FR3061431A1 - PROCESS FOR TREATING KERATIN FIBERS UTILIZING A BUTENEDIOIC ACID DERIVATIVE AND AN AMINO SILICONE - Google Patents

Abstract

The present invention relates to a process for treating keratinous fibers, in particular human keratinous fibers such as the hair, comprising a first step of applying a composition, comprising a derivative of butenedioic acid and an amino silicone, followed by a second step of heat treatment of keratinous fibers. The present invention also relates to the use of said composition for smoothing and / or straightening keratinous fibers, in particular human keratin fibers such as the hair.

Description

Holder (s):

L'OREAL Public limited company.

O Extension request (s):

(® Agent (s): CASALONGA.

FR 3 061 431 - A1 ® PROCESS FOR THE TREATMENT OF KERATINIC FIBERS USING A BUTENEDIOIC ACID DERIVATIVE AND AN AMINO SILICONE.

@) The present invention relates to a process for treating keratin fibers, in particular human keratin fibers such as the hair, comprising a first step of applying a composition, comprising a derivative of butenedioic acid and an amino silicone , followed by a second step of heat treatment of keratin fibers.

The present invention also relates to the use of said composition for the straightening and / or straightening of keratin fibers, in particular human keratin fibers such as the hair.

Process for the treatment of keratin fibers using a derivative of butenedioic acid and an amino silicone

The present invention relates to a method for treating keratin fibers, in particular human keratin fibers such as the hair, comprising a first step of applying a composition, comprising a derivative of butenedioic acid and an amino silicone, followed a second stage of heat treatment of keratin fibers.

The present invention also relates to the use of said composition for the straightening and / or straightening of keratin fibers, in particular human keratin fibers such as the hair.

Many people are not satisfied with the appearance of their hair. In particular, people with curly hair most often seek to obtain smooth hair.

The methods for straightening or straightening the hair generally involve reducing agents based on thiol or strong alkaline agents. These techniques are notably based on the breaking of the disulfide covalent bonds present in keratin fibers.

A first technique consists, firstly, in opening the disulphide bonds using a composition comprising a reducing agent. Then, in a second step, said disulphide bonds are reconstituted by applying to the hair, previously rinsed and put under tension, for example by means of curlers, an oxidizing composition also called “fixative”. This fixing step makes it possible to give the hair the desired shape.

A second technique consists in carrying out an anthionization operation, using a composition containing a base belonging to the family of hydroxides. Unlike the first technique, this second technique does not require a fixing step since the formation of lanthionine bonds is irreversible. It thus makes it possible to carry out the waving, the straightening, the straightening or the straightening of the hair. This technique is more particularly used for the straightening of naturally frizzy hair.

These two techniques have many drawbacks, however. They lead in particular to unpleasant odors during their implementation. In addition, they cause some discomfort to the scalp and significant degradation of the keratin fibers.

A new technique has recently been developed which consists in associating a heat treatment step with a step of applying a composition comprising formalin. This technique is particularly effective for giving a better appearance to damaged hair and / or for treating long hair and curly hair.

In fact, at a temperature which can reach 200 ° C. and above, for example by means of an iron, formalin crosslinks the proteins of keratin fibers by reaction on their nucleophilic sites. This technique is not ideal, however, since the use of formalin can be irritating and even toxic for some consumers.

This is the reason why we try to avoid the use of substances like formalin.

Consequently, there is a real need to provide new solutions for smoothing and / or straightening keratin fibers, in particular human keratin fibers such as the hair, which do not require the use of such substances.

These new solutions should in particular make it possible to obtain good loop relaxation and good volume control which are durable over time. These solutions must also respect the integrity of the hair and scalp, and in particular not irritate the latter.

In addition, these new straightening and / or straightening solutions must make it possible to preserve the color of the hair, in particular if the hair is colored, as well as their cosmetic qualities such as shine, a smooth feel, easy disentangling both in the state wet than dry.

The Applicant has surprisingly discovered that a process for treating keratin fibers, comprising a step of applying a composition comprising a particular derivative of butenedioic acid and an amino silicone, followed by a second step of heat treatment of keratin fibers made it possible to achieve the objectives set out above.

The subject of the present invention is in particular a process for treating keratin fibers, in particular human keratin fibers such as the hair, preferably bleached, comprising the following steps:

l) a first step of application to said keratin fibers of a composition comprising:

- one or more compounds chosen from the butenedioic acid derivatives of formula (I) below, as well as their addition salts, their optical isomers, their geometric isomers, their tautomers and their mixtures

R (I) formula (I), in which, Ri and R2, identical or different, represent, independently of one another, a hydrogen atom, an alkyl group, linear or branched, Ci to Cio, or a C2 to C10 linear or branched alkenyl group, said alkyl or alkenyl groups being:

optionally interrupted by one or more heteroatoms, such as O, S and NXR3), with R3 representing a hydrogen atom or an alkyl group, linear or branched C 1 to C 6, and / or optionally substituted by one or more radicals chosen from hydroxy, amino, mono or C1-C6 dialkylamino, C1-C6 alkoxy, and carboxy radicals; and

- one or more amino silicones;

followed by

2) a second step of heat treatment of said keratin fibers at a temperature greater than or equal to 100 ° C.

A step of mechanical treatment for straightening keratin fibers, such as brushing, preferably accompanied by heating with a hair dryer, may be carried out between the first and the second step of the process.

Another object of the present invention relates to a composition as defined in the first step of the process, said composition being aqueous at acidic pH.

The present invention also relates to the use of a composition as defined above for the straightening and / or straightening of keratin fibers, in particular human keratin fibers such as the hair.

The method according to the invention notably makes it possible to obtain good loop relaxation and better control of the volume. Indeed, the process brings a significant reduction in the volume of keratin fibers, while respecting their integrity.

The method according to the invention also makes it possible to impart a “snake” movement to the keratin fibers, characteristic of Brazilian smoothing, without however requiring the use of irritating and / or aggressive substances such as formalin.

The smoothing obtained by the process according to the present invention is durable over time and resists several shampoos.

Finally, the method according to the invention makes it possible to preserve the color of the keratin fibers, in particular if they are colored. The keratin fibers treated by the process according to the invention have good cosmetic qualities such as shine, a smooth and pleasant feel, as well as easy disentangling both in the wet state and in the dry state. The keratin fibers are also more disciplined and present a risk of reduced breakage.

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

In what follows, and unless otherwise indicated, the limits of a domain of values are included in this domain, in particular in the expressions "included between" and "going from ... to ...".

Furthermore, the expressions “at least one”, “at least two”, and “at least” used in the present description are respectively equivalent to the expressions “one or more”, “two or more” and “greater than or equal”.

The term “alkyl” means a saturated, linear or branched hydrocarbon group comprising from 1 to 10 carbon atoms, in particular from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms.

The term “alkenyl” or “alkenyl” means an unsaturated, linear or branched hydrocarbon group comprising from 2 to 10 carbon atoms, in particular from 2 to 6 carbon atoms, preferably from 2 to 4 carbon atoms, and comprising from 1 to 6 unsaturations, combined or not, preferably 1 to 2 unsaturations.

The term "alkoxy" or "alkoxy" means an alkyl-oxy group with the alkyl group as defined above.

The term “acids” is understood to mean mineral or organic acids such as the hydrochloric acid salts HCl; hydrobromic acid HBr; sulfuric acid H2SO4; (Ci-C6alkylsulfonic acids Alk-S (O) 2OH, such as methylsulfonic acid and ethylsulfonic acid; arylsulfonic acids Ar-S (O) 2ÛH, with Ar representing an aryl group in particular phenyl, such as the salts derived from benzene sulfonic acid and toluene sulfonic acid; (poly) (hydroxy) (Ci-C6) alkylcarboxylic acids, such as the salts of citric acid; succinic acid; tartaric acid ; lactic acid, (Ci-C 6 alkoxysulfinic acids Alk-OS (O) OH, such as the salts of methoxysulfinic acid and ethoxysulfinic acid; aryloxysulfinic acids, such as the salts of tolueneoxysulfinic acid and d phenoxysulfinic acid; phosphorous acid, such as phosphoric acid H3PO4; (CiC6alkylcarboxylic acid, such as acetic CH ₃ C (O) OH; triflic acid CF3SO3H and tetrafluoroboric acid HBF ₄ .

By “anionic counterion” is meant an anion or an anionic group derived from an organic or mineral acid salt counterbalancing the cationic charge of the compound; more particularly the anionic counterion is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates including Ci-C6 alkyl sulfonates: Alk-S (O) 2O 'such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S (O) 2O 'such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkylsulfates: Alk-OS (O) O 'such as methysulfate and ethylsulfate; x) arylsulfates: Ar-OS (O) O 'such as benzenesulfate and toluenesulfate; xi) alkoxysulfates: Alk-OS (O) 2O 'such as methoxy sulfate and ethoxysulfate; xii) aryloxysulfates: Ar-OS (O) 2O ', xiii) phosphates O = P (OH) ₂ -O \

O = P (O ') 2-OH O = P (O) ₃ , HO- [P (O) (O)] _w -P (O) (O) 2 with w being an integer; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate, xvii) disulfate disulfate (O =) 2S (O ') 2 or SO4 ² ' and monosulfate HSO4 '; the anionic counter ion, derived from an organic or mineral acid salt, ensures the electroneutrality of the molecule so it is understood that when the anion comprises several anionic charges then the same anion can be used for the electroneutrality of several cationic groups in the same molecule or can be used for the electroneutrality of several molecules; for example a compound which contains two cationic charges can contain either two anionic counter ions "monoloaded" or either contains an anionic counterion "bicharged" such as (O =) 2S (O ') 2 or O = P (O') 2 -OH ;

A) Composition

The compounds of formula (I)

The composition applied in the first step of the process for treating keratin fibers according to the present invention comprises one or more compounds chosen from the derivatives of butenedioic acid of formula (I) as defined above.

Preferably, Ri and R2, identical or different, represent, independently of one another, a hydrogen atom or an alkyl group, linear or branched, C 1 to C 10, optionally interrupted by one or more heteroatoms, such as O, S and N (R3).

Advantageously, Ri and R2, identical or different, represent independently of each other, a hydrogen atom or an alkyl group, linear or branched, Ci to C6, optionally substituted by one or more carboxy radicals.

According to an advantageous embodiment of the invention the diacids of formula (I) are such that Ri and R ₂ are identical.

Preferably Ri and R ₂ represent a hydrogen atom.

According to another particular embodiment of the invention Ri represents a hydrogen atom and R ₂ an alkyl group, linear or branched, Ci to C6 optionally substituted by a carboxy group

Preferably, the compound or compounds derived from butenedioic acid of formula (I) are chosen from maleic acid, citraconic acid, aconitic acid, their geometric isomers, their addition salts, and their mixtures.

The addition salts of the compound of formula (I), present in the composition according to the invention, are especially chosen from addition salts with an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates , tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.

The total amount of the compound or compounds of formula (I) present in the composition according to the invention preferably ranges from 1 to 20% by weight, and more preferably from 5 to 15% by weight, relative to the total weight of the composition.

Amino silicones

The composition applied in the first step of the process for treating keratin fibers according to the present invention further comprises one or more amino silicones.

By “amino silicone” is meant any silicone comprising at least one primary, secondary, tertiary amine function, a quaternary ammonium group, or else at least one imine function = NR _a with R _a representing a hydrogen atom or a chosen group from the groups (Ci-C6alkyl, aryl such as phenyl, and aryl (Ci-C4) alkyl such as benzyl.

Preferably, the amino silicone (s) used in the composition according to the present invention contain in their structure at least 4 silicon atoms.

In what follows, the term “silicone” is intended to denote, in accordance with general acceptance, all organosilicon polymers or oligomers with linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and / or by polycondensation of silanes suitably functionalized, and consisting essentially of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bond -Si-O-Si-), optionally substituted hydrocarbon groups, being directly linked via a carbon atom on said silicon atoms. The most common hydrocarbon groups are alkyl groups, in particular Ci-Cio, and in particular methyl, haloalkyl groups in particular fluoroalkyls in which the alkyl part is in Ci-Cio, aryl groups and in particular phenyl.

The amino silicones used in the composition according to the present invention can be chosen from the families of compounds (a) to (e) below:

(a) the compounds corresponding to the following formula (II):

(1 (4, (- 1) .., - 8.108, (- 1) .1.-108, (- 1), (1 (4,., 1, .- 08, (- 1) .., - (1 (4, (II) formula (II), in which,

- T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or C1-C8 alkyl, and preferably methyl, or C1-C6 alkoxy, preferably methoxy,

- a denotes the number 0 or an integer from 1 to 3, and preferably 0,

- b denotes 0 or 1, and in particular 1,

- m and n are whole numbers such that the sum (n + m) can vary in particular from 1 to 2,000 and in particular from 50 to 150, n being able to designate an integer from 0 to 1,999 and in particular from 49 to 149 and m being able to designate an integer from 1 to 2000, and in particular from 1 to 10,

- R ¹ is a monovalent group of formula

i) -C _q H ₂ qL in which q is an integer inclusive between 2 and 8 and L is an optionally quaternized amino group chosen from the groups:

-N (R ² ) -ALK-N (R ² ) ₂ ,

-N (R ² ) ₂ ,

-N ⁺ (R ² ) ₃ q-,

-n (r ² ) -alk-n ⁺ (r ² ) ₂ q;

wherein :

* R ² , identical or different, denote a hydrogen atom, a phenyl group, a benzyl group, or a C1-C20 alkyl group, * Q 'represents an anionic counter ion allowing the electroneutrality of the polymer, preferably a halide ion such as, for example, fluoride, chloride, bromide or iodide, and * ALK, represents a group (C 1 -C 6 alkylene, linear or branched, such as ethylene -CH ₂ -CH ₂ -; or then ii) -CqH _2q .iL 'in which q is an integer inclusive between 2 and 8 and L' is an optionally quaternized iminated group chosen from groups:

= N-ALK-N (R ² ) ₂ , = NR ² , = N ⁺ (R ² ) ₂ Q ', = N-ALK-N ⁺ (R ² ) ₃ Q' with ALK, R ² and Q 'such as defined for L.

In particular, the amino silicones corresponding to the definition of formula (II) are chosen from the compounds corresponding to the following formula (III) or (ΙΙΓ):

ίο

R 'ch ₃ çh ₃

R- -Yes- 0- -Yes ch ₃ ch ₃

O —If

AT

NH I

Ç ^H 3

O — Si — R

CH ₃ (ÇH ₂ ) ₂ nh ₂

Ç ^H 3

O — Si — R

CH ₃ (ΙΙΓ) formulas (III) or (ΙΙΓ), in which:

• R, R ', R, identical or different, denote a C1-C4 alkyl group, preferably CH ₃ , a C1-C4 alkoxy group, preferably methoxy, or OH, • A represents an alkylene group, linear or branched, in C3-C8, preferably in C3-C6, • A 'represents an alkylene group - (CR ^a R ^b ) _p -C (R ^c ) = with p representing an integer inclusive between 0 and 5, and R ^a , R ^b , and R ^c , identical or different, representing a hydrogen atom or a (Ci-C4) alkyl group, preferably R ^a , R ^b , and R ^c represent a hydrogen atom, • m and n, identical or different, are whole numbers depending on the molecular weight and the sum of which is between 1 and 2000.

According to a particular embodiment of the invention, the amino silicone (s) are of formula (III).

According to another preferred embodiment of the invention, the amino silicone (s) have the formula (ΙΙΓ).

According to one possibility, R, R 'and R, identical or different, each represent a C1-C4 alkyl or hydroxyl group, A represents a C3 alkylene group or A' represents a group -CH ₂ CH ₂ -CH = and m and n are such that the weight average molecular weight of the compound is between 5,000 and 500,000 approximately. Compounds of this type are named in the CTFA dictionary, amodimethicone.

According to another possibility, R, R ′ and R, identical or different, each represent a C1-C4 alkoxy or hydroxyl group, at least one of the R or R groups is an alkoxy group and A represents a C3 alkylene group or A 'represents a group -CH ₂ -CH ₂ -CH =. The hydroxy / alkoxy molar ratio is preferably between 0.2 / 1 and 0.4 / 1 and advantageously equal to 0.3 / 1. Furthermore, m and n are such that the weight-average molecular mass of the compound is between 2000 and 10 ⁶ . More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.

In this category of compounds, mention may be made, among others, of the product Belsil® ADM 652 sold by the company WACKER.

According to another possibility, R and R, different, each represent a C1-C4 alkoxy or hydroxyl group, at least one of the groups R and R being an alkoxy group, R 'representing a methyl group and A representing an alkylene group in C3 or A 'represents a group -CH ₂ -CH ₂ -CH =. The hydroxy / alkoxy molar ratio is preferably between 1 / 0.8 and 1 / 1.1, and advantageously is equal to 1 / 0.95. Furthermore, m and n are such that the weight-average molecular mass of the compound is between 2000 and 200000. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.

More particularly, mention may be made of the product FluidWR® 1300, sold by the company WACKER.

Note that the molecular mass of these silicones is determined by gel permeation chromatography (room temperature, polystyrene standard, μ styragem columns, eluent THF, flow rate of 1 mm / m, 200 μΐ of a 0.5% solution are injected by weight of silicone in THF and the detection is carried out by refractometry and UV-metry).

A product corresponding to the definition of formula (II) is in particular the polymer named in the CTFA dictionary trimethylsilylamodimethicone, corresponding to the following formula (IV):

CH

(CH

CH,

I

SiO

I

CH,

I

CHCH

I

CH.

formula (IV), in which n and m have the meanings given above in accordance with formula (II).

Such compounds are described, for example, in EP 95238. A compound of formula (II) is, for example, sold under the name Q2-8220 by the company OSI.

(b) the compounds corresponding to the following formula (V):

R ⁴ —CH2 - CHOH CH2 - N ⁺ (R ³ ) 3 Q

R ³

R— Si - R ³

Yes

R ³

R ³

I

If — R ³

R ³ (V) formula (V), in which,

R ³ represents a monovalent Ci-Cis hydrocarbon group, and in particular a Ci-Cis alkyl group, or C2-C18 alkenyl group, for example methyl,

R ⁴ represents a divalent hydrocarbon group, in particular a C1-Cis alkylene group or a divalent CiCis, for example C1-Cs alkyleneoxy group,

Q ′ is an anionic counter ion, in particular a halide ion, in particular chloride,

- r represents an average statistical value from 2 to 20 and in particular from 2 to 8,

- s represents an average statistical value from 20 to 200 and in particular from 20 to 50.

Such compounds are described more particularly in US patent 4185087.

A compound belonging to this class is that sold by the company UNION CARBIDE under the name Ucar Silicone ALE 56.

(c) quaternary ammonium silicones, in particular of formula (VI):

R ₇ ^2X r

he

If —r ₆ -ch ₂ -choh-ch ₂ -nr ₈

R ₇ R (VI) formula (VI), in which,

- R7, identical or different, represent a monovalent hydrocarbon group having from 1 to 18 carbon atoms, and in particular a C1-C18 alkyl group, a C2-C18 alkenyl group or a ring comprising 5 or 6 carbon atoms, for example methyl,

- R6 represents a divalent hydrocarbon group, in particular a C1-Cis alkylene group or a divalent CiCis, for example C1-Cs alkyleneoxy group linked to Si by an Si-C bond,

- Rs, identical or different, each represents a hydrogen atom, a monovalent hydrocarbon group having from 1 to 18 carbon atoms, and in particular a C1-Cis alkyl group, a C ₂ -Cis alkenyl group, a group -R6-NHCOR7,

X ′ is an anionic counter ion such as a halide ion, in particular chloride or an organic acid salt (acetate, etc.),

- r represents an average statistical value from 2 to 200 and in particular from 5 to 100.

These silicones are for example described in application EP-A0530974.

(d) amino silicones of formula (VII) or (VIE):

r- R. R, -1 | 1 H ₂ N- (C _m H _2m ) -N- (C _n H _2n ) -Si- -ο- -If - O- -Yes - - ^R 5 L r ₂ J x ^R 4

(VII)

Γ î ¹ Ί ^R 3 - H ₂ N- (C _m H _2m ) -N = (0 ^) - 8.- -ο- -If - O- -Yes - - ^R 5 L r ₂ J X ^R 4

(VIE) formulas (VII) and (VIE), in which:

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

- R5 denotes a C1-C4 alkyl group 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 such that the amine index is between 0.01 and 1 meq / g.

According to a particular embodiment of the invention, the amino silicone (s) are of formula (VII).

According to another particular embodiment of the invention, the amino silicone (s) have the formula (VU ’).

and (e) mixtures thereof.

When these compounds are used, a particularly advantageous embodiment is their joint use with surfactants chosen from cationic surfactants, nonionic surfactants, and mixtures thereof; and preferably cationic surfactants.

In other words, according to this particular embodiment, the composition applied in the first step of the process for treating keratin fibers according to the present invention further comprises one or more surfactants chosen from cationic surfactants, nonionic surfactants, and their mixtures; and preferably cationic surfactants.

For example, one can use the product sold under the name Cationic Emulsion DC 939 by the company DOW CORNING, which comprises, in addition to amodimethicone, a cationic surfactant which is trimethylketylammonium chloride and a nonionic surfactant, of formula C ₁₃ H ₂₇ - (OC ₂ H ₄ ) ₁₂ -OH, known under the name CTFA trideceth-12.

Another commercial product which can be used according to the invention is the product sold under the name Dow Corning Q2 7224 by the company Dow Corning, comprising, in combination with trimethylsilylamodimethicone of formula (IV) described above, a nonionic surfactant of formula: C ₈ H ₁₇ -C ₆ H ₄ - (OCH ₂ CH ₂ ) ₄₀ -OH, known under the name CTFA octoxynol-40, a second nonionic surfactant of formula: Ci2H25- (OCH ₂ -CH ₂ ) 6-OH, known as the name CTFA isolaureth-6, and propylene glycol.

Another commercial product which can be used according to the invention is the product sold under the name Wacker-Belsil ADM LOG 1 marketed by the company WACKER comprising, in the form of a microemulsion, an amodimethicone of formula (III) in combination with trideceth-5 and trideceth-10.

One can also use the product sold under the trade name Xiameter MEM 8299 emulsion by the company Dow Corning.

Other amino silicones can be used in the context of the invention such as the product referenced in the CTFA dictionary under the name POLYSILICONE-9.

Preferably, the amino silicone (s) are chosen from (i) polydi (Ci-C6) alkylsiloxanes, in particular polydimethylsiloxanes, with amino group (Ci-C6) alkylamino (Ci-C6) alkyl and / or amino ( Ci-C6) alkylimino (Ci-C6) alkyl, preferably polydimethylsiloxane with aminoethyliminopropyl and / or aminoethylaminopropyl group in particular in cationic emulsion;

(ii) polydi (Ci-C6) alkylsiloxanes, in particular poly-dimethylsiloxane with amino group (Ci-C6) alkylamino (Ci-C6) alkyl and / or amino (Ci-C6) alkyimino (Ci-C6) alkyl, preferably polydimethylsiloxane with aminoethyliminopropyl and / or aminoethylaminopropyl group (s) and (Ci-C6alkoxy group such as methoxy), and / or with hydroxy and α-ω-silanol group (s) preferably in aqueous cationic emulsion in particular as a cationic emulsion; preferably polydimethylsiloxane with aminoethylaminopropyl group (s), with methoxy and / or hydroxy group (s) and cationic AQ emulsion; and polydimethylsiloxane with aminoethyliminopropyl group (s) in nonionic microemulsion ( at 17%) protected (at 1%) from phenoxyethanol; and (iii) mixtures of amodimethicone (amino silicone) and surfactants in particular nonionic or cationic, preferably chosen from alkoxylated poly (Ci-Ce) alcohols, preferably polyethoxylated and the ammoniums with aliphatic chain RR'R ”R” 'N ⁺ , X with X', represents u n anionic ion in particular halide, and R, R ', R ”, identical or different, represent a group (Ci3061431

Côjalkyl, R ’” represents a (Cio-C3o) alkyl group such as the following associations:

- amodimethicone and trideceth-5, and trideceth-10 for example those marketed under the name of DC (R) 2-2899 by DOW CORNING;

- amodimethicone and trideceth-6, and the salts of cetrimonium, for example those sold under the name of Belsil ADM by Wacker;

- amodimethicone and trideceth-12, and the salts of cetrimonium.

Preferably, the amino silicone (s) are chosen from poly (di) (Ci-C6) alkylsiloxanes with imino (Ci-C6) alkyl groups or with (di) (Ci-C6) (alkyl) amino (Ci-C6) groups ) (C1-C6) alkylimino alkyl; more preferably among the polydi (Ci-C4) alkylsiloxanes with imino (Ci-C4) alkyl groups or with (di) (Ci-C4) (alkyl) amino (CiC4) alkylimino (Ci-C4) alkyl groups, and better still among polydimethylsiloxanes with imino (Ci-C4) alkyl groups or with amino (Ci-C3) alkylimino (Ci-C4) alkyl groups such as polydimethylsiloxanes with iminopropyl or aminoethyliminopropyl groups.

The total amount of the amino silicone (s) present in the composition according to the invention preferably ranges from 0.5 to 20% by weight, more preferably from 1 to 10% by weight, and better still from 2 at 5% by weight, relative to the total weight of the composition.

Preferably, the weight ratio between the total amount of the compound (s) of formula (I) and the total amount of the amino silicone (s) present in the composition according to the invention ranges from 0.1 to 10, more preferably from 0.5 to 5, better still from 1 to 4, and more particularly from 1.5 to 3 such as 2.8.

Alkaline agents

The composition applied in the first step of the process for treating keratin fibers according to the present invention may optionally further comprise one or more alkaline agents.

According to a particular embodiment, the composition according to the invention also comprises one or more alkaline agents.

The alkaline agent (s) can in particular be chosen from mineral, organic, hybrid alkaline agents and their mixtures.

The mineral alkaline agent (s) are preferably chosen from ammonia, alkali carbonates or bicarbonates such as sodium or potassium carbonates or bicarbonates, sodium or potassium hydroxides or their mixtures.

The organic alkaline agent (s) are preferably chosen from organic amines whose pKb at 25 ° C is less than 12, and preferably less than 10, even more advantageously less than

6. Note that this is the pKb corresponding to the highest basicity function. In addition, organic amines do not include a fatty chain, alkyl or alkenyl, comprising more than ten carbon atoms.

The organic alkaline agent (s) are preferably chosen from alkanolamines, in particular mono-, di- or trihydroxy (Ci-C6) alkylamines such as triethanolamine, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids, polyamines of formula (VIII) below and their mixtures:

NWN ^R '(VIII) formula (VIII), in which, W is a divalent C1 to C6 alkylene radical optionally substituted by one or more hydroxyl groups or a C1 to C6 alkyl radical, and / or optionally interrupted by one or more heteroatoms such as O, or NR _U ; R _x , R _y , R _z , R _t , and R _{u, which are} identical or different, represent a hydrogen atom, a C1-C6 alkyl or C1-C6 hydroxyalkyl radical, or C1-C6 aminoalkyl.

Examples of amines of formula (VIII) that may be mentioned are 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 to Cg carrying one or more hydroxy 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 be identical, C1 to C4.

Among compounds of this type, there may be mentioned monoethanolamine (MEA), diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N, N-dimethylethanolamine, 2-amino-2-methyl-1-propanol, triisopropanol-amine , 2-amino-2-methyl-1,3-propanediol, 3 amino- 1,2,2-propanediol, 3-dimethylamino-1,2-propanediol, trishydroxymethyl ami no-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 (IX), as well as their salts

R-CH ₂ -CH (NH ₂ ) -C (O) -OH (IX) formula (IX), in which, R represents a group chosen from imidazolyl, preferably imidazolyl-4-yl; aminopropyl; aminoethyl;

- (CH ₂ ) ₂ N (H) -C (O) -NH ₂ ; and - (CH ₂ ) ₂ -N (H) -C (NH) -NH ₂ .

The compounds corresponding to formula (IX) 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 balenine

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, acid

3-guanidino-propionic, 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.

Preferably, the alkaline agent (s) present in the composition according to the invention are chosen from ammonia, alkanolamines, amino acids in neutral or ionic form, in particular basic amino acids, and preferably corresponding to those of formula (IX).

More preferably, the alkaline agent (s) present in the composition according to the invention are chosen from ammonia, alkanolamines and their mixtures, and better still from ammonia, mono-, di- or tri-hydroxy ( Ci-C6) alkylamine, such as triethanolamine, and mixtures thereof.

The total amount of the alkaline agent (s), when it (s) is (are) present in the composition according to the invention, preferably ranges from 0.5 to 10% by weight, more preferably from 1 to 7 % by weight, and better still from 3 to 6% by weight, relative to the total weight of the composition.

Preferably, the weight ratio between the total amount of the compound (s) of formula (I) and the total amount of the alkaline agent (s), when they are present in the composition according to the invention, ranges from 1 to 5, more preferably from 1.5 to 3, and better still from 1.5 to 2.5.

The pH of the composition applied in the first step of the process for treating keratin fibers according to the present invention preferably ranges from 0.5 to 5, more preferably from 1 to 4, and better still from 1 to 1.5. It can be adjusted to the desired value by means of acidifying or alkaline agents usually used in the treatment of keratin fibers or even using conventional buffer systems.

Among the acidifying agents, there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.

The alkaline agents are such as those described above.

According to a particular embodiment, the composition applied in the first step of the process according to the invention comprises:

one or more compounds chosen from the derivatives of butenedioic acid of formula (I), as defined above, as well as their addition salts, their optical isomers, their geometric isomers, their tautomers and their mixtures,

one or more silicones, as defined above, and

- one or more alkaline agents;

said alkaline agents being in an amount such that the pH of said composition ranges from 0.5 to 5, more preferably from 1 to 4, and better still from 1 to 1.5.

Solvents

The composition applied in the first step of the process for treating keratin fibers according to the present invention may optionally further comprise water, an organic solvent or their mixtures.

Mention may be made, as organic solvent, of alkanols, linear or branched, of C ₂ to C ₄ , such as ethanol and isopropanol; glycerol; polyols and polyol ethers such as

2-butoxyethanol, propylene glycol, hexylene glycol, dipropylene glycol, propylene glycol monomethyl ether, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols or ethers such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

Non-silicone fats

The composition applied in the first step of the process for treating keratin fibers according to the present invention may optionally further comprise one or more non-silicone fatty substances.

By fatty substance is meant an organic compound insoluble in water at ordinary room temperature (25 ° C) and at atmospheric pressure (760 mm Hg), having a water solubility of less than 5%, preferably less at 1%, and even more preferably less than 0.1%. Non-silicone fatty substances generally have in their structure a hydrocarbon chain comprising at least 6 carbon atoms. In addition, fatty substances are generally soluble in organic solvents under the same conditions of temperature and pressure, such as, for example, chloroform, ethanol, benzene, petrolatum oil or decamethylcyclopentasiloxane.

The non-silicone fatty substance (s) of the invention are moreover not polyoxyethylenated and not polyglycerolated.

The term “non-silicone fatty substance” is understood to mean a fatty substance not comprising in its structure of Si-O-Si sequences.

The fatty substance (s) may be liquid or non-liquid at ambient temperature and at atmospheric pressure. The liquid fatty substances of the invention preferably have a viscosity less than or equal to 2 Pa.s, better less than or equal to 1 Pa.s and even better still less than or equal to 0.1 Pa.s at the temperature of 25 °. C and at a shear rate of 1 s' ¹ .

Advantageously, the non-silicone fatty substance (s) are chosen from C6 to C16 hydrocarbons, hydrocarbons with more than 16 carbon atoms, oils of vegetable or animal origin, triglycerides of vegetable origin or synthetic, fluorinated oils, fatty alcohols, fatty acid and / or fatty alcohol esters other than triglycerides, non-silicone waxes, different from solid fatty alcohols and solid synthetic esters, ceramides and their mixtures.

The term “fatty acid and fatty alcohol” denotes an acid, and respectively an alcohol, containing from 6 to 30 carbon atoms, and preferably from 8 to 22 carbon atoms.

As vegetable oil, there may be mentioned in particular sweet almond oil, avocado oil, castor oil, olive oil, liquid jojoba wax, sunflower oil, wheat germ oil, sesame oil, peanut oil, grape seed oil, soybean oil, rapeseed oil, safflower oil, coconut oil , corn oil, hazelnut oil, palm oil, apricot kernel oil, calophyllum oil, evening primrose oil, shea butter, rice bran, corn germ oil, passionflower oil and rye oil.

As animal oil, mention may in particular be made of perhydrosqualene.

As mineral oil, mention may in particular be made of paraffin oil and petrolatum oil.

Mention may in particular be made, as synthetic oil, of squalane, poly (a-olefins) such as isododecane or isohexadecane, transesterified vegetable oils, fluorinated oils and fatty esters.

The term “fatty esters” denotes the compounds of formula R _a COORb in which R _a represents the remainder of a higher linear or branched acid, hydroxylated or not, saturated or not, containing from 4 to 29 carbon atoms and Rb represents a chain linear or branched, saturated or unsaturated hydrocarbon containing from 3 to 30 carbon atoms, the total number of carbon atoms of the ester being greater than 10. By way of nonlimiting examples, mention may be made of purcellin (stearyl octanoate), isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-hexyldecyl laurate , 2-octyldecyl palmitate, myristate of 23061431 octyldodecyl, isostearyl neopentanoate or tridecyl neopentanoate.

The fluorinated oils can be partially hydrocarbon-based and / or silicone-based, such as for example those described in the document JP-A-2-295912.

The fatty alcohols can be chosen from fatty alcohols which are solid at ambient temperature and at atmospheric pressure (25 ° C., 1 atm), fatty alcohols which are liquid at ambient temperature and at atmospheric pressure (25 ° C., 1 atm), and their mixtures. .

The term “fatty alcohol” is intended to mean a long chain aliphatic alcohol comprising from 8 to 40 carbon atoms, and comprising at least one hydroxyl group OH. These fatty alcohols are neither oxyalkylenated nor glycerolated.

Preferably, the solid fatty alcohols are of structure R-OH with R denoting a linear alkyl group, optionally substituted by one or more hydroxy groups, comprising from 8 to 40, better still from 10 to 30, or even from 12 to 24 atoms, again better from 14 to 22 carbon atoms.

The solid fatty alcohols that can be used can be chosen from, alone or as a mixture:

- lauric or lauryl alcohol (1-dodecanol);

- myristic or myristylic alcohol (1-tetradecanol);

- cetyl alcohol (1-hexadecanol);

- stearyl alcohol (1-octadecanol);

- arachidyl alcohol (1-eicosanol);

- behenyl alcohol (1-docosanol);

- lignoceryl alcohol (1-tetracosanol);

- ceramic alcohol (1-hexacosanol);

- montanyl alcohol (1-octacosanol);

- myricylic alcohol (1-triacontanol).

Preferably, the solid fatty alcohol is chosen from cetyl alcohol, stearyl alcohol, behenyl alcohol and their mixtures such as cetylstearyl or cetearyl alcohol.

Liquid fatty alcohols, in particular those in Cio to C34 preferably have branched carbon chains or have one or more, preferably 1 to 3, unsaturations. They are more preferably branched and / or unsaturated, and contain from 12 to 40 carbon atoms; and are non-oxyalkylenated and non-glycerolated.

They preferably have the structure R-OH wherein R is preferably a branched alkyl group C12 to C24 alkenyl or C12 to _C2 4, R may be substituted with one or more hydroxy groups.

Preferably the liquid fatty alcohol of the invention is a branched saturated alcohol. More preferably, R does not contain a hydroxy group.

Mention may in particular be made of oleic alcohol, linoleic alcohol, linolenic alcohol, isocetyl alcohol, isostearyl alcohol, 2octyl-1-dodecanol, 2-butyl-octanol, 2-hexyl-1- decanol, 2decyl-1-tetradecanol, 2-tetradecyl-1-ketanol and mixtures thereof.

Preferably, the liquid fatty alcohol is 2-octyl-ldodecanol.

A wax, within the meaning of the present invention, is a lipophilic compound, solid at room temperature (about 25 ° C), with reversible solid / liquid state change, having a melting temperature above about 40 ° C and which can range up to 200 ° C, and having an anisotropic crystalline organization in the solid state. Animal and vegetable waxes include essential constituents of esters of carboxylic acids and long chain alcohols. In general, the size of the crystals of the wax is such that the crystals diffract and / or scatter light, giving the composition which comprises them a more or less opaque cloudy appearance. By bringing the wax to its melting temperature, it is possible to make it miscible with oils and to form a homogeneous mixture microscopically.

As waxes which can be used in the composition according to the present invention, mention may be made of waxes of animal origin such as beeswax, spermaceti, lanolin wax and lanolin derivatives, vegetable waxes such as sunflower, rice, apple, Carnauba, Candellila, Ouricury, Japanese wax, cocoa butter or cork or sugar cane waxes, mineral waxes, for example, paraffin, petrolatum, lignite or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, FischerTropsch waxes, and mixtures thereof.

Additional non-amino silicones

The composition applied in the first step of the process for treating keratin fibers according to the present invention can optionally further comprise one or more additional non-amino silicone (s).

The term “non-amino silicone” is understood to mean any silicone comprising no primary, secondary, tertiary or quaternary amine group, namely any silicone other than the amino silicones mentioned above.

The additional non-amino silicones which can be used in the composition according to the invention are in particular polyorganosiloxanes which can be in the form of aqueous solutions, that is to say solubilized, or optionally in the form of dispersions or micro-dispersions, or d 'aqueous emulsions. The polyorganosiloxanes can also be in the form of oils, waxes, resins or gums.

Organopolysiloxanes are defined in more detail in the work by Walter NOLL Chemistry and Technology of Silicones (1968) Academie Press.

Additional non-amino silicones can be volatile or non-volatile.

When they are volatile, the non-amino silicones are more particularly chosen from those having a boiling point of between 60 ° C. and 260 ° C., and more particularly still from:

(i) cyclic silicones containing from 3 to 7 silicon atoms and preferably 4 to 5.

This is, for example, octamethylcyclotetrasiloxane marketed in particular under the name of VOLATILE SILICONE 7207 by the company UNION CARBIDE or SILBIONE 70045 V 2 by the company RHODIA, decamethylcyclopentasiloxane marketed under the name of VOLATILE SILICONE 7158 by the company UNION CARBIDE, SILBIONE 70045 V 5 by the company RHODIA, as well as their mixtures.

Mention may also be made of cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type, such as the SILICONE VOLATILE FZ 3109 sold by the company UNION CARBIDE, with a chemical structure:

with :

with' :

CH ₃

ΟΙ -Si-C ₈ H ₁₇

Mention may also be made of mixtures of cyclic silicones with organic compounds derived from silicon, such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and of oxy1,2 (hexa-2, 2,2 ', 2', 3,3'-trimethylsilyloxy) bis-neopentane.

(ii) linear volatile silicones having 2 to 9 silicon atoms and having a viscosity less than or equal to 5 * 10 ' ⁶ m ² / s at 25 ° C. It is, for example, decamethyltetrasiloxane marketed in particular under the name SH 200 by the company TORAY SILICONE. Silicones included in this class are also described in the article published in Cosmetics and toiletries, Vol. 91, Jan. 76, P. 27-32 - TODD & BYERS Volatile Silicone fluids for cosmetics.

When the non-amino silicones are non-volatile, polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, gums and silicone resins, polyorganosiloxanes modified by organofunctional groups and their mixtures are preferably used.

These non-amino silicones are more particularly chosen from polyalkylsiloxanes among which mention may mainly be made of polydimethylsiloxanes with trimethylsilyl end groups (Dimethicone according to the CTFA name) having a viscosity of 5 * 10 ' ⁶ to 2.5 m ² / s at 25 ° C and preferably l * 10 ' ⁵ to 1 m ² / s. The viscosity of the silicones is for example measured at 25 ° C. according to standard ASTM 445 Appendix C.

Among these polyalkylsiloxanes, non-limiting examples that may be mentioned include the following commercial products:

- the SILBIONE oils of the 47 and 70,047 series or the MIRASIL oils sold by the company RHODIA such as, for example, the oil 70,047 V 500,000,

- the oils of the MIRASIL series sold by the company RHODIA,

- oils of the 200 series from the company DOW CORNING such as more particularly DC200 with a viscosity of 60,000 Cst,

- VISCASIL oils from GENERAL ELECTRIC and certain oils from the SF series (SF 96, SF 18) from GENERAL ELECTRIC.

Mention may also be made of polydimethylsiloxanes containing alpha-omega silanol groups (Dimethiconol according to the name CTFA) such as oils of the 48 series from the company RHODIA.

In this class of polyalkylsiloxanes, mention may also be made of the products sold under the names ABIL WAX 9800 and 9801 by the company GOLDSCHMIDT which are polyalkyl (C1-C20) siloxanes.

The polyalkylarylsiloxanes are particularly chosen from polydimethyl methylphenylsiloxanes, linear and / or branched polydimethyl diphenylsiloxanes with a viscosity of l * 10 ' ⁵ to 5 * 10' ² m ² / s at 25 ° C.

Among these polyalkylarylsiloxanes, there may be mentioned, by way of example, the products sold under the following names:

- SILBIONE oils of the 70 641 series from RHODIA,

- the oils of the RHODORSIL 70 633 and 763 series from the company RHODIA,

- DOW CORNING 556 COSMETIC GRAD FLUID oil from DOW CORNING,

- the silicones of the PK series from the company Bayer, such as the product PK20,

- the silicones of the PN and PH series from the company Bayer, such as the products PN1000 and PH1000,

- certain oils of the SF series from GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, SF 1265.

The silicone gums which can be present in the composition according to the invention are in particular polydiorganosiloxanes having high average molecular masses of between 200,000 and 1,000,000, used alone or as a mixture in a solvent. This solvent can be chosen from volatile silicones, polydimethylsiloxane oils (PDMS), polyphenylmethylsiloxane oils (PPMS), isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes or their mixtures.

The following products can more particularly be cited:

- polydimethylsiloxane gums,

- polydimethylsiloxane / methylvinylsiloxane gums,

- polydimethylsiloxane / diphenylsiloxane gums,

- polydimethylsiloxane / phenylmethylsiloxane gums,

- polydimethylsiloxane / diphenylsiloxane / methylvinylsiloxane gums.

More particularly usable products are the following mixtures:

- the mixtures formed from a polydimethylsiloxane hydroxylated at the end of the chain (called dimethiconol according to the nomenclature of the CTFA dictionary) and a cyclic polydimethylsiloxane (called cyclomethicone according to the nomenclature of the CTFA dictionary) such as the product Q2 1401 marketed by the DOW CORNING company,

- the mixtures formed from a polydimethylsiloxane gum with a cyclic silicone such as the product SF 1214 Silicone Fluid from the company GENERAL ELECTRIC, this product is an SF 30 gum corresponding to a dimethicone, having a number average molecular weight of 500 000, dissolved in SF 1202 Silicone Fluid oil corresponding to decamethylcyclopentasiloxane,

- mixtures of two PDMS of different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 from the company GENERAL ELECTRIC. The product SF 1236 is the mixture of an SE 30 gum defined above having a viscosity of 20 m ² / s and an SF 96 oil with a viscosity of

5 * 10 ' ⁶ m ² / s. This product preferably contains 15% of SE 30 gum and 85% of an SF 96 oil.

The organopolysiloxane resins optionally present in the composition according to the invention are crosslinked siloxane systems containing the units: R2S1O2 / 2, R3S1O1 / 2, RS1O3 / 2 and SiO 4/2 in which R represents a hydrocarbon group having 1 to 16 carbon atoms or a phenyl group. Among these products, those which are particularly preferred are those in which R denotes a C1 to C4 alkyl group, more particularly methyl, or a phenyl group.

Mention may be made, among these resins, of the product sold under the name Dow Corning 593 or those sold under the names Silicon Fluid SS 4230 and SS 4267 by the company General Electric and which are silicones of dimethyl / trimethyl siloxane structure.

Mention may also be made of the resins of the trimethylsiloxysilicate type sold in particular under the names X22-4914, X21-5034 and X21-5037 by the company Shinsetsu.

The organomodified non-amino silicones optionally present in the composition according to the invention are non-amino silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon group.

Among the non-amino organomodified silicones, mention may be made of polyorganosiloxanes comprising:

polyethyleneoxy and / or polypropyleneoxy groups optionally comprising C6 to C24 alkyl groups such as the products called dimethicone copolyol marketed by the company Dow Corning under the name DC 1248 or the oils SILWET L 722, L 7500, L 77, L 711 of the company UNION CARBIDE and the alkyl (C12) methicone copolyol marketed by the company DOW CORNING under the name Q2 5200,

- thiol groups such as the products marketed under the names GP 72 A and GP 71 of the company GENESEE,

- alkoxylated groups such as the product marketed under the name SILICONE COPOLYMER F-755 by SWS SILICONES and AB IL WAX 2428, 2434 and 2440 by the company GOLDSCHMIDT,

hydroxylated groups such as polyorganosiloxanes with a hydroxyalkyl function described in French patent application FR 2 589 476, acyloxyalkyl groups such as, for example, the polyorganosiloxanes described in patent US-A-4957732,

- anionic groups of the carboxylic type such as, for example, in the products described in patent EP 186 507 from the company CHISSO CORPORATION, or of alkylcarboxylic type such as those present in the product X-22-3701E from the company SHINETSU, 2- hydroxyalkylsulfonate, 2-hydroxyalkylthiosulfate such as the products sold by the company GOLDSCHMIDT under the names ABIL S201 and ABIL S255,

- hydroxyacylamino groups, such as the polyorganosiloxanes described in application EP 342 834. Mention may be made, for example, of the product Q2-8413 from the company Dow Corning.

The composition applied in the first step of the process for treating keratin fibers according to the present invention may optionally further comprise one or more additives, different from the compounds of the invention and among which mention may be made of cationic, anionic and nonionic surfactants , amphoteric or zwitterionic, cationic, anionic, nonionic, amphoteric polymers or their mixtures, dandruff agents, antiseborrhoeic agents, hair loss and / or regrowth agents, vitamins and pro-vitamins including panthenol, filters sun, mineral or organic pigments, sequestering agents, plasticizing agents, solubilizing agents, acidifying agents, mineral or organic thickening agents, in particular polymeric thickening agents, opacifying or pearlescent agents, antioxidant agents, hydroxy acids, perfumes, preservatives, p igments and ceramides.

Of course, those skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the compositions according to the invention are not, or not substantially, altered by the envisaged addition (s).

The above additives can generally be present in an amount for each of them between 0 and 20% by weight, relative to the total weight of the composition.

The composition applied in the first step of the process according to the present invention can be in the form of wax, paste, cream, gel, foam, spray or lotion.

B) Heat treatment

The method for treating keratin fibers according to the present invention further comprises a second step of heat treatment of keratin fibers at a temperature greater than or equal to 100 ° C.

The second step follows the first step. In other words, the composition, as defined above, is applied before the heat treatment of the keratin fibers.

Preferably, this step of heat treatment of keratin fibers is carried out at a temperature ranging from 100 ° C to 250 ° C, and better still from 180 ° C to 230 ° C.

Preferably, the heat treatment step is carried out for a period ranging from 2 seconds to 1 hour, preferably ranging from 5 seconds to 1 minute, per lock of hair.

This heat treatment step is generally carried out by means of a heating tool which can in particular be chosen from irons and steam irons.

By “iron” is meant, within the meaning of the present invention, a device for heating keratinous fibers bringing said fibers and the heating device into contact. The tip of the iron coming into contact with the keratin fibers generally has two flat surfaces. These two surfaces can be metallic or ceramic. In particular, these two surfaces can be smooth or notched or curved.

By "steam irons" is meant, within the meaning of the present invention, irons which comprise a device which emits water vapor and which applies this water vapor before, during or after straightening / straightening.

By way of example of irons which can be used in the smoothing process according to the invention, mention may be made of all types of flat iron with steam, and in particular, without limitation, those described in US Patents 5,957,140 and US 5,046,516.

The application of the steam iron can be carried out by successive separate touches of a few seconds, or by progressive displacement or sliding along the strands of keratin fibers, in particular of hair.

Preferably, the application of steam iron in the process according to the invention is carried out in continuous movement from the root to the tip of the hair, in one or more passages, in particular in two to twenty passages. The duration of each steam iron pass can range from 2 seconds to 1 minute.

Advantageously, water vapor is applied to the keratin fibers, in particular the hair, at a flow rate of less than 5 g / min, in particular between 1 and 4 g / min.

The application of steam can be carried out using any device known per se to generate the quantity of steam useful in the process of the invention. According to a particular embodiment, this device is portable, that is to say that the reservoir for generating the steam is in contact with the part of the device comprising the steam distribution orifices.

The step of applying the steam can be carried out, before, during or after the heating step, and preferably before.

Preferably said second step of the process according to the invention is carried out with a steampod steam straightener.

Preferably, the second heat treatment step further comprises a mechanical treatment carried out for example by means of a straightening iron.

Advantageously, the second stage of heat treatment of keratin fibers is carried out directly after application of the composition, without an intermediate rinsing stage.

Preferably, the second heat treatment step is carried out after an exposure time of the composition applied to the first step ranging from 5 minutes to 1 hour.

In a first embodiment of the method according to the invention, the composition is applied to wet or dry hair, preferably dry, with or without exposure time.

According to this first embodiment, the bath ratio of the applied formulation can vary from 0.1 to 10, more particularly from 0.2 to 5. By bath ratio, the meaning of the present invention is the ratio between the total weight of the composition applied and the total weight of keratin fibers to be treated.

The keratin fibers are then wrung or not, preferably wrung. One or more heating means are applied in a single or successive manner to the keratin fibers at a temperature advantageously greater than or equal to 100 ° C, preferably ranging from 100 ° C to 250 ° C, and more preferably from 180 ° C to 230 ° C for a time ranging from 5 seconds to one hour, preferably from 5 seconds to one minute, per lock of hair.

The hair then undergoes, or not, one or more of the following operations: rinsing, shampooing and treatment with a rinsed conditioner, drying, preferably using a helmet or a hair dryer.

Generally and preferably in the process according to the invention, the step of applying the composition to the keratin fibers is carried out on dry keratin fibers.

In a second 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 , have undergone other treatments capable of causing changes in crimping or for obtaining the desired shape or intensity.

Preferably, the method according to the invention does not include the application of a reducing composition either before, during or after the application of the composition which can be used in the method according to the invention.

This is particularly advantageous in the context of the present invention since it makes it possible to implement a method which is slightly aggressive for the hair.

The present invention also relates to a composition suitable for implementing the method of the invention, this composition being as defined above; said composition being aqueous and having an acidic pH.

By aqueous composition is meant a composition comprising at least 5% by weight of water, relative to the weight of this composition.

Preferably, the aqueous composition according to the invention comprises more than 10% by weight of water, and even more advantageously more than 20% by weight of water, relative to its total weight.

The present invention also relates to the use of a composition as defined above for the straightening and / or straightening of keratin fibers, in particular human keratin fibers such as the hair.

This composition can be very particularly used for straightening and / or straightening hair which has undergone a bleaching treatment.

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

EXAMPLES

I. Example 1: in vivo tests on models

a) Preparations of the compositions.

The composition according to the invention (A1) and the comparative composition (B1) were prepared from the ingredients, the amounts of which are mentioned, in percentage by weight relative to the total weight of each of the compositions, in the table below.

Al (invention) Bl (comparative) Maleic acid 10 10 Amodimethicone ⁽¹⁾ 10 - Distilled water Qsp 100 Qsp 100 pH 1 1

⁽¹⁾ Polydimethylsiloxane with aminoethyliminopropyl groups in cationic emulsion at 60% by weight in water (DOW CORNING 28299 CATIONIC EMULSION by DOW CORNING)

b) Protocol

The compositions (Al) and (Bl) thus obtained were applied to models at the rate of 20 grams of composition per half-head of natural white hair of Caucasian type.

Then, the locks underwent 5 successive brushing passes in position 2 (80 ° C) of the hair dryer with a round brush of medium diameter. Each of the locks was then separated into 2, and each part was subjected to 10 straightenings with a straightening iron using a comb at a temperature of 190 ° C for discolored locks or 210 ° C for natural locks. The locks were then passed 3 times using this same straightening iron.

The locks were then rinsed with water, then washed with a conventional commercial shampoo (Ultra-Soft® type).

Each lock was then pressed in different places so as not to touch the loop, then dried flat.

This smoothing protocol was also carried out on control locks, to which none of the compositions (Al) and (Bl) was applied.

The cosmetic properties, as well as the immediate smoothing and the respect of the color of the locks of hair were then evaluated by an expert in a sensory way (visual and touch) and a score was assigned according to the following criteria: no effect (-) , slight effect (+), marked effect (++), significant effect (+++) or very significant effect (++++).

c) Results

The results of the cosmetic properties obtained for natural hair are given in the following table (average value for 10 different half-heads).

Immediate smoothing Cosmetic Respect for color Al (invention) ++++ ₊₊₊₊ ++++ Bl (comparative) +++ +++ +++

The results obtained above show that the process according to the invention using the composition (Al) makes it possible to obtain immediate smoothing and gives better cosmetic properties than the comparative process using the composition (B1).

In addition, the method according to the invention respects the color of the treated hair better than the comparative method.

II.Example 2: in vitro tests on locks of hair

a) Preparation of the compositions

The composition according to the invention (A1) and the comparative composition (B2) were prepared from the ingredients, the amounts of which are mentioned, in percentage by weight relative to the total weight of each of the compositions, in the table below.

Al (invention) B2 (comparative) Maleic acid 10 - Amodimethicone ⁽¹⁾ 10 10 Distilled water Qsp 100 Qsp 100 PH 1 4

⁽²⁾ Polydimethylsiloxane with aminoethyliminopropyl groups in cationic emulsion at 60% by weight in water (DOW CORNING 28299 CATIONIC EMULSION by DOW CORNING)

b) Protocol

The compositions (Al) and (B2) thus obtained were applied to BRAZ (Brazilian) type IV locks (natural and / or discolored locks) wet according to a bath ratio of 2g / lg of lock, so that the locks are well impregnated.

Then, the locks underwent 5 successive brushing passes in position 2 (80 ° C) of the hair dryer with a round brush of medium diameter. Each of the locks was then separated into 2, and each part was subjected to 10 straightenings with a straightening iron using a comb at a temperature of 190 ° C for discolored locks or 210 ° C for natural locks. The locks were then passed 3 times using this same straightening iron.

The locks were then rinsed with water, then washed with a conventional commercial shampoo (Ultra-Soft® type).

Each lock was then pressed in different places so as not to touch the loop, then dried flat.

This smoothing protocol was also carried out on control locks, to which none of the compositions (Al) and (B2) was applied.

The immediate smoothing, as well as the properties of touch and discipline of the locks of hair were then evaluated by an expert in a sensory way (touch and visual) and a score was assigned according to the following criteria: no effect (-), effect slight (+), marked effect (++), significant effect (+++) or very significant effect (++++).

Then, the durability (or persistence) of these properties was evaluated after a cycle of 10 shampoos carried out for each of the locks tested. A global rating was assigned to sustainability according to the same criteria as above.

c) Results

The results obtained for the discolored and natural locks are given in the following tables 1 and 2 (average value for 4 different locks).

Table 1: discolored locks

Immediate smoothing To touch Disciplined Durability Al (invention) ++++ _{++++ ++++ ++++} B2 (comparative) + +++ + ++ Witness (water) - - - -

Table 2: natural wicks

Immediate smoothing To touch Disciplined Durability Al (invention) +++ +++ +++ +++ B2 (comparative) + +++ + ++ Witness (water) - - - -

The above results show that the process of the invention using the composition (Al) provides better straightening of the hair than the comparative process using the composition (B2). Smoothing with the process according to the invention is immediate and lasts longer than that obtained with the comparative process. Hair is also more disciplined.

III. Example 3: Evaluation of the friction and the flexibility of the wicks

a) Compositions

The compositions used are the compositions (A1), (B1) and (B2) described in Examples 1 and 2 above.

b) Protocol

The compositions (A1), (B1) and (B2) thus obtained were applied to bleached locks of wet Caucasian hair type II in a bath ratio of 2g / lg of lock, so that the locks were well impregnated.

Then, the locks underwent 5 successive brushing passes in position 2 (80 ° C) of the hair dryer with a medium diameter round brush. Each of the locks was then separated into 2, and each part was subjected to 10 straightenings with a straightening iron using a comb at a temperature of 190 ° C for discolored locks or 210 ° C for natural locks. The locks were then passed 3 times using this same straightening iron.

The locks were then rinsed with water, then washed with a conventional commercial shampoo (Ultra-Soft® type).

Each lock was then pressed in different places so as not to touch the loop, then dried flat.

This smoothing protocol was also carried out on control locks, to which none of the compositions (Al), (B1) and (B2) was applied.

c) Evaluation of friction

The hair strands obtained above were fixed to the sample holder of a Zwickiline Z2.5 material testing machine (ZWICK, Germany). A normal force of 0.5 N was applied to each of the wicks by pinching them in forceps covered with strips of disposable foam. The foam was removed and replaced after each measurement. A constant movement speed of 100 mm / min was imposed by the machine.

The force was recorded over time and represented in the form of a force / displacement curve reaching a plateau after a few seconds, then the average friction force on the plateau was recorded.

The impact of the application of the compositions (Al) and (B1) on the friction of the hair was obtained by comparing the average friction force of the strands of untreated hair (control strands) and the friction force of the strands treated with said compositions.

For wet measurements (wet friction force), the locks of hair were previously immersed in distilled water for one minute before carrying out the friction measurement as described above.

The friction values, in the wet and dry state, obtained for the process according to the invention using the composition (Al) and the comparative process using the composition (B1) are given in FIG. 1.

These results show that the process according to the invention, ie using a composition comprising maleic acid and amodimethicone simultaneously, results in a significant reduction in the friction of the wick, both wet and dry, compared to the comparative process in which only the maleic acid is used.

d) Assessment of flexibility

The locks of hair obtained above were subjected to bending at constant speed. The force (in Newton) applied to each of the wicks as a function of their displacement was then measured, thus making it possible to determine the maximum bending force for each of the wicks.

The higher the value of the applied force, the more rigid the wicks, i.e. the less flexible they are. Conversely, the lower the value of the applied force, the more flexible the wicks.

The flexibility values obtained for the process according to the invention using the composition (Al) and the comparative processes using the compositions (B1) and (B2) are given in FIG. 2.

These results show that the method according to the invention, implementing the combination of maleic acid and amodimethicone (Al), brings significantly more flexibility to the hair (both wet and dry) than the comparative methods in which maleic acid (B1) or amodimethicone (B2) are used alone. Indeed, the value of the maximum bending force obtained for the locks treated with the composition according to the invention (A1) is lower than that obtained for the locks treated with the comparative compositions (B1) and (B2).

e) Evaluation of the hydrophilic / hydrophobic balance

The strands of hair obtained above were immersed in water. The energy of penetration of the locks into the water was then measured, thereby determining the level of hydrophobicity of the locks.

FIG. 3 presents the results obtained for the process according to the invention using the composition (Al) and the comparative process using the composition (B1), in terms of the energy of penetration of the locks in the water. Figure 3 also shows the areas in which wicks are considered hydrophilic or hydrophobic.

These results show that the combination of maleic acid and amodimethicone makes it possible to restore a hydrophobic surface to hair, and in particular to bleached hair.

IV. EXAMPLE 4 In Vitro Assessment on Hair Strands

a) Preparation of the compositions

The composition according to the invention (A2) and the comparative composition (B3) were prepared from the ingredients, the amounts of which are mentioned, in percentage by weight relative to the total weight of each of the compositions, in the table below.

A2 (invention) B3 (comparative) Maleic acid 10 10 Amodimethicone ⁽¹⁾ 10 - Triethanolamine 5.1 4.6 Distilled water Qsp 100 Qsp 100 PH 1.5 1.5

⁽¹⁾ Polydimethylsiloxane with aminoethyliminopropyl groups in cationic emulsion at 60% by weight in water (DOW CORNING 28299 CATIONIC EMULSION by DOW CORNING)

b) Protocol

The compositions A2 and B3 thus obtained were applied to BRAZ type IV wicks (natural wicks) in a bath ratio of 2 g / lg of wick, so that the wicks are well impregnated. Then, the locks underwent 5 successive brushing passes in position 2 (80 ° C) of the hair dryer with a round brush of medium diameter. Each of the wicks was then separated into 2, and each part was subjected to 10 straightenings with a straightening iron using a comb at a temperature of 210 ° C for natural wicks. The locks were then passed 3 times using this same straightening iron.

The locks were then rinsed with water, then washed with a conventional commercial shampoo (Ultra-Soft® type).

Each lock was then pressed in different places so as not to touch the loop, then dried flat.

This smoothing protocol was also carried out on control locks, to which none of the compositions A2 and B3 was applied.

The immediate smoothing, as well as the properties of touch and discipline of the locks of hair were then evaluated by an expert in a sensory way (touch and visual) and a score was assigned according to the following criteria: no effect (-), effect slight (+), marked effect (++), significant effect (+++) or very significant effect (++++).

Then, the durability (or persistence) of these properties was evaluated after a cycle of 10 shampoos carried out for each of the locks tested. A global rating was assigned to sustainability according to the same criteria as above.

c) Results

The results obtained for natural locks are given in the following table (average value for 4 different locks).

Immediate smoothing To touch Disciplined Durability A2 (invention) +++ +++ +++ +++ B3 (comparative) ++ ++ ++ ++ Witness (water) - - - -

The above results show that the process of the invention using the composition (A2) provides better straightening of the hair than the comparative process using the composition (B3). Smoothing with the process according to the invention is immediate and lasts longer than that obtained with the comparative process. The hair is also more disciplined and has a better feel.

Claims (19)

1. Process for treating keratin fibers, in particular human keratin fibers such as the hair, preferably bleached, comprising the following steps: l) a first step of application to said keratin fibers of a composition comprising: one or more compounds chosen from the butenedioic acid derivatives of formula (I) below, as well as their addition salts, their optical isomers, their geometric isomers, their tautomers and their mixtures formula (I) in which, Ri and R2, identical or different, represent, independently of one another, a hydrogen atom, an alkyl group, linear or branched, C 1 to C 10, or an alkenyl group, linear or branched, C 2 to C 10 , said alkyl or alkenyl groups being: optionally interrupted by one or more heteroatoms, such as O, S and N (R3), with R3 representing a hydrogen atom or an alkyl group, linear or branched C1 to C6, and / or optionally substituted by one or more radicals selected from hydroxy, amino, mono or dialkylamino C1-C6, alkoxy C1-C6, and carboxy; and - one or more amino silicones; followed by 2) a second step of heat treatment of said keratin fibers at a temperature greater than or equal to 100 ° C. 2. Method according to claim 1, characterized in that Ri and R2, identical or different, represent independently of one another, a hydrogen atom or an alkyl group, linear or branched, C1 to C6, optionally substituted by one or more carboxy radicals. 3. Method according to any one of the preceding claims, characterized in that the compound or compounds of formula (I) are chosen from maleic acid, citraconic acid, aconitic acid, their geometric isomers, their salts d addition and mixtures thereof. 4. Method according to any one of the preceding claims, characterized in that the total amount of the compound or compounds of formula (I) ranges from 1 to 20% by weight, and preferably from 5 to 15% by weight, relative the total weight of the composition. 5. Method according to any one of the preceding claims, characterized in that the amino silicone (s) are chosen from the families of compounds (a) to (e) below: (a) the compounds corresponding to the following formula (II): ( ^R1 ), (T) 3., - If [OSi (T) 2] n- [OSi (T) b (R ¹ ) 2. _b ] _ln -OSi (T) _3. , - (R ¹ ), (II) formula (II), in which, - T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or C1-C8 alkyl, and preferably methyl, or C1-C6 alkoxy, preferably methoxy, - a denotes the number 0 or an integer from 1 to 3, and preferably 0, - b denotes 0 or 1, and in particular 1, - m and n are whole numbers such that the sum (n + m) can vary in particular from 1 to 2,000 and in particular from 50 to 150, n being able to designate an integer from 0 to 1,999 and in particular from 49 to 149 and m being able to designate an integer from 1 to 2000, and in particular from 1 to 10, - R ¹ is a monovalent group of formula i) -C _q H ₂ qL in which q is an integer inclusive between 2 and 8 and L is an optionally quaternized amino group chosen from the groups: -N (R ² ) -ALK-N (R ² ) ₂ , -N (R ² ) ₂ , -N ⁺ (R ² ) ₃ q-, -n (r ² ) -alk-n ⁺ (r ² ) ₂ q; wherein : * R ² , identical or different, denote a hydrogen atom, a phenyl group, a benzyl group, or a C1-C20 alkyl group, * Q 'represents an anionic counter ion allowing the electroneutrality of the polymer, preferably a halide ion such as, for example, fluoride, chloride, bromide or iodide, and * ALK, represents a group (C 1 -C 6 alkylene, linear or branched, such as ethylene -CH ₂ -CH ₂ -; or then ii) -CqH ₂ q_iL 'in which q is an integer inclusive between 2 and 8 and L' is an optionally quaternized iminated group chosen from groups: = N-ALK-N (R ² ) ₂ , = NR ² , = N ⁺ (R ² ) ₂ Q ', = N-ALK-N ⁺ (R ² ) ₃ Q' with ALK, R ² and Q 'such as defined for L; in particular, the amino silicones corresponding to the definition of formula (II) are chosen from the compounds corresponding to the following formula (III) or (ΙΙΓ): R 'ch ₃ çh ₃ R— -Yes- 0- -Yes ch ₃ ch ₃ O —If AT NH I Ç ^H 3 O — Si — R CH ₃ (ÇH ₂ ) ₂ nh ₂ Ç ^H 3 O — Si — R CH ₃ (ΙΙΓ) 5 formulas (III) or (ΙΙΓ), in which: • R, R ', R, identical or different, denote a C1-C4 alkyl group, preferably CH ₃ , a C1-C4 alkoxy group, preferably methoxy, or OH, • A represents an alkylene group, linear or branched, in C3-C8, from Preferably at C3-C6, • A 'represents an alkylene group - (CR ^a R ^b ) _p -C (R ^c ) = with p representing an integer inclusive between 0 and 5, and R ^a , R ^b , and R ^c , identical or different, representing a hydrogen atom or a (Ci-C4) alkyl group, preferably R ^a , R ^b , and R ^c represent a hydrogen atom, • m and n, identical or different, are whole numbers depending on the molecular weight and the sum of which is between 1 and 2000; (b) the compounds corresponding to the following formula (V): R ⁴ —CH2 - CHOH CH2 - N ⁺ (R ³ ) 3 Q R ³ R— Si - R ³ Yes R ³ R ³ I If — R ³ R ³ (V) formula (V), in which, R ³ represents a monovalent Ci-Cis hydrocarbon group, and in particular a Ci-Cis alkyl group, or C2-C18 alkenyl group, for example methyl, R ⁴ represents a divalent hydrocarbon group, in particular a C 1 -C 6 alkylene group or a divalent C 1 -C 8 alkyleneoxy group, for example C 1 -Cs, Q ′ is an anionic counter ion, in particular halide, in particular chloride, - r represents an average statistical value from 2 to 20 and in particular from 2 to 8, - s represents an average statistical value from 20 to 200 and in particular from 20 to 50; (c) quaternary ammonium silicones of formula (VI): 2X Ry I l ₊ Si - R ₆ -CH ₂ -CHOH-CH ₂ -NR ₈ Ry (VI) formula (VI), in which, - R7, identical or different, represent a monovalent hydrocarbon group having from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl group, a C2-C18 alkenyl group or a ring comprising 5 or 6 carbon atoms, for example methyl, - R6 represents a divalent hydrocarbon group, in particular a Ci-Cis alkylene group or a divalent CiCis, for example Ci-Cs alkyleneoxy group linked to Si by an Si-C bond, - Rs, identical or different, each represents a hydrogen atom, a monovalent hydrocarbon group having from 1 to 18 carbon atoms, and in particular a C1-Cis alkyl group, a C ₂ -Cis alkenyl group, a group -R6-NHCOR7, X 'is an anionic counter ion such as a halide ion, in particular chloride or an organic acid salt, - r represents an average statistical value from 2 to 200 and in particular from 5 to 100; (d) amino silicones of formula (VII) or (VU ’): r- R. R, -1 | 1 H ₂ N- (C _m H _2m ) -N- (C _n H _2n ) -Si- -o- -If - O- -Yes - - ^R 5 L r ₂ J X ^R 4 (VII) Γ î ¹ Ί r ₃ - H ₂ N- (C _m H _2m ) -N = (0 ^) - 81- -o- -If - O- -Yes - -R ₅ L r ₂ J X r ₄ (VIL) formulas (VII) and (VU ’), in which: - Ri, R ₂ , R3 and R4, identical or different, each denote a C1-C4 alkyl group or a phenyl group, - R5 denotes a C1-C4 alkyl group 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 such that the amine index is between 0.01 and 1 meq / g; and (e) mixtures thereof. 6. Method according to any one of the preceding claims, characterized in that the amino silicone (s) are chosen from poly (di) (Ci-C6) alkylsiloxanes with imino groups (CiC6alkyl or with groups (di) (Ci-C6 ) (alkyl) amino (Ci-C6) alkylimino (CiC6alkyl; preferably among polydi (Ci-C4) alkylsiloxanes with imino groups (Ci-C4) alkyl or with groups (di) (C 1 -C4) (alkyl) amino (CiC4) alkylimino (Ci-C4) alkyl, and more preferably from polydimethylsiloxanes with imino groups (Ci-C4) alkyl or with amino groups (Ci-C3) alkylimino (Ci-C4) alkyl such as polydimethylsiloxanes with iminopropyl groups or aminoethyliminopropyl. 7. Method according to any one of the preceding claims, characterized in that the composition applied in the first step of the method further comprises one or more surfactants chosen from cationic surfactants, nonionic surfactants, and mixtures thereof; and preferably cationic surfactants. 8. Method according to any one of the preceding claims, characterized in that the total amount of the amino silicone (s) ranges from 0.5 to 20% by weight, preferably from 1 to 10% by weight, and more preferably from 2 to 5% by weight, relative to the total weight of the composition. 9. Method according to any one of the preceding claims, characterized in that the weight ratio between the total amount of the compound (s) of formula (I) and the total amount of the amino silicone (s) ranges from 0.1 to 10, preferably from 0.5 to 5, more preferably from 1 to 4, and better still from 1.5 to 3. 10. Method according to any one of the preceding claims, characterized in that the composition applied in the first step of the method further comprises one or more alkaline agents. 11. Method according to claim 10, characterized in that the alkaline agent (s) are chosen from mineral, organic, hybrid alkaline agents and their mixtures; and more preferably from ammonia, alkali carbonates or bicarbonates such as sodium or potassium carbonates or bicarbonates, sodium or potassium hydroxides, organic amines chosen from alkanolamines, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids, polyamines of formula (VIII) and their mixtures: N-W-N \ R _t (wine) formula (VIII), in which, W is a divalent C1 to C6 alkylene radical optionally substituted by one or more hydroxyl groups or a C1 to C6 alkyl radical, and / or optionally interrupted by one or more heteroatoms such as O, or NR _U ; R _x , R _y , R _z , R _t , and R _{u, which may be} identical or different, represent a hydrogen atom, a C1-C6 alkyl or C1-C6 hydroxyalkyl radical, or a C1-C6 aminoalkyl radical. 12. Method according to claim 10 or 11, characterized in that the alkaline agent (s) are chosen from ammonia, alkanolamines and their mixtures, and preferably from ammonia, mono-, di- or tri-hydroxy (Ci-C6) alkylamines, such as triethanolamine, and mixtures thereof. 13. Method according to any one of claims 10 to 12, characterized in that the weight ratio between the total amount of the compound (s) of formula (I) and the total amount of the alkaline agent (s) ranges from 1 to 5, preferably from 1.5 to 3, and more preferably 1.5 to 2.5. 14. Method according to any one of the preceding claims, characterized in that the pH of the composition ranges from 0.5 to 5, preferably from 1 to 4, and more preferably from 1 to 1.5. 15. Method according to any one of the preceding claims, characterized in that the step of heat treatment of keratin fibers is carried out at a temperature ranging from 100 ° C to 250 ° C, and more preferably from 180 ° C to 230 ° vs. 16. Method according to any one of the preceding claims, characterized in that a mechanical treatment step for straightening the keratin fibers, such as brushing, preferably accompanied by heating with a hair dryer, is carried out between the first and the second step of the process. 17. Method according to any one of claims 1 to 15, characterized in that the step of heat treatment of keratin fibers is carried out directly after application of the composition, without an intermediate rinsing step. 18. Composition as defined in the first step of the process in any one of claims 1 to 14, characterized in that said composition is aqueous and has an acidic pH. 19. Use of the composition as defined in claim 18 for the straightening and / or straightening of keratin fibers, in particular human keratin fibers such as the hair. 1/2