GB2105190A - Light-screen compositions - Google Patents
Light-screen compositions Download PDFInfo
- Publication number
- GB2105190A GB2105190A GB08221133A GB8221133A GB2105190A GB 2105190 A GB2105190 A GB 2105190A GB 08221133 A GB08221133 A GB 08221133A GB 8221133 A GB8221133 A GB 8221133A GB 2105190 A GB2105190 A GB 2105190A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- light
- methoxycinnamic acid
- screen
- acid
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- -1 propyleneglycol di-(p-methoxycinnamic acid) ester Chemical class 0.000 claims description 43
- 150000002148 esters Chemical class 0.000 claims description 10
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229960004063 propylene glycol Drugs 0.000 description 11
- 235000013772 propylene glycol Nutrition 0.000 description 11
- 239000000473 propyl gallate Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002304 perfume Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000000475 sunscreen effect Effects 0.000 description 5
- 239000000516 sunscreening agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical class COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 3
- CGOJOQBYEAVATL-QPJJXVBHSA-N (e)-3-(4-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(\C=C\C(Cl)=O)C=C1 CGOJOQBYEAVATL-QPJJXVBHSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229940099259 vaseline Drugs 0.000 description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 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 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229940031766 diethanolamine cetyl phosphate Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GKKMCECQQIKAHA-UHFFFAOYSA-N hexadecyl dihydrogen phosphate;2-(2-hydroxyethylamino)ethanol Chemical compound OCCNCCO.CCCCCCCCCCCCCCCCOP(O)(O)=O GKKMCECQQIKAHA-UHFFFAOYSA-N 0.000 description 2
- VEZIKIAGFYZTCI-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(OC)C=C1 VEZIKIAGFYZTCI-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- DGPCSURYVBYWAT-UHFFFAOYSA-N propane-1,2,3-triol;tetradecanoic acid Chemical compound OCC(O)CO.CCCCCCCCCCCCCC(O)=O DGPCSURYVBYWAT-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 1
- CWLGEPSKQDNHIO-JOBJLJCHSA-N (e)-n-[(e)-benzylideneamino]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1/C=N/N=C/C1=CC=CC=C1 CWLGEPSKQDNHIO-JOBJLJCHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 description 1
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 description 1
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- LSHGMOIQPURPAK-UHFFFAOYSA-N 2-benzylidene-1,4,7,7-tetramethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C(C2=O)(C)CCC1(C)C2=CC1=CC=CC=C1 LSHGMOIQPURPAK-UHFFFAOYSA-N 0.000 description 1
- NFIHXTUNNGIYRF-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCCC NFIHXTUNNGIYRF-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
- PUYOAVGNCWPANW-UHFFFAOYSA-N 2-methylpropyl 4-aminobenzoate Chemical compound CC(C)COC(=O)C1=CC=C(N)C=C1 PUYOAVGNCWPANW-UHFFFAOYSA-N 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- HMKKFLSUPRUBOO-IUPFWZBJSA-N 3,4-dihydroxy-5-[3,4,5-tris[[(z)-octadec-9-enoyl]oxy]benzoyl]oxybenzoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC1=C(OC(=O)CCCCCCC\C=C/CCCCCCCC)C(OC(=O)CCCCCCC\C=C/CCCCCCCC)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(O)=O)O)=C1 HMKKFLSUPRUBOO-IUPFWZBJSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- CLYMRXIXIOOVOL-UHFFFAOYSA-N 4-amino-2-propylbenzoic acid Chemical compound CCCC1=CC(N)=CC=C1C(O)=O CLYMRXIXIOOVOL-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- 241000220438 Arachis Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-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
- 206010015150 Erythema Diseases 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- IUWVALYLNVXWKX-UHFFFAOYSA-N butamben Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1 IUWVALYLNVXWKX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- CMDKPGRTAQVGFQ-RMKNXTFCSA-N cinoxate Chemical compound CCOCCOC(=O)\C=C\C1=CC=C(OC)C=C1 CMDKPGRTAQVGFQ-RMKNXTFCSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004881 homosalate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 1
- SJOXEWUZWQYCGL-DVOMOZLQSA-N menthyl salicylate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1O SJOXEWUZWQYCGL-DVOMOZLQSA-N 0.000 description 1
- 229960004665 menthyl salicylate Drugs 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NBFQYHKHPBMJJV-UHFFFAOYSA-N risocaine Chemical compound CCCOC(=O)C1=CC=C(N)C=C1 NBFQYHKHPBMJJV-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- SJOXEWUZWQYCGL-UHFFFAOYSA-N salicylic acid menthyl ester Natural products CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1O SJOXEWUZWQYCGL-UHFFFAOYSA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Light-screen compositions contain a compound of the formula: <IMAGE> wherein R1 is hydrogen or C1-3-alkyl, R<2> is hydrogen or C1-7-alkyl, X is (-CH2)n or (-CH2OCH2-)p and m = 1-5, n = 0-4, and p = 1-3, in dissolved or dispersed form.
Description
SPECIFICATION
Light-screen compositions
The invention is concerned with novel light-screen compositions, which contain a compound of the formula
wherein R1 represents hydrogen of C1~3-alkyl, especially hydrogen or methyl, R2 represents hydrogen of
C1~7-alkyl, especially methyl, X stands for the grouping (-CH2-)n or(-CH2OCH2-)p and m = 1-5, especially 1, n = 0-4, especially 0, and p = 1-3, especially 1 or 2, in dissolved or dispersed form. The invention is also concerned with the use of compounds of formula I in dissolved or dispersed form as light-screen agents.
As C13-alkyl groups there come into consideration methyl, ethyl, propyl and i-propyl. Methyl is preferred.
The C47 groups can also be straight-chain or branched-chain and thus can be, for example, butyl, i-butyl, amyl, hexyl, heptyl, etc.
Preferred compounds of formula I are: Propyleneglycol di-(p-methoxycinnamic acid) ester, 1,3-butyleneg 1 ,3-butyleneglycol di-(p-methoxycinnamic acid) ester and
triethyleneglycol di-(p-methoxycinnamic acid) ester.
Other representative compounds of formula I are:
Ethyleneglycol di-(p-methoxycinnamic acid) ester,
trimethyleneglycol di-(p-methoxycinnamic acid) ester,
2,3-butyleneglycol di-(p-methoxycinnamic acid) ester, diethyleneglycol di-(p-methoxycinnamic acid) ester,
glycerine tri-(p-methoxycinnamic acid) ester, dipropyleneglycol di-(p-methoxycinnamic acid) ester,
2-methyl-2,4-pentanediol di-(p-methoxycinnamic acid) ester,
1,4-butanediol di-(p-methoxycinnamic acid) ester,
1,5-pentanediol di-(p-methoxycinnamic acid) ester,
1,6-hexanediol di-(p-methoxycinnamic acid) ester,
2,5-hexanediol di-(p-methoxycinnamic acid) ester and
sorbitol hexa-(p-methoxycinnamic acid) ester.
The compounds of formula I absorb the erythema-producing ultraviolet rays of the sun (between 280 and 320 mp) in a pronounced manner, i.e. they keep these rays away from the living epidermis cells. The compounds of formula I can accordingly be used as light-screen agents. The invention is also concerned with a process for the manufacture of a light-screen composition, which method comprises incorporating a compound of formula I into a base which is usual in cosmetics.
The cosmetic base usual for light-screen agents in the scope of the present invention can be any usual preparation which corresponds to the cosmetic requirements; for example, creams, emulsions, salves, (alcoholic) solutions, sprays, sticks, milks and the like, see also G.A. Nowak, Die Kosmetischen Präparate, 1 sot Edition 1969, 2nd Edition 1975 (Augsburg), which literature reference refers in detail to the solvents (in the present case especially polar solvents), solubilizers, emulsifiers, thickening agents, odorant substances, preserving agents, colouring substances and other possible adjuvant substances which can be used in the manufacture of cosmetic preparations. The light-screen action is, of course, also dependent on the base which is used.The intensity of the light-screen action also depends, in the case of the same base, on the concentration of active ingredient. Suitable concentrations are, for example, between 1-6%, preferably between 2-4%, especially about 3%, of a compound of formula I in the cosmetic preparation.
On the basis of their lipophility, the compounds I can be incorporated in sufficient concentration in oil-containing and fat-containing cosmetic preparations; They have more than optimum properties with regard to adequate fat solubility and pronounced absorption of the UV B-radiation. Furthermore, the compounds I as neutral substances have good skin compatibility.
The cosmetic preparations can also contain other light-absorbing substances, for example, other UV
A-filters and/or UV B-filters.
Examples of UV A-filters are: 4-Isopropyl-dibenzoylmethane, 4-(1,1 -dimethylethyl)-4'-methoxydibenzoylmethane,
dianisoylmethane and
hydroxybenzophenones (e.g. 2,4-dihydroxybenzophenone).
As UV B-filters, i.e. as substances having absorption maxima between about 290 and 320 nm, there can be named usual UV B-filters such as, for example, the following organic compounds belonging to the most diverse classes of substances:
(1) Derivatives of p-aminobenzoic acid such as, for example, ethyl p-aminobenzoate and other esters such as propyl p-aminobenzoate, butyl p-aminobenzoate and isobutyl p-aminobenzoate, ethyl pdimethylaminobenzoate, glyceryl p-aminobenzoate and amyl p-dimethylaminobenzoate.
(2) Derivatives of cinnamic acid such as, for example, 2-ethoxyethyl p-methoxycinnamate, 2-ethylhexyl p-methoxycinnamate, p-methoxycinnamic acid ester mixtures, cinnamic acid esters and ammonium salts of p-methoxycinnamic acid.
(3) Dibenzalazine.
(4) Heterocyclic nitrogen compounds such as derivatives of 2-phenylbenzimidazole (e.g. 2- phenylbenzimidazole-5-sulphonic acid).
(5) Derivatives of salicylic acid such as, for example, menthyl salicylate, homomenthyl salicylate and phenyl salicylate.
(6) Derivatives of benzophenone such as, for example, 4-phenylbenzophenone, isooctyl 4phenyl benzophenone-2-carboxylate and 2-hydroxy-4-methoxybenzophenone-5-su Iphonic acid.
(7) Derivatives of coumarin, such as, for example, 7-oxycoumarin, ss-umbelliferoneacetic acid and 6,7-dioxycoumarin.
(8) Derivatives of gallic acid such as, for example, digalloyl trioleate.
(9) Arylidenecycloalkanones such as, for example, benzylidenecamphor, p-tert.butylbenzylidenecamphor (preferred) and methylbenzylidenecamphor.
(10) Derivatives of anthranilic acid such as, for example, menthyl anthranilate.
(11) Hydroxyphenylbenztriazole.
The compounds listed under (2) are preferred, with 2-ethylhexyl p-methoxycinnamate being especially preferred.
The compounds of formula I are known or can be prepared according to methods known per se. Thereby, p-methoxycinnamic acid, conveniently in the form of a reactive derivative (e.g. the chloride) is esterified with the polyalcohol. Stoichiometric amounts of the acid and the alcohol are conveniently used. The acid derivative is conveniently dissolved in a solvent (e.g. a chlorinated hydrocarbon such as chloroform) and the alcohol, preferably dissolved in an amine such as dimethylaniline as the solvent, is added dropwise at a temperature of about 0-20". The mixture is thereupon preferably heated in order to complete the reaction.
The crude product is thereupon conveniently poured on to ice and purified by re-extraction and washing as well as recrystallization.
The compounds of formula I can also be prepared bytrans-esterification reactions. For this purpose, a lower alkyl ester of p-methoxycinnamic acid (e.g. the methyl or ethyl ester) is reacted with the desired polyalcohol (e.g. ethyleneglycol, glycerine etc) in the presence of a catalyst. Suitable catalysts are bases such as sodium methylate or sodium ethylate. The reaction temperataure is conveniently chosen so that the methyl or ethyl alcohol formed can be distilled off at atmospheric pressure.
The following Examples illustrate the preparation of the active ingredients and the compositions provided by the invention:
A. Preparation of the active substances
Example 1
100 g of p-methoxycinnamic acid chloride [prepared according to Farmacia (Bucharest) (1961)345-50; C.A. 568312 i] and 200 ml of chloroform are added to a 1 litre four-necked round flask which is fitted with a stirrer, thermometer, reflux condenser and dropping funnel. The mixture is cooled to 1 O"C and at this temperature while stirring there is allowed to drop in within 1 hour a mixture of 60.5 g of dimethylanaline and 19.1 g of propyleneglycol. The reaction is completed by heating to refluxtemperaturefor2 hours. After cooling, the mixture is poured on to ice.The mixture is taken up in 250 ml of chloroform and the dimethylaniline-HCI salt is washed out with 10% hydrochloric acid and then washed with water until it is neutral.
The solvent is evaporated and the residue (90 g of crude product) is recrystallized from acetone/water (4:1). There are obtained 50.1 g of propyleneglycol di-(p-methoxycinnamic acid) ester; m.p. 97-99"C; E310 = 46100,E= 1163.
Yield: 50.5% of theory.
Example 2
173 g of methyl-p-methoxycinnamate, 38 g of propyleneglycol, 9 of sodium methylate and 300 ml of dry xylene are added to a 1 litre round flask which is fitted with a stirrer and a tap headpiece. The mixture is warmed while stirring and resulting methanol is distilled off slowly (32 g). The mixture is held at reflux temperature for a further 5 hours. After cooling, it is neutralized with 5.5 g of acetic acid, taken up in ether and washed with water. After drying over sodium sulphate, the ether is distilled off. 177 g of crude product are obtained. After recrystallization from methanol, there is obtained propyleneglycol di-(pmethoxycinnamic acid) ester.
M.P.96-98 C.
Example 3
100 g of p-methoxycinnamic acid chloride and 200 ml of chloroform are added to a 1 lire four-necked flask which is fitted with a stirrer, thermometer, reflux condenser and dropping funnel. The mixture is cooled to 10 C and at this temperature while stirring there is allowed to drop in within 0.5 hour a mixture of 60.5 g of dimethylaniline and 15.5 g of glycerine. The reaction is completed by heating at reflux for 1 hour. After cooling, the mixture is poured on to ice. The mixture is taken up in 200 ml of chloroform and the dimethylaniline is washed out with 10% hydrochloric acid and then washed with water until it is neutral. The solvent is evaporated and the solid residue (113 g of crude product) is recrystallized from 200 ml of toluene.
There are obtained 51.1 g of glycerine tri-(p-methoxycinnamic acid) ester.
M.p. 104-1050C; e310 = 67970, E= 1187. Yield: 52.5% of theory.
Example 4
According to the process described in Examples 1 and 3, from 100 g of p-methoxycinnamic acid chloride and 37.5 g of treithyleneglycol in the presence of 60.5 g of dimethylaniline in chloroform there are obtained 81 g of triethyleneglycol di-(p-methoxycinnamic acid) ester: m.p. 82-83"C; E310 = 46900, E=995. Yield 69% of theory.
The following esters are prepared in an analogous manner:
Ethyleneglycol di-(p-methoxycinnamic acid) ester;
m.p. 147-149"C; E310 = 44932, E=1175.
Trimethyleneglycol di-(p-methoxycinnamic acid) ester; m.p. 140-1410C; c310 = 45150, E=1139.
1,3-Butyleneglycol di-(p-methoxycinnamic acid) ester; m.p. 97.5-99.5"C; E310 = 44780, E=1090.
2,3-Butyleneglycol di-(p-methoxycinnamic acid) ester; m.p. 154-156"C; E310 = 46260, E=127.
2-Methyl-2,4-pentanediol di-(p-methoxycinnamic acid) ester; m.p.100-101 C; E310 = 43368, E=989.
1,5-Pentanediol di-(p-methoxycinnamic acid) ester: m.p.76.5-78 C: E310 =47250,E=1115.
1,6-Hexanediol di-(p-methoxycinnamic acid) ester; m.p. 92.5-93.5"C; E310 = 47300, E=1080.
2,5-Hexanediol di-(p-methoxycinnamic acid) ester; m.p. 126.5-128.5"C; E310 = 44700, E=1020.
Diethyleneglycol di-(p-methoxycinnamic acid) ester; m.p. 77.5-78.5"C; E310 = 45000, E=1055.
B. Formulations
Example 5
Sun-screen cream, semi-fatty (olw)
Parts by weight (A) 4-(1 ,1 -Dimethylethyl)-4'-methoxy- dibenzoylmethane 1.5
Propyleneglycol di-(p-methoxy
cinnamic acid) ester 3.0
Stearic acid triply pressed 10.0 Cetyl alcohol 1.0
Glycerine monomyristate 5.0
Isopropyl adipate 7.0
Oleyl alcohol 4.0
Methyl and propyl p-aminobenzoic
acid (70/30) 0.25 (B) Diethanolamine cetyl phosphate 3.0 (C) Distilled water 59.25
Propyleneglycol 6.0 (D) Perfume q.s.
The combined components of (A) are heated to 85"C on a water-bath and thereupon (B) is added at this temperature. (C) is heated to 750C and added to (A) + (B). The resulting mixture is stirred. After cooling to 35"C, water losses are compensated where applicable and (D) is added.
Example 6
Sun-screen milk (ole) Parts by weight (A) Cetyl alcohol 2.0
Glycerine monomyristate 4.0
Arachis oil hydrogenated pharmacop. 2.0
Isopropyl adipate 5.0
Propyleneglycol di-(p-methoxy
cinnamic acid) ester 2.0-5.0 (B) Diethanolamine cetyl phosphate 3.0 (C) Distilled water 74.0-68.5
Propyleneglycol 3.0
Urea 5.0 (D) Perfume q.s.
Preserving agent q.s.
The mixture (A) is heated to 85"C on a water-bath and thereupon B is added at this temperature. The combined components of (C) are heated to 75"C and thereupon added to (A) + (B). The water losses are balanced after cooling to 25-30"C and then (D) is added. The mixture is stirred further until the temperature reached 25"C.
Example 7
Sun-screen cream for athletes (woo) Parts by weight (A) Propyleneglycol di-(p-methoxy
cinnamic acid) ester 1.5 4-(1,1-Dimethylethyl)-4'- methoxy-dibenzoylmethane 1.0
Sorbityl sesquioleate 9.0
Lanolin 1.0
Paraffin oil 8.0
Methyl and propyl p-aminobenzoic
acid ester (70/30) 0.25 (B) Isopropyl myristate 10.0
Aluminium stearate 0.1 (C) Magnesium sulphate 0.3
Propyleneglycol 3.0
Distilled water 67.35
Perfume 0.5
The aluminium stearate is carefully mixed with the isopropyl myristate and the resulting mixture (B) is added to the combined components of (A) which are heated to 80"C. To the hot mixture (A) + (B) there is slowly added the solution (C) which is heated to 750C. (A) + (B) + (C) is left to cool while stirring.At 40"C the water losses are balanced and the perfume is added. The mixture is thereupon homogenized.
Example 8
Sun-screen oil
Parts by weight
Propyleneglycol di-(p-methoxy
cinnamic acid) ester 4.0
Propyleneglycol dicaprylate and
dicaprate 26.0
Vaseline oil (d = 0.849 - 0.866) 70.0
oil-soluble colouring substance q.s.
Perfume (0.5 - 1%) q.s.
The combined components are heated to 80"C. The mixture is thereupon cooled and perfumed.
Example 9
Sun-screen stick
Parts by weight 4-( 1,1 -Dimethylethyl)-4'-methoxy- dibenzoylmethane 2.0
Propyleneglycol di-(p-methody)
cinnamic acid) ester 5.0
Oleyl alcohol (Satol) 17.0
Cracked hydrogenated castor oil 19.0
Microcrystalline wax 30.0
Vaseline oil 10.0
Methyl and propyl p-aminobenzoic
acid ester (70/30) 0.25
Vaseline 16.75
Perfume 0.5
The combined components are melted together and perfumed. The mixture is thereupon poured into moulds.
Claims (10)
1. A light-screen composition, which contains a compound of the formula
wherein R1 represents hydrogen of C1 ~3-alkyl, R2 represents hydrogen of C1 ~7-alkyl, X stands for the grouping (CH2)n or (CH2OCH2)p and m = 1-5, n = 0-4 and p = 1-3, in dissolved or dispersed form and, if desired, additional substances usual in light-screen compositions.
2. A light-screen composition in accordance with claim 1, wherein the content of compound of formula I in the light-screen composition amounts to 1-6 wt. %.
3. A light-screen composition according to claim 1 or claim 2, which contains propyleneglycol di-(p-methoxycinnamic acid) ester.
4. A light-screen composition according to claim 1 or claim 2, which contains 1,3-butyleneglycol di-(p-methoxycinnamic acid) ester.
5. A light-screen composition according to claim 1 or claim 2, which contains triethyleneglycol di-(p-methoxycinnamic acid) ester.
6. The use of compounds of the formula
wherein R1 represents hydrogen or C1~3-alkyl, R2 represents hydrogen of C1~7-alkyl, X stands for the grouping (-CH2-)n or (-CH20CH2-)p and m = 1-5, n = 0-4 and p = 1-3, in dissolved or dispersed form as a light-screen agent.
7. The use of propyleneglycol di-(p-methoxycinnamic acid) ester in dissolved or dispersed form as a light-screen agent.
8. The use of 1 ,3-butyleneglycol di-(p-methoxycinnamic acid) ester in dissolved or dispersed form as a light-screen agent.
9. The use of treithyleneglycol di-(p-methoxycinnamic acid) ester in dissolved or dispersed form as a light-screen agent.
10. A process for the manufacture of a light-screen composition, which process comprises incorporating a compound of the formula
wherein R1 represents hydrogen of C1 ~3-alkyl, R2 represents hydrogen or Cs ~7-alkyl, X stands for the grouping (-CH2-)n or (-CH2OCH2-)p and m = 1-5, n = 0-4 and p = 1-3, into a cosmetic base.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH478381A CH648753A5 (en) | 1981-07-22 | 1981-07-22 | Light protection. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2105190A true GB2105190A (en) | 1983-03-23 |
| GB2105190B GB2105190B (en) | 1985-07-17 |
Family
ID=4282465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08221133A Expired GB2105190B (en) | 1981-07-22 | 1982-07-21 | Light-screen compositions |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5824512A (en) |
| CH (1) | CH648753A5 (en) |
| DE (1) | DE3227250A1 (en) |
| FR (1) | FR2509990B1 (en) |
| GB (1) | GB2105190B (en) |
| NL (1) | NL8202949A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0791353A1 (en) * | 1996-02-26 | 1997-08-27 | Shiseido Company Limited | Ultraviolet absorbing composition |
| US20110086912A1 (en) * | 2009-10-09 | 2011-04-14 | Macgregor Alexander | Derivatives of Propane Diyl Dicinnamate |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6248612A (en) * | 1985-08-27 | 1987-03-03 | Narisu Keshohin:Kk | Cosmetic |
| US8968452B2 (en) * | 2011-04-27 | 2015-03-03 | Xerox Corporation | Phase change inks containing crystalline trans-cinnamic diesters and amorphous isosorbide oligomers |
| US8906150B2 (en) * | 2011-04-27 | 2014-12-09 | Xerox Corporation | Phase change inks containing crystalline trans-cinnamic diesters and polyterpene resins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2190917A (en) * | 1938-04-07 | 1940-02-20 | Dow Chemical Co | Ethylene dicinnamate |
| BE662111A (en) * | 1965-04-06 | 1965-08-02 | ||
| DE2744326A1 (en) * | 1977-10-01 | 1979-04-12 | Henkel Kgaa | Antiinflammatory agents for cosmetics - esp. sunscreen compsns., comprises hydroxy-cinnamic acid ester(s) |
| JPS5935941B2 (en) * | 1979-04-02 | 1984-08-31 | 株式会社資生堂 | UV absorber |
| DE3175184D1 (en) * | 1980-12-26 | 1986-09-25 | Ss Pharmaceutical Co | 2,3-butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
-
1981
- 1981-07-22 CH CH478381A patent/CH648753A5/en not_active IP Right Cessation
-
1982
- 1982-07-20 FR FR8212619A patent/FR2509990B1/en not_active Expired
- 1982-07-21 NL NL8202949A patent/NL8202949A/en not_active Application Discontinuation
- 1982-07-21 DE DE19823227250 patent/DE3227250A1/en not_active Withdrawn
- 1982-07-21 JP JP12744982A patent/JPS5824512A/en active Pending
- 1982-07-21 GB GB08221133A patent/GB2105190B/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0791353A1 (en) * | 1996-02-26 | 1997-08-27 | Shiseido Company Limited | Ultraviolet absorbing composition |
| US5849272A (en) * | 1996-02-26 | 1998-12-15 | Shiseido Co., Ltd. | Ultraviolet absorbing composition |
| US20110086912A1 (en) * | 2009-10-09 | 2011-04-14 | Macgregor Alexander | Derivatives of Propane Diyl Dicinnamate |
| US9061993B2 (en) * | 2009-10-09 | 2015-06-23 | Toronto Institute of Pharmaceutical Technology | Derivatives of propane diyl dicinnamate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2509990A1 (en) | 1983-01-28 |
| NL8202949A (en) | 1983-02-16 |
| JPS5824512A (en) | 1983-02-14 |
| FR2509990B1 (en) | 1985-08-09 |
| DE3227250A1 (en) | 1983-02-10 |
| GB2105190B (en) | 1985-07-17 |
| CH648753A5 (en) | 1985-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |