 2 to 10 and preferably from 2.5 to 6 moles of glycidol on an alpha-diol or a mixture of alpha-diols in C1O-Cl4, at the temperature of 120- 1800C and preferably from 140 to 1600C.

 According to a particular embodiment, the compounds prepared by condensation by alkaline catalysis of 3.5 moles of glycidol on a mixture of alpha-diols having from 10 to 14 carbon atoms are preferred.

 These compounds of formula (III) are obtained according to the process described in French patent No. 71-17206 (2,091,516).

 (4) Compounds prepared by condensation, in acid catalysis, from 2 to 10 and preferably from 2.5 to 6 moles of glycidol per mole of alcohol or alpha-diol containing 10 to 14 carbon atoms at a temperature of 50 to 120 "C, the glycidol being added slowly to the alcohol or to the alpha-diol.

 Among these compounds, that obtained by condensation of monochlorohydrin (2.5 moles) in the presence of sodium hydroxide on 1,2-dodecanediol is particularly preferred.

 These compounds are prepared according to the process described in French patent No. 72-40822 (2,169,787).

 (5) Poly (hydroxypropyl ether) compounds prepared by poly-addition of glycerol monochlorohydrin on an organic poly-hydroxylated compound in the presence of a strong base, by elimination as water is obtained by distillation.

 These compounds are more particularly described in French patent No. 84-19267 (No. 2,574,786).

 When the compositions according to the invention contain at least one surfactant, this is generally present at a concentration of between 0.5 and 10% by weight and preferably between 2 and 6% relative to the total weight of the composition.

 The reducing compositions are essentially aqueous, and are in the form of a lotion, thickened or not, a cream or a gel. The pH of these compositions varies between 5 and 10 and preferably between 6.5 and 9.5.

 An acid such as hydrochloric acid, phosphoric acid or citric acid can be used as acidifying agent and as a basifying agent a compound chosen from ammonia, mono, di, or triethanolamine, alkali carbonates or bicarbonates or ammonium.

 The reducing compositions according to the invention may also contain various conventional cosmetic adjuvants used in hair perms such as, for example, a softening agent, an opacifying agent, a sequestering agent, a treating agent, a perfume and / or a dye.

 The present invention also relates to a hair waving process in which a reducing composition as defined above is applied to wet hair previously wound on rollers having from 4 to 20 mm. in diameter, the composition possibly being able to be applied as the hair is rolled up; the reducing composition is then left to act for a time of 5 to 60 min., preferably 5 to 30 min. then abundantly rinsed after which an oxidizing composition is applied to the coiled hair, making it possible to reform the disulphide bonds of the keratin, for an exposure time of 2 to 10 min. After removing the rollers, rinse the hair thoroughly.

 The oxidation or oxidizing composition is of the type commonly used and contains as oxidizing agent for example hydrogen peroxide, an alkali bromate, a persalt or a mixture of alkali bromate and a persal.

 The concentration of hydrogen peroxide can vary from 1 to 10 volumes, but is preferably 8 volumes, the concentration of alkaline bromate is from 1 to 12% and that of parsley from 0.1 to 15% by weight relative to the total weight of the oxidizing composition.

 The pH of the oxidizing composition can vary between 2 and 8 but preferably between 3 and 6.

 The hydrogen peroxide can be stabilized for example by phenacetin, acetanilide, mono and trisodium phosphates or by 8-hydroxyquinoline sulfate.

 The oxidizing compositions can also contain basifying or acidifying agents, preserving agents, sequestering agents, opacifiers and optionally a cationic copolymer such as those defined above for the reducing composition.

 The present invention also relates to a hair straightening or straightening process in which a reducing composition according to the invention is applied to the hair, then the hair is subjected to mechanical deformation making it possible to fix them in their new shape , by a hair straightening operation with a wide tooth comb, with the back of a comb or by hand. After an exposure time of 5 to 60 min., In particular from 5 to 30 min., A new smoothing is then carried out, then rinsed thoroughly and the oxidizing or fixing composition is applied, which is left to act for 2 to 10 min. approximately then rinse the hair thoroughly.

 We will now give, by way of illustration and without any limiting character, several examples of reducing compositions according to the invention as well as methods for its implementation.

COMPOSITION EXAMPLES
EXAMPLE 1:
A permanent waving of the hair is produced by applying the following reducing composition to the whole of the hair.
-N-acetylcysteamine: ......................................... 8g
-Copolymer of vinylpyrrolidone / methacrylate
dimethylaminoethyl in aqueous solution at 20% by weight sold
by GAF under the name "Copolymer 845": îg
-Cocamidopropyl Betaine sold by the company GOLDSMIDT under
the name "Tégobétaine HS": ...................... 3g
-Monoethanolamine qs pH 7
- Colorant qs
-Perfume qs -Water qs ..................................... qsp îO0g
The hair is rolled up on rollers and then the composition is left to act for a period of 10 to 20 min. depending on the nature of the hair.

After rinsing, the following oxidizing composition is then applied to the reduced hair.
-Hydrogen peroxide in aqueous solution at 200 volumes 4.8g -Stabilizers: 0.05g
8-hydroxyquinoline sulfate
Phenacetin
- Citric acid ps ......... qs pH 3
-Perfume qs
-Colourant qs -Water qs .................................. qs 100g
The oxidizing composition is left to act for a period of 10 to 15 min., Then the hair is rinsed with a batting and the rollers are then removed.

 The hair exhibits an excellent hold in the perm over time.

According to the same procedure as that described in Example 1 above, permanent undulations were also produced using the following reducing and oxidizing compositions
EXAMPLE 2
Reducing composition
-N-acetylcysteamine: ....., ... ,, ............................ 6g
-Copolymer of vinylpyrrolidone / methacrylate
dimethylaminoethyl in aqueous solution at 20% by weight sold
by GAF under the name "Copolymer 845" ... 0.5g
-Non-ionic poly (hydroxypropyl ether) surfactant prepared by
condensation, in alkaline catalysis, of 3.5 moles of glycidol
on a mixture of alphadiols having 11 to 14 carbon atoms,
according to the process described in French patent n 71.17206
(2,091,516): ................................ 2g
- Ammonia qs pH 9
-Perfume qs
-Colourant qs -Water qs ................................ qs 100g
The reducing composition is left to act for a time of 10 to 20 minutes.

Oxidizing composition
-Hydrogen peroxide in aqueous solution at 200 volumes 4.8g
-Stabilizers: .................................... 0.05g
8-hydroxyquinoline sulfate
Phenacetin-Citric acid qs ....... qs pH 3
-Perfume qs
-Colourant qs -Water qs ................................... qs 100g
The oxidizing composition is left to act for 10 min.

EXAMPLE 3
Reducing composition
-N-acetylcysteamine: ...................................... 6g
-N-acetylcysteine 6g
-Copolymer of vinylpyrrolidone / dimethylamino methacrylate
ethyl in aqueous solution at 20% by weight sold by the
GAF company under the name "Copolymer 845" 0.8g
-Poly non-ionic surfactant (hydroxypropylether) prepared
by condensation, in alkaline catalysis, of 3.5 moles of glycidol
on a mixture of alphadiols having 11 to 14 carbon atoms,
according to the process described in French patent n 71.17206
(2.091.516) 4g
- Ammonia qs ............. qs pH 9
- Colorant qs
-Perfume qs -Water qs ..................................... qs 100g
The reducing composition is left to act for a time of 10 to 20 min.

Oxidizing composition
-Hydrogen peroxide in aqueous solution at 200 volumes 4.8g
-Stabilizers: ...................................... 0.05g
8-hydroxyquinoline sulfate,
Phenacetin-Citric acid qs ......... qs p11 3
-Perfume qs
-Colourant qs -Water qs ................................... qs 100g
The oxidizing composition is left to act for 10 min.

Claims (14)

 1. Reducing cosmetic composition for carrying out permanent deformation of the hair when cold, containing a combination of a reducing agent and a cationic polymer, characterized in that the reducing agent is N-acetylcysteamine and that the cationic polymer is a copolymer of 45 to 99.5 Z moles of N-vinylpyrrolidone and 55 to 0.5 Z moles of non-quaternized dialkyl (C1-C4) aminoalkyl (C1-C18) acrylate or methacrylate.  2. Composition according to claim 1 characterized in that the N-acetylcysteamine is present at a concentration between 0.1 and 15% by weight and preferably between 3 and 8% by weight relative to the total weight of the composition.  3. Composition according to claim 1 or 2 characterized in that the cationic copolymer is a copolymer of 80 to 99.5 moles Z of N-vinylpyrrolidone and from 0.5 to 20 moles% of dimé thylaminoé thyle methacrylate  4. Composition according to any one of the preceding claims, characterized in that the concentration of cationic copolymer is between 0.1 and 3% by weight and preferably between 0.5 and 2% (expressed as active material) relative to the total weight of the composition.  5. Composition according to any one of the preceding claims, characterized in that the N-acetylcysteamine is associated with cysteine or N-acetylcysteine, the latter being present at a concentration of between 0.1 and 10% and of preferably between 1.5 and 8% by weight relative to the total weight of the composition.  6. Composition according to any one of the preceding claims, characterized in that the reducing composition contains at least one surfactant of nonionic anionic or amphoteric type.  7. Composition according to claim 6 characterized in that the surfactant is of the nonionic poly (hydroxypropylether) type.  8. Composition according to any one of claims 6 or 7, characterized in that the surfactant is present at a concentration of between 0.5 and 10% by weight and preferably between 2 and 6% relative to the weight total of the composition.  9. Composition according to any one of the preceding claims, characterized in that its pH is between 5 and 10 and preferably 6.5 and 9.5.  10. Composition according to any one of the preceding claims, characterized in that it also contains at least one cosmetic adjuvant chosen from a softening agent, an opacifying agent, a sequestering agent, a treating agent, a perfume and / or a dye.  11. A method of permanent deformation of the hair consisting in a first step in reducing the disulfide bonds of keratin by applying to the hair a reducing composition, then in a second step in reforming said bonds by applying an oxidizing composition, characterized in that the reduction step is carried out using a reducing cosmetic composition as claimed in any one of claims 1 to 10.  12. Method according to claim II for waving hair, characterized in that the reducing composition is applied to wet hair, wound on rollers having 4 to 20mm in diameter.  13. The method of claim 11 for straightening or straightening the hair, characterized in that after application to the hair of the reducing composition, the latter are subjected to a smoothing operation using a comb .  14. Method according to any one of claims 11 to 13 characterized in that the reducing composition is allowed to act for a time between 5 and 60 min.