EP4267088A1 - Kosmetische zusammensetzung enthaltend ein copolymer auf basis von acetoacetat-funktionen - Google Patents

Kosmetische zusammensetzung enthaltend ein copolymer auf basis von acetoacetat-funktionen

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Publication number
EP4267088A1
EP4267088A1 EP21834810.0A EP21834810A EP4267088A1 EP 4267088 A1 EP4267088 A1 EP 4267088A1 EP 21834810 A EP21834810 A EP 21834810A EP 4267088 A1 EP4267088 A1 EP 4267088A1
Authority
EP
European Patent Office
Prior art keywords
composition
chosen
acrylate
monomer
methacrylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21834810.0A
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English (en)
French (fr)
Inventor
Laurent SABATIE
Julien PORTAL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
Priority claimed from FR2014085A external-priority patent/FR3117852B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP4267088A1 publication Critical patent/EP4267088A1/de
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/899—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates more particularly to the cosmetic field of keratin materials, and in particular to that of care and/or makeup for the skin and/or lips and/or eyelashes and/or eyebrows, and that of care, styling and/or coloring keratin fibers and preferably the hair. It thus aims to propose new compositions, in particular cosmetics, comprising a copolymer with acetoacetate units, which are particularly interesting with regard to their technical performance, in particular in terms of holding the deposits which they make it possible to obtain, and the sensory feelings which they provide the user with corresponding treatment methods, in particular cosmetics.
  • Cosmetic products conventionally require the implementation of one or more film-forming polymers in order to obtain a quality deposit of these products on keratin materials, and in particular satisfying the expectations detailed below.
  • the deposit formed does not transfer upon contact with the fingers or the clothing. It must also have good resistance in contact with water, in particular rain or during the shower or even perspiration as well as sebum, even in contact with fatty substances in food, in particular edible oils when this deposit is formed on the lips. In addition, this deposit must be comfortable or even shiny.
  • make-up products such as mascaras, eyeliners, eye shadows or lipsticks, and more particularly in their organic and in particular oily phases, dispersions of polymer particles of nanometric size , as a film-forming agent.
  • Document WO 2013/103528 proposes copolymers, unorganized in the particulate state, one of the monomers of which bears an acetoacetate function, in particular for applications capillaries.
  • Documents WO 93/24098 and WO 95/06454 describe aqueous dispersions containing copolymers, one of the monomers of which bears an acetoacetate function, intended for application to the nails.
  • As for the document WO 2014/098052 it proposes an acrylic resin emulsion for styling agents which has been stably dispersed by a poly(vinyl alcohol) resin. The compositions of these documents, however, exhibit unsatisfactory styling hold over time.
  • patent EP 1 392 222 it is also known from patent EP 1 392 222 to use a cosmetic composition for the care and/or treatment of keratin materials comprising a supramolecular polymer comprising a polymer backbone and at least two groups capable of forming at least three hydrogen bonds
  • patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer comprising a polymeric backbone and at least two groups capable of forming at least three hydrogen bonds and a surfactant or a hair conditioning agent.
  • the styling performance characteristics obtained over time or in water remain insufficient.
  • the polymers described above do not allow access to deposits, both on the keratin fibers and on the skin and the lips, which satisfy all of the aforementioned requirements, namely a very good resistance to water, in particular to shampoos for the hair, and/or to fatty substances, in particular for the lips, the wearing of which is also comfortable for the users, which make it possible to adjust the qualities of shine or invisibility and which, in the case of capillary use, provide very satisfactory styling hold.
  • compositions which are resistant to water and to fatty substances, in particular to sebum.
  • compositions making it possible to provide qualities of shine, invisibility and/or a volumizing effect.
  • the present invention aims precisely to meet all or part of these needs.
  • the present invention relates to a so-called “C1” composition, in particular cosmetic for keratin materials, and in particular for the care and/or makeup of the skin, lips, eyelashes and/or or the eyebrows and/or for caring for, styling and/or coloring keratin fibres, preferably the hair, comprising: i) at least one fatty phase; and ii) at least one copolymer, called “CP”, obtained by the polymerization of:
  • R a represents a hydrogen atom or a (C 1 -C 4 )alkyl group, linear or branched, preferably R a represents a methyl group,
  • R b and R c identical or different, represent a hydrogen atom or a (Ci-C 4 )alkyl group, linear or branched, preferably R b and R c represent a hydrogen atom,
  • R d represents a (C 1 -C 4 )alkyl group, linear or branched, preferably R d represents a methyl group
  • L represents a (C 1 -C 6 )alkylene group, linear or branched, or cycloalkylene, in particular L represents a (C 1 -C 4 )alkylene group, preferably L represents ethylene; and preferably the monomer (B) is chosen from acetoacetoxy ethyl acrylate, acetoacetoxy ethyl methacrylate, and mixtures thereof; and
  • the present invention relates to a so-called "C2" composition, in particular cosmetic for keratin materials, and in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and /or for care, styling and/or the coloring of keratin fibres, preferably the hair, comprising: i) at least one fatty phase; ii) at least one CP copolymer as defined previously; and iii) at least one crosslinking agent called “R” as defined below.
  • C2 so-called "C2" composition, in particular cosmetic for keratin materials, and in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and /or for care, styling and/or the coloring of keratin fibres, preferably the hair, comprising: i) at least one fatty phase; ii) at least one CP copolymer as defined previously; and iii) at least one crosslinking agent called “R” as defined below.
  • the present invention relates to a composition C2 comprising at least one crosslinking agent, called "R”, and optionally at least one cosmetic active ingredient, called “AC”, chosen from a) coloring agents chosen from pigments, direct dyes , and mixtures thereof, b) active ingredients for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • R crosslinking agent
  • AC cosmetic active ingredient
  • the present invention relates to a so-called “C3” composition, in particular cosmetic for keratin materials, and in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and /or for the care, styling and/or coloring of keratin fibres, preferably the hair, comprising: i) at least one fatty phase, ii) at least one CP copolymer as defined previously, iii) at least one agent crosslinker R as defined below, and iv) at least one cosmetic active ingredient, called "AC”, in particular chosen from a) coloring materials chosen from pigments, direct dyes, and mixtures thereof, b) care active ingredients keratin materials, preferably skin, c) UV filters, and d) mixtures thereof.
  • C3 cosmetic active ingredient
  • the present invention also relates to a composition C3, comprising at least one cosmetic active ingredient, called "AC", chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients care for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • AC cosmetic active ingredient
  • the present invention relates to a particularly cosmetic process for keratin materials, and in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratin fibres, preferably the hair, comprising a step of applying to said keratin materials a C1, C2 or C3, preferably C2 or C3 composition according to the invention.
  • a CP copolymer in accordance with the invention makes it possible to obtain cosmetic compositions C1, C2 or C3, in particular C2 or C3, leading to deposits for make-up of the skin, lips, eyelashes and/or eyebrows exhibiting good resistance to external attacks such as, for example, water, oils, in particular food oils, sweat and/or sebum and therefore have a very good resistance over time.
  • the deposits obtained with such compositions are also very comfortable.
  • composition C1, C2 or C3 in accordance with the invention makes it possible to obtain a deposit that is more resistant to external attacks such as, for example, water, oils, in particular food oils, sweat and/or sebum and therefore has a very good hold over time.
  • cosmetic compositions C1, C2 or C3, in particular C2 or C3, in accordance with the invention and more particularly intended for hair application make it possible to obtain deposits having a very good resistance to shampoos and to 'water.
  • the present invention relates to a particularly cosmetic process for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or for caring for, styling and/or coloring keratin fibers and preferably the hair, consisting in applying to said keratin materials a composition C1 according to the invention, optionally at least one crosslinking agent R, in particular according to the invention, and optionally at least one AC cosmetic active ingredient, said AC being chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients for the care of keratin materials, preferably the skin, c) UV filters , and d) mixtures thereof.
  • the present invention relates to a process for making up the skin, in particular the lips, comprising a step of applying to said skin at least one composition C1 or C2 or C3 according to the invention, and at least one dyestuff with in particular said method comprising at least the two successive steps consisting in applying sequentially to said skin i) at least one composition C1 according to the invention, and ii) a crosslinking agent R or a composition CR containing at at least one crosslinker R in particular according to the invention, it being understood that said composition C1 and/or said composition CR contains at least one dyestuff or said process comprising at least the three successive steps consisting in applying sequentially to the skin i) a composition CAC containing at least one coloring matter, ii) a composition C1 according to the invention, and iii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R in particular according to the invention with said composition C1 and/or said composition CR containing
  • the present invention relates to a care process, in particular non-therapeutic and cosmetic, for the skin, in particular of the face or the lips, comprising a step of applying to said skin at least one composition C1 or C2 or C3 according to the invention and at least one moisturizing cosmetic active ingredient; with in particular said method comprising at least the two successive steps consisting in applying sequentially to said skin: i) a composition C1 according to the invention, and ii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R in particular according to invention; it being understood that said composition C1 and/or said composition CR contains at least one hydrating cosmetic active ingredient, in particular glycerol, and optionally at least one coloring matter or said method comprising at least the three successive steps consisting in applying sequentially to the skin i) a composition CAC, ii) a composition C1 according to the invention, and iii) a crosslinking agent R or a composition CR containing at least
  • the present invention relates to a process for styling keratin fibers, in particular human keratin fibers, in particular hair, comprising a step of applying to said keratin fibers a composition C1, C2 or C3 according to the invention.
  • the present invention relates to a process for dyeing keratin fibers, preferably human keratin fibers such as the hair and the eyebrows, comprising a step of applying to said keratin fibers a composition C1, C2, or C3 according to the invention, and at least one coloring agent with in particular said method comprising at least the two successive steps consisting in applying sequentially to said fibers i) at least one composition C1 according to the invention, and ii) a crosslinker R or a composition CR containing at least one crosslinker R in particular according to the invention, it being understood that said composition C1 and/or said composition CR contains at least one dyestuff or said process comprising at least the three successive steps consisting of sequentially applying i) a composition CAC containing at least one dyestuff, ii) a composition C1 according to the invention and iii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R in particular according to
  • the present invention also relates to a kit, in particular cosmetic, for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows, and / or for the care, styling and / or coloring of keratin fibers and preferably the hair, comprising:
  • AC active agent is chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof , b) active ingredients for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • the present invention also relates to a kit, in particular cosmetic, for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or the care, styling and/or coloring of keratin fibers and preferably the hair, comprising:
  • a third compartment separate from the first and second compartments and containing at least one cosmetic active ingredient, called "AC", identical or different to that/those possibly contained in the first and/or second compartment(s); it being understood that the first and/or second compartments may also contain one or more identical or different AC cosmetic active ingredients, and that said AC active ingredient is chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • AC cosmetic active ingredient
  • keratin materials within the meaning of the present invention, is meant in particular the lips, the skin, the nails and the keratin fibres, in particular the eyelashes, the eyebrows and the hair, preferably the lips and/or the hair.
  • a composition according to the invention is generally suitable for application to keratin materials, in particular application to the skin, lips and/or keratin fibres, and therefore generally comprises a physiologically acceptable medium, that is to say compatible with keratin materials, in particular an application to the skin, the lips and/or the keratin fibers, in particular the human keratin fibers such as the hair.
  • composition C1 according to the invention contains i) at least one fatty phase, and ii) at least one copolymer CP as defined previously.
  • a composition according to the invention contains at least one CP copolymer obtained by the polymerization of 0% to 99% by weight of at least one monomer (A) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobomyl acrylate, isobomyl methacrylate, and mixtures thereof; 1% to 20% by weight of at least one monomer (B) of formula (I) as defined above, and of preferably chosen from acetoacetoxy ethyl acrylate, acetoacetoxy ethyl methacrylate, and mixtures thereof; and 0% to 99% by weight of at least one monomer (C) selected from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates, silicone macromonomers, and mixtures thereof , relative to the total weight of the monomers, it being understood that the so-called “CP” copolymer is obtained by polymerization of
  • Said CP copolymer can be a random, alternating (block) or gradient copolymer.
  • the copolymer is a random copolymer.
  • random copolymer a copolymer formed of macromolecules in which the sequential distribution of the monomer units (B), (A) if present, and (C) if present, obeys laws known statistics. In other words, in a random copolymer, the different monomers follow each other in any order.
  • Statistical copolymers are also called random copolymers.
  • the sequence of a random copolymer, formed from monomers A and B can be the following: A-A-B-A-B-B-B-B-B-A-A-B-A.
  • CP copolymer considered according to the invention is in particular devoid of monomeric unit different from a monomer (B), (A) and (C).
  • the copolymer CP is present in a composition C1, C2 or C3 according to the invention in a content ranging from 1% to 70% by weight, preferably ranging from 2% to 65% by weight, and more preferably ranging from 3% to 60% by weight, relative to the total weight of the composition.
  • the CP copolymer according to the invention may comprise at least one monomer (A) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobomyl acrylate, isobomyl, and mixtures thereof.
  • the CP copolymer according to the invention does not comprise monomer (A).
  • the CP copolymer according to the invention then consists of monomer(s) (B) and monomer(s) (C) 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 (A) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, and mixtures thereof, based on the total weight of the monomers.
  • A monomer chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, and mixtures thereof, based on the total weight of the monomers.
  • 2-Ethylhexyl acrylate also called 2-ethylhexyl prop-2-enoate
  • 2-ethylhexyl prop-2-enoate is a compound with the structural formula C 11 H 20 O 2 , and with the condensed structural formula:
  • 2-Ethylhexyl methacrylate also called 2-ethylhexyl 2-methylprop-2-enoate, is a compound with the molecular formula C 12 H 22 O 2 , and with the structural formula:
  • Isobornyl acrylate is a compound with the molecular formula C 13 H 20 O 2 , and with the semi-developed formula:
  • Isobornyl methacrylate is a compound with the molecular formula C 14 H 22 O 2 , and the structural formula: Mention may in particular be made, as isobornyl methacrylate, of that marketed under the name Isobomyl methacrylate by the company Sigma-Aldrich.
  • monomer (A) is at least 2-ethylhexyl acrylate and/or isobornyl acrylate.
  • the copolymer CP comprises at least one monomer (A) chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, and their mixtures, 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.
  • A monomer chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, and their mixtures
  • the CP copolymer 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 (B) of formula ( I): in which :
  • R a represents a hydrogen atom or a (C 1 -C 4 )alkyl group, linear or branched, preferably R a represents a methyl group,
  • R b and R c identical or different, represent a hydrogen atom or a (Ci-C 4 )alkyl group, linear or branched, preferably R b and R c represent a hydrogen atom,
  • R d represents a (C 1 -C 4 )alkyl group, linear or branched, preferably R d represents a methyl group
  • L represents a (C 1 -C 6 )alkylene group, linear or branched, or cycloalkylene, preferably L represents a (C 1 -C 4 )alkylene group, in particular ethylene.
  • the monomer (B) is chosen from acetoacetoxy ethyl acrylate, acetoacetoxy ethyl methacrylate, and mixtures thereof and preferably, the monomer (B) is acetoacetoxy ethyl methacrylate.
  • Acetoacetoxyethyl acrylate is a compound with the molecular formula C 9 H 12 O 5 , and with the condensed structural formula:
  • acetoacetoxyethyl acrylate of that marketed under the name Butanoic acid, 3-oxo-,2-[(1-oxo-2-propen-1-yl)oxy]ethyl ester by the company Alfa Chemistry.
  • Acetoacetoxyethyl methacrylate is a compound with the molecular formula C 10 H 14 O 5 , and with the condensed structural formula:
  • acetoacetoxyethyl methacrylate mention may in particular be made of that marketed under the name EastmanTM AAEM by the Eastman Company.
  • the copolymer comprises from 0% to 99% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates , silicone macromonomers, and mixtures thereof, relative to the total weight of the monomers.
  • C monomer chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates , silicone macromonomers, and mixtures thereof, relative to the total weight of the monomers.
  • the CP copolymer according to the invention does not comprise monomer (C).
  • the CP copolymer according to the invention then consists of monomer(s) (B) and monomer(s) (A) as defined above.
  • the monomer (C) is a C 1 -C 4 alkyl acrylate, in particular chosen from butyl acrylate, isobutyl acrylate, tert-butyl acrylate.
  • Butyl acrylate is a compound with the molecular formula C7H13O2 and the condensed structural formula:
  • butyl acrylate of that marketed under the name Butyl acrylate by the company Sigma Aldrich.
  • the monomer (C) is at least one monomer chosen from C 1 -C 4 alkyl acrylates and/or C 1 -C 4 alkyl methacrylates, preferably chosen from C 1 -C 4 alkyl acrylates, and more preferably the monomer (C) is at least butyl acrylate.
  • Isobutyl acrylate is a compound with the molecular formula C 7 H 12 O 2 and the semi-developed formula:
  • isobutyl acrylate of that marketed under the name isobutyl acrylate by the company Sigma Aldrich.
  • Tertio-butyl acrylate is a compound with the molecular formula C7H 12 O 2 and the semi-developed formula:
  • tert-butyl acrylate of that marketed under the name tert-butyl acrylate by the company Sigma Aldrich.
  • the monomer (C) is at least one silicone macromonomer.
  • silicone macromonomer is meant a silicone macromolecule with a terminal group which allows it to act as a monomer. Silicone macromonomers will contribute a single monomer unit to a chain of the terminated macromolecule.
  • silicone macromonomers they may in particular be polydimethylsiloxanes with a monoacryloyloxy or monomethacryloyloxy terminal group, and in particular those of formula (II): in which :
  • R 8 denotes a hydrogen atom or a methyl group, preferably methyl
  • R 9 denotes a divalent hydrocarbon group, linear or branched, preferably linear, having from 1 to 10 carbon atoms and optionally containing one or two ether bonds - O-; preferably ethylene, propylene or butylene;
  • - Rio denotes a linear or branched alkyl group having from 1 to 10 carbon atoms, in particular from 2 to 8 carbon atoms; preferably methyl, ethyl, propyl, butyl or pentyl;
  • - n denotes an integer ranging from 1 to 300, preferably ranging from 3 to 200.
  • They may in particular be polydimethylsiloxane methacrylates and in particular those marketed under the name MCR-M17 by Gelest Inc. or x-22-2475 and x-22-2426 by Shin Etsu.
  • the silicone macromonomers which are most particularly suitable for the invention have a weight-average molecular mass (Mw) ranging from 200 g.mol ⁇ 1 to 100,000 g.mol ⁇ 1 , and more preferably from 400 g.mol ⁇ 1 to 20,000 g. mol -1 .
  • the monomer ( C ) is at least one silicone macromonomer, more particularly chosen from silicone macromonomers having a glass transition temperature T g of less than or equal to 25°C, more particularly between -100°C and 25°C. C, and preferably between -90°C and 0°C.
  • the monomer (C) is at least one polydimethylsiloxane with a mono(meth)acryloyloxy end group.
  • the copolymer CP comprises from 0% to 45% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyls, 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 (C) chosen from alkyl acrylates C 1 -C 4 alkyl methacrylates, C 1 -C 4 alkyl methacrylates, silicone macromonomers, and mixtures thereof, relative to the total weight of the monomers, and at least one monomer (A) as defined above, more preferably 50% to 99% of at least one monomer (A) as defined previously.
  • the copolymer CP comprises from 80% to 99% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, d C 1 -C 4 alkyls, and preferably CP comprises from 80% to 99% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, alkyl methacrylates C 1 -C 4 relative to the total weight of the monomers, and no monomer (A) as defined above.
  • the copolymer CP comprises from 80% to 99% by weight of at least one monomer (C) chosen from silicone macromonomers, and their mixtures with C alkyl acrylates 1 -C 4 or with C 1 -C 4 alkyl methacrylates, relative to the total weight of the monomers, preferably 80% to 99% by weight of a mixture of at least one monomer (C) chosen from the silicone macromonomers and of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates and/or C 1 -C 4 alkyl methacrylates, relative to the total weight of the monomers, plus preferably, the copolymer CP comprises 80% to 99% by weight of a mixture of at least one monomer (C) chosen from silicone macromonomers and at least one monomer (C) chosen from C 1 alkyl acrylates -C 4 and/or C 1 -C 4 alkyl methacrylates, and no monomer (A) relative to the
  • the copolymer CP comprises more than 30% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, alkyl methacrylates C 1 -C 4 , and preferably CP comprises from 30.01% to 99% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates relative to the total weight of the monomers and at least one monomer (A) as defined above in a non-zero quantity and less than 50% relative to the total weight of the monomers.
  • C monomer chosen from C 1 -C 4 alkyl acrylates, alkyl methacrylates C 1 -C 4
  • CP comprises from 30.01% to 99% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates relative to the total weight of the monomers and at least one monomer (A) as defined above in
  • the monomers (C) preferably denote C 4 alkyl acrylates, C 4 alkyl methacrylates or mixtures of C 1 -C 3 alkyl acrylates and/or C 1 -C 3 alkyl methacrylates with C 4 alkyl acrylates or C 4 alkyl methacrylates.
  • the copolymer CP comprises more than 30% by weight of at least one monomer (C) chosen from silicone macromonomers and mixtures thereof with C 1 -C alkyl acrylates 4 or with C 1 -C 4 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 (C) chosen from silicone macromonomers and mixtures thereof with C 1 -C 4 alkyl acrylates or with C 1 -C 4 alkyl methacrylates, relative to the total weight of the monomers and at least one monomer (A) as defined previously in a non-zero quantity and less than 50% relative to the total weight of the monomers.
  • C monomer chosen from silicone macromonomers and mixtures thereof with C 1 -C alkyl acrylates 4 or with C 1 -C 4 alkyl methacrylates
  • the copolymer CP comprises more than 45% and less than 49% by weight of at least one monomer (C) chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates, silicone macromonomers, and mixtures thereof and preferably CP comprises from 45.01% to 48.99% by weight of at least one monomer (C) chosen from C alkyl acrylates 1 -C 4 , C 1 -C 4 alkyl methacrylates relative to the total weight of the monomers, and at least one monomer (A) as defined previously in an amount of 50 to 99% relative to the total weight of the monomers.
  • C monomer chosen from C 1 -C 4 alkyl acrylates, C 1 -C 4 alkyl methacrylates, silicone macromonomers, and mixtures thereof and preferably CP comprises from 45.01% to 48.99% by weight of at least one monomer (C) chosen from C alkyl acrylates 1 -C 4 , C 1 -C 4 alky
  • the monomers (C) preferably denote C 4 alkyl acrylates, C 4 alkyl methacrylates or mixtures of C 1 -C 3 alkyl acrylates and/or C 1 -C 3 alkyl methacrylates with C 4 alkyl acrylates or C 4 alkyl methacrylates.
  • the copolymer CP included in a composition C1, C2 or C3 according to the invention can be prepared by radical polymerization of at least one monomer (B) with at least one monomer (A) if present and/or at least one monomer (C) if present and as described previously.
  • the mixture of monomers to be polymerized generally in an organic medium having a boiling point greater than or equal to 60°C, can be formed at the very start of the polymerization reaction or be formed as the polymerization by gradually or sequentially adding certain monomers.
  • the polymerization of these monomers is carried out in the presence of an initiator.
  • organic medium suitable for the preparation of the copolymer mention may in particular be made of solvents such as isododecane, ethanol, ethyl acetate, tetrahydrofuran, methyltetrahydrofuran, or methyl ethyl ketone and mixtures thereof.
  • solvents such as isododecane, ethanol, ethyl acetate, tetrahydrofuran, methyltetrahydrofuran, or methyl ethyl ketone and mixtures thereof.
  • the synthesis medium is a mixture of several solvents, in particular two solvents of different boiling points.
  • the synthesis medium contains several solvents with different boiling points, in particular two solvents, it is possible, at the end of the synthesis of the copolymer CP, to eliminate the solvent or solvents with the lowest boiling points, optionally after adding a higher boiling point medium identical to or different from the highest boiling point solvent constituting the synthesis medium.
  • the synthesis medium is chosen such that the monomers (B) and (A) and/or (C) of the copolymer and the initiator are soluble therein.
  • the monomers are present in the synthesis solvent, before polymerization, in a content ranging from 5% to 45% by weight, relative to the total weight of the synthesis medium.
  • the monomers to be polymerized can be introduced into the synthesis medium before the start of the polymerization reaction, either gradually or sequentially, as the polymerization progresses.
  • This polymerization is carried out in the presence of an initiator, in particular of the peroxide or azo type.
  • the initiator can be chosen from tert-Butyl peroxy-2-ethylhexanoate, such as Trigonox 21S marketed by AkzoNobel, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, such as Trigonox 141 marketed by AkzoNobel, tert-butyl peroxypivalate, such as Trigonox 25C75 marketed by AkzoNobel, azobisisobutyronitrile (AIBN), 2,2'-azo-bis(2-amidinopropane) dihydrochloride (V50).
  • the initiator is tert-Butyl peroxy-2-ethylhexanoate, such as Trigonox 21S marketed by AkzoNobel.
  • the polymerization is carried out at a temperature ranging from 70°C to 110°C.
  • the synthesis of the copolymer CP is carried out in a mixture of two solvents with different boiling points, in particular in an isododecane and ethyl acetate mixture.
  • the solvent with the lowest boiling point, in particular ethyl acetate is eliminated, in particular by distillation.
  • a composition C1 is obtained comprising the copolymer CP in the solvent with the highest boiling point, in particular in isododecane.
  • the copolymers used have masses by weight of between more preferably between 10,000 g. mol′ 1 and 500000 g.mof′ct even more preferentially between 15000 g. mol -1 and 350000 g. mol -1.
  • CP copolymers implemented according to the invention, mention may in particular be made of the copolymers obtained by the copolymerization:
  • the present invention further relates to a composition, in particular cosmetic, for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratin fibers and preferably the hair, comprising a CP copolymer as defined above.
  • composition according to the invention can in particular be presented in the variants of compositions called C1, C2 and C3.
  • composition C1 may comprise, in addition to a fatty phase and a copolymer CP in accordance with the invention, at least one cosmetic active ingredient called "AC", chosen from a) coloring agents chosen from pigments, direct dyes, and their mixtures, b) active ingredients for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • AC cosmetic active ingredient
  • a composition C1 consists of a fatty phase and a CP copolymer in accordance with the invention, optionally at least one so-called “AC” cosmetic active ingredient chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof and optionally at least one cosmetically acceptable compound other than an AC cosmetic active agent.
  • AC cosmetic active ingredient chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof and optionally at least one cosmetically acceptable compound other than an AC cosmetic active agent.
  • a composition C2 comprises, in addition to a fatty phase and a copolymer CP in accordance with the invention, at least one crosslinking agent called “R” as defined below, and optionally at least one cosmetic active agent AC.
  • composition C2 is devoid of cosmetic active ingredient called “AC” in particular as defined below.
  • a composition C2 consists of a fatty phase and a copolymer CP in accordance with the invention, at least one crosslinking agent, called "R” as defined below and optionally a cosmetically acceptable compound different from an AC cosmetic active ingredient.
  • a composition C3 comprises, in addition to a fatty phase and a copolymer CP in accordance with the invention, at least one crosslinking agent, called “R” as defined below, and at least one cosmetic active agent AC.
  • crosslinking agent also called “R” denotes a compound capable of establishing with at least one acetoacetate function of the (co)polymer CP contained in a composition according to the invention: at least one covalent bond, at least one (dative) donor-acceptor type bond, and/or at least one coordination bond and thus to crosslink this (co)polymer.
  • crosslinking agent also called “R” denotes a compound capable of establishing at least one covalent bond with an acetoacetate function of the (co)polymer CP contained in a composition according to the invention and thus of crosslinking this (co)polymer.
  • crosslinking agent and “crosslinking agent” are equivalent.
  • a composition according to the invention is devoid of such a crosslinking agent R.
  • composition C1 as described previously comprises a copolymer CP and a fatty phase in accordance with the invention and is devoid of crosslinking agent R.
  • compositions according to the invention such as compositions C2 and C3 are obtained by mixing a composition C1 with at least one crosslinking agent R or a composition containing such a crosslinking agent and called “CR” composition.
  • a CR composition contains at least one crosslinking agent.
  • a CR composition does not contain a CP copolymer.
  • a CR composition can, on the other hand, comprise a fatty phase, an aqueous phase or can be in the form of a direct or inverse emulsion.
  • a CR composition can also comprise a so-called “AC” cosmetic active ingredient, chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients for caring for keratin materials, preferably the skin, c) UV screening agents, and d) mixtures thereof and in particular at least one coloring agent, more particularly at least one pigment.
  • composition C3 can be obtained either:
  • composition C 1 by mixing a composition C 1 with at least one crosslinking agent R or a composition containing such a crosslinking agent and called CR, and at least one cosmetic active ingredient AC, said AC being considered via a separate composition called "CAC", and/or via composition C1 and/or CR, or
  • composition C2 by mixing a composition C2 with at least one cosmetic active ingredient AC or a composition CAC, distinct from C2, containing said one cosmetic active ingredient AC.
  • CAC composition contains at least one cosmetic active ingredient chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients for caring for keratin materials, preferably the skin , c) UV filters, and d) mixtures thereof.
  • a CAC composition does not contain a CP copolymer.
  • a CAC composition also does not contain crosslinking agent R.
  • a CAC composition can, on the other hand, comprise a fatty phase, an aqueous phase or can be in the form of a direct or inverse emulsion.
  • a composition C3 can be obtained by mixing a composition C1 according to the invention with a composition CR comprising at at least one crosslinking agent R, said composition C1 and/or CR each possibly additionally containing at least one cosmetic active agent AC.
  • composition according to the invention contains at least one crosslinking agent
  • said crosslinking agent and said CP copolymer are preferably present in a mass ratio ranging from 5 to 40%.
  • a crosslinking agent R suitable for the invention can be chosen from compounds containing amine, thiol, alcohol, acrylate and/or carbonyl functions such as ketone and/or aldehyde functions, or a mixture thereof.
  • a cross-linking agent R can also designate a metal alkoxy or a metal salt or a derivative of rare earths.
  • the crosslinking agent R is chosen from (poly)amino, (poly)thiolated and/or (poly)hydroxylated, (poly)carbonylated, (poly)acrylates and mixtures thereof, and preferably chosen from (poly)amino and (poly)thiolated compounds and in particular as detailed below.
  • the crosslinking agent R is chosen from (poly)amino, (poly)thiolated and/or (poly)hydroxylated, (poly)carbonylated, (poly)acrylates and/or metal alkoxide compounds. , (Poly Khydroxy) (Ci-C6) metal alkylcarboxylate, rare earth derivatives and mixtures thereof, and preferably chosen from (poly)amino and (poly)thiolated compounds and in particular as detailed below.
  • (poly)amino, (poly)thiolated and/or (poly)hydroxylated, (poly)carbonyl and (poly)acrylate compounds is meant the compounds comprising respectively at least one amine, thiol and/or hydroxyl, carbonyl function such a ketone or aldehyde or acrylate function.
  • Alkoxide compounds Metal i-Côlalkylcarboxylates and rare earth derivatives are defined below.
  • the crosslinking agent R is chosen from (poly)amino compounds.
  • the (poly)amino compound can in particular be chosen from polyamino compounds having several primary amine and/or secondary amine groups or even from amino alkoxysilanes, and more particularly from amino alkoxysilane compounds, diamino compounds, triamino compounds, and their mixtures.
  • the (poly)amine compound can be a compound comprising from 2 to 20 carbon atoms, in particular a non-polymeric compound.
  • non-polymeric compound is meant a compound which is not directly obtained by a polymerization reaction of monomers.
  • (poly)amino compounds mention may in particular be made of N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, N-isopropyl 1,3-diaminopropane, N-cyclohexyl 1,3 -diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methyl bis(3-aminopropyl)amine, N-(3-aminopropyl) -1,4-diaminobutane, N,N-dimethyldipropylene triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylene diamine, 1,3-propylenediamine, 1,4-
  • the amino compound can also be chosen from amino alkoxysilanes, such as those of formula R′iSi(OR′2)z(R′3)x in which:
  • R'i is a hydrocarbon chain in CI-C ⁇ , linear or branched, saturated or unsaturated, cyclic or acyclic substituted by a group chosen from amine groups NH2 or NHR with R representing a C 1 -C 4 alkyl, an aryl or an aryloxy substituted by an amino group or by a C 1 -C 4 aminoalkyl group; R'i can be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group (CO), R'i being linked to the silicon atom directly via a carbon atom,
  • R' 2 and R' 3 identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms,
  • R' 1 is an acyclic chain.
  • R' 1 is a linear or branched, saturated or unsaturated, C1-C6 hydrocarbon chain, substituted by an amine group NH2 or NHR, with R representing a C1-C6 alkyl, a C3-C6 cycloalkyl or aromatic in CO.
  • R'i is a saturated linear C1-C6 hydrocarbon chain substituted by an amine group NH2.
  • R'i is a saturated linear C2-C4 hydrocarbon chain substituted by an amine group NH2.
  • R'2 represents an alkyl group comprising from 1 to 4 carbon atoms, preferably R'2 represents a linear alkyl group comprising from 1 to 4 carbon atoms, and more preferably R'2 represents the ethyl group.
  • R'3 represents an alkyl group comprising from 1 to 4 carbon atoms, preferably R'3 represents a linear alkyl group comprising from 1 to 4 carbon atoms, and more preferably R'3 represents the methyl group or ethyl.
  • z is equal to 3.
  • the amino alkoxysilane is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3 - (m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.
  • APTES 3-aminopropyltriethoxysilane
  • AETES 3-aminoethyltriethoxysilane
  • 3-aminopropylmethyldiethoxysilane N-(2-aminoethyl)-3-aminopropyltriethoxysilane
  • the amino alkoxy silane is chosen from 3-aminopropyltriethoxy silane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferably the amino alkoxysilane is 3-aminopropyl triethoxysilane (APTES).
  • APTES 3-aminopropyltriethoxy silane
  • AETES 3-aminoethyltriethoxysilane
  • APTES 3-aminopropylmethyldiethoxysilane
  • APTES 3-aminopropyl triethoxysilane
  • the (poly)amino compound is chosen from 3-aminopropyltriethoxysilane (APTES), N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, N-isopropyl 1 ,3-diaminopropane, N-cyclohexyl 1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methyl bis(3- aminopropyl)amine, N-(3-aminopropyl)-l,4- diaminobutane, N,N-dimethyldipropylene triamine, l,2-bis(3-aminopropylamino)ethane, N,N'-bis(3- aminopropyl)-1,3-propanediamine,
  • APTES 3-
  • the (poly)amine compound is chosen from ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, 3-aminopropyltriethoxy silane (APTES), and more preferably, the (poly)amine compound is ethylene diamine or 3-aminopropyltriethoxy silane (APTES).
  • APTES 3-aminopropyltriethoxy silane
  • the (poly)amino compound can also be chosen from amino polymers, in particular having a weight-average molecular weight ranging from 500 g.mol′ 1 to 1,000,000 g. mol 1 , preferably ranging from 500 g.mol 1 to 500,000 g.mol 1 , and preferentially ranging from 500 g.mol′ 1 to 100,000 g.mol′ 1 .
  • amino polymer mention may in particular be made of poly(alkylene (C2-C5) imines), and preferably polyethyleneimines and polypropyleneimines, in particular poly(ethylene imines), in particular that sold under the reference 46,852-3 by the Aldrich Chemical Company; poly(allylamine), in particular that sold under the reference 47,913-6 by the company Aldrich Chemical; polyvinylamines and their copolymers in particular with vinylamides, in particular vinylamine/vinylformamide copolymers such as those marketed under the name Lupamin® 9030 by the company BASF; polyamino acids having NH2 groups such as for example polylysine, in particular that sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular that sold by the company CarboMer Inc; polyvinyl amino alcohol, in particular that sold by the company CarboMer Inc, copolymers based on acrylamidopropyl laminate; chitosans, such as for example poly(D-Gluco
  • n and m are such that the weight-average molecular weight of the polydimethylsiloxane ranges from 1000 g.mol 1 to 55000 g. mol 1 .
  • polydimethylsiloxanes of formula (IV) mention may be made of those sold under the names “AMS-132”, “AMS-152”, “AMS-162”, “AMS-163”, “AMS-191” and “AMS -1203” by the company Gelest. in which the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol 1 .
  • AMS-132 AMS-152
  • AMS-162 AMS-163
  • AMS-191 AMS -1203
  • amino polymer there may also be mentioned the amodimethicones of formula
  • polyether amines in particular known under the reference Jeffamine from the company Hunstman; and in particular polyethylene glycol and/or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as for example those sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600 , ED-9000, ED-2003.
  • amino polymer mention may also be made of polytetrahydrofuran (or polytetramethylene glycol) ⁇ ,co-diamine, polybutadienes ⁇ ,co-diamine and polyamidoamine dendrimers (PAMAM) with terminal amine functions.
  • PAMAM polyamidoamine dendrimers
  • amino polymer mention may also be made of poly(meth)acrylates or poly(meth)acrylamides carrying lateral primary or secondary amine functions, such as poly(3-aminopropyl)methacrylamide, poly(2-aminoethyl) methacrylate.
  • amino polymer chitosans and polydimethylsiloxanes comprising primary amine groups at the end of the chain or on the side chains are preferably used.
  • the polyamino compounds are chosen from chitosans, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on the side chains, and APTES.
  • a composition C2 or C3 according to the invention comprises a crosslinking agent R chosen from (poly)amino compounds, in particular chosen from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups in chain end or on side chains, amodimethicones, polyglucosamines, and mixtures thereof.
  • R chosen from (poly)amino compounds, in particular chosen from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups in chain end or on side chains, amodimethicones, polyglucosamines, and mixtures thereof.
  • a C2 or C3 composition according to the invention comprises a crosslinking agent R chosen from chitosans, aminoalkoxysilanes and polydimethylsiloxanes comprising primary amine groups at the end of the chain or on the side chains, and even more preferably chosen from poly (D-Glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, A-(2-aminoethyl)-3-aminopropyltriethoxysilane and polydimethylsiloxanes containing groups at the end of the chain aminopropyl terminals, and even more preferably is 3-aminopropyl triethoxysilane (APTES).
  • R chosen from chitosans, aminoalkoxysilanes and polydimethylsiloxanes comprising primary amine groups at the end of the chain or on the side
  • the crosslinking agent is chosen from (poly)thiolated and/or (poly)hydroxylated compounds.
  • the (poly)thiolated and/or (poly)hydroxylated compound may in particular be organic or inorganic, preferably organic.
  • the (poly)thiolated and/or (poly)hydroxylated compound of the invention is chosen from fat-soluble or non-lipid-soluble compounds.
  • liposoluble compound is meant a compound that is soluble or miscible to at least 1% by weight in isododecane at 25°C.
  • the (poly)thiolated and/or (poly)hydroxylated compound is silicone, that is to say it comprises one or more hydroxy groups, or one or more thiol groups or one or more hydroxy groups and one or more thiol groups, it also comprises at least one siloxane chain.
  • the (poly)thiolated and/or (poly)hydroxylated compound is inorganic. Mention may be made, for example, of polythiol silicones and polythiol silicas.
  • the (poly)thiolated and/or (poly)hydroxylated compound used in a composition according to the invention may in particular be chosen from nonpolymeric (poly)thiolated and/or (poly)hydroxylated compounds.
  • non-polymeric compounds within the meaning of the present invention, is meant compounds which are not directly obtained by a polymerization reaction of monomers.
  • the (poly)thiolated and/or (poly)hydroxylated compound is organic, non-polymeric and of formula (VII) below as well as its solvates such as its hydrates: in which: p and q, identical or different, represent an integer, it being understood that the sum p + q is greater than or equal to 2, preferably the sum p + q is between 2 and 10 inclusive, preferably between 2 and 5;
  • L denotes a multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and/or silicon atoms, more particularly between 2 and 40 carbon and/or silicon atoms, even more particularly between 3 and 30 atoms carbon and/or silicon, preferably between 6 and 20 carbon atoms, linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated;
  • L being optionally interrupted and/or terminated by one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and their associations such as -O-, -OC(X)-, -N(R )-C(X)-,-Si(R c )(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl group such as methyl; and or
  • L being optionally substituted by one or more halogen atoms, or a group chosen from R a (R b )N-, -(X') a -C(X)-(X”) b -Ra;
  • X, X' and X identical or different, represent an oxygen or sulfur atom or an N(R b ) group; a, and b being 0 or 1, preferably the sum of a+b is 1;
  • R a and Rb which are identical or different, represent a hydrogen atom, or a (C 1 -C 6 )alkyl group, or aryl(C 1 -C 4 )alkyl such as benzyl, preferably R a and Rb represent a hydrogen atom;
  • R c and Rd which are identical or different, represent a (C 1 -C 6 )alkyl, aryl(Ci-C 4 )alkyl or (C 1 -C 6 )alkoxy group.
  • q is equal to 0 and p is an integer greater than or equal to 2, preferably p is an integer comprised from 2 to 10, preferably from 2 to 5.
  • the (poly)thiolated and/or (poly)hydroxylated compound is chosen from polyhydroxylated compounds.
  • polyhydroxylated compounds comprising from 2 to 20 carbon atoms, in particular nonpolymeric polyhydroxylated compound(s).
  • the (poly)thiolated and/or (poly)hydroxylated compound used according to the invention may be chosen from hydroxyalkoxysiloxane or thioalkoxysiloxane compounds, it being understood that these compounds may also comprise one or more primary or secondary amine groups.
  • a polyhydroxy compound used according to the invention is an organic compound comprising at least 2 hydroxy functions.
  • This compound may include other non-reactive chemical functions such as esters, amides, ketones, urethanes. It is possible to use a mixture of distinct polyhydroxy compounds.
  • the polyhydroxy compound used according to the invention is an inorganic compound comprising at least 2 hydroxy functions.
  • This compound may include other non-reactive chemical functions such as esters, amides, ketones, urethanes. It is possible to use a mixture of distinct polyhydroxy compounds such as a mixture of organic and inorganic polyhydroxy compound(s).
  • the thiolated and/or hydroxylated compound is chosen from polyhydroxylated, polythiolated, and polymeric polyhydroxylated and polythiolated compounds.
  • the polyhydroxy compound is a non-polymeric organic compound of formula (Vila) below:
  • L is as defined above, preferably L denotes a multivalent radical (at least divalent) comprising between 8 and 30 carbon and/or silicon atoms, preferably between 10 and 20 carbon and/or silicon atoms, linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, L possibly also being interrupted by one or more oxygen atoms, and/or comprising one or more functions chosen from amino, ether, thioether, ester, thioester, ketone, thioketone, amide and thioamide functions.
  • the polyhydroxy compound is preferably a diol compound.
  • L denotes a multivalent Cs-Cis radical, in particular linear.
  • the polyhydroxylated compound is a fat-soluble polyol, in particular a Cs-Cis diol, in particular linear.
  • the Cs-Cis chain is a hydrocarbon chain, that is to say formed of carbon and hydrogen.
  • the liposoluble polyol is a linear Cs-Ci6 diol, in particular Cio-Cu.
  • polyol of formula (Vila) mention may be made of 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol, 1,16-hexadecanediol, 1,18 -octadecanediol.
  • 1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol are used.
  • 1,12-dodecanediol is used.
  • the thiolated and/or hydroxylated compound is chosen from polythiolated compounds also called “polymercapto”.
  • the polythiolated compounds used according to the invention can be water-soluble or fat-soluble, preferably they are fat-soluble.
  • the thiolated and/or hydroxylated compound is chosen from polythiolated compounds, in particular polythiolated compounds comprising from 2 to 20 carbon atoms.
  • the thiolated and/or hydroxylated compound is thiolated, non-polymeric and of formula (VII) defined above, in which p is 0 and q is an integer greater than or equal to 2, preferably p is an integer comprised inclusively between 2 and 10, preferably between 2 and 5.
  • a polythiolated compound suitable for the invention is a non-polymeric organic compound of formula (VIIb):
  • the polythiolated compounds suitable for the invention are preferably dithiol compounds.
  • L denotes a multivalent Cs-Cis radical, in particular linear.
  • the fat-soluble polythiol is a Cs-Cis dithiol, in particular linear.
  • the Cs-Cis chain is a hydrocarbon chain, that is to say formed from carbon and hydrogen.
  • the liposoluble polythiol is a linear Cs-C16 diol, in particular C10-C14.
  • polyol of formula (VIIb) mention may be made of 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol, 1,18 - octadecanedithiol.
  • 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol are used.
  • 1,12-dodecanedithiol is used.
  • the thiolated and/or hydroxylated compound is thiolated and hydroxylated, non-polymeric and of formula (VII) as defined above, in which q and p are integers greater than or equal to 1, preferably the sum p+q is an integer comprised from 2 to 10, preferably from 2 to 5, and preferably q>p.
  • the thiolated and/or hydroxylated compound is chosen from (poly)hydroxylated and (poly)thiolated compounds, in particular (poly)hydroxylated and (poly)thiolated compounds comprising 2 to 20 carbon atoms, and in particular non-polymeric (poly)hydroxylated and (poly)thiolated compounds.
  • the thiolated and/or hydroxylated compound is chosen from hydroxylated and/or thiolated alkoxysiloxanes, such as those of formula (VIII) below: RVS ⁇ OR'aMR ⁇ (VIII ) in which :
  • R'i is a C1-C12 hydrocarbon chain, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by one or more groups chosen from the groups: hydroxy or thiol, preferably thiol, aryl, aryloxy, arylthio, arylamino, the aryl group being substituted by one or more hydroxy, thiol, hydroxy(Ci-C6)alkyl or thiol(Ci-C6)alkyl groups, preferably thiol(Ci-C6)alkyl, and
  • R' 1 is optionally interrupted in its hydrocarbon chain by one or more heteroatoms such as O, S, N, a carbonyl group (CO), or their combination such as ester — C(O)-O-, or amide -C(O)-N(H)-, R'i being bonded to the silicon atom directly via a carbon atom,
  • heteroatoms such as O, S, N, a carbonyl group (CO), or their combination such as ester — C(O)-O-, or amide -C(O)-N(H)-
  • R'2 and R'3, identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atom(s) such as methyl,
  • R′2 represents an alkyl group comprising from 1 to 4 carbon atoms.
  • R′2 represents a linear alkyl group comprising from 1 to 4 carbon atoms.
  • R′2 represents the ethyl group.
  • R′3 represents an alkyl group comprising from 1 to 4 carbon atoms.
  • R′3 represents a linear alkyl group comprising from 1 to 4 carbon atoms.
  • R′3 represents the methyl or ethyl group.
  • R'i is an acylique string.
  • R'i is a linear or branched, saturated or unsaturated, C1-C6 hydrocarbon chain, substituted by one or more hydroxy or thiol groups, preferably thiol.
  • R'i is a saturated linear C1-C6 hydrocarbon chain substituted by a hydroxy or thiol group, preferably thiol.
  • R'i is a saturated linear C2-C4 hydrocarbon chain substituted by a hydroxy or thiol, preferably thiol, group.
  • R'i is a saturated linear C1-C6 hydrocarbon chain substituted by a hydroxy or thiol group, preferably thiol
  • R'2 represents an alkyl group comprising from 1 to 4 carbon atoms
  • R'3 represents an alkyl group comprising from 1 to 4 carbon atoms.
  • z is equal to 3.
  • the alkoxysiloxanes (VIII) are chosen from those of the following formula (VIII'): in which
  • X represents an oxygen or sulfur atom, preferably sulfur
  • R 1 represents a (C 1 -C 6 )alkyl radical
  • R 2 and R 3 are chosen from: a (C 1 -C 6 )alkoxy group, in particular C 1 -C 4 ; a (C 1 -C 6 )alkyl group;
  • R 4 represents a hydrogen atom, or a (C 1 -C 6 )alkyl group such as methyl
  • L 1 represents a divalent, saturated, C1-C20 linear or branched hydrocarbon radical.
  • the alkoxysiloxanes (VIII) are chosen from those of the following formula (VIII”): in which :
  • X represents an oxygen or sulfur atom, preferably sulfur
  • R′ 1 denotes a (C 1 -C 6 )alkyl radical
  • R′ 2 and R′ 3 which are identical or different, preferably identical, are chosen from: a (C 1 -C 6 )alkoxy group, in particular C 1 -C 4 ; a (C 1 -C 6 )alkyl radical;
  • R 5 represents a hydrogen atom or a C 1 -C 4 alkyl group optionally substituted by an amino, thiol or hydroxy group;
  • R 4 represents a hydrogen atom or a C 1 -C 4 alkyl group, in particular methyl
  • L 2 represents a divalent hydrocarbon group, linear or branched saturated C1-C20, optionally interrupted by a heteroatom such as -NH-, optionally substituted by one or more hydroxy, thiol or amino groups.
  • the alkoxy silane of formula (VIII) is chosen from 4-(trimethoxysilyl)-1-butanol, 3-(trimethoxysilyl)-l-propanol, 3-(triethoxysilyl)-l-propanol, 11-(trimethoxysilyl)-l-undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)-ethanethiol, 3-(triethoxysilyl)-l-propanethiol, 2-(trimethoxysilyl)-ethanethiol , 3-(trimethoxysilyl)-1-propanethiol and 3-(dimethoxymethylsilyl)-1-propanethiol.
  • the alkoxy silane of formula (VIII) is chosen from 2-(triethoxy silyl)-ethanethiol (18236-15-2) and 3-(triethoxy silyl)-1-propanethiol (14814-09-6).
  • the thiol compound is a particle carrying at least two thiol groups. It is for example a silica functionalized by radicals, in particular of the alkyl type, substituted by thiol functions.
  • the thiolated compound can designate the particles marketed under the name SiliaMetS® Thiol by the company Silicycle or under the name SP-THIO-SILICA by the company Suprasciences.
  • the thiolated compound can be chosen from polythiol silicas prepared according to the procedure described in. J. Mater. Chem., 2007, 17, 3726-3732; J. Am. Chem. Soc., 2005, 127 (23), pp 8492-8498; 10.1109/ICBBE.2010.5517542; Chemical Engineering Journal, 2011, 171 (3), 1004-1011; Minerals Engineering, 2012, 35, 20-26; Colloids and Surfaces A: Physicochemical and Engineering Aspects, 380, (1-3), 229-233), Advanced Science, Engineering and Medicine, Volume 5, Number 9, September 2013, pp. 984-987(4).
  • the particle bearing at least two thiol groups can also be obtained by reaction of a silica particle such as the Sunsphere® particles marketed by Asahi Glass with mercapto alkylalkoxysilanes such as 3-mercaptopropyltriethoxysilane.
  • a silica particle such as the Sunsphere® particles marketed by Asahi Glass
  • mercapto alkylalkoxysilanes such as 3-mercaptopropyltriethoxysilane.
  • the thiolated compound is a particle bearing at least two thiol groups obtained by reacting a Sunsphere® silica particle marketed by Asahi Glass, preferably a 5 ⁇ m Sunsphere particle with 3-mercaptopropyltriethoxy silane according to the publication, Journal of Chromatography A, Volume 1217, Issue 47, 19 November 2010, Pages 7448-7454.
  • the polythiolated particles can be present in the form of latex carrying thiol groups such as those described in Colloids and Surfaces A: Physiochemical and Engineering Aspects 153, 1999, 421-427.
  • the thiolated compound is a particle coated with compound(s) carrying at least two thiol functions.
  • the (poly)thiolated and/or (poly)hydroxylated compound used in a composition according to the invention may in particular be chosen from polymeric (poly)thiolated and/or (poly)hydroxylated compounds.
  • the polymeric (poly)thiol and/or (poly)hydroxyl compounds can be homopolymers, copolymers, star, combe, brush and dendritics with hydroxy and/or thiol units.
  • the polymers can be of natural origin such as polysaccharides, polypeptides, or synthetic such as acrylics, polyesters, polyglycols.
  • the hydroxy and thiol units can be present as terminal or pendent groups.
  • Examples include the polymers described in the following scientific articles: Polymers containing groups of biological activity, CG Overberger et al, Polytechnic Institute of Brooklyn, http://pac.iupac.org/publications/pac/pdf/1962/pdf /0402x0521.pdf; EP 1 247 515 A2; U.S. 3,676,440; and EP 1,572,778.
  • the thiolated and/or hydroxylated polymers which may be suitable for the invention are preferably organic or silicone, more preferably of formula (IX): (HO)pPOLY(SH)q (IX) in which:
  • POLY denotes a polymeric radical, preferably carbonaceous or silicone
  • POLY being optionally interrupted by one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and their combinations such as -O-, -OC(X)-, -N(R)-C( X)-, -Si(R c )(Rd)-O- with R representing a hydrogen atom or a (C 1 -C 6 )alkyl group such as methyl; and or
  • POLY being optionally substituted by one or more halogen atoms, or a group chosen from R a (Rb)N- and -(X') a -C(X)-(X”)b-Ra;
  • X, X' and X identical or different, represent an oxygen atom, a sulfur atom, or an N(Rb) group; a, and b being 0 or 1, preferably the sum of a+b is 1;
  • R a and Rb which are identical or different, represent a hydrogen atom, or a (Ci-Cio)alkyl group, or aryl(C 1 -C 4 )alkyl such as benzyl, preferably R a and Rb represent a hydrogen; and
  • R c and Rd which are identical or different, represent a (Ci-Cio)alkyl, aryl(Ci- C4 )alkyl or (Ci-Cio)alkoxy group.
  • the thiolated and/or hydroxylated compound is chosen from (poly)hydroxylated polymers also called “polyol”.
  • the (poly)hydroxylated polymer(s) are chosen from those of formula (IX′):
  • POLY denotes a carbon or silicone polymeric radical, POLY possibly also containing one or more heteroatoms such as O, N, S and/or one or more functions chosen from amino functions, (thio)esters, (thio)ketones, ( thio)amides, (thio)ureas, (thio)carbamates, and/or be substituted by one or more (Ci-Cio)alkyl groups, linear or branched, (Ci-Cio)alkoxy, linear or branched, it being understood that when POLY is substituted, the hydroxy functions can be carried by the substituent(s).
  • heteroatoms such as O, N, S and/or one or more functions chosen from amino functions, (thio)esters, (thio)ketones, ( thio)amides, (thio)ureas, (thio)carbamates, and/or be substituted by one or more (Ci-Cio)alkyl groups, linear or branched, (Ci-Ci
  • the average molecular weight by molar weight of the polymer polyol compounds, such as those of formula (IX′), is generally between 500 and 400,000 g. mol 1 , preferably between 500 and 150000 g.mol 1 .
  • the (poly)hydroxylated polymers (IX′) can be polymer (di)ols, in particular polyolefin (poly)ols, polydi(Ci-C6)alkylsiloxane (poly)ols, polyester (poly)ols, more preferably the (poly)ols are diols.
  • the polyolefin (poly)ols can be polydienes with hydroxy ends, such as for example those described in FR-A-2782723. They can be chosen from (poly)ols derived from homopolymers and copolymers of polybutadiene, polyisoprene and poly(1,3-pentadiene). Preferably, they have a number-average molecular weight (Mn) of less than 7000 g.mol 1 , preferably between 1000 and 5000 g.mol 1 .
  • Mn number-average molecular weight
  • the compounds of formula (IX') are chosen from the polyolefins (poly)ols of formula (X) below: in which :
  • ALK4 and ALK5 identical or different, preferably different, represent a (C 1 -C 6 )alkylene group, linear or branched, optionally substituted by one or more hydroxy, thiol or amino groups, preferably ALK4 represents a group ( C 1 -C 6 )linear alkylene such as n-butylene, and ALK5 represents a branched (C3-C6)alkylene group such as i-butylene;
  • X represents an oxygen or sulfur atom or an N(Ra) group with Ra representing a hydrogen atom or a (Ci-Chalky) group, preferably X represents a hydroxy or thiol group, more preferably hydroxy;
  • n and m identical or different, represent an integer, with n + m representing an integer greater than or equal to 1.
  • the (poly)ols of formula (X) can in particular be chosen from polyolefins with hydroxy ends.
  • polyolefins with hydroxy ends mention may preferably be made of polyolefins, homopolymers or copolymers, with a,o hydroxy ends, such as polyisobutylenes with a,o hydroxy ends and the copolymers of formula (X′): [Chem 24] in particular those marketed by Mitsubishi under the POLYTAIL brand.
  • polyolefins homopolymers or copolymers
  • a,o hydroxy ends such as polyisobutylenes with a,o hydroxy ends and the copolymers of formula (X′): [Chem 24] in particular those marketed by Mitsubishi under the POLYTAIL brand.
  • hydrogenated polybutadienes diols are used.
  • the (poly)ols of formula (X) may in particular be chosen from polydialkylsiloxane (di)ols, particularly from those of formula (XI) below: [Chem 25] in which :
  • R a , and R b identical or different, preferably identical, represent a (C 1 -C 6 )alkyl group optionally substituted by one or more hydroxy, amino or thiol, (C 1 -C 6 )alkoxy groups such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C 4 )alkyl such as benzyl, or aryl(C 1 -C 4 )alkoxy such as benzoxy, preferably (C 1 -C 4 )alkyl such as methyl,
  • n represents an integer greater than or equal to 1, and more particularly the value of n is such that the weight-average molecular weight of the silicone is between 500 and 55,000 g. mol 1 ; particularly n is an integer comprised from 1 to 100, preferably comprised from 5 to 50, and preferentially comprised from 10 to 30, and
  • L 4 and L 5 identical or different, represent a covalent bond, or a hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, optionally cyclic, optionally interrupted by one or more heteroatoms such as oxygen , sulfur or nitrogen, in particular oxygen, more preferably a group (C 1 -C 6 )alkylene, (C 1 -C 6 )alkylene-oxy, oxy-(C 1 -C 6 )alkylene, (Ci-C6)alkylene -oxy(Ci-C6)alkylene, (Ci-C6)alkylene-oxy(Ci-C6)alkylenoxy or oxy(Ci-C6)alkylene-oxy(Ci-C6)alkylene,
  • X represents an oxygen or sulfur atom, preferably oxygen.
  • polydialkylsiloxane (di)ols of formula (XI) are chosen from polydimethylsiloxanes, in particular the polydiols of formula (XI′) below:
  • L 4 and L 5 are as defined above, preferably represent a divalent group chosen from -R2-, -O-R2-, -R2-O-, -R2-O-R'2-, preferably -R2 -O-R'2-, with R2 and R'2, identical or different, representing a (C2-C6)alkylene group, linear or branched, such as ethylene or propylene, and
  • n represents an integer comprised inclusively between 1 and 100, preferably between 5 and 50, and preferably between 10 and 30.
  • polydimethylsiloxane diols those sold under the names KF-6000, KF-6001, KF-6002, KF-6003 by the company Shin-Etsu Chemicals.
  • the polydimethylsiloxane diol of the following formula (XI”) is preferably used:
  • dimethiconols which are polydimethylsiloxanes having terminal OH functions. Mention may be made, for example, of that sold under the name “XIAMETER PMX-1502 FLUID” by the company Dow Corning.
  • the (poly)ols of formula (X) are chosen from the polyhydroxylated compounds of formula (XII) below: in which :
  • Ri independently represents a hydroxy group; an alkyl group having 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; an alkoxy group having 1 to 2 carbon atoms; or a -(CH2) s -Si(R4)3 group in which s denotes an integer ranging from 1 to 4 such as 2, and R4 independently denotes an alkoxy radical having from 1 to 2 carbon atoms; R′ 2 and R′′ 2 independently represent an alkyl group having 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; a denotes an integer ranging from 0 to 10, b denotes an integer ranging from 0 to 500, with a + b > 4.
  • PDMS polydimethylsiloxanes
  • terminal hydroxy functions such as the compounds sold by the company Shin Etsu under the name KF-9701 or X-21-5841, or those sold by the company Sigma Aldrich under the reference 481939 (Mn -550 g.mol 1 , -25 cSt), 481955 (-65 cSt), or 481963 (-750 cSt).
  • DMS-S12 (16-32 cSt), DMS-S15 (45-85 cSt), DMS-S21 (90-120 cSt), DMS-S27 (700- 800 cSt) or DMS-S31 (-1000 cSt).
  • the silicone(s) of formula (XII) used in the context of the invention are chosen from the compounds of formula (XII) in which:
  • Ri independently represents an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, and more particularly from 1 to 2 carbon atoms such as a methyl;
  • R′2 and R′′2 independently represent an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, and more particularly 1 to 2 carbon atoms such as methyl; b denotes an integer ranging from 0 to 10, a denotes an integer ranging from 0 to 5, with a + b > 4.
  • the polythiol compound is a thiolated polymeric compound.
  • the thiolated polymers used according to the invention can be obtained by polymerization, polycondensation of monomer units with thiol functions or protected thiols, optionally by co-polymerization or co-polycondensation of monomer units devoid of thiol functions or protected thiols.
  • the thiolated polymers used according to the invention can be obtained by adding hydrogen sulphide, its salts such as sodium hydrogen sulphide or potassium sulphide or else a group capable of forming a carbon-sulfur bond such as derivatives of thioureas, thiosulphate, on a polymer comprising at least one double bond.
  • the thiolated polymers used according to the invention can also be obtained by nucleophilic substitution of a leaving group present on a polymer chain (for example halogen such as chlorine, bromine, a sulphonic ester such as mesylate or tosyltate) by a compound comprising at least one sulfur atom such as those mentioned above.
  • a leaving group present on a polymer chain for example halogen such as chlorine, bromine, a sulphonic ester such as mesylate or tosyltate
  • a compound comprising at least one sulfur atom such as those mentioned above.
  • thiolated polymers used according to the invention can also be obtained by reaction of polymers comprising nucleophilic groups such as amines on electrophilic compounds comprising a sulfur atom such as 2-oxo-4-thiazolidine carboxylic acid, also known under the name of procysteine: N-acetyl homocysteine-thiolactone: actone:
  • the thiolated polymers used according to the invention are polymers that are soluble in cosmetic media, particularly in aqueous or aqueous-alcoholic media. They are more preferably obtained from amino polymers and their ammonium salts or polyhydroxylated polymers.
  • the thiolated polymers implemented according to the invention are polymers soluble in lipophilic media.
  • the polythiol compound is a polymeric compound of formula (XIII):
  • POLY denotes a carbonaceous and/or silicone, preferably silicone, polymeric radical, POLY possibly also containing one or more heteroatoms such as O, N, S and/or one or more functions chosen from the functions, (thio)esters, ( thio)ketones, (thio)amides, (thio)ureas, (thio)carbamates, and/or be substituted by one or more (Ci-Cio)alkyl groups, linear or branched, (Ci-Cio)alkoxy, linear or branched , it being understood that when POLY is substituted, the thiol functions may be carried by the substituent(s).
  • the average molecular weight by molar weight of the polythiol polymer compounds, such as those of formula (XIII), is generally between 500 and 400,000 g.mol 1 , preferably between 500 and 150,000 g.mol 1 .
  • the polythiolated compounds are chosen from the polyorganosiloxanes of formula (XIII'): in which :
  • R a and R b identical or different, preferably identical, represent a group (C 1 -C 4 )alkyl such as methyl, (C 1 -C 4 )alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C 1 -C 4 )alkyl such as benzyl, or aryl(C 1 -C 4 )alkoxy such as benzoxy, preferably (C 1 -C 4 )alkyl such as methyl,
  • n represents an integer greater than or equal to 1, and more particularly the value of n is such that the weight-average molecular weight of the silicone is between 500 and 55,000 g.mol 1 ; particularly n is an integer comprised from 1 to 100, preferably comprised from 5 to 50, and preferentially comprised from 10 to 30, and
  • L 4 and L 5 are as defined previously in formula (XII), in particular represent a covalent bond, a group (C 1 -C 6 )alkylene, (C 1 -C 6 )alkylene-oxy, oxy- ( C i -Cô)alkylene, (C i -Cô)alkylene-oxy (C i -Cô)alkylene, (C i -Cô)alkylene-oxy (C i -
  • polydimethylsiloxane thiols are chosen from those of formula (XIII”): in which :
  • L 4 and L 5 represent a hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, optionally cyclic, optionally interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, preferably L 4 and L 5 represent represent a (Ci-C6)alkylene, (C 1 -C 6 )alkylene-oxy, oxy-(C 1 -C 6 )alkylene, or (Ci-C6)alkylene-oxy(Ci - C6)alkylene, more preferably a divalent group chosen from -R.2-, -O-R2-, -R2-O-, -R2-O-R2-, preferably -R2-O-R2-, with R2 representing a linear or branched, preferably linear (C2-C6)alkylene group, such as ethylene or n-propylene;
  • n represents an integer ranging from 1 to 100, preferably from 5 to 50, and preferably from 10 to 30.
  • thiolated poly(C 1 -C 4 )alkylsiloxanes mention may be made of thiolated mercaptosiloxanes or siloxanes, in which the thiol functions are located at the chain ends, marketed by the company SHIN-ETSU under the reference X-22-167B and mercaptosiloxane, in which the mercapto functions are pendant, marketed by the company SHIN-ETSU under the reference KF-2001, or by polydimethylsiloxane in which the thiol functions are located at the chain ends by thio-n-propyl groups, 80-120 marketed by Gelest under the name DMS - SM 21, of formula (XIII'”):
  • polythiolated compounds are chosen from those of formula (XIV): in which :
  • R a , R b , and R d identical or different, preferably identical, represent a group (C 1 -C 6 ) alkyl optionally substituted by a hydroxy group, or amino, preferably (C 1 -C 4 ) alkyl such as methyl, (C 1 -C 4 )alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C 1 -C 4 )alkyl such as benzyl, or aryl(C 1 -C 4 )alkoxy such as than benzoxy, preferably (C 1 -C 4 )alkyl such as methyl,
  • R d can also represent a (C 1 -C 6 )alkyl group substituted by a (Ci-C 4 )alkylamino or amino group, or thiol, preferably (C 1 -C 4 )alkyl such as methyl;
  • ALK represents a hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, optionally cyclic, optionally interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen (in particular O), a group (thio )carbonyl C(X) with X representing O, or S, or their associations such as -O-, -OC(O)- or -C(O)-O-, preferably ALK represents a group (C 1 -C 6 )alkylene, more preferably (C 1 -C 4 )alkylene such as propylene;
  • n and m identical or different, representing an integer greater than 2 and more particularly the values of m and n are such that the weight-average molecular weight of the silicone is between 1000 and 55000 g. mol 1 .
  • the polydi(C 1 -C 4 )alkylsiloxanes of formula (XIV) are of the following formula (XIV'): wherein the values of n and m are such that the weight average molecular weight of the silicone is between 1000 and 55000 g. mol 1 .
  • silicone of formula (XIV′) mention may be made of those sold by the company Genesee Polymers under the names GP-367, GP-71-SS, GP-800 and GP-710.
  • the silicone of formula (XIV') is the compound GP-367 marketed by the company Genesee Polymers.
  • the polythiol silicones are in particular polydimethylsiloxanes comprising at least two thiol groups such as, for example, the products SMS-022, SMS-042 and SMS-992 sold by the company Gelest at https://www.gpcsilicones.com/products/silicone- fluids/mercapto-functional, https://www.shinetsusilicone-global.com/products/type/oil/detail/search/deg07. shtml, and 1053_Reactive
  • the thiolated compound is a particle bearing at least two thiol groups, such as a silica functionalized by radicals, for example of the alkyl type, substituted by thiol functions, or a particle covered with compound(s). ) carrying at least two thiol functions (coating), said particle possibly being a sphere, a fiber, a rod (rod) or an amorphous structure.
  • thiol groups such as a silica functionalized by radicals, for example of the alkyl type, substituted by thiol functions, or a particle covered with compound(s).
  • the hydroxylated and/or thiolated compound is chosen from polymer compounds of the hyperbranched polymer and dendrimer type.
  • “Hyperbranched polymers” are molecular constructs with a branched structure, usually around a core. Their structure is as a rule free of symmetry. Indeed, the basic units or monomers having been used for the construction of the hyperbranched polymer can be of different natures and their distribution is irregular. The branches of the polymer can be of different natures and lengths. The number of basic units, or monomers, can be different according to the different ramifications. While being asymmetric, hyperbranched polymers can possess an extremely branched structure, around a core; layers or successive generations of ramifications; a layer of terminal chains.
  • the degree of polymerization is less than 100%.
  • a terminal group T can be reacted on the hyperbranched polymer to obtain a particular function at the end of the chains.
  • hyperbranched polymers can be associated with each other, by a covalent bond or another type of bond, through their terminal groups. Such so-called bridged polymers fall within the definition of hyperbranched polymers according to the present invention.
  • bridged or “bridged” polymers fall within the definition of hyperbranched polymers according to the present invention.
  • “Dendrimers” are macromolecules made up of monomers that combine in a tree-like process around a central multifunctional core.
  • Dendrimers therefore have a fractal structure (or fractal molecule), consisting of a core, a determined number of generation of branches (or spindles), internal cavities from said ramifications of the molecule, and terminal functions.
  • fractal structure or fractal molecule
  • Dendrimers are structurally highly branched polymers and oligomers with a well-defined chemical structure.
  • Dendrimers can be in the form of a set of molecules of the same generation, sets called monodisperse; they can also be in the form of sets of different generations, called polydisperse.
  • the definition of dendrimers according to the present invention includes monodisperse as well as polydisperse sets of dendrimers.
  • the generations of branches are made up of structural units, which are identical for the same generation of branches and which can be identical or different for generations of different branches. All the junction points of the branches of the same generations are located at an equal distance from the core corresponds to one generation.
  • the generations of branches extend radially in a geometric progression from the core.
  • the terminal groups of a dendrimer of the N th generation are the terminal functional groups of the branches of the N th generation or called terminal generation.
  • the definition of dendrimers given above includes molecules with symmetrical branches; it also includes molecules with non-symmetrical branching, such as for example dendrimers whose branches are lysine groups, in which the branching of a generation of spindles on the previous one is done on the amines a and 8 of lysine, which leads to a difference in the length of the spindles of the different ramifications.
  • Dendrimers are also called dense star polymers, or “dense star polymer”, starburst polymers, or “starburst polymer”, rod-shaped dendrimers, or “rod-shaped dendrimer”, are included in the present definition of dendrimers .
  • the molecules called arborais and molecules in cascade also fall within the definition of dendrimers according to the present invention.
  • dendrimers can be associated with each other, by a covalent bond or another type of bond, through their terminal groups to give entities known as “bridged dendrimers”, “aggregates of dendrimers” or “bridged dendrimer”. Such entities are included in the definition of dendrimers according to the present invention.
  • Dendrimers can be in the form of a set of molecules of the same generation, sets called monodisperse; they can also take the form of sets of different generations, called polydisperse.
  • the definition of dendrimers according to the present invention includes monodisperse as well as polydisperse sets of dendrimers.
  • the thiolated compound used according to the invention denotes a non-polymeric organic compound and can be represented by the formula (XV): WtSHJn fXV) in which: n denotes an integer greater than or equal to 2, preferably between 2 and 10, preferably between 2 and 5, and
  • W denotes a multivalent (at least divalent) C2-C80 linear or branched or (hetero)cyclic, saturated radical, an aromatic radical, a heteroaromatic cyclic radical, W possibly also containing one or more heteroatoms such as O, N, S and / or one or more functions chosen from esters, ketones, amides, ureas, preferably esters or ketones, and/or be substituted by one or more linear or branched C1-C10 alkyl groups, linear or branched C1-C10 alkoxy groups, it being understood that when the radical W is substituted, the thiol functions can be carried by the substituent(s).
  • cyclic radical is meant a saturated monocyclic, hydrocarbon-based or heterocyclic radical, a saturated or aromatic polycyclic radical, for example biphenyl, or condensed cycles such as for example the naphthyl radical.
  • the molar mass of the compounds of formula (XV) is generally between 90 and 1500 g. mol 1 .
  • the compound with a thiol unit denotes, for example, 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 1,6-hexanedithiol, 1,7-heptanedithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 2,2-dimethyl-1,3-propanedithiol, 3 -methyl-1,5-pentanedithiol, 2-methyl-1,8-octanedithiol.
  • the compound with a thiol unit can be chosen, for example, from 1,1,1-tris(mercaptomethyl)ethane, 2-ethyl-2-mercaptomethyl-1,3-propanedithiol, 1,2 ,3-propanetrithiol.
  • the compound with a thiol unit can be chosen, for example, from: bis mercaptoalkyl C2-C12 ethers and sulphides such as bis(2-mercaptoethyljether, bis(2-mercaptoethyl)sulphide, bis -(2-mercaptoethylthio-3- mercaptopropanejsulphide, alkanes (C1-C5) bis (2-mercapto alkyl (Ci-Ojthio) or mercaptoalkanes (C1-C5) bis (2-mercapto alkyl (Ci-Csjthio) such as bis(2-mercaptoethylthiojmethane, l,2-bis(2-mercaptoethylthio)ethane, l,3-bis(2-mercaptoethylthiojpropane, l,2-bis(2-mercaptoethylthio)propanethiol, l,2-bis(2-mercap
  • compound (XV) is chosen from 1,2-bis(2-mercaptoethylthiojpropanethiol), 1,2,3-tris(2-mercaptoethylthio)propane and tetrakis(2-mercaptoethylthiomethyl ) methane.
  • the compound with a thiol unit of formula (XV) is such that n denotes an integer greater than or equal to 2 and W denotes a linear or branched multivalent (at least divalent) saturated hydrocarbon-based C3-C20 radical, preferably linear or branched C2-C12, said radical containing at least one ester function.
  • the compound with a thiol unit can be chosen from: esters of polyols (glycols, triols, tetraols, pentaols, hexaols) and of C1-C6 mercaptocarboxylic acid such as ethylene glycol bis(2 -mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(thioglycolate), trimethylolpropane tris (thioglycolate), trimethylolpropane tris (beta-mercaptopropionate), pentaerythritol tetrakis (thioglycolate), pentaerythritol tetrakis (P-mercaptopropionate), dipentaerylthritol hexakis (P-mercaptoproprionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(
  • the compound with a thiol unit is chosen from trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutanate), and dipentaerythritol hex-3-mercaptopropionate.
  • the compound with a thiol unit is pentaerythritol tetrakis(3-mercaptopropionate).
  • the compound with a thiol unit can be chosen from tetrakis(2-mercaptoethylthiomethyl)methane, bis-(2-mercaptoethylthio-3-mercaptopropanejsulphide.
  • the compound with a thiol unit can be chosen, for example, from 1,4-cyclohexane dithiol, 1,4-bis(mercaptomethyl) cyclohexane, 1,1-cyclohexane dithiol, 1,2- cyclohexane dithiol, l,l-bis(mercaptomethyl)cyclohexane, 2,5-dimercapto-1,4-dithiane.
  • the compound with a thiol unit can be chosen from polythiols of the isocyanurate class described in patents US Pat. No. 3,676,440 and US Pat.
  • the compound with a thiol unit is preferably tris((mercaptopropionyloxy)-ethyl)isocyanurate.
  • the compound with a thiol unit can be chosen, for example, from the following compounds: 1,2-dimercaptobenzene, 1-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl) benzene, 1,2-bis(2-mercaptoethyl)benzene, 1,3-bis(2-mercaptoethyl)benzene, 1,4-bis(2-mercaptoethyl)benzene, 1,2-bis(2- mercaptoethyleneoxy)benzene, 1,3-bis(2-mercaptoethyleneoxy)benzene, 1,4-bis(2-mercaptoethyleneoxy)benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1 ,3,5-tris(mercaptomethyl)benzene, 1,2,3-tris(mercaptomethyl)benzen
  • the compound (XV) is chosen from 1,2,3-triscaptobenzene, 1,2,4-triscaptobenzene, 1,3,5-triscaptobenzene, 1,2,3-tris (mercaptomethyl)benzene, l,2,4-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyl)benzene, l,2,3-tris(2-mercaptoethyl)benzene, l,2 ,4-tris(2- mercaptoethyl)benzene, l,3,5-tris(2-mercaptoethyl)benzene, l,2,3-tris(2-mercaptoethyleneoxy)benzene, l,2,4-tris(2-mercaptoethyleneoxy)benzene, 1,3,5-tris(2-mercaptoethyleneoxy)benzene, 1,2,3,4-tetramercaptobenzene, 1,2,3,5-tetramercaptobenzene, 1,2,
  • the thiolated and/or hydroxylated compound is chosen from triglyceride derivatives of hydroxylated and/or thiolated thiolated fatty acids, such as those of formula (XVI): in which :
  • R 1 , R 2 and R 3 identical or different, represent a hydrogen atom, a hydroxy group, or thiol, preferably thiol;
  • ALK 1 , ALK 2 , and ALK 3 which are identical or different, represent a (Ci-C3o)alkylene group optionally substituted by one or more hydroxy or thiol groups, preferably thiol;
  • X 1 , X 2 and X 3 identical or different, preferably identical, represent a group -C(Y)-Y - or -Y -C(Y)- with Y and Y , identical or different, preferably identical, represents a heteroatom such as O, S, and N, preferably O.
  • the compounds of formula (XVI) are such as:
  • R 1 , R 2 and R 3 represent a hydrogen atom
  • ALK 1 represents a group (Cio-C24) alkylene, particularly (Ci4-C2o) alkylene, preferably linear;
  • ALK 2 represents a represents a (Cio-C24)alkylene group, particularly (C14-C2o)alkylene, preferably linear, substituted by one or more thiol groups;
  • ALK 3 represents a represents a (Cio-C24)alkylene group, particularly (C14-C2o)alkylene, preferably linear, substituted by one or more thiol groups, preferably two thiol groups; and or
  • X 1 , X 2 and X 3 are identical and represent a -C(O)-O- or -OC(O)- group.
  • the compound with a thiol unit can be chosen, for example, from: triglycerides of fatty acids or vegetable oils modified with thiol groups by chemical reaction, such as, for example, thiolated soybean oils and hydroxylated soybean oils and thiolated, in particular the polymercaptan® products from Chevron Phillips, such as polymercaptan 407 (mercapto hydroxy soybean oil) and polymercaptan 358 (mercaptanised soybean oil) of formula (XVII) below:
  • the triglyceride derivatives of hydroxylated and/or thiolated thiolated fatty acids of formula (XVI) are such as those of formula (XVII) above.
  • the thiolated and/or hydroxylated compound is chosen from polyhydroxylated, polythiolated, or (poly)hydroxylated and (poly)thiolated compounds having several hydroxy and/or thiol groups, and having a weight average molecular weight ranging from 500 to 1,000,000 g. mol 1 , preferably ranging from 500 to 500000 g.mol' x , and preferably ranging from 500 to 100000 g.mol 1 .
  • the compounds of formula (XV) for which n denotes an integer greater than or equal to 3, preferably between 3 and 10 and more preferably between 3 and 5, will be preferred.
  • the compounds of formula (XV) are chosen from the compounds of the second embodiment, or from the compounds of the third embodiment, or from the compounds of the fourth embodiment such as in particular trimethylolpropane tris (2-mercaptoacetate), tris(3-mercaptopropionate)trimethylolpropane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutanate), dipentaerythritol hex-3-mercaptopropionate; or from the compounds of the fifth embodiment, or from the compounds of the seventh embodiment such as in particular tris((mercaptopropionyloxy)-ethyl)isocyanurate.
  • the compounds of formula (XV) are chosen from trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis( 3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutanate), dipentaerythritol hex-3-mercaptopropionate, and tris((mercaptopropionyloxy)-ethyl)isocyanurate.
  • the compound with a thiol unit according to the invention designates a polymeric compound and can be represented by the formula (XVIII):
  • n denotes an integer greater than or equal to 5, preferably comprised from 5 to 5000, preferably from 5 to 1000, and
  • POL denotes a multivalent (at least pentavalent) carbon or silicone polymeric radical, POL possibly also containing one or more heteroatoms such as O, N, S and/or one or more functions chosen from esters, ketones, amides, ureas, carbamates, and/or be substituted by one or more linear or branched Ci-Cio alkyl groups, linear or branched Ci-Cio alkoxy groups, it being understood that when POL is substituted, the thiol functions can be carried by the substituent(s) ( s).
  • the molar mass of the compounds of formula (XVIII) is generally between 500 and 400,000 g. mol 1 , preferably between 500 and 150,000 g. mol 1 .
  • POL denotes a multivalent radical of the homopolymer or copolymer type.
  • POL designates a polymeric radical of the star, comb, brush or dendritic type.
  • the POL radical can be of natural origin (such as polysaccharides, peptides) or synthetic (such as acrylic polymers, polyesters, polyglycols).
  • the thiol functions (-SH) can be terminal and/or pendent groups.
  • the thiolated compound of formula (XVIII) is such that POL denotes a hydrocarbon-based polymeric radical.
  • Examples include the polymers described in the following articles: Polymers containing groups of biological activity, CG Overberger et al, Polytechnic Institute of Brooklyn, http://pac.iupac.org/publications/pac/pdf/1962/pdf/ 0402x0521.pdf and Mercaptan-containing polymers, Advances in Polymer Science Volume 15, 1974, pp 61-90.
  • thiol unit of formula (XVIII) such as poly(vinylmercaptan), poly(4-mercaptostyrene), poly(vinylbenzylmercaptan), poly(4-mercaptostyrene)-co-poly(methylmethacrylate), as well as polymers containing amide functions such as thiolated poly(hexamethylene adipamide).
  • the compounds of formula (XVIII) also designate the proteins and peptides with thiol units, such as for example the structures represented in the following table:
  • the thiolated compounds of formula (XVIII) also denote the compounds of formula (XVIII) such that POL denotes a so-called dendrimer, branched or hyperbranched polymer radical and the thiol groups are terminal. Mention may be made, as examples, of the polymers described in the article Progress in Organic Coatings, Volume 63, Issue 1, July 2008, Pages 100-109.
  • Y represents an oxygen or sulfur atom, or an NR' group
  • X represents i) an oxygen atom or ii) a -N(R')- group in which R' is chosen from a) a hydrogen atom, b) a C1-C6 alkyl group, linear or branched , saturated or unsaturated, c) a mono- or poly-hydroxy-C1-C6 alkyl group, linear or branched, saturated or unsaturated, d) an amino-C1-C6 alkyl group OR a polyalkyleneimine group; preferably X represents —N(R′)— with R′ representing a hydrogen atom or a (Ci-C 4 )alkyl group such as methyl; and
  • A represents a (Ci-Ci2)alkylene group, linear, branched or cyclic, saturated or unsaturated; this group being optionally interrupted by one or more heteroatoms such as O, S, N and/or optionally substituted by one or more groups chosen from amino (-NH2), acylamino (-N(H)-C(O)-R) or aminoacyl (RN(H)-C(O)-) in which R represents a linear, branched or cyclic, saturated or unsaturated C1-C10 alkyl group, carboxy (- C(O)OH), ester (-C( O)-OR) in which R represents a linear, branched or cyclic, saturated or unsaturated C1-C10 alkyl group.
  • the thiolated polymers according to the invention are chosen from hyperbranched polymers, and in particular polyethyleneimine, comprising at least one group chosen from the groups of formula (XIX) as defined previously.
  • Y represents the oxygen atom.
  • the heteroatoms are chosen from oxygen or nitrogen (O and N).
  • A is a methylene, ethylene, propylene, methylpropylene, ethylpropylene, tetramethylene, pentamethylene, hexamethylene, and phenylene group.
  • A represents a radical corresponding to one of the following formulas (a) to (d):
  • R 1 , R 2 , R 3 , R' 1 , R' 2 , R' 3 and R' 4 , R'” 1 , R'” 2 identical or different, represent: the hydrogen atom; a C1-C6 alkyl radical, linear, branched or cyclic, saturated or unsaturated; an amino radical (-NH2); a carboxylic acid radical (-COOH); a C1-C10 alkylamino radical; a C1-C10 acylamino radical;
  • R 1 , R” 2 , R” 3 and R” 4 identical or different, represent the hydrogen atom or a C 1 -C 4 alkyl group, linear or branched, saturated or unsaturated; the arrows indicating the positions of the substitutions; and
  • the thiolated polymers are hyperbranched polymers and the dendrimers comprising functional groups of formula (XIX) such that A is chosen from:
  • Y represent an oxygen atom or an NH group.
  • A is the propylene group -CH2-CH2-CH2-, and Y represents an oxygen atom
  • the group of formula (XIX) then corresponding to the following formula (XX): HS-CH2-CH2-CH2 -C(O 3£- (XX) in which X is as defined in formula (XIX) preferably X represents -N(R')- with R' representing a hydrogen atom or a group (C 1 - C 4 ) alkyl such as methyl.
  • X is chosen from the oxygen atom and an NH group.
  • the thiolated polymers are as described in document FR 2 853 533, they are poly N-a- and N-e-lysine and ornithine of formula I, with a thiol function, which can be obtained from poly N-a- and N-e-lysine and ornithine by reaction with a thiolactone such as, for example, thiobutyrolactone (dihydrothiophen-2(3H)-one).
  • a thiolactone such as, for example, thiobutyrolactone (dihydrothiophen-2(3H)-one).
  • the hyperbranched polymers and the dendrimers useful in the invention contain functional groups corresponding to the formula (XXI): in which: p different from p' and p, p' are 0 or 1; n is 3 or 4; if p' is 0, then the neighboring NH is engaged in Ne polymerization; if p is 0, then the neighboring NH is engaged in Na polymerization; if p or p' equals 1, then R or R' represents -B-SH, with B representing a C1-C30 hydrocarbon chain, saturated or not, linear or branched which can be interrupted by one or more heteroatoms or groups, alone or in combinations, such as: -N/R 1 )-, -O-, -S(O) r -, -C(O)-, -C(S)-, -C/NR 1 )-, with r having a value of 0, 1 or 2, and/or by one or more aryl, hetero
  • Ri represents a hydrogen atom or a (Ci-Cs)alkyl, (Ci-Cs)acyl, (Ci-Cs/alkyloxycarbonyl, (Ci-Cs)alkyl amino-carbonyl or halo group;
  • B can also represent an aryl, heteroaryl, cycloalkyl or heterocycloalkyl group with 5, 6 or 7 members, optionally substituted; m represents an integer from 3 to 10000.
  • the degree of grafting of thiol functions is greater than or equal to 1%.
  • poly N-a- and N-e-lysine and ornithine corresponding to formula (XXI) have: 5 ⁇ m ⁇ 1000.
  • the “theoretical thiol function grafting rate” represents the theoretical percentage of lysine or ornithine unit carrying the thiol function in the compound of formula (XXI).
  • hyperbranched polymers By way of example of hyperbranched polymers, mention may very particularly be made of hyperbranched thiolated polyethyleneimines, such as those described in application EP103759, with a molecular molar mass of from 30 ⁇ 10 4 to 50 ⁇ 10 4 g.mol 1 .
  • the branched or hyper-branched dendrimers and polymer(s) bear thiol end groups such as “dendritic polythiols of the BoltomTM type” from the company BASF esterified with compounds such as thioglycolic acid and described in the literature.
  • Polypropylene ether glycol bis(P-mercaptopropionate) type polymers can also be used according to the invention. They are prepared by methods known to those skilled in the art. Mention may be made, for example, of the method of preparation by esterification reaction of polypropylene ether glycol such as Pluracol P201 marketed by the company Wyandotte Chemical Corp, and of P-mercaptopropionic acid.
  • the hydroxylated and/or thiolated polymers are polyethoxylated of formula (XXII) as well as their optical isomers, and their acid or base salts, as well as their solvates such as hydrates:
  • Ri, R2 and R3, identical or different, preferably identical represent a hydroxy (Ci-C6) alkyl or thio (Ci-C6) alkyl group, preferably thio (Ci-C6) alkyl;
  • R4 represents a hydrogen atom, or a hydroxy, thiol, amino group, or a (C 1 -C 6 )alkyl group, preferably (Ci -Chalky le such as ethyl;
  • Xi and X2 identical or different, preferably identical, represents an oxygen, sulfur or amino atom, preferably oxygen;
  • the thiolated polymer compounds of formula (XXII) are commercially available. Mention may be made, for example, of the products THIOCURE® from the company Bruno Brock, THIOCURE® ETTMP 1300 (Ethoxylated-Trimethylolpropan Tri-3-Mercaptopropionate (CAS# 345352-19-4) and THIOCURE® ETTMP 700 (Ethoxylated-Trimethylolpropan Tri-3- Mercaptopropionate (CAS no. 345352-19-4).
  • the crosslinking agent R is a (poly)thiolated and/or (poly)hydroxylated compound, in particular chosen from nonpolymeric (poly)thiolated and/or (poly)hydroxylated compounds such as the compounds polyhydroxylated (fat-soluble polyol), polythiolated compounds (dithiol compounds), hydroxylated and/or thiolated alkoxysiloxanes, silicas functionalized by radicals, in particular of the alkyl type, substituted by thiol functions, latices carrying thiol groups, particles coated with compound(s) carrying at least two thiol functions and polymeric (poly)thiol and/or (poly)hydroxyl compounds such as homopolymers, copolymers, star, combe, brush and dendritics with hydroxy and/or thiol units , preferably organic or silicone.
  • nonpolymeric (poly)thiolated and/or (poly)hydroxylated compounds such as the compounds polyhydroxylated (
  • the polymeric (poly)thiol and/or (poly)hydroxyl compounds are chosen from polymer (di)ols, in particular polyolefin (poly)ols, polydi(Ci-C6) alkyl siloxane (poly)ols, polyester (poly)ols, triglyceride derivatives of hydroxylated and/or thiolated thiolated fatty acids, amino thiols derived from dendrimers or from polyethyleneimines (PEI) and silicone thiols.
  • polymer (di)ols in particular polyolefin (poly)ols, polydi(Ci-C6) alkyl siloxane (poly)ols, polyester (poly)ols, triglyceride derivatives of hydroxylated and/or thiolated thiolated fatty acids, amino thiols derived from dendrimers or from polyethyleneimines (PEI) and silicone thi
  • the polymeric (poly)thiol and/or (poly)hydroxyl compounds are chosen from polydimethylsiloxane diols such as polydimethylsiloxanes with terminal hydroxy functions; thiolated poly(C 1 -C 4 )alkylsiloxanes such as polydimethylsiloxanes containing at least two thiol groups; and fatty acid triglycerides or vegetable oils modified with thiol groups by chemical reaction.
  • the (poly)thiolated and/or (poly)hydroxylated compounds used according to the invention are chosen from fat-soluble polyols, dithiol compounds, hydroxylated and/or thiolated alkoxysiloxanes, silicas functionalized with radicals, in particular of the alkyl type, substituted by thiol functions, latices bearing thiol groups, particles coated with compound(s) bearing at least two thiol functions, polyolefins (poly)ols, polydi(Ci-C6)alkylsiloxane (poly) ols, polyester (poly)ols, amino thiols derived from dendrimers or polyethyleneimines (PEI), silicone thiols, polydimethylsiloxane diols, thiolated poly(C 1 -C 4 )alkylsiloxanes and fatty acid triglycerides or vegetable oils modified with thiol groups by
  • the (poly)thiolated and/or (poly)hydroxylated compounds used according to the invention are chosen from polydimethylsiloxanes comprising at least two thiol groups.
  • the crosslinking agent R is a (poly)carbonyl compound.
  • the (poly)carbonyl compound is chosen from terephthalaldehyde,5,5-dimethyl-1,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4-acetylbenzaldehyde, 4,4-diformyltriphenylamine,2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarboxaldehyde, phthaldialdehyde, 1,3 -cyclohexanedione, 4,4'-biphenyldicarboxaldehyde, benzene - 1,3,5-tricarboxaldehyde, and oxidized inulin.
  • the (poly)carbonyl compound is chosen from terephthalaldehyde,5,5-dimethyl-1,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4-acetylbenzaldehyde, 4,4-diformyltriphenylamine,2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarboxaldehyde, phthaldialdehyde, 1,3-cyclohexanedione, 4,4'-biphenyldicarboxaldehyde, benzene-1,3,5-tricarboxaldehyde, oxidized inulin and terephthaldehyl,
  • the (poly)carbonyl compound is combined in its implementation with an amine catalyst as described for example in the articles Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510- 516 (2019), preferably the amine catalyst(s) are chosen from piperidine, DMAP (Dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4 -diazabicyclo[2.2.2]octane), DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably chosen from DBU (1,8-diazabicyclo[5.4.0]undec-7 -ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1 ,8-diazabicyclo[5.4.0
  • the crosslinking agent R is a (poly)acrylate compound.
  • the (poly)acrylate compound can be chosen from 1,3-butanedioldiacrylate, 1,4-butanedioldiacrylate, di(trimethylolpropane)tetraacrylate, glycerol 1,3-diglycerolate diacrylate, glycerol propoxylate (1PO/OH ) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivalyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO/OH) diacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.0 2,6 ]decanedimethanol
  • the (poly)acrylate compound is trimethylolpropane triacrylate.
  • the (poly)acrylate compound is combined in its implementation with at least one amine catalyst as described for example in the articles Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019), preferably the amine catalyst(s) are chosen from piperidine, DMAP (Dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO(1 ,4-diazabicyclo[2.2.2]octane) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably chosen from DBU (1,8-diazabicyclo[5.4.0]undec -7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-diazabicyclo[4.3.0]non-5-ene), and preferably the amine catalyst is DBU (1,8-diazabicyclo
  • the crosslinking agent R is a metal salt chosen from alkali metal salts, alkaline-earth metal salts such as magnesium salts, transition metal salts, salts of post transition such as aluminum or tin salts, metalloid salts such as boron salts, their hydrates and their mixtures.
  • the metal salt(s) is (are) chosen from post-transition metal salts such as aluminum salts, their hydrates and their mixtures.
  • metal salt is meant a salt resulting in particular from the action of an acid on a metal, in particular a transition or post-transition metal, metalloids, or alkali or alkali earth metals.
  • the metal salt(s) can be in the form of hydrates.
  • the metal salt(s) can be organic or inorganic.
  • organic metal salt is meant a salt resulting in particular from the action of an organic acid on a metal, in particular transition metals, post-transition metals, metalloids, or alkali metals or alkaline earth metals, preferably resulting from the action of a carboxylic acid on a metal.
  • the metal salt(s) is (are) chosen from organic metal salts, their hydrates and mixtures thereof.
  • organic metal salt is meant a salt resulting in particular from the action of an inorganic acid on a metal, in particular a transition or post-transition metal, metalloids, or alkali or alkali earth metals.
  • organic acid is meant an acid which does not contain any carbon atoms except carbonic acid.
  • the inorganic metal salt(s) can be chosen from halides such as chlorides, fluorides, iodides and bromides, carbonates, sulfates, phosphates, nitrates, perchlorates, their hydrates, and mixtures thereof.
  • Cross-linking agents (poly)(hydroxy)(Ci-C6)metal alkyl carboxylates
  • the crosslinking agent R is an organic metal salt derived from a carboxylic acid.
  • the crosslinking agent R is an organic metal salt chosen from metal (poly) (hydroxy) (Ci-C6) alkylcarboxylates of alkali metal, alkaline-earth salts, of transition metals, and of post-transition metals such as 'aluminum.
  • the metal (poly)(hydroxy)(Ci-C6)alkylcarboxylate implies that the (C1- C6 )alkyl group is optionally substituted by one or more hydroxy groups and one or more carboxy or carboxylate groups.
  • (poly)(hydroxy)(Ci-C6-alkylcarboxylate) of metal represents R a -C(O)-OM with M representing a transition metal such as titanium (Ti), or else a post transition metal such as aluminum (Al), and R a represents a linear or branched (C 1 -C 6 )alkyl group optionally substituted by at least one hydroxy group.
  • the metal salt(s) are organic, preferably chosen from citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, glycinates, tartrates, their hydrates and mixtures thereof. More preferably acetates, lactates or their mixtures such as aluminum acetate, or aluminum lactate.
  • the metal salt(s) are chosen from basic aluminum acetate, aluminum oxalate, hydrated or non-hydrated aluminum citrate, aluminum lactate, aluminium, aluminum glycinate and mixtures thereof. According to an even more preferred embodiment, the metal salt is basic aluminum acetate.
  • the crosslinking agent R is a compound chosen from the following metal alkoxides of formulas (XXIII a ), (XXIIIb), (XXIII C ) and (XXIIId) and mixtures thereof:
  • - M and M' identical or different, represent an atom chosen from alkaline earth metals, transition metals, metals of the lanthanide family, post transition metals such as aluminum or tin and metalloids such as boron; preferably transition metals such as Ti and post transition metals such as aluminum;
  • n' respectively represent the valences of the atoms represented by M and M';
  • - Ri and R' i identical or different, represent a hydrocarbon group, linear or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, said hydrocarbon group being optionally interrupted by 1 with 20 heteroatoms chosen from O, N, S and P, in particular O or N; and/or said hydrocarbon group being optionally substituted by one or more hydroxy or carbonyl groups;
  • R and R' identical or different, represent a hydrogen atom or a hydrocarbon group, linear, branched or cyclic, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms chosen from O, N, S and/or P, in particular O or N and/or the said hydrocarbon group being optionally substituted by one or more hydroxy or carbonyl groups;
  • - R" represents -O-, -NR2-, -S- or a divalent hydrocarbon group, linear, cyclic or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms chosen from O, N, S and P, in particular O or N, with R2 representing a hydrocarbon, linear, cyclic or branched, saturated or unsaturated, having 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms.
  • M and M' which are identical or different, represent an atom chosen from transition metals such as titanium or zirconium, or alino-earth metals such as magnesium, more preferably chosen from transition metals such as than titanium or zirconium, even more preferably titanium.
  • the organometallic compound(s) are chosen from the alkoxides of formula (XXIII a ) as defined previously.
  • the organometallic compound(s) are chosen from the alkoxides of formula (XXIIIa), in which:
  • - M represents an atom chosen from transition metals, metals of the lanthanide family, post-transition metals such as aluminum, tin, metalloids such as boron, or alkaline earth metals such as magnesium or calcium;
  • - n represents the valence of the atom represented by M
  • - Ri represents a hydrocarbon group, linear or branched, saturated, having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms.
  • the organometallic compound(s) are chosen from the alkoxides of formula (XXIIIa), in which:
  • M represents an atom chosen from transition metals such as zirconium or titanium, metals of the lanthanide family, post transition metals such as aluminum, tin, metalloids such as boron, and alkaline-earth metals such as magnesium, preferably M represents a titanium atom;
  • - n represents the valence of the atom represented by M, in particular 1, 2, 3 or 4, in particular 4;
  • - Ri represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t-butyl group.
  • the organometallic compound(s) are chosen from zirconium ethoxy of (Zr(OC2Ü5)4), zirconium propoxy of (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide Zr(OCH2CH2CH2CH3)4, zirconium tert-butoxide (Zr(OC(CH3)3)4), ethoxy titanium (Ti(OC 2 H 5 ) 4 ), titanium propoxide (Ti(OCH2CH2CH3)4), titanium isopropoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH 3 ) 3 ) 4 ), titanium 2 -ethylhexyloxy (Ti(OCH 2 CH(C 2 H5)(CH2) 3 CH 3 )4), and
  • the organometallic compound(s) are chosen from zirconium propoxide (Zr(OCH 2 CH 2 CH 3 )4), titanium propoxide (Ti(OCH 2 CH 2 CH 3 )4) , titanium butoxide (Ti(OCH 2 CH 2 CH 2 CH 3 )4) and mixtures thereof.
  • the crosslinking agent R is a compound of formula (XXIII a ) in which M represents an atom chosen from transition metals, in particular titanium such as titanium butoxide.
  • Cross-linking agents composed of metal belonging to the group of rare earths
  • the crosslinking agent R is a compound of a metal belonging to the group of rare earths M”, and in particular a salt of a metal belonging to the group of rare earths.
  • metal salt belonging to the group of rare earths is meant a salt resulting in particular from the action of an acid on a metal belonging to the group of rare earths.
  • the metal compound(s) belonging to the rare earth group can be in the form of hydrates.
  • the metal compound(s) belonging to the rare earth group can be organic or inorganic. They may or may not be in salt form.
  • organic salt of a metal belonging to the group of rare earths is meant a salt resulting in particular from the action of an organic acid, in particular a carboxylic acid, on a metal belonging to the group of rare earths.
  • inorganic salt of a metal belonging to the group of rare earths is meant a salt resulting in particular from the action of an inorganic acid on a metal belonging to the group of rare earths.
  • organic acid is meant an acid which does not contain any carbon atoms, except for carbonic acid.
  • a metal belonging to the group of rare earths M we can cite scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinum , terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium.
  • the metal or metals belonging to the group of rare earths are chosen from cerium, yttrium, ytterbium, lanthanum, europium, more preferably, the metal or metals belonging to the group of rare earths M′′ are chosen from cerium and yttrium.
  • the metal belonging to the group of rare earths M′′ is chosen from cerium, yttrium, ytterbium, lanthanum, europium and mixtures thereof. More preferably, the metal belonging to the group of rare earths is chosen from cerium, yttrium and mixtures thereof.
  • the metal belonging to the rare earth group M” is in the +III oxidation state.
  • the metal compound belonging to the rare earth group can be chosen from rare earth salts and rare earth complexes.
  • rare earth complex includes the combination of the metal M′′ with one or more ligands.
  • ligand is understood to mean an ion or a molecule carrying a group associating, by ionic bond and/or coordination bond, with the metal M”.
  • the same ligand can carry several groups which are associated by ionic bond and/or coordination.
  • the rare earth salts and complexes according to the invention are characterized in that they contain at least one metal atom M” belonging to the group of rare earths and that this is in the +III oxidation state.
  • the metal belonging to the rare earth group M can then be associated, via its electronic shell, with n anionic groups forming an ionic bond with M” and/or with n2 groups forming a coordination bond with M”.
  • the metal belonging to the rare earth group M′′ is associated with one or more anionic groups and/or one or groups forming a coordination bond.
  • the ligands associated with the metals belonging to the group of rare earths M′′ to form a corresponding rare earth complex are such as those described below. a) Typically, the ligand can be a mono-anionic ion, monatomic or not such as a nitrate, a hydroxyl (OH-) or a halide (chloride, bromide typically).
  • the resulting rare earth compound can then be M”Ch, M”(OH) 3 , M”(NO 3 ) 3 , and in particular CeNO 3 , YNO 3 , LaNO 3 , CeC1 3 , YC1 3 , LaC1 3 , more preferentially the rare earth halides in particular the halides of Ce and Y such as CeC1 3 , and YC1 3 .
  • the ligand can be an anionic di or tri ion such as phosphate or sulphate.
  • the ligand may contain one or more group(s) making a coordination bond and a function making an ionic bond.
  • the ligand can be a mono or polycarboxylate molecule, such as acetate or succinate.
  • the carboxylate function plays a role of an anionic group, through the hydroxyl of the carboxylic group and a role of group forming a coordination bond through the doublet of the oxygen of the carbonyl function .
  • the resulting rare earth compound may be M”(R-(COO) n ) 3 /n.
  • the ligand may, in addition to bearing one or more carboxylate(s), comprise other functions, such as hydroxyls or amines.
  • the ligand may consist wholly or partially of hydroxy carboxylic acids or amino carboxylic acids.
  • EDTA ethylenediaminetetraacetate
  • the ligand can carry a non-localized anionic charge, such as for example acetylacetonate.
  • the rare earth compound will then be M”(acetylacetonate) 3 or M”(acetylacetonate) 3 .7H2O where each acetonate binds to the metal M” through its two carbonyl functions, one acting as an anionic group, the other group linking by coordination.
  • the ligand can also be of the aromatic type, such as a phenol, a cyclopentadiene (Progress in the Science and Technology of the Rare Earths, published by Leroy Eyring and written by F. Gaume-Mahn, page 296), or a pyridine.
  • the rare earth compound may comprise one or more ligand(s) forming a coordination bond and one or more ligand(s) forming an ionic bond.
  • the rare earth compound may be yttrium dihydroxyacetate Y((OH)2acetate) (Synthesis and Properties of Yttrium Hydroxyacetate Sols by SS Balabanov, EM Gavrishchuk, and DA Permin, Inorganic Materials, 2012, Vol.
  • the compound of rare earths can be a mixed salt in which one of the cations M′′′ represents a different cation from the rare earth cation, such as, for example, an alkali or an alkali earth. or a cationic organic cation, in particular a quaternary amine (or ammonium), for example mono/bi/tri/tetra(C 1 -C 4 )alkylammonium, or mono/bi(C 1 -C 4 )alkyl imidazolium, (C 1 -C 4 )alkylpyridinium, more particularly the mixed salt rare earth compound is Li,Ce(SO4)2.
  • the compound or compounds belonging to the group of rare earths are chosen from salts of organic acids such as citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, tartrates, mesylates and methosulfates, in particular gluconates, their hydrates and mixtures thereof.
  • organic acids such as citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, tartrates, mesylates and methosulfates, in particular gluconates, their hydrates and mixtures thereof.
  • the metal salt(s) belonging to the group of rare earths are inorganic.
  • the inorganic metal salt(s) belonging to the rare earth group are chosen from halides such as chlorides, fluorides, iodides and bromides, carbonates, sulphates, phosphates, nitrates, perchlorates, their hydrates, and mixtures thereof.
  • the inorganic metal salt(s) belonging to the rare earth group are chosen from halides such as chlorides, fluorides, iodides and bromides, nitrates, their hydrates, and mixtures thereof. .
  • the inorganic metal salt(s) belonging to the group of rare earths are chosen from chlorides, nitrates, their hydrates, and mixtures thereof.
  • the compound or compounds belonging to the group of rare earths are chosen from Ce(N ⁇ 3)3, Y(N ⁇ 3)3, La(N ⁇ 3)3, CeCE, YCl3, LaCE and their mixtures.
  • the compound or compounds belonging to the group of rare earths are chosen from CeCh, YCl3 and mixtures thereof.
  • the crosslinking agent is chosen from (poly)amino, (poly)thiolated and/or (poly)hydroxylated, (poly)carbonyl, (poly)acrylate compounds, and mixtures thereof, and preferably chosen from (poly)amine and (poly)thiolated compounds, with in particular said (poly)amine being chosen from chitosans, aminoalkoxysilanes and polydimethylsiloxanes comprising primary amine groups at the end of the chain or on the side chains, and even more preferably chosen from poly(D-Glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxy silane (AETES), 3-aminopropylmethyldiethoxy silane, A-(2-aminoethyl)-3-aminopropyltriethoxysilane and polydimethylsiloxanes comprising at the end of the chain of the aminopropyl terminal groups
  • the cross-linking agent is chosen from i) (poly)amino compounds, ii) (poly)thiolated and/or (poly)hydroxylated compounds, iii) (poly)carbonyl compounds such as terephthaldehyde, iv) (poly)acrylates such as trimethylolpropane triacrylate, v) metal salts chosen from v a ) metal alkoxides such as titanium butoxide, Vb) metal (poly)(hydroxy)(Ci-C6)alkylcarboxylates, in particular of transition metals or post-transition metals, in particular aluminum, such as aluminum acetate, or aluminum lactate and v c ) the salts of metals belonging to the rare earth group, in particular the Ce or Y halides such than CeCE and YCl3 and vi) mixtures thereof, and preferably chosen from (poly)amino and (poly)thiolated compounds, with in particular said (poly)poly)th
  • the mixtures vi) can designate mixtures of compounds of the same type such as for example mixtures of (poly)amines i) of different structures, or mixtures of (poly)thiols ii) of different structures.
  • the mixtures vi) can also denote mixtures of compounds of different types such as for example mixtures consisting of one or more polyamines i) with one or more (poly)thiols ii).
  • the crosslinking agent R is a compound chosen from v a ) a (CI-C ⁇ ) alkoxy of a transition metal in particular titanium such as titanium butoxide, and Vb) a (poly) ( hydroxy) (Ci-C6) alkylcarboxylate of transition metal in particular aluminum such as aluminum acetate, or aluminum lactate.
  • the crosslinking agent R is a compound chosen from metal alkoxides of formula (XXIIL) as defined above, preferably of which the metal M is a transition metal, in particular of titanium such as titanium butoxide.
  • the crosslinking agent R is a compound chosen from iii) (poly)carbonyls such as terephthaldehyde or trimethylolpropane triacrylate.
  • compositions C1, C2 or C3 according to the invention contain a fatty phase, in particular a fatty phase comprising a hydrocarbon oil, preferably isododecane.
  • the hydrocarbon oil preferably isododecane
  • the hydrocarbon oil is predominantly present in the fatty phase of a composition according to the invention, relative to all of the constituents of said fatty phase.
  • the CR and CAC compositions can also contain a fatty phase suitable for the invention.
  • composition C1, C2 or C3 according to the invention or CR or CAC suitable for the invention may comprise at least one hydrocarbon-based oil, in particular volatile.
  • oil is meant a non-aqueous compound, immiscible with water, liquid at room temperature (20°C) and atmospheric pressure (760 mm Hg).
  • hydrocarbon oil is meant an oil formed essentially, or even consisting, of carbon and hydrogen atoms, and optionally of oxygen and nitrogen atoms, and not containing any silicon or fluorine. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • composition in accordance with the invention may comprise at least one hydrocarbon oil chosen from:
  • Cs-Cu hydrocarbon oils and in particular: branched Cs-Cu alkanes such as Cs-Cu isoalkanes (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane) , isodecane, dodecane, and for example the oils sold under the trade names Isopars or Permetyls, linear alkanes, for example such as n-dodecane (C12) and n-tetradecane (Cu) sold by Sasol respectively under the references Parafol 12-97 and Parafol 14-97, as well as their mixtures, the undecane-tridecane mixture, the mixtures of n-undecane (Ci 1) and n-tridecane (C13) obtained in Examples 1 and 2 of application W02008/155059 from Cognis, and mixtures thereof, and short-chain esters (having 3 to 8 carbon atoms in total), such as
  • oils of plant origin such as triglycerides consisting of esters of fatty acids and glycerol, the fatty acids of which may have chain lengths varying from C4 to C24, the latter possibly being linear or branched, saturated or unsaturated; these oils are in particular triglycerides of heptanoic acid or octanoic acid, or alternatively wheat germ, sunflower, grapeseed, sesame, corn, apricot, castor, shea, avocado, olive, soy, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower,nadooulier, passionflower, muscat rose; shea butter; or caprylic/capric acid triglycerides such as those sold by Stéarineries Du
  • hydrocarbons of mineral or synthetic origin, in particular petroleum jelly, polydecenes, hydrogenated polyisobutene, in particular Parleam®, squalane, paraffin oils, and mixtures thereof,
  • oils of formula R1COOR2 in which Ri represents the residue of a linear or branched fatty acid containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon chain in particular branched containing from 1 to 40 carbon atoms to provided that the sum of the numbers of carbon atoms in R1 and R2 is greater than or equal to 10, such as Purcellin's oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, benzoates C12 to C15 alcohols, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethyl-hexyl palmitate, isostearyl isostearate, 2-hexyl- laurate decyl, 2-octyl-decyl palmitate, 2-octyl-dodecyl myristate, heptanoates, oct
  • the hydrocarbon-based oil present in a composition according to the present invention is apolar, it is formed solely of carbon and hydrogen atoms.
  • the hydrocarbon-based oil is chosen from Cs-Cu hydrocarbon-based oils and mixtures thereof, and in a particularly preferred manner, the hydrocarbon-based oil is chosen from isododecane, cetiol UT, vegelight Silk, dodecane, and even more preferably the hydrocarbon oil comprises at least or is isododecane.
  • compositions C1, C2 and/or C3 according to the invention comprise at least one hydrocarbon-based oil, preferably chosen from Cs-Cu hydrocarbon-based oils and mixtures thereof, and more preferably is at least chosen from isododecane, cetiol UT, vegelight Silk, dodecane, and even more preferably is at least isododecane.
  • compositions C1, C2 and/or C3 according to the invention comprise at least one volatile hydrocarbon-based oil.
  • compositions C1, C2 and/or C3 according to the invention comprise at least one preferably volatile hydrocarbon-based oil and optionally one or more non-volatile oils preferably in a mass ratio of volatile oils/mass of non-volatile oils greater than or equal to 2, preferably greater than or equal to 3 more preferably greater than or equal to 4.
  • compositions C1, C2 and/or C3 according to the invention contain a fatty phase comprising isododecane, in particular a fatty phase mainly comprising isododecane with respect to all the constituents of said fatty phase such as an isododecane/octyldodecanol mixture or an isododecane/isononyl isononanoate mixture.
  • a composition according to the invention comprises from 15% to 98% by weight, in particular from 15 to 90% by weight, preferably from 40% to 90% or even from 40% to 85% by weight, of oil ( s) hydrocarbon(s) relative to the total weight of the composition.
  • a composition C1, C2 or C3 according to the invention may also comprise at least one non-volatile oil distinct from said hydrocarbon-based oil described above.
  • a composition according to the invention may comprise one or more silicone oils, fluorinated or not, or mixtures thereof.
  • it may be an oil chosen from:
  • - fatty alcohols having 12 to 26 carbon atoms such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol;
  • - silicone oils such as non-volatile, linear or cyclic polymethylsiloxanes (PDMS), liquid or pasty at room temperature such as cyclomethicones, dimethicones, optionally comprising a phenyl group, such as phenyl trimethicones, phenyltrimethylsiloxydiphenyl siloxanes, diphenylmethyldimethyltrisiloxanes, diphenyl dimethicones, phenyl dimethicones, polymethylphenyl siloxanes;
  • PDMS non-volatile, linear or cyclic polymethylsiloxanes
  • liquid or pasty at room temperature such as cyclomethicones, dimethicones, optionally comprising a phenyl group, such as phenyl trimethicones, phenyltrimethylsiloxydiphenyl siloxanes, diphenylmethyldimethyltrisiloxanes, diphenyl dimethicones, pheny
  • silicon oil means an oil comprising at least one silicon atom, and in particular at least one Si—O group.
  • fluorinated oil means an oil comprising at least one fluorine atom.
  • oils may be present in a content ranging from 0.01% to 60%, and better still from 0.1% to 50% by weight, relative to the total weight of the composition.
  • the non-volatile oil distinct from said hydrocarbon-based oil is chosen from non-volatile hydrocarbon-based oils, more preferably chosen from fatty alcohols having from 12 to 26 carbon atoms, synthetic esters and mixtures thereof.
  • a composition according to the invention advantageously comprises at least one non-volatile oil distinct from said hydrocarbon oil, preferably ranging from 0.01% to 60% by weight, and preferably from 0.1% to 50% by weight, of non-volatile oil distinct from said hydrocarbon oil, relative to the total weight of the composition.
  • composition C1, C2 or C3 according to the invention may also comprise at least one oil other than the oils mentioned above.
  • composition according to the invention may comprise hydrocarbon oils, silicone oils, fluorinated or not, or mixtures thereof, distinct from the oils mentioned above.
  • the oils may be volatile or non-volatile.
  • They can be of animal, vegetable, mineral or synthetic origin.
  • the oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example, in the form of hydroxyl or acid radicals.
  • compositions C1, C2 and/or C3 according to the invention can also comprise an aqueous phase.
  • the CR compositions containing at least one crosslinking agent and/or CAC containing at least one cosmetic active agent according to the invention can also comprise an aqueous phase and/or consist of an aqueous phase.
  • the aqueous phase of a composition according to the invention C1, C2 or C3 or of a CR or CAC composition suitable for the invention comprises water and optionally one or more solvent(s) miscible(s) with water.
  • a water suitable for the invention can be a floral water, such as cornflower water and/or a mineral water such as VITTEL water, LUCAS water or LA ROCHE POSAY water, a thermal and/or spring water.
  • water-miscible solvent in the present invention is meant a compound that is liquid at room temperature and miscible with water (miscibility in water greater than 50% by weight at 25° C. and atmospheric pressure).
  • the water-miscible solvents that can be used in the composition of the invention can also be volatile.
  • the aqueous phase of a composition according to the invention may comprise at least one C2-C32 polyol.
  • polyol it is necessary to understand, within the meaning of the present invention, any organic molecule comprising at least two free hydroxyl groups.
  • a polyol in accordance with the present invention is present in liquid form at ambient temperature.
  • a polyol suitable for the invention can be a compound of the alkyl type, linear, branched or cyclic, saturated or unsaturated, bearing on the alkyl chain at least two -OH functions, in particular at least three -OH functions, and more particularly least four -OH functions.
  • the polyols advantageously suitable for the formulation of a composition according to the present invention are those having in particular from 2 to 32 carbon atoms, preferably 3 to 16 carbon atoms.
  • the polyol can be chosen, for example, from ethylene glycol, pentaerythritol, trimethylolpropane, propylene glycol, 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 such as diglycerol, polyethylene glycols, and mixtures thereof.
  • a composition according to the invention is an anhydrous composition.
  • anhydrous composition is meant a composition containing less than 2% by weight of water, or even less than 0.5% of water, and in particular free of water. If necessary, such small amounts of water can in particular be introduced by ingredients of the composition which can contain residual amounts.
  • the compositions C1, C2 and/or C3 according to the invention or the compositions CR or CAC can comprise at least one water-miscible solvent, preferably at least one lower monoalcohol having 1 with 6 carbon atoms such as ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, 1 hexanol, and/or at least one glycol having from 2 to 8 atoms carbon such as ethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, and/or at least one C3-C4 ketone and/or at least one C2- C4 aldehyde, more preferably at least one lower monoalcohol having from 1 to 6 carbon atoms as defined above and even more preferably at least one lower monoalcohol chosen from ethanol and n-butanol, and even more preferably ethanol.
  • a water-miscible solvent preferably
  • the compositions C1, C2 and/or C3 according to the invention or the compositions CR or CAC are anhydrous (that is to say contain less of 5% by weight in particular less than 2% by weight or even less than 0.5% by weight of water) and comprise at least one lower monoalcohol having from 1 to 6 carbon atoms such as ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, hexanol and/or at least one glycol having from 2 to 8 carbon atoms such as ethylene glycol, propylene glycol, 1,3 -butylene glycol and dipropylene glycol, and/or at least one C3-C4 ketone and/or at least one C2- C4 aldehyde, preferably at least one lower monoalcohol having from 1 to 6 carbon atoms such as defined previously and more preferably at least one lower monoalcohol chosen from ethanol and
  • a composition according to the invention in particular C1 or C2 or a composition suitable for the invention as CR, may comprise one or more cosmetic active ingredient(s) called “AC”, chosen from: a) agents dyes chosen from pigments, direct dyes, and mixtures thereof, b) active agents for the care of keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • AC cosmetic active ingredient
  • composition C 1 can be introduced with the copolymer CP and/or with a separate CAC composition.
  • the cosmetic active agent(s) AC optionally present in a composition C2 can be introduced with the crosslinking agent R and/or a composition CR, and/or with a composition C1 and/or with a composition CAC.
  • a C3 composition according to the invention or a CAC composition suitable for the invention comprises one or more AC cosmetic active ingredient(s) chosen from a) coloring agents from pigments, direct dyes, and mixtures thereof , b) active ingredients for caring for keratin materials, preferably the skin, c) UV filters, and d) mixtures thereof.
  • the AC cosmetic active agents present in a C3 composition can be introduced therein in different ways depending on the protocol chosen to prepare this composition.
  • composition C3 can thus be introduced with at least one of the ingredients of composition C3, for example with the (co)polymer in composition C1 and/or with the crosslinker R or a distinct composition CR containing at least this crosslinking agent and/or with a composition CAC.
  • composition C3 is obtained from a composition C1
  • they may be present in this composition C1 and/or be implemented with a composition CAC.
  • this or these ACs may be present in this composition C2 and/or be implemented with a composition CAC.
  • one or more CAs identical or different, can be present in the compositions considered for preparing C3.
  • the same AC cosmetic active ingredient may be present in a C1 composition and/or in a C2 composition and/or in a CR composition and/or in a distinct CAC composition, it being understood that when several distinct cosmetic active ingredients are used, these can be introduced for all or part indifferently in C 1 and/or in C2 and/or in CR and/or in a distinct composition CAC.
  • composition C3 may be present simultaneously in a composition C1 and/or in a composition C2 and/or in a composition CR and/or in a separate composition CAC.
  • the at least one cosmetic agent is chosen from dyestuffs, preferably chosen from pigments, direct dyes and mixtures thereof.
  • a composition according to the invention as C1 or C2, or suitable for the invention as CR may also comprise at least one particulate or non-particulate coloring matter, water-soluble or not, and preferably in an amount of at least 0.01% by weight relative to the total weight of the composition under consideration.
  • a composition according to the invention C3, or suitable for the invention as CAC further comprises at least one coloring matter, whether particulate or not, water-soluble or not, and preferably in an amount of at least 0.01% by weight relative to the total weight of the composition under consideration.
  • composition C3 according to the invention comprises at least one dyestuff chosen from pigments, direct dyes, and mixtures thereof.
  • a CAC composition suitable for the invention comprises at least one dyestuff chosen from pigments, direct dyes, and mixtures thereof, preferably at least one pigment.
  • composition C1, C2, CR comprises at least one AC cosmetic active
  • said cosmetic active preferably comprises at least one coloring material chosen from pigments, direct dyes and mixtures thereof and more preferably at least one pigment .
  • composition C3 according to the invention comprises at least one pigment.
  • pigment within the meaning of the invention, is meant any compound capable of providing color to keratin materials. These compounds have a solubility in water at 25° C. and at atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.
  • a composition C1 or C2 according to the invention or a composition CR suitable for the invention may comprise at least one cosmetic active agent AC, said cosmetic active agent preferably comprising one or more pigment(s).
  • a composition C3 according to the invention or a composition CAC suitable for the invention comprises at least one cosmetic active agent AC, said cosmetic active agent preferably comprising one or more pigment(s).
  • said cosmetic active agent preferably comprising one or more pigment(s).
  • Mention may in particular be made, as pigments suitable for the invention, of the organic and/or inorganic pigments known to the art, in particular those which are described in the encyclopedia of chemical technology by Kirk-Othmer and in the encyclopedia of industrial chemistry by Ullmann.
  • These pigments can be synthetic or natural.
  • These pigments can be in the form of powder or pigment paste. They can be coated or uncoated.
  • These pigments can for example be chosen from mineral pigments, organic pigments, lakes, special effect pigments such as nacres or glitter, and mixtures thereof.
  • a pigment suitable for the invention can be chosen from mineral pigments.
  • mineral pigment we mean any pigment that meets the definition of the Ullmann encyclopedia in the chapter inorganic pigment.
  • a pigment is marketed for example under the reference Coverleaf NS or JS by the company Chemicals And Catalysts and has a contrast ratio close to 30.
  • An example of a pigment having this structure is that marketed by the Miyoshi company under the reference PC Ball PC-LL-100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
  • the pigments can be iron oxides and/or titanium dioxides.
  • a pigment suitable for the invention can be chosen from organic pigments.
  • organic pigment we mean any pigment that meets the definition of the Ullmann encyclopedia in the organic pigment chapter.
  • the white or colored organic pigments can 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 coded in the Color Index under the references CI 61565, 61570, 74260, orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, 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, the pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2,679,771.
  • organic pigment pigment pastes such as the products sold by the company HOECHST under the name:
  • COSMENYL YELLOW G Pigment YELLOW 1 (CI 11680);
  • ORANGE COSMENYL GR Pigment ORANGE 43 (CI 71105);
  • COSMENYL RED R Pigment RED 4 (CI 12085);
  • VIOLET COSMENYL RL Pigment VIOLET 23 (CI 51319);
  • COSMENYL BLUE A2R Pigment BLUE 15.1 (CI 74160);
  • GREEN COSMENYL GG Pigment GREEN 7 (CI 74260);
  • COSMENYL BLACK R Pigment BLACK 7 (CI 77266).
  • the pigments in accordance with the invention can also be in the form of composite pigments as described in patent EP 1 184426.
  • These composite pigments can be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixing of the organic pigments on the core, and at least one organic pigment at least partially covering the core.
  • the organic pigment can also be a lake.
  • lacquer is meant the dyes adsorbed on insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.
  • 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 (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 ( CI 42 090), FDC Red 4, D & C Red 6, D & C Red 22, D & C Red 28, D & C Red 30, D & C Orange 4, D & C Yellow 8, D & C Green 5 , D & C Red 17, D &
  • lacquers mention may be made of the product known under the following name: D & C Red 7 (CI 15 850:1).
  • the pigment may also be a special effect pigment.
  • special effect pigments we mean pigments which generally create a colored appearance (characterized by a certain nuance, a certain liveliness and a certain clarity) which is not uniform and changes according to the conditions of observation (light, temperature , viewing angles, etc.). They are therefore opposed to colored pigments which provide a uniform opaque, semi-transparent or classic transparent shade.
  • nacres it is necessary to understand colored particles of any shape, iridescent or not, in particular produced by certain molluscs in their shell or else synthesized, and which have a color effect by optical interference.
  • pearlescent pigments such as mica covered with titanium, or bismuth oxychloride
  • colored pearlescent pigments such as mica covered with titanium and iron oxides, mica covered with iron oxide, mica covered with titanium and in particular with ferric blue or chromium oxide, mica covered with titanium and an organic pigment as defined above as well as pearlescent pigments based on bismuth oxychloride.
  • They may also be particles of mica on the surface of which are superimposed at least two successive layers of metal oxides and/or of organic coloring matter.
  • pearlescent pigments mention may be made of Cellini nacres marketed by BASF (Mica-TiCh-lacquer), Prestige marketed by Eckart (Mica-TiCh), Prestige Bronze marketed by Eckart (Mica-Fe2O3) Colorona marketed by Merck (Mica- TiCE-Fe2O3).
  • particles comprising a borosilicate substrate coated with titanium oxide.
  • Particles with a glass substrate coated with titanium oxide are in particular sold under the name METASHINE MC1080RY by the company TOYAL.
  • nacres mention may also be made of polyethylene terephthalate flakes, in particular those marketed by the company Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver flakes).
  • silver flakes One can also consider multilayer pigments based on synthetic substrates such as alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.
  • the nacres in accordance with the invention are micas covered with titanium dioxide or iron oxide as well as bismuth oxychloride.
  • the special effect pigments can also be chosen from reflective particles, that is to say in particular particles whose size, structure, in particular the thickness of the layer or layers which constitute it and their physical and chemical natures, and the surface finish, allow them to reflect incident light.
  • This reflection may, where appropriate, have sufficient intensity to create on the surface of the composition or mixture, when the latter is applied to the support to be made up, highlights visible to the naked eye, that is i.e. brighter points that contrast with their surroundings by seeming to shine.
  • the reflective particles can be selected so as not to significantly alter the coloring effect generated by the coloring agents associated with them and more particularly so as to optimize this effect in terms of color rendering. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or copper color or reflection.
  • These particles can have various shapes, in particular be in the form of platelets or globular, in particular spherical.
  • the reflective particles may or may not have a multilayer structure and, in the case of a multilayer structure, for example at least one layer of uniform thickness, in particular of a reflective material.
  • the reflective particles do not have a multilayer structure, they can be composed for example of metal oxides, in particular titanium or iron oxides obtained by synthesis.
  • the reflective particles may for example comprise a natural or synthetic substrate, in particular a synthetic substrate at least partially coated with at least one layer of a reflective material, in particular of at least one metal or metallic material .
  • the substrate can be monomaterial, multimaterial, organic and/or inorganic.
  • the substrate of the reflective particles can be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, in particular aluminosilicates and borosilicates, synthetic mica and their mixtures, this list not being limiting.
  • the reflective material may comprise a layer of metal or of a metallic material.
  • a metallic material such as those marketed under the names Starbrite 1200 EAC® by the company Siberline and Metalure® by the company Eckart and glass particles covered with a metallic layer, in particular those described in the documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
  • reflective particles comprising a mineral substrate coated with a layer of metal
  • Particles with a glass substrate coated with silver, in the form of platelets are sold under the name MICROGLASS METASHINE REFSX 2025 PS by the company TOY AL.
  • Particles with a glass substrate coated with a nickel/chrome/molybdenum alloy are sold under the name CRYSTAL STAR GF 550, GF 2525 by this same company.
  • particles comprising a metal substrate such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze, titanium, said substrate being coated with at least one layer of at least one metal oxide such as titanium oxide, aluminum oxide, iron oxide, cerium, chromium oxide, silicon oxides and mixtures thereof.
  • a metal substrate such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze, titanium
  • said substrate being coated with at least one layer of at least one metal oxide such as titanium oxide, aluminum oxide, iron oxide, cerium, chromium oxide, silicon oxides and mixtures thereof.
  • Mention may be made, by way of example, of the aluminum, bronze or copper powders coated with SiO 2 marketed under the name VISIONAIRE by the company ECKART. Mention may also be made of pigments with an interference effect not fixed on a substrate, such as liquid crystals (Helicones HC from Wacker), holographic interference flakes (Geometric Pigments or Spectra f/x from Spectratek). Special effect pigments also include fluorescent pigments, whether fluorescent in daylight or which produce ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, marketed for example by the Quantum Dots Corporation. The variety of pigments which can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic and interference effects.
  • the size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 ⁇ m, preferably between 20 nm and 80 ⁇ m, and more preferably between 30 nm and 50 ⁇ m.
  • the pigments can be dispersed in the composition using a dispersing agent.
  • the dispersing agent serves to protect the dispersed particles against their agglomeration or flocculation.
  • This dispersing agent may be a surfactant, an oligomer, a polymer or a mixture of several of them, bearing one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can cling physically or chemically to the surface of the pigments.
  • These dispersants also have at least one functional group that is compatible or soluble in the continuous medium.
  • esters of 12-hydroxystearic acid in particular and of Cs to C20 fatty acid and of polyol such as glycerol, diglycerin, such as poly(12-hydroxystearic) acid stearate of molecular weight of approximately 750 g/mole such as that sold under the name Solsperse 21,000 by the company Avecia, the polygyceryl-2 dipolyhydroxy stearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel or the acid polyhydroxystearic such as that sold under the reference Arlacel P100 by the company Uniqema and their mixtures.
  • polyol such as glycerol, diglycerin
  • CTFA name poly(12-hydroxystearic) acid stearate of molecular weight of approximately 750 g/mole
  • CTFA name polygyceryl-2 dipolyhydroxy stearate
  • Dehymyls PGPH by the company Henkel
  • acid polyhydroxystearic
  • the pigments used in the composition can be surface-treated with an organic agent.
  • pigments previously surface-treated useful in the context of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electro-chemical, mechano-chemical or mechanical nature, with an organic agent such as those which are described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, p. 53-64 before being dispersed in the composition in accordance with the invention.
  • organic agents can for example be chosen from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; sodium, potassium, magnesium, iron, titanium, zinc or aluminum salts of fatty acids, for example aluminum stearate or laurate, aluminum dimyristate and aluminum salt of hydrogenated tallow glutamate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethylmethacrylates; polymers and copolymers containing acrylate units; alkanoamines; silicone compounds, for example silicones, in particular polydimethylsiloxanes; fluorinated organic compounds, for example perfluoroalkyl ethers, perfluoroalkyl phosphates, hexafluoropropylene polyoxides, perfluoropol
  • the surface-treated pigments useful in the composition may also have been treated with a mixture of these compounds and/or have undergone several surface treatments.
  • the surface-treated pigments useful in the context of the present invention can be prepared according to surface treatment techniques well known to those skilled in the art or found as such in commerce.
  • the surface treatments of the pigments are chosen from the following treatments: a PEG-Silicone treatment, for example the surface treatment AQ marketed by LCW; a Methicone treatment, for example the SI surface treatment marketed by LCW; a Dimethicone treatment, for example the Covasil 3.05 surface treatment marketed by LCW; a Dimethicone/Trimethylsiloxysilicate treatment, for example the Covasil 4.05 surface treatment marketed by LCW; a Magnesium Myristate treatment, for example the MM surface treatment marketed by LCW; an aluminum dimyristate treatment, for example the MI surface treatment marketed by Miyoshi; a Perfluoropolymethylisopropyl ether treatment, for example the FHC surface treatment marketed by LCW; an Isostearyl Sebacate treatment, for example the HS surface treatment marketed by Miyoshi; a perfluoroalkyl phosphate treatment, for example the PF surface treatment marketed by Daito;
  • the dispersing agent is present with organic or inorganic pigments in particulate form of sub-micron size in the dye composition.
  • sub-micron pigments whose particle size has been micronized by micronization method and whose average particle size is less than one micrometer (pm), in particular the average particle size is between 0.1 to 0.9 ⁇ m, and preferably from 0.2 to 0.6 ⁇ m.
  • the dispersing agent and the pigment(s) are present in a dispersant/pigment mass ratio comprised from 1:4 to 4:1, particularly from 1.5:3, 5 to 3.5:1, or better of 1.75:3 and 3:1.
  • the dispersing agent(s) can therefore have a silicone skeleton, such as silicone polyether and dispersants of the amino-silicone type, different from the alkoxysilanes previously described.
  • suitable dispersing agents mention may be made of: amino-silicones, that is to say silicones comprising one or more amino groups such as those marketed 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, by the company Genesee polymers, silicone acrylates such as those marketed under the names and references Tego® RC 902, Tego® RC 922, Tego® RC 1041, and Tego® RC 1043 by the company Evonik, polydimethylsiloxane (PDMS) silicones with carboxylic groups such as those marketed under the names and references X-22162 and X-22370 by the company Shin - Etsu, silicone
  • the dispersing agent(s) are of the amino-silicone type, different from the alkoxysilanes previously described and are cationic.
  • the pigment(s) is (are) chosen from inorganic, mixed inorganic-organic or organic pigments.
  • the pigment(s) according to the invention are organic pigments, preferably organic pigments surface-treated with an organic agent chosen from silicone compounds.
  • the pigment or pigments according to the invention are mineral pigments.
  • a composition C1 or C2 according to the invention or a composition CR suitable for the invention may comprise at least one cosmetic active agent AC, said cosmetic active agent preferably comprising one or more direct dye(s).
  • a C3 composition according to the invention or a CAC composition suitable for the invention comprises at least one AC cosmetic active, said cosmetic active preferably comprising one or more direct dye(s).
  • direct dye we mean natural and/or synthetic dyes, different from oxidation dyes. These are dyes that will diffuse superficially on the fiber. They can be ionic or nonionic, preferably cationic or nonionic.
  • direct dyes suitable for the invention mention may be made of azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes are preferably cationic direct dyes. Mention may be made of the cationic hydrazono dyes of formulas (A) and (B) below and the cationic azo dyes of formulas (C) and (D) below:
  • Het + represents a cationic heteroaryl radical, preferably with an endocyclic cationic charge such as imidazolium, indolium, or pyridinium, optionally substituted preferably by at least one (Ci-Cs)alkyl group such as methyl;
  • Ar + represents an aryl radical, such as phenyl or naphthyl, with an exocyclic cationic charge, preferably ammonium, particularly tri/Ci-Cs/alkyl-ammonium such as trimethylammonium;
  • Ar represents an aryl group, in particular phenyl, optionally substituted, preferably by one or more electron-donating groups such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, (di)(Ci-C8)(alkyl) amino optionally substituted on the alkyl group(s) by a hydroxyl group, aryl(Ci-C8)alkylamino, and N-(Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino optionally substituted or else Ar represents a julolidine group ;
  • Ar represents an optionally substituted (hetero)aryl group such as phenyl or pyrazolyl optionally substituted, preferably by one or more (Ci-C8)alkyl, hydroxyl, (di)(Ci-C8)(alkyl)amino, (Ci-C8)alkyl, Cs)alkoxy or phenyl;
  • Ra and Rb identical or different, representing a hydrogen atom or a (Ci-C8)alkyl group optionally substituted, preferably by a hydroxyl group; or else the substituent Ra with a substituent of Het+ and/or Rb with a substituent of Ar form together with the atoms which carry them a (hetero)cycloalkyl; particularly Ra and Rb, representing a hydrogen atom or a (C 1 -C 4 )alkyl group optionally substituted by a hydroxyl group;
  • Q- represents an organic or inorganic anionic counterion such as a halide or an alkyl sulfate.
  • direct dyes with cationic charge endocyclic azo and hydrazono of formula (A) to (D) as defined previously. More particularly, the cationic direct dyes with an endocyclic cationic charge described in patent applications WO 95/15144, WO 95/01772 and EP-714954.
  • R 1 represents a (C 1 -C 4 )alkyl group such as methyl
  • R 2 and R 3 identical or different, represent a hydrogen atom or a group (Ci -Chalky le such as methyl;
  • R 4 represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, (di)(Ci-C8)(alkyl)amino optionally substituted on the alkyl groups with a hydroxyl group; particularly R 4 is a hydrogen atom;
  • Z represents a CH group or a nitrogen atom, preferably CH;
  • Q- is an anionic counter ion as defined above, particularly a halide such as chloride or an alkyl sulphate such as methyl sulphate or mesyl sulphate.
  • the dyes of formula (E) and (F) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or their derivatives with Q- an anionic counterion as defined previously, particularly halide such as chloride or a alkyl sulfate such as methyl or mesyl sulfate.
  • the direct dyes can be chosen from anionic direct dyes.
  • the anionic direct dyes of the invention are dyes commonly called “acid” direct dyes for their affinity with alkaline substances.
  • anionic direct dyes any direct dye comprising in its structure at least one CO 2 R' 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 direct dyes can be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid triarylmethane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and acid natural dyes.
  • X, X’ and X identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group;
  • R represents a hydrogen atom, an alkyl group, an aryl group, (di)(alkyl)amino, aryl(alkyl)amino; preferably a phenylamino or phenyl group;
  • Ar-N N- with Ar representing an optionally substituted aryl group; preferably a phenyl optionally substituted by one or more alkyl, (O)2S(O-)-, M+ or phenylamino groups; or two contiguous groups R7 with Rs or Rs with R9 or R9 with R10 together form a fused group benzo A'; and R'7 with R's or R's with R'9 or R' 9 with R' 10 together form a fused benzo group B'; with A' and B' optionally substituted with one or more groups chosen from nitro; nitroso; (O) 2 S(O-)-, M+; hydroxy; mercapto; (di) (alkyl) amino; R°-C(X)-X'-;R°-X'-C(X)-;R°-X'-C(X)-X”-;
  • Ar-N N- and optionally substituted ary l(alkyl)amino; with M+, R°, X, X', X” and Ar as previously defined; and in which:
  • W represents a sigma bond G, an oxygen or sulfur atom, or a divalent radical -NR- with R as defined previously, or methylene -C(Ra)(Rb)- with identical or different Ra and Rb, representing a hydrogen atom or an aryl group, or else Ra and Rb form together with the carbon atom which carries them a spiro cycloalkyl; preferentially W represents a sulfur atom or Ra and Rb together form a cyclohexyl; it being understood that the formulas (G) and (G') comprise at least one sulphonate radical (O) 2 S(O-)-, M+ or a carboxylate radical (O)CO-, M+ on one of the rings A, A', B, B' or C; preferentially sodium sulphonate.
  • dyes of formula (G) include: 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
  • Ru represents a hydrogen atom, an alkyl group or a group - C(O)O-, M+ with M+ as defined previously;
  • Ris represents a hydrogen atom
  • Riô represents an oxo group in which case R' i6 is absent, or else Ris with Riô together form a double bond;
  • Ri7 and Ris identical or different, represent a hydrogen atom, or a group chosen from:
  • Ar-O-S(O)2- with Ar representing an optionally substituted aryl group; preferably a phenyl optionally substituted by one or more alkyl groups;
  • Ri9 and R20 together form either a double bond or a benzo group D', optionally substituted;
  • R21 represents a hydrogen atom, an alkyl or alkoxy group
  • R a and Rb which are identical or different, are as defined above, preferably R a represents a hydrogen atom and Rb represents an aryl group;
  • Y represents either a hydroxy group or an oxo group; represents a single bond when Y is an oxo group; and represents a double bond when Y represents a hydroxy group; it being understood that the formulas (H) and (H') comprise at least one sulphonate radical (O) 2 S(O-)-, M+ or a carboxylate radical -C(O)O-, M+ on one of the rings D or E ; preferentially sodium sulfonate.
  • dyes of formula (H) By way of example of dyes of formula (H), mention may be made of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and by way of example of dyes of formula (H'), mention may be made of: Acid Yellow 17.
  • Z' represents a hydrogen atom or a group NR28R29 with R28 and R29, which are identical or different, represent a hydrogen atom or a group chosen from: alkyl; polyhydroxyalkyl such as hydroxy ethyl; aryl optionally substituted by one or more particularly i) alkyl groups such as methyl, n-dodecyl, n-butyl; ii) (O)2S(O-)-, M+ with M+ as previously defined; iii) R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X”- with R°, X, X' and X “as defined previously, preferably R° represents an alkyl group; cycloakyl; in particular cyclohexyl;
  • Z represents a group chosen from hydroxy and NR′2sR′29 with R′28 and R′29, which are identical or different, represent the same atoms or groups as R28 and R29 as defined above; it being understood that the formulas (J) and (J') comprise at least one sulphonate radical (O) 2 S(O-)-, M+ or a carboxylate radical -C(O)O-, M+; preferentially sodium sulfonate.
  • dyes of formula (J) include: 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 #2; and by way of example of dyes of formula (J′), mention may be made of: Acid Black 48. d) nitro dyes of formulas (K) and (K′) below:
  • R30, R31 and R32 which are identical or different, represent a hydrogen or halogen atom, or a group chosen from: alkyl; alkoxy optionally substituted by one or more hydroxy groups, alkylthio optionally substituted by one or more hydroxy groups; hydroxy, mercapto; nitro, nitroso; polyhaloalkyl;
  • R30, R31 and R32 represent a hydrogen atom; and in which:
  • Rc and Rd identical or different, represent a hydrogen atom or an alkyl group
  • W is as previously defined; W particularly represents an -NH- group;
  • ALK represents a divalent linear or branched, C1-C6 alkylene group; particularly ALK represents a group -CH2-CH2-; n is 1 or 2; p represents an integer comprised inclusively between 1 and 5; q represents an integer comprised inclusively between 1 and 4; u is 0 or 1; when n is 1, J represents a nitro or nitroso group; especially nitro; when n is 2, J represents an oxygen or sulfur atom, or a divalent radical —S(O) m — with m representing an integer 1 or 2; preferably J represents an —SO 2 — radical;
  • M' represents a hydrogen atom or a cationic counterion
  • /c present or absent, represents a benzo group optionally substituted by one or more R30 groups as defined previously; it being understood that the formulas (K) and (K') comprise at least one sulfonate radical (O) 2 S(O-)-, M+ or a carboxylate radical -C(O)O-, M+; preferentially sodium sulphonate.
  • dyes of formula (K) mention may be made of: Acid Brown 13, Acid Orange 3; as examples of dyes of formula (K'), mention may be made of: Acid Yellow 1, Sodium salt of 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino 5-nitro benzene acid sulfonic acid, 2(4'-N,N(2”-hydroxyethyl)amino-2'-nitro)aniline ethane sulfonic acid, 4-P-hydroxyethylamino-3-nitrobenzene sulfonic acid; EXT D&C yellow 7. e) triarylmethane dyes of formula (L) below:
  • R33, R34, R35 and R36 which are 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 by an (O) m S(O-)-, M+ group with M+ and m as defined previously;
  • R37, R38, R39, R40, R41, R42, R43 and R44 identical or different, represent a hydrogen atom or a group chosen from: alkyl; alkoxy, alkylthio;
  • X, X’ and X identical or different, representing an oxygen, sulfur or NR atom 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 by one or more groups chosen from nitro; nitroso; (O)2S(O-)-, M+; hydroxy; mercapto; (di) (alkyl) amino; R°-C(X)-X'-;R°-X'-C(X)-; ix) R°-X'-C(X)-X”-; with M+, R°, X, X', X” as previously defined; particularly R37 to R40 represent a hydrogen atom, and R41 to R44, which are identical or different, represent a hydroxy or (O)2S(O-)-, M+ group; and when R43 with R44 together form a benzo group, it is preferentially substituted by a (O)2S(O-)- group; it is preferentially substituted by a (O)2S(O-)- group;
  • dyes of formula (L) By way of example of dyes of formula (L), 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, Acid Green 50. f) dyes derived from xanthene of formula (M) below: in which R45, R46, R47 and R48, identical or different, represent a hydrogen atom or a halogen atom and R49, R50, R51 and R52, identical or different, represent a hydrogen atom, halogen atom, or a group chosen from: alkyl; alkoxy, alkylthio; hydroxy, mercapto; nitro, nitroso;
  • G represents an oxygen or sulfur atom or an NRe group with Re as defined above; particularly G represents an oxygen atom;
  • L represents an O- alcoholate, M+; an S-, M+ thioalcoholate or an NRf group, 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 are identical or different, representing a hydrogen atom, an optionally substituted alkyl or aryl group; L' represents in particular an oxygen atom or a phenylamino group optionally substituted by one or more alkyl groups or (O) m S(O-)-, M+ with m and M+ as defined previously;
  • Q and Q' identical or different, represent an oxygen or sulfur atom; particularly Q and Q' represent an oxygen atom;
  • dyes of formula (M) include: Acid Yellow 73, Acid Red 51, Acid Red 52, Acid Red 87, Acid Red 92, Acid Red 95, Acid Violet 9.
  • G represents an oxygen or sulfur atom or an NRe group with Re as defined above; particularly G represents an oxygen atom;
  • Ri and Rh identical or different, represent a hydrogen atom or an alkyl group; it being understood that formula (N) comprises at least one sulphonate radical (O)2S(O-)-, M+ or a carboxylate radical -C(O)O-, M+; preferentially sodium sulphonate.
  • dyes of formula (N) By way of example of dyes of formula (N), mention may be made of: Acid Blue 74. h) dyes derived from quinoline of formula (O) below: in which :
  • R ⁇ I represents a hydrogen or halogen atom or an alkyl group
  • dyes of formula (O) include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.
  • the direct dyes are chosen from anionic direct dyes.
  • the dyestuffs preferably the pigments, can be present in concentrations ranging from 0.01 to 30% by weight, preferably from 0.02 to 20% by weight, more particularly from 0.05 to 15% with respect to the total weight of the composition containing them.
  • the direct dye(s) may be present in concentrations ranging from 0.001 to 10% by weight of the total weight of the composition, preferably from 0.005 to 5% by weight of the total weight of the composition which contains them.
  • the cosmetic active agent(s) AC in particular the dyestuff(s) and more particularly the pigment(s) are introduced into the compositions C1 under consideration to prepare the compositions C3.
  • a composition according to the invention C1, C2, or suitable for the invention, CR may comprise, as cosmetic active ingredient, at least one care active ingredient, and preferably in the amount of at least 0.01% by weight relative to the total weight of the composition under consideration.
  • a composition according to the invention C3, or suitable for the invention, CAC comprises, as cosmetic active ingredient, at least one care active ingredient, and preferably at a rate of at least 0.01% by weight relative to the total weight of the composition under consideration.
  • the care active may be at least one hydrophilic active and/or one lipophilic active, and preferably a hydrophilic active.
  • hydrophilic active means a water-soluble or water-dispersible active capable of forming hydrogen bonds.
  • the cosmetic care active(s) may in particular be chosen from:
  • vitamins and their derivatives in particular their esters, in particular tocopherol (vitamin E) and its esters (such as tocopherol acetate), ascorbic acid (vitamin C) and its derivatives;
  • humectants in particular urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, and xylitylgiucoside, and in particular glycerol;
  • - anti-ageing active agents in particular hyaluronic acid compounds, and in particular sodium hyaluronate, retinol and its derivatives, salicylic acid compounds and in particular n-octanoyl-5-salycilic acid (acid capryloyl salicylic), caffeine, adenosine, c-beta-d-xylopyranoside-2-hydroxy-propane and 3-hydroxy-2-pentylcyclopentylacetic acid sodium salt;
  • venotonics in particular polyphenols, and in particular escin, ruscus, diosmin, hesperidin, resveratrol, and
  • the at least one care active ingredient comprises at least one skin care active ingredient.
  • the at least one care active comprises at least one moisturizing agent (also called humectant) and preferably comprises at least glycerin.
  • a composition according to the invention C1, C2, or suitable for the invention, CR may comprise, as cosmetic active ingredient, at least one care active ingredient, and preferably at least a moisturizing agent (also called humectant).
  • a composition according to the invention C3, or suitable for the invention, CAC comprises, as cosmetic active ingredient, at least one care active ingredient, and preferably at least one moisturizing agent (also called humectant).
  • the care active is a moisturizing agent, and in particular is glycerin (glycerol).
  • the care active(s) may in particular be present, in the composition under consideration, in a content ranging from 0.01% to 30% by weight, relative to the weight of the composition, and preferably from 0.02% to 25% in weight.
  • the care active(s), in particular glycerin are introduced into the compositions C1.
  • a composition according to the invention C1 or C2, or suitable for the invention, CR may comprise, as cosmetic active ingredient, at least one UV filter.
  • a composition according to the invention C3, or suitable for the invention, CAC comprises, as cosmetic active ingredient, at least one UV filter.
  • the UV filter is a UV filter usually used in cosmetics. It can be chosen from the positive list contained in Annex VI of Regulation (EC) No. 1223/2009, which specifies the list of UV filters authorized in cosmetics.
  • UV filters suitable for the invention can be of different types.
  • They can be organic lipophilic, hydrophilic or insoluble.
  • lipophilic UV filter any cosmetic or dermatological filter capable of being completely dissolved in the molecular state in a liquid fatty phase or else of being dissolved in colloidal form (for example in micellar form) in a fatty phase. liquid.
  • hydrophilic UV filter any cosmetic or dermatological filter capable of being completely dissolved in the molecular state in a liquid aqueous phase or else of being dissolved in colloidal form (for example in micellar form) in an aqueous phase. liquid.
  • insoluble UV filter any cosmetic or dermatological filter which is neither defined as a lipophilic UV filter nor as a hydrophilic UV filter, and which is in the form of particles in the aqueous or liquid fatty phase.
  • the UV filters of the composition according to the invention can provide UVA and/or UVB photoprotection.
  • the compositions according to the invention can comprise at least one organic and/or inorganic UV filter (filters of UV radiation from sunlight).
  • a composition according to the invention C1 or C2, or suitable for the invention, CR may comprise, as cosmetic active ingredient, at least one UV filter chosen from hydrophilic organic UV filters, organic UV filters lipophilic filters, insoluble organic UV filters, mineral filters, and mixtures thereof.
  • composition according to the invention C3, or suitable for the invention, CAC may comprise, as cosmetic active ingredient, at least one UV filter chosen from hydrophilic organic UV filters, lipophilic organic UV filters, insoluble organic UV filters, mineral filters, and mixtures thereof.
  • compositions may comprise one or more UV screening agents chosen from bis-resorcinyltriazine derivatives, dibenzoylmethane derivatives, benzylidenecamphor derivatives, and mixtures thereof.
  • the organic UV filters can also be chosen from anthranilics; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenyl benzotriazole derivatives; benzalmalonate derivatives, in particular those cited in US Pat. No. 5,624,663; phenyl benzimidazole derivatives; imidazolines; derivatives of 4,4-diarylbutadienes; bis-benzoazolyl derivatives, as described in patents EP 6,693,23 and US 2,463,264; derivatives of p-aminobenzoic acid (P AB A); methylene bis-(hydroxyphenyl benzotriazole) derivatives, as described in applications US Pat. No. 5,237,071, US Pat.
  • benzoxazole derivatives as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 10162844; screening polymers and screening silicones such as those described in particular in application WO 93/04665; dimers derived from ⁇ -alkylstyrene such as those described in patent application DE 19855649; 4,4-diarylbutadienes as described in applications EP 0 967 200, DE 19746654, DE 19755649, EP 1 008 586, EP 1 133 980 and EP 133 981; derivatives of other merocyanins such as those described in applications WO 04006878, WO 05058269 and WO 06032741 and mixtures thereof.
  • the concentration of organic UV screening agents in the compositions according to the invention varies from 1% to 50%, preferably from 1% to 40% by weight, and again for example ranges from 5% to 35% by weight, relative to the total weight of the composition.
  • the compositions according to the invention can also comprise mineral UV screening agents which are generally pigments.
  • the pigments can be coated or uncoated. Coated pigments are pigments which have undergone one or more surface treatments of a chemical, electronic, mechanochemical and/or mechanical nature with compounds as described for example in Cosmetics & Toiletries, February 1990, Vol. 105, p.
  • 53-64 such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal alkoxides (titanium or aluminum), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • silicones are organosilicon polymers or oligomers with a linear or cyclic, branched or cross-linked structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consisting essentially of a repetition main units in which the silicon atoms are interconnected by oxygen atoms (siloxane bond), optionally substituted hydrocarbon radicals being directly bonded via a carbon atom on said silicon atoms.
  • sicones also encompasses the silanes necessary for their preparation, in particular the alkyl silanes.
  • the silicones used for coating the pigments suitable for the present invention are preferably chosen from the group containing alkyl silanes, polydialkylsiloxanes and polyalkylhydrogenosiloxanes. Even more preferentially, the silicones are chosen from the group containing octyl trimethyl silane, polydimethylsiloxanes and polymethylhydrogenosiloxanes.
  • the metal oxide pigments before their treatment with silicones, may have been treated with other surfactants, in particular with cerium oxide, alumina, silica, compounds of aluminum, silicon compounds, or mixtures thereof.
  • the mineral UV filters can be chosen from coated or uncoated pigments, and in particular from coated titanium oxide pigments, titanium oxides treated with a silicone, uncoated titanium oxide pigments, pigments pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and mixtures thereof.
  • titanium dioxide and cerium dioxide including the equal weight mixture of silica-coated titanium dioxide and cerium dioxide, sold by the company Ikeda under the name “Sunveil A ", as well as the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone such as the product "M 261” sold by the company Kemira or coated with alumina, silica and glycerine such than the “M 211” product sold by Kemira.
  • the pigments can be introduced into the compositions according to the invention as such or in the form of a pigment paste, that is to say mixed with a dispersant, as described for example in document GB 2206339.
  • compositions according to the invention are devoid of mineral UV filters.
  • the amount of mineral UV screening agent(s), present in the compositions according to the invention can range from 0.01% to 20% by weight, relative to the total weight of the composition. It ranges for example from 1% to 15% by weight, relative to the total weight of the composition.
  • the composition according to the invention also comprises one or more organic UV filters and one or more mineral UV filters.
  • compositions according to the invention comprise a combination of UV filters as described in patent FR 2 977 490, application WO 2013/004777 or application US 2014/0134120.
  • the water-soluble UV screening agent(s) are introduced into a composition according to the invention and in particular into a composition C3, by being mixed with the composition C1 if considered to prepare a composition C3 and/or with the composition CR containing at least one cross-linking agent.
  • the fat-soluble UV screening agent(s) are introduced into a composition according to the invention and in particular into a composition C3, via a separate composition CAC.
  • the inorganic or insoluble UV screening agent(s) are present in composition C1.
  • a composition according to the invention may also comprise one or more fillers, in particular in a content ranging from 0.01% to 30% by weight, relative to the total weight of the composition, preferably ranging from 0.01% to 20 % by weight relative to its total weight.
  • fillers is meant particles of any shape, colorless or white, mineral or synthetic, insoluble in the medium of the composition regardless of the temperature at which the composition is manufactured.
  • These fillers can in particular be used to modify the rheology or the texture of the composition.
  • talc talc
  • mica silica
  • silica kaolin
  • poly-P-alanine and polyethylene powders tetrafluoroethylene polymer powders (Teflon®), lauroyl-lysine, starch, boron nitride
  • polymeric hollow microspheres such as those of polyvinylidene chloride/acrylonitrile such as Expancel® (Nobel Industrie), acrylic acid copolymers, silicone resin microbeads (Tospearls® from Toshiba, for example), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate and hydro-carbonate, hydroxyapatite, barium sulphate, aluminum oxides, polyurethane powders, composite fillers, hollow silica microspheres, and glass or ceramic microcapsules. It is also possible to use particles, which have the shape of portions of hollow spheres, as described in patent applications JP-2003 128 788
  • a composition C1 or C2 or C3 according to the invention or CR or CAC suitable for the invention comprises at least one additional cosmetic active ingredient.
  • a composition according to the invention may also contain ingredients commonly used in cosmetics, such as thickeners, gelling agents, trace elements, softeners, sequestrants, perfumes, basifying or acidifying agents, dispersing agents, preservatives, surfactants, anti-hair loss agents, anti-dandruff agents, propellants, polar additives, film-forming polymers different from the CP copolymers of the invention, or mixtures thereof.
  • compositions comprising at least:
  • copolymer obtained by copolymerization of at least monomers of isobomyl acrylate and acetoacetoxyethyl methacrylate in isododecane, preferably a non-volatile oil distinct from isododecane chosen in particular from 2-octyl-1 -decanol and isononyl isononanoate and preferably at least one pigment, or
  • compositions comprising at least:
  • APTES 3-aminopropyl triethoxysilane
  • APTES 3-aminopropyl triethoxysilane
  • poly(D-Glucosamine) poly(D-Glucosamine)
  • a copolymer obtained by copolymerization of at least isobomyl acrylate and acetoacetoxyethyl methacrylate monomers in isododecane a crosslinking agent chosen from poly(D-Glucosamine), poly(dimethylsiloxane) with bis(3-aminopropyl) (PDMS-diNtk), bis-cetearyl amodimethicone, optionally at least one non-volatile oil distinct from isododecane, preferably chosen from isononyl isononanoate and 2-octyl-1- decanol, and preferably at least one pigment,
  • a crosslinking agent chosen from poly(D-Glucosamine), poly(dimethylsiloxane) with bis(3-aminopropyl) (PDMS-diNtk), bis-cetearyl amodimethicone, optionally at least one non-volatile oil distinct from isod
  • - a copolymer obtained by copolymerization of at least isobomyl acrylate, 2-ethylhexyl acrylate, PDMS methacrylate and acetoacetoxy ethyl methacrylate monomers in isododecane, a crosslinking agent chosen from poly(D - Glucosamine) and bis-cetearyl amodimethicone, and preferably at least one pigment, or
  • a composition C1, C2 or C3 in accordance with the invention may be in the form of a make-up product, in particular colored, for the skin, in particular a foundation, optionally having care properties, a blush, a blush or eyeshadow, a concealer, an eyeliner; a lip makeup product such as a lipstick, optionally having care properties, a lip gloss, lip pencils; a make-up product for appendages such as the nails, the eyelashes, in particular in the form of a mascara bar, the eyebrows and the hair, a temporary tattoo product for the skin of the body.
  • a composition C1, C2 or C3 according to the invention is in the form: either of a colored product for the lips; either a skin care product, possibly colored, in particular a cream or a fluid with moisturizing and/or filling and/or tightening effect properties; or either a hair product, in particular a hair coloring product or a styling product in particular devoid of coloring material, such as a hairspray, or a so-called “styling” product of the mousse or gel type.
  • composition according to the invention is not in the form of a patch.
  • compositions C1, C2 and C3 according to the invention can be applied directly as such to the target keratin material or even be formed directly on the surface of this keratin material.
  • 1-gesture application mode There are thus distinguished according to the invention three modes of implementation called “1-gesture application mode”, “2-gesture application mode” and “3-gesture application mode”.
  • the term "1-step method of application” means the direct application to the target keratin material of a single composition in accordance with the invention, namely a composition C1 according to the invention or a composition C2 or C3 according to the invention comprising at least one fatty phase, at least one copolymer CP and at least one crosslinking agent R as described above.
  • mode of application 2 gestures the successive application, on the target keratin material, of two different compositions, at least one of which according to the invention.
  • this 2-step mode of application covers the sequential application to a target keratin material, a) of a composition C1 optionally containing at least one cosmetic active ingredient AC, and P) of a second composition chosen from a composition CR containing at least one crosslinking agent R, and optionally at least one cosmetic active agent AC, as defined above, AC preferably being a dyestuff.
  • step a) is preferably followed by step P).
  • 3-step mode of application means the sequential application to a target keratin material, a) of a CAC composition comprising one or more cosmetic active ingredient(s), P) of a composition C1 and v) a composition CR comprising at least one crosslinking agent R as defined above.
  • step y) preferably constitutes the last step of said method and more preferably step a) is followed by step P) itself followed by step y).
  • composition C1 is conventionally qualified as a “base coat” and the composition which is superimposed on it, generally the composition CR, is qualified as a “top coat”.
  • “1 gesture” application mode According to one embodiment, a single composition C1 is applied to the keratin materials.
  • a single composition C2 or C3 is applied to the keratin materials.
  • a composition C1 is mixed with at least one crosslinking agent R or a composition CR and optionally with at least one cosmetic active agent AC or a distinct composition CAC before application to the keratin material.
  • the system remains fluid for a long enough time to allow application to keratin materials such as, for example, the skin or the hair.
  • composition C2 is prepared just before application to the keratin materials, for example by mixing a composition C1 and a crosslinking agent R or by mixing a composition C1 and a composition CR containing at least one crosslinker R.
  • the resulting composition C2 or C3 is applied to dry keratin materials.
  • the keratin materials can be dried after application of the resulting composition C2 or C3.
  • a persistent and non-sticky deposit is advantageously obtained.
  • the deposit obtained is also resistant to food oils, water and shampoos.
  • composition according to the invention can be implemented according to a so-called “2-step” mode of application.
  • step ii) is subsequent to step i).
  • compositions are applied to dry keratin materials.
  • the keratin materials can be dried after application of the compositions, in particular after application of each composition. After application of the two compositions, a persistent and non-sticky deposit is advantageously obtained. The deposit obtained is also resistant to food oils, water and shampoos.
  • composition according to the invention can be implemented according to a so-called “3-step” mode of application.
  • the keratinous materials are applied sequentially to i) a composition CAC containing at least one cosmetic active agent AC, in particular at least one coloring material, preferably at least one pigment, ii) a composition C1 comprising at least one copolymer CP as defined previously and iii) a crosslinking agent R or a composition CR comprising at least one crosslinking agent R, CR and R as described above, and distinct from the composition CAC.
  • a composition CAC containing at least one cosmetic active agent AC, in particular at least one coloring material, preferably at least one pigment
  • a composition C1 comprising at least one copolymer CP as defined previously and iii) a crosslinking agent R or a composition CR comprising at least one crosslinking agent R, CR and R as described above, and distinct from the composition CAC.
  • step iii) is subsequent to step ii).
  • a CAC composition comprising at least AC cosmetic active ingredient, in particular at least one dyestuff, and preferably at least one pigment, is applied to the keratin materials.
  • composition C1 as described above, comprising at least one copolymer CP and at least one fatty phase, preferably isododecane, as described above, is applied to the composition CAC.
  • compositions CAC and C1 are applied to the compositions CAC and C1.
  • compositions CAC, C1 and CR are prepared just before application to the keratin materials.
  • compositions are applied to dry keratin materials.
  • the keratin materials can be dried after application of the compositions, in particular after application of each composition.
  • compositions C1, C2, C3 and optionally the compositions CAC and CR can be applied to dry or wet keratin fibres, which may or may not have been rinsed out, as well as on all types of fibers, light or dark, natural or colored, permed, bleached or straightened.
  • the fibers are washed before application of one of the compositions C1, C2, C3 and optionally of a CAC and/or CR composition.
  • the application to the fibers can be implemented by any conventional means, in particular by means of a comb, a brush, a brush, a sponge or the fingers.
  • the compositions C1, C2, C3 and optionally the compositions CAC and CR are applied to the keratin fibers according to an exposure time of between 1 minute and 10 hours, in particular between 1 minute and 1 hour.
  • the keratin fibers may optionally undergo rinsing.
  • the keratin fibers are then optionally dried or left to dry, for example at a temperature greater than or equal to 30°C.
  • the fibers can be dried at a temperature greater than or equal to 40°C. According to a particular embodiment, the fibers can be dried at a temperature above 40°C and below 100°C.
  • the fibers are dried, they are dried, in addition to a supply of heat, with a flow of air.
  • a mechanical action on the locks can be exerted such as combing, brushing, the passage of the fingers. This operation can also be carried out once the fibers have dried, naturally or not.
  • the drying step can be implemented with a drying device such as a helmet, a hair dryer, a climazon, etc.
  • the drying temperature is between 40 and 110°C, preferably between 50 and 90°C.
  • a shaping step can be implemented with, for example, a straightening iron, the temperature for the shaping step is between 110 and 220°C, preferably between 140 and 200°C.
  • a final rinse and/or shampoo can optionally be carried out.
  • Such an implementation advantageously makes it possible to obtain persistent, non-sticky deposits that are resistant to fatty substances such as edible oils or sebum, and to water as well as to shampoos.
  • a 3-step application advantageously improves cosmeticity and brings shine and volume to keratin materials.
  • the present invention relates to a process, in particular cosmetic, for keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/ or for caring for, styling and/or coloring keratin fibres, and preferably the hair, comprising a step of applying to said keratin materials a composition C1 according to the invention, said composition containing at least one copolymer CP as defined above, at least one fatty phase i) and optionally at least one cosmetic active ingredient, called “AC”, chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients from care of keratin materials, preferably of the skin, c) UV filters, and d) mixtures thereof.
  • a composition C1 containing at least one copolymer CP as defined above, at least one fatty phase i) and optionally at least one cosmetic active ingredient, called “AC”, chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures
  • the present invention relates to a particularly cosmetic process for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or for caring for , styling and/or coloring keratin fibers and preferably hair, comprising a step of applying to said keratin materials a composition C2 or C3 according to the invention, said compositions containing at least one CP copolymer, at least a crosslinking agent R and at least one fatty phase as defined above and optionally at least one cosmetic active agent AC as defined above, in particular at least one dyestuff and in particular at least one pigment.
  • the present invention relates to a particularly cosmetic process for keratin materials, in particular for caring for and/or making up the skin, lips, eyelashes and/or eyebrows and/or for caring for, styling and/or coloring the keratin fibers and preferably the hair, comprising at least the steps consisting in:
  • composition C1 (a) bringing all or part of the surface of said keratin materials into contact with a composition C1 according to the invention, and preferably devoid of crosslinking agent and optionally containing at least one cosmetic active agent AC as defined above;
  • step (b) bringing all or part of said surface into contact with a CR composition distinct from said composition C1 and comprising at least one crosslinking agent, in particular a crosslinking agent R as defined above, and preferably devoid of copolymer CP as defined previously; with steps (a) and (b) being able to be carried out, simultaneously or sequentially and it being understood that said method can optionally implement at least one cosmetic active ingredient, called “AC”, contained in composition C1 and/or in composition CR and/or optionally in a composition separate from C1 and CR, called “CAC”, said AC being chosen from a) coloring agents chosen from pigments, direct dyes, and mixtures thereof, b) active ingredients for the care of keratin materials, preferably skin, c) UV filters, and d) mixtures thereof.
  • AC cosmetic active ingredient
  • the present invention relates to a process for making up the skin, in particular the lips, the eyelashes, the eyebrows, comprising a step of applying to the skin or the said lips or the eyelashes or the eyebrows, of a C3, in particular containing at least one dyestuff in particular as defined previously and more particularly at least one pigment.
  • the present invention relates to a process for making up the skin, in particular the lips, eyelashes or eyebrows, comprising at least the sequential application: of a composition C1 as described above, of a crosslinking agent R or of a composition CR containing at least one crosslinking agent R, it being understood that said composition C1 or composition CR contains at least one dyestuff as defined previously, preferably at least one pigment.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • the present invention relates to a process for making up the skin, in particular the lips, the eyelashes or the eyebrows, comprising at least the three successive steps consisting in applying sequentially i) a CAC composition containing at least one dye AC, ii) a composition C1, iii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R, it being understood said method uses at least one AC cosmetic active agent designating a coloring material, in particular a pigment.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • said make-up process comprises at least the steps consisting of: applying to the skin, in particular of the lips, the eyelashes or the eyebrows, a composition
  • CAC containing at least one AC coloring matter, in particular at least one pigment and optionally at least one care active ingredient as defined above, applying, in contact with said CAC composition applied to the skin, the eyelashes or the eyebrows, a composition C1, applying, in contact with said composition C1, applied in contact with said composition CAC, a crosslinking agent R or a composition CR comprising at least one crosslinking agent.
  • the present invention relates to a care process, in particular non-therapeutic and cosmetic, for the skin, in particular the face or the lips, comprising a step of applying to the skin at least one composition C1, C2 or C3 according to the invention.
  • the present invention relates to a care process, in particular non-therapeutic and cosmetic, for the skin, in particular the face or the lips, comprising a step of applying to the skin a composition C3, in particular containing at least one moisturizing cosmetic active ingredient, in particular glycerol, and optionally at least one coloring material as defined above.
  • the present invention relates to a care process, in particular non-therapeutic and cosmetic, for the skin, in particular the face or the lips, comprising the sequential application:
  • composition C1 and/or said composition CR contains at least one moisturizing cosmetic active ingredient such as glycerol and optionally at least one coloring matter.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • the present invention relates to a care process, in particular non-therapeutic and cosmetic, for the skin, in particular the face or the lips, comprising at least the sequential application:
  • CAC composition containing at least one AC cosmetic active ingredient
  • a crosslinking agent R or a composition CR comprising at least one crosslinking agent R
  • said method uses at least one cosmetic active AC designating a care active, in particular a moisturizing active, in particular glycerol and optionally at least one dyestuff as defined above.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • said method comprises at least the three successive steps consisting in: applying to said skin a CAC composition containing at least one AC cosmetic active ingredient, in particular at least one care active ingredient, preferably at least one moisturizing active ingredient such as glycerol, and optionally at least one dyestuff as defined above, applying, in contact with said CAC composition applied to the skin, a composition C1, applying, in contact with said composition C1, applied in contact with said CAC composition, a crosslinking agent R or a composition CR comprising at least one crosslinking agent R.
  • a CAC composition containing at least one AC cosmetic active ingredient, in particular at least one care active ingredient, preferably at least one moisturizing active ingredient such as glycerol, and optionally at least one dyestuff as defined above, applying, in contact with said CAC composition applied to the skin, a composition C1, applying, in contact with said composition C1, applied in contact with said CAC composition, a crosslinking agent R or a composition CR comprising at least one crosslinking agent R.
  • the present invention relates to a process for dyeing keratin fibers, preferably human keratin fibers such as the hair, comprising a step of applying to said keratin fibers a composition C1, C2 or C3 according to the invention, said composition C1, C2 or C3 containing at least one dyestuff, in particular as defined above.
  • the present invention relates to a process for dyeing keratin fibres, preferably human keratin fibers such as the hair, comprising a step of applying to said keratin fibers a composition C3 according to invention, said composition C3 containing at least one coloring agent, in particular as defined above.
  • the present invention relates to a process for dyeing keratin fibers, preferably human keratin fibers such as the hair, comprising at least the sequential application:
  • composition C 1 or composition CR contains at least one dyestuff as defined above, preferably at least one pigment.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • the present invention relates to a process for dyeing keratin fibres, preferably human keratin fibers such as the hair, comprising at least the three successive steps consisting in applying sequentially i) a CAC composition containing at at least one coloring matter AC, ii) a composition C1, iii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R, it being understood that said method uses at least one cosmetic active ingredient AC designating a coloring matter, in particular a pigment.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • said coloring process comprises at least the steps consisting of: applying to said keratin fiber a CAC composition containing at least one AC coloring material, in particular at least one pigment and optionally at least one care active ingredient as defined previously, applying, in contact with said CAC composition applied to the keratin fiber, a composition C1, applying, in contact with said composition C1, applied in contact with said CAC composition, a crosslinking agent R or a composition CR comprising at least one crosslinking agent.
  • the present invention relates to a process for styling keratin fibers, in particular human keratin fibers and in particular the hair, comprising a step of applying to the keratin fibers a composition C1, C2 or C3 as previously defined according to the invention.
  • the present invention relates to a process for styling keratin fibres, preferably human keratin fibers such as the hair, comprising a step of applying to said keratin fibers a composition C3 according to the invention.
  • said composition C3 optionally containing at least one cosmetic active agent AC, in particular a dyestuff as defined above.
  • the present invention relates to a process for styling keratin fibres, preferably human keratin fibers such as, comprising at least the sequential application:
  • composition C1 or composition CR optionally contains at least one cosmetic active agent AC, in particular a coloring material as defined above, preferably at least one pigment.
  • composition C1 is applied before the crosslinking agent R or the composition CR containing at least one crosslinking agent R.
  • the present invention relates to a process for styling keratin fibres, preferably human keratin fibers such as the hair, comprising at least the three successive steps consisting in applying sequentially i) a CAC composition containing at at least one cosmetic active agent AC, ii) a composition C1, iii) a crosslinking agent R or a composition CR containing at least one crosslinking agent R.
  • the composition C1 is applied before the crosslinking agent R or the composition CR containing at least one cross-linking agent R.
  • said styling method comprises at least the steps consisting of:
  • the present invention also relates to a kit, in particular cosmetic, for keratin materials, in particular for the care and/or makeup of the skin and/or the lips, the eyelashes, the eyebrows and/or for the care, styling and/or coloring of keratin fibers and preferably the hair, comprising: a first compartment containing at least one fatty phase as defined above and at least one CP copolymer, optionally at least one cosmetic active ingredient AC as defined above, and preferably devoid of crosslinking agent R; a second compartment distinct from the first and containing at least one crosslinking agent R, in particular as defined above, preferably devoid of copolymer CP; and optionally, a third compartment distinct from the first and second compartments and containing at least one AC cosmetic active ingredient, identical to or different from that/those optionally contained in the first and second compartments and as defined above; it being understood that the first and/or second compartments may also contain one or more identical or different AC cosmetic active agents and that said AC cosmetic active agent
  • Styling application Styling evaluation protocol
  • a 1g lock of 90% white natural hair is wrapped around a brush.
  • the wick is measured immediately after application and 24 hours later, after storage at room temperature.
  • composition is prepared just before application.
  • the wick is dried with a hair dryer.
  • the resistance to the shampoo(s) can then be evaluated visually and/or by measuring the colorimetric data of each of the locks with a spectrophotometer of the Minolta CM-3610d type.
  • a first composition is applied to dry hair according to a bath ratio of 0.5 g of composition per gram of hair.
  • the wick is dried with a hair dryer.
  • top coat a second composition, called “top coat”, is applied according to a bath ratio of 0.5 g of composition per gram of hair.
  • the wick is again dried with a hair dryer.
  • the wick can also be smoothed using a straightening iron at a temperature of 180°C, applying 10 passes evenly throughout the wick.
  • the resistance to the shampoo(s) can then be evaluated visually and/or by measuring the colorimetric data of each of the locks with a spectrophotometer of the Minolta CM-3610d type.
  • a composition comprising a pigment in a cosmetic medium such as water or isododecane is applied to dry hair.
  • the wick is dried with a hair dryer.
  • a composition called a “base coat”, is applied according to a bath ratio of 0.5 g of composition per gram of hair.
  • the wick is again dried with a hair dryer.
  • top coat a composition, called “top coat”, is applied according to a bath ratio of 0.5 g of composition per gram of hair.
  • the wick is once again dried with a hair dryer.
  • the resistance to the shampoo(s) can then be evaluated visually and/or by measuring the colorimetric data of each of the locks with a spectrophotometer of the Minolta CM-3610d type (Illuminant D65).
  • the colored locks of hair are combed then moistened under a trickle of water at 35°C before being passed between the fingers 5 times then wrung out between two fingers.
  • a standard shampoo (Garnier Ultra Doux®) is then applied evenly to the locks at the rate of 0.4 g of shampoo per gram of lock by gently kneading the locks lengthwise. 10 passes are made from root to tip.
  • the locks soaked in shampoo are rinsed under running water at 35°C, passing each lock between the fingers (15 passages) then wringing them between two fingers before the next shampoo. Once the desired number of shampoos is achieved, the locks of hair are combed and then dried with a hair dryer.
  • a*, b*, L* represents lightness
  • a* represents the green/red color axis
  • b* the blue/yellow color axis.
  • the rise in hair color obtained with a composition according to the invention is acceptable, and on the other hand if the subsequent hair coloring, that is to say say before shampoo is affected by successive shampoos.
  • the rise in color, or capacity of the fibers to be colored is evaluated by the variation in coloring between the locks of the colored keratin fibers and of the same keratin fibers before coloring.
  • the build-up of the color on the hair (AE), or the capacity of the fibers to be colored, is evaluated by the variation in coloring between the locks of the colored keratin fibers and the same fibers before coloring according to the following equation:
  • L*, a* and b* represent the values measured after coloring the keratin fibers and Lo*, ao* and bo* represent the values measured before coloring the keratin fibers which are at least 90% natural white hair (B N).
  • the persistence of the color, or the resistance of the color of the keratinous fibers vis-à-vis external attacks such as shampoos, is evaluated by the difference in rise AE before and after attacks, here successive shampoos, of said fibers. The lower the variation, the more the color persists.
  • a composition containing a polymer CP with acetoacetate functions according to the invention and a crosslinking agent R which can be either an amine compound or a thiolated compound is produced using a Speed Mix (2 minutes at 3500 revolutions per minute).
  • This composition is applied to a Bioskin-type vitro support (support simulating an elastomeric skin) using a film puller (wet thickness 100 ⁇ m). The deposit is left to dry for 24 hours.
  • the composition, of the “base coat” type, containing a polymer with acetoacetate functions is produced using a Speed Mixer (2 minutes at 3500 revolutions per minute).
  • This "base coat” is applied to a Bioskin-type vitro support (support simulating an elastomer skin) using a film puller (wet thickness 100 ⁇ m). The deposit is left to dry for 24 hours.
  • a composition, of the “top coat” type, containing an amine compound is then applied. After 24 hours of drying, the deposits obtained are evaluated according to points 5 to 7 below.
  • the resistance is evaluated according to the following scale:
  • the Bioskin® plate on which the deposit is located is manually stretched 10 times. The degree of fragmentation (or cracking) of the deposit is then observed in order to determine whether it is cohesive or not.
  • the fragmentation of the film is evaluated according to the following scale:
  • Example A Preparation of copolymer 1: Isobornyl acrylate/acetoacetoxyethyl methacrylate (90/10)
  • the medium is degassed with argon and then heated to 90°C with stirring (100 revolutions/minute).
  • reaction medium reaches the temperature of 90° C., 338 g of a mixture composed of 200 g of isododecane, 135 g of isobornyl acrylate monomer, and 3 g of Trigonox 21S initiator, are poured into 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.
  • This polymer is characterized by gel permeation chromatography (GPC). The results are detailed in the table below.
  • the medium is degassed with argon and then heated to 90°C with stirring (100 revolutions/minute).
  • 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 initiator Trigonox 21S, are poured in 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 eliminate the residual monomers.
  • Example C Preparation of Copolymer 3: Isobornyl Acrylate/Butyl Acrylate/Acetoacetoxyethyl Methacrylate (60/30/10)
  • the medium is degassed with argon and then heated to 90°C with stirring (100 revolutions/minute).
  • 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 butyl acrylate and 3 g of initiator Trigonox 21S, are poured in 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 eliminate the residual monomers.
  • Example D Preparation of Copolymer 4: Isobornyl Acrylate/2-Ethylhexyl Acrylate/PDMS Methacrylate/Acetoacetoxyethyl Methacrylate (60/25/5/10)
  • 90 g of isobornyl acrylate, 37.5 g of 2-ethylhexyl acrylate, 7.5 g of PDMS methacrylate, 30 g of acetoacetoxy ethyl methacrylate, 100 g of an isododecane/ethyl acetate (70/30) solvent, and 100 g of isododecane alone are introduced.
  • the medium is degassed with argon and then heated to 90° C. with stirring (100 revolutions/minute).
  • reaction medium reaches the temperature of 90° C.
  • 338 g of a mixture composed of 200 g of isododecane, 90 g of isobornyl acrylate, 37.5 g of 2-ethylhexyl acrylate, 7.5 g of PDMS methacrylate and 3 g of Trigonox 21s initiator are cast in 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 eliminate the residual monomers.
  • compositions of examples 1 and 2 according to the invention comprising copolymer 2, as prepared in example B above, are prepared from the contents indicated in the table below. The contents are expressed in percentage by weight, relative to the total weight of the composition.

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EP21834810.0A 2020-12-23 2021-12-16 Kosmetische zusammensetzung enthaltend ein copolymer auf basis von acetoacetat-funktionen Pending EP4267088A1 (de)

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FR2014085A FR3117852B1 (fr) 2020-12-23 2020-12-23 Composition cosmétique comprenant un copolymère à base de fonctions acétoacétates
FR2108536A FR3117855B1 (fr) 2020-12-23 2021-08-05 : Composition cosmétique comprenant un copolymère à base de fonctions acétoacétates
PCT/EP2021/086180 WO2022136104A1 (fr) 2020-12-23 2021-12-16 Composition cosmétique comprenant un copolymère à base de fonctions acétoacétates

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