WO2015014752A1 - Composition cosmétique solide comprenant une résine à base d'hydrocarbure, un copolymère séquencé à base d'hydrocarbure, une huile à base d'hydrocarbure apolaire non volatile et une huile de silicone non volatile - Google Patents

Composition cosmétique solide comprenant une résine à base d'hydrocarbure, un copolymère séquencé à base d'hydrocarbure, une huile à base d'hydrocarbure apolaire non volatile et une huile de silicone non volatile Download PDF

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WO2015014752A1
WO2015014752A1 PCT/EP2014/066060 EP2014066060W WO2015014752A1 WO 2015014752 A1 WO2015014752 A1 WO 2015014752A1 EP 2014066060 W EP2014066060 W EP 2014066060W WO 2015014752 A1 WO2015014752 A1 WO 2015014752A1
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Prior art keywords
hydrocarbon
weight
composition according
composition
styrene
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Inventor
Virginie PEREZ-NOWAK
Sophie FLETY
Nathalie Julien
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LOreal SA
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LOreal SA
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Priority to JP2016530458A priority Critical patent/JP6526655B2/ja
Priority to KR1020167005529A priority patent/KR20160035602A/ko
Priority to CN201480042985.2A priority patent/CN105451709A/zh
Publication of WO2015014752A1 publication Critical patent/WO2015014752A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks

Definitions

  • the present invention relates to a solid cosmetic composition for making up and/or caring for the lips or the skin, comprising a hydrocarbon-based resin, a hydrocarbon- based block copolymer, a non-volatile apolar hydrocarbon-based oil and at least one nonvolatile silicone oil that is incompatible with the hydrocarbon-based phase.
  • Lipsticks which have good colour persistence consist generally of mutually incompatible starting materials, which are compatibilized using volatile or semi-volatile solvent.
  • compositions have improved colour persistence properties when compared with other compositions
  • the use of volatile ingredients nevertheless involves several drawbacks associated, for example, with the increase in manufacturing cost brought about by the adaptation of the processes to the presence of these compounds, and also with the need to use devices that are leaktight with respect to these ingredients in order to condition and market the lipsticks.
  • the presence of volatile substances in the compositions is such that it is no longer possible to leave samples open on shelf displays.
  • the invention thus seeks to obtain the same colour persistence properties as lipsticks that have good colour persistence using the incompatibility of the starting materials, but without using any volatile or semi-volatile compatibilizer.
  • a subject of the present invention is a solid cosmetic composition, preferably for making up and/or caring for the skin or the lips, comprising, in a physiologically acceptable medium,
  • composition according to the invention is homogeneous and stable at room temperature.
  • stable composition especially means that it does not show any exudation or phase separation, in particular after 1 month or even 2 months at 47°C.
  • the composition is in solid form at 20°C.
  • the composition according to the invention is easy to apply to the skin and/or the lips.
  • the ease of application is especially reflected in terms of glidance and the ease of erosion.
  • the composition according to the invention is solid enough not to crack during application.
  • solid cosmetic composition means the form of the composition at 20°C, in opposition to fluid compositions (for example liquid lip compositions such as “gloss"), and in particular the term “solid” means a composition whose hardness at 20°C and at atmospheric pressure (760 mmHg) is greater than or equal to 30 Nm "1 when it is measured according to the protocol described below.
  • the composition according to the invention is a makeup composition, preferably for the lips, for example a solid lipstick, which may be, for example, in the form of a stick or cast in a jar or a dish.
  • the present invention relates to a cosmetic process for making up and/or caring for the lips, comprising the application to the lips and/or the skin of a cosmetic composition as defined previously.
  • the invention relates to a process preferably for making up the lips, comprising the application to the lips of a cosmetic composition as defined previously.
  • physiologically acceptable medium is intended to denote a medium that is particularly suitable for the application of a composition of the invention to the skin or the lips.
  • the physiologically acceptable medium is generally adapted to the nature of the support onto which the composition has to be applied, and also to the appearance under which the composition has to be packaged.
  • the composition comprises less than 4% and preferably less than 2% water.
  • the composition according to the invention is anhydrous.
  • the term "anhydrous" especially means that water is preferably not deliberately added to the compositions, but may be present in trace amounts in the various compounds used in the compositions.
  • composition according to the invention comprises at least one hydrocarbon- based resin.
  • the resin used in the composition according to the invention (also known as the tackifying resin) has a number-average molecular weight of less than or equal to 10 000 g/mol, especially ranging from 250 to 5000 g/mol, better still less than or equal to 2000 g/mol and especially ranging from 250 to 2000 g/mol.
  • Mn number-average molecular weights
  • the resin of the composition according to the invention is advantageously a tackifying resin.
  • tackifying resin Such resins are described especially in the Handbook of Pressure Sensitive Adhesive, edited by Donatas Satas, 3rd edition, 1989, pp. 609-619.
  • the hydrocarbon-based resin is chosen from low molecular weight polymers that may be classified, according to the type of monomer they comprise, as:
  • indene hydrocarbon-based resins preferably such as resins derived from the polymerization in major proportion of indene monomer and in minor proportion of a monomer chosen from styrene, methylindene and methylstyrene, and mixtures thereof. These resins may optionally be hydrogenated. These resins may have a molecular weight ranging from 290 to 1 150 g/mol.
  • indene resins examples include those sold under the reference Escorez 7105 by the company Exxon Chem., Nevchem 100 and Nevex 100 by the company Neville Chem., Norsolene S105 by the company Sartomer, Picco 6100 by the company Hercules and Resinall by the company Resinall Corp., or the hydrogenated indene/methylstyrene/styrene copolymers sold under the name "Regalite” by the company Eastman Chemical, in particular Regalite R 1 100, Regalite R 1090, Regalite R-7100, Regalite R1010 Hydrocarbon Resin and Regalite R1 125 Hydrocarbon Resin; - aliphatic pentanediene resins such as those derived from the majority polymerization of the 1 ,3-pentanediene (trans- or cis-piperylene) monomer and of minor monomer(s) chosen from isoprene, butene, 2-methyl-2-butene, penten
  • Such 1 ,3-pentanediene resins are sold, for example, under the references Piccotac 95 by the company Eastman Chemical, Escorez 1304 by the company Exxon Chemicals, Nevtac 100 by the company Neville Chem. or Wingtack 95 by the company Goodyear;
  • cyclopentanediene dimers such as those derived from the polymerization of first monomers chosen from indene and styrene, and of second monomers chosen from cyclopentanediene dimers such as dicyclopentanediene, methyldicyclopentanediene and other pentanediene dimers, and mixtures thereof.
  • These resins generally have a molecular weight ranging from 500 to 800 g/mol, for instance those sold under the reference Betaprene BR 100 by the company Arizona Chemical Co., Neville LX-685-125 and Neville LX-1000 by the company Neville Chem., Piccodiene 2215 by the company Hercules, Petro-Rez 200 by the company Lawter or Resinall 760 by the company Resinall Corp. ;
  • - diene resins of isoprene dimers such as terpenic resins derived from the polymerization of at least one monomer chosen from a-pinene, a-pinene and limonene, and mixtures thereof. These resins may have a molecular weight ranging from 300 to 2000 g/mol.
  • Such resins are sold, for example, under the names Piccolyte A1 15 and S125 by Hercules or Zonarez 7100 or Zonatac 105 Lite by Arizona Chem.
  • the hydrocarbon-based resin is chosen from indene hydrocarbon-based resins, aliphatic pentadiene resins, mixed resins of pentanediene and of indene, diene resins of cyclopentanediene dimers and diene resins of isoprene dimers, or mixtures thereof.
  • the composition comprises at least one compound chosen from hydrocarbon-based resins as described previously, especially indene hydrocarbon-based resins and aliphatic pentadiene resins, or mixtures thereof.
  • the hydrocarbon-based resin is chosen from indene hydrocarbon-based resins.
  • the resin is chosen from hydrogenated indene/methylstyrene styrene copolymers.
  • indene/methylstyrene/hydrogenated styrene copolymers such as those sold under the name Regalite by the company Eastman
  • the hydrocarbon-based resin is present in the composition according to the invention in a content ranging from 1 % to 45% by weight, preferably ranging from 1 % to 30% by weight, more preferentially ranging from 1 % to 25% by weight and even more advantageously between 1 % and 15% by weight relative to the total weight of the composition.
  • HYDROCARBON-BASED BLOCK COPOLYMER HYDROCARBON-BASED BLOCK COPOLYMER
  • composition according to the invention comprises, besides the resin, a hydrocarbon-based block copolymer, also known as a block copolymer, preferably a block copolymer that is soluble or dispersible in a liquid hydrocarbon-based phase as defined previously.
  • a hydrocarbon-based block copolymer also known as a block copolymer, preferably a block copolymer that is soluble or dispersible in a liquid hydrocarbon-based phase as defined previously.
  • the polymeric gelling agent is capable of thickening or gelling the hydrocarbon- based phase of the composition.
  • amorphous polymer means a polymer that does not have a crystalline form.
  • the polymeric gelling agent is also preferably film-forming, i.e. it is capable of forming a film when applied to the skin and/or the lips.
  • the hydrocarbon-based block copolymer may especially be a diblock, triblock, multiblock, radial or star copolymer, or mixtures thereof.
  • the copolymer may contain at least one block whose glass transition temperature is preferably less than 20°C, preferably less than or equal to 0°C, preferably less than or equal to -20°C and more preferably less than or equal to -40°C.
  • the glass transition temperature of the said block may be between -150°C and 20°C and especially between -100°C and 0°C.
  • the hydrocarbon-based block copolymer present in the composition according to the invention is an amorphous copolymer formed by polymerization of an olefin.
  • the olefin may especially be an elastomeric ethylenically unsaturated monomer.
  • olefins examples include ethylenic carbide monomers, especially containing one or two ethylenic unsaturations and containing from 2 to 5 carbon atoms, such as ethylene, propylene, butadiene, isoprene or pentadiene.
  • the hydrocarbon-based block copolymer is an amorphous block copolymer of styrene and of an olefin.
  • Block copolymers comprising at least one styrene block and at least one block comprising units chosen from butadiene, ethylene, propylene, butylene and isoprene or a mixture thereof are especially preferred.
  • the hydrocarbon-based block copolymer is hydrogenated to reduce the residual ethylenic unsaturations after the polymerization of the monomers.
  • the hydrocarbon-based block copolymer is an optionally hydrogenated copolymer, containing styrene blocks and ethylene/C 3 -C 4 alkylene blocks.
  • the composition according to the invention comprises at least one diblock copolymer, which is preferably hydrogenated, preferably chosen from styrene-ethylene/propylene copolymers, styrene-ethylene/butadiene copolymers and styrene-ethylene/butylene copolymers.
  • Diblock polymers are especially sold under the name Kraton® G1701 E by the company Kraton Polymers.
  • the composition according to the invention comprises at least one triblock copolymer, which is preferably hydrogenated, preferably chosen from styrene-ethylene/propylene-styrene copolymers, styrene- ethylene/butadiene-styrene copolymers, styrene-isoprene-styrene copolymers and styrene-butadiene-styrene copolymers.
  • Triblock polymers are especially sold under the names Kraton® G1650, Kraton® D1 101 , Kraton® D1 102 and Kraton® D1 160 by the company Kraton Polymers.
  • the hydrocarbon-based block copolymer is a styrene-ethylene/butylene-styrene triblock copolymer.
  • the composition according to the invention comprises a mixture of styrene-butylene/ethylene-styrene hydrogenated triblock copolymer and of ethylene-propylene-styrene hydrogenated star polymer, such a mixture possibly being especially in isododecane or in another oil.
  • styrene-butylene/ethylene-styrene hydrogenated triblock copolymer and of ethylene-propylene-styrene hydrogenated star polymer, such a mixture possibly being especially in isododecane or in another oil.
  • Such mixtures are sold, for example, by the company Penreco under the trade names Versagel® M5960 and Versagel® M5670.
  • a diblock copolymer such as those described previously is used as polymeric gelling agent, in particular a styrene-ethylene/propylene diblock copolymer or a mixture of diblock and triblock copolymers, as described previously.
  • the hydrocarbon-based block copolymer (or the mixture of hydrocarbon-based block copolymers) may be present in a content ranging from 0.1 % to 15% by weight, preferably ranging from 0.5% to 10% by weight and even more advantageously from 1 % to 5% by weight relative to the total weight of the composition. More particularly, the weight ratio of the hydrocarbon-based resin to the hydrocarbon-based block copolymer is between 1 and 10.
  • the weight ratio of the hydrocarbon-based resin to the hydrocarbon-based block copolymer is between 1 and 8 and even more particularly between 1 and 5.
  • composition according to the invention also comprises at least one non-volatile apolar hydrocarbon-based oil.
  • oif means a water-immiscible non-aqueous compound that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg).
  • non-volatile oil refers to an oil for which the vapour pressure at room temperature and atmospheric pressure is non-zero and less than 10 "3 mmHg (0.13 Pa).
  • 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.
  • hydrocarbon-based oils may be of plant, mineral or synthetic origin.
  • apolar oil is intended to mean an oil of which the solubility parameter at 25°C, ⁇ 3 , is equal to 0 (J/cm 3 ) 1 ' 2 .
  • the parameters ⁇ ⁇ , 8 h , 5 D and 8 a are expressed in (J/cm 3 ) 1 ⁇ 2 .
  • the non-volatile apolar hydrocarbon-based oil may be chosen from linear or branched hydrocarbons of mineral or synthetic origin, such as:
  • the composition according to the invention comprises at least one apolar oil preferably chosen from polybutenes; hydrogenated or non-hydrogenated polyisobutenes; hydrogenated or non-hydrogenated polydecenes; and mixtures thereof.
  • the composition according to the invention comprises a content of nonvolatile apolar hydrocarbon-based oil(s) ranging from 5% to 70% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises a total content of non-volatile apolar hydrocarbon-based oil(s) ranging from 10% to 60% by weight and preferably from 10% to 50% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises a silicone phase containing at least one non-volatile silicone oil that is incompatible with the hydrocarbon-based phase described previously, and comprising at least one hydrocarbon-based resin with a number-average molecular weight of less than or equal to 10 000 g/mol, at least one hydrocarbon-based block polymer and at least one non-volatile apolar hydrocarbon-based oil.
  • the term "incompatible oils” means that the mixing of these two oils does not lead to a homogeneous one-phase solution. The said mixing is performed with the same weight amount of each oil.
  • oils are said to be "incompatible" when mixing them leads to a separation of phases according to the following protocols:
  • the two oils to be evaluated are introduced (in the weight ratio desired for the composition) at room temperature into a conical-tipped plastic centrifuge tube (ref. Corning ® 15ml_ PET Centrifuge Tubes, Rack Packed with Plug Seal Cap, Sterile (Product #430055) which is placed in a Vortex Genie 2 machine. Stirring is performed at speed 10 for 10 seconds, followed by manual inversion of the tube before replacing it in the Vortex machine. This cycle is repeated three times in succession. The mixture is then left to stand at room temperature for 48 hours.
  • a conical-tipped plastic centrifuge tube (ref. Corning ® 15ml_ PET Centrifuge Tubes, Rack Packed with Plug Seal Cap, Sterile (Product #430055) which is placed in a Vortex Genie 2 machine. Stirring is performed at speed 10 for 10 seconds, followed by manual inversion of the tube before replacing it in the Vortex machine. This cycle is repeated three times in succession. The mixture is then left to stand at room temperature for 48 hours.
  • the mixture of the two oils (5 g/5 g) is placed in an oven at 50°C for 30 minutes before performing the three stirring cycles described previously.
  • the mixture is observed using a phase-contrast microscope, at room temperature (about 25°C). If a continuous phase and a dispersed phase in the form of drops are observed, the phases are said to be "separated" and the oils are considered as incompatible.
  • non-volatile silicone oil(s) present in the composition according to the invention may be chosen from phenylated or non-phenylated non-volatile silicone oils, optionally bearing a dimethicone fragment.
  • Non-volatile phenylated silicone oils may be chosen from phenylated or non-phenylated non-volatile silicone oils, optionally bearing a dimethicone fragment.
  • phenylated silicone oil or "phenyl silicone oil” denotes a silicone oil bearing at least one phenyl substituent.
  • phenylated silicone oils may be chosen from those which also bear at least one dimethicone fragment, or from those which do not bear one.
  • a dimethicone fragment corresponds to the following unit:
  • the non-volatile phenylated silicone oil may thus be chosen from:
  • the groups R which are monovalent or divalent, represent, independently of each other, a methyl or a phenyl, with the proviso that at least one group R represents a phenyl.
  • the phenyl silicone oil comprises at least three, for example at least four, at least five or at least six, phenyl groups.
  • phenyl silicone oils optionally bearing a dimethicone fragment corresponding to the following formula (II):
  • groups R represent, independently of each other, a methyl or a phenyl, with the proviso that at least one group R represents a phenyl.
  • the compound of formula (II) comprises at least three, for example at least four or at least five, phenyl groups.
  • Examples which may be mentioned include mixtures of triphenyl-, tetraphenyl- or pentaphenylorganopolysiloxanes.
  • phenyl silicone oils which do not bear a dimethicone fragment, corresponding to formula (II) in which at least 4 or at least 5 radicals R represent a phenyl radical, the remaining radicals representing methyls.
  • non-volatile phenyl silicone oils are preferably trimethylpentaphenyltrisiloxane or tetramethyltetraphenyltrisiloxane. They are in particular sold by Dow Corning under the reference PH-1555 HRI or Dow Corning 555 Cosmetic Fluid (chemical name: 1 ,3,5- trimethyl-1 ,1 ,3,5,5-pentaphenyltrisiloxane; INCI name: trimethylpentaphenyltrisiloxane), or the tetramethyltetraphenyltrisiloxane sold under the reference Dow Corning 554 Cosmetic
  • R-i to Rio independently of each other, are saturated or unsaturated, linear, cyclic or branched, preferably saturated or unsaturated, linear or branched, C1-C30 hydrocarbon- based radicals,
  • n, p and q are, independently of each other, integers between 0 and 900, with the proviso that the sum m+n+q is other than 0.
  • the sum m+n+q is between 1 and 100.
  • the sum m+n+p+q is between 1 and 900 and preferably between 1 and 800.
  • q is equal to 0.
  • Ri to Rio independently of each other, represent a linear or branched C1-C30 alkyl radical, preferably C1-C20 and more particularly Ci-Ci 6 alkyl, or a monocyclic or polycyclic C 6 -Ci 4 and in particular C10-C13 aryl radical, or an aralkyl radical, the alkyl part of which is preferably C1-C3 alkyl.
  • Ri to R10 may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • Ri to R10 may in particular be identical, and in addition may be a methyl radical.
  • R-i to R 6 independently of each other, are saturated or unsaturated, linear, cyclic or branched, preferably saturated or unsaturated, linear or branched, C1-C30 hydrocarbon- based radicals, a preferably C 6 -Ci 4 aryl radical or an aralkyl radical, the alkyl part of which is C1-C3 alkyl,
  • n and p are, independently of each other, integers between 0 and 100, with the proviso that the sum n+m is between 1 and 100.
  • Ri to R 6 independently of each other, represent a C1-C30, preferably d- C 2 o and in particular Ci-Ci 6 , alkyl radical, or a C 6 -Ci 4 aryl radical which is monocyclic (preferably C 6 ) or polycyclic and in particular C1 0 -C13, or an aralkyl radical (preferably the aryl part is C 6 aryl; the alkyl part is C1-C3 alkyl).
  • Ri to R 6 may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • Ri to R 6 may in particular be identical, and in addition may be a methyl radical.
  • m 1 or 2 or 3
  • the non-volatile phenylated silicone oil is chosen from phenylated silicone oils bearing at least one dimethicone fragment.
  • oils correspond to compounds of formula (VI) in which:
  • n and p are, independently of each other, integers between 1 and 100.
  • Ri to R 6 are methyl radicals.
  • the silicone oil is preferably chosen from a diphenyl dimethicone such as KF-54 from Shin Etsu, KF54HV from Shin Etsu, KF-50-300CS from Shin Etsu, KF-53 from Shin Etsu or KF-50-100CS from Shin Etsu.
  • a diphenyl dimethicone such as KF-54 from Shin Etsu, KF54HV from Shin Etsu, KF-50-300CS from Shin Etsu, KF-53 from Shin Etsu or KF-50-100CS from Shin Etsu.
  • phenyl silicone oils optionally bearing at least one dimethicone fragment correspond more particularly to formula (VII) below:
  • -OSiMe 3 and p is 0 or is between 1 and 1000, and m is between 1 and 1000.
  • m and p are such that the compound (VII) is a non-volatile oil.
  • non-volatile phenylated silicone bearing at least one dimethicone fragment p is between 1 and 1000 and m is more particularly such that the compound (VII) is a non-volatile oil.
  • Trimethylsiloxyphenyldimethicone sold in particular under the reference Belsil PDM 1000 by the company Wacker, may, for example, be used.
  • non-volatile phenylated silicone not bearing a dimethicone fragment
  • p is equal to 0 and m is between 1 and 1000, and in particular is such that the compound (VII) is a non-volatile oil.
  • Phenyltrimethylsiloxytrisiloxane sold in particular under the reference Dow Corning 556 Cosmetic Grade Fluid (DC556), may, for example, be used.
  • DC556 Cosmetic Grade Fluid
  • R independently of each other, represent a saturated or unsaturated, linear, cyclic or branched, preferably saturated or unsaturated, linear or branched, C1-C30 hydrocarbon- based radical; more particularly, R represent a C1-C30 alkyl radical, an aryl radical, preferably a C 6 -Ci 4 aryl radical, or an aralkyl radical, the alkyl part of which is Ci-C 3 alkyl,
  • n are, independently of each other, integers between 0 and 100, with the proviso that the sum n+m is between 1 and 100.
  • R independently of each other, represent a linear or branched Ci-C 30 and in particular a Ci-C 2 o, in particular C Ci 6 alkyl radical, a monocyclic or polycyclic C 6 - CM, and in particular C1 0 -C13, aryl radical, or an aralkyl radical of which preferably the aryl part is C 6 aryl and the alkyl part is C1-C3 alkyl.
  • the R may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • the R may in particular be identical, and in addition may be a methyl radical.
  • n 1 or 2 or 3
  • n is an integer between 0 and 100 and m is an integer between 1 and 100, with the proviso that the sum n+m is between 1 and 1 00, in formula (VI I I ).
  • R is a methyl radical.
  • a phenyl silicone oil of formula (VI I I ) with a viscosity at 25°C of between 5 and 1 500 mm 2 /s (i.e. 5 to 1 500 cSt), and preferably with a viscosity of between 5 and 1 000 mm 2 /s (i.e. 5 to 1 000 cSt), may be used.
  • diphenylsiloxyphenyl trimethicone oil when m and n are between 1 and 100
  • KF56 A from Shin Etsu
  • the Silbione 70663V30 oil from Rhone-Poulenc
  • phenyl silicone oils optionally bearing at least one dimethicone fragment corresponding to the following formula, and mixtures thereof:
  • Ri , R2, R 5 and R 6 which may be identical or different, are an alkyl radical containing 1 to 6 carbon atoms,
  • R 3 and R 4 which may be identical or different, are an alkyl radical containing from 1 to 6 carbon atoms or an aryl radical (preferably C 6 -Ci 4 ), with the proviso that at least one of R 3 and R 4 is a phenyl radical,
  • X is an alkyl radical containing from 1 to 6 carbon atoms, a hydroxyl radical or a vinyl radical,
  • n and p being an integer greater than or equal to 1 , chosen so as to give the oil a weight-average molecular weight of less than 200 000 g/mol, preferably less than 150 000 g/mol and more preferably less than 100 000 g/mol. f) and a mixture thereof.
  • non-phenylated silicone oil or "non-phenyl silicone oil” denotes a silicone oil which does not bear any phenyl substituents.
  • non-volatile non-phenylated silicone oils which may be mentioned include polydimethylsiloxanes; alkyl dimethicones; vinylmethyl methicones; and also silicones modified with aliphatic groups and/or with functional groups such as hydroxyl, thiol and/or amine groups.
  • dimethylsiloxane (INCI name) corresponds to a polydimethylsiloxane (chemical name).
  • these oils may be chosen from the following non-volatile non- phenylated silicone oils:
  • - PDMSs comprising aliphatic groups, in particular alkyl or alkoxy groups, which are pendent and/or at the end of the silicone chain, these groups each comprising from 2 to
  • - PDMSs comprising at least one aliphatic group and/or at least one functional group such as hydroxyl, thiol and/or amine groups,
  • the non-volatile non-phenylated silicone oil is preferably chosen from non-volatile dimethicone oils.
  • these non-volatile non-phenylated silicone oils are chosen from polydimethylsiloxanes; alkyl dimethicones and also PDMSs comprising at least one aliphatic group, in particular C 2 -C 2 4 alkyl groups and/or at least one functional group such as hydroxyl, thiol and/or amine groups.
  • the non-phenylated silicone oil may be chosen in particular from silicones of formula ( ⁇ ):
  • Ri , R2, R5 and R 6 are, together or separately, an alkyl radical containing 1 to 6 carbon atoms,
  • R 3 and R 4 are, together or separately, an alkyl radical containing from 1 to 6 carbon atoms, a vinyl radical, an amine radical or a hydroxyl radical,
  • X is an alkyl radical containing from 1 to 6 carbon atoms, a hydroxyl radical or an amine radical,
  • n and p are integers chosen so as to have a fluid compound, in particular whose viscosity at 25°C is between 9 centistokes (cSt) (9 x 10 "6 m 2 /s) and 800 000 cSt (i.e. between 8 mPa.s and 720 000 mPa.s).
  • cSt centistokes
  • non-volatile non-phenylated silicone oils which can be used according to the invention, mention may be made of those for which:
  • the substituents Ri to R 6 and X represent a methyl group
  • p and n are such that the viscosity is 500 000 cSt (i.e. 450 000 mPa.s), for example the product sold under the name SE30 by the company General Electric, the product sold under the name AK 500000 by the company Wacker, the product sold under the name Mirasil DM 500 000 by the company Bluestar, and the product sold under the name Dow Corning 200 Fluid 500 000 cSt (i.e. 450 000 mPa.s) by the company Dow Corning,
  • the substituents Ri to R 6 and X represent a methyl group
  • p and n are such that the viscosity is 60 000 cSt (54 000 mPa.s), for example the product sold under the name Dow Corning 200 Fluid 60 000 CS by the company Dow Corning, and the product sold under the name Wacker Belsil DM 60 000 by the company Wacker,
  • the substituents Ri to R 6 and X represent a methyl group
  • p and n are such that the viscosity is 100 cSt (i.e. 90 mPa.s) or 350 cSt (i.e. 315 mPa.s), for example the products sold respectively under the names Belsil DM100 and Dow Corning 200 Fluid 350 CS by the company Dow Corning,
  • the substituents Ri to R 6 represent a methyl group
  • the group X represents a hydroxyl group
  • n and p are such that the viscosity is 700 cSt (630 mPa.s), for example the product sold under the name Baysilone Fluid TO.7 by the company Momentive.
  • the silicone phase comprises at least two silicone oils chosen such that the mixture is incompatible with the hydrocarbon-based phase.
  • non-volatile silicone oils may be chosen, without preference, from silicone oils that are mutually compatible or incompatible.
  • the silicone phase comprises at least one phenylated non-volatile silicone oil not comprising a dimethicone fragment and at least one phenylated or non- phenylated silicone oil comprising a dimethicone fragment.
  • the content of non-volatile silicone oil(s) ranges between 10% and 50% by weight relative to the weight of the composition and preferably between 15% and 50% by weight relative to the weight of the composition.
  • the silicone phase comprises a content of phenylated or non-phenylated non-volatile oil, comprising a dimethicone fragment, of at least 5% by weight relative to the weight of the composition.
  • composition according to the invention also comprises at least one surfactant.
  • the surfactant(s) are especially present in a total content ranging from 0.1 % to 20% by weight, more particularly from 0.5% to 15% by weight and preferably from 1 % to 10% by weight relative to the total weight of the composition.
  • the surfactant(s) are chosen from silicone surfactants. Silicone surfactants
  • polyorganosiloxanes comprising at least one saturated or unsaturated hydrocarbon-based radical, optionally comprising one or more heteroatoms, for instance oxygen or sulfur, which hydrocarbon-based group may be substituted with at least one group comprising at least one hydroxyl, carboxylic, carboxylate, thiol, amine, sulfonate, sulfate, phosphate and/or hydroxypolyethylenoxy function.
  • hydrocarbon-based radical may correspond to formula II):
  • - p ranges from 0 to 5
  • q ranges from 0 to 100
  • r ranges from 0 to 50, with p or q being other than zero
  • the units (C 2 H 4 0) and (C 3 H 6 0) may be distributed randomly or in blocks, and
  • - X is a hydrogen or a C-i-C-io alkyl radical, optionally substituted with one or more functions of hydroxyl, thiol, amine, carboxylic, carboxylate, amide, phosphate, sulfate or sulfonate type.
  • p may range from 1 to 5, q from 1 to 100 and r from 1 to 50.
  • X may more particularly feature a hydrogen atom.
  • the organopolysiloxane may comprise as hydrocarbon-based radical at least one hydroxy-polyalkylenoxy radical and especially a hydroxy- polyethylenoxy radical.
  • organopolysiloxane used in the composition according to the invention may correspond to formula (I):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 represent, independently of each other, a linear, branched or cyclic, saturated or unsaturated Ci to C 6 alkyl radical,
  • - HP is a radical bearing at least one hydrocarbon-based group as defined previously
  • - LP is a lipophilic radical
  • - x ranges from 1 to 5000; y from 0 to 5000; z from 0 to 5000.
  • radical LP it may be chosen especially from branched, cyclic or linear Ci to C 40 alkyls, fluorine atoms, aryl or aryloxy radicals, Ci to C 40 hydrocarbyl acyl and hydroxypropylenoxy radicals.
  • the organopolysiloxane compound may be totally or partially fluorinated.
  • the lower dialkyi siloxy groups may be substituted with one or more fluorine atoms.
  • the organopolysiloxane belongs to the family of dimethicone polyethylene glycols and may be chosen especially from the group comprising dimethicone copolyols, more specifically from
  • dimethicone copolyol such as the product sold under the name Q2-5220 ® by the company Dow Corning;
  • dimethicone copolyol benzoate such as the product sold under the name Finsolv SLB 101 ® or 201 ® by the company Finetex;
  • composition may optionally comprise at least one additional hydrocarbon-based surfactant, more particularly chosen from nonionic hydrocarbon-based surfactants.
  • composition does not comprise any such additional surfactants.
  • ADDITIONAL OILS :
  • composition according to the invention may also comprise at least one additional polar non-volatile hydrocarbon-based oil.
  • polar oif means an oil whose solubility parameter at 25°C, 8 a , is other than 0 (J/cm 3 ) 1 ' 2 .
  • hydrocarbon-based non-volatile polar oil may be chosen from the list of oils below, and mixtures thereof:
  • hydrocarbon-based plant oils such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides or jojoba oil;
  • - 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 or neopentyl glycol diheptanoate;
  • R-i represents a linear or branched fatty acid residue comprising from 4 to 40 carbon atoms and R 2 represents a hydrocarbon-based chain, which is especially branched, containing from 4 to 40 carbon atoms, on condition that R-i + R 2 > 16, for instance purcellin oil (cetostearyl octanoate), isononyl isononanoate, Ci 2 to Ci 5 alkyl benzoate, 2-ethylhexyl palmitate, octyldodecyl neopentanoate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, oleyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates
  • R 1 represents a diol dimer residue obtained by hydrogenation of dilinoleic diacid
  • R 2 represents a hydrogenated dilinoleic diacid residue
  • h represents an integer ranging from 1 to 9
  • Viscoplast 14436H I NCI name: dilinoleic acid/butanediol copolymer
  • copolymers of polyols and of diacid dimers, and esters thereof, such as Hailuscent ISDA I NCI name: dilinoleic acid/butanediol copolymer
  • fatty alcohols containing from 12 to 26 carbon atoms which are preferably branched, for instance octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol and oleyl alcohol;
  • - C12-C22 higher fatty acids such as oleic acid, linoleic acid and linolenic acid, and mixtures thereof;
  • oils of plant origin such as sesame oil (820.6 g/mol);
  • dialkyl carbonates the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC ® by Cognis; and
  • these polar non-volatile oils are chosen from ester oils.
  • the said ester oil is chosen from synthetic esters of formula R1COOR2 in which Ri represents a linear or branched fatty acid residue containing from 4 to 40 carbon atoms and R 2 represents a hydrocarbon chain that is especially branched, containing from 4 to 40 carbon atoms, provided that R-i + R 2 > 16.
  • the composition according to the invention comprises at least one nonvolatile ester oil chosen from purcellin oil (cetostearyl octanoate), isononyl isononanoate, Ci2 to Ci 5 alkyl benzoate, 2-ethylhexyl palmitate, octyldodecyl neopentanoate, 2- octyldodecyl stearate, 2-octyldodecyl erucate, oleyl erucate, isostearyl isostearate, 2- octyldodecyl benzoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, 2-ethylhexyl palmitate, 2-hexyldecyl laurate,
  • the composition according to the invention comprises at least one non- volatile oil chosen from neopentanoic acid esters, preferably octyldodecyl neopentanoate.
  • the composition comprises one or more polar non-volatile oils
  • the total content thereof is such that the polar oil(s)/apolar oil(s) weight ratio is less than 1 and preferably less than 0.6.
  • composition may optionally comprise at least one volatile oil as additional oil.
  • Such a volatile oil may especially be a hydrocarbon-based oil or a silicone 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 volatile oils of the invention are volatile organic solvents and cosmetic oils that are liquid at room temperature, with a non-zero vapour pressure at room temperature and atmospheric pressure, ranging in particular 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.
  • volatile oils that may be mentioned include volatile hydrocarbon-based oils and especially volatile hydrocarbon-based oils with a flash point of less than or equal to 80°C (the flash point is in particular measured according to ISO Standard 3679), such as hydrocarbon-based oils containing from 8 to 14 carbon atoms, and especially:
  • C 8 -Ci 4 alkanes for instance C 8 -Ci 4 isoalkanes of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4,6- pentamethylheptane), isodecane, and, for example, the oils sold under the trade name Isopar or Permethyl,
  • the volatile solvent is preferably chosen from volatile hydrocarbon-based oils containing from 8 to 14 carbon atoms, and mixtures thereof.
  • ketones that are liquid at room temperature, such as methyl ethyl ketone or acetone
  • short-chain esters (containing from 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate
  • ethers that are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether
  • a volatile hydrocarbon-based oil with a flash point of greater than 80°C that may be mentioned is isohexadecane.
  • the composition comprises less than 5% and better still less than 2% by weight of volatile oil relative to the total weight of the composition.
  • the composition is free of volatile oil.
  • composition according to the invention is free of volatile oil.
  • composition according to the invention may optionally comprise one or more additional fatty substances, more particularly chosen from waxes and pasty fatty substances, or mixtures thereof.
  • additional fatty substances more particularly chosen from waxes and pasty fatty substances, or mixtures thereof.
  • composition according to the invention may comprise at least one wax.
  • the wax(es) under consideration in the context of the present invention are generally lipophilic compounds that are 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°C, which may be up to 200°C and especially up to 120°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.
  • the melting point corresponds to the temperature of the most endothermic peak observed on thermal analysis (DSC) as described in Standard ISO 1 1357-3; 1999.
  • the melting point of the wax may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name DSC Q2000 by the company TA Instruments.
  • DSC differential scanning calorimeter
  • the waxes have an enthalpy of fusion AHf of greater than or equal to
  • the waxes comprise at least one crystallizable part, which is visible by X- ray observation.
  • the measurement 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 120°C, at a heating rate of 10°C/minute, it is then cooled from 120°C to -20°C at a cooling rate of 10°C/minute and is finally subjected to a second temperature increase ranging from -20°C to 120°C at a heating rate of 5°C/minute.
  • a first temperature rise ranging from -20°C to 120°C, at a heating rate of 10°C/minute
  • - AHf the enthalpy of fusion of the wax, corresponding to the integral of the entire melting curve obtained. This enthalpy of fusion of the wax 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 wax may especially have a hardness ranging from 0.05 MPa to 15 MPa and preferably ranging from 6 MPa to 15 MPa.
  • the hardness is determined by measuring the compressive force, measured at 20°C using the texture analyser sold under the name TA- TX2i by the company Rheo, equipped with a stainless-steel cylinder with a diameter of 2 mm, travelling at a measuring speed of 0.1 mm/second, and penetrating the wax to a penetration depth of 0.3 mm.
  • the composition according to the invention comprises a wax content of between 0.5% and 30% by weight and preferably between 1 % and 25% by weight, relative to the total weight of the composition.
  • the composition according to the invention has a wax content of between 5% and 15% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises at least one apolar wax.
  • apolar wax means a wax whose solubility parameter at 25°C as defined below, 8 a , is equal to 0 (J/cm 3 ) 1 ⁇ 2 .
  • Apolar waxes are in particular hydrocarbon-based waxes constituted solely of carbon and hydrogen atoms, and free of heteroatoms such as N, O, Si and P.
  • hydrocarbon-based wax means a wax formed essentially from, or even constituted of, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and that does not contain any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • apolar wax is understood to mean a wax that is constituted solely of apolar wax, rather than a mixture also comprising other types of waxes that are not apolar waxes.
  • the composition according to the invention comprises at least one hydrocarbon-based apolar wax.
  • the said wax is chosen from microcrystalline waxes, paraffin waxes, ozokerite, polyethylene waxes and polymethylene waxes, and mixtures thereof.
  • Ozokerite Wax SP 1020 P An ozokerite that may be mentioned is Ozokerite Wax SP 1020 P.
  • microcrystalline waxes that may be used, mention may be made of Multiwax W 445 ® sold by the company Sonneborn, and Microwax HW ® and Base Wax 30540 ® sold by the company Paramelt.
  • microwaxes that may be used in the compositions according to the invention as apolar wax, mention may be made especially of polyethylene microwaxes such as those sold under the names Micropoly 200 ® , 220 ® , 220L ® and 250S ® by the company Micro Powders.
  • Polyethylene waxes that may be mentioned include Performalene 500-L Polyethylene and Performalene 400 Polyethylene sold by New Phase Technologies.
  • Polymethylene waxes that may be mentioned include the Polymethylene Wax (54°C) sold under the reference Cirebelle 303; the Polymethylene Wax (80°C) sold under the reference Cirebelle 108, sold by Cirebelle.
  • Polar waxes include the Polymethylene Wax (54°C) sold under the reference Cirebelle 303; the Polymethylene Wax (80°C) sold under the reference Cirebelle 108, sold by Cirebelle.
  • the composition according to the invention may comprise, besides the apolar wax, at least one polar wax.
  • polar wax means a wax whose solubility parameter at 25°C, 8 a , is other than 0 (J/cm 3 ) 1 ⁇ 2 .
  • polar wax means a wax whose chemical structure is formed essentially from, or even constituted of, carbon and hydrogen atoms, and comprising at least one highly electronegative heteroatom such as an oxygen, nitrogen, silicon or phosphorus atom.
  • the parameters ⁇ ⁇ , 8 h , 5 D and 8 a are expressed in (J/cm 3 ) 1 ⁇ 2 .
  • the polar waxes may especially be hydrocarbon-based, fluoro or silicone waxes.
  • the polar waxes are hydrocarbon-based waxes.
  • silicon wax means an oil comprising at least one silicon atom, and especially comprising Si-0 groups.
  • the polar wax is a hydrocarbon-based wax.
  • a wax chosen from ester waxes and alcohol waxes is in particular preferred.
  • ester wax means a wax comprising at least one ester function.
  • alcohol wax means a wax comprising at least one alcohol functional group, i.e. comprising at least one free hydroxyl (OH) group.
  • ester wax The following may especially be used as ester wax:
  • R-i and R 2 represent linear, branched or cyclic aliphatic chains, the number of atoms of which varies from 10 to 50, which may contain a heteroatom such as O, N or P and the melting point of which varies from 25°C to 120°C.
  • R-i and R 2 represent linear, branched or cyclic aliphatic chains, the number of atoms of which varies from 10 to 50, which may contain a heteroatom such as O, N or P and the melting point of which varies from 25°C to 120°C.
  • an ester wax of a C 2 o-C 4 o alkyl (hydroxystearyloxy)stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or as a mixture, or a C 2 o-C 4 o alkyl stearate.
  • Such waxes are especially sold under the names Kester Wax K 82 P ® , Hydroxypolyester K 82 P ® , Kester Wax
  • Use may also be made of a glycol and butylene glycol montanate (octacosanoate) such as the wax Licowax KPS Flakes (INCI name: glycol montanate) sold by the company Clariant. ii) Bis(1 ,1 ,1 -trimethylolpropane) tetrastearate, sold under the name Hest 2T-4S ® by the company Heterene.
  • octacosanoate such as the wax Licowax KPS Flakes (INCI name: glycol montanate) sold by the company Clariant.
  • ii) Bis(1 ,1 ,1 -trimethylolpropane) tetrastearate, sold under the name Hest 2T-4S ® by the company Heterene.
  • R 3 and R 5 are identical or different, preferably identical and represent a C 4 -C 30 alkyl group (alkyl group comprising from 4 to 30 carbon atoms) and R 4 represents a linear or branched C 4 -C 30 aliphatic group (alkyl group comprising from 4 to 30 carbon atoms) which may or may not contain one or more unsaturated groups, and preferably that is linear and unsaturated.
  • waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C 8 -C 32 fatty chains for example such as hydrogenated jojoba oil, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, and also the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol, such as those sold under the names Phytowax Ricin 16L64 ® and 22L73 ® by the company Sophim.
  • Such waxes are described in patent application FR- A-2792190 and the waxes obtained by hydrogenation of olive oil esterified with stearyl alcohol such as that sold under the name Phytowax Olive 18 L 57, or else; v) Beeswax, synthetic beeswax, polyglycerolated beeswax, carnauba wax, candelilla wax, oxypropylenated lanolin wax, rice bran wax, ouricury wax, esparto grass wax, cork fibre wax, sugar cane wax, Japan wax, sumach wax; montan wax, orange wax, laurel wax and hydrogenated jojoba wax.
  • the composition comprises a polar wax
  • it is candelilla wax.
  • Alcohol waxes that may be mentioned include for example the wax Performacol
  • the composition according to the invention comprises at least one polar wax, and especially a polar hydrocarbon-based wax
  • the polar wax(es)/apolar wax(es) weight ratio is less than 1 and preferably less than 0.4; more particularly, if the composition contains the same, the said weight ratio ranges from 0.05 to 0.4.
  • the composition in accordance with the invention is free of polar wax.
  • composition according to the invention may optionally comprise at least one solid fatty substance whose melting point is between 20 and 60°C and preferably between 23°C and 60°C, chosen from pasty fatty substances.
  • the term "pasty fatty substance” is intended to mean a lipophilic fatty compound that undergoes a reversible solid/liquid change in state, that exhibits an anisotropic crystal organization in the solid state, and that comprises, at a temperature of 20°C and preferably of 23°C, a liquid fraction and a solid fraction.
  • the starting melting point of the pasty compound may be less than
  • the liquid fraction of the pasty compound measured at 20°C and preferably at 23°C may represent 1 % to 97% by weight and preferably from 9% to 97% by weight of the compound.
  • This liquid fraction at 20°C and preferably at 23°C preferably represents between 15% and 85% and more preferably between 40% and 85% by weight.
  • the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the standard ISO 1 1357-3; 1999.
  • the melting point of a paste or of a 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 measurement protocol is as follows:
  • a sample of 5 mg of paste or wax (depending on the case) placed in a crucible is subjected to a first temperature rise passing from -20°C to 100°C, at the heating rate of 10°C/minute, then is cooled from 100°C to -20°C at a cooling rate of 10°C/minute and finally subjected to a second temperature rise passing from -20°C to 100°C at a heating rate of 5°C/minute.
  • the variation in the difference between the power absorbed by the empty crucible and the crucible containing the sample of paste or wax as a function of the temperature is measured.
  • the melting point of the compound is the value of the temperature corresponding to the tip of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
  • the liquid fraction by weight of the pasty compound at 20°C and preferably at 23°C is equal to the ratio of the heat of fusion consumed at 20°C and preferably 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 in order to pass 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 crystalline 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 Instrument, with a temperature rise of 5°C or 10°C per minute, according to standard ISO 1 1357-3:1999.
  • 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 20°C and preferably 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 20°C and preferably at 23°C, composed 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 way as the heat of fusion consumed at 20°C or 23°C.
  • the pasty fatty substance may be chosen from synthetic compounds and compounds of plant origin.
  • a pasty fatty substance may be obtained by synthesis from starting materials of plant origin.
  • lanolin and derivatives thereof, such as lanolin alcohol, oxyethylenated lanolins, acetylated lanolin, lanolin esters such as isopropyl lanolate, and oxypropylenated lanolins,
  • polydimethylsiloxanes of high molecular masses for instance polydimethylsiloxanes of high molecular masses, polydimethylsiloxanes containing side chains of the alkyl or alkoxy type containing from 8 to 24 carbon atoms, especially stearyl dimethicones,
  • the pasty fatty substance may be a polymer, especially a hydrocarbon-based polymer.
  • a preferred silicone and fluoro pasty fatty substance is polymethyltrifluoropropylmethylalkyldimethylsiloxane, manufactured under the name X22- 1088 by Shin-Etsu.
  • the composition advantageously comprises a compatibilizer such as short-chain esters, for instance isodecyl neopentanoate.
  • the liposoluble polyethers mention may be made especially of copolymers of ethylene oxide and/or of propylene oxide with C 6 -C 30 alkylene oxides.
  • 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.
  • block copolymers comprising C 6 -C 30 alkylene oxide blocks with a molecular weight ranging from 1000 to 10 000, for example a polyoxyethylene/polydodecylene glycol block copolymer such as the ethers of dodecanediol (22 mol) and of polyethylene glycol (45 oxyethylene or OE units) sold under the brand name Elfacos ST9 by Akzo Nobel.
  • a polyoxyethylene/polydodecylene glycol block copolymer such as the ethers of dodecanediol (22 mol) and of polyethylene glycol (45 oxyethylene or OE units) sold under the brand name Elfacos ST9 by Akzo Nobel.
  • esters the following are especially preferred:
  • - 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 those sold under the brand name Softisan 649 by the company Sasol;
  • Ci 6- 4o alcohol at least one Ci 6- 4o alcohol, at least one of the alcohols being a Guerbet alcohol, and
  • a diacid dimer formed from at least one unsaturated C-i 8 -4o fatty acid, such as the ester of a dimer of fatty acids and of tall oil comprising 36 carbon atoms and of a mixture i) of Guerbet alcohols comprising 32 carbon atoms and ii) of behenyl alcohol; the ester of a dimer of linoleic acid and of a mixture of two Guerbet alcohols, 2-tetradecyloctadecanol (32 carbon atoms) and 2-hexadecyleicosanol (36 carbon atoms);
  • a Guerbet alcohol is the reaction product of the Guerbet reaction, which is well known to those skilled in the art. It is a reaction for transforming a primary aliphatic alcohol into its ⁇ -alkyl dimeric alcohol with loss of one equivalent of water.
  • the aliphatic carboxylic acids described above generally comprise from 4 to 30 and preferably from 8 to 30 carbon atoms. They are 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 acids are preferably branched.
  • esters of aliphatic hydroxylated carboxylic acid are advantageously derived from an aliphatic hydroxylated carboxylic acid comprising 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 esters of aliphatic hydroxylated carboxylic acid are especially chosen from:
  • composition comprises at least one compound of this type, its content is between 0.5% and 30% by weight and preferably between 1 % and 20% by weight relative to the total weight of the said composition.
  • composition according to the invention preferably comprises at least one dyestuff (also known as a colouring agent), which may be chosen from water-soluble or liposoluble dyes, pigments and nacres, and mixtures thereof.
  • dyestuff also known as a colouring agent
  • composition according to the invention may also comprise one or more dyestuffs chosen from water-soluble dyes and pulverulent dyestuffs, for instance pigments, nacres and glitter flakes that are well known to those skilled in the art.
  • dyestuffs chosen from water-soluble dyes and pulverulent dyestuffs, for instance pigments, nacres and glitter flakes that are well known to those skilled in the art.
  • the dyestuffs may be present in the composition in a content ranging from 0.01 % to 30% by weight, relative to the weight of the composition, preferably from 0.1 % to 20% by weight.
  • pigments should be understood as meaning white or coloured, mineral or organic particles that are insoluble in an aqueous solution, which are intended to colour and/or opacify the resulting film.
  • the pigments may be present in a proportion of from 0.01 % to 20% by weight, especially from 0.1 % to 15% by weight and in particular from 0.2% to 10% by weight, relative to the total weight of the cosmetic composition.
  • mineral pigments that may be used in the invention, mention may be made of titanium oxides, zirconium oxides or cerium oxides, and also zinc oxides, iron oxides or chromium oxides, ferric blue, manganese violet, ultramarine blue and chromium hydrate. It may also be a pigment having a structure that may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type. Such a pigment is sold, for example, under the reference Coverleaf NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30.
  • the dyestuff may also comprise a pigment with a structure that may be, for example, of silica microsphere type containing iron oxide.
  • a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball PC- LL-100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
  • organic pigments that may be used in the invention, mention may be made of carbon black, pigments of D&C type, lakes based on cochineal carmine or on barium, strontium, calcium or aluminium, or alternatively the diketopyrrolopyrroles (DPPs) described in documents EP-A-542 669, EP-A-787 730, EP-A-787 731 and WO-A- 96/08537.
  • DPPs diketopyrrolopyrroles
  • the term "nacres” should be understood as meaning coloured particles of any form, which may or may not be iridescent, especially produced by certain molluscs in their shell, or alternatively synthesized, and which have a colour effect via optical interference.
  • the nacres may be chosen from nacreous pigments such as titanium mica coated with an iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye and also nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • nacres examples include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride.
  • nacres Timica, Flamenco and Duochrome (on mica base) sold by the company Engelhard are commercially available nacres that may be mentioned.
  • Timica, Flamenco and Duochrome (on mica base) sold by the company Engelhard are commercially available nacres that may be mentioned.
  • Timiron nacres sold by the company Merck
  • Prestige nacres on mica base sold by the company Eckart
  • Sunshine nacres on synthetic mica base sold by the company Sun Chemical.
  • the nacres may more particularly have a yellow, pink, red, bronze, orangey, brown, gold and/or coppery colour or tint.
  • nacres that may be used in the context of the present invention, mention may be made especially of the gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the name Passion orange (Colorona) and Matte orange (17449) (Microna); the brown nacres sold especially by the company Engelhard under the name Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the n
  • dyes should be understood as meaning compounds that are generally organic, which are soluble in fatty substances such as oils or in an aqueous-alcoholic phase.
  • the cosmetic composition according to the invention may also comprise water- soluble or liposoluble dyes.
  • the liposoluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, Sudan brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and quinoline yellow.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue.
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect as dyestuff.
  • This effect is different from a simple conventional hue effect, i.e. a unified and stabilized effect as produced by standard dyestuffs, for instance monochromatic pigments.
  • stabilized means lacking an effect of variability of the colour as a function of the angle of observation or alternatively in response to a temperature change.
  • this material may be chosen from particles with a metallic glint, goniochromatic colouring agents, diffractive pigments, thermochromic agents, optical brighteners, and also fibres, especially interference fibres. Needless to say, these various materials may be combined so as to afford the simultaneous manifestation of two effects, or even of a novel effect in accordance with the invention.
  • FILLERS FILLERS:
  • a composition according to the invention may also contain at least one or more filler(s).
  • fillers should be understood as meaning colourless or white, mineral or synthetic particles of any shape, which are insoluble in the medium of the composition, irrespective of the temperature at which the composition is manufactured. These fillers serve especially to modify the rheology or the texture of the composition.
  • the fillers may be mineral or organic and of any shape, platelet-shaped, spherical or oblong, irrespective of the crystallographic form (for example lamellar, cubic, hexagonal, orthorhombic, etc.). Mention may be made of talc, mica, silica, kaolin, bentone, fumed silica particles, optionally hydrophilic- or hydrophobic-treated, polyamide (Nylon ® ) powder (Orgasol ® from Atochem), poly-p-alanine powder and polyethylene powder, tetrafluoroethylene polymer (Teflon ® ) powders, lauroyllysine, starch, boron nitride, hollow polymer microspheres such as polyvinylidene chloride/acrylonitrile microspheres, for instance Expancel ® (Nobel Industrie), acrylic acid copolymer microspheres (Polytrap ® from the company Dow Corning) and silicone resin microbeads (for example Tospear
  • They may also be particles comprising a copolymer, the said copolymer comprising trimethylol hexyl lactone.
  • it may be a copolymer of hexamethylene diisocyanate/trimethylol hexyl lactone.
  • Such particles are especially commercially available, for example, under the name Plastic Powder D-400 ® or Plastic Powder D-800 ® from the company Toshiki.
  • the composition comprises at least one filler, and in particular chosen from fumed silica particles that have optionally been hydrophilic- or hydrophobic-treated, preferably hydrophobic-treated.
  • the composition comprises at least one filler known as Silica Dimethyl Silylate (according to the CTFA).
  • the hydrophobic groups may especially be dimethylsilyloxyl or polydimethylsiloxane groups, which are especially obtained by treating fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane.
  • Silicas thus treated are known as Silica Dimethyl Silylate according to the CTFA (6th edition, 1995). They are sold, for example, under the references Aerosil R972® and Aerosil R974® by Degussa, and Cab-O-Sil TS- 610® and Cab-O-Sil TS-720® by Cabot.
  • the composition contains between 0.01 % and 25% by weight and in particular between 0.1 % and 20% by weight of fillers relative to the total weight of the composition.
  • a composition according to the invention may furthermore comprise any ingredient conventionally used as additive in cosmetics and dermatology.
  • additives are advantageously chosen from antioxidants, thickeners, sweeteners, basifying or acidifying preserving agents, and mixtures thereof, and may be chosen advantageously from those proposed in Table 1 of the Codex Alimentarius.
  • composition in accordance with the invention may advantageously comprise at least one pentaerythrityl di-t-butyl hydroxycinnamate.
  • a composition according to the invention may also contain flavourings and/or fragrances.
  • cosmetic active agents that may be used in the invention, mention may be made of sunscreens, vitamins A, E, C and B3, provitamins such as D-panthenol, calmatives such as a-bisabolol, Aloe vera, allantoin, plant extracts or essential oils, protective or restructuring agents, refreshing agents such as menthol and derivatives thereof, emollients, moisturizers, antiwrinkle active agents and essential fatty acids, and mixtures thereof.
  • the amounts of each of these various ingredients are those conventionally used in the fields under consideration, and range, for example, from 0.01 % to 10% by weight relative to the total weight of the composition.
  • a composition in accordance with the invention may comprise at least one sunscreen, chosen from ethylhexyl salicylate and ethylhexyl methoxycinnamate, and mixtures thereof.
  • a composition in accordance with the invention comprises at least one of the additional compounds chosen from dyestuffs, pasty fatty substances, film-forming polymers, fillers, active agents and sunscreens.
  • composition according to the invention is in solid form.
  • it may be a cosmetic product for making up the skin or the lips, preferably the lips.
  • it is a lip balm and/or a lipstick.
  • This product may preferably be in the form of a stick or cast in a dish or in a jar. According to one preferred embodiment, it is a lipstick or a lip balm in stick form.
  • the hardness of the composition is measured according to the following protocol:
  • the lipstick is stored at 20°C for 24 hours before measuring the hardness.
  • the hardness may be measured at 20°C via the "cheese wire” method, which consists in transversely cutting a wand of product, which is preferably a circular cylinder, by means of a rigid tungsten wire 250 ⁇ in diameter, by moving the wire relative to the stick at a speed of 100 mm/minute.
  • the hardness of the samples of compositions of the invention is measured using a DFGS2 tensile testing machine from the company Indelco-Chatillon.
  • the measurement is repeated three times and then averaged.
  • the average of the three values read using the tensile testing machine mentioned above, noted Y, is given in grams. This average is converted into newtons and then divided by L which represents the longest distance through which the wire passes. In the case of a cylindrical wand, L is equal to the diameter (in metres).
  • the stick is stored for 24 hours at this new temperature before the measurement.
  • the composition according to the invention has, according to this first embodiment, a hardness at 20°C and at atmospheric pressure preferably greater than or equal to 40 Nm "1 .
  • the hardness at 20°C and at atmospheric pressure is greater than or equal to 60 Nm "1 .
  • the composition according to the invention especially has, according to this first embodiment, a hardness at 20°C of less than 500 Nm "1 , especially less than 400 Nm "1 and preferably less than 300 Nm "1 .
  • the composition has a hardness of between 60 and 150 Nm "1 .
  • Example 1 Lipstick in stick form
  • compositions of lipsticks in stick form were prepared.
  • composition composition composition composition
  • Trimethylpentaphenyltrisiloxane (viscosity: 175 cSt;
  • Cirebelle 108 sold by the company Cirebelle
  • Hydrocarbon mineral wax (C20/C60) (Ozokerite Wax
  • the waxes, the pasty compound, the hydrocarbon-based oils, the surfactant, the block copolymer and the resin are placed in a beaker and the temperature is raised to 100°C, homogenizing the whole using a Rayneri blender.
  • the temperature is lowered to 90°C.
  • composition is poured into a pre-siliconized mould at 42°C.
  • the surfactant-free formulation has a silicone edging at the centre and on the contours, showing the mutual incompatibility of the various constituents, this incompatibility prohibiting the production of a correct product.
  • composition (according to the invention and comparative composition) was applied on a half-lip.
  • composition according to the invention improves the wear of color.

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Abstract

La présente invention concerne une composition cosmétique solide, de préférence pour maquiller et/ou soigner la peau et/ou les lèvres, comprenant, dans un milieu physiologiquement acceptable, au moins une phase à base d'hydrocarbure comprenant : au moins une résine à base d'hydrocarbure présentant un poids moléculaire numérique moyen inférieur ou égal à 10 000 g/mole, au moins un polymère séquencé à base d'hydrocarbure, au moins une huile à base d'hydrocarbure apolaire non volatile, au moins une phase siliconée comprenant au moins une huile de silicone non volatile qui est incompatible avec la phase à base d'hydrocarbure et au moins un agent tensioactif. L'invention concerne également un procédé pour maquiller et/ou soigner la peau et/ou les lèvres, comprenant l'application d'une composition selon l'invention sur la peau et/ou les lèvres.
PCT/EP2014/066060 2013-07-31 2014-07-25 Composition cosmétique solide comprenant une résine à base d'hydrocarbure, un copolymère séquencé à base d'hydrocarbure, une huile à base d'hydrocarbure apolaire non volatile et une huile de silicone non volatile Ceased WO2015014752A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2016530458A JP6526655B2 (ja) 2013-07-31 2014-07-25 炭化水素系樹脂、炭化水素系ブロックコポリマー、不揮発性無極性炭化水素系油及び不揮発性シリコーン油を含む化粧用固体組成物。
KR1020167005529A KR20160035602A (ko) 2013-07-31 2014-07-25 탄화수소계 수지, 탄화수소계 블록 공중합체, 비휘발성 무극성 탄화수소계 오일 및 비휘발성 실리콘 오일을 포함하는 고체 화장료 조성물
CN201480042985.2A CN105451709A (zh) 2013-07-31 2014-07-25 包含基于烃的树脂、基于烃的嵌段共聚物、非挥发性非极性的基于烃的油和非挥发性硅油的固体化妆品组合物

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FR1357618 2013-07-31
FR1357618A FR3009193B1 (fr) 2013-07-31 2013-07-31 Composition cosmetique solide comprenant une resine hydrocarbonee, un copolymere sequence hydrocarbone, une huile hydrocarbonee apolaire non volatile et une huile siliconee non volatile

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JP2017114774A (ja) * 2015-12-21 2017-06-29 ロレアル グロー及びモイスチャー感をもたらす組成物
KR20180104738A (ko) * 2016-02-29 2018-09-21 로레알 다당 알킬 에테르 및 불상용성 오일들을 포함하는 조성물 및 이의 이용 방법
KR20180105222A (ko) * 2016-02-29 2018-09-27 로레알 다당 알킬 에테르 및 불상용성 실리콘 또는 플루오르화 오일을 포함하는 조성물 및 이의 이용 방법
WO2019205043A1 (fr) * 2018-04-26 2019-10-31 L'oreal Composition anhydre solide pour le soin et/ou le maquillage de matières kératiniques
US20210386654A1 (en) * 2018-12-27 2021-12-16 L'oreal Anhydrous composition for caring for and/or making up keratin materials

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KR102467005B1 (ko) * 2016-03-31 2022-11-14 로레알 케라틴 물질에 도포 후 다층 구조물을 형성할 수 있는 화장용 조성물

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JP2017114774A (ja) * 2015-12-21 2017-06-29 ロレアル グロー及びモイスチャー感をもたらす組成物
JP7066312B2 (ja) 2015-12-21 2022-05-13 ロレアル グロー及びモイスチャー感をもたらす組成物
KR20180104738A (ko) * 2016-02-29 2018-09-21 로레알 다당 알킬 에테르 및 불상용성 오일들을 포함하는 조성물 및 이의 이용 방법
KR20180105222A (ko) * 2016-02-29 2018-09-27 로레알 다당 알킬 에테르 및 불상용성 실리콘 또는 플루오르화 오일을 포함하는 조성물 및 이의 이용 방법
KR102231947B1 (ko) 2016-02-29 2021-03-25 로레알 다당 알킬 에테르 및 불상용성 실리콘 또는 플루오르화 오일을 포함하는 조성물 및 이의 이용 방법
KR102231949B1 (ko) 2016-02-29 2021-03-25 로레알 다당 알킬 에테르 및 불상용성 오일들을 포함하는 조성물 및 이의 이용 방법
WO2019205043A1 (fr) * 2018-04-26 2019-10-31 L'oreal Composition anhydre solide pour le soin et/ou le maquillage de matières kératiniques
CN111971024A (zh) * 2018-04-26 2020-11-20 莱雅公司 用于护理和/或化妆角蛋白材料的固体无水组合物
US20210386654A1 (en) * 2018-12-27 2021-12-16 L'oreal Anhydrous composition for caring for and/or making up keratin materials
EP3902512A4 (fr) * 2018-12-27 2022-12-21 L'oreal Composition anhydre pour le soin et/ou le maquillage de matières kératiniques
US12370135B2 (en) * 2018-12-27 2025-07-29 L'oreal Anhydrous composition for caring for and/or making up keratin materials

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CN105451709A (zh) 2016-03-30
KR20160035602A (ko) 2016-03-31
FR3009193A1 (fr) 2015-02-06
FR3009193B1 (fr) 2015-08-21
JP2016525559A (ja) 2016-08-25
JP6526655B2 (ja) 2019-06-05

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