CN1148165C - 化妆品用遮光组合物 - Google Patents
化妆品用遮光组合物 Download PDFInfo
- Publication number
- CN1148165C CN1148165C CNB981167918A CN98116791A CN1148165C CN 1148165 C CN1148165 C CN 1148165C CN B981167918 A CNB981167918 A CN B981167918A CN 98116791 A CN98116791 A CN 98116791A CN 1148165 C CN1148165 C CN 1148165C
- Authority
- CN
- China
- Prior art keywords
- screening composition
- cosmetic light
- formula
- chemical compound
- light
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000002537 cosmetic Substances 0.000 title claims abstract description 48
- 238000012216 screening Methods 0.000 title claims abstract description 32
- 150000001875 compounds Chemical group 0.000 claims abstract description 54
- 230000005855 radiation Effects 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- -1 methylidene, ethyl Chemical group 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 9
- 239000010936 titanium Substances 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012965 benzophenone Substances 0.000 claims description 6
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 229940024874 benzophenone Drugs 0.000 claims description 5
- 229940114081 cinnamate Drugs 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 5
- 229960001860 salicylate Drugs 0.000 claims description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- NONMDAWIWVXCAU-UHFFFAOYSA-N 1,3-diphenyl-2,2-di(propan-2-yl)propane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C(C)C)(C(C)C)C(=O)C1=CC=CC=C1 NONMDAWIWVXCAU-UHFFFAOYSA-N 0.000 claims description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 2
- KUVGPGJIFQKWNP-UHFFFAOYSA-N 2-methoxy-2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)(OC)C(=O)C1=CC=CC=C1 KUVGPGJIFQKWNP-UHFFFAOYSA-N 0.000 claims 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 4
- 229910052684 Cerium Inorganic materials 0.000 claims 4
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 4
- 230000031700 light absorption Effects 0.000 claims 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 1
- WQDGUYZIAJKLAB-UHFFFAOYSA-N octan-2-yl nitrite Chemical compound CCCCCCC(C)ON=O WQDGUYZIAJKLAB-UHFFFAOYSA-N 0.000 claims 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000004808 2-ethylhexylester Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- HEOCBCNFKCOKBX-RELGSGGGSA-N (1s,2e,4r)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)[C@]2(C)CC[C@H]\1C2(C)C HEOCBCNFKCOKBX-RELGSGGGSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229960001679 octinoxate Drugs 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 3
- 239000003605 opacifier Substances 0.000 description 3
- 229920005573 silicon-containing polymer Polymers 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- HIPQTCQUXOFTFI-UHFFFAOYSA-N 2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)C(=O)C1=CC=CC=C1 HIPQTCQUXOFTFI-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000498779 Myristica Species 0.000 description 2
- 235000009421 Myristica fragrans Nutrition 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- STORWMDPIHOSMF-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O STORWMDPIHOSMF-UHFFFAOYSA-N 0.000 description 2
- PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 229940031578 diisopropyl adipate Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229960004697 enzacamene Drugs 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001702 nutmeg Substances 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 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 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GUKJMRCPYSIVFI-KTKRTIGZSA-N (z)-2-(2,3-dihydroxypropyl)octadec-9-enoic acid Chemical class CCCCCCCC\C=C/CCCCCCC(C(O)=O)CC(O)CO GUKJMRCPYSIVFI-KTKRTIGZSA-N 0.000 description 1
- QJYBLGMKMPXOEI-UHFFFAOYSA-N 1,1'-biphenyl;prop-2-enoic acid Chemical compound OC(=O)C=C.C1=CC=CC=C1C1=CC=CC=C1 QJYBLGMKMPXOEI-UHFFFAOYSA-N 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
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 1
- VCLJODPNBNEBKW-UHFFFAOYSA-N 2,2,4,4,6,8,8-heptamethylnonane Chemical compound CC(C)(C)CC(C)CC(C)(C)CC(C)(C)C VCLJODPNBNEBKW-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
- 150000000369 2-ethylhexanols Chemical class 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- FFEXJZHLBZEWQA-UHFFFAOYSA-N 4-phenyl-1H-benzimidazole-2-sulfonic acid propane-1,2,3-triol Chemical compound OCC(O)CO.C=12NC(S(=O)(=O)O)=NC2=CC=CC=1C1=CC=CC=C1 FFEXJZHLBZEWQA-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- RIQIJXOWVAHQES-UNAKLNRMSA-N Tocoretinate Chemical compound C([C@@](OC1=C(C)C=2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC1=C(C)C=2OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C RIQIJXOWVAHQES-UNAKLNRMSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- ILIVOUPKYZNRBI-UHFFFAOYSA-L aluminum;magnesium;octadecanoate;hydroxide Chemical compound [OH-].[Mg+2].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O ILIVOUPKYZNRBI-UHFFFAOYSA-L 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical class CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical class CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- AALYHVPQQFBRJO-UHFFFAOYSA-N diethyl 2-[(4-butoxyanilino)methylidene]propanedioate Chemical compound CCCCOC1=CC=C(NC=C(C(=O)OCC)C(=O)OCC)C=C1 AALYHVPQQFBRJO-UHFFFAOYSA-N 0.000 description 1
- IHIPTCPIRSAXEZ-UHFFFAOYSA-N dimethyl 2-[(4-butoxyanilino)methylidene]propanedioate Chemical class CCCCOC1=CC=C(NC=C(C(=O)OC)C(=O)OC)C=C1 IHIPTCPIRSAXEZ-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical class COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000499 gel Substances 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
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 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
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- YBGZDTIWKVFICR-UHFFFAOYSA-N octinoxate Chemical compound CCCCC(CC)COC(=O)C=CC1=CC=C(OC)C=C1 YBGZDTIWKVFICR-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940116987 ppg-3 myristyl ether Drugs 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VRYGRLBNIVQXMY-UHFFFAOYSA-M sodium;acetic acid;chloride Chemical compound [Na+].[Cl-].CC(O)=O VRYGRLBNIVQXMY-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229950010156 tretinoin tocoferil Drugs 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 229940093633 tricaprin Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K8/18—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
- A61K8/40—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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
-
- 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
Abstract
本发明涉及一种化妆品用遮光组合物。该组合物用以保护人体皮肤或毛发不受紫外线辐射，它含有至少一种式I的化合物，其中R1代表C1-8的直链或支链烷基链，R2和R3各自代表C1-8的直链或支链烷基链。
Description
本发明涉及一种化妆品用遮光组合物、该化妆品用遮光组合物用于保护人体皮肤和毛发不受波长约在280-400nm之间的紫外线(UV)辐射的用途、含有该组合物的化合物及这些化合物用作UV滤光剂的用途。
众所周知，太阳光会加快皮肤的老化，甚至引发皮肤癌。这些不良的作用是由于UV辐射造成的。
现在已经发现，式I的化合物是优良的UV滤光剂，对皮肤具有亲和性和在光、热、湿气下的稳定性。
式I中R1代表C1-8的直链或支链烷基链，R2和R3各自代表C1-8的直链或支链烷基链。这些化合物对皮肤在紫外线辐射下有很强的保护作用，从而能延缓皮肤衰老，特别是这些紫外线滤光剂还具有突出的耐光性。
此外，还发现在那些UV A-滤光剂如4-叔丁基-4′-甲氧基二苯甲酰甲烷和那些UV B滤光剂之间，式I化合物的吸收达到最大值，并且，特别令人惊讶地增大了紫外线B滤光剂的保护作用，这些物质主要吸收能产生红斑的、波长约在290至320nm之间的紫外线B的辐射，虽然式I化合物的吸收最大值不在这个区间范围而是在约320至340nm之间，即紫外线A和紫外线B辐射的最大值之间。
既能为化妆品所用又能在这些区间范围内吸收的仅有的几种紫外线滤光剂是二苯酮和邻氨基苯甲酸酯。但是，许多配方设计师们都不采用这类化合物。原因很多，例如，和式I的化合物相比，它们的萃取率太低。
式I的烷氧基苯胺基亚甲基-丙二酸酯是已知的，可从美国专利3,079,366；W.O.Kermack，N.E.Storey，化学学会会刊(J.Chem.Soc)607(1950)以及T.Takahashi，S.Senda，日本药学学会会刊(J.Pharm.Soc.Jpn.)，71，1112(1952)等刊物中查到。具体公开的是甲氧基-乙氧基-和丁氧基-苯胺基亚甲基-丙二酸乙酯。但是，关于这些化合物用于化妆品目的的用途，尤其是将这些化合物用于护肤和护发方面，还未见到任何报导。
一种紫外线滤光剂在化妆品溶剂中应具有大的溶解度，以便在配制中可以适度地缩浓。例如，要在一种含水量70％的标准的水包油型(o/w)乳液中含6％紫外线滤光剂，在油相的溶解度必须达到20％。令人吃惊的是，已经发现式I的化合物在许多化妆品溶剂中的溶解度达到了20％。这些溶剂有辛酸癸酸甘油三酯，丙二醇二辛酸酯/二癸酸酯，C12-15烷基苯甲酸酯，丙二醇单异硬脂酸酯，二异丙基己二酸酯。
因此，本发明的目的是式I的新型化合物；含至少一种上述式I化合物，优选是与至少一种UVB滤光剂和至少一种UVA滤光剂联合用于化妆品目的的遮光剂；以及式I化合物作为遮光剂的用途，特别是用于化妆品目的的用途。
本发明提供的是一种用于保护人体皮肤和毛发使其抗紫外线辐射的化妆品用遮光组合物，该组合物在化妆品适用的载体中含有至少一种式I的化合物：
其中R1代表C1-8的直链或支链烷基链，R2和R3各自代表C1-8的直链或支链烷基链。
术语“C1-8的直链或支链烷基链”指的是甲基、乙基、正丙基、异丙基、正丁基、叔丁基、戊基、庚基、2-乙基-己基等基团。优选是化合物中的R2和R3各自代表甲基、乙基、戊基或2-乙基己基。R1基团优选的是甲基、乙基或正丁基。
因此，下列化合物是优选的：
化合物中R1、R2和R3都是甲基(实施例1)或乙基(实施例4)；或者R1是乙基而R2、R3是甲基(实施例2)或是2-乙基己基(实施例6)；或者R1是正丁基而R2和R3是甲基(实施例3)或乙基(实施例5)。最优是实施例4的化合物，其中R1、R2和R3都是乙基。
化妆品用遮光组合物含有按重量0.1％至10％的式I化合物是优选的，更优是含有按重量0.5％至5％的式I化合物，特别优是含有按重量1％至3％的式I化合物。
化妆品用遮光组合物还可以另外含有至少一种在约300至320nm之间具有最大吸收的紫外线B滤光剂，和至少一种在大于等于340nm区域、特别是在340至360nm之间时吸收量达到最大值的紫外线A滤光剂；尤其是在356nm时具最大吸收值的一种紫外线A滤光剂。具体地说，这种紫外线A滤光剂是4-叔丁基-4′-甲氧基二苯甲酰甲烷。通常紫外线A滤光剂选自下列化合物：2-甲基二苯甲酰甲烷；4-甲基-二苯甲酰甲烷；4-叔丁基二苯甲酰甲烷；2，4-二甲基-二苯甲酰甲烷；2，5-二甲基二苯甲酰甲烷；4，4′-二异丙基二苯甲酰甲烷；4-叔丁基-4′-甲氧基二苯甲酰甲烷；2-甲基-5-异丙基-4′-甲氧基二苯甲酰甲烷；2-甲基-5-丁基-4′-甲氧基二苯甲酰甲烷；2，4-二甲基-4′-甲氧基二苯甲酰甲甲烷；2，6-二甲基-4-叔丁基-4′-甲氧基二苯甲酰甲烷和对苯二亚甲基二樟脑磺酸。
紫外线B滤光剂至少是下列中的一种：肉桂酸酯、水杨酸酯、二苯酮、联二苯丙烯酸酯、三嗪、樟脑衍生物、聚合物紫外线吸收剂(特别是在US5,403,944中所述的那些)和精微(microfine)颜料。具体地说，该紫外线滤光剂是至少一种铯、铁、钛、锌或锆(特别是钛或锌)的颜料金属氧化物，和带有至少一个紫外线吸收基具有烃结构或硅氧烷结构的聚合物。
化妆品用遮光组合物、或式I的化合物的用途是保护人体皮肤或毛发不受紫外线的辐射。
下列式I的化合物是新的：
2-(4-庚氧基-苯胺基亚甲基)-丙二酸二乙酯，
2-(4-甲氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-丙氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-丁氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-戊氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-己氧基-苯胺基亚甲基)-丙二酸二甲酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二戊酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯戊基酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二-2-乙基-己基酯，和
2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯-2-乙基-己基酯。
以上这些化合物，每一种都可用作紫外线滤光剂，特别是用于前述的化妆品的目的。在这方面，特别引人关注的是下列化合物：
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二戊基酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯戊基酯，
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二-2-乙基-己基酯和
2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯-2-乙基-己基酯。
式I所代表的化合物(已知的和新的化合物)都可用常规的方法方便地制取，正如在美国专利3,079,366中所公开的，现简述如下：
在有溶剂或没有溶剂的条件下，用一种苯胺衍生物(C1-C8烷氧基苯胺)和一种适当取代的烷氧基亚烷基-丙二基衍生物进行反应。
在本发明的范围内用作遮光剂的化妆品可接受的载体，可以使用任何一种与该化妆品的要求相符合的常规制剂，例如：乳脂，洗液，乳剂，软膏，凝胶，溶液，喷剂，棒剂，和牛奶等，参见：Kosmetik，Entwicklung，Herstellungand Anwendung Kosmetischer Mittel，ed.Wilfried Umbach，Georg ThiemeVertrag Stuttgart-New York 1988；Sunscreens，Development，Evulation andRegulatory Aspects，ed.N.Y.Lowe，N.A.Shaat，Marcel Decker，Inc.New YorkBasel，1990。
由于具备亲脂性，式I的化合物可毫无困难的加到含油或含脂的化妆品制剂中。
这种新化合物的亲脂性满足了本发明要求的标准，即在化妆品溶剂中可溶性的要求。这些溶剂如Miglyol 812N(辛癸甘油三脂)，Miglyol 840(丙二醇二辛酸酯二癸酸酯)，Finsolv TN(含12-15个碳原子的烷基苯甲酸酯)，Prisorine 2034(丙二醇单异硬脂酸酯)或Crodamol DA(二异丙基己二酸酯)。针对这方面，特别优选的是实施例4的化合物。
化妆品用遮光剂适用的形式是油剂、洗液、胶体、固体棒、乳剂如乳脂、乳液，或者是离子或非离子两性类脂体的多泡分散剂、气溶胶、喷剂、泡沫状物，粉末、香波、护发素、发胶或粉底等。
如果保护头发的化妆品制剂是由至少一种式I化合物制备的，其适用的制剂可以是香波，护发素，洗液，胶体，乳剂、分散剂、发胶等等。所有这些制剂的制备都是本领域普通技术人员所熟知的。
普通技术人员已知的如油、蜡、醇、多元醇等普通溶剂都可用于上述这些形式的化妆品制剂。优选的溶剂是脂肪酸、酯、脂肪醇，还有乙醇、异丙醇、丙二醇、甘油等化合物也是适用的。
这种化妆品制剂还可以含有其它的辅助剂，如更大范围内的溶剂，增稠剂，软化剂，乳化剂，保湿剂，表面活性剂，防腐剂，消泡剂，香料，油，蜡，低级多元醇和一元醇，推进剂，聚硅氧烷，着色剂和颜料等。
该新型的遮光组合物或式I的化合物的一个重要的优点在于这样一个事实：即本领域的普通技术人员可以充分自由地选择有关材料用于前述的紫外线B和紫外线A辐射的过滤。但是，用于过滤紫外线A的最优选UV-A滤光剂是4-叔丁基-4′-甲氧基二苯甲酰甲烷，特别是它和2-(4-乙氧基-苯胺基亚甲基)-丙二酸二乙酯的结合使用。
进一步的优点、特性和详细情况公开在下列实施例中。
实施例1
2-(4-甲氧基-苯胺基亚甲基)-丙二酸二甲基酯
将17.4克(0.1摩尔)的二甲基甲氧基亚甲基丙二酸酯的70ml乙醇溶液在室温下边搅拌边滴到12.3克(0.1摩尔)对甲氧基苯胺的50毫升乙醇溶液中。在那个温度下再搅拌一个小时，将反应混合物用冰浴冷却，产品就自发地结晶。然后过滤，将粗产物固体物质分离出来，再用乙醇洗涤，得到12.9克标题化合物。这是一种白色固体，熔点为89-91℃，UV328nm(E＝899)。
实施例2
2-(4-乙氧基-苯胺基亚甲基)丙二酸二甲基酯
制备方法同实施例1，只是将上例中的对甲氧基苯胺用1当量的对乙氧基苯胺代替。得到19.8克标题化合物，一种白色固体，熔点为66-67℃，UV328nm(E＝879)。
实施例3
2-(4-丁氧基-苯胺基亚甲基)-丙二酸二甲基酯
a).制备2-(4-羟基-苯胺基亚甲基)丙二酸二甲酯
将26.1克(0.15摩尔)甲氧亚甲基丙二酸二甲酯的70毫升乙醇溶液在室温下滴加到16.4克(0.15摩尔)4-氨基苯酚的100毫升乙醇溶液中。在那个温度下再搅拌10分钟。过滤分离粗产品固体物质，用乙醇洗涤，得到34.3克白色固体备用，不必进一步纯化。
b).将3.9克(28毫摩尔)碳酸钾的50毫升二甲基甲酰胺溶液和7.3克(28毫摩尔)丁基碘在室温下边搅拌边滴加到7克(28毫摩尔)2-(4-羟基-苯胺基亚甲基)-丙二酸二甲酯的混合物中。将反应的混合物加热到80℃持续24小时。然后将反应的混合物倒进50毫升水中，用乙酸乙酯萃取三次。先用15％浓度的氢氧化钠溶液清洗有机层，然后再用水清洗，干燥，蒸发，得4.5克本例标题化合物，一种白色固体，熔点46-47℃，UV328nm(E＝685)。
实施例4
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二乙基酯
制备方法用实施例1，只是用1当量的对乙氧基苯胺代替对甲氧基苯胺，用1当量的二乙基乙氧基亚甲基丙二酸酯代替二甲基甲氧基亚甲基丙二酸酯。乙醇用己烷代替。可得到21克标题化合物，一种白色固体，熔点55-56℃，UV329NM(E＝802)。
实施例5
2-(4-丁氧基-苯胺基亚甲基)-丙二酸二乙基酯
制备方法同实施例3，只是例3中的二甲基甲氧基亚甲基丙二酸酯用1当量的二乙基乙氧基亚甲基丙二酸酯代替。得到3.1克标题化合物，一种白色固体，熔点54-55℃，UV329nm(E＝714)。
实施例6
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二-2-乙基-己基酯和2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯2-乙基-己基酯
将18.4克(60毫摩尔)的2-(4-乙氧基-苯胺基亚甲基)-丙二酸二乙酯和70毫升含430毫克4-异丙氧基钛的2-乙基-己醇的混合物在150℃下搅拌4小时。将反应的混合物减压浓缩(8℃，6毫巴(6×102Pa))至一黄色油。将这黄色油溶于100毫升乙酸乙酯和5毫升的水中，搅拌10分钟，在无水硫酸镁上干燥，然后将片状的混悬液过滤，减压浓缩。得26.8克黄色油。这两种标题产品采用己烷与乙酸乙酯之比为10∶1的洗脱剂，通过快速色谱法分离。得到23.6克2-(4-乙氧基-苯胺基亚甲基)-丙二酸二-2-乙基-己基酯，一种黄色油，UV 329nm(E＝567)，和1.8克2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙酯2-乙基-己酯，一种黄色油，UV329nm(E＝632)。
实施例7
2-(4-乙氧基-苯胺基亚甲基)-丙二酸二戊基酯和2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙基酯戊基酯
制备方法同实施例6，其中2-乙基-己醇用正戊醇代替。这两种标题产品的分离可通过快速色谱法，采用8∶1的己烷/乙酸乙酯作为洗脱剂。得到16.6克2-(4-乙氧基-苯胺基亚甲基)-丙二酸二戊基酯，这是一种黄色油，UV 329mm(E＝651)。得到2.5克2-(4-乙氧基-苯胺基亚甲基)-丙二酸乙基酯戊基酯，一种黄色油，UV 329nm(E＝725)。
实施例8
制剂的配方：油包水型乳液
| 成分 | 重量比(％) |
| A)实施例6的产品(二-2-乙基-己基酯)丁基甲氧基二苯甲酰甲烷(Parsol 1789)辛基甲氧基肉桂酸酯(Parsol CX)聚甘油基-3-二异硬脂酸酯甘油基油酸盐十六基醇矿物油椰子辛酸酯/癸酸酯用聚二甲基硅氧烷涂的二氧化钛辛基十二烷醇丁基羟基甲苯苯氧基乙醇和尼泊金甲酯和乙酯和丙酯和丁酯B)86％甘油苯基苯并咪唑磺酸(Parsol HS)二钠EDTA水 | 61.535321010220.10.6520.147.7 |
在85℃下将A部分和B部分各自混匀，然后在搅拌中将A、B两部分合并到一起。最后，如果必要，用10％氢氧化钾或10％柠檬酸，将pH值校正到7。
实施例9
制剂的配方：油包水型乳液(软乳脂)
| 成分 | 重量比(％) |
| A)实例4的产品POP-POE甘油基脱水山梨醇脂肪酸酯七甲基壬烷(Heptamethylnonane)石蜡PPG-(15)-十八烷醇和环甲基硅氧烷硅石丁基羟基甲苯苯氧基乙醇和尼泊金甲酯和乙酯和丙酯和丁酯B)氯化钠POE-30山梨醇86％甘油二钠EDTA水 | 555920.40.10.60.51.52.50.168.3 |
在85℃下A部分和B部分分别混合，然后搅拌中将两部分产品合并在一起。最后，如果必要，用10％的氢氧化钾或者10％的柠檬酸将pH值校正到7。
实施例10
配方：硅氧烷的水乳液(洗液)
| 成分 | 重量比(％) |
| 实施例5的产品环状聚二甲基硅氧烷五聚物和氢氧化铝镁硬脂酸盐环状聚二甲基硅氧烷和聚二甲基硅氧烷共聚醇环状聚二甲基硅氧烷PPG-3肉豆蔻基醚聚二甲基硅氧烷涂渍的二氧化钛C12-15烷基苯甲酸酯丁基羟基甲苯苯氧基乙醇和尼泊金甲酯和乙酯和丙酯和丁酯B)氯化钠乙酸生育酯二钠EDTA水 | 2910522100.10.60.520.156.7 |
在85℃下A部分和B部分各自混合，然后将A、B两部分搅拌合并。最后，如有必要，用10％的氢氧化钾或者10％的柠檬酸将pH值校正到7。
实施例11
制剂的配方：水包油型乳液
| 成分 | 重量比(％) |
| A)实施例4的产品辛基甲氧基肉桂酸酯(Parsol Mcx)丁基甲氧基二苯甲酰甲烷(Parsol 1789)4-甲基亚苄基樟脑(Parsol 5000)甘油基单肉豆蔻酸盐十六烷醇椰子辛酸酯癸酸酯异丙基肉豆蔻酸酯PVP-二十碳烯共聚物丁基羟基甲苯二钠EDTA苯氧基乙醇和尼泊金甲酯和乙酯和丙酯和丁酯B)PE-POP嵌段共聚物水Carbomer 981丙二醇 | 431.534115520.10.10.6238.71010 |
在85℃下A部分和B部分各自混合，然后搅拌合并。最后，必要的话，用10％氢氧化钾或者10％柠檬酸，将pH值校正至7。
实施例12
配方：水包油型乳液
| 成分 | 重量比(％) |
| A)实施例4的产品辛基甲氧基肉桂酸盐(Parsol MCX)丁基甲氧基二苯甲酰甲烷(Parsol 1789)4-甲基亚苄基樟脑(Parsol 5000)甘油基单肉豆蔻酸盐十六烷醇椰子辛酸酯癸酸酯辛酸癸酸甘油三酯PVP-二十碳烯共聚物丁基羟基甲苯二钠EDTA苯氧基乙醇和尼泊金甲酯和乙酯和丙酯和丁酯B)脱水山梨醇酯和蔗糖酯水碳水化合物基体981丙二醇 | 3.531.53415510.10.10.6448.21010 |
在85℃下A部分和B部分各自混合，然后在搅拌中将两部分并合。最后，用10％氢氧化钾和10％柠檬酸(必要时)将pH值校正至7。
实施例8，11和12的乳液，在全部约280nm至400nm区间内显示出宽范围的滤光作用，其中在约300至360nm的区间内具有较宽范围的稳定的最大值。
Claims (23)
1.一种用以保护人体皮肤或人体毛发免受紫外线辐射的化妆品用遮光组合物，该组合物在化妆品适用的载体中含有至少一种式I的化合物：
其中R1代表C1-8的直链或支链烷基链，
R2和R3各自独立地代表C1-8的直链或支链烷基链。
2.权利要求1的化妆品用遮光组合物，其中R1代表甲基、乙基或正丁基，R2和R3各自独立地代表甲基、乙基、戊基或2-乙基己基。
3.权利要求2的化妆品用遮光组合物，其中R1、R2和R3都是乙基。
4.权利要求1的化妆品用遮光组合物，含有0.1％至10％重量的式I的化合物。
5.权利要求2的化妆品用遮光组合物，含有0.1％至10％重量的式I的化合物。
6.权利要求3的化妆品用遮光组合物，含有0.1％至10％重量的式I的化合物。
7.权利要求4的化妆品用遮光组合物，含有0.5％至5％重量的式I的化合物。
8.权利要求5的化妆品用遮光组合物，含有0.5％至5％重量的式I的化合物。
9.权利要求6的化妆品用遮光组合物，含有0.5％至5％重量的式I的化合物。
10.权利要求7的化妆品用遮光组合物，含有1％至3％重量的式I的化合物。
11.权利要求8的化妆品用遮光组合物，含有1％至3％重量的式I的化合物。
12.权利要求9的化妆品用遮光组合物，含有1％至3％重量的式I的化合物。
13.权利要求1-12中任一项的化妆品用遮光组合物，另含有至少一种在300-320nm区具有吸收最大值的UV-B滤光剂和至少一种在≥340nm区具有吸收最大值的UV-A滤光剂。
14.权利要求13的化妆品用遮光组合物，其中所述UV-A滤光剂是在340至360mm之间具有吸收最大值的UV-A滤光剂。
15.权利要求13的化妆品用遮光组合物，其中UV-A滤光剂是下列化合物中的一种：2-甲基二苯甲酰基甲烷；4-甲基二苯甲酰基甲烷；4-叔丁基二苯甲酰基甲烷；2，4-二甲基二苯甲酰基甲烷；2，5-二甲基二苯甲酰基甲烷；4，4′-二异丙基二苯甲酰基甲烷；4-叔丁基-4′-甲氧基二苯甲酰基甲烷；2-甲基-5-异丙基-4′-甲氧基二苯甲酰基甲烷；2-甲基-5-叔丁基-4′-甲氧基二苯甲酰基甲烷；2，4-二甲基-4′-甲氧基二苯甲酰基甲烷；2，6-二甲基-4-叔丁基-4′-甲氧基二苯甲酰基甲烷；以及对苯二甲亚基二樟脑磺酸。
16.权利要求15的化妆品用遮光组合物，其中UV-A滤光剂是4-叔丁基-4′-甲氧基二苯甲酰基甲烷。
17.权利要求13的化妆品用遮光组合物，其中UV-B滤光剂是下列中的至少一种：肉桂酸酯，水杨酸酯，二苯酮，联苯基丙烯酸酯，三嗪，樟脑衍生物或铈、铁、钛、锌或锆的颜料金属氧化物，以及带有具有至少一个紫外光线吸收基的硅氧烷结构或烃结构的聚合物。
18.权利要求14的化妆品用遮光组合物，其中UV-B滤光剂是下列中的至少一种：肉桂酸酯，水杨酸酯，二苯酮，联苯基丙烯酸酯，三嗪，樟脑衍生物或铈、铁、钛、锌或锆的颜料金属氧化物，以及带有具有至少一个紫外光线吸收基的硅氧烷结构或烃结构的聚合物。
19.权利要求15的化妆品用遮光组合物，其中UV-B滤光剂是下列中的至少一种：肉桂酸酯，水杨酸酯，二苯酮，联苯基丙烯酸酯，三嗪，樟脑衍生物或铈、铁、钛、锌或锆的颜料金属氧化物，以及带有具有至少一个紫外光线吸收基的硅氧烷结构或烃结构的聚合物。
20.权利要求16的化妆品用遮光组合物，其中UV-B滤光剂是下列中的至少一种：肉桂酸酯，水杨酸酯，二苯酮，联苯基丙烯酸酯，三嗪，樟脑衍生物或铈、铁、钛、锌或锆的颜料金属氧化物，以及带有具有至少一个紫外光线吸收基的硅氧烷结构或烃结构的聚合物。
21.权利要求17-20中任一项的化妆品用遮光组合物，其中所述颜料金属氧化物是钛或锌的颜料金属氧化物。
22.权利要求1至21中任一项权利要求的化妆品用遮光组合物用以保护人体皮肤或人体毛发不受紫外线辐射的用途。
23.式I的化合物，其选自下列化合物：
2-(4-甲氧基-苯胺亚甲基)-丙二酸二甲酯，
2-(4-乙氧基-苯胺亚甲基)-丙二酸二甲酯，
2-(4-丁氧基-苯胺亚甲基)-丙二酸二甲酯，
2-(4-乙氧基-苯胺亚甲基)-丙二酸二戊酯，
2-(4-乙氧基-苯胺亚甲基)-丙二酸乙酯戊酯，
2-(4-乙氧基-苯胺亚甲基)-丙二酸二-2-乙基己酯，和
2-(4-乙氧基-苯胺亚甲基)-丙二酸乙酯2-乙基己酯。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97113446 | 1997-08-05 | ||
| EP97113446.5 | 1997-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1207290A CN1207290A (zh) | 1999-02-10 |
| CN1148165C true CN1148165C (zh) | 2004-05-05 |
Family
ID=8227170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB981167918A Expired - Fee Related CN1148165C (zh) | 1997-08-05 | 1998-08-03 | 化妆品用遮光组合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6069170A (zh) |
| EP (1) | EP0895776B1 (zh) |
| JP (1) | JPH11100318A (zh) |
| KR (1) | KR100543269B1 (zh) |
| CN (1) | CN1148165C (zh) |
| AU (1) | AU739558B2 (zh) |
| BR (1) | BR9802837A (zh) |
| CA (1) | CA2244556A1 (zh) |
| DE (1) | DE69815449T2 (zh) |
| DK (1) | DK0895776T3 (zh) |
| ES (1) | ES2198026T3 (zh) |
| ID (1) | ID20678A (zh) |
| NO (1) | NO312332B1 (zh) |
| TW (1) | TW516965B (zh) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19904329A1 (de) * | 1999-01-28 | 2000-08-03 | Cognis Deutschland Gmbh | Kosmetische und/oder pharmazeutische Zubereitungen |
| US6165451A (en) * | 1999-02-08 | 2000-12-26 | Roche Vitamins Inc. | Cosmetic light screening composition |
| EP1025836A1 (en) * | 1999-02-08 | 2000-08-09 | F. Hoffmann-La Roche Ag | Cosmetic light screening composition |
| DE19937299A1 (de) * | 1999-08-06 | 2001-02-15 | Cognis Deutschland Gmbh | Sonnenschutzmittel |
| DE10063946A1 (de) | 2000-12-20 | 2002-07-04 | Basf Ag | Verwendung von Lichtschutzmittelkombinationen, die als wesentlichen Bestandteil 2,2'-p-Phenylen-bis(3,1-benzoxazin-4-on) enthalten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| DE10063867A1 (de) * | 2000-12-21 | 2002-07-11 | Haarmann & Reimer Gmbh | Kosmetische Lichtschutzzubereitungen |
| DE10113058A1 (de) | 2001-03-15 | 2002-09-19 | Basf Ag | Verwendung von Lichtschutzmittelkombinationen, die als wesentlichen Bestandteil 2-(4-Alkoxy-anilinomethylen)-malonsäure-dialkylester enthalten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| DE10124332A1 (de) | 2001-05-18 | 2002-11-21 | Basf Ag | Kosmetische oder pharmazeutische Zubereitungen, die Enaminotriazine als Lichtschutzmittel enthalten und neue Enaminotriazine |
| DE10143963A1 (de) * | 2001-09-07 | 2003-03-27 | Basf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O-Emulsionen, enthaltend ein aminosubstituiertes Hydroxybenzophenon |
| DE10143964A1 (de) * | 2001-09-07 | 2003-03-27 | Basf Ag | Emulgatorarme oder emulgatorfreie Systeme vom Typ Öl-in-Wasser mit einem Gehalt an Stabilisatoren und einem aminosubstituierten Hydroxybenzophenon |
| DE10143962A1 (de) * | 2001-09-07 | 2003-03-27 | Basf Ag | Kosmetische und dermatologische Zubereitungen in Form von O/W-Emulsionen, enthaltend ein aminosubstituiertes Hydroxybenzophenon |
| DE10143960A1 (de) * | 2001-09-07 | 2003-03-27 | Basf Ag | Kosmetische und dermatologische Zubereitungen in Stiftform, enthaltend ein aminosubstituiertes Hydroxybenzophenon |
| JP4369203B2 (ja) * | 2003-03-24 | 2009-11-18 | 信越化学工業株式会社 | 反射防止膜材料、反射防止膜を有する基板及びパターン形成方法 |
| KR100857967B1 (ko) * | 2003-06-03 | 2008-09-10 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 반사 방지막 재료, 이것을 이용한 반사 방지막 및 패턴형성 방법 |
| KR100882409B1 (ko) * | 2003-06-03 | 2009-02-05 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 반사 방지용 실리콘 수지, 반사 방지막 재료, 이것을 이용한 반사 방지막 및 패턴 형성 방법 |
| KR101123520B1 (ko) | 2003-12-04 | 2012-03-13 | 디에스엠 아이피 어셋츠 비.브이. | 자외선 필터 활성을 갖는 미세캡슐 및 그의 제조방법 |
| WO2005092282A1 (en) | 2004-03-25 | 2005-10-06 | Dsm Ip Assets B.V. | Uv absorbing chromophores covalently bonded to hyperbranched polymers |
| EP1727516B1 (en) | 2004-03-26 | 2014-05-14 | DSM IP Assets B.V. | Composition comprising an hdac inhibitor in combination with a retinoid |
| US20080063674A1 (en) | 2004-06-28 | 2008-03-13 | Dsm Ip Assets B.V. | Cosmetic Composition Containing Protein Hydrolysates |
| US20080031909A1 (en) | 2004-12-10 | 2008-02-07 | Dsm Ip Assets B.V. | Encapsulated Cosmetic Materials |
| EP1879551A2 (de) | 2005-02-21 | 2008-01-23 | Basf Aktiengesellschaft | Wirkstoffzusammensetzung die wenigstens ein stickstoffatomhaltiges, hyperverzweigtes polymer enthält |
| KR101286782B1 (ko) | 2005-09-20 | 2013-07-17 | 디에스엠 아이피 어셋츠 비.브이. | 신규 카복실산 유도체 |
| EP1959914B1 (en) | 2005-12-09 | 2014-05-21 | DSM IP Assets B.V. | Cosmetic or dermatological compositions comprising modified titanium dioxide particles |
| EP2034977B1 (en) | 2006-04-21 | 2011-07-13 | DSM IP Assets B.V. | Use of opioid receptor antagonists |
| US8394500B2 (en) | 2006-06-16 | 2013-03-12 | Dsm Ip Assets B.V. | Compositions based on hyperbranched condensation polymers and novel hyperbranched condensation polymers |
| KR20090033470A (ko) | 2006-07-14 | 2009-04-03 | 디에스엠 아이피 어셋츠 비.브이. | 로즈힙 및 다른 활성 약품을 포함하는, 염증성 질환의 치료를 위한 조성물 |
| EP2190404A1 (en) | 2007-09-18 | 2010-06-02 | Fujifilm Manufacturing Europe B.V. | Uv absorbing compounds |
| EP2070524A1 (en) | 2007-12-11 | 2009-06-17 | DSM IP Assets B.V. | Compositions comprising Magnolol and/or Honokiol and glucosamine and use thereof for the treatment, co-treatment or prevention of inflammatory disorders |
| EP2070525A1 (en) | 2007-12-11 | 2009-06-17 | DSM IP Assets B.V. | Compositions comprising Magnolol and/or Honokiol and chondroitin and use thereof for the treatment, co-treatment or prevention of inflammatory disorders |
| WO2010094760A1 (en) | 2009-02-23 | 2010-08-26 | Dsm Ip Assets B.V. | Cajanus extracts and glucosamine for inflammatory disorders |
| US8951508B2 (en) | 2009-12-09 | 2015-02-10 | Dsm Ip Assets B.V. | Compound |
| KR20120115510A (ko) | 2009-12-09 | 2012-10-18 | 디에스엠 아이피 어셋츠 비.브이. | 신규 화합물 |
| US20120282201A1 (en) | 2009-12-09 | 2012-11-08 | Alexander Schlifke-Poschalko | Novel compounds |
| US20120282200A1 (en) | 2009-12-09 | 2012-11-08 | Alexander Schlifke-Poschalko | Uv absorbing dentritic polyether prepared by polymerization of oxetanes |
| US20120288456A1 (en) | 2009-12-09 | 2012-11-15 | Alexander Schlifke-Poschalko | Novel compound |
| WO2011070071A2 (en) | 2009-12-09 | 2011-06-16 | Dsm Ip Assets B.V. | Novel compound |
| CN102655849B (zh) | 2009-12-09 | 2015-04-15 | 帝斯曼知识产权资产管理有限公司 | 新颖的化合物 |
| US8883829B2 (en) | 2010-01-15 | 2014-11-11 | Dsm Ip Assets B.V. | 2-phenyl-1,2,3-benzotriazoles for UV radiation absorbance |
| WO2011121093A1 (en) | 2010-03-31 | 2011-10-06 | Dsm Ip Assets B.V. | Use of organic compounds in hair care |
| CN102844017B (zh) | 2010-04-12 | 2015-10-21 | 帝斯曼知识产权资产管理有限公司 | 含有藤黄酸、藤黄酸酯或藤黄酰胺的毛发护理组合物 |
| WO2012010624A2 (en) | 2010-07-23 | 2012-01-26 | Dsm Ip Assets B.V. | Topical use of steviol or derivatives in hair care |
| US20140044656A1 (en) | 2011-03-01 | 2014-02-13 | Dsm Ip Assets B.V. | Novel use |
| EP2522330A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and an edelweiss extract |
| EP2522331A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and niacinamide |
| EP2522329A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and arbutin |
| EP2522335A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and sodium-ascorbyl-phophate |
| EP2522332A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and magnesium-ascorbyl-phosphate |
| EP2522328A1 (en) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Use of resveratrol and ascorbyl-2-glucoside |
| WO2013041515A1 (en) | 2011-09-20 | 2013-03-28 | Dsm Ip Assets B.V. | Novel polyester based uv filters |
| WO2013104526A1 (en) | 2012-01-09 | 2013-07-18 | Dsm Ip Assets B.V. | Use of danielone and derivatives thereof in skin care |
| EP2623094A1 (en) | 2012-02-02 | 2013-08-07 | DSM IP Assets B.V. | Use of an edelweiss extract |
| EP3052202B1 (en) | 2013-10-04 | 2019-03-06 | DSM IP Assets B.V. | Skin tanning extract |
| EP2873414A1 (en) | 2013-11-19 | 2015-05-20 | DSM IP Assets B.V. | Use of an edelweiss extract in hair care for the prevention of hair graying |
| EP2873440A1 (en) | 2013-11-19 | 2015-05-20 | DSM IP Assets B.V. | Use of an edelweiss extract in hair care for stimulating hair growth |
| KR102487937B1 (ko) | 2014-10-17 | 2023-01-13 | 디에스엠 아이피 어셋츠 비.브이. | 10-하이드록시스테아르산을 포함하는 화장품 조성물의 용도 |
| KR102623466B1 (ko) | 2014-12-04 | 2024-01-09 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 유기 상 함유 조성물의 점도 개질 |
| EP3421096A1 (en) | 2017-06-30 | 2019-01-02 | Athenion AG | Method for solubilizing poorly water-soluble cosmetic agents |
| EP3709956A1 (en) | 2017-11-13 | 2020-09-23 | DSM IP Assets B.V. | Cosmetic or dermatological compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL279734A (zh) * | 1961-06-26 | |||
| US3515745A (en) * | 1967-10-05 | 1970-06-02 | Merck & Co Inc | Synthesis of arylamino methylenemalonates |
| DE1908548A1 (de) * | 1968-02-29 | 1970-11-05 | Warner Lambert Co | Chinolinderivate |
| NL190101C (nl) * | 1978-11-13 | 1993-11-01 | Givaudan & Cie Sa | Dibenzoylmethaanverbinding en tegen licht beschermend preparaat. |
| GB8422916D0 (en) * | 1984-09-11 | 1984-10-17 | May & Baker Ltd | Compositions of matter |
| GB9110123D0 (en) * | 1991-05-10 | 1991-07-03 | Dow Corning | Organosilicon compounds their preparation and use |
| DE4122475A1 (de) * | 1991-07-06 | 1993-01-07 | Basf Ag | Aminomethylencyanessigester |
| SK56097A3 (en) * | 1994-11-10 | 1998-07-08 | Basf Ag | 2-cyanoacrylic acid esters |
| US5639446A (en) * | 1996-09-20 | 1997-06-17 | 3V Inc. | Derivatives of benzoxazole useful as UV stabilizers |
-
1998
- 1998-07-24 US US09/122,117 patent/US6069170A/en not_active Expired - Fee Related
- 1998-07-30 DK DK98114262T patent/DK0895776T3/da active
- 1998-07-30 ES ES98114262T patent/ES2198026T3/es not_active Expired - Lifetime
- 1998-07-30 EP EP98114262A patent/EP0895776B1/en not_active Expired - Lifetime
- 1998-07-30 CA CA002244556A patent/CA2244556A1/en not_active Abandoned
- 1998-07-30 DE DE69815449T patent/DE69815449T2/de not_active Expired - Fee Related
- 1998-08-03 CN CNB981167918A patent/CN1148165C/zh not_active Expired - Fee Related
- 1998-08-04 KR KR1019980031729A patent/KR100543269B1/ko not_active IP Right Cessation
- 1998-08-04 JP JP10219930A patent/JPH11100318A/ja active Pending
- 1998-08-04 BR BR9802837-5A patent/BR9802837A/pt not_active Application Discontinuation
- 1998-08-04 AU AU78776/98A patent/AU739558B2/en not_active Ceased
- 1998-08-04 NO NO19983581A patent/NO312332B1/no not_active IP Right Cessation
- 1998-08-04 ID IDP981090A patent/ID20678A/id unknown
- 1998-10-01 TW TW087116339A patent/TW516965B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11100318A (ja) | 1999-04-13 |
| ES2198026T3 (es) | 2004-01-16 |
| ID20678A (id) | 1999-02-11 |
| CN1207290A (zh) | 1999-02-10 |
| KR100543269B1 (ko) | 2006-04-21 |
| CA2244556A1 (en) | 1999-02-05 |
| DE69815449D1 (de) | 2003-07-17 |
| TW516965B (en) | 2003-01-11 |
| NO983581D0 (no) | 1998-08-04 |
| EP0895776A2 (en) | 1999-02-10 |
| KR19990023356A (ko) | 1999-03-25 |
| EP0895776A3 (en) | 1999-04-28 |
| DK0895776T3 (da) | 2003-08-25 |
| US6069170A (en) | 2000-05-30 |
| NO983581L (no) | 1999-02-08 |
| DE69815449T2 (de) | 2004-02-12 |
| BR9802837A (pt) | 2000-01-11 |
| NO312332B1 (no) | 2002-04-29 |
| EP0895776B1 (en) | 2003-06-11 |
| AU739558B2 (en) | 2001-10-18 |
| AU7877698A (en) | 1999-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1148165C (zh) | 化妆品用遮光组合物 | |
| RU2203034C2 (ru) | Способ повышения устойчивости к уф-излучению светочувствительных солнечных фильтров, материал, устойчивый к уф-излучению, косметическая и/или дерматологическая композиция | |
| US6350894B1 (en) | Stable sunscreen composition containing dibenzoylmethane derivative, e.g., parsol 1789, and c12, c16, c18 branched chain hydroxybenzoate and/or c12, c16 branched chain benzoate stabilizers/solubilizers | |
| EP0832642B1 (en) | Derivatives of Benzoxazole useful as uv filters | |
| EP1701695B1 (en) | Merocyanine derivatives for cosmetic use | |
| US6193959B1 (en) | Light screening compositions | |
| KR101312777B1 (ko) | 벤조산 에스테르 화합물, 조성물, 이들의 용도 및 제조방법 | |
| US6602515B2 (en) | Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom | |
| US7465438B2 (en) | Solubilizing agents/solvents for organic UV filters | |
| US20030157035A1 (en) | Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom | |
| CN1306417A (zh) | 防晒制剂 | |
| AU745721B2 (en) | Light screening composition | |
| BR0316607B1 (pt) | Derivados de hidroxifenil benzofenona substituídos com amino, seu uso, e preparação cosmética. | |
| KR20100135793A (ko) | 이량체 벤질리덴 말로네이트 | |
| EP1210929B1 (de) | Kosmetische Mittel enthaltend Alkyl- oder Alkenylbernsteinsäurederivate | |
| AU629540B2 (en) | Use of diorganopolysiloxanes containing a 3-benzylidene- camphor functional group in cosmetics and new cosmetic compositions containing these compounds, intended for protecting the skin and hair | |
| EP1123934A1 (en) | Benzoxazole derivatives useful as UV filters | |
| EP0800813B1 (en) | Cosmetic sunscreening compositions | |
| CN1218661A (zh) | 含光稳定性紫外线滤光剂的化妆品和药品 | |
| CN1646091A (zh) | 氨基羟基二苯酮的有机硅氧烷衍生物及其在化妆品制备中作为uv－a滤光剂的用途 | |
| CN1668675A (zh) | 防晒制剂 | |
| EP0726757B1 (fr) | Composition dermato-cosmetique, notamment pour la photoprotection et procede de preparation | |
| EP0737508A1 (fr) | Utilisation d'un composé hydrofluorocarboné dans une émulsion, émulsion et composition comprenant un tel composé | |
| CN1141769A (zh) | 二羟基丙酮的用途 | |
| US5505936A (en) | Phosphoric diesters which absorb UV rays, method of preparing the same, and cosmetic compositions containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: DSMIP CAPITAL CO., LTD. Free format text: FORMER OWNER: HOFFMAN-LALUOAI LTD. Effective date: 20040903 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20040903 Address after: Holland Heerlen Patentee after: DSM IP Assets BV Address before: Basel Patentee before: F. Hoffmann-La Roche AG |
|
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |