WO2018115360A1 - Composition comprising baicalin, a fatty acid ester and an alkylpolyglycoside - Google Patents

Composition comprising baicalin, a fatty acid ester and an alkylpolyglycoside Download PDF

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Publication number
WO2018115360A1
WO2018115360A1 PCT/EP2017/084234 EP2017084234W WO2018115360A1 WO 2018115360 A1 WO2018115360 A1 WO 2018115360A1 EP 2017084234 W EP2017084234 W EP 2017084234W WO 2018115360 A1 WO2018115360 A1 WO 2018115360A1
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Prior art keywords
composition
composition according
weight
alkyl
carbon atoms
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PCT/EP2017/084234
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French (fr)
Inventor
Stéphane DOUEZAN
Angelina Roudot
Maud WILLIEN
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L'oreal
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Publication of WO2018115360A1 publication Critical patent/WO2018115360A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/16Emollients or protectives, e.g. against radiation
    • 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
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations

Definitions

  • Composition comprising baicalin, a fatty acid ester and an
  • the present invention relates to a composition, and in particular a cosmetic composition, comprising baicalin, a method for preparing such a composition, along with the uses of this composition.
  • baicalin causes yellowing of the cosmetic compositions comprising same, which is difficult to accept from a cosmetic standpoint.
  • a technical problem therefore resides in the obtaining of a cosmetic composition comprising baicalin, or an extract that contains it, that is cosmetically acceptable, and in particular, that minimizes yellowing as much as possible.
  • a cosmetic composition comprising baicalin, or an extract that contains it, that is cosmetically acceptable, and in particular, that minimizes yellowing as much as possible.
  • the shine of the skin is a problem that generally affects adolescents, but which can also occur at the age of an adult under the effect in particular of a hyper-production of androgens or external factors such as pollution.
  • the shine of the skin can also be linked to sweat, resulting from physical activity or climate conditions (heat, humidity).
  • the shine of the skin can be due to the association of two phenomena (sebum and sweat).
  • the obtaining of a matte effect of the skin is highly sought by users with oily or combination skins, as well as for cosmetic compositions intended to be used in hot and humid climates.
  • the reflections caused by excess sebum and/or sweat on the surface of the skin are indeed generally considered as unattractive.
  • Shiny skin also generally results in not as good stability of the makeup which as such tends to degrade during the course of the day.
  • Another technical problem resides as such in the obtaining of a cosmetic composition containing baicalin, which makes it possible to obtain a matte effect on the skin.
  • compositions in particular for makeup or care, comprising baicalin, or an extract containing it, which are fresh when applied, and not oily.
  • the inventors have now revealed that the association of at least one fatty acid ester that has at least 24 carbon atoms, with at least one alkylpolyglycoside, makes it possible to minimize the yellowing of the baicalin in the compositions that contain it. Furthermore, such compositions have good properties to mattify the oily and/or glistening skin. They are furthermore fresh and not oily when applied.
  • the present invention therefore has for object a composition, in particular a cosmetic and/or dermatological composition, comprising in a physiologically acceptable medium:
  • This invention also relates to the use, in particular cosmetic, of a composition according to the invention to reduce the pigmentation induced by UV rays.
  • This invention also relates to a cosmetic care and/or makeup method of the skin and/or of the lips and/or of the hair, comprising the topical application on the skin and/or the lips and/or the hair of the composition according to the invention.
  • This invention also relates to a cosmetic and/or beauty treatment method comprising the topical application on the skin and/or lips and/or hair of a composition according to the invention for combating or preventing photo-induced premature aging of the skin and/or lips and/or hair.
  • This invention also relates to a cosmetic and/or beauty treatment method comprising the topical application on the skin and/or lips of a composition according to the invention, for protecting the skin and/or lips and/or hair against sun rays.
  • this invention also relates to the use of an association of one or several alkylC8-C30(poly)glycosides, and of one or several fatty acid esters, said ester comprising at least 24 carbon atoms, in order to decrease the yellowing of a composition containing at least Baicalin and/or one of the derivatives thereof or a plant extract containing it.
  • compositions according to the invention comprise at least Baicalin or one of the derivatives thereof or a plant extract containing said compound.
  • Each R4, R5, Ra, Rb and Rc independently, designates H, a (C1 -C10)alkyl radial optionally substituted with 1 to 5 Ry groups, or a (C1 -C10)alkyl-O-(C1 -C10)alkyl radial, with each (C1 -C10)alkyl radical able to be substituted with 1 to 5 Ry groups;
  • Each Ry independently, designates Rq or a -(C2-C10)alkenyl, -(C2-C10)alkynyl, - (C3-C10)cycloalkyl, -(C8-C14)bicycloalkyl, -(C8-C14)tricycloalkyl, -(C5-C10)cycloalkenyl, - (C8-C14)tricycloalkenyl, phenyl, naphthyl, -(C14)aryl radical, with each one able to be substituted with one or several Rz radicals;
  • Rf is H, (C1 -C12) alkyl optionally substituted with 1 to 5 Ry radicals, (C1 -C12)alkyl- 0-(C1 -C12)alkyl, with each (C1 -C12)alkyl radical able to be substituted with 1 to 5 Ry groups;
  • Each Rz is -(C1 -C6)alkyl, -(C2-C6)alkenyl, -(C3-C8)cycloalkyl, - (C3-C8)cycloalkenyl, phenyl, an heterocycle having 3 to 5 branches, CH(halo)2 or C(halo)3; and
  • n 0, 1 , 2, 3, 4 or 5 as well as the salts thereof, the optical isomers thereof and/or the diastereoisomers thereof.
  • Certain compounds having formula (I) can have asymmetric centers and exist in various enantiomeric and diastereoisomeric forms.
  • a compound having formula (I) can be in the form of an optical isomer or a diastereoisomer.
  • the compounds having formula (I) also comprise the optical isomeric forms thereof, diastereoisomers and mixtures thereof, including racemic mixtures.
  • -(C1 -C10)alkyl means a non-cyclic saturated, linear or branched hydrocarbon chain having from 1 to 10 carbon atoms.
  • linear saturated - (C1 -C10)alkyl radicals mention can be made of: methyl, ethyl, n-propyl, n-butyl, -n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.
  • branched saturated -(C1 - C10)alkyl radicals mention can be made of isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4- methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3- dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2- dimethylhexyl, 3,3-dimethylpentyl, -3,3-dimethylhexyl, 4,4-dimethylhe
  • -(C2-C10)alkenyl means a non-cyclic unsaturated, linear or branched hydrocarbon chain having from 2 to 10 carbon atoms and comprising at least one double carbon-carbon bond.
  • -(C1 -C10)alkenyl radicals mention can be made of: 2-pentenyl 3-methyl-1 -butenyl, 2-methyl-2-butenyl, 2,3-dimethyl-2-butenyl, 1 -hexenyl, 2- hexenyl, -3-hexenyl, 1 -heptenyl, 2-heptenyl, -3-heptenyl, 1 -octenyl, -2-octenyl, 3-octenyl,
  • -(C2-C10)alkynyl means a non-cyclic unsaturated, linear or branched hydrocarbon chain having from 2 to 10 carbon atoms and comprising at least one triple carbon-carbon bond.
  • -(C1 -C10)alkynyl radicals mention can be made of: acetylenyl, propynyl, 1 -butynyl, 2-butynyl, 1 -pentynyl, 2-pentynyl, 3-methyl-1 -butynyl, 4- pentynyl, 1 -hexynyl, 2-hexynyl, 5-hexynyl, 1 -heptynyl, -2-heptynyl, 6-heptynyl, 1 -octynyl,
  • -(C3-C10)cycloalkyl means a saturated hydrocarbon cycle having from 3 to 10 carbon atoms.
  • -(C3-C10)cycloalkyl radicals mention can be made of: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.
  • -(C8-C14)bicycloalkyl means a hydrocarbon bicycle having from 8 to 14 carbon atoms and at least one saturated cycloalkyl cycle.
  • -(C8- C14)bicycloalkyl radicals mention can be made of: indanyl, 1 ,2,3,4-tetrahydronaphthyl, 5,6,7,8-tetrahydronaphthyl, perhydronaphthyl.
  • -(C8-C14)bicycloalkyl means a hydrocarbon tricycle having from 8 to 14 carbon atoms and at least one saturated cycloalkyl cycle.
  • -(C8- C14)tricycloalkyl radicals mention can be made of: pyrenyl, 1 ,2,3,4- tetrahydroanthracenyl, perhydroanthracenyl, aceanthrenyl, 1 ,2,3,4- tetrahydropenanthrenyl, 5,6,7,8-tetrahydrophenanthrenyl, perhydrophenanthrenyl
  • -(C5-C10)cycloalkenyl means a cyclic non-aromatic hydrocarbon radical having at least one double carbon-carbon bond in the cyclic system and from 5 to 10 carbon atoms.
  • -(C5-C10)cycloalkenyl radicals mention can be made of: cyclopentadienyl, cyclohexenyl, cyclohexadieenyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienyl, cyclooctenyl, cyclooctadienyl, cyclooctatrienyl, cyclooctatetraenyl, cyclononenyl, cyclononadienyl, cyclodecenyl, cyclodecadienyl.
  • -(C8-C14)bicycloalkenyl means a hydrocarbon bicycle having at least one double carbon-carbon bond in each cycle and from 8 to 14 carbon atoms.
  • -(C8-C14)bicycloalkenyl radicals mention can be made of: indenyl, pentalenyl, naphthalenyl, azulenyl, heptalenyl, 1 ,2,7,8-tetrahydronaphthalenyl.
  • -(C8-C14)tricycloalkenyl means a hydrocarbon tricycle having at least one double carbon-carbon bond in each cycle and from 8 to 14 carbon atoms.
  • -(C8-C14)tricycloalkenyl radicals mention can be made of: anthracenyl, phenalenyl, acenaphthalenyl, as-indacenyl, s-indacenyl.
  • -(C14)aryl means a 14-branch aromatic carbocycle such as anthryl and phenanthryl.
  • heterocycle having 3 to 5 branches means a saturated, unsaturated, aromatic or non-aromatic heteromonocycle having 3 to 5 branches having carbon atoms and heteroatoms.
  • a heterocycle with 3 or 4 branches can comprise up to 3 heteroatoms and a heterocycle with 5 branches up to 4 heteroatoms.
  • Each heteroatom is independently chosen from a nitrogen that can be quaternized, oxygen and sulfur including sulfoxide and sulfone.
  • the heterocycle can be attached by any heteroatom or carbon atom.
  • heterocycles with 3-5 branches mention can be made of: furyl, thiophenyl, pyrrolyl, oxazolyl, imidazolyl, thiazolyl, isoxazolyl, pyrazolyl, isothiazolyl, triazinyl, pyrrolidinonyl, pyrrolidinyl, hydantoinyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl.
  • halo means a halogen atom such as F(Fluorine), CI (Chlorine), Br (Bromine) and I (Iodine).
  • -CH(halo)2 means a methyl group wherein 2 of the hydrogens are replaced with a halogen atom. Mention can be made for example of: -CHF2, -CHCI2, - CHBr2, -CHBrCI, -CHCII and -CHI2.
  • -CH(halo)3 means a methyl group wherein 3 of the hydrogens are replaced with a halogen atom. Mention can be made for example of: -CF3, -CF2CI, -CCI3, -CBr3, -CFBr2 and -CI3.
  • salts of the compounds having formula (I) means a salt formed by an inorganic or organic acid or an inorganic or organic base.
  • acid salts mention can be made of sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, citrate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (i.e., 1 ,1 ' -methylene-bis-(2-hydroxy-3-naphthoate)) salts.
  • sulfate citrate, acetate, oxalate, chloride, bromide, iod
  • base salts examples include alkali metal hydroxides such as sodium, potassium and lithium; alkali earth-metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminum and zinc; ammonia and organic amines such as non-substituted or hydroxy-substituted mono-,di- or trialkylarnines; dicyclohexylamines; tributyl amines; pyridine; N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2-hydroxy-alkylarnines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2-hydroxy-tert-butylarnine ortris- (hydroxymethyl)methylamine, N,N-di-alkyl-N-(hydroxyalkyl)-amines, such as N,N- dimethyl-N-(2-hydroxyethyl)amine or tri-(2-(2-hydroxyethy
  • At least one of the X1 , X2, X3, X4, X5, Xa, Xb, Xc, Xd, Xe and Xf radicals is O.
  • At least one of the Y1 , Y2, Y3, Y4, Y5, Y6 radicals, independently, designates H.
  • At least one of the Y1 , Y2, Y3, Y4, Y6 radicals designates CH3.
  • R1 designates H or CH3.
  • n is equal to 5.
  • composition of the invention comprises Baicalin that satisfies the following general formula (II):
  • Baicalin may be used in solution form comprising a glycol alkyl having 2 to 7 carbon atoms, a polyol ether, and at least one anti-oxidant.
  • Such an organic compound may be obtained as described in EP1400579 (US2004/0067894) relating to the synthesis of tetrahydroxyflavones wherein the general formula comprises Baicalin.
  • Baicalin may be used in the form of an extract of plant origin.
  • Baicalin is a polyphenol (flavone) particularly extracted from skull cap root, in particular from Scutellaria Baicalensis) with INCI name: SCUTELLARIA BAICALENSIS ROOT EXTRACT. It comes from traditional Chinese medicine.
  • the various modes for preparing extracts are described in application WO2005044281 .
  • Baicalin is in particular available from MMP under the trade name BAICALIN 95 MM® from MMP.
  • Baicalin having formula (II) and/or one of the compounds having formula (I) is present in concentrations of active substance ranging from 0.01 % to 10% by weight, better from 0.1 % to 8% by weight, and more preferably from about 0.2% to about 5% by weight with respect to the total weight of the composition.
  • composition according to the invention also comprises at least one alkylC8- C30(poly)glycoside.
  • R1 is a linear or branched alkyl and/or alkenyl radical comprising about 8 to 30 carbon atoms, a alkylphenyl radical of which the linear or branched alkyl radical comprises from 8 to 24 carbon atoms
  • R2 is an alkylene radical comprising about from 2 to 4 carbon atoms
  • G is a sugar pattern comprising from 5 to 6 carbon atoms
  • t designates a value ranging from 0 to 10, preferably 0 to 4, preferably 0 to 3
  • v designates a value ranging from 1 to 15, preferably from 1 to 4.
  • each unit of the polyoside portion of the alkylpolyglycoside can be of isomeric a or ⁇ form, in L or D form, and the configuration of the saccharide remainder can be of the furanoside or pyranoside type.
  • the alkyl(poly)glycoside surfactants are compounds having the formula described hereinabove wherein R1 designates more particularly a saturated or unsaturated, linear or branched alkyl radical comprising from 12 to 24 carbon atoms, t designates a value ranging from 0 to 3 and more particularly equal to 0, G can designate glucose, fructose, galactose, maltose, maltotriose, lactose, cellobiose, mannose, ribose, dextran, talose, allose, xylose, levoglucan, cellulose or starch, preferably glucose.
  • the degree of polymerization i.e. the value of v in the formula hereinabove, can range from 1 to 5, preferably from 1 to 4.
  • the average degree of polymerization is more particularly between 1 and 2.5, preferably from 1 .05 to 2.5, and more preferably from 1 .1 to 2.
  • the glucosidic bonds between the sugar patterns are of the 1 -6 or 1 -4 and preferably 1 -4 type.
  • Use can in particular be made of Coco(poly)glucoside (for example MONTANOV 82® and MONTANOV S®), arachidyl(poly)glucoside (for example MONTANOV 202®), Myristyl(poly)glucoside (for example MONTANOV 14®), Cetylstearyl(poly)glucoside (for example MONTANOV 68®), C12-C20 alkyl(poly)glucosides (for example MONTANOV L®), lsostearyl(poly)glucoside (for example Montanov WO 18®) or octyldodecyl(poly)xyloside (for example FLUIDANOV 20X ®.
  • Coco(poly)glucoside for example MONTANOV 82® and MONTANOV S®
  • arachidyl(poly)glucoside such as the commercial product MONTANOV 202® from SEPPIC.
  • the content in alkyl(poly)glycosides varies from 0.05 to 10% by weight, preferably from 0.1 to 5% by weight, and more preferably from 0.2 to 1 %, better from 0.25 to 0.6% by weight with respect to the total weight of the composition.
  • Fatty acid esters comprising at least 24 carbon atoms
  • composition according to the invention also comprises at least one fatty acid ester, said ester comprising at least 24 carbon atoms.
  • esters of acids comprising at least 24 carbon atoms are in particular esters comprising two or three C12-C30 fat chains.
  • They are preferably solid at a temperature less than or equal to about 30°C.
  • fatty acid esters according to the invention are in particular chosen from:
  • R and R' identical or different, designate a saturated or unsaturated, linear or branched hydrocarbon group, comprising from 12 to 30 carbon atoms and preferably from 14 to 24 carbon atoms.
  • R and R' radicals can be hydroxylated.
  • R and R' are chosen in such a way that the compound having formula (III) is solid at a temperature less than or equal to about 30°C.
  • R and R' are identical and designate a C14-C24 alkyl group such as behenyl, stearyl arachidyl.
  • Preferred compounds having formula (III) are for example behenyl behenate, stearyl stearate, arachidyl arachidate, and more particularly behenyl behenate.
  • Use can in particular be made of glyceryl tristearate, glyceryl distearate, glycerine trihydroxystearate, glyceryl trisbehenate or glyceryl dibehenate.
  • the fatty acid esters according to the invention are generally present in the compositions according to the invention in concentrations ranging from 0.1 to 10% by weight with respect to the total weight of the composition, preferably from 0.2 to 8% by weight, and more preferably from 0.5 to 5% by weight with respect to the total weight of the composition.
  • composition according to the invention may further comprise at least one C8-40 fatty alcohol.
  • the alkylC 8 -C 30 (poly)glycoside is a mixture with at least one C8-40 fatty alcohol.
  • C8-40 fatty alcohol means a long-chain aliphatic alcohol comprising from 8 to 40 carbon atoms, and comprising at least one hydroxyl OH group.
  • the fatty alcohols are R-OH structures with R designating a linear alkyl group, optionally substituted with one or several hydroxy groups, comprising from 8 to 40, better from 10 to 30, even from 12 to 24 atoms, even better from 14 to 22 carbon atoms.
  • the fatty alcohols that can be used can be chosen from, alone or in a mixture, lauric or laurylic (1 -dodecanol) alcohol, myristic or myristylic (1 -tetradecanol) alcohol, cetylic (1 -hexadecanol) alcohol, stearylic (1 -octadecanol) alcohol, arachidylic (1 - eicosanol) alcohol, behenyl (1 -docosanol) alcohol, lignocerylic (1 -tetracosanol) alcohol, cerylic (1 -hexacosanol) alcohol, montanyl (1 -octacosanol) alcohol, and myricyl (1 - triacontanol).
  • the fatty alcohol is chosen from cetylic alcohol, stearylic alcohol, arachidylic alcohol, behenyl alcohol and mixtures thereof, and more preferably from arachidyl alcohol, behenyl alcohol and mixtures thereof.
  • the fatty alcohol or fatty alcohols are present in concentrations ranging from 0.01 % to 15% by weight, preferably from 0.1 % to 10% by weight, and more preferably from 0.5% to 5% by weight, with respect to the total weight of the composition.
  • the composition according to the invention can be cosmetic and/or dermatological, preferably cosmetic.
  • composition according to the invention is generally adapted to topical application on the skin and it therefore generally comprises a physiologically acceptable medium, in other words compatible with the skin and/or the integuments thereof.
  • a physiologically acceptable medium in other words compatible with the skin and/or the integuments thereof.
  • This is preferably a cosmetically acceptable medium, i.e. that has a pleasant color, odor and texture and which does not give rise to unacceptable discomfort (tingling, tightness, redness), liable to dissuade the consumer from using the composition.
  • composition according to the invention may have any of the dosage forms conventionally used for topical application and particularly in the form of dispersions of the lotion or gel type, emulsions of liquid or semi-liquid consistency such as milk, obtained by dispersing a fatty phase in an aqueous phase (O/W) or conversely (W/O), or suspensions or emulsions of soft, semi-solid or solid consistency such as cream or gel, or multiple emulsions (W/O/W or 0/W/O), microemulsions.
  • the composition according to the invention can as an alternative have the form of sticks. These compositions are prepared according to the usual methods.
  • compositions used according to the invention can be more or less fluid and have the appearance of a white or colored cream, of an ointment, of a milk, of a lotion, of a serum, of a paste or of a foam. They can also have a solid form, and for example have the form of a stick.
  • the compositions are liquid.
  • the cosmetic composition according to the invention may further comprises at least one organic and/or mineral sun filter (filters of UV rays from sunlight).
  • the UV filters is a UV filter routinely used in cosmetics. It may be chosen in the positive list contained in Annex VI of the Regulation (EC) N° 1223/2009, which specifies the list of UV filters authorized in cosmetics.
  • the UV filters of the composition according to the invention can be organic, lipophilic, hydrophilic or insoluble.
  • the UV filters of the composition according to the invention can provide a UVA and/or UVB photoprotection.
  • the composition further comprises at least one UV filter chosen from organic hydrophilic UV filters, organic lipophilic UV filters, insoluble organic UV filters, mineral filters or any of the mixtures thereof.
  • the composition may comprise one or several bis- resorcinyl triazine derivatives as described and prepared according to the syntheses indicated in patent applications EP-A-0775 698.
  • Examples of such compounds suitable for use include:
  • the composition may comprise one or several dibenzoylmethane derivatives. Particularly mention may be made of, but is not limited to:
  • the composition may comprise one or several benzylidene camphor derivatives. Mention can be made in particular of:
  • the composition can comprise one or several derivatives of ⁇ , ⁇ '-diphenylacrylate, such as etocrylene, sold under the trade name "UVINUL N35" by BASF; or octocrylene, sold in particular under the trade name "UVINUL N539" by BASF.
  • etocrylene sold under the trade name "UVINUL N35” by BASF
  • octocrylene sold in particular under the trade name "UVINUL N539” by BASF.
  • the organic UV filters can also be selected from anthranilics; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenyl benzotriazole derivatives; benzalmalonate derivatives particularly those cited in the patent US5624663; phenyl benzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis- benzoazolyl derivatives as described in the patents EP669323 and US 2,463,264; p- aminobenzoic acid (PABA) derivatives; methylene bis-(hydroxyphenyl benzotriazole) derivatives as described in the applications US5,237,071 , US 5,166,355, GB2303549, DE 197 26 184 and EP8931 19; benzoxazole derivatives as described in the patent applications EP0832642, EP1027883, EP1300137 and DE10162844; filter polymers and filter silicones such as those particularly described in the application WO-93/04
  • the quantity of the UV filter or filters, present in the composition according to the invention may range from 0.001 to 50% by weight, with respect to the total weight of the composition. It ranges for example from 1 to 50% by weight, or for example from 5 to 50% by mass, and for example ranges from 7 to 20% by mass with respect to the total mass of the composition.
  • the cosmetic composition according to the invention may further comprise at least one thickener.
  • thickener means a compound that introduced at 1 % by weight in pure water and at pH 7 and at 25°C has a viscosity greater than 1 1 ,000 Pa.s.
  • the viscosity is measured in Pa.s for a shear value of 0.001 s-1 using a HAAKE Mars rheometer with titanium sand-blasted cone-plate geometry 35 mm in diameter with an angle of 2°. The measurements are taken in imposed constrained equilibrium.
  • the thickeners according to the invention can be of natural or synthetic, mineral or organic origin.
  • the thickeners can be anionic, cationic, amphoteric or non-ionic polymers, associative or not.
  • one or a plurality of thickeners and/or gelling agents may be incorporated in the composition.
  • hydrophilic gelling agents mention may be made for example of optionally modified carboxyvinyl polymers, such as the products marketed under the trade names Carbopol (CTFA name: carbomer) and Pemulen (CTFA name: Acrylates/C 10-30 akyl acrylate crosspolymer) by Goodrich; polyacrylamides; 2- acrylamido 2-methylpropane sulfonic acid polymers and copolymers (AMPS), optionally cross-linked and/or neutralized, such as poly(2-acrylamido-2-methylpropanesulfonic acid) marketed by Hoechst under the trade name "Hostacerin AMPS" (CTFA name: Ammonium Polyacryldimethyltauramide); cross-linked anionic acrylamide/AMPS copolymers
  • the mineral thickeners can be chosen from clays, optionally modified, silicas, optionally modified, or mixtures thereof.
  • the mineral thickeners are chosen from lipophilic clays in particular modified hectorites; pyrogenic silica with a hydrophobic treatment; hydrophobic silica aerogels, or mixtures thereof.
  • the thickeners according to the invention are generally present in the composition according to the invention at a content ranging from 0.01 % to 20% by weight, preferably from 0.1 % to 10% by weight, and most preferably from 0.5% to 10% by weight, with respect to the total weight of the composition.
  • composition used according to the invention comprises an oil phase
  • the latter preferably contains at least one oil. It may further contain other fats.
  • composition according to the invention can as such also comprise at least one oil.
  • oils suitable for use in the composition of the invention mention may be made for example of:
  • hydrocarbon oils of plant origin such as liquid fatty acid triglycerides having 4 to 10 carbon atoms such as heptanoic or octanoic triglycerides or, for example the sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado oil, caprylic/capric acid triglycerides such as those sold by Stearineries Dubois or those sold under the trade names Miglyol "810", “812" and “818” by Dynamit Nobel, jojoba oil, shea butter oil;
  • liquid fatty acid triglycerides having 4 to 10 carbon atoms such as heptanoic or octanoic triglycerides or, for example the sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado oil, caprylic/cap
  • esters and synthetic esters in particular fatty acids, such as oils having formulas R1 COOR2 and R10R2 wherein R1 is the remainder of a fatty acid comprising from 8 to 29 carbon atoms, and R2 is a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, such as for example Purcellin oil, isononyl isononanoate, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl-malate, triisocetyl citrate; heptanoates, octanoates, de
  • hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polybutene such as Parleam; isododecane, isohexadecane;
  • - fatty alcohols having 8 to 26 carbon atoms such as cetyl alcohol, stearyl alcohol, and the mixture thereof (cetylstearyl alcohol), octyl dodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol;
  • silicone oils such as polymethylsiloxanes (PDMS), optionally volatile with a linear or cyclic silicone chain, liquid or pasty at ambient temperature, particularly cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl pendant or silicon chain-end groups, groups having 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenyl-siloxanes, diphenyl-dimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyltrimethyl- siloxysilicates, and polymethylphenylsiloxanes; and
  • hydrocarbon oil in the list of oils cited above denotes any oil comprising mostly carbon and hydrogen atoms, and optionally ester, ether, fluorinated, carboxylic acid and/or alcohol groups.
  • the proportion of oil can range from 2 to 50% by weight, and preferably from 5 to 30% by weights, more particularly from 7 to 20% by weight with respect to the total weight of the composition.
  • the other fats suitable for being present in the oil phase are for example fatty acids comprising 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, Carnauba or Candellila wax, paraffin wax, lignite wax or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-C1 -4- alkyldimethicone and trifluoropropyldimethicone; and silicon elastomers such as the products marketed under the trade names "KSG” by Shin-Etsu, under the trade names "Trefil", "BY29” or “EPSX” by Dow Corning or under the trade names "Gransil” by Grant Industries. These fats may be chosen in varied ways by those skilled in the art in order to prepare a composition having the properties,
  • the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion, preferably O/W.
  • the proportion of the fatty phase of the emulsion may range from 2 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.
  • the composition comprises at least one aqueous phase.
  • the composition according to the invention preferably comprises an aqueous phase comprising water and a water-soluble organic solvent, chosen for example from C2-C4 linear or branched alkanols, such as ethanol and isopropanol, propanol, butanol; polyols and polyol ethers such as 2-butoxyethanol, glycerol, diglycerol, propyleneglycol, dipropyleneglycol, butylene glycol, hexylene glycol, 1 ,3-propanediol, pentylene glycol, polyethyleneglycols, propyleneglycol monomethylether, monoethylether and monomethylether of diethyleneglycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof
  • a water-soluble organic solvent chosen for example from C2-C4 linear or branched alkanols, such as ethanol and isopropan
  • the composition generally comprises from 30 to 95% by weight of water with respect to the total weight of the composition.
  • the quantity of water-soluble organic solvents can range from for example 0 to 30% by weight, preferably from 0.5 to 20% by weight, better from 1 to 15% by weight, even better from 2 to 10% by weight and even better from 2 to 8% by weight relative to the total weight of the composition.
  • composition according to the invention can be a composition for the treatment, cleaning or makeup of the body or of the face, in particular, a treatment composition.
  • the skin treatment composition can for example be a cream, a gel or a fluid for the face.
  • the composition according to this invention can furthermore contain various adjuvants that are commonly used ion the cosmetics field, such as surfactants, emulsifiers; fillers; preservatives; sequestering agents; colorants; perfumes; pH agents.
  • the composition can further comprise at least one treatment agent.
  • This agent is preferably chosen from desquamating, anti-microbial, antiinflammatory, sebo-regulating, anti-oxidant, moisturizing agents and vitamins. Obviously, those skilled in the art will take care to choose these optional additional compounds, and/or the quantity thereof, such as the advantageous properties of the composition according to the invention are not, or are substantially not, altered by the envisaged addition.
  • the agent or agents used in the composition according to the invention can represent from 0.0001 to 20%, preferably from 0.001 to 10% and, better, from 0.01 to 5% of the total weight of the composition.
  • the invention further has for object a cosmetic care and/or makeup method of the skin, comprising the topical application on the skin of the composition according to the invention.
  • the invention also has for object the use of an association of one or several alkylC8-C30(poly)glycosides (compound(s) b), and of one or several fatty acid esters, said ester comprising at least 24 carbon atoms (compound(s) c), in order to decrease the yellowing of a composition containing at least Baicalin and/or one of the derivatives thereof or a plant extract containing it.
  • compositions A to C are comparative
  • compositions D and E are according to the invention.
  • the preparation protocol is as follows:
  • Phase A2 is heated to 70°C and introduced into the phase A1 .
  • the mixture obtained is yellow and limpid.
  • Phase B is heated to 70°C using a heating plate, then introduced into the phase A1 +A2 under stirring using a Moritz rotor stator. The stirring is maintained for 10 minutes. The preparation is brought to ambient temperature.
  • Phases C and D are successively introduced into the phase A1 +A2+B under Rayneri stirring.
  • the pH is adjusted to 5.5 ⁇ 0.3.
  • the matteness, freshness and greasy aspect are evaluated by a panel of sensory experts of 10 people. Each composition is applied on the forearm with a dose of 2mg/cm 2 . The product is spread by circular movements until penetration of the product (about 30 seconds). The evaluation of the freshness is carried out during the application. The evaluation of the matteness and of the greasy aspect is carried out after 2 minutes of drying:
  • Freshness is evaluated according to a scale ranging from 1 to 15, where 1 constitutes a non-fresh reference and 15 constitutes a very fresh reference.
  • Matteness is evaluated with the eye after 2 minutes of drying according to a scale ranging from 1 to 15, where 1 constitutes a very shiny reference and 15 constitutes a very matte reference.
  • the greasy aspect is evaluated with the finger after 2 minutes of drying according to a scale ranging from 1 to 15, where 1 constitutes a very greasy reference and 15 constitutes a hardly greasy reference.
  • the color of the formulas is evaluated after preparation of thin films on a contrast card.
  • the formulas are arranged within a circle of 2.2 cm in diameter and are leveled in order to obtain reproducible deposit thicknesses.
  • the colorimetric measurements are then taken using a Minolta CM2600D spectro-colorimeter with two points of the film. This operation is repeated twice, which leads to 4 experimental values per composition.
  • a * and b * express the shade of the compound.
  • Chroma value C * is, the more marked the intensity of the color of the product is.
  • composition A comparative composition
  • a formula comprising baicalin, Arlacel 165 and cetyl alcohol (which constitutes a conventional surfactant system)
  • the composition B contains the same surfactant system as the composition A, with in addition behenyl behenate.
  • the results are similar to those of the composition A.
  • composition C (comparative composition) contains, as the only surfactant, Montanov 202.
  • the results show a reduced yellow coloration, but strong shine and a greasy effect.
  • compositions D and E according to the invention are the only ones that show both a low yellow coloration, strong matteness (low shine), and a non-greasy finish.

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Abstract

This invention relates to a cosmetic and/or dermatological composition, comprising in a physiologically acceptable medium: a) at least Baicalin and/or one of the derivatives thereof or a plant extract containing it, b) one or several alkyl C8-C30(poly)glycosides, and c) one or several fatty acid esters, said ester comprising at least 24 carbon atoms.

Description

Composition comprising baicalin, a fatty acid ester and an
alkylpolyglycoside
The present invention relates to a composition, and in particular a cosmetic composition, comprising baicalin, a method for preparing such a composition, along with the uses of this composition.
Numerous cosmetic compositions comprising baicalin as an antioxidant or as a photoprotector, or an extract containing same, are known in the prior art. Patent application EP 27291 17 A1 in particular describes photoprotective compositions comprising baicalin.
However, one of the disadvantages resides in the fact that baicalin causes yellowing of the cosmetic compositions comprising same, which is difficult to accept from a cosmetic standpoint.
A technical problem therefore resides in the obtaining of a cosmetic composition comprising baicalin, or an extract that contains it, that is cosmetically acceptable, and in particular, that minimizes yellowing as much as possible. Furthermore, in the field of photoprotection, there is a constant need for compositions that make it possible to obtain a matte effect of the skin. Indeed, the shine of the skin, generally linked to a substantial secretion of sebum, is a problem that generally affects adolescents, but which can also occur at the age of an adult under the effect in particular of a hyper-production of androgens or external factors such as pollution. The shine of the skin can also be linked to sweat, resulting from physical activity or climate conditions (heat, humidity). The shine of the skin can be due to the association of two phenomena (sebum and sweat).
The obtaining of a matte effect of the skin is highly sought by users with oily or combination skins, as well as for cosmetic compositions intended to be used in hot and humid climates. The reflections caused by excess sebum and/or sweat on the surface of the skin are indeed generally considered as unattractive. Shiny skin also generally results in not as good stability of the makeup which as such tends to degrade during the course of the day. Another technical problem resides as such in the obtaining of a cosmetic composition containing baicalin, which makes it possible to obtain a matte effect on the skin.
Finally, there is a need for cosmetic compositions, in particular for makeup or care, comprising baicalin, or an extract containing it, which are fresh when applied, and not oily.
The inventors have now revealed that the association of at least one fatty acid ester that has at least 24 carbon atoms, with at least one alkylpolyglycoside, makes it possible to minimize the yellowing of the baicalin in the compositions that contain it. Furthermore, such compositions have good properties to mattify the oily and/or glistening skin. They are furthermore fresh and not oily when applied.
The present invention therefore has for object a composition, in particular a cosmetic and/or dermatological composition, comprising in a physiologically acceptable medium:
a) at least Baicalin and/or one of the derivatives thereof or a plant extract containing it,
b) one or several alkylC8-C30(poly)glycosides, and
c) one or several fatty acid esters, said ester comprising at least 24 carbon atoms.
This invention also relates to the use, in particular cosmetic, of a composition according to the invention to reduce the pigmentation induced by UV rays.
This invention also relates to a cosmetic care and/or makeup method of the skin and/or of the lips and/or of the hair, comprising the topical application on the skin and/or the lips and/or the hair of the composition according to the invention.
This invention also relates to a cosmetic and/or beauty treatment method comprising the topical application on the skin and/or lips and/or hair of a composition according to the invention for combating or preventing photo-induced premature aging of the skin and/or lips and/or hair.
This invention also relates to a cosmetic and/or beauty treatment method comprising the topical application on the skin and/or lips of a composition according to the invention, for protecting the skin and/or lips and/or hair against sun rays.
Finally, this invention also relates to the use of an association of one or several alkylC8-C30(poly)glycosides, and of one or several fatty acid esters, said ester comprising at least 24 carbon atoms, in order to decrease the yellowing of a composition containing at least Baicalin and/or one of the derivatives thereof or a plant extract containing it.
The constituents of the composition according to the invention shall now be described in more detail.
Baicalin and the derivatives thereof
The compositions according to the invention comprise at least Baicalin or one of the derivatives thereof or a plant extract containing said compound.
Baicalin and the derivatives thereof have been described, as well as their methods of preparation, in particular in application WO2005044281 . They satisfy the following general formula (I):
Figure imgf000004_0001
(1) wherein
Each X1 , X2, X3, X4, X5, Xa, Xb, Xc, Xd, Xe and Xf, independently, designate O or S;
Each Y1 , Y2, Y3, Y4, Y5, Y6, independently, designate H or a (C1 -C10)alkyl radical, in particular methyl;
Each R4, R5, Ra, Rb and Rc, independently, designates H, a (C1 -C10)alkyl radial optionally substituted with 1 to 5 Ry groups, or a (C1 -C10)alkyl-O-(C1 -C10)alkyl radial, with each (C1 -C10)alkyl radical able to be substituted with 1 to 5 Ry groups;
Each Ry, independently, designates Rq or a -(C2-C10)alkenyl, -(C2-C10)alkynyl, - (C3-C10)cycloalkyl, -(C8-C14)bicycloalkyl, -(C8-C14)tricycloalkyl, -(C5-C10)cycloalkenyl, - (C8-C14)tricycloalkenyl, phenyl, naphthyl, -(C14)aryl radical, with each one able to be substituted with one or several Rz radicals;
Each R1 R2, R3, independently, designates H or Rq or a -(C2-C10)alkenyl, -(C2- C10)alkynyl, -(C3-C10)cycloalkyl, -(C8-C14)bicycloalkyl, -(C8-C14)tricycloalkyl, -(C5- C10)cycloalkenyl, -(C8-C14)tricycloalkenyl, phenyl, naphthyl, -(C14)aryl radical, with each one able to be substituted with one or several Rz radicals;
Rf is H, (C1 -C12) alkyl optionally substituted with 1 to 5 Ry radicals, (C1 -C12)alkyl- 0-(C1 -C12)alkyl, with each (C1 -C12)alkyl radical able to be substituted with 1 to 5 Ry groups;
Each Rq, independently, is CN, OH, halogen, N3, N02, N(Rz)2, =NRz, CH=NRz,
NRzOH, ORz, CORz, C(0)Rz, 0(CO)ORz, SRz, S(0)Rz or S(0)2Rz;
Each Rz, independently, is -(C1 -C6)alkyl, -(C2-C6)alkenyl, -(C3-C8)cycloalkyl, - (C3-C8)cycloalkenyl, phenyl, an heterocycle having 3 to 5 branches, CH(halo)2 or C(halo)3; and
n is 0, 1 , 2, 3, 4 or 5 as well as the salts thereof, the optical isomers thereof and/or the diastereoisomers thereof.
Certain compounds having formula (I) can have asymmetric centers and exist in various enantiomeric and diastereoisomeric forms. A compound having formula (I) can be in the form of an optical isomer or a diastereoisomer. According to the invention, the compounds having formula (I) also comprise the optical isomeric forms thereof, diastereoisomers and mixtures thereof, including racemic mixtures.
The term "-(C1 -C10)alkyl" means a non-cyclic saturated, linear or branched hydrocarbon chain having from 1 to 10 carbon atoms. As examples of linear saturated - (C1 -C10)alkyl radicals, mention can be made of: methyl, ethyl, n-propyl, n-butyl, -n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl. As examples of branched saturated -(C1 - C10)alkyl radicals, mention can be made of isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4- methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3- dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2- dimethylhexyl, 3,3-dimethylpentyl, -3,3-dimethylhexyl, 4,4-dimethylhexyl, 2-ethylpentyl, 3- ethylpentyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentyl, 2-methyl-3- ethylpentyl, 2-methyl-4-ethylpentyl, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, -2- methyl-4-ethylhexyl, 2,2-diethylpentyl, 3,3-diehylhexyl, 2,2-diethylhexyl, 3,3-diethylhexyl. The term "-(C2-C10)alkenyl" means a non-cyclic unsaturated, linear or branched hydrocarbon chain having from 2 to 10 carbon atoms and comprising at least one double carbon-carbon bond. As examples of -(C1 -C10)alkenyl radicals, mention can be made of: 2-pentenyl 3-methyl-1 -butenyl, 2-methyl-2-butenyl, 2,3-dimethyl-2-butenyl, 1 -hexenyl, 2- hexenyl, -3-hexenyl, 1 -heptenyl, 2-heptenyl, -3-heptenyl, 1 -octenyl, -2-octenyl, 3-octenyl,
1 - nonenyl, 2-nonenyl, 3-nonenyl, 1 -decenyl, 2-decenyl, 3-decenyl.
The term "-(C2-C10)alkynyl" means a non-cyclic unsaturated, linear or branched hydrocarbon chain having from 2 to 10 carbon atoms and comprising at least one triple carbon-carbon bond. As examples of -(C1 -C10)alkynyl radicals, mention can be made of: acetylenyl, propynyl, 1 -butynyl, 2-butynyl, 1 -pentynyl, 2-pentynyl, 3-methyl-1 -butynyl, 4- pentynyl, 1 -hexynyl, 2-hexynyl, 5-hexynyl, 1 -heptynyl, -2-heptynyl, 6-heptynyl, 1 -octynyl,
2- octynyl, 7-octynyl, 1 -nonynyl, 2-nonynyl, 8-nonynyl, 1 -decynyl, 2-decynyl, 9-decynyl.
The term "-(C3-C10)cycloalkyl" means a saturated hydrocarbon cycle having from 3 to 10 carbon atoms. As examples of -(C3-C10)cycloalkyl radicals, mention can be made of: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.
The term "-(C8-C14)bicycloalkyl" means a hydrocarbon bicycle having from 8 to 14 carbon atoms and at least one saturated cycloalkyl cycle. As examples of -(C8- C14)bicycloalkyl radicals, mention can be made of: indanyl, 1 ,2,3,4-tetrahydronaphthyl, 5,6,7,8-tetrahydronaphthyl, perhydronaphthyl.
The term "-(C8-C14)bicycloalkyl" means a hydrocarbon tricycle having from 8 to 14 carbon atoms and at least one saturated cycloalkyl cycle. As examples of -(C8- C14)tricycloalkyl radicals, mention can be made of: pyrenyl, 1 ,2,3,4- tetrahydroanthracenyl, perhydroanthracenyl, aceanthrenyl, 1 ,2,3,4- tetrahydropenanthrenyl, 5,6,7,8-tetrahydrophenanthrenyl, perhydrophenanthrenyl
The term "-(C5-C10)cycloalkenyl" means a cyclic non-aromatic hydrocarbon radical having at least one double carbon-carbon bond in the cyclic system and from 5 to 10 carbon atoms. As examples of -(C5-C10)cycloalkenyl radicals, mention can be made of: cyclopentadienyl, cyclohexenyl, cyclohexadieenyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienyl, cyclooctenyl, cyclooctadienyl, cyclooctatrienyl, cyclooctatetraenyl, cyclononenyl, cyclononadienyl, cyclodecenyl, cyclodecadienyl.
The term "-(C8-C14)bicycloalkenyl" means a hydrocarbon bicycle having at least one double carbon-carbon bond in each cycle and from 8 to 14 carbon atoms. As examples of -(C8-C14)bicycloalkenyl radicals, mention can be made of: indenyl, pentalenyl, naphthalenyl, azulenyl, heptalenyl, 1 ,2,7,8-tetrahydronaphthalenyl.
The term "-(C8-C14)tricycloalkenyl" means a hydrocarbon tricycle having at least one double carbon-carbon bond in each cycle and from 8 to 14 carbon atoms. As examples of -(C8-C14)tricycloalkenyl radicals, mention can be made of: anthracenyl, phenalenyl, acenaphthalenyl, as-indacenyl, s-indacenyl.
The term "-(C14)aryl" means a 14-branch aromatic carbocycle such as anthryl and phenanthryl.
The term "heterocycle having 3 to 5 branches" means a saturated, unsaturated, aromatic or non-aromatic heteromonocycle having 3 to 5 branches having carbon atoms and heteroatoms. A heterocycle with 3 or 4 branches can comprise up to 3 heteroatoms and a heterocycle with 5 branches up to 4 heteroatoms. Each heteroatom is independently chosen from a nitrogen that can be quaternized, oxygen and sulfur including sulfoxide and sulfone. The heterocycle can be attached by any heteroatom or carbon atom. As examples of heterocycles with 3-5 branches, mention can be made of: furyl, thiophenyl, pyrrolyl, oxazolyl, imidazolyl, thiazolyl, isoxazolyl, pyrazolyl, isothiazolyl, triazinyl, pyrrolidinonyl, pyrrolidinyl, hydantoinyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl.
The term "halo" means a halogen atom such as F(Fluorine), CI (Chlorine), Br (Bromine) and I (Iodine).
The term "-CH(halo)2" means a methyl group wherein 2 of the hydrogens are replaced with a halogen atom. Mention can be made for example of: -CHF2, -CHCI2, - CHBr2, -CHBrCI, -CHCII and -CHI2. The term "-CH(halo)3" means a methyl group wherein 3 of the hydrogens are replaced with a halogen atom. Mention can be made for example of: -CF3, -CF2CI, -CCI3, -CBr3, -CFBr2 and -CI3. The term "salts of the compounds having formula (I)" means a salt formed by an inorganic or organic acid or an inorganic or organic base.
As examples of acid salts, mention can be made of sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, citrate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (i.e., 1 ,1 ' -methylene-bis-(2-hydroxy-3-naphthoate)) salts. As examples of base salts, mention can be made of alkali metal hydroxides such as sodium, potassium and lithium; alkali earth-metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminum and zinc; ammonia and organic amines such as non-substituted or hydroxy-substituted mono-,di- or trialkylarnines; dicyclohexylamines; tributyl amines; pyridine; N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2-hydroxy-alkylarnines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2-hydroxy-tert-butylarnine ortris- (hydroxymethyl)methylamine, N,N-di-alkyl-N-(hydroxyalkyl)-amines, such as N,N- dimethyl-N-(2-hydroxyethyl)amine or tri-(2-hydroxyethyl)arnine; N-methyl-D-glucamine; and amino acids such as arginine and lysine.
According to a preferred form of the invention, at least one of the X1 , X2, X3, X4, X5, Xa, Xb, Xc, Xd, Xe and Xf radicals is O.
According to a preferred form of the invention, at least one of the Y1 , Y2, Y3, Y4, Y5, Y6 radicals, independently, designates H.
According to a preferred form of the invention, at least one of the Y1 , Y2, Y3, Y4, Y6 radicals, independently, designates CH3.
According to a preferred form of the invention, R1 designates H or CH3. According to a preferred form of the invention, n is equal to 5.
According to a particularly preferred form, the composition of the invention comprises Baicalin that satisfies the following general formula (II):
Figure imgf000009_0001
(Π) or a plant extract that comprises it.
This compound is in particular described in the application WO2008/140440 particularly in solution form. Baicalin may be used in solution form comprising a glycol alkyl having 2 to 7 carbon atoms, a polyol ether, and at least one anti-oxidant. Such an organic compound may be obtained as described in EP1400579 (US2004/0067894) relating to the synthesis of tetrahydroxyflavones wherein the general formula comprises Baicalin.
Baicalin may be used in the form of an extract of plant origin. Baicalin is a polyphenol (flavone) particularly extracted from skull cap root, in particular from Scutellaria Baicalensis) with INCI name: SCUTELLARIA BAICALENSIS ROOT EXTRACT. It comes from traditional Chinese medicine. The various modes for preparing extracts are described in application WO2005044281 .
Baicalin is in particular available from MMP under the trade name BAICALIN 95 MM® from MMP.
Baicalin having formula (II) and/or one of the compounds having formula (I) is present in concentrations of active substance ranging from 0.01 % to 10% by weight, better from 0.1 % to 8% by weight, and more preferably from about 0.2% to about 5% by weight with respect to the total weight of the composition. AlkylC8-C30(Dolv)alvcosides
The composition according to the invention also comprises at least one alkylC8- C30(poly)glycoside.
These surfactants can be more particularly represented by the following general formula:
R10-(R20)t (G)v
wherein R1 is a linear or branched alkyl and/or alkenyl radical comprising about 8 to 30 carbon atoms, a alkylphenyl radical of which the linear or branched alkyl radical comprises from 8 to 24 carbon atoms; R2 is an alkylene radical comprising about from 2 to 4 carbon atoms; G is a sugar pattern comprising from 5 to 6 carbon atoms; t designates a value ranging from 0 to 10, preferably 0 to 4, preferably 0 to 3; and v designates a value ranging from 1 to 15, preferably from 1 to 4. Note furthermore that each unit of the polyoside portion of the alkylpolyglycoside can be of isomeric a or β form, in L or D form, and the configuration of the saccharide remainder can be of the furanoside or pyranoside type.
It is of course possible to use mixtures of alkylpolyosides, able to differ from one another by the nature of the alkyl pattern carried and/or the nature of the polyoside carrier chain.
According to a particular embodiment, the alkyl(poly)glycoside surfactants are compounds having the formula described hereinabove wherein R1 designates more particularly a saturated or unsaturated, linear or branched alkyl radical comprising from 12 to 24 carbon atoms, t designates a value ranging from 0 to 3 and more particularly equal to 0, G can designate glucose, fructose, galactose, maltose, maltotriose, lactose, cellobiose, mannose, ribose, dextran, talose, allose, xylose, levoglucan, cellulose or starch, preferably glucose. The degree of polymerization, i.e. the value of v in the formula hereinabove, can range from 1 to 5, preferably from 1 to 4. The average degree of polymerization is more particularly between 1 and 2.5, preferably from 1 .05 to 2.5, and more preferably from 1 .1 to 2.
The glucosidic bonds between the sugar patterns are of the 1 -6 or 1 -4 and preferably 1 -4 type. Use can in particular be made of Coco(poly)glucoside (for example MONTANOV 82® and MONTANOV S®), arachidyl(poly)glucoside (for example MONTANOV 202®), Myristyl(poly)glucoside (for example MONTANOV 14®), Cetylstearyl(poly)glucoside (for example MONTANOV 68®), C12-C20 alkyl(poly)glucosides (for example MONTANOV L®), lsostearyl(poly)glucoside (for example Montanov WO 18®) or octyldodecyl(poly)xyloside (for example FLUIDANOV 20X ®.
Preference is given to arachidyl(poly)glucoside such as the commercial product MONTANOV 202® from SEPPIC.
According to a particular embodiment of the invention, the content in alkyl(poly)glycosides varies from 0.05 to 10% by weight, preferably from 0.1 to 5% by weight, and more preferably from 0.2 to 1 %, better from 0.25 to 0.6% by weight with respect to the total weight of the composition.
Fatty acid esters comprising at least 24 carbon atoms
The composition according to the invention also comprises at least one fatty acid ester, said ester comprising at least 24 carbon atoms.
The esters of acids comprising at least 24 carbon atoms are in particular esters comprising two or three C12-C30 fat chains.
With the total number of carbon atoms of the ester ranging from 30 to 100, preferably from 40 to 80.
They are preferably solid at a temperature less than or equal to about 30°C.
The fatty acid esters according to the invention are in particular chosen from:
A) those responding to the following formula (III):
R-COO-R' (III)
wherein:
R and R', identical or different, designate a saturated or unsaturated, linear or branched hydrocarbon group, comprising from 12 to 30 carbon atoms and preferably from 14 to 24 carbon atoms.
The R and R' radicals can be hydroxylated. R and R' are chosen in such a way that the compound having formula (III) is solid at a temperature less than or equal to about 30°C. Preferably, R and R' are identical and designate a C14-C24 alkyl group such as behenyl, stearyl arachidyl. Preferred compounds having formula (III) are for example behenyl behenate, stearyl stearate, arachidyl arachidate, and more particularly behenyl behenate.
B) and C12-C30 di- or triesters of glycerol and of fatty acids:
Use can in particular be made of glyceryl tristearate, glyceryl distearate, glycerine trihydroxystearate, glyceryl trisbehenate or glyceryl dibehenate.
The fatty acid esters according to the invention are generally present in the compositions according to the invention in concentrations ranging from 0.1 to 10% by weight with respect to the total weight of the composition, preferably from 0.2 to 8% by weight, and more preferably from 0.5 to 5% by weight with respect to the total weight of the composition.
According to a particular embodiment, the composition according to the invention may further comprise at least one C8-40 fatty alcohol.
As such, according to a preferred embodiment, the alkylC8-C30(poly)glycoside is a mixture with at least one C8-40 fatty alcohol.
The term C8-40 fatty alcohol means a long-chain aliphatic alcohol comprising from 8 to 40 carbon atoms, and comprising at least one hydroxyl OH group.
Preferably, the fatty alcohols are R-OH structures with R designating a linear alkyl group, optionally substituted with one or several hydroxy groups, comprising from 8 to 40, better from 10 to 30, even from 12 to 24 atoms, even better from 14 to 22 carbon atoms.
The fatty alcohols that can be used can be chosen from, alone or in a mixture, lauric or laurylic (1 -dodecanol) alcohol, myristic or myristylic (1 -tetradecanol) alcohol, cetylic (1 -hexadecanol) alcohol, stearylic (1 -octadecanol) alcohol, arachidylic (1 - eicosanol) alcohol, behenyl (1 -docosanol) alcohol, lignocerylic (1 -tetracosanol) alcohol, cerylic (1 -hexacosanol) alcohol, montanyl (1 -octacosanol) alcohol, and myricyl (1 - triacontanol).
Preferably, the fatty alcohol is chosen from cetylic alcohol, stearylic alcohol, arachidylic alcohol, behenyl alcohol and mixtures thereof, and more preferably from arachidyl alcohol, behenyl alcohol and mixtures thereof.
Preferably, the fatty alcohol or fatty alcohols are present in concentrations ranging from 0.01 % to 15% by weight, preferably from 0.1 % to 10% by weight, and more preferably from 0.5% to 5% by weight, with respect to the total weight of the composition. The composition according to the invention can be cosmetic and/or dermatological, preferably cosmetic.
The composition according to the invention is generally adapted to topical application on the skin and it therefore generally comprises a physiologically acceptable medium, in other words compatible with the skin and/or the integuments thereof. This is preferably a cosmetically acceptable medium, i.e. that has a pleasant color, odor and texture and which does not give rise to unacceptable discomfort (tingling, tightness, redness), liable to dissuade the consumer from using the composition.
The composition according to the invention may have any of the dosage forms conventionally used for topical application and particularly in the form of dispersions of the lotion or gel type, emulsions of liquid or semi-liquid consistency such as milk, obtained by dispersing a fatty phase in an aqueous phase (O/W) or conversely (W/O), or suspensions or emulsions of soft, semi-solid or solid consistency such as cream or gel, or multiple emulsions (W/O/W or 0/W/O), microemulsions. The composition according to the invention can as an alternative have the form of sticks. These compositions are prepared according to the usual methods.
Furthermore, the compositions used according to the invention can be more or less fluid and have the appearance of a white or colored cream, of an ointment, of a milk, of a lotion, of a serum, of a paste or of a foam. They can also have a solid form, and for example have the form of a stick.
Preferably, the compositions are liquid. According to one advantageous embodiment, the cosmetic composition according to the invention may further comprises at least one organic and/or mineral sun filter (filters of UV rays from sunlight).
The UV filters is a UV filter routinely used in cosmetics. It may be chosen in the positive list contained in Annex VI of the Regulation (EC) N° 1223/2009, which specifies the list of UV filters authorized in cosmetics.
The UV filters of the composition according to the invention can be organic, lipophilic, hydrophilic or insoluble. The UV filters of the composition according to the invention can provide a UVA and/or UVB photoprotection.
According to one embodiment, the composition further comprises at least one UV filter chosen from organic hydrophilic UV filters, organic lipophilic UV filters, insoluble organic UV filters, mineral filters or any of the mixtures thereof. According to one embodiment, the composition may comprise one or several bis- resorcinyl triazine derivatives as described and prepared according to the syntheses indicated in patent applications EP-A-0775 698.
Examples of such compounds suitable for use include:
- 2,4-bis {[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxy-phenyl)-1 ,3,5- triazine;
- 2,4-bis{[4-(3-(2-propyloxy)-2-hydroxy-propyloxy)-2-hydroxy]-phenyl}-6-(4- methoxyphenyl)-1 ,3,5-triazine;
- 2,4-bis {[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-[4-(2-methoxyethyl-carboxyl)- phenylamino]-1 ,3,5-triazine;
2,4-bis {[4-tris(trimethylsiloxy-silylpropyloxy)-2-hydroxy]-phenyl}-6-(4- methoxyphenyl)-1 ,3,5-triazine;
2,4-bis {[4-(2"-methylpropenyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)- 1 ,3,5-triazine;
- 2,4-bis {[4-(1 ',1 ',1 ',3',5',5',5'-heptamethyltrisiloxy-2"-methylpropyloxy)-2-hydroxy]- phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazine.
2,4-bis{[4-(3-(2-propyloxy)-2-hydroxy-propyloxy]-2-hydroxy]-phenyl}-6-[(4- ethylcarboxyl)-phenylamino]-1 ,3,5-triazine;
- 2,4-bis {[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(1 -methylpyrrol-2-yl)-1 ,3,5- triazine.
More specifically, at least the compound 2,4-bis {[4-(2-ethyl-hexyloxy)-2-hydroxy]- phenyl}-6-(4-methoxy-phenyl)-1 ,3,5-triazine or Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (INCI name) such as the product sold under the trade name "TINOSORB S" by CIBA GEIGY.
According to one embodiment, the composition may comprise one or several dibenzoylmethane derivatives. Particularly mention may be made of, but is not limited to:
- 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 (also known under the name Avobenzone),
- 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.
According to one embodiment, the composition may comprise one or several benzylidene camphor derivatives. Mention can be made in particular of:
3-Benzylidene camphor manufactured under the name "MEXORYL SD" by
CHIMEX,
4-Methylbenzylidene camphor sold under the name "EUSOLEX 6300" by MERCK, Benzylidene Camphor Sulfonic Acid manufactured under the name "MEXORYL SL" by CHIMEX,
Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL
SO" by CHIMEX,
Polyacrylamidomethyl Benzylidene Camphor manufactured under the name "MEXORYL SW" by CHIMEX.
Terephthalylidene Dicamphor Sulfonic Acid marketed under the name MEXORYL SX by CHIMEX.
According to an embodiment, the composition can comprise one or several derivatives of β,β'-diphenylacrylate, such as etocrylene, sold under the trade name "UVINUL N35" by BASF; or octocrylene, sold in particular under the trade name "UVINUL N539" by BASF.
The organic UV filters can also be selected from anthranilics; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenyl benzotriazole derivatives; benzalmalonate derivatives particularly those cited in the patent US5624663; phenyl benzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis- benzoazolyl derivatives as described in the patents EP669323 and US 2,463,264; p- aminobenzoic acid (PABA) derivatives; methylene bis-(hydroxyphenyl benzotriazole) derivatives as described in the applications US5,237,071 , US 5,166,355, GB2303549, DE 197 26 184 and EP8931 19; benzoxazole derivatives as described in the patent applications EP0832642, EP1027883, EP1300137 and DE10162844; filter polymers and filter silicones such as those particularly described in the application WO-93/04665; dimers derived from a-alkylstyrene such as those described in the patent application DE19855649; 4,4-diarylbutadienes as described in the applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EP1 133980 and EP133981 ; other merocyanine derivatives such as those described in WO04006878, WO05058269 and WO06032741 and the mixtures thereof.
According to one embodiment, the quantity of the UV filter or filters, present in the composition according to the invention, may range from 0.001 to 50% by weight, with respect to the total weight of the composition. It ranges for example from 1 to 50% by weight, or for example from 5 to 50% by mass, and for example ranges from 7 to 20% by mass with respect to the total mass of the composition.
According to one advantageous embodiment, the cosmetic composition according to the invention may further comprise at least one thickener.
The terms thickener means a compound that introduced at 1 % by weight in pure water and at pH 7 and at 25°C has a viscosity greater than 1 1 ,000 Pa.s.
The viscosity is measured in Pa.s for a shear value of 0.001 s-1 using a HAAKE Mars rheometer with titanium sand-blasted cone-plate geometry 35 mm in diameter with an angle of 2°. The measurements are taken in imposed constrained equilibrium.
The thickeners according to the invention can be of natural or synthetic, mineral or organic origin.
The thickeners can be anionic, cationic, amphoteric or non-ionic polymers, associative or not.
Depending on the fluidity of the composition sought, one or a plurality of thickeners and/or gelling agents, particularly hydrophilic, i.e. soluble or dispersible in water, may be incorporated in the composition. By way of hydrophilic gelling agents, mention may be made for example of optionally modified carboxyvinyl polymers, such as the products marketed under the trade names Carbopol (CTFA name: carbomer) and Pemulen (CTFA name: Acrylates/C 10-30 akyl acrylate crosspolymer) by Goodrich; polyacrylamides; 2- acrylamido 2-methylpropane sulfonic acid polymers and copolymers (AMPS), optionally cross-linked and/or neutralized, such as poly(2-acrylamido-2-methylpropanesulfonic acid) marketed by Hoechst under the trade name "Hostacerin AMPS" (CTFA name: Ammonium Polyacryldimethyltauramide); cross-linked anionic acrylamide/AMPS copolymers, in the form of a W/O emulsion, such as those marketed under the name SEPIGEL 305 (C.T.F.A. name : Polyacrylamide/C13-14 lsoparaffin/Laureth-7) and under the name SIMULGEL 600 (C.T.F.A. name : Acrylamide / Sodium acryloyldimethyltaurate copolymer / Isohexadecane / Polysorbate 80) by SEPPIC; polysaccharide biopolymers such as xanthan gum, guar gum, alginates, modified celluloses; and mixtures thereof. The quantity of gelling agents is dependent on the end purpose.
The mineral thickeners can be chosen from clays, optionally modified, silicas, optionally modified, or mixtures thereof.
Preferably, the mineral thickeners are chosen from lipophilic clays in particular modified hectorites; pyrogenic silica with a hydrophobic treatment; hydrophobic silica aerogels, or mixtures thereof.
The thickeners according to the invention are generally present in the composition according to the invention at a content ranging from 0.01 % to 20% by weight, preferably from 0.1 % to 10% by weight, and most preferably from 0.5% to 10% by weight, with respect to the total weight of the composition.
Furthermore, when the composition used according to the invention comprises an oil phase, the latter preferably contains at least one oil. It may further contain other fats.
The composition according to the invention can as such also comprise at least one oil.
By way of oils suitable for use in the composition of the invention, mention may be made for example of:
- hydrocarbon oils of animal origin, such as perhydrosqualene;
- hydrocarbon oils of plant origin, such as liquid fatty acid triglycerides having 4 to 10 carbon atoms such as heptanoic or octanoic triglycerides or, for example the sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado oil, caprylic/capric acid triglycerides such as those sold by Stearineries Dubois or those sold under the trade names Miglyol "810", "812" and "818" by Dynamit Nobel, jojoba oil, shea butter oil;
- C6-C18 acid ,carbonates such as dioctyl carbonate;
- esters and synthetic esters, in particular fatty acids, such as oils having formulas R1 COOR2 and R10R2 wherein R1 is the remainder of a fatty acid comprising from 8 to 29 carbon atoms, and R2 is a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, such as for example Purcellin oil, isononyl isononanoate, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl-malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate;
- linear or branched hydrocarbons, of mineral or synthetic origin, such as paraffin oils, volatile or not, and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polybutene such as Parleam; isododecane, isohexadecane;
- fatty alcohols having 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol, and the mixture thereof (cetylstearyl alcohol), octyl dodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol;
- partially hydrocarbon and/or silicone fluorinated oils such as those described in the document JP-A-2-295912;
- silicone oils such as polymethylsiloxanes (PDMS), optionally volatile with a linear or cyclic silicone chain, liquid or pasty at ambient temperature, particularly cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl pendant or silicon chain-end groups, groups having 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenyl-siloxanes, diphenyl-dimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyltrimethyl- siloxysilicates, and polymethylphenylsiloxanes; and
- mixtures thereof.
The term "hydrocarbon oil" in the list of oils cited above denotes any oil comprising mostly carbon and hydrogen atoms, and optionally ester, ether, fluorinated, carboxylic acid and/or alcohol groups.
The proportion of oil can range from 2 to 50% by weight, and preferably from 5 to 30% by weights, more particularly from 7 to 20% by weight with respect to the total weight of the composition.
The other fats suitable for being present in the oil phase are for example fatty acids comprising 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, Carnauba or Candellila wax, paraffin wax, lignite wax or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-C1 -4- alkyldimethicone and trifluoropropyldimethicone; and silicon elastomers such as the products marketed under the trade names "KSG" by Shin-Etsu, under the trade names "Trefil", "BY29" or "EPSX" by Dow Corning or under the trade names "Gransil" by Grant Industries. These fats may be chosen in varied ways by those skilled in the art in order to prepare a composition having the properties, for example in respect of consistency or texture, sought.
According to a particular embodiment of the invention, the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion, preferably O/W.
The proportion of the fatty phase of the emulsion may range from 2 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.
Advantageously, the composition comprises at least one aqueous phase. The composition according to the invention preferably comprises an aqueous phase comprising water and a water-soluble organic solvent, chosen for example from C2-C4 linear or branched alkanols, such as ethanol and isopropanol, propanol, butanol; polyols and polyol ethers such as 2-butoxyethanol, glycerol, diglycerol, propyleneglycol, dipropyleneglycol, butylene glycol, hexylene glycol, 1 ,3-propanediol, pentylene glycol, polyethyleneglycols, propyleneglycol monomethylether, monoethylether and monomethylether of diethyleneglycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof
The composition generally comprises from 30 to 95% by weight of water with respect to the total weight of the composition.
The quantity of water-soluble organic solvents can range from for example 0 to 30% by weight, preferably from 0.5 to 20% by weight, better from 1 to 15% by weight, even better from 2 to 10% by weight and even better from 2 to 8% by weight relative to the total weight of the composition.
The composition according to the invention can be a composition for the treatment, cleaning or makeup of the body or of the face, in particular, a treatment composition.
The skin treatment composition can for example be a cream, a gel or a fluid for the face. The composition according to this invention can furthermore contain various adjuvants that are commonly used ion the cosmetics field, such as surfactants, emulsifiers; fillers; preservatives; sequestering agents; colorants; perfumes; pH agents.
Advantageously, the composition can further comprise at least one treatment agent. This agent is preferably chosen from desquamating, anti-microbial, antiinflammatory, sebo-regulating, anti-oxidant, moisturizing agents and vitamins. Obviously, those skilled in the art will take care to choose these optional additional compounds, and/or the quantity thereof, such as the advantageous properties of the composition according to the invention are not, or are substantially not, altered by the envisaged addition. The agent or agents used in the composition according to the invention can represent from 0.0001 to 20%, preferably from 0.001 to 10% and, better, from 0.01 to 5% of the total weight of the composition.
The invention further has for object a cosmetic care and/or makeup method of the skin, comprising the topical application on the skin of the composition according to the invention.
Finally, the invention also has for object the use of an association of one or several alkylC8-C30(poly)glycosides (compound(s) b), and of one or several fatty acid esters, said ester comprising at least 24 carbon atoms (compound(s) c), in order to decrease the yellowing of a composition containing at least Baicalin and/or one of the derivatives thereof or a plant extract containing it.
The invention will now be illustrated by the following non-limiting examples. In these examples, the quantities are indicated as a percentage by weight. The compounds are, according to the case, mentioned in chemical names or in CTFA names (International Cosmetic Ingredient Dictionary and Handbook).
EXAMPLES Example 1 :
The following 5 compositions were prepared: compositions A to C are comparative, and the compositions D and E are according to the invention.
The preparation protocol is as follows:
Preparation of phases A 1 and A2
The raw materials of A1 are carefully weighed beforehand using a balance (precision = 0.01 g), are heated to a temperature of 70°C using a water bath, and are mixed using a Rayneri mixer.
Phase A2
Phase A2 is heated to 70°C and introduced into the phase A1 . The mixture obtained is yellow and limpid.
Addition of the phase B and Emulsification
Phase B is heated to 70°C using a heating plate, then introduced into the phase A1 +A2 under stirring using a Moritz rotor stator. The stirring is maintained for 10 minutes. The preparation is brought to ambient temperature.
Addition of phases C and D
Phases C and D are successively introduced into the phase A1 +A2+B under Rayneri stirring.
The pH is adjusted to 5.5 ± 0.3.
Then, the matteness, freshness and greasy application are measured according to the following protocols:
Measurements of the matteness, freshness and greasiness of the compositions:
The matteness, freshness and greasy aspect are evaluated by a panel of sensory experts of 10 people. Each composition is applied on the forearm with a dose of 2mg/cm2. The product is spread by circular movements until penetration of the product (about 30 seconds). The evaluation of the freshness is carried out during the application. The evaluation of the matteness and of the greasy aspect is carried out after 2 minutes of drying:
Freshness: Freshness is evaluated according to a scale ranging from 1 to 15, where 1 constitutes a non-fresh reference and 15 constitutes a very fresh reference.
- Matteness: Matteness is evaluated with the eye after 2 minutes of drying according to a scale ranging from 1 to 15, where 1 constitutes a very shiny reference and 15 constitutes a very matte reference.
- The greasy aspect is evaluated with the finger after 2 minutes of drying according to a scale ranging from 1 to 15, where 1 constitutes a very greasy reference and 15 constitutes a hardly greasy reference.
Measurements of yellowing:
The color of the formulas is evaluated after preparation of thin films on a contrast card. The formulas are arranged within a circle of 2.2 cm in diameter and are leveled in order to obtain reproducible deposit thicknesses. The colorimetric measurements are then taken using a Minolta CM2600D spectro-colorimeter with two points of the film. This operation is repeated twice, which leads to 4 experimental values per composition. The results are expressed in the system (L*, a*, b*), wherein L* is the luminance, a* is the red-green axis (-a* = green, +a* = red) and b* is the yellow-blue axis (-b* =blue, +b* =yellow). As such, a* and b* express the shade of the compound. The Chroma value (C*) is calculated in the system CIE L*a*b* according to the formula C* = ((a*)A2+(b*)A2)A0.5.
The higher the Chroma value C* is, the more marked the intensity of the color of the product is.
The results obtained are indicated in the following table. As demonstrated by the results of the composition A (comparative composition), a formula comprising baicalin, Arlacel 165 and cetyl alcohol (which constitutes a conventional surfactant system), has a strong shine, a greasy finish, and a very strong yellow coloration. The composition B (comparative composition) contains the same surfactant system as the composition A, with in addition behenyl behenate. The results are similar to those of the composition A.
The presence of the behenyl behenate alone is therefore not enough to change the properties of shine, greasiness and the strong yellow coloration observed for the composition A.
The composition C (comparative composition) contains, as the only surfactant, Montanov 202. The results show a reduced yellow coloration, but strong shine and a greasy effect.
Finally, the compositions D and E according to the invention are the only ones that show both a low yellow coloration, strong matteness (low shine), and a non-greasy finish.
Figure imgf000024_0001
TOTAL 100.00 100.00 100.00 100.00 100.00
Matteness (Sensory expert panel score out of 15;
2.1 +/- 0.2
1 = Shiny; 15 = Not shiny) 6.8 +/- 1 .4 5.8 +/- 0.4 14.5 +/- 0.2 12.7 +/ -0.8
Freshness (Sensory expert panel score out of 15;
11.7 +/ -0.9 12.3 +/ -0.8 12.6 +/ -1 .5 11.9 +/ -0.3 10.9 +/ -1.8 1 = Not fresh; 15 = Fresh when applied)
Non-greasy finish (Sensory expert panel score
out of 15; 1 = Greasy finish; 15 = Non-greasy 1.7 +/- 0.2 2.8 +/- 0.2 7.8 +/- 0.4 14.1 +/- 0.3 12.6 +/- 1.2 finish)
L* 92 91.8 92 92 92.2 a* -6 -5.2 -3.1 -2 -2.4
Colorimetric evaluation of the
b* 14.7 12.8 5.7 4.8 5.1 compositions
C* 15.9 13.8 6.5 5.2 5.6
Color Very yellow Very yellow Pale yellow Pale yellow Pale yellow

Claims

1 . Composition comprising in a physiologically acceptable medium:
a) at least Baicalin and/or one of the derivatives thereof or a plant extract containing it,
b) one or several alkylC8-C30(poly)glycosides, and
c) one or several fatty acid esters, said ester comprising at least 24 carbon atoms.
2. Composition according to claim 1 , where Baicalin or one of the derivatives thereof is chosen for the compounds that satisfy the following formula (I):
Figure imgf000026_0001
(i) wherein
Each X1 , X2, X3, X4, X5, Xa, Xb, Xc, Xd, Xe and Xf, independently, designate O or S;
Each Y1 , Y2, Y3, Y4, Y5, Y6, independently, designate H or a (C1 -C10)alkyl radical, in particular methyl;
Each R4, R5, Ra, Rb and Rc, independently, designates H, a (C1 -C10)alkyl radial optionally substituted with 1 to 5 Ry groups, or a (C1 -C10)alkyl-O-(C1 -C10)alkyl radial, with each (C1 -C10)alkyl radical able to be substituted with 1 to 5 Ry groups;
Each Ry, independently, designates Rq or a -(C2-C10)alkenyl, -(C2-C10)alkynyl, - (C3-C10)cycloalkyl, -(C8-C14)bicycloalkyl, -(C8-C14)tricycloalkyl, -(C5-C10)cycloalkenyl, - (C8-C14)tricycloalkenyl, phenyl, naphthyl, -(C14)aryl radical, with each one able to be substituted with one or several Rz radicals;
Each R1 R2, R3, independently, designates H or Rq or a -(C2-C10)alkenyl, -(C2- C10)alkynyl, -(C3-C10)cycloalkyl, -(C8-C14)bicycloalkyl, -(C8-C14)tricycloalkyl, -(C5- C10)cycloalkenyl, -(C8-C14)tricycloalkenyl, phenyl, naphthyl, -(C14)aryl radical, with each one able to be substituted with one or several Rz radicals;
Rf is H, (C1 -C12) alkyl optionally substituted with 1 to 5 Ry radicals, (C1 -C12)alkyl- 0-(C1 -C12)alkyl, with each (C1 -C12)alkyl radical able to be substituted with 1 to 5 Ry groups;
Each Rq, independently, is CN, OH, halogen, N3, N02, N(Rz)2, =NRz, CH=NRz, NRzOH, ORz, CORz, C(0)Rz, 0(CO)ORz, SRz, S(0)Rz or S(0)2Rz;
Each Rz, independently, is -(C1 -C6)alkyl, -(C2-C6)alkenyl, -(C3-C8)cycloalkyl, - (C3-C8)cycloalkenyl, phenyl, an heterocycle having 3 to 5 branches, CH(halo)2 or C(halo)3; and
n is 0, 1 , 2, 3, 4 or 5 as well as the salts thereof, the optical isomers thereof and/or the diastereoisomers thereof.
3. Composition according to claim 1 or 2, comprising Baicalin that satisfies the following general formula (II):
Figure imgf000027_0001
(Π) or a plant extract that contains it, in particular extract from the skull cap root, in particular from Scutellaria Baicalensis with INCI name: SCUTELLARIA BAICALENSIS ROOT EXTRACT.
4. Composition according to any of the preceding claims, characterized in that the Baicalin having formula (II) and/or one of the compounds having formula (I) is present in concentrations of active substance ranging from 0.01 % to 10% by weight, better from 0.1 % to 8% by weight, and more preferably from about 0.2% to about 5% by weight with respect to the total weight of the composition.
5. Composition according to any of the preceding claims, characterized in that said fatty acid esters are chosen from: A) those responding to the following formula (III):
R-COO-R' (III)
wherein:
R and R', identical or different, designate a saturated or unsaturated, linear or branched hydrocarbon group, comprising from 12 to 30 carbon atoms and preferably from 14 to 24 carbon atoms, and
B) C12-C30 di- or triesters of glycerol and of fatty acids.
6. Composition according to any of the preceding claims, characterized in that said fatty acid esters are chosen from behenyl behenate, stearyl stearate, arachidyl arachidate, glyceryl tristearate, glyceryl distearate, glycerine trihydroxystearate, glyceryl trisbehenate and glyceryl dibehenate, and more particularly behenyl behenate.
7. Composition according to any of the preceding claims, characterized in that the fatty acid esters are present in concentrations ranging from 0.1 to 10% by weight with respect to the total weight of the composition, preferably from 0.2 to 8% by weight, and more preferably from 0.5 to 5% by weight with respect to the total weight of the composition.
8. Composition according to any of the preceding claims, characterized in that the alkylC8-C30(poly)glycoside(s) are represented by the following general formula:
R10-(R20)t (G)v
wherein R1 is a linear or branched alkyl and/or alkenyl radical comprising about 8 to 30 carbon atoms, a alkylphenyl radical of which the linear or branched alkyl radical comprises from 8 to 24 carbon atoms; R2 is an alkylene radical comprising about from 2 to 4 carbon atoms; G is a sugar pattern comprising from 5 to 6 carbon atoms; t designates a value ranging from 0 to 10, preferably 0 to 4, preferably 0 to 3; and v designates a value ranging from 1 to 15, preferably from 1 to 4.
9. Composition according to any of the preceding claims, characterized in that the alkylC8-C30(poly)glycoside(s) are present in a content ranging from 0.05 to 10% by weight, preferably from 0.1 to 5% by weight, and more preferably from 0.2 to 1 %, better from 0.25 to 0.6% by weight with respect to the total weight of the composition.
10. Cosmetic composition according to any of the preceding claims, characterized in that it further comprises at least one thickener.
1 1 . Cosmetic composition according to any of the preceding claims, characterized in that it further comprises at least one oil.
12. Cosmetic composition according to any of the preceding claims, characterized in that it further comprises at least one sun filter.
13. Cosmetic care and/or makeup method of the skin and/or of the lips and/or of the hair, comprising the topical application on the skin and/or the lips and/or the hair of the composition according to one of claims 1 to 12.
14. Use of a composition such as defined in any of the claims 1 to 12, in order to reduce the pigmentation induced by UV rays.
15. Use of an association of one or several alkylC8-C30(poly)glycosides, and of one or several fatty acid esters, said ester comprising at least 24 carbon atoms, in order to decrease the yellowing of a composition containing at least Baicalin and/or one of the derivatives thereof or a plant extract containing it.
PCT/EP2017/084234 2016-12-21 2017-12-21 Composition comprising baicalin, a fatty acid ester and an alkylpolyglycoside WO2018115360A1 (en)

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