CN1267213A - 双(间苯二酚基)三嗪衍生物在化妆品中的应用 - Google Patents
双(间苯二酚基)三嗪衍生物在化妆品中的应用 Download PDFInfo
- Publication number
- CN1267213A CN1267213A CN98808291A CN98808291A CN1267213A CN 1267213 A CN1267213 A CN 1267213A CN 98808291 A CN98808291 A CN 98808291A CN 98808291 A CN98808291 A CN 98808291A CN 1267213 A CN1267213 A CN 1267213A
- Authority
- CN
- China
- Prior art keywords
- formula
- alkyl
- hydrogen
- group
- separate
- 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
- 239000002537 cosmetic Substances 0.000 title claims abstract description 20
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims description 24
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 150000003918 triazines Chemical class 0.000 claims abstract description 5
- 241001465754 Metazoa Species 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 230000000254 damaging effect Effects 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 239000002250 absorbent Substances 0.000 claims description 20
- 230000002745 absorbent Effects 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 241001597008 Nomeidae Species 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 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 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000217 alkyl group 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
- 239000012965 benzophenone Substances 0.000 claims description 3
- 150000001907 coumarones Chemical class 0.000 claims description 3
- 239000003223 protective agent Substances 0.000 claims description 3
- WMJBVALTYVXGHW-UHFFFAOYSA-N 3,3-diphenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(=CC(=O)O)C1=CC=CC=C1 WMJBVALTYVXGHW-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001565 benzotriazoles Chemical class 0.000 claims description 2
- 150000001851 cinnamic acid derivatives Chemical class 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
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 2
- 229960000655 ensulizole Drugs 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 abstract description 2
- 239000006096 absorbing agent Substances 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 230000000475 sunscreen effect Effects 0.000 abstract 1
- -1 n-pro-pyl Chemical group 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229960001679 octinoxate Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- 150000003921 pyrrolotriazines Chemical class 0.000 description 6
- 230000037072 sun protection Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229940075529 glyceryl stearate Drugs 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007764 o/w emulsion Substances 0.000 description 3
- 238000001782 photodegradation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940086555 cyclomethicone Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229940100460 peg-100 stearate Drugs 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 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 1
- KWQZLTZOLKDIAQ-UHFFFAOYSA-N (2-aminoacetyl) 2-aminobenzoate Chemical compound NCC(=O)OC(=O)C1=CC=CC=C1N KWQZLTZOLKDIAQ-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 1
- AALXZHPCKJILAZ-UHFFFAOYSA-N (4-propan-2-ylphenyl)methyl 2-hydroxybenzoate Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)C1=CC=CC=C1O AALXZHPCKJILAZ-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- QHMVQKOXILNZQR-UHFFFAOYSA-N 1-methoxyprop-1-ene Chemical compound COC=CC QHMVQKOXILNZQR-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- OIQXFRANQVWXJF-UHFFFAOYSA-N 2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)C2=CC1=CC=CC=C1 OIQXFRANQVWXJF-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- KCYXUPSQDTWHIJ-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-2-cyanoprop-2-enoic acid Chemical compound C1=CC=C2OC(C=C(C(=O)O)C#N)=CC2=C1 KCYXUPSQDTWHIJ-UHFFFAOYSA-N 0.000 description 1
- KKJKXQYVUVWWJP-JLHYYAGUSA-N 4-[(e)-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C\C1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-JLHYYAGUSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- AVPJJMJNHHDVNN-UHFFFAOYSA-N 4-hydroxy-1H-triazin-6-one Chemical compound OC1=NN=NC(=C1)O AVPJJMJNHHDVNN-UHFFFAOYSA-N 0.000 description 1
- KXKOMABBABBLKI-UHFFFAOYSA-N 5-amino-3-benzylidene-1,4,7,7-tetramethylbicyclo[2.2.1]heptan-2-one Chemical compound NC1C2(C(C(C(C1)(C2(C)C)C)=O)=CC2=CC=CC=C2)C KXKOMABBABBLKI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YXYKIXHQDOQFFJ-UHFFFAOYSA-N C(CCCCCCCCCCC)ON(C1=CC=CC=C1)OCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCC)ON(C1=CC=CC=C1)OCCCCCCCCCCCCCC YXYKIXHQDOQFFJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- XETQTCAMTVHYPO-UHFFFAOYSA-N Isocamphan von ungewisser Konfiguration Natural products C1CC2C(C)(C)C(C)C1C2 XETQTCAMTVHYPO-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- MEWQFMZMPMAMTG-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCC MEWQFMZMPMAMTG-UHFFFAOYSA-N 0.000 description 1
- PNNXBWWSFIVKQW-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCC PNNXBWWSFIVKQW-UHFFFAOYSA-N 0.000 description 1
- FVXZXFWDTIMEMA-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCCC FVXZXFWDTIMEMA-UHFFFAOYSA-N 0.000 description 1
- CIGIRZIOSVQVKQ-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCCCC CIGIRZIOSVQVKQ-UHFFFAOYSA-N 0.000 description 1
- PHCRNOUPAWMIFE-UHFFFAOYSA-N [O].O(CCCCC)CCCCCCC Chemical compound [O].O(CCCCC)CCCCCCC PHCRNOUPAWMIFE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229930006742 bornane Natural products 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940025250 camphora Drugs 0.000 description 1
- 239000010238 camphora Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 229940082484 carbomer-934 Drugs 0.000 description 1
- 229940073669 ceteareth 20 Drugs 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SOROIESOUPGGFO-UHFFFAOYSA-N diazolidinylurea Chemical compound OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O SOROIESOUPGGFO-UHFFFAOYSA-N 0.000 description 1
- 229960001083 diazolidinylurea Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229960004697 enzacamene Drugs 0.000 description 1
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 1
- 229940068171 ethyl hexyl salicylate Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000003760 hair shine Effects 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
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 229960000201 isosorbide dinitrate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([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
- 239000000463 material Substances 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002958 pentadecyl 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])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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000036561 sun exposure Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
本发明给出用于保护人和动物的皮肤和毛发避免UV照射的损伤作用的式(1)的双(间苯二酚基)三嗪的用途,在式(1)中R1和R2相互独立为氢、C1-C18烷基、C2-C18链烯基、式-CH2-CH(-OH)-CH2-O-T1的基团、式(1a)的基团或式(1b)的基团;R3和R4相互独立为氢或C1-C5烷基;R5为羟基、未取代的由一个或几个OH基团取代的或C1-C5烷氧基、氨基、一-或二-C1-C5烷基氨基、M、式(1c)、(1d)、(1e)、(1f)、(1g)或(1h)的基团;R6为键、直链或支链C1-C4亚烷基或式(a)或(b)的基团;R7、R8和R9相互独立为C1-C18烷基、C1-C18烷氧基或式(1i)的基团;R10、R11和R12相互独立为C1-C14烷基,所述烷基为未取代的或由一个或几个OH基团取代;R13为氢、M、C1-C5烷基或式(c)的基团;R14为C1-C5烷基;M为金属阳离子;T1为氢或C1-C8烷基;m1为1—3;m2为2—14;及p1为0或1—5的数。根据本发明所用的化合物为非常有效的UVA吸收剂,部分为UVB范围的吸收剂,并特别适合在化妆品组合物、药用组合物和兽用组合物中用作防晒剂。
Description
本发明涉及用于保护人和动物的皮肤和毛发避免UV照射的损伤作用的选择的双(间苯二酚基)三嗪衍生物的用途,并涉及含有这些双(间苯二酚基)三嗪衍生物的化妆品制剂。
根据本发明所用的双(间苯二酚基)三嗪符合下式其中R1和R2相互独立为氢、支链C5-C18烷基、C2-C18链烯基、式-CH2-CH(-OH)-CH2-O-T1、式(1a)的基团或式(1b)的基团
R3和R4相互独立为氢或C1-C5烷基;R5为羟基、未取代的或由一个或几个OH基团取代的C1-C5烷氧基、氨基、一-或二-C1-C5烷基氨基、M、式(1c)的基团 R6为键、直链或支链C1-C4亚烷基或下式的基团或
R7、R8和R9相互独立为C1-C18烷基、C1-C18烷氧基或式(1i)的基团R10、R11和R12相互独立为C1-C14烷基,所述烷基为未取代的或由一个或几个OH基团取代;R13为氢、M、C1-C5烷基或式
的基团;R14为C1-C5烷基;M为金属阳离子;T1为氢或C1-C8烷基;m1为1-3;m2为2-14;及p1为0或1-5的数。
C1-C5烷基、C1-C8烷基和C1-C18烷基为直链或支链烷基,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、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-C5烷氧基和C1-C18烷氧基为直链或支链烷氧基,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、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-C18链烯基为,例如,烯丙基、甲代烯丙基、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-十二-2-烯基、异-十二烯基、正-十二-2-烯基或正十八-4-烯基。
一-或二-C1-C5烷基氨基的实例为甲基氨基、乙基氨基、丙基氨基、正丁基氨基、仲丁基氨基、叔丁基氨基、戊基氨基、二甲基氨基、二乙基氨基、二丙基氨基、二丁基氨基或甲基乙基氨基。
金属阳离子的实例为锂、钾、钠、钙、镁、铜或锌离子。
根据本发明,优选使用下式的双(间苯二酚基)化合物其中R15和R16相互独立为支链C5-C18烷基或式-CH2-CH(-OH)-CH2-O-T1;R17和R18相互独立为氢或C1-C5烷基;及T1为氢或C1-C5烷基。
特别重要的化合物为式(2)的那些化合物,其中R15和R16相互独立为支链C5-C18烷基或式-CH2-CH(-OH)-CH2-O-T1;R17和R18为氢;及T1为氢或C1-C5烷基;尤其是这样的式(2)化合物,其中R15和R16相互独立为支链C5-C18烷基;及R17和R18为氢。
特别优选式(2)的那些三嗪化合物,其中R15和R16有相同的意义。
被提及的式(1)化合物的实例为:2-(4’-甲基苯基)-4,6-双(2’-羟基-4’-正-辛氧基苯基)-1,3,5-三嗪;2-(2’,4’-二甲基苯基)-4,6-双(2’-羟基-4’-正-辛氧基苯基)-1,3,5-三嗪;2-苯基-4,6-双(2’-羟基-4’-正-辛氧基苯基)-1,3,5-三嗪;2-苯基-4,6-双(2’-羟基-4’-正-辛氧基苯基)-1,3,5-三嗪;2-苯基-4-{[4-(3-(2-丙氧基)-2-羟丙氧基)-2-羟基]苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2-(4’-甲基苯基)-4,6-双{[4-(2-乙基己氧基)-2-羟基]苯基}-1,3,5-三嗪;2-(2’,4’-二甲基苯基)-4,6-双{[4-(2-乙基己氧基)-2-羟基]苯基}-1,3,5-三嗪;2-苯基-4,6-双{[4-(2-乙基己氧基)-2-羟基]苯基}-1,3,5-三嗪;2-苯基-4,6-双{[4-(三(三甲基硅氧基甲硅烷基丙氧基)-2-羟基]苯基}-1,3,5-三嗪;2-苯基-4,6-双{[4-(2”甲基丙烯基氧基)-2-羟基]苯基}-1,3,5-三嗪;2-苯基-4,6-双{[4-(3-(2-丙氧基)-2-羟基丙氧基)-2-羟基]苯基}-1,3,5-三嗪;或2-苯基-4,6-双{[4-(2-乙基己氧基)-2-羟基]苯基}-1,3,5-三嗪。三嗪衍生物的其它实例列于表1:
根据本发明可以使用的双(间苯二酚基)三嗪可以以不同的方法制备,例如,采用芳族腈化合物作为原料化合物来制备。下式的二氯代三嗪化合物可以通过例如,使苄腈与双氰胺反应得到二氨基-三嗪化合物,接着将后者皂化为二羟基三嗪(互变异构体=-二酮),然后用亚硫酰氯将其转化为式(1k)的二氯代三嗪化合物来制备。然后,在Lewis酸(优选氯化铝)存在下,通过公知的间苯二酚的Friedel-Crafts酰化作用引入两个间苯二酚基团。在第三步,根据式(1)化合物中R1和R2的意义,通过烷基化或酸-催化的缩水甘油醚的加成反应,使在对位的游离羟基醚化。
根据本发明可以使用的三嗪衍生物的其它制备方法在EP-A-0775698中有描述。
根据本发明可以使用的式(1)的双(间苯二酚基)三嗪化合物特别适合用作UV滤光剂(filter),即防止对紫外线敏感的有机物质,特别是人和动物的皮肤和毛发免遭UV照射的有害作用。特别是这些化合物为非常有效的UVA吸收剂,部分为UVB范围的吸收剂并且可以以低成本进行生产。因此,这些化合物适合在化妆品组合物、药用组合物和兽用组合物中用作光的稳定剂。它们可以以溶解的及微粉化状态使用。
因此,本发明也涉及化妆品制剂,该制剂包含至少一种式(1)化合物以及化妆品学上相容的载体或辅助剂。
对于化妆品方面的用途,本发明的光稳定剂通常具有的平均粒度为0.02-2、优选0.05-1.5、最优选0.1-1.0m。根据本发明所用的可溶性UV吸收剂可以通过常用的方法,例如,采用喷射磨、球磨、震动磨或锤磨机进行研磨至所需的粒度。研磨优选在基于所述UV吸收剂的0.1-30%(重量)、优选0.5-15%(重量)的研磨助剂的存在下进行,所述研磨助剂,例如有烷基化的乙烯基吡咯烷酮聚合物、乙烯基吡咯烷酮-乙烯基乙酸酯共聚物、酰基谷氨酸酯或(优选)磷脂。
除了本发明的UV吸收剂外,所述化妆品制剂还可含有一种或一种以上的其它UV保护剂,例如,来自对-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、二苯基丙烯酯衍生物、苯并呋喃衍生物的有机UV吸收剂、含有一种或一种以上有机硅基的聚合的UV吸收剂、肉桂酸衍生物、樟脑衍生物、三苯胺基-s-三嗪衍生物、苯基苯并咪唑磺酸及其盐、邻氨基苯甲酸酯、苯并三唑衍生物和/或选自氧化铝-或二氧化硅-包被的二氧化钛、氧化锌或云母的无机微色素。
对-氨基苯甲酸衍生的化合物实例包括:
其中m、n和x具有相同的意义且每个最多为25;
下式的辛基二甲基PABA或下式的甘氨酰氨基苯甲酸酯
水杨酸衍生物化合物的实例:
下式的水杨酸高酯
式(9)的三乙醇氨基水杨酸酯
戊基-p-
式(10)的氨基苯甲酸二甲酯
二苯甲酮衍生物化合物的实例: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:丁基甲氧基二苯甲酰基甲烷[1-(4-叔丁基)-3-(4-甲氧基苯基)丙烷-1,3-二酮]。
二苯基丙烯酸酯衍生物化合物的实例: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etocrylene(乙基-2-氰基-3,3’-二苯基丙烯酸酯)。
肉桂酸酯化合物的实例:辛基甲氧基肉桂酸酯(4-甲氧基肉桂酸-2-乙基己基)、二乙醇氨基甲氧基肉桂酸酯(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)、2,5-二异丙基甲基肉桂酸酯或肉桂酸氨基衍生物。
樟脑衍生物化合物的实例:4-甲基-亚苄基樟脑[3-(4’-甲基)亚苄基莰-2-酮(benzylidenebornan-2-one)]、3-亚苄基-樟脑(3-亚苄基莰-2-酮)、聚丙烯酰氨基甲基亚苄基樟脑{N-[2(和4)-2-氧基亚莰烷-3-基甲基)苄基]丙烯酰胺聚合物}、trimonium亚苄基樟脑硫酸酯-[3-(4’-三甲基铵)亚苄基莰-2-酮甲基硫酸酯]、对苯二甲亚基(terephthalydene)二樟脑磺酸{3,3’-(1,4-亚苯基二次甲基)-双(7,7-二甲基)-2-氧代双环-[2.2.1]庚烷-1-甲磺酸}或其盐,或亚苄基樟脑磺酸[3-(4’-硫代)亚苄基莰-2-酮]或其盐。
三苯胺基-s-三嗪衍生物化合物的实例:辛基三嗪-[2,4,6-三苯胺基-(对-羰基-2’-乙基-1’-氧基)-1,3,5-三嗪],并且US-A-5332568、US-A-5252323、WO 93/17002、WO 97/03642和EP-A-0517104也描述了三苯胺基-s-三嗪衍生物。
苯并三唑化合物的实例2-(2-羟基-5-甲基苯基)苯并三唑。
新的化妆品制剂包含基于该制剂总重量的0.1-15%(重量)、优选0.5-10%(重量)的UV吸收剂或UV吸收剂的混合物以及化妆品学上相容的辅助剂。
所述化妆品制剂可以通过采用常用的方法将UV吸收剂与辅助剂物理混合来制备,例如将各单独的成分在一起搅拌。
新的化妆品制剂可以配制为油包水或水包油型乳剂,为醇包油洗剂、为离子或非离子两亲脂的多泡分散液、为凝胶、固体贴剂或气溶胶制剂。
当为油包水或水包油乳剂时,优选化妆品学上相容的辅助剂含有5-50%的油相、5-20%的乳化剂和30-90%的水。所述油相可以含有适合化妆品制剂的任何油,例如,一种或一种以上烃油、蜡、天然油、硅油、脂肪酸酯或脂肪醇。优选的一元-或多元醇为乙醇、异丙醇、丙二醇、己二醇、甘油和山梨醇。
对于本发明的化妆品制剂,有可能使用任何常规的乳化剂,例如一种或一种以上的天然衍生物的乙氧基化酯,例如氢化蓖麻油的聚乙氧基酯;或硅油乳化剂,例如硅氧烷多元醇;任选乙氧基化的脂肪酸皂;乙氧基化的脂肪醇;任选乙氧基化的脱水山梨醇酯;乙氧基化的脂肪酸或乙氧基化的甘油酯。
所述化妆品制剂还可含有其它成分,例如,润肤剂、乳剂稳定剂、皮肤湿润剂、晒黑促进剂、增稠剂如黄原胶、水分保持剂如甘油、防腐剂、香料和着色剂。
这种新的化妆品制剂的特点是其卓越的保护人的皮肤免遭日光有害作用的性能。
在下列实施例中,百分率以重量计。给出的双(间苯二酚基)三嗪化合物的量指纯品物质。
实施例:
用于化妆品避光的实施例
根据Deffey和Robson(J.Soc.Chem.40.127-133(1989))的方法,采用SPF分析仪(Optometrix,SPF290)测定光稳定剂。
为了测定光稳定性,将过滤物质溶于乙醇中(c=1·10-5-5·10-5M),并在搅拌下、在石英透明小容器中用金属卤化物灯(Macam)(IUVB=0.4-8.0mW/cm2)照射。为了转变为太阳光谱(CIE D65-norm昼光,标准化为IUVB=0.127mW/cm2),对波长拆分灯(wave-length-resolvedlamp)强度产生和在290-400nm范围的各UV吸收剂对应吸收值的积分进行计算,然后除以D65光强度产生和在290-400nm范围各UV吸收剂的对应吸收值的积分。将该因子乘以金属卤化物灯照射下降解的半衰期,得到日光照射下的对应的半衰期。通过在最大吸收值波长消光的UV-分光镜测定和随后的指数拟合确定在灯照射下光致降解的半衰期。因而,采用所述方法可得到在D65光照下光致降解的半衰期。实施例1:具有式(101)化合物的o/w乳剂λmax:356nm(乙醇)εmax:41400M-1cm-1(A):式(101)的三嗪UV吸收剂 4g芝麻油 10g甘油硬脂酸酯 4g硬脂酸 1g十六醇 0.5g聚山梨酸酯20 0.2g(B):丙二醇 4g对羟基苯甲酸丙酯 0.05g对羟基苯甲酸甲酯 0.15g三乙醇胺 0.1gCarbomer 934 0.1g水 加至100ml
乳剂的制备
相(A):
先将UV吸收剂溶于芝麻油中,然后加入(A)的其它成分并在一起混合。
相(B):
将对羟基苯甲酸丙酯和对羟基苯甲酸甲酯溶于丙二醇中。然后加入60ml水,将该混合物加热至70℃并于其中使Carbomer 934乳化。
乳剂:
用高机械能输入将(A)缓慢加入到B中。加水将该体积调节至100ml。
获得的防晒因子和光稳定性列于表1中。
表1: | 浓度 | 防晒因子*) | 光稳定性**)[h] |
式(101)化合物 | 4% | 7.1 | 6000 |
*)依据Difiey和Robson
**)D65光照下乙醇溶液中光致降解的半衰期
通过UV吸收剂浓度可改变防晒因子。
该结果证实所述活性物质有高的光稳定性,并且即使在低浓度下也可获得良好的防晒因子。
对UVA特征的其它物理测定:
表2:对UVA特征的其它物理测定:
式(101)化合物4%乳剂 | |
T(360)1 | 0.6% |
UVA/UVB比2 | 0.79 |
λcrit[nm]3 | 373 |
表2:含有新的油可溶性的滤光剂(101)和甲氧基肉桂酸辛酯
的防晒乳剂
相 | 组分 | %b.w. |
(A) | 去离子水 | 54.90 |
黄原胶,2%溶液 | 15.00 | |
丙二醇 | 1.50 | |
EDTA四钠 | 0.10 | |
(B) | 十四酸异丙酯 | 10.00 |
具有式(101)的三嗪UV-吸收剂 | 3.00 | |
(C) | 甲氧基肉桂酸辛酯 | 7.50 |
甘油硬脂酸酯(和)PEG-100硬脂酸酯 | 3.00 | |
环甲基硅酮 | 1.00 | |
Cetearyl醇(和)ceteareth-20(Amerchol) | 3.00 | |
(D) | 丙二醇(和)对羟基苯甲酸甲酯(和)对羟基苯甲酸丙酯(和)重氮烷基脲(diazolidinyl urea)(ISP) | 1.00 |
1于360nm处发射
2对290-320与320-400nm波长范围吸收曲线标准化面积之比
3当从290nm处开始积分并将290-400nm之间的面积定义为100%时,在吸收曲线下面积达到90%时的波长。
方法:依次将(A)的各成分混合并加热至75℃。混合(B)的成分,加热至75℃并搅拌至滤光剂溶解。然后将(C)加入B中并混合20分钟(=混合物(BC))。然后将(D)加入(BC)(=混合物(BCD))中。搅拌下将(A)加入(BCD)中并冷却至室温。
产生的SPF(防晒因子):16(根据实施例1的方法)
实施例3:含有新的式(102)的水可溶性滤光剂和甲氧基肉桂酸辛酯的防晒制剂Imax=352nm(乙醇)emax=39800M-1cm-1
相 | 组分 | %b.w. |
(A) | 具有式(102)的三嗪UV-吸收剂 | 4.00 |
Carbomer | 0.30 | |
(B) | 去离子水 | 57.93 |
(C) | 丙二醇 | 5.00 |
对羟基苯甲酸甲酯 | 0.20 | |
对羟基苯甲酸丙酯 | 0.10 | |
三乙醇胺 | 0.45 | |
EDTA四钠 | 0.02 | |
(D) | 甲氧基肉桂酸辛酯 | 5.00 |
甘油硬脂酸酯(和)PEG-100硬脂酸酯 | 1.00 | |
环甲基硅酮 | 5.00 | |
甘油硬脂酸酯 | 4.00 | |
硬脂酸 | 2.50 | |
异硬脂酸异硬脂酯 | 10.00 | |
氢化蓖麻油 | 2.00 | |
苯甲酸C12-15烷基酯 | 2.50 |
方法:将(A)悬浮于(B)中,当均匀时,依次加入(C)的组分(=混合物(ABC))。加热至85℃,在另外的容器中混合组分(D)并在混合下加热至85℃。当(ABC)和(D)都为85℃并均匀时,在剧烈搅拌下,将(D)缓慢加入ABC中。在最后加入D后15分钟,开始冷却处理并冷却至室温。
产生的SPF(防晒因子):12(根据实施例1的方法)
Claims (9)
1.下式的UV吸收剂在保护人和动物的皮肤和毛发避免UV照射的损伤作用中的用途其中R1和R2相互独立为氢、支链C5-C18烷基、C2-C18链烯基、式-CH2-CH(-OH)-CH2-O-T1、式(1a)的基团或式(1b)的基团
R3和R4相互独立为氢或C1-C5烷基;R5为羟基、未取代的或由一个或几个OH基团取代的C1-C5烷氧基、氨基、一-或二-C1-C5烷基氨基、M、式(1c)的基团 R6为链、直链或支链C1-C4亚烷基或下式的基团或
R7、R8和R9相互独立为C1-C18烷基、C1-C18烷氧基或式(1i)的基团R10、R11和R12相互独立为C1-C14烷基,所述烷基为未取代的或由一个或几个OH基团取代’R13为氢、M、C1-C5烷基或式
的基团;R14为C1-C5烷基;M为金属阳离子;T1为氢或C1-C8烷基;m1为1-3;m2为2-14;及p1为0或1-5的数。
3.权利要求2的用途,其中,在式(2)中,R15和R16相互独立为C1-C18烷基或式-CH2-CH(-OH)-CH2-O-T1;R17和R18为氢;及T1为氢或C1-C5烷基。
4.权利要求3的用途,其中,在式(2)中,R15和R16相互独立为支链C5-C18烷基;及R17和R18为氢。
5.权利要求2-4中任一项的用途,其中式(2)中的R15和R16有相同的意义。
7.化妆品制剂,它包括根据权利要求1的式(1)的UV吸收剂和化妆品学上相容的载体或辅助剂。
8.权利要求7的制剂,它包括其它的UV保护剂。
9.权利要求7或权利要求8的制剂,其中所述其它的UV保护剂为得自对-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、二苯基丙烯酸酯衍生物、苯并呋喃衍生物的有机UV吸收剂、含有一种或一种以上有机硅基的聚合的UV吸收剂、肉桂酸衍生物、樟脑衍生物、三苯胺基-s-三嗪衍生物、苯基苯并咪唑磺酸及其盐、邻氨基苯甲酸酯、苯并三唑衍生物和/或选自氧化铝-或二氧化硅-包被的二氧化钛、氧化锌或云母的无机微色素。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97810585.6 | 1997-08-20 | ||
EP97810585 | 1997-08-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1267213A true CN1267213A (zh) | 2000-09-20 |
CN1170522C CN1170522C (zh) | 2004-10-13 |
Family
ID=8230350
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB988082918A Expired - Fee Related CN1170522C (zh) | 1997-08-20 | 1998-08-08 | 双(间苯二酚基)三嗪衍生物在化妆品中的应用 |
Country Status (15)
Country | Link |
---|---|
US (1) | US6221342B1 (zh) |
EP (1) | EP1005325B1 (zh) |
JP (1) | JP3964133B2 (zh) |
KR (1) | KR100548980B1 (zh) |
CN (1) | CN1170522C (zh) |
AU (1) | AU747205B2 (zh) |
BR (1) | BR9811958B1 (zh) |
DE (1) | DE69827393T2 (zh) |
ES (1) | ES2232009T3 (zh) |
IL (1) | IL134244A0 (zh) |
MX (1) | MX224819B (zh) |
NZ (1) | NZ502708A (zh) |
PL (1) | PL338738A1 (zh) |
RU (1) | RU2223089C2 (zh) |
WO (1) | WO1999008653A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102010520A (zh) * | 2010-11-10 | 2011-04-13 | 大连化工研究设计院 | 含受阻胺基团的三嗪类光稳定剂 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100494448B1 (ko) * | 1996-06-04 | 2005-12-02 | 화브리까 에스파놀라 데 프로둑또스 뀌미꼬스 이 화르마세우띠꼬스 쏘시에떼 아노님 | 항히스타민활성을가지는신규한벤조이미다졸유도체 |
DE19817292A1 (de) * | 1998-04-18 | 1999-10-21 | Beiersdorf Ag | Stabile kosmetische oder dermatologische Zubereitungen in Form von W/O-Emulsionen enthaltend unsymmetrisch substituierte Triazinderivate |
FR2789579B1 (fr) | 1999-02-12 | 2002-02-01 | Oreal | Compositions cosmetiques pour la photoprotection de la peau et/ou des cheveux contenant un derive de benzotriazole et une bis-resorcinyl triazine |
FR2789580A1 (fr) * | 1999-02-12 | 2000-08-18 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
FR2789583B1 (fr) * | 1999-02-12 | 2002-02-01 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
DE19910477A1 (de) * | 1999-03-10 | 2000-09-14 | Beiersdorf Ag | Verwendung von Octocrylen zur Solubilisierung von 2,4-Bis-{[4-(2-Ethyl-hexyloxy-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazin in kosmetischen oder dermatologischen Lichtschutzmitteln |
AU774383B2 (en) | 1999-07-12 | 2004-06-24 | Ciba Specialty Chemicals Holding Inc. | Use of mixtures of micropigments for preventing tanning and for lightening skin and hair |
ATE318260T1 (de) * | 1999-12-23 | 2006-03-15 | Ciba Sc Holding Ag | Stabilisatormischung |
JP3950046B2 (ja) * | 2000-09-21 | 2007-07-25 | ファイザー・プロダクツ・インク | レゾルシノール誘導体 |
DE10130963A1 (de) * | 2001-06-27 | 2003-01-16 | Beiersdorf Ag | Verwendung von Bis-Resorcinyltriazinderivaten zur Verbesserung der Wirksamkeit von lipophilen Wirkstoffen in kosmetischen oder dermatologischen Zubereitungen |
US7534421B2 (en) | 2003-03-03 | 2009-05-19 | L'oreal | s-Triazine compounds bearing at least one para-aminobenzalmalonic salt substituent and photoprotective cosmetic compositions comprised thereof |
US20050012594A1 (en) * | 2003-07-17 | 2005-01-20 | Youngtack Shim | Key assemblies and methods |
US8691002B2 (en) | 2009-01-19 | 2014-04-08 | Basf Se | Organic black pigments and their preparation |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL299880A (zh) | 1962-10-30 | |||
CH480090A (de) * | 1962-10-30 | 1969-10-31 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Ultraviolettschutzmittel ausserhalb der Textilindustrie |
CH469053A (de) | 1963-07-26 | 1969-02-28 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Schutzmittel gegen Ultraviolettstrahlung für nichttextile organische Materialien |
GB9403451D0 (en) | 1994-02-23 | 1994-04-13 | Ciba Geigy Ag | Sunscreen compositions |
DE19543730A1 (de) | 1995-11-23 | 1997-05-28 | Ciba Geigy Ag | Bis-Resorcinyl-Triazine |
EP0878469B1 (de) * | 1997-05-16 | 2004-10-27 | Ciba SC Holding AG | Resorcinyl-Triazine |
-
1998
- 1998-08-08 CN CNB988082918A patent/CN1170522C/zh not_active Expired - Fee Related
- 1998-08-08 MX MXPA/A/2000/001709 patent/MX224819B/es active IP Right Grant
- 1998-08-08 IL IL13424498A patent/IL134244A0/xx unknown
- 1998-08-08 US US09/485,948 patent/US6221342B1/en not_active Expired - Fee Related
- 1998-08-08 NZ NZ502708A patent/NZ502708A/xx unknown
- 1998-08-08 ES ES98940270T patent/ES2232009T3/es not_active Expired - Lifetime
- 1998-08-08 RU RU2000104001/15A patent/RU2223089C2/ru not_active IP Right Cessation
- 1998-08-08 WO PCT/EP1998/005042 patent/WO1999008653A1/en active IP Right Grant
- 1998-08-08 EP EP98940270A patent/EP1005325B1/en not_active Expired - Lifetime
- 1998-08-08 JP JP2000509394A patent/JP3964133B2/ja not_active Expired - Fee Related
- 1998-08-08 PL PL98338738A patent/PL338738A1/xx unknown
- 1998-08-08 BR BRPI9811958-3A patent/BR9811958B1/pt not_active IP Right Cessation
- 1998-08-08 DE DE69827393T patent/DE69827393T2/de not_active Expired - Lifetime
- 1998-08-08 AU AU88644/98A patent/AU747205B2/en not_active Ceased
- 1998-08-08 KR KR1020007001667A patent/KR100548980B1/ko not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102010520A (zh) * | 2010-11-10 | 2011-04-13 | 大连化工研究设计院 | 含受阻胺基团的三嗪类光稳定剂 |
Also Published As
Publication number | Publication date |
---|---|
IL134244A0 (en) | 2001-04-30 |
CN1170522C (zh) | 2004-10-13 |
MX224819B (es) | 2004-12-23 |
NZ502708A (en) | 2002-12-20 |
US6221342B1 (en) | 2001-04-24 |
EP1005325B1 (en) | 2004-11-03 |
ES2232009T3 (es) | 2005-05-16 |
RU2223089C2 (ru) | 2004-02-10 |
DE69827393T2 (de) | 2005-11-10 |
JP3964133B2 (ja) | 2007-08-22 |
JP2001515025A (ja) | 2001-09-18 |
AU8864498A (en) | 1999-03-08 |
DE69827393D1 (de) | 2004-12-09 |
PL338738A1 (en) | 2000-11-20 |
KR20010023050A (ko) | 2001-03-26 |
BR9811958B1 (pt) | 2010-08-24 |
KR100548980B1 (ko) | 2006-02-03 |
AU747205B2 (en) | 2002-05-09 |
BR9811958A (pt) | 2000-08-15 |
WO1999008653A1 (en) | 1999-02-25 |
EP1005325A1 (en) | 2000-06-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1267213A (zh) | 双(间苯二酚基)三嗪衍生物在化妆品中的应用 | |
CN1117737C (zh) | 对称三嗪衍生物 | |
JP3040339B2 (ja) | ジベンゾイルメタンから誘導されたサンスクリーン剤の光安定化方法、これによって得られた光安定性化粧品サンスクリーン組成物、およびその使用 | |
JP7389536B2 (ja) | 微粒子有機uv吸収剤組成物 | |
KR101269995B1 (ko) | 광안정성 화장품 또는 피부학적 조성물 | |
ES2284634T3 (es) | Fotoestabilizacion de derivados de dibenzoilmetano. | |
EP0843996B1 (en) | Sun protecting cosmetic compositions comprising derivatives of dibenzoylmethane and of benzophenone | |
KR20100096212A (ko) | 미세화된 유기 uv 흡수제에 대한 분쇄 조제 | |
JP2016188213A (ja) | ナノスケール紫外線吸収剤の製造 | |
CN102448429B (zh) | 亚苄基丙二酸酯 | |
JP4750447B2 (ja) | シリコンクラスター又はゲルマニウムクラスターを含む紫外線吸収剤及び発光剤並びにそのクラスターを用いた皮膚外用剤 | |
KR102526363B1 (ko) | 화장료 썬스크린 조성물 | |
JPH11292748A (ja) | ジベンゾイルメタン、ベンゾフェノン及びトリアジンの各誘導体を含む日焼け防止化粧品組成物 | |
CN101686921B (zh) | 透射染料的晶型 | |
CN1208342A (zh) | 稳定的防晒组合物 | |
JP2007099699A (ja) | 日焼け止め化粧料 | |
CA2292132C (en) | Benzylidene-.gamma.-butyrolactones, process for their preparation and their use as uv absorber | |
ES2291155T3 (es) | Preparaciones cosmeticas o dermatologicas para proteccion de luz, con contenido en nitruro boro y 2-ciano-3,3-difenilacrilato de etilhexilo, asi como empleo nitruro boro para potenciar factor proteccion luz y/o rendimiento proteccion uv del agente cosm. o derm. proteccion de luz. | |
ES2202513T3 (es) | Uso de uno o varios monoesteres y diesteres formados por acidos alcanocarboxilicos ramificados y diglicerina o triglicerina como disolvente de derivados de triazina en formulaciones fotoprotectoras de tipo cosmetico y dermatologico. | |
CN1321145A (zh) | 用作遮光剂的由樟脑或乙内酰脲衍生物取代的二苯基化合物 | |
ES2706373T3 (es) | Preparación cosmética con sustancia de filtro UV-A y cetearilsulfato de sodio | |
CA2231083A1 (en) | Sun protecting cosmetic compositions comprising derivatives of dibenzoylmethane, of diphenylcyanoacrylic acid and of triazine | |
ES2621158T3 (es) | Preparación fotoprotectora en forma de una emulsión O/W con un factor de fotoprotección mayor o igual a 50 | |
ES2212848T3 (es) | Formulaciones cosmeticas y dermatologicas fotoprotectoras con un contenido en derivados de triazina y uno o varios esteres de acidos carboxilicos de cadena ramificada y alcoholes de cadena ramificada. | |
US6770269B1 (en) | Cosmetic and dermatological light-protective formulations containing triazine derivatives and one or several esters of unbranched-chain carboxylic acids and branched-chain alcohols |
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 | ||
C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20041013 Termination date: 20100808 |