FR2931659A1 - Process for permanent deformation of hair by implementing one or more reducing thiols e.g. thioglycolic acid and ammonium thioglycolate and polyphenol acids e.g. 2,3-dihydroxybenzoic acid and/or their precursors e.g. tannic acid - Google Patents

Abstract

Process of permanent deformation of hair by implementing one or more reducing thiols and one or more polyphenol acids and/or their precursors, is claimed. Independent claims are included for: (1) a reducing composition (a) comprising one or more reducing thiols further comprising one or more polyphenol acids and/or their precursors; and (2) a kit for permanent deformation of hair, comprising at least one container that contains the composition (a) comprising one or more reducing thiol and a container comprising an oxidizing composition (b).

Description

The present invention relates to a permanent deformation process of the hair avoiding the appearance of unpleasant odors comprising a reduction step using a thiolated reducer. The invention also relates to a reducing composition and a kit for implementing the method of the invention. One of the techniques commonly used to obtain a permanent deformation of the hair consists first of all in opening the disulfide bonds (SS) of the keratin (cysteine) with the aid of a composition containing a reducing agent, and then after having preferably rinsed the hair so treated, 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 also called fixing composition so as to give, ultimately, the desired shape to the hair.

This technique thus makes it possible to achieve either the waving of the hair, or their straightening or their curing or their smoothing. This new form, imposed on the hair by a chemical treatment, is durable over time for a few weeks and resists particularly the action of washing with water or shampoos and this as opposed to techniques using styling products resulting in temporary deformation, such as setting, such deformation disappearing styling or shampoo. The reduction step is generally carried out using a reducing composition comprising a compound carrying a thiol function.

For the purposes of the invention, the term thiol, thiol reducer or compound bearing a thiol functional group, an organic compound having a thiol -SH group attached to a carbon atom. However, it is known that after a hair reduction treatment using thiolated compounds, whether it is a perm or a smoothing, the hair has a residual thiol odor once dry even

a few days after the treatment. This smell is usually exacerbated when the hair is moistened during a shampoo for example. In the various applications using compounds bearing a thiol functional group, and more particularly in their cosmetic applications, the odor released by the products used is a real inconvenience for users. We tried to mask the smell with perfumes but, in general, the smell is too powerful to be masked significantly. For the user of hair product, this residual odor can be uncomfortable and may be a reason not to perform hair shaping treatment based on thiol reducers. The patent application WO 2000/032157 discloses a relaxing composition comprising a thiosulphate-based activator, an acidifier chosen in particular from citric acid, acetic acid, ascorbic acid and tannic acid and a catalyst. Thiosulfates are not thiolated compounds. In this document, only citric acid and ascorbic acid are exemplified. The patent application WO 1994/002114 discloses a method for preventing the formation of bad odors in a permanent deformation operation of the hair. This process consists, after the reduction step using cysteamine or one of its salts and after the oxidation step, to apply to the hair a post-treatment composition containing in combination in a cosmetic vehicle suitable (i) at least one mineral acid or a buffer mixture in a proportion such that the pH of said composition is between 3.5 and 5.5, ie an organic acid and (ii) at least one synthetic organic odorant compound . Among the organic acids mentioned are acetic acid, lactic acid, salicylic acid, cyclohexanecarboxylic acid, geranic acid and citronellic acid.

However, the solution proposed in the application WO 1994/002114 is not entirely satisfactory. Therefore, it would be interesting to provide

other products or methods of permanent deformation of the hair do not have the disadvantage of releasing an uncomfortable thiol odor or to provide methods for significantly reducing these residual odors.

The applicant has surprisingly discovered that the use of acidic polyphenols or acidic polyphenol precursors as an agent for suppressing bad odors in a permanent hair deformation process (permanent and smoothing product) comprising a step of reduction by a thiolated compound makes it possible to significantly reduce the residual thiol odors. Acidic polyphenol means a compound comprising in its structure one or more acid functions and one or more aromatic rings, the aromatic ring (s) carrying in total at least two hydroxyl groups, one or more of the hydroxy groups that can be etherified. . Preferably, none of the hydroxy groups are etherified. Preferably, at least one of the aromatic rings carries a total of at least two hydroxyl groups. The term "acid polyphenol precursor compound" means an acidic polyphenol compound which can be generated in situ by acid hydrolysis of a precursor, in particular of corresponding esters. The subject of the present invention is therefore a method of permanent hair deformation using one or more thiolated reducing agents and one or more acidic polyphenols and / or one or more acidic polyphenol precursors.

Preferably, this method of permanent deformation of the hair comprises at least one reduction step by application of a reducing composition (a) comprising one or more thiolated reducing agents and an oxidation step using an oxidizing composition (b) such that: - either a reducing composition (a) which contains as agent one or more acidic polyphenols and / or one or more acidic polyphenol precursors is applied,

or an oxidizing composition (b) which itself contains as agent one or more acidic polyphenols and / or one or more acidic polyphenol precursors, or it is applied to the hair before, during or after the step of reducing or oxidizing a composition (c) comprising one or more acidic polyphenols and / or one or more acidic polyphenol precursors. The present invention also relates to a reducing composition comprising one or more thiol reducers and one or more acidic polyphenols and / or one or more acidic polyphenol precursors. The present invention also relates to the use of one or more acidic polyphenols and / or one or more acidic polyphenol precursors as agents for suppressing odors in a reducing composition comprising one or more thiolated reducing agents or in the deformation process hair using one or more thiolated reducing agents. Finally, the present invention relates to a kit for performing a permanent deformation operation of the hair containing at least one container which comprises a reducing composition comprising one or more thiolated reducing agents (a) and a container comprising an oxidizing composition (b) characterized in that either said reducing composition (a) and / or the oxidizing composition (b) comprises or comprise one or more acidic polyphenols and / or one or more acidic polyphenol precursors, or said kit further comprises a container comprising a composition ( c) containing one or more acid polyphenols and / or one or more acidic polyphenol precursors. Preferably, the acidic polyphenols correspond to the type I compounds and the acidic polyphenol precursors correspond to the compounds of the type II, Xq COOH) p (I) (HO n A XOCCOOR (XQ'COO A 'COO) RS' (II) \ U OH_, w

in which: the groups A and A 'represent, independently of one another, an aromatic or heteroaromatic group, fused or otherwise, from 1 to 100 members, optionally substituted with groups other than the hydroxyl, carboxylic acid or ester groups; n represents an integer ranging from 2 to 50, n 'represents an integer ranging from 1 to 50, p represents an integer ranging from 0 to 50, p' and p "represent 0 or 1, p being at less than 1 for compounds of type I and the sum (p "+ p ') being equal to 1 for compounds of type II, - q and q' represent independently of each other 0 or 1, in where q and / or q 'are 1, - X represents an optionally branched and / or substituted 1- to 10-membered alkylene chain, - u represents 0 or 1, - w represents a number from 1 to 5, - s represents 0, 1, 2, 3, 4 or 5, - t represents 0 or 1, - R represents a linear, branched, or cyclic alkyl chain, ev terminally interrupted by a heteroatom selected from nitrogen, oxygen, sulfur and / or phosphorus, optionally

interrupted by a double or a triple bond and / or optionally substituted, and - R 'represents a ring derived from a sugar and in this case, preferably, glucose.

By link is meant the C-C, C = C, CaC, C-heteroatom, C = heteroatom, heteroatom-heteroatom linkages. The heteroatom may be chosen from nitrogen, oxygen, sulfur and / or phosphorus atoms. The substituent or substituents of the groups A, X and R are chosen from: one or more hydrogen atoms, one or more halogen atoms such as chlorine, bromine, iodine or fluorine, one or more several C1-C6 alkyl groups, one or more C1-C6 alkoxy groups, one or more cyano (CN) groups, one or more C1-C6 COalkyl groups, or one or more C1-C6 alkyl groups. ) phenyl, - one or more nitro groups (NO2), - one or more C1-C6 alkoxycarbonyl groups, - one or more hydroxyl groups (OH), - one or more amino groups (NH2), - one or more alkyl groups. C1-C6 amino, one or more optionally branched C1-C6 amino dialkyl groups, one or more optionally branched hydroxyalkyl (C1-C6) amino groups, one or more optionally branched dihydroxyalkyl (C1-C6) amino groups, one or more optionally branched aminoalkyl (C1-C6) amino groups,

one or more optionally branched diaminoalkyl (C1-C6) amino groups, one or more optionally branched hydroxyalkyl (C1-C6) alkyl (C1-C6) alkyl groups, one or more aminoalkyl (C1-C6) alkyl (C1) groups. -C6) amino optionally branched, - one or more optionally branched aminoalkyl (C1-C6) hydroxyalkyl (C1-C6) amino groups, - one or more optionally branched hydroxy (C1-C6) alkyl groups, - one or more aminoalkyl groups. (C1-C6) optionally branched, - one or more optionally branched alkyl (C1-C6) aminoalkyl (C1-C6) groups, - one or more optionally branched dialkyl (C1-C6) aminoalkyl (C1-C6) groups, - one or one or more optionally branched mono or dihydroxyalkyl (C1-C6) aminoalkyl - (C1-C6) groups, - one or more amino groups substituted by one or two optionally branched haloalkyl (C1-C6) groups, - one or more alkyl groups (C1 -C6) aminoalkyl (C1-C6) amino optionally branched, - one or more optionally branched dialkyl (C1-C6) aminoalkyl (C1-C6) amino groups, - one or more hydroxy (C1-C6) alkyl (C1-C6) alkyl aminoalkyl (C1-C6) amino groups optionally branched, - one or more optionally branched aminoalkyl (C1-C6) aminoalkyl (C1-C6) amino groups, - one or more optionally branched hydroxyalkyl (C1-C6) groups, - one or more optionally (C1-C6) aminoalkyl groups. branched, - one or more optionally substituted benzyl rings,

one or more optionally substituted benzylalkyl (C1-C6) groups, one or more ammonium groups -NH3, one or more optionally branched mono, di or trialkyl (C1-C6) ammonium groups, one or more carboxylic acid groups, one or more optionally branched carboxyalkyl groups (C1-C6), one or more sulphonate groups (S03-), one or more optionally branched sulphoalkyl (C1-C6) groups, one or more (C1-C6) alkyl groups. optionally branched carbonylalkyl (C1-C6), - one or more acetamide groups, - one or more aryloxy groups, - one or more (C1-C6) alkylaryloxy groups, - one or more acetylene groups (CH = CH2), - an or one or more (ethylene) carbonyl (CO-CH = CH 2) groups, one or more (C 1 -C 6) alkoxycarbonyl (C 1 -C 6) alkyl groups, or one or more (C 1 -C 6) hydroxyalkoxycarbonylalkyl (C 1 -C 6) groups. C6), one or more (C1-C6) alkoxycarbonyl groups one or more aminoalkoxy (C1-C6) carbonyl (C1-C6) alkyl groups, one or more formyl groups, one or more optionally branched C1-C6 acyl groups, two adjacent groups may form an adjacent ring aromatic or heteroaromatic, substituted or unsubstituted, - two adjacent groups can form a -O-CpH2p-O- type cycle where p is an integer equal to 1 or 2. According to preferred embodiments, the compounds of type I and II Of the invention have the following characteristics alone or in combination:

- A and / or A 'represent a benzene group, - n and n' are independently of each other from 2 to 5 and even more preferably from 2 to 3, - p ranges from 1 to 10 and even more preferably from 1 to 3, - q and / or q 'represent 0, - R' represents a ring derived from a sugar. The following list illustrates the compounds I preferentially used in the process of the invention: 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, gentisic acid (2,5-dihydroxybenzoic acid) ), 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,3,4-trihydroxybenzoic acid, gallic acid (3,4,5-trihydroxybenzoic acid), caffeic acid, 2-hydroxy-3-methoxybenzoic acid, 2-hydroxy-4-methoxybenzoic acid, 2- hydroxy-5-methoxybenzoic acid, - syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid). The compounds II which are preferably used are corilagin, tannic acid and propyl gallate. Preferably, tannic acid is used. According to preferred embodiments, the method of the invention also comprises the following characteristics alone or in combination: the acid polyphenol (s) and / or their precursors are present in a concentration ranging from 0.01 to 10%, preferably from 0.05 to 5%, better still from 0.1 to 3%, by weight relative to the total weight of the composition, - the pH of the composition (c) is between 2 and 12 and preferably between 3 and 11

As indicated above, various methods of application can be envisaged. According to one embodiment, the composition (c) comprising one or more acid polyphenols and / or one or more precursors is applied before the reducing composition, an intermediate rinsing being intercalable. According to another embodiment, the reducing composition (a) itself contains one or more acid polyphenols and / or one or more acidic polyphenol precursors. According to this embodiment, the hair is rinsed after application of the reducing composition and, in a third step, the hair is oxidized by an oxidizing composition. According to another embodiment, the composition (c) is applied after the application of the reducing composition (a) and before the application of the oxidizing composition (b). In this case, preferably rinsing with water between each application.

According to another embodiment, the oxidizing composition (b) itself contains one or more acidic polyphenols and / or one or more acidic polyphenol precursors. According to the preferred embodiment of the invention, the composition (c) is applied after application of the reducing composition (a) and the oxidizing composition (b). Preferably, the hair is rinsed with water after application of the reducing composition and after application of the oxidizing composition. According to this embodiment, the composition (c) may be applied in a rinsed manner or not, preferably in a rinsed manner.

The exposure time of the composition comprising one or more acidic polyphenols and / or one or more acidic polyphenol precursors is between 2 minutes and 1 hour. The application temperature of the composition comprising one or more acid polyphenols and / or one or more acidic polyphenol precursors is between room temperature (25 ° C. to 10 ° C.) and 220 ° C., and preferably between room temperature. ambient and 80 ° C.

In practice, this operation can be conducted by means of a hairdressing helmet, a hair dryer, straightening iron or curling iron, an infrared dispenser and other conventional heating devices.

The composition comprising one or more acidic polyphenols and / or one or more acidic polyphenol precursors preferably comprises one or more additives traditionally used for the treatment of hair. Among the additives that may be used include, for example, surfactants, thickeners, conditioning or treating agents, pH modifying agents and antioxidants. These additives each represent a concentration of 0 to 20% relative to the total weight of the composition. The surfactants used are those commonly used in permanent compositions and may be of nonionic, anionic, cationic or amphoteric type. Mention may in particular be made of alkyl sulphates, alkyl benzene sulphates, alkyl ether sulphates, alkyl sulphonates, quaternary ammonium salts, alkyl betaines, oxyethylenated alkylphenols, fatty acid alkanolamides, oxyethylenated fatty acid esters and nonionic surfactants. ionic compounds of the hydroxypropyl ether family. The thickening agents may be polymeric or non-polymeric. The thickening polymers may be associative or not. Preferably, the thickening polymers used are chosen from cellulose derivatives. It is possible to use volatile or non-volatile silicones, linear or cyclic, or mixtures thereof, polydimethylsiloxanes, quaternized polyorganosiloxanes, those described in French Patent Application 2,535,730, polyorganosiloxanes containing an aminoalkyl group modified with alkoxycarbonylalkyl groups. as described in US Pat. No. 4,749,732, polyorganosiloxanes such as copolymers of

polydimethylsiloxane-polyoxyalkyl such as dimethicone copolyol, polydimethylsiloxanes with end-groups stearoxy- (stearoxydimethicone), polydimethylsiloxane dialkylammonium acetate copolymers or copolymers polydimethylsiloxane polyalkyletain described in GB-A-2 197 352, polysiloxanes organomodified with mercapto or mercapto-alkyl groups as described in FR-B-1 530 369 and EP-A-0 295 780, as well as silanes such as steroxy-trimethylsilane. It is also possible to use other treating ingredients such as waxes, chitosan and its derivatives, fatty alcohols, non-thickening and non-silicone polymers chosen from cosmetically acceptable polymers which may be cationic, anionic or nonionic polymers or amphoteric, preferably cationic, swelling and penetration agents to enhance the effectiveness of the reducing agent such as urea and its derivatives, solvents such as monoalcohols such as ethanol, isopropanol or benzyl alcohol or polyols such as glycerol or propylene glycol or alkyl ethers of alkylene glycol or dialkylene glycol, such as, for example, propylene glycol monomethylethyl ether, dipropylene glycol monomethyl ether or propylene carbonate, and other compounds such as fatty alcohols, derivatives of lanolin, ceramides and in particular ceramides themselves, glycoceramides es, the pseudoceramides described in particular in FR-A-95/1399, and in DOWNING Journal of Lipid Research, Vol. 35, p. 2060, 1994, or in FR-A-2,673,197, EP-A-0227994, WO-94/07844, WO-92/05674, the contents of which are included by reference, active ingredients such as pantothenic acid or panthenol, anti-hair loss agents, anti-dandruff agents, suspending agents, sequestering agents, opacifying agents, dyes, sunscreens, as well as perfumes and preservatives.

The composition (c) may further contain one or more pH modifiers such as alkaline agents. These alkaline agents

may in particular be chosen from ammonia, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, 1,3-propanediamine, an alkaline or ammonium bicarbonate carbonate, an organic carbonate such as guanidine carbonate or else an alkaline hydroxide, used alone or as a mixture. As thiolated reducer suitable for the invention, reference is made to patent FR 2 679 448 listing a number of these compounds. The thiolated reducing agent may especially be chosen from thioglycolic acid, thiolactic acid, ammonium thiolactate, cysteine, N-acetyl-L-cysteine, cysteamine, thioglycerol and glycerol thioglycolate, or one of their cosmetically acceptable salts, such as, more particularly, hydrochlorides, hydrobromides, citrates, acetates and sulphates. Thioglycolic acid is preferably used and even more preferably its salified form ammonium thioglycolate, or cysteine.

The reducing composition may also contain other known reducing agents. The reducing agent is used in proportions sufficient to reduce the disulfide bonds and, preferably, in proportions of between 1 and 25%, in particular of 3 to 25% by weight relative to the total weight of the reducing composition. In general, before rinsing or applying the oxidizing composition, the hair on which the reducing composition, this so as to allow time for the reducer to act properly on the hair. The oxidizing agents that may be used in the oxidizing composition may especially be chosen from hydrogen peroxide or hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates. The use of hydrogen peroxide is particularly preferred.

The concentration of hydrogen peroxide can vary from 1 to 10 volumes, but preferably is of the order of 6 to 8 volumes. The exposure time of the oxidizing composition may vary from 5 to 30 minutes, in particular from 5 to 15 minutes.

The reducing and oxidizing compositions may furthermore also contain alkaline agents, surfactants or treating agents as defined above. Another object of the invention is constituted by a kit for carrying out a permanent deformation operation of the hair containing at least one container which comprises a reducing composition comprising one or more thiolated reducing agents (a) and a container comprising an oxidizing composition (b) characterized in that: - either said reducing composition (a) and / or the oxidizing composition (b) comprises or comprise one or more acidic polyphenols and / or one or more acidic polyphenol precursors, or said kit further comprises a container comprising a composition (c) containing one or more acidic polyphenols and / or one or more acidic polyphenol precursors. The following examples are intended to illustrate the invention without being limiting in nature.

Examples

In all of the following examples, a perm for colored hair was made. Reducing Composition: Ammonium bicarbonate 2.7 g Ammonia at 20% NH3 0.11 g Cysteine 0.5 g Ammonium thioglycolate 1.8 g Hexadimethrin chloride 1 g Sodium pyrolidone carboxylate 1.5 g PEG- 11 methylether dimethicone 1.5 g Hydroxyethylcellulose 0.8 g Sodium cocoamphopropionate 0.6 g sequestering agent qs Conservative agent q.s. Perfume q.s. Water q.s. 100 g The reducing composition was applied for 15 minutes and then rinsed with clear water. The oxidizing composition is then applied to the hair. Oxidizing composition:

- Hydrogen peroxide 6 volumes, pH = 2.3

After fixing (pause for 5 minutes at room temperature), the hair is rinsed with clean water. The post-treatments given as examples below are then applied. These are applied rinsed on damp hair for a period of 3 minutes at room temperature. After the post-treatment, the hair is rinsed with clean water. The action of the post-treatments is compared with that of an identical post-treatment not containing the acidic polyphenol or its precursor but containing citric acid so that the pH of the post-treatment and the reference is identical. The residual odor is judged olfactory by a panel of 5 people.

Post-treatments 1 to 6: Post-Post- Post- Post- Post- Post- treatment treatment treatment treatment treatment treatment 1 2 3 4 5 6 (comparative) Tannic acid 1% - - - - - Gallic acid - 1% - - - - Caffeic acid - - 1% - - - Gentisic acid - - - 1% - 3,5- - - - - 1% - dihydroxybenzoic acid Citric acid - - - - - 1% Distilled water qs 100% qs 100% qs 100% qs 100% qs 100% qs 100% A panel of 5 people significantly feels a decrease in the residual permanent odor on hair post-treated with post-treatments 1 to 5 according to the invention compared to post-treated hair by a post-treatment composition 6 comprising citric acid. This test demonstrates the best performance obtained in terms of residual odor reduction thanks to the process of the invention using acid polyphenols compared to a composition comprising

Post-treatments 7 to 11: Post-treatment 7 Tannic acid (ingredient of the invention) 10/0 Chlorhexidine hydrochloride 0.03% of citric acid. 0/0 methyl p-hydroxybenzoate 0.2 0/0 di-glycerine 20/0 Behenyl trimethyl ammonium chloride solution in a mixture 3% water / isopropanol (79% MA) Ricinoleic alcohol 20% N-oleyl -dihydrosphingosine 4 0/0 Cetyl stearyl alcohol (C16 / C18 50/50) 0.5 16 Tocopheryl acetate 0.01 0/0 Trideceth 12 and cetrimonium chloride (3 and 6% MA) 3% Polysorbate 20 0.2 0 / 0 sterilized distilled water qs 100 0/0 Post-treatment 8 Tannic acid (ingredient of the invention) 1 0/0 Chlorhexidine hydrochloride 0.03 0/0 methyl p-hydroxybenzoate 0.2 0/0 Behenyl chloride trimethylammonium in solution in a mixture of 4% water / isopropanol (79% MA) Hydroalcoholic extract (ethanol / glyceride) of blooming buds of 0.2% rosemary not stabilized (11% MA) Polyethylene glycol (180%) 2 0 / 0 cetearyl alcohol 4 0/0 cetyl palmitate 0.8% Amodimethicone / trideceth-6 / cetrimonium (57.5% / 4.92% / 1% MA) 1.8% Sterilized distilled water qs 100 0/0 Post-treatment 9 Tannic acid (ingredient of the invention) 10/0 Chlorhexidine hydrochloride 0.02 0/0 methyl p-hydroxybenzoate 0.2 0/0 Behenyl trimethyl ammonium chloride solution in a mixture 1.5 0/0 water / isopropanol (79% MA) Cetearyl alcohol 2.5% Potato starch modified with 2 - 1.5% chloroethylaminodipropionic acid neutralized with sodium hydroxide (86% MA) Glycerol 1 0/0 Amodimethicone / trideceth-6 / cetrimonium chloride (57.5% 2.5% / 4.92% / 1% MA) Myristyl / cetyl / stearyl myristate / palmitate / stearate 0.5% Oxylethylenated and oxypropylenated polymethylmethylauroxy / methylsiloxane PM 0, 25% 25,000 (35/3) (18OE / 18OP) (70% MA) Sterilized distilled water qs 100% 0/0 Post-treatment 10 Tannic acid (ingredient of the invention) 0.1% Chlorhexidine hydrochloride 0, 0.2% di-glycerine 0.2% Polyquaternium-10 0.4% Sodium Lauryl Ether Sulfate (2.2 EO) (70% MA) 6.43% Coproacid Monoisopropanolamide 1 0/0 glycol Distearate 1 0/0 Acid ethylene diamine tetracetic disodium salt dihydrate 0.26 0/0 Carboxyvinyl polymer synthesized in an acetate mixture 5% ethyl / cyclohexane Phenoxy-2-ethanol 0.5% sodium N-cocoyl amidoethyl N-ethoxycarboxymethyl glycinate 10 / 0 Sodium chloride 1 0/0 Hexylene glycol 1 0/0 Sterilized distilled water qs 100 0/0 Post-treatment 11 Tannic acid (ingredient of the invention) 1% Chlorhexidine hydrochloride 0.03 0/0 p-hydroxybenzoate of methyl 0.3 0/0 Cetearyl alcohol 8% Myristate / palmitate / myristyl stearate / cetyl / stearyl 1.5% Phenoxy-2-ethanol 0.5% Polyethylene glycol (150 EO) 0 0/0 Polydimethylsiloxane alpha omega dihydroxy / 10% cyclopentadimethyl siloxane mixture (14.7% / 85.3%) 15% methyl terminated SMDI / polyethylene glycol copolymer (methyl 3% C18) in a maltodextrin / water matrix Pregelatinized hydroxypropyl cornstarch phosphate 0.2 0/0 Polyquaternium-37 / oil mineral / PPG-1 Trideceth-6 (50% / 37% / 6% 1 0/0 MA) Candelilla wax 2 0/0 Sterilized distilled water qs 100 0/0

For each of the post-treatments 7 to 11, a panel of 5 persons significantly felt a decrease in the residual permanent odor on post-treated hair compared to the hair not post-treated or post-treated by the previous witness.

Claims (15)

Revendications1. A method of permanently deforming the hair using one or more thiol reducers and one or more acid polyphenols and / or one or more acidic polyphenol precursors. 2. permanent deformation process according to claim 1 which comprises at least one reduction step by application of a reducing composition (a) comprising one or more thiolated reducing agents and an oxidation step using an oxidizing composition ( b), characterized in that: - either a reducing composition (a) which contains itself one or more acidic polyphenols and / or one or more precursors of acidic polyphenols is applied to the hair, or it is applied to the hair an oxidizing composition (b) which itself contains one or more acidic polyphenols and / or one or more acidic polyphenol precursors, or is applied to the hair before, during or after the reduction or oxidation step; composition (c) comprising one or more acidic polyphenols and / or one or more acidic polyphenol precursors. 3. Process according to claim 1 or 2, characterized in that the acidic polyphenols correspond to the type I compounds and the acidic polyphenol precursors correspond to the compounds of the type II, XqCOOH) p (I) (HO n A XqùCOOùR (Xq wherein: the groups A and A 'represent, independently of one another, an aromatic or heteroaromatic group, condensed or not, from 1 to 10 carbon atoms; 100-membered ring, optionally substituted by groups other than hydroxy, carboxylic acid or ester groups, n represents an integer ranging from 2 to 50, n 'represents an integer ranging from 1 to 50, p represents an integer ranging from 0 to 50, p 'and p "represent 0 or 1, p being at least equal to 1 for compounds of type I and the sum (p" + p') being equal to 1 for compounds of type II, q and q 'represent independently of each other 0 or 1, in the case where q and / or q' represent 1, - X represents is an optionally branched and / or substituted 1- to 10-membered alkylene chain; - u represents 0 or 1; - w represents a number from 1 to 5; - s represents 0, 1, 2, 3, 4 or 5; t represents 0 or 1, - R represents a linear, branched or cyclic alkyl chain, optionally interrupted by a heteroatom selected from nitrogen, oxygen, sulfur and / or phosphorus atoms, optionally interrupted by a double or a triple bond and / or optionally substituted, and - R 'represents a ring derived from a sugar, preferably glucose. 4. Method according to claim 3, characterized in that the substituent or substituents of the groups A, X or R are chosen from: - one or more hydrogen atoms, - one or more halogen atoms such as chlorine, bromine, iodine or fluorine, one or more C1-C6 alkyl groups, one or more C1-C6 alkoxy groups, one or more cyano (CN) groups, one or more C1-C6 alkyl groups. C6, one or more (C1-C6) alkyl phenyl groups, one or more nitro (NO2) groups, one or more C1-C6 alkoxycarbonyl groups, one or more hydroxyl (OH) groups, one or more amino groups (NH2), one or more C1-C6 alkyl groups, one or more optionally branched C1-C6 aminoalkyl groups, one or more optionally branched hydroxyalkyl (C1-C6) amino groups, one or more optionally branched dihydroxyalkyl (C1-C6) amino groups, - one or more groups optionally branched aminoalkyl (C1-C6) amino, - one or more optionally branched diaminoalkyl (C1-C6) amino groups, - one or more optionally branched hydroxyalkyl (C1-C6) alkyl (C1-C6) amino groups, - one or more a plurality of optionally branched aminoalkyl (C1-C6) alkyl (C1-C6) alkyl groups, - one or more optionally branched aminoalkyl (C1-C6) hydroxyalkyl (C1-C6) amino groups, - one or more hydroxy (C1-C6) alkyl groups. ) optionally branched, - one or more optionally branched (C1-C6) aminoalkyl groups, one or more optionally branched (C1-C6) alkylalkyl (C1-C6) alkyl groups, - one or more (C1-C6) alkylalkyl dialkyl groups (C1-C6) optionally branched, - one or more optionally branched mono or dihydroxyalkyl (C1-C6) aminoalkyl (C1-C6) groups, - one or more amino groups substituted with one or two groups, optionally haloalkyl (C1-C6) branched, - one or more groupings optionally branched alkyl (C1-C6) aminoalkyl (C1-C6) amino, - one or more optionally branched dialkyl (C1-C6) aminoalkyl (C1-C6) amino groups, - one or more hydroxy (C1-C6) alkyl groups optionally branched alkyl (C1-C6) aminoalkyl (C1-C6) amino, - one or more optionally branched aminoalkyl (C1-C6) aminoalkyl (C1-C6) amino groups, - one or more optionally branched hydroxyalkyl (C1-C6) groups one or more optionally branched aminoalkyl (C1-C6) groups, one or more optionally substituted benzyl rings, one or more optionally substituted (C1-C6) benzylalkyl groups, one or more ammonium groups -NH3, one or more a plurality of optionally branched mono, di or trialkyl (C1-C6) ammonium groups, one or more carboxylic acid groups, one or more optionally branched (C1-C6) carboxyalkyl groups, one or more sulphonate (SO3-) groups, one or more sulphurious groups oalkyl (C1-C6) optionally branched, - one or more optionally branched (C1-C6) alkyl (C1-C6) carbonylalkyl groups, - one or more acetamide groups, - one or more aryloxy groups, - one or more alkyl groups ( C1-C6) aryloxy, - one or more acetylene groups (CH = CH2), - one or more (ethylene) carbonyl groups (CO-CH = CH2), - one or more (C1-C6) alkoxy carbonyl alkyl groups (C1 -C6), one or more hydroxyalkoxy (C1-C6) carbonyl (C1-C6) alkyl groups, one or more (C1-C6) alkoxycarbonyl groups, and one or more (C1-C6) alkylalkoxycarbonylalkyl (C1-C6) alkyl groups. C1-C6), - one or more formyl groups, - one or more optionally branched C1-C6 acyl groups, - two adjacent groups can form an aromatic or heteroaromatic adjacent ring, substituted or unsubstituted, - two adjacent groups can form a ring of type -O-CpH2p-O- where p is an integer of 1 or 2. 5. Method according to any one of claims 1 to 4, characterized in that the acid polyphenol is chosen from: - 2,3-dihydroxybenzoic acid, - 2,4-dihydroxybenzoic acid, - gentisic acid (2,5-dihydroxybenzoic acid), 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,3-acid, 4-trihydroxy benzoic acid, - gallic acid (3,4,5-trihydroxy benzoic acid), - caffeic acid, - 2-hydroxy-3-methoxybenzoic acid, - 2-hydroxy-4- acid methoxybenzoic acid, 2-hydroxy-5-methoxybenzoic acid, syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid). 6. Method according to any one of claims 1 to 4, characterized in that the acidic polyphenol precursor is selected from tannic acid, corilagin, propyl gallate. 7. Process according to claim 6, characterized in that the acidic polyphenol precursor is tannic acid. 8. Process according to any one of the preceding claims, characterized in that the acid polyphenol (s) and / or their derivatives are present in a concentration ranging from 0.01 to 10%, preferably from 0.05 to 5%, better from 0.1 to 3%, by weight relative to the total weight of the composition. 9. Process according to any one of the preceding claims, characterized in that the pH of the composition (c) is between 2 and 12 and preferably between 3 and 11. 10. Process according to any one of the preceding claims, characterized in that the composition (c) is applied after the application of the reducing composition (a) and the oxidizing composition (b). 11. Process according to any one of the preceding claims, characterized in that the reducing composition (a) comprises one or more thiolated reducing agents chosen from thioglycolic acid, ammonium thioglycolate, glycerol thioglycolate and thiolactic acid. ammonium thiolactate, cysteamine, cysteine, N-acetyl-L-cysteine, preferably thioglycolic acid and even more preferably its salified form ammonium thioglycolate. 12. Process according to any one of the preceding claims, characterized in that the oxidizing composition (b) comprises one or more oxidizing agents chosen from hydrogen peroxide, urea peroxide and alkali metal bromates, for example from sodium, persalts such as perborates and persulfates. 13. Reducing composition comprising one or more thiolated reducing agents characterized in that it further comprises one or more acidic polyphenols and / or one or more acidic polyphenol precursors. 14. Use of one or more acidic polyphenols and / or one or more acidic polyphenol precursors as agents for suppressing odors in a reducing composition comprising one or more thiolated reducing agents or in a process of permanent hair deformation involving one or more thiolated reducing agents. 15. Kit for performing a permanent deformation operation of the hair containing at least one container which comprises a reducing composition comprising one or more thiolated reducing agents (a) and a container comprising an oxidizing composition (b) characterized in that: - either said composition reducing agent (a) and / or the oxidizing composition (b) comprises or comprising one or more acid polyphenols and / or one or more acidic polyphenol precursors, or said kit further comprises a container comprising a composition (c) containing one or more several acidic polyphenols and / or one or more acidic polyphenol precursors.