CN1104476C - 羟苯基三嗪类化合物 - Google Patents
羟苯基三嗪类化合物 Download PDFInfo
- Publication number
- CN1104476C CN1104476C CN97109694A CN97109694A CN1104476C CN 1104476 C CN1104476 C CN 1104476C CN 97109694 A CN97109694 A CN 97109694A CN 97109694 A CN97109694 A CN 97109694A CN 1104476 C CN1104476 C CN 1104476C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- phenyl
- group
- formula
- cyclohexyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
- 239000001301 oxygen Substances 0.000 claims abstract description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920005613 synthetic organic polymer Polymers 0.000 claims abstract description 9
- -1 Phenyl Chemical group 0.000 claims description 177
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 34
- 238000000576 coating method Methods 0.000 claims description 34
- 239000011248 coating agent Substances 0.000 claims description 33
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000005466 alkylenyl group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 206010019332 Heat exhaustion Diseases 0.000 claims description 3
- 206010019345 Heat stroke Diseases 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 2
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- 230000000254 damaging effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 37
- 238000000034 method Methods 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical group 0.000 description 29
- 239000002585 base Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 20
- 239000008199 coating composition Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 229960003742 phenol Drugs 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 239000002994 raw material Substances 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 239000002966 varnish Substances 0.000 description 14
- 239000004925 Acrylic resin Substances 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000004743 Polypropylene Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 13
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000004922 lacquer Substances 0.000 description 12
- 239000003973 paint Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000005336 cracking Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 229920001903 high density polyethylene Polymers 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 229960001755 resorcinol Drugs 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 229940035422 diphenylamine Drugs 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 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 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 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 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 239000004640 Melamine resin Substances 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
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- 239000000460 chlorine Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 5
- 150000002366 halogen compounds Chemical class 0.000 description 5
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- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
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- 150000008065 acid anhydrides Chemical class 0.000 description 3
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- 239000003963 antioxidant agent Substances 0.000 description 3
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- 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
- C07D251/24—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 three ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Printing Methods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH783/96 | 1996-03-26 | ||
| CH783/1996 | 1996-03-26 | ||
| CH78396 | 1996-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1171422A CN1171422A (zh) | 1998-01-28 |
| CN1104476C true CN1104476C (zh) | 2003-04-02 |
Family
ID=4195088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97109694A Expired - Lifetime CN1104476C (zh) | 1996-03-26 | 1997-03-25 | 羟苯基三嗪类化合物 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5959008A (enExample) |
| JP (1) | JP4332819B2 (enExample) |
| KR (1) | KR100448332B1 (enExample) |
| CN (1) | CN1104476C (enExample) |
| AU (1) | AU731977B2 (enExample) |
| BE (1) | BE1012428A3 (enExample) |
| BR (1) | BR9701462B1 (enExample) |
| CA (1) | CA2200807C (enExample) |
| CH (1) | CH692739A5 (enExample) |
| DE (1) | DE19712277B4 (enExample) |
| ES (1) | ES2130985B1 (enExample) |
| FR (1) | FR2747122B1 (enExample) |
| GB (1) | GB2312210B (enExample) |
| IT (1) | IT1290823B1 (enExample) |
| NL (1) | NL1005651C2 (enExample) |
| SE (1) | SE523139C2 (enExample) |
| TW (1) | TW449610B (enExample) |
| ZA (1) | ZA975233B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH692739A5 (de) * | 1996-03-26 | 2002-10-15 | Ciba Sc Holding Ag | Polymerzusammensetzungen enthaltend 2-Hydroxyphenyl-1,3,5-triazine als UV-Absorber sowie neue 2-Hydroxyphenyl-1,3,5-triazine |
| US20020165298A1 (en) | 1996-04-02 | 2002-11-07 | Dieter Reinehr | Amino- and hydroxysubstituted triphenyl-s-triazines as stabilizers |
| US6117997A (en) * | 1997-11-19 | 2000-09-12 | Ciba Specialty Chemicals Corporation | Hydroxyphenyltriazines |
| US6051164A (en) * | 1998-04-30 | 2000-04-18 | Cytec Technology Corp. | Methods and compositions for protecting polymers from UV light |
| 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 |
| WO1999067223A2 (en) * | 1998-06-22 | 1999-12-29 | Cytec Tech Corp | Trisaryl-1,3,5-triazine ultraviolet light absorbers containing hindered phenols |
| CO5231248A1 (es) * | 2000-07-26 | 2002-12-27 | Ciba Sc Holding Ag | Articulos transparentes de polimero de baja consistencia |
| TWI316513B (en) * | 2001-07-02 | 2009-11-01 | Ciba Sc Holding Ag | Highly compatible hydroxyphenyltriazine uv-absorbers |
| US6855269B2 (en) * | 2001-11-09 | 2005-02-15 | Cytec Technology Corp. | Phenyl ether-substituted hydroxyphenyl triazine ultraviolet light absorbers |
| AU2002348236A1 (en) * | 2001-12-27 | 2003-07-24 | Cytec Technology Corp. | Uv stabilized thermoplastic olefins |
| US6893722B2 (en) | 2002-04-29 | 2005-05-17 | Exxonmobil Oil Corporation | Cationic, amino-functional, adhesion-promoting polymer for curable inks and other plastic film coatings, and plastic film comprising such polymer |
| WO2004076419A1 (en) | 2003-02-26 | 2004-09-10 | Ciba Specialty Chemicals Holding Inc. | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
| US7595011B2 (en) | 2004-07-12 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Stabilized electrochromic media |
| JP4800726B2 (ja) * | 2005-03-31 | 2011-10-26 | 大日本印刷株式会社 | 耐候剤組成物 |
| EP2167570A1 (en) | 2007-06-29 | 2010-03-31 | Basell Poliolefine Italia S.R.L. | An irradiated polyolefin composition comprising a non - phenolic stabilizer |
| DE102007050192A1 (de) * | 2007-10-20 | 2009-04-23 | Bayer Materialscience Ag | Zusammensetzung mit UV-Schutz |
| EP2450401B1 (de) | 2008-09-05 | 2013-04-17 | THOR GmbH | Flammschutzzusammensetzung enthaltend ein Phosphonsäurederivat |
| CN102264825B (zh) | 2008-12-22 | 2014-07-02 | 巴斯夫欧洲公司 | 改善耐刮性的方法及相关产品和用途 |
| EP2387600B1 (en) | 2009-01-19 | 2014-04-02 | Basf Se | Organic black pigments and their preparation |
| CN102471090B (zh) | 2009-07-07 | 2015-11-25 | 巴斯夫欧洲公司 | 钾铯钨青铜颗粒 |
| DE102010028062A1 (de) * | 2010-04-22 | 2011-10-27 | Evonik Degussa Gmbh | Verfahren zur Herstellung vernetzter organischer Polymere |
| WO2014066358A1 (en) | 2012-10-23 | 2014-05-01 | Basf Se | Ethylenically unsaturated oligomers containing polymer stabilizer groups |
| US10428204B2 (en) | 2013-09-27 | 2019-10-01 | Basf Se | Polyolefin compositions for building materials |
| WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| ES2632783T3 (es) | 2014-12-19 | 2017-09-15 | Evonik Degussa Gmbh | Sistemas de redes de cubierta para láminas de encapsulación que comprenden compuestos de bis-(alquenilamidas) |
| JP6771538B2 (ja) | 2015-07-20 | 2020-10-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 難燃性ポリオレフィン物品 |
| CN105693641A (zh) * | 2015-12-29 | 2016-06-22 | 新秀化学（烟台）有限公司 | 一种三嗪紫外线吸收剂的制备方法 |
| CN105884704A (zh) * | 2016-04-26 | 2016-08-24 | 郑绍军 | 一类长支碳链三嗪紫外吸收剂化合物及其制备方法 |
| CN107805224A (zh) * | 2017-11-15 | 2018-03-16 | 利安隆（中卫）新材料有限公司 | 制备含有醚键的混合长碳链三嗪紫外线吸收剂的方法 |
| CN112771108B (zh) | 2018-08-22 | 2023-05-05 | 巴斯夫欧洲公司 | 稳定的滚塑聚烯烃 |
| US20230220239A1 (en) | 2019-03-18 | 2023-07-13 | Basf Se | Uv curable compositions for dirt pick-up resistance |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
| WO2021064116A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Compositions with polymeric or oligomeric hydroxy phenyl triazine uv filter |
| CN119156377A (zh) | 2022-05-06 | 2024-12-17 | 巴斯夫欧洲公司 | Uv光稳定剂 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0644469A1 (fr) * | 1993-09-16 | 1995-03-22 | Eta SA Fabriques d'Ebauches | Pièce d'horlogerie à affichage analogique présentant au moins un mode d'affichage universel de l'heure |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812500A (en) * | 1987-09-30 | 1989-03-14 | Shell Oil Company | Polyolefin compositions for water pipes and for wire and cable coatings |
| JP2505033B2 (ja) * | 1988-11-28 | 1996-06-05 | 東京応化工業株式会社 | 電子線レジスト組成物及びそれを用いた微細パタ―ンの形成方法 |
| DE69030362T2 (de) * | 1989-12-05 | 1997-10-23 | Ciba Geigy Ag | Stabilisiertes organisches Material |
| EP0434619B1 (de) * | 1989-12-21 | 1995-09-06 | Ciba SC Holding AG | Verfahren zum Einbau von O-Hydroxyphenyl-S-triazinen in organische Polymere |
| DE59106390D1 (de) * | 1990-02-16 | 1995-10-12 | Ciba Geigy Ag | Gegen Schädigung durch Licht, Wärme und Sauerstoff stabilisierte Ueberzugsmittel. |
| KR100187320B1 (ko) * | 1991-02-21 | 1999-04-01 | 월터 클리웨인 | 광, 산소 및 열에 대해 안정화된 도료 |
| EP0520938B1 (de) * | 1991-06-03 | 1997-09-24 | Ciba SC Holding AG | UV-Absorber enthaltendes photographisches Material |
| EP0530135A1 (de) * | 1991-06-03 | 1993-03-03 | Ciba-Geigy Ag | UV-Absorber enthaltendes photographisches Material |
| DE4120174A1 (de) * | 1991-06-19 | 1992-12-24 | Hoechst Ag | Strahlungsempfindliche sulfonsaeureester und deren verwendung |
| BE1006797A5 (fr) * | 1992-12-03 | 1994-12-13 | Ciba Geigy Ag | Absorbeurs d'uv. |
| GB2278115B (en) * | 1993-05-17 | 1997-08-06 | Ciba Geigy Ag | 2-(2-Hydroxyphenyl)-1,3-pyrimidine derivatives and their use as stabilizers for coating compositions |
| TW270131B (enExample) * | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| DE59409837D1 (de) * | 1993-11-23 | 2001-09-27 | Ciba Sc Holding Ag | o-Hydroxyphenyl-s-triazine enthaltende stabilisierte Polymere |
| US5672704A (en) * | 1994-10-04 | 1997-09-30 | Ciba-Geigy Corporation | 2-Hydroxyphenyl-s-Triazines substituted with ethylenically unsaturated moieties |
| DK0815089T3 (da) * | 1995-03-15 | 2003-02-03 | Ciba Sc Holding Ag | Biphenyl-substituerede triaziner som lysstabilisatorer |
| EP0743309B1 (de) * | 1995-05-18 | 2003-09-10 | Ciba Specialty Chemicals Holding Inc. | o-Hydroxyphenyl-s-triazine als UV-Stabilisatoren |
| CH692739A5 (de) * | 1996-03-26 | 2002-10-15 | Ciba Sc Holding Ag | Polymerzusammensetzungen enthaltend 2-Hydroxyphenyl-1,3,5-triazine als UV-Absorber sowie neue 2-Hydroxyphenyl-1,3,5-triazine |
-
1997
- 1997-03-17 CH CH00638/97A patent/CH692739A5/de not_active IP Right Cessation
- 1997-03-19 SE SE9701012A patent/SE523139C2/sv not_active IP Right Cessation
- 1997-03-20 AU AU16441/97A patent/AU731977B2/en not_active Expired
- 1997-03-21 US US08/828,200 patent/US5959008A/en not_active Expired - Lifetime
- 1997-03-21 GB GB9705854A patent/GB2312210B/en not_active Expired - Lifetime
- 1997-03-21 BE BE9700253A patent/BE1012428A3/fr active
- 1997-03-24 CA CA002200807A patent/CA2200807C/en not_active Expired - Lifetime
- 1997-03-24 DE DE19712277.9A patent/DE19712277B4/de not_active Expired - Lifetime
- 1997-03-25 BR BRPI9701462-1A patent/BR9701462B1/pt not_active IP Right Cessation
- 1997-03-25 FR FR9703596A patent/FR2747122B1/fr not_active Expired - Lifetime
- 1997-03-25 CN CN97109694A patent/CN1104476C/zh not_active Expired - Lifetime
- 1997-03-25 ZA ZA9702533A patent/ZA975233B/xx unknown
- 1997-03-25 IT IT97MI000689A patent/IT1290823B1/it active IP Right Grant
- 1997-03-25 TW TW086103743A patent/TW449610B/zh not_active IP Right Cessation
- 1997-03-25 ES ES009700638A patent/ES2130985B1/es not_active Expired - Fee Related
- 1997-03-26 NL NL1005651A patent/NL1005651C2/nl not_active IP Right Cessation
- 1997-03-26 KR KR1019970010541A patent/KR100448332B1/ko not_active Expired - Lifetime
- 1997-03-26 JP JP11329997A patent/JP4332819B2/ja not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0644469A1 (fr) * | 1993-09-16 | 1995-03-22 | Eta SA Fabriques d'Ebauches | Pièce d'horlogerie à affichage analogique présentant au moins un mode d'affichage universel de l'heure |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4332819B2 (ja) | 2009-09-16 |
| BE1012428A3 (fr) | 2000-11-07 |
| ITMI970689A1 (it) | 1998-09-25 |
| ZA975233B (en) | 1997-09-26 |
| CN1171422A (zh) | 1998-01-28 |
| AU731977B2 (en) | 2001-04-12 |
| SE523139C2 (sv) | 2004-03-30 |
| DE19712277B4 (de) | 2014-11-06 |
| SE9701012D0 (sv) | 1997-03-19 |
| FR2747122B1 (fr) | 2003-01-17 |
| ES2130985A1 (es) | 1999-07-01 |
| DE19712277A1 (de) | 1997-10-30 |
| KR970065611A (ko) | 1997-10-13 |
| CA2200807C (en) | 2007-04-17 |
| IT1290823B1 (it) | 1998-12-11 |
| GB2312210A (en) | 1997-10-22 |
| CH692739A5 (de) | 2002-10-15 |
| ES2130985B1 (es) | 2000-03-01 |
| GB9705854D0 (en) | 1997-05-07 |
| TW449610B (en) | 2001-08-11 |
| MX9702211A (es) | 1998-05-31 |
| AU1644197A (en) | 1997-10-02 |
| US5959008A (en) | 1999-09-28 |
| NL1005651C2 (nl) | 2000-06-19 |
| GB2312210B (en) | 1998-08-19 |
| BR9701462B1 (pt) | 2008-11-18 |
| FR2747122A1 (fr) | 1997-10-10 |
| CA2200807A1 (en) | 1997-09-26 |
| NL1005651A1 (nl) | 1997-09-30 |
| SE9701012L (sv) | 1997-11-04 |
| JPH1045729A (ja) | 1998-02-17 |
| KR100448332B1 (ko) | 2004-12-04 |
| BR9701462A (pt) | 1998-08-25 |
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