WO2020260641A1 - Méthode de traitement de matières kératiniques mettant en œuvre un polymère acrylique anhydride dans une dispersion huileuse, un plastifiant et un composé amine - Google Patents

Méthode de traitement de matières kératiniques mettant en œuvre un polymère acrylique anhydride dans une dispersion huileuse, un plastifiant et un composé amine Download PDF

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WO2020260641A1
WO2020260641A1 PCT/EP2020/068111 EP2020068111W WO2020260641A1 WO 2020260641 A1 WO2020260641 A1 WO 2020260641A1 EP 2020068111 W EP2020068111 W EP 2020068111W WO 2020260641 A1 WO2020260641 A1 WO 2020260641A1
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group
alkyl
chosen
composition
pigments
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Julien PORTAL
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LOreal SA
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LOreal SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—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
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—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 to a process for treating keratin materials, preferably human skin, in particular the lips, or to a process for treating keratin fibres, notably human keratin fibres such as the hair, in at least two steps involving, in a first stage, the application to said materials of an oily dispersion A) comprising i) particles of copolymers of alkyl acrylates and of anhydride acrylics, ii) stabilizers, iii) one or more hydrocarbon- based oils; and then, in a second stage, the application to said materials of a composition (B) comprising iv) one or more amine compounds, it being understood that the process of the invention uses v) one or more plasticizers, and vi) one or more cosmetic active agents chosen from a) dyes and/or pigments, b) active agents for caring for keratin materials, preferably the skin, and c) UV-screening agents and also d) mixtures thereof; ingredients v) and vi
  • Non-permanent dyeing or direct dyeing consists in dyeing keratin fibres with dye compositions containing direct dyes. These dyes are coloured and colouring molecules that have affinity for keratin fibres. They are applied to the keratin fibres for a time necessary to obtain the desired colouring, and are then rinsed out.
  • the standard dyes that are used are, in particular, dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, xanthene, acridine, azine or triarylmethane type, or natural dyes.
  • Some of these dyes may be used under lightening conditions, which enables the production of colourings that are visible on dark hair.
  • Another dyeing method consists in using pigments.
  • pigments Specifically, the use of pigment on the surface of keratin fibres generally makes it possible to obtain visible colourings on dark hair, since the surface pigment masks the natural colour of the fibre.
  • the use of pigment for dyeing keratin fibres is described, for example, in patent application FR 2 741 530, which recommends using, for the temporary dyeing of keratin fibres, a composition comprising at least one dispersion of film-forming polymer particles including at least one acid function and at least one pigment dispersed in the continuous phase of said dispersion.
  • patent EP 1 392 222 it is also known practice from patent EP 1 392 222 to use a cosmetic composition for caring for and/or treating keratin materials, comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds, and from patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds and a surfactant or a hair-conditioning agent.
  • Cosmetic products often require the use of a film-forming polymer to obtain a deposit of the product on keratin materials that has good cosmetic properties.
  • WO 2010/046229 describes dispersions in isododecane of acrylic polymers stabilized with stabilizing polymers. In the prepared by reversible chain-transfer controlled radical polymerization.
  • FR 1 362 795 describes the use of dispersions of surface-stabilized polymer particles containing hydrocarbon-based oils for making up the lips and the eyelashes.
  • the aim of the present invention is to provide a method for treating keratin fibres that has good resistance to attacking factors such as brushing, does not leach, is resistant to sweat, light and bad weather, and is fast with respect to shampoo washing and to the various attacking factors to which said fibres may be subjected, without degrading said fibres, and while keeping the keratin fibres perfectly individualized.
  • Another aim of the present invention is to provide a method for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin, which has good resistance to external attacking factors, and over time, of the action of the cosmetic active agent(s) such as the tensioning, care or ultraviolet (UV) protection effect, but also good persistence of makeup such as lip makeup.
  • the technical problem has been solved by the process of the invention, which is a process for treating keratin materials, preferably human keratin materials, in particular the skin and more preferentially facial skin such as the lips, or keratin fibres, notably human keratin fibres such as the hair, comprising:
  • composition (B) which is preferably anhydrous, comprising:
  • the process of the invention uses v) one or more plasticizers, and vi) one or more cosmetic active agents chosen from a) dyes and/or pigments, b) active agents for caring for keratin materials, notably the skin, and c) UV-screening agents, and also d) mixtures thereof, ingredients v) and vi) possibly being found in composition (A), and/or in composition (B), and/or in another composition (C).
  • one or more plasticizers and vi) one or more cosmetic active agents chosen from a) dyes and/or pigments, b) active agents for caring for keratin materials, notably the skin, and c) UV-screening agents, and also d) mixtures thereof, ingredients v) and vi) possibly being found in composition (A), and/or in composition (B), and/or in another composition (C).
  • This process for treating keratin materials in at least two successive steps using, during a first step, the oily dispersion (A) as defined above and then, during a following step, a composition (B) comprising one or more amine compounds as defined above and optionally a composition (C), makes it possible to obtain a treatment of said keratin materials that is notably resistant to sweat, to shower gels, to water and to fatty substances, in particular plant or animal food oils, and more particularly plant oils such as olive oil, sunflower oil, walnut oil, hazelnut oil, etc.
  • the keratin fibre treatment process of the present patent application is also suitable for making up the skin or the lips, such as foundations and lipsticks.
  • a subject of the present patent application is also a process, notably a cosmetic process, for caring for or making up the skin or the lips, more particularly facial skin, in particular wrinkled skin, comprising the topical application to the skin or the lips of the compositions, notably the cosmetic compositions, (A) and (B) and optionally (C) as described previously.
  • a cosmetic process for caring for or making up the skin or the lips, more particularly facial skin, in particular wrinkled skin, comprising the topical application to the skin or the lips of the compositions, notably the cosmetic compositions, (A) and (B) and optionally (C) as described previously.
  • a subject of the invention is also a process, notably a cosmetic process, for caring for the skin, more particularly facial skin, in particular wrinkled skin, comprising the topical application to the skin of the compositions, notably the cosmetic compositions, (A) and (B) and optionally (C), as described previously.
  • a cosmetic process for caring for the skin, more particularly facial skin, in particular wrinkled skin, comprising the topical application to the skin of the compositions, notably the cosmetic compositions, (A) and (B) and optionally (C), as described previously.
  • the process of the present patent application is in particular intended for smoothing human facial and/or bodily skin and/or for reducing or eliminating the signs of skin ageing, in particular for reducing or eliminating wrinkles and/or fine lines of the skin.
  • a subject of the invention is also the cosmetic use, as a skin tensioning agent, in particular for wrinkled-skin, of the compositions, notably the cosmetic compositions, (A) and (B) and optionally (C) as described previously.
  • tensioning agent means compounds that are capable of having a noticeable tensioning effect, i.e. of smoothing out the skin and immediately, reducing the wrinkles and fine lines, or even making them disappear.
  • the tensioning effect may be characterized by an in vitro shrinkage test.
  • - an“alkyl radical ⁇ ’ is a linear or branched saturated CrCs, in particular C 1 -C 6 , preferably Ci- C4 hydrocarbon-based group such as methyl, ethyl, isopropyl and tert-butyl;
  • - an“alkylene radical ⁇ ’ is a linear or branched divalent saturated CrCs, in particular C 1 -C 6 , preferably C 1 -C 4 hydrocarbon-based group such as methylene, ethylene or propylene;
  • - a“cycloalkyl ⁇ ’ radical is a saturated cyclic hydrocarbon-based group comprising from 1 to 3 rings, preferably 2 rings, and comprising from 3 to 13 carbon atoms, preferably between 5 and 10 carbon atoms, such as cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, or isobornyl, the cycloalkyl radical possibly being substituted with one or more (CrC4)alkyl groups such as methyl; preferably, the cycloalkyl group is an isobornyl group.
  • cyclic radical is a cyclic saturated or unsaturated, aromatic or non-aromatic hydrocarbon-based group comprising from 1 to 3 rings, preferably 1 ring, and comprising from 3 to 10 carbon atoms, such as cyclohexyl or phenyl;
  • - an“aryl ⁇ ’ radical is a cyclic unsaturated aromatic hydrocarbon-based radical comprising from 6 to 12 carbon atoms, which is mono- or bicyclic, fused or unfused; preferably, the aryl group comprises 1 ring and to 6 carbon atoms, such as phenyl;
  • - an“a/y/oxy” radical is an aryl-oxy, i.e. aryl-O-, radical, with aryl as defined previously, preferably phenoxy;
  • an“ aryl(Ci-C4)alkox y” radical is an aryl-(Ci-C 4 )alkyl-0-, radical, preferably benzoxy;
  • olysaccharides refers to a polysaccharide sugar which is a polymer constituted of several saccharides bonded together via O-oside bonds, said polymers being constituted of monosaccharide units as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6; in particular, the monosaccharide units are linked together via a 1 ,4 or 1 ,6 bond as a (alpha) or b (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from a certain number of saccharides (or monosaccharides) having the general formula: - [Cx(H 2 0)y)]n- where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive and preferably x
  • Ri and R 2 represent a hydrogen atom.
  • the process of the invention involves at least one oily dispersion (A) of i) particles of at least one polymer surface-stabilized with ii) at least one stabilizer in a preferably anhydrous medium, also containing iii) at least one hydrocarbon-based oil.
  • the dispersions according to the invention are constituted of particles, which are generally spherical, of at least one surface-stabilized polymer, in a non-aqueous medium.
  • the particle(s) of the dispersion of the process of the invention are constituted of one or more ethylenic copolymers of a) (CrC4)alkyl (Ci-C4)(alkyl)acrylate and of b) an ethylenically unsaturated anhydride compound.
  • the ethylenically unsaturated anhydride compound is a cyclic compound, which is preferably 5- or 6-membered, and comprising
  • the polymer constituting the particles i) is a copolymer of acrylate:
  • the polymer of the particles is a polymer of C1-C4 alkyl
  • the monomers a) are preferably chosen from methyl (meth)acrylate, ethyl
  • a C1-C4 alkyl acrylate monomer is advantageously used.
  • a) is chosen from methyl acrylate and ethyl acrylate.
  • the polymer of the particles also comprises an ethylenically unsaturated anhydride monomer b).
  • the ethylenically unsaturated anhydride compound(s) b) of the invention are chosen from derivatives of maleic anhydride (lb) and itaconic anhydride (lib):
  • R a , R b and R c which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group; preferably, R a , R b , and R c represent a hydrogen atom.
  • R a , R b , and R c represent a hydrogen atom.
  • the polymer(s) of the particles comprise, or essentially consist of, from 80 to 99.99% by weight of monomer a) and from 0.01 to 20% by weight of monomer b), relative to the total weight of the polymer.
  • the polymer of the particles may be chosen from:
  • the polymer of the particles is a non-crosslinked polymer.
  • the polymer of the particles of the dispersion preferably has a number-average molecular weight ranging from 2000 to 10 000 000.
  • the polymer of the particles may be present in the dispersion in an amount ranging from 20% to 60% by weight relative to the total weight of the dispersion (A), in particular between 21% and 58.5% by weight relative to the total weight of the dispersion (A), preferably ranging from 30% to 50% by weight relative to the total weight of the dispersion (A), more preferentially ranging from 36% to 42% by weight relative to the total weight of the dispersion (A).
  • the dispersion (A) according to the invention also comprises one or more stabilizers ii). Preferably, only one type of stabilizer ii) is used in the invention.
  • the stabilizer(s) of the invention are constituted of ethylenic polymers chosen from c) polymers of (C3-Ci2)cycloalkyl (Ci-C 6 )(alkyl)acrylate monomers; and d)
  • the stabilizer ii) is an isobornyl (meth)acrylate polymer chosen from isobornyl (meth)acrylate homopolymer and statistical copolymers of isobornyl
  • (meth)acrylate and C 1 -C 4 alkyl (meth)acrylate which are preferably present in an isobornyl (meth)acrylate/Ci-C4 alkyl (meth)acrylate weight ratio of greater than 4; advantageously, said weight ratio ranges from 4.5 to 19.
  • the defined weight ratio makes it possible to obtain a polymer dispersion that is stable, notably after storage for seven days at room temperature.
  • the stabilizer is chosen from:
  • the sum of ii) stabilizer(s) + i) particle(s) of polymer(s) present in the dispersion (A) comprises from 10% to 50% by weight of copolymers d) and from 50% to 90% by weight of polymers c), relative to the total weight of the sum of ii) stabilizer(s) + i) particle(s) of polymer(s).
  • the sum of ii) stabilizer(s) + ii) particle(s) of polymer(s) present in the dispersion comprises from 15% to 30% by weight of copolymers d) and from 70% to 85% by weight of polymers c), relative to the total weight of the sum of ii) stabilizer(s) + i) particle(s) of polymer(s).
  • the dispersion (A) according to the invention comprises one or more identical or different, preferably identical, hydrocarbon-based oils.
  • o/7 means a fatty substance that is liquid at room temperature (25°C) and at atmospheric pressure.
  • hydrocarbon-based oiT means an oil formed essentially from, or even constituted of, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain hydroxy, ester, ether, carboxylic acid, amine and/or amide groups.
  • the hydrocarbon-based oil may be volatile or non-volatile.
  • the hydrocarbon-based oil(s) are volatile or are a mixture of different volatile oils, more preferentially chosen from isododecane and octyldodecanol.
  • the hydrocarbon-based oil(s) are a mixture of a volatile oil and a non-volatile oil.
  • volatile oit' refers to an oil (or non-aqueous medium) that can evaporate on contact with the skin in less than one hour, at room temperature and at atmospheric pressure.
  • the volatile oil is a volatile cosmetic oil, which is liquid at room temperature, notably having a non-zero vapour pressure, at room temperature and at atmospheric pressure, in particular having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10 3 to 300 mmHg), preferably ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and preferentially ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg);
  • non-volatile oit refers to an oil with a vapour pressure of less than 0.13 Pa.
  • Volatile silicone oils that may be mentioned include volatile linear or cyclic silicone oils, notably those with a viscosity ⁇ 8 centistokes (cSt) (8 c 10 6 m 2 /s), and notably containing from 2 to 10 silicon atoms and in particular from 2 to 7 silicon atoms, these silicones optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils that may be used in the invention, mention may notably be made of dimethicones with viscosities of 5 and 6 cSt, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane,
  • heptamethylhexyltrisiloxane heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.
  • non-volatile silicone oils mention may be made of linear or cyclic nonvolatile polydimethylsiloxanes (PDMSs); polydimethylsiloxanes including alkyl, alkoxy and/or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenyl silicones, phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones,
  • diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsiloxysilicates and pentaphenyl silicone oils other than the plasticizers v) of the invention are diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsiloxysilicates and pentaphenyl silicone oils other than the plasticizers v) of the invention.
  • the hydrocarbon-based oil may be chosen from hydrocarbon-based oils containing from 8 to 14 carbon atoms, and notably:
  • C S -CM alkanes for instance C S -CM isoalkanes of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane and, for example, the oils sold under the trade names Isopar or Permethyl,
  • esters containing from 3 to 8 carbon atoms in total
  • ethyl acetate methyl acetate
  • propyl acetate n-butyl acetate
  • oils of plant origin such as triglycerides consisting of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are notably heptanoic acid or octanoic acid triglycerides, or alternatively wheatgerm oil, sunflower oil, grapeseed oil, sesame seed oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cotton oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil or musk rose oil; shea butter; or
  • hydrocarbons of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam®, squalane and liquid paraffins, and mixtures thereof;
  • oils of formula RIC(0)-0-R 2 in which Ri represents a linear or branched fatty acid residue including from 1 to 40 carbon atoms and R2 represents an, in particular branched, hydrocarbon-based chain containing from 1 to 40 carbon atoms, on the condition that Ri + R2 > 10, for instance purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12 to C15 alcohol benzoates, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, isostearyl isostearate, 2-hexyldecyl laurate, 2-octyldecyl palmitate, 2-octyldodecyl myristate, alcohol or polyalcohol heptanoates, octanoates, decanoates or ricinole
  • - fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol and 2- undecylpentadecanol.
  • the dispersion (A), in addition to the hydrocarbon-based oil, may comprise a silicone oil. If silicone oil is present in the dispersion (A), it is preferably present in an amount which does not exceed 10% by weight relative to the weight of the dispersion (A), more particularly in an amount of less than 5% and more preferentially 2%.
  • silicone oil means an oil comprising at least one silicon atom and notably at least one Si- O group.
  • the silicone oil may be volatile or non-volatile.
  • the dispersion (A) comprises a hydrocarbon-based oil in a content ranging from 60 to 100% by weight of the total weight of the oils present in the composition and from 0 to 40% by weight of silicone oil.
  • the composition contains as oil only a hydrocarbon-based oil.
  • the hydrocarbon-based oil(s) of the invention are apolar, i.e. formed solely of carbon and hydrogen atoms.
  • the hydrocarbon-based oils are preferably chosen from hydrocarbon-based oils containing from 8 to 14 carbon atoms, which are in particular volatile, more particularly the apolar oils, described previously.
  • the hydrocarbon-based oil(s) of the invention are isododecane.
  • the hydrocarbon-based oil(s) are a mixture of non-volatile and volatile oil; preferably, the mixture comprises isododecane as volatile oil.
  • the non-volatile oil is a phenyl silicone oil, preferably chosen from pentaphenyl silicone oils other than the plasticizers v) of the invention.
  • compositions used in the process, (B) and (C) also comprise at least one oil as defined previously, notably a hydrocarbon-based oil.
  • the polymer particles of the dispersion preferably have a number-mean size ranging from 5 to 500 nm, notably ranging from 10 to 400 nm and better still ranging from 20 to 300 nm.
  • the final particle size is preferably greater than 100 nm.
  • the number-mean size ranges from 100 nm to 500 nm, more particularly ranges from 150 nm to 400 nm and even more particularly ranges from 160 nm to 300 nm.
  • the mean particle size is determined via standard methods known to those skilled in the art.
  • a Malvern brand NanoZS model laser particle size analyser (which is particularly suitable for submicron dispersions) makes it possible to measure the size distribution of these samples.
  • the operating principle of this type of machine is based on dynamic light scattering (DLS), also known as quasi-elastic light scattering (QELS) or photon correlation spectroscopy (PCS).
  • DLS dynamic light scattering
  • QELS quasi-elastic light scattering
  • PCS photon correlation spectroscopy
  • the sample is pipetted into a disposable plastic cuvette (four transparent faces, side length of 1 cm and volume of 4 ml_) placed in the measuring cell.
  • the data are analysed on the basis of a cumulative method which leads to a unimodal particle size distribution characterized by an intensity-mean diameter d(nm) and a size polydispersity factor Q.
  • the results may also be expressed in the form of statistical data such as D10; D50 (median), D90 and mode.
  • Nanoparticle Tracking Analysis NTA
  • LS laser scattering
  • AES acoustic extinction spectroscopy
  • the dispersion according to the invention may be prepared in the following manner: [0084] The polymerization is performed in“dispersion", i.e. by precipitation of the polymer being formed, with protection of the particles formed with one or more stabilizers, preferably one stabilizer.
  • the stabilizing polymer (or stabilizer ii)) is prepared by mixing the constituent monomer(s) of the stabilizing polymer c) or d) with vii) a free-radical initiator, in a solvent known as the synthesis solvent, and by polymerizing these monomers;
  • the constituent monomer(s) of the polymer of the particles i) are added to the stabilizing polymer formed in the preceding step and polymerization of these added monomers is performed in the presence of the free-radical initiator.
  • the polymerization may be performed in an apolar organic solvent (synthesis solvent), followed by adding the non-volatile hydrocarbon-based oil (which should be miscible with said synthesis solvent) and selectively distilling off the synthesis solvent.
  • synthesis solvent apolar organic solvent
  • the plasticizer(s) v) are added during the first step. According to another variant, the plasticizer(s) v) are added during the second step or after the second step.
  • the plasticizer(s) v) are added after the second step.
  • the cosmetic agent(s), preferably the pigment(s), are added during the first step.
  • the cosmetic agent(s), preferably the pigment(s) are added during the second step or after the second step.
  • a synthesis solvent which is such that the monomers of the stabilizing polymer and the free-radical initiator are soluble therein, and the polymer particles obtained are insoluble therein, so that they precipitate therein during their formation, is thus chosen.
  • the synthesis solvent is chosen which is apolar and organic, preferably chosen from alkanes such as heptane or cyclohexane.
  • the non-aqueous medium is a volatile hydrocarbon-based oil iii
  • the polymerization may be performed directly in said oil, which thus also acts as synthesis solvent.
  • the monomers should also be soluble therein, as should the free-radical initiator, and the polymer of the particles which is obtained should be insoluble therein.
  • the cosmetic agent(s) v), preferably the pigment(s), may be added during the first step.
  • the dye(s) and/or pigment(s) are added during the second step or after the second step.
  • a synthesis solvent which is such that the monomers of the stabilizing polymer and the free-radical initiator are soluble therein, and the polymer particles obtained are insoluble therein, so that they precipitate therein during their formation, is thus chosen.
  • the synthesis solvent is chosen which is apolar and organic, preferably chosen from alkanes such as heptane or cyclohexane.
  • the non-aqueous medium is a volatile hydrocarbon-based oil iii
  • the polymerization may be performed directly in said oil, which thus also acts as synthesis solvent.
  • the monomers should also be soluble therein, as should the free-radical initiator, and the polymer of the particles which is obtained should be insoluble therein.
  • the monomers are preferably present in the synthesis solvent, before polymerization, in a proportion of 5% to 45% by weight.
  • the total amount of the monomers may be present in the solvent before the start of the reaction, or part of the monomers may be added gradually as the polymerization reaction proceeds.
  • the polymerization is preferentially performed in the presence vii) of one or more free-radical initiators, notably of the type such as:
  • tert-butyl peroxy-2-ethylhexanoate Trigonox 21S
  • 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane Trigonox 141
  • tert-butyl peroxypivalate Trigonox 25C75 from AkzoNobel; or
  • azo in particular chosen from AIBN: azobisisobutyronitrile; V50: 2,2'-azobis(2- amidinopropane) dihydrochloride.
  • the polymerization is preferably performed at a temperature ranging from 70 to 110°C and at atmospheric pressure.
  • the polymer particles i) are surface-stabilized, when they are formed during the polymerization, by means of the stabilizer ii).
  • the stabilization may be performed by any known means, and in particular by direct addition of the stabilizer ii), during the polymerization.
  • the stabilizer ii) is preferably also present in the mixture before polymerization of the monomers of the polymer of the particles i). However, it is also possible to add it continuously, notably when the monomers of the polymer of the particles i) are also added continuously.
  • From 10% to 30% by weight and preferably from 15% to 25% by weight of the stabilizer(s) may be used relative to the total weight of monomers used (stabilizer ii) + polymer particles i)).
  • the polymer particle dispersion (A) advantageously comprises from 30% to 65% by weight of solids relative to the total weight of said dispersion and preferably from 40% to 60% by weight relative to the total weight of said dispersion.
  • composition according to the invention preferably comprises a content of polymers of particle i) + dispersing polymers ii) ranging from 1 % to 50% by weight and preferably ranging from 2% to 30% by weight relative to the total weight of composition (A).
  • the dispersion (A) according to the invention is an anhydrous composition.
  • anhydrous dispersion or composition refers to a dispersion or composition containing less than 2% by weight of water, or even less than 0.5% of water, and notably free of water. Where appropriate, such small amounts of water may notably be introduced by ingredients of the composition that may contain residual amounts thereof.
  • the dispersion (A) is in inverse emulsion, i.e. of water-in-oil type (W/O).
  • the composition comprises one or more surfactants, which are preferably nonionic.
  • the inverse emulsions of (A) are preferably chosen in makeup, notably in mascaras.
  • Composition (B) of the process of the invention comprises one or more amine compounds iv).
  • the amine compounds used in the process of the invention are chosen from: e) polyamines bearing several primary amine and/or secondary amine groups, and f) amino alkoxysilanes,
  • the amine compound(s) used in the process according to the invention are notably chosen from amino alkoxysilane compounds, diamine compounds and triamine compounds.
  • compound(s) particularly comprise from 2 to 20 carbon atoms;
  • compound(s) are notably non-polymeric.
  • non-polymeric compound(s) refers to one or more compounds which is or are not directly obtained via a monomer polymerization reaction.
  • Polyamine compounds that may notably be mentioned include 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, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1 ,4-diaminobutane, N,N-dimethyldipropylenetriamine, 1 ,2-bis(3- aminopropylamino)ethane, N,N’-bis(3-aminopropyl)-1 ,3-propanediamine,
  • ethylenediamine 1 ,3-propylenediamine, 1 ,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine and spermidine.
  • the amine compound(s) iv) are chosen from f) amino alkoxysilanes such as those of formula (IVa):
  • R'i is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C10 hydrocarbon- based chain, substituted with one or more groups chosen from the following groups: i) primary amine NH2 or secondary amine N(H)R with R representing a (CrC4)alkyl group, ii) aryl or aryloxy substituted with an amino or (Ci-C4)alkylamino group or with a C1-C4 aminoalkyl group, and iii) aldehyde -C(0)-H, carboxyl -C(0)-OH, amide -C(0)-NH 2 or urea -NH-C(0)-NH 2 ; R' I is optionally interrupted in its hydrocarbon-based chain with one or more heteroatoms (notably O, S, NH), a carbonyl group (CO), or a combination thereof such as ester -C(0)-0-, or amide -C(0)-NH-, R'i being bonded
  • R’2 and R’3 which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms,
  • 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 an 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 a methyl or ethyl group.
  • R'i is an acyclic chain.
  • R’1 is a linear or branched, saturated or unsaturated C1-C6 hydrocarbon-based chain substituted with an amine NH2 or N(H)R group, with R representing a C1-C6 alkyl group, C3-C6 cycloalkyl, or C 6 aromatic.
  • R'i is a saturated linear C1-C6 hydrocarbon-based chain substituted with an amine group NH2.
  • R'i is a saturated linear C2-C4 hydrocarbon-based chain substituted with an amine group N H2.
  • R'i is a saturated linear C1-C6 hydrocarbon-based chain substituted with an amine group NH2.
  • 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 amino alkoxysilane of formula (IVa) 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 aminopropyltriethoxysilane
  • AETES 3-aminoethyltriethoxysilane
  • 3- aminopropylmethyldiethoxysilane N-(2-aminoethyl)-3-aminopropyltriethoxysilane
  • 3-(m- aminophenoxy)propyltrimethoxysilane 3-(
  • the amino alkoxysilane (IVa) is chosen from 3- aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3- aminopropylmethyldiethoxysilane and N-(2-aminoethyl)-3-aminopropyltriethoxysilane.
  • the amino alkoxysilane (IVa) is 3-aminopropyltriethoxysilane
  • the amine compound(s) are 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, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1 ,4- diaminobutane, N,N-dimethyldipropylenetriamine, 1 ,2-bis(3-aminopropylamino)ethane, N,N’-bis(3-aminopropyl)-1 ,3-propan
  • APTES 3- amino
  • the amine compound is chosen from ethylenediamine, 1 ,3- propylenediamine, 1 ,4-butylenediamine and 3-aminopropyltriethoxysilane (APTES).
  • APTES 3-aminopropyltriethoxysilane
  • the amine compound is ethylenediamine or 3- aminopropyltriethoxysilane (APTES).
  • the amine compound(s) may also be chosen from e) polyamines bearing several primary amine and/or secondary amine groups and in particular amine polymers, notably having a weight-average molecular weight ranging from 500 to 1 000 000, preferably ranging from 500 to 500 000, and preferentially ranging from 500 to 100 000.
  • amine or polyamine polymers e use may be made of poly((C2- C5)alkyleneimines), and in particular:
  • polyethyleneimines and polypropyleneimines notably poly(ethyleneimine)s (for example the product sold under the reference 46,852-3 by the company Aldrich Chemical);
  • polyamino acids containing NH2 groups such as polylysine, for example the product sold by the company JNC Corporation (formerly Chisso); aminodextran, such as the product sold by the company CarboMer Inc;
  • polydi(Ci-C4)alkylsiloxanes in particular polydimethylsiloxanes, comprising amine groups at the chain end or on side chains, are particularly end or side amino(Ci-C 6 )alkyl groups such as aminopropyl, more particularly those of formula (IVb) or (IVc) or (IVd):
  • R a and R b which may be identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, (CrC4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Ci-C4)alkoxy such as benzoxy, preferably (CrC4)alkyl such as methyl, R c and R' c , which may be identical or different, preferably identical, represent a hydrogen atom, a (Ci-C4)alkyl group, an amino(Ci-C4)alkyl or (Ci-C4)alkylamino(Ci-C4)alkyl group, preferably a hydrogen atom or an amino(Ci-C4)alkyl group such as aminoethyl; X represents a covalent bond, an oxygen
  • polydi(Ci-C4)alkylsiloxanes of formula (IVb) are of formula (IV’b) or (IV"b) below:
  • formula (IVb) the value of n is such that the weight-average molecular weight of the silicone is between 500 and 55 000.
  • aminosilicone (IVb) or (IVb) mention may be made of those sold under the names DMS-A1 1 , DMS-A12, DMS-A15, DMS-A21 , DMS-A31 , DMS-A32 and DMS-A35 by the company Gelest;
  • ALK and ALK' are identical and represent a (CrC4)alkylene group such as propylene
  • R c and R' c are identical and represent an amino(Ci-C4)alkyl group such as aminoethyl
  • Dimethoxysilyl Ethylenediaminopropyl Dimethicone (RN: 71750-80-6), under the trade name GP-RA-157, sold by Genesee Polymers.
  • R a , R b , and R d which may be identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, (CrC4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Cr C4)alkoxy such as benzoxy, preferably (CrC4)alkyl such as methyl, R d may also represent a (CrC 6 )alkyl group substituted with a (Ci-C4)alkylamino or amino group, R c represents a hydrogen atom or a (CrC4)alkyl group, preferably a hydrogen atom; ALK represents a (Ci- C 6 )alkylene group, preferably (CrC4)alkylene such as propylene; n and m
  • polydi(Ci-C4)alkylsiloxanes of formula (IVc) have the formula (IV’c) below:
  • formula (IV’c) the values of n and m are such that the weight-average molecular weight of the silicone is between 1000 and 55 000.
  • silicone (IVc) 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;
  • R a and R b which may be identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, (CrC4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Ci-C4)alkoxy such as benzoxy, preferably (CrC4)alkyl such as methyl, and R d represents a (Ci-Ce)alkyl group optionally substituted with a (Ci-C4)alkylamino or amino group, preferably (Ci- C4)alkyl, such as isobutyl, tert-butyl or n-butyl, R c represents a hydrogen atom or a (Ci- C4)alkyl group, preferably a hydrogen atom;
  • ALK represents a (Ci-Ce)alkylene group,
  • polydi(Ci-C4)alkylsiloxanes of formula (IVd) have the formula (IV’d) below:
  • formula (IV’d) the value of n is such that the weight-average molecular weight of the silicone is between 500 and 3000.
  • silicones (IVd) mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest;
  • R a and R b which may be identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, (CrC4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Ci-C4)alkoxy such as benzoxy, preferably (CrC4)alkyl such as methyl,
  • - R c represents a hydrogen atom or a (CrC4)alkyl group, preferably a hydrogen atom, - R e represents a hydroxyl, (CrC4)alkoxy, amino or (Ci-C4)alkylamino group,
  • R f represents a (CrC4)alkyl group such as methyl, a (CrC4)alkoxy group such as methoxy, a hydroxyl or -0-(SiR 2 ) > cR’ group with R representing a (CrC4)alkyl or (CrC4)alkoxy group and R' representing a (CrC4)alkoxy or hydroxyl group; preferably, R f represents a (Ci- C4)alkyl, (CrC4)alkoxy or -0-(SiR 2 ) > cR’ group with R representing a (CrC4)alkyl group such as methyl and R' a hydroxyl or (CrC4)alkoxy group such as methoxy;
  • R 9 represents a hydrogen atom or a (Ci-Ce)alkyl group
  • ALK and ALK' which may be identical or different, represent a (Ci-Ce)alkylene group, preferably (CrC4)alkylene such as ethylene or propylene; n and m, which may be identical or different, represent an integer greater than 2, p and x are integers greater than or equal to 0; preferably, p is between 2 and 20 and more particularly the values of m, n, p and x are such that the weight-average molecular weight of the silicone is between 2000 and 700 000, preferentially between 5000 and 500 000.
  • - ALK represents a (Ci-Ce)alkylene group, preferably ethylene
  • - ALK represents a (Ci-Ce)alkylene group, preferably propylene
  • n and p are such that the weight-average molecular weight of the compound is between approximately 5000 and 500 000; preferably, p represents an integer of between 8 and 20;
  • the amodimethicones of formula (IVe) are chosen from those of formula:
  • R a and R b which may be identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, (CrC4)alkoxy such as methoxy, preferably (CrC4)alkyl such as methyl,
  • R c represents a hydrogen atom or a (CrC4)alkyl group, preferably a hydrogen atom
  • R 9 represents a hydrogen atom or a (CrC4)alkyl group
  • R f represents a (CrC4)alkyl group such as methyl, a (CrC4)alkoxy group such as methoxy, or -0-(SiR 2 ) > cR' with R representing a (CrC4)alkyl group such as methyl and R’ a hydroxyl or (CrC4)alkoxy group such as methoxy;
  • R 9 represents a hydrogen atom or a (Ci-Ce)alkyl group
  • - ALK represents a (Ci-Ce)alkylene group, preferably ethylene
  • - ALK represents a (Ci-Ce)alkylene group, preferably propylene
  • n is an integer greater than or equal to 0; preferably, the values of m, n and x are such that the weight-average molecular weight of the silicone is between 2000 and 700 000, preferentially between 5000 and 500 000.
  • polyether amines known notably under the reference Jeffamine from the company Huntsman; and notably: polyethylene glycol and/or polypropylene glycol a,w-diamines (bearing a chain-end amine function), such as those sold under the names Jeffamine D- 230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003; - polytetrahydrofuran (or polytetramethylene glycol) a,w-diamines, polybutadiene a,w- diamines;
  • PANAM polyamidoamine
  • poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine side functions such as poly(3-aminopropyl)methacrylamide or poly(2-aminoethyl) methacrylate.
  • polyamine compounds bearing several amino polymer primary amine and/or secondary amine groups e use is preferably made of polydi(Ci-C4)alkylsiloxanes comprising primary amine groups at the chain end or on side chains.
  • the polyamine compounds e) used in the process according to the invention are chosen from polydi(Ci-C4)alkylsiloxanes comprising primary amine groups at the chain end and/or on side chains.
  • the amine compound(s) iv) are chosen from polysaccharide(s) bearing amine group(s), and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the polysaccharide(s) bearing amine group(s) have an average molecular weight MW of less than or equal to 400 kDa, particularly less than 200 kDa.
  • the polysaccharide(s) bearing amine group(s) have a low average molecular weight MW i.e. an MW ⁇ 100 kDa, preferentially an average MW which is ⁇ 40 kDa, more preferentially an average MW which is between 1 kDa and 30 kDa inclusive, even more preferentially an average MW which is between 3 kDa and 28 kDa inclusive.
  • the polysaccharide(s) bearing amine group(s) of the invention are of natural animal or plant origin, or else are derived from synthesis, semisynthesis or biosynthesis.
  • the polysaccharide(s) bearing amine group(s) are chosen from those containing C5-C7 saccharide units and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • polysaccharide(s) bearing amine group(s) of the invention are C 6 saccharide units bearing amine group(s); these polysaccharides bearing amine group(s) are then referred to as polyhexosamines.
  • polysaccharide bearing amine group(s) of the invention are of b (beta) anomeric configuration and/or of D configuration.
  • polysaccharide with amine group(s) b) are linked together between the atoms of carbon 1 of one saccharide unit and of carbon 4 of the other saccharide unit, denoted (1 4), such as the polysaccharide bearing amine group(s) of formula (B) below, and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
  • each saccharide unit may be identical or different;
  • - n is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, and more particularly between 5 and 2500, preferentially between 10 and 2300;
  • R a , R b and R c which may be identical or different, represent i) a hydroxyl group, ii) a (Ci- C4)alkoxy group, the alkyl group of which may be optionally substituted, notably with one or more hydroxyl groups, iii) a carboxyl group, and iv) a group NR1 R2, with Ri and R2 as defined previously; in particular, Ri and R2 are chosen from a hydrogen atom and -C(0)-R’i in which R'i is as defined previously; preferably Ri and R2 represent i) a hydrogen atom or ii) -C(O)- R'i with R'i representing a (CrC4)alkyl group such as methyl;
  • At least one of the radicals R a , R b or R c of at least one saccharide unit represents a group NR1 R2 and that at least one of the groups NR1 R2 of at least one saccharide unit represents an NH2 group; preferably, R a of at least one saccharide unit represents a group NR1 R2 with Ri which represents a hydrogen atom and R2 is chosen from i) a hydrogen atom or ii) a group -C(0)-R'i , and R b and R c represent a hydroxyl group, it being understood that at least one of the groups NR1 R2 of at least one saccharide unit represents an NH2 group.
  • polysaccharide(s) bearing amine group(s) of the invention are of formula (Bi) below, and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
  • - R’ represents a hydrogen atom or a (Ci-C4)alkylcarbonyl group such as acetyl CH 3 -C(0)-
  • - R" represents a hydrogen atom or a (CrC4)alkyl group optionally substituted with a carboxyl group such as -CH(CC>2H)-CH3;
  • - n is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300;
  • At least one saccharide unit bears an NH2 amino group and at least one other saccharide unit bears at least one N(H)-R' group with R' representing a (Ci-C4)alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • the saccharide units of formula (B) or (Bi) are of D configuration, also referred to as D-glucopyran.
  • the units of formula (B) or (Bi) are particularly of b (beta) anomeric configuration.
  • the polysaccharides of the invention are chosen from the compounds of formula (B ⁇ ) below and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates:
  • R a , R b , and R c are as defined for (B) previously;
  • each saccharide unit may be identical or different;
  • - n is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300;
  • At least one of the radicals R a , R b or R c of at least one saccharide unit represents a group NR1R2 and that at least one of the groups NR1R2 of at least one saccharide unit represents an NH2 group; preferably, at least one saccharide unit bears an R a amino NH2 group and at least one other saccharide unit bears an R a group which represents -N(H)-R' with R' representing a (Ci-C4)alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • the polysaccharide(s) bearing amine group(s) of the invention are chosen from chitin and chitosan and derivatives thereof, preferably chitosan.
  • polysaccharide(s) bearing amine group(s) of the invention are chosen from those of formula (B 3 ) below, and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates: [00173] [Chem. 16]
  • - n is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300;
  • polysaccharide(s) bearing amine group(s) of the invention are chosen from chitosans, salified with organic acid, preferentially with carboxylic acid, in particular (Ci-C 6 )alkylcarboxylic acid such as acetic acid.
  • composition (B) of the process of the invention are chosen from those of formulae (IVb) and (IVe) as defined previously and even more preferentially (IV’b) and (IV’e) as defined previously.
  • composition (B) also comprises one or more hydrocarbon-based oils iii) as defined previously.
  • hydrocarbon-based oils contained in dispersion (A) and in composition (B) are identical.
  • the hydrocarbon-based oil(s) of composition (B) are chosen from hydrocarbon-based oils containing from 8 to 14 carbon atoms, in particular the apolar oils, described previously. Even more preferentially, the hydrocarbon-based oil(s) of composition (B) are isododecane.
  • composition (B) is aqueous or aqueous-alcoholic, preferably aqueous.
  • aqueous-alcoholic refers to a mixture of water and of a linear or branched C2-C4 alkanol, preferably water and ethanol.
  • composition (B) is aqueous or aqueous-alcoholic and preferably also comprises one or more
  • composition (B) is aqueous and comprises one or more alkoxysilanes f) as defined previously in emulsion in water, in particular of water-in-oil (W/O) type.
  • composition (B) is aqueous and comprises one or more polyamines e) as defined previously in emulsion of oil-in-water (O/W) type.
  • the amine compound(s) used in the process according to the invention are used in a mole ratio of amine group of the amine compound iv)/ethylenically unsaturated anhydride compound anhydride b) as defined previously ranging from 0.01 to 10, preferably ranging from 0.1 to 5, preferentially ranging from 0.1 to 2 and more preferentially ranging from 0.1 to 1.
  • the at least two-step process of the invention makes it possible to obtain deposits of cosmetic agents and in particular of pigments which have good resistance to the external attacking factors to which keratin materials may be subjected, notably good resistance to water and soap, shower gels and food oils.
  • the process of the invention makes it possible to trap non-volatile compounds, notably oils, in order, for example, to improve the cosmeticity, or to give sheen to keratin materials, preferably the skin, notably facial skin such as the lips, and to do so in a manner that is resistant to external attacking factors.
  • non-volatile compounds notably oils
  • Non-volatile oils include: hydrocarbon-based oils of animal origin such as perhydrosqualene; hydrocarbon-based plant oils such as liquid triglycerides of fatty acids of 4 to 10 carbon atoms, such as heptanoic or octanoic acid triglycerides, or alternatively sunflower oil, corn oil, soybean oil, grapeseed oil, sesame oil, apricot oil, macadamia oil, castor oil, avocado oil, caprylic/capric acid triglycerides, jojoba oil, shea butter oil; linear or branched hydrocarbons, of mineral or synthetic origin such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam; synthetic esters and ethers, notably of fatty acids, for instance purcellin oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecy
  • polymethylsiloxanes which are liquid or pasty at room temperature, for instance cyclomethicones or dimethicones, optionally including a phenyl group, for instance phenyl trimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenylmethyldimethyltrisiloxanes, diphenyl dimethicones, phenyl dimethicones, polymethylphenylsiloxanes; mixtures thereof.
  • PDMSs polymethylsiloxanes
  • oils may be present in a content ranging from 0.01% to 60% by weight and better still from 0.1% to 50% by weight relative to the total weight of dispersion (A).
  • Dispersion (A) and compositions (B) and (C) according to the invention may also comprise one or more dyestuffs chosen from liposoluble dyes and pulverulent dyestuffs, for instance the pigments, nacres and glitter flakes that are well known to those skilled in the art.
  • the dyestuffs may be present in the composition in a content ranging from 0% to 30% by weight, relative to the weight of the dispersion or composition which comprises them, preferably from 0% to 10% by weight.
  • Dispersion (A) and compositions (B) and (C) according to the invention may also comprise one or more fillers, notably in a content ranging from 0.01% to 30% by weight, relative to the weight of the dispersion or composition which comprises them.
  • plasticizer or“plasticizing agent” means an organic chemical compound, which is in solid state or in liquid state, at room temperature and at atmospheric pressure, and which is added to a composition comprising different types of polymerizable ingredients (monomers) to make the polymer more supple, more flexible, and/or to improve its mechanical strength.
  • Plasticizers are known to those skilled in the art; mention may be made, for example, of“Plasticizers”, Encyclopedia of polymer Science and Technology, Helmut Reinecke, Rodrigo Navarro, Monica Perez, https://doi.org/10.1002/0471440264.pst245.pub215 September 2011.
  • the plasticizers have a molecular weight of between 200 and 1000 g/mol, particularly between 300 and 700, preferably between 350 and 600.
  • the agents are also organic compounds consisting of carbon and hydrogen atoms and of one or more heteroatoms chosen from oxygen, sulfur and silicon atoms, in particular chosen from oxygen and silicon atoms, preferably at least 3 heteroatoms, even more preferentially between 4 and 10 heteroatoms, and which may contain one or more aryl groups such as benzyl.
  • they comprise one or more groups chosen from esters, phthalate, benzoate, sulfonate, citrates and siloxanes.
  • the plasticizer(s) of the invention are chosen from those of the phthalate, ester, citrate, benzoate and siloxane families.
  • the plasticizer(s) are chosen from compounds (V) and (VI) below:
  • R h and R 1 which may be identical or different, represent a group from among: (CrC2o)alkyl, aryl such as phenyl, aryl(Ci-C4)alkyl such as benzyl, preferably (CrC4)alkyl such as n-butyl;
  • - n is 1 , 2 or 3, preferably 2;
  • - L represents a group from among: a) divalent, trivalent or tetravalent C1-C10 alkyl, preferably trivalent (C2-Cs)alkyl, said divalent, trivalent or tetravalent alkyl possibly being optionally substituted with one or more hydroxyl groups, b) divalent or trivalent cycloalkyl, or c) divalent, trivalent or tetravalent aryl, preferably divalent or trivalent phenyl; preferably, L represents a group a);
  • R j which may be identical or different, preferably identical, represents a group from among: (Ci-Cio)alkyl, aryl such as phenyl, aryl(Ci-C4)alkyl such as benzyl, preferably aryl such as phenyl,
  • R k which may be identical or different, preferably identical, represents a hydrogen atom or a hydroxyl, (Ci-Ce)alkyl or (Ci-Ce)alkoxy group,
  • - L' represents a group chosen from a) divalent C2-C10 alkyl, preferably divalent (C4-Cs)alkyl, which may be optionally substituted with one or more hydroxyl groups, and/or interrupted with one or more oxygen atoms, and/or interrupted with one or more divalent groups - Si(R j )(R k )- with R j and R k as defined previously, b) divalent or trivalent cycloalkyl, c) divalent, trivalent or tetravalent aryl, and d) -Si(R j )(R k )-; preferably, L' represents a group d) - Si(R j )(R k )-.
  • the compounds of formula (V) are chosen from the compounds of formula (V):
  • R h and R 1 which may be identical or different, represent a group from among: (Ci-Ce)alkyl, aryl(Ci-C4)alkyl such as benzyl, preferably (CrC4)alkyl such as n-butyl;
  • - n is 1 or 2, preferably 2;
  • - L represents a group from among: a) divalent, trivalent or tetravalent C2-C6 alkyl, preferably trivalent (C2-Cs)alkyl, said alkyl possibly being optionally substituted with one or more hydroxyl groups, preferably substituted with a hydroxyl group.
  • the compounds of formula (VI) are chosen from the compounds of formula (VI'):
  • R j which may be identical or different, preferably identical, represents a group from among: aryl such as phenyl, aryl(Ci-C4)alkyl such as benzyl, preferably aryl such as phenyl, and
  • R k which may be identical or different, preferably identical, represents a (Ci-Ce)alkyl and preferably (CrC4)alkyl group such as methyl.
  • the plasticizer(s) of the invention are chosen from: di-n-hexyl phthalate (DnHP), diisoheptyl phthalate, (DIHP), diheptyl phthalate (DnHP), bis(2- ethylhexyl) phthalate (DEHP), diheptylnonyl phthalate (DnHNP), di-n-octyldecyl phthalate (DNODP), diheptylnonylundecyl phthalate (DnHNUP), diisononyl phthalate (DINP), dinonyl phthalate (DNP), di-n-nonyl phthalate (DnNP) diisodecyl phthalate (DIDP), di-n- nonyldecylundecyl phthalate (DnNDUP), dinonylundecyl phthalate (DnNUP), diundecyl phthalate
  • the plasticizer(s) v) of the invention may be present in composition (A) and/or in composition (B), and/or in another composition (C).
  • the plasticizer(s) of the invention are present in composition (A).
  • the plasticizer(s) are in an amount of between 5% and 50% by weight relative to the total weight of the polymer(s) a) to d) of the particles.
  • the plasticizers are in an amount of between 0.5% and 30% by weight, in particular between 1 % and 20%, preferably from 1.5% to 10% by weight relative to the total weight of composition (A), and/or in composition (B), and/or in another composition (C), preferably relative to the total weight of composition (A).
  • the cosmetic active agent(s) vi)
  • the cosmetic active agent(s) of the invention are chosen from a) pigments, b) active agents for caring for keratin materials, preferably the skin, and c) UV-screening agents, and also d) mixtures thereof.
  • the cosmetic active agent(s) vi) of the invention are chosen from a) dyes and/or pigments.
  • the cosmetic active agent(s) vi) of the invention are chosen from b) active agents for caring for keratin materials, preferably skincare active agents.
  • the cosmetic active agent(s) vi) of the invention are chosen from c) UV-screening agents.
  • dispersion (A) and/or composition (B) and/or composition (C) of the invention comprise vi) one or more cosmetic active agents.
  • dispersion (A) comprises vi) one or more cosmetic active agents, preferably one or more pigments.
  • composition (B) comprises vi) one or more cosmetic active agents, preferably one or more pigments.
  • composition (C) comprises vi) one or more cosmetic active agents, preferably one or more pigments.
  • the hair dye(s) more particularly represent from 0.001 % to 10% by weight and preferably from 0.005% to 5% by weight of the total weight of the composition which comprises them.
  • dispersion (A) and/or composition (B) and/or composition (C) of the invention comprise vi) one or more hair dyes and/or pigments.
  • dispersion (A) comprises vi) one or more hair dyes.
  • composition (B) comprises vi) one or more hair dyes.
  • composition (C) comprises vi) one or more hair dyes.
  • hair dyes refers to oxidation dyes, direct dyes and direct dyes used for dyeing keratin fibres, notably human keratin fibres such as the hair.
  • oxidation bases are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases and the corresponding addition salts, optionally combined with coupling agents, in particular chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based coupling agents and heterocyclic coupling agents and also the corresponding addition salts;
  • direct dyes notably azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes may be anionic, cationic or neutral.
  • - natural dyes notably chosen from hennotannic acid, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orcein, and also extracts or decoctions containing these natural dyes.
  • the hair dye(s) more particularly represent from 0.001% to 10% by weight and preferably from 0.005% to 5% by weight of the total weight of the composition which comprises them.
  • dispersion (A) comprises vi) one or more cosmetic active agents, in particular one or more pigments.
  • composition (B) comprises vi) one or more cosmetic active agents, in particular one or more pigments.
  • composition (C) comprises vi) one or more cosmetic active agents, in particular one or more pigments.
  • igment ' refers to any pigment, of synthetic or natural origin, which gives colour to keratin materials.
  • solubility of the pigments in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01 %.
  • the pigments that may be used are notably chosen from the organic and/or mineral pigments known in the art, notably those described in Kirk-Othmer’s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry. Pigments that may notably be mentioned include organic and mineral pigments such as those defined and described in Ullmann's Encyclopedia of Industrial Chemistry "Pigment organics", 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20 371 and ibid, "Pigments, Inorganic, 1. General” 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheiml 0.1002/14356007.a20_243.pub3 [00227] These pigments may be in pigment powder or paste form. They may be coated or uncoated.
  • the pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof.
  • the pigment may be a mineral pigment.
  • the term“mineral pigment” refers to any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on inorganic pigments.
  • the pigment may be an organic pigment.
  • organic pigment refers to any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on organic pigments.
  • the organic pigment may notably be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references Cl 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references Cl 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100
  • the pigment(s) used are pigment pastes of organic pigments such as the products sold by the company Hoechst under the name:
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may be composed notably of particles including:
  • the term "lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.
  • Examples of lakes that may be mentioned include the products known under the following names: D & C Red 21 (Cl 45 380), D & C Orange 5 (Cl 45 370), D & C Red 27 (Cl 45 410), D & C Orange 10 (Cl 45 425), D & C Red 3 (Cl 45 430), D & C Red 7 (Cl 15 850:1), D & C Red 4 (Cl 15 510), D & C Red 33 (Cl 17 200), D & C Yellow 5 (Cl 19 140), D & C Yellow 6 (Cl 15 985), D & C Green (Cl 61 570), D & C Yellow 10 (Cl 77 002), D & C Green 3 (Cl 42 053) or D & C Blue 1 (Cl 42 090).
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.
  • D&C Red 21 (Cl 45 380), D&C Orange 5 (Cl 45 370), D&C Red 27 (Cl 45 410), D&C Orange 10 (Cl 45 425), D&C Red 3 (Cl 45 430), D&C Red 4 (Cl 15 510), D&C Red 33 (Cl 17 200), D&C Yellow 5 (Cl 19 140), D&C Yellow 6 (Cl 15 985), D&C Green (Cl 61 570), D&C Yellow 10 (Cl 77 002), D&C Green 3 (Cl 42 053), D&C Blue 1 (Cl 42 090).
  • the pigment(s) may also be pigments with special effects.
  • pigments with special effects refers to pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.
  • pigments with special effects include those with a low refractive index, such as fluorescent, photochromic or thermochromic pigments, and those with a higher refractive index, such as nacres or glitter flakes.
  • examples of pigments with special effects that may be mentioned include nacreous pigments such as titanium mica coated with an iron oxide, mica coated with an iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye notably of the abovementioned type, and also nacreous pigments based on bismuth oxychloride. They may also be mica particles, at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • the nacres may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or tint.
  • nacres that may be used in the context of the present invention, mention may notably be made of the gold-coloured nacres sold notably by the company Engelhard under the name Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold notably by the company Merck under the names Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona), by the company Eckart under the name Prestige Bronze and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold notably by the company Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the names Passion orange (Colorona) and Matte orange (17449) (Microna); the brown-tinted nacres sold notably by the company Engelhard under the names Nu-antique copper 340XB (Cloisonne).
  • Sunstone G012 (Gemtone); the black nacres with a golden tint sold notably by the company Engelhard under the name Nu-antique bronze 240 AB (Timica); the blue nacres sold notably by the company Merck under the names Matte blue (17433) (Microna), Dark Blue (117324) (Colorona); the white nacres with a silvery tint sold notably by the company Merck under the name Xirona Silver; and the golden-green pinkish-orange nacres sold notably by the company Merck under the name Indian summer (Xirona), and mixtures thereof.
  • multilayer pigments based on synthetic substrates such as alumina, silica, sodium calcium borosilicate or calcium aluminium borosilicate, and aluminium, may be envisaged.
  • Pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or
  • Pigments with special effects also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots
  • the size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.
  • the pigments may be dispersed in the product by means of a dispersant.
  • dispersant ' refers to a compound which can protect the dispersed particles from agglomerating or flocculating.
  • This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments.
  • These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. Said agent may be charged: it may be anionic, cationic, zwitterionic or neutral.
  • the dispersants used are chosen from esters of 12-hydroxystearic acid, more particularly, and of Cs to C20 fatty acids and of polyols such as glycerol or diglycerol, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2
  • CTFA name dipolyhydroxystearate sold under the reference Dehymyls PGPH by the company Henkel
  • polyhydroxystearic acid such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof.
  • polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185 and DC2-5225 C.
  • the pigments used in the cosmetic composition according to the invention may be surface-treated with an organic agent.
  • the pigments that have been surface-treated beforehand are pigments that have totally or partially undergone a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature, with an organic agent such as those described notably in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention.
  • organic agents may be chosen, for example, from amino acids; waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and derivatives thereof, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol and lauric acid and derivatives thereof; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polysaccharides, for example chitosan, cellulose and derivatives thereof; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; proteins; alkanolamines; silicone compounds, for example silicones,
  • polydimethylsiloxanes alkoxysilanes, alkylsilanes and siloxysilicates; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.
  • the surface-treated pigments that are useful in the cosmetic composition according to the invention may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.
  • the surface-treated pigments that are useful in the context of the present invention may be prepared according to surface-treatment techniques that are well known to those skilled in the art, or may be commercially available as is.
  • the surface-treated pigments are coated with an organic layer.
  • the organic agent with which the pigments are treated may be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.
  • the surface treatment may thus be performed, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is notably described in patent US 4 578 266.
  • An organic agent covalently bonded to the pigments will preferably be used.
  • the agent for the surface treatment may represent from 0.1 % to 50% by weight, preferably from 0.5% to 30% by weight and even more preferentially from 1 % to 10% by weight relative to the total weight of the surface-treated pigments.
  • the surface treatments of the pigments are chosen from the following treatments:
  • PEG-silicone treatment for instance the AQ surface treatment sold by LCW;
  • a chitosan treatment for instance the CTS surface treatment sold by LCW;
  • methicone treatment for instance the SI surface treatment sold by LCW;
  • dimethicone treatment for instance the Covasil 3.05 surface treatment sold by LCW;
  • a dimethicone/trimethyl siloxysilicate treatment for instance the Covasil 4.05 surface treatment sold by LCW
  • a lauroyllysine treatment for instance the LL surface treatment sold by LCW
  • - a lauroyllysine dimethicone treatment for instance the LL/SI surface treatment sold by LCW
  • a magnesium myristate treatment for instance the MM surface treatment sold by LCW;
  • an aluminium dimyristate treatment such as the Ml surface treatment sold by Miyoshi;
  • an isostearyl sebacate treatment for instance the HS surface treatment sold by Miyoshi;
  • an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment for instance the FSA surface treatment sold by Daito;
  • a polymethylhydrosiloxane/perfluoroalkyl phosphate treatment for instance the FS01 surface treatment sold by Daito;
  • a lauroyllysine/aluminium tristearate treatment for instance the LL-AISt surface treatment sold by Daito;
  • an octyltriethylsilane treatment for instance the OTS surface treatment sold by Daito;
  • an octyltriethylsilane/perfluoroalkyl phosphate treatment for instance the FOTS surface treatment sold by Daito;
  • an acrylate/dimethicone copolymer treatment for instance the ASC surface treatment sold by Daito;
  • an isopropyl titanium tri isostearate treatment for instance the ITT surface treatment sold by Daito;
  • microcrystalline cellulose and carboxymethylcellulose treatment for instance the AC surface treatment sold by Daito;
  • a cellulose treatment for instance the C2 surface treatment sold by Daito;
  • an acrylate copolymer treatment for instance the APD surface treatment sold by Daito; a perfluoroalkyl phosphate/isopropyl titanium triisostearate treatment, for instance the PF + ITT surface treatment sold by Daito.
  • composition in accordance with the present invention may furthermore comprise one or more surface-untreated pigments.
  • the pigment(s) are mineral pigments.
  • the pigment(s) are chosen from nacres.
  • the dispersant is present with organic pigments in dispersion (A), and/or composition (B) and/or (C) or with inorganic pigments in particulate form of submicron size.
  • submicron or“submicronic” refers to pigments having a particle size that has been micronized by a micronization method and having a mean particle size of less than a micrometre (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.
  • the dispersant and the pigment(s) are present in an amount (dispersant:pigment) of between 0.5:1 and 2: 1 , particularly between 0.75:1 and 1.5:1 or better still between 0.8:1 and 1.2:1.
  • the dispersant is suitable for dispersing the pigments and is compatible with a condensation-curable formulation.
  • the term“compatible” means, for example, that said dispersant is miscible in the oily phase of the composition or of the dispersion containing the pigment(s), and it does not retard or reduce the curing.
  • the dispersant is preferably cationic.
  • the dispersant(s) may therefore have a silicone backbone, such as silicone polyether and dispersants of aminosilicone type.
  • silicone backbone such as silicone polyether and dispersants of aminosilicone type.
  • suitable dispersants that may be mentioned are:
  • - aminosilicones i.e. silicones comprising one or more amino groups such as those sold under the names and references: BYK LPX 21879 by BYK, GP-4, GP-6, GP-344, GP-851 , GP-965, GP-967 and GP-988-1 , sold by Genesee Polymers,
  • Tego ® RC 902 Tego ® RC 922, Tego ® RC 1041 , and Tego ® RC 1043, sold by Evonik,
  • PDMS polydimethylsiloxane
  • carboxylic groups such as X- 22162 and X-22370 by Shin-Etsu
  • epoxy silicones such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695 by Genesee Polymers, or Tego ® RC 1401 , Tego ® RC 1403, Tego ® RC 1412 by Evonik.
  • the dispersant(s) are of aminosilicone type and are positively charged.
  • dispersants bearing chemical groups that are capable of reacting with the reagents of the oily phase and are thus capable of improving the 3D network formed from the aminosilicones.
  • dispersants of epoxy silicone pigments can react chemically with the aminosilicone prepolymer amino group(s) to increase the cohesion of the aminosilicone film comprising the pigment(s).
  • the pigments v) of the invention are chosen from carbon black, iron oxides, notably red and black iron oxides, and micas coated with iron oxide,
  • triarylmethane pigments notably blue and purple triaryl methane pigments, such as Blue 1 Lake
  • azo pigments notably red azo pigments, such as D&C Red 7
  • an alkali metal salt of lithol red such as the calcium salt of lithol red B.
  • the amount of pigments ranges from 0.5% to 40% and preferably from 1 % to 20% relative to the weight of the composition and dispersion comprising them.
  • the process of the invention is a process for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin such as the lips, comprising:
  • composition (B) comprising:
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (B) comprising:
  • the process of the invention is a process for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin such as the lips, comprising:
  • composition (B) comprising:
  • one or more amine compounds chosen from e) and f) as defined previously and vi) one or more cosmetic agents, preferably one or more pigments; and optionally one or more polar protic solvents such as water.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (B) comprising:
  • one or more amine compounds chosen from e) and f) as defined previously; and vi) one or more dyes and/or pigments and optionally one or more polar protic solvents such as water.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (B) comprising:
  • the process of the invention is a process for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin such as the lips, comprising:
  • composition (B) comprising: vi) one or more cosmetic active agents, preferably pigments, and iv) one or more amine compounds chosen from e) and f) as defined previously and optionally iii) one or more hydrocarbon-based oils as defined previously and optionally one or more polar protic solvents such as water;
  • composition (C) comprising v) one or more plasticizers and optionally iii) one or more hydrocarbon-based oils as defined previously.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (B) comprising:
  • amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water;
  • composition (C) comprising one or more plasticizers; and vi) one or more dyes and/or pigments and optionally iii) one or more hydrocarbon-based oils as defined previously.
  • the process of the invention is a process for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin such as the lips, comprising:
  • an oily dispersion comprising: 1) one or more particles constituted of one or more ethylenic copolymers a) and b) as defined previously;
  • composition (C) comprising: v) one or more plasticizers and vi) one or more cosmetic active agents, preferably pigments; followed by the application to said materials of a composition (B) comprising iv) one or more amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (C) comprising v) one or more plasticizers; and vi) one or more cosmetic active agents, preferably dyes and/or pigments and optionally iii) one or more hydrocarbon-based oils as defined previously;
  • composition (B) comprising iv) one or more amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (B) comprising: v) one or more plasticizers and iv) one or more amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water;
  • composition (C) comprising vi) one or more cosmetic agents, preferably dyes and/or pigments and optionally iii) one or more hydrocarbon-based oils as defined previously.
  • the process of the invention is a process for treating keratin materials, in particular the skin, preferably human skin and more preferentially facial skin such as the lips, comprising:
  • composition (C) comprising v) one or more cosmetic active agents, preferably pigments, and optionally iii) one or more hydrocarbon-based oils as defined previously;
  • composition (B) comprising iv) one or more amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water.
  • the process of the invention is a process for treating keratin fibres, in particular human keratin fibres, preferably the hair, comprising:
  • composition (C) comprising v) one or more cosmetic active agents, preferably pigments, and optionally iii) one or more hydrocarbon-based oils as defined previously;
  • composition (B) comprising iv) one or more amine compounds chosen from e) and f) as defined previously and optionally one or more polar protic solvents such as water.
  • the cosmetic agent(s) vi) as defined previously, in particular the pigments are in a composition (C).
  • composition may be applied simultaneously with composition (A), or with composition (B).
  • composition (C) is applied after step 1), i.e. after the application of composition (A); more preferentially, compositions (A) and (B) do not comprise any hair dye and a composition (C) comprising one or more hair dyes v) as defined previously is applied after step 1) of the process of the invention, followed by the application to the keratin materials of composition (B).
  • compositions (B) and (C) are cosmetic, i.e. they comprise only cosmetically acceptable ingredients.
  • dispersion (A) and compositions (B) and (C) are anhydrous.
  • composition (B) are anhydrous, and composition (C) is aqueous.
  • composition (B) is aqueous or aqueous-alcoholic.
  • composition (C) is aqueous or aqueous-alcoholic.
  • dispersion (A) is anhydrous and composition (B) and composition (C) are aqueous or aqueous-alcoholic, preferably aqueous.
  • Compositions (B) and (C) and dispersion (A) according to the invention may comprise a cosmetic additive chosen from water, fragrances, preserving agents, fillers, oils, waxes, surfactants, moisturizers, vitamins, ceramides, antioxidants, free-radical scavengers, polymers, thickeners and dyestuffs.
  • a cosmetic additive chosen from water, fragrances, preserving agents, fillers, oils, waxes, surfactants, moisturizers, vitamins, ceramides, antioxidants, free-radical scavengers, polymers, thickeners and dyestuffs.
  • compositions (B) and (C) and dispersion (A) according to the invention may also comprise other dyestuffs, such as liposoluble dyes or water-soluble dyes.
  • This dyestuff may be present in a content ranging from 0.01 % to 30% by weight, relative to the total weight of the composition containing them, preferably from 0.01% to 10% by weight.
  • the liposoluble dyes are, for example, Sudan Red, D&C Red 17, D&C Green 6, b-carotene, soybean oil, Sudan Brown, D&C Yellow 1 1 , D&C Violet 2, D&C Orange 5, quinoline yellow and annatto.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue.
  • dispersion (A) and compositions (B) and (C) according to the invention are anhydrous compositions.
  • the first step of the process of the invention is the application of dispersion (A) in one or more volatile apolar solvents, notably isododecane.
  • step 2) follows step 1) without intermediate rinsing or drying.
  • a waiting time of between 1 minute and 6 hours, in particular between 10 minutes and 5 hours, more particularly between 30 minutes and 4 hours, and preferably about 3 hours, before applying composition (B).
  • the keratin materials are preferably dried naturally.
  • the first step is the step of applying the oily dispersion (A) and the second step is that of applying composition (C) and the third step is that of applying composition (B) between the application of composition (C) as defined previously (step 2) and the step of applying composition (B) (step 3)
  • the keratin materials are preferably dried naturally.
  • the keratin materials are preferably dried naturally.
  • a subject of the invention is also a kit or device with several separate compartments comprising:
  • composition (B) as defined previously
  • composition (C) as defined previously.
  • composition packaging assembly is, in a known manner, any packaging that is suitable for storing cosmetic compositions (notably a bottle, tube, spray bottle or aerosol bottle).
  • a subject of the invention is also the oily dispersion (A) as defined previously comprising v) one or more plasticizers and vi) the cosmetic agent(s) as defined previously.
  • a subject of the invention is also the oily dispersion (A) which is in an inverse emulsion (W/O) as defined previously.
  • oily dispersions (A) are formed as a whole [particles i) + stabilizer ii)] containing:
  • ethylenically unsaturated anhydride compound b) (such as maleic anhydride)
  • isobornyl acrylate is polymerized in isododecane/ethyl acetate (60/40) in the presence of a small amount of ethyl acrylate and of a radical initiator (T21S).
  • T21S a radical initiator
  • the isobornyl acrylate/ethyl acrylate mass ratio is 92/8.
  • the rest of the ethyl acrylate and the maleic anhydride are added in the presence of isododecane/ethyl acetate (60/40) and of the radical initiator Trigonox 21 S (T21S).
  • the polymer After stripping, the polymer is at a solids content of 52% in the isododecane.
  • the ratios employed to obtain the stabilizer and the particulate core are summarized in the table below:
  • Step 1
  • sododecane added between the two steps:
  • Step 2
  • isododecane/ethyl acetate 60/40
  • the medium is heated to 90°C and ethyl acrylate/maleic anhydride, isododecane/ethyl acetate (60/40) and T21S are poured in over 2 hours.
  • the medium is milky.
  • the mixture is left stirring for at least 7 hours at 90°C.
  • compositions (A1) to (A5) in a bath ratio of 0.5 g of formulation/g of hair;
  • the lock is dried with a hairdryer
  • compositions (A1) to (A5) After application of compositions (A1) to (A5), application of composition (B), in a bath ratio of 0.5 g of formulation/g of hair;
  • the lock is dried with a hairdryer
  • the colour build-up on hair thus corresponds to the variation in colouring between the locks of non-dyed NG hair (natural grey hair containing 90% white hairs) and the dyed hair, which is measured by (DE) according to the following equation:
  • NG hair, and L0*, aO* and bO* represent the values measured before dyeing. The higher the DE value, the better the build-up of the colouring.

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  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
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  • Cosmetics (AREA)

Abstract

La présente invention concerne une méthode de traitement de matières kératiniques, de préférence de la peau humaine, en particulier des lèvres, ou une méthode de traitement de fibres kératiniques, notamment de fibres kératiniques humaines telles que les cheveux, en au moins deux étapes comportant, dans un premier temps, l'application, sur lesdites matières, d'une dispersion huileuse (A) comprenant i) des particules de copolymères d'acrylates d'alkyle et d'acryliques d'anhydride, ii) des stabilisants, iii) une ou plusieurs huiles hydrocarbonées ; puis, dans un second temps, l'application, sur lesdites matières, d'une composition (B) comprenant iv) un ou plusieurs composés amines, étant entendu que la méthode de l'invention met en œuvre v) un ou plusieurs plastifiants, et vi) un ou plusieurs agents actifs cosmétiques choisis parmi a) des colorants et/ou des pigments, b) des agents actifs de soin de matières kératiniques, de préférence de la peau, et c) des agents filtrant les UV et également d) des mélanges de ces derniers ; les principes v) et vi) se trouvant éventuellement dans la composition (A) et/ou dans la composition (B) et/ou dans une autre composition (C). L'invention concerne également un kit à compartiments multiples, comprenant les principes i) à vi). L'invention concerne également une dispersion huileuse anhydre (A) comprenant v) un ou plusieurs plastifiants. La méthode de l'invention permet d'obtenir un traitement desdites matières kératiniques qui est notamment résistant à la sueur, aux gels douche, à l'eau et aux substances grasses, en particulier aux huiles alimentaires végétales ou animales. Selon la présente invention, la méthode de traitement de matières kératiniques est également appropriée pour maquiller la peau ou les lèvres, telles que des fonds de teint et des rouges à lèvres.
PCT/EP2020/068111 2019-06-28 2020-06-26 Méthode de traitement de matières kératiniques mettant en œuvre un polymère acrylique anhydride dans une dispersion huileuse, un plastifiant et un composé amine Ceased WO2020260641A1 (fr)

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FR1907117A FR3097757B1 (fr) 2019-06-28 2019-06-28 : procede de traitement de matieres keratiniques mettant en œuvre un polymere acrylique d’anhydride en dispersion huileuse, d’un plastifiant, et d’un compose amine

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FR3129596A1 (fr) * 2021-12-01 2023-06-02 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre un composé portant une fonction chimique réactive, un alcoxysilane, un agent colorant et éventuellement un composé choisi parmi les sels métalliques, les composés de métal appartenant au groupe des terres rares et les alcoxydes métalliques

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FR3127695B1 (fr) * 2021-10-05 2024-07-12 Oreal Dispersion huileuse comprenant une particule polymerique, un agent stabilisant a groupe alkyle en c9-c22, et un plastifiant procede de traitement des matieres keratiniques mettant en œuvre la dispersion huileuse

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FR3129596A1 (fr) * 2021-12-01 2023-06-02 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre un composé portant une fonction chimique réactive, un alcoxysilane, un agent colorant et éventuellement un composé choisi parmi les sels métalliques, les composés de métal appartenant au groupe des terres rares et les alcoxydes métalliques

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