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WO2018206457A1 - Utilisation d'une composition tinctoriale à base de silicones aminées et de copolymères issus de la polymérisation d'au moins un monomère d'acide crotonique ou d'un dérivé d'acide crotonique, pour limiter le transfert - Google Patents

Utilisation d'une composition tinctoriale à base de silicones aminées et de copolymères issus de la polymérisation d'au moins un monomère d'acide crotonique ou d'un dérivé d'acide crotonique, pour limiter le transfert Download PDF

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Publication number
WO2018206457A1
WO2018206457A1 PCT/EP2018/061583 EP2018061583W WO2018206457A1 WO 2018206457 A1 WO2018206457 A1 WO 2018206457A1 EP 2018061583 W EP2018061583 W EP 2018061583W WO 2018206457 A1 WO2018206457 A1 WO 2018206457A1
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Prior art keywords
vinyl
crotonic acid
composition
weight
chosen
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PCT/EP2018/061583
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English (en)
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David Seneca
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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
    • A61K8/18—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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • 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

Definitions

  • the present invention relates to the use of a composition for dyeing keratin fibers, comprising at least one copolymer derived from the polymerization of at least one crotonic acid monomer or crotonic acid derivative and at least one pigment for limiting transfer.
  • compositions for temporarily dyeing and/or making up the hair may also lead to a hair feel that is uncosmetic and/or not natural; the hair thus dyed may in particular lack softness and/or suppleness and/or individualization.
  • compositions for the temporary dyeing of keratin materials, especially the hair which have the advantage of forming a transfer-resistant deposit, which in particular does not become deposited, at least partly, onto supports with which said compositions are placed in contact, such as the skin (in particular the hands and the face) and/or clothing.
  • compositions for dyeing keratin fibers especially human keratin fibers such as the hair, comprising at least one copolymer derived from the polymerization of at least one crotonic acid monomer or crotonic acid derivative and of at least one vinyl ester monomer, at least one pigment and at least one amino silicone for limiting transfer.
  • compositions for dyeing keratin fibers especially human keratin fibers such as the hair, comprising (i) one or more copolymers derived from the polymerization of at least one crotonic acid monomer or crotonic acid derivative and of at least one vinyl ester monomer, (ii) one or more pigments and (iii) at least one amino silicone for limiting transfer.
  • limiting transfer means reducing the transfer of said composition applied to keratin fibers onto supports with which the composition comes into contact, such as the skin (in particular the hands and the face) and/or textile supports such as clothing, sheets, pillowcases and/or towels.
  • the transfer of said composition applied to keratin fibers onto supports with which the composition comes into contact is reduced by at least 50%, preferentially at least 70%>, better still at least 90% and preferably 99% so as to totally prevent the transfer of said composition from the keratin fibers onto the supports with which the composition comes into contact.
  • the term "limiting transfer” means reducing the transfer of said composition onto supports with which it comes into contact, such as the skin (in particular the hands and the face) and/or clothing by at least 50%, preferably at least 70%, better still 90% and preferably 99% so as to totally prevent the transfer of the composition onto the supports with which it comes into contact.
  • composition according to the invention comprises at least one copolymer derived from the polymerization of at least one crotonic acid monomer or crotonic acid derivative and of at least one vinyl ester monomer, preferably at least two different vinyl ester monomers.
  • the copolymer according to the invention is chosen from copolymers derived from the polymerization of at least one crotonic acid monomer and of at least one vinyl ester monomer, preferably at least two different vinyl ester monomers.
  • crotonic acid derivative preferably means a crotonic acid ester or a crotonic acid amide.
  • crotonic acid derivative preferably means a crotonic acid ester or amide, in particular:
  • the crotonic acid esters of formula CH3CH CHCOOR'l with R'l representing a linear, branched or cyclic, saturated or unsaturated, optionally aromatic (aryl, aralkyl or alkylaryl) carbon-based and especially hydrocarbon-based (alkyl) chain, containing 1 to 30 carbon atoms, optionally comprising one or more functions chosen from -OH, -OR' with R C1-C6 alkyl (alkoxy), -CN, -X (halogen, especially CI, F, Br or I); mention may be made, for example, of methyl crotonate and ethyl crotonate,
  • crotonic acid amides of formula CH 3 CH CHCONR2R"2 with R * 2 and R"2, which may be identical or different, representing hydrogen or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based and especially hydrocarbon-based (alkyl) chain, containing 1 to 30 carbon atoms, optionally comprising one or more functions chosen from -OH, -OR with R * C1-C6 alkyl (alkoxy), -CN, -X (halogen, especially CI, F, Br or I).
  • crotonic acid derivative preferably means a crotonic acid ester or amide, in particular:
  • the crotonic acid esters of formula CH 3 CH CHCOORl with R'l representing a linear, branched or cyclic, saturated or unsaturated, optionally aromatic such as an aryl, aralkyl or alkylaryl, carbon-based and especially hydrocarbon-based chain such as an alkyl, containing 1 to 30 carbon atoms, optionally comprising one or more functions chosen from -OH, -OR with R C1-C6 alkyl such as an alkoxy, -CN, -X such as a halogen, especially CI, F, Br or I; mention may be made, for example, of methyl crotonate and ethyl crotonate,
  • the crotonic acid amides of formula CH 3 CH CHCONR2R"2 with R * 2 and R"2, which may be identical or different, representing hydrogen or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based and especially hydrocarbon-based chain such as an alkyl, containing 1 to 30 carbon atoms, optionally comprising one or more functions chosen from -OH, -OR' with R C1-C6 alkyl such as an alkoxy, -CN, -X such as a halogen, especially CI, F, Br or I.
  • vinyl acetate vinyl propionate, vinyl butyrate (or butanoate), vinyl ethylhexanoate, vinyl neononanoate, vinyl neododecanoate, vinyl neodecanoate, vinyl pivalate, vinyl cyclohexanoate, vinyl benzoate, vinyl 4-tert-butylbenzoate and vinyl trifluoroacetate.
  • the copolymer according to the invention is chosen from copolymers derived from the polymerization of at least one crotonic acid monomer and of at least two different vinyl ester monomers, said vinyl ester monomers preferably being chosen from vinyl acetate, vinyl propionate, vinyl butyrate (or butanoate), vinyl ethylhexanoate, vinyl neononanoate, vinyl neododecanoate, vinyl neodecanoate, vinyl pivalate, vinyl cyclohexanoate, vinyl benzoate, vinyl 4-tert-butylbenzoate and vinyl trifluoroacetate, preferably from vinyl acetate, vinyl propionate and vinyl neodecanoate, better still from vinyl acetate and vinyl neodecanoate.
  • vinyl ester monomers preferably being chosen from vinyl acetate, vinyl propionate, vinyl butyrate (or butanoate), vinyl ethylhexanoate, vinyl neononanoate, vinyl
  • the copolymer according to the invention is chosen from copolymers derived from the polymerization of crotonic acid, vinyl acetate and vinyl propionate, copolymers derived from the polymerization of crotonic acid, vinyl acetate and vinyl neodecanoate, and mixtures thereof.
  • the copolymer of the composition according to the invention is a crotonic acid/vinyl acetate/vinyl neodecanoate terpolymer.
  • copolymers according to the invention may optionally comprise other monomers such as allylic or methallylic esters, or vinyl ethers. These polymers may optionally be grafted or crosslinked.
  • Luviset® CA 66 sold by the company BASF
  • Aristoflex® A60 sold by the company Clariant
  • Mexomere® PW or PAM sold by the company Chimex (INCI name VA / vinyl butyl benzoate / crotonates copolymer).
  • the total amount of copolymer(s) of crotonic acid or crotonic acid derivative according to the invention may range from 0.05% to 15% by weight relative to the weight of the composition, preferably from 0.1% to 10% by weight relative to the weight of the composition, preferably from 1% to 5% by weight relative to the weight of the composition.
  • the composition comprises one or more pigments.
  • pigment is understood to mean white or colored particles of any shape which are insoluble in the composition in which they are present.
  • the pigments that may be used are especially chosen from the organic and/or mineral pigments known in the art, especially those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry.
  • These pigments may be natural, of natural origin, or not. These pigments may be in pigment powder or paste form. They may be coated or uncoated.
  • the pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects, such as nacres or glitter flakes, and mixtures thereof.
  • the pigment may be a mineral pigment.
  • mineral pigment means any pigment that satisfies the definition in Ullmann's encyclopedia in the chapter on inorganic pigments. Mention may be made, among mineral pigments of use in the present invention, of ochres, such as red ochre (clay (in particular kaolinite) and iron hydroxide (for example hematite)), brown ochre (clay (in particular kaolinite) and limonite) or yellow ochre (clay (in particular kaolinite) and goethite); titanium dioxide, optionally surface-treated; zirconium or cerium oxides; zinc, (black, yellow or red) iron or chromium oxides; manganese violet, ultramarine blue, chromium hydrate and ferric blue; or metal powders, such as aluminum powder or copper powder.
  • ochres such as red ochre (clay (in particular kaolinite) and iron hydroxide (for example hematite)), brown
  • alkaline earth metal carbonates such as calcium carbonate or magnesium carbonate
  • silicon dioxide such as calcium carbonate or magnesium carbonate
  • quartz any other compound used as inert filler in cosmetic compositions, provided that these compounds contribute color or whiteness to the composition under the conditions under which they are employed.
  • the pigment may be an organic pigment.
  • organic pigment means any pigment that satisfies the definition in Ullmann's encyclopedia in the chapter on organic pigments.
  • the organic pigment may especially be chosen from nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • Use may also be made of any mineral or organic compound that is insoluble in the composition and standard in the cosmetics field, provided that these compounds give the composition color or whiteness under the conditions under which they are used, for example guanine, which, according to the refractive index of the composition, is a pigment.
  • guanine which, according to the refractive index of the composition, is a pigment.
  • the white or colored organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100, 45380, 45410,
  • pigmentary pastes of organic pigments such as the products sold by the company Hoechst under the names:
  • Cosmenyl FB Pigment Red 5 (CI 12490);
  • 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 especially of particles comprising a mineral core, at least one binder, which provides for the attachment of the organic pigments to the core, and at least one organic pigment which at least partially covers the core.
  • the organic pigment may also be a lake.
  • the term "lake” means dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the mineral substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate and aluminum.
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570), D&C Yellow 1 O (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090).
  • D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570
  • the pigment may also be a pigment with special effects.
  • pigments with special effects means pigments that generally create a colored 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 thus contrast with colored pigments that afford a standard uniform opaque, semi- transparent or transparent shade.
  • pigment with special effects those with a low refractive index, such as fluorescent or photochromic pigments, and those with a high refractive index, such as nacres, interference pigments or glitter flakes.
  • pigments with special effects include nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as mica coated with titanium and iron oxides, mica coaeted with iron oxide, mica coated with titanium and especially with ferric blue or with chromium oxide, mica coated with titanium and with an organic pigment of the abovementioned type, and also nacreous pigments based on bismuth oxychloride.
  • Nacreous pigments that may be mentioned include the Cellini nacres sold by Engelhard (mica-Ti02-lake), Prestige sold by Eckart (mica-Ti02), Prestige Bronze sold by Eckart (mica-Fe203), and Colorona sold by Merck (mica-Ti02-Fe203).
  • particles comprising a borosilicate substrate coated with titanium oxide.
  • Particles comprising a glass substrate coated with titanium oxide are sold in particular under the name Metashine MC1080RY by the company Toyal.
  • nacres examples include polyethylene terephthalate flakes, especially those sold by the company Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver flakes).
  • multilayer pigments based on synthetic substrates such as alumina, silica, calcium sodium borosilicate, calcium aluminum borosilicate and aluminum.
  • the pigments with special effects may also be chosen from reflective particles, i.e. especially from particles whose size, structure, especially the thickness of the layer(s) of which they are made and their physical and chemical nature, and surface state, allow them to reflect incident light. This reflection may, if appropriate, have an intensity sufficient to create, at the surface of the composition or mixture, when the latter is applied to the substrate to be made up, highlight points visible to the naked eye, that is to say more luminous points which contrast with their surroundings by appearing to sparkle.
  • the reflective particles may be selected so as not to significantly alter the coloring effect generated by the coloring agents with which they are combined, and more particularly so as to optimize this effect in terms of color rendition. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery color or glint.
  • These particles may have varied forms and may especially be in platelet or globular form, in particular in spherical form.
  • the reflective particles may or may not have a multilayer structure, and, in the case of a multilayer structure, may have, for example, at least one layer of uniform thickness, especially of a reflective material.
  • the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, especially titanium or iron oxides obtained synthetically.
  • the reflective particles may comprise, for example, a natural or synthetic substrate, especially a synthetic substrate at least partially coated with at least one layer of a reflective material, especially of at least one metal or metallic material.
  • the substrate may be made of one or more organic and/or mineral materials.
  • the reflective material may comprise a layer of metal or of a metallic material.
  • Particles comprising a glass substrate coated with silver, in the form of platelets are sold under the name Microglass Metashine REFSX 2025 PS by Toyal.
  • Particles with a glass substrate coated with nickel/chromium/molybdenum alloy are sold under the name Crystal Star GF 550 and GF 2525 by this same company.
  • Use may also be made of particles comprising a metal substrate, such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze or titanium, said substrate being coated with at least one layer of at least one metal oxide, such as titanium oxide, aluminum oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof. Examples that may be mentioned include aluminum powder, bronze powder or copper powder coated with Si02 sold under the name Visionaire by the company Eckart.
  • Pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or interference holographic glitter flakes (Geometric Pigments or Spectra f7x from Spectratek).
  • Pigments with special effects also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots Corporation.
  • Quantum dots are luminescent semiconductive nanoparticles capable of emitting, under light excitation, irradiation with a wavelength of between 400 nm and 700 nm. These nanoparticles are known from the literature. In particular, they may be synthesized according to the processes described, for example, in US 6 225 198 or US 5 990 479, in the publications cited therein and also in the following publications: Dabboussi B.O. et al, "(CdSe)ZnS core-shell quantum dots: synthesis and characterization of a size series of highly luminescent nanocrystallites", Journal of Physical Chemistry B, vol. 101, 1997, pp.
  • pigments that may be used in the present invention makes it possible to obtain a wide range of colors, and also particular optical effects such as metallic effects or interference effects.
  • the size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 ⁇ , preferably between 20 nm and 80 ⁇ and even more preferably between 30 nm and 50 ⁇ .
  • the pigments may be dispersed in the product by means of a dispersant.
  • the dispersant serves to protect the dispersed particles against agglomeration or flocculation.
  • This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments.
  • These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium.
  • 12-hydroxystearic acid esters and C8 to C20 fatty acid esters of polyols such as glycerol or diglycerol are used, such as poly(12- hydroxystearic acid) stearate with a molecular weight of about 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or polyhydroxystearic acid such as the product sold under the reference Arlacel PI 00 by the company Uniqema, and mixtures thereof.
  • poly(12- hydroxystearic acid) stearate with a molecular weight of about 750 g/mol such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Hen
  • dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185 and DC2-5225 C.
  • the pigments used in the 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 especially in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention.
  • organic agents can, for example, be chosen from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminum salts of fatty acids, for example aluminum stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers comprising acrylate units; alkanolamines; silicone compounds, for example silicones or polydimethylsiloxanes; fluorinated organic compounds, for example perfluoroalkyl ethers; or 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
  • 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 in the required form. Preferably, the surface-treated pigments are coated with an organic layer.
  • the organic agent with which the pigments are treated may be deposited on the pigments by evaporation of solvent, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.
  • the surface treatment may thus be performed, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is especially described in patent US 4 578 266.
  • 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 pigment.
  • the surface treatments of the pigments are chosen from the following treatments:
  • a PEG-silicone treatment for instance the AQ surface treatment sold by LCW
  • a methicone treatment for instance the SI surface treatment sold by LCW
  • dimethicone treatment for instance the Covasil 3.05 surface treatment sold by LCW;
  • dimethicone/trimethyl siloxysilicate treatment for instance the Covasil 4.05 surface treatment sold by LCW;
  • a magnesium myristate treatment for instance the MM surface treatment sold by LCW;
  • an aluminum dimyristate treatment such as the MI surface treatment sold by Miyoshi;
  • an isostearyl sebacate treatment for instance the HS surface treatment sold by Miyoshi;
  • a perfluoroalkyl phosphate treatment for instance the PF surface treatment sold by Daito
  • - an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment for instance the FSA surface treatment sold by Daito
  • a polymethylhydrogenosiloxane/perfluoroalkyl phosphate treatment for instance the FS01 surface treatment sold by Daito
  • - an acrylate/dimethicone copolymer treatment for instance the ASC surface treatment sold by Daito;
  • an isopropyl titanium triisostearate treatment for instance the ITT surface treatment sold by Daito;
  • an acrylate copolymer treatment for instance the APD surface treatment sold by Daito;
  • a perfluoroalkyl phosphate/isopropyl titanium triisostearate treatment for instance the PF + ITT surface treatment sold by Daito.
  • the pigment is chosen from mineral or mixed mineral-organic pigments.
  • the amount of pigment(s) may range from 0.01% to 30% by weight, more particularly from 0.05% to 20% by weight, preferably from 0.1% to 15% by weight and preferably from 1% to 10% by weight relative to the total weight of the composition.
  • composition of the invention may contain colored or coloring species other than the pigments according to the invention, such as direct dyes or dye precursors.
  • the composition also comprises at least one amino silicone.
  • the silicones may be solid or liquid at 25°C and atmospheric pressure (1.013> ⁇ 10 5 Pa), and volatile or nonvolatile.
  • the silicones that may be used may be soluble or insoluble in the composition according to the invention; they may be in the form of oil, wax, resin or gum; silicone oils are preferred.
  • the composition contains one or more silicones that are liquid at 25°C and atmospheric pressure (1.013 x l0 5 Pa).
  • amino silicone denotes any silicone comprising at least one primary, secondary or tertiary amine or a quaternary ammonium group.
  • the weight-average molecular masses of these amino silicones may be measured by gel permeation chromatography (GPC) at room temperature (25°C), as polystyrene equivalent.
  • the columns used are ⁇ styragel columns.
  • the eluent is THF and the flow rate is 1 ml/min. 200 ⁇ of a 0.5% by weight solution of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • the amino silicone(s) that may be used in the context of the invention are chosen from: a) the polysiloxanes corresponding to formula (A):
  • - G which may be identical or different, denotes a hydrogen atom or a phenyl, OH alkyl, for example methyl, or Ci-Cs alkoxy, for example methoxy, group, a, which may be identical or different, denotes 0 or an integer from 1 to 3, in particular 0, - b denotes 0 or 1 , in particular 1 ,
  • - R' which may be identical or different, denotes a monovalent radical of formula -C q H 2q L in which q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups:
  • R which may be identical or different, denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based radical, for example a C1-C20 alkyl radical
  • Q denotes a linear or branched group of formula C r H 2r , r being an integer ranging from 2 to 6, preferably from 2 to 4
  • A- represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide or iodide.
  • the amino silicones are chosen from the amino silicones of formula (B).
  • the amino silicones of formula (B) are chosen from amino silicones corresponding to formulae (C), (D), (E), (F) and/or (G) below.
  • the amino silicones corresponding to formula (B) are chosen from the silicones known as "trimethylsilyl amodimethicone" corresponding to formula (C):
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (D) below:
  • n denotes a number from 0 to 999 and in particular from 49 to 249 and more particularly from 125 to 175, and for m to denote a number from 1 to 1000 and in particular from 1 to 10, and more particularly from 1 to 5;
  • - Rl, R2 and R3, which may be identical or different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals Rl to R3 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxyl/alkoxy mole ratio preferably ranges from 0.2: 1 to 0.4:1 and preferably from 0.25:1 to 0.35: 1 and more particularly equals 0.3: 1.
  • the weight-average molecular mass (Mw) of these silicones preferably ranges from 2000 to 1 000 000 and more particularly from 3500 to 200 000.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (E) below: in which:
  • - p and q are numbers such that the sum (p + q) ranges from 1 to 1000, in particular from 50 to 350 and more particularly from 150 to 250; it being possible for p to denote a number from 0 to 999 and in particular from 49 to 349 and more particularly from 159 to 239, and for q to denote a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5;
  • Rl and R2 which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals Rl or R2 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy mole ratio generally ranges from 1 : 0.8 to 1 : 1.1 and preferably from 1 :0.9 to 1 : 1 and more particularly equals 1 :0.95.
  • the weight-average molecular mass (Mw) of the silicone preferably ranges from 2000 to 200 000, even more particularly from 5000 to 100 000 and more particularly from 10 000 to 50 000.
  • the commercial products comprising silicones of structure (D) or (E) may include in their composition one or more other amino silicones of which the structure is different from formula (D) or (E).
  • a product containing amino silicones of structure (D) is sold by the company Wacker under the name Belsil® ADM 652.
  • a product containing amino silicones of structure (E) is sold by Wacker under the name Fluid WR 1300®.
  • the oil-in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or nonionic.
  • the numerical mean size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nm.
  • use may be made according to the invention of the amino silicone microemulsions of formula (E) sold under the names Finish CT 96 E® or SLM 28020® by the company Wacker.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (F) below:
  • - m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
  • - A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 2000 to 1 000 000 and even more particularly from 3500 to 200 000.
  • a silicone corresponding to this formula is, for example, the Xiameter MEM 8299 Emulsion from Dow Corning.
  • the amino silicones corresponding to formula (B) are chosen from the silicones of formula (G) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 500 to 1 000 000 and even more particularly from 1000 to 200 000.
  • a silicone corresponding to this formula is, for example, DC2-8566 Amino Fluid from Dow Corning. amino silicones corresponding to formula (H)
  • R 5 represents a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a d-d 8 alkyl or C 2 -ds alkenyl, for example methyl, radical;
  • - Re represents a divalent hydrocarbon-based radical, in particular a d-d 8 alkylene radical or a divalent Ci-Cis, for example Ci-Cs, alkyleneoxy radical linked to the Si via an SiC bond;
  • - Q- is an anion such as a halide, especially chloride, ion or an organic acid salt, especially acetate;
  • - r represents a mean statistical value ranging from 2 to 20 and in particular from 2 to 8;
  • - s represents a mean statistical value ranging from 20 to 200 and in particular from 20 to 50.
  • - R 7 which may be identical or different, represent a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a d-d 8 alkyl radical, a C 2 -ds alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example a methyl radical;
  • - Re represents a divalent hydrocarbon-based radical, in particular a d-d 8 alkylene radical or a divalent Ci-Cis, for example d-d, alkyleneoxy radical linked to the Si via an SiC bond;
  • R-8 which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a d-ds alkyl radical, a C 2 -ds alkenyl radical or a radical -R6-NHCOR7;
  • - X- is an anion such as a halide, especially chloride, ion or an organic acid salt, especially acetate;
  • - r represents a mean statistical value ranging from 2 to 200 and in particular from 5 to 100.
  • R 2 , R3 and R 4 which may be identical or different, denote a Ci-C 4 alkyl radical or a phenyl group,
  • R5 denotes a Ci-C 4 alkyl radical or a hydroxyl group
  • - n is an integer ranging from 1 to 5, integer ranging from 1 to 5, and x is chosen such that the amine number ranges from 0.01 to 1 meq/g.
  • the multiblock polyoxyalkylenated amino silicones of the type (AB)n, A being a polysiloxane block and B being a polyoxyalkylenated block comprising at least one amine group.
  • Said silicones are preferably constituted of repeating units of the following general formulae: [-(SiMe 2 0) x SiMe 2 - R -N(R")- R * -0(C 2 H40)a(C3H60)b -R * -N(H)-R-] or alternatively
  • - a is an integer greater than or equal to 1 , preferably ranging from 5 to 200 and more particularly ranging from 10 to 100;
  • - b is an integer between 0 and 200, preferably ranging from 4 to 100 and more particularly between 5 and 30;
  • - x is an integer ranging from 1 to 10 000 and more particularly from 10 to 5000;
  • - R" is a hydrogen atom or a methyl
  • R which may be identical or different, represent a divalent linear or branched C 2 -Ci 2 hydrocarbon-based radical, optionally including one or more heteroatoms such as oxygen; preferably, R denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a -CH 2 CH 2 CH 2 OCH 2 CH(OH)CH 2 - radical; preferentially R denotes a -CH 2 CH 2 CH 2 OCH 2 CH(OH)CH 2 - radical;
  • R which may be identical or different, represent a linear or branched C 2 -Ci 2 divalent hydrocarbon-based radical, optionally comprising one or more heteroatoms such as oxygen; preferably, R denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical, or a -CH 2 CH 2 CH 2 OCH 2 CH(OH)CH 2 - radical; preferentially, R' denotes -CH(CH 3 )-CH 2 -.
  • the siloxane blocks preferably represent 50 mol% to 95 mol% of the total weight of the silicone, more particularly from 70 mol% to 85 mol%.
  • the amine content is preferably between 0.02 and 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular mass (Mw) of the silicone is preferably between 5000 and 1 000 000 and more particularly between 10 000 and 200 000.
  • the amino silicone(s) have the INCI name amodimethicone.
  • the amino silicone(s) are present in a total amount of at least 0.1 % by weight relative to the total weight of the composition, more preferably at least 0.15%, more preferentially at least 0.3%>, more preferably at least 0.5%>, better still at least 0.75%> and even better still 1% by weight relative to the total weight of the composition.
  • the amino silicone(s) are present in a total amount ranging from 0.1% to 15% by weight relative to the total weight of the composition, more preferably from 0.15% to 10%, more preferentially from 0.3% to 7% by weight, even more preferably from 0.5% to 5% by weight, better still from 0.75%> to 4% by weight and even better still from 1% to 3% by weight relative to the total weight of the composition.
  • the weight ratio of the total amount of copolymer(s) of crotonic acid or crotonic acid derivative according to the invention to the total amount of amino silicone(s) ranges from 0.1 to 30, more preferentially from 0.5 to 25 and better still from 1 to 20.
  • the composition according to the invention comprises at least one thickener, preferably chosen from natural polymers, carboxyvinyl polymers such as homopolymers or copolymers of acrylic and/or methacrylic acid and/or ester, which are preferably crosslinked, crosslinked thickening polyacrylamides and associative polymers comprising at least one hydrophilic unit and at least one fatty chain.
  • thickener preferably chosen from natural polymers, carboxyvinyl polymers such as homopolymers or copolymers of acrylic and/or methacrylic acid and/or ester, which are preferably crosslinked, crosslinked thickening polyacrylamides and associative polymers comprising at least one hydrophilic unit and at least one fatty chain.
  • the term “thickener” refers to a compound which, by its presence at a concentration of 0.05% by weight, increase the viscosity of a composition into which it is introduced by at least 20 cps, preferably by at least 50 cps, at room temperature (25°C), at atmospheric pressure and at a shear rate of 1 s "1 (the viscosity may be measured using a cone/plate viscometer, a Haake R600 rheometer or the like).
  • the thickeners may be chosen especially from carboxyvinyl polymers such as crosslinked acrylic acid homopolymers (carbomer) such as those sold under the name Carbopol by the company Goodrich, polyacrylates and polymethacrylates such as the products sold under the names Lubrajel or Norgel by the company Guardian or under the name Hispagel by the company Hispano Chimica; polyacrylamides such as the product sold under the name Sepigel 305 by the company SEPPIC; polysaccharides such as alginates, cellulose and derivatives thereof, especially carboxymethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose and microcrystalline cellulose; natural gums such as xanthan gum, guar gum, locust bean gum, acacia gum, scleroglucans, chitin and chitosan derivatives, carrageenans; or clays such as montmorillonite, bentones and magnesium aluminum silicates (Veegum).
  • carboxyvinyl polymers such as crosslinked acrylic acid
  • the composition comprises at least one thickener chosen from crosslinked acrylic and/or methacrylic acid polymers.
  • the composition comprises at least one thickener chosen from crosslinked acrylic acid homopolymers.
  • the thickener may be present in the composition in a total content ranging from 0.01% to 10% by weight relative to the weight of the composition, preferably from 0.1% to 5% by weight relative to the weight of the composition, preferably from 0.4% to 2% by weight relative to the weight of the composition.
  • composition according to the invention advantageously comprises water, which may preferably be present in a content ranging from 20% to 98% by weight relative to the weight of the composition.
  • the composition according to the invention may also comprise one or more fatty substances, preferably chosen from silicones and non-silicone fatty substances that are liquid at 30°C and at atmospheric pressure, better still from silicones and triglyceride oils of plant origin.
  • the total content of fatty substances may range from 0.01% to 20%> by weight, preferably from 0.05%> to 15% by weight and better still from 0.1 % to 10% by weight relative to the total weight of the composition.
  • compositions may also comprise at least one agent commonly used in cosmetics, for example chosen from reducing agents, organic solvents, softeners, antifoams, moisturizers, UV-screening agents, peptizers, solubilizers, fragrances, anionic, cationic, nonionic or amphoteric surfactants, proteins and vitamins.
  • agent commonly used in cosmetics for example chosen from reducing agents, organic solvents, softeners, antifoams, moisturizers, UV-screening agents, peptizers, solubilizers, fragrances, anionic, cationic, nonionic or amphoteric surfactants, proteins and vitamins.
  • the above additives are generally present in an amount for each of them of between 0.01% and 20% by weight relative to the weight of the composition.
  • the composition according to the invention may especially be in the form of a suspension, a dispersion, a gel, an emulsion, especially an oil-in- water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W or polyol/O/W or 0/W/O), in the form of a cream, a mousse, a stick, a dispersion of vesicles, especially of ionic or nonionic lipids, or a two-phase or multiphase lotion.
  • the composition is in the form of a gel.
  • a person skilled in the art may select the appropriate presentation form, and also the method for preparing it, on the basis of his general knowledge, taking into account first the nature of the constituents used, especially their solubility in the support, and secondly the application envisaged for the composition.
  • composition according to the invention may comprise one or more organic solvents.
  • organic solvents examples include lower C1-C4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol mono methyl ether and diethylene glycol monoethyl ether and mo no methyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxy ethanol, and mixtures thereof.
  • lower C1-C4 alkanols such as ethanol and isopropanol
  • polyols and polyol ethers for instance 2-butoxyethanol, propylene glycol, propylene glycol mono methyl ether and diethylene glycol monoethyl ether and mo no methyl ether
  • aromatic alcohols for instance benzyl alcohol or phenoxy ethanol, and mixtures thereof.
  • the composition according to the invention comprises one or more organic solvents.
  • the organic solvents are present in proportions preferably inclusively between 0.1% and 40% by weight approximately relative to the total weight of the dye composition, more preferentially between 1% and 30% by weight approximately and even more particularly inclusively between 5% and 25% by weight relative to the total weight of the composition.
  • composition described above may be used on wet or dry keratin fibers, and also on any type of fair or dark, natural or dyed, permanent- waved, bleached or relaxed keratin fibers.
  • the application to the fibers may be performed via any standard means, in particular using a comb, a fine brush, a coarse brush or with the fingers.
  • the fibers After application of the composition, the fibers maybe left to dry naturally or dried, for example at a temperature above or equal to 30°C.
  • the drying if it is performed, may be performed immediately after the application.
  • the fibers are dried, they are dried, in addition to supplying heat, with a flow of air.
  • a mechanical action may be exerted on the locks, such as combing, brushing or running the fingers through. This operation may similarly be performed once the fibers have been dried, naturally or otherwise.
  • the drying step of the process of the invention may be performed with a hood, a hairdryer, a straightening iron, a Climazon, etc.
  • the drying temperature is between 30°C and 110°C and preferably between 50 and 90°C.
  • the drying temperature is between 110 and 220°C and preferably between 140 and 200°C.
  • Example 1 Composition examples: Example 1 :
  • compositions (g AM/100g)
  • compositions E and F are applied on the locks of Yak hair at a rate of lg of composition applied per gram of locks of hair. After application, the locks of hair are combed, dried with a hair-drier and then combed again.
  • the lock stays horizontal.
  • the lock of hair is agglomerated into packs, not individualized and with not good suppleness.
  • the touch is rigid and not natural.
  • the lock of hair falls with a "curtain” effect, the lock of hair is well individualized. Moreover, the touch is suppleness and natural.
  • the lock of hair treated with composition E according to the invention has a more natural behaviour, the hairs are well individualized and have a good suppleness compared to the lock of hair treated with comparative composition F.

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Abstract

La présente invention concerne l'utilisation d'une composition pour la teinture des fibres kératiniques, comprenant (i) un ou plusieurs copolymères issus de la polymérisation d'au moins un monomère d'acide crotonique ou d'un dérivé d'acide crotonique et d'au moins un monomère d'ester vinylique, (ii) un ou plusieurs pigments et (iii) au moins une silicone aminée pour limiter le transfert.
PCT/EP2018/061583 2017-05-12 2018-05-04 Utilisation d'une composition tinctoriale à base de silicones aminées et de copolymères issus de la polymérisation d'au moins un monomère d'acide crotonique ou d'un dérivé d'acide crotonique, pour limiter le transfert Ceased WO2018206457A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020254009A1 (fr) * 2019-06-19 2020-12-24 Henkel Ag & Co. Kgaa Procédé de coloration d'une matière kératinique
CN114786643A (zh) * 2019-12-13 2022-07-22 莱雅公司 基于巴豆酸共聚物和脂肪胺的气溶胶头发染色装置
US11931449B2 (en) 2019-12-16 2024-03-19 L'oreal Hair dyeing process using at least one silicone comprising at least one carboxylic acid anhydride group, at least one amino silicone and at least one pigment and/or direct dye

Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1222944A (fr) 1958-04-15 1960-06-14 Hoechst Ag Polymères greffés et leur procédé de préparation
FR1564110A (fr) 1967-03-23 1969-04-18
FR1580545A (fr) 1967-07-28 1969-09-05
FR2265781A1 (fr) 1974-04-01 1975-10-24 Oreal
FR2265782A1 (fr) 1974-04-01 1975-10-24 Oreal
US4185087A (en) 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
FR2439798A1 (fr) 1978-10-27 1980-05-23 Oreal Nouveaux copolymeres utilisables en cosmetique, notamment dans des laques et lotions de mises en plis
US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
JPH0517710A (ja) 1991-07-08 1993-01-26 Kansai Paint Co Ltd メタリツク塗料とその塗装法
FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
FR2709418A1 (fr) * 1993-09-01 1995-03-10 Mitsubishi Pencil Co Teinture capillaire.
JPH07258460A (ja) 1994-03-22 1995-10-09 Teijin Chem Ltd 樹脂組成物
FR2741530A1 (fr) 1995-11-23 1997-05-30 Oreal Utilisation pour la coloration temporaire des cheveux ou poils d'animaux d'une composition a base d'une dispersion de polymere filmogene et d'un pigment non-melanique
JPH09188830A (ja) 1996-01-05 1997-07-22 Nisshin Steel Co Ltd 高光輝性メタリック顔料
FR2750601A1 (fr) * 1996-07-02 1998-01-09 Oreal Nouvelles compositions capillaires comprenant des agents de coloration cristaux liquides (cl) et leur utilisation
JPH10158541A (ja) 1996-11-27 1998-06-16 Nisshin Steel Co Ltd 耐候性，光輝性に優れたダークシルバー色メタリック顔料
JPH10158450A (ja) 1996-11-28 1998-06-16 Shin Etsu Polymer Co Ltd 食品包装用ポリ塩化ビニル樹脂組成物
US5990479A (en) 1997-11-25 1999-11-23 Regents Of The University Of California Organo Luminescent semiconductor nanocrystal probes for biological applications and process for making and using such probes
US6159486A (en) * 1997-01-24 2000-12-12 L'oreal Water-in-oil emulsion, composition containing the emulsion and use thereof
US6225198B1 (en) 2000-02-04 2001-05-01 The Regents Of The University Of California Process for forming shaped group II-VI semiconductor nanocrystals, and product formed using process
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
US20050063933A1 (en) * 2003-06-17 2005-03-24 Sabine Vrignaud Cosmetic hair composition comprising isoeicosane and at least one nonsilicone fixing polymer
US20130149358A1 (en) * 2011-12-07 2013-06-13 Avon Products, Inc. Wash Resistant Compositions Containing Aminosilicone
US20160136084A1 (en) * 2013-06-20 2016-05-19 L'oreal Composition comprising a combination of an acrylic polymer and an amino silicone

Patent Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1222944A (fr) 1958-04-15 1960-06-14 Hoechst Ag Polymères greffés et leur procédé de préparation
FR1564110A (fr) 1967-03-23 1969-04-18
FR1580545A (fr) 1967-07-28 1969-09-05
FR2265781A1 (fr) 1974-04-01 1975-10-24 Oreal
FR2265782A1 (fr) 1974-04-01 1975-10-24 Oreal
US4185087A (en) 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
FR2439798A1 (fr) 1978-10-27 1980-05-23 Oreal Nouveaux copolymeres utilisables en cosmetique, notamment dans des laques et lotions de mises en plis
US4578266A (en) 1983-07-29 1986-03-25 Revlon, Inc. Silicone-based cosmetic products containing pigment
JPH0517710A (ja) 1991-07-08 1993-01-26 Kansai Paint Co Ltd メタリツク塗料とその塗装法
FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
FR2709418A1 (fr) * 1993-09-01 1995-03-10 Mitsubishi Pencil Co Teinture capillaire.
JPH07258460A (ja) 1994-03-22 1995-10-09 Teijin Chem Ltd 樹脂組成物
US6106577A (en) * 1995-11-23 2000-08-22 L'oreal Use of a composition containing a film-forming polymer dispersion and non-melanic pigment for temporarily dyeing human or animal hair
FR2741530A1 (fr) 1995-11-23 1997-05-30 Oreal Utilisation pour la coloration temporaire des cheveux ou poils d'animaux d'une composition a base d'une dispersion de polymere filmogene et d'un pigment non-melanique
JPH09188830A (ja) 1996-01-05 1997-07-22 Nisshin Steel Co Ltd 高光輝性メタリック顔料
FR2750601A1 (fr) * 1996-07-02 1998-01-09 Oreal Nouvelles compositions capillaires comprenant des agents de coloration cristaux liquides (cl) et leur utilisation
JPH10158541A (ja) 1996-11-27 1998-06-16 Nisshin Steel Co Ltd 耐候性，光輝性に優れたダークシルバー色メタリック顔料
JPH10158450A (ja) 1996-11-28 1998-06-16 Shin Etsu Polymer Co Ltd 食品包装用ポリ塩化ビニル樹脂組成物
US6159486A (en) * 1997-01-24 2000-12-12 L'oreal Water-in-oil emulsion, composition containing the emulsion and use thereof
US5990479A (en) 1997-11-25 1999-11-23 Regents Of The University Of California Organo Luminescent semiconductor nanocrystal probes for biological applications and process for making and using such probes
US6225198B1 (en) 2000-02-04 2001-05-01 The Regents Of The University Of California Process for forming shaped group II-VI semiconductor nanocrystals, and product formed using process
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
US20050063933A1 (en) * 2003-06-17 2005-03-24 Sabine Vrignaud Cosmetic hair composition comprising isoeicosane and at least one nonsilicone fixing polymer
US20130149358A1 (en) * 2011-12-07 2013-06-13 Avon Products, Inc. Wash Resistant Compositions Containing Aminosilicone
US20160136084A1 (en) * 2013-06-20 2016-05-19 L'oreal Composition comprising a combination of an acrylic polymer and an amino silicone

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
COSMETICS AND TOILETRIES, vol. 105, February 1990 (1990-02-01), pages 53 - 64
DABBOUSSI B.O. ET AL.: "CdSe)ZnS core-shell quantum dots: synthesis and characterization of a size series of highly luminescent nanocrystallites", JOURNAL OF PHYSICAL CHEMISTRY B, vol. 101, 1997, pages 9463 - 9475
PENG, XIAOGANG ET AL.: "Epitaxial growth of highly luminescent CdSe/CdS core/shell nanocrystals with photostability and electronic accessibility", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 119, no. 30, pages 7019 - 7029
WALTER NOLL: "Chemistry and Technology of Silicones", 1968, ACADEMIC PRESS

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020254009A1 (fr) * 2019-06-19 2020-12-24 Henkel Ag & Co. Kgaa Procédé de coloration d'une matière kératinique
CN114025739A (zh) * 2019-06-19 2022-02-08 汉高股份有限及两合公司 用于染色角蛋白材料的方法
US11786452B2 (en) 2019-06-19 2023-10-17 Henkel Ag & Co. Kgaa Method for dyeing keratinous material
CN114786643A (zh) * 2019-12-13 2022-07-22 莱雅公司 基于巴豆酸共聚物和脂肪胺的气溶胶头发染色装置
US11931449B2 (en) 2019-12-16 2024-03-19 L'oreal Hair dyeing process using at least one silicone comprising at least one carboxylic acid anhydride group, at least one amino silicone and at least one pigment and/or direct dye

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