JPS6351318A - Ultraviolet absorber and cosmetic containing same - Google Patents
Ultraviolet absorber and cosmetic containing sameInfo
- Publication number
- JPS6351318A JPS6351318A JP19594586A JP19594586A JPS6351318A JP S6351318 A JPS6351318 A JP S6351318A JP 19594586 A JP19594586 A JP 19594586A JP 19594586 A JP19594586 A JP 19594586A JP S6351318 A JPS6351318 A JP S6351318A
- Authority
- JP
- Japan
- Prior art keywords
- isocoumarin
- cosmetic
- compound
- ultraviolet rays
- ultraviolet
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract description 13
- 239000006097 ultraviolet radiation absorber Substances 0.000 title claims abstract description 7
- -1 methylenedioxy Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000006096 absorbing agent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 230000000694 effects Effects 0.000 abstract description 17
- IQZZFVDIZRWADY-UHFFFAOYSA-N isocoumarin Chemical compound C1=CC=C2C(=O)OC=CC2=C1 IQZZFVDIZRWADY-UHFFFAOYSA-N 0.000 abstract description 16
- 238000010521 absorption reaction Methods 0.000 abstract description 9
- 150000002512 isocoumarins Chemical class 0.000 abstract description 4
- 230000005855 radiation Effects 0.000 abstract description 4
- 206010040880 Skin irritation Diseases 0.000 abstract description 2
- 230000000172 allergic effect Effects 0.000 abstract description 2
- 231100000475 skin irritation Toxicity 0.000 abstract description 2
- 230000036556 skin irritation Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- 210000003491 skin Anatomy 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000009931 harmful effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000000475 sunscreen effect Effects 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- NIAQWGIIDXSIJJ-UHFFFAOYSA-N 3-(4-ethoxyphenyl)isochromen-1-one Chemical compound C1=CC(OCC)=CC=C1C1=CC2=CC=CC=C2C(=O)O1 NIAQWGIIDXSIJJ-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 206010041303 Solar dermatitis Diseases 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 206010042496 Sunburn Diseases 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229960001679 octinoxate Drugs 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- PDHSAQOQVUXZGQ-JKSUJKDBSA-N (2r,3s)-2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2h-chromene-5,7-diol Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC)=CC=C(O)C(O)=C1 PDHSAQOQVUXZGQ-JKSUJKDBSA-N 0.000 description 1
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- AKHSBAVQPIRVAG-UHFFFAOYSA-N 4h-isochromene-1,3-dione Chemical compound C1=CC=C2C(=O)OC(=O)CC2=C1 AKHSBAVQPIRVAG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 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 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960004881 homosalate Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 1
- UQDVHJGNIFVBLG-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O UQDVHJGNIFVBLG-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- 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
- 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
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
Landscapes
- 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)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野コ
本発明は、290〜400nmの有害な紫外線に対して
吸収効果を有する「イソクマリン」誘導体、及びそれを
含有し、日焼は防止効果の優れた化粧料の提供に関する
。Detailed Description of the Invention [Industrial Application Field] The present invention contains an "isocoumarin" derivative that has an absorption effect on harmful ultraviolet rays of 290 to 400 nm, and contains it, and has an excellent sunburn prevention effect. related to the provision of cosmetics.
[従来の技術]
太陽光線中の紫外線は、ヒト皮膚に有害な作用を有する
事が知られている。即ち290〜320nn1(UVI
3紫外線と略記する)の紫外線は、角yit1[1胞を
雪道して乳UJ[fまでたつし、日光紅斑の主たる原因
となり、メラニン発生作用も発現する。[Prior Art] Ultraviolet rays in sunlight are known to have harmful effects on human skin. That is, 290-320nn1 (UVI
Ultraviolet rays (abbreviated as 3 ultraviolet rays) pass through the cornea yit1[1] to the milk UJ[f, are the main cause of solar erythema, and also exhibit melanin-producing effects.
又、これより長波長の320〜400間紫外線(UVA
紫外線と略記する)は真皮まで浸透し、メラニン発生作
用を有しているため皮膚の黒化が生じる。In addition, ultraviolet rays (UVA) with longer wavelengths between 320 and 400
Ultraviolet rays (abbreviated as ultraviolet rays) penetrate into the dermis and have a melanin-producing effect, causing skin darkening.
さらにUVA紫外線、UVB紫外線の慢性的な照射は、
皮膚の老化を促進し、しみ、しわの発生など態形9を及
ぼすとも言われている。Furthermore, chronic irradiation with UVA and UVB ultraviolet rays
It is also said that it accelerates skin aging and causes Form 9, such as the appearance of age spots and wrinkles.
この様に、ヒト皮膚の及ぼす影響が明らかになるにつれ
て、これら紫外線から皮Hを保護する化合物の開発が今
まで以上に望まれるようになった。As the effects on human skin become clearer, the development of compounds that protect skin H from these ultraviolet rays has become more desirable than ever.
[発明が解決しようとする問題点コ
従来より、日光紅斑に対する防御方法は、鋭′g、研究
され、UVB吸収剤として数多くの化合物が開発され公
知となっている。しかしながら、これらの化合物のOV
A紫外線に対する吸収効果は非常に低く、太陽光線中の
紫外線の一部を吸収するにすぎない。太陽光線中の紫外
線から皮膚を保護するためには、UVB吸収剤の他に、
UVA吸収剤が必要となり、このUVA吸収剤の開発も
介意検討されている。[Problems to be Solved by the Invention] Methods for protecting against solar erythema have been intensively researched, and many compounds have been developed and known as UVB absorbers. However, the OV of these compounds
The absorption effect for ultraviolet A radiation is very low, and only a portion of the ultraviolet radiation in sunlight is absorbed. In addition to UVB absorbers, in order to protect the skin from ultraviolet rays in the sun,
A UVA absorber is required, and the development of this UVA absorber is also being considered.
UVB吸収剤、UVA吸収剤を併用する事により、外見
上、太陽光線中の紫外線を完全に吸収することは可能で
ある。しかしながら、これら複数の活性成分の組合せは
、太陽光線により予期せぬ光反応が進行する場合もある
事、また、紫外線吸収剤の全量が増大するため、安全性
に問題が住する場合もある。現在繁用されている紫外線
吸収剤のうち、幅広い紫外線を吸収するものとしては、
2−ハイドロキシ−4−メトキシベンゾフェノンが存在
するがUVA紫外線、UVB紫外線いずれに対してもそ
の吸収効果は弱く、十分な効果を期待する事は困難であ
る。By using a UVB absorber and a UVA absorber in combination, it is possible to completely absorb ultraviolet rays in sunlight. However, the combination of these multiple active ingredients may cause safety problems because unexpected photoreactions may proceed due to sunlight and the total amount of ultraviolet absorber increases. Among the UV absorbers commonly used today, those that absorb a wide range of UV rays include:
Although 2-hydroxy-4-methoxybenzophenone exists, its absorption effect on both UVA and UVB ultraviolet rays is weak, and it is difficult to expect a sufficient effect.
この様に、太陽光線中の紫外線を吸収し皮膚を保護する
化合物が望まれているにもかかわらず、この要望を満足
する化合物が無いのが現状である。As described above, although there is a desire for a compound that absorbs ultraviolet rays in sunlight and protects the skin, there is currently no compound that satisfies this demand.
期待される化合物としては、太陽光線中の紫外線を可能
な限り吸収し、無害で、光に対して安定性に優れたもの
でなければならない。本発明者はこれらの観点から鋭意
研究の結果、「イソクマリン」誘導体が特に適している
ことを見出し本発明を完成するに至った。The desired compound must absorb as much of the ultraviolet rays in sunlight as possible, be harmless, and have excellent stability against light. As a result of intensive research from these viewpoints, the present inventors found that "isocoumarin" derivatives are particularly suitable, and completed the present invention.
[問題点を解決するための手段]
即ち、本発明は、UVA紫外線及びUVB紫外線を実際
上完全に吸収し、また紫外線に対して安定性の良い「イ
ソクマリン」誘導体、及びそれらのうちの一種又は二種
以上を含有する事を特徴とする日焼は止め化粧料に関す
る。[Means for Solving the Problems] That is, the present invention provides "isocoumarin" derivatives that practically completely absorb UVA and UVB ultraviolet rays and are highly stable against ultraviolet rays, and one or more of them. The present invention relates to a sunscreen cosmetic characterized by containing two or more types.
以下、本発明の構成について詳述する。Hereinafter, the configuration of the present invention will be explained in detail.
本本発明の紫外線吸収剤は下記一般式(1)にて示され
る。The ultraviolet absorber of the present invention is represented by the following general formula (1).
す
(但し、Rは炭素数1〜4のアルキル基、炭素数1〜4
のアルコキシ基、メチレンジオキシ基、フェノキシ基を
表し、nは1又は2の整数を表す。)本発明に通用され
る化合物を合成する方法としては一般公知の方法(R几
、5hinen 、W、R,Knox、J。(However, R is an alkyl group having 1 to 4 carbon atoms,
represents an alkoxy group, methylenedioxy group, or phenoxy group, and n represents an integer of 1 or 2. ) As a method for synthesizing the compound applicable to the present invention, a generally known method (R. K., K., Knox, J.).
Org 、Chem、、16 、1064 (1951
) ) 、例えばホモフクル酸無水物とアルキル置換ベ
ンゼンあるいはアルコキシ置換ベンゼンを無水ベンゼン
又は無水ニトロベンゼン中で無水塩化アルミニウムを触
媒としたフリーデルクラフト反応を行うことにより容易
に得ることが出来る。Org, Chem, 16, 1064 (1951
) ), for example, can be easily obtained by performing a Friedel-Crafts reaction of homofucric anhydride and alkyl-substituted benzene or alkoxy-substituted benzene in anhydrous benzene or anhydrous nitrobenzene using anhydrous aluminum chloride as a catalyst.
本発明の化合物はそれ自体UVA紫外線及びUVB紫外
線を完全に吸収する能力を有しているものであり、日焼
は止め化粧料として十分な効果を発揮する。しかしなが
ら、非常に光線に対して過敏な人においては、わずかの
紫外線も有害であり、他の紫外線吸収剤を併用する事も
可能である。他の吸収剤例えば、ジベンゾイルメタン誘
導体として4.4″−ジメトキシジベンヅイルメタン、
4−メトキシ−4’−t−プチルジベンヅイルメタンな
ど、ベンゾフェノン誘導体として2−ハイドロキシ−4
−メトキシベンゾフェノン、2−ハイドロキシ−4−メ
トキシヘンシフエノン−5−スルホン酸など、その他ウ
ロカニン酸、p−アミノ安息香M、2−エチルへキシル
−P−ジメチルアミノベンゾエート、2−エチルへキシ
ル−P−メトキシシンナメート、モノ−2−エチルヘキ
サノイル−ジーP−メトキシシンナモイルプロパン、2
−エチルへキシルサリチレート、ホモメンチル゛サルチ
レートなどが挙げられる。The compound of the present invention itself has the ability to completely absorb UVA ultraviolet rays and UVB ultraviolet rays, and exhibits sufficient effects as a sunscreen cosmetic. However, for people who are extremely sensitive to light, even a small amount of UV rays can be harmful, so it is also possible to use other UV absorbers in combination. Other absorbents such as 4.4″-dimethoxydibenzylmethane as a dibenzoylmethane derivative;
2-Hydroxy-4 as a benzophenone derivative such as 4-methoxy-4'-t-butyldibenzylmethane
-Methoxybenzophenone, 2-hydroxy-4-methoxyhensiphenone-5-sulfonic acid, etc., other urocanic acid, p-aminobenzoic acid, 2-ethylhexyl-P-dimethylaminobenzoate, 2-ethylhexyl-P -methoxycinnamate, mono-2-ethylhexanoyl-di-P-methoxycinnamoylpropane, 2
-Ethylhexyl salicylate, homomenthyl salicylate, etc.
本発明の紫外線吸収剤の配合量は、目的とする日焼は防
止の程度により、また使用される季節により変化するが
、一般的には0.5〜10重量%、好ましくは0.5〜
5重量重量%者ある。The blending amount of the ultraviolet absorber of the present invention varies depending on the degree of prevention of sunburn and the season in which it is used, but it is generally 0.5 to 10% by weight, preferably 0.5 to 10% by weight.
5% by weight.
本発明に係る化粧料には、上記一般式(1)にて示され
る化合物のほか、化粧料として一般的に使用される添加
剤、例えば、固体状あるいは液状パラフィン、クリスタ
ルオイル、セレシン、オヅケライト、モノクンロウなど
の炭化水素類、シリコン油類、オリーブ、地ロウ、カル
ナバロウ、ラノリンのような植物性もしくは動物性油脂
やロウ、さらにステアリン酸、バルミチン酸、オレイン
酸、グリセリンモノステアリン酸エステル、グリセリン
ジステアリン酸エステル、グリセリンモノオレイン酸エ
ステル、イソプロピルミリスチン酸エステル、イソプロ
ピルステアリン酸エステルの如き脂肪酸およびそのエス
テル類、分岐脂肪酸の一価アルコール又は多価アルコー
ルエステル類、エチルアルコール、イソプロピルアルコ
ール、セチルアルコール、ステアリルアルコール、パル
ミルアルコールなどのアルコール類、グリコール、グリ
セリン、ソルビトールなどの多価アルコール、乳化剤又
は可溶化剤として非イオン界面活性剤、アニオン界面活
性剤、カチオン界面活性剤など、その他、必要に応じて
防腐剤、着色剤、香料などがあげられる。In addition to the compound represented by the above general formula (1), the cosmetic according to the present invention includes additives commonly used in cosmetics, such as solid or liquid paraffin, crystal oil, ceresin, ozkerite, Hydrocarbons such as monoclonal wax, silicone oils, vegetable or animal fats and waxes such as olive, earth's wax, carnauba wax, and lanolin, as well as stearic acid, valmitic acid, oleic acid, glycerin monostearate, and glycerin distearate. esters, fatty acids and their esters such as glycerin monooleate, isopropyl myristate, isopropyl stearate, monohydric or polyhydric alcohol esters of branched fatty acids, ethyl alcohol, isopropyl alcohol, cetyl alcohol, stearyl alcohol, Alcohols such as palmyl alcohol, polyhydric alcohols such as glycol, glycerin, and sorbitol, nonionic surfactants, anionic surfactants, cationic surfactants as emulsifiers or solubilizers, and preservatives as necessary. Coloring agents, fragrances, etc.
本発明の化粧料の性状は、例えば液状、乳液、スティ、
り状なと、その効果を発現できる性状であればいずれで
も良い。The properties of the cosmetics of the present invention include, for example, liquid, milky lotion, stickiness,
It may be in any shape as long as it can exhibit the effect.
本発明について、実施例を挙げて更に具体的に説明する
。The present invention will be described in more detail with reference to Examples.
実)fE例(o 3− (4°−メトキシフェニル)
イソクマリンの合成
ホモフタル酸無水物15g、アニソール80dの溶液に
16gの無水塩化アルミニウムを加えよく攪拌する。こ
の混合液を攪拌しながら除々に80°Cまで加熱し、こ
の温度で3時間攪拌を継続する。冷後、100−の水を
加え、濃塩酸で酸性とし、ベンゼンI○0−を加えて有
機層を分離する。有機層を10%′炭酸ナトリウム水溶
液で洗浄し乾燥した後、減圧下にベンゼン、アニソール
を留去する。残渣にエタノール30.Jを加え再結晶と
すると純粋な3−(4°−メトキシフェニル)イソクマ
リン2.3gが得られる。Actual) fE example (o 3- (4°-methoxyphenyl)
Synthesis of isocoumarin 16 g of anhydrous aluminum chloride is added to a solution of 15 g of homophthalic anhydride and 80 d of anisole and stirred well. This mixed solution is gradually heated to 80° C. while stirring, and stirring is continued at this temperature for 3 hours. After cooling, 100 - of water is added, acidified with concentrated hydrochloric acid, benzene I○0 - is added and the organic layer is separated. After washing the organic layer with a 10% aqueous sodium carbonate solution and drying, benzene and anisole were distilled off under reduced pressure. Add 30% ethanol to the residue. When recrystallized by adding J, 2.3 g of pure 3-(4°-methoxyphenyl)isocoumarin is obtained.
mp 116〜117゛、 121〜122℃(二重融
点)本発明に係る他の化合物も実施例(1)と同様の操
作により合成することができる。mp 116-117°, 121-122°C (double melting point) Other compounds according to the present invention can also be synthesized by the same procedure as in Example (1).
実施例(2)本発明の化合物の紫外線吸収効果比較化合
物として2−ハイドロキシ−4−メトキシベンゾフェノ
ンを用い、99.5%エタノ〜ル(試薬特級)溶媒中L
OP (W/ V )濃度での紫外線吸収効果(光吸度
)を表1に示した。Example (2) Ultraviolet absorption effect of the compound of the present invention Using 2-hydroxy-4-methoxybenzophenone as a comparison compound, L in 99.5% ethanol (reagent grade) solvent
Table 1 shows the ultraviolet absorption effect (light absorbance) at OP (W/V) concentration.
表1 紫外線吸収効果
290 0.69 0.65 0.6
5300 0.97 0.92. 0.
39310 1.04 0.9B
0.35320 0.95 0.90
0.40330 0.55 0.52
0.42340 0.52 0.49
0.34350 0.53 (15
00,203600,460,430,11
3700,330,310,03
3800,180,170,00
*1 1−(4’−メトキシフェニル)イソクマリン
*2 3−(4” −エトキシフェニル)イソクマリン
*32−ハイドロキシ−4−メトキシベンゾフェノン
これらの結果は、本発明化合物がUVA紫外線、UVB
紫外線に対して、比較化合物2−ハイドロキシ−4−メ
トキシベンゾフェノンより吸収効果が強く、日焼は止め
効果の高い事を示している。Table 1 Ultraviolet absorption effect 290 0.69 0.65 0.6
5300 0.97 0.92. 0.
39310 1.04 0.9B
0.35320 0.95 0.90
0.40330 0.55 0.52
0.42340 0.52 0.49
0.34350 0.53 (15
00,203600,460,430,11 3700,330,310,03 3800,180,170,00 *1 1-(4'-methoxyphenyl)isocoumarin*2 3-(4''-ethoxyphenyl)isocoumarin*32- Hydroxy-4-methoxybenzophenone These results demonstrate that the compound of the present invention
It has a stronger absorption effect on ultraviolet rays than the comparative compound 2-hydroxy-4-methoxybenzophenone, indicating that it has a high sun protection effect.
実施例(3)本発明化合物の紫外線に対する安定性(実
験方法)
99.5%エタノール(試薬特級)溶媒中、本発明化合
物並びに比較化合物を0.1%(W/V)になるように
熔解し、キセノンフェードメーターを用いて、15時間
、30時間紫外線を照射した。Example (3) Stability of the compound of the present invention against ultraviolet light (experimental method) The compound of the present invention and the comparative compound were dissolved in a 99.5% ethanol (reagent grade) solvent to a concentration of 0.1% (W/V). Then, using a xenon fade meter, ultraviolet rays were irradiated for 15 hours and 30 hours.
紫外線照射前後の紫外線吸収効果を比較し、残存率から
安定性を評価した。残存率は以下のようにして計算した
。The UV absorption effect before and after UV irradiation was compared, and the stability was evaluated from the residual rate. The survival rate was calculated as follows.
(以下余白) 安定性の評価は次の基準により行った(表2)。(Margin below) The stability was evaluated based on the following criteria (Table 2).
表2 安定性の評価基準
評価点 残存率
○ 残存率95%以上
△ 残存率90%以上
× 残存率90%以下
上記のようにして測定した紫外線に対する安定性評価結
果を表3に示した。Table 2 Stability Evaluation Criteria Evaluation Points Residual rate ○ Residual rate 95% or more Δ Residual rate 90% or more × Residual rate 90% or less Table 3 shows the stability evaluation results against ultraviolet rays measured as described above.
表3
(以下余白)
*I 3−(4“−メトキシフェニル)イソクマリン
*2 3−(4’ −エトキシフェニル)イソクマリ
ン
*3 3− (3’ 、4’ −メチレンジオキシフ
ェニル)イソクマリン
*42−エチルへキシル−P−メトキシシンナメート
表3の結果より、紫外線吸収剤として繁用されている2
−エチルへキシル−P−メトキシシンナメートと比較し
、本発明化合物は紫外線に対する安定性の優れているこ
とが明らかである。Table 3 (blank below) *I 3-(4"-methoxyphenyl)isocoumarin*2 3-(4'-ethoxyphenyl)isocoumarin*3 3-(3',4'-methylenedioxyphenyl)isocoumarin*42- Ethylhexyl-P-methoxycinnamate From the results in Table 3, 2 is frequently used as an ultraviolet absorber.
-Ethylhexyl-P-methoxycinnamate It is clear that the compounds of the present invention have superior stability against ultraviolet light.
以下に本発明について、別の実施例を挙げてさらに説明
するが、これにより本発明が限定されるものでは無い。The present invention will be further described below with reference to other examples, but the present invention is not limited thereby.
配合材はfflffi%で示す。Compounding materials are shown in fffffi%.
実施例(4)透明液状油
3− (4’ −エトキシフェニル)2,0%イソク
マリン
イソプロピルミリステート15 %
オリーブ油 %香料
通量(!!法)
50”〜60’にて油ベースを攪拌しながら、3−(4
′ −エトキシフェニル)イソクマリンを加え熔解し、
室温まで自然冷却する。Example (4) Clear liquid oil 3-(4'-ethoxyphenyl) 2.0% Isocoumarin Isopropyl myristate 15% Olive oil % Fragrance
Amount (!! method) While stirring the oil base at 50” to 60’, add 3-(4
′-ethoxyphenyl)isocoumarin was added and dissolved,
Cool naturally to room temperature.
実施例(5)クリーム
3−(4° −メトキシフェニル) 5 %インク
マリン
ジエチレングリコール七ノ 2 %ステアレ
ート
ステアリン酸 1.5%セチル
アルコール 0.5%ベンジルアル
コール 6.0%トリエタノールアミ
ン 1.0%精製水
84.0%香料
適量酸化防止剤、防腐剤 適量(
!1法)
油性部分を65°Cに加熱熔解して、同温度に加熱した
精製水を加え、攪拌しなから35°Cになった時、香料
、酸化防止剤、防腐剤を加え、室温になるまで攪拌を継
続する。Example (5) Cream 3-(4°-methoxyphenyl) 5% Ink Marine Diethylene Glycol Seven 2% Stearate Stearic Acid 1.5% Cetyl Alcohol 0.5% Benzyl Alcohol 6.0% Triethanolamine 1.0 %purified water
84.0% fragrance
Appropriate amount Antioxidant, preservative (appropriate amount)
! Method 1) Melt the oily part by heating to 65°C, add purified water heated to the same temperature, and when the temperature reaches 35°C without stirring, add fragrances, antioxidants, and preservatives, and let it cool to room temperature. Continue stirring until the mixture is mixed.
実施例(6) ヘアクリーム
3−(3″、4゛ −メチレンジオキ 0.5%ジフェ
ニル)イソクマリン
ミツロウ 1.0%流動パ
ラフィン 50 %ステアリン酸
3.09Aソルビタンセスキ
オレート2.2%
ポリオキシエチレンソルビタン゛ 1.8%モノウ
ラレート
精製水 41.5%香料
適量酸化防止剤、防腐剤
適量(製法)
実施例(4)と同様に製造した。Example (6) Hair Cream 3-(3″, 4″-methylene dioxy 0.5% diphenyl) isocoumarin beeswax 1.0% liquid paraffin 50% stearic acid 3.09A sorbitan sesquiolate 2.2% polyoxyethylene sorbitan゛ 1.8% monourarate purified water 41.5% fragrance
Appropriate amounts of antioxidants and preservatives (Production method) Produced in the same manner as in Example (4).
実施例(7) 日焼は止めスチックファンデイション
3−(4’−メトキシフェニル)4.0%イソクマリン
二酸化チタン 16.0カオリン
10.0雲母末
10.0亜鉛華
4.5酸化鉄(赤)1.4
酸化鉄(黄)4.0
酸化鉄(黒) 0・1固型パラ
フイン 5.0カルナバロウ
3.0流動パラフイン
34.0イソプロピルミリスチン酸エステル
5.0ソルビタンセスキオレイン酸 3.0エ
ステル
香料 適量(製法)
二酸化チタン、カオリン、雲母末、酸化鉄をブレンダー
でよく混合する(粉末部)。粉末部に流動パラフィンの
一部とソルビタンセスキオレイン酸エステルを加え、ホ
モミキサーで均一に分散し、他の成分を加熱融解してこ
れに加え、よくかきまぜる。これを容器に流し込み冷却
する。Example (7) Sunscreen stick foundation 3-(4'-methoxyphenyl) 4.0% isocoumarin titanium dioxide 16.0 kaolin 10.0 mica powder
10.0 zinc white
4.5 Iron oxide (red) 1.4 Iron oxide (yellow) 4.0 Iron oxide (black) 0.1 Solid paraffin 5.0 Carnauba wax
3.0 liquid paraffin
34.0 Isopropyl myristate ester
5.0 Sorbitan sesquioleic acid 3.0 Ester fragrance Appropriate amount (manufacturing method) Mix titanium dioxide, kaolin, mica powder, and iron oxide thoroughly in a blender (powder part). Add a portion of liquid paraffin and sorbitan sesquioleic acid ester to the powder portion, disperse uniformly with a homomixer, heat and melt the other components, add to this, and stir well. Pour this into a container and cool it.
なお、本発明に係る化粧料には、皮膚刺:敞性、アレル
ギー性は認められず、皮膚に対する安全性は極めて高い
ものであった。In addition, the cosmetics according to the present invention had no skin irritation, no allergic properties, and was extremely safe for the skin.
Claims (1)
のアルコキシ基、メチレンジオキシ基、フェノキシ基を
表し、nは1又は2の整数を表す。) 2 上記一般式(1)により示される紫外線吸収剤の一
種又は二種以上を含有することを特徴とする化粧料。[Claims] 1. An ultraviolet absorber represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (However, R is an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
represents an alkoxy group, methylenedioxy group, or phenoxy group, and n represents an integer of 1 or 2. ) 2 A cosmetic material containing one or more types of ultraviolet absorbers represented by the above general formula (1).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19594586A JPS6351318A (en) | 1986-08-21 | 1986-08-21 | Ultraviolet absorber and cosmetic containing same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19594586A JPS6351318A (en) | 1986-08-21 | 1986-08-21 | Ultraviolet absorber and cosmetic containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6351318A true JPS6351318A (en) | 1988-03-04 |
Family
ID=16349585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP19594586A Pending JPS6351318A (en) | 1986-08-21 | 1986-08-21 | Ultraviolet absorber and cosmetic containing same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6351318A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02108614A (en) * | 1988-10-18 | 1990-04-20 | Sansho Seiyaku Co Ltd | Agent for external application |
-
1986
- 1986-08-21 JP JP19594586A patent/JPS6351318A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02108614A (en) * | 1988-10-18 | 1990-04-20 | Sansho Seiyaku Co Ltd | Agent for external application |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4867964A (en) | Cosmetic composition containing hydroxylated chalcone derivatives and its use for protecting the skin and the hair against luminous radiations, new hydroxylated chalcone derivatives employed and process for their preparation | |
US3781417A (en) | Light protection agent for cosmetic purposes | |
JP2634179B2 (en) | Filterable cosmetic composition | |
US4710373A (en) | Long wavelength ultraviolet ray absorber | |
KR100294726B1 (en) | Benzophenone derivatives, UV absorbers and external skin preparations | |
JPS63165310A (en) | Light-stable cosmetic composition | |
US5718906A (en) | Light-stable cosmetic composition | |
US4837010A (en) | Long wave UV ray absorber | |
JPS6311343B2 (en) | ||
JPS6351318A (en) | Ultraviolet absorber and cosmetic containing same | |
JPH01135887A (en) | Ultraviolet ray absorber composition | |
JPH049355A (en) | Cinnamic acid derivative, uv absorber and dermatic external drug containing the same | |
JP2646257B2 (en) | UV absorber | |
JPH08245356A (en) | Method for utilizing dihydroxyacetone | |
JPS6351320A (en) | Ultraviolet absorber and cosmetic containing same | |
JPH07238275A (en) | Ultraviolet light absorber and skin external preparation containing the same blended therein | |
JPS6351319A (en) | Ultraviolet absorber and cosmetic containing same | |
JPH0717983A (en) | 5-allylpentadienoic acid silicon derivative, ultraviloet rays absorbent and skin external agent compounded with the same | |
JPH01249885A (en) | Antioxidant for lipid | |
JPH05186429A (en) | Benzylidenehydantoin derivative and skin external preparation blended with the same | |
JPS6410491B2 (en) | ||
JP2780091B2 (en) | Long wavelength UV absorber | |
JPH03287588A (en) | Benzophenone derivative, ultraviolet absorber and dermatic agent for external use | |
JP2646256B2 (en) | UV absorber | |
JPS62161753A (en) | Polyvalent metallic salt of benzophenone derivative and cosmetic containing same |