FR2895240A1 - Cosmetic and/or dermatologic composition, useful to protect skin and/or superficial body growths, comprises alpha-cyano-beta-diphenylacrylic acid ester, triamine derivative, dibenzoylmethane derivative and paramethoxycinnamic acid ester - Google Patents
Cosmetic and/or dermatologic composition, useful to protect skin and/or superficial body growths, comprises alpha-cyano-beta-diphenylacrylic acid ester, triamine derivative, dibenzoylmethane derivative and paramethoxycinnamic acid ester Download PDFInfo
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- FR2895240A1 FR2895240A1 FR0513332A FR0513332A FR2895240A1 FR 2895240 A1 FR2895240 A1 FR 2895240A1 FR 0513332 A FR0513332 A FR 0513332A FR 0513332 A FR0513332 A FR 0513332A FR 2895240 A1 FR2895240 A1 FR 2895240A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 239000002537 cosmetic Substances 0.000 title claims abstract description 26
- -1 alpha-cyano-beta-diphenylacrylic acid ester Chemical class 0.000 title claims abstract description 13
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 title claims abstract description 11
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 230000021332 multicellular organism growth Effects 0.000 title claims abstract description 6
- 150000007974 melamines Chemical class 0.000 claims abstract description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 3
- 230000005855 radiation Effects 0.000 claims description 10
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 7
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 claims description 6
- 230000000475 sunscreen effect Effects 0.000 claims description 6
- 239000000516 sunscreening agent Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000003094 microcapsule Substances 0.000 claims description 5
- 230000000295 complement effect Effects 0.000 claims description 4
- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- GMUDCCCPVSCMPS-UHFFFAOYSA-N 3,4-diethyl-2-hexoxyphenol;2-methoxyphenol;triazine Chemical compound C1=CN=NN=C1.COC1=CC=CC=C1O.CCCCCCOC1=C(O)C=CC(CC)=C1CC GMUDCCCPVSCMPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 claims description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 230000010534 mechanism of action Effects 0.000 abstract 1
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 description 21
- 229960005193 avobenzone Drugs 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 11
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 9
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 8
- 229960000601 octocrylene Drugs 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 6
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 4
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 3
- 229960001679 octinoxate Drugs 0.000 description 3
- 230000037072 sun protection Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004904 UV filter Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- MXOAEAUPQDYUQM-QMMMGPOBSA-N (S)-chlorphenesin Chemical compound OC[C@H](O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-QMMMGPOBSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 1
- FBNAWLJSQORPAX-UHFFFAOYSA-N 4-methyl-3-propan-2-ylphenol Chemical compound CC(C)C1=CC(O)=CC=C1C FBNAWLJSQORPAX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- JDRSMPFHFNXQRB-CMTNHCDUSA-N Decyl beta-D-threo-hexopyranoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)C(O)[C@H](O)C1O JDRSMPFHFNXQRB-CMTNHCDUSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010019345 Heat stroke Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 208000007180 Sunstroke Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 1
- 229960004101 bemotrizinol Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940083936 c20-22 alcohols Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960003993 chlorphenesin Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 229940073499 decyl glucoside Drugs 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- PKPOVTYZGGYDIJ-UHFFFAOYSA-N dioctyl carbonate Chemical compound CCCCCCCCOC(=O)OCCCCCCCC PKPOVTYZGGYDIJ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000005338 frosted glass Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 229940048869 o-cymen-5-ol Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- 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
-
- 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
-
- 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
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
Abstract
Description
Compositions cosmétiques et dermatologiques pour la protection solaireCosmetic and dermatological compositions for sun protection
La présente invention se rapporte au domaine de la protection de la peau et en particulier à celui de la protection solaire. The present invention relates to the field of protection of the skin and in particular to that of sun protection.
L'invention a plus précisément pour objet de nouvelles compositions cosmétiques et/ou dermatologiques, destinées à la protection de la peau et/ou des phanères contre les rayonnements ultraviolets (UV), en particulier les rayonnements solaires. The subject of the invention is more specifically new cosmetic and / or dermatological compositions intended for the protection of the skin and / or integuments against ultraviolet (UV) radiation, in particular solar radiation.
L'invention a spécifiquement pour objet de nouvelles compositions cosmétiques et/ou dermatologiques, couvrant un large spectre d'absorption UV, constituées de l'association de plusieurs filtres dans un support cosmétiquement et/ou dermatologiquement acceptable. The invention specifically relates to novel cosmetic and / or dermatological compositions, covering a broad spectrum of UV absorption, consisting of the combination of several filters in a cosmetically and / or dermatologically acceptable support.
L'invention a également pour objet l'utilisation de ces compositions pour la protection 15 solaire de la peau et/ou des phanères des adultes et des enfants. The invention also relates to the use of these compositions for the solar protection of the skin and / or superficial body growths of adults and children.
Les rayonnements UV, en particulier les rayonnements solaires, peuvent provoquer des altérations de la peau telles que l'érythème (coup de soleil), le vieillissement prématuré, la perte d'élasticité et les cancers cutanés. En outre, l'insolation peut être la cause de 20 phénomènes d'allergie. Ces rayonnements doivent donc être filtrés lors de l'exposition au soleil. UV radiation, especially solar radiation, can cause skin damage such as erythema (sunburn), premature aging, loss of elasticity and skin cancer. In addition, sunstroke can be the cause of 20 allergy phenomena. This radiation must be filtered during exposure to the sun.
Dans le spectre solaire, trois catégories de rayonnement peuvent être distinguées parmi les UV: In the solar spectrum, three categories of radiation can be distinguished among UV:
25 • Les UVA: 320 - 400 nm • Les UVB: 290 - 320 nm • Les UVC: inférieurs à 290 nm • UVA: 320 - 400 nm • UVB: 290 - 320 nm • UVC: less than 290 nm
Les UVC sont majoritairement filtrés par la couche d'ozone. Cependant, afin d'assurer une protection solaire optimale, les normes actuelles exigent des produits anti-UV une large 30 couverture du spectre UVA et UVB, entre 290 et 400 nm. UVCs are mostly filtered by the ozone layer. However, in order to provide optimal sun protection, current standards require broad UV and UVA spectrum coverage products between 290 and 400 nm.
Une solution à ce problème technique consiste à associer différents filtres UV possédant des pics d'absorption maximale judicieusement décalés, afin d'obtenir une absorption continue et suffisante sur toute la largeur du spectre concerné (290-400 nm). A cette fin, pour assurer une excellente couverture du spectre UVB, il semble particulièrement intéressant d'utiliser au moins trois filtres UVB différents : One solution to this technical problem consists in associating different UV filters having judiciously offset maximum absorption peaks, in order to obtain a continuous and sufficient absorption over the entire width of the spectrum concerned (290-400 nm). To this end, to ensure excellent coverage of the UVB spectrum, it seems particularly advantageous to use at least three different UVB filters:
Un ester d'acide a-cyano-(3,(3'diphénylacrylique, en particulier l'a-cyano-40 (3,(3'diphényl-acrylate de 2-éthylhexyle, également appelé Octocrylène (OCR). Son pic d'absorption maximale se situe à 303 nm. An α-cyano- (3, 3'-diphenylacrylic acid ester, in particular α-cyano-40 (3, 3'-diphenyl-2-ethylhexyl acrylate, also called Octocrylene (OCR). maximum absorption is 303 nm.
Un ester de l'acide paraméthoxycinnamique, en particulier le paraméthoxycinnamate de 2-éthylhexyle, également appelé Ethyl Hexyl 45 Methoxycinnamate (OMC). Son pic d'absorption maximale se situe à 308 nm. An ester of paramethoxycinnamic acid, particularly 2-ethylhexyl paramethoxycinnamate, also called Ethyl Hexyl Methoxycinnamate (OMC). Its peak absorption peak is 308 nm.
Un dérivé de 1,3,5-triazine-2,4,6-triamine, en particulier la 2,4,6-tris[p-(2'éthylhexyl-l'-oxycarbonyl)anilino]-1,3,5-triazine, également appelée Ethyl Hexyl Triazone (EHT). Son pic d'absorption maximale se situe à 312 nm. 35 Par ailleurs, pour assurer la protection vis-à-vis des UVA, les dérivés de dibenzoylméthane constituent des filtres très efficaces, en particulier le 4-tert-butyl-4'-méthoxy-dibenzoylméthane, également appelé Butylmethoxydibenzoylmethane (BMDBM). Son pic d'absorption maximale se situe à 358 nm. A 1,3,5-triazine-2,4,6-triamine derivative, especially 2,4,6-tris [p- (2-ethylhexyl-1-oxycarbonyl) anilino] -1,3,5 -triazine, also called Ethyl Hexyl Triazone (EHT). Its peak absorption peak is 312 nm. In addition, to protect against UVA, dibenzoylmethane derivatives are very effective filters, especially 4-tert-butyl-4'-methoxy-dibenzoylmethane, also called butylmethoxydibenzoylmethane (BMDBM). Its peak absorption peak is 358 nm.
Ces filtres UVA et UVB sont connus et commercialisés, notamment sous les dénominations suivantes : - OCR : Parsol 340, Eusolex 1020 ; - OMC : Parsol MCX, Eusolex 2292 ; - EHT : Uvinul T150 ; - BMDBM : Parsol 1789, Eusolex 9020 ; L'association de ces quatre filtres, en raison du décalage judicieux de leurs pics d'absorption maximale, devrait donc permettre une excellente couverture de l'ensemble du spectre UVA-UVB. These UVA and UVB filters are known and marketed, especially under the following names: OCR: Parsol 340, Eusolex 1020; - WTO: Parsol MCX, Eusolex 2292; - EHT: Uvinul T150; BMDBM: Parsol 1789, Eusolex 9020; The combination of these four filters, due to the judicious shift of their maximum absorption peaks, should therefore allow excellent coverage of the entire UVA-UVB spectrum.
Cependant, la Demanderesse a constaté que le BMDBM, en présence des 3 filtres UVB et sous irradiation UV, présentait l'inconvénient de se dégrader. La couverture UV théorique n'était donc plus obtenue. However, the Applicant has found that the BMDBM, in the presence of 3 UVB filters and under UV irradiation, had the disadvantage of degrading. The theoretical UV coverage was no longer obtained.
Cette dégradation du BMDBM a été imputée à la présence d'OMC, en raison d'une réaction chimique entre ces deux composants. Ce résultat est en accord avec les données de la littérature ; le brevet EP0815835 (l'Oréal) revendique en effet des compositions solaires contenant, entre autres, du BMDBM et caractérisées par l'absence d'OMC. This degradation of BMDBM was attributed to the presence of WTO, due to a chemical reaction between these two components. This result is in agreement with the data of the literature; Patent EP0815835 (l'Oréal) claims indeed solar compositions containing, inter alia, BMDBM and characterized by the absence of OMC.
L'invention a donc pour objet la réalisation de nouvelles compositions cosmétiques et/ou dermatologiques couvrant un large spectre d'absorption UV et présentant une bonne photostabilité. L'invention réside dans le fait que l'on a pu associer, sans compromettre la stabilité de la composition, les filtres solaires suivants : The invention therefore relates to the production of new cosmetic and / or dermatological compositions covering a broad UV absorption spectrum and having good photostability. The invention lies in the fact that it was possible to associate, without compromising the stability of the composition, the following sunscreens:
- un ester d'acide a-cyano-f3,(3'diphénylacrylique, notamment l'a-cyanof3,f3'diphényl-acrylate de 2-éthylhexyle (OCR), - un dérivé de 1,3,5-triazine-2.4,6-triamine, notamment la 2,4,6-tris[p-(2'éthylhexyl-1'-oxycarbonyl)anilino]-1,3.5-triazine (EHT), an α-cyano-β, 3'-diphenylacrylic acid ester, in particular α-cyanofl, 3'-diphenyl-2-ethylhexyl acrylate (OCR), a 1,3,5-triazine-2,4 derivative; 6-triamine, especially 2,4,6-tris [p- (2-ethylhexyl-1'-oxycarbonyl) anilino] -1,3,5-triazine (EHT),
un dérivé de dibenzoylméthane, notamment le 4-tert-butyl-4'-méthoxydiben-40 zoylméthane (BMDBM), a dibenzoylmethane derivative, especially 4-tert-butyl-4'-methoxydiben-40-ylmethane (BMDBM),
- un ester de l'acide paraméthoxycinnamique, en particulier le paraméthoxycinnamate de 2-éthylhexyle (OMC), an ester of paramethoxycinnamic acid, in particular 2-ethylhexyl paramethoxycinnamate (OMC),
45 à la condition que l'ester d'acide paraméthoxycinnamique et/ou le dérivé de dibenzoylméthane soient sous forme micro-encapsulée, notamment dans des matériaux polymères organiques ou minéraux, en particulier dans des oxydes inorganiques. With the proviso that the paramethoxycinnamic acid ester and / or the dibenzoylmethane derivative are in microencapsulated form, especially in organic or inorganic polymeric materials, particularly in inorganic oxides.
Des compositions solaires contenant du paraméthoxycinnamate de 2-éthylhexyle ou du 4-50 tert-butyl-4'-méthoxydiben-zoylméthane micro-encapsulés ont précédemment été décrites dans la demande PCT WO03/011239 (Merck AG).35 Selon une forme préférentielle de l'invention, les microcapsules sont composées d'un gel de silice. Solar compositions containing 2-ethylhexyl paramethoxycinnamate or microencapsulated 4-50 tert-butyl-4'-methoxydibenzoylmethane have previously been described in PCT application WO03 / 011239 (Merck AG). According to a preferred form of the invention, the microcapsules are composed of a silica gel.
Selon une forme davantage préférée de l'invention, on utilise l'OMC micro-encapsulé commercialisé sous la dénomination Eusolex UV-PearlsTM OMC. According to a more preferred form of the invention, the microencapsulated OMC marketed under the name Eusolex UV-Pearls ™ OMC is used.
L'utilisation d'OMC et/ou de BMDBM sous une forme micro-encapsulée permet d'empêcher ces deux composés de réagir l'un avec l'autre, évitant en particulier la 10 dégradation du BMDBM. The use of OMC and / or BMDBM in a microencapsulated form makes it possible to prevent these two compounds from reacting with each other, in particular avoiding the degradation of BMDBM.
Préférentiellement, les compositions selon l'invention ont des teneurs en OCR et en EHT comprises chacune entre 0,1 et 20% du poids total de la composition et, d'une manière davantage préférée, entre 0,5 et 10% du poids total de la composition. Dans le cas des compositions contenant du BMDBM sous forme libre, les compositions selon l'invention ont préférentiellement une teneur en BMDBM comprise entre 0,1 et 10% du poids total de la composition et, d'une manière davantage préférée, entre 0,5 et 5% du poids total de la composition. 20 Dans le cas des compositions contenant de l'OMC sous forme libre, les compositions selon l'invention ont préférentiellement une teneur en OMC comprise entre 0,1 et 10% du poids total de la composition et, d'une manière davantage préférée, entre 0,5 et 5% du poids total de la composition. Dans les formes micro-encapsulées, la teneur en principe actif s'échelonne préférentiellement de 33 à 40% en masse par rapport à la masse totale de microcapsules. Preferably, the compositions according to the invention have OCR and EHT contents each comprised between 0.1 and 20% of the total weight of the composition and, more preferably, between 0.5 and 10% of the total weight. of the composition. In the case of compositions containing BMDBM in free form, the compositions according to the invention preferably have a BMDBM content of between 0.1 and 10% of the total weight of the composition and, more preferably, between 0, 5 and 5% of the total weight of the composition. In the case of compositions containing OMC in free form, the compositions according to the invention preferably have a content of OMC of between 0.1 and 10% of the total weight of the composition and, more preferably, between 0.5 and 5% of the total weight of the composition. In microencapsulated forms, the content of active ingredient preferably ranges from 33 to 40% by weight relative to the total mass of microcapsules.
Dans le cas des compositions contenant du BMDBM sous forme micro-encapsulée, les 30 compositions selon l'invention ont une teneur en BMDBM micro-encapsulé préférentiellement comprise entre 0,1 et 30% du poids total de la composition, d'une manière davantage préférée entre 1 et 30% du poids total de la composition et d'une manière encore davantage préférée entre 1 et 15% du poids total de la composition. In the case of compositions containing BMDBM in microencapsulated form, the compositions according to the invention have a content of BMDBM microencapsulated preferentially between 0.1 and 30% of the total weight of the composition, in a manner more preferred between 1 and 30% of the total weight of the composition and even more preferably between 1 and 15% of the total weight of the composition.
35 Dans le cas des compositions contenant de l'OMC sous forme micro-encapsulée, les compositions selon l'invention ont une teneur en OMC micro-encapsulé préférentiellement comprise entre 0,1 et 30% du poids total de la composition, d'une manière davantage préférée entre 1 et 30% du poids total de la composition et d'une manière encore davantage préférée entre 1 et 15% du poids total de la composition. 40 L'association des quatre composés précédemment évoqués permet de couvrir de façon satisfaisante la gamme des UVA-UVB. Toutefois, on peut choisir de renforcer la protection solaire résultante par l'ajout d'un ou de plusieurs filtres solaires complémentaires. 45 En tant que filtre complémentaire, on peut utiliser les dérivés du benzotriazole-2-yl-phénol, notamment le 2,2'-méthylène-bis-{6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tétraméthylbutyl) -phénol}, également connu sous la dénomination INCI Methylene-Bis Benzotriazolyl Tetramethylbutylphenol (MBBT). Ce composé présente une absorption maximale en UVB 50 à 305 nm. Il est aussi un filtre UVA efficace. Il est notamment commercialisé sous la dénomination Tinosorb M. 15 25 On peut également utiliser des dérivés de la 1,3,5-triazine tels que la Bis-ethyl Hexyloxyphenol Methoxyphenol Triazine (dénomination INCI). Ce composé présente une absorption importante sur une large gamme du spectre UVA-UVB. Il est notamment commercialisé sous la dénomination Tinosorb S. In the case of compositions containing OMC in microencapsulated form, the compositions according to the invention have a microencapsulated OMC content preferably of between 0.1 and 30% of the total weight of the composition, more preferably between 1 and 30% of the total weight of the composition and even more preferably between 1 and 15% of the total weight of the composition. The combination of the four previously mentioned compounds makes it possible to satisfactorily cover the range of UVA-UVB. However, one can choose to strengthen the resulting sunscreen by adding one or more complementary sunscreens. As a supplementary filter, benzotriazol-2-yl-phenol derivatives, especially 2,2'-methylene-bis- {6- (2H-benzotriazol-2-yl) -4- (1, 1,3,3-tetramethylbutyl) phenol}, also known as INCI Methylene-Bis Benzotriazolyl Tetramethylbutylphenol (MBBT). This compound has a maximum absorption of UVB 50 at 305 nm. It is also an effective UVA filter. It is especially marketed under the name Tinosorb M. It is also possible to use 1,3,5-triazine derivatives such as Bis-ethyl Hexyloxyphenol Methoxyphenol Triazine (INCI name). This compound has significant absorption over a wide range of the UVA-UVB spectrum. It is especially marketed under the name Tinosorb S.
De même, on peut utiliser l'ester hexylique d'acide 2-(4-Diéthylamino-2-hydroxybenzoyl)-benzoïque, également connu sous la dénomination INCI Diethylamino Hydroxybenzoyl Hexyl Benzoate. Il s'agit d'un filtre UVA performant dont l'absorption maximale se situe à 354 nm. Il est notamment commercialisé sous la dénomination Uvinul A Plus. Similarly, 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, also known as INCI Diethylamino Hydroxybenzoyl Hexyl Benzoate, may be used. It is a powerful UVA filter with a maximum absorption of 354 nm. It is marketed in particular under the name Uvinul A Plus.
Ces exemples ne sont pas limitatifs des filtres UV complémentaires pouvant être incorporés dans les compositions selon l'invention. These examples are not limiting of the complementary UV filters that may be incorporated in the compositions according to the invention.
Les compositions réalisées selon l'invention pourront contenir en outre un ou plusieurs excipients ou véhicules adaptés à l'application sur la peau et/ou les phanères, comme par exemple des agents épaississants, des agents émulsionnants, des tensioactifs et/ou des parfums. The compositions produced according to the invention may also contain one or more excipients or vehicles suitable for application to the skin and / or integuments, such as thickeners, emulsifiers, surfactants and / or perfumes.
Les compositions pourront se présenter sous toute forme applicable sur la peau et/ou les phanères, comme par exemple les gels, les lotions, les émulsions, les dispersions, les laits, les crèmes, les onguents, les mousses, les bâtons (sticks), les sprays et/ou les aérosols. The compositions may be in any form applicable to the skin and / or integuments, such as, for example, gels, lotions, emulsions, dispersions, milks, creams, ointments, mousses, sticks , sprays and / or aerosols.
L'invention a également pour objet l'utilisation à des fins cosmétiques des compositions selon l'invention, pour protéger la peau et/ou les phanères des rayonnement UV, en particulier des rayonnements solaires. A cette fin, les compositions selon l'invention seront appliquées sur la peau et/ou les phanères en quantité efficace, de préférence à raison de 1 à 6 applications par jour. The subject of the invention is also the use for cosmetic purposes of the compositions according to the invention for protecting the skin and / or the integuments from UV radiation, in particular solar radiation. For this purpose, the compositions according to the invention will be applied to the skin and / or superficial body growths in an effective amount, preferably at a rate of 1 to 6 applications per day.
Les exemples suivants illustrent l'invention sans toutefois la limiter : The following examples illustrate the invention without limiting it:
Exemple 1 : Composition cosmétique anti-UV Ingrédients (Nomenclature INCI) % massique C20-22 Alkyl phosphate / C20-22 alcohols 0,5-6 Butylmethoxydibenzoylmethane (BMDBM) 5 Ethyl Hexyl Triazone (EHT) Octocrylene (OCT) 5-20 Dicaprylyl carbonate Tricontanyl/PVP 2 Eau thermale d'Uriage 10 Tetrasodium EDTA 0,2 Xanthan gum 0,01-0 Benzoic acid 0,2 Glycerin Ethyl Hexyl Methoxycinnamate (OMC) micro-encapsulé 3 Sodium Hydroxide 0,02 MBBT/Aqua/Decyl glucoside/Propylene glycol/ 12 Xanthan gum Chlorphenesin o-Cymen-5-ol Cyclomethicone Exemple 2 : Comparaison de la dégradation du BMDBM libre dans des compositions contenant de l'OMC libre ou encapsulé Example 1: Anti-UV Cosmetic Composition Ingredients (INCI Nomenclature)% by mass C20-22 Alkyl Phosphate / C20-22 Alcohols 0.5-6 Butylmethoxydibenzoylmethane (BMDBM) Ethyl Hexyl Triazone (EHT) Octocrylene (OCT) 5-20 Dicaprylyl carbonate Tricontanyl / PVP 2 Uriage Thermal Water 10 Tetrasodium EDTA 0.2 Xanthan gum 0.01-0 Benzoic acid 0.2 Glycerin Ethyl Hexyl Methoxycinnamate (OMC) microencapsulated 3 Sodium Hydroxide 0.02 MBBT / Aqua / Decyl glucoside / Propylene glycol / 12 Xanthan gum Chlorphenesin o-Cymen-5-ol Cyclomethicone Example 2: Comparison of the degradation of free BMDBM in compositions containing free or encapsulated OMC
Deux compositions cosmétiques A et B ont été préparées. La composition A est réalisée selon l'invention, avec de l'OMC micro-encapsulé. Ce dernier contenant environ 37% d'OMC en masse, la composition B contient une quantité d'OMC libre équivalente à la quantité d'OMC présente dans la composition A. Composition A B OMC micro-encapsulé 14,30% - OMC libre - 5% EHT 5% 5% BMDBM 5% 5% OCR 5% 5% MBBT 12% 12% Les deux compositions sont soumises au protocole suivant : Pour chaque produit solaire, quatre étalements sont réalisés sur des lames de verre dépoli. Two cosmetic compositions A and B were prepared. Composition A is produced according to the invention with micro-encapsulated OMC. The latter containing about 37% of OMC by weight, the composition B contains a quantity of free OMC equivalent to the amount of OMC present in the composition A. Microencapsulated OMC AB composition 14.30% - free OMC - 5 % EHT 5% 5% BMDBM 5% 5% OCR 5% 5% MBBT 12% 12% Both compositions are subject to the following protocol: For each solar product, four spreads are made on frosted glass slides.
La quantité est de 2 0,2 mg/cm2. Deux lames (témoin TA) sont conservées à l'obscurité et à 20 C. Deux lames sont irradiées avec l'appareil SUNTEST CPS+. La puissance de l'irradiation est de 550 W/m2, la durée est de 60 minutes. La température est de 40-45 C. La dose reçue est de 19,8 J/cm2, ce qui correspond à environ quatre fois la dose minimale érythrémateuse. The amount is 0.2 mg / cm 2. Two slides (TA control) are kept in the dark at 20 C. Two slides are irradiated with the SUNTEST CPS +. The power of the irradiation is 550 W / m2, the duration is 60 minutes. The temperature is 40-45 C. The dose received is 19.8 J / cm2, which corresponds to approximately four times the minimum erythrematous dose.
Les lames sont ensuite immergées dans un volume connu d'éthanol et traitées par ultrasons durant 10 minutes. The slides are then immersed in a known volume of ethanol and sonicated for 10 minutes.
Le dosage du BMDBM résiduel est ensuite effectué par HPLC ; les résultats sont exprimés 25 par le pourcentage résiduel de filtres après 60 minutes d'irradiation. Le 100% est constitué par la valeur obtenue dans le témoin TA. Composition A B BMDBM résiduel après irradiation 91% 85% The residual BMDBM assay is then performed by HPLC; the results are expressed as the residual percentage of filters after 60 minutes of irradiation. The 100% is constituted by the value obtained in the control TA. Composition A B BMDBM residual after irradiation 91% 85%
On constate une dégradation significative du BMDBM en présence d'OMC libre 30 (composition B). La présence d'OMC sous forme micro-encapsulée (composition A) conduit en revanche à une bonne stabilité du BMDBM. There is a significant degradation of BMDBM in the presence of free OMC (composition B). The presence of OMC in microencapsulated form (composition A) leads on the other hand to a good stability of the BMDBM.
Claims (17)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0513332A FR2895240A1 (en) | 2005-12-26 | 2005-12-26 | Cosmetic and/or dermatologic composition, useful to protect skin and/or superficial body growths, comprises alpha-cyano-beta-diphenylacrylic acid ester, triamine derivative, dibenzoylmethane derivative and paramethoxycinnamic acid ester |
| ES06026641.8T ES2543195T3 (en) | 2005-12-26 | 2006-12-22 | Photoprotective compositions that reduce the risks of skin sensitization |
| PT60266418T PT1815844E (en) | 2005-12-26 | 2006-12-22 | Photoprotecting compositions with reduced risk of skin sensitisation |
| EP20060026641 EP1815844B1 (en) | 2005-12-26 | 2006-12-22 | Photoprotecting compositions with reduced risk of skin sensitisation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0513332A FR2895240A1 (en) | 2005-12-26 | 2005-12-26 | Cosmetic and/or dermatologic composition, useful to protect skin and/or superficial body growths, comprises alpha-cyano-beta-diphenylacrylic acid ester, triamine derivative, dibenzoylmethane derivative and paramethoxycinnamic acid ester |
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| FR2895240A1 true FR2895240A1 (en) | 2007-06-29 |
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| FR0513332A Pending FR2895240A1 (en) | 2005-12-26 | 2005-12-26 | Cosmetic and/or dermatologic composition, useful to protect skin and/or superficial body growths, comprises alpha-cyano-beta-diphenylacrylic acid ester, triamine derivative, dibenzoylmethane derivative and paramethoxycinnamic acid ester |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108042796A (en) * | 2018-01-04 | 2018-05-18 | 江西华文科创文化发展有限公司 | A kind of composition for removing free radical and preparation method and application |
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| CN108042796A (en) * | 2018-01-04 | 2018-05-18 | 江西华文科创文化发展有限公司 | A kind of composition for removing free radical and preparation method and application |
| CN108042796B (en) * | 2018-01-04 | 2021-11-30 | 江西华文科创文化发展有限公司 | Composition for removing free radicals and preparation method and application thereof |
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