FR3075610A1 - PROCESS FOR THE TREATMENT OF KERATIN FIBERS USING A PARTICULAR CYCLIC POLYCARBONATE AND COMPOSITION COMPRISING A PARTICULAR CYCLIC POLYCARBONATE AND A COMPOUND COMPRISING AN AMINO GROUP - Google Patents

Abstract

The present invention relates to a process for treating keratinous fibers, in particular human keratinous fibers, and more particularly hair, using one or more compounds of formula (I) below:

Description

PROCESS FOR TREATING KERATINIC FIBERS USING A PARTICULAR CYCLIC POLYCARBONATE AND COMPOSITION

COMPRISING A PARTICULAR CYCLIC POLYCARBONATE AND A COMPOUND COMPRISING AN AMINE GROUP

The present invention relates to a process for treating keratin fibers, in particular human keratin fibers, in particular for shaping keratin fibers, and in particular for straightening / straightening the hair, using at least one particular cyclic polycarbonate or a composition comprising it or them and a compound comprising at least one amine group, in particular primary or secondary, preferably primary.

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 reduction 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 care such as conditioners or masks, or leave-in care. such as serums, treatment creams or balms, disciplining foams. Hair drying is facilitated, with a significantly shortened blow-drying 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 exposure time. In addition, they may be contraindicated on excessively sensitized hair and may not be compatible with the same day application of other treatments such as colorings or bleaches. They are also smelly.

Another technology is based on the use of compositions based on formaldehyde (or formaldehyde) and its derivatives. The particularity of these treatments is that they are robust, perfectly compatible with all 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 may 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 was thus 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, combined 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 damage to the hair fibers, it has also been proposed to use compositions comprising weak acids at alkaline pH associated with 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 also 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 Applicants have now discovered that the application of a particular cyclic polycarbonate to the keratin fibers makes it possible to achieve the desired properties of lasting shaping.

Thus, an object of the present invention is a method for treating keratin fibers, in particular human keratin fibers, in particular the hair, comprising the application to said keratin fibers of a composition A comprising one or more compounds of formula (I ) next :

(ALK) - (Q) - (Z) ₇ - (Y) - (ALK ') _n - (W) - T

O) as well as its acid or base salts, organic or mineral, its optical, geometric isomers, and solvates such as hydrates,

Formula (I) in which:

• R ¹ , R ² , R ³ , and R ⁴ , identical or different, represent a hydrogen atom, a (Ci-Ce) alkyl group, particularly (Ci-C4) alkyl, it being understood that one of the R groups ¹ , R ² , R ³ or R ⁴ denotes the chain - (ALK) m- (Q) q- (Z) z- (Y) y- (ALK ') p (W) w-; preferably R ¹ , R ² , and R ³ denote a hydrogen atom, and R ⁴ denotes the chain: - (ALK) m- (Q) q- (Z) z- (Y) _r (ALK ') _p - (W) _w -;

• ALK and ALK ', identical or different, represent a (Ci-Ci2) alkylene group optionally substituted and / or interrupted by one or more heteroatoms such as oxygen, sulfur, or NR ⁸ with R ⁸ as defined below, in particular

ALK and ALK ’represent (Ci-Ce) alkylene, preferably (Ci-C4) alkylene, such as methylene;

• Q, Y, and W, identical or different, represent an oxygen, sulfur or NR ⁸ atom, with R ⁸ representing a hydrogen atom or a (CiC4) alkyl or benzyl group, preferably oxygen or NR ⁸ such as NH;

• Z represents a carbonyl group C = O, thiocarbonyl C = S, imino C = NR ⁸ with

R ⁸ as defined above, preferably carbonyl, • m, p, q, z, y, and w, identical or different, represent 0 or 1; preferably m = 1 and p, q, z, y, and w, identical or different, represent 0 or 1;

• n represents an integer inclusive between 1 and 4, in particular n is 1, 2 or 3, preferably 1 or 2, more preferably n = 1;

• T represents, when u is 1, a hydrogen atom or a (CiC6) alkyl group, or else T represents, when u is greater than or equal to 2, a polyvalent group, said polyvalent group being chosen, when u = 2 , among:

oi) (Ci-Cioo) alkylene optionally interrupted by one or more oxygen or sulfur atoms and / or by one or more NR radicals with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and / or by one or more radicals - Si (R ' ¹ ) (R' ² ) - with R ' ¹ , R' ² identical or different, representing a hydrogen atom, hydroxy, (Ci-C4) alkyl, (Ci-C4 ) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said alkylene radical denotes a (C1Cioo) alkylene radical optionally interrupted by one or more oxygen atoms and / or by one or more radicals -SiMe2, o ii ) (C2-Cioo) alkenylene optionally interrupted by one or more oxygen and sulfur atoms and / or by one or more NR radicals with R representing a hydrogen atom or a C1C4 alkyl radical such as NH and / or by one or more radicals - Si (R ' ¹ ) (R' ² ) - with R ' ¹ , R' ² identical or different, representing a hydrogen, hydroxy atom, (Ci-C4) alkyl, (Ci-C4) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said alkenylene radical denotes a (C1-C100) alkenylene radical optionally interrupted by one or more oxygen atoms and / or by one or more radicals -SiMe2, o iii) (hetero) arylene such as phenylene as 1,3-phenylene, o iv) (hetero) cycloalkylene, said polyvalent group being chosen, when u = 3 or 4, from :

o i) a saturated or unsaturated, linear or branched multivalent (trivalent or tetravalent) hydrocarbon radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms;

o ii) a (hetero) cyclic radical, aromatic or not, multivalent (trivalent or tetravalent), preferably containing 5 or 6 carbon atoms;

• u represents an integer inclusive between 1 and 4, preferably 2 or 3, it being understood that:

- T is divalent when u is 2, is trivalent when u is 3, and tetravalent when u is 4;

- when u is equal to 1 then m + p + q + z + y greater than or equal to 1;

- when u is 2, 3 or 4 then the following reasons:

O.

(ALK) - (Q) - (Z) _z - (Y) - (ALKj— (W) - are the same or different.

Another object of the invention is a composition A comprising one or more compounds of formula (I) defined above as well as its acid or base salts, organic or mineral, its optical, geometric isomers and solvates such as hydrates, and one or more compound (s) comprising at least one amine group.

The process of the invention makes it possible in particular to obtain a relaxation of curls, lasting in particular with respect to shampoos, while limiting the degradation of the hair. It also allows good control of hair volume and 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:

“compound comprising at least one amine group” means a compound comprising at least one primary amino group -NH2, secondary> NH or tertiary -N <and not comprising a carbonate function -O-CO-O-, preferably said compound comprises at least one primary or secondary amine group, more preferably said compound comprises at least one primary amine group;

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 H2SO4, iv) alkylsulfonic acids: Alk-S (O) 2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S (O) 2OH 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 H3PO4; xiii) acetic acid CHsC (O) OH; xiv) triflic acid CF3SO3H 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 ethylenic unsaturations, conjugated or not, such as ethylenyl, npropylenyl, isopropylenyl, butylenyl, n-pentylenyl, n-hexylenyl;

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

"alkylene" means a linear or branched divalent hydrocarbon containing from 1 to 8 carbon atoms, in particular from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as methylene, ethylene, n-propylene , n-butylene, n-pentylene, n-hexylene;

“alkenylene” means a hydrocarbon radical as defined for “alkenyl”;

by “(hetero) arylene” is meant a divalent “aryl” or divalent “heteroaryl” group, said aryl or heteroaryl groups being as defined below;

by “(hetero) cycloalkylene” is meant a divalent “cycloalkyl” or divalent “heterocycloalkyl” group, said cycloalkyl or heterocycloalkyl groups being as defined below;

by “optionally substituted” preceded by alkyl, alkenyl, alkylene, alkenylene or alkoxy groups, it is meant that said groups can be substituted on the hydrocarbon radical by one or more groups, identical or different, chosen from i) hydroxy, ii) thiol, iii) halogen, iv) (Ci-C4) alkoxy,

v) hydroxy (C2-C4) alkoxy; vi) (di) (hydroxy (Ci-C4) (alkyl) amino, vii) cyano, viii) nitro (so), ix) R _a -Z _a -C (Zb) -Z _c -, and x) R _a -Z _a -S (O) tZ _c - with Zb, representing an oxygen or sulfur atom, or a group NR _a ', Z _a and Z _c , identical or different, representing a bond, an oxygen atom , sulfur, or a group NR _a ; R _a , representing a hydrogen atom, a (CiC4) alkyl group and R _a · representing a hydrogen atom or an alkyl group and t is 1 or 2;

an “aryl” radical represents a mono or polycyclic carbon group, condensed or not, comprising from 6 to 22 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl; more preferably the aryl radical is a phenyl;

a “heteroaryl radical” represents a mono or polycyclic group, condensed or not, comprising from 5 to 22 links, from 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atom, and of which at at least one cycle is aromatic; preferably heteroaryl is selected from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyle, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyle, naphthooxazolyle, naphthopyrazolyle, oxadiazolyl, oxazolyl, oxazolopyridyl , phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyle, pyridyle, pyridinoimidazolyle, pyrrolyle, quinolyle, tetrazolyle, thiadiazolyle, thiazolyle, thiazolopyridinyle, thiazoylimidazolyle, thiopyrylyly;

a “heterocyclic radical” is a radical which may contain one or two unsaturations but not aromatic, mono or polycyclic, condensed or not, containing from 5 to 22 links, comprising from 1 to 6 heteroatoms chosen from the nitrogen atom, oxygen, and sulfur;

a “heterocÿcloalkyl radical” is a heterocyclic radical comprising at least one saturated ring and at least one heteroatom chosen from the nitrogen, oxygen and sulfur atoms;

the “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical can be substituted by at least one substituent carried by a carbon atom, chosen from:

a C1-C16, preferably C1-C6 alkyl radical, optionally substituted by one or more radicals chosen from hydroxyl, C1-C2 alkoxy, (poly) hydroxy-C2-C4, acylamino, amino radicals substituted by two identical or different C1-C4 alkyl radicals, optionally carrying at least one hydroxyl group or, the two radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, preferably 5 or 6-membered, saturated or unsaturated, optionally substituted optionally comprising another heteroatom identical or different from nitrogen;

a halogen atom;

a hydroxyl group;

a C1-C2 alkoxy radical;

a C2-C4 (poly) hydroxyalkoxy radical;

an amino radical;

a 5- or 6-membered heterocÿcloalkyl radical;

an optionally cationic 5- or 6-membered heteroaryl radical, preferably imidazolium, and optionally substituted by a (C1-C4) alkyl radical, preferably methyl;

an amino radical substituted by one or two identical or different C1-C6 alkyl radicals optionally carrying at least:

i) a hydroxyl group, ii) an amino group optionally substituted by one or two optionally substituted C1-C3 alkyl radicals, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 chain links, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen, iii) a 5- or 6-membered heteroaryl radical optionally substituted by a (C1-C4) alkyl radical, preferably methyl;

an acylamino radical (-NR-C (O) -R ') in which the radical R is a hydrogen atom, a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a C1-C2 alkyl radical;

a carbamoyl radical ((R) 2N-C (O) -) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group;

an alkylsulfonylamino radical (R'-S (O) 2-N (R) -) in which the radical R represents a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group and the radical R 'represents a C1-C4 alkyl radical, a phenyl radical; an aminosulfonyl radical ((R) 2N-S (O) 2-) in which the radicals R, which may or may not be identical, represent a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group, a carboxylic radical in acid or salified form (preferably with an alkali metal or ammonium, substituted or not); a cyano group;

a polyhaloalkyl group, preferably trifluoromethyl;

preferably, the “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical can be substituted by at least one substituent carried by a carbon atom, chosen from a C1-C6 alkyl radical, a d atom 'halogen; a C1-C2 alkoxy radical; a polyhaloalkyl group, preferably trifluoromethyl, more preferably from a C1-C6 alkyl radical;

the cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent chosen from groups:

hydroxyl;

C1-C4 alkoxy, C2-C4 (poly) hydroxyalkoxy; C1-C4 alkyl;

alkylcarbonylamino (RC (O) -N (R ') -) in which the radical R' is a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group and the radical R is a radical C1-C2 alkyl, amino optionally substituted by one or two identical or different C1-C4 alkyl groups themselves optionally bearing at least one hydroxyl group, said alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;

alkylcarbonyloxy (RC (O) -O-) in which the radical R is a C1-C4 alkyl radical, amino group optionally substituted by one or two identical or different C1-C4 alkyl groups themselves optionally bearing at least a hydroxyl group, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from nitrogen;

alkoxycarbonyl (RGC (O) -) in which the radical R is a C1-C4 alkyl radical, G is an oxygen atom, or an amino group optionally substituted by a C1-C4 alkyl group itself optionally bearing '' at least one hydroxyl group, said alkyl radical possibly forming, with the nitrogen atom to which it is attached, a heterocycle comprising from 5 to 7 links, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or not from l 'nitrogen;

preferably, the cyclic or heterocyclic part of a non-aromatic radical may be substituted by at least one substituent chosen from C1-C4 alkoxy, (C2-C4) (poly) hydroxyalkoxy, C1-C4 alkyl groups; and more preferably by at least one C1-C4 alkyl radical such as methyl;

a cyclic, heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, can also be substituted by one or more oxo groups;

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 method according to the invention comprises a step of applying a composition A.

Composition A comprises one or more compound (s) of formula (I) as defined above.

According to one embodiment, u is 1 and T represents a hydrogen atom or an i) (Ci-Ce) alkyl group.

According to another embodiment u is greater than or equal to 2, preferably equal to 2 or 3, and T represents a di or trivalent group chosen from ii) (Ci-Ce) alkylene, iv) (hetero) arylene, and v ) cycloalkylene.

According to another embodiment u is equal to 2 and T represents a (CiCioo) alkylene radical optionally interrupted by one or more oxygen, sulfur atoms and / or by one or more NR radicals with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and / or by one or more radicals - Si (R ' ¹ ) (R' ² ) - with R ' ¹ , R' ² identical or different, representing a hydrogen atom , hydroxy, (Ci-C4) alkyl, (Ci-C4) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said alkylene radical denotes a (Ci-Cwo) alkylene radical optionally interrupted by one or more atoms of oxygen and / or by one or more radicals -SiMe2. According to this embodiment, T preferably represents a radical T1 of formula - (CH2) xi- [O- (CH2) x2-] x3 (O) x4- with x1 = 0 to 10, x2 = 2 or 3, x3 = 1 to 50 preferably 3 to 20, x4 = 0 or 1 or a T2 radical of formula - (CH2) yi [Si (R ' ¹ ) (R' ² ) -O-] y2- Si (R ' ¹ ) (R ' ² ) - (CH2) y3 - with y1 = 0 to 10, y2 = 1 to 50 preferably 3 to 20, y3 = 0 to 10 preferably 1 to 5 and R' ¹ , R ' ² identical or different , representing a radical (Ci-C4) alkyl such as methyl.

According to another embodiment u is equal to 2 and T represents a divalent (hetero) arylene group, preferably arylene such as phenylene, more particularly 1,3-phenylene.

According to another embodiment u is equal to 2 and T represents a divalent group, cycloalkylene, preferably cyclohexylene preferably substituted by one or more C1-C4 alkyl radicals such as methyl.

According to another embodiment u is equal to 2 and T represents a divalent C1-C4 alkylene group such as methylene, ethylene, butylene.

According to another embodiment u is equal to 3 and T represents i) a saturated or unsaturated, preferably saturated, linear or branched trivalent hydrocarbon radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms ii ) a trivalent (hetero) cyclic radical, aromatic or not, preferably aromatic, containing 5 or 6 carbon atoms, preferably 6 carbon atoms, such as a 1,3,5-trivalent phenyl radical.

More preferably, composition A comprises one or more compound (s) of formulas (I) as defined above in which u is 2, Q represents

an oxygen atom, ALK and ALK ’represent a (Ci-C4) alkylene, such methylene. than according to an advantageous mode the compounds of formula (I) are such that u worth 2 and: - m = 1; - ALK represents a (C1-C4) alkylene, such as methylene; - Q represents an oxygen atom; - q = 0 or 1; - Z represents a carbonyl; - Z = 0 or 1; - Y represents N H; - y = 0 or 1; - ALK ’represents a C1-C4) alkylene, such as methylene; - p = 0 or 1; - w = 0. according to an advantageous mode the compounds of formula (I) are such that u worth

and:

(ALK) - (Q) - (Z) _z - (Y) - (ALK ¹ ) - (W) -

- one of the patterns is such that m + p is an integer greater than or equal to 1, preferably m is 1 and p is 0, and preferably q = z = y = 1; and, 2 Jn (ALK) - (Q) - (Z) _z - (Y) - (ALK ¹ ) - (W) - d *

- the other reason is such that m + p is worth

0, preferably the other pattern is such that m + p + q + z + y + w is 0.

According to a preferred embodiment, the compound or compounds of formula (I) is (are) chosen from the following compounds:

the B

If

lj with t integer between 1 and 50, preferably between 3 and 30, more preferably between 5 and 20;

Ik with r integer between 1 and 50, preferably between 3 and 30, more preferably between 5 and 20;

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, composition A comprises one or more compounds of formula (I) in a content ranging from 0.01 to 50%, in particular from 0.05 to 30%, more particularly from 0.1 to 20%, preferably from 0.5 to 15%, and more preferably from 1 to 10% by weight relative to the total weight of the composition.

Composition A used in the process of the invention can also comprise one or more solvents, identical or different, chosen from organic solvents.

By organic solvent is meant an organic substance capable of dissolving another substance without chemically modifying it.

The organic solvents are preferably chosen from liquid compounds at a temperature of 25 ° C and under 105 Pa (760mm Hg).

Preferably, the organic solvent (s) are chosen from monoalcohols and polyols.

By "monoalcohol" is meant an organic compound comprising a single "hydroxy" group (-OH), the organic compound can be aliphatic, acyclic, linear or branched.

Advantageously, the said monoalcohol (s) comprise from 2 to 4 carbon atoms.

Preferably, the said monoalcohol (s) are chosen from ethanol, propanol, isopropanol, butanol, and a mixture of these compounds, and preferably the said monoalcohol (s) are chosen from ethanol, isopropanol, and a mixture of these compounds, and more preferably, said monoalcohol is ethanol.

When they are present in composition A, the monoalcohols are present in an amount inclusive between 1 and 60%, preferably between 10 and 50%, more preferably between 20 and 50% by weight relative to the total weight of the composition .

By "polyols" is meant an organic compound comprising at least two hydroxy groups (-OH), carried by different carbon atoms, this compound being able to be aliphatic, acyclic, linear or branched.

More particularly, the polyol (s) which can be used according to the invention comprise from 2 to 30 hydroxy groups, more preferably from 2 to 10 hydroxy groups, even more preferably from 2 to 3 hydroxy groups.

The polyol or polyols which can be used according to the invention generally contain at least three carbon atoms.

Preferably, the said polyol (s) which can be used according to the invention are chosen from polyols comprising at least three carbon atoms and ethylene glycol, and preferably from propylene glycol, 1,3-propanediol, 1,3 -butylene glycoi, pentane-1,2-diol, dipropÿlene glycoi, hexylene glycoi, pentylene glycoi, glycerol, ethylene glycoi, and a mixture of these compounds, and more preferably among propylene glycoi, 1,3-propanediol, and a mixture of these compounds.

When they are present in composition A, the polyols are present in an amount inclusive between 1 and 50%, preferably between 5 and 30%, more preferably between 5 and 15% by weight relative to the total weight of the composition .

According to a particularly preferred embodiment, composition A comprises ethanol.

Preferably, composition A according to the invention is aqueous or hydroalcoholic.

Preferably, composition A 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 composition.

According to a particular form of the invention, composition A also contains one or more compound (s) comprising one or more amine group (s). The amine groups can be primary, secondary, or tertiary amine groups.

According to a particular embodiment of the invention, the compound (s) comprising one or more amine group (s) can be chosen from:

- amino silicones;

- amino derivatives of alkoxysilane;

- organic amines that do not contain a silicon atom;

- non-silicone polymers comprising one or more amine group (s).

Amino silicone

By “amino silicone” is meant any silicone comprising at least one primary, secondary or tertiary amine function.

The weight average molecular weights of these amino silicones can be measured by gel permeation chromatography (GPC) at room temperature (25 ° C) in polystyrene equivalent. The columns used are μ styragel columns. The eluent is THF, the flow rate is 1 ml / min. 200 μΙ of a 0.5% by weight silicone solution in THF are injected. Detection is done by refractometry and UVmetry.

Preferably, the amino silicone (s) capable of being used in the context of the invention are chosen from:

a) the polysiloxanes corresponding to formula (A):

O (A) in which x 'and y' are whole numbers such that the weight average molecular weight (Mw) is between approximately 5,000 and 500,000;

b) amino silicones corresponding to formula (B):

R'aG3-a-Si (OSiG2) n- (OSiGbR'2-b) m-O-SiG3-a-R'a (B) in which:

- G, identical or different, denotes a hydrogen atom, a phenyl, OH, C1-Cs alkyl group, for example methyl, or C1-Cs alkoxy group, for example methoxy,

- a, identical or different, denotes 0 or an integer from 1 to 3, in particular 0,

- b denotes 0 or 1, in particular 1,

- m and n are numbers such that the sum (n + m) varies from 1 to 2000, in particular from 50 to 150, n being able to designate a number from 0 to 1999, and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10;

- R ', identical or different, denotes a monovalent radical of formula -CqH2qL in which q is a number ranging from 2 to 8, and L is an optionally quaternized amino group chosen from the groups:

-N (R) ₂ ; -N ⁺ (R) ₃ A-; -NR-QN (R) ₂ and-NR-QN ⁺ (R) 3 A-, in which R, identical or different, denotes hydrogen, phenyl, benzyl, or a monovalent saturated hydrocarbon radical, for example a C1C20 alkyl radical ; Q denotes a group of formula C _r H2r, linear or branched, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A- represents a cosmetically acceptable anion, in particular halide such as fluoride, chloride, bromide or iodide.

Preferably, the amino silicones are chosen from the amino silicones of formula (B). Preferably, the amino silicones of formula (B) are chosen from the amino silicones corresponding to the following formulas (C), (D), (E), (F), and / or (G).

According to a first embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones called trimethylsilylamodimethicone corresponding to formula (C):

(CH ₃ ) ₃ If

CH,

I

O - Si - i ch ₃ ch ₃

I

O —Si (CH ₂ ) ₃

OSi (CH ₃ ) ₃

NH (ÇH ₂ ) ₂ (C) nh ₂ in which m and n are numbers such that the sum (n + m) varies from 1 to 10 2000, in particular from 50 to 150, n being able to designate a number from 0 to 1999, and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10.

According to a second embodiment, the amino amino silicones corresponding to formula (B) are chosen from the silicones of formula (D) below:

CH ₃

R ₁ -If ch ₃ ch ₃

O - SiCH, ï '

O —If - (ÇH ₂ ) ₃

NH (ÇH ₂ ) ₂

Hh ₃

O — Si — R ₃ ch ₃ (D) nh ₂ in which:

- m and n are numbers such that the sum (n + m) varies from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200; n being able to designate a number from 0 to 999 and in particular from 49 to 249 and more particularly from 125 to 175 and m being able to designate a number from 1 to 1000, in particular from 1 to 10, more particularly from 1 to 5;

- R1, R2, R3, identical or different, represent a hydroxy or C1-C4 alkoxy radical, at least one of the radicals R1 to R3 denoting an alkoxy radical.

Preferably the alkoxy radical is a methoxy radical.

The hydroxy / alkoxy molar ratio preferably ranges from 0.2: 1 to 0.4: 1 and preferably from 0.25: 1 to 0.35: 1 and more particularly is equal to 0.3: 1.

The weight average molecular mass (Mw) of these silicones preferably ranges from 2000 to 1,000,000, more particularly from 3,500 to 200,000.

According to a third embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones of formula (E) below:

ch ₃

R ₁ -Si— ch ₃

Ç ^H 3 o —Sich ₃

O —If - (ÇH ₂ ) ₃

NH (ÇH ₂ ) ₂

Hh ₃

O — Si — R ₂ ch ₃ (E) nh ₂ in which:

- p and q are numbers such that the sum (p + q) varies from 1 to 1000, in particular from 50 to 350, and more particularly from 150 to 250; p being able to designate a number from 0 to 999 and in particular from 49 to 349 and more particularly from 159 to 239 and q being able to designate a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5;

- R1, R2, different, represent a hydroxy or C1-C4 alkoxy radical, at least one of the radicals R1 or R2 denoting an alkoxy radical.

Preferably the alkoxy radical is a methoxy radical.

The hydroxy / alkoxy molar ratio generally ranges from 1: 0.8 to 1: 1.1 and preferably from 1: 0.9 to 1: 1 and more particularly is equal to 1: 0.95.

The weight average molecular mass (Mw) of the silicone preferably ranges from 2000 to 200,000 and even more particularly from 5,000 to 100,000 and more particularly from 10,000 to 50,000.

Commercial products comprising silicones of structure (D) or (E) may include in their composition one or more other amino silicones whose structure is different from formulas (D) or (E).

A product containing amino silicones of structure (D) is offered by the company WACKER under the name BELSIL® ADM 652.

A product containing amino silicones of structure (E) is offered by WACKER under the name Fluid WR 1300®

Among the amino silicones of formula (E), there may also be mentioned the product Belsil ADM Log 1 from WACKER.

When these amino silicones are used, a particularly advantageous embodiment is their use in the form of an oil in water emulsion. The oil-in-water emulsion can comprise one or more surfactants. The surfactants can be of any kind but preferably cationic and / or nonionic. The number average size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometers. Preferably, in particular as amino silicones of formula (E), microemulsions are used whose average particle size ranges from 5 nm to 60 nanometers (limits included) and more particularly from 10 nm to 50 nanometers (limits included). Thus, one can use according to the invention the amino silicone microemulsions of formula (E) proposed under the names FINISH CT 96 E® or SLM 28020® by the company WACKER.

According to a fourth embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones of the following formula (F):

ch ₃

HO If—

CH,

CH,

CH,

Yes

CH,

If · i

AT

NH (CH _? )

2/2

Ç ^H 3

O-Si-OH

CH, (F)

NH.

in which :

- m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10;

- A denotes a linear or branched alkylene radical having 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.

The weight average molecular mass (Mw) of these amino silicones preferably ranges from 2000 to 1000000 and even more particularly from 3500 to 200000.

A silicone corresponding to this formula is for example the XIAMETER MEM

8299 EMULSION from DOW CORNING.

According to a fifth embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones of the following formula (G):

CH,

H ₃ C-Si—

CH,

CH,

Yes

CH,

CH,

O —If i

AT

NH (CH _? )

2'2

CH,

O-Si-CH

CH, (G)

NH, in which:

- m and n are numbers such that the sum (n + m) varies from 1 to 2000 and in particular from 50 to 150, n being able to designate a number from 0 to 1 999 and in particular of

49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10;

- A denotes a linear or branched alkylene radical having 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched.

The weight average molecular weight (Mw) of these amino silicones preferably ranges from 500 to 1,000,000 and even more particularly from 1,000 to 200,000.

A silicone corresponding to this formula is for example DC2-8566 Amino

Fluid by DOW CORNING.

c) amino silicones of formula (J):

Ri R | 1 H ₂ N- (C _m H _2m ) -NH- (C _n H _2n ) -Si- -0- -If - O- -Yes - - ^R 5 (J) L r ₂ J x ^R 4 3

in which :

- Ri, R2, R3 and R4, identical or different, denote a C1-C4 alkyl radical or a phenyl group,

- R5 denotes a C1-C4 alkyl radical or a hydroxyl group,

- n is an integer varying from 1 to 5,

- m is an integer varying from 1 to 5, and

- X is chosen in such a way that the amine index varies from 0.01 to 1 meq / g.

d) multiblock polyoxyalkylenated amino silicones, of type (AB) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group.

Said silicones preferably consist of repeating units of the following general formulas:

[- (SiMe ₂ O) xSiMe ₂ - R -N (R) - R'-O (C ₂ H ₄ O) a (C3H6O) b-R'-N (H) -R-] or [- ( SiMe ₂ O) xSiMe ₂ - R -N (R) - R '- O (C ₂ H ₄ O) a (C3H ₆ O) b-] in which:

- A is an integer greater than or equal to 1, preferably ranging from 5 to 200, more particularly ranging from 10 to 100;

- b is an integer between 0 and 200, preferably ranging from 4 and 100, more particularly between 5 and 30;

- x is an integer ranging from 1 to 10,000, more particularly from 10 to 5,000;

- R is a hydrogen atom or a methyl;

- R, identical or different, represent a divalent hydrocarbon radical in C2-C12, linear or branched, optionally comprising one or more heteroatoms such as oxygen; preferably, R denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a radical -CH2CH2CH2OCH2CH (OH) CH2-; preferably R denotes a radical -CH ₂ CH2CH2OCH ₂ CH (OH) CH2-;

- R ', identical or different, represent a divalent hydrocarbon radical in C2-C12, linear or branched, optionally comprising one or more heteroatoms such as oxygen; preferably, R 'denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a radical -CH ₂ CH2CH2OCH ₂ CH (OH) CH2-; preferably R 'denotes -CH (CH ₃ ) -CH ₂ -.

The siloxane blocks preferably represent 50 and 95 mol% of the total weight of the silicone, more particularly from 70 to 85 mol%.

The level of amine is preferably between 0.02 and 0.5 meq / g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.

The weight-average molecular mass (Mw) of the silicone is preferably between 5,000 and 1,000,000, more particularly between 10,000 and 200,000.

Mention may in particular be made of the silicones sold under the names Silsoft A-843 or Silsoft A + by Momentive.

e) and mixtures thereof.

Preferably, the amino silicone (s) that can be used in the process according to the invention is or are chosen from amino silicones of formula (B) and polyoxyalkylenated multiblock amino silicones, of type (AB) n, more preferably among the amino silicones of formula (C), (D), (E), (F), (G) and the polyoxyalkylenated multiblock amino silicones of type (AB) n, A being a block polysiloxane and B being a polyoxyalkylenated block comprising at least one amine group.

Even more preferably, the amino silicone (s) which can be used in the process according to the invention is or are chosen from amino silicones of formulas (E), amino silicones of formulas (F), and multiblock polyoxyalkylenated amino silicones of type (AB) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group.

Amino derivatives of alkoxysilane

Composition A can contain one or more compound (s) comprising one or more amine group (s), said amino compounds possibly being amino derivatives of alkoxysilane.

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

RiSI (OR ₂ ) z (R ₃ ) x (OH) _y (C ') formula (C') in which:

Ri is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon chain substituted with a group chosen from groups:

- NH ₂ or NHR amine (R = C1-C20 alkyl, in particular C1-C6 optionally substituted by a radical containing a silicon atom, C3-C40 cycloalkyl or C6-C30 aromatic),

an aryl or aryloxy group substituted and / or interrupted by at least one amino group or by at least one C1-C4 aminoalkyl group;

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

• R ₂ and R3, 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 ’) containing 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, R3 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 Ri is an acyclic chain.

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

Preferably, Ri represents an alkyl group, and even more preferably a linear alkyl group, comprising from 1 to 6 carbon atoms or a C1-C6 aminoalkyl group.

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

Preferably, Ri is a saturated or unsaturated, linear or branched C1-C6 hydrocarbon chain, substituted by an NH2 or NHR amine group (R = C1-C20 alkyl, especially 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 3 aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminyl aminopropyltriethoxysilane or their oligomers and / or their hydrolysis products.

According to a particularly preferred embodiment, the amino derivative (s) of alkoxysilane is 3-aminopropyl triethoxysilane (APTES) or its oligomers and / or its hydrolysis products.

Organic amines not containing a silicon atom

Composition A can contain one or more compound (s) comprising one or more amine group (s), said amino compounds possibly being organic amines not comprising a silicon atom.

The organic amines which do not contain a silicon atom can be chosen from:

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

- amino acids,

- the compounds of formula (A ’) below:

% / ^R =

N-W-N

R ^Z \ y ^R * (A ')

Formula (A ') in which W is a (Ci-C6) 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 , 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, in Ci-Cs 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, sulfonic, 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.

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.

Non-silicone polymers comprising one or more amine groups.

The non-silicone polymers comprising one or more amine group (s) can be chosen from polyamines.

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 the backbone of which comprises or is substituted by one or more than one amino group or amino acid group.

The polyamines can be chosen, for example, from polyethyleneimines (PEI) and polyvinylamines, alkylenediamines such as C36-alkylene diamine sold under the reference Priamine 1075® by CRODA.

In a particularly advantageous manner, composition A according to the invention comprises one or more amino silicones, preferably chosen from amino silicones of formulas (E), aluminum silicones of formulas (F), and polyoxyalkylenated amino silicones of multiblock type (AB ) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group, better among polyoxyalkylenated multiblock amino silicones.

According to one embodiment, composition A can comprise one or more compound (s) comprising one or more amine group (s), preferably in a total amount included between 0.01 and 10%, in particular between 0.1 and 7%, more particularly between 0.1 and 4% by weight relative to the total weight of composition A.

According to a particularly advantageous embodiment, composition A comprises one or more silicone (s), preferably amine (s), as defined above in an amount inclusive between 0.01 and 10%, in particular between 0.1 and 7%, more particularly between 0.1 and 4% by weight relative to the total weight of the composition.

The pH of composition A of the invention can be less than or equal to 8, in particular when composition A comprises one or more amine group (s) chosen from amino derivatives of alkoxysilane, the organic amines not comprising an atom of silicon, non-silicone polymers comprising one or more amine group (s).

Preferably, the pH of the composition ranges from 1 to 7 and more preferably from 7.

The pH can be adjusted by a compound known to a person skilled in the art.

The method according to the invention can also comprise the application of a composition B, distinct from composition A, which comprises one or more compound (s) comprising one or more amine group (s) as defined above.

Composition B can be applied before or after composition A.

Preferably, when composition B comprises one or more compound (s) comprising one or more amine group (s) chosen from amine derivatives of alkoxysilane, organic amines comprising no silicon atom and polymers non-silicone comprising one or more amine group (s), composition B is applied before composition A.

Preferably, when composition B comprises one or more compound (s) comprising one or more amine group (s) chosen from amino silicones, composition B is applied after composition A.

Preferably, composition B does not contain a compound of formula (I).

Preferably, composition B comprises at least one compound comprising one or more amine group (s) chosen from amino silicones, preferably chosen from amino silicones of formulas (E), amino silicones of formulas (F) , and multiblock polyoxyalkylenated amino silicones, as well as amino derivative (s) of alkoxysilane, preferably 3-aminopropyl triethoxysilane (APTES) or its oligomers and / or its hydrolysis products, polyethyleneimines.

According to another embodiment, the method according to the invention can also comprise a step of applying a composition C comprising one or more alkaline agent (s) different from the compound (s) comprising one or more group ( s) amine.

The alkaline agent (s) different from the compound (s) comprising one or more amine group (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,

the carbonates, bicarbonates or hydrogen carbonates of alkali or alkaline-earth metals, preferably lithium, calcium, sodium, potassium,

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

- ammonia.

According to a preferred embodiment, the alkaline agent different from the compounds comprising one or more amine group (s) is chosen from hydroxides of alkali or alkaline earth metals, preferably of calcium, sodium, potassium buffered with one or several amino acids such as glycine.

The alkaline agent (s) different from the compounds comprising one or more amine groups can be applied before, simultaneously or after composition A, preferably before.

According to the invention, the alkaline agent (s) different from the compounds comprising one or more amine group (s) is (are) in composition C preferably in a concentration of 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, compositions B and C are aqueous or hydroalcoholic.

According to a particular embodiment of the invention, the pH of compositions B and C is basic, i.e. greater than or equal to 7.5.

According to a particular embodiment of the invention, the compositions B and C used in the process of the invention have a pH ranging from 9.0 to 11.0.

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

Compositions B and C can be buffered.

By “organic acid” is meant an acid, ie a compound capable of releasing an H ⁺ cation or proton, or HLO * in aqueous media, which comprises at least one C1-C20 hydrocarbon chain, optionally unsaturated, linear or branched, a group (hetero) cycloalkyl, or (hetero) aryl and at least one acidic chemical function being chosen in particular from carboxy C (O) OH, sulfuric SO3H, SO2H, and phosphoric PO3H2, PO4H2.

More particularly, the acids used are chosen from hydrochloric acid HCl, hydrobromic acid HBr, sulfuric acid H2SO4, alkylsulfonic acids: (Ci-Ce) Alk-S (O) 2OH such as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids: Ar-S (O) 2OH such as benzene sulfonic acid and toluene sulfonic acid; (Ci-C6) alkoxysulfinic acids: Alk-O-S (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; phosphoric acid H3PO4; triflic acid CF3SO3H and tetrafluoroboric acid HBF4 and the carboxylic acid (s) of formula (K) below

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-Ce) alkyl or polyvalent (Ci-Ce) 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 compositions A, B and C used in the process according to the invention may also comprise at least one usual cosmetic ingredient different from the previously described compounds, in particular chosen from surfactants, in particular nonionic or cationic surfactants, fatty substances solid or liquid, thickeners, in particular polysaccharide thickeners, non-silicone cationic polymers, silicones, solvents, polar or non-polar, sunscreens; 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 entering into 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, especially 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 can 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.

A hair rinsing step can be provided between the application of compositions A and B and / or C.

The compositions of the invention can be applied to dry or wet keratin fibers, preferably on dry or damp hair, preferably on damp 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. A hair rinse can optionally be provided after the application of the last composition and optionally after the application time.

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

According to a particular form of the invention, the method for treating keratin fibers, in particular human keratin fibers, in particular the hair, comprises the application of a composition A optionally containing one or more compounds comprising one or more group (s ) amine.

According to another particular form of the invention, the method for treating keratin fibers, in particular human keratin fibers, in particular the hair, comprises the application

1) of a composition A optionally containing one or more compounds comprising one or more amine group (s), and

2) of a composition B containing one or more compounds comprising one or more amine group (s);

3) and optionally a composition C as defined above, it being understood that steps 1) and 2) or even 1) and 2) and 3) can be carried out simultaneously or sequentially, preferably 1) then 2) when the composition B comprises an amino silicone, preferably without rinsing step of composition A before the application of composition B.

The step of applying the compositions which has just been described can be followed by a step of heat treatment of keratin fibers.

The heat treatment step for keratin fibers is generally carried out at a temperature ranging from 40 ° C to 250 ° C, preferably ranging from 60 ° C to 250 ° C.

Preferably, the heat treatment step has a duration ranging from 5 seconds to 1 hour, preferably ranging from 5 seconds to 1 minute, per lock of hair.

This heat treatment step is generally carried out using a heating tool such as a straightening iron, a curling iron, a crimping iron, a stirring iron, a steam iron, a helmet, a hair dryer, a infrared heating system or a heated curler.

The method according to the invention can also include a step of 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 preferred embodiment, composition A is applied first to the hair. Composition A is applied with a bathing ratio of the composition which can vary from 0.1 to 10, more particularly from 0.2 to 5. Composition A can be applied to damp hair. The step of applying composition A 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. This exposure time can be carried out under heat, in particular under an occlusive system, such as a heated curler. The hair can then be wrung out to remove the excess composition. Rinsing of the hair can then be provided after the application of the composition and possibly after the application time. The hair can then be towel-dried or not, preferably towel-dried. Composition B comprising one or more amino silicones is then applied to the hair. Composition B is applied with a bath ratio of the composition which can vary from 0.1 to 10, more particularly from 0.2 to 5. The hair can then be dried with a hair dryer. The method according to the invention can also include a step of shaping the hair using an iron or even a curler.

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

According to one embodiment, the method according to the invention is carried out one or more times, spaced or not by one or more cosmetic treatments, preferably spaced by one or more shampoos, and this to treat hair that has grown back, will have undergone other treatments capable of causing changes in crimping or for obtaining the desired shape or intensity of shape.

The invention also relates to a kit comprising, on the one hand, a composition A as defined above and, on the other hand, a composition B as defined above, and optionally a composition C as defined above.

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

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.

A1 A2 B1 IPDA dicarbonate (Formule le) 5 5 - PEG-40 / PPG-8 Methylaminopropyl / hydroxypropyl dimethicone copolymer * 0.6 0.6

Ethanol 46.5 47.5 49 Water Qs 100 qs 100 Qs 100

*: Silsoft A + LT from Momentive

Volume control

According to a first example, composition A1 is applied to a lock of natural Caucasian curly hair of type IV crimp, of 2.7 g, 27 cm, has been treated as follows:

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 is applied at the rate of 2.7 g per wick, the wick is left for 30 minutes in contact with composition A1. The wick is then wrung to remove the excess composition, then it is dried with a hair dryer. It is then smoothed with flat pliers brought to 230 ° C which are passed ten times over the wick. In parallel, composition B1 is applied at the rate of 2.7 g by the same type of wick, the wick is left for 30 minutes in contact with composition B1. The wick is then wrung to remove the excess composition, then it is dried with a hair dryer. It is then smoothed with flat pliers brought to 230 ° C which are passed ten times over the wick.

The volume of the locks thus treated is evaluated after 5 shampoos. It is found that the composition A1 according to the invention makes it possible to obtain a good afterglow to the shampoos of the volume reduction, improved compared to the lock treated with the composition B1.

Hydrophobicity measurement

According to a second example, the hydrophobicity of locks of hair treated with the method according to the invention is evaluated.

The surface of natural hair is hydrophobic, due to the presence of natural lipids, the most common of which is 18-methylicosanoic acid. These surface lipids are grafted to the epicuticle by a thioester bond, providing the natural hair with lubrication which facilitates its disentangling and styling. In damaged hair, environmental conditions (eg exposure to UV) or exposure to cosmetic treatments (eg discoloration) can cleave these thioester bonds, which leads to a loss of lipids on the surface, replaced by sulfonic acid functions. This makes the surface of the hair more hydrophilic and compromises its natural lubrication. ¹

Therefore, a highly desirable property of the hair is the hydrophobicity of its surface.

To assess this hydrophobicity, we use standardized strands of hair 27 cm long straight brown natural hair. Natural locks are subjected to the process of sensitization by bleaching to produce locks constituting a model of damaged hair.

Composition A2 is applied to a lock of damaged hair thus obtained at the rate of 2.7 g per lock, the lock is left in contact with composition A2 for 15 minutes. Then, composition B1 is then applied to this lock, at a rate of 2.7 g per lock. The wick is then wrung to remove the excess compositions, then it is dried with a hair dryer. It is then smoothed with flat pliers brought to 230 ° C which are passed ten times over the wick.

According to a control method, composition B1 is applied to a lock of damaged hair obtained as described above, at a rate of 2.7 g per lock. The wick is then wrung to remove the excess compositions, then it is dried with a hair dryer. It is then smoothed with flat pliers brought to 230 ° C which are passed ten times over the wick.

The hair is then gathered into 1.5 g locks by weighing using a precision balance (Perkin-Elmer). The wick is cut into wicks of

3.5 cm long using razor blades. A plastic cable tie is attached to the middle of each wick to prevent slipping of the fibers. The 3.5 cm wick is fixed in the sample holder of a Zwickiline Z2.5 mechanical testing machine (Zwick, Germany) equipped with a 100 Newtons measurement cell (N). The wick is immersed at a constant speed of 100 mm / min in a beaker filled with MilliQ® water. The water is changed between each measurement after careful cleaning of the beaker. The force necessary to fully penetrate the brush into the water is recorded and represented in the form of a force curve / ¹ Popescu and Hocker, Chem. Soc. Rev., 2007, 36, 1282-1291 displacement. Upon entering the water, the wick resists immersion, causing an increase in the force exerted by the testing machine to ensure constant movement. The area under this curve is used to determine the total immersion energy. By subtracting from it the value measured for a cable clamp alone, we obtain a value of immersion energy which is correlated to the contact angle of the water at the surface of the hair measured by the method of Willhelmy. ²

The value measured for the lock treated according to the invention, after 1 shampoo, is 0.024 mJ, and after 10 shampoos, 0.023 mJ.

The value measured for the lock treated according to the control process, after 1 10 shampoo is 0.025 mJ, and after 10 shampoos, 0.015 mJ.

After 10 shampoos, it is found that the hydrophobicity of the surface of the hair treated with the method according to the invention is improved.

The composition and the method according to the invention therefore make it possible to obtain a curl relaxation, to reduce the volume of the hair and to improve the afterglow with several shampoos of the volume reduction, while retaining good cosmeticity of the hair, in particular a smooth feel of the hair.

² Neumann and Good, Techniques of Measuring Contact Angles, in Surface and colloid science, Vol. 11: experimental methods, 1979, Springer US, pp31-91

Claims (27)

1. Process for treating keratin fibers, in particular human keratin fibers, in particular the hair, comprising the application of a composition A comprising one or more compounds of formula (I) below: (ALK) - (Q) - (Z) - (Y) - (ALK ') - (W) As well as its acid or base salts, organic or mineral, its optical, geometric isomers and solvates such as hydrates, Formula (I) in which: • R ^1. , R ² , R ³ , and R ⁴ , identical or different, represent a hydrogen atom, a (Ci-CeJalkyle, particularly (Ci-C4) alkyl group, it being understood that one of the groups R ¹ , R ² , R ³ or R ⁴ denotes the chain - (ALK) n, - (Q) q- (2) z- (Y) y- (ALK ') p (W) w-; preferably R ¹ , R ² , and R ³ denote a hydrogen atom, and R ⁴ denotes the chain: - (ΑίΚ) π, - (Ο) _η - (Ζ) ^ (Υ) τ (ΑίΚ ') ρ- (νν) «- ; ALK and ALK ', identical or different, represent a (Ci-Ci ₂ ) alkylene group optionally substituted and / or interrupted by one or more heteroatoms such as oxygen, sulfur, or NR ^B with R ⁸ as defined below, in particular ALK and ALK 'represent (Ci-C6) alkene, preferably (CiC ^ ankylene, such as methylene; • Q, Y, and W, identical or different, represent an oxygen, sulfur or NR ⁸ atom, with R ⁸ representing a hydrogen atom or a group (C _r Cijalkyl or benzyl, preferably oxygen or NR ⁸ such as NH; • Z represents a carbonyl group C = O, thiocarbonyl C = S, imino C = NR ⁸ with R ⁸ as defined above, preferably carbonyl, • m, p, q, z, y, and w, identical or different, represent 0 or 1; preferably m = 1 and p, q, z, y, and w, identical or different, represent 0 or 1; • n represents an integer inclusive between 1 and 4, in particular n is 1, 2 or 3, preferably 1 or 2, more preferably n = 1; • T represents, when u is 1, a hydrogen atom or a (CiC ₆ ) alkyl group, or else T represents, when u is greater than or equal to 2, a polyvalent group, said polyvalent group being chosen, when u = 2, among: oi) (Gi "CIOO) alkylene optionally interrupted by one or more oxygen atoms, sulfur atoms and / or by one or more radicals NR with R representing a hydrogen atom or an alkyl radical such as NH ₄ CiC and / or by one or more radicals - Si (R ' ¹ ) (R' ² ) - with R ' ¹ , R' ² identical or different, representing a hydrogen atom, hydroxy, (Ci-C ₄ ) alkyl, (Gi -C ₄ ) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said alkylene radical denotes a (GiCioo) alkylene radical optionally interrupted by one or more oxygen atoms and / or by one or more -SiMe radicals ₂ , o il) (Cz-Cioojalkénylène optionally interrupted by one or more oxygen or sulfur atoms and / or by one or more NR radicals with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and / or by one or more radicals - Si (R ' ¹ ) (R' ² ) - with R '\ R' ² identical or different, representing a hydrogen atom, hydroxy, (Ci-C4) alkyl, (CiC ₄ ) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said alkenylene radical designated a (C1-C100) alkenylene radical optionally interrupted by one or more atoms of oxygen and / or by one or more -SiMez radicals, o iii) (hetero) arÿlene such as phenylene as 1,3-phenylene, o iv) (hetero) cycloalkylene, said polyvalent group being chosen, when u = 3 or 4, among: oi) a saturated or unsaturated, linear or branched multivalent (trivalent or tetravalent) hydrocarbon radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms; o ii) a (hetero) cyclic radical, aromatic or not, multivalent (trivalent or tetravalent), preferably containing 5 or 6 carbon atoms; • u represents an integer inclusive between 1 and 4, preferably 2 or 3, it being understood that: - T is divalent when u is 2, is trivalent when u is 3, and tefravait when u is 4; - when u is equal to 1 then m + p + q + z + y greater than or equal to 1; when u is 2, 3 or 4 then the following reasons: not R '(ALK) - (Q> - (Z) - (Y) - (ALK ¹ ) - (W) - are the same or different. 2. - Method according to claim 1 wherein the compound or compounds of formula (I) are such that u is greater than or equal to 2, preferably equal to 2 or 3 and T represents a di or trivalent group chosen from ii) ( Ci-C ₆ ) aikylène, iv) (hetero) arylene, and v) cycloalkyiene. 3. - Method according to claim 1 wherein the compound or compounds of formula (i) are such that u is equal to 2 and T represents a radical (Ci-Cioo) alkylene optionally interrupted by one or more ox atomesgene atoms, sulfur and / or by one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and / or by one or more radicals-Si (R ' ¹ ) (R' ² ) - with R ' ¹ , R ¹² identical or different, representing a hydrogen atom, hydroxy, (Ci-C4) alkyl, (Ci-C4) alkoxy, preferably C1-C4 alkyl, such as methyl, preferably said radical alkylene denotes a (Ci-Cioo) alkylene radical optionally interrupted by one or more oxygen atoms and / or by one or more radicals -SiMez 4. - Method according to the preceding claim wherein T represents a radical Tl of formula - (CH2) _x i- [O- (CH2) x2-] x3 (O) x4- with x1 = 0 to 10, x2 = 2 or 3, x3 = 1 to 50 preferably 3 to 20, x4 = 0 or 1 or a radical T2 of formula - (CH2) yi- [Si (R ' ¹ ) (R' ² ) -O-] y2Si (R ' ¹ ) (R ' ² ) - (CH2) y3 - with y1 = 0 to 10, y2 = 1 to 50 preferably 3 to 20, y3 = 0 to 10 preferably 1 to 5 and R' ¹ , R ' ² identical or different, representing a (C1Ç4) alkyl radical such as methyl. 5. - Method according to claim 1 in which the compound or compounds of formula (I) are such that u is equal to 2 and T represents: a divalent (hetero) arylene group, preferably arylene, such as phenylene, more particularly 1,3-phenylene, a divalent group, cycloalkyiene, preferably cyclohexyiene, preferably substituted by one or more C1-C4 alkyl radicals such as methyl, or - a divalent C1-C4 alkylene group such as methylene, ethylene, butylene. 6. - Method according to claim i wherein the compound or compounds of formula (I) are such that u is equal to 3 and T represents i) a saturated trivalent hydrocarbon radical 5 or unsaturated, preferably saturated, linear or branched containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms ii) a trivalent (hetero) cyclic radical, aromatic or not preferably aromatic, containing 5 or 6 atoms of carbon, preferably 6 carbon atoms such as a trivalent phenyl radical in 1, 3, 5. 7. - Method according to any one of the preceding claims in which: .gold! R X z ^ OC: (ALK) - (Q) - (Z) ₂ - (Y) - (ALK ·) - (W); R * - one of the patterns is such that m + p is an integer greater than or equal to 1, preferably m is 1 and p is 0, and preferably q = z = y = 1; and ~ ^ (ALK) ~ (Q) - (Z) - (Y) - (ALK ') - (W) - R ³ - the other pattern ^K is such that m + p is 0, preferably the other pattern is such that m + p + q + z + y + w is 0. 8. - Method according to any one of the preceding claims in which the compound or compounds of formula (I) are chosen from the following compounds: 0 'ld j-c 3Λ the If r ° rA <0 \ i · —ô r ° ig lh t between 1 and 50, preferably between 3 and 30, more preferably between 15 5 and 20; ο ° s Ik r integer between 1 and 50, preferably between 3 and 30, more preferably between 5 and 20; 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. 9. - Process according to any one of the preceding claims, in which the composition A comprises one or more compounds of formula (I) in a content ranging from 0.01 to 50%, in particular from 0.05 to 30%, more particularly from 0.1 to 20%, preferably from 0.5 to 15%, and more preferably from 1 to 10% by weight relative to the total weight of the composition. 10. - Method according to any one of the preceding claims, in which the composition A also comprises one or more organic solvents, identical or different, preferably chosen from: - monoalcohols comprising a hydroxy group and preferably from 2 to 4 carbon atoms, the monoalcohols preferably being chosen from ethanol, propanol, risopropahol, butanol, and a mixture of these compounds, and more preferably from ethanol, isopropanol, and a mixture of these compounds, and more preferably, said monoalcool is ethanol; polyols comprising from 2 to 30 hydroxy groups, more preferably from 2 to 10 hydroxy groups, more preferably still from 2 to 3 hydroxy groups. 11. - Method according to the preceding claim, wherein the organic solvent (s) is (are) chosen (s) from monoalcohols and polyols comprising two hydroxy groups, preferably from ethanol and polyols comprising two hydroxy groups and at least three carbon atoms, more preferably from ethanol, propylene glycol (1,2-propanediol); 1,3-propanediol; 1,3-butylene glycol; pentane-1,2-diol; dipropylene glycol; hexylene glycol; pentylene glycol; butylene glycol; glycerol; ethylene glycol and mixtures thereof. 12. - Method according to any one of the preceding claims, in which the composition A comprises one or more monoalcohols in an amount included inclusively between 1 and 60%, preferably between 10 and 50%, more preferably between 20 and 50% by weight. relative to the total weight of composition A. 13. - Method according to any one of the preceding claims wherein the composition A comprises one or more polyols in an amount inclusive between 1 and 50%, preferably between 5 and 30%, more preferably between 5 and 15% by weight relative to the total weight of composition A. 14. - Method according to any one of the preceding claims, in which the composition A also comprises one or more compound (s) comprising one or more groups) amine. 15. - Process according to claim 14, in which the composition A comprises one or more compound (s) comprising one or more groups) amine in a content ranging from 0.01 to 10% ₇ in particular from 0.1 to 7% , more particularly from 0.1 to 4% by weight relative to the total weight of the composition. 16. - Method according to any one of the preceding claims, which comprises a step of applying a composition B, distinct from composition A, comprising one or more compounds comprising one or more groups) amine before or after the step of application of composition A. 17. - Method according to any one of claims 14 to 16, in which the compound (s) comprising one or more groups) amine is (are) chosen (s) from: - amino silicones; - amino derivatives of alkoxysilane; - organic amines that do not contain a silicon atom; - non-silicone polymers comprising one or more groups) amine, preferably from amino silicones. 18. - Method according to claim 17 wherein the silicone (s) amihée (s) is (are) chosen (s) from; â) the polysiloxanes corresponding to formula (A): wherein x 'and y' are whole numbers such that the weight average molecular weight (Mw) is between about 5,000 and 500,000; b) amino silicones corresponding to formula (B); R ' _a G ₃ - _a -Si (OSiG2) r, - (OSiG _b R' ₂ .b) m-0-SiG3- _a -R ^, a (B) in which: - G, identical or different, denotes a hydrogen atom, phenyl, OH, Ci-C _alkyl, for example methyl, or alkoxy-C _B, for example methoxy, - a, identical or different, denotes 0 or an integer from 1 to 3, in particular 0, - b denotes 0 or 1, in particular 1, - m and n are numbers such that the sum (n + m) varies from 1 to 2000, in particular from 50 to 150, n being able to designate a number from 0 to 1999, and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10; - R ', identical or different, denotes a monovalent radical of formula -CqH2qL in which q is a number ranging from 2 to 8, and L is an optionally quaternized amine group chosen from the groups: -N (R) ₂ ; -N * (R) s A-; -NR-QN (R) ₂ and-NR-QN ⁺ (R) ₃ A-, in which R, identical or different, denotes hydrogen, phenyl, benzyl, or a monovalent saturated hydrocarbon radical, for example a C1-alkyl radical C20; Q denotes a group of formula C _r H _2r , linear or branched, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A- represents a cosmetically acceptable anion, in particular halide such as fluoride, chloride, bromide or iodide. c) amino silicones of formula (J): Γ? ¹ Ί ^R 3 Ί I HZN-îc NH ^ ^ hj-Si -0- 0: i 0: r " ol I U ol I Lr, j X ^R 4 (J) in which: 5 - Ri, Rz, R3 and R4, identical or different, denote a C1-C4 alkyl radical or a phenyl group, - Rs denotes a C1-C4 alkyl radical or a hydroxyl group, - n is an integer varying from 1 to 5, - m is an integer varying from 1 to 5, and 10 - x is chosen such that the amine index varies from 0.01 to 1 meq / g. d) polyoxyalkylenated muitibloc amino silicones, of type (AB) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group, Preferably among the amino silicones of formula (B) and polyoxÿaikylénées muitibloc amino silicones, of type (AB) n. 19. - Method according to any one of claims 17 to 18 in which the amino silicone (s) is (are) chosen from: 20 - the silicones called trimethylsilylamodimethicone corresponding to formula (C): (CH ₃ ) ₃ If CH, I ³ ΓΝ Οι CH, I ³ U bl | U ol | ch ₃ jCH ₂ ) ₃ not NH (ÇH ₂ ) ₂ nh ₂ OSi (CH ₃ ) ₃ (G) in which m and n are numbers such that the sum (n + m) varies from 1 to 2000, in particular from 50 to 150, n being able to designate a number from 0 to 1999, and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10. - the silicones of formula (D) below: CH -SiCH CH, O - If · O —If · 3 L_ CH, (ÇH ₂ ) ₃ NH (Ç ^H z> ₂ NH, CH, -O-Si-R, CH, (D) in which: - m and n are numbers such that the sum (n + m) varies from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200; n being able to designate a number of 0 5 to 999 and in particular from 49 to 249 and more particularly from 125 to 175 and m being able to designate a number from 1 to 1000, in particular from 1 to 10, more particularly from 1 to 5; - R1, R2, R3, identical or different, represent a hydroxy or C1-C4 alkoxy radical, at least one from radicals R1 to R3 denoting an alkoxy radical. 10 - the silicones of formula (E) below: Rj-Si— ch ₃ ch ₃ O— - Yes, Ç ^H 3 O - If ⁴ - (çh ₂ ) ₃ NH ÇH ₃ O — Si — R ₂ ch ₃ (E) (ÇH ₂ ) ₂ nh ₂ in which: - p and q are numbers such that the summation (p + q) varies from 1 to 1000, in particular from 50 to 350, and more particularly from 150 to 250; p can designate a number from 0 to 999 and in particular from 49 to 349 and more particularly from 159 to 239 and q being able to designate a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5; - R1, R2, different, represent a hydroxy or C1-C4 alkoxy radical, at least one of the radicals R1 or R2 denoting an alkoxy radical. - the silicones of the following formula (F); p HO-Si— I CH, OCH Yes' CH, OCH -SiI AT I NH (Ç ^H 2) ₂ NH, ch ₃ -O-Si-OH CH, (F) in which; 5 - m and n are numbers such that the summation (n + m) varies from 1 to 2000 and in particular from 50 to 150, n being able to designate a number from 0 to 1999 and in particular from 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10; - A denotes a linear or branched alkylene radical having 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear, - the silicones of the following formula (G): CH, CH, CH, H ₃ C-SiOSi CH, CH, -Sii AT I NH (ÇH ₂ ) ₂ NH, -O-Si-CH CH, (G) in which: - m and ή are numbers such that! a sum (n + m) varies from 1 to 2000 and particular eri 15 from 50 to 150, n being able to designate a number from 0 to 1 999 and in particular of 49 to 149 and m being able to designate a number from 1 to 2000, and in particular from 1 to 10; - A denotes a linear or branched alkylene radical having 4 to 8 carbon atoms and preferably 4 carbon atoms; - multiblock polyoxyalkylene amino silicones, of type (AB) n, A being a polysiloxane block and B being A polyoxyalkylenated block comprising at least one amine group, and very particularly the amino silicone (s) which can be used ) in the process according to the invention is or are chosen from among the amino silicones of formulas (E), the amino silicones of formulas (F), and the polyblalkylated amino silicones of type (AB) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group. 20. - Method according to claim 17, in which the amino derivatives of alkoxysilane are chosen from the compounds of formula (C) below and / or their oligomers: RiSi (OR2) ₂ (R3) x (OH) _y (C) formula (C) in which: • Ri is a Ci-Ce hydrocarbon chain, linear or branched, saturated or unsaturated, cyclic or acyclic substituted by a group chosen from groups: - NH2 or NHR amine (R = C1-C20 alkyl, in particular C-i-Cë optionally substituted by a radical containing a silicon atom, C3-C40 cycloalkyl or aromatic eh Ce-C ^ o), an aryl or aryloxy group substituted and / or interrupted by at least one amino group or by at least one C1-C4 aminoalkyl group; Ri can be interrupted by a heteroatom (O, S, NH) or a carbonyl group (CO), • R ₂ and R3 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. 21. - Method according to the preceding claim, in which the amino derivative (s) of alkoxysilane is (are) chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyiiriiriethoxysilane (AETES), 3 aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3- (m-aminophenoxy) propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N- (2 aminoethylaminomethyl) phenethyltrimethoxysiiane, better among 3 aminopropyltriethethysilane) ( ), le 3 aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3 ~ aminopréropyltriéthoxysilane or their oligomers and / or their hydrolysis products, even better, among 3aminopropyl triethoxysilane and its oligomers and / or its hydrolysis products. 22. - Method according to any one of claims 16 to 21, in which composition B is applied to keratin fibers, in particular the hair, before or after composition A, preferably before composition A when composition B comprises a or more compound (s) comprising one or more amine group (s) chosen from amine derivatives of alkoxysilane, organic amines not comprising a silicon atom and non-silicone polymers comprising one or more group (s) ) amine, and preferably after composition A when composition B comprises one or more compound (s) comprising one or more amine group (s) chosen) from amino silicones. 23. - Method according to any one of the preceding claims, which further comprises a step of applying a composition C comprising an aicafin agent different from the compounds comprising one or more amine group (s) chosen from ammonia, hydroxides of alkali or alkaline earth metals such as sodium or post potassium, carbonates, phosphates of alkali or alkaline earth metals such as sodium or post potassium. 24. - Method according to claim 23, wherein the composition C is applied to the keratin fibers, in particular the hair, before, simultaneously, or after the composition A, preferably before the composition A. 25. - Method according to any one of the preceding claims, characterized in that the application to the hair of the composition (s) is followed by a heat treatment step at a temperature of 40 ° C to 25G ° C, preferably from 60 ° C to 250 ° e. 26.— Composition including: - one or more compounds of formula (I) fel (s) as defined) in any one of claims 1 to 9; - one or more compound (S) comprising at least one amine group tef (s) as defined in any one of Claims 17 to 21, preferably chosen from amino silicones, and even more preferably from amino silicones of formulas (E), the amino silicones of formulas (F), and the polyoxyalkylenated multiblock amino silicones of type (AB) n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group; - optionally, one or more organic solvent (s) as defined in any of claims 10 to 13. 27. - Composition according to the preceding claim in which the pH is less than or equal to 8, preferably ranges from 1 to 7 and more preferably from 2 to 7.