AU757142B2 - Diresorcinyl-alkoxy- and -aryloxy-S-triazines - Google Patents
Diresorcinyl-alkoxy- and -aryloxy-S-triazines Download PDFInfo
- Publication number
- AU757142B2 AU757142B2 AU23653/99A AU2365399A AU757142B2 AU 757142 B2 AU757142 B2 AU 757142B2 AU 23653/99 A AU23653/99 A AU 23653/99A AU 2365399 A AU2365399 A AU 2365399A AU 757142 B2 AU757142 B2 AU 757142B2
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- Australia
- Prior art keywords
- formula
- compound
- alkyl
- compound according
- radical
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 238000002360 preparation method Methods 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 150000003918 triazines Chemical class 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 51
- -1 2-decylhexadecyl radical Chemical class 0.000 claims description 44
- 239000002537 cosmetic Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000003381 stabilizer Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 230000009931 harmful effect Effects 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract 4
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- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 abstract 1
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- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 16
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 239000006096 absorbing agent Substances 0.000 description 13
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- 239000002904 solvent Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
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- 230000000475 sunscreen effect Effects 0.000 description 6
- 239000000516 sunscreening agent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
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- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 5
- 238000001256 steam distillation Methods 0.000 description 5
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- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical group CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 239000004359 castor oil Substances 0.000 description 2
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- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 2
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- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
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- 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
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- OIQXFRANQVWXJF-ACCUITESSA-N (2e)-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-ACCUITESSA-N 0.000 description 1
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
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- 229910015900 BF3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 150000003904 phospholipids Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 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
- LOIYMIARKYCTBW-UHFFFAOYSA-N urocanic acid Chemical compound OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
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- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810314 | 1998-04-09 | ||
| EP98810314 | 1998-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2365399A AU2365399A (en) | 1999-10-21 |
| AU757142B2 true AU757142B2 (en) | 2003-02-06 |
Family
ID=8236034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU23653/99A Ceased AU757142B2 (en) | 1998-04-09 | 1999-04-08 | Diresorcinyl-alkoxy- and -aryloxy-S-triazines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6111103A (enExample) |
| EP (1) | EP0949251B1 (enExample) |
| JP (1) | JP2000063366A (enExample) |
| KR (1) | KR100589869B1 (enExample) |
| CN (1) | CN1168722C (enExample) |
| AT (1) | ATE427304T1 (enExample) |
| AU (1) | AU757142B2 (enExample) |
| BR (1) | BR9901088A (enExample) |
| DE (1) | DE59914993D1 (enExample) |
| IL (1) | IL129349A0 (enExample) |
| NZ (1) | NZ334934A (enExample) |
| SG (1) | SG75939A1 (enExample) |
| ZA (1) | ZA992565B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000026435A (ja) | 1998-05-07 | 2000-01-25 | Ciba Specialty Chem Holding Inc | トリスレゾリシニルトリアジン |
| DE19846771A1 (de) * | 1998-10-10 | 2000-04-13 | Beiersdorf Ag | Verwendung von Triglyceridwachsen zur Verstärkung des Lichtschutzfaktors und/oder der UV-A-Schutzleistung kosmetischer oder dermatologischer Lichtschutzmittel |
| FR2799965B1 (fr) * | 1999-10-22 | 2002-10-31 | Oreal | Emulsions sans emulsionnant contenant au moins un filtre uv organique insoluble |
| WO2002060882A2 (en) * | 2001-01-31 | 2002-08-08 | Roche Vitamins Ag | Process for the preparation of 2-(disubstituted-amino)-4,6-diaryl triazines |
| 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 |
| EP1342745A1 (de) * | 2002-03-05 | 2003-09-10 | Lofo High Tech Film GmbH | Verfahren zur Herstellung von Polyolefinfolien |
| AU2004206724B2 (en) * | 2003-01-20 | 2010-06-24 | Basf Se | Triazine derivatives as UV absorbers |
| CN101636455B (zh) | 2007-03-15 | 2013-11-27 | 巴斯夫欧洲公司 | 基于间苯二酚基三嗪衍生物的热敏涂料组合物 |
| FR2917609B1 (fr) * | 2007-06-22 | 2012-11-16 | Oreal | Composition de maquillage comprenant un compose hydroxyle. |
| CN101784620B (zh) | 2007-08-22 | 2013-05-29 | 巴斯夫欧洲公司 | 激光敏感涂料组合物 |
| US8900414B2 (en) | 2007-11-07 | 2014-12-02 | Datalase, Ltd. | Fiber products |
| EP2349734B1 (en) | 2008-10-27 | 2018-03-28 | DataLase Ltd | Aqueous laser-sensitive composition for marking substrates |
| EP2210887A1 (en) * | 2009-01-14 | 2010-07-28 | Isdin, S.A. | Bis resorcinyl triazine derivatives as protecting agents against UV radiation |
| CN102292397B (zh) | 2009-01-19 | 2014-12-10 | 巴斯夫欧洲公司 | 有机黑色颜料及其制备 |
| CN107635977B (zh) * | 2015-05-18 | 2020-10-20 | 帝斯曼知识产权资产管理有限公司 | 用于制备三嗪的方法 |
| JP6837147B2 (ja) * | 2018-03-30 | 2021-03-03 | 株式会社Adeka | 粒状紫外線吸収剤および樹脂組成物 |
| US12289992B2 (en) | 2018-10-05 | 2025-04-29 | Samsung Display Co., Ltd. | Display apparatus and light absorber included in display apparatus |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364749A (en) * | 1991-06-03 | 1994-11-15 | Ciba-Geigy Corporation | Photographic material containing UV absorber |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE558354A (enExample) * | 1956-06-15 | |||
| NL6400510A (enExample) * | 1964-01-23 | 1965-07-26 | ||
| CH473818A (de) * | 1964-03-18 | 1969-06-15 | Ciba Geigy | Verfahren zur Herstellung von neuen Hydroxyphenyl-1,3,5-triazinen und deren Verwendung |
| US3542752A (en) * | 1966-02-07 | 1970-11-24 | American Cyanamid Co | Chemical compositions |
| US4547113A (en) * | 1984-06-19 | 1985-10-15 | The Procter & Gamble Company | Continuous motion spiral stacker |
| EP0165608B1 (de) * | 1984-06-22 | 1991-01-02 | Ilford Ag | Hydroxyphenyltriazine, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber |
| FR2674851B1 (fr) * | 1991-04-04 | 1995-02-10 | Oreal | Derives s-triaziniques portant des substituants benzylidene camphre, compositions cosmetiques filtrantes et leur utilisation pour proteger la peau et les cheveux du rayonnement ultraviolet. |
| FR2674850B1 (fr) * | 1991-04-04 | 1993-07-02 | Oreal | Derives s-triaziniques portant des substituants benzalmalonates, compositions cosmetiques filtrantes les contenant et leur utilisation pour proteger la peau et les cheveux du rayonnement ultraviolet. |
| JPH0525029A (ja) * | 1991-07-22 | 1993-02-02 | Daikyo Rubber Seiko:Kk | 日焼け止め用化粧品 |
| US5298030A (en) * | 1992-02-21 | 1994-03-29 | Ciba-Geigy Corporation | Process for the photochemical and thermal stabilization of undyed and dyed or printed polyester fiber materials |
| JPH06308666A (ja) * | 1993-04-20 | 1994-11-04 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料及び画像形成方法 |
| JP3026244B2 (ja) * | 1993-10-19 | 2000-03-27 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JPH07330743A (ja) * | 1994-06-10 | 1995-12-19 | Kao Corp | Ｏ−ベンザルマロネート置換基を有するｓ−トリアジン誘導体及びその製造法並びにこれを含有する紫外線吸収剤及び化粧料 |
| GB9611614D0 (en) * | 1996-06-04 | 1996-08-07 | Ciba Geigy Ag | Process for inhibiting the effect of flourescent whitening agents |
-
1999
- 1999-03-25 SG SG1999001415A patent/SG75939A1/en unknown
- 1999-03-30 NZ NZ334934A patent/NZ334934A/xx unknown
- 1999-04-01 EP EP99810280A patent/EP0949251B1/de not_active Expired - Lifetime
- 1999-04-01 AT AT99810280T patent/ATE427304T1/de not_active IP Right Cessation
- 1999-04-01 DE DE59914993T patent/DE59914993D1/de not_active Expired - Lifetime
- 1999-04-06 US US09/287,029 patent/US6111103A/en not_active Expired - Fee Related
- 1999-04-06 IL IL12934999A patent/IL129349A0/xx not_active IP Right Cessation
- 1999-04-07 KR KR1019990011973A patent/KR100589869B1/ko not_active Expired - Fee Related
- 1999-04-07 ZA ZA9902565A patent/ZA992565B/xx unknown
- 1999-04-08 AU AU23653/99A patent/AU757142B2/en not_active Ceased
- 1999-04-08 CN CNB991056558A patent/CN1168722C/zh not_active Expired - Fee Related
- 1999-04-09 JP JP11102490A patent/JP2000063366A/ja active Pending
- 1999-04-09 BR BR9901088-7A patent/BR9901088A/pt not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364749A (en) * | 1991-06-03 | 1994-11-15 | Ciba-Geigy Corporation | Photographic material containing UV absorber |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA992565B (en) | 1999-10-11 |
| AU2365399A (en) | 1999-10-21 |
| NZ334934A (en) | 2000-09-29 |
| KR100589869B1 (ko) | 2006-06-15 |
| MX9903313A (enExample) | 1999-12-01 |
| EP0949251B1 (de) | 2009-04-01 |
| BR9901088A (pt) | 2000-05-02 |
| MX209164B (enExample) | 2002-07-23 |
| ATE427304T1 (de) | 2009-04-15 |
| DE59914993D1 (de) | 2009-05-14 |
| IL129349A0 (en) | 2000-02-29 |
| CN1232027A (zh) | 1999-10-20 |
| US6111103A (en) | 2000-08-29 |
| EP0949251A1 (de) | 1999-10-13 |
| JP2000063366A (ja) | 2000-02-29 |
| CN1168722C (zh) | 2004-09-29 |
| KR19990082993A (ko) | 1999-11-25 |
| SG75939A1 (en) | 2000-10-24 |
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| FGA | Letters patent sealed or granted (standard patent) |