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WO2023111268A1 - Procédé de coloration capillaire, comprenant l'application d'un composé (poly)carbodiimide de formule spécifique, d'un polymère acrylique de silicone, de deux composés ayant des paramètres de solubilité de hansen spécifiques et d'un agent colorant - Google Patents

Procédé de coloration capillaire, comprenant l'application d'un composé (poly)carbodiimide de formule spécifique, d'un polymère acrylique de silicone, de deux composés ayant des paramètres de solubilité de hansen spécifiques et d'un agent colorant Download PDF

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Publication number
WO2023111268A1
WO2023111268A1 PCT/EP2022/086355 EP2022086355W WO2023111268A1 WO 2023111268 A1 WO2023111268 A1 WO 2023111268A1 EP 2022086355 W EP2022086355 W EP 2022086355W WO 2023111268 A1 WO2023111268 A1 WO 2023111268A1
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radical
group
chosen
composition
weight
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PCT/EP2022/086355
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English (en)
Inventor
Chrystel POURILLE
Alexis LIARD
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L'oreal
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Publication of WO2023111268A1 publication Critical patent/WO2023111268A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • TITLE Hair dyeing process, comprising the application of a (poly)carbodiimide compound of specific formula, a silicone acrylic polymer, two compounds with specific Hansen solubility parameters and a colouring agent
  • the present invention relates to a hair dyeing process, comprising the application to the hair of a composition C comprising a (poly)carbodiimide compound of specific formula, a silicone acrylic copolymer, at least two compounds with specific Hansen solubility parameters and a colouring agent.
  • Another colouring method consists in using pigments.
  • the use of pigment on the surface of keratinous fibres generally makes it possible to obtain visible colourings on dark hair, since the surface pigment masks the natural colour of the fibre.
  • the colourings obtained via this colouring method have the drawback of having poor resistance to shampoo washing and also to external agents such as sebum, perspiration, brushing and/or rubbing.
  • a hair dyeing process which has the advantage of obtaining a uniform coloured coating on the hair, while at the same time forming a coating that is persistent with respect to shampoo washing and to the various attacking factors to which the hair may be subjected such as brushing and/or friction without degradation of the cosmetic properties of the hair.
  • the aim of the present invention is to develop a hair dyeing process which has the advantage of obtaining a smooth and uniform coloured coating on the hair, while at the same time forming a coating that is persistent with respect to shampoo washing and to the various attacking factors to which the hair may be subjected such as brushing and/or friction without degradation of the cosmetic properties of the hair.
  • One subject of the present invention is thus a hair dyeing process, comprising the application to the hair of at least one composition C comprising:
  • coloured coatings are obtained on the hair that make it possible to obtain a colouring that is visible on all types of hair in a manner that is persistent with respect to shampoo washing, while at the same time preserving the physical qualities of the hair.
  • a coating may be resistant to the external attacking factors to which the hair may be subjected, such as blow-drying and perspiration. It makes it possible in particular to obtain a uniform deposit.
  • the compositions used in the context of the hair dyeing process according to the invention also make it possible to obtain good solubility of said silicone acrylic copolymer.
  • the term “ colouring that is persistent with respect to shampoo washing ' means that the colouring obtained persists after one shampoo wash, preferably after three shampoo washes, more preferentially after five shampoo washes.
  • a/ least one means one or more. Unless otherwise indicated, the limits of a range of values are included in that range, notably in the expressions “between” and “ranging from ... to ...”.
  • the invention is not limited to the illustrated examples.
  • the characteristics of the various examples may notably be combined within variants which are not illustrated.
  • an “alkyl” radical denotes a linear or branched saturated radical containing, for example, from 1 to 20 carbon atoms;
  • an “aminoalkyl” radical denotes an alkyl radical as defined previously, said alkyl radical comprising an NH2 group;
  • hydroxyalkyl radical denotes an alkyl radical as defined previously, said alkyl radical comprising an OH group;
  • an “alkylene” radical denotes a linear or branched divalent saturated C2-C4 hydrocarbon-based group such as methylene, ethylene or propylene;
  • cycloalkyl or “alicycloalkyl” radical denotes a cyclic saturated monocyclic or bicyclic, preferably monocyclic, hydrocarbon-based group comprising from 1 to 3 rings, preferably 2 rings, and comprising from 3 to 24 carbon atoms, in particular comprising from 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 norbomyl, in particular cyclopropyl, cyclopentyl or cyclohexyl, it being understood that the cycloalkyl radical may be substituted with one or more (Ci-C4)alkyl groups such as methyl; preferably, the cycloalkyl radical is then an isobornyl group;
  • cycloalkylene denotes a divalent cycloalkyl group with “cycloalkyl” as defined previously, preferably of C3-C12;
  • an “aryl” radical is a monocyclic, bicyclic or tricyclic, fused or non-fused, unsaturated and aromatic hydrocarbon-based cyclic radical, comprising from 6 to 14 carbon atoms, preferably between 6 and 12 carbon atoms; preferably, the aryl group comprises 1 ring of 6 carbon atoms such as phenyl, naphthyl, anthryl, phenanthryl and biphenyl, it being understood that the aryl radical may be substituted with one or more (Ci-C4)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 previously; preferably, arylene represents phenylene;
  • a “heterocyclic” radical denotes a saturated or unsaturated, non-aromatic or aromatic, monocyclic or polycyclic hydrocarbon-based radical, comprising one or more heteroatoms, preferably from 1 to 5 atoms chosen from O, S or N, including from 3 to 20 ring members, preferably between 5 and 10 ring members, such as imidazolyl, pyrrolyl and furanyl;
  • a “'helerocycloalkylene” radical is a divalent heterocyclic group with “'heterocyclic” as defined previously;
  • an “ury/oxy” radical denotes an aryl-oxy with “aryl” as defined previously;
  • an “alkoxy” radical denotes an alkyl-oxy radical with “alkyl” as defined previously;
  • an “acyloxy” radical denotes an ester radical R-C(O)-O- with R being an alkyl group as defined previously;
  • a “reactive” group is a group that is capable of forming a covalent bond with another identical or different group, by chemical reaction.
  • keratinous hair fibres means the hair. In other words, the terms “keratinous hair fibres” and “hair” are equivalent in the continuation of the description.
  • hair means head hair. This term does not correspond to bodily hairs, the eyebrows or the eyelashes.
  • Composition C used in the context of the process according to the invention comprises at least one (poly)carbodiimide compound of specific formula (II) as defined above.
  • the composition may comprise at least two different (poly)carbodiimide compounds, present as a mixture in the composition.
  • hydrocarbon-based radical means a saturated or unsaturated, linear or branched radical containing from 1 to 300 carbon atoms, preferably from 1 to 250 carbon atoms, more preferentially from 1 to 200 carbon atoms.
  • the hydrocarbon-based radical is a saturated linear radical.
  • the hydrocarbon-based radical may comprise one or more cyclic groups.
  • the hydrocarbon-based radical may be interrupted with one or more heteroatom(s), in particular chosen from O, S or N and/or substituted with one or more cation(s), anion(s) or zwitterion(s) or cationic group(s) such as ammonium, anionic group(s) such as carboxylate, or zwitterionic group(s), and/or comprising a metal ion which may be incorporated in the form of a salt.
  • heteroatom(s) means an oxygen O, sulfur S or nitrogen N atom, and also halogen atoms such as Cl, F, Br and I.
  • the heteroatom is included in the chain of the hydrocarbon-based radical, the heteroatom is preferably chosen from oxygen O, sulfur S or nitrogen N atoms.
  • X 1 and X 2 independently represent an oxygen atom.
  • R 1 and R 2 are independently chosen from dialkylamino alcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed, and mixtures thereof.
  • R 1 and R 2 are independently chosen from groups (i) to (iv) below: (i) the compound of formula (III) below: R 7 -O-C(O)-C(R 8 )(H)- (III), in which R 7 represents a C 1 -C 3 alkyl group and R 8 represents a hydrogen atom or a C 1 - C 3 alkyl group; preferably, R 7 is a methyl and R 8 is a hydrogen atom or a methyl.
  • R 9 represents a C 1 -C 4 alkyl group
  • R 10 represents a hydrogen atom or a C 1 -C 4 alkyl group
  • p denotes an integer ranging from 1 to 3; preferably, R 9 is a methyl, ethyl or butyl, R 10 is a hydrogen atom or a methyl and p is equal to 1.
  • R 1 and R 2 independently represent a compound of formula (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 preferentially a methyl, Ri4 represents a hydrogen atom or a C1-C4 alkyl group, preferably a hydrogen atom and q denotes an integer ranging from 4 to 30.
  • Ri and R2 are different and one of the radicals Ri or R2 represents a compound of formula (IV) as described above and the other radical Ri or R2 represents a compound of formula (VI) as described above.
  • R9 is a methyl, ethyl or butyl and Rio is a hydrogen atom or a methyl and p is equal to 1.
  • R13 is a methyl, ethyl or butyl and R14 is a hydrogen atom or a methyl and q denotes an integer ranging from 4 to 30.
  • Ri and R2 are identical and represent a compound of formula (VI) in which R13 represents a C1-C4 alkyl group or a phenyl, preferably a C1-C4 alkyl group, more preferentially a methyl, R14 represents a hydrogen atom or a C1-C4 alkyl group, preferably a hydrogen atom and q denotes an integer ranging from 4 to 30.
  • n denotes an integer ranging from 1 to 20, more preferentially from 2 to 20.
  • z denotes an integer ranging from 1 to 20, more preferentially from 2 to 20.
  • w is equal to 1.
  • w is equal to 1
  • n+z denotes an integer ranging from 4 to 10.
  • Li is chosen from a Ci-Cis divalent aliphatic hydrocarbon-based radical such as methylene, ethylene and propylene, a C3-C15 cycloalkylene radical such as cyclopentylene, cycloheptylene and cyclohexylene, a C3-C12 heterocycloalkylene group such as imidazolene, pyrrol ene and furanylene, or a C6-C14 arylene group such as phenylene, and mixtures thereof.
  • a Ci-Cis divalent aliphatic hydrocarbon-based radical such as methylene, ethylene and propylene
  • a C3-C15 cycloalkylene radical such as cyclopentylene, cycloheptylene and cyclohexylene
  • a C3-C12 heterocycloalkylene group such as imidazolene, pyrrol ene and furanylene
  • a C6-C14 arylene group such as phenylene
  • Li may be chosen from a radical derived from tolylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, 2,2,4- trimethylhexamethylene diisocyanate, 1,12-dodecane diisocyanate, norbornane diisocyanate, 2,4-bis(8-isocyanatooctyl)-l,3-dioctylcyclobutane, 4,4’- dicyclohexylmethane diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, 1,5-napththylene diisocyanate, 4,4 ’-diphenylmethane diisocyanate, 4,4’- diphenyldimethylmethane diisocyanate and phenylene diisocyanate, and mixtures thereof.
  • Li is chosen from a C3-C15 cycloalkylene radical or a C6-C14 arylene group, and mixtures thereof, such as the compounds of formula (VII) below:
  • L1 is 4,4-dicyclohexylenemethane corresponding to formula (VIII) below: (VIII).
  • L1 is not the m-tetramethylxylylene radical represented by formula (IX) below: (IX).
  • E independently represents a group chosen from: - -O-R 3 -O-; -S-R 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-based radical optionally interrupted with one or more heteroatom(s); - R 5 independently represents a covalent bond or a saturated divalent hydrocarbon- based radical, optionally interrupted with one or more heteroatom(s); and - R 6 independently represents a hydrogen atom or a hydrocarbon-based radical, optionally interrupted with one or more heteroatom(s).
  • R 3 and R 4 are independently chosen from a C 6 -C 14 arylene radical such as phenylene, a C 3 -C 12 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or branched C 1 -C 18 alkylene radical such as methylene and ethylene, optionally interrupted with one or more heteroatom(s), and mixtures thereof. More preferentially, R 3 and R 4 are independently chosen from a linear or branched C 1 -C 18 alkylene radical such as methylene, butylene, propylene, ethylene, optionally interrupted with one or more heteroatom(s).
  • R 5 is chosen from a C 6 -C 14 arylene radical such as phenylene, a C 3 -C 12 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or branched C 1 -C 18 alkylene radical such as methylene and ethylene, optionally interrupted with one or more heteroatom(s), and mixtures thereof.
  • arylene radical such as phenylene
  • C 3 -C 12 cycloalkylene radical such as cyclopropylene and cyclobutylene
  • a linear or branched C 1 -C 18 alkylene radical such as methylene and ethylene, optionally interrupted with one or more heteroatom(s), and mixtures thereof.
  • R 6 is chosen from a C 6 -C 14 arylene radical such as phenylene, a C 3 -C 12 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or branched C 1 -C 18 alkylene radical such as methylene and ethylene, optionally interrupted with one or more heteroatom(s), and mixtures thereof.
  • E represents a group -O-R 3 -O- in which R 3 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 with one or more heteroatom(s), and mixtures thereof.
  • E represents a group -O-R 3 -O- in which R 3 represents a linear or branched C 1 -C 18 alkylene radical such as methylene, butylene, propylene, ethylene, optionally interrupted with one or more heteroatom(s).
  • the (poly)carbodiimide compound is a copolymer derived from ⁇ -methylstyryl isocyanates of formula (X) below: (X), in which R independently represents an alkyl group containing from 1 to 24 carbon atoms, a cycloalkyl group containing from 3 to 24 carbon atoms or an aryl group containing from 6 to 24 carbon atoms, and n denotes an integer ranging from 2 to 100.
  • R independently represents an alkyl group containing from 1 to 24 carbon atoms, a cycloalkyl group containing from 3 to 24 carbon atoms or an aryl group containing from 6 to 24 carbon atoms
  • n denotes an integer ranging from 2 to 100.
  • alkyl group is as defined previously.
  • cycloalkyl group is as defined previously.
  • n may denote an integer ranging from 2 to 50, preferably from 3 to 30 and even more preferentially from 5 to 10.
  • the (poly)carbodiimide compound is a compound of formula (XI) below: (XI), in which R independently represents an alkyl group containing from 1 to 24 carbon atoms, a cycloalkyl group containing from 3 to 24 carbon atoms or an aryl group containing from 6 to 24 carbon atoms.
  • R independently represents an alkyl group containing from 1 to 24 carbon atoms, a cycloalkyl group containing from 3 to 24 carbon atoms or an aryl group containing from 6 to 24 carbon atoms.
  • the “alkyl group”, the “cycloalkyl group” and the “aryl group” are as defined previously.
  • the (poly)carbodiimide compound is 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 chosen from dialkylamino alcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed, and mixtures thereof, preferably monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed, more preferentially the compound of formula (VI) as described previously in which R 13 represents a C 1 -C 4 alkyl group or a phenyl, preferably a C 1 -C 4 alkyl group, more preferentially a methyl, R 14 represents a hydrogen atom or a C 1 -C 4 alkyl group, preferably a hydrogen atom, and q denotes an integer ranging from 4 to 30
  • the (poly)carbodiimide compound is 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 chosen from dialkylamino alcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl 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; - L 1 is chosen from a C 1 -C 18 divalent aliphatic hydrocarbon-based radical, a C 3 -C 15 cycloalkylene radical, a C 3 -C 12 heterocycloalkylene group or a C 6 -C 14 arylene group, and mixtures thereof; - E independently represents a group chosen from: - -O-R 3 -O-; -S-R 4 -
  • the (poly)carbodiimide compound is 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 hydroxyl 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: - -O-R 3 -O-; -S-R 4 -S-; -R 5 -N(R 6 )-R 4 -N(R 6 )-R 5 -; in which R 3 and R 4 are independently chosen from a C 6 -C 14 arylene radical, a C 3 -C 12 cycloalkylene radical, a linear or branched C 1
  • the (poly)carbodiimide compound is 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 preferentially a methyl, R 14 represents a hydrogen atom or a C 1 -C 4 alkyl group, 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, cycloh
  • the (poly)carbodiimide compound is 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 preferentially a methyl, R 14 represents a hydrogen atom or a C 1 -C 4 alkyl group, 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, cycloh
  • the (poly)carbodiimide compound is a compound of formula (XII) below: (XII), in which LI is 4, 4-di cyclohexylenemethane, n and z denote an integer ranging from 2 to 20, with n+z ranging from 4 to 10, E represents a group -O-R3-O- in which R3 represents a linear or branched Ci-Cis alkylene radical such as methylene, propylene, butylene, ethylene, optionally interrupted with one or more heteroatom(s), and r and s denote an integer ranging from 4 to 30.
  • the total amount of the (poly)carbodiimide compound(s) ranges from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, more preferentially from 0.2% to 10% by weight, even more preferentially from 0.5% to 8% and better still from 1% to 6% by weight, relative to the total weight of composition C.
  • Composition C employed within the context of the process according to the invention comprises one or more silicone acrylic copolymers.
  • said silicone acrylic copolymer(s) comprise:
  • PDMS polydimethylsiloxane
  • polydimethylsiloxanes (also referred to by the abbreviation PDMS), in accordance with general acceptance, means any organosilicon polymer or oligomer with a linear structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes and consisting essentially of a repetition of main units in which the silicon atoms are linked together via oxygen atoms (Si-O-Si siloxane bond), including methyl radicals directly linked via a carbon atom to said silicon atoms.
  • PDMS polydimethylsiloxanes
  • the PDMS chains that may be used to obtain the copolymer used according to the invention include at least one polymerizable radical group, preferably located on at least one of the ends of the chain, i.e. the PDMS may have, for example, a polymerizable radical group on each of the two ends of the chain or may have a polymerizable radical group on one end of the chain and a trimethyl silyl terminal group on the other end of the chain.
  • polymerizable radical group means a radical that is capable of polymerizing with other polymerizable radical groups or monomers.
  • the polydimethylsiloxane unit comprises at least one polymerizable radical group.
  • the polymerizable radical group comprises at least one vinyl group.
  • the polydimethylsiloxane (PDMS) unit comprises at least one polymerizable radical group comprising a vinyl group, preferably at least two polymerizable radical groups comprising a vinyl group, preferably located on at least one of the chain ends.
  • said silicone acrylic copolymer(s) comprise at least one acrylic or methacrylic or crotonic unit, i.e. at least one unit comprising a carboxylic group.
  • carboxylic group means a COOH or COO- functional group, it being possible for the counterion of the COO- group to be chosen from alkali metals, alkaline-earth metals and quaternary ammoniums.
  • said silicone acrylic copolymer(s) comprise:
  • PDMS polydimethylsiloxane
  • composition comprises one or more silicone acrylic copolymers comprising:
  • 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
  • PDMS polydimethylsiloxane
  • crotonate unit means a unit derived from a crotonic acid monomer or a salt thereof.
  • alkyl crotonate unit means a unit derived from a crotonic acid ester monomer, bearing a saturated, linear or branched alkyl radical containing from 1 to 20 carbon atoms.
  • vinyl alkyl ester unit means a unit derived from a vinyl ester monomer bearing a saturated, linear or branched alkyl radical containing from 2 to 20 carbon atoms.
  • vinyl acetate unit means a unit derived from a vinyl acetate monomer.
  • said 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 20 carbon atoms, preferably from 2 to 18 carbon atoms, and
  • PDMS polydimethylsiloxane
  • said silicone acrylic copolymer(s) comprise:
  • alkyl radical being a linear or branched, saturated radical containing from 6 to 16 carbon atoms
  • PDMS polydimethylsiloxane
  • composition comprises one or more silicone acrylic copolymer(s) comprising:
  • alkyl radical being a linear or branched, saturated radical containing from 2 to 20 carbon atoms, preferably from 2 to 18 carbon atoms;
  • PDMS polydimethylsiloxane
  • the composition comprises one or more silicone acrylic copolymer(s) comprising:
  • alkyl radical being a linear or branched, saturated radical containing from 6 to 16 carbon atoms
  • PDMS polydimethylsiloxane
  • the total amount of silicone acrylic copolymer(s) ranges from 0.1% to 30% by weight, preferably from 0.5% to 20% by weight, more preferentially from 1% to 15% by weight and better still from 2% to 10% by weight relative to the total weight of composition C.
  • Composition C used in the process according to the invention comprises at least two compounds having the following Hansen solubility ⁇ parameters: ⁇ h ranging from 5 to 40 MPa 1/2 and ⁇ p ranging from 4 to 14 Mpa 1/2 .
  • Said compounds are defined by specific solubility parameters in the three- dimensional solubility space according to Hansen (The three-dimensional solubility parameters, J. Paint Technol., 39, page 105 (1967)).
  • Hansen the change in internal energy upon vaporization is considered to be the sum of three contributions, the first due to hydrogen bonding (subscript h), the second to dipolar interactions (subscript p) and the third to dispersion forces (subscript d).
  • said compounds have a ⁇ h ranging from 10 to 35 Mpa 1/2 , preferably from 10 to 30 Mpa 1/2 , more preferentially from 12 to 30 Mpa 1/2 .
  • said compounds have a ⁇ p ranging from 5 to 13 Mpa 1/2 , preferably from 6 to 13 Mpa 1/2 .
  • said compounds are chosen from ethanol, methylpropanediol, tert-butanol, isopropanolamine, pentylene glycol, aminomethylpropanol, caprylyl glycol, triethanolamine, thioglycolic acid, hexylene glycol, 1,2-hexanediol, thiolactic acid, ethylhexylglycerol, ethanolamine, butylene glycol, dipropylene glycol, propan-2- ol, glycerol and mixtures thereof, preferably from ethanol, hexylene glycol, glycerol, methylpropanediol, dipropylene glycol and mixtures thereof.
  • said compounds are chosen from ethanol, hexylene glycol, dipropylene glycol, methylpropanediol and mixtures thereof.
  • the total amount of compounds having the Hansen solubility ⁇ parameters according to the invention ranges from 1% to 50% by weight, preferably from 2% to 40% by weight, more preferentially from 5% to 30% by weight, better still from 10% to 25% by weight relative to the total weight of composition C.
  • Colouring agent Composition C used in the context of the process according to the invention comprises one or more colouring agent(s) chosen from pigments, direct dyes and mixtures thereof.
  • composition C used in the context of the process according to the invention comprises one or more pigments.
  • composition B according to the invention comprises one or more pigments.
  • pigment refers to any pigment that gives colour to keratinous materials. Their solubility in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.
  • the pigments that may be used are notably chosen from the organic and/or mineral pigments known in the art, notably those described in Kirk-Othmer’ s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry.
  • They may be natural, of natural origin, or non-natural.
  • These pigments may be in pigment powder or paste form. They may be coated or uncoated.
  • the pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof.
  • the pigment may be a mineral pigment.
  • mineral pigment refers to any pigment that satisfies the definition in Ullmann’s encyclopaedia in the chapter on inorganic pigments.
  • the pigment may be an organic pigment.
  • organic pigment refers to any pigment that satisfies the definition in Ullmann’s encyclopaedia in the chapter on organic pigments.
  • the organic pigment may notably be chosen from nitroso, nitro, azo, xanthene, pyrene, quinoleine, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470
  • pigment pastes of organic pigments such as the products sold by the company Hoechst under the names:
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426.
  • These composite pigments may be composed notably of particles including a mineral core, at least one binder for attaching the organic pigments to the core, and at least one organic pigment which at least partially covers the core.
  • the organic pigment may also be a lake.
  • the term “lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the mineral substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate and aluminium.
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green 5 (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090).
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green 5 (CI 61
  • the pigment may also be a pigment with special effects.
  • pigments with special effects means pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.
  • pigments with special effects exist: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.
  • pigments with special effects include nacreous pigments such as mica covered with titanium or with bismuth oxychloride, coloured nacreous pigments such as mica covered with titanium and with iron oxides, mica covered with iron oxide, mica covered with titanium and notably with ferric blue or with chromium oxide, mica covered with titanium and with an organic pigment as defined previously, and also nacreous pigments based on bismuth oxychloride.
  • Nacreous pigments that may be mentioned include the nacres Cellini sold by BASF (mica-TiCh-lake), Prestige sold by Eckart (mica-TiCh), Prestige Bronze sold by Eckart (mica-Fe2O3) and Colorona sold by Merck (mica-TiO2-Fe2O3).
  • particles including a borosilicate substrate coated with titanium oxide.
  • Particles comprising a glass substrate coated with titanium oxide are notably sold under the name Metashine MC1080RY by the company Toyal.
  • nacres examples include polyethylene terephthalate glitter flakes, notably those sold by the company Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver glitter flakes). It is also possible to envisage multilayer pigments based on synthetic substrates, such as alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.
  • the pigments with special effects may also be chosen from reflective particles, i.e. notably from particles whose size, structure, notably the thickness of the layer(s) of which they are made and their physical and chemical nature, and surface state, allow them to reflect incident light.
  • This reflection may, where appropriate, have an intensity sufficient to create at the surface of the composition or of the mixture, when it is applied to the support to be made up, highlight points that are visible to the naked eye, i.e. brighter points that contrast with their environment, making them appear to sparkle.
  • the reflective particles may be selected so as not to significantly alter the colouring effect generated by the colouring agents with which they are combined, and more particularly so as to optimize this effect in terms of colour rendition. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or tint. These particles may have varied forms and may notably be in platelet or globular form, in particular in spherical form.
  • the reflective particles may or may not have a multilayer structure and, in the case of a multilayer structure, may have, for example, at least one layer of uniform thickness, notably of a reflective material.
  • the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, notably titanium or iron oxides obtained synthetically.
  • the reflective particles may include, for example, a natural or synthetic substrate, notably a synthetic substrate at least partially coated with at least one layer of a reflective material, notably of at least one metal or metallic material.
  • the substrate may be made of one or more organic and/or mineral materials.
  • glasses More particularly, it may be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, notably aluminosilicates and borosilicates, and synthetic mica, and mixtures thereof, this list not being limiting.
  • the reflective material may include a layer of metal or of a metallic material.
  • Reflective particles are notably described in documents JP-A-09188830, JP- A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
  • reflective particles including a mineral substrate coated with a layer of metal
  • Particles with a silver-coated glass substrate in the form of platelets, are sold under the name Microglass Metashine REFSX 2025 PS by the company Toyal.
  • Particles with a glass substrate coated with nickel/chromium/molybdenum alloy are sold under the names Crystal Star GF 550 and GF 2525 by this same company.
  • Use may also be made of particles comprising a metal substrate, such as silver, aluminium, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze or titanium, said substrate being coated with at least one layer of at least one metal oxide, such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.
  • a metal substrate such as silver, aluminium, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze or titanium
  • said substrate being coated with at least one layer of at least one metal oxide, such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.
  • Pigments with special effects also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots Corporation.
  • pigments that may be used in the present invention makes it possible to obtain a wide range of colours, and also particular optical effects such as metallic effects or interference effects.
  • the size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.
  • the pigments may be dispersed in the composition by means of a dispersant.
  • the dispersant serves to protect the dispersed particles against their agglomeration or flocculation.
  • This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments.
  • These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium.
  • esters of 12-hydroxy stearic acid in particular and of C8 to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by Henkel, or else polyhydroxystearic acid such as the product sold under the reference Arlacel Pl 00 by Uniqema, and mixtures thereof.
  • poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol such as the product sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by Henkel, or else polyhydroxystea
  • dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185 and DC2-5225 C.
  • the pigments used in the composition may be surface-treated with an organic agent.
  • the pigments surface-treated beforehand that are useful in the context of the invention are pigments which have been completely or partially subjected to a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature with an organic agent, such as those described notably in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention.
  • organic agents may be chosen, for example, from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and derivatives thereof, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol and lauric acid and derivatives thereof; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; alkanolamines; silicone compounds, for example silicones, notably polydimethylsiloxanes; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.
  • waxes for example carnauba wax and beeswax
  • the surface-treated pigments that are useful in the composition may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.
  • the surface-treated pigments that are useful in the context of the present invention may be prepared according to surface-treatment techniques that are well known to those skilled in the art, or may be commercially available as is.
  • the surface-treated pigments are coated with an organic layer.
  • the organic agent with which the pigments are treated may be deposited on the pigments by evaporation of solvent, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.
  • the surface treatment may thus be performed, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is notably described in patent US 4 578 266.
  • An organic agent covalently bonded to the pigments will preferably be used.
  • the agent for the surface treatment may represent from 0.1% to 50% by weight of the total weight of the surface-treated pigment, preferably from 0.5% to 30% by weight and even more preferentially from 1% to 20% by weight of the total weight of the surface-treated pigment.
  • the surface treatments of the pigments are chosen from the following treatments:
  • PEG-silicone treatment for instance the AQ surface treatment sold by LCW;
  • methicone treatment for instance the SI surface treatment sold by LCW;
  • a dimethicone treatment for instance the Covasil 3.05 surface treatment sold by LCW
  • a dimethicone/trimethyl siloxysilicate treatment for instance the Covasil 4.05 surface treatment sold by LCW
  • a magnesium myristate treatment for instance the MM surface treatment sold by LCW;
  • an aluminium dimyristate treatment such as the MI surface treatment sold by Miyoshi;
  • an isostearyl sebacate treatment for instance the HS surface treatment sold by Miyoshi;
  • an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment for instance the FSA surface treatment sold by Daito;
  • a polymethylhydrogenosiloxane/perfluoroalkyl phosphate treatment for instance the FS01 surface treatment sold by Daito;
  • an acrylate/dimethicone copolymer treatment for instance the ASC surface treatment sold by Daito;
  • an isopropyl titanium triisostearate treatment for instance the ITT surface treatment sold by Daito;
  • an acrylate copolymer treatment for instance the APD surface treatment sold by Daito;
  • the dispersant is present with organic or mineral pigments in submicron-sized particulate form in composition B.
  • micron or “submicronic” refers to pigments having a particle size that has been micronized by a micronization method and having a mean particle size of less than a micrometre (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.
  • pm micrometre
  • the dispersant and the pigment(s) are present in an amount (dispersantpigment), according to a weight ratio, of between 1 :4 and 4: 1, particularly between 1.5:3.5 and 3.5:1 or better still between 1.75:3 and 3: 1.
  • the dispersant(s) may therefore have a silicone backbone, such as silicone polyether and dispersants of amino silicone type other than the amino silicones mentioned below.
  • silicone backbone such as silicone polyether and dispersants of amino silicone type other than the amino silicones mentioned below.
  • suitable dispersants that may be mentioned are:
  • - aminosilicones i.e. silicones comprising one or more amino groups such as those sold under the names and references: BYK LPX 21879 by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, sold by Genesee Polymers,
  • Tego® RC 902 Tego® RC 922, Tego® RC 1041, and Tego® RC 1043, sold by Evonik
  • PDMS polydimethylsiloxane
  • carboxyl groups such as X-22162 and X-22370 by Shin-Etsu
  • epoxy silicones such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695 by Genesee Polymers, or Tego® RC 1401, Tego® RC 1403, Tego® RC 1412 by Evonik.
  • the dispersant(s) are of amino silicone type other than the amino silicones mentioned below and are cationic.
  • the pigment(s) are chosen from mineral, mixed mineral-organic or organic pigments.
  • the pigment(s) are organic pigments, preferentially organic pigments surface-treated with an organic agent chosen from silicone compounds.
  • the pigment(s) are mineral pigments.
  • the pigment(s) are chosen from iron oxides, notably red, brown or black iron oxides.
  • iron oxides examples include the iron oxide sold by the company Sun Chemical under the name SunPuro® Red Iron Oxide.
  • Direct dye Composition C used in the context of the process according to the invention may comprise one or more direct dyes.
  • direct dye means natural and/or synthetic dyes, other than oxidation dyes. These are dyes that will spread superficially on the fibre. They may be ionic or nonionic, preferably cationic or nonionic.
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes are preferably cationic direct dyes.
  • - Het+ represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, which is optionally substituted, preferentially with at least one (C 1 -C 8 ) alkyl group such as methyl
  • - Ar+ represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(C 1 - C 8 )alkylammonium, such as trimethylammonium
  • - Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as i) optionally substituted (C 1 -C 8 )al
  • the dyes of formulae (XV) and (XVI) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof with Q’ being an anionic counterion as defined previously, particularly a halide such as chloride, or an alkyl sulfate such as methyl sulfate or mesyl.
  • the direct dyes may be chosen from anionic direct dyes.
  • the anionic direct dyes of the invention are dyes commonly referred to as “acid” direct dyes owing to their affinity for alkaline substances.
  • anionic direct dye means any direct dye including in its structure at least one CO 2 R or SO 3 R substituent with R denoting a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion.
  • the anionic dyes may be chosen from direct nitro acid dyes, azo acid dyes, azine acid dyes, triarylmethane acid dyes, indoamine acid dyes, anthraquinone acid dyes, indigoid dyes and natural acid dyes.
  • R7, Rs, R9, Rio, R’7, R’s, R’9 and R’10 which may be identical or different, represent a hydrogen atom or a group chosen from:
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • R representing a hydrogen atom or an alkyl, aryl, (di)(alkyl)amino or aryl(alkyl)amino group; preferentially a phenylamino or phenyl group;
  • R’ represents an optionally substituted alkyl or aryl group, X’ as defined previously;
  • aryl(alkyl)amino optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2S(O')-, M + and iv) alkoxy with M + as defined previously;
  • - cycloalkyl notably cyclohexyl
  • Ar-N N- with Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted with one or more alkyl, (O)2S(O')-, M + or phenylamino groups; - or alternatively two contiguous groups R?
  • W represents a sigma bond c, an oxygen or sulfur atom, or a divalent radical i) -NR- with R as defined previously, or ii) methylene -C(Ra)(Rb)- with Ra and Rb, which may be identical or different, representing a hydrogen atom or an aryl group, or alternatively Ra and Rb form, together with the carbon atom that bears them, a spiro cycloalkyl; preferentially, W represents a sulfur atom or Ra and Rb together form a cyclohexyl; it being understood that formulae (XIX) and (XIX’) comprise at least one sulfonate radical (O)2S(O')-, M + or one carboxylate radical (O)CO'-, M + on one of the rings A, A’, B, B’ or C; preferentially sodium sulfonate.
  • dyes of formula (XIX) mention may be made of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment Red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3, Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2, Food Yellow 3 or Sunset Yellow; and, as examples of dyes of formula (XIX’), mention may be made of: Acid Red 111, Acid Red 134, Acid Yellow 38; b) the pyrazolone anionic azo dyes of formulae (XX) and (XX’):
  • Rn, R12 and RB which may be identical or different, represent a hydrogen or halogen atom, an alkyl group or -(O)2S(O‘), M + with M + as defined previously;
  • - Ri4 represents a hydrogen atom, an alkyl group or a group -C(O)O", M + with M + as defined previously;
  • - Ris represents a hydrogen atom
  • Ri6 represents an oxo group, in which case R’i6 is absent, or alternatively Ris with Rie together form a double bond;
  • R17 and Ris which may be identical or different, represent a hydrogen atom, or a group chosen from:
  • Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted with one or more alkyl groups;
  • R’ 16, R’ 19 and R’20 which may be identical or different, represent a hydrogen atom or an alkyl or hydroxyl group
  • R21 represents a hydrogen atom or an alkyl or alkoxy group
  • Ra and Rb which may be identical or different, are as defined previously; preferentially, Ra represents a hydrogen atom and Rb represents an aryl group; - Y represents either a hydroxyl group or an oxo group;
  • formulae (XX) and (XX’) comprise at least one sulfonate radical (O)2S(O')-, M + or one carboxylate radical -C(O)O", M + on one of the rings D or E; preferentially sodium sulfonate.
  • dyes of formula (XX) mention may be made of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and as examples of dyes of formula (XX’), mention may be made of: Acid Yellow 17; c) the anthraquinone dyes of formulae (XXI) and (XXI’): (XXI’), in which formulae (XXI) and (XXI’):
  • R22, R23, R24, R25, R26 and R27 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from: - alkyl;
  • - Z’ represents a hydrogen atom or a group NR28R29 with R28 and R29, which may be identical or different, representing a hydrogen atom or a group chosen from:
  • - aryl optionally substituted with one or more groups, particularly i) alkyl such as methyl, n-dodecyl, n-butyl; ii) (O)2S(O')-, M + with M + as defined previously; iii) R°-C(X)-X’-, R°-X’-C(X)-, R°-X’-C(X)-X”- with R°, X, X’ and X” as defined previously, preferentially R° represents an alkyl group;
  • - cycloalkyl notably cyclohexyl
  • - Z represents a group chosen from hydroxyl and NR’2sR’29 with R’28 and R’29, which may be identical or different, representing the same atoms or groups as R28 and R29 as defined previously; it being understood that formulae (XXI) and (XXI’) comprise at least one sulfonate radical (O)2S(O')-, M + or one carboxylate radical C(O)O", M + ; preferentially sodium sulfonate.
  • dyes of formula (XXI) mention may be made of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT Violet No. 2; and, as an example of a dye of formula (XXT), mention may be made of: Acid Black 48. d) the nitro dyes of formulae (XXII) and (XXII’):
  • R30, R31 and R32 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • alkoxy optionally substituted with one or more hydroxyl groups, alkylthio optionally substituted with one or more hydroxyl groups;
  • R30, R31 and R32 represent a hydrogen atom
  • Rc and Rd which may be identical or different, represent a hydrogen atom or an alkyl group
  • - W is as defined previously; W particularly represents an -NH- group; - ALK represents a linear or branched divalent C 1 -C 6 alkylene group; in particular, ALK represents a -CH 2 -CH 2 - group; - n is 1 or 2; - p represents an integer inclusively between 1 and 5; - q represents an integer inclusively between 1 and 4; - u is 0 or 1; - when n is 1, J represents a nitro or nitroso group; particularly nitro; - when n is 2, J represents an oxygen or sulfur atom, or a divalent radical – S(O) m – with m representing an integer 1 or 2; preferentially, J represents an –SO 2 – radical; - M’ represents a hydrogen atom or a cationic counterion; - , which may be present or absent, represents a benzo group optionally substituted with one or more groups R30 as defined previously; it being understood that formulae (XXII
  • dyes of formula (XXII) mention may be made of: Acid Brown 13 and Acid Orange 3; as examples of dyes of formula (XXII’), mention may be made of: Acid Yellow 1, the sodium salt of 2,4-dinitro-1-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2-(4’-N,N-(2”-hydroxyethyl)amino-2’- nitro)anilineethanesulfonic acid, 4- ⁇ -hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C Yellow 7; e) the triarylmethane dyes of formula (XXIII):
  • R33, R34, R35 and R36 which may be identical or different, represent a hydrogen atom or a group chosen from alkyl, optionally substituted aryl and optionally substituted arylalkyl; particularly an alkyl and benzyl group optionally substituted with a group (O) m S(O')-, M + with M + and m as defined previously;
  • R37, R38, R39, R40, R41, R42, R43 and R44 which may be identical or different, represent a hydrogen atom or a group chosen from:
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • R41 with R42 or R42 with R43 or R43 with R44 together form a fused benzo group: I’; with I’ optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2S(O')-, M + ; iv) hydroxyl; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X’-; viii) R°-X’-C(X)- and ix) R°-X’- C(X)-X”-; with M + , R°, X, X’ and X” as defined previously; in particular, R37 to R40 represent a hydrogen atom, and R41 to R44, which may be identical or different, represent a hydroxyl group or (O)2S(O')-, M + ; and when R43 with R44 together form a benzo group: I’; with I’
  • dyes of formula (XXIII) mention may be made of: Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid Green 3; Acid Green 5 and Acid Green 50. f) the xanthene-based dyes of formula (XXIV):
  • R45, R46, R47 and R48 which may be identical or different, represent a hydrogen or halogen atom
  • R49, Rso, R51 and R52 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • R49, Rso, Rsi and R52 represent a hydrogen or halogen atom
  • - G represents an oxygen or sulfur atom or a group NRe with Re as defined previously; particularly, G represents an oxygen atom; - L represents an alkoxide O', M + ; a thioalkoxide S', M + or a group NRf, with Rf representing a hydrogen atom or an alkyl group, and M + as defined previously; M + is particularly sodium or potassium;
  • L’ represents an oxygen or sulfur atom or an ammonium group: N + RfRg, with Rf and Rg, which may be identical or different, representing a hydrogen atom or an optionally substituted alkyl or aryl group; L’ particularly represents an oxygen atom or a phenylamino group optionally substituted with one or more alkyl or (O)mS(O')-, M + groups with m and M + as defined previously;
  • Q and Q’ which may be identical or different, represent an oxygen or sulfur atom; particularly, Q and Q’ represent an oxygen atom;
  • dyes of formula (XXIV) mention may be made of: Acid Yellow 73; Acid Red 51; Acid Red 52; Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9. g) the indole-based dyes of formula (XXV):
  • R53, R54, R55, R56, R57, Rss, R59 and Reo which may be identical or different, represent a hydrogen atom or a group chosen from:
  • dyes of formula (XXV) mention may be made of: Acid Blue 74; h) the quinoline-based dyes of formula (XXVI): (XXVI), in which formula (XXVI): - R 61 represents a hydrogen or halogen atom or an alkyl group; - R 62 , R 63 and R 64 , which may be identical or different, represent a hydrogen atom or a group (O) 2 S(O-)-, M + with M + representing a hydrogen atom or a cationic counterion; or alternatively R 61 with R 62 , or R 61 with R 64 , together form a benzo group optionally substituted with one or more groups (O) 2 S(O-)-, M + with M + representing a hydrogen atom or a cationic counterion; it being understood that formula (XXVI) comprises at least one sulfonate radical (O) 2 S(O-)-, M + , preferentially sodium sulf
  • dyes of formula (XXVI) mention may be made of: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.
  • natural direct dyes that may be used according to the invention, mention may be made of lawsone, jugl one, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orceins.
  • Use may also be made of extracts or decoctions containing these natural dyes and notably henna-based poultices or extracts.
  • the direct dyes are chosen from anionic direct dyes.
  • the colouring agent(s) may be present in a total amount ranging 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 colouring agent(s) are chosen from pigments.
  • the pigment(s) may be present in a total amount ranging from 0.05% to 20% by weight, preferably from 0.1% to 15% by weight and better still from 0.5% to 10% by weight, relative to the total weight of composition C.
  • the direct dye(s) may be present in a total amount ranging from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight, relative to the total weight of composition C.
  • Composition C used in the context of the process according to the invention may also comprise at least one non-carboxylic anionic thickener.
  • non-carboxylic agent means an agent which does not comprise any carboxylic acid functions (-COOH) or carboxylate functions (-COO").
  • thickener means a compound which increases the viscosity of a composition into which it is introduced to a concentration of 0.05% by weight relative to the total weight of the composition, by at least 20 cps, preferably by at least 50 cps, at room temperature (25°C), at atmospheric pressure and at a shear rate of 1 s' 1 (the viscosity may be measured using a cone/plate viscometer, a Haake R600 rheometer or the like).
  • non-carboxylic anionic thickener(s) are chosen from non- carboxylic anionic polymers, more preferentially from anionic polymers bearing (a) sulfonic group(s).
  • anionic polymer means a polymer comprising one or more anionic or anionizable groups, and not comprising any cationic or cationizable groups.
  • non-carboxylic anionic thickener(s) are chosen from anionic polymers including at least one ethylenically unsaturated monomer bearing a sulfonic group, in free form or partially or totally neutralized form.
  • These polymers may be crosslinked or non-crosslinked. They are preferably crosslinked.
  • These polymers may be associative or non-associative, preferably non- associative.
  • sociative polymers are polymers that are capable, in an aqueous medium, of reversibly associating with each other or with other molecules.
  • Their chemical structure more particularly comprises at least one hydrophilic zone and at least one hydrophobic zone.
  • hydrophobic group means a radical or polymer with a saturated or unsaturated, linear or branched hydrocarbon-based chain, comprising at least 8 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms and more preferentially from 18 to 30 carbon atoms.
  • the hydrocarbon-based group is derived from a monofunctional compound.
  • the hydrophobic group may be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol or decyl alcohol. It may also denote a hydrocarbon-based polymer, for instance polybutadiene.
  • the ethylenically unsaturated monomers bearing a sulfonic group are notably chosen from vinylsulfonic acid, styrenesulfonic acid, (meth)acrylamido(Ci- C22)alkylsulfonic acids, N-(Ci-C22)alkyl(meth)acrylamido(Ci-C22)alkylsulfonic acids such as undecylacrylamidomethanesulfonic acid, and also partially or totally neutralized forms thereof.
  • (Meth)acrylamido(Ci-C22)alkylsulfonic acids for instance acrylamidomethanesulfonic acid, acrylamidoethanesulfonic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, methacrylamido-2-methylpropanesulfonic acid, 2-acrylamido-n-butanesulfonic acid, 2-acrylamido-2,4,4-trimethylpentanesulfonic acid, 2-methacrylamidododecylsulfonic acid or 2-acrylamido-2,6-dimethyl-3-heptanesulfonic acid, and also partially or totally neutralized forms thereof, will more preferentially be used.
  • APMS 2-Acrylamido-2-methylpropanesulfonic acid
  • 2-acrylamido-2-methylpropanesulfonic acid copolymers mention may be made of partially or totally neutralized crosslinked copolymers of 2- acrylamido-2-methylpropanesulfonic acid and of acrylamide; mention may be made in particular of the product described in Example 1 of EP 503 853, and reference may be made to said document as regards these polymers.
  • copolymers of 2-acrylamido-2- methylpropanesulfonic acid or salts thereof and of hydroxyethyl acrylate such as the compound sold under the name Sepinov EMT 10 by the company SEPPIC (INCI name: hydroxyethylacrylate/sodium acryloyldimethyl taurate copolymer).
  • the associative AMPS polymers may notably be chosen from statistical associative AMPS polymers modified by reaction with a C6-C22 n-monoalkylamine or di-n-alkylamine, and such as those described in patent application WO 00/31154 (forming an integral part of the content of the description). These polymers may also contain other ethylenically unsaturated hydrophilic monomers chosen, for example, from (meth)acrylic acid derivatives, such as esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, or mixtures of these compounds.
  • the preferred polymers of this family are chosen from associative copolymers of AMPS and of at least one ethylenically unsaturated hydrophobic monomer.
  • copolymers may also contain one or more ethylenically unsaturated monomers not including a fatty chain, such as (meth)acrylic acid derivatives, notably esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, or mixtures of these compounds.
  • (meth)acrylic acid derivatives notably esters thereof obtained with monoalcohols or mono- or polyalkylene glycols
  • (meth)acrylamides vinylpyrrolidone, or mixtures of these compounds.
  • - terpolymers including from 10 mol% to 90 mol% of acrylamide units, from 0.1 mol% to 10 mol% of AMPS units and from 5 mol% to 80 mol% of n-(Ce- Cis)alkylacrylamide units, such as those described in patent US-5 089 578.
  • copolymers of totally neutralized AMPS and of dodecyl methacrylate and also crosslinked and non-crosslinked copolymers of AMPS and of n-dodecylmethacrylamide, such as those described in the Morishima articles mentioned above.
  • the non-carboxylic anionic thickener(s) are chosen from the sodium 2-acrylamido-2-methylpropanesulfonate/hydroxyethyl acrylate copolymer sold by the company SEPPIC (INCI name: hydroxyethyl aery late/ sodium acryloyldimethyl taurate copolymer).
  • the total amount of the non-carboxylic anionic thickener(s) ranges from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight, better still from 0.1% to 5% by weight and even better still from 0.1% to 3% by weight relative to the total weight of composition C.
  • Composition C used in the context of the process according to the invention may also comprise at least one amino silicone.
  • amino silicone' denotes any silicone including at least one primary, secondary or tertiary amine or a quaternary ammonium group.
  • the amino silicone is different from the silicone acrylic copolymer.
  • 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 p styragel columns.
  • the eluent is THF and the flow rate is 1 ml/min. 200 pl of a 0.5% by weight solution of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • the amino silicone(s) that may be used in the context of the invention are chosen from: a) the polysiloxanes corresponding to formula (A): in which x’ and y’ are integers such that the weight-average molecular weight (Mw) is between 5000 and 500000 approximately; b) the amino silicones corresponding to formula (B): R’aG3-a-Si(OSiG2)n-(OSiGbR’2-b)m-O-SiG3-a-R’a (B) in which: - G, which may be identical or different, denotes a hydrogen atom or a group from among phenyl, OH, C 1 -C 8 alkyl, for example methyl, or C 1 -C 8 alkoxy, for example methoxy; - 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
  • the amino silicone(s) are chosen from the amino silicones of formula (B).
  • the amino silicones of formula (B) are chosen from the amino silicones corresponding to formulae (C), (D), (E), (F) and/or (G) below.
  • the amino silicones corresponding to formula (B) are chosen from the silicones known as “trimethyl silyl amodimethicone” corresponding to formula (C): 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.
  • amino silicones corresponding to formula (B) are chosen from the silicones of formula (D) below: in which:
  • n + 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, 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;
  • Ri, R2 and R3, which may be identical or different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals Ri to R3 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy 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.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (E) 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 and 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;
  • Ri and R2 which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals Ri or R2 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy 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 (D) or (E) may include in their composition one or more other amino silicones the structure of which is different from formula (D) or (E).
  • a product containing amino silicones of structure (D) is sold by the company Wacker under the name Belsil® ADM 652.
  • a product containing amino silicones of structure (E) is sold by Wacker under the name Fluid WR 1300® or under the name Belsil® ADM LOG 1.
  • the oil- in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or non-ionic.
  • the number-average size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometers.
  • use is made of microemulsions with a mean particle size ranging from 5 nm to 60 nm (limits included) and more particularly from 10 nm to 50 nm (limits included).
  • use may be made according to the invention of the amino silicone microemulsions of formula (E) sold under the names Finish CT 96 E® or SLM 28020® by the company Wacker.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (F) below: in which:
  • n + 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 formula (B) is, for example, the Xiameter MEM 8299 Emulsion from Dow Corning (INCI name: amodimethicone and trideceth-6 and cetrimonium chloride).
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (G) below: in which:
  • n + 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 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 Coming; c) the amino silicones corresponding to formula (H): in which:
  • - Rs represents a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a Ci-Cis alkyl or C2-C18 alkenyl radical, for example methyl;
  • - Re represents a divalent hydrocarbon-based radical, notably a Ci-Cis alkylene radical or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy radical linked to the Si via an SiC bond;
  • - Q" is an anion such as a halide ion, notably chloride, or an organic acid salt, notably acetate;
  • - r represents a mean statistical value ranging from 2 to 20 and in particular from 2 to 8;
  • - s represents a mean statistical value ranging from 20 to 200 and in particular from 20 to 50.
  • Such amino silicones are notably described in patent US 4185087.
  • - R 7 which may be identical or different, represent a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl radical, a C 2 -C 18 alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example methyl;
  • - R 6 represents a divalent hydrocarbon-based radical, notably a C 1 -C 18 alkylene radical or a divalent C 1 -C 18 , for example C 1 -C 8 , alkyleneoxy radical linked to the Si via an SiC bond;
  • - R 8 which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a C 1 -C 18 alkyl radical, a C 2 -C 18 alkenyl radical or a radical -R 6 -NHC
  • silicones are described, for example, in patent application EP-A 0530 974; in which: - R 1 , R 2 , R 3 and R 4 , which may be identical or different, denote a C 1 -C 4 alkyl radical or a phenyl group, - R 5 denotes a C 1 -C 4 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; f) multiblock polyoxyalkylene amino silicones, of the type (AB) n , A being a polysiloxane block and B being a polyoxyalkylene block including at least one amine group.
  • Said silicones are preferably formed from repeating units having the following general formulae: [-(SiMe 2 O) x SiMe 2 -R-N(R”)- R’-O(C 2 H 4 O) a (C 3 H 6 O) b -R’-N(H)-R-] or alternatively [-(SiMe 2 O)xSiMe 2 - R -N(R”)- R’ - O(C 2 H 4 O) a (C 3 H 6 O) 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 between 0 and 200, preferably ranging from 4 to 100 and more particularly between 5 and 30; - x is an integer ranging from 1 to 10000 and more particularly from 10 to 5000; - R’’ is a hydrogen atom or a methyl; - R, which may be identical or different, represent a linear or
  • the siloxane blocks preferably represent between 50 mol% and 95 mol% of the total weight of the silicone, more particularly from 70 mol% to 85 mol%.
  • the amine content is preferably between 0.02 and 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular mass (Mw) of the silicone is preferably between 5000 and 1 000 000 and more particularly between 10 000 and 200 000.
  • the amino silicones of formula (B) are chosen from the amino silicones corresponding to formula (E).
  • composition C used in the context of the process according to the invention comprises at least one amino silicone.
  • composition C used in the context of the process according to the invention comprises at least one amino silicone having the INCI name amodimethicone, which is preferably introduced in emulsion or microemulsion form with surfactants.
  • composition C used in the context of the process according to the invention comprises at least one amino silicone having the INCI name amodimethicone as an emulsion or microemulsion with surfactants, having the INCI names trideceth-5 and trideceth-10.
  • the amino silicone(s) may be present in a total amount ranging from 0.01% to 20%, preferably from 0.05% to 15%, more preferentially from 0.1% to 10% and even more preferentially from 0.2% to 8% by weight relative to the total weight of composition C.
  • Composition C used in the context of the process according to the invention may be aqueous, the water content may range from 1% to 70% by weight, preferably from 10% to 65% by weight and more preferentially from 20% to 65% by weight, relative to the total weight of composition C.
  • Composition C used in the context of the process according to the invention may contain any adjuvant or additive usually used.
  • Composition C used in the context of the process according to the invention may notably be in the form of a suspension, a dispersion, a gel, an emulsion, notably an oil-in-water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W or polyol/O/W or O/W/O), in the form of a cream, a mousse, a stick, a dispersion of vesicles, notably of ionic or nonionic lipids, or a two-phase or multi-phase lotion.
  • O/W oil-in-water
  • W/O water-in-oil
  • W/O multiple emulsion
  • a cream, a mousse, a stick a dispersion of vesicles, notably of ionic or nonionic lipids, or a two-phase or multi-phase lotion.
  • a person skilled in the art may select the appropriate presentation form, and also the method for preparing it, on the basis of his general knowledge, taking into account firstly the nature of the constituents used, notably their solubility in the support, and secondly the intended application of the composition.
  • the hair dyeing process according to the invention may also comprise the application to the hair of a composition D comprising at least one silicone compound comprising at least one carboxylic group.
  • the silicone compound comprising at least one carboxylic group is a silicone compound different from the silicone acrylic copolymer and from the amino silicone as described previously.
  • carboxylic group means a COOH or COO" functional group, the counterion of the COO" group possibly being chosen from alkali metals, alkaline-earth metals and quaternary ammoniums.
  • the silicones that may be used may be soluble or insoluble in composition D; they may be in the form of oil, wax, resin or gum; silicone oils and gums are preferred.
  • the silicone compound(s) comprising at least one carboxylic group are chosen from the organosiloxanes of formula (XXVII) below:
  • - R1 independently represents an alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms; a hydroxyl group; an alkoxy group containing from 1 to 20 carbon atoms or an aryl group containing from 6 to 12 carbon atoms; - R2 independently represents a group R4-COOM with R4 representing a linear or branched alkylene group containing from 1 to 20 carbon atoms, preferably from 4 to 16 carbon atoms, optionally interrupted with at least one heteroatom chosen from a sulfur atom, a nitrogen atom, an oxygen atom and mixtures thereof, and M representing a hydrogen atom; an alkali metal or alkaline-earth metal or a quaternary ammonium NR’3, with R’, which may be identical or different, representing H or alkyl containing from 1 to 4 carbon atoms; a pyrrolidine radical comprising a carboxylic group COOH or a group Ra-(ORb)
  • the silicone compound(s) comprising at least one carboxylic group may be chosen from the organosiloxanes of formula (XXVIII) below: (XXVIII), in which: - R1 independently represents a linear or branched alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms and better still from 1 to 6 carbon atoms, preferentially methyl; - R4 independently represents a linear or branched alkylene group containing from 1 to 20 carbon atoms, preferably from 4 to 16 carbon atoms, optionally interrupted with at least one heteroatom chosen from a sulfur atom, a nitrogen atom, an oxygen atom and mixtures thereof; or a divalent group R a -(OR b ) x - with R a representing a linear or branched alkylene group containing from 1 to 4 carbon atoms, R b representing an alkylene group containing from 1 to 4 carbon atoms, and x being an integer ranging from 1 to
  • - R1 independently represents an alkyl group containing from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, more preferentially a methyl
  • - R4 represents a linear or branched, saturated or unsaturated alkylene group containing from 1 to 20 carbon atoms, preferably from 4 to 16 carbon atoms, optionally interrupted with at least one heteroatom chosen from a sulfur atom, a nitrogen atom, an oxygen atom and mixtures thereof; or a divalent group Ra-(ORb)x- with R a representing a linear or branched alkylene group containing from 1 to 4 carbon atoms, R b representing an alkylene group containing from 1 to 4 carbon atoms, and x being an integer ranging from 1 to 200;
  • - M represents a hydrogen atom, an alkali metal or alkaline-earth metal or a quaternary ammonium NR’3, with R’, which may be identical or different, representing H or an alkyl containing
  • - n denotes an integer ranging from 1 to 1000;
  • organosiloxanes of formula (XXVIII) mention may be made of polydimethylsiloxanes (PDMS) bearing a carboxyl end function, such as the compounds sold by the company Momentive under the trade name Silform INX (INCI name: Bis-Carboxydecyl Dimethicone).
  • PDMS polydimethylsiloxanes bearing a carboxyl end function
  • organosiloxanes of formula (XXIX) mention may be made of polydimethylsiloxanes (PDMS) bearing a carboxyl side function, such as the compounds sold by the company Shin-Etsu under the trade name X-22-3701E.
  • PDMS polydimethylsiloxanes bearing a carboxyl side function
  • organosiloxanes of formula (XXX) mention may be made of polydimethylsiloxanes (PDMS) bearing a carboxyl end function, such as the compounds sold by the company Shin-Etsu under the trade name X-22-3710.
  • PDMS polydimethylsiloxanes bearing a carboxyl end function
  • organosiloxanes of formula (XXXI) mention may be made of the compounds sold by the company Grant Industries under the trade name Grandsil SiW- PCA-10 (INCI name: Dimethicone (and) PC A Dimethicone (and) Butylene Glycol (and) Decyl Glucoside).
  • the silicone compounds comprising a carboxylic group may correspond, for example, to the compounds described in the patent application EP 186 507 in the name of Chisso Corporation, introduced herein by reference.
  • the silicone compound(s) comprising at least one carboxylic group are chosen from the organosiloxanes of formula (XXVIII), the organopolysiloxanes of formula (XXIX) and mixtures thereof.
  • silicone compound(s) comprising at least one carboxylic group are chosen from the organopolysiloxanes of formula (XXVIII) below:
  • - R1 independently represents a linear or branched alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms and better still from 1 to 6 carbon atoms, preferentially methyl
  • - R4 independently represents a linear or branched alkylene group containing from 1 to 20 carbon atoms, preferably from 4 to 16 carbon atoms, optionally interrupted with at least one heteroatom chosen from a sulfur atom, a nitrogen atom, an oxygen atom and mixtures thereof; or a divalent group R a -(OR b ) x - with R a representing a linear or branched alkylene containing from 1 to 4 carbon atoms, R b representing an alkylene group containing from 1 to 4 carbon atoms, and x being an integer ranging from 1 to 200;
  • - M independently represents a hydrogen atom, an alkali metal or alkaline-earth metal or a quaternary ammonium NR’ 3
  • the total amount of the 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 preferentially from 0.5% to 10% by weight and better still from 1% to 5% by weight relative to the total weight of composition D.
  • Oils Composition D may comprise one or more oils.
  • composition D comprises one or more oils. More preferentially, composition D comprises one or more oils chosen from alkanes.
  • oil means a fatty substance that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013 ⁇ 10 5 Pa). The oil may be volatile or non-volatile.
  • volatile oil refers to an oil that can evaporate on contact with the skin in less than one hour, at room temperature and atmospheric pressure.
  • the volatile oil is a cosmetic volatile oil, which is liquid at room temperature. More specifically, a volatile oil has an evaporation rate of between 0.01 and 200 mg/cm 2 /min, limits included (see protocol for measuring the evaporation rate indicated in the text below).
  • non-volatile oil refers to an oil that remains on the skin or the keratinous fibre at room temperature and atmospheric pressure. More specifically, a non-volatile oil has an evaporation rate of strictly less than 0.01 mg/cm 2 /min (see protocol for measuring the evaporation rate indicated in the text below).
  • the composition comprises one or more oils chosen from Ce-Ci6 alkanes and/or mixtures thereof.
  • Ce-Ci6 alkanes they may be linear or branched, and possibly cyclic.
  • Cs-Ci6 alkanes such as Cs-Ci6 isoalkanes (also known as isoparaffins), isododecane, isodecane or isohexadecane, and for example the oils sold under the Isopar or Permethyl trade names, and mixtures thereof.
  • linear alkanes preferably of plant origin, comprising from 7 to 15 carbon atoms, in particular from 9 to 14 carbon atoms and more particularly from 11 to 13 carbon atoms.
  • linear alkanes that are suitable for use in the invention, mention may be made of n-heptane (C7), n-octane (C8), n-nonane (C9), n-decane (CIO), n-undecane (Cl l), n-dodecane (C12), n-tridecane (C13), n-tetradecane (C14) and n-pentadecane (Cl 5), and mixtures thereof, and in particular the mixture of n- undecane (Cl l) and n-tridecane (C13) described in Example 1 of patent application WO 2008/155 059 by the company Cognis.
  • alkanes that are suitable for use in the invention, mention may be made of the alkanes described in patent applications WO 2007/068 371 and WO 2008/155 059. These alkanes are obtained from fatty alcohols, which are themselves obtained from coconut kernel oil or palm oil.
  • the composition comprises isododecane.
  • isododecane sold under the reference Isododecane by Ineos.
  • composition D comprises one or more oils chosen from Cs-Ci6 alkanes, more preferentially from isododecane, isohexadecane, tetradecane and/or mixtures thereof.
  • composition D comprises isododecane.
  • Composition D may comprise one or more oils present in a total amount of between 30% and 99% by weight, preferably between 50% and 99% by weight and better still between 70% and 99% by weight, relative to the total weight of composition D.
  • Composition D may comprise at least one colouring agent chosen from pigments, direct dyes and mixtures thereof as described previously.
  • composition C and the optional composition D described above may be used on wet or dry hair, and also on any type of fair or dark, natural or coloured, permanent- waved, bleached or relaxed hair.
  • composition C and the optional composition D are applied simultaneously to the keratinous fibres.
  • the optional composition D is applied to the hair after applying composition C to the hair.
  • the optional composition D is applied to the hair before applying composition C to the hair.
  • composition D is applied to the hair after applying composition C to the hair.
  • the hair is washed before applying composition C and composition D.
  • a washing, rinsing, draining or drying step is performed after applying composition C to the hair and optionally before applying composition D to the hair.
  • a drying step is performed after applying composition C to the hair and optionally before applying the optional composition D to the hair.
  • the application to the hair may be performed via any standard means, in particular using a comb, a fine brush, a coarse brush, a sponge or with the fingers.
  • composition C and/or of composition C followed by the optional composition D to the hair is generally performed at room temperature (between 15 and 25°C).
  • composition C After applying composition C to the hair, it is possible to wait for between 1 minute and 6 hours, in particular between 1 minute and 2 hours, more particularly between 1 minute and 1 hour, more preferentially between 1 minute and 30 minutes, before, for example, applying composition D to the hair or, for example, a washing, rinsing, draining or drying step.
  • composition C there is no leave-on time after applying composition C to the hair and before applying the optional composition D to the hair.
  • the hair may be left to dry or may be dried, for example at a temperature of greater than or equal to 30°C.
  • the process according to the invention may thus comprise a step of applying heat to the keratinous fibres using a heating tool.
  • the heat application step of the process of the invention may be performed using a hood, a hairdryer, a straightening iron, a curling iron, a Climazon, etc.
  • the heat application step of the process of the invention is performed using a hairdryer.
  • the step of applying heat to the hair takes place after applying composition C and the optional composition D to the hair.
  • a mechanical action may be exerted on the locks, such as combing, brushing or running the fingers through.
  • the temperature is preferably between 30°C and 110°C, preferentially between 50°C and 90°C.
  • the temperature is preferably between 110°C and 220°C, preferably between 140°C and 200°C.
  • the method of the invention involves a step (cl) of applying heat using a hood, a hairdryer or a Climazon, preferably a hairdryer, and a step (c2) of applying heat using a straightening or curling iron, preferably a straightening iron.
  • Step (cl) may be performed before step (c2).
  • the hair may be dried, for example at a temperature above or equal to 30°C. According to a particular embodiment, this temperature is above 40°C. According to a particular embodiment, this temperature is above 45°C and below 110°C.
  • the hair is dried, it is dried, in addition to a supply of heat, with a flow of air.
  • This flow of air during drying makes it possible to improve the strand separation of the coating.
  • step (c2) the passage of the straightening or curling iron, preferably the straightening iron, may be performed at a temperature ranging from 110°C to 220°C, preferably between 140°C and 200°C.
  • a shaping step may be performed, for example with a straightening iron; the temperature for the shaping step is between 110 and 220°C, preferably between 140 and 200°C.
  • the invention is a hair dyeing process comprising the following steps: i) the application to the hair of at least one composition C comprising:
  • At least one colouring agent chosen from pigments, direct dyes, and mixtures thereof chosen from pigments, direct dyes, and mixtures thereof; and then ii) optionally a leave-on time of said composition C on the hair of from 1 minute to 30 minutes, preferably from 1 to 20 minutes, and then iii) optionally a step of washing, rinsing, draining or drying said hair, and then iv) optionally, the application to the hair of at least one composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously; and then v) optionally a leave-on time of said composition D on the hair of from 1 minute to 30 minutes, preferably from 1 to 20 minutes, and then vi) optionally a step of washing, rinsing, draining or drying the hair.
  • composition C also comprises at least one amino silicone and/or at least one non-carboxylic anionic thickening, as described previously.
  • the dyeing process comprises a step iv) of applying to the hair a composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously.
  • the step of applying composition C to the hair is repeated several times.
  • the dyeing process according to the invention is a process for dyeing the hair, which consists in extemporaneously mixing, 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 compounds as described previously;
  • composition B comprising one or more silicone acrylic copolymers as described previously, and at least two compounds having Hansen solubility parameters 6 as described above, composition A and/or composition B comprising at least one colouring agent chosen from pigments, direct dyes, and mixtures thereof; composition A and/or composition B optionally comprising at least one amino silicone as described previously and/or at least one non-carboxylic anionic thickener as described previously.
  • the dyeing process also comprises the application to the hair of at least one composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously, said composition D being applied to the hair before and/or after the application of composition C to the hair.
  • composition B comprises at least one colouring agent chosen from pigments, direct dyes, and mixtures thereof.
  • composition A does not comprise at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • compositions A and B are mixed preferably less than 15 minutes before application to the hair, more preferentially less than 10 minutes before application, better still less than 5 minutes before application.
  • composition A and composition B preferably ranges from 0.1 to 10, preferentially from 0.2 to 5 and better still from 0.5 to 2, or even from 0.6 to 1.5. In a particular embodiment, the weight ratio between composition A and composition B is equal to 1.
  • the hair dyeing process is a hair dyeing process which consists in extemporaneously mixing, 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 as described previously;
  • composition B comprising one or more silicone acrylic copolymers as described previously, at least two compounds having Hansen solubility parameters 6 as described above, and at least one colouring agent chosen from pigments, direct dyes, and mixtures thereof; composition A and/or composition B optionally comprising at least one amino silicone as defined previously and/or at least one non-carboxylic anionic thickener as described previously, and
  • composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously, said composition D being applied to the hair before and/or after the application of composition C to the hair.
  • composition A optionally comprises at least one amino silicone as described previously.
  • composition A comprises at least one amino silicone as described previously.
  • composition A optionally comprises at least one non-carboxylic anionic thickener as previously described.
  • composition A comprises at least one non-carboxylic anionic thickener as previously described.
  • composition B does not comprise at least one amino silicone as previously described.
  • composition B does not comprise at least one non-carboxylic anionic thickener as described previously.
  • the total amount of the (poly)carbodiimide compound(s) is preferably from 0.01% to 40% by weight, more preferentially from 0.1% to 30% by weight, better still from 0.5% to 20% by weight, even more preferentially from 1% to 12% by weight, relative to the total weight of composition A.
  • the total amount of the silicone acrylic copolymer(s) is preferably from 2% to 60% by weight, more preferentially from 5% to 40% by weight, better still from 5% to 20% by weight, relative to the total weight of composition B.
  • the total amount of compounds having the Hansen solubility parameters 6 as defined above ranges from 1% to 60% by weight, preferably from 2% to 50% by weight, more preferentially from 5% to 45% by weight, better still from 10% to 45% by weight, relative to the total weight of composition B.
  • the amino silicone(s) may be present in a total amount 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% by weight, relative to the total weight of composition A.
  • the non-carboxylic anionic thickener(s) may be present in a total amount ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight, better still from 0.1% to 5% by weight, and even better still from 0.1% to 3% by weight, relative to the total weight of composition A.
  • the present invention also relates to a device for dyeing the hair, comprising one or more compartments containing:
  • composition C comprising: a) one or more (poly)carbodiimide compound(s) as described previously, b) one or more silicone acrylic copolymers as described previously, c) at least two compounds having Hansen solubility parameters 6 as described above, and d) at least one colouring agent chosen from pigments, direct dyes, and mixtures thereof, and
  • composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously.
  • the present invention also relates to a device for dyeing the hair, comprising several compartments containing:
  • composition A comprising: a) one or more (poly)carbodiimide compound(s) as described previously,
  • composition B comprising: b) one or more silicone acrylic copolymers as described previously, and c) at least two compounds having Hansen solubility parameters 6 as described above, and composition A and/or composition B comprising: d) at least one colouring agent chosen from pigments, direct dyes, and mixtures thereof, and
  • composition D comprising at least one silicone compound comprising at least one carboxylic group as described previously.
  • the (poly)carbodiimide(s) of the invention are accessible via synthetic methods known to those skilled in the art starting from commercial products or reagents that can be synthesized according to chemical reactions that are also known to those skilled in the art. Mention may be made, for example, of the book Sciences of Synthesis - Houben - Weyl Methods of Molecular Transformations, 2005, Georg Thiem Verlag Kg, Rudigerstrasse 14, D-70469 Stuttgart, or the American patent US 4 284 730 or the Canadian patent application CA 2 509 861.
  • the process for preparing the (poly)carbodiimides of the invention involves, in a first step, a diisocyanate reagent (1):
  • a carboimidation catalyst (2) such as those described in US 4 284 730, notably phosphorus-based catalysts particularly chosen from phospholene oxides and phospholene sulfoxides, diaza- and oxaza-phospholane
  • compound (3) reacts with 1 molar equivalent (1 eq.) of nucleophilic reagent Ri-Xi-H and then 0.5 eq. of reagent H-E-H with Ri, Xi and E as defined previously, to give the “symmetrical” compound (4) according to the invention:
  • the (poly)carbodiimide compounds may be purified via conventional methods known to those skilled in the art, such as extraction with water and water-immiscible organic solvent, precipitation, centrifugation, filtration and/or chromatography.
  • Example 1 Process for synthesizing the (poly)carbodiimide compound
  • the reaction medium was heated at 140°C under nitrogen for 4 hours, the reaction being monitored by infrared spectroscopy by means of the absorption of the isocyanate functions between 2200 and 2300 cm' 1 , and then cooled to 120°C.
  • a mixture of 5.3 g of polyethylene glycol monomethyl ether and 1.2 g of 1,4- butanediol are introduced with stirring into the reaction medium.
  • the temperature of 120°C is maintained until the isocyanate functions have totally disappeared, monitored by infrared spectroscopy at 2200-2300 cm' 1 , and is then cooled to room temperature.
  • reaction medium After cooling to room temperature, the reaction medium is poured dropwise with vigorous stirring into a 500 mL glass beaker containing 85 g of distilled water, to give the desired product in the form of a translucent yellow liquid.
  • compositions A, B, C, D and E as described below were prepared: the amounts are expressed as g of raw material as obtained/100 g, unless otherwise mentioned, in Table 1 below.
  • the cloudiness was evaluated visually by a trained panel of five people during a lined test in which a score from 1 to 5 was attributed (the result corresponds to an average of the notes attributed), according to the following grading scale as described in Table 2:
  • solubility of the compositions comprising at least two compounds having Hansen solubility parameters ⁇ according to the invention is very satisfactory in aqueous medium.
  • the compositions comprising at least two compounds having Hansen solubility parameters ⁇ according to the invention afford good solubility to the silicone acrylic copolymer.
  • Example 3 Compositions F, G1, G2 and G3 as described below were prepared: the amounts are expressed in g of raw material as is per 100g, unless otherwise mentioned.
  • “AM” means active material.
  • [Table 4] (2) synthesized according to the synthetic process described in example 1 (containing 40% active material in water), (3) sold by the company SEPPIC under the name SEPINOV EMT10, (4) sold by the company Wacker under the name BELSIL ADM LOG 1 (containing 15% active material). [Table 5]
  • composition F is mixed with each of the compositions Gl, G2 and G3 in a 50/50 mass ratio to obtain three compositions Hl, H2 and H3.
  • composition Hl is a comparative process.
  • processes using compositions H2 and H3 are processes according to the invention.
  • composition I as described below was prepared: the amounts are expressed as g of starting material as obtained/100 g.
  • compositions Hl, H2 and H3 are applied to locks of dry natural hair containing 90% white hairs, in a proportion of 0.8 g of composition per gram of lock.
  • the locks of hair are then disentangled and dried with a hairdryer, and then combed.
  • composition I is applied to said locks of dry hair treated beforehand with compositions Hl, H2 and H3, in a proportion of 0.5 g of composition per gram of lock.
  • the locks of hair are then dried with a hairdryer at moderate heat, and then stored at a temperature of 22°C and a humidity of 35% for 24 hours.
  • the locks of hair thus coloured are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the colouring obtained with respect to shampoo washes, according to the shampoo washing protocol described below.
  • the coloured locks of hair are combed, moistened with water at 35°C and then passed between the fingers five times for 5 seconds. The locks of hair are then squeezed dry between two fingers.
  • a standard shampoo (Garnier Ultra Doux) is applied uniformly to the coloured locks, in a proportion of 0.4 g of standard shampoo per gram of locks, the locks of hair being massaged gently along the length (6 passes) for 15 seconds, from the root to the end.
  • the locks of hair are then placed on a watch glass and left to stand for 1 minute.
  • the locks of hair are rinsed with water while passing the lock between the fingers (15 passes).
  • the locks of hair are then squeezed dry between two fingers before the next shampoo wash.
  • the persistence of the colour of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600A colorimeter (illuminant D65, angle 10°, specular component included).
  • L* represents the intensity of the colour
  • a* indicates the green/red colour axis
  • b* the blue/yellow colour axis.
  • the persistence of the colouring is evaluated by the colour difference AE between the coloured locks before shampooing, then after having undergone five shampoo washes according to the protocol described above. The lower the AE value, the more persistent the colour with respect to shampoo washing.
  • the AE value is calculated according to the following equation:
  • L*a*b* represent the values measured after colouring the hair and after performing the shampoo washes
  • Lo*ao*bo* represent the values measured after colouring the hair but before shampoo washing.
  • the locks of hair treated by means of the processes according to the invention and washed with five shampoo washes have lower AE values than those of the locks treated by means of the comparative process.
  • the coloured coating obtained by means of the processes according to the invention shows improved persistence with respect to shampoo washing.

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Abstract

La présente invention concerne un procédé de coloration capillaire, comprenant l'application sur les cheveux d'une composition C comprenant : - un ou plusieurs composés (poly)carbodiimide de formule spécifique (II) ; - un ou plusieurs copolymères acryliques de silicone ; - au moins deux composés ayant les paramètres de solubilité de Hansen suivants δ: δh allant de 5 à 40 MPa1/2 et δp allant de 4 à 14 MPa1/2 ; et - un ou plusieurs agents de coloration choisis parmi les pigments, les colorants directs et leurs mélanges.
PCT/EP2022/086355 2021-12-16 2022-12-16 Procédé de coloration capillaire, comprenant l'application d'un composé (poly)carbodiimide de formule spécifique, d'un polymère acrylique de silicone, de deux composés ayant des paramètres de solubilité de hansen spécifiques et d'un agent colorant WO2023111268A1 (fr)

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