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WO2025132075A1 - Procédé de coloration de fibres kératiniques comprenant l'application d'au moins un amino alcoxysilane, un polymère porteur de fonctions acétoacétate et un agent colorant - Google Patents

Procédé de coloration de fibres kératiniques comprenant l'application d'au moins un amino alcoxysilane, un polymère porteur de fonctions acétoacétate et un agent colorant Download PDF

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Publication number
WO2025132075A1
WO2025132075A1 PCT/EP2024/086208 EP2024086208W WO2025132075A1 WO 2025132075 A1 WO2025132075 A1 WO 2025132075A1 EP 2024086208 W EP2024086208 W EP 2024086208W WO 2025132075 A1 WO2025132075 A1 WO 2025132075A1
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composition
carbon atoms
weight
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Inventor
Arnaud Bonnamy
Laurent SABATIE
Fabien BROTHIER
Marie GRACIA
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LOreal SA
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LOreal SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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
    • A61K8/72—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
    • 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

Definitions

  • the present invention relates to the field of the cosmetic treatment of keratin fibres and notably to the dyeing of keratin fibres, preferably the hair.
  • the aim of the invention is thus to offer novel dyeing processes comprising the application to said keratin fibres of a polymer bearing acetoacetate units, which offer excellent technical performance, particularly in terms of the persistence of the colourings they afford.
  • the subject of the present invention is a process for dyeing keratin fibres such as the hair, comprising the application to the keratin fibres of at least one composition A comprising at least one amino alkoxysilane chosen from the compounds of formula (I) or (T) and the application to the keratin fibres of at least one composition B, different from composition A, comprising at least one polymer P comprising repeating units obtained from at least one monomer of formula (III).
  • Said composition A and/or composition B comprise at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • Another dyeing method consists in using pigments. Specifically, the use of pigments on the surface of keratin fibres generally makes it possible to obtain colourings that are visible on dark hair, since the surface pigment masks the natural colour of the fibre. However, the colourings obtained via this dyeing method have the drawback of having poor resistance to shampoo washing and also to external agents such as sebum, perspiration, brushing and/or rubbing.
  • hair makeup products have recently been developed, proposing temporary hair dyeing that lasts after one to three shampoos washes. They are a particularly attractive alternative for consumers to permanent hair dyeing, provided that the colouring effect is effectively guaranteed to last after contact with water and a few shampoo washes. This requirement may notably be satisfied by the use of effective film-forming agents.
  • FR 2 741 530 proposes for this purpose, for the temporary dyeing of keratin fibres, the use of a dispersion of film-forming polymer particles including at least one acidic function and at least one pigment dispersed in the continuous phase of said dispersion.
  • the colourings obtained via this dyeing method nevertheless have the drawback of being removed too quickly on shampoo washing.
  • step a) is performed before step b).
  • the process according to the invention affords smooth, uniformly coloured coatings. It provides visible colouring on all types of fibres, which is resistant to water and thus notably to shampoo washing and sebum.
  • a coating may be resistant to the various external attacking factors to which keratin fibres may be subjected, for instance blow-drying, brushing, friction and perspiration.
  • the term “less than” and, respectively, the term “greater than” refer to an open range which is strictly less, or, respectively, strictly greater, and thus that the limits are not included;
  • 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 “hair” means head hair. This term does not correspond to bodily hairs, to the eyebrows or to the eyelashes.
  • 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;
  • hydroxyalkyl radical denotes an alkyl radical as defined previously, said alkyl radical comprising an OH group;
  • alkylene denotes a linear or branched divalent saturated C1-C10 hydrocarbon-based group such as methylene, ethylene or propylene;
  • cycloalkyF or "alicycloalkyF radical denotes a cyclic saturated monocyclic or polycyclic, 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 particularly from 3 to 20 carbon atoms, even more particularly from 3 to 12 carbon atoms, preferably between 5 and 10 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl or isobornyl, in particular cyclopropyl, cyclopentyl or cyclohexyl, it being understood that the cycloalkyl radical may be substituted with one or more (Ci-C4)alkyl groups such as methyl; preferably, the cycloalkyl radical is then an isobomyl group;
  • an “aryl” radical is a monocyclic, bicyclic or tricyclic, fused or non-fused, unsaturated and aromatic hydrocarbon-based cyclic radical, comprising from 6 to 30 carbon atoms, preferably between 6 and 14 carbon atoms, more preferentially between 6 and 12 carbon atoms; preferably, the aryl group comprises 1 ring of 6 carbon atoms such as phenyl, naphthyl, anthryl, phenanthryl and biphenyl, it being understood that the aryl radical may be substituted with one or more (Ci-C4)alkyl groups such as methyl, preferably tolyl, xylyl, or methylnaphthyl; preferably, the aryl group represents phenyl;
  • an “aryloxy” radical denotes an aryl-oxy radical with “aryl” as defined previously;
  • an “alkoxy” radical denotes an alkyl-oxy radical with “alkyl” as defined previously.
  • composition A is not limited to the examples illustrated. The characteristics of the various examples may notably be combined within variants which are not illustrated.
  • Composition A is not limited to the examples illustrated. The characteristics of the various examples may notably be combined within variants which are not illustrated.
  • the process according to the invention comprises at least the application a) to keratin fibres of at least one composition A comprising at least one amino alkoxysilane chosen from the compounds of formula (I) or (I’), oligomers thereof and/or mixtures thereof.
  • composition A comprises at least one amino alkoxy silane chosen from the compounds of formula (I) or (I’) hereinbelow, oligomers thereof and/or mixtures thereof.
  • 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 1 to 20 carbon atoms, preferably from 1 to 6 carbon atoms and notably from 1 to 4 carbon atoms, notably an ethyl group, it being understood that if Ra does not represent an alkoxy group, then Rb and Rc cannot simultaneously represent a hydrogen atom;
  • Rd and Re which may be identical or different, represent a hydrogen atom; 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; a cycloalkyl group containing from 3 to 20 carbon atoms; an aryl group containing from 6 to 12 carbon atoms; an aminoalkyl group containing from 1 to 20 carbon atoms;
  • - A independently represents a linear or branched alkylene group containing from 1 to 10 carbon atoms, which may be interrupted with at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH;
  • - r denotes an integer ranging from 0 to 1.
  • alkoxysilanes of formula (I), oligomers thereof and/or mixtures thereof mention may notably be made of 3 -aminopropyltri ethoxy silane (APTES), 3- aminopropylmethyldiethoxysilane (APMDES), 3-ureidopropyltrimethoxysilane and N-cy cl ohexy 1 aminomethy Itri ethoxy sil ane .
  • APTES 3 -aminopropyltri ethoxy silane
  • APIMDES 3- aminopropylmethyldiethoxysilane
  • 3-ureidopropyltrimethoxysilane and N-cy cl ohexy 1 aminomethy Itri ethoxy sil ane .
  • APTES may be purchased, for example, from the company Dow Coming under the name Xiameter OFS-6011 Silane or from the company Momentive Performance Materials under the name Silsoft A-l 100 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 -Ureidopropyltrimethoxy silane 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 (E), oligomers thereof and/or mixtures thereof mention may notably be made of N,N-bis[3- (trimethoxysilyl)propyl]ethylenediamine (CAS RN: 74956-86-8), Nl,Nl-bis[3- (triethoxysilyl)propyl]-l,2-ethanediamine (CAS RN: 457065-96-2), 1,2- ethanediamine, Nl-[3-(triethoxysilyl)propyl]-Nl-[3-(trimethoxysilyl)propyl]- (CAS RN: 1638528-78-5), and mixtures thereof.
  • the alkoxysilane(s) of formula (I) are chosen from the compounds of formula (I) below: in which:
  • Ra 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;
  • Rb and Re 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;
  • Rd and Re which are identical, represent a hydrogen atom or Rd denotes a hydrogen atom and Re denotes a Cs-G, cycloalkyl radical such as cyclohexyl;
  • the alkoxysilane(s) of formula (I) are chosen from the compounds of formula (I) in which Ra represents an ethoxy group, Rb and Re are identical and represent ethyl, Rd and Re represent a hydrogen atom, A represents propylene and r denotes an integer equal to 0.
  • the alkoxysilane of formula (I) is 3- aminopropyltriethoxysilane (APTES).
  • the amino alkoxysilane(s) of formulae (I) and/or formula (I’), oligomers thereof and/or mixtures thereof are present in composition A in a total amount ranging from 0.1% to 60% by weight, more preferentially 0.1% to 40% by weight, even more preferentially 0.5% to 30% by weight, better still 0.75% to 25% by weight, better still 1% to 20% by weight and even better still 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 are present in composition A in a total amount ranging from 0.1% to 60% by weight, more preferentially 0.1% to 40% by weight, even more preferentially from 0.5% to 30% by weight, better still from 0.75% to 25% by weight, better still from 1% to 20% by weight and even better still from 5% to 15% by weight, relative to the total weight of composition A.
  • the total content of 3 -aminopropyltri ethoxy silane in composition A ranges from 0.1% to 60% by weight, more preferentially 0.1% to 40% by weight, even more preferentially from 0.5% to 30% by weight, better still from 0.75% to 25% by weight, better still from 1% to 20% by weight and even better still from 5% to 15% by weight, relative to the total weight of composition A.
  • composition A comprises at least one amino alkoxy silane chosen from said compounds of formula (I) or (I’) as described above, oligomers thereof and/or mixtures thereof, and at least one non-amino alkoxy silane chosen from said compounds 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
  • - Re 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; it being understood that if Ra and Re do not represent an alkoxy group, then Rb cannot represent a hydrogen atom;
  • - k denotes an integer ranging from 0 to 5, preferably ranging from 0 to 3;
  • Rf represents a hydrogen atom; an alkyl group containing from 1 to 10 carbon atoms and notably from 1 to 4 carbon atoms; or a group of formula (Ila) below: in which R n represents a hydroxyl group (OH); an alkyl group containing from 1 to 10 carbon atoms, preferably a methyl.
  • non-amino alkoxy silanes of formula (II), oligomers thereof and/or mixtures thereof mention may notably be made of tetraethoxy silane (TEOS), methyltrimethoxysilane (MTMS), methyltriethoxysilane (MTES), dimethyldiethoxysilane (DMDES), diethyldiethoxysilane, dipropyldiethoxysilane, propyltri ethoxy sil ane, i sobuty Itri ethoxy sil ane, pheny Itri ethoxy sil ane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, benzyltriethoxysilane, benzylmethyldiethoxysilane, dibenzyldiethoxysilane, acetoxymethyltriethoxysilane, octytri ethoxy sil ane (OTES) and mixtures thereof.
  • TEOS tetra
  • 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.
  • non-amino alkoxysilane(s) of formula (II), oligomers thereof and/or mixtures thereof are such that:
  • Ra 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;
  • - Re 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 ranging from 0 to 3, preferably equal to 0;
  • Rf represents a hydrogen atom or an alkyl group containing from 1 to 10 carbon atoms and notably from 1 to 4 carbon atoms such as a methyl or an ethyl.
  • non-amino 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;
  • - Re 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;
  • Rf represents an alkyl group containing from 1 to 10 carbon atoms and notably from 1 to 4 carbon atoms such as a methyl or an ethyl.
  • the non-amino alkoxysilane(s) of formula (II) are methyltrimethoxysilane (MTMS), octytriethoxysilane (OTES), methyltriethoxysilane (MTES), and mixtures thereof; more preferentially methyltrimethoxysilane (MTMS) and/or methyltriethoxysilane (MTES).
  • composition A comprises at least one amino alkoxy silane chosen from said compounds of formula (I) as described above, oligomers thereof and/or mixtures thereof, and at least one nonamino alkoxysilane chosen from said compounds of formula (II), oligomers thereof and/or mixtures thereof.
  • composition A preferably comprises at least one amino alkoxysilane chosen from said compounds of formula (I) as described above, and at least one non-amino alkoxy silane chosen from said compounds of formula (II).
  • composition A more preferentially comprises 3- aminopropyltriethoxysilane as amino alkoxysilane, and at least one non-amino alkoxysilane chosen from methyltrimethoxysilane, methyltriethoxysilane, octytri ethoxy silane, and mixtures thereof.
  • composition A more particularly comprises 3- aminopropyltriethoxysilane as amino alkoxysilane, and methyltriethoxysilane as non- amino alkoxysilane.
  • the non-amino alkoxysilane(s) of formula (II), oligomers thereof and/or mixtures thereof are present in composition A in a total amount ranging from 0.1% to 20% by weight, more preferentially from 0.5% to 15%, even more preferentially from 1% to 10% by weight, better still from 1% to 5% by weight, relative to the total weight of composition A.
  • composition A comprises methyltrimethoxysilane (MTMS), methyltriethoxysilane (MTES), octytriethoxysilane (OTES) or mixtures thereof
  • MTMS methyltrimethoxysilane
  • MTES methyltriethoxysilane
  • OTES octytriethoxysilane
  • the total content of methyltrimethoxysilane (MTMS), methyltriethoxysilane (MTES), octytriethoxysilane (OTES) and/or mixtures thereof, in composition A ranges from 0.1% to 20% by weight, more preferentially from 0.5% to 15%, even more preferentially from 1% to 10% by weight, better still from 1% to 5% by weight, relative to the total weight of composition A.
  • amino alkoxysilane(s) in composition A are chosen from said compounds of formula (I), oligomers thereof, and mixtures thereof.
  • oligomer means compound(s) including at least two silicon atoms, obtained by oligomerization or polymerization of compounds of formula (I), (f) or (II).
  • the total content of alkoxysilane(s) in composition A ranges from 0.1% to 60% by weight, more preferentially from 1% to 50% by weight, even more preferentially from 2% to 40% by weight, better still from 3% to 30% by weight, even better still from 5% to 20% by weight, relative to the total weight of composition A.
  • the alkoxy silane(s) in composition A are chosen from 3- aminopropyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, octytri ethoxy silane (OTES), and mixtures thereof
  • the total content of alkoxysilane(s) in composition A ranges from 1% to 50% by weight, even more preferentially from 2% to 40% by weight, better still from 3% to 30% by weight, even better still from 5% to 20% by weight, relative to the total weight of composition A.
  • composition A used in the process according to the invention may also comprise at least one organic solvent.
  • organic solvents examples include C1-C4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance glycerol, 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether and diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • C1-C4 alkanols such as ethanol and isopropanol
  • polyols and polyol ethers for instance glycerol, 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether and diethylene glycol monoethyl ether and monomethyl ether
  • aromatic alcohols for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the organic solvent(s) are chosen from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether or monoethyl ether, diethylene glycol monomethyl ether or monoethyl ether, benzyl alcohol, phenoxyethanol, and mixtures thereof.
  • composition A comprises ethanol.
  • the total content of organic solvent(s) in composition A ranges from 1% to 30% by weight, preferably from 2% to 20% by weight and more preferentially from 5% 15% by weight, relative to the total weight of composition A.
  • composition A comprises water.
  • the total water content of composition A ranges from 10% to 98% by weight, more preferentially from 40% to 95% by weight, even more preferentially from 50% to 92% by weight, better still from 60% to 90% by weight and even better still from 70% to 90% by weight, relative to the total weight of composition A.
  • Composition B is a composition of Composition B:
  • the process according to the invention comprises at least the application b) to the keratin fibres of at least one composition B comprising at least one polymer P comprising repeating units obtained from at least one monomer of formula (III) below: in which:
  • R b and R c which may be identical or different, represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group,
  • R d represents a linear or branched (Ci-C4)alkyl group
  • - L represents a linear or branched (Ci-Ce)alkylene, or cycloalkylene, group.
  • R a represents a hydrogen atom or a methyl group, more preferentially a methyl group
  • R b and R c preferably represent a hydrogen atom
  • R d preferably represents a methyl group
  • L preferably represents a (Ci-C4)alkylene group, and more preferentially L represents ethylene.
  • the monomer of formula (III) is chosen from acetoacetoxyethyl acrylate, acetoacetoxyethyl methacrylate, and mixtures thereof.
  • the polymer(s) P may be chosen from homopolymers, i.e. polymers formed entirely from repeating units of a single monomer of formula (III), and copolymers obtained by copolymerization of at least two monomers, at least one of which is of formula (III).
  • the polymer(s) P are chosen from “CP” copolymers, obtained by polymerization of:
  • copolymers CP are obtained by polymerization of at least one monomer (2) with at least one monomer (1) and/or at least one monomer (3).
  • Said copolymer CP may be a statistical, alternating (block) or gradient copolymer.
  • the copolymer CP is a statistical copolymer.
  • the term “statistical copolymer” means a copolymer formed of macromolecules in which the sequential distribution of the monomer units (2), (1) if present, and (3) if present, obeys known statistical laws. In other words, in a statistical copolymer, the various monomers follow each other in any order.
  • Statistical copolymers are also known as random copolymers.
  • the sequence of a statistical copolymer, formed from monomers A and B may be as follows A-A-B-A-B-B-B-B-A-A-B-A.
  • copolymer CP according to the present invention is in particular free of monomer units different from monomers (2), (1) and (3) defined above.
  • the copolymer CP according to the invention does not comprise any monomer (1).
  • the copolymer CP according to the invention then consists of monomer(s) (2) and monomer(s) (3) as defined above.
  • the copolymer CP comprises from 50% to 99% by weight, and preferably from 55% to 95% by weight, of at least one monomer (1) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobomyl acrylate, isobomyl methacrylate, and mixtures thereof, relative to the total weight of the monomers.
  • 2-Ethylhexyl acrylate also known as 2-ethylhexyl prop-2-enoate, is a compound of empirical formula C11H20O2, and of structural formula:
  • 2-ethylhexyl methacrylate mention may notably be made of the product sold under the name 2-Ethylhexyl methacrylate by the company Sigma- Aldrich.
  • Isobornyl acrylate is a compound of empirical formula C13H20O2, and of structural formula:
  • Isobornyl methacrylate is a compound of empirical formula C14H22O2, and of structural formula:
  • monomer (1) is at least 2-ethylhexyl acrylate and/or isobomyl acrylate.
  • the copolymer CP comprises at least one monomer (1) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobomyl acrylate, isobornyl methacrylate, and mixtures thereof, in an amount of less than 50% relative to the total weight of the monomers, preferably between 0.01% and 49.9% relative to the total weight of the monomers.
  • the copolymer CP comprises from 1% to 20% by weight, and preferably from 5% to 15% by weight, relative to the total weight of the monomers, of at least one monomer (2) of formula (III): in which:
  • R a represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, R a represents a methyl group,
  • R b and R c which may be identical or different, represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, R b and R c represent a hydrogen atom,
  • R d represents a linear or branched (Ci-C4)alkyl group; preferably, R d represents a methyl group, and
  • L represents a linear or branched (Ci-Ce)alkylene or cycloalkylene group; preferably, L represents a (Ci-C4)alkylene group, in particular ethylene.
  • the monomer (2) is chosen from acetoacetoxyethyl acrylate, acetoacetoxyethyl methacrylate, and mixtures thereof, and preferably, monomer (2) is acetoacetoxyethyl methacrylate.
  • Acetoacetoxy ethyl acrylate is a compound of empirical formula C9H12O5, and of structural formula:
  • acetoacetoxyethyl acrylate mention may notably be made of the product sold under the name Butanoic acid, 3-oxo-2-[(l-oxo-2-propen-l-yl)oxy]ethyl ester by the company Alfa Chemistry.
  • Acetoacetoxyethyl methacrylate is a compound of empirical formula C10H14O5, and of structural formula:
  • acetoacetoxyethyl methacrylate mention may notably be made of the product sold under the name EastmanTM AAEM by the company Eastman.
  • the copolymer comprises from 0% to 99% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates, C1-C4 alkyl methacrylates, silicone macromonomers and mixtures thereof, relative to the total weight of the monomers.
  • the copolymer CP according to the invention does not comprise any monomer (3).
  • the copolymer CP according to the invention then consists of monomer(s) (2) and monomer(s) (1) as defined above.
  • the C1-C4 alkyl acrylates and C1-C4 alkyl methacrylates that may be used as monomers (3), mention may be made in particular of methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, tertbutyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate and mixtures thereof.
  • the monomer (3) is a C1-C4 alkyl acrylate, in particular chosen from butyl acrylate, isobutyl acrylate and tert-butyl acrylate.
  • Butyl acrylate is a compound of empirical formula C7H13O2 and of structural formula:
  • Isobutyl acrylate is a compound of empirical formula C7H12O2 and of structural formula:
  • tert-butyl acrylate mention may notably be made of the product sold under the name tert-Butyl acrylate by the company Sigma-Aldrich.
  • silicone macromonomer means a silicone macromolecule bearing an end group that enables it to act as a monomer.
  • the silicone macromonomers will provide a single monomer unit to a chain of the finished macromolecule.
  • R9 denotes a linear or branched, preferably linear, divalent hydrocarbonbased group containing from 1 to 10 carbon atoms and optionally containing one or two -O- ether bonds; preferably ethylene, propylene or butylene;
  • - Rio denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms, notably from 2 to 8 carbon atoms; preferably methyl, ethyl, propyl, butyl or pentyl;
  • - n denotes an integer ranging from 1 to 300, preferentially ranging from 3 to 200.
  • polydimethylsiloxane methacrylates may notably be polydimethylsiloxane methacrylates and in particular the products sold under the name MCR-M17 by Gelest Inc. or x-22-2475 and x-22- 2426 by Shin-Etsu.
  • the silicone macromonomers that are most particularly suitable for use in the invention have a weight-average molecular mass (Mw) ranging from 200 g.mol' 1 to 100 000 g.mol' 1 , and more preferentially from 400 g.mol' 1 to 20 000 g.mol' 1 .
  • Mw weight-average molecular mass
  • monomer (3) is at least one silicone macromonomer, more particularly chosen from silicone macromonomers with a glass transition temperature T g of less than or equal to 25°C, more particularly between -100°C and 25°C, and preferably between -90°C and 0°C.
  • the monomer (3) is at least one polydimethylsiloxane bearing a mono(meth)acryloyloxy end group.
  • the copolymer CP comprises from 0% to 45% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates, C1-C4 alkyl methacrylates, silicone macromonomers, and mixtures thereof, relative to the total weight of the monomers, preferably from 0% to 45% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates, C1-C4 alkyl methacrylates, silicone macromonomers, and mixtures thereof, relative to the total weight of the monomers, and at least one monomer (1) as defined previously, more preferentially 50% to 99% of at least one monomer (1) as defined previously.
  • the copolymer CP comprises from 80% to 99% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates and C1-C4 alkyl methacrylates, and preferably the copolymer CP comprises from 80% to 99% by weight of at least one monomer (3) chosen from Ci- C4 alkyl acrylates and C1-C4 alkyl methacrylates relative to the total weight of the monomers, and no monomer (1) as defined previously.
  • the copolymer CP comprises from 80% to 99% by weight of at least one monomer (3) chosen from silicone macromonomers, and mixtures thereof with C1-C4 alkyl acrylates or with Ci- C4 alkyl methacrylates, relative to the total weight of the monomers, preferably 80% to 99% by weight of a mixture of at least one monomer (3) chosen from silicone macromonomers and at least one monomer (3) chosen from Ci-C4-alkyl acrylates and/or Ci-C4-alkyl methacrylates, relative to the total weight of the monomers; more preferentially, the copolymer CP comprises 80% to 99% by weight of a mixture of at least one monomer (3) chosen from silicone macromonomers and at least one monomer (3) chosen from C1-C4 alkyl acrylates and/or C1-C4 alkyl methacrylates, and no monomer (1) relative to the total weight of the monomers.
  • the copolymer CP comprises more than 30% by weight of at least one monomer (3) chosen from Ci- C4 alkyl acrylates and C1-C4 alkyl methacrylates, and preferably CP comprises from 30.01% to 99% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates and C1-C4 alkyl methacrylates relative to the total weight of the monomers and at least one monomer (1) as defined previously in a non-zero amount and less than 50% relative to the total weight of the monomers.
  • the monomers (3) preferably denote C4 alkyl acrylates, C4 alkyl methacrylates or mixtures of C1-C3 alkyl acrylates and/or C1-C3 alkyl methacrylates with C4 alkyl acrylates or C4 alkyl methacrylates.
  • the copolymer CP comprises more than 30% by weight of at least one monomer (3) chosen from silicone macromonomers and mixtures thereof with C1-C4 alkyl acrylates or with Ci- C4 alkyl methacrylates, relative to the total weight of the monomers, and preferably CP comprises from 30.01% to 99% by weight of at least one monomer (3) chosen from silicone macromonomers and mixtures thereof with C1-C4 alkyl acrylates or with Ci- C4 alkyl methacrylates, relative to the total weight of the monomers, and at least one monomer (1) as defined previously in a non-zero amount and less than 50% relative to the total weight of the monomers.
  • the copolymer CP comprises more than 45% and less than 49% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates, C1-C4 alkyl methacrylates, silicone macromonomers, and mixtures thereof and preferably CP comprises from 45.01% to 48.99% by weight of at least one monomer (3) chosen from C1-C4 alkyl acrylates and C1-C4 alkyl methacrylates relative to the total weight of the monomers, and at least one monomer (1) as previously defined in an amount of from 50% to 99% relative to the total weight of the monomers.
  • the monomers (3) preferably denote C4 alkyl acrylates, C4 alkyl methacrylates or mixtures of C1-C3 alkyl acrylates and/or C1-C3 alkyl methacrylates with C4 alkyl acrylates or C4 alkyl methacrylates.
  • copolymer CP according to the present invention is preferably obtained by copolymerization of:
  • composition B according to the invention comprises the polymer(s) P in a total content ranging from 1% to 30% by weight, more preferentially from 2% to 20% by weight, and even more preferentially ranging from 5% to 15% by weight, relative to the total weight of composition B.
  • composition B according to the invention comprises the polymer(s) CP chosen from isobutyl acrylate, tert-butyl acrylate and acetoacetoxyethyl methacrylate copolymer and/or isobornyl acrylate, 2- ethylhexyl acrylate and acetoacetoxyethyl methacrylate copolymer
  • the total content of copolymer(s) CP is in the range from 1% to 30% by weight, more preferentially from 2% to 20% by weight, and even more preferentially from 5% to 15% by weight, relative to the total weight of composition B.
  • composition B is different from composition A described previously.
  • composition B does not comprise the same ingredients as composition A.
  • composition B does not comprise any alkoxysilane of formula (I), (I’) or (II) as described previously.
  • Composition B is preferably anhydrous.
  • anhydrous composition means a composition comprising an amount of water of less than 5% by weight, preferably less than 3% by weight relative to the weight of the composition. Preferably, this water content is less than 1% by weight, better still less than 0.5% or even less than 0.3% by weight, relative to the weight of the composition. More particularly, the composition does not comprise any water (0%).
  • said anhydrous composition does not comprise any water added during its preparation, the residual water that may be present possibly originating from the starting materials used during the preparation.
  • Non-amino silicones are non-amino silicones:
  • composition B also comprises at least one non-amino silicone, i.e. at least one silicone other than amino silicones.
  • silicone 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-), optionally substituted hydrocarbon-based radicals being directly linked via a carbon atom to said silicon atoms.
  • non-amino silicones are different from the polymers P, and also from the non-amino alkoxysilanes and/or oligomers thereof described previously.
  • amino silicone denotes any silicone including at least one primary, secondary or tertiary amine group and/or at least one quaternary ammonium group.
  • the non-amino silicones that may be used may be volatile or non-volatile.
  • non-amino silicones that may be used may be soluble or insoluble in composition B according to the invention; they may be in oil, wax, resin or gum form; silicone oils and silicone resins are preferred.
  • the volatile silicones may be chosen from those with a boiling point of between 60°C and 260°C (at atmospheric pressure) and more particularly from: i) cyclic polydialkylsiloxanes including from 3 to 7 and preferably 4 to 5 silicon atoms, such as
  • Volatile Silicone FZ 3109 sold by the company Union Carbide;
  • cyclic silicones with silicon-based organic compounds such as the mixture of octamethylcyclotetrasiloxane and of tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and of oxy-1,1’- bis(2,2,2’,2’,3,3’-hexatrimethylsilyloxy)neopentane; ii) linear polydialkylsiloxanes containing 2 to 9 silicon atoms, which generally have a viscosity of less than or equal to 5> ⁇ 10' 6 m 2 /s at 25°C, such as decamethyltetrasiloxane.
  • non-volatile silicones mention may be made, alone or as a mixture, of polydialkylsiloxanes and notably polydimethylsiloxanes (PDMS), polydiarylsiloxanes, poly alkylaryl siloxanes, silicone gums and resins, and also organopolysiloxanes (or organomodified polysiloxanes, or alternatively organomodified silicones) which are polysiloxanes including in their structure one or more organofunctional groups, generally attached via a hydrocarbon-based group, and preferably chosen from aryl groups, alkoxy groups and polyoxyethylene or polyoxypropylene groups.
  • PDMS polydimethylsiloxanes
  • organopolysiloxanes or organomodified polysiloxanes, or alternatively organomodified silicones
  • the organomodified silicones may be polydiarylsiloxanes, notably polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organofunctional groups mentioned previously.
  • the polyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes.
  • organopolysiloxanes including:
  • polyoxyethylene and/or polyoxypropylene groups optionally including C6- C24 alkyl groups, such as dimethicone copolyols, and notably those sold by the company Dow Coming under the name DC 1248 or the oils Silwet® L 722, L 7500, L 77 and L 711 from the company Union Carbide; or alternatively (C12)alkylmethicone copolyols, and notably those sold by the company Dow Corning under the name Q2- 5200;
  • hydroxylated groups for instance polyorganosiloxanes bearing a hydroxyalkyl function
  • - acyloxyalkyl groups such as the polyorganosiloxanes described in patent US-A-4 957 732; - anionic groups of the carboxylic acid type, as described, for example, in EP 186 507, or of the alkylcarboxylic type, such as the product X-22-3701E from the company Shin-Etsu; or alternatively of the 2-hydroxy alkyl sulfonate or 2- hydroxyalkylthiosulfate type, such as the products sold by the company Goldschmidt under the names Abil® S201 and Abil® S255.
  • the silicones may also be chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes bearing trimethyl silyl end groups.
  • polydialkylsiloxanes mention may be made of the following commercial products:
  • oils of the 200 series from the company Dow Corning, such as DC200 with a viscosity of 60 000 mm 2 /s;
  • CTFA dimethiconol
  • Products that may be used more particularly in accordance with the invention are mixtures such as:
  • CTFA dimethiconol
  • CFA cyclic polydimethylsiloxane
  • the polyalkylarylsiloxanes are chosen particularly from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity ranging from I * 10' 5 to 5* 10' 2 m 2 /s at 25°C.
  • oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • the silicone resin(s) according to the invention may be chosen from silicone resins with a molecular weight of between 300 and 100 000 g/mol, preferably between 300 and 50 000 g/mol, more preferentially between 300 and 30 000 g/mol.
  • molecular weight means the average molecular weight (Mw).
  • silicone resins also known as siloxane resins
  • MDTQ silicone resins
  • silicone resins that may be used in composition B according to the invention, use may be made, for example, of silicone resins of MQ type, of T type or of MQT type.
  • Resin MK® such as Belsil PMS MK®: polymer comprising CH3SiO3/2 repeating units (T units), which may also comprise up to 1% by weight of (CH 3 ) 2 SiO 2 2 units (D units) and having an average molecular weight of about 10 000 g/mol, or
  • Resins comprising MQT units that are notably known are those mentioned in US 5 110 890.
  • a preferred form of resins of MQT type are MQT-propyl (also known as MQTPr) resins.
  • MQT-propyl resins Such resins that may be used in the compositions according to the invention are notably the resins described and prepared in patent application WO 2005/075 542, the content of which is incorporated herein by reference.
  • the MQ-T-propyl resin preferably comprises the units:
  • a hydrocarbon-based radical notably alkyl
  • the siloxane resin comprises the units:
  • R1 and R3 independently representing an alkyl group containing from 1 to 8 carbon atoms
  • R1 preferably being a methyl group and R3 preferably being a propyl group
  • a being between 0.05 and 0.5 and preferably between 0.15 and 0.4
  • c being greater than zero, preferably between 0.15 and 0.4
  • d being between 0.05 and 0.6, preferably between 0.2 and 0.6 or alternatively between 0.2 and 0.55
  • a + b + c + d 1, and a, b, c and d being mole fractions, provided that more than 40 mol% of the groups R3 of the siloxane resin are propyl groups.
  • siloxane resins that may be used according to the invention may be obtained via a process comprising the reaction of:
  • an MQ resin comprising at least 80 mol% of units (R13SiOi/2) a and (SiO 4 / 2 )d,
  • R1 representing an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, a and d being greater than zero, the ratio a/d being between 0.5 and 1.5;
  • R3 representing an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, c being greater than zero, on condition that at least 40 mol% of the groups R3 are propyl groups, in which the mass ratio A/B is between 95/5 and 15/85 and preferably the mass ratio A/B is 30/70.
  • the mass ratio A/B is between 95/5 and 15/85.
  • the ratio A/B is less than or equal to 70/30. These preferred ratios have proven to afford comfortable deposits.
  • composition B according to the invention comprises at least one non-amino silicone chosen from polydialkylsiloxanes, notably cyclic polydialkylsiloxanes containing from 3 to 7 silicon atoms, trimethylsilyl-terminated polydimethylsiloxanes, dimethylsilanol-terminated polydimethylsiloxanes (dimethiconols); silicone resins, notably MQ-type resins and T-type resins, notably polymethylsilsesquioxane resins; and mixtures thereof.
  • polydialkylsiloxanes notably cyclic polydialkylsiloxanes containing from 3 to 7 silicon atoms, trimethylsilyl-terminated polydimethylsiloxanes, dimethylsilanol-terminated polydimethylsiloxanes (dimethiconols); silicone resins, notably MQ-type resins and T-type resins, notably polymethylsilsesquioxane resins;
  • composition B according to the invention comprises the nonamino silicone(s) in a total content ranging from 0.5% to 25% by weight, more preferentially from 1% to 20% by weight, and even more preferentially ranging from 2% to 15% by weight, relative to the total weight of composition B.
  • the total content of non-amino silicone(s) chosen from polydialkylsiloxanes; silicone resins, notably MQ type resins and T type resins, in composition B ranges from 0.5% to 25% by weight, more preferentially from 1% to 20% by weight, and even more preferentially ranging from 2% to 15% by weight, relative to the total weight of composition B.
  • the total content of non-amino silicone(s) chosen from cyclic polydialkylsiloxanes including from 3 to 7 silicon atoms, trimethylsilyl-terminated polydimethylsiloxanes, dimethylsilanol-terminated polydimethylsiloxanes (dimethiconols), polymethylsilsesquioxane resins; and mixtures thereof, in composition B ranges from 0.5% to 25% by weight, more preferentially from 1% to 20% by weight and even more preferentially ranges from 2% to 15% by weight, relative to the total weight of composition B.
  • composition B also comprises at least one hydrocarbon-based oil.
  • hydrocarbon-based oil means an oil formed essentially from, or even consisting of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • branched Cs-Ci6 alkanes such as Cs-Ci6 and preferably Cs-Cu isoalkanes (also known as isoparaffins), such as isododecane (also known as 2, 2, 4, 4, 6- pentamethylheptane), isodecane and, for example, the oils sold under the Isopar or Permethyl trade names, linear Cs-Ci6 alkanes, for instance n-dodecane (C12) and n-tetradecane (C14) sold by Sasol under the references, respectively, Parafol 12-97 and Parafol 14-97, and also mixtures thereof, the undecane-tridecane mixture, mixtures of n-undecane (C11) and of n-tridecane (C13) obtained in examples 1 and 2 of patent application WO 2008/155059 from the company Cognis, and mixtures thereof,
  • C3-C8 esters containing from 3 to 8 carbon atoms in total
  • oils of plant origin such as triglycerides constituted of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are notably heptanoic acid or octanoic acid triglycerides, or alternatively wheatgerm oil, sunflower oil, grapeseed oil, sesame oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil or musk rose oil; shea butter
  • hydrocarbons of mineral or synthetic origin comprising more than 16 carbon atoms, in particular petroleum jelly, poly decenes, hydrogenated polyisobutene, in particular Parleam®, squalane and liquid paraffins, and mixtures thereof,
  • oils of formula R1COOR2 in which Ri represents a linear or branched fatty acid residue including from 1 to 40 carbon atoms and R2 represents a, notably branched, hydrocarbon-based chain containing from 1 to 40 carbon atoms, on condition that the sum of the number of carbon atoms in Ri and R2 is greater than or equal to 10, for instance purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12 to C15 alkyl benzoates, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, isostearyl isostearate, 2-hexyldecyl laurate, 2-octyldecyl palmitate, 2-octyldodecyl myristate, alcohol or polyalcohol heptanoates, o
  • - fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol and 2 -undecylpentadecanol .
  • the hydrocarbon-based oil present in composition B according to the present invention is apolar, consisting only of carbon and hydrogen atoms.
  • the hydrocarbon-based oil is chosen from:
  • esters such as ethyl acetate, methyl acetate, propyl acetate or butyl acetate;
  • the total content of hydrocarbon-based oil(s) in composition B ranges from 5% to 80% by weight, more preferentially from 10% to 75% by weight, even more preferentially from 20% to 70% by weight and better still from 35% to 65% by weight relative to the total weight of composition B.
  • the total content of hydrocarbon-based oil(s) chosen from branched Cs-Cu alkanes, short-chain C3-C8 esters and mixtures thereof, in composition B ranges from 5% to 80% by weight, more preferentially from 10% to 75% by weight, even more preferentially from 20% to 70% by weight, and better still from 35% to 65% by weight relative to the total weight of composition B.
  • composition B also comprises at least one alcohol chosen from monoalcohols and polyols; more preferentially from Ci-Ce monoalcohols and C2-C6 polyols.
  • C1-C4 alkanols such as ethanol and isopropanol.
  • polyols use may be made of glycerol, propylene glycol, ethylene glycol, pentaerythritol, trimethylolpropane, 1,3-propanediol, pentane- 1,2-diol, caprylyl glycol (octane- 1,2-diol), butylene glycol, isoprene glycol, pentylene glycol, hexylene glycol, glycerol, polyglycerols, such as glycerol oligomers like diglycerol, polyethylene glycols, and mixtures thereof.
  • the alcohol(s) are chosen from ethanol, hexylene glycol, and mixtures thereof.
  • composition B also comprises at least one alcohol chosen from monoalcohols and polyols; even more preferentially Ci-Ce monoalcohols and C2- Ce polyols; and better still from ethanol, hexylene glycol, and mixtures thereof.
  • composition D also comprises at least one alcohol chosen from monoalcohols and polyols; even more preferentially Ci-Ce monoalcohols and C2- Ce polyols; and better still from ethanol, caprylyl glycol, and mixtures thereof.
  • the total content of alcohol(s) in composition B ranges from 5% to 60% by weight, preferably from 10% to 50% by weight, more preferentially from 15% to 40% by weight, relative to the total weight of composition B.
  • composition A and/or composition B comprise at least one colouring agent chosen from pigments, direct dyes and mixtures thereof.
  • the colouring agent(s) are chosen from pigments.
  • composition B according to the invention comprises at least one pigment.
  • 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 (i.e. gram of pigment per litre of water).
  • 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, special-effect pigments 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, titanium oxide and stannic oxide (tin 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, fluoran, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470
  • pigment pastes of organic pigments such as the products sold by the company Hoechst under the names:
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426.
  • These composite pigments may notably be composed of particles including an inorganic 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 inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green 5 (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090).
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green 5 (CI 61
  • the pigment may also be a special-effect pigment.
  • special-effect pigments 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.
  • special -effect pigments those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.
  • nacreous pigments such as mica coated with titanium or with bismuth oxychloride
  • coloured nacreous pigments such as mica covered with titanium and with iron oxides, mica covered with iron oxide, mica covered with titanium and notably with ferric blue or with chromium oxide, mica covered with titanium and with an organic pigment as defined previously, and also nacreous pigments based on bismuth oxychloride.
  • Nacreous pigments that may be mentioned include the nacres Cellini sold by BASF (mica-TiCh-lake), Prestige sold by Eckart (mica-TiCE), Prestige Bronze sold by Eckart (mica-Fe2O3) Syncrystal sold by Eckart (Mica-TiCE-SnCh) and Colorona sold by Merck (mica-TiO2-Fe2O3).
  • particles including a borosilicate substrate coated with titanium oxide.
  • Particles comprising a glass substrate coated with titanium oxide are notably sold under the name Metashine MC1080RY by the company Toyal.
  • nacres examples include polyethylene terephthalate glitter flakes, notably those sold by the company Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver glitter flakes). It is also possible to envisage multilayer pigments based on synthetic substrates, such as alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.
  • the special-effect pigments may also be chosen from reflective particles, i.e. notably from particles whose size, structure, notably the thickness of the layer(s) of which they are made and their physical and chemical nature, and surface state, allow them to reflect incident light.
  • This reflection may, where appropriate, have an intensity sufficient to create at the surface of the composition or of the mixture, when it is applied to the support to be made up, highlight points that are visible to the naked eye, i.e. more luminous points that contrast with their environment making them appear to sparkle.
  • the reflective particles may be selected so as not to significantly alter the colouring effect generated by the colouring agents with which they are combined, and more particularly so as to optimize this effect in terms of colour rendition. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or tint.
  • These particles may have varied forms and may notably be in platelet or globular form, in particular in spherical form.
  • the reflective particles may or may not have a multilayer structure and, in the case of a multilayer structure, may have, for example, at least one layer of uniform thickness, notably of a reflective material.
  • the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, notably titanium or iron oxides obtained synthetically.
  • the reflective particles may include, for example, a natural or synthetic substrate, notably a synthetic substrate at least partially coated with at least one layer of a reflective material, notably of at least one metal or metallic material.
  • the substrate may be made of one or more organic and/or mineral materials.
  • glasses More particularly, it may be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, notably aluminosilicates and borosilicates, and synthetic mica, and mixtures thereof, this list not being limiting.
  • Reflective particles are notably described in JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
  • reflective particles including a mineral substrate coated with a layer of metal
  • Particles with a silver-coated glass substrate in the form of platelets, are sold under the name Microglass Metashine REFSX 2025 PS by the company Toyal.
  • Particles with a glass substrate coated with 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.
  • 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 pigments may be dispersed in the composition by means of a dispersant.
  • esters of 12-hydroxy stearic acid in particular and of Cs to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly( 12-hydroxy stearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or polyhydroxystearic acid such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof.
  • poly( 12-hydroxy stearic acid) stearate with a molecular weight of approximately 750 g/mol such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Hen
  • dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185 and DC2-5225 C.
  • the pigments used in the composition may be surface-treated with an organic agent.
  • the pigments surface-treated beforehand that are useful in the context of the invention are pigments which have been completely or partially subjected to a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature with an organic agent, such as those described notably in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention.
  • organic agents may be chosen, for example, from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and derivatives thereof, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol and lauric acid and derivatives thereof; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; alkanolamines; silicone compounds, for example silicones, notably polydimethylsiloxanes; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.
  • waxes for example carnauba wax and beeswax
  • the surface-treated pigments that are useful in the composition may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.
  • the surface-treated pigments that are useful in the context of the present invention may be prepared according to surface-treatment techniques that are well known to those skilled in the art, or may be commercially available as is.
  • the surface-treated pigments are coated with an organic layer.
  • the organic agent with which the pigments are treated may be deposited on the pigments by evaporation of solvent, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.
  • the surface treatment may thus be performed, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is notably described in patent US 4 578 266.
  • An organic agent covalently bonded to the pigments will preferably be used.
  • the agent for the surface treatment may represent from 0.1% to 50% by weight 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:
  • PEG-silicone treatment for instance the AQ surface treatment sold by LCW;
  • methicone treatment for instance the SI surface treatment sold by LCW;
  • 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;
  • an isostearyl sebacate treatment for instance the HS surface treatment sold by Miyoshi;
  • an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment for instance the FSA surface treatment sold by Daito;
  • a polymethylhydrogenosiloxane/perfluoroalkyl phosphate treatment for instance the FS01 surface treatment sold by Daito;
  • an acrylate/dimethicone copolymer treatment for instance the ASC surface treatment sold by Daito;
  • an isopropyl titanium triisostearate treatment for instance the ITT surface treatment sold by Daito;
  • an acrylate copolymer treatment for instance the APD surface treatment sold by Daito;
  • PF + ITT surface treatment sold by Daito.
  • the dispersant is present with organic or inorganic pigments in submicron-sized particulate form in the dye composition.
  • micron-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 (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.
  • the dispersant and the pigment(s) are present in an amount (dispersantpigment) 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 aminosilicone type, different from the alkoxysilanes of formula (I) or formula (I’) described previously in the patent application.
  • a silicone backbone such as silicone polyether and dispersants of aminosilicone type, different from the alkoxysilanes of formula (I) or formula (I’) described previously in the patent application.
  • suitable dispersants that may be mentioned are:
  • silicones i.e. silicones comprising one or more amine groups such as those sold under the names and references: BYK LPX 21879 by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, sold by Genesee Polymers,
  • Tego® RC 902 Tego® RC 922, Tego® RC 1041 and Tego® RC 1043, sold by Evonik
  • PDMS polydimethyl siloxane
  • carboxylic 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.
  • direct dye means natural and/or synthetic dyes, other than oxidation dyes. These are dyes which will spread superficially on the fibre. They may be ionic, for example cationic or anionic, or nonionic.
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes 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.
  • the term “anionic direct dye” means any direct dye including in its structure at least one CO2R or SO3R 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.
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • Ar-N N- with Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted with one or more alkyl, (O)2S(O )-, M + or phenylamino groups;
  • dyes of formula (XIX) mention may be made of Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment Red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Acid Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3, Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2, Food Yellow 3 or Sunset Yellow; and, as examples of dyes of formula (XIX’), mention may be made of: Acid Red 111, Acid Red 134, Acid Yellow 38; b) the pyrazolone anionic azo dyes of formulae (XX) and (XX’): in which formulae
  • - Rie represents an oxo group, in which case R’i6 is absent, or alternatively R15 with Rie together form a double bond;
  • R17 and Ris which may be identical or different, represent a hydrogen atom, or a group chosen from:
  • Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted with one or more alkyl groups; - R19 and R20 together form either a double bond, or a benzo group D’, which is optionally substituted;
  • R’ 16, R’ 19 and R’20 which may be identical or different, represent a hydrogen atom or an alkyl or hydroxyl group
  • Ra and Rb which may be identical or different, are as defined previously; preferentially, Ra represents a hydrogen atom and Rb represents an aryl group;
  • - Y represents either a hydroxyl group or an oxo group
  • formulae (XX) and (XX’) comprise at least one sulfonate radical (O)2S(O )-, M + or one carboxylate radical -C(O)O', M + on one of the rings D or E; preferentially sodium sulfonate.
  • dyes of formula (XX) mention may be made of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and as examples of dyes of formula (XX’), mention may be made of: Acid Yellow 17; c) the anthraquinone dyes of formulae (XXI) and (XXI’):
  • - Z’ represents a hydrogen atom or a group NR28R29 with R28 and R29, which may be identical or different, representing a hydrogen atom or a group chosen from:
  • - aryl optionally substituted with one or more groups, particularly i) alkyl such as methyl, n-dodecyl, n-butyl; ii) (O)2S(O )-, M + with M + as defined previously; iii) R°-C(X)-X’-, R°-X’-C(X)-, R°-X’-C(X)-X”- with R°, X, X’ and X” as defined previously, preferentially R° represents an alkyl group;
  • - cycloalkyl notably cyclohexyl
  • - Z represents a group chosen from hydroxyl and NR’28R’29 with R’28 and R’29, which may be identical or different, representing the same atoms or groups as R28 and R29 as defined previously; it being understood that formulae (XXI) and (XXI’) comprise at least one sulfonate radical (O)2S(O )-, M + or one carboxylate radical -C(O)O', M + ; preferentially sodium sulfonate.
  • dyes of formula (XXI) mention may be made of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT Violet No. 2; and, as an example of a dye of formula (XXI’), mention may be made of: Acid Black 48; d) the nitro dyes of formulae (XXII) and (XXII’):
  • R30, R31 and R32 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • alkoxy optionally substituted with one or more hydroxyl groups, alkylthio optionally substituted with one or more hydroxyl groups;
  • R30, R31 and R32 represent a hydrogen atom
  • Rc and Rd which may be identical or different, represent a hydrogen atom or an alkyl group
  • W is as defined previously; W particularly represents an -NH- group;
  • ALK represents a linear or branched divalent Ci-Ce alkylene group; in particular, ALK represents a -CH2-CH2- group;
  • - p represents an integer inclusively between 1 and 5;
  • - q represents an integer inclusively between 1 and 4; - u is 0 or 1;
  • J represents a nitro or nitroso group; particularly nitro
  • J represents an oxygen or sulfur atom, or a divalent radical -S(O)m- with m representing an integer 1 or 2; preferentially, J represents an -SO2- radical;
  • - M’ represents a hydrogen atom or a cationic counterion; , which may be present or absent, represents a benzo group optionally substituted with one or more groups R30 as defined previously; it being understood that formulae (XXII) and (XXII’) comprise at least one sulfonate radical (O)2S(O )-, M + or one carboxylate radical -C(O)O', M + ; preferentially sodium sulfonate.
  • dyes of formula (XXII) mention may be made of: Acid Brown 13 and Acid Orange 3; as examples of dyes of formula (XXII’), mention may be made of: Acid Yellow 1, the sodium salt of 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2-(4’-N,N-(2”-hydroxyethyl)amino-2’- nitro)anilineethanesulfonic acid, 4-P-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C Yellow 7; e) the triarylmethane dyes of formula (XXIII):
  • R33, R34, R35 and R36 which may be identical or different, represent a hydrogen atom or a group chosen from alkyl, optionally substituted aryl and optionally substituted arylalkyl; particularly an alkyl and benzyl group optionally substituted with a group (O) m S(O )-, M + with M + and m as defined previously;
  • R37, R38, R39, R40, R41, R42, R43 and R44 which may be identical or different, represent a hydrogen atom or a group chosen from:
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • R41 with R42 or R42 with R43 or R43 with R44 together form a fused benzo group: I’; with I’ optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2S(O )-, M + ; iv) hydroxyl; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X’-; viii) R°-X’-C(X)- and ix) R°-X’- C(X)-X”-; with M + , R°, X, X’ and X” as defined previously; in particular, R37 to R40 represent a hydrogen atom, and R41 to R44, which may be identical or different, represent a hydroxyl group or (O)2S(O )-, M + ; and when R43 with R44 together form a benzo group: I’; with I’
  • dyes of formula (XXIII) mention may be made of: Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid Green 3; Acid Green 5 and Acid Green 50. f) the xanthene-based dyes of formula (XXIV):
  • R45, R46, R47 and R48 which may be identical or different, represent a hydrogen or halogen atom
  • R49, R50, R51 and R52 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • R49, R50, R51 and R52 represent a hydrogen or halogen atom
  • - L represents an alkoxide O', M + ; a thioalkoxide S', M + or a group NRf, with Rf representing a hydrogen atom or an alkyl group, and M + as defined previously; M + is particularly sodium or potassium;
  • L’ represents an oxygen or sulfur atom or an ammonium group: N + RfRg, with Rf and Rg, which may be identical or different, representing a hydrogen atom or an optionally substituted alkyl or aryl group; L’ particularly represents an oxygen atom or a phenylamino group optionally substituted with one or more alkyl or (O) m S(O')-, M + groups with m and M + as defined previously;
  • Q and Q’ which may be identical or different, represent an oxygen or sulfur atom; particularly, Q and Q’ represent an oxygen atom;
  • dyes of formula (XXIV) mention may be made of: Acid Yellow 73; Acid Red 51; Acid Red 52; Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9; g) the indole-based dyes of formula (XXV):
  • R53, R54, R55, R56, R57, R58, R59 and Reo which may be identical or different, represent a hydrogen atom or a group chosen from:
  • X, X’ and X which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group;
  • G represents an oxygen or sulfur atom or a group NRe with Re as defined previously; in particular, G represents an oxygen atom;
  • formula (XXIII) comprises at least one sulfonate radical (O)2S(O )-, M + or one carboxylate radical -C(O)O', M + ; preferentially sodium sulfonate.
  • dyes of formula (XXVI) mention may be made of: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.
  • the direct dyes are chosen from anionic direct dyes.
  • the total content of colouring agent(s) in composition A and/or composition B ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, even more preferentially from 0.005% to 10% by weight, better still from 0.5% to 10% by weight, even better still from 1% to 10% by weight, relative to the total weight of composition A and/or composition B.
  • the total content of colouring agent(s) in composition B ranges from 0.001% to 20% by weight, more preferentially from 0.005% to 15% by weight, even more preferentially from 0.005% to 10% by weight, better still from 0.5% to 10% by weight, even better still from 1% to 10% by weight, relative to the total weight of composition B.
  • the total content of pigment(s) in composition A and/or composition B ranges from 0.05% to 20% by weight, more preferentially from 0.1% to 15% by weight, better still from 0.5% to 10% by weight, relative to the total weight of composition A and/or composition B.
  • Composition C is a composition having Composition C:
  • the process according to the invention may optionally also comprise at least one step c) of applying to keratin fibres at least one composition C, comprising at least one amino alkoxysilane chosen from the compounds of formula (I) or (I’) as described above, oligomers thereof and/or mixtures thereof.
  • composition C is different from composition B.
  • composition C is identical to or different from composition A; preferably identical.
  • composition C according to the invention preferably comprises at least one amino alkoxy silane chosen from said compounds of formula (I) or (T) as described above, more preferentially of formula (I), and optionally also at least one non-amino alkoxysilane chosen from said compounds of formula (II) as described above.
  • composition A and/or composition C 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 B comprises at least one polymer P as described previously and at least one pigment as described previously.
  • composition C is different from composition B;
  • steps a) and b), and optionally c), are performed sequentially.
  • step c) when it is performed, step c) is performed after steps a) and b), step a) having been performed before step b).
  • step a) is performed before step b).
  • step a) is performed first, followed by step b) and finally step c).
  • compositions A and/or B, and/or optionally C, to keratin fibres may be performed on said fibres, which may be wet or dry.
  • the keratin fibres are hair.
  • the composition according to the invention may be applied to all types of light or dark, natural or dyed, permanent- waved, bleached or relaxed hair.
  • the application to the hair is generally performed at room temperature (between 15 and 25°C).
  • the process according to the invention may also comprise a step d) of applying heat to the keratin fibres using a heating device.
  • a step d) is preferably performed between steps a) and b) or between steps b) and a), more preferentially between steps a) and b).
  • a step d) may preferably be performed between steps a) and c) or between steps b) and c), more preferentially between steps b) and c).
  • Such a device may be, for example, a hood, a hair dryer, a straightening or curling iron, a Climazon, etc.
  • step d) of applying heat is performed using a hair dryer.
  • 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 dyeing process according to the invention may optionally also comprise a step e) of rinsing the keratin fibres.
  • drying step refers to the application of water to the keratin fibres.
  • a rinsing step e) is performed between steps a) and b).
  • composition C after application of composition C to the keratin fibres, it is preferable to observe a leave-on time of 10 seconds to 20 minutes, notably 20 seconds to 10 minutes, preferably 30 seconds to 5 minutes of composition C on said fibres.
  • the process for dyeing keratin fibres, preferably the hair comprises the following steps in this order: a) a step of applying to the keratin fibres at least one composition A, e) a step of rinsing the keratin fibres, di) a step of applying heat to the keratin fibres using a heating device, b) a step of applying to the keratin fibres at least one composition B, different from composition A, dz) a step of applying heat to the keratin fibres using a heating device, and then c) optionally a step of applying to the keratin fibres at least one composition C.
  • 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.
  • Example 1 Preparation of copolymer CPI - Isobutyl acrylate/tert-butyl acrylate/acetoacetoxyethyl methacrylate (25/65/10)
  • Example 2 Preparation o f copolymer CP2 - Isobornyl acrylate /2-ethylhexyl acrylate/acetoacetoxyethyl methacrylate (60/30/10)
  • 90 g of isobornyl acrylate monomer, 45 g of 2-ethylhexyl acrylate, 30 g of acetoacetoxyethyl methacrylate, 100 g of an isododecane/ethyl acetate (70/30) solvent and 100 g of isododecane alone are introduced into a 1 L pilot reactor.
  • the medium is degassed with argon and then heated to 90°C with stirring (100 rpm).
  • reaction medium reaches the temperature of 90°C, 338 g of a mixture composed of 200 g of isododecane, 90 g of isobornyl acrylate, 45 g of 2-ethylhexyl acrylate and 3 g of Trigonox 21 S initiator are poured in over one hour.
  • reaction medium is maintained for 7 hours at 90°C. The next day, the reaction medium is stripped with 2 x 200 ml of cold isododecane to remove the residual monomers.
  • This copolymer CP2 is characterized by GPC:
  • compositions are prepared (in g/100 g of starting material in unmodified form): [Table 1]
  • Composition Bl according to the invention is applied by finger to a lock of dry natural hair containing 90% white hair strands, at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 2 minutes at room temperature. The lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • the colouring obtained (at To) is then evaluated according to the protocol below. Once the colouring at To has been evaluated, the lock of hair undergoes the following sebum/shampoo washing cycle three times:
  • the colouring obtained (at Tic) is then evaluated according to the protocol below.
  • the sebum composition used comprises: 6.7% by weight of octyl dodecanol, 28% by weight of oleic acid, 13.7% by weight of hydrogenated polyisobutene, 22.9% by weight of oleyl erucate and 28.7% by weight of triisostearin.
  • Protocol P2 Al and then Bl
  • Composition Al according to the invention is applied by finger to a lock of dry natural hair containing 90% white hair strands, at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is then rinsed and dried with a hairdryer for 2 minutes.
  • Composition B 1 is then applied by finger to the lock of hair at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 2 minutes at room temperature. The lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • the colouring obtained (at To) is then evaluated according to the protocol below.
  • the lock of hair is left for 2 minutes at room temperature. The lock of hair is not rinsed.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • Composition A2 according to the invention is applied by finger to a lock of dry natural hair containing 90% white hair strands, at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is then rinsed and dried with a hairdryer for 2 minutes.
  • Composition B 1 is then applied by finger to the lock of hair at a rate of 0.6 g of composition per gram of hair.
  • composition C2 is then applied by finger to the lock of hair at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • the colouring obtained (at To) is then evaluated according to the protocol below.
  • Protocol P5 (Comparative) : B2 alone
  • Composition B2 according to the invention is applied by finger to a lock of dry natural hair containing 90% white hair strands, at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • the colouring obtained (at To) is then evaluated according to the protocol below.
  • the colouring obtained (at Tic) is then evaluated according to the protocol below.
  • Protocol P6 Al and then B2 and then Cl
  • Composition Al according to the invention is applied by finger to a lock of dry natural hair containing 90% white hair strands, at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is then rinsed and dried with a hairdryer for 2 minutes.
  • Composition B2 is then applied to the lock of hair at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 2 minutes at room temperature.
  • the lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • Composition Cl is then applied by finger to the lock of hair at a rate of 0.6 g of composition per gram of hair.
  • the lock of hair is left for 5 minutes at room temperature.
  • the lock of hair is not rinsed.
  • the lock of hair is then dried with a hairdryer for 2 minutes.
  • the colouring obtained (at To) is then evaluated according to the protocol below.
  • the colouring obtained (at Tic) is then evaluated according to the protocol below.
  • L* represents the intensity of the colour
  • a* indicates the green/red colour axis
  • b* the blue/yellow colour axis.
  • the persistence of the colouring is evaluated by the colour difference AE between the dyed locks before shampoo washing, then after having undergone the shampoo washing/sebum cycle three times according to the protocol described above.
  • the AE value is calculated according to the following equation:
  • the coloured keratin fibre coatings obtained via processes P2, P3, P4 and P6, according to the invention have better persistence with respect to shampoo washing and sebum than the coloured keratin fibre coatings obtained via the comparative dyeing processes Pl and P5.

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  • Cosmetics (AREA)

Abstract

La présente invention concerne le domaine du traitement cosmétique des fibres kératiniques et notamment la coloration des fibres kératiniques, de préférence les cheveux. Le but de l'invention est donc de proposer de nouveaux procédés de coloration comprenant l'application sur lesdites fibres kératiniques d'un polymère porteur d'unités acétoacétate, qui offrent d'excellentes performances techniques, notamment en termes de persistance des colorations qu'elles procurent. Plus précisément, la présente invention a pour objet un procédé de coloration des fibres kératiniques telles que les cheveux, comprenant l'application sur les fibres kératiniques d'au moins une composition A comprenant au moins un amino alcoxysilane choisi parmi les composés de formule (I) ou (I') et l'application sur les fibres kératiniques d'au moins une composition B, différente de la composition A, comprenant au moins un polymère P comprenant des motifs répétitifs obtenus à partir d'au moins un monomère de formule (III). Ladite composition A et/ou ladite composition B comprennent au moins un agent colorant choisi parmi les pigments, les colorants directs et leurs mélanges.
PCT/EP2024/086208 2023-12-20 2024-12-13 Procédé de coloration de fibres kératiniques comprenant l'application d'au moins un amino alcoxysilane, un polymère porteur de fonctions acétoacétate et un agent colorant Pending WO2025132075A1 (fr)

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FR2314565A FR3157192A1 (fr) 2023-12-20 2023-12-20 Procédé de coloration des fibres kératiniques comprenant l’application d’au moins un alcoxysilane aminé, un polymère à fonctions acétoacétates et un agent colorant
FRFR2314565 2023-12-20

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WO2025132075A1 true WO2025132075A1 (fr) 2025-06-26

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PCT/EP2024/086208 Pending WO2025132075A1 (fr) 2023-12-20 2024-12-13 Procédé de coloration de fibres kératiniques comprenant l'application d'au moins un amino alcoxysilane, un polymère porteur de fonctions acétoacétate et un agent colorant

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FR (1) FR3157192A1 (fr)
WO (1) WO2025132075A1 (fr)

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FR3117794A1 (fr) * 2020-12-23 2022-06-24 L'oreal Dispersion aqueuse d’un copolymère spécifique et ses applications cosmétiques
WO2022136104A1 (fr) * 2020-12-23 2022-06-30 L'oreal Composition cosmétique comprenant un copolymère à base de fonctions acétoacétates
FR3127403A1 (fr) * 2021-09-28 2023-03-31 L'oreal Composition comprenant au moins une silicone de formule (I), au moins une silicone de formule (II), au moins un polymère filmogène hydrophobe choisi parmi les copolymères à base de résine de silicone et de silicone fluide

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