CN1355686A - 微细颜料混合物 - Google Patents
微细颜料混合物 Download PDFInfo
- Publication number
- CN1355686A CN1355686A CN00808933A CN00808933A CN1355686A CN 1355686 A CN1355686 A CN 1355686A CN 00808933 A CN00808933 A CN 00808933A CN 00808933 A CN00808933 A CN 00808933A CN 1355686 A CN1355686 A CN 1355686A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- formula
- represent
- group
- filtering agent
- 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 50
- 239000002537 cosmetic Substances 0.000 claims abstract description 25
- 241001465754 Metazoa Species 0.000 claims abstract description 4
- 230000005855 radiation Effects 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims description 84
- -1 acrylic acid diphenyl ester Chemical class 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 67
- 238000001914 filtration Methods 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 238000002360 preparation method Methods 0.000 claims description 31
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 17
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001768 cations Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 241001597008 Nomeidae Species 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 235000006708 antioxidants Nutrition 0.000 claims description 14
- 150000003921 pyrrolotriazines Chemical class 0.000 claims description 14
- 230000004927 fusion Effects 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000001449 anionic compounds Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000001023 inorganic pigment Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 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 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 150000001565 benzotriazoles Chemical class 0.000 claims description 5
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940067631 phospholipid Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229960004555 rutoside Drugs 0.000 claims description 4
- 239000011732 tocopherol Substances 0.000 claims description 4
- 229960001295 tocopherol Drugs 0.000 claims description 4
- LAXWTHPUJQUILB-UHFFFAOYSA-N 1h-benzimidazole;1h-imidazole Chemical class C1=CNC=N1.C1=CC=C2NC=NC2=C1 LAXWTHPUJQUILB-UHFFFAOYSA-N 0.000 claims description 3
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 229940025250 camphora Drugs 0.000 claims description 3
- 239000010238 camphora Substances 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000003628 erosive effect Effects 0.000 claims description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 3
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003904 phospholipids Chemical class 0.000 claims description 3
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- 229930003799 tocopherol Natural products 0.000 claims description 3
- 235000010384 tocopherol Nutrition 0.000 claims description 3
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 claims description 3
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229920002079 Ellagic acid Polymers 0.000 claims description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000001654 beetroot red Substances 0.000 claims description 2
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229940106189 ceramide Drugs 0.000 claims description 2
- 229960002852 ellagic acid Drugs 0.000 claims description 2
- 229940114124 ferulic acid Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000002378 plant sterols Nutrition 0.000 claims description 2
- 229940069949 propolis Drugs 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 229940048109 sodium methyl cocoyl taurate Drugs 0.000 claims description 2
- 229940035936 ubiquinone Drugs 0.000 claims description 2
- 229940032912 zephiran Drugs 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims 1
- DHHFDKNIEVKVKS-FMOSSLLZSA-N Betanin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC(C[C@H]2C([O-])=O)=C1[N+]2=C\C=C\1C=C(C(O)=O)N[C@H](C(O)=O)C/1 DHHFDKNIEVKVKS-FMOSSLLZSA-N 0.000 claims 1
- DHHFDKNIEVKVKS-MVUYWVKGSA-N Betanin Natural products O=C(O)[C@@H]1NC(C(=O)O)=C/C(=C\C=[N+]/2\[C@@H](C(=O)[O-])Cc3c\2cc(O)c(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)c3)/C1 DHHFDKNIEVKVKS-MVUYWVKGSA-N 0.000 claims 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims 1
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims 1
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 claims 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims 1
- SHCRKMNTWSCEBT-UHFFFAOYSA-N N1N=NC=C2N=CC=C21 Chemical group N1N=NC=C2N=CC=C21 SHCRKMNTWSCEBT-UHFFFAOYSA-N 0.000 claims 1
- 241000241413 Propolis Species 0.000 claims 1
- 235000012677 beetroot red Nutrition 0.000 claims 1
- 235000002185 betanin Nutrition 0.000 claims 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims 1
- 235000017471 coenzyme Q10 Nutrition 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 235000004132 ellagic acid Nutrition 0.000 claims 1
- 235000001785 ferulic acid Nutrition 0.000 claims 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims 1
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 claims 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims 1
- 235000010388 propyl gallate Nutrition 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002640 tocopherol group Chemical group 0.000 claims 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims 1
- 235000012141 vanillin Nutrition 0.000 claims 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims 1
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- 239000004904 UV filter Substances 0.000 abstract 1
- 230000001627 detrimental effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000037072 sun protection Effects 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 67
- 239000000049 pigment Substances 0.000 description 52
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 38
- 239000000839 emulsion Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000002585 base Substances 0.000 description 29
- 229920001577 copolymer Polymers 0.000 description 28
- 235000011187 glycerol Nutrition 0.000 description 27
- 239000012964 benzotriazole Substances 0.000 description 25
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 23
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 23
- 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 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229960001679 octinoxate Drugs 0.000 description 21
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 19
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 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 16
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 16
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 238000000227 grinding Methods 0.000 description 12
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 12
- 239000004205 dimethyl polysiloxane Substances 0.000 description 11
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000516 sunscreening agent Substances 0.000 description 8
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- 238000006471 dimerization reaction Methods 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920005573 silicon-containing polymer Polymers 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004408 titanium dioxide Substances 0.000 description 6
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Abstract
本发明涉及超细有机紫外滤除剂混合物的用途,用于保护人体和动物的皮肤和头发不受紫外线辐射的有害侵蚀。本发明还涉及所述混合物在化妆品和药物制剂中的用途。根据本发明,所使用的超细混合物覆盖了较宽的紫外线范围,因此具有极好的防日晒特性。
Description
本发明涉及超细有机紫外滤除剂混合物的用途,用于保护人和动物的皮肤和头发不受紫外线的有害侵蚀,以及其在化妆品和药物制剂中的用途。
众所周知,当某些有机紫外滤除剂例如微溶性苯并三唑化合物或三嗪化合物作为单一化合物以超细形式存在时具有突出的紫外滤除剂特性。然而,根据其特殊的、物质特异的特性,这类化合物总是吸收、反射或散射某一部分的有害紫外线。
人们对这样的一种防光剂极感兴趣,它能覆盖较宽范围的紫外光谱并且具有良好的防紫外光特性。
因此,本发明的目的是提供一种超细有机紫外滤除剂,利用这种滤除剂覆盖较宽范围的紫外光并且能良好地防止紫外线。
令人惊奇地发现:至少两种超细紫外滤除剂的混合物能够实现这一目的。
因此,本发明的目的是提供超细有机紫外滤除剂混合物的用途,用于保护人和动物的皮肤和头发不受紫外线的有害侵蚀。
适用于本发明的紫外滤除剂是有机化合物,在某些情况下是难溶性有机化合物,例如三嗪衍生物,尤其是羟苯基三嗪化合物或苯并三唑衍生物、含乙烯基的酰胺、肉桂酸衍生物、磺化苯并咪唑、费歇尔碱衍生物、二苯基丙二酸二腈、草酰胺、樟脑衍生物、二苯基丙烯酸酯、对氨基苯甲酸(PABA)和其衍生物、水杨酸酯、二苯甲酮和其他用作紫外滤除剂的已知物质。
根据本发明,适用的、优选的三嗪衍生物是对应于式(1)的化合物式中:
R1、R2和R3彼此独立地代表氢;OH;C1-18烷氧基;-NH2;-NH-R4;-N(R4)2;-OR4,
R4代表C1-5烷基;苯基;苯氧基;苯胺基;吡咯并,其中苯基、苯氧基、苯胺基或吡咯并可是未被取代的或可被一个、两个或三个OH基团、羧基、-CO-NH2、C1-5烷基或C1-5烷氧基取代;亚甲基樟脑基团;式-(CH=CH)mC(=O)-OR4基团;式的基团或其对应的碱金属盐,铵盐,一-、二-或三-C1-4-烷基铵盐、一-、二-或三-C2-4-链烷醇铵盐、或其C1-3烷基酯;或式(1a)的基团
R′,R″和R″′,彼此独立地代表未取代的或被一个或多个OH基团取代的C1-14烷基:R6代表氢;M;C1-5烷基;或式
的基团;M代表金属阳离子;T1代表氢;或C1-8烷基;m代表0或1m2代表1-4;和m3代表2-14。其他优选的适用于本发明的三嗪衍生物是对应于式(2)的化合物
式中:
R7和R8彼此独立地代表C1-18烷基;C2-18链烯基;式-CH2-CH(-OH)-CH2-O-T1的基团;或
R7和R8代表式(2a)的基团R9代表直接键;直链或支链的C1-4亚烷基或式的基团;R10、R11和R12彼此独立地代表C1-18烷基;C1-18烷氧基或下式的基团R13代表C1-5烷基;m1代表1-4;p1代表0-5;A1代表式(2b)、(2c)的基团;或式(2d)的基团R14代表氢;C1-10烷基、
;或式-CH2-CH(-OH)-CH2-O-T1基团;R15代表氢;M;C1-5烷基;或式
基团;R16代表氢;或甲基;T1代表氢;或C1-8烷基;Q1代表C1-18烷基;M代表金属阳离子;m2和m3彼此独立地代表1-4;和n1代表1-16。更特别优选的式(2)三嗪衍生物是对应于下式的化合物式中:R17和R18彼此独立地代表C3-18烷基;或-CH2-CH(-OH)-CH2-O-T1;R19代表C1-10烷基或式(2a1)或(2a2)的基团
R20代表氢;M;C1-5烷基;-NH-C1-5烷基;优选-NH-叔烷基;或式-(CH2)m-O-T2的基团;
T1和T2彼此独立地代表氢;或C1-5烷基;和
m代表1-4.
特别优选的是式(2a)和(2b)的化合物,
式中:R17和R18彼此独立地代表C1-18烷基;或-CH2-CH(-OH)-CH2-O-T1;
R19代表C1-10烷基;
和式(2c)和(2d)的化合物,
式中:R17和R18彼此独立地代表C1-18烷基或-CH2-CH(-OH)-CH2-O-T1;和
T1代表氢;或C1-5烷基。
在上述化合物中,感兴趣地是式(2a)-(2d)的三嗪化合物,式中R17和R18具有同样的含义。
式中:
R21代表C1-30烷基;C2-30链烯基;未被取代的或被C1-5烷基一次取代或多次取代的C5-12环烷基;C1-5烷氧基-C1-12烷基;氨基-C1-12烷基;C1-5-一烷基氨基-C1-12烷基;C1-5二烷基氨基-C1-12烷基;式的基团;其中
R22,R23和R24彼此独立地代表氢;-OH;C1-30烷基、C2-30链烯基,R25代表氢;或C1-5烷基;m1代表0或1;和n1代表1-5。优选的化合物是对应于式(4)的化合物式中:或-O-2-乙基己基;-O-(CH2)3-N(C2H5)2;和r和s彼此独立地代表0-20。例如,适用于本发明的三嗪衍生物是对应于式(5)-(24)的化合物
此外,包括2,4,6-三(二异丁基-4′-氨基亚苄基丙二酸)-s-三嗪和2,4-双(二异丁基-4-氨基亚苄基丙二酸)-6-(4′-氨基亚苄基樟脑)-s-三嗪。
特别适用于本发明的三嗪化合物例如是EP-A-0818450中公开的化合物,例如式(24b)的化合物更特别优选的适用于本发明的三嗪衍生物是对应于式(25)的化合物式中:R27,R28和R29彼此独立地代表下式的基团
R30代表氢;碱金属;铵基-N(R33)4,
R33代表氢;C1-5烷基;或具有1-10个氧化乙烯单元并且端部OH基团可被C1-5醇醚化的聚氧乙烯基团;
R31代表氢;-OH;或C1-6烷氧基;
R32代表氢或-COOR30;和
n代表0或1。
如果R30代表碱金属,那么优选代表钾,更优选代表钠。
(R33)4特别代表一-、二-或三-C1-4烷基铵盐、一-、二-或三-C2-4链烷醇铵盐或其C1-3烷基酯。
如果R33代表C1-3烷基,那么优选代表C1-2烷基,优选代表甲基,和如果R33代表聚氧乙烯基,那么它优选含有2-6个氧化乙烯单元。
优选的适用于本发明的苯并三唑化合物是对应于式(26)的化合物
式中:
T1代表C1-5烷基或优选代表氢;和
T2代表C1-5烷基,优选代表叔丁基,或苯基取代的C1-4烷基,优选α,α-二甲基苄基。
式中:
T2具有式(26)中代表的含义。
式中:
T2具有式(26)代表的含义,并且优选甲基、叔丁基或异辛基。
优选适用于本发明的含乙烯基的酰胺是对应于式(29)的化合物
(29)R33-(Y)m-CO-C(R34)=C(R35)-N(R36)(R37)
式中:
R33代表C1-5烷基,优选甲基或乙基,或必要时被一个、两个或三个OH基团、C1-5烷基、C1-5烷氧基或CO-OR33取代的苯基;
R34、R35、R36和R37彼此独立代表C1-5烷基、优选甲基或乙基;或氢;
Y代表-NH或-O-;和
m具有上述含义。
优选的式(29)化合物是4-甲基-3-戊烯-2-酮、3-甲基-氨基-2-丁烯酸乙基酯、3-甲基氨基-1-苯基-2-丁烯-1-酮和3-甲基氨基-1-苯基-2-丁烯-1-酮。
式中:
R38代表氢或C1-5烷氧基,优选甲氧基或乙氧基;
R39代表氢或C1-5烷基,优选甲基或乙基;和
R40代表-(CONH)m苯基,其中m具有上述含义并且苯基必要时被一个、两个或三个OH基团、C1-3烷基、C1-3烷氧基或CO-OR30取代。
R40优选地代表苯基、4-甲氧基苯基或苯基氨基羰基。
其他优选的肉桂酸衍生物是2-乙基己基-4-甲氧基肉桂酸酯或-异戊酸酯或特别是在US-A-5 601 811和WO97/00851中公开的肉桂酸衍生物。优选的适用于本发明的磺化苯并咪唑是对应于式(31)的化合物
式中:
M代表氢或碱金属,优选钠,碱土金属,例如镁或钙或锌。
优选的适用于本发明的费歇尔碱醛(Fischer-Base-Aldehyde)是对应于式(32)的化合物,式中:R41代表氢;C1-5烷基;C1-18烷氧基;或卤素;R42代表C1-8烷基;C5-7环烷基;或C6-10芳基;R43代表C1-18烷基或式(32a)的基团R44代表氢;或式
的基团;R45代表
C1-18烷氧基;或式(32b)的基团R46和R47彼此独立地代表氢;或C1-5烷基;R48代表氢;C1-5烷基;C5-7环烷基;苯基;苯基-C1-3烷基;R49代表C1-18烷基;X代表卤素;式(32c)
或(32d)
的基团;和n代表0;或1。其他优选的适用化合物是对应于式(33)的化合物
式中:
R50,R51,R52,R53,R54彼此独立地代表氢、C1-8烷基或C5-10环烷基;
R55代表氢;C1-8烷基;C5-10环烷基;羟基;C1-8烷氧基;COOR56;或CONR57R58;
R56,R57和R58彼此独立地代表氢或C1-6烷基;
X和Y彼此独立地代表氢;-CN;CO2R59;CONR59R60;或COR59;
其中基团X和Y还可以代表C1-8烷基、C5-10烷基,尤其是苯基,或具有5-6个环上原子的杂芳基,此外,X和Y或
R50可与基团X和Y之一一起完整地形成5-7元环,它们可含有至多3个杂原子,尤其是氧和/或氮,其中环原子尤其可以被外向环双键合的氧(羰基氧)和/或被C1-8烷基和/或被C5-10环烷基取代和/或可含有C=C-双键;
Z代表氢;铵;碱金属离子;尤其是锂、钠、钾、1/2当量的碱土金属离子,优选钙、镁或用于中和游离酸基团的有机含氮碱的阳离子,
R59和R60彼此独立地代表氢、C1-8烷基或C5-10环烷基;和
n和m彼此独立地代表0或1。
R63和R64彼此独立地代表C1-5烷基,尤其是乙基。
其他优选的适用于本发明的化学类紫外滤除剂化合物包括:
-对氨基苯甲酸衍生物(PABA),尤其是2-乙基己基-4-二甲基氨基苯甲酸酯;
-水杨酸衍生物,尤其是2-乙基己基水杨酸酯;水杨酸三甲环己酯(Homosalate);和水杨酸异丙酯;
-二苯甲酮衍生物,尤其是2-二苯甲酮、3-二苯甲酮和4-二苯甲酮;
-二苯甲酰甲烷衍生物,尤其是1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-丙-1,3-二酮或丁基甲氧基二苯甲酰基甲烷;
-丙烯酸二苯酯,尤其是2-乙基己基-2-氰基-3,3-二苯基丙烯酸酯、2-氰基-3,3′-二苯基丙烯酸乙基酯和3-(苯并呋喃基)-2-氰基丙烯酸酯;
-3-咪唑-4-基丙烯酸和3-咪唑-4-基丙烯酸酯;
-苯并呋喃衍生物,尤其是在EP-A-582189、US-A-5338539,和US-A-5518713中公开的对-氨基苯基苯并呋喃衍生物;
-樟脑衍生物,尤其是3-(4′-甲基)亚苄基莰烷-2-酮、3-亚苄基莰烷-2-酮、N-[2(和)4]-2-氧亚龙脑-3-基甲基)苄基]丙烯酰胺聚合物、3-(4′-三甲基铵)亚苄基莰烷-2-酮-甲基硫酸酯、3,3′-(1,4-亚苯基二次甲基)-双(7,7-二甲基-2-氧代二环-[2.2.1]庚基-1-甲基磺酸)和其盐、3-(4′-硫代)亚苄基莰烷-2-酮和其盐;以及
-甲基-邻-氨基苯甲酸酯。
优选使用下列有机紫外滤除剂混合物:
-亚甲基双-苯并三唑基四甲基丁酚和辛基三嗪酮的混合物;
-辛基三嗪酮和亚甲基双-苯并三唑基四甲基丁酚的混合物;
-2-[(2,4-甲氧基)-苯基]-4,6-双[(2-羟基-4-甲氧基)-苯基]-(1,3,5)-三嗪和亚甲基双-苯并三唑基四甲基丁酚的混合物;
-亚甲基双-苯并三唑基四甲基丁酚和二辛基丁酰胺(Dioctybutamido)三嗪酮的混合物;
-亚甲基双-苯并三唑基四甲基丁酚和辛基-2,2′-亚甲基双-[6-(2H-苯并三唑-2-基)-4-甲酚的混合物;
-辛基三嗪酮和三间苯二酚基三嗪的混合物;
-亚甲基双-苯并三唑基四甲基丁酚,二辛基丁酰胺三嗪酮和式(37)化合物的混合物。
在上述定义的基团中,C1-18烷基代表直链或支链的烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、异戊基或叔戊基、庚基、辛基、异辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十七烷基或十八烷基。
C1-18烷氧基是直链或支链烷基,例如甲氧基、乙氧基、正-丙氧基、异丙氧基、正-丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基或十八烷氧基。
C2-18链烯基代表例如烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正-戊-2,4-二烯基、3-甲基-丁-2-烯基、正-辛-2-烯基、正-十二碳-2-烯基、异十二烯基、正-十二碳-2-烯基或正-十八碳-4-烯基。
适用于本发明的超细有机紫外滤除剂混合物的制备可按各种方法进行。
一方面,在超细颗粒(超细化)的制备过程中,可以将至少两种上述有机紫外滤除剂作为单一物质混合。
另一种可能的制备方法是将已经超细化的紫外滤除剂单一物质紧密混合。
第三种可能的制备方法是将至少两种上述紫外滤除剂一起熔融。冷却熔融体后,形成一种均匀的复合物,按一般的方式和方法超细化。
本发明的另一主题是由至少两种有机紫外滤除剂组成的均匀复合物。
本发明的再一主题是通过将一种或多种无机超细颜料熔融在一种或多种有机紫外滤除剂中获得的复合物。
超细颜料的实例是例如TiO2、ZnO、氧化铁或其他的无机氧化物,云母或其他合适的无机矿物,也包括有机酸的Ti盐、碱土金属盐或锌盐。
因此,这些无机超细颜料(TiO2,ZnO)中的一些颜料可以同时抑制不期望有的光催化特性并且还完全地利用了它们的有效特性。
有利的是,将上述无机紫外滤除剂熔融在亚甲基双-苯并三唑四甲基丁酚中。接着按常规方法超细化如此获得的复合物。
本发明的又一主题是通过将至少两种电中性的有机紫外滤除剂与带阳离子或阴离子电荷的化合物熔融获得的复合物。
为此,将带阳离子或阴离子电荷的化合物与对应的呈电中性的有机紫外滤除剂熔融,然后进行冷却。用该方法,在随后的超细化步骤中,可以制备具有持久带正电荷或负电荷的有机紫外滤除剂颜料。用这种处理方式极为有效地防止了防晒剂中粒径<1微米时可发生的超细颗粒的团聚。不处理时通常具有令人厌恶效果的颗粒“涂覆”在一些情况下将变得多余。
可采用紫外滤除剂或其他的化合物作为带阳离子或阴离子电荷的化合物,这种化合物具有一个或多个阳离子或阴离子基团,例如:
-N,N,N-三甲基-4-(2-氧代亚龙脑-3-基甲基)-苯胺甲基硫酸酯;
-樟脑苄烷铵(benzalkonium)硫酸二甲酯;
-脂肪胺;
-甜菜碱,例如椰油酰胺丙基甜菜碱;
-季铵化合物(Quats),例如蓖麻油酰胺丙基trimodium硫酸二甲酯、Quarternium 18,或十六烷基三甲基溴化铵;
-山萮酸和其它有机酸,例如异硬脂酸,柠檬酸单甘油酯或甲基椰油基牛磺酸钠;
-磷脂,例如磷脂酰胆碱、磷脂酰丝氨酸或烷基氧化胺;
-神经酰胺和假神经酰胺和植物甾醇。
最后提到的化合物赋予超细紫外滤除剂疏油特性。
复合物中阳离子或阴离子化合物的含量按紫外滤除剂的重量计为0.001-5重量%,优选0.01-3重量%。
本发明的再一个主题是通过将至少一种微溶或不溶性紫外滤除剂与抗氧化剂熔融获得的复合物。
为此,将微溶或不溶性有机紫外滤除剂与抗氧化剂一起熔融,冷却,接着按常规方法超细化。
适用于本发明的抗氧化剂包括全部的具有清扫特性的有机物质,这种物质能与有机紫外滤除剂一起熔融。人们获得了一种新型的超细颜料,这种颜料对其表面同时提供防紫外线作用和抗氧化作用。这种特性是化妆品防晒剂希望有的,因为在紫外线和光的影响下,不仅会对制剂而且会对皮肤形成有害的自由基,会导致所谓的Mallorca-Akne或皮肤的早期老化。向超细化的紫外滤除剂中添加了抗氧化剂,除了在受紫外线破坏中起保护作用外,同时还能防止防晒剂中组分的光化学分解。
复合物中抗氧化剂的含量按紫外滤除剂的重量计一般在0.001-30重量%,优选0.01-3重量%之间。
如果超细颜料中除了含有有机紫外滤除剂外,还含有上述的光催化活性无机超细颜料,例如二氧化钛、氧化锌(被涂覆也行)或其他合适的无机氧化物,例如氧化铁,则含有这些抗氧化剂是特别有利的。
抗氧化剂的实例包括下列的化合物:
-生育酚,例如α-生育酚(CAS59-02-9)、乙酸生育酚酯、维生素E琥珀酸酯,-鞣花酸
-没食子酸丙酯(CAS121-79-9)-N-丁基化羟基甲苯(BHT:CAS 128-37-0);-丁基化羟基茴香醚(BHA);-2,4,6-三(3,5-二-叔丁基-4-羟基苄基)(CAS1709-70-2)
-四-[亚甲基-3-(3′,5′-二-叔丁基-4-′羟基苯基)丙酸酯]甲烷(CAS 6683-19-8):-式
的化合物;-式
的化合物;
-香草醛;
-泛醌;
-阿魏酸和阿魏酸衍生物;
-芸香亭酸和芸香亭酸衍生物;
-尿刊酸和尿刊酸衍生物;和
-蜂胶。
优选使用下列抗氧化剂和有机紫外滤除剂的混合物:
-亚甲基双-苯并三唑四甲基丁酚,辛基三嗪酮,二氧化钛和生育酚的混合物,
-2,2′-亚甲基双-[6-(2H-苯并三唑-2-基)-4-甲酚,辛基三嗪酮,三间苯二酚三嗪和维生素E的混合物,
化合物的混合物。
本发明的又一主题是通过将可熔融的化妆品、植物和药物活性组分熔融在有机滤除剂中获得的复合物。
超细紫外滤除剂通常可用作高活性物质,尤其是化妆品和/或药物活性物质的载体。这类复合物的优点是能从固体中释放(缓慢释放)出活性物质。缓慢的释放确保了在紫外颜料的总利用时效中高活性物质,例如消炎剂、预防性活性物质或痕量元素,例如Zn2+或Mg2+的均匀活性。
可使用的活性物质的实例包括:
-抗维生物作用并且同时起消炎作用的活性物质,例如三氯生或二氯生;
-消炎活性物质,例如法呢醇、泛醇或鳄梨油;
-具有脱汗剂和/或止汗剂作用的活性物质,例如蓖麻醇酸锌和烷基柠檬酸酯;
-十一烯酸和其衍生物(例如二乙醇酰胺)
-十一酸锌;
-2-巯基吡啶氧化物,例如2-巯基吡啶氧化钠;
-熔融的香料或香料混合物,例如薄荷醇、香叶醇等;这些香料包含在超细颜料和制剂中,赋予其永久和均匀浓度的香味。
可采用对于超细颗粒适用的所有已知方法制备超细颜料混合物,例如:
-采用硬质的研磨介质例如,硅酸锆和保护表面活性剂或保护聚合物在水或合适的有机溶剂中进行湿磨;
-对含有合适的溶剂,例如水或有机溶剂的悬浮液或溶剂为水、乙醇、二氯乙烷、甲苯、N-甲基吡咯烷酮等的真溶液(echte Lsungen)等进行喷雾干燥。
-按RESS法(快速膨胀超临界溶液)膨胀超临界的流体(例如CO2),所述流体中溶解了紫外滤除剂或将液态的二氧化碳与含有一种或多种紫外滤除剂在适当有机溶剂中的溶液一起进行膨胀;
-从适当的溶剂中再沉积,包括从超临界的流体中(GASR法=气体抗溶剂再结晶/PCA法=用压缩的抗溶剂沉积)。
制备本发明超细有机紫外吸收剂时的研磨设备可使用喷嘴式磨机、球磨机、振动磨机或锤式磨机,优选高速搅拌磨机。研磨最好是在研磨助剂,例如烷基化乙烯吡咯烷酮聚合物、乙烯吡咯烷酮-乙酸乙烯酯共聚物、酰基谷氨酸盐(glutamate)、烷基聚葡糖苷、Ceteareth-25或尤其是磷脂的存在下进行。
如此制备的超细颜料和超细颜料的混合物具有的平均粒度一般为0.02-2纳米,优选0.05-1.5纳米,更优选0.1-1.0纳米。
根据其亲油性,可将它们单独地或与其他的可溶性有机紫外吸收剂一起按已知方法较好地合并入含油和含脂肪的化妆品制剂,例如油、O/W-乳剂或W/O-乳剂、蜡笔或凝胶中。
令人惊奇地是,在使用少量或完全未使用可溶性紫外吸收剂的情况下,制备了具有相同或改进型保护作用的制剂。
本发明的再一个主题是提供一种化妆品制剂,它包含超细颜料、必要时的一种或多种抗氧化剂和/或无机颜料和/或阳离子或阴离子化合物以及化妆品相容性的载体或助剂的混合物。
根据本发明,化妆品制剂含有各种化妆品用的添加剂。尤其包括下列添加剂:
-护肤剂,例如块状或液体皂、合成洗涤剂或洗膏形式的清洗和洁净皮肤的制剂,
-浴用制品,例如液态(泡沫浴、乳液、淋浴用制剂)或固态的浴用制品,例如洗浴香精块和浴盐;
-护肤剂,例如护肤乳状液、多相乳状液或护肤油;
-化妆用的护肤剂,例如日霜或粉霜形式的面部化妆品、面部粉霜(散装的和压制的)、胭脂或乳剂化妆品、护眼制剂,例如眼睑轮廓制剂、睫毛油、眼线膏、眼霜或眼睛固定霜;护唇制品,例如唇笔、唇膏、唇轮廓笔、护指甲制品,例如指甲油、去指甲油、指甲硬化剂或指甲脱膜剂;
-内膜护剂(Intimpflegemittel),例如Intim洗液或Intim喷剂;
-护脚制剂,例如足浴、爽脚粉、爽脚乳和/或香足胶、特种的脱汗剂和止汗剂或去茧剂;
-防光剂,例如防晒乳、防晒露、防晒霜、防晒油、防晒液或热带用品(Tropicals)、预先变黑剂或日晒后修整用化妆品;
-皮肤变黑剂,例如自行变黑乳;
-脱颜料剂,例如皮肤漂白制剂或皮肤变亮制剂;
-驱虫剂,例如驱虫油、驱虫露、驱虫喷雾剂或驱虫笔;
-除臭剂,例如除臭喷雾剂、泵喷雾剂(Pumpsprays)除臭凝胶、除臭笔或除臭棍;
-止汗剂,例如止汗笔、止汗乳或止汗棍;
-洁净和护理脏皮肤的制剂,例如合成洗涤剂(固态的或液态的)、换肤剂或擦洗剂或Peeling-Masken;
-化学形式的脱毛剂,例如脱毛粉、液态脱毛剂、霜状或膏状脱毛剂、凝胶状或气溶胶泡沫状脱毛剂;
-剃须剂,例如剃须皂、泡沫剃须霜、不起沫的剃须霜、剃须起沫剂、剃须凝胶、用于干剃除(Trockenrasur)的剃须前制剂、剃须后的制剂或剃须后的护肤蜜;
-香料制剂,例如香水(科隆水、化妆水、香水、化妆香料、香料)、香料油或香料霜;
-护理牙、假牙和口腔的制剂,例如牙膏、凝胶-牙膏、牙粉、漱口腔浓缩物、防牙菌斑漱口液、修复净化剂或修复助剂;
-头发处理用的化妆品制剂,例如香波形式的洗发剂、头发调理剂、护发剂,例如预处理剂、洗发水、头发整理霜、头发整理凝胶、润发脂、美发喷剂、Kurpackungen、Intensivharrkuren、头发变形用制剂,例如做成永久波浪形的烫发剂(热烫、中度烫、冷烫)、直发剂、液态固发剂、头发起沫剂、头发喷雾剂、烫黄色头发用制剂,例如过氧化氢溶液、增亮香波、烫黄色头发霜、烫黄色头发粉、烫黄色头发乳浆剂或烫黄色头发油、临时、半临时或永久性染发剂、含有自氧化染料的制剂,或天然染发剂,例如指甲花或春黄菊属植物。
所列举的最终制剂可以以各种表现形式提供,例如:
-以W/O-、O/W-、O/W/O-、W/O/W-、PIT-乳液和所有超细乳状液的液态制剂形式,
-以凝胶形式,
-以油、霜、乳或露的形式,
-以粉、漆、片剂或化妆品形式,
-以笔的形式,
-以喷雾剂(用驱动气体喷雾或泵喷)或气溶胶形式,
-以泡沫形式,或
-以膏状形式。
本发明化妆品用制剂优选含有其他的在UVB范围内吸收紫外线的物质。这里,滤除剂物质的总量按组合物的总量计为0.1-30重量%,优选0.5-10重量%,更优选1-6重量%。
尤其考虑使用油溶性的、未超细化的化合物作为其他的UVB滤除剂,例如选自对氨基苯甲酸衍生物、水杨酸衍生物、二苯甲酮衍生物、二苯甲酰基甲烷衍生物、丙烯酸二苯酯衍生物、苯并呋喃衍生物、含有一种或多种有机硅基团的聚合的紫外吸收剂、肉桂酸衍生物、樟脑衍生物、三苯胺基-s-三嗪衍生物、苯基苯并咪唑磺酸和其盐、邻氨基苯甲酸酯、苯并三唑衍生物的有机紫外吸收剂,和/或选自用氧化铝或二氧化硅涂覆的二氧化钛、氧化锌或云母的无机超细颜料。-对氨基苯甲酸衍生物化合物的实例是:4-氨基苯甲酸(PABA);式
的乙基二羟基丙基-PABA;式
的PEG-25-PABA,式中:m,n和x具有同样的含义并且分别不高于25;式
的辛基二甲基PABA;或式的甘氨酰氨基苯甲酸酯。-水杨酸衍生物化合物的实例是:式
的高基水杨酸酯;式
的三乙醇胺水杨酸酯;式(10)
的对二甲基氨基苯甲酸戊酯;式
的水杨酸辛酯;或式
的4-异丙基苄基水杨酸酯。
-二苯甲酮衍生物化合物的实例是:
二苯甲酮-3-(2-羟基-4-甲氧基二苯甲酮)、二苯甲酮-4-(2-羟基-4-甲氧基二苯甲酮-5-磺酸)或二苯甲酮-8-(2,2′-二羟基-4-甲氧基二苯甲酮)。
-二苯甲酰基甲烷衍生物化合物的实例是:
丁基甲氧基二苯甲酰基甲烷-[1-(4-叔丁基)-3-(4-甲氧基苯基)丙-1,3-二酮]。
-二苯基丙烯酸酯化合物的实例是:
氰双苯丙烯酸辛酯-(2-乙基己基-2-氰基-3,3′-二苯基丙烯酸酯)或etocrylen-(乙基-2-氰基-3,3′-二苯基丙烯酸酯)。
-苯并呋喃衍生物化合物的实例是:
3-(苯并呋喃基)-2-氰基丙烯酸酯、2-(2-苯并呋喃基)-5-叔丁基苯并噁唑或2-(对-氨基苯基)苯并呋喃和特别是下式的化合物-含有一种或多种有机硅基团的聚合紫外吸收剂化合物的实例是:亚苄基丙二酸酯衍生物,尤其是下式的化合物式中:R24代表氢或甲氧基和r大约为7;下式的化合物
-肉桂酸酯化合物的实例是:
辛基甲氧基肉桂酸酯(4-甲氧基肉桂酸-2-乙基己基酯)、二乙醇胺甲氧基肉桂酸(4-甲氧基肉桂酸的二乙醇胺盐)、异戊基-对-甲氧基肉桂酸酯(4-乙氧基肉桂酸-2-异戊基酯)、2,5-二异丙基甲基肉桂酸酯或肉桂酸酰胺衍生物。
-樟脑衍生物化合物的实例是:
4-甲基-亚苄基樟脑[3-(4′-甲基)亚苄基-莰烷-2-酮]、3-亚苄基樟脑(3-亚苄基-莰烷-2-酮)、聚丙烯酰胺基甲基亚苄基樟脑{N-[2(和4)-2-氧亚龙脑-3-基-甲基)苄基]丙烯酰胺聚合物}、Trimonium-亚苄基-樟脑硫酸盐-[3-(4′-三甲基铵)-亚苄基-莰烷-2-酮-甲基硫酸酯]、对苯二亚甲基(Terephthalyden)二樟脑-磺酸{3,3′-(1,4-亚苯基二次甲基)-双-(7,7-二甲基-2-氧代-二环-[2.2.1]庚基-1-甲基磺酸}或其盐、或亚苄基樟脑-磺酸[3-(4′-硫代)亚苄基莰烷-2-酮]或其盐。
-三苯胺基-s-三嗪衍生物化合物的实例是:
辛基三嗪-[2,4,6-三苯胺基-(对-羰-2′-乙基-1′-氧)-1,3,5-三嗪、以及US-A-5332568、US-A-5252323、WO93/17002和WO97/03642和EP-A-0517104中描述的三苯胺基-s-三嗪衍生物。
-苯并三唑化合物的实例是:
2-(2-羟基-5-甲基-苯基)苯并三唑。
下面的实施例旨在说明本发明,而不是对其限制。化妆品活性物质主要按INCI命名法命名(INIC=化妆品组分国际标准)。
实施例1
将50份亚甲基双-苯并三唑基四甲基丁酚和50份辛基三嗪酮与由硅酸锆-沙子组成的研磨介质、保护表面活性剂(烷基聚葡糖苷)和水一起在钢珠磨机(Perl-Mühle)中研磨成d50为190纳米的混合超细颜料。在分离出研磨介质后,用混合超细颜料的悬浮液制备防晒制剂。
实施例2
将32份辛基三嗪酮,1份十六烷基三甲基溴化铵和66份亚甲基双-苯并三唑基四甲基丁酚一起均匀熔融。快速冷却到室温并且机械(锤式破碎机)磨碎凝固的熔融体。将由此获得的粉末悬浮在水中,添加癸苷并与研磨助剂(‘重质沙’)一起超细化成直径d50为200纳米的颗粒。在分离出研磨助剂后,获得超细的紫外吸收剂复合物的含水悬浮液。用柠檬酸调节该悬浮液成弱酸性并可用于制备化妆品和药物制剂。
实施例3
将25份2-[(2,4-甲氧基)-苯基]-4,6-双-[(2-羟基-4-甲氧基)-苯基]-(1,3,5)-三嗪,74份亚甲基双-苯并三唑基四甲基丁酚和1份四-[亚甲基-3-(3′,5′-二-叔丁基-4′-羟苯基)丙酸酯]甲烷一起均匀熔融。快速冷却至室温并机械(锤式破碎机)磨碎凝固的熔融体。将由此获得的粉末悬浮在水中,先添加癸苷,在研磨步骤之后添加Ceteareth-25并与研磨助剂(‘重质沙’)一起超细化成直径d50为190纳米的颗粒。在分离出研磨助剂后,获得超细的紫外吸收剂复合物的含水悬浮液,用该悬浮液可制备化妆品和药物制剂。
实施例4
将25份二辛基丁酰胺三嗪酮溶解在75份熔融的亚甲基双-苯并三唑基四甲基丁酚中。快速冷却后,机械破碎混合物至细粉末,然后与由硅酸锆-沙子组成的研磨介质、保护表面活性剂(磷脂)和水一起研磨成d50为300纳米的超细颜料。用分离出研磨介质的超细颜料悬浮液制备防晒制剂。
实施例5
将24份辛基三嗪酮,5份二氧化钛和1份生育酚混合在75份熔融的亚甲基双-苯并三唑基四甲基丁酚中。快速冷却后,机械破碎混合物至细粉末,然后与由硅酸锆-沙子组成的研磨介质、保护表面活性剂(烷基聚苷)和水一起研磨成超细颜料。用分离出研磨介质的超细颜料悬浮液制备防晒制剂。
在下面的实施例6-11中,按与实施例1和2类似的方法制备具有下列组成的超细复合物悬浮液:
实施例6
60份2,2′-亚甲基双-[6-(2H-苯并三唑-2-基)-4-甲酚,20份辛基三嗪酮,19份三间苯二酚基三嗪和1份维生素E,用柠檬酸调节至pH6.5。
实施例7
实施例8
实施例9
实施例11
50份亚甲基双-苯并三唑基四甲基丁酚,10份二辛基丁酰胺三嗪酮(在pH<5时研磨,用柠檬酸调节至pH6.5)和20份式(102)的化合物。
实施例12:O/W-防晒露
A %
聚甘油基-3甲基葡糖二硬脂酸酯 | 2.0 |
油酸癸酯 | 5.7 |
棕榈酸异丙酯 | 6.0 |
辛酸/癸酸甘油三酯 | 7.5 |
B
甘油 | 3.0 |
Phenonip | 0.5 |
水 | 69.3 |
C
丙烯酸聚合物(Carbomer) | 0.2 |
棕榈酸异丙酯 | 0.8 |
D
实施例2的超细颜料 | 5.0 |
E
NaOH(10%) | 按需要 |
实施例13:O/W-乳剂
%
十六烷基磷酸钾 2.00
Tricontanyl PVP 1.00
辛酸/癸酸甘油三酯 5.00
Cetearyl异壬酸酯 5.00
C12-15烷基苯甲酸酯 5.00
硬脂酸甘油酯 3.00
十六醇 1.00
苯氧基乙醇 & 对羟基苯甲酸酯 1.00
辛基甲氧基肉桂酸酯 5.00
聚二甲基硅氧烷 0.10
去离子水 64.15
丙烯酸聚合物(Carbopol 981) 0.10
甘油 3.00
NaOH(10%) 1.00
实施例1的超细颜料 4.00
实施例14:O/W-乳剂:
%
Cetearyl醇 & 磷酸二(十六烷)酯
& 十六烷基聚氧乙烯醚-10磷酸酯 6.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.20去离子水 64.70丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.65实施例3的超细颜料 4.00
实施例15:O/W-乳剂:
%肉豆蔻酸异丙酯 & 三月桂基醚(trilaureth) 5.00-4磷酸酯Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 2.00C12-15烷基苯甲酸酯 5.00硬脂酸甘油酯 2.00十六醇 1.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.10去离子水 66.30丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.50实施例4的超细颜料 4.00
实施例16:O/W-乳剂
%硬脂基乳酸钠Tricontanyl PVP 1.50Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00硬脂酸甘油酯 3.50十六醇 2.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.20去离子水 63.60丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.10实施例6的超细颜料 4.00
实施例17:O/W-乳剂:
%Cetearyl醇 & Cetearyl硫酸钠 5.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.10去离子水 65.90甘油 3.00NaOH(10%) 0.30实施例9的超细颜料 4.00
实施例18:O/W-乳剂:
%月桂基苷 & 聚甘油基-2二羟基硬脂酸酯& 甘油 3.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 4.00Cetearyl异壬酸酯 4.00C12-15烷基苯甲酸酯 5.00硬脂酸甘油酯 2.00十六醇 3.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.20去离子水 64.49丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.21实施例8的超细颜料 4.00
实施例19:O/W-乳剂:
%Cetaryl苷 & Cetearyl醇 4.50Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基三嗪酮 3.004-甲基亚苯基樟脑 3.00聚二甲基硅氧烷 0.20去离子水 64.65Steareth-10烯丙基醚(丙烯酸酯共聚物)5.00甘油 3.00NaOH(10%) 1.00实施例2的超细颜料 4.00
实施例20:O/W-乳剂:
%Cetearyl苷 5.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00氰双苯丙烯酸辛酯 3.00辛基甲氧基肉桂酸酯 4.00聚二甲基硅氧烷 0.20去离子水 63.15丙烯酸聚合物(Carbopol 981) 0.50甘油 3.00NaOH(10%) 0.15实施例2的超细颜料 4.00
实施例21:O/W-乳剂:
%聚甘油基-10 Petastearate &山萮醇& 硬脂酰月桂酸钠 2.50辛酸/癸酯甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00硬脂酸甘油酯 3.00Cetearyl醇 2.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.20去离子水 64.75丙烯酸聚合物(Carbopol 981) 0.15甘油 3.00NaOH(10%) 0.40实施例9的超细颜料 4.00
实施例22:O/W-乳剂:
%棕榈酸 & 硬脂酸 1.80硬脂酸甘油酯SE 3.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00硬脂酸甘油酯 0.50苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基二甲基PABA 5.00聚二甲基硅氧烷 0.10去离子水 64.15丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.50实施例1的超细颜料 4.00
实施例23:O/W-乳剂:
%硬脂酸甘油酯 & PEG 100硬脂酸酯 3.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00Cetearyl醇 3.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.10去离子水 64.60丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.20实施例3的超细颜料 4.00
实施例24:O/W-乳剂:
%Steareth-2 2.50Steareth-21 1.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00十六醇 1.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00邻氨基苯甲酸甲酯 3.00辛基甲氧基肉桂酸酯 4.00聚二甲基硅氧烷 0.10去离子水 63.95丙烯酸聚合物(Carbopol 981) 0.20甘油 3.00NaOH(10%) 0.25实施例4的超细颜料 4.00
实施例25:O/W-乳剂:
%硬脂酸甘油酯 & Cetareth-20 & Cetareth-12 &Cetaryl醇 &棕榈酸十六烷酯 5.00Tricontanyl PVP 1.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.004-甲基亚苄基樟脑 5.00聚二甲基硅氧烷 0.10去离子水 65.60丙烯酸聚合物(Carbopol 981) 0.10甘油 3.00NaOH(10%) 0.20实施例3的超细颜料 4.00
实施例26:O/W-乳剂:
%磷酸辛基癸酯 3.00Tricontanyl PVP 1.00辛酸/癸酯甘油三酯 5.00Cetearyl异壬酸酯 5.00C12-15烷基苯甲酸酯 5.00苯氧基乙醇 & 对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.10去离子水 64.50椰油基谷氨酸钠 0.60Fteareth-10烯丙基醚/丙烯酸酯共聚物 0.50甘油 3.00NaOH(10%) 2.30实施例4的超细颜料 4.00实施例27:O/W-乳剂:
%聚甘油基-3甲基葡萄糖二硬脂酸酯 2.00Tricontanyl PVP 1.00生育酚 & 棕榈酸抗坏血酸酯 &抗坏血酸 & 柠檬酸 & PEG-8 0.05油酸癸酯 4.50棕榈酸异丙酯 6.00辛酸/癸酸甘油三酯 5.00硬脂酸甘油酯 1.00Cetearyl醇 1.002-[(2,4-甲氧基)-苯基]-4,6-双-[(2-羟基-4-甲氧基)-苯基]-(1,3,5)-三嗪 2.00辛基甲氧基肉桂酸酯 3.00去离子水 63.12苯氧基乙醇 & 对羟基苯甲酸酯 0.80丙二醇 3.00丙烯酸聚合物(Carbopol 981) 0.20NaOH(10%) 0.33Scleroglucan 1.00实施例2的超细颜料 3.00二氧化钛 3.00
实施例2:O/W-乳剂:
%甲基葡萄糖倍半硬脂酸酯 2.50Tricontanyl PVP 1.00生育酚 & 棕榈酸抗坏血酸酯& 抗坏血酸 & 柠檬酸 & PEG-8 0.05油酸癸酯 4.00棕榈酸异丙酯 6.00辛酸/癸酸甘油三酯 5.00硬脂酸甘油酯 1.00Cetearyl醇 1.002-[(2,4-甲氧基)-苯基]-4,6-双-[(2-羟基-4-甲氧基)-苯基]-(1,3,5)-三嗪 2.00辛基甲氧基肉桂酸酯 5.00去离子水 63.12苯氧基乙醇 & 对羟基苯甲酸酯 0.80丙烯酸聚合物(Carbopol 981) 0.20甘油 3.00NaOH(10%) 0.33Scleroglucan 1.00实施例1的超细颜料 4.00
实施例29:唇膏
%甘油 10.00PEG-45 & 十二烷基甘油共聚物 1.50Quaternium-18澎润土 2.00微晶蜡 2.00蜂蜡 2.00硬脂酸甘油酯SE 53.00Pentaerythrithil硬脂酸酯 & 癸酸酯& 辛酸酯己二酸酯 4.00蓖麻子油 4.00亚甲基双-苯并三唑基四甲基丁酚 5.00实施例2的超细颜料 5.00二氧化钛 5.00氧化锌 5.00辛基甲氧基肉桂酸酯 4.00Eucerinum anhydricum 加至100实施例30:W/O-乳剂
%PEG-30二聚羟基硬脂酸酯 2.00异硬脂醇 20.00异硬脂酸 10.00辛基三嗪酮 3.00去离子水 58.75甘油 5.00甲基对羟基苯甲酸酯 0.17丙基对羟基苯甲酸酯 0.03MgSO4×7H2O 0.75实施例2的超细颜料 4.00
实施例31:O/W-乳剂
%A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0油酸癸酯 5.7棕榈酸异丙酯 5.0辛酸/癸酸甘油三酯 6.5辛基甲氧基肉桂酸酯 5.0B 甘油 3.0Phenonip 0.5去离子水 62.9C 丙烯酸聚合物141 0.2棕榈酸异丙酯 0.8D 50%实施例8的悬浮液 8.0E NaOH(10%) 视需要
实施例32:O/W-乳剂
%A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0油酸癸酯 5.7棕榈酸异丙酯 5.0辛酸/癸酸甘油三酯 6.5B 甘油 3.0Phenonip 0.5去离子水 62.9C 丙烯酸聚合物141 0.2棕榈酸异丙酯 0.8D 实施例2的悬浮液 6.0E NaOH(10%) 视需要
实施例33:(O/W-乳剂)
%A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0油酸癸酯 5.7棕榈酸异丙酯 5.0辛酸/癸酸甘油三酯 6.5辛基三嗪酮 2.0B 甘油 3.0Phenonip 0.5水 62.3C 丙烯酸聚合物141 0.2棕榈酸异丙酯 0.8D 2,2′-亚甲基双-(6-(2H-苯并三唑基-2-基)-4-(1,1,3,3-四甲基丁基)酚-超细颜料-悬浮液(50%) 8.0辛基三嗪酮-超细颜料悬浮液(50%) 4.0E NaOH(10%) 视需要
实施例34:O/W-乳剂
%A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0油酸癸酯 5.7棕榈酸异丙酯 5.0辛基三嗪酮 2.0辛酸/癸酸甘油三酯 6.5B甘油 3.0Phenonip 0.5水 68.3C 丙烯酸聚合物141 0.2棕榈酸异丙酯 0.8D 实施例2的超细颜料 6.0E NaOH(10%) 视需要
实施例35:W/O-乳剂
%PEG-30二聚羟基硬脂酸酯(Arlacel P 135) 3.00PEG-22/十二烷基乙二醇共聚物(Elfzcos ST 37) 1.00微晶蜡 1.00氢化蓖麻子油 0.50硬脂酸镁 1.00硬脂酸辛酯 15.00椰油甘油酯 2.00矿物油 3.00苯氧基乙醇&对羟基苯甲酸酯 1.00辛基甲氧基肉桂酸酯 5.00聚二甲基硅氧烷 0.10水 54.40硫酸镁(MgSO4×7H2O) 1.00丙二醇 4.0050%实施例3的悬浮液 8.00
实施例36:W/O-乳剂
%甲氧基PEG-22/十二烷乙二醇共聚物(Elfacos E 200) 3.00PEG-22/十二烷乙二醇共聚物(Elfacos ST 37) 3.00羟基二十八烷基羟基硬脂酸酯(Elfacos C 26) 3.00硬脂酸辛酯 15.00椰油甘油酯 2.00矿物油 3.00苯氧基乙醇&对羟基苯甲酸酯 1.004-甲基亚苄基樟脑 3.00二辛基丁酰胺三嗪酮 3.00聚二甲基硅氧烷 0.20水 53.00苯基苯并咪唑磺酸 3.00硫酸镁(MgSO4×7H2O) 0.80丙二醇 4.00实施例5的超细颜料 3.00
实施例37:W/O-乳剂
%聚甘油基-2二聚羟基硬脂酸酯(Dehymuls PGPH) 2.00PEG-30二聚羟基硬脂酸酯(Arlacel P 135) 2.00羟基二十八烷基羟基硬脂酸酯(Elfacos C 26) 2.00硬脂酸锌 1.00硬脂酸辛酯 15.00椰油甘油酯 2.00矿物油 3.00苯氧基乙醇&对羟基苯甲酸酯 1.002,4-双-{[4-(2-乙基己氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)1,3,5)-三嗪 2.00水杨酸辛酯 3.00聚二甲基硅氧烷 0.20水 56.70硫酸镁(MgSO4×7H2O) 1.00丙二醇 4.00实施例6的超细颜料 5.00
实施例38:W/O-乳剂
%聚甘油基-2-二聚羟基硬脂酸酯(Dehymuls PGPH) 3.00油酸甘油酯(Monomuls 90-O 18) 1.00辛酸/癸酸甘油三酯 6.00辛基十二烷醇 6.00Cetearyl异壬酸酯 5.00乙酸生育酚酯 1.00白蜂蜡 1.20甘油(86%) 5.00Phenonip 0.50辛基甲氧基肉桂酸酯 4.00辛基三嗪酮 3.00实施例3的超细颜料 5.00水 加至100
实施例39:W/O-乳剂
%聚甘油基-2-二聚羟基硬脂酸酯(Dehymuls PGPH) 3.00油酸甘油酯(Monomuls 90-O 18) 1.00辛酸/癸酸甘油三酯 6.00辛基十二烷醇 6.00Cetearyl异壬酸酯 5.00辛基甲氧基肉桂酸酯 3.00乙酸生育酚酯 1.00白蜂蜡 1.20甘油(86%) 5.00Phenonip 0.50实施例10的超细颜料 5.00水 加至100
实施例40:O/W-乳剂
%Tego Care CG 90(Goldschmidt AG) 6.00Cetearyl醇 1.50硬脂酸甘油酯 0.50辛基癸醇 7.00辛酸/癸酸甘油三酯 5.00Cetearyl异壬酸酯 6.00辛基甲氧基肉桂酸酯 3.00去离子水 51.14丙烯酸聚合物 0.20NaOH(45%) 1.13甘油 5.00甲基对羟基苯甲酸酯 0.17丙基对羟基苯甲酸酯 0.03对苯二亚甲基(Terephthalyden)-二莰烷-磺酸 1.50实施例5的超细颜料(50%的悬浮液) 12.00实施例41:O/W-超细乳剂
%Ceteareth-12 8.0Cetearyl醇 4.0Cetearyl异壬酸酯 20.0丁基甲氧基二苯甲酰基甲烷 2.0去离子水 加至100.0丙烯酸聚合物 0.2防腐剂 视需要硫酸镁(MgSO4×7H2O) 3.0实施例9的超细颜料(50%悬浮液) 8.0
实施例42:O/W/O-乳剂
%聚甘油基-2-聚羟基硬脂酸酯 5.0矿物油 12.5硬脂酸 2.0Cetearyl异壬酸酯 12.5甲基亚苄基樟脑 2.0homosalate 2.0去离子水 加至100.0丙烯酸聚合物 0.2防腐剂 视需要NaOH 视需要实施例2的超细颜料(50%悬浮液) 8.0
实施例43:O/W-乳剂
%甘油硬脂酸酯/聚乙二醇(MG100)-硬脂酸酯 3.0十六烷醇/硬脂醇-20EO(Eumulgin B 2) 1.0十六烷醇/硬脂醇(Lanette O) 2.0辛酸/癸酸甘油三酯(Myritol 318) 4.0二辛醚(Dicaprylether) 6.0矿物油和Quartenium-18 Hectorite 3.0甘油硬脂酸酯,十六烷醇/硬脂醇、棕榈酸十六烷酯,椰油甘油酯(Cutina CBS) 2.04-甲基亚苄基樟脑 1.0辛基三嗪酮 2.0去离子水 加至100.0甘油,85% 3.0防腐剂 视需要镁铝硅酸盐(Vegum Ultra) 0.3NaOH 视需要实施例2的超细颜料(50%悬浮液) 10.0
Claims (31)
1.超细有机紫外滤除剂混合物的用途,用于保护人和动物的皮肤和头发不受紫外线辐射的有害侵蚀。
2.根据权利要求1的用途,其特征在于:所述的有机紫外滤除剂选自三嗪衍生物或苯并三唑衍生物、含乙烯基的酰胺、肉桂酸衍生物、磺化苯并咪唑、费歇尔碱衍生物、二苯基丙二酸二腈、草酰胺、樟脑衍生物、丙烯酸二苯酯、对氨基苯甲酸(PABA)和其衍生物、水杨酸酯和二苯甲酮。
式中:
R1、R2和R3彼此独立地代表氢;OH;C1-18烷氧基;-NH2;-NH-R4;-N(R4)2;-OR4,
R4代表C1-5烷基;苯基;苯氧基;苯胺基;吡咯并,其中苯基、苯氧基、苯胺基或吡咯并可是未被取代的或可被一个、两个或三个OH基团、羧基、-CO-NH2、C1-5烷基或C1-5烷氧基取代;亚甲基樟脑基团;式-(CH=CH)mC(=O)-OR4基团;式的基团或其对应的碱金属盐,铵盐,一-、二-或三-C1-4-烷基铵盐、一-、二-或三-C2-4-链烷醇铵盐、或其C1-3烷基酯;或式(1a)的基团R5代表氢;未取代的或被一个或多个OH基团取代的C1-5烷基;C1-5烷氧基;氨基;一-或二-C1-5烷基氨基;M;式 ;其中
R′,R″和R″′彼此独立地代表未取代的或被一个或多个OH基团取代的C1-14烷基;R6代表氢;M;C1-5烷基;或式
的基团;
M代表金属阳离子;
T1代表氢;或C1-8烷基;
m代表0或1
m2代表1-4;和
m3代表2-14。
式中:
R7和R8彼此独立地代表C1-18烷基;C2-18链烯基;式-CH2-CH(-OH)-CH2-O-T1的基团;或
R7和R8代表式(2a)的基团R9代表直接键;直链或支链的C1-4亚烷基或式
的基团;R10、R11和R12彼此独立地代表C1-18烷基;C1-18烷氧基或式R13代表Cl-5烷基;m1代表1-4;p1代表0-5;A1代表式(2b)的基团;或式
的基团;R1-4代表氢;C1-10烷基、
或式-CH2-CH(-OH)-CH2-O-T1基团;R15代表氢;M;C1-5烷基;或式基团;R16代表氢;或甲基;T1代表氢;或C1-8烷基;Q1代表C1-18烷基;M代表金属阳离子;
m2和m3彼此独立地代表1-4;和
n1代表1-16。
8.根据权利要求1或2的用途,其特征在于:有机紫外滤除剂选自式(24a)的三嗪衍生物
12.根据权利要求1或2的用途,其特征在于:有机紫外滤除剂选自式(28)的苯并三唑衍生物式中:T2代表C1-4烷基或苯基取代的C1-5烷基。
14.根据权利要求1或2的用途,其特征在于:有机紫外滤除剂选自式(33)的化合物
式中:
R50,R51,R52,R53,R54彼此独立地代表氢、C1-8烷基或C5-10环烷基;
R55代表氢;C1-8烷基;C5-10环烷基;羟基;C1-8烷氧基;COOR56;或CONR57R58;
R56,R57和R58彼此独立地代表氢或C1-6烷基;
X和Y彼此独立地代表氢;-CN;CO2R59;CONR59R60;或COR59;
其中基团X和Y还可以代表C1-8烷基、C5-10烷基,或具有5-6个环原子的杂芳基,此外,X和Y或R50可与基团X和Y之一一起完整地形成5-7元环,该环可含有至多3个杂原子,环原子可以被外向环双键合的氧和/或被C1-8烷基和/或被C5-10环烷基取代和/或可含有C=C-双键;
Z代表氢;铵;碱金属离子;或用于中和游离酸基团的有机含氮碱的阳离子,
R59和R60彼此独立地代表氢、C1-8烷基或C5-10环烷基;和
n和m彼此独立地代表0或1。
15.权利要求1-14任一项定义的适用于本发明的有机紫外滤除剂混合物的制备方法,其特征在于:将以超细形式存在的紫外滤除剂彼此间进行致密的混合。
16.权利要求1-14任一项定义的适用于本发明的有机紫外滤除剂混合物的制备方法,其特征在于:超细化以至少两种单一物质的混合物形式存在的有机紫外滤除剂。
17.权利要求1-14任一项定义的适用于本发明的有机紫外滤除剂混合物的制备方法,其特征在于:将至少两种单一物质一起熔融,冷却熔融体并接着将形成的复合物超细化。
18.通过一起熔融至少两种权利要求1-14任一项定义的有机紫外滤除剂获得的复合物。
19.权利要求1-14任一项所述的用途,其特征在于:另外向混合物中添加无机颜料。
20.根据权利要求19的用途,其特征在于:无机颜料选自TiO2、ZnO、氧化铁、云母和有机酸的钛盐或锌盐。
21.通过一起熔融至少两种权利要求1-14任一项定义的有机紫外滤除剂和至少一种权利要求19或20定义的无机颜料获得的复合物。
22.根据权利要求1-14任一项的用途,其特征在于:另外向混合物中添加抗氧化剂。
24.通过一起熔融至少两种权利要求1-14任一项定义的有机紫外滤除剂和至少一种权利要求22或23定义的抗氧化剂和必要时加入的一种或多种无机颜料获得的复合物。
25.根据权利要求1-14任一项的用途,其特征在于:向混合物中添加阳离子或阴离子化合物。
26.根据权利要求24的用途,其特征在于:阳离子或阴离子化合物选自樟脑苄烷铵硫酸二甲酯、脂肪胺、甜菜碱、季铵化合物、柠檬酸单甘油酯、甲基椰油基牛磺酸钠、磷脂、神经酰胺和植物甾醇。
27.通过一起熔融至少两种权利要求1-14任一项定义的有机紫外滤除剂和至少一种权利要求25和26定义的阳离子或阴离子化合物获得的复合物。
28.根据权利要求1-14任一项的用途,其特征在于:另外向混合物中添加药物或化妆品活性物质。
29.含有由至少两种权利要求1-14任一项定义的有机紫外滤除剂,必要时的一种或多种抗氧化剂和/或无机颜料和/或阳离子或阴离子化合物,以及化妆品相容性的载体或助剂构成的混合物的化妆品制剂。
30.根据权利要求29的化妆品制剂,其特征在于:还含有油溶性的未超细化的紫外滤除剂。
31.含有由至少两种权利要求1-14任一项定义的有机紫外滤除剂,必要时的一种或多种抗氧化剂和/或无机颜料和/或阳离子或阴离子化合物,以及药物相容性的载体或助剂构成的混合物的药物制剂。
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-
2000
- 2000-06-08 IL IL14677800A patent/IL146778A0/xx unknown
- 2000-06-08 ES ES00949173T patent/ES2333197T3/es not_active Expired - Lifetime
- 2000-06-08 DE DE50015768T patent/DE50015768D1/de not_active Expired - Lifetime
- 2000-06-08 BR BR0011766-8A patent/BR0011766A/pt not_active Application Discontinuation
- 2000-06-08 WO PCT/EP2000/005314 patent/WO2000078277A1/de not_active Application Discontinuation
- 2000-06-08 KR KR1020017016207A patent/KR100759240B1/ko active IP Right Grant
- 2000-06-08 US US10/018,199 patent/US6746666B1/en not_active Expired - Lifetime
- 2000-06-08 CN CNB008089337A patent/CN1221244C/zh not_active Expired - Lifetime
- 2000-06-08 JP JP2001504342A patent/JP4744754B2/ja not_active Expired - Lifetime
- 2000-06-08 AU AU62626/00A patent/AU778175B2/en not_active Expired
- 2000-06-08 MX MXPA01013101 patent/MX231178B/es active IP Right Grant
- 2000-06-08 EP EP00949173A patent/EP1187598B1/de not_active Expired - Lifetime
- 2000-06-08 AT AT00949173T patent/ATE446124T1/de not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100424081C (zh) * | 2003-03-24 | 2008-10-08 | 西巴特殊化学制品控股公司 | 均三嗪衍生物 |
CN101529245B (zh) * | 2006-10-26 | 2011-12-28 | 西巴控股有限公司 | 用于光致变色体系的光吸收层 |
Also Published As
Publication number | Publication date |
---|---|
ES2333197T3 (es) | 2010-02-18 |
AU778175B2 (en) | 2004-11-18 |
AU6262600A (en) | 2001-01-09 |
CN1221244C (zh) | 2005-10-05 |
EP1187598A1 (de) | 2002-03-20 |
KR20020013584A (ko) | 2002-02-20 |
US6746666B1 (en) | 2004-06-08 |
DE50015768D1 (de) | 2009-12-03 |
MX231178B (es) | 2005-10-10 |
IL146778A0 (en) | 2002-07-25 |
EP1187598B1 (de) | 2009-10-21 |
JP4744754B2 (ja) | 2011-08-10 |
ATE446124T1 (de) | 2009-11-15 |
JP2003502354A (ja) | 2003-01-21 |
MXPA01013101A (es) | 2002-06-04 |
BR0011766A (pt) | 2002-03-05 |
KR100759240B1 (ko) | 2007-09-18 |
WO2000078277A1 (de) | 2000-12-28 |
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