WO2013007647A1 - Cosmetic compositions in the form of water-in-oil emulsions including a jasmonic acid derivative - Google Patents

Cosmetic compositions in the form of water-in-oil emulsions including a jasmonic acid derivative Download PDF

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Publication number
WO2013007647A1
WO2013007647A1 PCT/EP2012/063284 EP2012063284W WO2013007647A1 WO 2013007647 A1 WO2013007647 A1 WO 2013007647A1 EP 2012063284 W EP2012063284 W EP 2012063284W WO 2013007647 A1 WO2013007647 A1 WO 2013007647A1
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Prior art keywords
composition
composition according
oil
water
company
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PCT/EP2012/063284
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French (fr)
Inventor
Pascal Arnaud
Pascale GIGNON
Mathilde GUEDON
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L'oreal
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Application filed by L'oreal filed Critical L'oreal
Priority to KR1020147003160A priority Critical patent/KR102002099B1/en
Priority to CN201280043183.4A priority patent/CN103796627B/en
Priority to RU2014104514/15A priority patent/RU2587320C2/en
Priority to BR112014000318-1A priority patent/BR112014000318B1/en
Publication of WO2013007647A1 publication Critical patent/WO2013007647A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/064Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes

Definitions

  • This invention relates to skincare and/or makeup compositions. More specifically, the invention relates to cosmetic compositions in the form of water-in-oil emulsions, including a jasmonic acid derivative.
  • These products usually contain active ingredients recognized for their anti- aging activity and colored particles such as pigments or nacres enabling the signs of aging to be hidden.
  • anti-aging active ingredients it is possible to cite alpha-hydroxy acids such as lactic acid and citric acid, beta-hydroxy acids such as salicylic acid, and also jasmonic acid derivatives in particular described in the application EP 1 333 021 .
  • jasmonic acid derivatives have the advantage of being well tolerated and of not causing skin discomfort such as tingling, tightness or redness.
  • compositions in the form of a W/O emulsion that are stable and that have good cosmetic application properties.
  • This invention is intended to provide water-in-oil emulsions intended for use in skincare and/or makeup compositions.
  • This invention is intended to provide skincare and/or makeup compositions in the form of water-in-oil emulsions that are stable over time.
  • This invention is intended to provide skincare and/or makeup compositions having a good compromise between stability and cosmetic properties.
  • composition including a physiologically acceptable medium containing:
  • Ri represents a radical COOR 3 , with R 3 designating a hydrogen atom or a C1 -C4 alkyl radical, optionally substituted by one or more hydroxyl groups; .
  • R 2 represents a hydrocarbon radical, saturated or unsaturated, and linear with 1 to 18 carbon atoms, or branched or cyclic with 3 to 18 carbon atoms; as well as their optical isomers and corresponding salts;
  • composition is in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fat phase,
  • aqueous phase represents 40% to 55%, in particular 42% to 52%, and preferably 44% to 50%, by weight with respect to the total weight of said composition.
  • compositions according to the invention are cosmetic compositions intended for skincare and/or makeup.
  • the emulsions obtained have good stability over time, a pleasant appearance and, during application, comfortable sensation properties.
  • stable emulsion refers to an emulsion that, after 7 days of storage at room temperature (20-22 °C), does not show any macroscopic change in color, odor or viscosity.
  • compositions of the invention include at least one jasmonic acid derivative of formula (I) as defined above.
  • compositions of the invention may include mixtures of compounds of formula (I).
  • the "alkyl" radicals Cx-Cy represent saturated hydrocarbon radicals, in a straight or branched chain, including from x to y carbon atoms, preferably 1 to 12, or 1 to 4 carbon atoms (they may typically be represented by the formula C n H 2 n + i , with n representing the number of carbon atoms). It is possible in particular to cite, when they are linear, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl and decyl radicals.
  • R 3 is chosen from the group consisting of H, methyl, ethyl, optionally substituted by a hydroxyl and propyl group, optionally substituted by one or two hydroxyl group(s).
  • R 3 When R 3 represents an alkyl group, it may be substituted by one or more hydroxyl group(s), the or said hydroxyl group(s) capable of being bound in the terminal position of the alkyl radical and/or in the lateral position.
  • R 3 may be a -CH 2 -CH(OH)-CH 3 group or a -CH 2 -CH 2 -CH 2 OH group or a -CH 2 -CH(OH)- CH 2 OH group.
  • compositions of the invention include a compound of formula (I), in which Ri is chosen from the group consisting of: -COOH, -COOCH 3 , -COO-CH 2 -CH 3 , -COO-CH 2 -CH(OH)-CH 2 OH, -COOCH 2 -CH 2 - CH 2 OH and -COOCH 2 -CH(OH)-CH 3 .
  • compositions of the invention may include a compound of formula (I), in which R 2 is a hydrocarbon radical, linear, saturated or unsaturated, having 2 to 7 carbon atoms.
  • R 2 may represent an alkyl radical, linear or branched, including 1 to 18 carbon atoms, or preferably 2 to 7 carbon atoms.
  • R 2 is chosen from the group consisting of pentyl, pentenyl, hexyl and heptyl radicals.
  • compositions of the invention include a compound of formula (I), in which is -COOH.
  • a particular jasmonic acid derivative compound used in the compositions of the invention responds to the following formula (II):
  • R 2 represents an alkyl group, linear or branched, including 1 to 18 carbon atoms, or preferably 2 to 7 carbon atoms.
  • R 2 is chosen from the group consisting of pentyl, pentenyl, hexyl and heptyl radicals.
  • compositions of the invention include a compound of formula (I) chosen from among 3-hydroxy-2-pentyl- cyclopentane acetic acid or 3-hydroxy-2-pentyl-cyclopentane acetic acid sodium salt.
  • the compounds of formula (I) may comprise one or more asymmetric carbon atoms. They may therefore be in the form of enantiomers or diastereoisomers. These enantiomers or diastereoisomers as well as mixtures thereof, including racemic mixtures, are part of the invention.
  • the compounds of formula (I) may be in the basic state or in the form of acid addition salts. Such addition salts are part of the invention.
  • the salts of the compounds capable of being used according to the invention are in particular chosen from the metal alkaline salts, such as sodium or potassium; the metal alkaline-earth salts, such as calcium, magnesium or strontium, the metal salts, such as zinc, aluminum, manganese and copper; the ammonium salts of formula NH 4 + ; the quaternary ammonium salts; the organic amine salts, such as, for example, methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2- hydroxyethylamine, bis-(2-hydroxyethyl)amine and tri-(2-hydroxyethyl)amine salts; or lysine and arginine salts.
  • the salts chosen from sodium, potassium, magnesium, strontium, copper, manganese and zinc are used. More preferably, sodium salt is used.
  • the compound of formula (I) is brought to the aqueous phase and in a content ranging from 0.001 % to 10%, in particular from 0.1 % to 8%, and preferably from 0.5% to 5% by weight with respect to the total weight of said composition.
  • the coloring agent present in the compositions of the invention is chosen, for example, from the group consisting of pigments, dyes and interferential particles.
  • the coloring agent is chosen from the pigments.
  • Such a cosmetic composition according to the invention may advantageously incorporate at least one dye chosen from organic or inorganic coloring materials, in particular of the pigment or nacre type conventionally used in cosmetic compositions, fat-soluble or water-soluble dyes, materials with a specific optical effect and mixtures thereof.
  • pigment refers to inorganic or organic white or colored particles, insoluble in an aqueous solution, intended to color and/or opacify the resulting film.
  • the pigments may be present in an amount of 0.1 % to 40% by weight, in particular 1 % to 30% by weight, and in particular 5% to 15% by weight with respect to the total weight of the cosmetic composition.
  • the composition of the invention includes at least titanium oxides and iron oxides.
  • a pigment is sold, for example, under the reference name COVERLEAF NS or JS by the CHEMICALS AND CATALYSTS company and has a contrast ratio of around 30.
  • the coloring material may also comprise a pigment having a structure that can be, for example, of the silica microsphere type containing iron oxide.
  • a pigment having this structure is that sold by the MIYOSHI company under the reference name PC BALL PC-LL-100 P, with this pigment being comprised of silica microspheres containing yellow iron oxide.
  • nacre refers to colored particles of any shape, iridescent or not, in particular, produced by certain mollusks in their shell or produced synthetically, and which have an optical interference color effect.
  • the nacres may be present in an amount of 0.1 % to 30% by weight, in particular, from 0.5% to 20% by weight and, in particular, from 1 % to 15% by weight with respect to the total weight of the cosmetic composition.
  • the nacres may be chosen from pearlescent pigments, such as bismuth oxychloride, titanium mica coated with an iron oxide, titanium mica covered with bismuth oxychloride, titanium mica covered with chromium oxide, titanium mica covered with an organic dye, as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles with a surface on which at least two successive layers of metal oxides and/or organic coloring materials are superimposed.
  • nacres natural mica covered with titanium oxide, iron oxide, natural pigment or bismuth oxychloride.
  • TIMICA FLAMENCO
  • DUOCHROME nacres (mica-based) sold by the ENGALHARD company
  • the TIMIRON nacres sold by the MERCK company
  • the PRESTIGE mica- based nacres sold by the ECKART company
  • the synthetic SUNCHINE mica- based nacres sold by the SUN CHEMICAL company synthetic SUNCHINE mica- based nacres sold by the SUN CHEMICAL company.
  • the nacres may more specifically have a yellow, pink, red, bronze, orange, brown and/or copper reflection or color.
  • nacres capable of being implemented in the context of this invention
  • it is possible to cite colored nacres in particular, sold by the ENGELHARD company, 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 in particular by the Merck company under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the Engelhard company under the name Super Bronze (Cloisonne); the orange nacres sold in particular by the Engelhard company under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the Merck company under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); the brown nacres sold in particular by the Engelhard company under the name Nu-Antique Copper 340XB (Cloisonne) and Brown CL4509 (Chrom
  • the cosmetic composition according to the invention may also include water- soluble or fat-soluble dyes.
  • the fat-soluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, ⁇ -carotene, soya oil, Sudan Brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and Quinoline Yellow.
  • the water-soluble dyes are, for example, beet juice and caramel.
  • the dyes may be present in an amount of 0.001 % to 5% by weight, in particular 0.01 % to 3% by weight, and in particular 0.025% to 1 % by weight, with respect to the total weight of the cosmetic composition.
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
  • This effect is different from a simple conventional tint effect, i.e. unified and stabilized as produced by the conventional coloring materials such as, for example, monochromatic pigments.
  • stabilized means lacking an effect of color variability with the angle of view or in response to a temperature change.
  • this material may be chosen from particles with a metallic sheen, goniochromatic coloring agents, diffracting pigments, thermochromic agents, optical brightening agents, as well as fibers, in particular, interferential fibers.
  • these different materials may be combined so as to provide a simultaneous appearance of two effects, or even a new effect according to the invention.
  • the particles with a metallic sheen capable of being used in the invention are in particular chosen from:
  • - particles comprising an organic or inorganic substrate, made of a single material or of multiple materials, covered at least partially by at least one layer with a metallic sheen, including at least one metal and/or at least one metal derivative, and mixtures of said particles.
  • metals capable of being present in said particles it is possible to cite, for example, Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te, Se and mixtures or alloys thereof.
  • Ag, Au, Cu, Al, Zn, Ni, Mo, Cr, and mixtures or alloys thereof are preferred metals.
  • metal derivatives refers to compounds derived from metals, in particular oxides, fluorides, chlorides and sulfides.
  • metal powders or alloy mixtures such as those of reference 2844 sold by the RADIUM BRONZE company
  • metal pigments for example, aluminum or bronze, such as those sold under the name ROTOSAFE 700 of the ECKART company, silica-coated aluminum particles sold under the name VISIONAIRE BRIGHT SILVER of the ECKART company and metal alloy particles, such as silica-coated bronze powders (copper and zinc alloy) sold under the name VISIONAIRE BRIGHT NATURAL GOLD of the ECKART company.
  • They may also be particles comprising a glass substrate such as those sold by the NIPPON SHEET GLASS company under the names MICROGLASS METASHINE.
  • the goniochromatic coloring agent may be chosen, for example, among the interferential multilayer structures and the liquid crystal coloring agents.
  • symmetrical interferential multilayer structures that can be used in compositions produced according to the invention are, for example, the following structures: Al/Si0 2 /Al/Si0 2 /Al, pigments having this structure and sold by the DUPONT DE NEMOURS company; Cr/MgF 2 /AI/MgF 2 /Cr, pigments having this structure and sold under the name CHROMAFLAIR by the FLEX company; MoS 2 /Si0 2 /AI/Si0 2 /MoS 2 ; Fe 2 0 3 /Si0 2 /Al/Si0 2 /Fe 2 0 3, and
  • these pigments may be pigments with a silica / titanium oxide / tin oxide structure sold under the name XIRONA MAGIC by the MERCK company, pigments with a silica / brown iron oxide structure sold under the name XIRONA INDIAN SUMMER by the MERCK company and pigments with a silica /titanium oxide / mica / tin oxide structure sold under the name XIRONA CARRIBEAN BLUE by the MERCK company. It is also possible to cite the INFINITE COLORS pigments of the SHISEIDO company. According to the thickness and the nature of the different layers, different effects are obtained.
  • the color changes from golden-green to gray-red for Si0 2 layers from 320 to 350nm; from red to golden for Si0 2 layers from 380 to 400nm; from violet to green for Si0 2 layers from 410 to 420nm; from copper to red for Si0 2 layers from 430 to 440nm.
  • pigments with a multilayer polymeric structure those sold by the 3M company under the name COLOR GLITTER.
  • liquid crystal goniochromatic particles it is possible to use, for example, those sold by the CHENIX company, as well as that sold under the name HELICONE ® HC by the WACKER company.
  • goniochromatic coloring agents may be present in the composition in a content ranging from 0.01 % to 30% by weight, in particular from 0.1 % to 20% by weight with respect to the total weight of said composition.
  • composition according to the invention includes a physiologically acceptable medium.
  • physiologically acceptable medium refers to a medium particularly suitable for the application of a composition of the invention on the skin or on the lips.
  • the physiologically acceptable medium is generally adapted to the type of support on which the composition must be applied, as well as the form in which the composition is to be packaged.
  • compositions of the invention are in the form of a W/O emulsion containing a dispersed aqueous phase and a continuous oily phase.
  • composition according to the invention comprises an amount of aqueous phase that varies from 40% to 55% by weight with respect to the total weight of the composition.
  • the aqueous phase content is less than 40%, the emulsion is no longer stable, and when the aqueous phase content is greater than 55%, the application properties are degraded.
  • the aqueous phase includes water and any other water-soluble compound that might be present, such as, in particular, water-soluble additives and solvents.
  • water-soluble solvents it is possible to cite, in particular, alcohols comprising 2 to 8 carbon atoms, in particular from 2 to 6 carbon atoms such as ethanol.
  • polyols it is possible to cite, for example, glycerol, butylene glycol and polyethylene glycols.
  • the aqueous phase may also contain other additives such as water-soluble active ingredients, preservatives, salts, gelling agents, fillers, water-soluble or water- dispersible polymers, water-soluble dyes, and so on.
  • Fatty phase may also contain other additives such as water-soluble active ingredients, preservatives, salts, gelling agents, fillers, water-soluble or water- dispersible polymers, water-soluble dyes, and so on.
  • a cosmetic composition according to this invention may include at least one liquid and/or solid fatty phase.
  • composition of the invention may include at least one liquid fatty phase, in particular at least one oil as mentioned below.
  • oils refers to any fatty body in liquid form at room temperature (20- 25°C) and atmospheric pressure. These oils may be of animal, plant, mineral or synthetic origin.
  • the fatty phase of the compositions of the invention includes at least one volatile oil and/or at least one non-volatile oil.
  • the fatty phase of the compositions of the invention includes at least one volatile oil.
  • the fatty phase of the compositions of the invention may include a mixture of multiple volatile oils.
  • volatile oil refers to any non-aqueous medium capable of evaporating from the skin or lips, in less than one hour, at room temperature and atmospheric pressure.
  • the volatile oil is a volatile cosmetic oil, liquid at room temperature. More specifically, a volatile oil has an evaporation rate of between 0.01 and 200mg/cm 2 /min, inclusive.
  • the volatile oils may be hydrocarbon-based, silicone-based or fluorine-based.
  • silicon oil refers to an oil including at least one silicon atom, and in particular at least on Si-0 group.
  • fluorine oil refers to an oil including at least one fluorine atom.
  • hydrocarbon oil refers to an oil containing primarily hydrogen and carbon atoms.
  • the oils may optionally include oxygen, nitrogen, sulfur and/or phosphorus atoms, for example, in the form of hydroxyl or acid radicals.
  • the volatile oils may be chosen from hydrocarbon oils having 8 to 16 carbon atoms, and in particular branched C 8 -Ci 6 alkanes (also called isoparaffins or isoalkanes), such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, and, for example, the oils sold under the trade names ISOPARS ® or PERMETHYLS ® .
  • linear C 9 -Ci 7 alkanes such as dodecane (Ci 2 ) and tetradecane (C ), sold respectively under the names PARAFOL ® 12-97 and PARAFOL ® 14-97 (Sasol), and, as alkanes obtained according to the method described in the international application WO 2007/068371 A1 , such as the undecane (Cn) and tridecane (Ci 3 ) mixture sold under the name CETIOL ® UT (Cognis).
  • isododecane and the undecane (Cn) and tridecane (Ci 3 ) mixture are preferred.
  • volatile oils such as, for example, volatile linear or cyclic silicones, in particular those having a viscosity below or equal to 8 centistokes (cSt) (8 x 10 "6 m 2 /s), and having, in particular, from 2 to 10 silicon atoms, and in particular from 2 to 7 silicon atoms, in which these silicones optionally comprise alkyl or alkoxyl groups having from 1 to 10 carbon atoms.
  • volatile linear or cyclic silicones in particular those having a viscosity below or equal to 8 centistokes (cSt) (8 x 10 "6 m 2 /s), and having, in particular, from 2 to 10 silicon atoms, and in particular from 2 to 7 silicon atoms, in which these silicones optionally comprise alkyl or alkoxyl groups having from 1 to 10 carbon atoms.
  • cSt centistokes
  • a volatile silicone oil that can be used in the invention, in particular, dimethicones with a viscosity of 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.
  • silicone oil it is possible to cite linear or cyclic silicone oils having from 2 to 7 silicon atoms, in which these silicones optionally comprise alkyl or alkoxyl groups having from 1 to 10 carbon atoms.
  • dodecamethyl pentasiloxane is preferred.
  • Non-volatile oils for example, nonafluoromethoxybutane or perfluoromethylcyclopentane, and mixtures thereof.
  • the fatty phase of the compositions of the invention includes at least one non-volatile oil.
  • the fatty phase of the compositions of the invention may include a mixture of a plurality of non-volatile oils.
  • non-volatile oil is intended to mean an oil remaining on the skin or keratin fiber at ambient temperature and atmospheric pressure. More specifically, a non-volatile oil has an evaporation rate strictly below 0.01 mg/cm 2 /min.
  • the non-volatile oils may, in particular, be chosen from among the non-volatile hydrocarbon, fluorine and/or silicone oils.
  • oils of plant origin such as phytostearyl esters, for instance phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate (AJINOMOTO, ELDEW PS203), triglycerides constituted of fatty acid esters of glycerol, in particular in which the fatty acids may have chain lengths ranging from C 4 to C 36 , and in particular from Ci 8 a C 36 , it being possible for these oils to be linear or branched, and saturated or unsaturated; these oils may in particular be heptanoic or octanoic triglycerides, shea oil, alfalfa oil, poppy seed oil, pumpkin oil, millet oil, barley oil, quinoa oil, rye oil, candlenut oil, passionflower oil, shea butter, aloe oil, sweet almond oil, peach kernel oil, groundnut oil, argan oil, avocado oil,
  • John's Wort oil monoi oil, hazelnut oil, apricot kernel oil, nut oil, olive oil, evening primrose oil, palm oil, blackcurrant seed oil, kiwi seed oil, grape seed oil, pistachio oil, pumpkin oil, winter squash oil, quinoa oil, musk rose oil, sesame oil, soya oil, sunflower oil, castor oil and watermelon oil, and mixtures thereof, or alternatively caprylic/capric acid triglycerides, for instance those sold by the STEARINERIES DUBOIS company or those sold under the names MIGLYOL 810 ® , 812 ® and 818 ® by the DYNAMIT NOBEL company,
  • - synthetic ethers having from 10 to 40 carbon atoms
  • - synthetic esters for instance oils of formula RiCOOR 2 , in which Ri represents a linear or branched fatty acid residue containing from 1 to 40 carbon atoms, and R 2 represents a hydrocarbon-based chain, in particular a branched chain, containing from 1 to 40 carbon atoms provided that Ri et R 2 is greater than or equal to 10.
  • the esters may in particular be selected from fatty acid and alcohol esters, for instance: cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactacte, octyl hydroxystearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-ethylhexy
  • - fatty alcohols that are liquid at ambient temperature, with a branched and/or unsaturated carbon chain having from 12 to 26 carbon atoms, for instance 2- octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol and 2-undecylpentadecanol,
  • oils of higher molar mass having in particular a molar mass ranging from approximately 400 to approximately 10,000 g/mol, in particular from approximately 650 to approximately 10,000 g/mol, in particular from approximately 750 to approximately 7500 g/mol, and more particularly ranging from approximately 1000 to approximately 5000 g/mol.
  • oils of higher molar mass that can be used in the invention, mention may in particular be made of the oils selected from:
  • esters of C 2 4-C 28 branched fatty acids or fatty alcohols • esters of C 2 4-C 28 branched fatty acids or fatty alcohols
  • fluorine oils optionally partially hydrocarbon-based and/or silicone-based, such as fluorosilicone oils, fluorinated polyethers or fluorinated silicones, as described in document EP-A-847 752;
  • silicone oils such as polydimethylsiloxanes (PDMS) which are non-volatile and linear or cyclic; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups which are pendant or at the end of the silicone chain, said groups having from 2 to 24 carbon atoms; phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl-trimethylsiloxy-diphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl-trisiloxanes or (2-phenylethyl)trimethylsiloxysilicates, and
  • linear or branched hydrocarbons of mineral or synthetic origin, paraffin oils or petroleum jelly are preferably used.
  • hydrocarbon oils of plant origin it is possible to cite, preferably, plant oils, such as sweet almond oil, jojoba oil or macadamia nut oil.
  • isodecyl neopentanoate or isononyl isononanoate is used in particular, and among the synthetic ethers, dicapryl ether is preferably used.
  • the fatty phase of the compositions of the invention represents a percentage ranging from 15% to 70%, and preferably ranging from 20% to 50% with respect to the total weight of the composition.
  • one or more thickeners or gelling agents may be incorporated into a composition of the invention.
  • a thickener or gelling agent suitable for the invention may be hydrophilic, i.e. water-soluble or water-dispersible.
  • hydrophilic gelling agents mention may in particular be made of water- soluble or water-dispersible thickening polymers.
  • Said polymers may in particular be selected from: modified or unmodified carboxyvinyl polymers, such as the products sold under the name Carbopol (CTFA name: carbomer) by the Goodrich company; polyacrylates and polymethacrylates, such as the products sold under the names
  • polysaccharide biopolymers such as xanthan gum, guar gum, carob gum, gum acacia, scleroglucans, chitin derivatives and chitosan derivatives, carrageenans, gellans, alginates, or celluloses such as microcrystalline cellulose, carboxymethylcellulose, hydroxymethylcellullose and hydroxypropylcellulose; and mixtures thereof.
  • a thickener or gelling agent suitable for the invention may be lipophilic, it may be inorganic or organic.
  • modified clays such as modified magnesium silicate (Bentone gel VS38 of RHEOX), modified hectorites such as hectorite modified with a Ci 0 to C 22 fatty acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride, for instance the product sold under the name Bentone 38V ® by the ELEMENTIS company or that sold under the name "Bentone 38 CE" by the RHEOX company or that sold under the name Bentone Gel V5 5V by the ELEMENTIS company.
  • modified clays such as modified magnesium silicate (Bentone gel VS38 of RHEOX), modified hectorites such as hectorite modified with a Ci 0 to C 22 fatty acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride, for instance the product sold under the name Bentone 38V ® by the ELEMENTIS company or that sold under the name "Bentone 38 CE" by the RHE
  • the polymeric organic lipophilic gelling agents are, for example partially or totally cross-linked elastomeric organopolysiloxanes with a three-dimensional structure, such as those sold under the names KSG6 ® , KSG16 ® and KSG18 ® by the SHIN-ETSU company, Trefil E-505C ® and Trefil E-506C ® by the DOW-CORNING company, Gransil SR-CYC ® , SR DMF10 ® , SR-DC556 ® , SR 5CYC gel ® , SR DMF 10 gel ® and SR DC 556 gel ® by the GRANT INDUSTRIES company, SF 1204 ® and JK 1 13 ® by the GENERAL ELECTRIC company; ethylcellulose, such as the product sold under the name Ethocel ® by the DOW CHEMICAL company; polyamide-type polycondensates resulting from condensation between a dicarboxylic acid containing at least 32 carbon
  • Block copolymers of the "diblock", “triblock” or “radial” type, of the polystyrene/polyisoprene or polystyrene/polybutadiene type such as those sold under the name Luvitol HSB ® by the BASF company, of the polystyrene/copoly(ethylene-propylene) type, such as those sold under the name Kraton ® by the SHELL CHEMICAL Company or of the polystyrene/copoly(ethylene- butylene) type
  • blends of triblock and radial (star) copolymers in isododecane such as those sold by the PENRECO company under the name Versagel ® for instance the mixture of butylene/ethylene/styrene triblock copolymer and of ethylene/propylene/styrene star copolymer in isododecane (Versagel M 5960).
  • esters of dextrin and of a fatty acid such as dextrin palmitates, in particular such as those sold under the names Rheopearl TL ® or Rheopearl KL ® by the CHIBA FLOUR company
  • hydrogenated plant oils such as hydrogenated castor oil
  • fatty alcohols in particular C 8 to C 2 6, and more particularly C 12 to C 2 2, fatty alcohols, for instance myristyl alcohol, cetyl alcohol, stearyl alcohol and behenyl alcohol.
  • a composition may comprise thickeners in a content with respect to active material of from 0.01 % to 40% by weight, especially from 0.1 % to 20% by weight, in particular from 0.3% to 15% by weight, relative to the total weight of the composition.
  • the composition includes at least one lipophilic thickener, in particular at least one modified hectorite, such as a hectorite modified by a Ci 0 to C 22 fatty acid ammonium chloride, advantageously in a content ranging from 0.1 % to 5% by weight, in particular 0.5% to 2% by weight of active material with respect to the total weight of said composition
  • a composition according to the invention may also comprise at least one filler, of organic or inorganic nature, which makes it possible in particular to confer thereon additional properties of mattness, covering power and/or improved stability or staying power.
  • the filler content may range from 0.1 % to 20% by weight, and in particular from 1 % to 12% by weight with respect to the total weight of said composition.
  • filler should be understood to mean colorless or white solid particles of any shape, which are in a form that is insoluble or dispersed in the medium of the composition. Inorganic or organic in nature, they make it possible to confer body or rigidity on the composition, and/or softness, and uniformity on the makeup.
  • the fillers used in the compositions according to the present invention may be of lamellar, globular or spherical form, or in the form of fibers or in any other intermediate form between these defined forms.
  • the fillers may or may not be surface-coated, and in particular they may be surface-treated with silicones, amino acids, fluorinated derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.
  • inorganic fillers mention may be made of talc, mica, silica, hollow silica microspheres, kaolin, calcium carbonate, magnesium carbonate, hydroxyapatite, boron nitride, glass or ceramic microcapsules, composites of silica and of titanium dioxide, such as the TSG series sold by Nippon Sheet Glass.
  • organic fillers examples include polyamide powder (Nylon ® Orgasol of Atochem), polyethylene powder, polymethyl methacrylate powder, polytetrafluoroethylene powder (Teflon), acrylic acid copolymer powder (Polytrap of the Dow Corning company), lauroyl lysine, hollow polymeric microspheres such as those of polyvinylidene/acrylonitrile chloride, for instance Expancel (Nobel Industry), hexamethylene diisocyanate/Trimethylol hexyllactone copolymer powder (Plastic Powder of Toshiki), silicone resin microbeads (Tospearl of Toshiba, for example) synthetic or natural micronized waxes, metal soaps derived from organic carboxylic acids having 8 to 22 carbon atoms, and preferably from 12 to 18 carbon atoms, for example, zinc stearate, magnesium stearate or lithium stearate, zinc laurate, magnesium myristate Polypore ® L 200 (Nylon ® Org
  • it may be a polymer of hexamethylene diisocyanate/trimethylol hexyllactone.
  • Such particles are in particular commercially available, for example under the name PLASTIC POWDER D-400 ® or PLASTIC POWDER D-800 ® of the TOSHIKI company and mixtures thereof.
  • the composition includes at least one cross-linked elastomeric organopolysiloxane powder coated with silicone resin.
  • This filler also enables the composition of the invention to be thickened and/or gelled.
  • the cross-linked elastomeric organopolysiloxane powder(s) coated with silicone resin may be present in a content ranging from 0.5% to 12% by weight, advantageously from 2% to 10% by weight and preferably from 7% to 9% by weight with respect to the total weight of said composition.
  • cross-linked elastomeric organopolysiloxane powders coated with silicone resin in particular silsesquioxane resin, as described for example in the patent US 5 538 793.
  • Such elastomer powders are sold under the names KSP-100 ® , KSP-101 ® , KSP-102 ® , KSP-103 ® , KSP-104 ® and KSP-105 ® by the SHIN ETSU company; mention may also be made of cross-linked elastomeric organopolysiloxane powder coated with silicone resin such as hybrid silicone powders functionalized by fluoroalkyi groups, in particular sold under the name "KSP-200" by the Shin Etsu company; or hybrid silicone powders functionalized by phenyl groups, in particular sold under the name "KSP- 300" by the Shin Etsu company.
  • Emulsifier are sold under the names KSP-100 ® , KSP-101 ® , KSP-102 ® , KSP-
  • composition of the invention may also include one or more emulsifiers.
  • emulsifiers it is possible to cite, in particular, polyhydroxylated and polyoxyalkylene glycol fatty acid emulsifiers.
  • the polyhydroxylated and polyoxyalkylene glycol fatty acid ester is a fatty acid and polyethylene glycol ester.
  • the fatty acid and polyoxyalkylene glycol ester may be a monoester or a polyester, in particular a diester or a triester.
  • the fatty acid may include 12 to 20 carbon atoms, and preferably 14 to 18 carbon atoms. It may be chosen in particular from oleic acid, palmitic acid, stearic acid and mixtures thereof.
  • the polyethylene glycol may include from 4 to 50 moles of ethylene oxide and more preferably 20 to 40 moles of ethylene oxide.
  • an ester is used, preferably a diester, of polyethylene glycol including 20 to 40 moles of ethylene oxide and polyhydroxylated fatty acid, in which said polyhydroxylated fatty acid includes 14 to 18 carbon atoms, in particular polyhydroxystearic acid.
  • the fatty acid and polyoxyalkylene glycol ester is in the form of a sequenced polymer, preferably with an ABA structure, comprising poly(hydroxylated ester) and polyethylene glycol sequences.
  • the fatty acid ester of said polymer has a chain comprising 12 to 20 carbon atoms, and preferably 14 to 18 carbon atoms.
  • the polyethylene glycol sequences of said emulsifying polymer as defined above preferably comprise 4 to 50 moles of ethylene oxide, and more preferably 20 to 40 moles of ethylene oxide.
  • a compound particularly suitable for producing the compositions of the invention is polyethylene glycol dipolyhydroxystearate with 30 moles of ethylene oxide sold under the trade name "CITHROL DPHS-SO-(MV)" by the Croda company.
  • the polyoxyalkylene glycol is generally present in compositions according to the invention in an amount capable of ranging from 0.1 % to 15% by weight with respect to the total weight of the composition, and preferably 0.5% to 10% by weight, and better yet 1 % to 5% by weight with respect to the total weight of the composition.
  • the composition of the invention may include, in addition to the polyoxyalkylene glycol and polyhydroxylated fatty acid ester emulsifier, an additional emulsifier (or surfactant), also called a co-emulsifier.
  • an additional emulsifier or surfactant
  • This co-emulsifier does not alone enable, in the absence of a polyoxyalkylene glycol and polyhydroxylated fatty acid ester, the composition of the invention to be stabilized.
  • the additional emulsifier may be chosen, for example, from the non-ionic emulsifiers derived from polyol-fatty acid, polyolefins with a succinic end, and mixtures thereof.
  • polystyrene resins with a succinic end it is possible to cite, in particular, polyisobutylenes with an esterified succinic end and salts thereof, in particular diethanolamine salts, such as the products sold under the names Lubrizol 2724, Lubrizol 2722 and Lubrizol 5603 by the Lubrizol company.
  • the additional emulsifier is chosen from the polyol-fatty acid esters.
  • polyol-fatty acid ester refers to polyol- fatty acid esters in which the fatty acid includes a C 6 -C 22 , and preferably Ci 6 -C 20 , alkyl chain, and the polyol is chosen from glycerol, polyglycerol, sorbitan, and mixtures thereof.
  • the fatty acid may also be in a polymeric form, as is the case of the polyhydroxystearic acid (12-hydroxystearic acid polymer).
  • the polyol-fatty acid ester is a Ci 6 -C 2 o ester of fatty acid and glycerol and/or sorbitan, and mixtures thereof.
  • Ci 6 -C 20 linear or branched chain fatty acid it is possible to cite stearic acid, isostearic acid, lauric acid, myristic acid, palmitic acid.
  • Ci 6 -C 20 fatty acid polymer it is possible to cite 12-polyhydroxystearic acid.
  • stearic, isostearic or 12-polyhydroxystearic acid or mixtures thereof will be used.
  • polyglycerols refers to compounds of formula:
  • the degree of condensation n ranges from 1 to 1 1 , preferably from 2 to 6 and even more preferably from 3 to 6.
  • the polyol-fatty acid ester contains 2 to 10 moles (units) of polyols, preferably 2 to 4 moles of polyols, in articular 2 to 4 units of glycerol or a mixture of polyglycerols (glycerol, di-, tri-, tetra-, penta-, oligoglycerols). Even more preferably, the polyol-fatty acid ester contains 4 moles (or units) of polyol, in particular 4 moles (or units) of glycerol.
  • said polyol-fatty acid ester is also a fatty acid ester, of dicarboxylic acid having 2 to 16 carbon atoms, preferably 8 to 14 carbon atoms, such as azelaic acid, sebacic acid, dodecanedioic acid, and preferably sebacic acid (Ci 0 ), and polyol.
  • esters of isostearic acid and of polyols and mixtures thereof in particular esters of isostearic acid and glycerol and/or sorbitan, such as, for example, polyglycerol isostearate (4 moles) (INCI name: Polyglyceryl-4 Isostearate) sold under the name Isolan GI34 ® by the Goldschmidt company, polyglycerol diisostearate (3 moles) sold under the name Lameform TGI ® by the Cognis company; polyglycerol distearate (2 moles) sold under the name Emalex PGSA ® by the Nihon emulsion company; polyglycerol monoisostearate (10 moles) sold under the name Nikkol Decaglyn 1 -IS by the Nihon Surfactant company (INCI name: Polyglyceryl-10 isostearate); polyglycerol isostearate (4 moles) (INCI name: Polyglyceryl-4 Isostearate) sold
  • silicone surfactants such as dimethicone copolyols and alkyl dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name "DC 5225 C” by the Dow Corning company, Laurylmethicone copolyol sold under the name “Dow Corning 5200 Formulation Aid” by the Dow Corning company and Cetyl dimethicone copolyol sold under the name Abil EM 90 ® by the Goldschmidt company.
  • the additional emulsifier is chosen from the fatty acid esters, preferably Ci 6 -C 20 , in particular stearic acid or isostearic acid, and polyol, chosen from glycerol and/or sorbitan.
  • the additional emulsifier may be present in a content (dry matter) ranging from 0.05% to 5% by weight with respect to the total weight of the composition, and preferably from 0.1 to 1 % by weight with respect to the total weight of the composition.
  • the composition according to the invention includes less than 2%, preferably less than 1 % and even more preferably less than 0.5% of additional emulsifier, and it can in particular be free of additional emulsifier.
  • composition of the invention may also include at least one silicone emulsifier.
  • compositions according to the invention include a silicone emulsifier (or surfactant) chosen from the oxyethylene and oxypropylene polydimethylsiloxanes also called dimethicone copolyols, the oxyethylene and oxypropylene alkylpolydimethylsiloxanes (also called alkyldimethicone copolyols) of which the alkyl chain includes fewer than 12 carbon atoms, and mixtures thereof.
  • a silicone emulsifier or surfactant chosen from the oxyethylene and oxypropylene polydimethylsiloxanes also called dimethicone copolyols
  • the oxyethylene and oxypropylene alkylpolydimethylsiloxanes also called alkyldimethicone copolyols
  • the silicone surfactant comprises polyoxyethylene and polyoxypropylene chains grafted onto the main chain (polyoxyethylene and polyoxypropylene side or pendant chains).
  • the (alkyl)polydimethylsiloxanes used in the emulsion according to the invention advantageously have polyoxyethylene and polyoxypropylene side chains with the following formula:
  • - Rio represents a hydrogen atom, an alkyl radical, linear or branched, having 1 to 12 carbon atoms, preferably a hydrogen atom,
  • - a varies from 1 to 100, preferably from 2 to 50 and more preferably from 10 to 30,
  • - b varies from 1 to 100, preferably from 2 to 50, and more preferably from 10 to 30,
  • Le number average molecular weight of the silicone emulsifier is generally greater than or equal to 15,000, preferably greater than or equal to 30,000 and capable of ranging from 40,000 to 100,000, in particular from 50,000 to 100,000.
  • OE/OP 18/18 oxyethylene and oxypropylene polydimethylsiloxane
  • the INCI name is PEG/PPG 18/18 dimethicone
  • sold in a mixture with a polydimethylsiloxane under the trade reference X-22-671 1 D by the Shin Etsu company or under the name ES-5226 DM by the Dow Corning company (INCI name: Dimethicone / PEG/PPG-18/18 Dimethicone).
  • the silicone emulsifier is generally present in the compositions according to the invention in a content capable of ranging from 0.1 % to 15% by weight, with respect to the total weight of the composition, preferably from 0.5% to 10% by weight, and more preferably from 1 % to 5% by weight with respect to the total weight of the composition.
  • a cosmetic composition according to the invention may also further comprise any additive normally used in the field under consideration, for example selected from gums, anionic, cationic, amphoteric or nonionic surfactants, silicone surfactants, gums, resins, dispersants, semicrystalline polymers, antioxidants, essential oils, preservatives, fragrances, neutralizing agents, antiseptics, anti-UV protective agents, cosmetic active agents, such as vitamins, hydrating agents, emollients or collagen-protecting agents, and mixtures thereof.
  • any additive normally used in the field under consideration for example selected from gums, anionic, cationic, amphoteric or nonionic surfactants, silicone surfactants, gums, resins, dispersants, semicrystalline polymers, antioxidants, essential oils, preservatives, fragrances, neutralizing agents, antiseptics, anti-UV protective agents, cosmetic active agents, such as vitamins, hydrating agents, emollients or collagen-protecting agents, and mixtures thereof.
  • a person skilled in the art can adjust the type and amount of additives present in the compositions according to the invention by means of routine operations, so that the desired cosmetic properties and stability properties for these compositions are not affected by the additives.
  • composition of the invention may also include at least one UV filter.
  • UV filters As a non-limiting illustration of UV filters, it is possible to cite the following families: anthranilates, in particular methyl anthranilate; benzophenones, in particular benzophenone-1 , benzophenone-3, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, and preferably Benzophenone-2 (Oxybenzone), or Benzophenone-4 (Uvinul MS40 ® available from BASF); benzylidene-camphors, in particular 3-benzylidene-camphor, benzylidene- camphor-sulfonic acid, camphor benzalkonium methosulfate, polyacrylamidomethyl benzylidene camphor, terephthalylidene dicamphor sulfonic acid, and preferably 4- methylbenzylidene camphor (Eusolex 6300 ® available from Merck); benzimidazoles, in particular benzimida
  • composition of the invention includes a UV filter chosen from the cinnamates.
  • octylmethoxycinnamate also called ethyl hexyl methoxycinnamate is preferably used.
  • the quantity of filters is dependent on the desired end use. It may range, for example, from 1 to 20% by weight and more preferably from 2 to 10% by weight with respect to the total weight of the composition.
  • a cosmetic composition of the invention may be in the form of a liquid or fluid foundation, a hot-poured foundation product, a body makeup product, a concealer, an eye shadow, or a makeup base.
  • a skincare composition according to the invention may in particular be a sunscreen composition, a skincare cream, a serum or a deodorant.
  • the composition of the invention is in the form of a foundation.
  • composition according to the invention may be applied by any means enabling a uniform distribution, in particular using a finger, or a cotton ball, a rod, a brush, gauze, a spatula or a buffer, or by spraying, and can be removed by rinsing with water or using a gentle detergent.
  • composition of the invention may be implemented so as to improve the general state of the epidermis, in particular the skin, and in particular to maintain or restore its physiological functions and/or its aesthetic appearance.
  • composition of the invention may advantageously be implemented in order to fight aging of the epidermis, to maintain and/or stimulate hydration and/or to combat drying of the skin, to improve skin tone, maintain or restore flexibility and elasticity of the skin, improve mineralization of the epidermis, improve vitality of the epidermis, facilitate inter-cellular exchanges, and fight chapping and a cracking appearance of the skin.
  • composition according to the invention may be intended for a cosmetic and/or dermatological application.
  • the invention also relates to the cosmetic use, in particular non-therapeutic, in a cosmetic composition for skincare and/or makeup, of at least one coloring agent and at least one jasmonic acid derivative compound of formula (I) as defined above, with said composition being in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fatty phase,
  • said aqueous phase represents from 40% to 55% by weight with respect to the total weight of said composition
  • the invention also relates to the cosmetic use, in particular non-therapeutic, of at least one coloring agent and at least one jasmonic acid derivative compound of formula (I) as defined above in a composition, with said composition being in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fatty phase,
  • said aqueous phase represents from 40% to 55% by weight with respect to the total weight of said composition
  • the invention also relates to a cosmetic treatment method including the application on the skin of a composition as defined above.
  • the invention also relates to a non-therapeutic skincare and/or makeup method including a step of applying at least one layer of a composition as defined above on the skin.
  • the invention also relates to a skin makeup method in which a composition as defined above is applied.
  • stable emulsion refers to an emulsion that, after 7 days of storage at room temperature (20-22 ⁇ ⁇ ) does not show any macroscopic change.
  • the stabilities are carried out on 300g of product, packaged in a 660ml jar that is hermetically sealed by an aluminum lid.
  • fluid foundations 1 to 7 make it possible to show that, when the aqueous phase content is less than 40%, the stability of the foundation is inadequate.
  • phase A1 The constituents of phase A1 are weighed into the main beaker, then homogenized using a Moritz mixer at a speed of 1200-1400 rpm at room temperature.
  • Phase A2 followed by phase A3 are then added, which have been previously prepared by mashing by hand, and, finally, phase A4 is added, while agitating for 15 minutes until homogenization.
  • Phase A5 is prepared separately by grinding three times, in a three-roll mill, the mixture of pigments and cyclohexasiloxane.
  • Phase A5 is added to the main beaker while progressively increasing the agitation speed of the Moritz mixer to 1400-1500 rpm, then the agitation is continued for 20 minutes.
  • phase B The constituents of phase B are weighed separately, with the exception of the jasmonic acid derivative and the phenoxyethanol. It is homogenized using a magnetic mixer at a temperature of around 30-35°C, then the jasmonic acid derivative and the phenoxyethanol are incorporated.
  • the emulsification is produced by pouring phase B into the main beaker and progressively increasing the agitation speed to 4000 rpm, and then maintaining it at that speed for 10 minutes.
  • the comparison of the fluid foundation examples 1 and 8 shows that, when the aqueous phase content is greater than 55%, the cosmetic properties of the foundation are not as good.
  • Titanium dioxide coated with aluminum stearoyl glutamate 10.22 10.22
  • phase A1 The constituents of phase A1 are weighed into the main beaker, then homogenized with a Moritz mixer at a speed of 1500 rpm at room temperature.
  • Phase A2 followed by phase A3 are then added, which have been previously prepared by mashing by hand, and, finally, phase A4 is added, while agitating for 15 minutes until homogenization.
  • Phase A5 is prepared separately by grinding three times, in a three-roll mill, the mixture of pigments and cyclohexasiloxane.
  • Phase A5 is added to the main beaker while progressively increasing the agitation speed of the Moritz mixer to 1600 rpm, then the agitation is continued for 20 minutes.
  • phase B The constituents of phase B are weighed separately, with the exception of the jasmonic acid derivative and the phenoxyethanol. It is homogenized using a magnetic mixer at a temperature of around 30-35°C, then the jasmonic acid derivative and the phenoxyethanol are incorporated. Then the emulsification is produced by pouring phase B into the main beaker and progressively increasing the agitation speed to 4000 rpm, and then maintaining it at that speed for 10 minutes.
  • the agitation speed is then slightly reduced and the ethanol and the perfume are added.
  • the mixture is agitated again for two minutes and the product is packaged in a glass jar.
  • example 1 invention
  • example 8 comparative

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Abstract

This invention relates to a composition including a physiologically acceptable medium containing at least one coloring agent; and at least one jasmonic acid derivative compound, in which said composition is in the form of a water-in-oil emulsion, and said aqueous phase represents 40% to 55% by weight with respect to the total weight of said composition.

Description

COSMETIC COMPOSITIONS IN THE FORM OF WATER-IN-OIL EMULSIONS INCLUDING A JASMONIC ACID DERIVATIVE
This invention relates to skincare and/or makeup compositions. More specifically, the invention relates to cosmetic compositions in the form of water-in-oil emulsions, including a jasmonic acid derivative.
Consumers look for cosmetic skincare or makeup products that can be easily and quickly spread on the skin in the form of a deposit that should not be thick, but that should instead blend as much as possible with the support, and they also look for anti-aging products.
Consumers are therefore increasingly looking for cosmetic products that combine foundation makeup properties and skincare properties, in particular for fighting the effects of aging.
These products usually contain active ingredients recognized for their anti- aging activity and colored particles such as pigments or nacres enabling the signs of aging to be hidden.
Among anti-aging active ingredients, it is possible to cite alpha-hydroxy acids such as lactic acid and citric acid, beta-hydroxy acids such as salicylic acid, and also jasmonic acid derivatives in particular described in the application EP 1 333 021 .
These jasmonic acid derivatives have the advantage of being well tolerated and of not causing skin discomfort such as tingling, tightness or redness.
However, the addition of these compounds to cosmetic formulations, in particular in the form of emulsions, may significantly alter their stability and cause a phase change.
To overcome this disadvantage, it is possible to increase, in the case of water- in-oil emulsions (W/O), the dispersed aqueous phase content, which enables stability to be improved by increasing viscosity. However, if the water content is too high, the cosmetic application properties of the composition are altered.
There is therefore a need to provide compositions in the form of a W/O emulsion that are stable and that have good cosmetic application properties.
This invention is intended to provide water-in-oil emulsions intended for use in skincare and/or makeup compositions.
This invention is intended to provide skincare and/or makeup compositions in the form of water-in-oil emulsions that are stable over time. This invention is intended to provide skincare and/or makeup compositions having a good compromise between stability and cosmetic properties.
This invention relates to a composition including a physiologically acceptable medium containing:
- at least one coloring agent; and
- at least one jasmonic acid derivative compound with the following formula (I):
Figure imgf000003_0001
in which:
. Ri represents a radical COOR3, with R3 designating a hydrogen atom or a C1 -C4 alkyl radical, optionally substituted by one or more hydroxyl groups; . R2 represents a hydrocarbon radical, saturated or unsaturated, and linear with 1 to 18 carbon atoms, or branched or cyclic with 3 to 18 carbon atoms; as well as their optical isomers and corresponding salts;
wherein said composition is in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fat phase,
wherein said aqueous phase represents 40% to 55%, in particular 42% to 52%, and preferably 44% to 50%, by weight with respect to the total weight of said composition.
The compositions according to the invention are cosmetic compositions intended for skincare and/or makeup.
The emulsions obtained have good stability over time, a pleasant appearance and, during application, comfortable sensation properties.
The term "stable emulsion" refers to an emulsion that, after 7 days of storage at room temperature (20-22 °C), does not show any macroscopic change in color, odor or viscosity.
Jasmonic acid derivatives
The compositions of the invention include at least one jasmonic acid derivative of formula (I) as defined above.
The compositions of the invention may include mixtures of compounds of formula (I). According to this invention, the "alkyl" radicals Cx-Cy represent saturated hydrocarbon radicals, in a straight or branched chain, including from x to y carbon atoms, preferably 1 to 12, or 1 to 4 carbon atoms (they may typically be represented by the formula CnH2n+i , with n representing the number of carbon atoms). It is possible in particular to cite, when they are linear, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl and decyl radicals. It is possible in particular to cite, when they are branched or substituted by one or more alkyl radicals, isopropyl, tert-butyl, 2- ethylhexyl, 2-methylbutyl, 2-methylpentyl, 1 -methylpentyl and 3-methylheptyl radicals.
According to an embodiment, in formula (I), R3 is chosen from the group consisting of H, methyl, ethyl, optionally substituted by a hydroxyl and propyl group, optionally substituted by one or two hydroxyl group(s).
When R3 represents an alkyl group, it may be substituted by one or more hydroxyl group(s), the or said hydroxyl group(s) capable of being bound in the terminal position of the alkyl radical and/or in the lateral position. For example R3 may be a -CH2-CH(OH)-CH3 group or a -CH2-CH2-CH2OH group or a -CH2-CH(OH)- CH2OH group.
According to an embodiment, the compositions of the invention include a compound of formula (I), in which Ri is chosen from the group consisting of: -COOH, -COOCH3, -COO-CH2-CH3, -COO-CH2-CH(OH)-CH2OH, -COOCH2-CH2- CH2OH and -COOCH2-CH(OH)-CH3.
According to an embodiment, the compositions of the invention may include a compound of formula (I), in which R2 is a hydrocarbon radical, linear, saturated or unsaturated, having 2 to 7 carbon atoms.
In formula (I), R2 may represent an alkyl radical, linear or branched, including 1 to 18 carbon atoms, or preferably 2 to 7 carbon atoms.
According to an embodiment, in formula (I), R2 is chosen from the group consisting of pentyl, pentenyl, hexyl and heptyl radicals.
According to an embodiment, the compositions of the invention include a compound of formula (I), in which is -COOH.
A particular jasmonic acid derivative compound used in the compositions of the invention responds to the following formula (II):
Figure imgf000004_0001
in which R2 represents an alkyl group, linear or branched, including 1 to 18 carbon atoms, or preferably 2 to 7 carbon atoms.
According to an embodiment, in formula (II), R2 is chosen from the group consisting of pentyl, pentenyl, hexyl and heptyl radicals.
According to a particular embodiment, the compositions of the invention include a compound of formula (I) chosen from among 3-hydroxy-2-pentyl- cyclopentane acetic acid or 3-hydroxy-2-pentyl-cyclopentane acetic acid sodium salt.
The compounds of formula (I) may comprise one or more asymmetric carbon atoms. They may therefore be in the form of enantiomers or diastereoisomers. These enantiomers or diastereoisomers as well as mixtures thereof, including racemic mixtures, are part of the invention.
The compounds of formula (I) may be in the basic state or in the form of acid addition salts. Such addition salts are part of the invention.
The salts of the compounds capable of being used according to the invention are in particular chosen from the metal alkaline salts, such as sodium or potassium; the metal alkaline-earth salts, such as calcium, magnesium or strontium, the metal salts, such as zinc, aluminum, manganese and copper; the ammonium salts of formula NH4 +; the quaternary ammonium salts; the organic amine salts, such as, for example, methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2- hydroxyethylamine, bis-(2-hydroxyethyl)amine and tri-(2-hydroxyethyl)amine salts; or lysine and arginine salts. Preferably, the salts chosen from sodium, potassium, magnesium, strontium, copper, manganese and zinc are used. More preferably, sodium salt is used.
According to a particular embodiment, in the compositions of the invention, the compound of formula (I) is brought to the aqueous phase and in a content ranging from 0.001 % to 10%, in particular from 0.1 % to 8%, and preferably from 0.5% to 5% by weight with respect to the total weight of said composition.
Coloring agent
The coloring agent present in the compositions of the invention is chosen, for example, from the group consisting of pigments, dyes and interferential particles.
According to an embodiment, the coloring agent is chosen from the pigments.
Such a cosmetic composition according to the invention may advantageously incorporate at least one dye chosen from organic or inorganic coloring materials, in particular of the pigment or nacre type conventionally used in cosmetic compositions, fat-soluble or water-soluble dyes, materials with a specific optical effect and mixtures thereof.
The term pigment refers to inorganic or organic white or colored particles, insoluble in an aqueous solution, intended to color and/or opacify the resulting film.
The pigments may be present in an amount of 0.1 % to 40% by weight, in particular 1 % to 30% by weight, and in particular 5% to 15% by weight with respect to the total weight of the cosmetic composition.
As inorganic pigments that can be used in the invention, it is possible to cite titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides, Prussian blue, manganese violet, ultramarine blue and chromium hydrate. Preferably, the composition of the invention includes at least titanium oxides and iron oxides.
It may also be a pigment having a structure that can be, for example, of the sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is sold, for example, under the reference name COVERLEAF NS or JS by the CHEMICALS AND CATALYSTS company and has a contrast ratio of around 30.
The coloring material may also comprise a pigment having a structure that can be, for example, of the silica microsphere type containing iron oxide. An example of a pigment having this structure is that sold by the MIYOSHI company under the reference name PC BALL PC-LL-100 P, with this pigment being comprised of silica microspheres containing yellow iron oxide.
The term "nacre" refers to colored particles of any shape, iridescent or not, in particular, produced by certain mollusks in their shell or produced synthetically, and which have an optical interference color effect.
The nacres may be present in an amount of 0.1 % to 30% by weight, in particular, from 0.5% to 20% by weight and, in particular, from 1 % to 15% by weight with respect to the total weight of the cosmetic composition.
The nacres may be chosen from pearlescent pigments, such as bismuth oxychloride, titanium mica coated with an iron oxide, titanium mica covered with bismuth oxychloride, titanium mica covered with chromium oxide, titanium mica covered with an organic dye, as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles with a surface on which at least two successive layers of metal oxides and/or organic coloring materials are superimposed.
It is also possible to cite, as examples of nacres, natural mica covered with titanium oxide, iron oxide, natural pigment or bismuth oxychloride. Among the nacres available on the market, it is possible to cite TIMICA, FLAMENCO and DUOCHROME nacres (mica-based) sold by the ENGALHARD company, the TIMIRON nacres sold by the MERCK company, the PRESTIGE mica- based nacres sold by the ECKART company and the synthetic SUNCHINE mica- based nacres sold by the SUN CHEMICAL company.
The nacres may more specifically have a yellow, pink, red, bronze, orange, brown and/or copper reflection or color.
As examples of nacres capable of being implemented in the context of this invention, it is possible to cite colored nacres, in particular, sold by the ENGELHARD company, 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 in particular by the Merck company under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the Engelhard company under the name Super Bronze (Cloisonne); the orange nacres sold in particular by the Engelhard company under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the Merck company under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); the brown nacres sold in particular by the Engelhard company under the name Nu-Antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the copper-tinted nacres sold in particular by the Engelhard company under the name Copper 340A (Timica); the red-tinted nacres sold in particular by the Merck company under the name Sienna Fine (17386) (Colorona); the yellow-tinted nacres sold in particular by the Engelhard company under the name Yellow (4502) (Chromalite); the gold-tinted red nacres sold in particular by the Engelhard company under the name Sunstone G012 (Gemtone); the pink nacres sold in particular by the Engelhard company under the name Tan Opale G005 (Gemtone); the gold-tinted black nacres sold in particular by the Engelhard company under the name Nu-Antique Bronze 240 AB (Timica), the blue nacres sold in particular by the Merck company under the name Matte Blue (17433) (Microna), the silver-tinted white nacres sold in particular by the Merck company under the name Xirona Silver, and the golden-green pink-orange nacres sold in particular by the Merck company under the name Indian Summer (Xirona), and mixtures thereof.
The cosmetic composition according to the invention may also include water- soluble or fat-soluble dyes. The fat-soluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, β-carotene, soya oil, Sudan Brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and Quinoline Yellow. The water-soluble dyes are, for example, beet juice and caramel.
The dyes may be present in an amount of 0.001 % to 5% by weight, in particular 0.01 % to 3% by weight, and in particular 0.025% to 1 % by weight, with respect to the total weight of the cosmetic composition.
The cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
This effect is different from a simple conventional tint effect, i.e. unified and stabilized as produced by the conventional coloring materials such as, for example, monochromatic pigments. In the sense of the invention "stabilized" means lacking an effect of color variability with the angle of view or in response to a temperature change.
For example, this material may be chosen from particles with a metallic sheen, goniochromatic coloring agents, diffracting pigments, thermochromic agents, optical brightening agents, as well as fibers, in particular, interferential fibers. Of course, these different materials may be combined so as to provide a simultaneous appearance of two effects, or even a new effect according to the invention.
The particles with a metallic sheen capable of being used in the invention are in particular chosen from:
- particles of at least one metal and/or at least one metal derivative,
- particles comprising an organic or inorganic substrate, made of a single material or of multiple materials, covered at least partially by at least one layer with a metallic sheen, including at least one metal and/or at least one metal derivative, and mixtures of said particles.
Among the metals capable of being present in said particles, it is possible to cite, for example, Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te, Se and mixtures or alloys thereof. Ag, Au, Cu, Al, Zn, Ni, Mo, Cr, and mixtures or alloys thereof (for example, bronzes and brasses) are preferred metals.
The term "metal derivatives" refers to compounds derived from metals, in particular oxides, fluorides, chlorides and sulfides.
As an illustration of these particles, it is possible to cite aluminum particles, such as those sold under the names STARBRITE 1200 EAC® by the SIBERLINE company and METALURE® by the ECKART company.
It is also possible to cite copper metal powders or alloy mixtures, such as those of reference 2844 sold by the RADIUM BRONZE company, metal pigments, for example, aluminum or bronze, such as those sold under the name ROTOSAFE 700 of the ECKART company, silica-coated aluminum particles sold under the name VISIONAIRE BRIGHT SILVER of the ECKART company and metal alloy particles, such as silica-coated bronze powders (copper and zinc alloy) sold under the name VISIONAIRE BRIGHT NATURAL GOLD of the ECKART company.
They may also be particles comprising a glass substrate such as those sold by the NIPPON SHEET GLASS company under the names MICROGLASS METASHINE.
The goniochromatic coloring agent may be chosen, for example, among the interferential multilayer structures and the liquid crystal coloring agents.
Examples of symmetrical interferential multilayer structures that can be used in compositions produced according to the invention are, for example, the following structures: Al/Si02/Al/Si02/Al, pigments having this structure and sold by the DUPONT DE NEMOURS company; Cr/MgF2/AI/MgF2/Cr, pigments having this structure and sold under the name CHROMAFLAIR by the FLEX company; MoS2/Si02/AI/Si02/MoS2; Fe203/Si02/Al/Si02/Fe203, and
Fe203/Si02/Fe203/Si02/Fe203, pigments having these structures and sold under the name SICOPEARL by the BASF company; MoS2/Si02/mica-oxide/Si02/MoS2; Fe203/Si02/mica-oxyde/Si02/Fe203; Ti02/Si02/Ti02 and Ti02/Al203/Ti02 ; SnO/Ti02/Si02/Ti02/SnO; Fe203/Si02/Fe203; SnO/mica/Ti02/Si02/Ti02/mica/SnO, pigments having these structures and sold under the name XIRONA by the MERCK company (Darmstadt). For example, these pigments may be pigments with a silica / titanium oxide / tin oxide structure sold under the name XIRONA MAGIC by the MERCK company, pigments with a silica / brown iron oxide structure sold under the name XIRONA INDIAN SUMMER by the MERCK company and pigments with a silica /titanium oxide / mica / tin oxide structure sold under the name XIRONA CARRIBEAN BLUE by the MERCK company. It is also possible to cite the INFINITE COLORS pigments of the SHISEIDO company. According to the thickness and the nature of the different layers, different effects are obtained. Thus, with the structure Fe203/Si02/Al/ Si02/Fe203, the color changes from golden-green to gray-red for Si02 layers from 320 to 350nm; from red to golden for Si02 layers from 380 to 400nm; from violet to green for Si02 layers from 410 to 420nm; from copper to red for Si02 layers from 430 to 440nm.
It is possible to cite, as an example of pigments with a multilayer polymeric structure, those sold by the 3M company under the name COLOR GLITTER. As liquid crystal goniochromatic particles, it is possible to use, for example, those sold by the CHENIX company, as well as that sold under the name HELICONE® HC by the WACKER company.
These goniochromatic coloring agents may be present in the composition in a content ranging from 0.01 % to 30% by weight, in particular from 0.1 % to 20% by weight with respect to the total weight of said composition.
Physiologically acceptable medium
In addition to the compounds mentioned above, a composition according to the invention includes a physiologically acceptable medium.
The term "physiologically acceptable medium" refers to a medium particularly suitable for the application of a composition of the invention on the skin or on the lips.
The physiologically acceptable medium is generally adapted to the type of support on which the composition must be applied, as well as the form in which the composition is to be packaged.
The compositions of the invention are in the form of a W/O emulsion containing a dispersed aqueous phase and a continuous oily phase.
Aqueous phase
The composition according to the invention comprises an amount of aqueous phase that varies from 40% to 55% by weight with respect to the total weight of the composition.
When the aqueous phase content is less than 40%, the emulsion is no longer stable, and when the aqueous phase content is greater than 55%, the application properties are degraded.
The aqueous phase includes water and any other water-soluble compound that might be present, such as, in particular, water-soluble additives and solvents.
As water-soluble solvents, it is possible to cite, in particular, alcohols comprising 2 to 8 carbon atoms, in particular from 2 to 6 carbon atoms such as ethanol.
As polyols, it is possible to cite, for example, glycerol, butylene glycol and polyethylene glycols.
The aqueous phase may also contain other additives such as water-soluble active ingredients, preservatives, salts, gelling agents, fillers, water-soluble or water- dispersible polymers, water-soluble dyes, and so on. Fatty phase
A cosmetic composition according to this invention may include at least one liquid and/or solid fatty phase.
In particular, a composition of the invention may include at least one liquid fatty phase, in particular at least one oil as mentioned below.
The term oil refers to any fatty body in liquid form at room temperature (20- 25°C) and atmospheric pressure. These oils may be of animal, plant, mineral or synthetic origin.
According to an embodiment, the fatty phase of the compositions of the invention includes at least one volatile oil and/or at least one non-volatile oil.
Volatile oils
According to an embodiment, the fatty phase of the compositions of the invention includes at least one volatile oil. The fatty phase of the compositions of the invention may include a mixture of multiple volatile oils.
The term "volatile oil" refers to any non-aqueous medium capable of evaporating from the skin or lips, in less than one hour, at room temperature and atmospheric pressure. The volatile oil is a volatile cosmetic oil, liquid at room temperature. More specifically, a volatile oil has an evaporation rate of between 0.01 and 200mg/cm2/min, inclusive.
To measure this evaporation rate, 15g of oil or a mixture of oils to be tested are introduced into a crystallizer, 7cm in diameter, placed on a scale located in a large 0.3m3 chamber temperature-controlled at a temperature of 25qC, and humidity-controlled with a relative humidity of 50%. The liquid is left to evaporate freely, without stirring, by providing ventilation with a fan (PAPST-MOTOREN, reference 8550 N, rotating at 2700 rpm) positioned vertically above the crystallizer containing the solvent, with the blades directed toward the crystallizer and at a distance of 20cm from the base of the crystallizer. The mass of oil remaining in the crystallizer is measured at regular intervals. The evaporation rates are expressed in mg of oil evaporated per surface area unit (cm2) and per time unit (minute).
The volatile oils may be hydrocarbon-based, silicone-based or fluorine-based.
According to the invention, the term "silicone oil" refers to an oil including at least one silicon atom, and in particular at least on Si-0 group.
The term "fluorine oil" refers to an oil including at least one fluorine atom. The term "hydrocarbon oil" refers to an oil containing primarily hydrogen and carbon atoms.
The oils may optionally include oxygen, nitrogen, sulfur and/or phosphorus atoms, for example, in the form of hydroxyl or acid radicals.
The volatile oils may be chosen from hydrocarbon oils having 8 to 16 carbon atoms, and in particular branched C8-Ci6 alkanes (also called isoparaffins or isoalkanes), such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, and, for example, the oils sold under the trade names ISOPARS®or PERMETHYLS®.
It is also possible to cite, as a hydrocarbon volatile oil, linear C9-Ci7 alkanes, such as dodecane (Ci2) and tetradecane (C ), sold respectively under the names PARAFOL® 12-97 and PARAFOL® 14-97 (Sasol), and, as alkanes obtained according to the method described in the international application WO 2007/068371 A1 , such as the undecane (Cn) and tridecane (Ci3) mixture sold under the name CETIOL® UT (Cognis).
Among the volatile hydrocarbon oils, isododecane and the undecane (Cn) and tridecane (Ci3) mixture are preferred.
It is also possible to use, as volatile oils, volatile silicones, such as, for example, volatile linear or cyclic silicones, in particular those having a viscosity below or equal to 8 centistokes (cSt) (8 x 10"6 m2/s), and having, in particular, from 2 to 10 silicon atoms, and in particular from 2 to 7 silicon atoms, in which these silicones optionally comprise alkyl or alkoxyl groups having from 1 to 10 carbon atoms. It is possible to cite, as a volatile silicone oil that can be used in the invention, in particular, dimethicones with a viscosity of 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.
More specifically, as a volatile silicone oil, it is possible to cite linear or cyclic silicone oils having from 2 to 7 silicon atoms, in which these silicones optionally comprise alkyl or alkoxyl groups having from 1 to 10 carbon atoms.
As preferred examples, it is possible to cite decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane and dodecamethyl pentasiloxane.
Among the volatile silicone oils, dodecamethyl pentasiloxane is preferred.
It is possible to cite, as a volatile fluorine oil, for example, nonafluoromethoxybutane or perfluoromethylcyclopentane, and mixtures thereof. Non-volatile oils
According to an embodiment, the fatty phase of the compositions of the invention includes at least one non-volatile oil. The fatty phase of the compositions of the invention may include a mixture of a plurality of non-volatile oils.
The term "non-volatile oil" is intended to mean an oil remaining on the skin or keratin fiber at ambient temperature and atmospheric pressure. More specifically, a non-volatile oil has an evaporation rate strictly below 0.01 mg/cm2/min.
The non-volatile oils may, in particular, be chosen from among the non-volatile hydrocarbon, fluorine and/or silicone oils.
It is possible to cite, as a non-volatile hydrocarbon oil:
- hydrocarbon oils of animal origin, such as perhydrosqualene,
- hydrocarbon oils of plant origin, such as phytostearyl esters, for instance phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate (AJINOMOTO, ELDEW PS203), triglycerides constituted of fatty acid esters of glycerol, in particular in which the fatty acids may have chain lengths ranging from C4 to C36, and in particular from Ci8 a C36, it being possible for these oils to be linear or branched, and saturated or unsaturated; these oils may in particular be heptanoic or octanoic triglycerides, shea oil, alfalfa oil, poppy seed oil, pumpkin oil, millet oil, barley oil, quinoa oil, rye oil, candlenut oil, passionflower oil, shea butter, aloe oil, sweet almond oil, peach kernel oil, groundnut oil, argan oil, avocado oil, baobab oil, barrage oil, broccoli oil, calendula oil, camelina oil, canola oil, carrot oil, safflower oil, hemp oil, rapeseed oil, cotton seed oil, coconut oil, marrow seed oil, wheat germ oil, jojoba oil, lily oil, macadamia oil, corn oil, meadowfoam oil, St. John's Wort oil, monoi oil, hazelnut oil, apricot kernel oil, nut oil, olive oil, evening primrose oil, palm oil, blackcurrant seed oil, kiwi seed oil, grape seed oil, pistachio oil, pumpkin oil, winter squash oil, quinoa oil, musk rose oil, sesame oil, soya oil, sunflower oil, castor oil and watermelon oil, and mixtures thereof, or alternatively caprylic/capric acid triglycerides, for instance those sold by the STEARINERIES DUBOIS company or those sold under the names MIGLYOL 810®, 812® and 818® by the DYNAMIT NOBEL company,
- linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, polybutenes, hydrogenated polyisobutene such as Parleam, squalane;
- synthetic ethers having from 10 to 40 carbon atoms; - synthetic esters, for instance oils of formula RiCOOR2, in which Ri represents a linear or branched fatty acid residue containing from 1 to 40 carbon atoms, and R2 represents a hydrocarbon-based chain, in particular a branched chain, containing from 1 to 40 carbon atoms provided that Ri et R2 is greater than or equal to 10. The esters may in particular be selected from fatty acid and alcohol esters, for instance: cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactacte, octyl hydroxystearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-ethylhexyl 4-diheptanoate and palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol 2-diethylhexanoate, and mixtures thereof, Ci2-Ci5 alkyl benzoates, hexyl laurate, neopentanoic acid esters, for instance isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, or octyldodecyl neopentanoate, isononanoic acid esters, for instance isononyl isononanoate, isotridecyl isononanoate and octyl isononanoate, hydroxylated esters such as isostearyl lactate and diisostearyl malate;
- polyol esters and pentaerythritol esters, for instance dipentaerythrityl tetrahydroxystearate/tetraisostearate,
- esters of diol dimers and diacid dimers, such as Lusplan DD-DA5® and Lusplan DD-DA7®, sold by the NIPPON FINE CHEMICAL company and described in the application US 2004-175338,
- copolymers of a diol dimer and of a diacid dimer and esters thereof, such as copolymers of dilinoleyl diol dimers/dilinoleic dimers and esters thereof, for instance Plandool-G,
- copolymers of polyols and of diacid dimers, and esters thereof, such as Hailuscent ISDA, or the copolymer of dilinoleic acid/butanediol,
- fatty alcohols that are liquid at ambient temperature, with a branched and/or unsaturated carbon chain having from 12 to 26 carbon atoms, for instance 2- octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol and 2-undecylpentadecanol,
- Ci2-C22, higher fatty acids, such as oleic acid, linoleic acid or linolenic acid, and mixtures thereof, and,
- dialkyl carbonates, the two alkyl chains possibly being identical or different, such as the dicaprylyl carbonate sold under the name CETIOL CC®, by COGNIS, - oils of higher molar mass having in particular a molar mass ranging from approximately 400 to approximately 10,000 g/mol, in particular from approximately 650 to approximately 10,000 g/mol, in particular from approximately 750 to approximately 7500 g/mol, and more particularly ranging from approximately 1000 to approximately 5000 g/mol. As oils of higher molar mass that can be used in the invention, mention may in particular be made of the oils selected from:
• lipophilic polymers,
• linear fatty acid esters having a total carbon number ranging from 35 to 70,
• hydroxylated esters,
• aromatic esters,
• esters of C24-C28 branched fatty acids or fatty alcohols,
• silicone oils,
• oils of plant origin,
• and mixtures thereof;
- fluorine oils optionally partially hydrocarbon-based and/or silicone-based, such as fluorosilicone oils, fluorinated polyethers or fluorinated silicones, as described in document EP-A-847 752;
- silicone oils, such as polydimethylsiloxanes (PDMS) which are non-volatile and linear or cyclic; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups which are pendant or at the end of the silicone chain, said groups having from 2 to 24 carbon atoms; phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl-trimethylsiloxy-diphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl-trisiloxanes or (2-phenylethyl)trimethylsiloxysilicates, and
- mixtures thereof.
Among the linear or branched hydrocarbons, of mineral or synthetic origin, paraffin oils or petroleum jelly are preferably used.
Among the hydrocarbon oils of plant origin, it is possible to cite, preferably, plant oils, such as sweet almond oil, jojoba oil or macadamia nut oil.
Among the synthetic oils such as synthetic esters, isodecyl neopentanoate or isononyl isononanoate is used in particular, and among the synthetic ethers, dicapryl ether is preferably used.
Among the non-volatile silicone oils, polydimethylsiloxanes, phenyltrimethicone or alkyldimethicones such as cetyl dimethicone are preferably used. According to an embodiment, the fatty phase of the compositions of the invention represents a percentage ranging from 15% to 70%, and preferably ranging from 20% to 50% with respect to the total weight of the composition. Thickeners
Depending on the fluidity of the composition that it is desired to obtain, one or more thickeners or gelling agents may be incorporated into a composition of the invention.
A thickener or gelling agent suitable for the invention may be hydrophilic, i.e. water-soluble or water-dispersible.
As hydrophilic gelling agents, mention may in particular be made of water- soluble or water-dispersible thickening polymers. Said polymers may in particular be selected from: modified or unmodified carboxyvinyl polymers, such as the products sold under the name Carbopol (CTFA name: carbomer) by the Goodrich company; polyacrylates and polymethacrylates, such as the products sold under the names
Lubrajel and Norgel by the GUARDIAN company or under the name Hispagel by the H ISPANO CH IMICA company; polyacrylamides; 2-acrylamido-2- methylpropanesulfonic acid polymers and copolymers, which are optionally cross- linked and/or neutralized, such as the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by the CLARIANT company under the name "Hostacerin AMPS" (CTFA name: ammonium polyacryldimethyltauramide); cross-linked anionic acrylamide/AMPS copolymers, in the form of a W/O emulsion, such as those sold under the name SEPIGEL 305 (CTFA name: Polyacrylamide/C13-14 lsoparaffin/Laureth-7) and under the name SIMULGEL 600 (CTFA name: Acrylamide/Sodium acryloyldimethyltaurate copolymer/lsohexadecane/Polysorbate
80) by the SEPPIC company; polysaccharide biopolymers, such as xanthan gum, guar gum, carob gum, gum acacia, scleroglucans, chitin derivatives and chitosan derivatives, carrageenans, gellans, alginates, or celluloses such as microcrystalline cellulose, carboxymethylcellulose, hydroxymethylcellullose and hydroxypropylcellulose; and mixtures thereof.
A thickener or gelling agent suitable for the invention may be lipophilic, it may be inorganic or organic.
As lipophilic thickeners, mention may, for example, be made of modified clays, such as modified magnesium silicate (Bentone gel VS38 of RHEOX), modified hectorites such as hectorite modified with a Ci0 to C22 fatty acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride, for instance the product sold under the name Bentone 38V® by the ELEMENTIS company or that sold under the name "Bentone 38 CE" by the RHEOX company or that sold under the name Bentone Gel V5 5V by the ELEMENTIS company.
The polymeric organic lipophilic gelling agents are, for example partially or totally cross-linked elastomeric organopolysiloxanes with a three-dimensional structure, such as those sold under the names KSG6®, KSG16® and KSG18® by the SHIN-ETSU company, Trefil E-505C® and Trefil E-506C® by the DOW-CORNING company, Gransil SR-CYC®, SR DMF10®, SR-DC556®, SR 5CYC gel®, SR DMF 10 gel® and SR DC 556 gel® by the GRANT INDUSTRIES company, SF 1204® and JK 1 13® by the GENERAL ELECTRIC company; ethylcellulose, such as the product sold under the name Ethocel® by the DOW CHEMICAL company; polyamide-type polycondensates resulting from condensation between a dicarboxylic acid containing at least 32 carbon atoms and an alkylene diamine, and in particular ethylene diamine, in which the polymer comprises at least one terminal carboxylic acid group esterified or amidified with at least one monoalcohol or one monoamine containing from 12 to 30 carbon atoms, and linear and saturated, and in particular ethylenediamine/stearyl dilinoleate copolymers such as the product sold under the name Uniclear 100 VG® by the ARIZONA CHEMICAL company; galactomannans containing from one to six, and in particular from two to four, hydroxyl groups per monosaccharide, substituted with a saturated or unsaturated alkyl chain, such as guar gum alkylated with Ci to C6 alkyl chains, and in particular Ci to C3 alkyl chains, and mixtures thereof. Block copolymers of the "diblock", "triblock" or "radial" type, of the polystyrene/polyisoprene or polystyrene/polybutadiene type, such as those sold under the name Luvitol HSB® by the BASF company, of the polystyrene/copoly(ethylene-propylene) type, such as those sold under the name Kraton® by the SHELL CHEMICAL Company or of the polystyrene/copoly(ethylene- butylene) type, blends of triblock and radial (star) copolymers in isododecane, such as those sold by the PENRECO company under the name Versagel® for instance the mixture of butylene/ethylene/styrene triblock copolymer and of ethylene/propylene/styrene star copolymer in isododecane (Versagel M 5960).
Among the lipophilic gelling agents that can be used in a cosmetic composition of the invention, mention may also be made of esters of dextrin and of a fatty acid, such as dextrin palmitates, in particular such as those sold under the names Rheopearl TL® or Rheopearl KL® by the CHIBA FLOUR company, hydrogenated plant oils, such as hydrogenated castor oil, fatty alcohols, in particular C8 to C26, and more particularly C12 to C22, fatty alcohols, for instance myristyl alcohol, cetyl alcohol, stearyl alcohol and behenyl alcohol.
According to an embodiment, a composition may comprise thickeners in a content with respect to active material of from 0.01 % to 40% by weight, especially from 0.1 % to 20% by weight, in particular from 0.3% to 15% by weight, relative to the total weight of the composition.
According to a preferred embodiment, the composition includes at least one lipophilic thickener, in particular at least one modified hectorite, such as a hectorite modified by a Ci0 to C22 fatty acid ammonium chloride, advantageously in a content ranging from 0.1 % to 5% by weight, in particular 0.5% to 2% by weight of active material with respect to the total weight of said composition
Fillers
A composition according to the invention may also comprise at least one filler, of organic or inorganic nature, which makes it possible in particular to confer thereon additional properties of mattness, covering power and/or improved stability or staying power.
The filler content may range from 0.1 % to 20% by weight, and in particular from 1 % to 12% by weight with respect to the total weight of said composition.
The term "filler" should be understood to mean colorless or white solid particles of any shape, which are in a form that is insoluble or dispersed in the medium of the composition. Inorganic or organic in nature, they make it possible to confer body or rigidity on the composition, and/or softness, and uniformity on the makeup.
The fillers used in the compositions according to the present invention may be of lamellar, globular or spherical form, or in the form of fibers or in any other intermediate form between these defined forms.
The fillers may or may not be surface-coated, and in particular they may be surface-treated with silicones, amino acids, fluorinated derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.
As examples of inorganic fillers, mention may be made of talc, mica, silica, hollow silica microspheres, kaolin, calcium carbonate, magnesium carbonate, hydroxyapatite, boron nitride, glass or ceramic microcapsules, composites of silica and of titanium dioxide, such as the TSG series sold by Nippon Sheet Glass.
As examples of organic fillers, mention may be made of polyamide powder (Nylon® Orgasol of Atochem), polyethylene powder, polymethyl methacrylate powder, polytetrafluoroethylene powder (Teflon), acrylic acid copolymer powder (Polytrap of the Dow Corning company), lauroyl lysine, hollow polymeric microspheres such as those of polyvinylidene/acrylonitrile chloride, for instance Expancel (Nobel Industry), hexamethylene diisocyanate/Trimethylol hexyllactone copolymer powder (Plastic Powder of Toshiki), silicone resin microbeads (Tospearl of Toshiba, for example) synthetic or natural micronized waxes, metal soaps derived from organic carboxylic acids having 8 to 22 carbon atoms, and preferably from 12 to 18 carbon atoms, for example, zinc stearate, magnesium stearate or lithium stearate, zinc laurate, magnesium myristate Polypore® L 200 (Chemdal Corporation), cross-linked elastomeric organopolysiloxane powders coated with silicone resin, in particular silsesquioxane resin, as described for example in the patent US 5 538 793, polyurethane powders, in particular, cross-linked polyurethane powders including a copolymer, in which said copolymer includes hexyllactone trimethylol. In particular, it may be a polymer of hexamethylene diisocyanate/trimethylol hexyllactone. Such particles are in particular commercially available, for example under the name PLASTIC POWDER D-400® or PLASTIC POWDER D-800® of the TOSHIKI company and mixtures thereof.
According to a particular embodiment of the invention, the composition includes at least one cross-linked elastomeric organopolysiloxane powder coated with silicone resin. The presence of this filler also enables the composition of the invention to be thickened and/or gelled.
The cross-linked elastomeric organopolysiloxane powder(s) coated with silicone resin may be present in a content ranging from 0.5% to 12% by weight, advantageously from 2% to 10% by weight and preferably from 7% to 9% by weight with respect to the total weight of said composition.
In particular, mention may be made of cross-linked elastomeric organopolysiloxane powders coated with silicone resin, in particular silsesquioxane resin, as described for example in the patent US 5 538 793. Such elastomer powders are sold under the names KSP-100®, KSP-101 ®, KSP-102®, KSP-103®, KSP-104® and KSP-105® by the SHIN ETSU company; mention may also be made of cross-linked elastomeric organopolysiloxane powder coated with silicone resin such as hybrid silicone powders functionalized by fluoroalkyi groups, in particular sold under the name "KSP-200" by the Shin Etsu company; or hybrid silicone powders functionalized by phenyl groups, in particular sold under the name "KSP- 300" by the Shin Etsu company. Emulsifier
The composition of the invention may also include one or more emulsifiers.
As emulsifiers, it is possible to cite, in particular, polyhydroxylated and polyoxyalkylene glycol fatty acid emulsifiers.
Preferably, the polyhydroxylated and polyoxyalkylene glycol fatty acid ester is a fatty acid and polyethylene glycol ester.
The fatty acid and polyoxyalkylene glycol ester may be a monoester or a polyester, in particular a diester or a triester.
The fatty acid may include 12 to 20 carbon atoms, and preferably 14 to 18 carbon atoms. It may be chosen in particular from oleic acid, palmitic acid, stearic acid and mixtures thereof.
The polyethylene glycol may include from 4 to 50 moles of ethylene oxide and more preferably 20 to 40 moles of ethylene oxide.
According to an embodiment, an ester is used, preferably a diester, of polyethylene glycol including 20 to 40 moles of ethylene oxide and polyhydroxylated fatty acid, in which said polyhydroxylated fatty acid includes 14 to 18 carbon atoms, in particular polyhydroxystearic acid.
In particular, the fatty acid and polyoxyalkylene glycol ester is in the form of a sequenced polymer, preferably with an ABA structure, comprising poly(hydroxylated ester) and polyethylene glycol sequences.
The fatty acid ester of said polymer has a chain comprising 12 to 20 carbon atoms, and preferably 14 to 18 carbon atoms.
The polyethylene glycol sequences of said emulsifying polymer as defined above preferably comprise 4 to 50 moles of ethylene oxide, and more preferably 20 to 40 moles of ethylene oxide.
A compound particularly suitable for producing the compositions of the invention is polyethylene glycol dipolyhydroxystearate with 30 moles of ethylene oxide sold under the trade name "CITHROL DPHS-SO-(MV)" by the Croda company.
The polyoxyalkylene glycol is generally present in compositions according to the invention in an amount capable of ranging from 0.1 % to 15% by weight with respect to the total weight of the composition, and preferably 0.5% to 10% by weight, and better yet 1 % to 5% by weight with respect to the total weight of the composition.
According to an embodiment, the composition of the invention may include, in addition to the polyoxyalkylene glycol and polyhydroxylated fatty acid ester emulsifier, an additional emulsifier (or surfactant), also called a co-emulsifier. This co-emulsifier does not alone enable, in the absence of a polyoxyalkylene glycol and polyhydroxylated fatty acid ester, the composition of the invention to be stabilized.
The additional emulsifier may be chosen, for example, from the non-ionic emulsifiers derived from polyol-fatty acid, polyolefins with a succinic end, and mixtures thereof.
As polyolefins with a succinic end, it is possible to cite, in particular, polyisobutylenes with an esterified succinic end and salts thereof, in particular diethanolamine salts, such as the products sold under the names Lubrizol 2724, Lubrizol 2722 and Lubrizol 5603 by the Lubrizol company.
Preferably, the additional emulsifier is chosen from the polyol-fatty acid esters.
The term "polyol-fatty acid ester" according to the invention refers to polyol- fatty acid esters in which the fatty acid includes a C6-C22, and preferably Ci6-C20, alkyl chain, and the polyol is chosen from glycerol, polyglycerol, sorbitan, and mixtures thereof. The fatty acid may also be in a polymeric form, as is the case of the polyhydroxystearic acid (12-hydroxystearic acid polymer).
According to a particular embodiment, the polyol-fatty acid ester is a Ci6-C2o ester of fatty acid and glycerol and/or sorbitan, and mixtures thereof.
As examples of a Ci6-C20 linear or branched chain fatty acid, it is possible to cite stearic acid, isostearic acid, lauric acid, myristic acid, palmitic acid. As an example of a Ci6-C20 fatty acid polymer, it is possible to cite 12-polyhydroxystearic acid.
Preferably, stearic, isostearic or 12-polyhydroxystearic acid or mixtures thereof will be used.
The term polyglycerols refers to compounds of formula:
Figure imgf000021_0001
in which the degree of condensation n ranges from 1 to 1 1 , preferably from 2 to 6 and even more preferably from 3 to 6.
According to a particular embodiment, the polyol-fatty acid ester contains 2 to 10 moles (units) of polyols, preferably 2 to 4 moles of polyols, in articular 2 to 4 units of glycerol or a mixture of polyglycerols (glycerol, di-, tri-, tetra-, penta-, oligoglycerols). Even more preferably, the polyol-fatty acid ester contains 4 moles (or units) of polyol, in particular 4 moles (or units) of glycerol.
According to a preferred embodiment, said polyol-fatty acid ester is also a fatty acid ester, of dicarboxylic acid having 2 to 16 carbon atoms, preferably 8 to 14 carbon atoms, such as azelaic acid, sebacic acid, dodecanedioic acid, and preferably sebacic acid (Ci0), and polyol.
As examples of polyol-fatty acid esters that can be used in the composition of the invention, it is possible to cite esters of isostearic acid and of polyols and mixtures thereof, in particular esters of isostearic acid and glycerol and/or sorbitan, such as, for example, polyglycerol isostearate (4 moles) (INCI name: Polyglyceryl-4 Isostearate) sold under the name Isolan GI34® by the Goldschmidt company, polyglycerol diisostearate (3 moles) sold under the name Lameform TGI® by the Cognis company; polyglycerol distearate (2 moles) sold under the name Emalex PGSA® by the Nihon emulsion company; polyglycerol monoisostearate (10 moles) sold under the name Nikkol Decaglyn 1 -IS by the Nihon Surfactant company (INCI name: Polyglyceryl-10 isostearate); polyglyceryl-4 diisostearate polyhydroxystearate sebacate sold under the name ISOLAN GPS by Goldschmidt; the mixture of sorbitan isostearate and glycerol isostearate, such as the product sold under the name Arlacel 986 by the ICI company, the mixture of sorbitan isostearate and polyglycerol isostearate (3 moles) sold under the name Arlacel 1690 by the Uniquema company, the mixture of sorbitan isostearate and polyglycerol isostearate (3 moles) sold under the name Arlacel 1690® by the Uniquema company and mixtures thereof.
It is also possible to cite silicone surfactants such as dimethicone copolyols and alkyl dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name "DC 5225 C" by the Dow Corning company, Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by the Dow Corning company and Cetyl dimethicone copolyol sold under the name Abil EM 90® by the Goldschmidt company.
Preferably, the additional emulsifier is chosen from the fatty acid esters, preferably Ci6-C20, in particular stearic acid or isostearic acid, and polyol, chosen from glycerol and/or sorbitan.
The additional emulsifier may be present in a content (dry matter) ranging from 0.05% to 5% by weight with respect to the total weight of the composition, and preferably from 0.1 to 1 % by weight with respect to the total weight of the composition. According to another embodiment, the composition according to the invention includes less than 2%, preferably less than 1 % and even more preferably less than 0.5% of additional emulsifier, and it can in particular be free of additional emulsifier.
The composition of the invention may also include at least one silicone emulsifier.
The compositions according to the invention include a silicone emulsifier (or surfactant) chosen from the oxyethylene and oxypropylene polydimethylsiloxanes also called dimethicone copolyols, the oxyethylene and oxypropylene alkylpolydimethylsiloxanes (also called alkyldimethicone copolyols) of which the alkyl chain includes fewer than 12 carbon atoms, and mixtures thereof.
Preferably, the silicone surfactant comprises polyoxyethylene and polyoxypropylene chains grafted onto the main chain (polyoxyethylene and polyoxypropylene side or pendant chains).
The (alkyl)polydimethylsiloxanes used in the emulsion according to the invention advantageously have polyoxyethylene and polyoxypropylene side chains with the following formula:
-(CxH2x)-(OC2H4)a-(OC3H6)b-OR10
in which
- Rio represents a hydrogen atom, an alkyl radical, linear or branched, having 1 to 12 carbon atoms, preferably a hydrogen atom,
- a varies from 1 to 100, preferably from 2 to 50 and more preferably from 10 to 30,
- b varies from 1 to 100, preferably from 2 to 50, and more preferably from 10 to 30,
- x varies from 1 to 5.
Le number average molecular weight of the silicone emulsifier is generally greater than or equal to 15,000, preferably greater than or equal to 30,000 and capable of ranging from 40,000 to 100,000, in particular from 50,000 to 100,000.
As an example of a silicone compound belonging to this family, it is possible to cite oxyethylene and oxypropylene polydimethylsiloxane (OE/OP 18/18) of which the INCI name is PEG/PPG 18/18 dimethicone, sold in a mixture with a polydimethylsiloxane under the trade reference X-22-671 1 D by the Shin Etsu company or under the name ES-5226 DM by the Dow Corning company (INCI name: Dimethicone / PEG/PPG-18/18 Dimethicone).
The silicone emulsifier is generally present in the compositions according to the invention in a content capable of ranging from 0.1 % to 15% by weight, with respect to the total weight of the composition, preferably from 0.5% to 10% by weight, and more preferably from 1 % to 5% by weight with respect to the total weight of the composition.
Additives
A cosmetic composition according to the invention may also further comprise any additive normally used in the field under consideration, for example selected from gums, anionic, cationic, amphoteric or nonionic surfactants, silicone surfactants, gums, resins, dispersants, semicrystalline polymers, antioxidants, essential oils, preservatives, fragrances, neutralizing agents, antiseptics, anti-UV protective agents, cosmetic active agents, such as vitamins, hydrating agents, emollients or collagen-protecting agents, and mixtures thereof.
A person skilled in the art can adjust the type and amount of additives present in the compositions according to the invention by means of routine operations, so that the desired cosmetic properties and stability properties for these compositions are not affected by the additives.
UV Filters
The composition of the invention may also include at least one UV filter.
As a non-limiting illustration of UV filters, it is possible to cite the following families: anthranilates, in particular methyl anthranilate; benzophenones, in particular benzophenone-1 , benzophenone-3, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-9, benzophenone-12, and preferably Benzophenone-2 (Oxybenzone), or Benzophenone-4 (Uvinul MS40® available from BASF); benzylidene-camphors, in particular 3-benzylidene-camphor, benzylidene- camphor-sulfonic acid, camphor benzalkonium methosulfate, polyacrylamidomethyl benzylidene camphor, terephthalylidene dicamphor sulfonic acid, and preferably 4- methylbenzylidene camphor (Eusolex 6300® available from Merck); benzimidazoles, in particular benzimidazilate (Neo Heliopan AP® available from Haarmann and Reimer), phenylbenzimidazole sulfonic acid (Eusolex 232® available from Merck); benzotriazoles, in particular drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutylphenol (Tinosorb M® available from Ciba); cinnamates, in particular cinoxate, DEA methoxycinnamate, diisopropyl methylcinnamate, glyceryl ethylhexanoate dimethoxycinnamate, isopropyl methoxycinnamate, isoamylcinnamate, and preferentially ethocrylene (Uvinul N35® available from BASF), octyl methoxycinnamate (Parsol MCX® available from Hoffmann La Roche), or octocrylene (Uvinul 539® available from BASF): dibenzoylmethanes, in particular butylmethoxydibenzoylmethane (Parsol 1789®); imidazolines, in particular ethylhexyl dimethoxybenzylidene dioxoimidazoline; PABAs, in particular ethyl dihydroxypropyl PABA, ethylhexyldimethyl PABA, glyceryl PABA, PABA and PEG-25 PABA, and preferentially diethylhexylbutamidotriazone (Uvasorb HEB® available from 3V Sigma), ethylhexyltriazone (Uvinul T150® available from BASF) or ethyl PABA (benzocaine); salicylates, in particular dipropylene glycol salicylate, ethylhexyl salicylate, homosalate, or TEA salicylate; triazines, in particular anisotriazine (Tinosorb S® from Ciba); drometrizole trisiloxane, zinc oxide, titanium dioxide, and zinc, iron, zirconium or cerium oxide, coated or not.
Preferably, cinnamates, salicylates and mixtures thereof, or titanium dioxide are preferably used. According to an embodiment, the composition of the invention includes a UV filter chosen from the cinnamates.
According to a particular embodiment, octylmethoxycinnamate, also called ethyl hexyl methoxycinnamate is preferably used.
The quantity of filters is dependent on the desired end use. It may range, for example, from 1 to 20% by weight and more preferably from 2 to 10% by weight with respect to the total weight of the composition.
In particular, a cosmetic composition of the invention may be in the form of a liquid or fluid foundation, a hot-poured foundation product, a body makeup product, a concealer, an eye shadow, or a makeup base.
A skincare composition according to the invention may in particular be a sunscreen composition, a skincare cream, a serum or a deodorant.
Preferably, the composition of the invention is in the form of a foundation.
The composition according to the invention may be applied by any means enabling a uniform distribution, in particular using a finger, or a cotton ball, a rod, a brush, gauze, a spatula or a buffer, or by spraying, and can be removed by rinsing with water or using a gentle detergent.
The composition of the invention may be implemented so as to improve the general state of the epidermis, in particular the skin, and in particular to maintain or restore its physiological functions and/or its aesthetic appearance.
Thus, the composition of the invention may advantageously be implemented in order to fight aging of the epidermis, to maintain and/or stimulate hydration and/or to combat drying of the skin, to improve skin tone, maintain or restore flexibility and elasticity of the skin, improve mineralization of the epidermis, improve vitality of the epidermis, facilitate inter-cellular exchanges, and fight chapping and a cracking appearance of the skin.
A composition according to the invention may be intended for a cosmetic and/or dermatological application.
The invention also relates to the cosmetic use, in particular non-therapeutic, in a cosmetic composition for skincare and/or makeup, of at least one coloring agent and at least one jasmonic acid derivative compound of formula (I) as defined above, with said composition being in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fatty phase,
in which said aqueous phase represents from 40% to 55% by weight with respect to the total weight of said composition,
in order to prevent skin aging.
The invention also relates to the cosmetic use, in particular non-therapeutic, of at least one coloring agent and at least one jasmonic acid derivative compound of formula (I) as defined above in a composition, with said composition being in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fatty phase,
in which said aqueous phase represents from 40% to 55% by weight with respect to the total weight of said composition,
in order to prevent skin aging.
The invention also relates to a cosmetic treatment method including the application on the skin of a composition as defined above.
The invention also relates to a non-therapeutic skincare and/or makeup method including a step of applying at least one layer of a composition as defined above on the skin.
The invention also relates to a skin makeup method in which a composition as defined above is applied.
EXAMPLES
Definition of stability
According to the invention, the term "stable emulsion" refers to an emulsion that, after 7 days of storage at room temperature (20-22 <Ό) does not show any macroscopic change.
The stabilities are carried out on 300g of product, packaged in a 660ml jar that is hermetically sealed by an aluminum lid.
A - Influence of the aqueous phase content on stability
The examples of fluid foundations 1 to 7 make it possible to show that, when the aqueous phase content is less than 40%, the stability of the foundation is inadequate.
EXAMPLES 1-7 mass %
Cetyl PEG/PPG-10/1 dimethicone sold under the reference ABIL EM 90 by the
3.00 Goldschmidt company
Polyglycerol isostearate 4 sold under the reference ISOLAN Gl 34 by the Goldschmidt
1.00 company
Dimethicone + PEG/PPG/-18/18 dimethicone sold under the reference X-22-671 1 D by
1 .07
A1 the Shin Etsu company
Ethyl hexyl methoxycinnamate 7.50
Phenyltrimethicone sold under the reference DC 556 by the Dow Corning company Q
2cSt dimethicone R
Cyclohexasiloxane S
A2 Bismuth oxychloride 2.00
2cSt dimethicone 6.00
A3 Microspheres (methyl vinylidene/acrylonitrile/methacrylate chloride copolymer)
expanded by isobutane sold under the reference Expancel 551 DE 40 D42 by the 0.20
Akzo Nobel company
A4 Synthetic mica (fluorphlogopite) 1 .44
Cyclohexasiloxane 6.00
Yellow iron oxide coated with aluminum stearoyl glutamate 2.03
A5 Red iron oxide coated with aluminum stearoyl glutamate 0.58
Black iron oxide coated with aluminum stearoyl glutamate 0.17
Titanium dioxide coated with aluminum stearoyl glutamate 10.22
B Deionized water T
Butylene glycol u
1 ,3-Propanediol V
Phenoxyethanol w
Magnesium sulfate X
Sorbitol Y Sodium salt of 3- hydroxy-2-pentyl-cyclopentane acetic acid in a water/dipropylene
6.20 glycol mixture (32/48/20)
c Ethanol Z
D Perfume 0.05
TOTAL 100%
Procedure
The constituents of phase A1 are weighed into the main beaker, then homogenized using a Moritz mixer at a speed of 1200-1400 rpm at room temperature.
Phase A2 followed by phase A3 are then added, which have been previously prepared by mashing by hand, and, finally, phase A4 is added, while agitating for 15 minutes until homogenization.
Phase A5 is prepared separately by grinding three times, in a three-roll mill, the mixture of pigments and cyclohexasiloxane.
Phase A5 is added to the main beaker while progressively increasing the agitation speed of the Moritz mixer to 1400-1500 rpm, then the agitation is continued for 20 minutes.
The constituents of phase B are weighed separately, with the exception of the jasmonic acid derivative and the phenoxyethanol. It is homogenized using a magnetic mixer at a temperature of around 30-35°C, then the jasmonic acid derivative and the phenoxyethanol are incorporated.
Then the emulsification is produced by pouring phase B into the main beaker and progressively increasing the agitation speed to 4000 rpm, and then maintaining it at that speed for 10 minutes.
The agitation speed is then slightly reduced and the ethanol and the perfume are added. The mixture is agitated again for two minutes and the product is packaged in a glass jar. Stability results
Figure imgf000029_0001
These results show that the composition is stable when the aqueous ph percentage is greater than 40%.
B - Influence of the aqueous phase content on cosmetic properties
The comparison of the fluid foundation examples 1 and 8 shows that, when the aqueous phase content is greater than 55%, the cosmetic properties of the foundation are not as good.
Ex. 1
Ex. 8 (Comparative) (Invention)
mass % mass %
Cetyl PEG/PPG-10/1 dimethicone sold under the reference ABIL EM 90 by the
A1 3.00 3.00
Goldschmidt company
Polyglycerol isostearate 4 sold under the reference ISOLAN Gl 34 by the Goldschmidt
1.00 1.00 company
Dimethicone + PEG/PPG/-18/18 dimethicone sold under the reference X-22-6711 D by
1.07 1.07 the Shin Etsu company
Ethyl hexyl methoxycinnamate 7.50 7.50
Phenyltrimethicone sold under the reference DC 556 by the Dow Corning company 8.00 - 2cSt dimethicone 2.00 -
A2 Bismuth oxychloride 2.00 2.00
2cSt dimethicone 6.00 6.00
A3 Microspheres (methyl vinylidene/acrylonitrile/methacrylate chloride copolymer)
expanded by isobutane sold under the reference Expancel 551 DE 40 D42 by the 0.20 0.20
Akzo Nobel company
A4 Synthetic mica (fluorphlogopite) 1.44 1.44
Cyclohexasiloxane 6.00 6.00
Yellow iron oxide coated with aluminum stearoyl glutamate 2.03 2.03
A5 Red iron oxide coated with aluminum stearoyl glutamate 0.58 0.58
Black iron oxide coated with aluminum stearoyl glutamate 0.17 0.17
Titanium dioxide coated with aluminum stearoyl glutamate 10.22 10.22
Deionized water 25.64 28.67
Butylene glycol 5.00 7.06
1 ,3- Propanediol 5.00 7.06
B Phenoxyethanol 0.70 0.99
Magnesium sulfate 0.70 0.99
Sorbitol 0.50 0.71
Sodium salt of 3- hydroxy-2-pentyl-cyclopentane acetic acid in a water/dipropylene
6.20 6.20 glycol mixture (32/48/20)
C Ethanol 5.00 7.06
D Perfume 0.05 0.05
TOTAL 100% 100%
Total aqueous phase 46.76 % 56,76 %
Procedure of example 8
The constituents of phase A1 are weighed into the main beaker, then homogenized with a Moritz mixer at a speed of 1500 rpm at room temperature.
Phase A2 followed by phase A3 are then added, which have been previously prepared by mashing by hand, and, finally, phase A4 is added, while agitating for 15 minutes until homogenization.
Phase A5 is prepared separately by grinding three times, in a three-roll mill, the mixture of pigments and cyclohexasiloxane.
Phase A5 is added to the main beaker while progressively increasing the agitation speed of the Moritz mixer to 1600 rpm, then the agitation is continued for 20 minutes.
The constituents of phase B are weighed separately, with the exception of the jasmonic acid derivative and the phenoxyethanol. It is homogenized using a magnetic mixer at a temperature of around 30-35°C, then the jasmonic acid derivative and the phenoxyethanol are incorporated. Then the emulsification is produced by pouring phase B into the main beaker and progressively increasing the agitation speed to 4000 rpm, and then maintaining it at that speed for 10 minutes.
The agitation speed is then slightly reduced and the ethanol and the perfume are added. The mixture is agitated again for two minutes and the product is packaged in a glass jar.
Sensory evaluation
We asked a panel of 4 women, between the ages of 20 to 50 years, to apply the two foundations, one on each half of their face.
This evaluation showed found that the foundation of example 1 (invention) is easier to apply, smoother and more comfortable. The foundation of example 8 (comparative) gives a more powdered makeup result, which has a tendency to increase the visibility of raised imperfections (pores, wrinkles). After application, it leads to a harder and stickier film.
In the end, the women on the panel prefer the foundation of example 1 (invention).

Claims

1. Composition including a physiologically acceptable medium containing:
- at least one coloring agent; and
- at least one jasmonic acid derivative compound with the following formula (I):
Figure imgf000032_0001
in which:
. Ri represents a radical COOR3, with R3 designating a hydrogen atom or a C1 -C4 alkyl radical, optionally substituted by one or more hydroxyl groups; . R2 represents a hydrocarbon radical, saturated or unsaturated, and linear with 1 to 18 carbon atoms, or branched or cyclic with 3 to 18 carbon atoms; as well as their optical isomers and corresponding salts;
wherein said composition is in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fat phase,
wherein said aqueous phase represents 40% to 55%, in particular 42% to 52%, and preferably 44% to 50%, by weight with respect to the total weight of said composition.
2. Composition according to claim 1 , which, in formula (I), Ri is chosen from the group consisting of: -COOH, -COOCH3, -COO-CH2-CH3, -COO-CH2- CH(OH)-CH2OH, -COOCH2-CH2-CH2OH et -COOCH2-CH(OH)-CH3.
3. Composition according to claim 1 or 2, which, in formula (I), R2 is a hydrocarbon radical, linear, saturated or unsaturated, having 2 to 7 carbon atoms.
4. Composition according to any one of claims 1 to 3, in which, in formula
Figure imgf000032_0002
5. Composition according to any one of claims 1 to 4, in which, in formula (I), R2 is chosen from the group consisting of pentyl, pentenyl, hexyl and heptyl radicals.
6. Composition according to any one of claims 1 to 5, in which the compound of formula (I) is 3-hydroxy-2-pentyl-cyclopentane acetic acid or 3- hydroxy-2-pentyl-cyclopentane acetic acid sodium salt.
7. Composition according to any one of claims 1 to 6, in which the compound of formula (I) is brought to the aqueous phase and in a content ranging from 0.001 % to 10%, in particular from 0.1 % to 8%, and preferably from 0.5% to 5% by weight with respect to the total weight of said composition.
8. Composition according to any one of claims 1 to 7, in which the coloring agent is chosen from the group consisting of pigments, dyes and interferential particles.
9. Composition according to claim 8, in which the coloring agent is chosen from the pigments.
10. Composition according to any one of claims 1 to 9, in which the aqueous phase includes water, as the case may be, in a mixture with water-soluble additives and/or solvents.
11. Composition according to any one of claims 1 to 10, in which the aqueous phase includes des additives chosen from the group consisting of water- soluble active ingredients, preservatives, salts, gelling agents, fillers, water-soluble or water-dispersible polymers, and mixtures thereof.
12. Composition according to any one of claims 1 to 1 1 , including at least one UV filter, in which said UV filter is preferably chosen from the cinnamates, and is preferably ethylhexyl methoxycinnamate.
13. Composition according to any one of claims 1 to 12, in the form of a fluid foundation.
14. Non therapeutic cosmetic use of at least one coloring agent and at least one jasmonic acid derivative compound with the following formula (I):
Figure imgf000034_0001
in which:
. Ri represents a radical COOR3, with R3 designating a hydrogen atom or a C1 -C4 alkyl radical, optionally substituted by one or more hydroxyl groups; . R2 represents a hydrocarbon radical, saturated or unsaturated, and linear with 1 to 18 carbon atoms, or branched or cyclic with 3 to 18 carbon atoms; as well as their optical isomers and corresponding salts;
in a composition being in the form of a water-in-oil emulsion including an aqueous phase dispersed in a fat phase,
wherein said aqueous phase represents 40% to 55% by weight with respect to the total weight of said composition,
for preventing skin aging.
15. Non-therapeutic skincare and/or makeup method including a step of applying, on the skin, at least one layer of a composition according to any one of claims 1 to 13.
PCT/EP2012/063284 2011-07-08 2012-07-06 Cosmetic compositions in the form of water-in-oil emulsions including a jasmonic acid derivative WO2013007647A1 (en)

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KR1020147003160A KR102002099B1 (en) 2011-07-08 2012-07-06 Cosmetic compositions in the form of water-in-oil emulsions including a jasmonic acid derivative
CN201280043183.4A CN103796627B (en) 2011-07-08 2012-07-06 Comprise the cosmetic composition of the water-in-oil emulsion form of jasmonic acid derivative
RU2014104514/15A RU2587320C2 (en) 2011-07-08 2012-07-06 Cosmetic composition in form of water-in-oil emulsions containing jasmonic acid derivative
BR112014000318-1A BR112014000318B1 (en) 2011-07-08 2012-07-06 COMPOSITION, NON THERAPEUTIC COSMETIC USE AND NON THERAPEUTIC SKIN AND / OR MAKEUP CARE METHOD

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FR1156228A FR2977486B1 (en) 2011-07-08 2011-07-08 COSMETIC COMPOSITIONS IN THE FORM OF WATER-IN-OIL EMULSIONS COMPRISING A JASMONIC ACID DERIVATIVE
FR1156228 2011-07-08
US201161510225P 2011-07-21 2011-07-21
US61/510225 2011-07-21

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US9034833B1 (en) 2013-12-20 2015-05-19 L'oreal Anti-aging composition containing high levels of a jasmonic acid derivative
US9237998B2 (en) 2013-12-20 2016-01-19 L'oreal Carrier system for water-soluble active ingredients
US9539198B2 (en) 2013-12-20 2017-01-10 L'oreal Photoprotection composition containing high levels of water-soluble UV filters
US9545373B2 (en) 2013-12-20 2017-01-17 L'oreal Translucent cosmetic composition in the form of a water-in-oil emulsion
US9943477B2 (en) 2013-12-20 2018-04-17 L'oreal Emulsion compositions containing a novel preservative system
WO2019232096A1 (en) * 2018-05-29 2019-12-05 Rr Health, Llc Compositions for topical treatment
US20190374446A1 (en) * 2016-12-21 2019-12-12 L'oreal Water-in-oil emulsion comprising a particular emulsifying system, a lipophilic clay, and an organopolysiloxane elastomer powder coated with a silicone resin
RU2767935C2 (en) * 2016-01-08 2022-03-22 Эвергрин Лэнд Лимитед Aqueous composition containing lipophilic composition
US20220273552A1 (en) * 2021-02-28 2022-09-01 L'oreal Hair cosmetic compositions

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FR3015235B1 (en) * 2013-12-19 2016-01-15 Oreal BIPHASE COMPOSITION COMPRISING A CUCURBIC ACID DERIVATIVE
FR3015236B1 (en) * 2013-12-23 2016-01-22 Oreal OILY COMPOSITION COMPRISING A CUCURBIC ACID COMPOUND AND A DIVALENT SALT

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EP1333021A2 (en) 2002-02-04 2003-08-06 L'oreal Compositions containing derivatives of jasmonic acid and their use for stimulating skin peeling
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US9034833B1 (en) 2013-12-20 2015-05-19 L'oreal Anti-aging composition containing high levels of a jasmonic acid derivative
US9237998B2 (en) 2013-12-20 2016-01-19 L'oreal Carrier system for water-soluble active ingredients
US9539198B2 (en) 2013-12-20 2017-01-10 L'oreal Photoprotection composition containing high levels of water-soluble UV filters
US9545373B2 (en) 2013-12-20 2017-01-17 L'oreal Translucent cosmetic composition in the form of a water-in-oil emulsion
US9943477B2 (en) 2013-12-20 2018-04-17 L'oreal Emulsion compositions containing a novel preservative system
RU2767935C2 (en) * 2016-01-08 2022-03-22 Эвергрин Лэнд Лимитед Aqueous composition containing lipophilic composition
US20190374446A1 (en) * 2016-12-21 2019-12-12 L'oreal Water-in-oil emulsion comprising a particular emulsifying system, a lipophilic clay, and an organopolysiloxane elastomer powder coated with a silicone resin
JP2020502187A (en) * 2016-12-21 2020-01-23 ロレアル Water-in-oil emulsion containing organopolysiloxane elastomer powder coated with specific emulsification system, lipophilic clay and silicone resin
WO2019232096A1 (en) * 2018-05-29 2019-12-05 Rr Health, Llc Compositions for topical treatment
US20220273552A1 (en) * 2021-02-28 2022-09-01 L'oreal Hair cosmetic compositions

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FR2977486B1 (en) 2013-08-30
CN103796627B (en) 2016-03-30
CN103796627A (en) 2014-05-14
BR112014000318B1 (en) 2019-02-12
KR20140047698A (en) 2014-04-22
FR2977486A1 (en) 2013-01-11
KR102002099B1 (en) 2019-07-19
BR112014000318A2 (en) 2018-06-19
RU2587320C2 (en) 2016-06-20
RU2014104514A (en) 2015-08-20

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