WO2020260488A1

WO2020260488A1 - Process for repairing keratin fibers using a particular cyclic polycarbonate and an amino silicone and uses

Info

Publication number: WO2020260488A1
Application number: PCT/EP2020/067885
Authority: WO
Inventors: Andrew Greaves
Original assignee: L'oreal
Priority date: 2019-06-27
Filing date: 2020-06-25
Publication date: 2020-12-30
Also published as: FR3097754A1; FR3097754B1

Abstract

The present invention relates to a process for repairing keratin fibers, comprising the application to the keratin fibers of at least one particular carbonate ester and of at least one amino silicone.

Description

PROCESS FOR REPAIRING KERATIN FIBERS USING A PARTICULAR CYCLIC POLYCARBONATE AND AN AMINO SILICONE AND USES

FIELD OF THE INVENTION

BACKGROUND OF THE INVENTION

Hair is generally damaged and embrittled by the action of external atmospheric agents such as light, sunlight and bad weather, and also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving, relaxing and repeated washing. Hair is thus damaged by these various factors and may in the long run become dry, coarse, brittle or dull or split and/or limp.

Thus, to overcome these drawbacks, it is common practice to resort to hair treatments which make use of compositions intended for conditioning the hair appropriately by giving it satisfactory cosmetic properties, notably smoothness, sheen, a soft feel (a natural feel, the hair is no longer coarse), suppleness, lightness, good disentangling properties leading to easy combing, and good manageability of the hair which is thus easy to shape.

These haircare compositions may be, for example, conditioning shampoos, hair conditioners, masks or sera. However, the effect obtained fades out in the course of successive shampoo washes and does not show satisfactory persistence with respect to shampooing.

Nevertheless, the results obtained are not always satisfactory in terms of repairing keratin fibers, notably split fibers.

There is thus a real need to develop a composition and a process for treating keratin fibers, notably human keratin fibers such as the hair, which is capable of repairing split ends in a long-lasting manner.

SUMMARY OF THE INVENTION

According to a first aspect, a subject of the present invention is a process for repairing keratin fibers, comprising:

(i) a step consisting in applying to the keratin fibers at least a) one compound of formula (I) below: in which formula (I):

R¹, R², R³ and R⁴, which may be identical or different, represent a hydrogen atom or a (CrC₆)alkyl and particularly (CrC4)alkyl group, it being understood that one of the groups R¹, R², R³ or R⁴ denotes a chain -(ALK)_m-(Q)_q-(Z)_z-(Y)y-(ALK')p-(W)_w-;

preferentially, R¹, R² and R³ denote a hydrogen atom, and R⁴ denotes the chain:

- (A L K) _m- (Q)_q- (Z)_z- (Y) _y- (A L K') _p- (W)_w- ;

ALK and ALK', which may be identical or different, represent a (CrCi2)alkylene group optionally substituted and/or interrupted with one or more heteroatoms such as oxygen, sulfur, or NR⁸ with R⁸ as defined below; in particular, ALK and ALK' represent (CrC₆)alkylene, preferably (CrC4)alkylene, such as methylene;

Q, Y and W, which may be identical or different, represent an oxygen or sulfur atom or NR⁸, with R⁸ representing a hydrogen atom or a (CrC4)alkyl or benzyl group, preferably oxygen or NR⁸ such as NH;

Z represents a carbonyl C=0, thiocarbonyl C=S or imino C=NR⁸ group with R⁸ as defined previously, preferably carbonyl,

m, p, q, z, y and w, which may be identical or different, represent 0 or 1 ; preferably, m = 1 and p, q, z, y and w, which may be identical or different, represent 0 or 1 ;

n represents an integer ranging from 1 to 4; in particular, n is equal to 1 , 2 or 3, preferably 1 or 2; more preferentially, n = 1 ;

T represents a polyvalent group, said polyvalent group being chosen, when u = 2, from:

i) (Ci-Cioo)alkylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl, (Ci- C4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals,

ii) (C2-Cioo)alkenylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl, (Ci- C4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkenylene radical denotes a (C2-Cioo)alkenylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals,

iii) (hetero)arylene such as phenylene, for instance 1 ,3-phenylene,

iv) (hetero)cycloalkylene,

said polyvalent group being chosen, when u = 3 or 4, from:

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

ii) a multivalent (trivalent or tetravalent) aromatic or nonaromatic (hetero)cyclic radical preferably containing 5 or 6 carbon atoms;

u represents an integer ranging from 2 to 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;

- the following units:

are identical or different; and

(ii) a step consisting in applying to the keratin fibers at least b) one amino silicone.

According to a second aspect, a subject of the present invention is the use of at least one compound of formula (I) as defined above in combination with at least one amino silicone for repairing keratin fibers.

According to a third aspect, a subject of the present invention is the use of a composition (Ci) comprising:

a) at least one compound of formula (I) as defined above; and

b) at least one amino silicone; for repairing keratin fibers.

According to a fourth aspect, a subject of the present invention is a multi-compartment device comprising:

- a first compartment containing a composition (C_å) comprising a) at least one compound of formula (I) as defined above, and

- a second compartment containing a composition (C₃) different from composition (C₂), composition (C₃) comprising b) at least one amino silicone. DETAILED DESCRIPTION OF THE INVENTION In the following text, unless indicated otherwise:

the term "keratin fibers" means fibers of human or animal origin such as head hair, bodily hair, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferentially the hair.

when compounds are mentioned in the present patent application, this also includes the optical isomers thereof, the geometrical isomers thereof, the tautomers thereof, the salts thereof or the solvates thereof, alone or as a mixture. In particular, the term "compound of formula (I)" also means the corresponding salts thereof.

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

the term“alkyl” means a linear or branched hydrocarbon-based 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 or n-hexyl, preferably methyl;

the term“alkenyl” means a linear or branched hydrocarbon-based 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 conjugated or non-conjugated ethylenic unsaturations, such as ethylenyl, n-propylenyl, isopropylenyl, butylenyl, n- pentylenyl or n-hexylenyl;

the term“ alkox y” means an alkyl-oxy group with“alkyk as defined previously;

the term“alkylene” means a linear or branched divalent hydrocarbon-based radical 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 or n- hexylene;

the term“alkenylene" means a hydrocarbon-based radical as defined for“alkenyf’ the term“(hetero)arylene” means a divalent "aryl" or divalent "heteroaryl" group, said aryl or heteroaryl groups being as defined below;

the term“(hetero)cycloalkylene” means a divalent "cycloalkyl" or divalent

"heterocycloalkyl" group, said cycloalkyl or heterocycloalkyl groups being as defined below;

the term“optionally substituted’ preceded by the alkyl, alkenyl, alkylene, alkenylene or alkoxy groups means that said groups may be substituted on the hydrocarbon-based radical with one or more groups, which may be identical or different, chosen from i) hydroxyl, ii) thiol, iii) halogen, iv) (CrC4)alkoxy, v) hydroxy(C2-C4)alkoxy; vi)

(di)(hydroxy(Ci-C4)(alkyl)amino, vii) cyano, viii) nitro(so), ix) R_a-Z_a-C(Z_b)-Z_c-, and x) R_a- Z_a-S(0)_t-Z_c- with Z_b representing an oxygen or sulfur atom or a group NR_a', Z_a and Z_c, which may be identical or different, representing a bond, an oxygen or sulfur atom, or a group NR_a; R_a representing a hydrogen atom or a (Ci-C4)alkyl group and R_a· representing a hydrogen atom or an alkyl group and t is 1 or 2;

an "a/y radical represents a monocyclic or fused or nonfused polycyclic carbon- based group comprising from 6 to 22 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl; more preferentially, the aryl radical is a phenyl; a“heteroaryl radicaP' represents a 5- to 22-membered monocyclic or fused or nonfused polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl and xanthyl;

a " heterocyclic radicaP' is a 5- to 22-membered, monocyclic or fused or nonfused polycyclic radical which may contain one or two unsaturations but is not aromatic, including from 1 to 6 heteroatoms chosen from nitrogen, oxygen and sulfur;

a“heterocycloalkyl radicaP’ is a heterocyclic radical comprising at least one saturated ring and at least one heteroatom chosen from nitrogen, oxygen and sulfur;

the "aryP' or "heteroaryP' radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:

- a C1-C16 and preferably C Cs alkyl radical optionally substituted with one or more radicals chosen from hydroxyl, C1-C2 alkoxy, (poly)hydroxy(C2-C4)alkoxy, acylamino, amino substituted with two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered and preferably 5- or 6-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom;

- a halogen atom;

- a hydroxyl group;

- a C1-C2 alkoxy radical;

- a (poly)hydroxy(C2-C4)alkoxy radical; - an amino radical;

- a 5- or 6-membered heterocycloalkyl radical;

- an optionally cationic 5- or 6-membered heteroaryl radical, preferentially imidazolium, optionally substituted with a (CrC₄)alkyl radical, preferentially methyl;

- an amino radical substituted with one or two identical or different C₁-C₆ alkyl radicals, optionally bearing at least:

i) a hydroxyl group,

ii) an amino group optionally substituted with one or two optionally substituted C₁-C₃ alkyl radicals, said alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom,

iii) a 5- or 6-membered heteroaryl radical, optionally substituted with a (CrC₄)alkyl radical, preferentially methyl;

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

- a carbamoyl radical ((R)₂N-C(0)-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C₁-C₄ alkyl radical optionally bearing at least one hydroxyl group;

- an alkylsulfonylamino radical (R’-S(0)₂-N(R)-) in which the radical R represents a hydrogen atom or a C₁-C₄ alkyl radical optionally bearing at least one hydroxyl group and the radical R' represents a C₁-C₄ alkyl radical or a phenyl radical; an aminosulfonyl radical ((R)₂N-S(0)₂-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C₁-C₄ alkyl radical optionally bearing at least one hydroxyl group;

- a carboxylic radical in acid or salified (preferably with an alkali metal or a substituted or unsubstituted ammonium) form;

- a cyano group;

- a polyhaloalkyl group, preferentially trifluoromethyl;

preferably, the“a/y/" or“heteroaryP' radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from a C₁-C₆ alkyl radical, a halogen atom; a C₁-C₂ alkoxy radical; a polyhaloalkyl group, preferentially trifluoromethyl, more preferentially from a C₁-C₆ alkyl radical;

the cyclic or heterocyclic part of a nonaromatic radical may be substituted with at least one substituent chosen from the following groups:

- hydroxyl;

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

- alkylcarbonylamino (R-C(O)-N(R')-) in which the radical R’ is a hydrogen atom or a Ci- C₄ alkyl radical optionally bearing at least one hydroxyl group, and the radical R is a Ci- C₂ alkyl radical or an amino radical optionally substituted with one or two C₁-C₄ alkyl groups, which may be identical or different, themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;

- alkylcarbonyloxy (R-C(O)-O-) in which the radical R is a C₁-C₄ alkyl radical or an amino group optionally substituted with one or two identical or different C₁-C₄ alkyl groups themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;

- alkoxycarbonyl (R-G-C(O)-) in which the radical R is a C₁-C₄ alkyl radical, G is an oxygen atom or an amino group optionally substituted with 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 saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;

preferably, the cyclic or heterocyclic part of a nonaromatic radical may be substituted with at least one substituent chosen from C1-C4 alkoxy, (poly)hydroxy(C2-C4)alkoxy or C1-C4 alkyl groups; more preferentially with at least one C1-C4 alkyl radical such as methyl;

a cyclic or heterocyclic radical, or a nonaromatic part of an aryl or heteroaryl radical, may also be substituted with one or more oxo groups;

the expressions“at least one” and“one or more" are synonymous and may be used interchangeably.

Process for repairing keratin fibers

According to a first aspect, a subject of the present invention is a process for repairing keratin fibers as defined above.

Steps (i) and (ii) may be performed sequentially in this order, that is to say (i) then (ii) or in the reverse order, that is to say (ii) then (i), preferably (i) then (ii).

Preferably, steps (i) and (ii) are performed simultaneously. The process according to the present invention comprises (i) a step consisting in applying to the keratin fibers at least a) one compound of formula (I) as defined above.

Compound(s) of formula (I)

According to one embodiment, u is equal to 2 or 3 and T represents a divalent 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 (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl, (CrC4)alkyl or (Ci- C4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals. According to this embodiment, T preferably represents a radical T1 of formula -(CH₂)_xi-[0-(CH₂)_x2-]_x3 (0)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)-0-]_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 and R'², which may be identical or different, representing a (CrC4)alkyl radical 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 cycloalkylene group, preferably cyclohexylene, preferably substituted with 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 or 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-based radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, ii) an aromatic or nonaromatic, preferably aromatic, trivalent (hetero)cyclic radical containing 5 or 6 carbon atoms, preferably 6 carbon atoms, such as a trivalent 1 ,3,5- phenyl radical.

More preferentially, u is 2, Q represents an oxygen atom, and ALK and ALK’ represent a (CrC4)alkylene, such as methylene.

According to an advantageous embodiment, the compound of formula (I) is such that u is 2 and: - m = 1 ;

- ALK represents a (CrC4)alkylene, such as methylene;

- Q represents an oxygen atom;

- q = 0 or 1 ;

- Z represents a carbonyl;

- z = 0 or 1 ;

- Y represents NH;

- y = 0 or 1 ;

- ALK’ represents a (CrC4)alkylene, such as methylene;

- p = 0 or 1 ;

- w = 0.

According to an advantageous embodiment, the compound of formula (I) is such that u is 2 and:

- one of the units:

is such that m + p is an integer greater than or equal to 1 ; preferably, m is 1 and p is 0, and preferentially q = z = y = 1 ; and

- the other unit:

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

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

le If

O

u

with t being an integer ranging from 1 to 50, preferably from 3 to 30 and more preferentially from 5 to 20;

with r being an integer ranging from 1 to 50, preferably from 3 to 30 and more preferentially from 5 to 20;

1m with s being an integer ranging from 4 to 30, preferably from 5 to 10;

and mixtures thereof.

The process according to the present invention also comprises (ii) a step consisting in applying to the keratin fibers at least b) one amino silicone.

Amino silicone(s):

The term“amino silicone” means any silicone including at least one primary or secondary amine function.

The weight-average molecular masses of these amino silicones may be measured by gel permeation chromatography (GPC) at room temperature (25°C), as polystyrene equivalent. The columns used are m styragel columns. The eluent is THF and the flow rate is 1 ml/minute. 200 mI of a 0.5% by weight solution of silicone in THF are injected. Detection is performed by refractometry and UV-metry.

Preferably, the amino silicones that may be used in the context of the invention are chosen from:

a) the polysiloxanes of formula (A) below:

in which x' and y' are integers such that the weight-average molecular weight (Mw) ranges from 5000 to 500 000;

b) the amino silicones of formula (B) below:

R'aG3-a-Si(0SiG₂)n-(0SiGbR'2-b)m-0-SiG3-a-R'a (B)

in which:

- G, which may be identical or different, denotes a hydrogen atom or a phenyl, OH, Ci- Cs alkyl, for example methyl, or C Cs alkoxy, for example methoxy, group,

- a, which may be 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 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;

- R', which may be 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 following groups:

-N(R")₂; -N⁺(R")₃ A-; -NR"-Q-N(R")₂ and -NR"-Q-N⁺(R")₃ A-,

in which R", which may be identical or different, denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based radical, for example a C1-C20 alkyl radical; Q denotes a linear or branched group of formula C_rH_2r, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A- represents a cosmetically acceptable anion, notably a halide such as fluoride, chloride, bromide or iodide;

c) the amino silicones of formula (C) below:

in which:

- Ri , R₂, R₃ and R4, which may be 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 ranging from 1 to 5,

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

- x is chosen such that the amine number ranges from 0.01 to 1 meq/g;

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

e) and mixtures thereof.

Multiblock polyoxyalkylenated amino silicones of the type (AB)n

The multiblock polyoxyalkylenated amino silicones of the type (AB)n are preferably formed from repeating units having the following general formulae:

[-(SiMe₂0)_xSiMe₂ - R -N(R")- R'-0(C₂H₄0)_a(C₃H₆0)_b -R'-N(H)-R-]

or alternatively

[-(SiMe₂0)_xSiMe₂ - R -N(R")- R' - 0(C₂H₄0)_a(C₃H₆0)_b -]

in which:

- a is an integer greater than or equal to 1 , preferably ranging from 5 to 200 and more particularly ranging from 10 to 100; - b is an integer ranging from 0 to 200, preferably ranging from 4 to 100 and more particularly ranging from 5 to 30;

- x is an integer ranging from 1 to 10 000 and more particularly from 10 to 5000;

- R" is a hydrogen atom or a methyl;

- R, which may be identical different, represent a linear or branched divalent C2-C12 hydrocarbon-based radical, optionally including 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

-CH₂CH₂CH₂0CH₂CH(0H)CH₂-; preferentially, R denotes a radical

-CH₂CH2CH20CH₂CH(0H)CH2-;

- R’, which may be identical or different, represent a linear or branched divalent C2-C12 hydrocarbon-based radical, optionally including 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

-CH₂CH2CH20CH₂CH(0H)CH2-; preferentially, R’ denotes -CH(CH₃)-CH₂-.

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

The amine content preferably ranges from 0.02 to 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly from 0.05 to 0.2.

The weight-average molecular mass (Mw) of the silicone preferably ranges from 5000 to 1 000 000 and more particularly from 10 000 to 200 000.

Mention may notably be made of the silicones sold under the name Silsoft A-843 or Silsoft A+ by Momentive.

Preferably, the amino silicones are chosen from the amino silicones of formula (B). Amino silicone(s) of formula (B)

The amino silicones of formula (B) may be chosen from the amino silicones corresponding to formulae (D), (E), (F), (G), (H), (J) and (K) below, and mixtures thereof.

According to a first embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones known as "trimethylsilyl amodimethicone" corresponding to formula (D): in which m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10.

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

in which:

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

- R1 , R2 and R3, which may be identical or different, represent a hydroxyl 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/a I koxy mole 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 and more particularly from 3500 to 200 000. According to a third embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones of formula (F) below:

in which:

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

- R1 and R2, which are different, represent a hydroxyl 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/a I koxy mole 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, even more particularly from 5000 to 100 000 and more particularly from 10 000 to 50 000.

The commercial products comprising silicones of structure (E) or (F) may include in their composition one or more other amino silicones whose structure is different from formula (E) or (F).

A product containing amino silicones of structure (E) is sold by the company Wacker under the name Belsil® ADM 652.

A product containing amino silicones of structure (F) is sold by the company Wacker under the name Fluid WR 1300®.

Among the amino silicones of formula (F), mention may also be made of the product Belsil ADM Log 1 from Wacker.

When these amino silicones are used, one particularly advantageous embodiment consists in using them in the form of an oil-in-water emulsion. The oil-in-water emulsion may comprise one or more surfactants. The surfactants may be of any nature but are preferably cationic and/or nonionic. The number-mean size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometers. Preferably, notably as amino silicones of formula (E), use is made of microemulsions with a mean particle size ranging from 5 nm to 60 nanometers (limits included) and more particularly from 10 nm to 50 nanometers (limits included). Thus, use may be made according to the invention of the amino silicone microemulsions of formula (E) sold under the name 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 formula (G) below:

in which:

- m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;

- A denotes a linear or branched alkylene radical containing from 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 1 000 000 and even more particularly from 3500 to 200 000.

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 formula (H) below: in which:

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

The weight-average molecular mass (Mw) of these amino silicones preferably ranges from 500 to 1 000 000 and even more particularly from 1000 to 200 000.

A silicone corresponding to this formula is, for example, DC2-8566 Amino Fluid from Dow Corning.

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

in which:

- m and n are numbers ranging from 1 to 5000, and in particular n possibly denoting a number ranging from 10 to 2000 and notably from 100 to 1000, and in particular m possibly denoting a number from 1 to 100; - Ri and R2, which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated alkyl radical comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, preferably from 12 to 20 carbon atoms;

- A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms; this radical is preferably branched.

Preferably, A comprises from 3 to 6 carbon atoms, better still 4 carbon atoms;

preferably, A is branched. In particular, A denotes the following divalent radicals: -CH2CH2CH2- or -CH₂CH(CH₃)CH₂-.

Preferably, Ri and R2, which may be identical or different, represent a saturated linear alkyl radical comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms, preferably 12 to 20 carbon atoms; in particular, Ri and R2 denote dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl radicals;

preferably, Ri and R2, which may be identical or different, are chosen from hexadecyl and octadecyl radicals.

Preferably, the amino silicone(s) of formula (J) are such that:

- n is a number ranging from 10 to 2000 and notably from 100 to 1000;

- m is a number ranging from 1 to 100;

- Ri and R2, which may be identical or different, represent a saturated linear alkyl radical comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and preferably from 12 to 20 carbon atoms; chosen in particular from dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl radicals; preferably, Ri and R2, which may be identical or different, are chosen from hexadecyl and octadecyl radicals; and

- A comprises from 3 to 6 carbon atoms and preferably 4 carbon atoms; preferably, A is branched; more preferentially, A is chosen from the following divalent radicals: -CH2CH2CH2- and -CH₂CH(CH₃)CH₂-.

The amino silicones of formula (J) that are particularly preferred are those

corresponding to the INCI name Jb/s-cetearylamodimethicone. In particular, the amino silicones of formula (J) correspond to the silicone sold by the company Momentive under the name Silsoft AX.

According to a seventh embodiment, the amino silicones corresponding to formula (B) are chosen from the silicones of formula (K) below: in which the value of n is such that the weight-average molecular weight (Mw) of the silicone ranges from 500 to 55 000.

As examples of amino silicone corresponding to formula (K), mention may be made of those sold under the names DMS-A11 , DMS-A12, DMS-A15, DMS-A21 , DMS-A31 , DMS-A32 and DMS-A35 by the company Gelest, and under the reference 481688 from Aldrich.

Preferably, the amino silicones of formula (B) are chosen from the amino silicones of formulae (J) and (K), and mixtures thereof.

Additional features of the process

Preferably, steps (i) and (ii) of the process are performed simultaneously by applying to the keratin fibers a composition (Ci) comprising:

a) the compound(s) of formula (I) as defined above; and

b) the amino silicone(s).

Composition (Ci) may optionally comprise at least one organic solvent, preferably chosen from:

- isododecane;

- monoalcohols comprising a hydroxyl group and a Ci-Ce(alkyl) and preferably Ci- C4(alkyl) group such as methyl, ethyl or (iso)propyl;

- polyols comprising from 2 to 30 hydroxyl groups and a (C2-Cs)alkyl group, preferably a (C2-C4)alkyl group; and mixtures thereof.

More preferentially, the organic solvent is chosen from monoalcohols and polyols comprising two hydroxyl groups, even more preferentially from ethanol and polyols comprising two hydroxyl groups and at least three carbon atoms, most preferentially from ethanol, propylene glycol (1 ,2-propanediol); 1 ,3-propanediol; 1 ,3-butylene glycol; 1 ,2-pentanediol; dipropylene glycol; hexylene glycol; pentylene glycol; butylene glycol; glycerol; ethylene glycol, and mixtures thereof.

Composition (Ci) may comprise a total content of compounds of formula (I) ranging from 0.01 % to 20%, preferably from 0.05% to 15%, more preferentially from 0.1% to 10%, even more preferentially from 0.5% to 5%, most preferentially from 1% to 5% by weight relative to the total weight of composition (Ci). Composition (Ci) may comprise a total content of amino silicone(s) ranging from 0.1% to 85%, preferably from 0.5% to 20%, more preferentially from 1 % to 10% by weight relative to the total weight of composition (Ci).

Composition (Ci) may comprise a total content of organic solvents ranging from 0% to 99%, preferably from 20% to 95% by weight, more preferentially from 50% to 80% by weight relative to the total weight of composition (Ci).

The pH of composition (Ci) may be less than or equal to 10; preferably, the pH of composition (Ci) may range from 3 to 9; more preferentially, the pH of composition (Ci) may range from 4 to 8. The pH of the composition may be adjusted with a compound known to those skilled in the art.

Alternatively, steps (i) and (ii) may be performed by applying to the keratin fibers:

- a composition (C_å) comprising a) the compound(s) of formula (I) as defined above; and

- a composition (C₃) comprising b) the amino silicone(s)

- composition (C_å) is applied before composition (C3) or composition (C3) is applied before composition (C2), preferably composition (C_å) is applied before composition (C3). Preferably, composition (C_å) does not comprise any amino silicone and composition (C3) does not comprise any compound of formula (I).

Compositions (C_å) and/or (C3) may optionally comprise at least one organic solvent.

The organic solvents as defined above may also be used in compositions (C_å) and/or (Cs).

Compositions (Ci), (C_å) and (C3) used in the process according to the invention may also comprise at least one common cosmetic ingredient other than the compounds described previously, notably chosen from surfactants, notably nonionic or cationic surfactants, solid or liquid fatty substances, thickeners, nonsilicone cationic polymers, silicones, polar or apolar solvents, sunscreens; moisturizers; antidandruff agents;

antioxidants; chelating agents; nacreous agents and opacifiers; plasticizers or coalescers; fillers; fragrances; silanes other than the amine derivatives of alkoxysilane; crosslinking agents. Needless to say, the compositions may comprise several cosmetic ingredients featured in the above list.

Depending on their nature and the intended use of the composition, the usual cosmetic ingredients may be present in usual amounts, which may be readily determined by a person skilled in the art and which may be, for each ingredient, between 0.01% and 80% by weight. A person skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the compositions of the present invention.

Compositions (Ci), (C_å) and (C3) used in the process according to the invention may be in any presentation form conventionally used, and notably in the form of an aqueous, alcoholic or aqueous-alcoholic or oily solution or suspension; a solution or a dispersion of the lotion or serum type; an emulsion, notably of liquid or semiliquid consistency of the O/W, W/O or multiple type; a suspension or emulsion of soft consistency of the (O/W) or (W/O) cream type; an aqueous or anhydrous gel, or any other cosmetic form. These compositions may be packaged in pump-action bottles or in aerosol containers, so as to apply the composition in vaporized (lacquer) form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for treating the hair. In these cases, the composition preferably comprises at least one propellant.

Compositions (Ci), (C_å) and (C3) which have just been described may be applied to keratin fibers. The bath ratio of the applied compositions, i.e. the weight amount of applied composition relative to the weight of treated keratin fibers, may range from 0.01 to 10, preferably from 0.1 to 5, more preferentially from 0.2 to 3. The term "bath ratio" means the ratio between the total weight of the applied composition and the total weight of keratin fibers to be treated.

Compositions (Ci), (C_å) and (C3) of the invention may be applied to wet or dry keratin fibers, preferably wet or dry hair, preferably to dry hair.

In particular, the step of application of each of the compositions (Ci), (C_å) and (C3) may be followed by a leave-on time. The leave-on time, namely the time of contact of the composition on the hair, is preferably at least 30 seconds, preferably between 1 and 30 minutes. Rinsing of the hair may optionally be envisaged after applying the last composition and optionally the leave-on time.

The hair may then optionally be wrung dry, preferably wrung dry.

Heat treatment step

Preferably, the process according to the present invention also comprises, following the set of steps (i) and (ii), a step (iii) of heat treatment of the keratin fibers at a temperature ranging from 40°C to 230°C, preferably from 60°C to 190°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 performed using a heating tool such as a straightening iron, a curling iron, a crimping iron, a waving iron, a steam iron, a hood, a hairdryer, an infrared heating system or a heating roller, preferably using a straightening iron. In the case where the heat treatment step is performed using a heating tool such as a straightening iron, a curling iron, a crimping iron, a waving iron or a steam iron, the keratin fibers may be dried beforehand, naturally or using a hairdryer.

Uses According to a second aspect, a subject of the present invention is the use of at least one compound of formula (I) as defined above in combination with at least one amino silicone as defined above for repairing keratin fibers, preferably for repairing hair, most preferentially for repairing split ends.

According to a third aspect, a subject of the present invention is the use of a

composition (Ci) as defined above for repairing keratin fibers, preferably for repairing hair, most preferentially for repairing split ends.

The technical features concerning compound(s) of formula (I) and the amino silicone(s) described above in the context of the process according to the present invention also apply to the uses of these compounds.

The technical features concerning composition (Ci) described in the context of the process according to the present invention also apply to composition (Ci) in the context of the use thereof.

Device

- a first compartment containing a composition (C_å) comprising a) the compound(s) of formula (I) as defined above, and

- a second compartment containing a composition (C₃) different from composition (C₂), composition (C₃) comprising b) the amino silicone(s).

Preferably, composition (C2) does not comprise any amino silicone and composition (C3) does not comprise any compound of formula (I).

The technical features concerning compositions (C_å) and (C3) described in the context of the process according to the present invention also apply to compositions (C_å) and (C3) included in the multi-compartment device.

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

Examples

Example 1

The following compositions were prepared. [Table 1]

¹ Amodimethicone-Reference Silsoft AX from the company Momentive

² Poly(dimethylsiloxane)bis(3-aminopropyl) terminated (PDMS = 25 KDa)-Reference DMS-A31 from the company Gelest

3 Polypropylene oxide) biscyclocarbonate from the company Specific Polymers (MW

500-800 g/mol) of formula Im

⁴ Phloroglucinol tricyclocarbonate CAS No. 1980062-58-5 from the company Specific Polymers of formula If

⁵ Polypropylene oxide) from the company Sigma reference 202312 (MW -725 g/mol) Split end hair repair study

Protocol

Evaluation of the repair of the keratin fibers was performed using an optical microscope (175 X optical“mightyscope 1.3M digital microscope” model sold by the company Aven Inc., USA - aveninc.com).

Each fiber to be evaluated selected for the study is a natural fiber 15 cm long and naturally split in two longitudinally at the end (split-end hair) sold by the company IHIP (Glendale, NY 11385, USA).

The end of each fiber is observed before treatment and after treatment by microscope. The treatment of the fibers consists in placing five split fibers (marked with a piece of adhesive tape and numbered (root side)) in a lock of hair of about 200 fibers and the lock is then soaked in the test composition (bath ratio of 2 g of composition per gram of hair) for 30 seconds, draining by finger and finally leaving suspended to dry it naturally. A heat treatment with a straightening iron at 190°C (Babyliss PRO, EP technology 5.0 sold by the company Babyliss) is performed three times successively.

After treatment, an evaluation is made with a light microscope to see if the fiber is repaired, i.e. if the two parts of the end of the fiber are united.

Next, the lock is shampooed five times. A shampoo wash cycle consists in soaking the lock in an aqueous 15% sodium laureth sulfate solution for 15 seconds and then soaking the lock in a bath of clean water for 15 seconds, and then leaving it suspended to dry it naturally.

After the five shampoo washes, an evaluation is made with a light microscope to see if the fiber is repaired, i.e. if the two parts of the end of the fiber are united. Results

The number of repaired fibers for each of the test compositions is indicated in the table below:

[Table 2]

Thus, the process according to the present invention enables the keratin fibers to be repaired, especially the split ends of the hair. The repair of the fibers is resistant to repeat shampooing.

Example 2

The following compositions were prepared: [Table 3]

⁴ Phloroglucinol tricyclocarbonate CAS No. 1980062-58-5 from the company Specific

Polymers of formula If

⁶ Propylene carbonate CAS 108-32-7 from Sigma Aldrich reference :310328 Split end hair repair study

Protocol

The evaluation of the repair of keratin fibers was carried out using an optical microscope (model 175 X optical "mightyscope 1.3M digital microscope" marketed by the company Aven Inc, USA - aveninc.com). Each fiber used in the study is a natural fiber 15 cm long and naturally split in two, longitudinally at the tip (split-end hair "forked hair") marketed by IHIP (Glendale, NY 11385, USA).

The tip of each fiber was observed before treatment and after treatment under a microscope. The treatment of the fibers consists of placing 5 split fibers (marked with a piece of duct tape and numbered (at the root end)) in a hair strand of about 200 fibers and then applying the composition to be tested (0.4g composition per gram of hair).

The hair was massaged for 30 seconds, combed and then a thermal treatment with a flat iron at 190 degrees Celsius (Babyliss PRO EP technology 5.0 marketed by Babyliss) was carried out 3 times in succession. After treatment, the optical microscope was used to see if the fiber was repaired, i.e. if the two parts of the end of the fiber were combined. Then the hair was shampooed five times. A shampoo cycle involves soaking the hair in a 15% sodium laureth sulfate aqueous solution for 15 seconds, then soaking the hair in a clean water bath for 15 seconds, then letting it hang to dry in the open air. After the five shampoos, the optical microscope was used to see if the fiber was repaired, i.e. if the two parts of the end of the fiber were combined the hair was repaired.

[Table 4]

Claims

1. A process for repairing keratin fibers, comprising:

(i) a step consisting in applying to the keratin fibers at least a) one compound of formula (I) below:

in which formula (I):

- (A L K) _m- (Q)_q- (Z)_z- (Y) _y- (A L K') _p- (W)_w- ;

i) (Ci-Cioo)alkylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1 -C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl,

(CrC4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals, ii) (C2-Cioo)alkenylene optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl, (Ci- C4)alkyl or (CrC4)alkoxy, preferably a C1-C4 alkyl such as methyl; preferably, said alkenylene radical denotes a (C2-Cioo)alkenylene radical optionally interrupted with one or more oxygen atoms and/or with one or more -SiMe2 radicals,

iii) (hetero)arylene such as phenylene, for instance 1 ,3-phenylene,

iv) (hetero)cycloalkylene,

said polyvalent group being chosen, when u = 3 or 4, from:

u represents an integer ranging from 2 to 4, preferably 2 or 3,

it being understood that:

- the following units:

are identical or different; and

2. The process as claimed in claim 1 , in which the compound of formula (I) is such that u is equal to 2 or 3 and T represents a divalent or trivalent group chosen from ii) (Ci- C₆)alkylene, iv) (hetero)arylene and v) cycloalkylene.

3. The process as claimed in claim 1 , in which the compound of formula (I) is such that u is equal to 2 and T represents a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen or sulfur atoms and/or with one or more radicals NR with R representing a hydrogen atom or a C1-C4 alkyl radical such as NH and/or with one or more radicals— Si(R'¹)(R'²)- with R'¹ and R'², which may be identical or different, representing a hydrogen atom, hydroxyl, (CrC4)alkyl or (CrC4)alkoxy, preferably a Ci- C4 alkyl such as methyl; preferably, said alkylene radical denotes a (Ci-Cioo)alkylene radical optionally interrupted with one or more oxygen atoms and/or with one or more - SiMe2 radicals.

4. The process as claimed in the preceding claim, in which T represents a radical T1 of formula -(CH₂)_xi-[0-(CH₂)_x2-]_x3 (0)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)-0-]_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 and R'², which may be identical or different, representing a (CrC4)alkyl radical such as methyl.

5. The process as claimed in claim 1 , in which the compound of formula (I) is 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 cycloalkylene group, preferably cyclohexylene, preferably substituted with one or more C1-C4 alkyl radicals such as methyl, or

- a divalent C₁-C₄ alkylene group such as methylene, ethylene or butylene.

6. The process as claimed in claim 1 , in which the compound of formula (I) is such that u is equal to 3 and T represents i) a saturated or unsaturated, preferably saturated, linear or branched trivalent hydrocarbon-based radical containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, ii) an aromatic or nonaromatic, preferably aromatic, trivalent (hetero)cyclic radical containing 5 or 6 carbon atoms, preferably 6 carbon atoms, such as a trivalent 1 ,3,5-phenyl radical.

7. The process as claimed in any one of the preceding claims, in which the compound of formula (I) is such that u is 2 and:

- one of the units:

- the other unit: is such that m + p is 0; preferably, the other unit is such that m+p+q+z+y+w is 0.

8. The process as claimed in any one of the preceding claims, in which the compound of formula (I) is chosen from the following compounds:

!e If

O

u

1m with s being an integer ranging from 4 to 30, preferably from 5 to 10;

and mixtures thereof.

9. The process as claimed in any one of the preceding claims, in which the process is a process for repairing hair, preferably a process for repairing split ends.

10. The process as claimed in any one of the preceding claims, characterized in that the process also comprises, following the set of steps (i) and (ii), a step (iii) of heat treatment of the keratin fibers at a temperature ranging from 40°C to 230°C, preferably from 60°C to 190°C.

11. The process as claimed in any one of the preceding claims, in which the amino silicone is chosen from:

a) the polysiloxanes of formula (A) below:

b) the amino silicones of formula (B) below:

R'aG3-a-Si(0SiG₂)n-(0SiGbR'2-b)m-0-SiG3-a-R'a (B)

in which:

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 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10; - R', which may be 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 following groups:

-N(R")₂; -N⁺(R")₃ A-; -NR"-Q-N(R")₂ and -NR"-Q-N⁺(R")₃ A-,

c) the amino silicones of formula (C) below:

in which:

- Ri , R₂, R₃ and R₄, which may be 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 ranging from 1 to 5,

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

- x is chosen such that the amine number ranges from 0.01 to 1 meq/g,

e) and mixtures thereof,

preferably from the amino silicones of formula (B).

12. The process as claimed in any of the preceding claims, in which the amino silicone is chosen from:

- the silicones known as“trimethylsilylamodimethicone” corresponding to formula (D): in which m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10;

- the silicones of formula (E) below:

in which:

- R1 , R2 and R3, which may be identical or different, represent a hydroxyl or C1 -C4 alkoxy radical, at least one of the radicals R1 to R3 denoting an alkoxy radical;

- the silicones of formula (F) below: in which:

- R1 and R2, which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals R1 or R2 denoting an alkoxy radical;

- the silicones of formula (G) below:

in which:

- A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms;

- the silicones of formula (H) below: in which:

- the silicones of formula (J) below:

171

in which:

- m and n are numbers ranging from 1 to 5000, and in particular n possibly denoting a number ranging from 10 to 2000 and notably from 100 to 1000, and in particular m possibly denoting a number from 1 to 100;

- Ri and R2, which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated alkyl radical comprising from 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, preferably from 12 to 20 carbon atoms;

- A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms; this radical is preferably branched;

- the silicones of formula (K) below: in which the value of n is such that the weight-average molecular weight (Mw) of the silicone ranges from 500 to 55 000;

- and mixtures thereof, preferably from the silicones of formulae (J) and (K) and mixtures thereof.

13. The process as claimed in any one of the preceding claims, in which steps (i) and (ii) are performed simultaneously by applying to the keratin fibers a composition (Ci) comprising:

a) the compound(s) of formula (I); and

b) the amino silicone(s); and

c) optionally at least one organic solvent, preferably chosen from:

- isododecane;

- polyols comprising from 2 to 30 hydroxyl groups and a (C2-Cs)alkyl group, preferably a (C2-C4)alkyl group, and mixtures thereof,

more preferentially from monoalcohols and polyols comprising two hydroxyl groups, even more preferentially from ethanol and polyols comprising two hydroxyl groups and at least three carbon atoms, most preferentially from ethanol, propylene glycol (1 ,2- propanediol); 1 ,3-propanediol; 1 ,3-butylene glycol; 1 ,2-pentanediol; dipropylene glycol; hexylene glycol; pentylene glycol; butylene glycol; glycerol; ethylene glycol, and mixtures thereof.

14. The process as claimed in claim 13, in which composition (Ci) comprises a total content of compounds of formula (I) from 0.01 % to 20%, preferably from 0.05% to 15%, more preferentially from 0.1% to 10%, even more preferentially from 0.5% to 5%, most preferentially from 1% to 5% by weight relative to the total weight of composition (Ci).

15. The process as claimed in claim 13 or 14, in which composition (Ci) comprises a total content of amino silicones from 0.1 % to 85%, preferably from 0.5% to 20%, more preferentially from 1% to 10% by weight relative to the total weight of composition (Ci).

16. The process as claimed in any one of claims 13 to 15, in which composition (Ci) comprises a total content of organic solvents ranging from 0% to 99%, preferably ranging from 20% to 95% by weight, more preferentially ranging from 50% to 80% by weight, relative to the total weight of composition (Ci).

17. The process as claimed in any one of claims 13 to 16, in which the pH of composition (Ci) is less than or equal to 10, preferably the pH of composition (Ci) may range from 3 to 9 and more preferentially the pH of composition (Ci) may range from 4 to 8.

18. The process as claimed in any one of the preceding claims, in which steps (i) and (ii) are performed by applying to the keratin fibers:

- a composition (C_å) comprising a) the compound(s) of formula (I); and

- a composition (C₃) comprising b) the amino silicone(s);

it being understood that:

- composition (C_å) is applied before composition (C₃) or composition (C₃) is applied before composition (C₂).

19. The use of at least one compound of formula (I) as defined in any one of claims 1 to 18 in combination with at least one amino silicone as defined in any one of claims 1 to 18 for repairing keratin fibers, preferably for repairing hair, most preferentially for repairing split ends.

20. The use of a composition (Ci) as defined in any one of claims 13 to 17 for repairing keratin fibers, preferably for repairing hair, most preferentially for repairing split ends.

21. A multi-compartment device comprising:

- a first compartment containing a composition (C_å) comprising a) the compound(s) of formula (I) as defined in any one of claims 1 to 12; and

- a second compartment containing a composition (C3) different from composition (C2), composition (C3) comprising b) the amino silicone(s) as defined in any one of claims 1 to 12.