FR3060341A1 - PROCESS FOR TREATING KERATINIC MATERIALS USING A COMPOSITION COMPRISING A THIOLACTONE-LIKE COMPOUND AND A COMPOSITION COMPRISING AN ALKALINE AGENT AND / OR AN ALCOXYSILANE AMINOUS DERIVATIVE - Google Patents

Abstract

The present invention relates to a method for treating keratinous substances, in particular hair using a first composition comprising one or more alkaline agents and / or one or more amino derivatives of alkoxysilane and a second composition comprising one or more thiolactone-type compounds. .

Description

® FRENCH REPUBLIC

NATIONAL INSTITUTE OF INDUSTRIAL PROPERTY © Publication number: 3,060,341 (to be used only for reproduction orders)

©) National registration number: 16 62987

COURBEVOIE © Int Cl ⁸ : A 61 K8 / 49 (2017.01), A 61 Q 5/00

A1 PATENT APPLICATION

©) Date of filing: 21.12.16. (© Applicant (s): L'OREAL Société anonyme— FR. (© Priority: @ Inventor (s): NEIGHBOR Sébastien, DAUBRESSE Nicolas and CHAUMONTET Manon. (43) Date of public availability of the request: 22.06.18 Bulletin 18/25. ©) List of documents cited in the report preliminary research: Refer to end of present booklet (© References to other national documents ©) Holder (s): LOREAL Société anonyme. related: ©) Extension request (s): (© Agent (s): LOREAL Société anonyme.

(64) PROCESS FOR TREATING KERATINIC MATERIALS USING A COMPOSITION COMPRISING A THIOLACTONE COMPOUND AND A COMPOSITION COMPRISING AN ALKALINE AGENT AND / OR AN ALCOXYSILANE DERIVATIVE.

The present invention relates to a process for treating keratin materials, in particular hair, using a first composition comprising one or more alkaline agents and / or one or more amino derivatives of alkoxysilane and a second composition comprising one or more compounds of thiolactone type.

FR 3 060 341 - A1

PROCESS FOR TREATING KERATINIC MATERIAL USING

WORKING WITH A COMPOSITION COMPRISING A THIOLACTONE TYPE COMPOUND AND A COMPOSITION COMPRISING AN ALKALINE AGENT AND / OR AN ALCOXYSILANE DERIVATIVE

The present invention relates to a process for treating keratin materials, in particular human keratin fibers, using a composition comprising at least one alkaline agent and / or at least one amino derivative of alkoxysilane and a composition comprising at least one compound of the type thiolactone, in particular for shaping keratin fibers, and in particular for straightening / straightening hair.

In the hair sector, consumers wish to have compositions which make it possible to bring a temporary change to their hair, and this by aiming for good staying power of the effect achieved. In general, we want the change to persist in shampoos for at least 15 days, or more depending on the nature of the change.

Heat treatments are generally used to permanently modify the shape of the hair. These treatments allow a visual modification of the appearance of the hairstyle, associating a decrease in the degree of crimp, a reduction in the overall volume of the hair, a reduction in frizz, a gain in discipline, a smoother visual appearance, a substantial gain. shine, resistance to humidity and heat for maintaining the hairstyle all day.

In addition, this type of treatment has the advantage of facilitating the daily maintenance of the hair, with the use of less care products, in particular rinse-out treatments such as conditioners or masks, or leave-in treatments. such as serums, care creams or balms, disciplining foams. Hair drying is facilitated, with a significantly shortened brushing time and a reduction in the daily use of flat tweezers, both in time and in intensity. This thus limits the risk of damage to the hair by combined factors of mechanical and thermal stress.

Several technologies are associated with these heat treatments. A first technology is based on the use of compositions based on thiol reducers. These technologies require strict compliance with the application conditions recommended by suppliers, in particular in terms of quantity and break time. In addition, they may be contraindicated on overly sensitized hair and may not be compatible with the same day application of other treatments such as coloring or bleaching. They are also smelly.

Another technology is based on the use of compositions based on formalin (or formaldehyde) and its derivatives. The particularity of these treatments is that they are robust, perfectly compatible with all the other conventional hair treatments, such as the thiolated straightening mentioned above, the alkaline straightening, coloring or bleaching of all types, carried out before or after. They give the hair excellent discipline, very strong shine and ease of daily care. However, in case of repeated applications, new damage to the hair appears which can lead to hair breakage. In addition, for toxicological reasons, the use of some of these compounds is now prohibited and / or regulated. It is therefore increasingly sought to avoid the use of such substances, which can prove to be aggressive for the hair and other keratin materials.

Another technology is based on the use of acid-based compositions, and more particularly on the use of glyoxylic acid. It has thus been proposed, by application WO 2011/104282, a new process for semi-permanent straightening of the hair, consisting in applying an alpha-ketoacid solution to the hair for 15 to 120 minutes, then drying and finally straightening with iron, at a temperature of about 200 ° C, the hair. The alphaketoacid used is preferably glyoxylic acid. However, it has been found that glyoxylic acid may not be well tolerated, especially when the scalp is sensitive and / or irritated. Its volatility, amplified by the use of heat from iron, can also be a problem. Furthermore, the compositions of the prior art can alter the hair and / or alter the color, and more particularly cause undesirable changes in artificial colorings such as oxidation colors.

Treatments have also been proposed using a composition comprising a base associated with a heat treatment for straightening the hair. Such treatments make it possible to obtain good relaxation of the curls but can lead to alterations of the hair fiber. Document EP 1 837 010 describes in particular a smoothing / straightening process using a composition comprising soda and a heat treatment. Document WO 2007/144707 describes a smoothing / straightening process using a composition comprising a non-hydroxylated base such as monoethanolamine, ethylene diamine, associated with a heat treatment. Document WO 2009/117344 also describes a smoothing / straightening process using a composition comprising a non-hydroxylated base and a protein denaturant associated with a heat treatment. To limit alterations in the hair fibers, it has also been proposed to use compositions comprising weak acids at alkaline pH associated with a heat treatment. The document WO 2010/049434 describes for example a smoothing / straightening process in which a composition comprising a dicarboxylic acid such as maleic acid and a heat treatment is applied.

There is still a need to develop a process for treating keratinous materials, in particular keratin fibers such as the hair, more particularly a process for shaping the hair, in particular for straightening the hair, in an effective and lasting manner by limiting the degradation of the hair, in particular residual with respect to successive shampoos.

The Applicant has now discovered that the use of a first composition comprising an alkaline agent and / or an amino derivative of alkoxysilane and of a second composition comprising at least one compound of thiolactone type made it possible to achieve the desired setting properties. in durable form.

Thus, an object of the present invention is a process for treating keratin materials, in particular human keratin fibers such as the hair, using a first composition comprising one or more alkaline agents and / or one or more amino derivative (s) (s) of alkoxysilane and a second composition comprising one or more compound (s), chosen (s) from the compounds of formula (I) below:

(I)

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Formula (I) in which:

• Y represents an oxygen, sulfur atom or an NR group with R representing a hydrogen atom, a (Ci-C ₆ ) alkyl or hydroxy (CiC ₆ ) alkyl group, preferably Y represents an oxygen atom ;

• Ri, R ₂ , R ₃ , R4, R5 and R ₆ , identical or different, represent:

i) a hydrogen atom, ii) hydroxy, iii) amino -NR'R ”, with R 'and R”, identical or different, represent a hydrogen atom, a (Ci-C ₆ ) alkyl or hydroxy group (Ci-C ₆₎ alkyl;

iv) cyano,

v) - (Y ') pC (Y ”) - (Y”') _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are 0 or 1, preferably with p + q = 0 or 1, Y ', Y ”and Y'”, identical or different, represent an oxygen, sulfur, NR atom with R as defined above, preferably Y ', Y ”and Y” represent the oxygen atom, vi) (Ci-C ₆ ) optionally substituted alkyl, vii) (C ₂ -C ₆ ) optionally substituted alkenyl, viii) (Ci-C ₆ ) alkoxy optionally substituted, preferably said alkyl, alkenyl or alkoxy groups being optionally substituted by one or more groups chosen from hydroxy and - (O) _t -C (O) -R ₈ with t valant 0 or 1, R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkyl, d) (Ci-C ₆ ) alkoxy, e) (di) (Ci-C ₆ ) (alkyl) amino, f) (di) hydroxy (Ci-C ₆₎ alkylamino;

or :

ix) R-ι and R ₃ together form a covalent bond;

x) R-ι and R ₂ , and / or R ₃ and R ₄ , and / or R ₅ and R ₆ form together with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R ₉ and R ₁₀ represents a) a hydrogen atom, or a group chosen from b) hydroxy, c) (Ci-C ₆ ) alkyl optionally substituted by one or more hydroxy groups, and d) (C ₂ -C ₆ ) alkenyl, e) - (Y ') _p -C (Y ”) - (Y'”) _q -R ₇ with Y ', Y ”, Y'”, p, q, and R ₇ are as previously defined;

• n represents an integer inclusive between 0 and 6, particularly inclusive inclusive between 0 and 4, more particularly inclusive inclusive between 0 and 3, preferably n is 1 or 2, and more preferably n is 1; Being heard that :

- when n is greater than or equal to 2, then the contiguous groups C (R ₅ ) -R ₆ can be identical or different.

The process of the invention makes it possible in particular to obtain a good relaxation of curls, lasting in particular with respect to shampoos, while limiting the degradation of the hair. It also limits the formation of frizz in the presence of moisture.

Other characteristics and advantages of the invention will appear more clearly on reading the description and the examples which follow.

In what follows unless stated otherwise:

by “organic or mineral acid salt” is meant cosmetically acceptable organic or mineral acid salts, more particularly the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H ₂ SO ₄ , iv) alkylsulfonic acids: Alk-S (O) ₂ OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S (O) ₂ OH such as benzene sulfonic acid and toluene sulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-OS (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H ₃ PO ₄ ; xiii) acetic acid CH ₃ C (O) OH; xiv) triflic acid CF ₃ SO ₃ H and xv) tetrafluoroboric acid HBF ₄ ;

by “alkyl”, a linear or branched hydrocarbon radical containing from 1 to 8 carbon atoms, in particular from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl, preferably methyl;

by “alkenyl”, a linear or branched hydrocarbon radical containing from 2 to 8 carbon atoms, in particular from 2 to 6 carbon atoms, preferably from 2 to 4 carbon atoms, and comprising at least one or more unsaturations, conjugates or not, such as ethylenyl, n-propylene, isopropylenyl, butylene, n-pentylene, n-hexylene;

by alkoxy is meant an alkyl oxy group with “alkyl” or “alkenyl”, as defined above;

by “optionally substituted” preceded by alkyl, alkenyl or alkoxy groups, it is meant that said groups can be substituted on the hydrocarbon radical by one or more, identical or different, groups chosen from i) hydroxy, ii) thiol, iii) halogen, iv) (Ci-C ₄ ) alkoxy, v) hydroxy (C ₂ C ₄ ) alkoxy; vi) (di) (hydroxy (Ci-C ₄ ) (alkyl) amino, vii) cyano, viii) nitro (so), ix) Ra-Z _a -C (Z _b ) -Z _c -, and x) R _a -Z _a -S (O) tZ _c - with Z _b , representing an oxygen or sulfur atom, or a group NR _a ', Z _a and Z _c , identical or different, representing a bond, an atom d oxygen, sulfur, or NR _a; R _a , representing a hydrogen atom, a (Ci-C ₄ ) alkyl group and R _a · representing a hydrogen atom or an alkyl group and t is 1 or 2;

moreover, the addition salts which can be used in the context of the invention are in particular chosen from addition salts with a cosmetically acceptable base such as the basifying agents as defined below as the alkali metal hydroxides such as sodium hydroxide , potash, ammonia, amines or alkanolamines;

The term “straightening” includes, according to the invention, the straightening, straightening or straightening of Caucasian or African hair. The term "straightening" includes, according to the invention, straightening, straightening or straightening Caucasian or African hair.

the expression "at least one" is equivalent to "one or more"; and the expression "inclusive" for a range of concentrations means that the bounds of the range are part of the defined range.

The first composition used in the process according to the invention comprises one or more alkaline agent (s) and / or one or more amino derivative (s) of alkoxysilane.

The alkaline agent (s) can be chosen from:

- hydroxides of alkali or alkaline-earth metals, preferably lithium, calcium, sodium, potassium buffered with one or more amino acids such as glycine,

- carbonates, bicarbonates or hydrogen carbonates, carbonates buffered with bicarbonate to obtain a pH <12.0,

- phosphates of alkali or alkaline earth metals such as lithium, calcium, sodium or potassium,

- ammonia,

- alkanolamines such as mono-, di- and triethanolamines, mono-, diet tri- (hydroxymethyl) aminomethane as well as their derivatives,

- amino acids,

- alkaline polyamino acids or alkaline polyamino acids, such as polylysines, polyarginines,

- polyamines such as polyethyleneimines (PEI), polyvinylamines, the compounds of formula (A) below:

N-W-N

R.

R,

Formula (A) in which W is a (Ci-C ₆ ) alkylene group such as propylene optionally substituted by a hydroxy, amino group or a C1-C4 alkyl radical; R _x , R _y , R _z and R _t , which are identical or different, represent a hydrogen atom, a C1-C4 alkyl or C1-C4 hydroxyalkyl radical.

Examples of amines of formula (A) that may be mentioned include 1,3 diaminopropane, 1,3 diamino 2 propanol, spermine, spermidine.

By alkanolamine is meant an organic amine comprising a primary, secondary or tertiary amine function, and one or more alkyl groups, linear or branched, C ₁ -C ₈ carrying one or more hydroxyl radicals.

Particularly suitable for carrying out the invention are the organic amines chosen from alkanolamines such as mono-, di- or tri-alkanolamines, comprising one to three hydroxyalkyl radicals, which may or may not be C1-C4.

Among compounds of this type, there may be mentioned monoethanolamine (MEA), diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, Ν, Ν-dimethylethanolamine, 2-amino-2-methyl-1-propanol, triisopropanol -amine, 2-amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino1,2-propanediol, tris-hydroxymethylamino-methane.

More particularly, the amino acids which can be used are of natural or synthetic origin, in their L, D or racemic form and comprise at least one acid function chosen more particularly from the carboxylic, sulphonic, phosphonic or phosphoric acid functions. Amino acids can be in neutral or ionic form.

As amino acids which can be used in the present invention, mention may in particular be made of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine , glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine threonine, tryptophan, tyrosine and valine.

Advantageously, the amino acids are basic amino acids comprising an additional amine function possibly included in a cycle or in a ureido function.

Such basic amino acids are preferably chosen from those corresponding to the following formula (B), as well as their salts

R-CH ₂ -CH (NH ₂ ) -C (O) -OH (B)

Formula (B) in which R represents a group chosen from: imidazolyl, preferably 5-imidazolyl; - (CH ₂ ) ₃ -NH ₂ ; - (CH ₂ ) ₂ -NH ₂ ; - (CH ₂ ) ₂ N (H) -C (O) -NH ₂ ; and (CH ₂ ) ₂ -N (H) -C (NH) -NH ₂ .

The compounds corresponding to formula (B) are histidine, lysine, arginine, ornithine, citrulline.

The organic amine can also be chosen from organic amines of heterocyclic type. Mention may in particular be made, in addition to the histidine already mentioned in the amino acids, pyridine, piperidine, imidazole, triazole, tetrazole, benzimidazole.

By “poly” amines or “poly” amino acids is meant alkaline agents comprising at least two amino or amino acid groups linked to the same molecule, in particular these are polymers whose backbone comprises or is substituted by one or more than one amino group or amino acid group.

The organic amine can also be chosen from the amino acid dipeptides. As amino acid dipeptides which can be used in the present invention, mention may in particular be made of carnosine, anserine and whale

The organic amine can also be chosen from compounds comprising a guanidine function. As amines of this type which can be used in the present invention, there may be mentioned in addition to the arginine already mentioned as amino acid, creatine, creatinine, 1,1-dimethylguanidine, 1,1-diethylguanidine, glycocyamine, metformin, agmatine, n-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2 - ([amino (imino) methyl] amino) ethane-1-sulfonic acid.

Mention may be made, as hybrid compounds, of the salts of the amines mentioned above with acids such as carbonic acid, hydrochloric acid.

One can in particular use guanidine carbonate or monoethanolamine hydrochloride.

The amino derivative (s) of alkoxysilane can be chosen from the compounds corresponding to formula (C) below and / or their oligomers and / or their hydrolysis products:

R ^ KORzMRsMOHjy (C) formula (II) in which:

• R! is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-C ₆ hydrocarbon chain substituted by a group chosen from groups:

- NH ₂ or NHR amine (R = C ₁ -C ₂₀ , in particular C ₁ -C ₆ alkyl optionally substituted with a radical comprising a silicon atom, C ₃ -C ₄₀ cycloalkyl or C ₆ -C ₃₀ aromatic),

- an aryl group or aryloxy substituted and / or interrupted by at least one amino group or at least one aminoalkyl group in Ci-C _4;

can be interrupted by a heteroatom (O, S, NH) or a carbonyl group (CO).

• R ₂ and R _{3, which are} identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms, • y denotes an integer ranging from 0 to 3, and • z denotes an integer ranging from 0 to 3, and • x denotes an integer ranging from 0 to 2, with z + x + y = 3.

The term “oligomer” means the polymerization products of the compounds of formula (C) comprising from 2 to 10 silicon atoms.

Preferably, R ₂ represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably the ethyl group.

Preferably, R ₃ represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably methyl or ethyl groups.

Preferably R (is an acyclic chain.

Preferably, the compound of formula (C) only has one silicon atom in its structure.

Preferably, R (represents an alkyl group, and even more preferably a linear alkyl group comprising from 1 to 6 carbon atoms or an aminoalkyl group in Ci-C _6.

Preferably z varies from 1 to 3. Even more preferably z is equal to 3.

Preferably R (is a linear or branched, saturated or unsaturated, C1-C6 hydrocarbon chain, substituted by an amine group NH2 or NHR (R = C1-C20 alkyl, in particular C1-C6, C3-C40 cycloalkyl or aromatic in C6-C30);

Preferably, the first composition comprises at least one compound of formula (C) chosen from 3-aminopropyltriethoxysilane (APTES), 3 aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N- (2 aminoethyl) -3-aminopropyltriethoxysilane, 3 - (aminophenoxy) propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N- (2 aminoethylaminomethyl) phenethyltrimethoxysilane, better among the 3 aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), aminoethyl 3-ethyl aminopropyltriethoxysilane or their oligomers and / or their hydrolysis products.

According to a particularly preferred embodiment, the first composition comprises 3-aminopropyl triethoxysilane (APTES) or its oligomers and / or its hydrolysis products.

According to the invention, the alkaline agent (s) and / or the amino derivative (s) of alkoxysilane used (s) is (are) in the first composition preferably in a concentration inclusive between 0.01 and 40% by weight, preferably between 0.1 and 30%, better between 1 and 20% by weight relative to the total weight of the composition.

Preferably, the first composition is aqueous.

According to a particular embodiment of the invention, the pH of the first composition according to the invention is basic, i.e. greater than or equal to 7.5.

According to a particular embodiment of the invention, the first composition of the invention has a pH ranging from 9.0 to 11.0.

The pH can be adjusted by an organic or mineral acid.

The composition can be buffered.

By “organic acid” is meant an acid, ie a compound capable of releasing a cation or proton H ⁺ , or H3O ⁺ in aqueous media, which comprises at least one hydrocarbon chain in Ci-C20, optionally unsaturated, linear or branched, a group (hetero) cycloalkyl, or (hetero) aryl and at least one acidic chemical function being in particular chosen from carboxy C (O) OH, sulfuric SO ₃ H, SO ₂ H, and phosphoric PO ₃ H ₂ , PO ₄ H ₂ .

More particularly, the acids used are chosen from hydrochloric acid HCl, hydrobromic acid HBr, sulfuric acid H ₂ SO ₄ , alkylsulfonic acids: (Ci-C ₆ ) Alk-S (O) ₂ OH such as d ' methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar-S (O) ₂ OH such as benzene sulfonic acid and toluene sulfonic acid; (C ₁ -C ₆ ) alkoxysulfinic acids: Alk-OS (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; phosphoric acid H ₃ PO ₄ ; triflic acid CF ₃ SO ₃ H and tetrafluoroboric acid HBF ₄ and the carboxylic acid (s) of formula (K) below

O,

OH

LHO Jt (K)

Formula (K) or a salt thereof in which:

A represents a monovalent group when t is worth 0 or polyvalent when t is greater than or equal to 1, hydrocarbon comprising from 1 to 50 carbon atoms, saturated or unsaturated, cyclic or non-cyclic, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms and / or optionally substituted in particular by one or more hydroxy groups; preferably A represents a monovalent (Ci-C ₆ ) alkyl or polyvalent (Ci-C ₆ ) alkylene group optionally substituted by one or more hydroxy groups.

Particularly the carboxylic acids (s) of formula (K) as defined above and preferably the acid or acids used is or are an alpha hydroxy acid such as lactic, glycolic, tartaric or citric acids.

The second composition used in the process according to the invention comprises one or more compounds of formulas (I), of thiolactone type.

According to a particular embodiment of the invention, the compound or compounds of formula (I) are such that n is 1 or 2 and preferably of formula (la):

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Formula (la) in which:

• Ri, R ₂ , R ₃ , R4, R5 and R ₆ , identical or different, represent:

i) a hydrogen atom, ii) hydroxy, iii) cyano, iv) amino -NR'R ”, R 'and R”, identical or different, representing a hydrogen atom, a group (Ci-C ₆ ) alkyl or hydroxy (Ci-C ₆₎ alkyl;

v) - (Y ') pC (O) - (Y ”) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are equal to 0 or 1, with Y 'and Y ”, identical or different, representing an oxygen atom or NR with R as defined above, with preferably p + q = 0 or 1, vi) (Ci-C ₆ ) alkyl optionally substituted by one or more groups chosen from hydroxy and -C (O) -R ₈ with R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkoxy, vii) (C ₂ -C ₆ ) alkenyl, viii) (Ci-C ₆ ) alkoxy, or else:

ix) Rt and R ₂ , and / or R ₃ and R ₄ , and / or R ₅ and R ₆ form together with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R ₉ and R ₁₀ represents a) a hydrogen atom, or a group chosen from b) hydroxy, c) (Ci-C ₆ ) alkyl.

According to a particular embodiment of the invention, the compound or compounds of formula (I) are such that n is 1 and preferably of formula (a):

Rï „(the)

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Formula (a) in which:

• Rt, R ₂ , R ₃ , R ₄ , R5 and R ₆ , identical or different, are as previously defined, in particular represent:

i) a hydrogen atom, ii) hydroxy, iii) cyano, iv) amino -NR'R ”, R 'and R”, identical or different, representing a hydrogen atom, a group (Ci-C ₆ ) alkyl or hydroxy (Ci-C ₆₎ alkyl;

v) - (Y ') pC (O) - (O) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are equal to 0 or 1, with Y 'representing an oxygen atom or NR with R as defined above, with p + q = 0 or 1, vi) (Ci-C ₆ ) optionally substituted alkyl, vii) (C ₂ -C ₆ ) alkenyl, viii) (Ci-C ₆ ) alkoxy, said alkyl groups being optionally substituted by one or more groups chosen from hydroxy and - (O) _t -C (O) -R ₈ with t valant 0 or 1, R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkyl, d) (Ci-C ₆ ) alkoxy, e) (di) (Ci-C6) (alkyl) amino, f ) (di) hydroxy (C1-C6) alkylamino; or :

ix) R-ι and R ₂ , and / or R ₃ and R ₄ , and / or R ₅ and R ₆ form together with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R _g and R ₁₀ represents i) a hydrogen atom, or a group chosen from ii) hydroxy, iii) (Ci-C ₆ ) alkyl optionally substituted by one or more hydroxy groups - in particular R ₃ and R ₄ together with the oxygen atom form an oxo group and / or in particular R-ι and R ₂ , together represent with the carbon atom = C (R ₉ ) -Ri ₀ .

According to a particular embodiment of the invention, the compound or compounds of formula (I) are such that n is 1 or 2 and is of formula (lb):

(lb)

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Formula (lb) in which:

• R ₂ , R ₄ , R5 and R ₆ , identical or different, represent:

i) a hydrogen atom, ii) hydroxy, iii) cyano, iv) amino -NR'R ”, R 'and R”, identical or different, representing a hydrogen atom, a group (Ci-C ₆ ) alkyl or hydroxy (Ci-C ₆₎ alkyl;

v) - (Y ') pC (O) - (O) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are 0 or 1, with p + q = 0 or 1, with Y 'representing an oxygen atom or NR with R as defined above, vi) (Ci-C ₆ ) alkyl optionally substituted by one or more groups chosen from hydroxy and - C (O) -R ₈ with R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkoxy, vii) (C ₂ -C ₆ ) alkenyl, viii) (Ci -C ₆ ) alkoxy, or then:

ix) R ₅ and R ₆ together form with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R _g and R ₁₀ represents a hydrogen atom or a group ( Ci-C ₆ ) alkyl.

According to a particular embodiment of the invention, the compound (s) of

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Formula (s) in which:

Ru and R-12, identical or different, representing a hydrogen atom, or a (Ci-C ₆ ) alkyl group, such as methyl, or ethyl. More preferably Ru and R ₁₂ represent a hydrogen atom.

According to a particular embodiment, the compounds of formula (e) are chosen from:

116

117

118

119

120

121

122

As well as basic, organic or mineral salts, optical isomers, and solvates such as hydrates.

According to a more particular embodiment of the invention, the compound or compounds of formula (I) are of formula (a) or (Ib) and n is 1.

More preferably, the compounds of formula (I) of the invention are chosen from the following compounds:

106

110

111

116

123 ο

ο

ο

ο

127

130

152

152

OH

245

246

247

248

257

258

As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates;

Preferably, the compound (s) of formula (I) is (are) chosen (s) from the compounds of formula (38) to (122) and (153) to (258), preferably from the compounds of formulas (38) to (42b), (70) to (71), (86) to (87), (90) to (95), (153) to (163), more preferably among the compounds of formulas (38), (42 bis), (42 ter), (71), (82), (89), (107 '), (153), (163).

The process for the preparation of the compound of formula (I'b) is defined according to the following synthetic scheme:

ui consists in reacting in step i) 3-butene-1,2,3-tricarboxylic acid (A) with at least one molar equivalent of thiolacetic acid in particular in an aprotic organic solvent, preferably halogenated such as dichloromethane , or THF type ether, more particularly by heating the reaction medium until solvent reflux, preferably at a temperature between 40 ° C. and 80 ° C., to lead to compound (B), in step ii) compound (B) reacts with a strong, organic or inorganic acid such as hydrochloric acid, in particular in a polar protic solvent such as water, more particularly by heating until the solvent refluxes, preferably at a temperature between 60 and 90 ° C, to lead to thiolactone (C).

According to a particular embodiment, the second composition comprises one or more compound (s) of formula (I) as defined above in an amount inclusive between 0.01 and 50%, in particular between 0, 1 and 30%, more particularly between 1 and 25%, preferably between 2 and 20%, more preferably between 5 and 15% by weight relative to the total weight of the second composition.

According to a particular embodiment of the invention, the second composition used in the process according to the invention further comprises a thiol reducing agent such as thioglycolic or non-thiol acid.

Preferably, the second composition used in the process according to the invention is aqueous.

Preferably, the second composition comprises water at a concentration ranging from 10 to 99.5%, better from 30 to 95%, even better from 40 to 90% by weight relative to the total weight of the second composition.

The pH of the second composition of the invention may be less than or equal to 7. Preferably, the pH of the composition ranges from 1 to 6 and more preferably from 2 to 6.

The pHs can be adjusted by an organic or mineral acid as described above, or by an alkaline agent chosen from mineral or organic or hybrid alkaline agents or their mixtures as described above.

The first and second compositions used in the process according to the invention may also comprise at least one usual cosmetic ingredient, in particular chosen from surfactants, in particular nonionic or cationic surfactants, solid or liquid fatty substances, thickeners, in particular polysaccharide thickeners, non-silicone cationic polymers, silicones, solvents, polar or apolar, sun filters; moisturizers; anti-dandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizers or coalescing agents; the charges; the perfumes; silanes other than amino derivatives of alkoxysilane; crosslinking agents. The compositions can obviously comprise several cosmetic ingredients appearing in the list above.

Depending on their nature and the destination of the compositions, the usual cosmetic ingredients can be present in usual amounts, easily determinable by a person skilled in the art, and which can be understood, for each ingredient, between 0.01 to 80% by weight. A person skilled in the art will take care to choose the ingredients used in the composition, as well as their quantities, so that they do not harm the properties of the compositions of the present invention.

The compositions used in the process according to the invention can be in all the galenical forms conventionally used, and in particular in the form of an aqueous, alcoholic or hydroalcoholic, or oily solution or suspension; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O / W, W / O or multiple type; a suspension or emulsion of soft consistency of the cream type (O / W) or (W / O); an aqueous or anhydrous gel, or any other cosmetic form.

These compositions may be packaged in pump dispensers or in aerosol containers, in order to ensure application of the composition in vaporized form (lacquer) or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a foam, for the treatment of hair. In these cases, the composition preferably comprises at least one propellant.

The compositions which have just been described can be applied to the hair. The bath ratio of the compositions applied, that is to say the amount by weight of composition applied relative to the weight of hair treated, can vary from 0.1 to 10, more particularly from 0.2 to 5, and from preferably between 0.5 and 3. Bath ratio means the ratio between the total weight of the composition applied and the total weight of keratin fibers to be treated.

The first composition can be applied to the hair before, after or simultaneously with the second composition. Preferably, the first composition comprising one or more alkaline agents and / or one or more amino derivative (s) of alkoxysilane as described above is applied to the hair before the second composition comprising at least one compound of formula ( I) as described above.

A hair rinsing step can be provided between the application of the two compositions.

According to a preferred embodiment, the first composition is applied before the second composition, preferably with a step of rinsing the first composition before the application of the second composition.

The first and / or second composition of the invention can be applied to dry or wet keratin materials, preferably on dry or damp hair, preferably on dry hair.

In particular, the step of applying each of the two compositions can be followed by an exposure time. The exposure time, namely the contact time of the composition on the hair, is preferably at least 5 minutes, preferably between 10 and 60 minutes, preferably between 15 and 45 minutes. Rinsing of the hair may possibly be provided after the application of the last composition and possibly of the exposure time.

The hair can then be towel-dried or not, preferably towel-dried.

The step for applying the compositions which has just been described can be followed by a step for shaping the hair.

The shaping step can be a straightening / straightening step or even a step for curling the hair.

This shaping step can be carried out using a hair curler, a curling iron or a straightening iron (also called flat pliers).

When the shaping step is carried out using an iron, it can be carried out at a temperature of at least 100 ° C.

Preferably, the iron is used at a temperature of at least 100 ° C, preferably at a temperature between, limits included, 100 ° C and 300 ° C, preferably between 120 ° C and 280 ° C, more preferably between 150 ° C and 250 ° C, and even better, between 200 and 250 ° C.

According to a particular embodiment, a straightening iron is used. In this embodiment, straightening with a straightening iron is carried out in several passes over the hair, in general 3 to 10 passes.

According to a particular embodiment, the method of the invention comprising the steps of applying the compositions according to the invention to the hair, then of straightening with iron is carried out one or more times, spaced or not by one or more several cosmetic treatments, preferably a shampoo, until the desired shape or intensity of shape is obtained.

According to a particular embodiment of the invention, a composition comprising an oxidizing agent can be applied to the hair, after the shaping step. This oxidation step can be followed by rinsing the hair.

According to a particular embodiment of the invention, the process for treating keratin materials of the invention does not use a thiol reducing agent such as thiolactic acid, preferably the process does not use a reducing agent.

According to a particular embodiment, the process for treating keratin materials does not use an anthionization step.

The following examples serve to illustrate the invention without, however, being limiting.

Examples

The following compositions were produced from the ingredients indicated in the tables below, all the quantities being indicated in percent by weight of active material relative to the total weight of the composition.

First compositions A1 to A3 according to the invention

A1 A2 A3 Aminopropyltriethoxysilane 5 20 10 Lactic acid 1 Water Qs 100 Qs 100 QS 100 PH 10 11 11

Second composition B1 according to the invention

B1 Thiolactone 38 5 Ethanol 30 Water Qs 100

For each example, a lock of natural Caucasian curly hair of type IV crimp, 2.7 g, 20 or 27 cm was treated as follows:

P1, P2, P3 and P4 processes according to the invention:

Process P1

The locks are wet, a shampoo is applied (DOP chamomile based on sodium laureth sulfate, cocobetaine, glycerin and cocamide MEA) at a rate of 400 mg per lock. The locks are kneaded then rinsed under running water, wrung out with a finger and dried with a hair dryer.

Composition A1 (2.7g) is applied to a lock of dry hair (2.7g). After 10 minutes, the lock is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer. Composition B1 (2.7g) is applied, then, after 30 minutes, the lock is dried with a hair dryer (without brushing) and then smoothed by ten passes of flat pliers with a passage speed of 10 cm.s' ¹ .

P2 process

The P2 process differs from the P1 process in that the wick is smoothed by ten passages of flat pliers with a passage speed of 13.5 cm.s ' ¹ (instead of 10 cm.s' ¹ ).

P3 process

The locks are wet, a shampoo is applied (DOP chamomile based on sodium laureth sulfate, cocobetaine, glycerin and cocamide MEA) at a rate of 400 mg per lock. The locks are kneaded then rinsed under running water, wrung out with a finger.

Composition A2 (2.7g) is applied to a lock of damp hair (2.7g). After 10 minutes, the lock is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer. Composition B1 (2.7 g) is applied, then, after 30 minutes, the lock is dried with a hair dryer (without brushing) and then smoothed by ten passes of flat pliers with a passage speed of 10 cm.s' ¹ .

P4 process

The locks are wet, a shampoo is applied (DOP chamomile based on sodium laureth sulfate, cocobetaine, glycerin and cocamide MEA) at a rate of 400 mg per lock. The locks are kneaded then rinsed under running water, wrung out with a finger.

Composition A3 (2.7g) is applied to a lock of damp hair (2.7g). After 10 minutes, the lock is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer. Composition B1 (2.7 g) is applied, then, after 30 minutes, the lock is dried with a hair dryer (without brushing) and then smoothed by ten passes of flat pliers with a passage speed of 10 cm.s' ¹ .

Control processes T1, T2, T3 and T4

T1 and T2 processes

The T1 and T2 processes differ from the P1 and P2 processes respectively by the fact that composition A1 is not applied, composition B1 being directly applied to dry hair.

T3 process

The locks are wet, a shampoo is applied (DOP chamomile based on sodium laureth sulfate, cocobetaine, glycerin and cocamide MEA) at a rate of 400 mg per lock. The locks are kneaded then rinsed under running water, wrung out with a finger and dried with a hair dryer.

Composition A1 (2.7g) is applied to a lock of dry hair (2.7g). After 30 minutes, the wick is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer. The wick is smoothed by ten passages of flat pliers with a passage speed of 10 cm.s' ¹ .

T4 process

The locks are wet, a shampoo is applied (DOP chamomile based on sodium laureth sulfate, cocobetaine, glycerin and cocamide MEA) at a rate of 400 mg per lock. The locks are kneaded then rinsed under running water, wrung out with a finger and dried with a hair dryer.

Composition A1 (2.7g) is applied to a lock of dry hair (2.7g). After 10 minutes, the lock is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer., Application of composition A then of a placebo of composition B:

Composition A1 (2.7g) is applied to a lock of dry hair (2.7g). After 10 minutes, the lock is rinsed with running water (15 passages of 1 second followed by a wringing between the fingers) and dried with a hair dryer. A composition C comprising 70% water and 30% ethanol (2.7 g) is applied, then, after 30 minutes, the lock is dried with a hair dryer (without brushing) and then smoothed by ten passages of flat-nosed pliers with a passage speed of 10 cm.s' ¹ .

Each lock is then evaluated according to two main criteria for an indication of the smoothing performance, over time:

I - Level of relaxation after 1 shampoo and natural drying

II - Level of relaxation after 5 cycles of shampooing and natural drying

The level of relaxation is evaluated using a set of reference wicks, with the following notations:

: no relaxation: medium relaxation: good level of relaxation: very good level of relaxation

The results are as follows:

Example T1 T2 T3 T4 1 2 3 4 Criterion 1 1 2 1 1 3 2 3 3 Criterion II 1 1 1 1 2 2 2 2

The method according to the invention therefore makes it possible to improve the relaxation of curls, and the persistence of several relaxation shampoos.

Claims (18)

1. - Process for treating keratin materials, in particular human keratin fibers such as the hair, using a first composition comprising one or more alkaline agents and / or one or more amino derivatives of alkoxysilane and a second composition comprising one or several compound (s) chosen from the following compounds of formula (I): (I) As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates; Formula (I) in which: • Y represents an oxygen, sulfur atom or an NR group with R representing a hydrogen atom, a (Ci-C ₆ ) alkyl or hydroxy (CiC ₆ ) alkyl group, preferably Y represents an oxygen atom ; • Ri, R ₂ , R ₃ , R4, R5 and R ₆ , identical or different, represent: i) a hydrogen atom, ii) hydroxy, iii) amino -NR'R ”, with R 'and R”, identical or different, represent a hydrogen atom, a (Ci-C ₆ ) alkyl or hydroxy group (Ci-C ₆₎ alkyl; iv) cyano, v) - (Y ') _P -C (Y ”) - (Y'”) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, equal to 0 or 1, Y ', Y ”and Y” ”, identical or different, represent an oxygen or sulfur atom, NR with R as defined above, preferably Y', Y” and Y '” represent the oxygen atom, vi) (Ci-C ₆ ) optionally substituted alkyl, vii) (C ₂ -C ₆ ) optionally substituted alkenyl, viii) (Ci-C ₆ ) optionally substituted alkoxy, preferably said alkyl groups , alkenyl or alkoxy being optionally substituted by one or more groups chosen from hydroxy and - (O) _t -C (O) -R ₈ with t valant 0 or 1, R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkyl, d) (Ci-C ₆ ) alkoxy, e) (di) (Ci-C6) (alkyl) amino, f) (di) hydroxy (Ci-C6) alkylamino ; or : ix) R-ι and R ₃ together form a covalent bond; x) R-ι and R ₂ , and / or R ₃ and R ₄ , and / or R ₅ and R ₆ form together with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R ₉ and R ₁₀ represents a) a hydrogen atom, or a group chosen from b) hydroxy, c) (Ci-C ₆ ) alkyl optionally substituted by one or more hydroxy groups, and d) (C ₂ -C ₆ ) alkenyl, e) - (Y ') _p -C (Y ”) - (Y'”) qR ₇ with Y ', Y ”, Y'”, p, q, and R ₇ are such that previously defined; • n represents an integer inclusive between 0 and 6, particularly inclusive inclusive between 0 and 4, more particularly inclusive inclusive between 0 and 3, preferably n is 1 or 2, and more preferably 1; Being heard that : - when n is greater than or equal to 2, then the contiguous groups C (R ₅ ) -R ₆ can be identical or different. 2. - Method according to claim 1 wherein, the compound or compounds of formula (I) are such that n is 1 or 2 and preferably of formula (la): As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates; Formula (la) in which: • Ri, R ₂ , R ₃ , R ₄ , R ₅ and R ₆ , identical or different, represent: i) a hydrogen atom, ii) hydroxy, iii) amino -NR'R ”, with R 'and R”, identical or different, represent a hydrogen atom, a (Ci-C ₆ ) alkyl or hydroxy group (Ci-C ₆₎ alkyl; iv) cyano, v) - (Y ') pC (O) - (Y ”) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are equal to 0 or 1, with Y 'and Y ”, identical or different, representing an oxygen atom or NR with R as defined above, with preferably p + q = 0 or 1, vi) (Ci-C ₆ ) alkyl optionally substituted by one or more groups chosen from hydroxy and -C (O) -R ₈ with R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkoxy, vii) (C2 -C ₆ ) alkenyl, viii) (Ci-C ₆ ) alkoxy, or else: ix) R-ι and R ₂ , and / or R ₃ and R ₄ , and / or R ₅ and R ₆ form together with the carbon atom which carry them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R ₉ and R ₁₀ represents a) a hydrogen atom, or a group chosen from b) hydroxy, c) (Ci-C ₆ ) alkyl. 3. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are such that n is 1 and of formula (a): As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates; Formula (l'b) in which: • Ri, R ₂ , R ₃ , R ₄ , R ₅ and R ₆ , identical or different, are as defined in claim 1, in particular represent: i) a hydrogen atom, ii) hydroxy, iii) amino -NR'R, with R 'and R ”, identical or different, represent üh hydrogen atom, a group (C ^ OeJalkyle or hydroxy (Ci-C ₆ ) alkyl; iv) cyano, v) - (Y ') _p -C (0) - (O) _q -R ₇ with R ₇ representing a hydrogen atom, an (C _r C _e ) alkyl group, p and q, identical or different, are equal 0 or 1, with p + q = 0 or 1, with Y 'representing an oxygen atom or NR with R as defined above; vi) (Ci-C ₆ ) optionally substituted alkyl, vii) (C2-C ₆ ) alkenyl, viii) (CrC ₆ ) alkoxy, said alkyl groups being optionally substituted by one or more groups chosen from pafmi hydroxy and - (O) _r C (O) -R ₈ with t valant 0 or 1, R _s represents a) a hydrogen atom, b) a hydroxy group, c) (CrC ₆ ) alkyl, d) (C _r C ₆ ) alkoxy, e ) (df) (C _r C6) (alkyl) amino, f) (dÎ) hydrQxy (Ci-C ₈ ) alkylamino; or : ix) Ri and R ₂ , and / or R ₃ and R4, and / or R ₅ and Rg form together with the carbon atom which carry them a double bond oxo = O or -C (R ₉ ) -R ₁₀ with R ₉ and Rio represents i) a hydrogen atom, or a group chosen from ii) hydroxy, iii) (Ci-C ₆ ) alkyl optionally substituted by one or more hydroxy groups in particular R ₃ and R4 form together with the carbon atom an oxo group and / or in particular Ri and R ₂ , together represent with the carbon atom = C (R ₉ ) -R ₁₀ . 4. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are such that n is 1 and of formula (le): As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates; Formula (s) in which: Ru and R-12, identical or different, representing a hydrogen atom, or a (Ci-C ₆ ) alkyl group, such as methyl, or ethyl, preferably Ru and R ₁₂ represent a hydrogen atom. 5. - Process according to claim 1, in which the compound or compounds of formula (I) are such that n is 1 or 2 and of formula (Ib): (Ib) As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates; Formula (Ib) in which: • R ₂ , R ₄ , R ₅ and R ₆ , identical or different, represent: i) a hydrogen atom, ii) hydroxy, iii) iv) amino -NR'R ”, R 'and R”, identical or different, representing a hydrogen atom, a (Ci-C ₆ ) alkyl group or hydroxy (Ci-C ₆₎ alkyl; iv) cyano, v) - (Y ') pC (O) - (O) _q -R ₇ with R ₇ representing a hydrogen atom, a (Ci-C ₆ ) alkyl group, p and q, identical or different, are 0 or 1, with p + q = 0 or 1, with Y 'representing an oxygen atom or NR with R as defined above, vi) (Ci-C ₆ ) alkyl optionally substituted by one or more groups chosen from hydroxy and - C (O) -R ₈ with R ₈ represents a) a hydrogen atom, b) a hydroxy group, c) (Ci-C ₆ ) alkoxy, vii) (C ₂ -C ₆ ) alkenyl, viii) (Ci -C ₆ ) alkoxy, or then: ix) R ₅ and R ₆ form together with the carbon atom which carries them a double bond oxo = 0 or = C (R ₉ ) -Ri ₀ with R ₉ and R ₁₀ represents a hydrogen atom or a group ( Ci-C ₆ ) alkyl. 6. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are of formula (a) or (lb) and n is 1. 5 7. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are chosen from the following compounds: OH OH 152 152 ’ 157 158 252 256 265 266 267 As well as their acid or base salts, organic or mineral, their optical isomers, their geometric isomers, their tautomers and their solvates such as hydrates. 8. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) are chosen from the compounds of formula (38) to (122) and (153) to (258), preferably from the compounds of formulas (38) to (42b), (70) to (71), (86) to (87), (90) to (95), (153) to (163), more preferably among the 10 compounds of formulas (38), (42 bis), (42 ter), (71), (82), (89), (107 ’), (153), (163). 9. - Method according to any one of the preceding claims, in which the compound or compounds of formula (I) is (are) in an amount included between 0.01 and 50% inclusive, in particular between 0.1 and 30 %, more 15 particularly between 1 and 25%, preferably between 2 and 20%, more preferably between 5 and 15% by weight relative to the total weight of the second composition. 10. - Method according to any one of the preceding claims, in which the pH of the second composition is less than or equal to 7, preferably ranges from 1 to 6 and more preferably from 2 to 6. 11. - Method according to any one of the preceding claims, in which the second composition does not comprise thiolated reducing agents such as thiolactic acid, preferably does not comprise a reducing agent. 12. - Method according to any one of the preceding claims, in which the first composition comprises an alkaline agent chosen from ammonia, hydroxides of alkali or alkaline earth metals such as sodium or postassium, carbonates, phosphates alkali or alkaline earth metals such as sodium or postassium, alkanolamines such as mono-, di- and triethanolamines, mono-, di- and tri- (hydroxymethyl) aminomethane as well as their derivatives, amino acids, alkaline polyamino acids, such as polylysines, polyarginines, polyamines such as polyethyleneimines (PEI), polyvinylamines, the compounds of formula (A) below: N-W-N (A) Formula (A) in which W is a group (CfCejatkylène such as propylene optionally substituted by a hydroxy, amino group or a C ₄ -C ₄ alkyl radical; Rx, R _y , R _?, R _t , identical or different, represent a hydrogen atom, an alkyl radical Ci-C ₄ hydroxyalkyl or Ct-C _4. 13. - Method according to any one of the preceding claims, in which the first composition comprises one or more amino derivatives of alkoxysilane corresponding to the following formula (C) and / or their oligomers: RtSifQRzMRaMOFQy (C) formula (C) in which: • R ₄ is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-Cb hydrocarbon chain substituted by a group chosen from groups: - amine NH ₂ or NHR (R = C1-C20, especially C _r optionally substituted by a radical containing a silicon atom, cycloalkyl C ₃ -C _4D or aromatic C13-C30), - an aryl group or aryloxy substituted and / or interrupted by at least one amino group or at least one aminoalkyl group in Ci-C _4; R-, which can be interrupted by a heteroatom (O, S, NH) or a group 5 carbonyl (CO), • R ₂ and R _{3, which may be} identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms, • y denotes an integer ranging from 0 to 3, and • z denotes an integer ranging from 0 to 3, and 10 · x denotes an integer ranging from 0 to 2, with z + x + y-3. 14. - Method according to any one of the preceding claims, in which the first composition comprises at least one compound chosen from 315 aminûpropyltriéthoxysilane (APTËS), 3-aminoethyltriethoxysilane (ÀETES), 3 aminopropylméthyldiéthoxysiiane, N- (2-aminoethyl ) -3-aminopropyltriethoxysilane, the 3- (m-aminophenoxy) propyltrimethoxysilane, p-aminophenyltrirnethoxysilane, N- (2 aminoethylaminimethyl) phenethyltrimethoxysilane, better among 3 aminopropyltnethoxysilane (APTES), 3-aminomethyltriethoxysilane (AETES), -3-aminDpropyItriethoxysilane or their oligomers and / or their hydrolysis products; 15. Method according to any one of the preceding claims, characterized in that the first composition comprises at least one compound chosen from 325 aminopropyl triethoxysilane and its oligomers and / or its hydrolyzed products. 16. - Method according to any one of the preceding claims, in which the alkaline agent (s) and / or amino derivative (s) of alkoxysilane is found in the first composition. concentration inclusive between 0.01 and 40% in 30 weight, preferably between 0.1 and 30%, better between 1 and 20% by weight relative to the total weight of the composition. 17. Method according to any one of the preceding claims, in which the first composition is applied to keratin materials, in particular the 35 hair, before, after or simultaneously with the second composition, preferably before the second composition. 18, - Method according to any one of the preceding claims, characterized in that the application to the hair of the first and second compositions is followed by a step of shaping the hair by a heat treatment at a 5 temperature of at least 100 ° C., preferably of a straightening / straightening step carried out by means of a smoothing iron at a temperature between, limits included, 100 ° C. and 300 ° C., preferably between 120 ° C and 280 ° C, more preferably between 150 ° C and 250 ° C, and even better, between 180 ° C and 230 ° C.