EP2501359A1 - A cosmetic or dermatological composition with low stickiness, containing a lipophilic active ingredient - Google Patents

A cosmetic or dermatological composition with low stickiness, containing a lipophilic active ingredient

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Publication number
EP2501359A1
EP2501359A1 EP09796101A EP09796101A EP2501359A1 EP 2501359 A1 EP2501359 A1 EP 2501359A1 EP 09796101 A EP09796101 A EP 09796101A EP 09796101 A EP09796101 A EP 09796101A EP 2501359 A1 EP2501359 A1 EP 2501359A1
Authority
EP
European Patent Office
Prior art keywords
composition
weight
derivatives
volatile
wax particles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09796101A
Other languages
German (de)
French (fr)
Inventor
Kazuhiko Maruyama
Mika Inoue
Kazushige Hara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP2501359A1 publication Critical patent/EP2501359A1/en
Withdrawn legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K8/0241Containing particulates characterized by their shape and/or structure
    • 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
    • A61K8/31Hydrocarbons
    • 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
    • A61K8/34Alcohols
    • 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
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • 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
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/34Free of silicones
    • 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
    • A61K2800/41Particular ingredients further characterized by their size
    • A61K2800/412Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • A61K2800/60Particulates further characterized by their structure or composition
    • A61K2800/65Characterized by the composition of the particulate/core
    • A61K2800/652The particulate/core comprising organic material

Definitions

  • the present invention relates to a cosmetic or dermatological composition in the form of emulsion containing an aqueous phase and an oily phase, which comprises one or more of lipophilic cosmetic or dermatological active ingredients among others, wherein sticky feeling which may be caused by the active ingredient can be reduced and a good feeling on use of the composition can be obtained.
  • the present invention also relates to a method for reducing sticky feeling on keratinous material such as the skin and/or the hair, which may be caused by a lipophilic cosmetic or dermatological active ingredient applied on the keratinous material.
  • ingredients used in a cosmetic or dermatological composition are liposoluble.
  • a liposoluble active ingredient is added to a cosmetic or dermatological composition, a sticky feeling due to the active ingredient may often be caused after applying the composition on the skin or the hair and feeling on use of the composition will be deteriorated.
  • JP-A-2008-24.7897 discloses a UV protecting cosmetic composition comprising (a) 2-ethylhexyl 2-ethylhexanoate and/or isononyl 2-ethylhexanoate, (b) a UV-absorbing agent , and (c) a UV-scattering agent, and (d) a silicone oil in the form of an O/W emulsion or a W/O emulsion, which can provide a good feel on use with reduced sticky feeling.
  • JP-A-2007-131612 discloses a UV-protecting cosmetic composition comprising a lipophilic UV filter and the use of an
  • alkylaryl-1, 3-propanedione-silicone derivative to improve the sticky feeling caused by the UV filter.
  • a combination of one or more of lipophilic cosmetic or dermatological active ingredients, a non-alcoholic volatile solvent which is different from a cyclomethicone, a volatile alcohol, wax particles, and a non-volatile compound having at least one hydrophilic functional group, in a cosmetic or dermatological composition in the form of emulsion containing an aqueous phase and an oily phase can reduce the sticky feeling which may be caused by the lipophilic active ingredients and improve the feeling on use of the composition
  • the use of the above-mentioned combination of ingredients in a cosmetic or dermatological composition makes it possible to provide the resulting cosmetic or dermatological composition with a non-fatty and non-sticky feeling, often together with good spreading of the active ingredient, a non-glossy effect and a smooth feeling.
  • the term "sticky feeling" is used herein to indicate a property of a cosmetic or dermatological composition which gives sticky or tacky feeling to the skin and/or the hair, when the composition is applied.
  • the present invention features a cosmetic or dermatological composition in the form of an emulsion, containing an aqueous phase and an oily phase, wherein the composition comprises:
  • the composition of the present invention comprises a volatile cyclomethicone in an amount less than 1% by weight relative to the total amount of the composition, and more preferably comprises no volatile cyclomethicones .
  • the composition of the present invention comprises one or more lipophilic cosmetic or dermatological active ingredients.
  • the "cosmetic or dermatological active ingredient” is a compound or a composition which can provide cosmetically or dermatologically beneficial effects when the composition containing the same is applied, in particular, to keratinous material such as the skin or the hair.
  • the term "lipophilic" of lipophilic active ingredient means herein that the active ingredient is able to be totally dissolved in the oily phase of the present composition or able to be dispersed in a colloidal form, such as in a miscellar form, in the oily phase of the composition.
  • lipophilic cosmetic or dermatological active ingredients are as follows, but not limited to:
  • Aminophenol and Aminophenol derivatives which is herein also referred to "aminophenols", ' salicylic acid derivatives such as described below; 2-amino-4-alkylaminopyrimidine-3-oxide
  • aminophenol derivatives mentioned above are more particularly the derivatives of formula (1) below, but not limited to these particular examples:
  • R' is a radical chosen from the group made up of the following radicals (a) , (b) and (c) :
  • R 1 represents a hydrogen atom or an optionally hydroxylated, saturated or unsaturated, linear or branched Ci to C 6 alkyl radical
  • R 2 represents a hydrogen atom or a radical chosen from saturated or unsaturated, linear, cyclic or branched Ci to C 30 , in particular Ci2 to C30 alkyl radicals, which are optionally hydroxylated
  • R 3 represents a radical chosen from saturated or unsaturated, linear, cyclic or branched, including fused polycyclic, Ci to C30, in particular C i2 to C 30 alkyl radicals, which are optionally hydroxylated.
  • R 2 or R 3 radicals containing from 1 to 30 carbon atoms mention may advantageously be made of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, octyl, nonyl, 2-ethylhexyl, dodecyl, hexadecyl, behenyl, octadecyl and 2-butyloctyl radicals.
  • These radicals preferably contain from 1 to 12 carbon atoms .
  • the alkyl radical generally contains from 1 to 6 carbon atoms.
  • a .lower alkyl radical mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl and hexyl radicals
  • a radical having one or more ethylenic ⁇ unsaturations such as more particularly an allyl radical, is preferred.
  • the alkyl radical is cyclic, mention may in particular be made of a cyclohexyl, cholesteryl or tert-butylcyclohexyl radical.
  • the radical preferably contains from 1 to 6 carbon atoms and from 1 to 5 hydroxyl groups.
  • a radical preferably containing 1 or 3 carbon atoms, in particular a hydroxymethyl , 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl radical is preferred.
  • polyhydroxyalkyl radicals a radical containing from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as a
  • alkoxylated radicals are alkyl radicals, as in particular described above, preceded by an oxygen atom.
  • aminophenol derivatives used in the present invention are those for which at least one and preferably all of the conditions below are met:
  • - the -OH function on the phenyl radical is in the ortho-position or, advantageously, in the para-position
  • R' is chosen from a radical of formula (a) or (b) .
  • linear or branched alkyl radicals R 1 mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl or hexyl radicals.
  • the aminophenol derivative preferably used in the composition of the present invention is a para-aminophenol derivative; even more preferably, it is N-ethoxycarbonyl-4-para-aminophenol of formula (la):
  • N-cholesteryloxycarbonyl-4-para-aminophenol of formula (lb) or else N-cholesteryloxycarbonyl-4-para-aminophenol of formula (lb) :
  • These derivatives may have a more or less long hydrocarbon chain, preferably alkoxycarbonyl chain, attached to the nitrogen atom.
  • salicylic acid derivatives which can be used as the lipophilic cosmetic or dermatological active ingredients are the derivative of formula (2) :
  • R"i represents a hydroxyl radical or an ester of formula
  • R" 4 is a saturated or unsaturated aliphatic radical containing from 1 to 26 carbon atoms, and preferably from 1 to 18 carbon atoms, or an amine or thiol function optionally substituted with an alkyl radical containing from 1 to 18 carbon atoms, and preferably from 1 to 12 carbon atoms,
  • R" 2 and R"3, independently of one another, are in the 3-, 4-, 5- or 6-position on the benzene ring and represent, independently of one another, a hydrogen atom or a radical:
  • n and m independently of one another, are each an integer equal to 0 or 1, provided that R" 2 and R" 3 are not simultaneously hydrogen atoms,
  • R"5 represents a hydrogen, a linear, branched or cyclized, saturated aliphatic radical containing from 1 to 18 carbon atoms, or an unsaturated radical containing from 3 to 18 carbon atoms, bearing one to nine conjugated or unconjugated double bonds, it being possible for the radicals to be substituted with at least one substituent chosen from halogen atoms (fluorine, chlorine, bromine or iodine), and the following radicals: trifluoromethyl, hydroxyl in free form or esterified with an acid containing from 1 to 6 carbon atoms, or carboxyl in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms, or an aromatic radical containing from 6 to 10 carbon atoms.
  • halogen atoms fluorine, chlorine, bromine or iodine
  • the salicylic acid derivative is such that R" 5 represents a saturated aliphatic radical containing from 3 to 15 carbon atoms.
  • the salicylic acid derivative is such that R"i represents a hydroxyl radical.
  • the salicylic acid derivative is such that R" 5 is in the 5-position on the benzene ring and R" 2 represents a hydrogen atom.
  • the salicylic acid derivatives are derivatives of 5-n-octanoylsalicylic acid, 5-n-decanoylsalicylic acid, 5-n-dodecanoylsalicylic acid,
  • 5-propanoylsalicylic acid 5-n-hexadecanoylsalicylic acid, 5-n-oleoylsalicylic acid, 5-benzoylsalicylic acid, monovalent and divalent salts thereof, and mixtures thereof.
  • salicylic acid derivatives in topical compositions, for example, as a keratolytic agent for treating acne or as an anti-ageing agent; the patent applications published as FR-A-2 581 542 and EP-A-378 936 describe such derivatives.
  • Salicylic acid derivatives are highly advantageous in particular for preventing or repairing the principal manifestations of skin ageing, namely fine lines and wrinkles, disruption of the "grain" of the skin, modification of the complexion of the skin and loss of firmness and of tonicity of the skin.
  • the use of these derivatives poses a problem insofar as, when they are introduced without modification into topical compositions, they are not solubilized and remain in the crystalline state, rendering the use of the composition containing them ineffective for the treatment of the skin.
  • a lipophilic UV filter can preferably be used as a lipophilic cosmetic or dermatological active ingredient in the composition of the present invention.
  • anthranilic acid derivatives beta, beta-diphenylacrylate derivatives, benzylidene camphor derivatives, phenylbenzimidazole derivatives, benzotriazole derivatives, triazines, bis-resorcinyl triazines, imidazoline derivatives, benzalmalonates ,
  • UV filters 4.4-diarylbutadiene derivatives, benzoxazole derivatives, merocyanines , dephenylbutadiene malonates or malononitriles , chalcones, and a combination of two or more of the aforementioned compounds.
  • UV filters are known in the art. The more detailed description about UV filters is presented below.
  • the UV filter used for the present invention may be selected from the group consisting of lipophilic UVA filters, lipophilic UVB filters, lipophilic UV filters which can act as both UVA and UVB filters, and a combination thereof.
  • UVA filters which absorb UV light in the range of wavelength from 320 to 400 nm, mention may be made of the following compounds, but hot limited to:
  • dibenzoylmethanes such as: 2-methyldibenzoylmethane
  • PARSOL 1789, UVINUL A+, or a combination thereof is particularly preferred to be used as a lipophilic UVA filter (s) in the .composition of the present invention.
  • UVB filters which absorb UV light in the range of wavelength from 280 to 320 nm, mention may be made of, but not limited to:
  • Para-aminobenzoic acid derivatives such as para-aminobenzoates (PABA), for example, Ethyl PABA (para-aminobenzoate) , Ethyl Dihydroxypropyl PABA, Ethylhexyl Dimethyl PABA, marketed under the name "ESCALOL 597" by ISP;
  • PABA para-aminobenzoates
  • Ethyl PABA para-aminobenzoate
  • Ethyl Dihydroxypropyl PABA Ethylhexyl Dimethyl PABA
  • Dipropyleneglycol Salicylate marketed under the name “DIPSAL” by SCHER, and TEA Salicylate, marketed “ under the name “NEO HELIOPAN TS” by Symrise;
  • Cinnamic acid derivatives such as Ethylhexyl Methoxycinnamate, marketed under the name "PARSOL CX” by DSM NUTRITIONAL PRODUCTS, Isopropyl ethoxy cinnamate, Isoamyl Methoxy cinnamate, marketed under the name "NEO HELIOPAN E 1000" by Symrise, Dii ' sopropyl ethylcinnamate, Cinoxate, and Glyceryl Ethylhexanoate
  • Octocrylene marketed under the name "UVINUL N539” by BASF
  • Etocrylene marketed under the name "UNIVUL N35” by BASF
  • Benzylidene camphor derivatives such as 3-Benzylidene camphor, marketed under the name “MEXORYL SD” from CHIMEX, ethylbenzylidene camphor, marketed under the name “EUSOLEX 6300” by MERCK, and Polyacrylamidomethyl Benzylidene Camphor, marketed under the name “MEXORYL SW” by CHIMEX, and Terephthalylidene Dicamphor Sulfonic Acid, marketed under the name "Mexoryl SX” by Chimex;
  • Triazines such as Ethylhexyl triazone, marketed under the name “UVINUL T150” by BASF, Diethylhexyl Butamido Triazone, marketed under the name “UVASORB HEB” by SIGMA 2V, 2 , 4 , 6-tris (dineopentyl 4 ' -aminobenzalmalonate) -s-triazine, 2,4, 6-tris (diisobutyl
  • Imidazoline derivatives such as Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate
  • Benzalmalonates such as Polyorganosiloxane containing a benzalmalonate moiety, for example, Polysilicone-15, marketed under the name "Parsol SLX" by DSM NUTRITIONAL PRODUCTS,
  • one or more lipophilic UVB filters selected from the group consisting of Ethylhexyl triazone, Diethylhexyl Butamido Triazone, Octocrylene, Homosalate, Ethylhexyl Salicylate, and Ethylhexyl Methoxycinnamate as a lipophilic cosmetic or dermatological ingredient in the composition.
  • UVA and UVB filters Lipophilic compounds which act as UVA and UVB filters can also be used in the composition with or without another UV filter.
  • UVA and UVB filters are non-limited examples of UVA and UVB filters:
  • Benzophenone derivatives such as Benzophenone-1 marketed under the name "UVINUL 400" by BASF, Benzophenone-2 marketed under the name “UNIVUL 500” by BASF, Benzophenone-3 or Oxybenzone marketed under the name “UVINUL M40” by BASF, Benzophenone-6 marketed under the name “Helisorb 11” by Norquay, Benzophenone-8 marketed under the name "Spectra-Sorb UV-24” by American Cyanamid, Benzophenone-10 , Benzophenone-11 , and Benzophenone-12 ;
  • Drometrizole Trisiloxane marketed under the name "Silatrizole” by Rhodia Chimie
  • Methoxyphenyl Triazine may be preferably used as a UVA and UVB filter in the composition of the present invention.
  • UV filters can be used alone or as a combination of two or more UV filters.
  • a combination-of a UVA filter and a UVB filter can be preferably employed.
  • the total amount of lipophilic cosmetic or dermatological active ingredients contained in the composition of the present invention is not limited to a particular amount but is preferably at least 5% by weight, in particular in the range from 5% to 30% by weight, and more preferably in the range from 10% to 20% by weight relative to the total amount of the composition of the present invention. ⁇ By using one or more of intended lipophilic cosmetic or
  • a non-alcoholic volatile solvent refers to a
  • the non-alcoholic volatile solvent is in the form of liquid at room temperature, and has a vapor pressure more than 0(zero),
  • room temperature means 25 °C herein.
  • non-alcoholic volatile solvent which is different from a cyclomethicone is used in the present invention. This does not mean to exclude the use of cyclomethicone together with the
  • non-alcoholic volatile solvent which is different from a cyclomethicone
  • cyclomethicone such as a linear silicone oil, for instance, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane,
  • decamethyltetrasiloxane (L4 ) KF96A from Shin-Etsu Chemical
  • polydimethylsiloxanes such as those marketed under the name "DC 200 (1.5 cSt)", “DC 200 (5 cSt)”, and “DC 200 ( 3 cSt) " by Dow Corning Corporation
  • R represents a C2-C4 alkyl group wherein one or more hydrogen atoms may be substituted by a halogen atom(s) selected from a fluorine atom and a chlorine atom.
  • R represents a C2-C4 alkyl group wherein one or more hydrogen atoms may be substituted by a halogen atom(s) selected from a fluorine atom and a chlorine atom.
  • Examples of the compounds of formula I are 3-butyl-l, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane, 3-propyl-l, 1,1,3,5,5, 5-heptamethyltrisiloxane, and
  • Fluorinated volatile oils for example, perfluoropolyethers , perfluoroalkanes such as perfluorodecaline and
  • perfluoroadamantanes perfluoroalkylphosphates (monoesters, diesters and triesters) ; and fluorinated esters oils.
  • the amount of non-alcoholic volatile solvent which is different from a cyclomethicone and present in the composition of the present invention is typically in the range from 5 to 20% by weight, more preferably 7 to 15% by weight relative to the total amount of the composition, but not limited thereto.
  • the volatile alcohol used in the composition of the present invention is preferably selected from monoalcohols , particularly alkylmonoalcohols, in particular, C 1 -C5 lower alkylmonoalcohols, that is, alkylmonoalcohols having 1 to 5 carbon atoms such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol . Ethanol and isopropanol are preferred. Ethanol is particularly preferred.
  • Viscosity of the volatile alcohol preferably- is in the range from 0.3 to 3 mPa.s at 20 °C, as measured using a HAAKE Rheostress 600 machine with a spindle having a diameter of 60 mm, an angle of 2° and a sand-blasted coating at a shear rate of 200 s "1 at 20°C.
  • the amount of the volatile alcohol present in the composition is not limited to a particular amount, but preferably is in the range from 0.5 to 20% by weight, more preferably from 1 to 10% by weight relative to the total amount of the composition of the present invention .
  • Wax particles are not limited to a particular amount, but preferably is in the range from 0.5 to 20% by weight, more preferably from 1 to 10% by weight relative to the total amount of the composition of the present invention .
  • the wax particles also referred to as "microwaxes" herein, used for the composition of the present invention are a wax which is in the form of small particles and typically present in the oily phase of the composition.
  • the mean size by volume of the wax particles is preferably in the range from 0.5 to 30 micrometers, in particular from 1 to 20 micrometers, and more particularly from 5 to 10 micrometers, which is measured according to AST D 4464.
  • microwaxes having such a mean particle size in combination with other ingredients b) to e) in the composition of the present invention, the sticky feeling which may be caused by a lipophilic cosmetic or dermatological active ingredient can be effectively reduced and a good feeling on use of the composition can be obtained often together with improved extendibility of the composition and smooth feeling on the skin or the hair.
  • the term "wax” means a compound that is solid or substantially solid at 25 °C and whose melting point is generally greater than 35 ° C.
  • the wax which constitutes the wax particles is not limited to a particular wax and may be any types of waxes, such as synthetic waxes and waxes of natural origin.
  • one or more selected from the group consisting of natural wax particles, synthetic wax particles, and a combination thereof can be used in the composition of the present invention.
  • one or more wax particles selected from the group consisting of carnauba wax particles, synthetic wax particles, polyethylene wax particles, and a combination thereof can be used in the composition of the present invention.
  • Micro Powders such as those marketed under the names "Micropoly 200 ® “, “Micropoly 220 ® “, “Micropoly 220L ® “, and “Micropoly 250S ® “ ' by Micro Powders, which have a mean particle size of 6.0 to 8.0, 7.0 to 9.0, 8.0 to 10.0, or 2.0 to 4.0, respectively.
  • the amount of wax particles present in the composition of the present invention is not limited to a specific amount, but preferably, is in the range from 0.5 to 20% by weight, more preferably from 1 to 10% by weight relative to the total weight of the composition.
  • Non-volatile compounds used for the present invention typically have a vapor pressure of less than 10 ⁇ 3 mmHg (0.13 Pa).
  • the non-volatile compounds preferably have an evaporation speed such that the evaporated amount after 30 minutes is less than 0.07 mg/cm 2 .
  • hydrophilic functional group means a functional group which can form a hydrogen bond with a water molecule .
  • hydrophilic functional groups include a hydroxyl or alcohol group, an amino group which include a primary, a secondary and a tertiary amino group, and a carboxyl group.
  • Non-volatile compounds having two or more hydroxyl groups are preferred and those having 2 to 12 carbon atoms are particularly preferred to be used as ingredient e) .
  • non-volatile compounds having at least one hydrophilic functional group mention may be made of glycerin, propylene glycol, dipropylene glycol, tripropylene glycol, diglycerin, ethylene glycol, triethylene glycol, isoprene glycol, diglycerin, pentylene glycol, hexylene glycol, sorbitol, mannitol, D-glucose, sucrose, D-fructose, xylitol, " lactose, maltose, maltitol, trehalose, hydroxyethyl urea, and a combination of two or more of the aforementioned compounds.
  • the amount of the non-volatile compound having at least one hydrophilic functional group present in the composition of the present invention is not limited to a particular amount, but preferably is in the range 1 from 0.5 to 20% by weight, and more preferably from 1 to 10% by weight relative to the total weight of the composition. f ) Other ingredients
  • a cosmetic or dermatological composition of the present invention in the form of an emulsion containing an aqueous phase and an oily phase may optionally contain one or more additional ingredients which are commonly used in a cosmetic or dermatological composition in addition to ingredients a) to e) .
  • fillers ; polymers; propellants; acidifying or basifying agents; pigments; dyes; inorganic photoprotective agents and any other ingredients commonly used in a cosmetic or dermatological composition .
  • the fatty substances may be an oil.
  • oil means a compound that is lipophilic liquid at room temperature. Oils that may be mentioned include mineral oils (paraffin); vegetable oils (sweet almond oil, macadamia oil, grapeseed oil or jojoba oil) ; synthetic oils, for instance perhydrosqualene, fatty alcohols, fatty acids or fatty esters (for instance the C12-C15 alkyl benzoate marketed under the name "Finsolv TN" of "Witconol TN” by Witco, octyl palmitate, isonohyl isononanoate, isopropyl lanolate and triglycerides, including capric/caprylic acid triglycerides), dialkyl carbonate such as dicaprylyl carbonate, oxyethylenated or oxypropylenated fatty esters and ethers; silicone oils
  • Oil containing at least one amide structure such as those disclosed in US7,357,920, the disclosure of which is incorporated herein by reference, can also be used.
  • one or more thickeners selected from the group consisting of hydrophilic thickeners and lipophilic thickners may be added to the composition of the present invention in order to Ddify the rheological properties the
  • Hydrophilic thickeners that may be mentioned include carboxyvinyl polymers such as the Carbopol products (carbomers) and the Pemulen products (acrylate/Cio-3o-alkylacrylate copolymer) ;
  • polyacrylamides for instance the crosslinked copolymers marketed under the name "Sepigel 305" (CTFA name: polyacrylamide/Ci 3 -i 4 isoparaffin/Laureth 7) or "Simulgel 600" (CTFA name:
  • 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers which are optionally crosslinked and/or neutralized, for instance the poly (2-acrylamido-2-methylpropanesulfonic acid) marketed by Hoechst under the name "Hostacerin AMPS” (CTFA name: ammonium polyacryldimethyltauramide) ; cellulose-based derivatives such as hydroxyethylcellulose; polysaccharides and especially gums such as xanthan gum; and mixtures thereof.
  • CTFA name ammonium polyacryldimethyltauramide
  • Lipophilic thickeners that may be mentioned include modified clays such as hectorite and its derivatives, for instance the products marketed under the name "Bentone”.
  • a hydrophilic cosmetic or dermatological active ingredient may optionally be used in addition to ingredients a) to e) mentioned above.
  • the term "hydrophilic" active ingredient means herein that the active ingredient ' is able to be dissolved in the aqueous phase of the present composition or able to be dispersed in a colloidal form, such as in a miscellar form, in the aqueous phase of the present composition.
  • Hydrophilic cosmetic or dermatological active ingredients which are known in the art, such as ascorbic acid and derivative thereof, may be used.
  • an inorganic photoprotective agent may be used together with the lipophilic cosmetic or dermatological active ingredient.
  • An inorganic photoprotective agent used for the present invention may be selected from among pigments and even more preferably nanopigments (mean size of the primary particles: generally from 5 run to 100 nm and preferably from 10 nm to 50 nm) of treated or untreated metal oxides such as, for example, nanopigments of titanium oxide (amorphous or crystallized in rutile and/or anatase form) , of iron oxide, of zinc oxide, of zirconium oxide or of cerium oxide.
  • the treated nanopigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53-64, such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal (titanium or aluminum) alkoxides, polyethylene, silicones, proteins (collagen or elastin) , alkanolamines, silicon oxides, metal oxides, sodium
  • hexametaphosphate alumina or glycerol.
  • composition at least one agent for artificially tanning and/or browning the skin.
  • the cosmetic or dermatological composition of the present invention is in the form of an emulsion containing an aqueous phase and an oily phase.
  • Each phase comprises a physiologically acceptable medium.
  • the aqueous phase comprises water.
  • the physiologically acceptable medium of the oily phase is commonly selected from fatty substances such as oils as mentioned above.
  • the compositions of the present invention may be prepared in accordance with a common technique known in the art, in particular those intended for the preparation of emulsions.
  • the composition may be in particular in the form of a simple or complex emulsion, for example, an oil-in-water (O/W) , a water-in-oil (W/O) , an oil-in-water-in-oil (0/W/O) a or water-in-oil-in-water (W/O/W) emulsion, and preferably in the form of a water-in-oil or an oil-in-water emulsion. If one or more of the ingredients contained in the composition tend to separate over time, it may be advantageous to mix the composition uniformly before use.
  • composition of the present invention may be in any desired form which includes, but not limited to, a cream, a lotion, a milky lotion, a water-in-oil fluid, a gel, and a cream-gel.
  • the composition may also be packaged as an aerosol using a propellant and be in the form of a mousse or a spray.
  • compositions according to the invention are preferably in the form of an oil-in-water emulsion (O/W emulstion) or a water-in-oil emulsion (W/O emulsion) .
  • a water-in-oil emulsion is most preferred since the composition of the present invention in the form of a water-in-oil fluid can have excellent sensory characteristics such as extremely light spreadability on use without giving a sticky feeling to the skin and/or the hair.
  • an emulsifier selected from among amphoteric, anionic, cationic and nonioni.c emulsifiers or a mixture of two or more emulsifiers may be used to prepare an emulsion.
  • emulsifying surfactants that may be used for the preparation of the composition of the present invention in the form of a W/O emulsion, mention may be made of sorbitan, glycerol or sugar alkyl esters or ethers; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, marketed under the name "DC 5225 C" by Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol marketed under the name "Dow Corning 5200 Formulation Aid” by Dow Corning; cetyldimethicone copolyol, such as Cetyl PEG/PPG-10/1 Dimethicone and the product marketed under the name "Abil EM 90R” by Goldschmidt, and the mixture of cetyldimethicone copolyol, of p lyglyceryl isost
  • co-emulsifiers may also be added thereto, which may be selected advantageously from among the group comprising polyol alkyl esters .
  • Polyol alkyl esters that may especially be mentioned include glycerol and/or sorbitan esters, for example polyglyceryl isostearate, such as the product marketed under the name "Isolan GI 34" by Goldschmidt, sorbitan isostearate, such as the product marketed under the name "Arlacel 987" by ICI, sorbitan glyceryl isostearate, such as the product marketed under the name "Arlacel 986" by ICI, and mixtures thereof.
  • polyglyceryl isostearate such as the product marketed under the name "Isolan GI 34" by Goldschmidt
  • sorbitan isostearate such as the product marketed under the name "Arlacel 987” by ICI
  • sorbitan glyceryl isostearate such as the product
  • emulsifiers examples include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; polyoxyethylglycol dipolyhydroxystearate such as PEG-30
  • Dipolyhydroxystearate oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alkyl ethers; sugar esters, for instance sucrose stearate; fatty alkyl ethers of sugars, especially polyalkylglucosides (APG) such as decylglucoside and
  • APG polyalkylglucosides
  • laurylglucoside marketed, for example, by Henkel under the respective names "Plantaren 2000” and “Plantaren 1200", cetostearyl glucoside optionally as a mixture with cetostearyl alcohol, marketed, for example, under the name “Montanov 68" by SEPPIC, under the name “Tegocare CG90” by Goldschmidt and under the name “Emulgade KE3302” by Henkel, and also arachidyl glucoside, for example in the form of a mixture of arachidyl alcohol, behenyl alcohol and arachidyl glucoside, marketed under the name "Montanov 202" by SEPPIC; and a block copolymer having a polypropylene glycol block and a polyethylene glycol block such as "Poloxamer 407".
  • composition of the present invention in the form of an emulsion is typically prepared by mixing an aqueous phase containing water and a hydrophilic ngredient ( s ) and an oily phase containing a lipophilic cosmetic or dermatological active ingredient in an appropriate physiologically acceptable medium such as an oil, preferably under the presence of a surfactant.
  • a conventional method and an apparatus which are known in the art for preparing an emulsion can be employed.
  • composition of the present invention can be used in a wide variety of applications, such as personal care products, for instance cosmetics containing one or more cosmetic active ingredients for making up, caring and/or protecting the skin, the lips and/or the hair, and dermatological compositions such as quasi-drug and pharmaceutical compositions containing one or more lipophilic dermatological active ingredients.
  • composition of the present invention in the form of an emulsion comprises:
  • glycerol as component e) in an amount of 1 to 15% by weight, and preferably 3 to 10% by weight, relative to the total weight of the composition.
  • composition of the present invention is characterized in that it can provide a non-sticky feeling on use, often together with good spreading of the active ingredient, a non-glossy effect and a smooth feeling even without using a volatile cyclomethicone which is well known as an ingredient to improve feeling on use. Therefore, in another embodiment of the present invention, the composition of the invention comprises a volatile cyclomethicone in an amount less than 1% by weight of the total amount of the composition, and preferably comprises no volatile cyclomethicone.
  • the present invention provides a method for reducing a sticky feeling which may be caused by a lipophilic cosmetic or dermatological active ingredient contained in a cosmetic or dermatological composition in the form of an emulsion comprising an aqueous phase and an oily phase, by using a combination of ingredients b) , c) , d) and e) as described above.
  • a cosmetic or dermatological composition which has a low sticky feeling on use by using only a small amount of a volatile cyclomethicone such as less than 1% by weight relative to the total weight of the composition or without using any volatile cyclomethicone.
  • Synthetic wax is a synthetic hydrocarbon wax in the form of spherical particles having an average diameter, that is, a mean size by volume of 6 to 8 ⁇ , which was measured according to ASTM D4464. Preparation method for the compositions according to the example and comparative examples is as follows:
  • the aqueous phase (Phase C) was prepared by mixing all ingredients for phase C listed in Table 1 at room temperature.
  • the oily phase (Phase A) was prepared by mixing all- ingredients for phase A listed in Table 1 at 65 ° C in a turbine mixer which has a turbine type impeller . After cooling phase A to room temperature, phase C was added to phase A, and the resulting mixture was emulsified by using the turbine mixer to obtain a water-in-oil emulsion composition. Then, the resulting emulsion composition was allowed to cool to room temperature.
  • the powder phase (phase B) was introduced and mixed into the emulsion by using the turbine mixer to disperse the powders, that is, wax particles in the emulsion to obtain the emulsion composition comprising the wax particles.
  • non-slippery effect and “feeling after use” of the example and comparative examples.
  • Each panelist took each sample in their hands, then applied separate products on the right and left sides of their faces to evaluate non-glossy effect, non-slippery effect, and good feeling after use for each sample, and graded from l(poor) to 5 (excellent) for each effect, which was then classified in the following 4 categories based on the average of the grade:
  • “excellent” for the “non-glossy effect” means that the applied lotion provides no or only a little glossy appearance.
  • “Excellent” for the “non-slippery effect” means that the composition can be spread smooth on the skin with a good slippery feeling, but not too slippery.
  • “Excellent” of the "good feeling after use” means that the lotion provides a good feeling on the skin without giving an unpleasant sticky feeling.
  • composition of the present invention can easily be spread uniformly over the skin or the hair.

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Abstract

The purpose of the present invention is to provide a cosmetic or dermatological composition wherein a sticky feeling on use, which may be caused due to a lipophilic active ingredient contained in the composition, is reduced and a good feeling on touch of the composition is obtained. This purpose was accomplished by using a) at least 5% by weight of one or more of lipophilic cosmetic or dermatological active ingredients relative to the total amount of the composition; b) a non-alcoholic volatile solvent which is different from a cyclomethicone; c) a volatile alcohol; d) wax particles; and e) a non-volatile compound having at least one hydrophilic functional group.

Description

DESCRIPTION
A COSMETIC OR DERMATOLOGICAL COMPOSITION WITH LOW STICKINESS,
CONTAINING A LIPOPHILIC ACTIVE INGREDIENT
TECHNICAL FIELD
The present invention relates to a cosmetic or dermatological composition in the form of emulsion containing an aqueous phase and an oily phase, which comprises one or more of lipophilic cosmetic or dermatological active ingredients among others, wherein sticky feeling which may be caused by the active ingredient can be reduced and a good feeling on use of the composition can be obtained.
The present invention also relates to a method for reducing sticky feeling on keratinous material such as the skin and/or the hair, which may be caused by a lipophilic cosmetic or dermatological active ingredient applied on the keratinous material.
BACKGROUND ART
It is well known to incorporate a cosmetic or dermatological active ingredient such as a UV filter or a vitamin into a cosmetic or dermatological composition. Many types of these active
ingredients used in a cosmetic or dermatological composition are liposoluble. When a liposoluble active ingredient is added to a cosmetic or dermatological composition, a sticky feeling due to the active ingredient may often be caused after applying the composition on the skin or the hair and feeling on use of the composition will be deteriorated.
JP-A-2008-24.7897 discloses a UV protecting cosmetic composition comprising (a) 2-ethylhexyl 2-ethylhexanoate and/or isononyl 2-ethylhexanoate, (b) a UV-absorbing agent , and (c) a UV-scattering agent, and (d) a silicone oil in the form of an O/W emulsion or a W/O emulsion, which can provide a good feel on use with reduced sticky feeling. JP-A-2007-131612 discloses a UV-protecting cosmetic composition comprising a lipophilic UV filter and the use of an
alkylaryl-1, 3-propanedione-silicone derivative to improve the sticky feeling caused by the UV filter.
DISCLOSURE OF INVENTION
However, it is still desired an alternative method to reduce the sticky feeling of a cosmetic or dermatological composition, which is due to a lipophilic cosmetic or dermatological active ingredient in the composition and to provide a composition with a good feel on use.
It has now been discovered, surprisingly, that the use of a combination of one or more of lipophilic cosmetic or dermatological active ingredients, a non-alcoholic volatile solvent which is different from a cyclomethicone, a volatile alcohol, wax particles, and a non-volatile compound having at least one hydrophilic functional group, in a cosmetic or dermatological composition in the form of emulsion containing an aqueous phase and an oily phase can reduce the sticky feeling which may be caused by the lipophilic active ingredients and improve the feeling on use of the composition That is, the use of the above-mentioned combination of ingredients in a cosmetic or dermatological composition makes it possible to provide the resulting cosmetic or dermatological composition with a non-fatty and non-sticky feeling, often together with good spreading of the active ingredient, a non-glossy effect and a smooth feeling. The term "sticky feeling" is used herein to indicate a property of a cosmetic or dermatological composition which gives sticky or tacky feeling to the skin and/or the hair, when the composition is applied.
Thus, the present invention features a cosmetic or dermatological composition in the form of an emulsion, containing an aqueous phase and an oily phase, wherein the composition comprises:
a) at least 5% by weight of one or more of lipophilic cosmetic or dermatological active ingredients relative to the total amount of the composition; b) a non-alcoholic volatile solvent which is different from a cyclomethicone;
c) a volatile alcohol;
d) wax ' particles ; and
e) a non-volatile compound having at least one hydrophilic functional group.
Preferably, the composition of the present invention comprises a volatile cyclomethicone in an amount less than 1% by weight relative to the total amount of the composition, and more preferably comprises no volatile cyclomethicones .
[Definitions] a) Lipophilic cosmetic or dermatological active ingredients
The composition of the present invention comprises one or more lipophilic cosmetic or dermatological active ingredients. The "cosmetic or dermatological active ingredient" is a compound or a composition which can provide cosmetically or dermatologically beneficial effects when the composition containing the same is applied, in particular, to keratinous material such as the skin or the hair. The term "lipophilic" of lipophilic active ingredient means herein that the active ingredient is able to be totally dissolved in the oily phase of the present composition or able to be dispersed in a colloidal form, such as in a miscellar form, in the oily phase of the composition.
Examples of the lipophilic cosmetic or dermatological active ingredients are as follows, but not limited to:
Aminophenol and Aminophenol derivatives, which is herein also referred to "aminophenols", ' salicylic acid derivatives such as described below; 2-amino-4-alkylaminopyrimidine-3-oxide
derivatives, in particular
2-amino-4-dodecylaminopyrimidine-3-oxide; DHEA
(dehydroepiandrosterone) , derivatives thereof, and chemical precursors thereof, such as 7-hydroxy-DHEA and 7-keto-DHEA; cholesterols and derivatives thereof, such as esters thereof; vegetable sterols such as phytosterols and sitosterols, and esters thereof; triterpenic pentacyclic acids; hydroxystilbenes such as 4-hydroxystilbenes; flavonoids; UV filters; carotenoids such as retiol, for example, vitamin A and derivatives thereof, lycopen, and carotens; perfumes and essential oils; hormones; vitamins such as vitamin E; ceramides; and a combination of two or more of the aforementioned compounds.
The aminophenol derivatives mentioned above are more particularly the derivatives of formula (1) below, but not limited to these particular examples:
in which R' is a radical chosen from the group made up of the following radicals (a) , (b) and (c) :
(a) -CO-NR1^
(b) -CO-O-R3
(c) -S02R3
-where R1 represents a hydrogen atom or an optionally hydroxylated, saturated or unsaturated, linear or branched Ci to C6 alkyl radical, R2 represents a hydrogen atom or a radical chosen from saturated or unsaturated, linear, cyclic or branched Ci to C30 , in particular Ci2 to C30 alkyl radicals, which are optionally hydroxylated, and R3 represents a radical chosen from saturated or unsaturated, linear, cyclic or branched, including fused polycyclic, Ci to C30, in particular Ci2 to C30 alkyl radicals, which are optionally hydroxylated.
In formula (1), among the linear or branched R2 or R3 radicals containing from 1 to 30 carbon atoms, mention may advantageously be made of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, octyl, nonyl, 2-ethylhexyl, dodecyl, hexadecyl, behenyl, octadecyl and 2-butyloctyl radicals. These radicals preferably contain from 1 to 12 carbon atoms . Even more preferably, the alkyl radical generally contains from 1 to 6 carbon atoms. As a .lower alkyl radical, mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl and hexyl radicals
When it is unsaturated, a radical having one or more ethylenic · unsaturations , such as more particularly an allyl radical, is preferred.
When the alkyl radical is cyclic, mention may in particular be made of a cyclohexyl, cholesteryl or tert-butylcyclohexyl radical. When it is hydroxylated, the radical preferably contains from 1 to 6 carbon atoms and from 1 to 5 hydroxyl groups. Among monohydroxyalkyl radicals, a radical preferably containing 1 or 3 carbon atoms, in particular a hydroxymethyl , 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl radical, is preferred.
Among polyhydroxyalkyl radicals, a radical containing from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as a
2, 3-dihydroxypropyl , 2,3, 4-trihydroxybutyl,
2, 3, 4, 5-tetrahydroxypentyl or 2, 3, 4, 5, 6-pentahydroxyhexyl radical, is preferred.
The alkoxylated radicals are alkyl radicals, as in particular described above, preceded by an oxygen atom.
Preferably*, the aminophenol derivatives used in the present invention are those for which at least one and preferably all of the conditions below are met:
- the -OH function on the phenyl radical is in the ortho-position or, advantageously, in the para-position,
- R' is chosen from a radical of formula (a) or (b) .
Among the linear or branched alkyl radicals R1, mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl or hexyl radicals.
The aminophenol derivative preferably used in the composition of the present invention is a para-aminophenol derivative; even more preferably, it is N-ethoxycarbonyl-4-para-aminophenol of formula (la):
or else N-cholesteryloxycarbonyl-4-para-aminophenol of formula (lb) :
These aminophenol derivatives, and the process for preparing them, are described in the patent applications published as WO 99/10318 and WO 99/32077.
These derivatives may have a more or less long hydrocarbon chain, preferably alkoxycarbonyl chain, attached to the nitrogen atom.
The salicylic acid derivatives which can be used as the lipophilic cosmetic or dermatological active ingredients are the derivative of formula (2) :
in which
R"i represents a hydroxyl radical or an ester of formula
-0-CO-R**4
in which R"4 is a saturated or unsaturated aliphatic radical containing from 1 to 26 carbon atoms, and preferably from 1 to 18 carbon atoms, or an amine or thiol function optionally substituted with an alkyl radical containing from 1 to 18 carbon atoms, and preferably from 1 to 12 carbon atoms,
R"2 and R"3, independently of one another, are in the 3-, 4-, 5- or 6-position on the benzene ring and represent, independently of one another, a hydrogen atom or a radical:
-(0)n-(C0)m-R"5 in which n and m, independently of one another, are each an integer equal to 0 or 1, provided that R"2 and R"3 are not simultaneously hydrogen atoms,
and R"5 represents a hydrogen, a linear, branched or cyclized, saturated aliphatic radical containing from 1 to 18 carbon atoms, or an unsaturated radical containing from 3 to 18 carbon atoms, bearing one to nine conjugated or unconjugated double bonds, it being possible for the radicals to be substituted with at least one substituent chosen from halogen atoms (fluorine, chlorine, bromine or iodine), and the following radicals: trifluoromethyl, hydroxyl in free form or esterified with an acid containing from 1 to 6 carbon atoms, or carboxyl in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms, or an aromatic radical containing from 6 to 10 carbon atoms.
Preferably, the salicylic acid derivative is such that R"5 represents a saturated aliphatic radical containing from 3 to 15 carbon atoms.
Preferably, the salicylic acid derivative is such that R"i represents a hydroxyl radical.
Preferably, the salicylic acid derivative is such that R"5 is in the 5-position on the benzene ring and R"2 represents a hydrogen atom.
According to a preferred embodiment of the invention, the salicylic acid derivatives are derivatives of 5-n-octanoylsalicylic acid, 5-n-decanoylsalicylic acid, 5-n-dodecanoylsalicylic acid,
5-n-octylsalicylic acid, 5-n-heptyloxysalicylic acid,
4-n-heptyloxysalicylic acid, 5-tert-octylsalicylic acid,
3-tert-butyl-5-methylsalicylic acid,
3-tert-butyl-6-methylsalicylic acid, 3, 5-diisopropylsalicylic acid, 5-butoxysalicylic acid, 5-octyloxysalicylic acid,
5-propanoylsalicylic acid, 5-n-hexadecanoylsalicylic acid, 5-n-oleoylsalicylic acid, 5-benzoylsalicylic acid, monovalent and divalent salts thereof, and mixtures thereof.
Very particular preference is given to employing the
2-hydroxy-5-octanoylbenzoic acid available for sale under the trade name Mexoryl SAB by the company Chimex; such corresponding to the following formula:
It is known practice to use salicylic acid derivatives in topical compositions, for example, as a keratolytic agent for treating acne or as an anti-ageing agent; the patent applications published as FR-A-2 581 542 and EP-A-378 936 describe such derivatives.
Salicylic acid derivatives are highly advantageous in particular for preventing or repairing the principal manifestations of skin ageing, namely fine lines and wrinkles, disruption of the "grain" of the skin, modification of the complexion of the skin and loss of firmness and of tonicity of the skin. However, the use of these derivatives poses a problem insofar as, when they are introduced without modification into topical compositions, they are not solubilized and remain in the crystalline state, rendering the use of the composition containing them ineffective for the treatment of the skin.
It is possible to use one cosmetic or dermatological active ingredient or a combination of two or more cosmetic or
dermatological active ingredients in the composition of the present invention . in particular, a lipophilic UV filter can preferably be used as a lipophilic cosmetic or dermatological active ingredient in the composition of the present invention. The following are examples of the lipophilic UV filters which can be preferably used in the present invention, but not limited to: dibenzoylmethane derivatives, which is referred to as "dibenzoylmethanes", para-aminobenzoid acid derivatives, salicylic acid derivatives, cinnamic acid derivatives, benzophenone derivatives, aminobenzophenone derivatives,
anthranilic acid derivatives, beta, beta-diphenylacrylate derivatives, benzylidene camphor derivatives, phenylbenzimidazole derivatives, benzotriazole derivatives, triazines, bis-resorcinyl triazines, imidazoline derivatives, benzalmalonates ,
4.4-diarylbutadiene derivatives, benzoxazole derivatives, merocyanines , dephenylbutadiene malonates or malononitriles , chalcones, and a combination of two or more of the aforementioned compounds. These UV filters are known in the art. The more detailed description about UV filters is presented below.
The UV filter used for the present invention may be selected from the group consisting of lipophilic UVA filters, lipophilic UVB filters, lipophilic UV filters which can act as both UVA and UVB filters, and a combination thereof.
[Lipophilic UVA filters]
As lipophilic UVA filters, which absorb UV light in the range of wavelength from 320 to 400 nm, mention may be made of the following compounds, but hot limited to:
- Dibenzoylmethane derivatives, also referred to as
"dibenzoylmethanes", -such as: 2-methyldibenzoylmethane,
4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane,
4-tert-butyldibenzoylmethane, 2, 4-dimethyldibenzoylmethane,
2.5-dimethyldibenzoylmethane, 4, 4' -diisopropyldibenzoylmethane, 4, 4' -dimethoxydibenzoylmethane,
4-tert-butyl-4 ' -methoxydibenzoylmethane,
2-methyl-5-isopropyl-4 ' -methoxydibenzoylmethane,
2-methyl-5-tert-butyl-4' -methoxydibenzoylmethane,
2, 4-dimethyl-4' -methoxydibenzoylmethane,
2.6-dimethyl-4-tert-butyl-4' -methoxydibenzoylmethane .
4-tert-butyl-4 ' -methoxydibenzoylmethane or Butyl Methoxy
Dibenzoylmethane, marketed under the name "PARSOL 1789" by DSM NUTRITIONAL PRODUCTS, which has the following formula: [chemical formula 1]
is particularly preferred.
- Aminobenzophehone derivatives, such as n-hexyl
2- (4-diethylamino-2-hydroxybenzoyl) benzoate, marketed under the name "UVINUL A+" by BASF;
- Anthranilic acid derivatives, such as Menthyl anthranilate, marketed under the name "NEO HELIPAN MA" by Symrise; and
- 4 , -Diarylbutadiene derivatives, such as
1, 1-dicarboxy (2,2' -dimethylpropyl) -4, 4-diphenylbutadiene, and diphenyl butadinene malonates and malononitriles;
- Chalcone and derivatives thereof, also referred to as "chalcones" .
In particular, PARSOL 1789, UVINUL A+, or a combination thereof is particularly preferred to be used as a lipophilic UVA filter (s) in the .composition of the present invention.
[Lipophilic UVB filters]
As lipophilic UVB filters which absorb UV light in the range of wavelength from 280 to 320 nm, mention may be made of, but not limited to:
- Para-aminobenzoic acid derivatives, such as para-aminobenzoates (PABA), for example, Ethyl PABA (para-aminobenzoate) , Ethyl Dihydroxypropyl PABA, Ethylhexyl Dimethyl PABA, marketed under the name "ESCALOL 597" by ISP;
- Salicylic acid derivatives, such as Homosalate, marketed under the name "Eusolex HMS" by Rona/EM industries, Ethylhexyl Salicylate, marketed under the name "NEO HELIOPAN OS" by Symrise,
Dipropyleneglycol Salicylate, marketed under the name "DIPSAL" by SCHER, and TEA Salicylate, marketed" under the name "NEO HELIOPAN TS" by Symrise;
- Cinnamic acid derivatives, such as Ethylhexyl Methoxycinnamate, marketed under the name "PARSOL CX" by DSM NUTRITIONAL PRODUCTS, Isopropyl ethoxy cinnamate, Isoamyl Methoxy cinnamate, marketed under the name "NEO HELIOPAN E 1000" by Symrise, Dii'sopropyl ethylcinnamate, Cinoxate, and Glyceryl Ethylhexanoate
Dimethoxycinnamate;
- β, β (beta, beta) -Diphenylacrylate derivatives, such as
Octocrylene, marketed under the name "UVINUL N539" by BASF, and Etocrylene, marketed under the name "UNIVUL N35" by BASF;
- Benzylidene camphor derivatives, such as 3-Benzylidene camphor, marketed under the name "MEXORYL SD" from CHIMEX, ethylbenzylidene camphor, marketed under the name "EUSOLEX 6300" by MERCK, and Polyacrylamidomethyl Benzylidene Camphor, marketed under the name "MEXORYL SW" by CHIMEX, and Terephthalylidene Dicamphor Sulfonic Acid, marketed under the name "Mexoryl SX" by Chimex;
- Phenylbenzimidazole derivatives, such as
phenylbenzimidazolesulfonic acid marketed in particular under the name "Eusolex 232" by Merck, disodium phenyl dibenzimidazole tetrasulfonate marketed under the name "Neo Heliopan AP" by Haarmann and Reimer;
- Triazines, such as Ethylhexyl triazone, marketed under the name "UVINUL T150" by BASF, Diethylhexyl Butamido Triazone, marketed under the name "UVASORB HEB" by SIGMA 2V, 2 , 4 , 6-tris (dineopentyl 4 ' -aminobenzalmalonate) -s-triazine, 2,4, 6-tris (diisobutyl
4 ' -aminobenzalmalonate) -s-triazine, 2 , 4-bis (dineopentyl
4' -aminobenzalmalonate) -6- (n-butyl 4' -aminobenzoate) -s-triazine,
2, 4-bis (n-butyl
4' -aminobenzoate) -6- (aminopropyltrisiloxane) -s-triazine;
- Imidazoline derivatives, such as Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate;
- Benzalmalonates , such as Polyorganosiloxane containing a benzalmalonate moiety, for example, Polysilicone-15, marketed under the name "Parsol SLX" by DSM NUTRITIONAL PRODUCTS,
Di-neopentyl 4 ' -methoxybenzalmalonate; and
- Merocyanines, such as
Octyl-5-N, -diethylamino-2-phenylsulfonyl-2 , 4-pentadienoate .
It is preferred to use one or more lipophilic UVB filters selected from the group consisting of Ethylhexyl triazone, Diethylhexyl Butamido Triazone, Octocrylene, Homosalate, Ethylhexyl Salicylate, and Ethylhexyl Methoxycinnamate as a lipophilic cosmetic or dermatological ingredient in the composition.
[Lipophilic UVA and UVB filters]
Lipophilic compounds which act as UVA and UVB filters can also be used in the composition with or without another UV filter. The following are non-limited examples of UVA and UVB filters:
- Benzophenone derivatives, such as Benzophenone-1 marketed under the name "UVINUL 400" by BASF, Benzophenone-2 marketed under the name "UNIVUL 500" by BASF, Benzophenone-3 or Oxybenzone marketed under the name "UVINUL M40" by BASF, Benzophenone-6 marketed under the name "Helisorb 11" by Norquay, Benzophenone-8 marketed under the name "Spectra-Sorb UV-24" by American Cyanamid, Benzophenone-10 , Benzophenone-11 , and Benzophenone-12 ;
- Benzotriazole derivatives such as Drometrizole Trisiloxane marketed under the name "Silatrizole" by Rhodia Chimie and
Bumetrizole marketed under the name "TINOGUARTD AS" by CIBA-GEIGY;
- Bis-resorcinyl triazines, such as Bis-Ethylhexyloxyphenyl methoxyphenyl Triazine marketed under the name "TINOSORB S" by CIBA-GEIGY; and
- Benzoxazole derivatives, such as
2, -bis [5- ( 1-dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1, 3, 5-triazine marketed under the name
"Uvasorb K2A" by Sigma 3V.
Drometrizole Trisiloxane and/or Bis-Ethylhexyloxyphenol
Methoxyphenyl Triazine may be preferably used as a UVA and UVB filter in the composition of the present invention.
The above-listed UV filters can be used alone or as a combination of two or more UV filters. A combination-of a UVA filter and a UVB filter can be preferably employed.
The total amount of lipophilic cosmetic or dermatological active ingredients contained in the composition of the present invention is not limited to a particular amount but is preferably at least 5% by weight, in particular in the range from 5% to 30% by weight, and more preferably in the range from 10% to 20% by weight relative to the total amount of the composition of the present invention. By using one or more of intended lipophilic cosmetic or
dermatological active ingredients in an amount described above together with ingredients b) to e) in the composition of the present invention, it will be possible to obtain desired cosmetic and/or dermatological effects due to the active ingredients and to afford reduced sticky feeling on use to the composition. b) Non-alcoholic volatile solvents
The term "a non-alcoholic volatile solvent" refers to a
non-alcoholic solvent wherein more than 95% by weight of the solvent is able to evaporate in less than one hour at room temperature (25 °C) under atmospheric pressure (760 mmHg = 1013xl05 Pa) upon contact to a keratinous material such as the skin or the hair. Typically, the non-alcoholic volatile solvent is in the form of liquid at room temperature, and has a vapor pressure more than 0(zero),
particularly from 0.13 Pa to 40,000 Pa (10~3 to 300 mmHg), more particularly from 1.3 Pa to 13, 000 Pa (0.01 to 100 mmHg), and more preferably from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg) at room temperature. The term "room temperature" means 25 °C herein.
A "non-alcoholic volatile solvent" which is different from a cyclomethicone is used in the present invention. This does not mean to exclude the use of cyclomethicone together with the
"non-alcoholic volatile solvent". Cyclomethicone is an INCI name, which represents cyclic dimethyl polysiloxane compounds of the formula (CH3)2nOnSin where n = 3-7.
As examples of the non-alcoholic volatile solvent which is different from a cyclomethicone, mention may be made of, but not limited to: (i) Hydrocarbons having from 8 to 16 carbon atoms, more particularly isoalkanes having 8 to 16 carbon atoms, that is, C8-Ci6 (isoparaffins) , such as isododecane (or 2, 2, 4, 4, 6-pentamethylheptane) , isodecane, isohexadecane, for example, the hydrocarbons sold under the name "Isopers" or "Permethyls"; branched esters having 8 to 16 carbon atoms such as isohexyl neopentanoate, and a mixture thereof; Petroleum distillates such as "Shell Sol T" marketed by Shell Chemicals; linear alkanes such as those described in WO2007/068371.
(ii) Volatile silicone oils which are different from a
cyclomethicone, such as a linear silicone oil, for instance, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane,
decamethyltetrasiloxane (L4 ) , KF96A from Shin-Etsu Chemical, polydimethylsiloxanes such as those marketed under the name "DC 200 (1.5 cSt)", "DC 200 (5 cSt)", and "DC 200 ( 3 cSt) " by Dow Corning Corporation, and linear alkyltrisiloxanes of formula (I):
(CH3) 3Si-0-Si (CH3) (R) -O-Si (CH3) 3 (D in which, R represents a C2-C4 alkyl group wherein one or more hydrogen atoms may be substituted by a halogen atom(s) selected from a fluorine atom and a chlorine atom. Examples of the compounds of formula I are 3-butyl-l, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane, 3-propyl-l, 1,1,3,5,5, 5-heptamethyltrisiloxane, and
3-ethyl-l, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane, which has a butyl, a propyl, or an ethyl group as R of formula I, respectively.
(iii) Fluorinated volatile oils, for example, perfluoropolyethers , perfluoroalkanes such as perfluorodecaline and
perfluoroadamantanes ; perfluoroalkylphosphates (monoesters, diesters and triesters) ; and fluorinated esters oils.
The amount of non-alcoholic volatile solvent which is different from a cyclomethicone and present in the composition of the present invention is typically in the range from 5 to 20% by weight, more preferably 7 to 15% by weight relative to the total amount of the composition, but not limited thereto. c) Volatile alcohols
The term "a volatile alcohol" refers to a compound which has at least one hydroxyl group, wherein more than 95% by weight of the compound is able to evaporate in less than one hour at room temperature (25 °C) under atmospheric pressure (760 mmHg = 1013xl05 Pa) upon contact with a keratinous material such as the skin or the hair.
The volatile alcohol used in the composition of the present invention is preferably selected from monoalcohols , particularly alkylmonoalcohols, in particular, C1-C5 lower alkylmonoalcohols, that is, alkylmonoalcohols having 1 to 5 carbon atoms such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol . Ethanol and isopropanol are preferred. Ethanol is particularly preferred. Viscosity of the volatile alcohol preferably- is in the range from 0.3 to 3 mPa.s at 20 °C, as measured using a HAAKE Rheostress 600 machine with a spindle having a diameter of 60 mm, an angle of 2° and a sand-blasted coating at a shear rate of 200 s"1 at 20°C.
The amount of the volatile alcohol present in the composition is not limited to a particular amount, but preferably is in the range from 0.5 to 20% by weight, more preferably from 1 to 10% by weight relative to the total amount of the composition of the present invention . d) Wax particles
The wax particles, also referred to as "microwaxes" herein, used for the composition of the present invention are a wax which is in the form of small particles and typically present in the oily phase of the composition. The mean size by volume of the wax particles is preferably in the range from 0.5 to 30 micrometers, in particular from 1 to 20 micrometers, and more particularly from 5 to 10 micrometers, which is measured according to AST D 4464. By using microwaxes having such a mean particle size in combination with other ingredients b) to e) in the composition of the present invention, the sticky feeling which may be caused by a lipophilic cosmetic or dermatological active ingredient can be effectively reduced and a good feeling on use of the composition can be obtained often together with improved extendibility of the composition and smooth feeling on the skin or the hair. The term "wax" means a compound that is solid or substantially solid at 25 °C and whose melting point is generally greater than 35 °C. The wax which constitutes the wax particles is not limited to a particular wax and may be any types of waxes, such as synthetic waxes and waxes of natural origin. Therefore, one or more selected from the group consisting of natural wax particles, synthetic wax particles, and a combination thereof can be used in the composition of the present invention. In particular, it is preferable to use one or more wax particles selected from the group consisting of carnauba wax particles, synthetic wax particles, polyethylene wax particles, and a combination thereof.
As the microwaxes which can be used in the composition of the present invention, mention may be made of microwaxes of carnauba waxes, such as those marketed under the name "MicroCare 350®" by Micro Powders, which has a mean particle size of 6.0-8.0 micrometers; synthetic wax microwaxes, such as those marketed under the name "MicroEase 114S®" by Micro Powders, which has a mean particle size of 6.0 to 8.0 micrometers; microwaxes composed of a mixture of carnauba wax and polyethylene wax, such as those marketed under the name "MicroCare 300®" and "MicroCare 310®" by Micro Powders, which have a mean particle size of 4.5 to 5.5, or 4.0 to 6.0 respectively; microwaxes composed of a mixture of carnauba wax and a synthetic wax, such as those marketed under the name "MicroCare 325®" by Micro Powders, which has a mean particle size of 4.5. to 5.5 micrometers; and polyethylene microwaxes, such as those marketed under the names "Micropoly 200®", "Micropoly 220®", "Micropoly 220L®", and "Micropoly 250S®"'by Micro Powders, which have a mean particle size of 6.0 to 8.0, 7.0 to 9.0, 8.0 to 10.0, or 2.0 to 4.0, respectively.
The amount of wax particles present in the composition of the present invention is not limited to a specific amount, but preferably, is in the range from 0.5 to 20% by weight, more preferably from 1 to 10% by weight relative to the total weight of the composition. e) Non-volatile compounds having at least one hydrophilic functional group ■The term "non-volatile compound" means a compound, wherein more than 50% of the weight of the compound is maintained on keratinous material such as the skin and the hair at 25 °C under atmospheric pressure (760 mmHg = 1013xl05 Pa) for 3 hours after the compound is applied to the keratinous material . Non-volatile compounds used for the present invention typically have a vapor pressure of less than 10~3 mmHg (0.13 Pa). The non-volatile compounds preferably have an evaporation speed such that the evaporated amount after 30 minutes is less than 0.07 mg/cm2.
The term "hydrophilic functional group" means a functional group which can form a hydrogen bond with a water molecule . As typical examples of hydrophilic functional groups, mention may be made of, but not limited to, a hydroxyl or alcohol group, an amino group which include a primary, a secondary and a tertiary amino group, and a carboxyl group. Non-volatile compounds having two or more hydroxyl groups are preferred and those having 2 to 12 carbon atoms are particularly preferred to be used as ingredient e) . As examples of preferred non-volatile compounds having at least one hydrophilic functional group, mention may be made of glycerin, propylene glycol, dipropylene glycol, tripropylene glycol, diglycerin, ethylene glycol, triethylene glycol, isoprene glycol, diglycerin, pentylene glycol, hexylene glycol, sorbitol, mannitol, D-glucose, sucrose, D-fructose, xylitol," lactose, maltose, maltitol, trehalose, hydroxyethyl urea, and a combination of two or more of the aforementioned compounds.
The amount of the non-volatile compound having at least one hydrophilic functional group present in the composition of the present invention is not limited to a particular amount, but preferably is in the range1 from 0.5 to 20% by weight, and more preferably from 1 to 10% by weight relative to the total weight of the composition. f ) Other ingredients
A cosmetic or dermatological composition of the present invention in the form of an emulsion containing an aqueous phase and an oily phase may optionally contain one or more additional ingredients which are commonly used in a cosmetic or dermatological composition in addition to ingredients a) to e) .
As examples of such additional ingredients, mention may be made of, but not limited to, conventional cosmetic adjuvants selected especially from among fatty substances; organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners; softeners; humectants; opacifiers; stabilizers; preservative; emollients; silicones; anti-foams; fragrances; preservatives; anionic, cationic, nonionic, zwitterionic or amphoteric surfactants;
hydrophilic cosmetic or dermatological active ingredients;
fillers; polymers; propellants; acidifying or basifying agents; pigments; dyes; inorganic photoprotective agents and any other ingredients commonly used in a cosmetic or dermatological composition .
The fatty substances may be an oil. The term "oil" means a compound that is lipophilic liquid at room temperature. Oils that may be mentioned include mineral oils (paraffin); vegetable oils (sweet almond oil, macadamia oil, grapeseed oil or jojoba oil) ; synthetic oils, for instance perhydrosqualene, fatty alcohols, fatty acids or fatty esters (for instance the C12-C15 alkyl benzoate marketed under the name "Finsolv TN" of "Witconol TN" by Witco, octyl palmitate, isonohyl isononanoate, isopropyl lanolate and triglycerides, including capric/caprylic acid triglycerides), dialkyl carbonate such as dicaprylyl carbonate, oxyethylenated or oxypropylenated fatty esters and ethers; silicone oils
(cyclomethicones and polydimethylsiloxanes such as dimethicone) or fluoro oils, and polyalkylenes . Oil containing at least one amide structure such as those disclosed in US7,357,920, the disclosure of which is incorporated herein by reference, can also be used.
If desired, one or more thickeners selected from the group consisting of hydrophilic thickeners and lipophilic thickners may be added to the composition of the present invention in order to Ddify the rheological properties the
Hydrophilic thickeners that may be mentioned include carboxyvinyl polymers such as the Carbopol products (carbomers) and the Pemulen products (acrylate/Cio-3o-alkylacrylate copolymer) ;
polyacrylamides, for instance the crosslinked copolymers marketed under the name "Sepigel 305" (CTFA name: polyacrylamide/Ci3-i4 isoparaffin/Laureth 7) or "Simulgel 600" (CTFA name:
acrylamide/sodium acryloyldimethyltaurate
copolymer/isohexadecane/polysorbate 80) by SEPPIC;
2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, which are optionally crosslinked and/or neutralized, for instance the poly (2-acrylamido-2-methylpropanesulfonic acid) marketed by Hoechst under the name "Hostacerin AMPS" (CTFA name: ammonium polyacryldimethyltauramide) ; cellulose-based derivatives such as hydroxyethylcellulose; polysaccharides and especially gums such as xanthan gum; and mixtures thereof.
Lipophilic thickeners that may be mentioned include modified clays such as hectorite and its derivatives, for instance the products marketed under the name "Bentone".
In the composition of the present invention, a hydrophilic cosmetic or dermatological active ingredient may optionally be used in addition to ingredients a) to e) mentioned above. The term "hydrophilic" active ingredient means herein that the active ingredient' is able to be dissolved in the aqueous phase of the present composition or able to be dispersed in a colloidal form, such as in a miscellar form, in the aqueous phase of the present composition. Hydrophilic cosmetic or dermatological active ingredients which are known in the art, such as ascorbic acid and derivative thereof, may be used.
As fillers or polymers which may be added to the composition of the present invention, mention may be made of, but not limited to, natural fibers such as silk, cellulose, and wool; synthetic fibres such as polyamide which is also referred to as "Nylon®", and rayon; and particles or beads of polymers such as polyamides, polyacrylates, and polymethylsilsesquioxane .
As described above, an inorganic photoprotective agent may be used together with the lipophilic cosmetic or dermatological active ingredient. An inorganic photoprotective agent used for the present invention may be selected from among pigments and even more preferably nanopigments (mean size of the primary particles: generally from 5 run to 100 nm and preferably from 10 nm to 50 nm) of treated or untreated metal oxides such as, for example, nanopigments of titanium oxide (amorphous or crystallized in rutile and/or anatase form) , of iron oxide, of zinc oxide, of zirconium oxide or of cerium oxide.
The treated nanopigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53-64, such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal (titanium or aluminum) alkoxides, polyethylene, silicones, proteins (collagen or elastin) , alkanolamines, silicon oxides, metal oxides, sodium
hexametaphosphate, alumina or glycerol.
Many particular pigments and nanopigments which can be used are disclosed in US7,357,920 which is incorporated by reference in its entirety.
It is also possible to use in the present composition at least one agent for artificially tanning and/or browning the skin.
[Formulation of the composition of the present invention]
The cosmetic or dermatological composition of the present invention is in the form of an emulsion containing an aqueous phase and an oily phase. Each phase comprises a physiologically acceptable medium. In particular, the aqueous phase comprises water. The physiologically acceptable medium of the oily phase is commonly selected from fatty substances such as oils as mentioned above. The compositions of the present invention may be prepared in accordance with a common technique known in the art, in particular those intended for the preparation of emulsions. The composition may be in particular in the form of a simple or complex emulsion, for example, an oil-in-water (O/W) , a water-in-oil (W/O) , an oil-in-water-in-oil (0/W/O) a or water-in-oil-in-water (W/O/W) emulsion, and preferably in the form of a water-in-oil or an oil-in-water emulsion. If one or more of the ingredients contained in the composition tend to separate over time, it may be advantageous to mix the composition uniformly before use.
The composition of the present invention may be in any desired form which includes, but not limited to, a cream, a lotion, a milky lotion, a water-in-oil fluid, a gel, and a cream-gel. The composition may also be packaged as an aerosol using a propellant and be in the form of a mousse or a spray.
The compositions according to the invention are preferably in the form of an oil-in-water emulsion (O/W emulstion) or a water-in-oil emulsion (W/O emulsion) . A water-in-oil emulsion is most preferred since the composition of the present invention in the form of a water-in-oil fluid can have excellent sensory characteristics such as extremely light spreadability on use without giving a sticky feeling to the skin and/or the hair.
Methods for preparing an emulsion are known in the art. A person skilled in the art can employ any desired method. In addition, an emulsifier selected from among amphoteric, anionic, cationic and nonioni.c emulsifiers or a mixture of two or more emulsifiers may be used to prepare an emulsion.
As emulsifying surfactants that may be used for the preparation of the composition of the present invention in the form of a W/O emulsion, mention may be made of sorbitan, glycerol or sugar alkyl esters or ethers; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, marketed under the name "DC 5225 C" by Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol marketed under the name "Dow Corning 5200 Formulation Aid" by Dow Corning; cetyldimethicone copolyol, such as Cetyl PEG/PPG-10/1 Dimethicone and the product marketed under the name "Abil EM 90R" by Goldschmidt, and the mixture of cetyldimethicone copolyol, of p lyglyceryl isostearate (4 mol) and. of hexyl laurate, marketed under the name "Abil WE 09" by Goldschmidt. One or more
co-emulsifiers may also be added thereto, which may be selected advantageously from among the group comprising polyol alkyl esters . Polyol alkyl esters that may especially be mentioned include glycerol and/or sorbitan esters, for example polyglyceryl isostearate, such as the product marketed under the name "Isolan GI 34" by Goldschmidt, sorbitan isostearate, such as the product marketed under the name "Arlacel 987" by ICI, sorbitan glyceryl isostearate, such as the product marketed under the name "Arlacel 986" by ICI, and mixtures thereof.
For the O/W emulsions, examples of emulsifiers that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; polyoxyethylglycol dipolyhydroxystearate such as PEG-30
Dipolyhydroxystearate; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alkyl ethers; sugar esters, for instance sucrose stearate; fatty alkyl ethers of sugars, especially polyalkylglucosides (APG) such as decylglucoside and
laurylglucoside marketed, for example, by Henkel under the respective names "Plantaren 2000" and "Plantaren 1200", cetostearyl glucoside optionally as a mixture with cetostearyl alcohol, marketed, for example, under the name "Montanov 68" by SEPPIC, under the name "Tegocare CG90" by Goldschmidt and under the name "Emulgade KE3302" by Henkel, and also arachidyl glucoside, for example in the form of a mixture of arachidyl alcohol, behenyl alcohol and arachidyl glucoside, marketed under the name "Montanov 202" by SEPPIC; and a block copolymer having a polypropylene glycol block and a polyethylene glycol block such as "Poloxamer 407". The composition of the present invention in the form of an emulsion is typically prepared by mixing an aqueous phase containing water and a hydrophilic ngredient ( s ) and an oily phase containing a lipophilic cosmetic or dermatological active ingredient in an appropriate physiologically acceptable medium such as an oil, preferably under the presence of a surfactant. For mixing an aqueous phase and an oily phase to prepare an emulsion, a conventional method and an apparatus which are known in the art for preparing an emulsion can be employed.
The composition of the present invention can be used in a wide variety of applications, such as personal care products, for instance cosmetics containing one or more cosmetic active ingredients for making up, caring and/or protecting the skin, the lips and/or the hair, and dermatological compositions such as quasi-drug and pharmaceutical compositions containing one or more lipophilic dermatological active ingredients.
In the most preferred embodiment, the composition of the present invention in the form of an emulsion comprises:
A) one or more lipophilic cosmetic or dermatological active ingredients, more preferably UV filters, which are described above as component a) in an amount of 5 to 30% by weight, preferably 15 to 30% by weight in total;
B) dimethicone as component b) in an amount of 5 to 20% by weight;
C) ethanol as component c) in an amount of 1 to 15% by weight, and preferably 3 to 10% by weight;
D) wax particles selected from synthetic wax particles, natural wax particles and a combination thereof, which have a mean size by volume in the range from 0.5 to 30 micrometers, preferably from 1 to 20 micrometers, and more preferably 5 to 10 micrometers as component d) ;
E) glycerol as component e) in an amount of 1 to 15% by weight, and preferably 3 to 10% by weight, relative to the total weight of the composition.
The composition of the present invention is characterized in that it can provide a non-sticky feeling on use, often together with good spreading of the active ingredient, a non-glossy effect and a smooth feeling even without using a volatile cyclomethicone which is well known as an ingredient to improve feeling on use. Therefore, in another embodiment of the present invention, the composition of the invention comprises a volatile cyclomethicone in an amount less than 1% by weight of the total amount of the composition, and preferably comprises no volatile cyclomethicone.
In addition, in a further embodiment, the present invention provides a method for reducing a sticky feeling which may be caused by a lipophilic cosmetic or dermatological active ingredient contained in a cosmetic or dermatological composition in the form of an emulsion comprising an aqueous phase and an oily phase, by using a combination of ingredients b) , c) , d) and e) as described above. In this method, it is possible to obtain a cosmetic or dermatological composition which has a low sticky feeling on use by using only a small amount of a volatile cyclomethicone such as less than 1% by weight relative to the total weight of the composition or without using any volatile cyclomethicone.
In order to further illustrate the present invention and the advantages thereof, the following specific examples are given. It should be understood that the examples are intended only as illustrative and in nowise limitative. In the examples, all parts and percentages are given by weight, unless otherwise indicated.
EXAMPLES
[Example 1] Sunscreen lotion
Sunscreen compositions in the form of a water-in-oil emulsion were prepared by using the ingredients shown in Table 1 below. The composition of the present invention (Example) contains a synthetic wax in the form of particles, alcohol denat . , and glycerin- among other ingredients. However, each of Comparative Examples 1 to 3 does not comprise any one of them. Table Γ
"Concentration %" in Table 1 indicates "% by weight"
"Synthetic wax" is a synthetic hydrocarbon wax in the form of spherical particles having an average diameter, that is, a mean size by volume of 6 to 8 μπι, which was measured according to ASTM D4464. Preparation method for the compositions according to the example and comparative examples is as follows:
The aqueous phase (Phase C) was prepared by mixing all ingredients for phase C listed in Table 1 at room temperature. The oily phase (Phase A) was prepared by mixing all- ingredients for phase A listed in Table 1 at 65 ° C in a turbine mixer which has a turbine type impeller . After cooling phase A to room temperature, phase C was added to phase A, and the resulting mixture was emulsified by using the turbine mixer to obtain a water-in-oil emulsion composition. Then, the resulting emulsion composition was allowed to cool to room temperature. The powder phase (phase B) was introduced and mixed into the emulsion by using the turbine mixer to disperse the powders, that is, wax particles in the emulsion to obtain the emulsion composition comprising the wax particles.
[Evaluation of the example and comparative examples]
Five professional panelists evaluated "non-glossy effect",
"non-slippery effect" and "feeling after use" of the example and comparative examples. Each panelist took each sample in their hands, then applied separate products on the right and left sides of their faces to evaluate non-glossy effect, non-slippery effect, and good feeling after use for each sample, and graded from l(poor) to 5 (excellent) for each effect, which was then classified in the following 4 categories based on the average of the grade:
"excellent" (5.0 to 4.0), "good" (3.9 to 3.0), "fair" (2.9 to 2.0), or "poor" (1.9 to 1.0). In these evaluations of the example and comparative examples, "excellent" for the "non-glossy effect" means that the applied lotion provides no or only a little glossy appearance. "Excellent" for the "non-slippery effect" means that the composition can be spread smooth on the skin with a good slippery feeling, but not too slippery. "Excellent" of the "good feeling after use" means that the lotion provides a good feeling on the skin without giving an unpleasant sticky feeling.
The results are shown in Table 2. Table 2
As shown in Table 2, excellent non-glossy and non-slippery effects, and a good feeling after use without giving an unpleasant sticky feeling can be obtained with the composition of the present invention, even though it comprises a lipophilic cosmetic or dermatological active ingredient which may cause a sticky feeling on use, compared to Comparative Examples 1 to 3. These results clearly show that the use of a combination of ingredients a) to e) in a composition in the form of an emulsion can reduce stickiness which may be caused by a lipophilic cosmetic or dermatological active ingredient a) contained in the composition.
In addition, it has been found that the composition of the present invention can easily be spread uniformly over the skin or the hair.
The results shown above which were obtained by using ingredients b) to e) together with ingredient a) in a cosmetic or dermatological composition in the form of an emulsion is not limited to the case in which a lipophilic UV filter is used as an active ingredient a) . The effects of the present invention can be obtained for any lipophilic cosmetic or dermatological active ingredients.

Claims

1. A cosmetic or dermatological composition in the form of an emulsion, containing an aqueous phase and an oily phase, wherein the composition comprises:
a) at least 5% by weight of one or more of lipophilic cosmetic or dermatological active ingredients relative to the total amount of the composition; .
b) a non-alcoholic volatile solvent which is different from a cyclomethicone;
c) a volatile alcohol;
d) wax particles; and
e) a non-volatile compound having at least one hydrophilic functional group.
2. The composition according to claim 1, wherein the composition comprises a volatile cyclomethicone in an amount less than 1% by weight relative to the total amount of the composition, and preferably comprises no volatile cyclomethicones .
3. The composition according to claim 1 or 2, wherein the composition comprises:
the lipophilic cosmetic or dermatological active ingredients a) in an amount of 5 to 30% by weight, and more preferably 10 to 20% by weight;
the non-alcoholic volatile solvent b) in an amount of 5 to 20% by weight, and more preferably from 7 to 15% by weight;
the volatile alcohol c) in an amount of 0.5 to 20% by weight, and more preferably 1 to 10% by weight;
the wax particles d) in an amount of 0.5 to 20% by weight, and more preferably 1 to 10% by weight;
the non-volatile compound having at least one hydrophilic functional group e) in an amount of 0.5 to 20% by weight, and more preferably 1 to 10% by weight relative to the total weight of the composition.
4. The composition according to any one of claims 1 to 3, wherein the hydrophilic functional group of the non-volatile compound e) is one or more selected from the group consisting of hydroxyl, amino, and carboxyl groups.
5. The composition according to any one of claims 1 to 4, wherein the one or more of lipophilic cosmetic or dermatological active ingredients a) are selected from the group consisting of aminophenols; salicylic acid derivatives;
2-amino-4-alkylaminopyrimidine-3-oxide derivatives, in
particular 2-amino-4-dodecylaminopyrimidine-3-oxide;
dehydroepiandrosterone, derivatives thereof, and chemical precursors thereof; cholesterol and esters thereof, phytosterols, sitosterols and esters thereof; triterpene pentacyclic acids; hydroxystilbens; flavonoids; UV filters; carotenoids such as Vitamin A and derivatives thereof, lycopen, and carotens; perfumes or essential oils; hormones; Vitamin E; and ceramides.
6. The composition according to claim 5, wherein the lipophilic cosmetic or dermatological active ingredient a) is one or more UV filters .
7. The composition according to claim 5, wherein the one or more of UV filters are selected from the group consisting of
dibenzoylmethanes, para-aminobenzoic acid derivatives, salicylic acid derivatives, cinnamic acid derivatives, benzophenone derivatives, aminobenzophenone derivatives, anthranilic acid derivatives, β, β-diphenylacrylate derivatives, berizylidene camphor derivatives, phenyl benzimidazole derivatives,
benzotriazole derivatives, triazines, bis-resorcinyl triazines, imidazolines derivatives, benzalmalonates, 4 , 4-diarylbutadiene derivatives, benzoxazole derivatives, merocyanines, diphenyl butadiene malonates or malononitriles , chalcones, and a combination of two or more of the aforementioned compounds.
8. The composition according to any one of claims 1 to 7, wherein the non-alcoholic volatile solvent b) is selected from the group consisting of linear or branched hydrocarbons having from 8 to 16 carbon atoms, branched esters having from 8 to 16 carbon atoms, volatile linear silicone oils, volatile fluorinated oils, and a mixture thereof.
9. The composition according to any one of claims 1 to 8, wherein the volatile alcohol c) is selected from the group consisting of alkylmonoalcohols - having 1 to 5 carbon atoms.
10. The composition according to any one of claims 1 to 9, wherein the wax particles d) have a mean size by volume in the range from 0.5 to 30 micrometers, in particular from 1 to 20 micrometers, and more particular from 5 to 10 micrometers.
11. The composition according to any one of claims 1 to 8, wherein the wax particles d) are selected from the group consisting of natural wax particles, synthetic wax particles, and a combination thereof.
12. The composition according to claim 9, wherein the wax particles d) are selected from the group consisting of carnauba wax particles, synthetic wax particles, polyethylene wax particles , and a combination thereof.
13. The composition according to any one of claims 1 to 12, wherein the non-volatile compound having at least one hydrophilic functional group e) is selected from the group consisting of glycerin, propylene glycol, dipropylene glycol, tripropylene glycol, diglycerin, ethylene glycol, triethylene glycol, isoprene glycol, diglycerin, pentylene glycol, hexylene glycol, sorbitol, mannitol, D-glucose, sucrose, D-fructose, xylitol, lactose, maltose, maltitol, trehalose, and hydroxyethyl urea.
14. The composition according to claim 1, wherein the composition comprises:
A) one or more UV filters as component a) in an amount of 5 to 30% by weight in total;
B) dimethicone as component b) in an amount of 5 to 20% by weight;
C) ethanol as component c) in an amount of 1 to 15% by weight;
D) wax particles selected from synthetic wax particles, natural wax particles and a combination thereof, which have a mean size by volume in the range from 0.5 to 30 micrometers as component d) ; E) glycerol as component e) in an amount of 1 to 15% by weight, relative to the total amount of the composition;
wherein the composition contains no cyclomethicones or contains a cyclomethicone in an amount 1% or less by weight relative to the total weight of the composition.
EP09796101A 2009-11-20 2009-11-20 A cosmetic or dermatological composition with low stickiness, containing a lipophilic active ingredient Withdrawn EP2501359A1 (en)

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PCT/JP2009/070080 WO2011061864A1 (en) 2009-11-20 2009-11-20 A cosmetic or dermatological composition with low stickiness, containing a lipophilic active ingredient

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JP (1) JP5819299B2 (en)
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CN102655839B (en) 2014-11-12

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