WO2010149493A2 - Composition cosmetique comportant un copolymere styrene/acrylate et une resine silicone - Google Patents

Composition cosmetique comportant un copolymere styrene/acrylate et une resine silicone Download PDF

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Publication number
WO2010149493A2
WO2010149493A2 PCT/EP2010/058054 EP2010058054W WO2010149493A2 WO 2010149493 A2 WO2010149493 A2 WO 2010149493A2 EP 2010058054 W EP2010058054 W EP 2010058054W WO 2010149493 A2 WO2010149493 A2 WO 2010149493A2
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weight
composition according
makeup
oil
care composition
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PCT/EP2010/058054
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English (en)
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WO2010149493A3 (fr
Inventor
Roberto Cavazzuti
Claudia Barba
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L'oreal
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Publication of WO2010149493A3 publication Critical patent/WO2010149493A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • 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
    • A61K8/84—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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • Cosmetic composition comprising a styrene/acrylate copolymer and a silicone resin
  • the present invention relates to a cosmetic makeup or care composition
  • a cosmetic makeup or care composition comprising at least one styrene/acrylate copolymer, which is intended in particular for making up and caring for keratin materials (skin and integuments) .
  • the invention relates to a composition for caring for or making up the skin, including the lips, or integuments such as the eyelashes, the eyebrows, the hair and the nails.
  • This composition may be in the form of mascara, eyeliner, a lip product, a makeup rouge, an eye shadow, a foundation, a body makeup product, a concealer product, an antisun composition, a skin colouring composition or a skincare product.
  • Products for making up or caring for human skin or lips such as eyeliners, foundations or lipsticks, or for the eyelashes, for instance mascaras
  • mascaras generally contain fatty substances such as waxes and oils, pigments and/or fillers, and optionally additives such as cosmetic or dermatological active agents.
  • these compositions leave a film thereon, which does not always have good water resistance, for example when bathing or taking a shower, and/or resistance to tears and/or perspiration and/or sebum and/or rubbing with the fingers or against clothing. The film is thus weakened and the makeup no longer has good staying power over time.
  • these compositions also have the drawback of transferring, i.e. of becoming at least partly deposited, leaving marks on certain supports with which they may come into contact, and especially a glass, a cup, a cigarette, an item of clothing or the skin. This results in mediocre persistence of the applied film, making it necessary regularly to freshen the application of the makeup composition. Moreover, the appearance of unacceptable marks, especially on blouse collars, may put certain women off using this type of makeup.
  • one subject of the present invention is a makeup and/or care composition, especially for the skin and/or the lips, comprising, in a cosmetically acceptable support, at least one fatty phase, at least one silicone resin and at least one styrene/acrylate copolymer.
  • Another subject of the invention is the use of a cosmetic makeup or care composition comprising at least one fatty phase, at least one styrene/alkyl acrylate copolymer and at least one silicone resin, for obtaining a film of good staying power and/or that is resistant to water and/or resistant to rubbing and/or resistant to perspiration and/or resistant to sebum and/or that has transfer-resistance properties.
  • a subject of the invention is also a cosmetic process for making up or caring for keratin materials, especially the skin and/or the lips, which consists in applying thereto a composition as described previously.
  • composition according to the invention comprises at least one styrene/acrylate copolymer.
  • the styrene/acrylate copolymer is a tert-butylstyrene/Cl-ClO alkyl methacrylate/Cl-C10 alkyl acrylate copolymer. More preferably, it is a copolymer of tert-butylstyrene/Cl-ClO alkyl methacrylate/Cl-C10 alkyl acrylate and of a vinylaromatic monomer other than tert-butylstyrene .
  • the lipophilic polymer may be a copolymer derived from the polymerization of: a) 10% to 55% by weight, relative to the total weight of monomers, of para-tert-butylstyrene, b) 20% to 80% by weight of Cl-ClO alkyl methacrylate monomer, c) 2% to 25% by weight of Cl-ClO alkyl acrylate monomer, d) from 0 to 40% by weight of a vinylaromatic monomer other than para-tert-butylstyrene.
  • alkyl denotes a linear or branched saturated aliphatic radical, the alkyl group possibly being substituted, for example with a cycloalkyl group.
  • the alkyl group of the Cl-ClO alkyl methacrylate monomer may be linear or branched and may preferably comprise from 1 to 4 carbon atoms and better still 4 carbons.
  • Cl-ClO alkyl methacrylates that may be mentioned include methyl methacrylate, ethyl methacrylate, propyl methacrylate, isobutyl methacrylate and n-butyl methacrylate.
  • the methacrylate monomer that is particularly preferred is isobutyl methacrylate .
  • the alkyl group of the Cl-ClO alkyl acrylate monomer may be linear or branched and may preferably comprise from 2 to 8 carbon atoms and better still 8 carbon atoms.
  • Cl-ClO alkyl acrylates examples include propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, pentyl acrylate, hexyl acrylate and 2-ethylhexyl acrylate.
  • the acrylate monomer that is particularly preferred is 2- ethylhexyl acrylate.
  • the vinylaromatic monomer optionally present in the copolymer may be chosen from vinylaromatic monomers other than tert-butylstyrene, which are known to undergo radical polymerization.
  • the vinylaromatic monomers that may especially be used include those containing from 8 to 20 carbon atoms and better still those containing from 4 to 14 carbon atoms.
  • Such monomers are, for example, styrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 2-methylstyrene (or ortho- methylstyrene) , 3-methylstyrene, 4-methylstyrene (or para-methylstyrene) , 4-propylstyrene, 4-cyclohexyl- styrene, 4-dodecylstyrene, 2-ethyl-4-benzylstyrene and 4- (phenylbutyl) styrene .
  • Styrene, para-methylstyrene or ortho-methylstyrene, and mixtures thereof may preferably be used.
  • the vinylaromatic monomer that is particularly preferred is para-methylstyrene.
  • the crosslinking monomer may be present in the copolymer in a content ranging from 0.1% to 10% by weight relative to the total weight of monomer mixture in the copolymer.
  • the said copolymer may be present in the composition in a content ranging from 0.5% to 40% by weight, preferably from 1% to 30% by weight and better still from 5% to 25% by weight relative to the total weight of the composition.
  • the fatty phase of the composition according to the invention allows the said styrene/acrylate copolymer to be readily incorporated into the composition .
  • composition according to the invention comprises at least one silicone resin.
  • a polydimethylsiloxane is not a silicone resin.
  • silicone resins also known as siloxane resins
  • MDTQ siloxane resins
  • the letter "M” represents the Monofunctional unit of formula RlR2R3SiOl/2, the silicon atom being connected to only one oxygen atom in the polymer comprising this unit.
  • the letter “D” means a Difunctional unit RlR2SiO2/2 in which the silicon atom is connected to two oxygen atoms .
  • the letter “T” represents a Trifunctional unit of formula RlSiO3/2.
  • R represents a hydrocarbon-based radical (especially alkyl) containing from 1 to 10 carbon atoms, a phenyl group, a phenylalkyl group or a hydroxyl group.
  • the letter "Q" means a tetrafunctional unit SiO4/2 in which the silicon atom is linked to four oxygen atoms, which are themselves linked to the rest of the polymer.
  • silicone resins that may be used in the compositions according to the invention, use may be made, for example, of silicone resins of MQ type, of T type or of MQT type.
  • silicone resins of MQ type examples include: the alkyl siloxysilicates of formula [ (Rl) 3SiOi /2 ]x (SiO 4/2 ) y (MQ units) in which x and y are integers ranging from 50 to 80, and such that the group Rl represents a radical as defined previously, and is preferably an alkyl group containing from 1 to 8 carbon atoms, preferably a methyl group, as examples of solid silicone resins of MQ type of trimethyl siloxysilicate type, mention may be made of those sold under the reference SRlOOO by the company General Electric, under the reference TMS 803 by the company Wacker, or under the name KF-7312J by the company Shin- Etsu or DC749 or DC593 by the company Dow Corning, - as silicone resins comprising MQ siloxysilicate units, mention may also be made of phenylalkylsiloxysilicate resins, such as phenylpropy
  • silicone resins of type T examples include: the polysilsesquioxanes of formula (RSi ⁇ 3 / 2)x (units T) in which x is greater than 100 and such that the group R is an alkyl group containing from 1 to 10 carbon atoms.
  • Polymethylsilsesquioxane resins that may preferably be used are those in which R represents a methyl group, for instance those sold: by the company Wacker under the reference Resin MK, such as Belsil PMS MK: polymer comprising CH3SiO3/2 repeating units (units T) , which may also comprise up to 1% by weight of (CH 3 ) 2SiO2/2 units (units D) and having an average molecular weight of about 10 000, by the company Shin-Etsu under the reference KR-220L, which are composed of units T of formula CH3SiO3/2 and have Si-OH (silanol) end groups, under the reference KR-242A, which comprise 98% of units T and 2% of dimethyl units D and have Si-OH end groups, or alternatively under the reference KR-251 comprising 88% of units T and 12% of dimethyl units D and have Si-OH end groups.
  • Resin MK such as Belsil PMS MK: polymer comprising CH
  • MQT resins Resins comprising MQT units that are especially known are those mentioned in document US 5 110 890.
  • a preferred form of resins of MQT type are MQT- propyl (also known as MQT pr ) resins.
  • MQT- propyl also known as MQT pr
  • Such resins that may be used in the compositions according to the invention are especially the resins described and prepared in patent application WO 2005/075 542, the content of which is incorporated herein by reference.
  • the MQ-T-propyl resin comprises the following units:
  • a hydrocarbon-based radical especially alkyl
  • the siloxane resin comprises the following units:
  • R 1 and R 3 independently representing an alkyl group containing from 1 to 8 carbon atoms
  • Ri preferably being a methyl group and R 3 preferably being a propyl group
  • a being between 0.05 and 0.5 and preferably between 0.15 and 0.4
  • c being greater than 0 and preferably between 0.15 and 0.4
  • d being between 0.05 and 0.6, preferably between 0.2 and 0.6, or alternatively between 0.2 and 0.55
  • a + b + c + d l, on condition that more than 40 mol% of the groups R 3 of the siloxane resin are propyl groups.
  • the siloxane resins that may be used according to the invention may be obtained via a process comprising the reaction of:
  • an MQ resin comprising at least 80 mol% of units (R 1 3 SiOi/ 2 )a and (SiO 4 /2)d R 1 representing an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, a and d being greater than 0, the ratio a/d being between 0.5 and 1.5; and
  • T-propyl resin comprising at least 80 mol% of units (R 3 Si0 3 /2)c
  • R 3 representing an alkyl group containing from 1 to 8 carbon atoms, an aryl group, a carbinol group or an amino group, c being greater than 0, on condition that at least 40 mol% of the groups R 3 are propyl groups, in which the mass ratio A/B is between 95/5 and 15/85 and the mass ratio A/B is preferably 30/70.
  • the mass ratio A/B is between 95/5 and 15/85.
  • the ratio A/B is less than or equal to 70/30.
  • the siloxane resin is present in the composition in a total resin solids content ranging from 1% to 80% by weight, preferably ranging from 2% to 70% by weight and better still ranging from 3% to 60% by weight relative to the total weight of the composition .
  • the siloxane resin is present in the composition in a total resin solids content ranging from 1% to 40% by weight, preferably ranging from 2% to 30% by weight and better still ranging from 3% to 25% by weight relative to the total weight of the composition .
  • the silicone resin/styrene/acrylate copolymer mass ratio is between 1/10 and 10/1 and preferably between 1/5 and 1/1.
  • the fatty phase of the composition according to the invention may comprise at least one solid fatty substance such as a pasty substance or a wax .
  • the composition comprises at least one wax.
  • the wax under consideration in the context of the present invention is generally a lipophilic compound that is solid at room temperature (25°C), with a solid/liquid reversible change of state, having a melting point of greater than or equal to 30 0 C, which may be up to 200 0 C and in particular up to 120 0 C.
  • the waxes that are suitable for the invention may have a melting point of greater than or equal to 45°C and in particular greater than or equal to 55°C. or the purposes of the invention, the melting point corresponds to the temperature of the most endothermic peak observed by thermal analysis (DSC) as described in standard ISO 11357-3; 1999.
  • the melting point of the wax may be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name MDSC 2920 by the company TA Instruments .
  • the measuring protocol is as follows:
  • a sample of 5 mg of wax placed in a crucible is subjected to a first temperature rise ranging from -20°C to 100 0 C, at a heating rate of 10°C/minute, it is then cooled from 100°C to -20 0 C at a cooling rate of 10°C/minute and is finally subjected to a second temperature increase ranging from -20 0 C to 100 0 C at a heating rate of 5°C/minute.
  • the variation of the difference in power absorbed by the empty crucible and by the crucible containing the sample of wax is measured as a function of the temperature.
  • the melting point of the compound is the temperature value corresponding to the top of the peak of the curve representing the variation in the difference in absorbed power as a function of the temperature.
  • waxes that are suitable for the invention, mention may be made especially of hydrocarbon-based waxes, for instance beeswax, lanolin wax, Chinese insect waxes, rice bran wax, carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumach wax; montan wax, orange wax and lemon wax, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, the waxes obtained by Fischer-Tropsch synthesis and waxy copolymers, and also esters thereof.
  • hydrocarbon-based waxes for instance beeswax, lanolin wax, Chinese insect waxes, rice bran wax, carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumach wax; montan wax, orange wax and lemon wax, microcrystalline waxes, paraffins and ozokerite; polyethylene waxe
  • waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched C8-C32 fatty chains are examples of waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched C8-C32 fatty chains.
  • isomerized jojoba oil such as the trans-isomerized partially hydrogenated jojoba oil manufactured or sold by the company Desert Whale under the commercial reference Iso-Joj oba-50 ® , hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and bis (1, 1, 1-trimethylol- propane) tetrastearate sold under the name Hest 2T-4S by the company Heterene.
  • silicone waxes C30-45 alkyl dimethicone
  • fluoro waxes C30-45 alkyl dimethicone
  • Phytowax ricin 16L64 ® and 22L73 ® by the company Sophim may also be used. Such waxes are described in patent application FR-A-2 792 190.
  • a wax that may be used is a C20-C40 alkyl (hydroxystearyloxy) stearate (the alkyl group containing from 20 to 40 carbon atoms), alone or as a mixture.
  • microwaxes that may be used in the compositions according to the invention, mention may be made especially of carnauba microwaxes, such as the product sold under the name MicroCare 350 ® by the company Micro Powders, synthetic microwaxes, such as the product sold under the name MicroEase 114S ® by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and polyethylene wax, such as the products sold under the names Micro Care 300 ® and 310 ® by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and of synthetic wax, such as the product sold under the name Micro Care 325® by the company Micro Powders, polyethylene microwaxes, such as the products sold under the names Micropoly 200®, 220®, 220L® and 250S® by the company Micro Powders, and polytetrafluoroethylene microwaxes, such as the products sold under the names Microslip 519® and 519 L® by the company Micro Powders.
  • composition according to the invention may have a wax content ranging from 0.1% to 30% by weight, and in particular it may contain from 0.5% to 15% and more particularly from 1% to 10% by weight of wax relative to the total weight of the composition.
  • composition according to the invention is free of wax.
  • composition according to the invention may comprise another solid fatty substance such as at least one pasty compound.
  • the term "pasty” refers to a lipophilic fatty compound that undergoes a reversible solid/liquid change of state and that comprises in the solid state an anisotropic crystal organization, and comprises, at a temperature of 23°C, a liquid fraction and a solid fraction.
  • the starting melting point of the pasty compound is less than 23°C.
  • the liquid fraction of the pasty compound measured at 23°C may represent 9% to 97% by weight of the compound. This liquid fraction at 23°C preferably represents between 15% and 85% and more preferably between 40% and 85% by weight.
  • the liquid fraction by weight of the pasty compound at 23°C is equal to the ratio of the heat of fusion consumed at 23°C to the heat of fusion of the pasty compound.
  • the heat of fusion of the pasty compound is the heat consumed by the compound to change from the solid state to the liquid state.
  • the pasty compound is said to be in the solid state when all of its mass is in solid form.
  • the pasty compound is said to be in the liquid state when all of its mass is in liquid form.
  • the heat of fusion of the pasty compound is equal to the area under the curve of the thermogram obtained using a differential scanning calorimeter (DSC) , such as the calorimeter sold under the name MDSC 2920 by the company TA Instruments, with a temperature rise of 5 or 10 0 C per minute, according to standard ISO 11357- 3:1999.
  • DSC differential scanning calorimeter
  • the heat of fusion of the pasty compound is the amount of energy required to make the compound change from the solid state to the liquid state. It is expressed in J/g.
  • the heat of fusion consumed at 23°C is the amount of energy absorbed by the sample to change from the solid state to the state that it has at 23°C, constituted of a liquid fraction and a solid fraction.
  • the liquid fraction of the pasty compound, measured at 32°C preferably represents from 30% to 100% by weight of the compound, preferably from 50% to 100% and more preferably from 60% to 100% by weight of the compound.
  • the temperature of the end of the melting range of the pasty compound is less than or equal to 32°C.
  • the liquid fraction of the pasty compound measured at 32°C is equal to the ratio of the heat of fusion consumed at 32°C to the heat of fusion of the pasty compound.
  • the heat of fusion consumed at 32°C is calculated in the same manner as the heat of fusion consumed at 23°C.
  • the pasty compound is preferably chosen from synthetic compounds and compounds of plant origin.
  • a pasty compound may be obtained by synthesis from starting materials of plant origin.
  • the pasty compound may advantageously be chosen from: lanolin and derivatives thereof, - polymer or non-polymer silicone compounds, polymer or non-polymer fluoro compounds, vinyl polymers, especially:
  • oligomers which are homopolymers and copolymers of vinyl esters containing C8-C30 alkyl groups
  • oligomers which are homopolymers and copolymers of vinyl ethers containing C8-C30 alkyl groups, liposoluble polyethers resulting from the polyetherification between one or more C2-C100 and preferably C2-C50 diols, - polyol ethers chosen from ethers of pentaerythritol and of polyalkylene glycol, ethers of fatty alcohol and of sugar, and mixtures thereof, the pentaerythrityl ether of polyethylene glycol comprising 5 oxyethylene units (5 OE) (CTFA name: PEG-5 Pentaerythrityl
  • the pentaerythrityl ether of polypropylene glycol comprising 5 oxypropylene units (5 OP) CTFA name: PPG-5 Pentaerythrityl Ether
  • 5 OP oxypropylene units
  • PEG-5 Pentaerythrityl Ether PPG-5 Pentaerythrityl Ether
  • soybean oil sold under the name Lanolide by the company Vevy, in which mixture the constituents are in a 46/46/8 weight ratio: 46% of PEG-5
  • Pentaerythrityl Ether 46% of PPG-5 Pentaerythrityl Ether and 8% of soybean oil, esters, and mixtures thereof.
  • a preferred fluorinated and silicone-based pasty compound is polymethyl trifluoropropyl methylalkyl dimethylsiloxane, manufactured under the name X22-1088 by Shin-Etsu.
  • the preferred liposoluble polyethers are, in particular, copolymers of ethylene oxide and/or of propylene oxide with C6-C30 long-chain alkylene oxides, more preferably such that the weight ratio of the ethylene oxide and/or propylene oxide to the alkylene oxides in the copolymer is from 5/95 to 70/30.
  • this family mention will be made especially of copolymers such that the long-chain alkylene oxides are arranged in blocks with an average molecular weight from 1000 to
  • a polyoxyethylene/polydodecyl glycol block copolymer such as ethers of dodecanediol
  • esters that are especially preferred are : - esters of a glycerol oligomer, especially diglycerol esters, in particular condensates of adipic acid and of glycerol, for which some of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic acid and isostearic acid, and 12-hydroxystearic acid, especially such as the product sold under the brand name Softisan 649 by the company Sasol, arachidyl propionate sold under the brand name Waxenol 801 by Alzo, phytosterol esters, fatty acid triglycerides and derivatives thereof, - pentaerythritol esters, non-crosslinked polyesters resulting from polycondensation between a linear or branched C 4 -C 5 O dicarboxylic acid or polycarboxylic acid and a C2-C50 diol or polyol
  • the aliphatic carboxylic acid contains from 4 to 30 and preferably from 8 to 30 carbon atoms. It is preferably chosen from hexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, hexyldecanoic acid, heptadecanoic acid, octadecanoic acid, isostearic acid, nonadecanoic acid, eicosanoic acid, isoarachidic acid, octyldodecanoic acid, heneicosanoic acid and docosanoic acid, and mixtures thereof.
  • the aliphatic carboxylic acid is preferably branched.
  • the aliphatic hydroxycarboxylic acid ester is advantageously derived from a hydroxylated aliphatic carboxylic acid containing from 2 to 40 carbon atoms, preferably from 10 to 34 carbon atoms and better still from 12 to 28 carbon atoms, and from 1 to 20 hydroxyl groups, preferably from 1 to 10 hydroxyl groups and better still from 1 to 6 hydroxyl groups.
  • the aliphatic hydroxycarboxylic acid ester is chosen from: a) partial or total esters of saturated linear monohydroxylated aliphatic monocarboxylic acids; b) partial or total esters of unsaturated monohydroxylated aliphatic monocarboxylic acids; c) partial or total esters of saturated monohydroxylated aliphatic polycarboxylic acids; d) partial or total esters of saturated poly- hydroxylated aliphatic polycarboxylic acids; e) partial or total esters of C2 to C16 aliphatic polyols that have reacted with a monohydroxylated or polyhydroxylated aliphatic monocarboxylic or polycarboxylic acid, and mixtures thereof.
  • the aliphatic esters of an ester are advantageously chosen from: the ester resulting from the esterification reaction of hydrogenated castor oil with isostearic acid in proportions of 1 to 1 (1/1) or hydrogenated castor oil monoisostearate, - the ester resulting from the esterification reaction of hydrogenated castor oil with isostearic acid in proportions of 1 to 2 (1/2) or hydrogenated castor oil diisostearate, the ester resulting from the esterification reaction of hydrogenated castor oil with isostearic acid in proportions of 1 to 3 (1/3) or hydrogenated castor oil triisostearate, and mixtures thereof.
  • the composition has a total content of pasty fatty substances ranging from 0.5% to 50% by weight, preferably from 1% to 40% and better still from
  • Liquid fatty phase Liquid fatty phase
  • the composition according to the invention comprises at least one oil.
  • oil means a non-aqueous water- immiscible compound that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg) .
  • Non-volatile oil
  • the composition according to the invention comprises at least one non-volatile oil.
  • the non-volatile oils may be hydrocarbon-based oils and/or silicone oils and/or fluoro oils.
  • non-volatile oil means an oil that remains on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 ⁇ 3 mmHg (0.13 Pa) .
  • a non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm 2 .
  • These oils may be of plant, mineral or synthetic origin .
  • the non-volatile oil may be present in a content ranging from 0.1% to 70% by weight, preferably ranging from 0.5% to 60% by weight and preferentially ranging from 1% to 50% by weight relative to the total weight of the non-volatile liquid fatty phase.
  • Non-volatile hydrocarbon-based oils that may especially be mentioned include:
  • hydrocarbons of mineral or synthetic origin such as liquid paraffin or derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam ® sold by the company Nippon Oil Fats, and squalane, and mixtures thereof;
  • - fatty acid esters in particular of 4 to 22 carbon atoms, and especially of octanoic acid, heptanoic acid, lanolic acid, oleic acid, lauric acid or stearic acid, for instance propylene glycol dioctanoate, propylene glycol monoisostearate, poly- 2-glyceryl diisostearate or neopentyl glycol diheptanoate,
  • R1COOR2 the oils of formula R1COOR2 in which Ri represents a linear or branched fatty acid residue comprising from 1 to 40 carbon atoms and R2 represents a hydrocarbon-based chain, which is especially branched, containing from 1 to 40 carbon atoms, on condition that Ri + R2 ⁇ 11, for instance Purcellin oil (cetostearyl octanoate) , isononyl isononanoate, C12 to Ci 5 alkyl benzoates, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, isopropyl myristate, isopropyl palmitate, butyl stearate, hex
  • - fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon- based chain containing from 8 to 26 carbon atoms, for instance oleyl alcohol, linoleyl alcohol or linolenyl alcohol, isostearyl alcohol or octyldodecanol;
  • - Cs-C26 higher fatty acids such as oleic acid, linoleic acid, linolenic acid or isostearic acid;
  • the non-volatile oil is a non-volatile ester oil such as those mentioned previously.
  • the non-volatile oil is a linear or branched hydrocarbon.
  • the non-volatile silicone oils that may be used in the first and/or second composition according to the invention may be: - phenyl silicone oils (the term "phenyl silicone” means an organopolysiloxane substituted with at least one phenyl group), for instance phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxydiphenyl- siloxanes, diphenyl dimethicones, diphenyl methyl diphenyltrisiloxanes and 2-phenylethyl trimethylsiloxy silicates, dimethicones or phenyl trimethicones with a viscosity of less than or equal to 100 cSt, and mixtures thereof,
  • the silicone oil corresponds to the formula:
  • the groups R represent, independently of each other, a methyl or a phenyl.
  • the said organopolysiloxane comprises at least three phenyl groups for example at least four or at least five.
  • Mixtures of the phenyl organopolysiloxanes described previously may be used. Examples that may be mentioned include mixtures of triphenyl, tetraphenyl or pentaphenyl organopoly- siloxane .
  • the silicone oil corresponds to the formula
  • a phenyl silicone is especially trimethylpentaphenyltrisiloxane (or 1, 3, 5-trimethyl- 1, 1, 3, 5, 5-pentaphenyltrisiloxane) sold under the reference PH-1555 HRI by the company Dow Corning.
  • the reference Dow Corning 554 Cosmetic Fluid may also be used.
  • the oil (s) represent from 0.1% to 90%, better still from 1% to 80% and even better still from 5% to 70% of the total weight of the composition.
  • the non-volatile oil (s) represent from 0.1% to 90%, better still from 1% to 80% and even better still from 5% to 70% of the total weight of the composition.
  • the non-volatile oil may be chosen from glossy oils.
  • the glossy oil is preferably an oil of high molar mass ranging from 650 to 10 000 g/mol and preferably between 750 and 7500 g/mol.
  • the glossy oils are preferably non-volatile.
  • oil means a non-aqueous water- immiscible compound that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg) .
  • non-volatile oil means an oil that remains on keratin materials at room temperature and atmospheric pressure for at least several hours and that especially has a vapour pressure of less than 10 ⁇ 3 mmHg (0.13 Pa) .
  • a non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined previously, the amount evaporated after 30 minutes is less than 0.07 mg/cm 2 .
  • the glossy oil (s) represent from 0.1% to 80%, better still from 1% to 60% and even better still from 5% to 50% of the total weight of the composition.
  • the glossy oil preferably has a high molecular weight ranging from 650 to 10 000 g/mol, and preferably between 750 and 7500 g/mol.
  • the glossy oil may be chosen from:
  • R 1 represents a diol dimer residue obtained by hydrogenation of dilinoleic diacid
  • R 2 represents a hydrogenated dilinoleic acid residue
  • the glossy oil may also be a triglyceride oligomer of a hydroxylated fatty acid and of a saturated diacid.
  • a hydroxylated fatty acid triglyceride such as hydrogenated castor oil
  • a saturated diacid such as hydrogenated castor oil
  • the oligomer may be a mixture of several oligomers.
  • saturated diacids that may be used, mention may be made of sebacic acid (or
  • the oligomer may be an oligoester in which the monomers are represented by the triglyceride (A) and diacid (B) formulae below:
  • Ri represents a saturated or unsaturated, linear or branched alkylene group containing, for example, from 1 to 18 carbon atoms
  • R2 represents a saturated or unsaturated, linear or branched alkyl group containing, for example, from 1 to 12 carbon atoms
  • Ri preferably represents a group - (CH 2 ) n ⁇ , in which n may range from 1 to 20 and especially from 3 to 16, for example from 6 to 12;
  • R2 preferably represents a group - (CH 2 ) m -CH 3 , in which m may range from 0 to 11 and especially from 2 to 11, for example from 3 to 9.
  • H represents the alkyl residue of 12-hydroxystearic acid, which is a major component of hydrogenated castor oil
  • Xi is a linear or branched alkylene group, for instance a linear alkylene group -(CH 2 )X- in which x may range from 1 to 30 and especially from 3 to 15.
  • the average degree of polymerization of the oligomer may range between 3 and 12.
  • the oligoester of hydrogenated castor oil and of sebacic acid is sold especially by the company Croda under various names depending on the degree of polymerization .
  • the oligoesters formed from hydrogenated castor oil and sebacic acid the one with a degree of polymerization of about 4.6 is available under the trade name Cromadol CWS-5 and that with a degree of polymerization of about 9.5 is available under the trade name Cromadol CWS-IO, sold by Croda Japan K. K.
  • the oligomer may be present in the composition according to the invention in a content ranging from 0.1% to 50% by weight, particularly from 0.1% to 40% by weight, more particularly from 0.5% to 30% by weight, and for example from 1% to 20% by weight, relative to the total weight of the composition.
  • the glossy oil has a refractive index of greater than or equal to 1.45 and especially ranging from 1.45 to 1.6.
  • the glossy oil (s) represent from 0.1% to 80%, better still from 1% to 60% and even better still from 5% to 50% of the total weight of the composition.
  • composition according to the invention may comprise at least one volatile oil.
  • volatile oil means an oil that is capable of evaporating on contact with keratin materials in less than one hour, at room temperature and atmospheric pressure (760 mmHg) .
  • the volatile organic solvent (s) and the volatile oils of the invention are volatile organic solvents and cosmetic oils, which are liquid at room temperature, having a non-zero vapour pressure, at room temperature and atmospheric pressure, in particular ranging from 0.13 Pa to 40 000 Pa (10 ⁇ 3 to 300 mmHg) , in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • oils may be hydrocarbon-based oils, silicone oils or fluoro oils, or mixtures thereof.
  • the volatile oil is a volatile silicone oil.
  • silicon oil means an oil comprising at least one silicon atom and especially comprising Si-O groups.
  • the volatile silicone oil may be chosen from linear or cyclic silicone oils such as linear or cyclic polydimethylsiloxanes (PDMS) containing from 3 to 7 silicon atoms.
  • oils that may be mentioned include octyl trimethicone, hexyl trimethicone, decamethylcyclopentasiloxane (cyclopentasiloxane or D5) , octamethylcyclotetrasiloxane (cyclotetradimethyl- siloxane or D4), dodecamethylcyclohexasiloxane (D6) , decamethyltetrasiloxane (L4), KF 96 A from Shin-Etsu, the polydimethylsiloxanes such as those sold under the reference DC 200 (1.5 cSt) , DC 200 (5 cSt) and DC 200 (3 cSt) by Dow Corning.
  • the volatile oil is a volatile hydrocarbon-based oil.
  • hydrocarbon-based oil means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • the volatile hydrocarbon-based oils may be chosen from hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially C8-C16 branched alkanes, for instance C8-C16 isoalkanes of petroleum origin (also known as isoparaffins) , for instance isododecane (also known as 2,2,4,4,6- pentamethylheptane) , isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, C8-C16 branched esters, isohexyl neopentanoate, and mixtures thereof.
  • C8-C16 branched alkanes for instance C8-C16 isoalkanes of petroleum origin (also known as isoparaffins)
  • isododecane also known as 2,2,4,4,6- pentamethylheptane
  • isodecane isohexadecane
  • isohexadecane
  • ketones that are liquid at room temperature, such as methyl ethyl ketone, acetone
  • short-chain esters containing from 3 to 8 carbon atoms in total
  • ethers that are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether
  • the volatile oil may also be chosen from fluoro oils such as perfluoropolyethers, perfluoroalkanes, for instance perfluorodecalin, perfluoroadamantanes, perfluoroalkyl phosphate monoesters, diesters and triesters, and fluoro ester oils.
  • fluoro oils such as perfluoropolyethers, perfluoroalkanes, for instance perfluorodecalin, perfluoroadamantanes, perfluoroalkyl phosphate monoesters, diesters and triesters, and fluoro ester oils.
  • the composition may also comprise at least one dyestuff, for instance pulverulent compounds and/or liposoluble dyes, for example in a proportion of from 0.01% to 50% of the total weight of the composition.
  • the pulverulent compounds may be chosen from pigments and/or nacres and/or fillers usually used in cosmetic or dermatological compositions.
  • the pulverulent compounds represent from 0.1% to 25% and better still from 1% to 20% of the total weight of the composition.
  • the pigments may be white or coloured, and mineral and/or organic.
  • mineral pigments that may be mentioned are titanium dioxide, optionally surface- treated, zirconium oxide or cerium oxide, and also iron oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • organic pigments that may be mentioned are carbon black, pigments of D&C type, and lakes based on cochineal carmine or on barium, strontium, calcium or aluminium.
  • the nacreous pigments may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as titanium mica with iron oxides, titanium mica with, especially, ferric blue or chromium oxide, titanium mica with an organic pigment of the abovementioned type and also nacreous pigments based on bismuth oxychloride.
  • the fillers may be chosen from those that are well known to a person skilled in the art and that are commonly used in cosmetic compositions.
  • compositions may also contain any additive usually used in such compositions, such as thickeners, fragrances, preserving agents, surfactants, lipophilic or hydrophilic film-forming polymers, dissolved or dispersed in the composition, especially dispersed in an aqueous medium or an oily medium as described in documents EP-A-749 747 and EP-A-749 746.
  • additives such as thickeners, fragrances, preserving agents, surfactants, lipophilic or hydrophilic film-forming polymers, dissolved or dispersed in the composition, especially dispersed in an aqueous medium or an oily medium as described in documents EP-A-749 747 and EP-A-749 746.
  • Treated silicas and liposoluble alkylated guar gums may also be used.
  • the composition may advantageously comprise less than 3% and better still less than 1% by weight of water relative to the total weight of the composition, or may even be totally anhydrous. It may then be in the form of an oily gel, an oily liquid, a paste, a product cast as a stick or wand, or in a dish, or alternatively in the form of powder.
  • the composition may also comprise at least one aqueous phase and may then be in the form of a water-in-oil, oil-in-water, wax-in-water or water-in-wax emulsion, or a vesicular dispersion containing ionic and/or nonionic lipids.
  • the water content may range from 10% to 95% by weight relative to the total weight of the composition.
  • the composition according to the invention is in liquid form. According to a second embodiment, the composition according to the invention is in solid form.
  • solid characterizes the state of the composition at room temperature (25°C) and at atmospheric pressure (760 mmHg) .
  • the composition according to the invention has, when it is solid, a hardness of between 30 and 300 g, or even from 50 to 200 g.
  • the measurement is performed according to the following protocol:
  • the hardness of the samples is measured after an interval of 24 hours.
  • the hardness of the samples of compositions of the invention expressed in grams, is measured using a DFGS2 tensile testing machine sold by the company Indelco-Chatilion .
  • the hardness corresponds to the maximum shear force exerted by a rigid tungsten wire 250 ⁇ m in diameter, advancing at a rate of 100 mm/minute.
  • the composition according to the invention comprises less than 3% and better still less than 1% by weight of water relative to the total weight of the composition. More preferably, the composition is totally anhydrous.
  • anhydrous especially means that water is preferably not deliberately added to the composition, but may be present in trace amount in the various compounds used in the composition.
  • compositions for topical application may especially constitute a cosmetic, dermatological, hygiene or pharmaceutical composition for protecting, caring for or treating the skin, especially for the face, the neck, the hands or the body (for example a care cream, an antisun oil or a body gel) , a makeup composition, an antisun composition or an artificial tanning composition.
  • the makeup composition may especially be a mascara, an eyeliner, a lip product (lipstick in the form of a stick or a liquid (gloss) ) , a makeup rouge, an eye shadow, a foundation, a concealer product, a body makeup product or an antisun product.
  • the invention is illustrated in greater detail in the examples that follow.
  • Propyl resin a propyl silsesquioxane resin at 74.8% by weight in toluene.
  • the propyl silsesquioxane resin was obtained by hydrolysis of propyltrichlorosilane .
  • An MQ resin, a T propyl resin, xylene and IM KOH in water in the proportions presented in Table 1 are introduced into a 3-necked flask equipped with a stirrer, a temperature probe and Dean-Stark apparatus mounted with a condenser.
  • Xylene is pre-introduced into the Dean-Stark apparatus so as to ensure maintenance of a level of solids of 50% in the reactor.
  • the mixture in the reactor is refluxed (between 100 and 140 0 C) for at least 3 hours. Any water formed in the reaction mixture is continuously removed and trapped in the form of an azeotrope in the Dean-Stark apparatus. After refluxing for 3 hours, the water is removed from the apparatus and heating is continued for a further 30 minutes.
  • Composition 1
  • Composition 2
  • Composition 4 Procedure : Disperse the pigment Red 7 in part of phase B in a three-roll mill. Disperse the MQ resin in the isododecane at room temperature (pregel) .
  • phase D Add the microcrystalline wax and the rest of phase B with stirring using a Rayneri blender at 98°C, and, after the wax has melted, add phase D and the mixture of isododecane and MQ resin, while cooling to 80 0 C.
  • compositions 1 to 5 The staying power of compositions 1 to 5 is measured according to the following protocol:
  • the transfer index of the deposit obtained with the composition according to the invention is determined according to the measuring protocol described below.
  • a support (40 mm x 70 mm rectangle) consisting of an acrylic coating (hypoallergenic acrylic adhesive on polyethylene film sold under the name Blenderme ref . FH5000-55113 by the company 3M Sante) bonded onto a layer of polyethylene foam that is adhesive on the face opposite that onto which the adhesive tape is fixed (foam layer sold under the name RE40X70EP3 by the company Joint Technique Lyonnais Ind.) is prepared.
  • the L* o a*ob*o colour of the support, on the acrylic coating face, is measured using a Minolta CR 300 colorimeter.
  • the support thus prepared is preheated on a hotplate maintained at a temperature of 40 0 C such that the surface of the support is maintained at a temperature of 33°C ⁇ 1°C. While leaving the support on the hotplate, the composition is applied over the entire non-adhesive surface of the support (i.e. to the surface of the acrylic coating) by spreading it out using a fine brush to obtain a deposit of about 15 ⁇ m of the composition, and it is then left to dry for 10 minutes.
  • the support is then bonded via its adhesive face (adhesive face of the foam layer) to an anvil 20 mm in diameter and equipped with a screw pitch.
  • a sample of the support/deposit assembly is then cut out using a punch 18 mm in diameter.
  • the anvil is then screwed onto a press (Statif Manuel Imada SV-2 from the company Someco) equipped with a tensile testing machine (Imada DPS-20 from the company Someco) .
  • a strip 33 mm wide and 29.7 cm long is drawn on a sheet of white photocopier paper with a basis weight of 80 g/m 2 , a first line is marked 2 cm from the edge of the sheet, then a second line is marked 5 cm from the edge of the sheet, the first and second lines thus delimiting a box on the strip; a first mark and a second mark located in the strip at reference points 8 cm and 16 cm, respectively, from the second line is then applied. 20 ⁇ l of water are placed on the first mark and 10 ⁇ l of refined sunflower oil (sold by the company Lesieur) are placed on the second mark.
  • the sheet of white paper is placed on the bed of the press and the sample placed on the box of the strip of paper is then pressed at a pressure of about 300 g/cm 2 exerted for 30 seconds.
  • the press is lifted and the sample is again moved to just after the second line (i.e. next to the box), a pressure of about 300 g/cm 2 is again exerted and, once the contact has been made, the paper is moved in a rectilinear manner at a speed of 1 cm/s, over the entire length of the strip such that the sample passes through the water and oil deposits.
  • the transfer index of the composition is equal to the ratio:
  • the measurement is performed on 6 supports in succession and the transfer value corresponds to the mean of the 6 measurements obtained with the 6 supports .
  • Compositions 4 and 5 outside the invention respectively comprising 15% of MQ resin and 15% of MQT pr resin, and free of styrene/acrylate copolymer, have a transfer index of about 90.
  • the composition thus makes it possible to obtain very good transfer index values whilst significantly reducing the amount of silicone resin in the composition .

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Abstract

La présente invention concerne une composition pour le maquillage et/ou les soins de matières kératiniques, comportant au moins une phase grasse, au moins une résine silicone et au moins un copolymère styrène/acrylate. La composition peut produire un film avec un très bon maintien qui présente de bonnes propriétés de résistance au transfert. Le film obtenu est particulièrement résistant à l’eau et à l’huile.
PCT/EP2010/058054 2009-06-25 2010-06-09 Composition cosmetique comportant un copolymere styrene/acrylate et une resine silicone WO2010149493A2 (fr)

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FR0954344A FR2947175B1 (fr) 2009-06-25 2009-06-25 Composition cosmetique comprenant un copolymere styrene/acrylate et une resine siliconee
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US22249109P 2009-07-02 2009-07-02
US61/222,491 2009-07-02

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013048919A1 (fr) * 2011-09-30 2013-04-04 L'oreal S.A. Compositions cosmétiques comprenant des substances permettant de former des films en latex
WO2014202655A1 (fr) * 2013-06-20 2014-12-24 L'oreal Composition comprenant une combinaison d'un polymère acrylique, d'un copolymère de silicone et d'un acide aminé ou dérivé d'acide aminé
WO2014202658A1 (fr) * 2013-06-20 2014-12-24 L'oreal Composition comprenant une combinaison d'un polymère acrylique et d'un amino-silicone
FR3007288A1 (fr) * 2013-06-20 2014-12-26 Oreal Composition comprenant l'association d'un polymere acrylique, d'un copolymere silicone et d'un polymere epaississant particulier
WO2016140812A1 (fr) * 2015-03-03 2016-09-09 L'oreal Composition de mascara longue tenue
US9585831B2 (en) 2012-12-24 2017-03-07 Conopco, Inc. Cosmetic composition
WO2017107066A1 (fr) * 2015-12-22 2017-06-29 L'oreal Composition pour éclaircir ou blanchir des matières kératiniques
WO2017141919A1 (fr) * 2016-02-15 2017-08-24 株式会社コーセー Substance cosmétique à émulsion de type eau-dans-l'huile
KR20190098205A (ko) * 2016-12-22 2019-08-21 로레알 실리콘 폴리아미드, 실리콘 수지 및 분산된 수성상을 포함하는 고체 미용 조성물
KR20190098192A (ko) * 2016-12-21 2019-08-21 로레알 실리콘 수지 및 비휘발성 실리콘 오일을 포함하는 직접 유화액의 형태인 조성물, 및 이를 이용하는 방법
US10441527B2 (en) 2015-04-08 2019-10-15 Dow Silicones Corporation Fluid compositions and personal care
WO2021222764A1 (fr) 2020-04-30 2021-11-04 L'oreal Émulsions eau dans l'huile contenant un tensioactif, une gomme de silicone et/ou un latex, et une résine siloxysilicate
FR3112949A1 (fr) 2020-07-29 2022-02-04 L'oreal Emulsions eau dans l’huile contenant du latex et une resine de siloxysilicate
FR3113588A1 (fr) 2020-08-28 2022-03-04 L'oreal Emulsions eau dans huile contenant un tensioactif a faible hlb, une gomme de silicone et une resine de siloxysilicate
FR3130134A1 (fr) 2021-12-14 2023-06-16 L'oreal Émulsions eau dans huile comprenant un tensioactif, un polymère acrylique et un organosiloxane
FR3130136A1 (fr) 2021-12-14 2023-06-16 L'oreal Émulsions eau dans l’huile comprenant un tensioactif, un polymère vinylique soluble dans l’eau et un organosiloxane

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3007285B1 (fr) * 2013-06-20 2015-06-19 Oreal Procede densification des fibres keratiniques a base de polymere acrylique et de compose silicone particuliers
FR3060385B1 (fr) * 2016-12-21 2020-01-03 L'oreal Composition comprenant de l’eau, une resine siliconee, une huile siliconee non volatile et procede la mettant en oeuvre

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5662892A (en) * 1996-03-15 1997-09-02 The Procter & Gamble Company Personal care compositions containing hydrophobic linear copolymer and hydrophobic, volatile, branched hydrocarbon solvent
EP1018334A1 (fr) * 1999-01-06 2000-07-12 L'oreal Composition cosmétique comprenant un copolymère styrène/acrylate et une phase grasse
EP1101488A2 (fr) * 1997-04-28 2001-05-23 L'oreal Composition cosmétique ou dermatologique comprenant un polymère filmogène, procédé de maquillage et de traitement non therapeutique
WO2004073626A2 (fr) * 2003-02-14 2004-09-02 Revlon Consumer Products Corporation Compositions cosmetiques contenant des polymeres de siloxane
EP1870075A1 (fr) * 2006-06-20 2007-12-26 L'Oréal Mascara comprenant au moins 21% de cire et une charge
EP2008644A2 (fr) * 2007-06-18 2008-12-31 Beiersdorf AG Mascara à base de copolymères de styrol/acrylate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5662892A (en) * 1996-03-15 1997-09-02 The Procter & Gamble Company Personal care compositions containing hydrophobic linear copolymer and hydrophobic, volatile, branched hydrocarbon solvent
EP1101488A2 (fr) * 1997-04-28 2001-05-23 L'oreal Composition cosmétique ou dermatologique comprenant un polymère filmogène, procédé de maquillage et de traitement non therapeutique
EP1018334A1 (fr) * 1999-01-06 2000-07-12 L'oreal Composition cosmétique comprenant un copolymère styrène/acrylate et une phase grasse
WO2004073626A2 (fr) * 2003-02-14 2004-09-02 Revlon Consumer Products Corporation Compositions cosmetiques contenant des polymeres de siloxane
EP1870075A1 (fr) * 2006-06-20 2007-12-26 L'Oréal Mascara comprenant au moins 21% de cire et une charge
EP2008644A2 (fr) * 2007-06-18 2008-12-31 Beiersdorf AG Mascara à base de copolymères de styrol/acrylate

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Publication number Priority date Publication date Assignee Title
EP2760424A4 (fr) * 2011-09-30 2015-07-15 Oréal L Compositions cosmétiques comprenant des agents formant film de latex
WO2013048919A1 (fr) * 2011-09-30 2013-04-04 L'oreal S.A. Compositions cosmétiques comprenant des substances permettant de former des films en latex
US9402800B2 (en) 2011-09-30 2016-08-02 L'oreal Cosmetic compositions comprising latex film formers
US10449138B2 (en) 2012-12-24 2019-10-22 Conopco, Inc. Cosmetic composition
US9585831B2 (en) 2012-12-24 2017-03-07 Conopco, Inc. Cosmetic composition
KR20160021876A (ko) * 2013-06-20 2016-02-26 로레알 아크릴 중합체, 실리콘 공중합체 및 아미노산 또는 아미노산 유도체의 조합물을 포함하는 조성물
KR102256772B1 (ko) 2013-06-20 2021-05-28 로레알 아크릴 중합체, 실리콘 공중합체 및 아미노산 또는 아미노산 유도체의 조합물을 포함하는 조성물
CN105283168A (zh) * 2013-06-20 2016-01-27 莱雅公司 包含丙烯酸系聚合物和氨基硅酮的组合的组合物
CN105283224A (zh) * 2013-06-20 2016-01-27 莱雅公司 包含丙烯酸系聚合物、硅酮共聚物和氨基酸或氨基酸衍生物的组合的组合物
KR20160021871A (ko) * 2013-06-20 2016-02-26 로레알 아크릴 중합체 및 아미노 실리콘의 조합을 포함하는 조성물
WO2014202655A1 (fr) * 2013-06-20 2014-12-24 L'oreal Composition comprenant une combinaison d'un polymère acrylique, d'un copolymère de silicone et d'un acide aminé ou dérivé d'acide aminé
FR3007286A1 (fr) * 2013-06-20 2014-12-26 Oreal Composition comprenant l'association d'un polymere acrylique, d'un copolymere silicone et d'un amino-acide ou derive d'amino-acide
US10159639B2 (en) 2013-06-20 2018-12-25 L'oreal Composition comprising a combination of an acrylic polymer and an amino silicone
FR3007288A1 (fr) * 2013-06-20 2014-12-26 Oreal Composition comprenant l'association d'un polymere acrylique, d'un copolymere silicone et d'un polymere epaississant particulier
FR3007287A1 (fr) * 2013-06-20 2014-12-26 Oreal Composition comprenant l'association d'un polymere acrylique et d'une silicone aminee
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US10441527B2 (en) 2015-04-08 2019-10-15 Dow Silicones Corporation Fluid compositions and personal care
CN108430433A (zh) * 2015-12-22 2018-08-21 莱雅公司 用于增白或美白角蛋白材料的组合物
WO2017107066A1 (fr) * 2015-12-22 2017-06-29 L'oreal Composition pour éclaircir ou blanchir des matières kératiniques
JPWO2017141919A1 (ja) * 2016-02-15 2018-12-06 株式会社コーセー 油中水型乳化化粧料
WO2017141919A1 (fr) * 2016-02-15 2017-08-24 株式会社コーセー Substance cosmétique à émulsion de type eau-dans-l'huile
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TWI698257B (zh) * 2016-02-15 2020-07-11 日商高絲股份有限公司 油包水型乳化化妝料
KR20180108640A (ko) * 2016-02-15 2018-10-04 가부시키가이샤 코세 유중수형 유화 화장료
CN108601722A (zh) * 2016-02-15 2018-09-28 高丝股份有限公司 油包水型乳化化妆品
CN108601722B (zh) * 2016-02-15 2021-06-11 高丝股份有限公司 油包水型乳化化妆品
JP2020514262A (ja) * 2016-12-21 2020-05-21 ロレアル シリコーン樹脂及び不揮発性シリコーン油を含む、直接エマルションの形態の組成物、並びにこの組成物を使用する方法
KR102291906B1 (ko) * 2016-12-21 2021-08-24 로레알 실리콘 수지 및 비휘발성 실리콘 오일을 포함하는 직접 유화액의 형태인 조성물, 및 이를 이용하는 방법
KR20190098192A (ko) * 2016-12-21 2019-08-21 로레알 실리콘 수지 및 비휘발성 실리콘 오일을 포함하는 직접 유화액의 형태인 조성물, 및 이를 이용하는 방법
KR102297952B1 (ko) 2016-12-22 2021-09-03 로레알 실리콘 폴리아미드, 실리콘 수지 및 분산된 수성상을 포함하는 고체 미용 조성물
KR20190098205A (ko) * 2016-12-22 2019-08-21 로레알 실리콘 폴리아미드, 실리콘 수지 및 분산된 수성상을 포함하는 고체 미용 조성물
WO2021222764A1 (fr) 2020-04-30 2021-11-04 L'oreal Émulsions eau dans l'huile contenant un tensioactif, une gomme de silicone et/ou un latex, et une résine siloxysilicate
FR3112949A1 (fr) 2020-07-29 2022-02-04 L'oreal Emulsions eau dans l’huile contenant du latex et une resine de siloxysilicate
FR3113588A1 (fr) 2020-08-28 2022-03-04 L'oreal Emulsions eau dans huile contenant un tensioactif a faible hlb, une gomme de silicone et une resine de siloxysilicate
FR3130134A1 (fr) 2021-12-14 2023-06-16 L'oreal Émulsions eau dans huile comprenant un tensioactif, un polymère acrylique et un organosiloxane
FR3130136A1 (fr) 2021-12-14 2023-06-16 L'oreal Émulsions eau dans l’huile comprenant un tensioactif, un polymère vinylique soluble dans l’eau et un organosiloxane

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FR2947175B1 (fr) 2011-07-29

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