WO2023187157A1 - Procédé de teinture capillaire comprenant l'application d'une composition c comprenant un composé métallique - Google Patents

Procédé de teinture capillaire comprenant l'application d'une composition c comprenant un composé métallique Download PDF

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WO2023187157A1
WO2023187157A1 PCT/EP2023/058454 EP2023058454W WO2023187157A1 WO 2023187157 A1 WO2023187157 A1 WO 2023187157A1 EP 2023058454 W EP2023058454 W EP 2023058454W WO 2023187157 A1 WO2023187157 A1 WO 2023187157A1
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carbon atoms
composition
chosen
formula
weight
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PCT/EP2023/058454
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Alexis LIARD
Arnaud Bonnamy
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L'oreal
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    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; 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
    • A61K8/81—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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • 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
    • 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
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • the present invention relates to a process for dyeing keratin fibres such as the hair, comprising a step of applying to the keratin fibres at least one composition C comprising at least one metal compound, a step of applying to the keratin fibres at least one composition A comprising at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’), and at least one alkoxysilane of formula (II), and a step of applying to the keratin fibres at least one composition B comprising at least one film- forming polymer.
  • composition A and/or composition B comprise at least one colouring agent chosen from pigments, direct dyes and mixtures thereof. Steps i), ii) and iii) are performed successively i), then ii), then iii) or else ii), then i), then iii) or else ii), then iii) then i).
  • Context of the invention In the field of dyeing keratin fibres, in particular human keratin fibres, it is already known practice to dye keratin fibres via various techniques using direct dyes or pigments for non-permanent dyeing, or dye precursors for permanent dyeing.
  • a subject of the present invention is a process for dyeing keratin fibres such as the hair, comprising: i) a step of applying to the keratin fibres at least one composition C comprising at least one metal compound, ii) a step of applying to the keratin fibres at least one composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described below, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described below, oligomers thereof and/or mixtures thereof, and iii) a step of applying to the keratin fibres at least one composition B comprising: - at least one film-forming polymer, composition A and/or composition B comprising at least one colouring agent chosen from pigments, direct dyes and mixtures thereof; it being understood that steps i), ii) and iii) are performed successively i), then
  • the present invention also relates to a device for dyeing keratin fibres such as the hair, comprising several compartments containing: - in a first compartment, a composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described below, oligomers thereof and/or mixtures thereof, - at least one alkoxysilane of formula (II) as described below, oligomers thereof and/or mixtures thereof, - in a second compartment, a composition B according to the invention comprising: - at least one film-forming polymer, and - in a third compartment, a composition C comprising at least one metal compound, composition A and/or composition B comprising at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • a composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described below, oligomers thereof and/or mixtures thereof,
  • coloured coatings are obtained on the hair that make it possible to obtain a shampoo-fast colouring that is visible on all types of hair, while at the same time preserving the physical qualities of the keratin fibres.
  • a coating may be resistant to the external attacking factors to which the hair may be subjected, such as blow-drying and perspiration.
  • the term “shampoo-fast colouring” means that the colouring obtained persists after at least one shampoo wash.
  • the term “at 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 ...”.
  • keratin fibres particularly means human keratin fibres such as head hair, eyelashes, eyebrows, and bodily hair, preferentially head hair, eyebrows and eyelashes, even more preferentially head hair.
  • the term “the hair” means head hair. This term does not correspond to bodily hairs, the eyebrows or the eyelashes.
  • uccessive steps means steps performed in the indicated order.
  • sicone denotes any organosilicon polymer or oligomer of linear or cyclic, branched or crosslinked 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 (siloxane bond -Si-O-Si-), hydrocarbon-based radicals which are optionally substituted being directly linked via a carbon atom to said silicon atoms.
  • an “alkyl” radical denotes a linear or branched saturated radical containing, for example, from 1 to 30 carbon atoms
  • - an “aminoalkyl” radical denotes an alkyl radical as defined previously, said alkyl radical comprising an NH2 group
  • - a “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 C 1 -C 10 hydrocarbon-based group such as methylene, ethylene or propylene
  • - a “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 40 carbon atoms, in particular comprising from 3 to 24 carbon atoms, more
  • Composition A Alkoxysilane of formula (I) or of formula (I’):
  • Composition A according to the invention comprises at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) below, oligomers thereof and/or mixtures thereof: in which: - Ra represents an alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, more preferentially from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms such as a methyl, said alkyl group being optionally substituted with an aryl group; an alkoxy group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms such as an ethoxy; or an aryl group containing from 6 to 12 carbon atoms; - Rb and Rc, which may be identical or different, represent a hydrogen atom; an alkyl group containing from
  • alkoxysilanes of formula (I), oligomers thereof and/or mixtures thereof mention may notably be made of 3-aminopropyltriethoxysilane (APTES), 3- aminopropylmethyldiethoxysilane (APMDES), 3-ureidopropyltrimethoxysilane and N- cyclohexylaminomethyltriethoxysilane.
  • APTES may be purchased, for example, from the company Dow Corning under the name Xiameter OFS-6011 Silane or from the company Momentive Performance Materials under the name Silsoft A-1100 or from the company Shin-Etsu under the name KBE-903.
  • the compounds of formula (I) may also denote Dynasylan SIVO 210 or Dynasylan 1505 sold by the company Evonik.
  • 3-Ureidopropyltrimethoxysilane may be purchased, for example, from the company Gelest under the reference SIU9058.0.
  • N-Cycloheylaminomethyltriethoxysilane may be purchased, for example, from the company Wacker under the name Geniosil XL 926.
  • alkoxysilanes of formula (I’) oligomers thereof and/or mixtures thereof, mention may notably be made of N,N-bis[3-(trimethoxysilyl)propyl]ethylenediamine (CAS RN: 74956-86-8), N1,N1-bis[3-(triethoxysilyl)propyl]-1,2-ethanediamine (CAS RN: 457065-96-2), 1,2-ethanediamine, N1-[3-(triethoxysilyl)propyl]-N1-[3- (trimethoxysilyl)propyl]- (CAS RN: 1638528-78-5), and mixtures thereof.
  • N,N-bis[3-(trimethoxysilyl)propyl]ethylenediamine CAS RN: 74956-86-8
  • N1,N1-bis[3-(triethoxysilyl)propyl]-1,2-ethanediamine CAS RN: 457065-96-2
  • the alkoxysilane(s), oligomers thereof and/or mixtures thereof are chosen from the compounds of formula (I) below: in which: - R a represents an alkyl group containing from 1 to 10 carbon atoms, notably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms, preferably a methyl, or an alkoxy group containing from 1 to 4 carbon atoms, preferably from 1 to 2 carbon atoms, preferably an ethoxy; - R b and R c , which may be identical or different, represent an alkyl group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, such as an ethyl; - R d and R e , which are identical, represent a hydrogen atom or R d denotes a hydrogen atom and R e denotes a C 5 -C 6 cycloalkyl radical such as cyclohexyl; - A independently represents a linear
  • the alkoxysilane(s), oligomers thereof and/or mixtures thereof are chosen from compounds of formula (I) in which R a represents an ethoxy group, R b and R c are identical and represent ethyl, Rd and Re represent a hydrogen atom, A represents propyl and r denotes an integer equal to 0.
  • the alkoxysilane of formula (I), oligomers thereof and/or mixtures thereof is 3-aminopropyltriethoxysilane (APTES).
  • alkoxysilane(s) of formula (I) or of formula (I’), oligomers thereof and/or mixtures thereof may be present in a total amount ranging from 0.1% to 40% by weight, preferably from 0.5% to 30% by weight, preferentially from 0.75% to 25% by weight, better still from 1% to 20% by weight and even better still from 1.5% to 15% by weight, relative to the total weight of composition A.
  • the alkoxysilane(s) of formula (I), oligomers thereof and/or mixtures thereof is (are) present in a total amount ranging from 0.1% to 40% by weight, preferably from 0.5% to 30% by weight, preferentially from 0.75% to 25% by weight, better still from 1% to 20% by weight and even better still from 1.5% to 15% by weight, relative to the total weight of composition A.
  • Composition A comprises at least one alkoxysilane of formula (II) below, oligomers thereof and/or mixtures thereof: in which: - Ra represents an alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, more preferentially from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms such as a methyl, said alkyl group being optionally substituted with an aryl group; an alkoxy group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms such as an ethoxy; or an aryl group containing from 6 to 12 carbon atoms; - Rb represents a hydrogen atom or an alkyl group containing from 1 to 20 carbon atoms, preferably from 1 to 6 carbon atoms and notably from 1 to 4 carbon atoms, notably an ethyl group; - R
  • alkoxysilanes of formula (II), oligomers thereof and/or mixtures thereof mention may notably be made of tetraethoxysilane (TEOS), methyltrimethoxysilane (MTMS), methyltriethoxysilane (MTES), dimethyldiethoxysilane (DMDES), diethyldiethoxysilane, dipropyldiethoxysilane, propyltriethoxysilane, isobutyltriethoxysilane, phenyltriethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, benzyltriethoxysilane, benzylmethyldiethoxysilane, dibenzyldiethoxysilane, acetoxymethyltriethoxysilane and mixtures thereof.
  • TEOS tetraethoxysilane
  • MTMS methyltrimethoxysilane
  • MTES methyltrieth
  • TEOS may be purchased, for example, from the company Evonik under the name Dynasylan® A or Dynasylan® A SQ.
  • MTES may be purchased, for example, from the company Evonik under the name Dynasylan® MTES.
  • DMDES may be purchased, for example, from the company Gelest under the reference SID3404.0.
  • the alkoxysilane(s) of formula (II), oligomers thereof and/or mixtures thereof are such that: - R a represents an alkoxy group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms such as a methoxy or an ethoxy; or an alkyl group containing from 1 to 10 carbon atoms optionally substituted with an aryl group, preferably 1 to 2 carbon atoms optionally substituted with an aryl group; - Rb represents an alkyl group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, in particular from 1 to 2 carbon atoms, such as a methyl or an ethyl; - R c represents an alkoxy group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms, such as a methoxy or an ethoxy;
  • the alkoxysilane(s) of formula (II), oligomers thereof and/or mixtures thereof are such that: - Ra represents an alkyl group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, in particular from 1 to 2 carbon atoms, such as a methyl or an ethyl; - Rb represents an alkyl group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, in particular from 1 to 2 carbon atoms, such as a methyl or an ethyl; - R c represents an alkoxy group containing from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms and in particular from 1 to 2 carbon atoms, such as a methoxy or an ethoxy; - k denotes an integer equal to 0; - Rf represents an alkyl group containing from 1 to 10 carbon atoms and notably from 1 to 4 carbon atoms such as
  • the alkoxysilane of formula (II), oligomers thereof and/or mixtures thereof is methyltrimethoxysilane (MTMS) or methyltriethoxysilane (MTES).
  • the alkoxysilane(s) of formula (II), oligomers thereof and/or mixtures thereof may be present in a total amount ranging from 0.5% to 90% by weight, preferably from 1% to 75%, preferentially from 3% to 45% by weight and better still from 5% to 40% by weight, relative to the total weight of composition A.
  • Organic solvents Composition A according to the invention may comprise one or more organic solvents.
  • composition A according to the invention comprises ethanol.
  • the organic solvent(s) may be present in a total amount ranging from 1% to 70% by weight, preferably from 5% to 55% by weight and more preferentially from 10% to 50% by weight, relative to the total weight of the composition according to the invention.
  • Composition B Film-forming Composition B according to the invention comprises at least one film-forming polymer.
  • the film-forming polymer(s) are chosen from hydrophilic film-forming polymers, hydrophobic film-forming polymers, and mixtures thereof.
  • the term “polymer” means a compound corresponding to the repetition of one or more units (these units being derived from compounds known as monomers). This or these unit(s) are repeated at least twice and preferably at least three times.
  • hydrophobic polymer means a polymer that has a solubility in water at 25°C of less than 1% by weight.
  • hydrophilic polymer means a polymer that has a solubility in water at 25°C of greater than or equal to 1% by weight.
  • film-forming polymer refers to a polymer that is capable of forming, by itself or in the presence of an auxiliary film-forming agent, a macroscopically continuous film on a support, notably on keratin materials, and preferably a cohesive film. According to a preferred embodiment, the film-forming polymer(s) are chosen from hydrophobic film-forming polymers.
  • the hydrophobic film-forming polymer is a polymer chosen from the group comprising: - film-forming polymers that are soluble in an organic solvent medium, in particular liposoluble polymers; this means that the polymer is soluble or miscible in the organic medium and forms a single homogeneous phase when it is incorporated into the medium; - film-forming polymers that are dispersible in an organic solvent medium, which means that the polymer forms an insoluble phase in the organic medium, the polymer remaining stable and/or compatible once incorporated into this medium.
  • such polymers may be in the form of non-aqueous dispersions of polymer particles, preferably dispersions in silicone oils or hydrocarbon-based oils; in one embodiment, the non-aqueous polymer dispersions comprise polymer particles stabilized on their surface with at least one stabilizer; these non-aqueous dispersions are often referred to as NADs; - film-forming polymers in the form of aqueous dispersions of polymer particles, which means that the polymer forms an insoluble phase in water, the polymer remaining stable and/or compatible once incorporated into the water, the polymer particles possibly being stabilized at their surface with at least one stabilizer. These polymer particles are often referred to as latices; in this case, the composition must comprise an aqueous phase.
  • hydrophobic film-forming polymers that may be used in the composition of the present invention, mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin, and mixtures thereof.
  • Hydrophobic film-forming polymers that may be mentioned in particular include acrylic polymers, polyurethanes, polyesters, polyamides, polyureas, cellulose-based polymers such as nitrocellulose, silicone polymers, polymers of acrylamide type, and polyisoprenes.
  • Nonionic hydrophobic film-forming polymers, amphoteric hydrophobic film-forming polymers, anionic hydrophobic film-forming polymers or cationic hydrophobic film- forming polymers may be used.
  • the hydrophobic film-forming polymer(s) according to the invention are chosen from acrylic acid copolymers, methacrylic acid copolymers, acrylic acid ester homopolymers or copolymers, methacrylic acid ester homopolymers or copolymers, acrylic acid amide homopolymers or copolymers, methacrylic acid amide homopolymers or copolymers, vinylpyrrolidone copolymers, vinyl alcohol copolymers, vinyl acetate copolymers, ethylene homopolymers or copolymers, propylene homopolymers or copolymers, styrene homopolymers or copolymers, polyurethanes, polyesters and/or polyamides.
  • the hydrophobic film-forming polymer may be chosen from homopolymers and copolymers of olefins such as cycloolefins; butadiene; isoprene; styrene; vinyl ethers, esters or amides; (meth)acrylic acid esters or amides containing a linear, branched or cyclic C 1 -C 20 alkyl group, a C 6 -C 10 aryl group or a C 2 -C 6 hydroxyalkyl group.
  • olefins such as cycloolefins; butadiene; isoprene; styrene; vinyl ethers, esters or amides; (meth)acrylic acid esters or amides containing a linear, branched or cyclic C 1 -C 20 alkyl group, a C 6 -C 10 aryl group or a C 2 -C 6 hydroxyalkyl group.
  • the hydrophobic film-forming polymer may notably be chosen from homopolymers and copolymers which may be obtained from monomers chosen from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, ethyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, benzyl acrylate and phenyl acrylate, or mixtures thereof.
  • the hydrophobic film-forming polymer may notably be chosen from the homopolymers and copolymers that may be obtained from amides of acid monomers; mention may be made of (meth)acrylamides, and notably N-alkyl(meth)acrylamides, in particular of C 2 - C 12 alkyl, such as N-ethylacrylamide, N-t-butylacrylamide or N-octylacrylamide; N- (C1-C4)dialkyl(meth)acrylamides and perfluoroalkyl (meth)acrylates.
  • the hydrophobic film-forming polymer(s) according to the invention are chosen from anionic copolymers.
  • the anionic copolymers according to the invention are copolymers of acrylic acid, methacrylic acid or (meth)acrylic acid esters containing a linear, branched or cyclic C 1 -C 6 alkyl group, as described under the INCI name Acrylates.
  • Such copolymers are sold by the company Rohm & Haas under the name Aculyn®33.
  • Copolymers of unsaturated ethylenic acid esters of alkoxylated fatty alcohols may also be used according to the invention.
  • Such unsaturated ethylenic acid esters are in particular of acrylic acid, methacrylic acid and itaconic acid, and of alkoxylated fatty alcohols in particular such as steareth-20 and ceteth-20.
  • Examples that may be mentioned include Aculyn®22 (Acrylates/Steareth-20 Methacrylate Copolymer), Aculyn®28 (Acrylates/Beheneth-25 Methacrylate Copolymer), Structure 2001® (Acrylates/Steareth-20 Itaconate Copolymer), Structure 3001® (Acrylates/Ceteth-20 Itaconate Copolymer), Structure Plus® (Acrylates/Aminoacrylates C10-30 Alkyl PEG-20 Itaconate Copolymer), Carbopol® 1342, 1382, Ultrez 20, Ultrez 21 (Acrylates/C10-30 Alkyl acrylate Crosspolymer), Synthalen W2000® (Acrylates/Palmeth-25 Acry
  • the hydrophobic film-forming polymer may also be chosen from homopolymers and copolymers that may be obtained from vinyl monomers. Mention may be made of homopolymers or copolymers of N-vinylpyrrolidone, vinylcaprolactam, vinyl-N-(C1- C6)alkylpyrroles, vinyloxazoles, vinylthiazoles, vinylpyrimidines or vinylimidazoles.
  • vinylpyrrolidone copolymers that may be used in the invention, mention may be made of the VP/vinyl laurate copolymer, the VP/vinyl stearate copolymer, the butylated polyvinylpyrrolidone (PVP) copolymer, the VP/hexadecene copolymer sold by ISP under the name Ganex V216, the VP/eicosene copolymer sold by ISP under the name Ganex V220, the VP/triacontene copolymer or the VP/acrylic acid/lauryl methacrylate copolymer.
  • PVP polyvinylpyrrolidone
  • the hydrophobic film-forming polymer may also be chosen from homopolymers and copolymers that may be obtained from olefins such as ethylene, propylene, butenes, isoprene, butadienes.
  • the hydrophobic film-forming polymer according to the invention is a block copolymer comprising at least one block consisting of styrene units or styrene derivatives (for example methylstyrene, chlorostyrene or chloromethylstyrene).
  • the copolymer comprising at least one styrene block may be a diblock or triblock copolymer, or even a multiblock, star or radial copolymer.
  • the copolymer comprising at least one styrene block may also comprise, for example, an alkylstyrene (AS) block, an ethylene/butylene (EB) block, an ethylene/propylene (EP) block, a butadiene (B) block, an isoprene (I) block, an acrylate (A) block or a methacrylate (MA) block, or a combination of these blocks.
  • AS alkylstyrene
  • EB ethylene/butylene
  • EP ethylene/propylene
  • B butadiene
  • I isoprene
  • A acrylate
  • MA methacrylate
  • the copolymer comprising at least one block consisting of styrene units or styrene derivatives may be a diblock or triblock copolymer, and in particular of the polystyrene/polyisoprene or polystyrene/polybutadiene type, such as those sold or manufactured under the name Luvitol HSB by the company BASF SE.
  • the hydrophobic film-forming polymer(s) according to the invention are chosen from vinylpyrrolidone (co)polymers, vinyl alcohol (co)polymers, vinyl acetate (co)polymers, carboxyvinyl (co)polymers, acrylic acid (co)polymers, methacrylic acid (co)polymers, acrylic acid ester (co)polymers, ethylene (co)polymers, acrylamide (co)polymers and mixtures thereof. More preferentially, the hydrophobic film-forming polymer(s) are chosen from vinylpyrrolidone copolymers, acrylamide copolymers, acrylic acid ester homopolymers or copolymers, ethylene homopolymers or copolymers and mixtures thereof.
  • the film-forming polymer(s) are chosen from hydrophilic film-forming polymers.
  • Nonionic hydrophilic film-forming polymers, anionic hydrophilic film-forming polymers or cationic hydrophilic film-forming polymers may be used.
  • the hydrophilic film-forming polymer may be chosen from vinylpyrrolidone (co)polymers, vinyl alcohol (co)polymers, vinyl acetate polymers, carboxyvinyl (co)polymers, acrylic acid (co)polymers, methacrylic acid (co)polymers, natural gums, polysaccharides and/or acrylamide (co)polymers.
  • the hydrophilic film-forming polymer is chosen from vinylpyrrolidone (PVP) homopolymers and/or vinylpyrrolidone copolymers, more preferentially vinylpyrrolidone (PVP) homopolymers.
  • PVP vinylpyrrolidone
  • Examples that may be mentioned include the vinylpyrrolidone (PVP) homopolymers sold under the name Luviskol® K by the company BASF SE, in particular Luviskol® K 90 or Luviskol® K 85 by the company BASF SE.
  • the polymer PVP K30 sold by the company Ashland Inc. (ISP, POI Chemical) may also be used.
  • PVP K30 is a polyvinylpyrrolidone polymer that is soluble in cold water, having the CAS number 9003-39-8 and a molecular weight of 40000 g/mol.
  • Other vinylpyrrolidone homopolymers that are suitable for use in the invention are sold under the trade names Luvitec K 17, Luvitec K 30, Luvitec K 60, Luvitec K 80, Luvitec K 85, Luvitec K 90 and Luvitec K 115 by the company BASF SE.
  • Vinylpyrrolidone/vinylcaprolactam/DMAPA acrylate copolymers may be sold by the company Ashland Inc. under the trade name Aquaflex® SF-40. Vinylpyrrolidone/DMAPA acrylates copolymers may be sold by the company Ashland Inc. under the trade name Styleze CC-10.
  • vinylpyrrolidone copolymers mention may be made of copolymers obtained by reaction of N-vinylpyrrolidone with at least one monomer chosen from N- vinylformamide, vinyl acetate, ethylene, propylene, acrylamide and vinylcaprolactam.
  • the hydrophilic film-forming polymer(s) are chosen from vinylpyrrolidone (PVP) homopolymers, vinylpyrrolidone/vinyl acetate copolymers, vinylpyrrolidone/styrene copolymers, vinylpyrrolidone/ethylene copolymers, vinylpyrrolidone/propylene copolymers, vinylpyrrolidone/vinylcaprolactam copolymers, vinylpyrrolidone/vinylformamide copolymers, vinylpyrrolidone/vinyl alcohol copolymers, and mixtures thereof.
  • PVP vinylpyrrolidone
  • vinylpyrrolidone/vinyl acetate copolymers vinylpyrrolidone/styrene copolymers
  • vinylpyrrolidone/ethylene copolymers vinylpyrrolidone/propylene copolymers
  • vinylpyrrolidone/vinylcaprolactam copolymers vinylpyrrolidone/vinylform
  • the film-forming polymer(s) are chosen from vinylpyrrolidone (PVP) homopolymers, vinylpyrrolidone/vinyl acetate copolymers, vinylpyrrolidone/styrene copolymers, vinylpyrrolidone/ethylene copolymers, vinylpyrrolidone/propylene copolymers, vinylpyrrolidone/vinylcaprolactam copolymers, vinylpyrrolidone/vinylformamide copolymers, vinylpyrrolidone/vinyl alcohol copolymers, acrylamide copolymers, acrylic acid ester homopolymers or copolymers, ethylene homopolymers or copolymers and mixtures thereof.
  • PVP vinylpyrrolidone
  • the film-forming polymer(s) are chosen from vinylpyrrolidone (PVP) homopolymers, acrylamide copolymers, acrylic acid ester homopolymers or copolymers, ethylene homopolymers or copolymers and mixtures thereof.
  • the film-forming polymer(s) may be present in a total amount ranging from 0.1% to 30% by weight, preferably from 0.5% to 25% by weight and better still from 1% to 20% by weight, relative to the total weight of composition B.
  • Amino silicone Composition A and/or composition B may comprise at least one amino silicone.
  • the term “amino silicone” denotes any silicone including at least one primary, secondary, tertiary amine or a quaternary ammonium group.
  • 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 ⁇ styragel columns.
  • the eluent is THF and the flow rate is 1 ml/min.200 ⁇ l 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’ a G 3-a -Si(OSiG 2 ) n -(OSiG b R’ 2-b ) m -O-SiG 3-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,
  • 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 of formulae (C), (D), (E), (F) and (G) below and/or amino silicones comprising at least one unit of formula (L), in particular the amino silicones of formula (N) below.
  • the amino silicones corresponding to formula (B) are chosen from the silicones known as “trimethylsilyl 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.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (D) below: in which: - m and n are numbers such that the sum (n + m) ranges from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200; n possibly denoting a number from 0 to 999, 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; - R 1 , R 2 and R 3 , which may be identical or different, represent a hydroxyl or C 1 -C 4 alkoxy radical, at least one of the radicals R 1 to R 3 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 1000000 and more particularly from 3500 to 200000.
  • 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; - R 1 and R 2 , which are different, represent a hydroxyl or C 1 -C 4 alkoxy radical, at least one of the radicals R 1 or R 2 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 200000, even more particularly from 5000 to 100000 and more particularly from 10 000 to 50000.
  • 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 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.
  • these amino silicones are used, one particularly advantageous embodiment consists in using them in the form of an oil-in-water emulsion.
  • the oil-in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or nonionic.
  • the number-average size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nm.
  • amino silicones of formula (E) 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).
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (F) below: in which: - m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and notably from 49 to 149, and m possibly denoting a number from 1 to 2000 and notably from 1 to 10; - A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 2000 to 1000000 and even more particularly from 3500 to 200000.
  • Another 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: - 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 1000000 and even more particularly from 1000 to 200000.
  • a silicone corresponding to this formula is, for example, DC2-8566 Amino Fluid from Dow Corning;
  • - 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;
  • - Q- is an anion such as a halide ion, notably chloride, or an organic acid salt, notably
  • Said silicones are preferably formed from repeating units having the following general formulae: [-(SiMe 2 O)xSiMe 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
  • 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 1000000 and more particularly between 10000 and 200000. Mention may notably be made of the silicones sold under the name Silsoft A-843 or Silsoft A+ by Momentive.
  • - A represents a hydroxyl, -O-Si(CH 3 ) 3 , -O-Si(CH 3 ) 2 OH or -O-Si(CH 3 ) 2 OCH 3 group
  • - D represents a hydrogen atom or a -Si(CH 3 ) 3 , -Si(CH 3 ) 2 OH or -Si(CH 3 ) 2 OCH 3 group
  • - b, n and c independently of each other, are integers between 0 and 100 with n > 0 and b+c > 0, and at least one of the following conditions is met:
  • A represents a hydroxyl group (OH) or D represents a hydrogen atom.
  • amino silicones comprising at least one unit of formula (L):
  • the amino silicone according to the invention comprises at least one unit having the formula (L) below:
  • the amino silicone according to the invention comprises at least one unit of formula (L) and at least one unit of formula (M) below: (M).
  • the amino silicone according to the invention is an amino silicone substituted with at least one 4-morpholinomethyl group.
  • - R 1 represents a -CH 3 , OH, -OCH 3 , -O-CH 2 CH 3 , -O-CH 2 CH 2 CH 3 or -O-CH(CH 3 ) 2 group
  • - R 2 represents a -CH 3 , OH or -OCH 3 group
  • - B represents a hydroxyl
  • -O-Si(CH 3 ) 3 -O-Si(CH 3 ) 2 OH or -O-Si(CH 3 ) 2 OCH 3 group
  • - D represents a hydrogen atom or a -Si(CH 3 ) 3 , -Si(CH 3
  • the amino silicones of formula (B) are chosen from the amino silicones of formula (D) or amino silicones comprising at least one unit of formula (L), in particular the amino silicones of formula (N).
  • composition A and/or composition B comprise(s) at least one amino silicone chosen from the amino silicones of formula (D) or amino silicones comprising at least one unit of formula (L), in particular the amino silicones of formula (N).
  • the amino silicone(s) may be present in a total amount ranging from 0.1% to 35%, preferably from 1% to 25%, more preferentially from 3% to 20% and even more preferentially from 5% to 17% by weight, relative to the total weight of composition A and/or composition B.
  • Non-associative nonionic cellulose-based Composition A and/or composition B according to the invention may comprise at least one nonionic cellulose-based polymer, which is preferably non-associative.
  • the non-associative nonionic cellulose-based polymer is different from the film- forming polymers mentioned previously.
  • the term “cellulose-based polymer” means any polysaccharide polymer having, in its structure, sequences of glucose residues joined together via beta-1,4 bonds.
  • non-associative cellulose-based polymer means that the cellulose-based polymers do not include any C 8 -C 30 fatty chains.
  • the non-associative nonionic cellulose-based polymers may be chosen from (C 1 - C 4 )alkylcelluloses, such as methylcelluloses and ethylcelluloses (for example Ethocel Standard 100 Premium from Dow Chemical); hydroxy(C 1 -C 4 )alkylcelluloses, such as hydroxymethylcelluloses, hydroxyethylcelluloses and hydroxypropylcelluloses; mixed hydroxy(C 1 -C 4 )alkyl-(C 1 -C 4 )alkylcelluloses, such as hydroxypropylmethylcelluloses (for example Methocel E4M from Dow Corning), hydroxyethylmethylcelluloses, hydroxyethylethylcelluloses (for example Bermocoll E 481 FQ from AkzoNobel), and hydroxbutylmethylcelluloses, and also mixtures thereof.
  • C 1 - C 4 )alkylcelluloses such as methylcelluloses and ethylcelluloses (for example Ethocel
  • the non-associative nonionic cellulose-based polymer(s) are chosen from hydroxy(C 1 -C 4 )alkylcelluloses. More preferentially, the non-associative nonionic cellulose-based polymer(s) are hydroxyethylcellulose and/or hydroxypropylcellulose. More preferentially, composition A and/or composition B comprise(s) hydroxyethylcellulose and/or hydroxypropylcellulose. In particular, mention may be made of the hydroxyethylcellulose sold by the company Ashland Inc. under the trade name Natrosol 250 HR PC.
  • composition A and/or composition B according to the invention comprise(s) at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • composition A according to the invention comprises at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • composition A and/or composition B according to the invention comprise(s) one or more pigments.
  • the colouring agent(s) are chosen from pigments.
  • pigment refers to any pigment that gives colour to keratin 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% by weight.
  • 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 encyclopedia in the chapter on inorganic pigments.
  • mineral pigments that are useful in the present invention, mention may be made of iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.
  • the pigment may be an organic pigment.
  • organic pigment refers to any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on organic pigments.
  • the organic pigment may notably be chosen from nitroso, nitro, azo, xanthene, pyrene, 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
  • Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by the company Hoechst under the names: - Cosmenyl Yellow 10G: Yellow 3 pigment (CI 11710); - Cosmenyl Yellow G: Yellow 1 pigment (CI 11680); - Cosmenyl Orange GR: Orange 43 pigment (CI 71105); - Cosmenyl Red R: Red 4 pigment (CI 12085); - Cosmenyl Carmine FB: Red 5 pigment (CI 12490); - Cosmenyl Violet RL: Violet 23 pigment (CI 51319); - Cosmenyl Blue A2R: Blue 15.1 pigment (CI 74160); - Cosmenyl Green GG: Green 7 pigment (CI 74260); - Cosmenyl Black R: Black 7 pigment (CI 77266).
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1184426.
  • These composite pigments may notably be composed 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 45380), D&C Orange 5 (CI 45370), D&C Red 27 (CI 45410), D&C Orange 10 (CI 45425), D&C Red 3 (CI 45430), D&C Red 4 (CI 15510), D&C Red 33 (CI 17200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15985), D&C Green 5 (CI 61570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42053), D&C Blue 1 (CI 42090).
  • An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15850:1).
  • the pigment may also be a pigment with special effects.
  • the term “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 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 Cellini nacres sold by BASF (mica-TiO2-lake), Prestige sold by Eckart (mica-TiO2), Prestige Bronze sold by Eckart (mica-Fe2O3), and Colorona sold by Merck (mica-TiO2-Fe2O3).
  • nacres 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.
  • examples of nacres that may also be mentioned include polyethylene terephthalate glitter flakes, notably those sold by the company Meadowbrook Inventions under the name Silver 1P 0.004X0.004 (silver glitter flakes).
  • 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.
  • 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.
  • the reflective 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.
  • the reflective material may include a layer of metal or of a metallic material. Reflective particles are notably described in JP-A-09188830, JP-A-10158450, JP-A- 10158541, JP-A-07258460 and JP-A-05017710. Again as an example of reflective particles including a mineral substrate coated with a layer of metal, mention may also be made of particles including a silver-coated borosilicate substrate.
  • 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 a 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.
  • interference pigments which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or interference holographic glitter flakes (Geometric Pigments or Spectra f/x from Spectratek).
  • Special effect pigments 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.
  • the variety of 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 5 nm and 200 ⁇ m, preferably between 7 nm and 80 ⁇ m and more preferentially between 10 nm and 50 ⁇ m.
  • 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.
  • esters of 12-hydroxystearic 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 21000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or else polyhydroxystearic acid such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof.
  • CFA name polyglyceryl-2 dipolyhydroxystearate
  • 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 totally 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; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; alkanolamines; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.
  • waxes for example carnauba wax and beeswax
  • fatty acids, fatty alcohols and derivatives thereof such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl
  • 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 4578266.
  • 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, relative to 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, relative to the total weight of the surface-treated pigment.
  • the surface treatments of the pigments are chosen from the following treatments: - a PEG-silicone treatment, for instance the AQ surface treatment sold by LCW; - a 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, for instance the MI surface treatment sold by Miyoshi; - a perfluoropolymethyl isopropyl ether treatment, for instance the FHC surface treatment sold by LCW; - an isostearyl sebacate treatment, for instance the HS surface treatment sold by Miyoshi; - a perfluoroalkyl phosphate treatment, for instance the PF surface treatment sold
  • the dispersant is present with organic or mineral pigments in submicron-sized particulate form in the dye composition.
  • the term “submicron-sized” 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 ( ⁇ m), in particular between 0.1 and 0.9 ⁇ m, and preferably between 0.2 and 0.6 ⁇ m.
  • the dispersant and the pigment(s) are present in an amount (dispersant:pigment) 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 thus have a silicone backbone, such as silicone polyether and dispersants of amino silicone type, different from the amine silicones or alkoxysilanes of formula (I) or formula (I’) described previously in the application.
  • a silicone backbone such as silicone polyether and dispersants of amino silicone type, different from the amine silicones or alkoxysilanes of formula (I) or formula (I’) described previously in the application.
  • 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, - silicone acrylates such as Tego® RC 902, Tego® RC 922, Tego® RC 1041, and Tego® RC 1043, sold by Evonik, - polydimethylsiloxane (PDMS) silicones bearing 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.
  • PDMS polydimethylsiloxane
  • the dispersant(s) are of amino silicone type, different from the amino silicones or alkoxysilanes of formula (I) or of formula (I’) described previously in the application and are cationic.
  • the pigment(s) is (are) chosen from mineral, mixed mineral-organic or organic pigments.
  • the pigment(s) according to the invention are organic pigments.
  • the pigment(s) according to the invention are mineral pigments.
  • Composition A and/or composition B 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.
  • 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.
  • the dyes of formulae (VII) and (VIII) 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 mesityl.
  • 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.
  • dyes of formula (IX) 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 (IX’), mention may be made of: Acid Red 111, Acid Red 134, Acid Yellow 38.
  • dyes of formula (X) mention may be made of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and as an example of a dye of formula (X’), mention may be made of: Acid Yellow 17; c) the anthraquinone dyes of formulae (XI) and (XI’):
  • dyes of formula (XI) 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 (XI’), mention may be made of: Acid Black 48; d) the nitro dyes of formulae (XII) and (XII’): in which formulae (XII) and (XII’): - R 30 , R 31 and R 32 , which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from: - alkyl; - alkoxy optionally substituted with one or more hydroxyl groups, alkylthio optionally substituted with one or more hydroxyl groups; - hydroxyl, mercapto; - nitro, nitroso; - polyhaloal
  • dyes of formula (XII) mention may be made of: Acid Brown 13 and Acid Orange 3; as examples of dyes of formula (XII’), 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 (XIII): in which formula (XIII): - R 33 , R 34 , R 35 and R 36 , 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
  • dyes of formula (XIII) 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 (XIV):
  • dyes of formula (XIV) 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 (XV): - R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 , which may be identical or different, represent a hydrogen atom or a group chosen from: - alkyl; - alkoxy, alkylthio; - hydroxyl, mercapto; - nitro, nitroso; - R°-C(X)-X’-, R°-X’-C(X)-, R°-X’-C(X)-X’’- with R° representing a hydrogen atom or an alkyl or aryl group; X, X’ and X’’, which may be identical or different, representing an oxygen or sulfur atom, or NR with R
  • dyes of formula (XV) mention may be made of: Acid Blue 74. h) the quinoline-based dyes of formula (XVI): - R 61 represents a hydrogen or halogen atom or an alkyl group; - R62, R63 and R64, which may be identical or different, represent a hydrogen atom or a group (O)2S(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 (XVI) comprises at least one sulfonate radical (O) 2 S(O-)-, M + , preferentially sodium sulfonate.
  • dyes of formula (XVI) 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, juglone, 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 and better still from 0.005% to 10% by weight, relative to the total weight of composition A and/or composition B.
  • 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 A and/or composition B.
  • the direct dye(s) may be present in a total amount ranging from 0.001% to 10% by weight of the total weight of the composition, preferably from 0.005% to 5% by weight of the total weight of composition A and/or composition B.
  • composition A and/or composition B according to the invention may comprise water.
  • water is present in a content ranging from 0.1% to 95% by weight, more preferentially from 1% to 90% by weight and better still from 10% to 85% by weight, relative to the total weight of composition A and/or composition B.
  • the pH of composition A and/or composition B is preferably alkaline.
  • composition A and/or composition B may comprise an alkaline agent.
  • composition A and/or composition B according to the invention comprises an alkaline agent. The pH of the compositions is measured at room temperature.
  • alkaline agents examples include aqueous ammonia, alkanolamines, and/or basic amino acids.
  • the alkanolamine(s) are chosen from monoethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N- dimethylaminoethanolamine, 2-amino-2-methyl-1-propanol, triisopropanolamine, 2- amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino-1,2- propanediol and tris(hydroxymethylamino)methane.
  • the alkanolamine(s) are chosen from monoethanolamine and/or 2- amino-2-methyl-1-propanol.
  • the amino acid(s) are chosen from aminocarboxylic acids such as alpha- aminocarboxylic acid.
  • basic amino acid means amino acids having an isoelectric point of greater than 7.
  • composition A may comprise an inorganic alkaline agent, preferably chosen from ammonium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and/or potassium carbonate.
  • an inorganic alkaline agent preferably chosen from ammonium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, sodium metasilicate, potassium silicate, sodium carbonate and/or potassium carbonate.
  • composition A and/or composition B comprise(s) an alkaline agent chosen from aqueous ammonia, monoethanolamine, 2-amino-2-methyl-1-propanol, arginine and/or lysine.
  • Composition A and/or Composition B may (may) also comprise acidifying agents to adjust the pH.
  • the acidifying agents are chosen from citric acid, lactic acid, acetic acid and/or mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.
  • Additives: Composition A and/or composition B may also contain any commonly used adjuvant or additive.
  • additives that may be contained in the composition, mention may be made of reducing agents, thickeners different from the polymers described previously, softeners, antifoams, moisturizers, UV-screening agents, peptizers, dispersants, fragrances, anionic, cationic, nonionic or amphoteric surfactants, proteins, vitamins, preserving agents, waxes and mixtures thereof.
  • composition A and/or composition B 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, an anhydrous liquid or an anhydrous gel.
  • composition A according to the invention is an anhydrous liquid or an anhydrous gel.
  • composition B according to the invention is a dispersion.
  • 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 composition A and/or composition B.
  • Metal Composition C according to the invention comprises at least one metal compound.
  • the term “metal compound” means a compound comprising at least one atom chosen from metals.
  • composition C comprises at least one metal compound, the metal(s) being chosen from transition metals, metals from the group of the lanthanide family, aluminium, boron, tin, bismuth, alkali metals and alkaline-earth metals such as magnesium, and mixtures thereof.
  • the metal compound(s) comprise(s) at least one metal chosen from titanium, tin, aluminium, zirconium, and mixtures thereof, better still titanium, aluminium and mixtures thereof.
  • composition C comprises at least one metal compound, the metal(s) being chosen from titanium, tin, aluminium, zirconium, and mixtures thereof, better still titanium, aluminium and mixtures thereof.
  • the metal compound(s) are different from the colouring agents as described above.
  • the metal compound(s) are chosen from organometallic compounds.
  • the organometallic compound(s) is (are) preferably chosen from the metal alkoxides of formulae (XVIIa), (XVIIb), (XVIIc) and (XVIId) below and mixtures thereof: M-(OR 1 ) n (XVIIa) R-M (OR 1 ) n-1 (XVIIb) (R 1 O) n-1 -M-R”-M’-(OR 1 ) n-1 (XVIIc) RR’-M-(OR 1 ) n-2 (XVIId) in which: - M and M’, independently of each other, represent an atom chosen from transition metals, metals from the lanthanide group of the Periodic Table, aluminium, boron, tin, bismuth, alkali metals and alkaline-earth metals such as magnesium, preferably titanium
  • the organometallic compound(s) is (are) chosen from the metal alkoxides of formula (XVIIa), in which: - M represents an atom chosen from transition metals, the metals of the lanthanide group of the Periodic Table, aluminium, boron, tin, bismuth, alkali metals and alkaline- earth metals such as magnesium, preferably titanium or aluminium; - n represents the valency of the atom; - R 1 , which may be identical or different, represent a linear or branched saturated hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms.
  • formula (XVIIa) in which: - M represents an atom chosen from transition metals, the metals of the lanthanide group of the Periodic Table, aluminium, boron, tin, bismuth, alkali metals and alkaline- earth metals such as magnesium, preferably titanium or aluminium; - n represents the valency of
  • the organometallic compound(s) is (are) chosen from the metal alkoxides of formula (XVIIa), in which: - M represents an atom chosen from titanium, tin, bismuth, aluminium and zirconium, preferably titanium or aluminium; - n represents the valency of the atom; - R1 represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t- butyl group.
  • formula (XVIIa) in which: - M represents an atom chosen from titanium, tin, bismuth, aluminium and zirconium, preferably titanium or aluminium; - n represents the valency of the atom; - R1 represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t- butyl group
  • the organometallic compound(s) is (are) chosen from the tetraalkoxytitanium compounds of formula (XVIII) below: Ti(OR 3 ) y (OR 4 ) 4-y (XVIII) in which: - R 3 and R 4 represent, independently of each other, a linear or branched alkyl radical containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, and - y is an integer ranging from 3 to 4.
  • formula (XVIII) Ti(OR 3 ) y (OR 4 ) 4-y (XVIII) in which: - R 3 and R 4 represent, independently of each other, a linear or branched alkyl radical containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, and - y is an integer ranging from 3 to 4.
  • organometallic compounds based on aluminium and notably aluminium di-s-butoxide ethylacetoacetate organometallic compounds based on tin and notably tin bis(2- ethylhexanoate), tin bis(neodecanoate), tin di-n-butylbis(2,4-pentanedionate), di-n- butyldiacetoxytin, tin dimethyldineodecanoate, tin dimethylhydroxy(oleate), dioctylauryltin, dioctyldilauryltin, tin(II) oleate and mixtures thereof, organometallic compounds based on zirconium and notably zirconium ethoxide, zirconium propoxide, zirconium isopropoxide, zirconium butoxide, zirconium tert-butoxid
  • the metal compound is titanium butoxide. Titanium butoxide may be purchased, for example, from Shin-Etsu under the name D- 25.
  • the metal compound is a metal salt.
  • the metal salt(s) are chosen from transition metal salts, alkali metal salts, alkaline-earth metal salts such as magnesium salts, aluminium salts, boron salts, tin salts, hydrates thereof and mixtures thereof, more preferentially titanium salts, aluminium salts, hydrates thereof and mixtures thereof.
  • the term “metal salt” means a salt resulting notably from the action of at least one acid on a metal.
  • the metal salt(s) may be in the form of hydrates.
  • the metal salt(s) may be organic or inorganic.
  • organic metal salt means a salt notably obtained from the action of an organic acid on a metal.
  • mineral metal salt means a salt notably obtained from the action of a mineral acid on a metal.
  • inorganic acid means an acid which does not include any carbon atoms, apart from carbonic acid.
  • the mineral metal salt(s) are chosen from halides such as chlorides, fluorides, iodides and bromides, carbonates, sulfates, phosphates, nitrates, perchlorates, hydrates thereof, and mixtures thereof.
  • the mineral metal salt(s) are chosen from aluminium sulfate, hydrated or non-hydrated aluminium chloride and mixtures thereof.
  • the metal salt(s) are organic, more preferentially chosen from citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, glycinates, tartrates,benzoates, hydrates thereof, and mixtures thereof.
  • the metal salt(s) are chosen from titanium citrate, aluminium acetate, aluminium lactate, hydrated or non-hydrated aluminium citrate, aluminium glycinate, aluminium benzoate and mixtures thereof.
  • composition C according to the invention may comprise one or more organic solvents.
  • organic solvent examples that may be mentioned include alkanes containing from 8 to 16 carbon atoms, and notably branched C 8 to C 16 alkanes such as C 8 to C 16 isoalkanes of petroleum origin (also called isoparaffins) such as isododecane (also called 2,2,4,4,6- pentamethylheptane), isodecane or isohexadecane.
  • Cyclic silicones may also be mentioned.
  • the cyclic silicone is chosen from polydialkylsiloxanes, notably polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes including at least one functional group chosen from aryl groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the cyclic silicones are volatile.
  • the cyclic silicones may be more particularly chosen from those having a boiling point of between 60°C and 260°C, and even more particularly from cyclic polydialkylsiloxanes including from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes including from 3 to 7 and preferably 4 to 5 silicon atoms.
  • octamethylcyclotetrasiloxane sold notably under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia
  • decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide
  • Silbione® 70045 V5 by Rhodia
  • Mention may also be made of cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as Silicone Volatile® FZ 3109 sold by the company Union Carbide, of formula: Mention may also be made of mixtures of cyclic polydialkylsiloxanes with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1’-bis(2,2,2’,2’,3,3’- hexatrimethylsilyloxy)neopentane.
  • cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type such as Silicone Volatile® FZ 3109 sold by the company Union Carbide, of formula: Mention may also be made of mixtures of
  • the cyclic silicones are chosen from cyclic polydialkylsiloxanes including from 3 to 7 and preferably from 4 to 5 silicon atoms as mentioned above.
  • the organic solvent(s) are chosen from branched C 8 to C 16 alkanes, cyclic silicones and mixtures thereof, more particularly from cyclic polydialkylsiloxanes including from 3 to 7 silicon atoms, better still from 4 to 5 silicon atoms.
  • the organic solvents may be present in a total amount ranging from 40% to 99.8% by weight, relative to the total weight of composition C, preferably from 50% to 99.5% by weight, relative to the total weight of composition C.
  • Composition C may comprise an amino silicone as described previously.
  • a subject of the present invention is a process for dyeing keratin fibres such as the hair, comprising: i) a step of applying to the keratin fibres at least one composition C comprising at least one metal compound as described previously, ii) a step of applying to the keratin fibres at least one composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and iii) a step of applying to the keratin fibres at least one composition B comprising: - at least one film-forming polymer as described previously; composition A and/or composition B comprising at least one colouring agent chosen from pigments, direct dyes and mixtures thereof; it being understood that steps i), ii) and ii
  • composition A, composition B and/or composition C according to the invention are compositions for dyeing keratin fibres, such as the hair.
  • Composition A, composition B and composition C are applied sequentially.
  • composition C is first applied to the keratin fibres, followed by composition A in a second stage, followed by composition B in a third stage, i.e. i), then ii), then iii).
  • composition A is first applied to the keratin fibres followed by composition C in a second stage, followed by composition B in a third stage, i.e. ii), then i), then iii).
  • the process for dyeing keratin fibres such as the hair comprises: i) application to the keratin fibres of composition C comprising at least one metal compound as described previously, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition C on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, v) optionally a leave-on time
  • the process for dyeing keratin fibres such as the hair comprises: i) application to the keratin fibres of composition C comprising at least one metal compound as described previously, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition C on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, v) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds
  • the process for dyeing keratin fibres such as the hair comprises: i) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application to the keratin fibres of composition C comprising at least one metal compound as described previously, v) optionally a leave-on time of
  • the process for dyeing keratin fibres such as the hair comprises: i) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application to the keratin fibres of composition C comprising at least one metal compound as described previously, v) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds
  • the process for dyeing keratin fibres such as the hair comprises: i) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application of composition B according to the invention comprising: - at least one film-forming polymer as described previously; v) optionally a leave-on
  • the process for dyeing keratin fibres such as the hair comprises: i) application to said keratin fibres of composition A according to the invention comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) application of composition B according to the invention comprising: - at least one film-forming polymer as described previously, and - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, v) optionally a leave-
  • compositions A, B and C according to the invention may be used on wet or dry keratin fibres, and also on any type of fair or dark, natural or dyed, permanent-waved, bleached or relaxed fibres. According to a particular embodiment of the process of the invention, the fibres are washed before applying compositions A, B and C according to the invention.
  • the application of compositions A, B and C according to the invention to the keratin fibres may be performed via any standard means, in particular using a comb, a fine brush, a coarse brush or with the fingers.
  • the dyeing process i.e.
  • compositions A, B and C according to the invention to the keratin fibres is generally performed at room temperature (between 15 and 25°C).
  • room temperature between 15 and 25°C.
  • the process for dyeing keratin fibres such as the hair comprises: i) application to the keratin fibres of composition C comprising at least one metal compound as described previously, ii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition C on said fibres, iii) optionally a step of washing, rinsing, draining or drying said fibres, iv) preparing composition A according to the invention by mixing a first composition A’ and a second composition A’’, in which the first composition A’ comprises: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and the second composition A’’ comprises: - at least one colouring agent
  • composition A’ preferably comprises a low water content or is anhydrous.
  • composition A’ comprises a water content of between 0.001% and 10% by weight, better still between 0.5% and 9% by weight, more preferentially between 1% and 8% by weight, relative to the weight of composition A’.
  • Composition A’’ may also contain water.
  • the process for dyeing keratin fibres such as the hair comprises: i) the preparation of composition A according to the invention by mixing a first composition A’ and a second composition A’’, in which the first composition A’ comprises: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and the second composition A’’ comprises: - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, ii) application to said keratin fibres of composition A according to the invention, iii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iv) optionally a step of washing, rinsing, drain
  • the process for dyeing keratin fibres such as the hair comprises: i) the preparation of composition A according to the invention by mixing a first composition A’ and a second composition A’’, in which the first composition A’ comprises: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, and the second composition A’’ comprises: - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, ii) application to said keratin fibres of composition A according to the invention, iii) optionally a leave-on time of from 10 seconds to 20 minutes, notably from 20 seconds to 10 minutes, preferably from 30 seconds to 5 minutes, of composition A on said fibres, iv) optionally a step of washing, rinsing, drain
  • the keratin fibres may be subjected to a drying step, for example using a hairdryer.
  • the drying step may be performed for a period of between 20 seconds and 5 minutes.
  • the drying step may be performed using absorbent paper, a hairdryer or a styling hood or by drying naturally.
  • the drying step is performed using a hairdryer at a temperature greater than or equal to 30°C, more particularly at a temperature above 30°C and below 110°C.
  • compositions A, B and C according to the invention After applying compositions A, B and C according to the invention to the keratin fibres, there may be a waiting time of at least 10 seconds, preferably at least 30 seconds, before the step of drying the keratin fibres.
  • the process according to the invention may comprise a step of applying heat to the keratin fibres using a heating tool.
  • the process according to the invention does not comprise a step of applying heat to the keratin fibres using a heating tool in addition to the possible drying step.
  • 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 and/or a straightening iron, more preferentially using a hairdryer.
  • 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 present invention also relates to a device for dyeing keratin fibres such as the hair, comprising several compartments containing: - in a first compartment, a composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, - in a second compartment, a composition B according to the invention comprising: - at least one film-forming polymer as described previously, and - in a third compartment, a composition C comprising at least one metal compound as described previously, composition A and/or composition B comprising at least one colouring agent chosen
  • the dyeing device is a device for dyeing keratin fibres such as the hair, comprising several compartments containing: - in a first compartment, a composition A’ comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, - in a second compartment, a composition A’’ comprising: - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, - in a third compartment, a composition B comprising: - at least one hydrophobic film-forming polymer as described previously, - in a fourth compartment, a composition C comprising at least one metal compound as described previously.
  • a composition A’ comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as
  • the dyeing device is a device for dyeing keratin fibres such as the hair, comprising several compartments containing: - in a first compartment, a composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and - at least one alkoxysilane of formula (II) as described previously, oligomers thereof and/or mixtures thereof, - in a second compartment, a composition B comprising: - at least one hydrophobic film-forming polymer as described previously, and - at least one colouring agent chosen from pigments, direct dyes and mixtures thereof, and - in a third compartment, a composition C comprising at least one metal compound as described previously.
  • a composition A comprising: - at least one alkoxysilane chosen from the compounds of formula (I) or of formula (I’) as described previously, oligomers thereof and/or mixtures thereof, and
  • Example in the examples the temperature is given in degrees Celsius and corresponds to room temperature (20-25°C), unless otherwise indicated, and the pressure is atmospheric pressure, unless otherwise indicated.
  • compositions are prepared (in g/100 g of unmodified starting material, AM: Active Material): [Table 1] [Table 2] [Table 3] [Table 4] [Table 5] (1) Sold under the trade name KBE-903 by the company Shin-Etsu; (2) Synthetic fluorphlogopite (and) titanium dioxide (and) tin oxide sold under the trade name Syncrystal Silk Silver by the company Eckart (3) Sold under the trade name Ecosmooth Satin by the company Dow Corning, (4) Sold under the trade name PVP K30L by the company ISP (Ashland) (5) Sold under the trade name Dermacryl 79 by the company Akzo Nobel (6) Sold under the trade name D-25 by the company Shin-Etsu.
  • Protocol Two distinct protocols are applied to the locks of hair: - either composition C is applied to the locks of hair (process according to the invention), - or composition C is not applied to the locks of hair (comparative process).
  • composition C is applied with the fingers to dry chestnut-brown locks of hair (HT4), in a proportion of 1 g of composition per gram of lock. The locks of hair are left for 5 minutes at room temperature. The locks of hair are then drained dry between the fingers.
  • Compositions A1’ and A1’’ are mixed in a 50/50 ratio to obtain composition A1.
  • Composition A1 is applied to locks of hair treated with composition C and to locks of hair not treated with composition C (dry chestnut-brown locks of hair (HT4)), in a proportion of 1 g of composition per gram of lock. The locks of hair are left for 2 minutes at room temperature.
  • Composition B1 is then applied to the locks of hair treated with composition A1 + C, in a proportion of 1 g of composition per gram of lock.
  • Composition B1 is also applied to the locks of hair treated only with composition A1, in a proportion of 1 g of composition per gram of lock. The locks of hair are left for 5 minutes at room temperature. The locks of hair are then dried with a hairdryer for 2 minutes. The locks of hair are left at room temperature for 24 hours.
  • composition A2 is applied with the fingers to locks of dry chestnut-brown hair (HT4), in a proportion of 1 g of composition per gram of lock. The locks of hair are left for 5 minutes at room temperature. The locks of hair are then wiped with an absorbent paper and not dried.
  • Composition C is applied with the fingers to some locks of hair treated with composition A2, in a proportion of 1 g of composition per gram of lock. The locks of hair are left for 2 minutes at room temperature. The locks of hair are then drained dry between the fingers.
  • Composition B2 is then applied to the locks of hair treated with composition A2 + C and to locks of hair treated only with composition A2, in a proportion of 1 g of composition per gram of lock.
  • the locks of hair are left for 2 minutes at room temperature.
  • the locks of hair are then dried with a hairdryer for 2 minutes.
  • the locks of hair are left at room temperature for 24 hours.
  • the locks of hair thus dyed are then subjected to a shampoo wash so as to evaluate the fastness (persistence) of the colouring obtained with respect to shampoo washing, according to the shampoo washing protocol described below.
  • Shampoo washing protocol The locks of hair are washed with a standard shampoo (Garnier Ultra Doux).
  • the locks of hair are then rinsed, combed and dried with a hairdryer.
  • the next shampoo wash is performed on the locks obtained after the application of the hairdryer.
  • the ⁇ E value is calculated according to the following equation: [Math.1]
  • L*a*b* represent the values measured after dyeing the hair and after performing a shampoo wash
  • L0*a0*b0* represent the values measured after dyeing the hair but before shampooing.
  • [Table 6] The locks of hair dyed with compositions C + A1 + B1 according to the invention, and washed with a shampoo show low ⁇ E values compared to the locks of hair dyed with compositions A1 + B1 only.
  • the locks of hair dyed with compositions A2 + C + B2 according to the invention, and washed with a shampoo show low ⁇ E values compared to the locks of hair dyed with compositions A2 + B2 only.
  • the coloured coating of the keratin fibres obtained with the compositions C + A1 + B1 according to the invention or with the compositions A2 + C + B2 according to the invention shows good shampoo-fastness.
  • the locks of hair dyed with compositions C + A1 + B1 according to the invention or with compositions A2 + C + B2 according to the invention and washed with a shampoo show good colour persistence.

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Abstract

La présente invention concerne un procédé de teinture de fibres de kératine telles que les cheveux, comprenant une étape consistant à appliquer sur les fibres de kératine au moins une composition C comprenant au moins un composé métallique, une étape consistant à appliquer sur les fibres de kératine au moins une composition A comprenant au moins un alcoxysilane sélectionné parmi les composés de formule (I) ou de formule (I'), et au moins un alcoxysilane de formule (II), et une étape consistant à appliquer sur les fibres de kératine au moins une composition B comprenant au moins un polymère filmogène, une composition A et/ou une composition B comprenant au moins un colorant sélectionné parmi des pigments, des colorants directs et leurs mélanges. Les étapes i), ii) et iii) sont effectuées successivement i), puis ii), puis iii), ou bien ii), puis i), puis iii), ou bien ii), puis iii), puis i).
PCT/EP2023/058454 2022-03-31 2023-03-31 Procédé de teinture capillaire comprenant l'application d'une composition c comprenant un composé métallique WO2023187157A1 (fr)

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US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
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WO2020035362A1 (fr) * 2018-08-16 2020-02-20 Henkel Ag & Co. Kgaa « procédé pour la coloration de matériau kératinique, comprenant l'utilisation d'un composé organique du silicium, un polymère de silicone et un composé chromogène »
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WO2021013517A1 (fr) * 2019-07-19 2021-01-28 Henkel Ag & Co. Kgaa Procédé de coloration d'une matière kératinique comprenant l'application d'un composé organosilicié, d'un pigment à effet coloré et d'un réactif de scellement i
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WO2021028095A1 (fr) * 2019-08-14 2021-02-18 Henkel Ag & Co. Kgaa Procédé de décoloration de matières kératiniques colorées à l'aide d'un composé organosilicié et d'un pigment
WO2021028094A1 (fr) * 2019-08-14 2021-02-18 Henkel Ag & Co. Kgaa Procédé de décoloration de matières kératiniques colorées à l'aide d'un composé organosilicié et d'un pigment
WO2022161663A1 (fr) * 2021-01-27 2022-08-04 Henkel Ag & Co. Kgaa Procédé de coloration de matière kératinique comprenant l'utilisation d'un composé organo-silicié, un composé colorant, un réactif d'étanchéité et un agent de post-traitement

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US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
JPH0517710A (ja) 1991-07-08 1993-01-26 Kansai Paint Co Ltd メタリツク塗料とその塗装法
FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO1995001772A1 (fr) 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
WO1995015144A1 (fr) 1993-11-30 1995-06-08 Ciba-Geigy Ag Colorants cationiques pour fibres keratiniques
JPH07258460A (ja) 1994-03-22 1995-10-09 Teijin Chem Ltd 樹脂組成物
EP0714954A2 (fr) 1994-11-03 1996-06-05 Ciba-Geigy Ag Colorants cationiques glyoxalin azoiques
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WO2021028095A1 (fr) * 2019-08-14 2021-02-18 Henkel Ag & Co. Kgaa Procédé de décoloration de matières kératiniques colorées à l'aide d'un composé organosilicié et d'un pigment
WO2021028094A1 (fr) * 2019-08-14 2021-02-18 Henkel Ag & Co. Kgaa Procédé de décoloration de matières kératiniques colorées à l'aide d'un composé organosilicié et d'un pigment
WO2022161663A1 (fr) * 2021-01-27 2022-08-04 Henkel Ag & Co. Kgaa Procédé de coloration de matière kératinique comprenant l'utilisation d'un composé organo-silicié, un composé colorant, un réactif d'étanchéité et un agent de post-traitement

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