FR3130616A1 - Hair coloring process comprising the application of a (poly)carbodiimide compound, a silicone acrylic copolymer, a surfactant and a coloring agent - Google Patents

Abstract

Title: Process for coloring hair comprising the application of a (poly)carbodiimide compound, a silicone acrylic copolymer, a surfactant and a coloring agent The present invention relates to a process for coloring hair comprising the application to the hair of at least one composition C comprising: a) one or more (poly)carbodiimide compounds; and b) one or more silicone acrylic copolymers, c) one or more surfactants, and d) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof.

Description

Hair coloring process comprising the application of a (poly)carbodiimide compound, a silicone acrylic copolymer, a surfactant and a coloring agent

The present invention relates to a hair dyeing process comprising the application to the hair of at least one composition C comprising one or more (poly)carbodiimide compounds; one or more silicone acrylic copolymers; one or more surfactants and; and at least one coloring agent.

In the field of coloring hair keratin fibers, in particular human hair, it is already known to color hair keratin fibers by different techniques using direct dyes or pigments for non-permanent colorings or dye precursors for permanent colorings .

There are basically three types of hair coloring process:
a) so-called permanent coloring which has the function of bringing a significant modification of the natural color and which uses oxidation dyes which penetrate the hair fiber and form the dye by a process of oxidative condensation;
b) non-permanent, semi-permanent or direct coloring, which does not involve the process of oxidative condensation and resists 4 or 5 shampoos; consists in dyeing the keratin fibers with dye compositions containing direct dyes;
c) temporary coloring which gives rise to a modification of the natural color of the hair which holds from one shampoo to another and which is used to embellish or correct a shade already obtained. It can also be likened to a “make-up” process.

Another coloring method is to use pigments. Indeed, the use of pigment on the surface of keratin fibers generally makes it possible to obtain visible colorings on dark hair since the pigment on the surface masks the natural color of the fiber. However, the colorings obtained by this method of coloring have the disadvantage of having a low resistance to shampoos as well as to external agents such as sebum, perspiration, brushing and/or rubbing.

There therefore remains a need to have a hair coloring process, which has the advantage of obtaining a homogeneous colored coating on the hair, while forming a coating that is resistant to shampoos and to the various attacks that the hair may suffer such as than brushing and/or rubbing without degrading the cosmetic properties of the hair.

Thus, the object of the present invention is to develop a hair coloring process which has the advantage of obtaining a homogeneous and smooth colored coating on the hair, while forming a coating that is resistant to shampoos and to the various attacks that the hair can be subjected to such brushing and/or rubbing without degradation of the cosmetic properties of the hair.

A subject of the present invention is therefore a hair dyeing process comprising the application to the hair of at least one composition C comprising:
a) one or more (poly)carbodiimide compounds;
b) one or more silicone acrylic copolymers,
c) one or more surfactants, and
d) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof.

Thanks to the hair coloring process according to the invention, colored sheathings are obtained on the hair making it possible to obtain a visible coloring on all types of hair in a shampoo-retentive manner while preserving the physical qualities of the hair.

Such a sheathing can be resistant to the external aggressions that the hair can undergo, such as brushing and perspiration. In particular, it makes it possible to obtain a homogeneous deposit.

By “ shampoo-resisting coloration ” is meant within the meaning of the present invention that the coloration obtained persists after shampooing.

By “ hair keratinous fibres ”, we mean the hair. In other words, the expressions “keratin hair fibers” and “hair” are equivalent in the remainder of the description.

Within the meaning of the present invention, the term " hair " means the hair of the head. This term does not correspond to body hair, eyebrows, or eyelashes

The expression " at least one " means one or more.

Unless otherwise indicated, the limits of a range of values are included in this range, in particular in the expressions “included between” and “ranging from … to …”.

The invention is not limited to the examples illustrated. The characteristics of the various examples can in particular be combined within variants that are not illustrated.

Within the meaning of the present invention and, unless otherwise indicated,
- an “ alkyl ” radical denotes a saturated linear or branched radical containing, for example, from 1 to 20 carbon atoms;
- an “ aminoalkyl ” radical denotes an alkyl radical as defined above, said alkyl radical comprising an NH ₂ group;
- a “ hydroxyalkyl ” radical denotes an alkyl radical as defined above, said alkyl radical comprising an OH group;
- an “ alkylene ” radical designates a divalent C ₂ -C ₄ saturated hydrocarbon group, linear or branched, such as methylene, ethylene or propylene;
- a " cycloalkyl " or " alicycloalkyl " radical denotes a mono or bicyclic saturated cyclic hydrocarbon group, preferably monocyclic, comprising from 1 to 3 rings, preferably 2 rings, and comprising from 3 to 24 carbon atoms, in particular comprising 3 to 20 carbon atoms, more particularly from 3 to 13 carbon atoms, even more particularly from 3 to 12 carbon atoms, preferably between 5 and 10 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, or norbornyl , in particular cyclopropyl, cyclopentyl or a cyclohexyl. it being understood that the cycloalkyl radical can be substituted by one or more (C ₁ -C ₄ )alkyl groups such as methyl, preferably the cycloalkyl radical is then an isobornyl group,
- a “ cycloalkylene ” radical designates a divalent cycloalkyl group with “ cycloalkyl ” as defined above, preferably C ₃ -C ₁₂ ;
- an “ aryl ” radical is an unsaturated and aromatic hydrocarbon cyclic radical, comprising from 6 to 14 carbon atoms, preferably between 6 and 12 carbon atoms, mono/bi/ or tri/cyclic, fused or not, preferably the aryl group comprises 1 ring with 6 carbon atoms such as phenyl, naphthlyl, , anthryl, phenanthryl and biphenyl, it being understood that the aryl radical can be substituted by one or more (C ₁ -C ₄ )alkyl groups such as methyl, preferably tolyl, xylyl, or methylnaphthyl, preferably the aryl group represents phenyl;
- an " arylene " radical is a divalent aryl radical with " aryl " as defined above preferably arylene represents phenylene;
- a “ heterocyclic ” radical designates a mono or polycyclic, saturated or unsaturated, non-aromatic or aromatic hydrocarbon radical, comprising one or more heteroatoms, preferably of 1 to 5 atoms chosen from O, S or N, comprising from 3 to 20 chains of preferably between 5 and 10 members such as imidazolyl, pyrrolyl and furanyl;
- a “ heterocycloalkylene ” radical is a divalent heterocyclic group with “ heterocyclic ” as defined previously;
- an “ aryloxy ” radical denotes an aryl-oxy radical with “ aryl ” as defined previously;
- an “ alkoxy ” radical denotes an alkyl-oxy radical with “ alkyl ” as defined above;
- an " acyloxy " radical denotes an ester radical RC(O)-O- with R an alkyl group as defined above;
- a “reactive” group is a group capable of forming a covalent bond with another group, identical or different, by chemical reaction.

Unless otherwise indicated, when compounds are mentioned in the present application, it is also meant their optical isomers, their geometric isomers, their tautomers, their salts, alone or as a mixture.

Claims (22)

Hair dyeing process comprising the application to the hair of at least one composition C comprising:
a) one or more (poly)carbodiimide compounds; And
b) one or more silicone acrylic copolymers,
c) one or more surfactants, and
d) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof. Process according to Claim 1, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (I) below:
(I)
in which :
- X ₁ and X ₂ represent, independently, an oxygen atom O, a sulfur atom S or an NH group;
- R ₁ and R ₂ independently represent a group chosen from a hydrocarbon radical, preferably alkyl, optionally interrupted by one or more heteroatom(s), a group chosen from alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl groups , carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulphonylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkylepoxide such as propylepoxide or butylepoxide, and azacyclopropane, and a hydrocarbon radical é, preferably alkyl, optionally interrupted by one or several heteroatom(s) and by one or more groups chosen from alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acyl groups pentadienylalkylsilyl, maleimidoalkylsilyl, sulphonylalkylsilyl, (meth) acrylalkyl, crotonylalkyl, alkylepoxide such as propylepoxide or butylepoxide, and azacyclopropane;
- n denotes an integer ranging from 1 to 1000; And
- A is a monomer chosen from the compounds below:

Process according to Claim 1, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (II) below:
(II),
in which
- X ₁ and X ₂ represent, independently, an oxygen atom O, a sulfur atom S or an NH group;
- R ₁ and R ₂ independently represent a hydrocarbon radical optionally interrupted by one or more heteroatom(s);
- n and z denote an integer ranging from 1 to 20, with n+z≥2 and w denotes an integer ranging from 1 to 3;
- L ₁ independently represents a C ₁ -C ₁₈ divalent aliphatic hydrocarbon radical, a C ₃ -C ₁₅ cycloalkylene radical, a C ₃ -C ₁₂ heterocycloalkylene group, or a C ₆ -C ₁₄ arylene group, and their mixtures;
- E independently represents a group chosen from:
-OR ₃ -O-; -SR ₄ -S-; -R ₅ -N(R ₆ )-R ₄ -N(R ₆ )-R ₅ -,
in which R ₃ and R ₄ independently represent a divalent hydrocarbon radical optionally interrupted by one or more heteroatom(s);
- R ₅ independently represents a covalent bond or a divalent saturated hydrocarbon radical, optionally interrupted by one or more heteroatom(s);
- R ₆ independently represents a hydrogen atom, or a hydrocarbon radical optionally interrupted by one or more heteroatom(s). Process according to Claim 3, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (II) in which:
- X ₁ and X ₂ independently represent an oxygen atom;
- R ₁ and R ₂ are chosen independently from dialkylamino alcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, and mixtures thereof;
- n and z denote an integer ranging from 1 to 20, with n+z ≥ 2 and w is equal to 1;
- L1 is chosen from a divalent C ₁ -C ₁₈ aliphatic hydrocarbon radical, a C ₃ -C ₁₅ cycloalkylene radical, a C ₃ -C ₁₂ heterocycloalkylene group, or a C ₆ -C ₁₄ arylene group, and their mixtures;
- E independently represents a group chosen from:
- -OR ₃ -O-; -SR ₄ -S-; -R ₅ -N(R ₆ )-R ₄ -N(R ₆ )-R ₅ -;
in which R3 and R4 are chosen independently from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatoms ( s), and mixtures thereof;
- when R ₅ is not a covalent bond, R ₅ is chosen from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof; And
- R ₆ is chosen from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatom(s), and their mixtures. Process according to Claim 3 or 4, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (II) in which:
- X ₁ and X ₂ independently represent an oxygen atom;
- R ₁ and R ₂ are independently monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed;
- n and z denote an integer ranging from 1 to 20, with n+z ≥ 2 and w is equal to 1;
- L ₁ is a C ₃ -C ₁₅ cycloalkylene radical;
- E independently represents a group chosen from:
-OR ₃ -O-; -SR ₄ -S-; -R ₅ -N(R ₆ )-R ₄ -N(R ₆ )-R ₅ -;
in which R ₃ and R ₄ are chosen independently from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof;
- when R ₅ is not a covalent bond, R ₅ is chosen from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof; And
- R ₆ is chosen from a C ₆ -C ₁₄ arylene radical, a C ₃ -C ₁₂ cycloalkylene radical, a linear or branched C ₁ -C ₁₈ alkylene radical, optionally interrupted by one or more heteroatom(s), and their mixtures. Process according to any one of Claims 3 to 5, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (II) in which:
-X₁ and X₂independently represent an oxygen atom;
-R₁and R₂, independently represent the compound of formula (VI) below:
R₁₃-[O-CH₂-C(H)(R)₁₄)]_q- (VI),
in which R₁₃represents a C-alkyl group₁-VS₄or phenyl, preferably C-alkyl₁-VS₄, more preferably a methyl, R₁₄represents a hydrogen atom or a C-alkyl group₁-VS₄, preferably a hydrogen atom and q denotes an integer ranging from 4 to 30;
- n and z denote an integer ranging from 2 to 20, with n+z ranging from 4 to 10 and w is equal to 1;
- I₁is a C cycloalkylene radical₃-VS₁₅such as cyclopentylene, cycloheptylene, cyclohexylene and 4,4-dicyclohexylene methane, and
- E represents an -O-R group₃-O- in which R₃is selected from a C arylene radical₆-VS₁₄, a C cycloalkylene radical₃-VS₁₂, a linear or branched C alkylene radical₁-VS₁₈, optionally interrupted by one or more heteroatom(s), and mixtures thereof. Process according to any one of Claims 3 to 6, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (II) in which:
- X ₁ and X ₂ independently represent an oxygen atom;
- R ₁ and R ₂ independently represent the compound of formula (VI) below:
R ₁₃ -[O-CH ₂ -C(H)(R ₁₄ )] _q - (VI),
in which R ₁₃ represents a C ₁ -C ₄ alkyl group or a phenyl, preferably a C ₁ -C ₄ alkyl group, more preferably a methyl, R ₁₄ represents a hydrogen atom or a C ₁ alkyl group -C ₄ , preferably a hydrogen atom and q denotes an integer ranging from 4 to 30;
- n and z denote an integer ranging from 2 to 20, with n+z ranging from 4 to 10, and w is equal to 1;
- L ₁ is a C ₃ -C ₁₅ cycloalkylene radical such as cyclopentylene, cycloheptylene, cyclohexylene and 4,4-dicyclohexylene methane, preferably 4,4-dicyclohexylene methane; And
- E represents an -OR ₃ -O- group in which R ₃ represents a linear or branched C ₁ -C ₁₈ alkylene radical such as methylene, propylene, butylene, ethylene, optionally interrupted by one or more heteroatom(s) . Process according to any one of Claims 3 to 7, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (XII) below:
(XII),
in which L ₁ is 4,4-dicyclohexylene methane, n and z denote an integer ranging from 2 to 20, with n+z ranging from 4 to 10, E represents a -OR ₃ -O- group in which R ₃ represents a linear or branched C ₁ -C ₁₈ alkylene radical such as methylene, propylene, butylene ethylene, optionally interrupted by one or more heteroatom(s), and r and s denote an integer ranging from 4 to 30. Process according to any one of the preceding claims, characterized in that the total quantity of the (poly)carbodiimide compound(s) ranges from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight , more preferably from 0.2 to 10% by weight, even more preferably from 0.5 to 8% by weight, better still from 1 to 6% by weight relative to the total weight of composition C. Process according to any one of the preceding claims, characterized in that the silicone acrylic copolymer(s) comprise:
- at least one acrylic or methacrylic or crotonic pattern; And
- at least one polydimethylsiloxane unit (PDMS). Process according to any one of the preceding claims, characterized in that the silicone acrylic copolymer(s) comprise:
- at least one crotonic unit and at least one unit chosen from an alkyl crotonate unit, the alkyl radical being a linear or branched, saturated radical containing from 1 to 20 carbon atoms; a vinyl acetate unit; a vinyl alkyl ester unit, the alkyl radical being a linear or branched, saturated radical containing from 2 to 20 carbon atoms; and mixtures thereof; And
- at least one polydimethylsiloxane unit (PDMS). Process according to any one of the preceding claims, characterized in that the silicone acrylic copolymer(s) comprise:
- at least one crotonic unit, at least one vinyl acetate unit and at least one vinyl alkyl ester unit, the alkyl radical being a linear or branched, saturated radical containing from 2 to 18 carbon atoms, preferably from 6 to 16 carbon atoms , And
- at least one polydimethylsiloxane unit (PDMS) comprising at least one polymerizable radical group a vinyl group. Process according to any one of the preceding claims, characterized in that the total quantity of silicone acrylic copolymer(s) ranges from 0.1 to 30% by weight, preferably from 0.5 to 20% by weight, more preferably from 1 to 15% by weight, better still from 2 to 10% by weight relative to the total weight of composition C. Process according to any one of the preceding claims, characterized in that composition C comprises one or more surfactants chosen from anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants and mixtures thereof, more preferably chosen from anionic surfactant, nonionic surfactants and mixtures thereof. Process according to Claim 14, characterized in that composition C comprises one or more surfactants chosen from C ₆ -C ₂₄ alkyl sulphates, in particular C ₁₂ -C ₂₀ alkyl sulphates, C ₆ -C ₂₄ alkyl ether sulphates, in particular C ₁₂ -C ₂₀ ; preferably comprising from 2 to 20 ethylene oxide units; polyethoxylated C ₈ -C ₃₀ fatty alcohols, polyoxyethylenated C ₈ -C ₃₀ fatty acid esters, these compounds preferably having 2 to 150 moles of ethylene oxide, and mixtures thereof, better chosen from alkyl ether sulphates C ₆ -C ₂₄ , in particular C ₁₂ -C ₂₀ ; preferably comprising from 2 to 20 ethylene oxide units; polyethoxylated C ₈ -C ₃₀ fatty alcohols preferably having 2 to 150 moles of ethylene oxide and mixtures thereof. Process according to any one of the preceding claims, characterized in that the surfactant(s) are present in a total quantity varying from 0.01% to 20%, preferably from 0.1 to 15 %, more preferably from 0.5 to 12%, more preferably still from 1 to 10% by weight relative to the total weight of composition C. Process according to any one of the preceding claims, characterized in that the total quantity of coloring agent(s) ranges from 0.001 to 20% by weight, preferably from 0.005 to 15% by weight, relative to the total weight of composition C, preferably the coloring agent(s) are chosen from pigments. Process according to any one of the preceding claims, characterized in that it further comprises a step of applying to the hair a composition D comprising at least one silicone compound comprising at least one carboxylic group. Process according to Claim 18, characterized in that the total quantity of silicone compound(s) comprising at least one carboxylic group ranges from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight , more preferably from 0.5 to 10% by weight, better still from 1 to 5% by weight relative to the total weight of composition D. Process according to Claim 18 or 19, characterized in that composition D additionally comprises one or more oil(s), preferably chosen from C ₈ -C ₁₆ alkanes, more preferably from isododecane, isohexadecane, tetradecane and/or mixtures thereof. Process according to any one of Claims 1 to 17, characterized in that it consists in mixing extemporaneously at the time of use at least two compositions A and B to obtain a composition C and in applying composition C to the hair, with :
- composition A comprising one or more (poly)carbodiimide compound(s) as defined according to any one of claims 2 to 8;
- composition B comprising one or more silicone acrylic copolymer(s) as defined according to any one of claims 10 to 12, and one or more surfactants as defined ) according to any one of claims 14 or 15,
composition A and/or composition B comprising at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof. Device for coloring hair comprising several compartments containing:
- in a first compartment, a composition A comprising:
a) one or more (poly)carbodiimide compound(s) as defined according to any one of claims 2 to 8,
-in a second compartment, a composition B comprising:
b) one or more silicone acrylic copolymers as defined according to any one of claims 10 to 12, and
c) one or more surfactants as defined according to any one of claims 14 or 15, and
composition A and/or composition B comprising
d) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof and
- optionally in a third compartment, a composition D comprising at least one silicone compound comprising at least one carboxylic group as defined according to any one of claims 18 to 20.