WO2002049596A2 - Composition filtrante contenant un filtre du type derive du dibenzoylmethane, le p-methyl-benzylidene camphre et un compose 4,4-diarylbutadiene - Google Patents
Composition filtrante contenant un filtre du type derive du dibenzoylmethane, le p-methyl-benzylidene camphre et un compose 4,4-diarylbutadiene Download PDFInfo
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- WO2002049596A2 WO2002049596A2 PCT/FR2001/003636 FR0103636W WO0249596A2 WO 2002049596 A2 WO2002049596 A2 WO 2002049596A2 FR 0103636 W FR0103636 W FR 0103636W WO 0249596 A2 WO0249596 A2 WO 0249596A2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- the invention relates to a cosmetic or dermatological composition, for topical use, in particular for the photoprotection of the skin and the hair, characterized in that it comprises, in a cosmetically acceptable carrier:
- the invention also relates to a method for improving the photostability of p-methyl-benzylidene camphor in the presence of a UV filter of the type derived from dibenzoylmethane, comprising adding an effective amount of at least one 4,4-diarylbutadiene compound .
- UV-A rays with wavelengths between 320 and 400 nm, which cause browning of the skin, are capable of inducing an alteration of the latter, in particular in the case of skin. sensitive or skin continuously exposed to solar radiation.
- UV-A rays cause in particular a loss of elasticity in the skin and the appearance of wrinkles, leading to premature skin aging. They promote the triggering of the erythematous reaction or amplify this reaction in certain subjects and can even be the cause of phototoxic or photoallergic reactions.
- UV-A rays For aesthetic and cosmetic reasons such as the conservation of the natural elasticity of the skin for example, more and more people wish to control the effect of UV-A rays on their skin. It is therefore desirable to also filter UV-A radiation.
- UV-A filters a particularly interesting family of UV-A filters is currently constituted by dibenzoylmethane derivatives, and in particular 4-tert-butyl-4'-methoxydibenzoyl methane, which indeed have a strong intrinsic absorption power.
- dibenzoylmethane derivatives which are now products well known per se as active filters in UV-A, are described in particular in French patent applications FR-A-2326405 and FR-A-2440933, as well as in European patent application EP-A-0114607;
- 4- ter-butyl-4'-methoxydibenzoyl methane is also currently offered for sale under the trade name "PARSOL 1789" by the company HOFFMANN LAROCHE.
- the present invention therefore relates to a cosmetic or dermatological composition, for topical use, in particular for the photoprotection of the skin and the hair, characterized in that it comprises, in a cosmetically acceptable carrier:
- the invention also relates to a method for improving the photostability of p-methyl-benzylidene camphor in the presence of a UV filter of the type derived from dibenzoylmethane, comprising adding at least one 4,4-diarylbutadiene compound in an effective amount allowing '' improve the photostability of p-methylbenzylidene camphor.
- effective amount of 4,4-diarylbutadiene according to the invention is meant an amount sufficient to obtain a notable and significant improvement in the photostability of p-methyl-benzylidene camphor of the photoprotective cosmetic composition.
- This minimum quantity of photostabilizing agent to be used which may vary depending on the nature of the cosmetically acceptable support selected for the composition, can be determined without any difficulty by means of a conventional test for measuring photostability.
- 4,4-diarylbutadiene compound is meant any molecule comprising at least one 4,4-diarylbutadiene chromophore group. This can be in the form of a simple compound, an oligomer or a polymer having on the chain grafts containing the chromophore group.
- cosmetic compositions can be produced containing at least one dibenzoylmethane derivative in combination with p-methylbenzylidene camphor, the concentration of p-methyl-benzylidene camphor remains relatively constant even if these compositions are subjected to the action of light.
- compositions targeted by the present invention therefore contain camphor p-methylbenzylidene in combination with at least one dibenzoylmethane derivative.
- the dibenzoylmethane derivatives targeted by the present invention are products already well known per se and described in particular in documents FR-A- 2 326 405, FR-A- 2 440 933 and EP-A- 0 114 607 , documents, the lessons of which are, as far as the very definition of these products is concerned, completely included for reference in the present description.
- dibenzoylmethane derivatives more particularly targeted by the present invention, there may be mentioned, without limitation:
- Another preferred dibenzoylmethane derivative according to the present invention is 4-isopropyldibenzoylmethane, a filter sold under the name of "EUSOLEX 8020" by the company Merck, and corresponding to the following structural formula (II):
- the dibenzoylmethane derivative (s) are present in the compositions according to the invention at levels which are preferably ranging from 0.5 to 15% by weight and more preferably from 1% to 10% by weight, relative to the total weight of composition.
- Camphor p-methylbenzylidene is a liposoluble filter known per se, absorbing in UV-B and sold in particular under the trade name "EUSOLEX 6300" by the company Merck. It is present in the compositions according to the invention at contents which are preferably ranging from 0.5 to 15% by weight and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
- the diene system is of configuration Z, Z; Z, E; E, Z or E, E or mixtures of said configurations and where: - R 1 and R 2 , identical or different, denote hydrogen, a C1-C20 alkyl radical, linear or branched; a C 2 -C 10 alkenyl radical; a d-C12 alkoxy radical; a C3-C10 cycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a linear or branched C 1 -C 20 alkoxycarbonyl radical; a linear or branched C 1 -C 12 monoalkylamino radical; a linear or branched C ⁇ -C 12 dialkylamino radical; aryl; a heteroaryl or a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue;
- R 3 denotes a COOR 5 group; COR 5 ; CONR 5 R 6 ; CN; alkyl C ⁇ -C 2 o, linear or branched; a C 2 -C 10 alkenyl radical; a C 3 -C 10 cycloalkyl radical; a C 7 -C 10 bicycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a C7-C10 bicycloalkenyl radical; C ⁇ -Ci ⁇ aryl; a C 3 -C 7 heteroaryl;
- R 4 denotes a COOR 6 group; COR 6 ; CONR 5 R 6 ; CN; a linear or branched C 1 -C 20 alkyl radical; a C 2 -C 10 alkenyl radical; a C 3 -C 10 cycloalkyl radical; a C 7 -C 10 bicycloalkyl radical; cycloalkenyl C 3 -C 10; ; a C 7 -C 10 bicycloalkenyl radical; aryl; heteroaryl;
- R 5 and R 6 identical or different, denote hydrogen; [X] p -R 7 , C ⁇ -C 6 -aikylene- SO3Y; CrCe-alkylene-POsY; C ⁇ -C 6 -alkylene-N (R °) 3 + A ' ; a linear or branched C1-C20 alkyl radical; a C2-C 10 alkenyl radical; a cycloalkyl radical in C 3 -C 1 0; a C7-C10 bicycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a C 7 -C 10 bicycloalkenyl radical; aryl; heteroaryl;
- - X denotes a group -CH 2 -CH 2 -Z-, -CHzCHzCHsZ-, -CH (CH 3 ) -CH 2 -Z-, -CH 2 -CH 2 -CH 2 -CH 2 -Z-, -CH 2 -CH (CH 2 CH 3 ) -Z-;
- - Y denotes hydrogen, Na + , K + , Mg 2+ , Ca 2+ , Li + , Al 3+ , -N (R 8 ) 4 +
- - Z denotes O or NH
- R 7 and R 8 identical or different, denote hydrogen, an alkyl radical in C ⁇ -C 6 , linear or branched; a linear or branched C 2 -C 6 alkenyl radical; a linear or branched CC 6 acyl radical;
- R 9 denotes hydrogen, an alkyl radical in C ⁇ ⁇ C 6 , linear or branched; a C 2 -C 6 alkenyl radical;
- - n varies from 1 to 3; - p varies from 0 to 150.
- C ⁇ -C 2 o alkyl radicals there may be mentioned for example: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyle, 1, 1- dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethytbutyl, 2-ethylbutyl, 1, 2,2- trimethylpropyl
- alkenyl groups C 2 -C1 0, there may be mentioned for example: ethenyl, n-propenyl, 1-methylethenyl, n-butenyl, 1-méthylpropènyIe, 2-methylpropenyl, 1, 1-diméthyléthènyle, n-pentenyl, 1- methylbutenyl, 2-methylbutenyl, 3-methylbutenyl, 2,2-dimethylpropenyl, 1-ethylpropenyl, n-hexenyl, 1, 1-dimethylpropenyl, 1, 2-dimethylpropenyl, 1 -methylpentenyl,
- radicals R 1 and R 2 there may be mentioned: methoxy, n-propoxy, 1-methylpropoxy, n-pentoxy, 3-methylbutoxy,
- C 3 -C 10 cycloalkyl radicals for the radicals R 6 and R 7 there may be mentioned for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyle, 1-ethylcyclopropyle, 1-propylcyclopropyle, 1-butylcyclopropyle, 1 -pentylcyclopropyle, 1-methyl-1-butylcyclopropyle, 1, 2-dimethylcyclypropyle, 1-methyl-2-ethylcyclopropyle, cyclooctyle, cyclononyl or cyclodecyl.
- cyclobutenyl As C 3 -C 10 cycloalkylene radicals having one or more double bonds, for the radicals R 6 and R 7 , there may be mentioned: cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1, 3-cyclohexadienyl, 1, 4-cyclohexadienyl, cycloheptenyl, cycloheptatrienyl, cyciooctenyl, 1,5-cyclooctadienyl, cycloctetraenyl, cyclononenyl or cyclodecenyl.
- the cycloalkyl or cycloalkylene radicals can comprise one or more substituents (preferably from 1 to 3) chosen, for example, from halogen such as chlorine, fluorine or bromine; cyano; nitro; amino; C ⁇ -C 4 -alkylamino; C- ⁇ -C 4 dialkylamino; C1-C alkyl; C ⁇ -C -alkoxy; hydroxy; they may also contain from 1 to 3 heteroatoms such as sulfur, oxygen or nitrogen, the free valencies of which may be saturated with hydrogen or a C- ⁇ -C 4 alkyl radical.
- acyl radicals mention may be made, for example, of formyl, acetyl, propionyl or n-butyryl.
- bicycloalkyl or bicycloalkylene groups are chosen, for example, from bicyclic terpenes such as derivatives of pinane, bornane, pinene or camphor or adamantane.
- the aryl groups are preferably chosen from phenyl or naphthyl rings, which may contain one or more substituents (preferably from 1 to 3) chosen, for example, from halogen such as chlorine, fluorine or bromine; cyano; nitro; amino; CrC -alkylamino; C- ⁇ -C 4 dialkylamino; CrC 4 alkyl; CrC 4 -alkoxy; hydroxy. More particularly preferred are phenyl, methoxyphenyl and naphthyl.
- the heteroaryl groups generally comprise one or more heteroatoms chosen from sulfur, oxygen or nitrogen.
- the water-solubilizing groups are, for example, carboxylate, sulfonate groups and more particularly their salts with physiologically acceptable cations such as the alkali metal salts or the trialkylammonium salts such as the tri (hydroxyalkyl) ammonium or 2-methylpropan-1-ol salts -2- ammonium. Mention may also be made of ammonium groups such as alkylammoniums and their salified forms with physiologically acceptable anions.
- diene system is of configuration Z, Z; Z, E; E, Z or E, E or mixtures of said configurations and where:
- R 1 and R 2 identical or different, denote hydrogen, a C1-Cs alkyl radical; a C1-C5 alkoxy radical; a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue;
- R 3 denotes a COOR 5 group; CONR 5 R 6 ; CN;
- R 4 denotes a COOR 6 group; CONR 5 R 6 ;
- R 5 denotes hydrogen; [X] p -R 7 ; C ⁇ -C 6 -alkylene-SO 3 Y; C ⁇ -C 6 -alkylene-N (R 0 ) 3 + A " ;
- R 6 denotes [X] p -R 7 ; C ⁇ -C 6 -alkylene-SO 3 Y; C 1 -C 6 -alkylene-N (R 8 ) 3 + A ' ;
- - X denotes a group -CH 2 -CH 2 -O-, -CH 2 CH 2 CH 2 O-, -CH (CH 3 ) -CH 2 -O-, - A denotes Cl, Br, I, SO 4 R 9 ;
- - Y denotes hydrogen, Na + , K + , Mg 2+ , Ca 2+ , Li + , Al 3+ , -N (R 8 ) 4 +
- R 7 , R 8 and R 9 identical or different, denote hydrogen, a C 1 -C 3 alkyl radical, linear or branched;
- diene system is of configuration Z, Z; Z, E; E, Z or E, E or mixtures of said configurations and where:
- R 1 and R 2 identical or different, denote hydrogen, a C- ⁇ -C 8 alkyl radical; a C1-C5 alkoxy radical;
- R 3 denotes a COOR 5 group; CONR 5 R 6 ; CN;
- R 4 denotes a COOR 6 group; CONR 5 R 6 ;
- R 5 denotes hydrogen; [X] p -R 7 ; C ⁇ -C 6 -alkyIène-SO 3 Y; C ⁇ -C 6 -alkylene-N (R 8 ) 3 + A " ;
- R 6 denotes [X] p -R 7 ; C C6-alkylene-SO 3 Y; C 1 -C 6 -alkylene-N (R 8 ) 3 + A-;
- - X denotes a group -CH 2 -CH 2 -O-, -CH 2 CH 2 CH 2 O-, -CH (CH 3 ) -CH 2 -O-,
- - Y denotes hydrogen, Na + , K + , Mg 2+ , Ca 2+ , Li + , Al 3+ , -N (R 8 ) 4 +
- R 7 , R 8 and R 9 which may be identical or different, denote hydrogen, a linear or branched C 1 -C 3 alkyl radical;
- - p varies from 0 to 50.
- diene system is of configuration Z, Z; Z, E; E, Z or E, E or mixtures of said configurations and where:
- R 1 and R 2 identical or different, denote hydrogen, a C- ⁇ -C 8 alkyl radical; a C1-C5 alkoxy radical;
- R 3 denotes a COOR 5 group; CONR 5 R 6 ; CN;
- R 4 denotes a COOR 6 group; CONR 5 R 6 ;
- R 5 denotes hydrogen; [X] p -R 7 ; d-Ce-alkylene-SOsY; C ⁇ -C 6 -alkylene-N (R 8 ) 3 + A " ;
- R 6 denotes [X] p -R 7 ; C Ce-alkylene-SOsY; C 1 -C 6 -alkylene-N (R 8 ) 3 + A-;
- - X denotes a group -CH 2 -CH 2 -O-, -CH 2 CH 2 CH 2 O-, -CH (CH 3 ) -CH 2 -O-, - A denotes Cl, Br, I, SO 4 R 9 ;
- - Y denotes hydrogen, Na + , K + , Mg 2+ , Ca 2+ , Li + , Al 3+ , -N (R 8 ) 4 +
- R 7 , R 8 and R 9 which may be identical or different, denote hydrogen, a linear or branched C 1 -C 3 alkyl radical;
- diene system is of configuration Z, Z; Z, E; E, Z or E, E or mixtures of said configurations and where:
- Y 'de notes a group -O- or -NR 10 -
- R 10 denotes hydrogen; a linear or branched C 1 -C 20 alkyl radical; a C 2 -C 10 alkenyl radical; a cycloalkyl radical in C 3 -C 1 0; a C 7 -C 10 bicycloalkyl radical; a C3-C10 cycloalkenyl radical; a C 7 -C 10 bicycloalkenyl radical; aryl; heteroaryl; - X 'denotes a linear or branched, aliphatic or cycloaliphatic polyol residue comprising from 2 to 10 hydroxy groups and of valence q; the carbon chain of said residue being able to be interrupted by one or more sulfur or oxygen atoms; one or more imine groups; one or more dC alkylimino;
- X ' is a polyol residue containing from 2 to 10 hydroxyl groups and in particular:
- R 1 and R 2 identical or different, denote hydrogen, a C ⁇ -C ⁇ 2 alkyl radical; a C ⁇ -C 8 alkoxy radical; a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue;
- R 3 denotes a COOR 5 group; CONR 5 R 6 ; CN; a cycloalkyl radical in C 3 -C 10; a C 7 -C 10 bicycloalkyl radical;
- R 5 and R 6 identical or different, denote a C 1 -C 20 alkyl radical , linear or branched; a C 3 -C 1 cycloalkyl radical; a C 7 -C 10 bicycloalkyl radical; naphthyl or optionally substituted phenyl;
- - X 'de notes a polyol residue comprising from 2 to 6 hydroxy groups and more particularly from 2 to 4.
- the 4,4-diarylbutadiene compounds in accordance with the invention are preferably present in the composition of the invention in proportions ranging from 0.5 to 15% by weight and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
- compositions in accordance with the invention may comprise, in addition, other complementary organic UV filters active in UVA and or UVB (absorbers), water-soluble or iiposoluble or else insoluble in the cosmetic solvents commonly used.
- the additional organic UV filters are chosen in particular from anthranilates; salicylic derivatives, camphor derivatives other than p-methyl-benzylidene camphor; triazine derivatives such as those described in patent applications US 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469 and EP933376; benzophenone derivatives; ⁇ , ⁇ '-diphenylacry!
- UVINUL 400 Benzophenone-1 sold under the trade name "UVINUL 400" by BASF
- UVINUL D50 Benzophenone-2 sold under the trade name "UVINUL D50" by BASF
- UVINUL M40 Benzophenone-3 or Oxybenzone, sold under the trade name "UVINUL M40" by BASF,
- UVINUL MS40 Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF
- UVINUL DS-49 Benzophenone-9 sold under the trade name UVINUL DS-49 "by BASF,
- UVASORB HEB Diethylhexyl Butamido Triazone sold under the trade name "UVASORB HEB” by SIGMA 3V,
- the more particularly preferred soluble organic UV filters are chosen from the following compounds:
- the cosmetic compositions according to the invention may also contain pigments or even nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of coated or uncoated metal oxides such as for example titanium oxide nanopigments (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are moreover alumina and / or aluminum stearate. Such metallic oxide nanopigments, coated or uncoated, are in particular described in patent applications EP-A-0518772 and EP-A-0518773.
- coated or uncoated metal oxides such as for example titanium oxide nanopigments (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se.
- Conventional coating agents are moreover alumina and / or
- compositions according to the invention may also contain artificial tanning and / or browning agents for the skin (self-tanning agents), such as for example dihydroxyacetone (DHA).
- artificial tanning and / or browning agents for the skin such as for example dihydroxyacetone (DHA).
- DHA dihydroxyacetone
- compositions of the invention may also comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers, emollients, silicones, ⁇ -hydroxy acids, defoamers, moisturizers, vitamins, insect repellents, perfumes, preservatives, surfactants, anti-inflammatories, substance P antagonists, fillers, polymers, propellants, basifying or acidifying agents, dyes or any other ingredient usually used in cosmetics, in particular for the manufacture of sunscreen compositions in the form of emulsions.
- conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers, emollients, silicones, ⁇ -hydroxy acids, defoamers, moisturizers, vitamins, insect repellents, perfumes
- the fatty substances can consist of an oil or a wax or their mixtures.
- oil is meant a compound which is liquid at room temperature.
- wax is intended to mean a compound which is solid or substantially solid at room temperature, and the melting point of which is generally greater than 35 ° C.
- They also include fatty acids, fatty alcohols and fatty acid esters, linear or cyclic such as derivatives of benzoic, trimellitic and hydroxy-benzoic acid.
- oils mention may be made of mineral oils (paraffin); vegetable (sweet almond oil, macadamia oil, blackcurrant seed, jojoba); synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the benzoate of C 12 -C 15 alcohols sold under the trade name "Finsolv TN" by the company Finetex, octyl palmitate, lanolate d 'isopropyl, triglycerides including those of capric / caprylic acids), fatty esters and ethers oxyethylenated or oxypropylenated; silicone (cyclomethicone, polydimethysiloxanes or PDMS) or fluorinated, polyalkylenes.
- mineral oils paraffin
- vegetable sweet almond oil, macadamia oil, blackcurrant seed, jojoba
- synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the benzoate of C 12
- waxy compounds there may be mentioned paraffin, carnauba wax, beeswax, hydrogenated castor oil.
- organic solvents mention may be made of lower alcohols and polyols.
- compositions of the invention can be prepared according to techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of the oil-in-water or water-in-oil type.
- compositions can be presented in particular in the form of a simple or complex emulsion (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk, a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
- a simple or complex emulsion O / W, W / O, O / W / O or W / O / W
- a cream gel such as a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
- the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins. J. Mol. Biol. 13, 238 (1965), FR2315991 and FR2416008).
- the cosmetic composition of the invention can be used as a composition for protecting the human epidermis or the hair against ultraviolet rays, as a sunscreen composition or as a make-up product.
- the cosmetic composition according to the invention when used for the protection of the human epidermis against UV rays, or as an antisun composition, it may be in the form of a suspension or of dispersion in solvents or fatty substances, in the form of nonionic vesicular dispersion or alternatively in the form of an emulsion, preferably of the oil-in-water type, such as a cream or a milk, in the form of an ointment, gel, cream gel, solid stick, powder, stick, aerosol foam or spray.
- the cosmetic composition according to the invention when used for protecting the hair against UV rays, it can be in the form of a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion and constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
- a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
- composition When the composition is used as an eyelash, eyebrow or skin makeup product, such as epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush, mascara or liner also called “eyeliner", it can be in solid or pasty, anhydrous or aqueous form, such as oil in water or water in oil emulsions, nonionic vesicular dispersions or even suspensions.
- eyelash eyebrow or skin makeup product
- anhydrous or aqueous form such as oil in water or water in oil emulsions, nonionic vesicular dispersions or even suspensions.
- the aqueous phase (comprising in particular hydrophilic filters) generally represents from 50 to 95% by weight, preferably from 70 at 90% by weight, relative to the whole of the formulation
- the oily phase (comprising in particular the lipophilic filters) from 5 to 50% by weight, preferably from 10 to 30% by weight, relative to the whole of the formulation
- the (co) emulsifier (s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, relative to the whole of the formulation.
- an object of the invention is the use of a composition as defined above for the manufacture of a cosmetic or dermatological composition intended for the protection of the skin and / or the hair against radiation ultraviolet, especially solar radiation.
- Another object of the present invention resides in a process for improving the stability with respect to UV radiation of p-methyl-benzylidene camphor in the presence of a UV filter of the type derived from dibenzoylmethane, consisting in adding an effective amount of at least one 4,4-diaryIbutadiene as defined above.
- Another object of the present invention consists in the use of a UV filter of the 4,4-diarylbutadiene type as defined above in the preparation of a cosmetic or dermatological composition comprising at least one UV filter of the type derived from dibenzoylmethane and at least p-methyl benzylidene camphor in order to improve the stability against UV rays p-methyl-benzylidene camphor.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2002218389A AU2002218389A1 (en) | 2000-12-18 | 2001-11-20 | Filtering composition containing a filter of the type derived from dibenzoylmethane, p-methyl-benzylidene camphor and a diarylbutadiene compound |
EP01271204A EP1359894A2 (fr) | 2000-12-18 | 2001-11-20 | Composition filtrante contenant un filtre du type derive du dibenzoylmethane, le p-methyl-benzylidene camphre et un compose 4,4-diarylbutadiene |
JP2002550938A JP2004517095A (ja) | 2000-12-18 | 2001-11-20 | ジベンゾイルメタンから誘導されたタイプの遮蔽剤とp−メチル−ベンジリデンショウノウとジアリールブタジエン化合物を含有する遮蔽組成物 |
US10/463,433 US20040062727A1 (en) | 2000-12-18 | 2003-06-18 | Photostable photoprotective UV-screening compositions comprising dibenzoylmethane/methyl-benzylidenecamphor/diarylbutadiene compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0016521A FR2818129B1 (fr) | 2000-12-18 | 2000-12-18 | Composition filtrante photostable contenant un filtre uv du type derive du dibenzoylmethane, le p-methyl-benzylidene camphre et un compose 4,4-diarylbutadiene |
FR00/16521 | 2000-12-18 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/463,433 Continuation US20040062727A1 (en) | 2000-12-18 | 2003-06-18 | Photostable photoprotective UV-screening compositions comprising dibenzoylmethane/methyl-benzylidenecamphor/diarylbutadiene compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002049596A2 true WO2002049596A2 (fr) | 2002-06-27 |
WO2002049596A3 WO2002049596A3 (fr) | 2003-09-04 |
Family
ID=8857816
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2001/003636 WO2002049596A2 (fr) | 2000-12-18 | 2001-11-20 | Composition filtrante contenant un filtre du type derive du dibenzoylmethane, le p-methyl-benzylidene camphre et un compose 4,4-diarylbutadiene |
Country Status (6)
Country | Link |
---|---|
US (1) | US20040062727A1 (fr) |
EP (1) | EP1359894A2 (fr) |
JP (1) | JP2004517095A (fr) |
AU (1) | AU2002218389A1 (fr) |
FR (1) | FR2818129B1 (fr) |
WO (1) | WO2002049596A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004315824A (ja) * | 2003-04-14 | 2004-11-11 | L'oreal Sa | 少なくとも一のジブロック又はトリブロックコポリマー及び4,4−ジアリールブタジエンを含有する水性光保護組成物、その用途 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2440933A1 (fr) * | 1978-11-13 | 1980-06-06 | Givaudan & Cie Sa | Derive du dibenzoylmethane utilisable comme agent de protection contre la lumiere |
FR2607700A1 (fr) * | 1986-12-08 | 1988-06-10 | Oreal | Composition cosmetique photostable contenant un filtre uv-a et un filtre uv-b, son utilisation pour la protection de la peau contre les rayons uv et procede de stabilisation du filtre uv-a par le filtre uv-b |
DE19746654A1 (de) * | 1997-08-13 | 1999-02-18 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
DE19755649A1 (de) * | 1997-12-15 | 1999-06-17 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
US5985250A (en) * | 1995-12-08 | 1999-11-16 | Societe L'oreal S.A. | Stabilised sunscreen compositions |
EP0967200A1 (fr) * | 1998-06-26 | 1999-12-29 | Basf Aktiengesellschaft | 4,4-Diarylbutadiènes comme filtres UV hydrosolubles et photostables pour préparations cosmétiques et pharmaceutiques |
EP1008586A1 (fr) * | 1998-12-11 | 2000-06-14 | Basf Aktiengesellschaft | Diarylbutadiènes oligomères |
DE10007017A1 (de) * | 2000-02-16 | 2001-08-23 | Cognis Deutschland Gmbh | Sonnenschutzmittel |
EP1133981A2 (fr) * | 2000-03-15 | 2001-09-19 | Basf Aktiengesellschaft | Utilisation des combinaisons des agents de protection solaire contenant 4,4-Diarylbutadienes comme filtres photostabiles contre les rayonnements UV dans des préparations cosmétiques et pharmaceutiques |
-
2000
- 2000-12-18 FR FR0016521A patent/FR2818129B1/fr not_active Expired - Fee Related
-
2001
- 2001-11-20 WO PCT/FR2001/003636 patent/WO2002049596A2/fr not_active Application Discontinuation
- 2001-11-20 AU AU2002218389A patent/AU2002218389A1/en not_active Abandoned
- 2001-11-20 JP JP2002550938A patent/JP2004517095A/ja active Pending
- 2001-11-20 EP EP01271204A patent/EP1359894A2/fr not_active Withdrawn
-
2003
- 2003-06-18 US US10/463,433 patent/US20040062727A1/en not_active Abandoned
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2440933A1 (fr) * | 1978-11-13 | 1980-06-06 | Givaudan & Cie Sa | Derive du dibenzoylmethane utilisable comme agent de protection contre la lumiere |
FR2607700A1 (fr) * | 1986-12-08 | 1988-06-10 | Oreal | Composition cosmetique photostable contenant un filtre uv-a et un filtre uv-b, son utilisation pour la protection de la peau contre les rayons uv et procede de stabilisation du filtre uv-a par le filtre uv-b |
US5985250A (en) * | 1995-12-08 | 1999-11-16 | Societe L'oreal S.A. | Stabilised sunscreen compositions |
DE19746654A1 (de) * | 1997-08-13 | 1999-02-18 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
DE19755649A1 (de) * | 1997-12-15 | 1999-06-17 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
EP0967200A1 (fr) * | 1998-06-26 | 1999-12-29 | Basf Aktiengesellschaft | 4,4-Diarylbutadiènes comme filtres UV hydrosolubles et photostables pour préparations cosmétiques et pharmaceutiques |
EP1008586A1 (fr) * | 1998-12-11 | 2000-06-14 | Basf Aktiengesellschaft | Diarylbutadiènes oligomères |
DE10007017A1 (de) * | 2000-02-16 | 2001-08-23 | Cognis Deutschland Gmbh | Sonnenschutzmittel |
EP1133981A2 (fr) * | 2000-03-15 | 2001-09-19 | Basf Aktiengesellschaft | Utilisation des combinaisons des agents de protection solaire contenant 4,4-Diarylbutadienes comme filtres photostabiles contre les rayonnements UV dans des préparations cosmétiques et pharmaceutiques |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004315824A (ja) * | 2003-04-14 | 2004-11-11 | L'oreal Sa | 少なくとも一のジブロック又はトリブロックコポリマー及び4,4−ジアリールブタジエンを含有する水性光保護組成物、その用途 |
US7316809B2 (en) | 2003-04-14 | 2008-01-08 | L'oreal | Aqueous photoprotective compositions comprising diblock or triblock copolymers and 4,4-diarylbutadiene UV-A sunscreens |
Also Published As
Publication number | Publication date |
---|---|
JP2004517095A (ja) | 2004-06-10 |
FR2818129A1 (fr) | 2002-06-21 |
AU2002218389A1 (en) | 2002-07-01 |
EP1359894A2 (fr) | 2003-11-12 |
FR2818129B1 (fr) | 2004-02-27 |
US20040062727A1 (en) | 2004-04-01 |
WO2002049596A3 (fr) | 2003-09-04 |
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