TWI391393B - 往長波長偏移之苯并三唑紫外線吸收劑及其用途 - Google Patents
往長波長偏移之苯并三唑紫外線吸收劑及其用途 Download PDFInfo
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- TWI391393B TWI391393B TW095103077A TW95103077A TWI391393B TW I391393 B TWI391393 B TW I391393B TW 095103077 A TW095103077 A TW 095103077A TW 95103077 A TW95103077 A TW 95103077A TW I391393 B TWI391393 B TW I391393B
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- carbon atoms
- branched
- alkyl
- phenyl
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- 239000006096 absorbing agent Substances 0.000 title claims abstract description 41
- 239000012964 benzotriazole Substances 0.000 title abstract description 15
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000011368 organic material Substances 0.000 claims abstract description 15
- -1 benzylidene, p-xylylene Chemical group 0.000 claims description 119
- 125000004432 carbon atom Chemical group C* 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 238000000576 coating method Methods 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 32
- 239000000463 material Substances 0.000 claims description 32
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
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- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
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- 125000004429 atom Chemical group 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 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 7
- 150000001540 azides Chemical class 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001565 benzotriazoles Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
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- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
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- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
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- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
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- 238000002360 preparation method Methods 0.000 abstract description 10
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- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 1
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
- XRXMSAXBKVILLN-UHFFFAOYSA-N n,n,n',n'-tetraphenylbut-2-ene-1,4-diamine Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)CC=CCN(C=1C=CC=CC=1)C1=CC=CC=C1 XRXMSAXBKVILLN-UHFFFAOYSA-N 0.000 description 1
- DDLNUIWJEDITCB-UHFFFAOYSA-N n,n-di(tetradecyl)hydroxylamine Chemical compound CCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCC DDLNUIWJEDITCB-UHFFFAOYSA-N 0.000 description 1
- DHXOCDLHWYUUAG-UHFFFAOYSA-N n,n-didodecylhydroxylamine Chemical compound CCCCCCCCCCCCN(O)CCCCCCCCCCCC DHXOCDLHWYUUAG-UHFFFAOYSA-N 0.000 description 1
- OTXXCIYKATWWQI-UHFFFAOYSA-N n,n-dihexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC OTXXCIYKATWWQI-UHFFFAOYSA-N 0.000 description 1
- ITUWQZXQRZLLCR-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC ITUWQZXQRZLLCR-UHFFFAOYSA-N 0.000 description 1
- WQAJFRSBFZAUPB-UHFFFAOYSA-N n,n-dioctylhydroxylamine Chemical compound CCCCCCCCN(O)CCCCCCCC WQAJFRSBFZAUPB-UHFFFAOYSA-N 0.000 description 1
- GMBXBKNMMIWUED-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-4-yl)-3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanamide Chemical compound C1C(C)(C)NC(C)(C)CC1NCCC(=O)NC1CC(C)(C)NC(C)(C)C1 GMBXBKNMMIWUED-UHFFFAOYSA-N 0.000 description 1
- KESXDDATSRRGAH-UHFFFAOYSA-N n-(4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C=C1 KESXDDATSRRGAH-UHFFFAOYSA-N 0.000 description 1
- ZLUHLPGJUZHFAR-UHFFFAOYSA-N n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]naphthalen-1-amine Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=CC2=CC=CC=C12 ZLUHLPGJUZHFAR-UHFFFAOYSA-N 0.000 description 1
- UBINNYMQZVKNFF-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine oxide Chemical compound C=1C=CC=CC=1C=[N+]([O-])CC1=CC=CC=C1 UBINNYMQZVKNFF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DARUEKWVLGHJJT-UHFFFAOYSA-N n-butyl-1-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-1-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC(Cl)=NC(N2C(CC(CC2(C)C)NCCCC)(C)C)=N1 DARUEKWVLGHJJT-UHFFFAOYSA-N 0.000 description 1
- BYYFPVDBAHOLDX-UHFFFAOYSA-N n-dodecyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCCCCC)C1=CC=CC=C1 BYYFPVDBAHOLDX-UHFFFAOYSA-N 0.000 description 1
- LRUUZFQPCUFYPV-UHFFFAOYSA-N n-dodecyldodecan-1-imine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCC LRUUZFQPCUFYPV-UHFFFAOYSA-N 0.000 description 1
- GBMIPYGHTZRCRH-UHFFFAOYSA-N n-ethylethanimine oxide Chemical compound CC[N+]([O-])=CC GBMIPYGHTZRCRH-UHFFFAOYSA-N 0.000 description 1
- AXFITEGIVIRXAM-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine;n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC AXFITEGIVIRXAM-UHFFFAOYSA-N 0.000 description 1
- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
- FHAFFFSIDLDWQA-UHFFFAOYSA-N n-hexadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCC FHAFFFSIDLDWQA-UHFFFAOYSA-N 0.000 description 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- QXJGVICBAANVMZ-UHFFFAOYSA-N n-octyloctan-1-imine oxide Chemical compound CCCCCCCC[N+]([O-])=CCCCCCCC QXJGVICBAANVMZ-UHFFFAOYSA-N 0.000 description 1
- CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 description 1
- MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 0.000 description 1
- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
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- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
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- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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
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- 239000007800 oxidant agent Substances 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
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- 239000002985 plastic film Substances 0.000 description 1
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- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229910052917 strontium silicate Inorganic materials 0.000 description 1
- QSQXISIULMTHLV-UHFFFAOYSA-N strontium;dioxido(oxo)silane Chemical compound [Sr+2].[O-][Si]([O-])=O QSQXISIULMTHLV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- OLBWDGJTEXRJLY-UHFFFAOYSA-N tetradecyl 3-(2,2,4,4-tetramethyl-21-oxo-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-20-yl)propanoate Chemical compound O1C2(CCCCCCCCCCC2)N(CCC(=O)OCCCCCCCCCCCCCC)C(=O)C21CC(C)(C)NC(C)(C)C2 OLBWDGJTEXRJLY-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 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
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 150000003918 triazines Chemical class 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
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 229920001866 very low density polyethylene Polymers 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
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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Description
本發明係有關於一種新穎的苯并三唑紫外線吸收劑,其具有向長波長偏移的吸收光譜,在波長達到410-420nm處有明顯的吸收。本發明其它方面為它們的製備方法、一種含有此新型UV吸收劑的UV安定組成物,以及將此新化合物作為有機材料的UV光安定劑之使用。
含有芳香基團的聚合性基材,例如以芳香族環氧化物、芳香族聚酯或芳香族(多元)異氰酸酯為基礎的黏著劑及塗覆用樹脂對於波長達到約410至420nm的紫外光/可見光有高度的敏感性。
用一UV吸收層在上面保護此黏著劑或塗層乃是極度困難的,因為極小量的輻射-即使在大約410nm附近-穿透吸收UV的頂塗層即足以造成保護性塗層的離層及剝離。
典型的應用是汽車用塗層,通常是兩層金屬性汽車用塗層,其中往長波長偏移的UV吸收劑有極大的用處。
今日的汽車用塗層已在鋼板上直接塗覆一層抗腐蝕性陽離子電塗層。由於陽離子樹脂的光敏感性明顯偏向紅光(達400-410nm),因此用習知的UV吸收劑無法充分地保護該陽離子電塗層。
為了更好地保護這些敏感層,已有人嚐試將苯并三唑UV吸收劑朝向長波長偏移。例如,美國專利第5,436,349號揭露苯并三唑UV吸收劑,其在苯環的5位置被烷基磺醯基
取代。但是,吸收的偏移仍不夠大,不足以保護此種高度敏感的材料。
舉例來說,美國專利第6,166,218號揭露了苯并三唑UV吸收劑,其在苯環的5位置被一CF3基取代,也造成稍微向長波長偏移的吸收,並且提高了光化學安定性。然而,此吸收的偏移仍不足以保護光化學敏感度達到410nm的材料。
令人驚訝的是,現已發現,當苯并三唑UV吸收劑的苯環是苯二甲酸酐或醯亞胺系統的一部份時,能觀察到吸收的大量偏移,最大約20-30nm,延伸至420nm。化合物意外地維持光化學安定,且在典型塗覆應用時,最終並未呈現遷移。
本發明的一個方面是式(I)或(II)之化合物
其中R1為氫、1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至4個1至4碳原子的烷基取代的該苯基或該苯烷基;或R1為基或為基
其中L是1至12碳原子的伸烷基、2至12碳原子的亞烷基、亞苄基(benzylidene)、伸對苯二甲基(p-xylylene)或5至7碳原子的伸環烷基;R2為1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;或被一或多個-OH-,-OCO-R11,-OR14-,-NCO或-NH2基或其混合物所取代的該烷基,或被一或多個-O-,-NH-或-NR14-基或其混合物插入的該烷基或該烯基,其可為未被取代的或被一或多個-OH,-OR14或-NH2基或其混合物所取代者;其中R11是氫、直鏈或支鏈C1-C18烷基、C5-C12環烷基、直鏈或支鏈C3-C8烯基、苯基、萘基或C7-C15苯烷基;及R14是氫、1至24碳原子的直鏈或支鏈烷基;或R2是-OR14、-C(O)-O-R14基、-C(O)-NHR14或-C(O)-NR14R’14其中R’14意義相同於R14;或R2是-SR13、-NHR13或-N(R13)2;或R2是-(CH2)m-CO-X1-(Z)p-Y-R15其中X1是-O-或-N(R16)-,Y是-O-或-N(R17)-或一直接鍵,Z是C2-C12-伸烷基、插入有1至3個氮原子的C4-C12伸烷基、氧原子或其混合物,或是C3-C12伸烷基、伸丁烯基、伸丁炔基、伸環己基或伸苯基,其中每一個可額外被一羥基
取代;或以下基團
其中*代表一個鍵
或當Y是一個直接鍵時,Z亦可為一直接鍵;m是0、1或2,p是1,或當X與Y分別為-N(R16)-與-N(R17)-時,p亦為0,R15是氫、C1-C12烷基、基或基
或-CO-C(R18)=C(H)R19或,當Y是-N(R17)-,與R17共同形成-CO-CH=CH-CO-基,其中R18是氫或甲基,R19是氫、甲基或-CO-X1-R20,其中R20是氫、C1-C12烷基或下式的基團;
或
R5、R6、R7及R8獨立地為氫、鹵素、CN、NO2或NH2;R13是1至20碳原子之烷基、2至20碳原子之羥烷基、3至18碳原子之烯基、5至12碳原子之環烷基、7至15碳原子之苯烷基、苯基或萘基,此二者皆可被一或兩個1至4碳原子的烷基取代;R16與R17彼此獨立地為氫、C1-C12烷基、嵌插1至3氧原子的C3-C12烷基,或為環己基或C7-C15苯烷基,且當Z為伸乙基時R16與R17也共同形成伸乙基;X是O或NE1,其中E1是氫、直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C18烯基、C2-C6炔基、C5-C12環烷基、苯基、萘基或C7-C15苯烷基;或該直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C24烯基、C5-C12環烷基、C2-C6炔基可被一或多個-F-、-OH-、-OR22、-NH2、-NHR22、-N(R22)2、-NHCOR23、NR22COR23、-OCOR24、-COR25、-SO2R26、-PO(R27)n(R28)2-n、-Si(R29)n(R30)3-n、-Si(R22)3、-N+(R22)3A-、-S+(R22)2A-、環氧乙烷基或其混合物取代;該直鏈或支鏈C1-C24烷基、直鏈或支鏈之未經取代或經取代之C2-C24烯基、C5-C12環烷基或C2-C6炔基亦可嵌插
一或多個-O-、-S-、-NH-或-NR22-基或其組合;該苯基、萘基或C7-C15苯烷基亦可被一或多個鹵素、-CN-、-CF3、-NO2、-NHR22、-N(R22)2、-SO2R26、-PO(R27)n(R28)2-n、-OH-、-OR22、-COR25、-R25所取代;其中n是0、1或2;R22是直鏈或支鏈C1-C18烷基、直鏈或支鏈C2-C18烯基、C5-C10環烷基、苯基、萘基、C7-C15苯烷基,或兩個R22當接到N或Si原子時可與其所連接的原子共同形成吡咯烷(pyrrolidine)、哌啶(piperidine)或嗎啉(morpholine)環;R23是氫、OR22、NHR22、N(R22)2或與R22相同意義,R24是OR22、NHR22、N(R22)2或與R22相同意義,R25是氫、OH、OR22、NHR22或N(R22)2、O-縮水甘油基或與R22相同意義,R26是OH、OR22、NHR22或N(R22)2,R27是NH2、NHR22或N(R22)2,R28是OH或OR22,R29是Cl或OR22,R30是直鏈或支鏈C1-C18烷基;或E1是或基其中
R1至R8如上述定義,且Q是直鏈或支鏈C2-C12伸烷基、插入有一或多個-O-、-NH或NR14原子的C2-C12伸烷基、C5-C10伸環烷基、伸對苯基或下列基團,
其中*代表一個鍵。
鹵素舉例來說,為氟、氯、溴或碘。氯為較佳。
當任一個取代基是1至24碳原子的直鏈或支鏈烷基時,舉例來說,此基團為甲基、乙基、異丙基、正丁基、異丁基、第二丁基、叔丁基、叔戊基、2-乙基己基、第三辛基、十二烷基、叔-十二烷基、十三烷基、正十六烷基、正十六烷基或二十烷基。
當任一個取代基是2至18碳原子的直鏈或支鏈烯基時,舉例來說,此基團為烯丙基、戊烯基、己烯基或油烯基。較佳者為3至16碳原子的烯基,特別是3至12碳原子,例如2至6碳原子的烯基。
當任一個取代基是5至12碳原子的環烷基時,舉例來說,此基團為環戊基、環己基、環庚基、環辛基及環十二烷基。C1-C4烷基取代之C5-C8環烷基為,例如,甲基環戊基、二甲基環戊基、甲基環己基、二甲基環己基、三甲基
環己基或叔丁基環己基。
當任一基團為7至15碳原子的苯烷基時,此基團為,例如,苯甲基、苯乙基、α-甲基苯甲基或α,α-二甲基苯甲基。
當苯基被烷基取代時,其為,例如,甲苯基及二甲苯基。
被一或多個-O-基取代及/或被一或多個-OH-取代的的烷基,舉例來說,可為-(OCH2CH2)wOH或-(OCH2CH2)wO(C1-C24烷基)其中w是1至12。
嵌插了一或多個-O-的烷基可衍生自環氧乙烷單元或環氧丙烷單元或二者的混合。
當烷基嵌插了-NH或-NR14-,該基團係類似於上述嵌插了-O-的基團的衍生。較佳的是伸乙基二胺(ethylenediamine)重覆單元。
例如,CH3-O-CH2CH2、CH3-NH-CH2CH2、CH3-N(CH3)-CH2、CH3-O-CH2CH2-O-CH2CH2、CH3-(O-CH2CH2-)2O-CH2CH2-、CH3-(O-CH2CH2-)3O-CH2CH2-或CH3-(O-CH2CH2-)4O-CH2CH2-。
舉例來說,伸烷基為伸乙基、伸丁基、伸己基、2-甲基-1,4-伸丁基、伸己基、伸辛基、伸十甲基及伸十二甲基。
伸環烷基例如伸環戊基、伸環己基、伸環庚基、伸環辛基及伸環十二烷基。伸環己基為較佳。
嵌插了氧、NH或-NR14-的伸烷基例如-CH2CH2-O-CH2CH2-、-CH2CH2-NH-CH2CH2-、-CH2CH2-N(CH3)-CH2CH2-、-CH2CH2-O-CH2CH2-O-CH2CH2-、-CH2CH2-(O-CH2
CH2-)2O-CH2CH2-、-CH2CH2-(O-CH2CH2-)3O-CH2CH2-、-CH2CH2-(O-CH2CH2-)4O-CH2CH2-或-CH2CH2-NH-CH2CH2-。
Q基團為直鏈或支鏈C1-C12伸烷基、C5-C10伸環烷基、伸對苯基或下列基團
其中*代表一個鍵。
該基團可衍生自現有的二胺,例如,所謂的端氨基聚氧化丙烯醚(Jeffamines)。二胺的例子有乙烯二胺、丙烯二胺、2-甲基-1,5-伸戊基二胺、異佛爾酮二胺(isophorondiamine)或1,2-二氨基環己烷。
相似地,Z基團亦可衍生自同樣的現有的二胺或衍生自相對應的二醇類。
典型的端氨基聚氧化丙烯醚(Jeffamines)的例子有D-2000其中x是33.1或ED-2003其中a+c是5且b是39.5。
關於式(I)或(II)之化合物,其中
R1為氫、1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至4個1至4碳原子的烷基取代的該苯基或該苯烷基;或R1為基或基其中L是1至12碳原子的伸烷基、2至12碳原子的亞烷基、亞苄基(benzylidene)、伸對苯基二甲基(p-xylylene)或5至7碳原子的伸環烷基;R2為1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;或R2為-(CH2)m-CO-X1-(Z)p-Y-R15其中X1是-O-,Y是-O-或一直接鍵,Z是C2-C12伸烷基、插入有1至3個氮原子、氧原子或其混合物的C4-C12伸烷基,或當Y是一個直接鍵時,Z亦可為一直接鍵;m是2,p是1,R15是氫、C1-C12烷基、或
或基
R5、R6、R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C18烯基、C2-C6炔基、C5-C12環烷基、苯基、萘基或C7-C15苯烷基;或該直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C24烯基、C5-C12環烷基、C2-C6炔基可被一或多個-F-、-OH-、-OR22、-NH2、-NHR22、-N(R22)2、-NHCOR23、NR22COR23、-OCOR24、-COR25、-SO2R26、-PO(R27)n(R28)2-n、-Si(R29)n(R30)3-n、-Si(R22)3、-N+(R22)3A-、-S+(R22)2A-、環氧乙烷基或其混合物取代;該直鏈或支鏈C1-C24烷基、直鏈或支鏈之未經取代或經取代之C2-C24烯基、C5-C12環烷基或C2-C6炔基亦可嵌插一或多個-O-、-S-、-NH-或-NR22-基或其組合;該苯基、萘基或C7-C15苯烷基亦可被一或多個鹵素、-CN-、-CF3、-NO2、-NHR22、-N(R22)2、-SO2R26、-PO(R27)n(R28)2-n、-OH-、-OR22、-COR25、-R25所取代;其中n是0、1或2;R22是直鏈或支鏈C1-C18烷基、直鏈或支鏈C2-C18烯基、
C5-C10環烷基、苯基或萘基,C7-C15苯烷基,或兩個R22當接到N或Si原子時可與其所連接的原子共同形成吡咯烷、哌啶或嗎啉環;R23是氫、OR22、NHR22、N(R22)2或與R22相同意義,R24是OR22、NHR22、N(R22)2或與R22相同意義,R25是氫、OH、OR22、NHR22或N(R22)2、O-縮水甘油基或與R22相同意義,R26是OH、OR22、NHR22或N(R22)2,R27是NH2、NHR22或N(R22)2,R28是OH或OR22,R29是Cl或OR22,R30是直鏈或支鏈C1-C18烷基;或E1是或基其中R1至R8如上述定義,且Q是直鏈或支鏈C2-C12伸烷基、C5-C10伸環烷基或伸對苯基或下列基團
例如,在式(I)或(II)之化合物中R1為氫、1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至4個1至4碳原子的烷基取代的該苯基或該苯烷基;R2為1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;或R2為-(CH2)2-CO-O-(Z)-O-R15其中Z是C2-C12伸烷基、插入有1至3個氧原子的C4-C12伸烷基;R15是氫、C1-C12烷基、或或基
R5、R6、R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、直鏈或支鏈C1-C24烷基、C5-C12環烷基、苯基、C7-C15苯烷基;或該直鏈或支鏈C1-C24烷基或C5-C12環烷基可被一或多個-F-、-OH-、-OR22、-NH2、-NHR22、-N(R22)2
取代;該苯基或C7-C15苯烷基亦可被一或多個鹵素、-CN-、-CF3、-OH-、-OR22、-COR22、-R22所取代;其中R22是直鏈或支鏈C1-C18烷基、直鏈或支鏈C2-C18烯基、C5-C10環烷基、C6-C16苯基或萘基、C7-C15苯烷基;或E1是或基其中R1至R8如上述定義,且Q是C2-C12伸烷基、C5-C7伸環烷基、伸對苯基或下列基團
特別要關注的是式(I)或(II)之化合物,其中R1為氫、1至12碳原子的直鏈或支鏈烷基或7至15碳原子的苯烷基;R2為1至12碳原子的直鏈或支鏈烷基或7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;
R5與R6為氫,或其中一個是Cl或Br;R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、未被取代的或被1至4個OH取代的直鏈或支鏈C1-C6烷基、未被取代的或被F、CF3、CN或Cl取代的苯基,或C7-C9苯烷基。
概括來說,式(I)之化合物為較佳。
可使用的個別化合物係例如化合物1b及2c
本發明之另一方面是一用來製備式(I)或式(II)之化合物的方法
其中取代基R1至R8係如申請專利範圍第1項所定義,該
方法包含將式(III)、(IV)或(V)的化合物
,其中W是鹵素或氮
與式(X)的一種疊氮化物反應
其中M是一個n價的金屬陽離子或P+(R105)4,R101、R102、R103、R104彼此獨立各為氫或C1-C18烷基,R105為C1-C18烷基,且R是1、2或3。
依據本發明,此方法之較佳反應條件如下:此反應可在熔融態中或在一溶劑中進行。特別令人感興趣的是在一溶劑中進行反應的一種製備式I或式II之化合物的方法。
適當的溶劑例如偶極質子惰性溶劑(dipolar aprotic solvents)、質子溶劑、脂肪族或芳香族羧酸的酯類、醚類、
鹵化烴類、芳香族溶劑、胺類及烷氧基苯類。
偶極質子惰性溶劑的例子有二烷基亞碸,例如二甲基亞碸;甲醯胺類,例如甲醯胺、二甲基甲醯胺或N,N-二甲基乙醯胺;內醯胺類,例如N-甲基吡咯烷酮;磷酸醯胺(phosphoric amides),例如六甲基磷酸三醯胺;烷基化脲,例如N,N’-二甲基伸乙基脲、N,N’-二甲基伸丙基脲或N,N,N’,N’-四甲基脲;以及腈類,例如乙腈或苯甲腈。
質子溶劑的例子有聚伸烷基二醇,例如聚乙二醇;聚伸烷基二醇單醚,例如二乙二醇單甲醚,及水,後者本身或與一或多種上述溶劑的單相混合物或兩相混合物亦可加入相轉移催化劑,例如四烷基銨鹽、四烷基鏻鹽或環狀醚。相樣的相轉移催化劑亦可用於兩相系統中的固態/液態形式。
較佳的脂肪族或芳香族羧酸的酯類,舉例來說,有醋酸丁酯、醋酸環己酯及苯甲酸甲酯。
較佳的醚類如二烷基醚、特別是二丁醚、四氫呋喃、二噁烷及(多)-伸烷基二醇二烷基醚。
鹵化烴例如二氯甲烷及氯仿。
芳香溶劑仾如甲苯、氯苯及硝基苯。
適當的胺溶劑例如三乙基胺、三丁基胺及苯甲基二甲基胺。
較佳的烷氧基苯例如苯甲醚及苯乙醚。
製備式I之化合物的方法亦可在離子性或超臨界流體中進行,例如流體二氧化碳。
特別令吾人感興趣的是在一種偶極質子惰性溶劑進行的製備式I或式II之化合物的方法。
反應溫度可在很大範圍內調整,但所選擇的溫度係使得能夠發生令人滿意的轉化率,此溫度較佳地從10℃到200℃,特別是20℃至150℃
其它苯并三唑化合物的類似的製程已被揭露於WO02/24668。
在較佳的製備式I或式II之化合物的方法中,式III、IV或式V之化合物的量相對於式X之疊氮化物的量的莫耳比例為1:1至1:3,特別是1:1至1:2,例如1:1至1:1.3。當存在有也能與疊氮化物反應的官能性側基團時,式IX之疊氮化物的過量也就隨著增加。
在一具體實施例中,反應係在一催化劑之存在下進行。
此催化劑包括,例如,銅(I)或銅(II)或其它過渡金屬的鹽類,以鐵、鈷、鎳、鈀、鉑、金或鋅等為基礎。不同於過渡金屬鹽,其陰離子的範圍相當大,也可使用這些金屬的金屬錯合物及金屬錯合物鹽。較佳係使用銅(I)及銅(II)的氯化物、溴化物及碘化物,特別佳的是使用溴化銅(I)。
催化劑的有利的使用量為0.01至10重量%,特別是0.1至5重量%,例如以所用的化合物III、IV或V的重量為基礎的0.1至5重量%。
反應可在一外加的鹼的存在下,或在一鹼性pH緩衝系統的存在下進行。適當的pH緩衝系統包括,舉例來說,鹼金屬或鹼土金屬氫氧化物;鹼金屬或鹼土金屬醇鹽;鹼金
屬或鹼土金屬羧酸鹽,例如醋酸鹽或碳酸鹽;鹼金屬或鹼土金屬磷酸鹽;三級胺,例如,三乙基胺或三丁基胺;以及未經取代的或經取代的吡啶。
一些式III、式IV或V的起始化合物可從文獻中得知,或可以例1及例2所述步驟相同的方式來製備。
然而,也可以藉習用的方法來製備這種苯并三唑。步驟通常包括令一經取代的鄰硝基苯胺(W則為NO2)進行重氮化作用,然後令所得的重氮鎓鹽與一經取代的苯酚進行偶合,並使重氮苯中間體還原成對應的所希望得到的苯并三唑。這些苯並三唑的起始物有一部份已為商品項目,或可藉一般有機合成法來製備。
製備苯并三唑的其它方法例如Science of Synthesis 13.13,575-576中所提供者。
還原法不僅可藉水合作用來達到,亦可藉其它方法,例如EP 0 751 134中所述者。欲造成氫轉移,可將一些試劑與一催化劑共同使用,該試劑例如甲酸或其鹽類、次膦酸(phosphinic acid)或其鹽類或連二磷酸的鹼金屬鹽或銨鹽。該催化劑,舉例來說,是一種貴重金屬。
本發明之苯並三唑常可用於各種基材中作為紫外線吸收劑。因此,本發明的另一方面是一種對光引發之降解呈現安定之組成物,其包含,(a)一收到光引發之降解的有機材料,以及(b)上述式I或式II之化合物。
概言之,式I或式II之化合物的存在量,以有機材料的
重量為基礎,為0.1%至30%,較佳地0.5%至15%,更佳地為1%至10%,以重量計。
就一方面來說,該有機材料是一種記錄材料。
依據本發明之記錄材料適合用於壓感性複製系統、使用微型膠囊照相複製系統、熱感性複製系統、照相材料及噴墨印刷。
本發明之記錄材料的特徵是其品質,特別是有關於對光的快速,有超出預期的改良。
本發明之記錄材料的構造有其特殊的用途。其包括有一常用的載體,例如塗覆了一或多層的紙或塑膠膜。這些層含有適當的必要成份,視材料的類型而定,若為照相材料,則為鹵化銀乳劑、偶染體、染料或類似物。特別視用於噴墨印刷的材料具有一層特別能吸收墨水的層在常用的載體上。未經塗覆的紙也可以用於噴墨印刷。在這種狀況下,紙係同時作為載體材料及吸墨層使用。適當的用於噴墨印刷的材料則如美國專利第5,073,448號(併入本文作為參考資料)中所述。
記錄材料亦可為透明的,例如,作為投影片之用。
式I或II之化合物可早在carder material製造之時就加入其中,例如,在製造紙的時候,可加入紙漿中。第二種應用的方法是用式I或式II之化合物的水溶液來噴灑carder material以將該化合物加至塗層組成物中。
適合投影用之透明記錄材料的所用的塗層組成物不能含有任何會散射光線的粒子,例如顏料及填料。
與染料結合的塗層組合物可含有數種其它添加劑,例如抗氧化劑、光安定劑(也包括不屬於本發明之紫外線吸收劑的UV吸收劑)、黏性提高劑、螢光增亮劑、殺蟲劑及抗靜電劑。
塗層材料通常依下述製備:水溶性成份,例如,黏結劑,係溶在水中並攪拌在一起。固體成份,例如填充劑及其它上述的添加劑,則分散在這水性介質中。分散作用較佳地可藉助下列設備來達成:例超音波取樣器、渦輪攪拌器、勻化器、膠粉磨、顆粒磨、砂磨機、高速攪拌器及類似者。式I或式II之化合物可很容易地加入塗層組成物中。
本發明之記錄材料較佳地含有1至5000mg/m2的,特別是50至1200mg/m2式I之化合物。
如前所述,本發明之記錄材料範圍相當廣。舉例來說,式I或式II之化合物亦被用於壓感性複製系統中。它們可被加入紙中以保護其中的微囊包裝的染料前驅物免照到光,或者加到顯影層的黏結劑中以保護其中所形成的染料。
使用光敏性微型膠囊,藉由壓力來顯影的照相複製系統敘述於美國專利第4,416,966號、第4,483,912號、第4,352,200號、第4,535,050號、第4,536,463號、第4,551,407號、第4,562,137號、第4,608,330號,也敘述於EP-A 139,479、EP-A 162,664、EP-A 164,931、EP-A 237,024、EP-A 237,025或EP-A 260,129。在這些系統中,此化合物可被置於染料接受層中。然而此化合物亦可被置於給予層以保護
染料前驅物免照到光。
可被安定的照相材料為照相染料及含有此染料及其前驅物的層,例如相紙及薄膜。適當的材料例如美國專利第5,364,749號(併入本文作為參考資料)中所敘述者。式I或式II之化合物在此係作為一紫光線過濾件,防止靜電閃光。在彩色照相材料中,偶合劑及染料亦被保護以防光化學分解。
此化合物可被用於各種彩色照相材料。舉例來說,它們可被用於彩色紙、彩色反轉紙、直接正像彩色材料、彩色負片、彩色正片、彩色反轉片等等。其中,較佳地係被用於含有反轉基材或能形成正像的照相彩色材料。
彩色照相記錄材料通常在一載體上含有對藍色敏感及/或對綠色敏感及/或對紅色敏感的乳膠層,若需要的話,尚含有一保護層,該化合物較佳地不是在綠色敏感層中就是在紅色敏感層中,或是在綠色敏感層與紅色敏感層之間的一層中,或在鹵化銀乳膠層上方的一層中。
依據光聚合理論、光塑化理論或微型膠囊的破裂,式I或式II之化合物可被用於記錄材料,或者用在使用熱感性及光感性偶氮鎓鹽、含氧化劑之隱色染料或含路易士酸的染料內酯的例子中。
再者,它們可被用在染料擴散轉印、熱臘轉印及非字模印刷的紀錄材料,以及用於靜電式、電刻式、電泳式、磁變式及雷射電子照相型印刷機及帶筆記錄儀。在這些當中,用在染料擴散轉印的記錄材料為較佳者,如同在
EP-A-507,734中所述。
它們亦可被用於墨水中,例如用於噴墨印刷,例如美國專利第5,098,477號中所敘述。
在本發明的另一具體實施例中,有機材料是一種天然的、半合成的或合成的聚合物。
下面列出這些聚合物的例子。
1.單烯類或二烯類的聚合物,例如聚丙烯、聚異丁烯、聚丁-1-烯、聚-4-甲基戊-1-烯、聚乙烯環己烷、聚異戊二烯或聚丁二烯,以及環烯類的聚合物,例如環戊烯或降冰片烯、聚乙烯(選擇性地可為交聯的),例如高密度聚乙烯(HDPE)、高密度及高分子量聚乙烯(HDPE-HMW)、高密度及超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、線性低密度聚乙烯(LLDPE)、VLDPE及ULDPE。聚烯烴類,即前段舉例之單烯聚合物,較佳地為聚乙烯及聚丙烯,可藉不同的方法製備,特別是下列方法:
a)自由基聚合反應(一般係在高壓及高溫下)。
b)催化聚合反應,所用的催化劑通常含有一或多個週期表第IVb、Vb、VIb或VIII族的金屬。這些金屬通常具有一或多於一個配位根,通常是氧化物、鹵化物、醇鹽、酯類、醚類、胺類、烷基、烯基及/或芳香基,其可為π-或σ-配位者。這些金屬錯合物可為自由狀態或為固定在基材上,通常是在活化的氯化鎂、氯化鈦(III)、氧化鋁或氧化矽上。這些催化劑在聚合介質中
是可溶的或是不可溶的。這些催化劑本身即可使用於聚合反應中,也可添加額外的活化劑,通常為烷基金屬、金屬氫化物、金屬烷基鹵化物、金屬烷基氧化物或金屬烷基噁烷,該金屬為週期表第Ia、IIa及/或IIIa族的元素。活化劑可藉由酯類、醚類、胺類或甲矽烷醚基而方便地進行改質。這些催化劑系統通常稱為Phillips、Standard Oil Indiana,Ziegler(-Natta),TNZ(Dupont),金屬茂(metallocene)或單一位置催化劑(SSC)。
2.第1項所述聚合物的混合物,例如聚丙烯與聚異丁烯的混合物、聚丙烯與聚乙烯的混合物(例如PP/HDPE,PP/LDPE)及不同型的的聚乙烯的混合物(例如LDPE/HDPE)。
3.單烯烴及二烯烴與彼此的共聚物或與其它二烯基單體的共聚物,例如乙烯/丙烯共聚物、線性低密度聚乙烯(LLDPE)及其與低密度聚乙烯(LDPE)的混合物、聚丙烯/丁-1-烯共聚物、聚丙烯/異丁烯共聚物、乙烯/丁-1-烯共聚物、乙烯/己烯共聚物、乙烯/甲基戊烯共聚物、乙烯/庚烯共聚物、乙烯/辛烯共聚物、乙烯/乙烯基環己烷共聚物、乙烯/環烯烴共聚物(例如乙烯/降冰片烯,如COC)、乙烯/1-烯烴共聚物,其中1-烯烴乃是原位生成;丙烯/丁二烯共聚物、異丁烯/異戊二烯共聚物、乙烯/乙烯基環己烯共聚物、乙烯/烷基丙烯酸酯共聚物、乙烯/烷基甲基丙烯酸酯共聚物、乙烯/乙烯基醋酸酯共聚
物或乙烯/丙烯酸共聚物及它們的鹽類(離聚物),以及乙烯與丙烯及一種二烯例如己二烯、二環戊二烯或亞乙基-降冰片烯的三聚物;以及這些共聚物與彼此所形成之混合物及與上述第1項中所述之聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-醋酸乙酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA,及交替型或無規型聚烷撐/一氧化碳共聚物及其與其它聚合物的混合物,例如聚醯胺。
4.烴樹脂(例如C5-C9)包括其加氫改質(例如增黏劑)及聚伸烷基與澱粉的混合物。
1)-4)項的同聚物及共聚物可以具有任何立體構造,包括間規立構的、等規的、半等規的或無規立構的,其中無規立構聚合物為較佳。亦包括立體塊規(stereoblock)聚合物。
5.聚苯乙烯、聚(對甲基苯乙烯)、聚(α-甲基苯乙烯)。
6.芳香族同聚物及共聚物,其係衍生自乙烯基芳香族單體,包括苯乙烯、α-甲基苯乙烯、乙烯甲苯的所有異構物,特別是對乙烯甲苯,乙基苯乙烯的所有異構物、丙基苯乙烯、乙烯基聯苯、乙烯基萘及乙烯基蒽及其混合物。同聚物及共聚物可以具有任何立體構造,包括間規立構的、等規的、半等規的或無規立構的;其中無規立構聚合物為較佳。亦包括立體塊規(stereoblock)聚合物。
6a.共聚物,包括前述的乙烯基芳香族單體及共聚單體,選自於:乙烯、丙烯、二烯、腈類、酸類、順丁烯二酸酐、
順丁烯二醯亞胺、乙烯基醋酸酯及氯乙烯或丙烯酸衍生物及其混合物,例如苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/乙烯(異分子聚合物)、苯乙烯/烷基甲基丙烯酸酯、苯乙烯/丁二烯/烷基丙烯酸酯、苯乙烯/丁二烯/烷基甲基丙烯酸酯、苯乙烯/順丁烯二酸酐、苯乙烯/丙烯腈/丙烯酸甲酯;苯乙烯共聚物與另一聚合物之高衝擊強度混合物,例如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三聚物;以及苯乙烯之嵌塊共聚物例如苯乙烯/丁二烯/苯乙烯、苯乙烯/異戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6b.從上述聚合物之加氫反應所得的氫化芳香族聚合物,特別是包括無規立構的聚苯乙烯的加氫反應所製得的聚環己基乙烯(PCHE),通常稱為聚乙烯環己烷(PVCH)。
6c.從上述6a所提之聚合物之加氫反應所得的氫化芳香族聚合物。
同聚物及共聚物可以具有任何立體構造,包括間規立構的、等規的、半等規的或無規立構的;其中無規立構聚合物為較佳。亦包括立體塊規(stereoblock)聚合物。
7.乙烯基芳香族單體的接枝共聚物,例如苯乙烯或α-甲基苯乙烯,例如苯乙烯接在聚丁二烯上,苯乙烯接在聚丁二烯-苯乙烯上或聚丁二烯-丙烯腈共聚物上;苯乙烯與丙烯腈(或甲基丙烯腈)接在聚丁二烯上;苯乙烯、丙烯腈及甲基丙烯酸甲酯接在聚丁二烯上;苯乙烯與順丁烯二酸酐接在聚丁二烯上;苯乙烯、丙烯腈及順丁烯二
酸酐或順丁烯二醯亞胺接在聚丁二烯上;苯乙烯及順丁烯二醯亞胺接在聚丁二烯;苯乙烯與丙烯酸烷基酯或甲基丙烯酸烷基酯接在聚丁二烯上;苯乙烯與丙烯腈接在乙烯/丙烯/二烯三聚物上;苯乙烯與丙烯腈接在聚丙烯酸烷基酯上或聚甲基丙烯酸烷基酯上、苯乙烯與丙烯腈接在丙烯酸酯/丁二烯共聚物上,以及其與6)中所列的共聚物的混合物,例如已知之ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含鹵素的聚合物,例如聚氯丁烯、氯化橡膠、異丁烯-異戊二烯的氯化及溴化共聚物(鹵代丁基橡膠)、氯化及磺醯氯化聚乙烯、乙烯與氯化乙烯的共聚物、環氧丙烷同聚物及共聚物,特別是含鹵素之乙烯基化合物的聚合物,例如聚氯乙烯、聚偏氯乙烯、聚氟乙烯、聚偏氟乙烯,以及其共聚物,例如氯乙烯/偏氯乙烯、氯乙烯/醋酸乙烯酯或偏氯乙烯/醋酸乙烯共聚物。
9.衍生自α,β-不飽和酸的聚合物及其衍生物,例如聚丙烯酸酯及聚甲基丙烯酸酯;聚甲基丙烯酸甲酯、聚丙烯醯胺及聚丙烯腈,其係經過丙烯酸丁酯給予衝擊改質。
10.第9項所提的單體與彼此的共聚物或與其它不飽和單體之共聚物,例如丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷酯共聚物、丙烯腈/丙烯酸烷氧基烷酯或丙烯腈/鹵化乙烯共聚物或丙烯腈/甲基丙烯酸烷酯/丁二烯三聚物。
11.衍生自不飽和醇類與胺類之聚合物或其醯基衍生物或其縮醛,例如聚乙烯醇、聚醋酸乙烯酯、聚硬脂酸乙烯
酯、聚苯甲酸乙烯酯、聚順丁烯二酸乙烯酯、聚乙烯丁縮醛、聚苯二甲酸丙烯酯或聚丙烯三聚氰胺;以及它們與上述第1項所提之烯烴的共聚物。
12.環狀醚的同聚物及共聚物,例如聚伸烷基二醇、聚環氧乙烷、聚環氧丙烷或其與二縮水甘油醚的共聚物。
13.聚縮醛例如聚甲醛以及含有環氧乙烷作為共聚單體的聚甲醛;以熱塑性聚氨酯、丙烯酸酯或MBS改質之聚縮醛。
14.聚二苯醚及硫化物,及聚二苯醚與苯乙烯聚合物或聚醯胺之混合物。
15.聚氨酯,一種是衍生自端羥基聚醚、聚酯或聚丁二烯之聚氨酯,另一種是衍生自脂肪族或芳香族聚異氰酸酯,以及其先驅物。
16.聚醯胺及共聚醯胺,衍生自二胺及二羧酸及/或衍生自氨基羧酸或對應之內醯胺,例如聚醯胺4、聚醯胺6、聚醯胺6/6、6/10、6/9、6/12、4/6、12/12、聚醯胺11、聚醯胺4、來自於間苯二甲胺(m-xylene diamine)及己二酸之芳香族聚醯胺;由1,6-己二胺(hexamethylenediamine)及異苯二甲酸(isophthalic)或/及對苯二甲酸(terephthalic acid)所製備之聚醯胺,其或含有一彈性體作為改性質,或者不含該彈性體,例如聚-2,4,4-三甲基己撐對苯二甲醯胺(poly-2,4,4-trimethylhexamethylene terephthalamide)或聚間苯撐異苯二甲醯胺(poly-m-phenylene isophthalamide);以及上述聚醯胺與聚烯烴之嵌塊共聚
物、烯烴共聚物、離聚物或化學鍵結或接枝之彈性體;或上述聚醯胺與聚醚之嵌塊共聚物,例如與聚乙二醇、聚丙二醇或聚四伸甲基二醇之嵌塊共聚物;以及經過EPDM或ABS改性之聚醯胺或共聚醯胺;及加工過程中凝結的聚醯胺(RIM聚醯胺系統)。
17.聚脲、聚醯亞胺、聚醯胺-醯亞胺、聚醚醯亞胺、聚酯醯亞胺、聚乙內醯脲及聚苯并咪唑。
18.聚酯,衍生自二羧酸類及二醇類及/或衍生自羥羧酸或對應之內酯,例如聚對苯二甲酸乙二醇酯、聚對苯二甲酸丁二醇酯、聚-1,4-二羥甲基環己烷對苯二甲酸酯(poly-1,4-dimethylolcyclohexane terephthalate)、聚伸烷基萘二甲酸酯(PAN)及聚羥基苯甲酸酯,以及衍生自端羥基聚醚的嵌塊共聚醚酯;以及經過聚碳酸酯或MBS改性之聚酯。
19.聚碳酸酯或聚酯碳酸酯。
20.聚酮類。
21.聚碸類、聚醚碸及聚醚酮。
22.交聯之聚合物,一種是衍生自醛類,另一種是衍生自苯酚、脲及三聚氰胺,例如酚/甲醛樹脂、脲/甲醛樹脂及三聚氰胺/甲醛樹脂。
23.乾性及非乾性醇酸樹脂。
24.不飽和聚酯樹脂,衍生自飽和與不飽和二羧酸,並以多元醇及乙烯基化合物作為交聯劑,以及其低可燃性之含鹵素改性體。
25.可交聯之丙烯酸樹脂,衍生自經取代的丙烯酸酯,例如環氧丙烯酸酯、尿烷丙烯酸酯或聚酯丙烯酸酯。
26.醇酸樹脂、聚酯樹脂及丙烯酸酯樹脂,其係以三聚氰胺樹脂、脲樹脂、異氰酸酯、三聚異氰酸酯、聚異氰酸酯或環氧樹脂進行交聯。
27.交聯之環氧樹脂,衍生自脂肪族、環脂族、雜環或芳香族縮水甘油基化合物,例如雙酚A及雙酚F之二縮水甘油醚產物,其係以常用的硬化劑如酸酐或胺類進行交聯,含加速劑或不含加速劑。
28.天然聚合物例如纖維素、橡膠、明膠及其它的化學改質之同系列衍生物,例如纖維素醋酸酯、丙酸纖維素及丁酸纖維素,或者纖維素醚例如甲基纖維素;以及松香及它們的衍生物。
29.前述聚合物的混合物,例如PP/EPDM、聚醯胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/熱塑性PUR、PC/熱塑性PUR、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA 6.6及共聚物PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
舉例來說,該聚合物是一種熱塑性聚合物。
在另一實施例中,有機材料是一種塗層,特別是汽車塗層。用於塗層中之樹脂通常是交聯的聚合物,例如,一種是衍生自醛類者,另一種是衍生自苯酚、脲及三聚氰胺
者,例如,苯酚/甲醛樹脂、尿素/甲醛樹脂及三聚氰胺/甲醛樹脂。
也可以使用不飽和聚酯樹脂,其乃衍生自飽和與不飽和二羧酸之共聚酯並以多元醇及乙烯基化合物作為交聯劑,以及它們的低可燃性之含鹵素改性體。
較好用的是可交聯之丙烯酸樹脂,衍生自經取代的丙烯酸酯,例如環氧丙烯酸酯、尿烷丙烯酸酯或聚酯丙烯酸酯。
也可以用醇酸樹脂、聚酯樹脂及丙烯酸酯樹脂,其係以三聚氰胺樹脂、脲樹脂、異氰酸酯、三聚異氰酸酯、聚異氰酸酯或環氧樹脂進行交聯。
衍生自脂肪族、環脂族、雜環或芳香族縮水甘油基化合物之交聯環氧樹脂,例如雙酚A及雙酚F之二縮水甘油醚產物,其係以常用的硬化劑如酸酐或胺類進行交聯,含加速劑或不含加速劑。
塗層材料亦可為一種可藉輻射固化之組成物,含有烯化不飽和單體或寡聚物以及一種多元不飽和脂肪族寡聚物。
依據本發明,對於光的作用可被安定化的醇酸樹脂清漆乃是特別用塗覆汽車的習用烤漆(汽車罩面噴漆),例如以醇酸樹脂/三聚氰胺樹脂為基礎的清漆以及醇酸/丙烯酸/三聚氰胺樹脂(見H.Wagner與H.F.Sarx所著的“Lackkunstharze”(1977),99-123頁)。其它交聯劑包括glycouril樹脂,嵌塊異氰酸酯或環氧樹脂。
還需注意的是本發明之化合物可用於非酸催化之熱固性樹脂,例如環氧樹脂、環氧-聚酯樹脂、乙烯基樹脂、醇酸樹酯、丙烯酸樹脂及聚酯樹脂,視需要用矽改性,異氰酸酯或三聚異氰酸酯樹脂。環氧樹脂與環氧-聚酯樹脂係以習用的交聯劑來交聯,例如酸、酸酐、胺及類似物。因此,環氧化物可被用來作為各種丙烯酸或聚酯樹脂系統的交聯劑,這些樹脂系統係已被主幹構造上的反應性基改質。
想得到水溶性塗層、可與水混合的塗層或可以水分散的塗層時,則形成存在於樹脂中之酸基的銨鹽。粉末塗層組成物可藉由將甲基丙烯酸縮水甘油酯與選定的醇成份反應而製備。
在一具體實施例中,上述塗層係被施用在一基材上,該基材是對波長大於380nm的電磁輻射具有敏感性。
典型的感光基材是,例如,貼在一金屬基材上之陰極沈積塗層。此種塗層通常用於汽車工業。
所謂對大於380nm波長的電磁輻射有敏感性,包括UV或可見光,例如波長達到440nm,較佳地達到420nm,特別是達到410nm的範圍。
在各種使用式(I)或(II)作為安定劑,以防止紫外光及可見光的有害的影響的有機材料中,亦可存在有其它安定劑及添加劑。
舉例如下。
1. 抗氧化劑
1.1. 烷基化單苯酚,例如2,6-二叔丁基-4-甲基苯酚、2-叔
丁基-4,6-二甲基苯酚、2,6-二叔丁基-4-乙基苯酚、2,6-二叔丁基-4-正丁基苯酚、2,6-二叔丁基-4-異丁基苯酚、2,6-二環戊基-4-甲基苯酚、2-(α-甲基環己基)-4,6-二甲基-苯酚、2,6-二-十八烷基-4-甲基苯酚、2,4,6-三環己基苯酚、2,6-二叔丁基-4-甲氧基甲基苯酚、線性或有分枝側鏈的壬基苯酚,例如2,6-二-壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十三烷-1’-基)苯酚及其混合物。
1.2. 烷基硫代甲基苯酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二辛基硫代甲基-6-乙基苯酚、2,6-十二烷基硫代甲基-4-壬基苯酚。
1.3. 氫醌及烷基化氫醌,例如2,6-二叔丁基-4-甲氧基苯酚、2,5-二叔丁基氫醌、2,5-二叔戊基氫醌、2,6-二苯基-4-十八烷基氧苯酚、2,6-二叔丁基氫醌、2,5-二叔丁基-4-羥基苯甲醚氫醌、3,5-二叔丁基-4-羥基苯甲醚、3,5-二叔丁基-4-羥基苯基硬脂酸酯、雙(3,5-二叔丁基-4-羥苯基)己二酸酯。
1.4. 生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(維它命E)。
1.5. 羥化硫代二苯基醚,例如2,2’-硫代雙(6-叔丁基-4-甲基苯酚)、2,2’-硫代雙(4-辛基苯酚)、4,4’-硫代雙(6-叔丁基-3-甲基苯酚)、4,4’-硫代雙(6-叔丁基-2-甲基苯酚)、
4,4’-硫代雙(3,6-二-第二戊基苯酚)、4,4’-雙(2,6-二甲基-4-羥苯基)二硫化物。
1.6. 亞烷基雙酚,例如2,2’-伸甲基雙(6-叔丁基-4-甲基苯酚)、2,2’-伸甲基雙(6-叔丁基-4-乙基苯酚)、2,2’-伸甲基雙[4-甲基-6-(α-甲基環己基)苯酚]、2,2’-伸甲基雙(4-甲基-6-環己基苯酚)、2,2’-伸甲基雙(6-壬基-4-甲基苯酚)、2,2’-伸甲基雙(4,6-二-叔丁基苯酚)、2,2’-亞乙基雙(4,6-二-叔丁基苯酚)、2,2’-亞乙基雙(6-叔丁基-4-異丁基苯酚)、2,2’-伸甲基雙[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-伸甲基雙[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-伸甲基雙(2,6-二叔丁基苯酚)、4,4’-伸甲基雙(6-叔丁基-2-甲基苯酚)、1,1-雙(5-叔丁基-4-羥基-2-甲基苯基)丁烷、2,6-雙(3-叔丁基-5-甲基-2-羥基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羥基-2-甲基苯基)丁烷、1,1-雙((5-叔丁基-4-羥基-2-甲基-苯基)-3-正十二烷基氫硫基丁烷、乙二醇雙[3,3-雙(3’-叔丁基-4’-羥苯基)丁酸酯]、雙(3-叔丁基-4-羥基-5-甲基苯基)二環戊二烯、雙[2-(3’-叔丁基-2’-羥基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]對苯二甲酸酯、1,1-雙-(3,5-二甲基-2-羥基苯基)丁烷、2,2-雙(3,5-二-叔丁基-4-羥苯基)丙烷、2,2-雙(5-叔丁基-4-羥基-2-甲基苯基)-4-正十二烷基氫硫基丁烷、1,1,5,5-四-(5-叔丁基-4-羥基-2-甲基苯基)戊烷。
1.7. O-,N-及S-苄基化合物,例如3,5,3’,5’-四-叔丁基-4.4’-
二羥基二苄基醚、十八烷基-4-羥基-3,5-二甲基苄基氫硫基醋酸酯、十三烷基-4-羥基-3,5-二-叔丁基苄基氫硫基醋酸酯、三(3,5-二-叔丁基-4-羥基苄基)胺、雙(4-叔丁基-3-羥基-2,6-二甲基苄基)二硫代對苯二甲酸酯、雙(3,5-二-叔丁基-4-羥基-苄基)硫化物、異辛基-3,5-二-叔丁基-4-羥基苄基氫硫基醋酸酯。
1.8. 羥基苄基化丙二酸酯,例如二-十八烷基-2,2-雙(3,5-二-叔丁基-2-羥基苄基)丙二酸酯、二-十八烷基-2-(3-叔丁基-4-羥基-5-甲基苄基)丙二酸酯、二-十二烷基氫硫基乙基-2,2-雙(3,5-二-叔丁基-4-羥基苄基)丙二酸酯、雙[4-(1,1,3,3-四甲基丁基)苯基]-2,2-雙(3,5-二-叔丁基-4-羥基苄基)丙二酸酯。
1.9. 芳香族羥基苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羥基-苄基)-2,4,6-三甲基苯、1,4-雙(3,5-二-叔丁基-4-羥基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二-叔丁基-4-羥基苄基)苯酚。
1.10. 三嗪化合物,例如2,4-雙(辛基氫硫基)-6-(3,5-二-叔丁基-4-羥基-苯胺基)-1,3,5-三嗪、2-辛基氫硫基-4,6-雙(3,5-二-叔丁基-4-羥基苯胺基)-1,3,5-三嗪、2-辛基氫硫基-4,6-雙(3,5-二-叔丁基-4-羥基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二-叔丁基-4-羥基苯胺基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羥基苄基)三聚異氰酸酯、1,3,5-三(4-叔丁基-3-羥基-2,6-二甲基苄基)三聚異氰酸酯、2,4,6-三-(3,5-二-叔丁基-4-羥基苯基乙
基)-1,3,5-三嗪、1,3,5-三(3,5-二-叔丁基-4-羥基苯基丙醯基)-六氫-1,3,5-三嗪、1,3,5-三(3,5-二-環己基-4-羥基苄基)三聚異氰酸酯。
1.11. 苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羥基苄基膦酸酯、二乙基-3,5-二-叔丁基-4-羥基苄基膦酸酯、二-十八烷基3,5-二-叔丁基-4-羥基苄基膦酸酯、二-十八烷基-5-叔丁基-4-羥基-3-甲基苄基膦酸酯、3,5-二-叔丁基-4-羥基苄基膦酸的鈣鹽。
1.12. 醯胺基苯酚,例如4-羥基月桂醯替苯胺、4-羥基硬脂醯替苯胺、辛基N-(3,5-二-叔丁基-4-羥基苯基)氨基甲酸酯。
1.13. β-(3,5-二-叔丁基-4-羥基苯基)丙酸與一元醇或多元醇所產生的酯類,該一元醇或多元醇例如甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、季戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)草醯胺、3-噻十一烷醇、3-噻十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷-2,6,7-三噁二環[2.2.2]辛烷。
1.14. β-(5-叔丁基-4-羥基-3-甲基苯基)丙酸與一元醇或多元醇所產生的酯類,該一元醇或多元醇例如甲醇、乙醇、正辛醇、異辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、季戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羥基乙基)
三聚異氰酸酯、N,N’-雙(羥基乙基)草醯胺、3-噻十一烷醇、3-噻十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷-2,6,7-三噁二環[2.2.2]辛烷;3,9-雙[2-{3-(3-叔丁基-4-羥基-5-甲基苯基)丙醯氧基}-1,1-二甲基乙基]-2,4,8,10-四噁螺[5.5]十一烷。
1.15. β-(3,5-二-環己基-4-羥基苯基)丙酸與一元醇或多元醇所產生的酯類,該一元醇或多元醇例如甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、季戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)草醯胺、3-噻十一烷醇、3-噻十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷-2,6,7-三噁二環[2.2.2]辛烷。
1.16. 3,5-二-叔丁基-4-羥基苯基醋酸與一元醇或多元醇所產生的酯類,該一元醇或多元醇例如甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、季戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)草醯胺、3-噻十一烷醇、3-噻十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷-2,6,7-三噁二環[2.2.2]辛烷。
1.17. β-(3,5-二-叔丁基-4-羥基苯基)丙酸的醯胺類,例如N,N’-雙(3,5-二-叔丁基-4-羥基苯基丙醯基)伸己基二醯胺、N,N’-雙(3,5-二-叔丁基-4-羥基苯基丙醯基)伸丙
基二醯胺、N,N’-雙(3,5-二-叔丁基-4-羥基苯基丙醯基)醯肼、N,N’-雙[2-(3-[3,5-二-叔丁基-4-羥基苯基]丙醯氧基)乙基]草醯胺(Naugard®XL-1,Uniroyal提供)。
1.18. 抗壞血酸(維它命C)
1.19. 胺類抗氧化劑,例如N,N’-二-異丙基-伸對苯基二胺、N,N’-二-第二丁基-伸對苯基二胺、N,N’-雙(1,4-二甲基戊基)-伸對苯基二胺、N,N’-雙(1-乙基-3-甲基戊基)-伸對苯基二胺、N,N’-雙(1-甲基庚基)-伸對苯基二胺、N,N’-二-環己基-伸對苯基二胺、N,N’-二苯基-伸對苯基二胺、N,N’-雙(2-萘基)-伸對苯基二胺、N-異丙基-N’-苯基-伸對苯基二胺、N-(1,3-二甲基丁基)-N’-苯基-伸對苯基二胺、N-(1-甲基庚基)-N’-苯基-伸對苯基二胺、N-環己基-N’-苯基伸對苯基二胺、4-(對甲苯氨磺醯)二苯基胺、N,N’-二甲基-N,N’-二-第二丁基-伸對苯基二胺、二苯基胺、N-烯丙基二苯基胺、4-異丙氧基二苯基胺、N-苯基-1-萘基胺、N-(4-叔辛基苯基)-1-萘基胺、N-苯基-2-萘基胺、辛基化二苯基胺,例如p,p’-二-叔辛基二苯基胺、4-正丁基-氨基苯酚、4-丁醯基氨基苯酚、4-壬醯基氨基苯酚、4-十二烷醯氨基苯酚、4-十八烷醯基氨基苯酚、雙(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲基氨基甲基苯酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-雙[(2-甲基苯基)氨基]乙烷、1,2-雙(苯基氨基)丙烷、(鄰甲苯基)雙胍、雙
[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化N-苯-1-萘基胺、單烷基化與二烷基化之叔丁基/叔辛基二苯基胺的混合物、單烷基化與二烷基化之壬基二苯基胺的混合物、單烷基化與二烷基化之十二烷基二苯基胺的混合物、單烷基化與二烷基化異丙基/異己基二苯基胺的混合物、單烷基化與二烷基化叔丁基二苯基胺的混合物、2,3-二氫-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪(phenothiazine)、單烷基化與二烷基化叔丁基/叔辛基吩噻嗪之混合物、單烷基化與二烷基化叔辛基吩噻嗪之混合物、N-烯丙基吩噻嗪、N,N,N’,N’-四苯基-1,4-二氨基丁-2-烯。
2. 紫外線吸收劑及光安定劑
2.1. 2-(2’-羥基苯基)苯并三唑,例如2-(2’-羥基-5’-甲基苯基)苯并三唑、2-(3’,5’-二-叔丁基-2’-羥基苯基)苯并三唑、2-(5’-叔丁基-2’-羥基苯基)苯并三唑、2-(2’-羥基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二-叔-丁基-2’-羥基苯基)-5-氯-苯并三唑、2-(3’-叔丁基-2’-羥基-5’-甲基苯基)-5-氯-苯並三唑、2-(3’-第二丁基-5’-叔丁基-2’-羥基苯基)、2-(2’-羥基-4’-辛氧基苯基)苯并三唑、2-(3’,5’-二-叔戊基-2’-羥基苯基)苯并三唑、2-(3’,5’-雙-(α,α-二甲基苄基)-2’-羥基苯基)苯並三唑、2-(3’-叔丁基-2’-羥基-5’-(2-辛氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)-羰基乙基]-2’-羥基苯基)-5-氯-苯并三唑、2-(3’-叔
丁基-2’-羥基-5’-(2-甲氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-叔丁基-2’-羥基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羥基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羥基苯基)苯并三唑、2-(3’-十二烷基-2’-羥基-5’-甲基苯基)苯并三唑、2-(3’-叔丁基-2’-羥基-5’-(2-異辛氧基碳基乙基)苯基苯并三唑、2,2’-伸甲基-雙[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羥基苯基]-2H-苯并三唑與聚乙二醇300的轉酯化產物;
其中R=3’-叔丁基-4’-羥基-5’-2H-苯并三唑-2-基苯基,2-[2’-羥基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)-苯基]-苯并三唑;2-[2’-羥基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)-苯基]-苯并三唑。
2.2. 2-羥基二苯甲酮,例如4-羥基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2’,4’-三羥基及2’-羥基-4,4’-二甲氧基衍生物。
2.3. 經取代或未經取代的苯甲酸的酯類,例如4-叔丁基-苯基水楊酸酯、苯基水楊酸酯、辛基苯基水楊酸酯、二苯甲醯間苯二酚、雙(4-叔丁基苯甲醯)間苯二酚、苯甲醯間苯二酚、2,4-二-叔丁基苯基-3,5-二-叔丁基-4-羥基苯甲酸酯、十六烷基3,5-二-叔丁基-4-羥基苯甲
酸酯、十八烷基3,5-二-叔丁基-4-羥基苯甲酸酯、2-甲基-4,6-二-叔丁基苯基3,5-二-叔丁基-4-羥基苯甲酸酯。
2.4. 丙烯酸酯類,例如乙基-α-氰基-β,β-二苯基丙烯酸酯、異辛基α-氰基-β,β-二苯基丙烯酸酯、甲基α-甲氧甲醯基肉桂酸酯、甲基α-氰基-β-甲基對甲氧基肉桂酸酯、丁基α-氰基-β-甲基對甲氧基肉桂酸酯、甲基α-甲氧甲醯基對甲氧基肉桂酸酯、N-(β-甲氧甲醯基-β-氰基乙烯基)-2-甲基二氫化吲哚、新戊基四(α-氰基-β,β-二苯基丙烯酸酯)。
2.5. 鎳化合物,例如2,2’-硫代-雙[4-(1,1,3,3-四甲基丁基)苯酚]的鎳錯合物,例如1:1或1:2錯合物,含或不含額外配位基,例如正丁基胺、三乙醇胺或N-環己基二乙醇胺,二丁基二硫代氨基甲酸鎳、單烷基酯例如甲酯或乙酯的鎳鹽、4-羥基-3,5-二-叔丁基苄基膦酸的鎳鹽、酮肟的鎳錯合物,例如2-羥基-4-甲基苯基十一烷基酮肟、1-苯基-4-月桂醯-5-羥基吡唑的鎳錯合物,含或不含額外的配位基。
2.6. 空間位阻的胺類,例如雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二-叔丁基-4-羥基苄基丙二酸酯、1-(2-羥基乙基)-2,2,6,6-四甲基-4-羥基哌啶與琥
珀酸的縮合物、N,N’-雙(2,2,6,6-四甲基-4-哌啶基)己撐二胺與4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的線性或環狀縮合物、三(2,2,6,6-四甲基-4-哌啶基)氮川三醋酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、1,1’-(1,2-乙烷二基)-雙(3,3,5,5-四甲基哌嗪酮)、4-苯甲醯基-2,2,6,6-四甲基哌啶、4-硬脂氧基-2,2,6,6-四甲基哌啶、雙(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羥基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮螺[4.5]癸烷-2,4-二酮、雙(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N’-雙(2,2,6,6-四甲基-4-哌啶基)伸己基二胺與4-嗎啉代-2,6-二氯-1,3,5-三嗪的線性或環狀縮合物、2-氯-4,6-雙(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪與1,2-雙(3-氨基丙基氨基)乙烷的縮合物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪與1,2-雙(3-氨基丙基氨基)乙烷的縮合物、8-乙醯基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮螺[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、4-十六烷氧基-與4-硬脂氧基-2,2,6,6-四甲基哌啶、N,N’-雙(2,2,6,6-四甲基-4-哌啶基)伸己基二胺與4-環己基氨基-2,6-二氯-1,3,5-三嗪的縮合物、1,2-雙(3-氨基丙基氨基)乙烷與2,4,6-三氯-1,3,5-三嗪的縮
合物,以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS Reg.No.[136504-96-6]);1,6-己二胺與2,4,6-三氯-1,3,5-三嗪的縮合物,以及N,N-二丁基胺與4-丁基氨基-2,2,6,6-四甲基哌啶的縮合物(CAS Reg.No.[192268-64-7]);N-2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀銑酵亞胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀銑酵亞胺、2-十一烷基-7,7,9,9-四甲基-1-噁-3,8-二氮-4-氧代-螺[4,5]癸烷、7,7,9,9-四甲基-2-環十一烷基-1-噁-3,8-二氮-4-氧代螺[4,5]癸烷與環氧氯丙烯(epichlorohydrin)的反應產物、1,1-雙(1,2,2,6,6-五甲基-4-哌啶基氧羰基)-2-(4-甲氧基苯基)乙烯、N,N’-雙-甲醯基-N,N’-雙(2,2,6,6-四甲基-4-哌啶基)伸己基二胺、4-甲氧基伸甲基丙二酸與1,2,2,6,6-五甲基-4-羥基哌啶的二酯、聚[甲基丙基-3-氧-4-(2,2,6,6-四甲基-4-哌啶基)]矽氧烷、順丁烯二酸酐-α-烯烴共聚物與2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反應產物、2,4-雙[N-(1-環己氧基-2,2,6,6-四甲基哌啶-4-基)-N-丁基氨基]-6-(2-羥基乙基)氨基-1,3,5-三嗪、1-(2-羥基-2-甲基丙氧基)-4-十八烷醯氧基-2,2,6,6-四甲基吡啶、5-(2-乙基己烷醯)-氧甲基-3,3,5-三甲基-2-嗎啉酮、Sanduvor(Clariant;CAS Reg.No.106917-31-1)、5-(2-乙基己烷醯)氧甲基-3,3,5-三甲基-2-嗎啉酮、2,4-雙-[(1-環己氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪與N,N’-雙(3-胺基丙基)伸乙基二
胺的反應產物、1,3,5-三(N-環己基-N-(2,2,6,6-四甲基哌啶-3-酮-4-基)氨基)s-三嗪、1,3,5-三(N-環己基-N-(1,2,2,6,6-五甲基哌啶-3-酮-4-基)氨基)s-三嗪。
2.7. 草醯胺類,例如4,4’-二辛氧基草醯替苯胺、2,2’-二乙氧基草醯替苯胺、2,2’-二辛氧基-5,5’-二-叔丁草醯替苯胺、2,2’-二-十二烷氧基-5,5’-二-叔丁草醯替苯胺、2-乙氧基-2’-乙基草醯替苯胺、N,N’-雙(3-二甲基氨基丙基)草醯胺、2-乙氧基-5-叔丁基-2’-乙草醯替苯胺及其與2-乙氧基-2’-乙基-5,4’-二-叔丁草醯替苯胺的混合物、鄰-與對-甲氧基雙取代之草醯胺之混合物以及鄰-與對-乙氧基雙取代之草醯胺之混合物。
2.8. 2-(2-羥基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羥基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羥基-4-辛氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羥基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪、2,4-雙(2-羥基-4-丙氧基-苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羥基-4-辛氧基苯基)-4,6-雙(4-甲基苯基)-1,3,5-三嗪、2-(2-羥基-4-十二烷氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羥基-4-十三烷氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羥基-4-(2-羥基-3-丁氧基丙氧基)苯基]-4,6-雙(2,4-二甲基)-1,3,5-三嗪、2-[2-羥基-4-(2-羥基-3-辛氧基丙氧基)苯基]-4,6-雙(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羥基丙氧基)-2-羥基苯基]-4,6-雙
(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羥基-4-(2-羥基-3-十二烷氧基丙氧基)苯基]-4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羥基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羥基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羥基-4-(3-丁氧基-2-羥基丙氧基)苯基]-1,3,5-三嗪、2-(2-羥基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羥基-4-[3-(2-乙基己基-1-氧)-2-羥基丙氧基]苯基}-4,6-雙(2,4-二甲基苯基)1,3,5-三嗪、2,4-雙(4-[2-乙基己氧基]-2-羥苯基)-6-(4-甲氧基苯基)-1,3,5-三嗪。
3. 金屬去活性劑,例如N,N’-二苯基草醯胺、N-水楊醛-N’-水楊醯基肼、N,N’-雙(水楊醯基)肼、N,N’-雙(3,5-二-叔丁基-4-羥基苯基丙醯基)肼、3-水楊醯基氨基-1,2,4-三唑、雙(苯亞甲基)草醯基二肼、草醯替苯胺、間苯二醯基二醯肼、癸二醯基二苯基醯肼、N,N’-二乙醯基己二醯基二醯肼、N,N’-雙(水楊醯基)草醯二醯肼、N,N’-雙(水楊醯基)硫代丙醯基二醯肼。
4. 亞磷酸酯與亞膦酸酯,例如三苯基亞磷酸酯、二苯基烷基亞磷酸酯、苯基二烷基亞磷酸酯、三(壬基苯基)亞磷酸酯、三-月桂基亞磷酸酯、三-十八烷基亞磷酸酯、二-硬脂基季戊四醇二亞磷酸酯、三(2,4-二-叔丁基苯基)亞磷酸酯、二異癸基季戊四醇二亞磷酸酯、雙(2,4-二-叔丁基苯基)季戊四醇二亞磷酸酯、雙(2,4-二枯基苯基)季戊四醇二亞磷酸酯、雙(2,6-二-叔丁基-4-甲基苯基)季戊
四醇二亞磷酸酯、二異癸氧基季戊四醇二亞磷酸酯、雙(2,4-二叔丁基-6-甲基苯基)季戊四醇二亞磷酸酯、雙(2,4,6-三(叔丁基苯基)季戊四醇二亞磷酸酯、三硬脂酸酯山梨糖醇三亞磷酸酯、四(2,4-二-叔丁基苯基)4,4’-伸二苯基二亞膦酸酯、6-異辛烷基-2,4,8,10-四-叔丁基-12H-二苯[d,g]-1,3,2-二噁phosphocin、雙(2,4-二-叔丁基-6-甲基苯基)甲基亞磷酸酯、雙(2,4-二-叔丁基-6-甲基苯基)乙基亞磷酸酯、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯[d,g]-1,3,2-二噁phosphocin、2,2’,2”-氮川-[三乙基三(3,3’,5,5’-四-叔丁基-1,1’-二苯基-2,2’-二基)亞膦酸酯]、2-乙基己基(3,3’,5,5’-四-叔丁基-1,1’-二苯基-2,2’-二基)亞膦酸酯、5-丁基-5-乙基-2-(2,4,6-三-叔丁基苯氧基)-1,3,2-二噁phosphirane。
特別好的是下列的亞磷酸酯:三(2,4-二-叔丁基苯基)亞磷酸酯(Irgafos®168,Ciba Specialty Chemicals Inc.),三(壬基苯基)亞磷酸酯,
5. 羥基胺,例如N,N-二苄基羥基胺、N,N-二乙基羥基胺、N,N-二辛基羥基胺、N,N-二月桂基羥基胺、N,N-二-十四烷基羥基胺、N,N-二-十六烷基羥基胺、N,N-二-十八烷基羥基胺、N-十六烷基-N-十八烷基羥基胺、N-十七烷基-N-十八烷基羥基胺、衍生自氫化牛脂胺的N,N-二烷基羥基胺。
6. 硝酮,例如,N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、N-辛基-α-庚基硝酮、N-月桂基-α-十一烷基硝酮、N-十四烷基-α-十三烷基硝酮、N-十六烷基-α-十五烷基硝酮、N-十八烷基-α-十七烷基硝酮、N-十六烷基-α-十七烷基硝酮、N-十八烷基-α-十五烷基硝酮、N-十七烷基-α-十七烷基硝酮、N-十八烷基-α-十六烷基硝酮、從衍生自氫化牛脂胺之N,N-二烷基羥基胺所衍生的硝酮。
7. 含硫協同劑,例如二月桂基硫代二丙酸酯、二肉荳蔻基硫代二丙酸酯、二硬脂基硫代二丙烯酯或二硬脂基二硫化物。
8. 過氧化物淨化劑,例如β-硫代二丙酸的酯類,例如月桂基酯、硬脂基酯、肉荳蔻基酯或十三烷酯、氫硫基苯并咪唑或2-氫硫基苯并咪唑的鋅鹽、二丁基二硫代氨基甲酸鋅、二-十八烷基二硫化物、季戊四醇四(β-十二烷基氫硫基)丙酸酯。
9. 聚醯胺安定劑,例如銅鹽結合碘化物及/或磷化合與二價錳的鹽。
10. 鹼性共安定劑,例如三聚氰胺、聚乙烯基吡咯烷酮、二氰
二醯胺、氰尿酸三烯丙酯、尿素衍生物、聯氨衍生物、胺類、聚醯胺、聚氨基甲酸酯、鹼金屬鹽及高級脂肪酸之鹼土金屬鹽,例如硬脂酸鈣、硬脂酸鋅、山俞酸鎂、硬脂酸鎂、篦麻油酸鈉及棕櫚酸鉀、焦基茶酚銻或焦基茶酚鋅。
11. 成核劑,例如無機物質,例如滑石、金屬氧化物,例如二氧化鈦或氧化鎂、磷酸鹽、碳酸鹽或鹼土金屬的硫酸鹽;有機化合物,例如單羧酸或多元羧酸及其鹽類,例如4-叔丁基苯甲酸、己二酸、二苯基醋酸、琥珀酸鈉或苯甲酸鈉;聚合化合物,例如離子共聚物(離聚物)。特佳者為1,3:2,4-雙(3’,4’-二甲基苯亞甲基山梨糖醇)、1,3:2,4-二(對甲基-二-苯亞甲基)山梨糖醇,以及1,3:2,4-二(苯亞甲基)山梨糖醇。
12. 填充材料及強化劑,例如碳酸鈣、矽酸鹽、玻璃纖維、玻璃珠、石棉絲、滑石、高領土、雲母、硫酸鋇、金屬氧化物及氫氧化物、碳黑、石墨、木粉及纖維粉或其它天然產物的粉末或纖維、合成纖維。
13. 其它添加劑,例如塑化劑、潤滑劑、乳化劑、顏料、流變添加劑、催化劑、流量控制劑、螢光增白劑、耐火劑、抗靜電劑及發泡劑。
14. 苯並呋喃酮及吲哚酮,例如以下專利所揭露者:美國專利第4,325,863號;美國專利第4,338,244號;美國專利第5,175,312號;美國專利第5,216,052號;美國專利第5,252,643號;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839;EP-A-0591102;
EP-A-1291384或3-[4-(2-乙醯氧基乙氧基)苯基]-5,7-二-叔丁基苯並呋喃-2-酮、5,7-二-叔丁基-3-[4-(2-硬脂醯氧-乙氧基)苯基]苯並呋喃-2-酮、3,3’-雙[5,7-二-(叔丁基-3-(4-[2-羥基乙氧基]苯基)苯并呋喃-2-酮、5,7-二-叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙醯氧-3,5-二甲基苯基)-5,7-二-叔丁基苯並呋喃-2-酮、3-(3,5-二甲基-4-三甲基乙醯氧基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(2-乙醯基-5-異辛基苯基)-5-異辛基-苯并呋喃-2-酮。
較佳地,上述組成物還含有一空間位阻的胺安定劑,以及/或一紫外線吸收劑,其係選自於下列所組成的組群中:s-三嗪、草醯替苯胺、羥基二苯甲酮、苯甲酸酯、α-氰基丙烯酸酯及不同於上式(I)或(II)的苯并三唑。
當添加額外的紫外線吸收劑時,它們的添加量較佳地係為0.1%至30%,更佳地為0.5%至15%,最佳為1%至10%(以重量計),以有機材料的重量為基礎。
式I或式II之紫外線吸收劑的總量及/或位阻胺安定劑,舉例來說,為0.5%至15%(以重量計),以有機材料的重量為基礎。
位阻胺光安定劑及不同類紫外線吸收劑的例子已提供於前述。
特佳之紫外線吸收劑為下列的s-嗪及苯並三唑;
;G1=CH(CH3)-COO-C2H5
=下列的混合物a)R1=R2=CH(CH3)-COO-C8H17,R3=R4=H;b)R1=R2=R3=CH(CH3)-COO-C8H17,R4=H;c)R1=R2=R3=R4=CH(CH3)-COO-C8H17
羥基苯基三嗪紫外線吸收劑是已知的,有部份已是商品項目。
最適當的苯并三唑紫外線吸收劑可以下列商品名買到:TINUVIN 384(RTM)、TINUVIN 928(RTM)、TINUVIN 900(RTM)、TINUVIN 328(RTM)及TINUVIN 1130(RTM)。
成份(c)之立體位阻胺化合物較佳地係選自於下列商品所購成的組群:DASTIB 845(RTM)、TINUVIN 770(RTM)、TINUVIN 765(RTM)、TINUVIN 144(RTM)、TINUVIN 123(RTM)、TINUVIN292(RTM)、TINUVIN 152(RTM)、TINUVIN 144(RTM)、MART LA 52(RTM)、MARK LA 57(RTM)、MARK LA 62(RTM)、MARK LA 67(RTM)、HOSTAVIN N 20(RTM)、HOSTAVIN N24(RTM)、SANDUVOR 3050(RTM)、SANDUVOR 3058(RTM)、DIACETAM 5(RTM)、SUMISORB TM 61(RTM)、UVINUL 4049(RTM)、SANDUVOR PR 31(RTM)、GOODRITE UV 3034(RTM)、GOODRITE UV 3150(RTM)、GOODRITE UV 3159(RTM)、GOODRITE 3110 x 128(RTM)、UVINUL 4050
H(RTM)、CHIMASSORB 944(RTM)、CHIMASSORB 2020 (RTM)、CYASORB UV 3346(RTM)、CYASORB UV 3529(RTM)、DASTIB 1082(RTM)、CHIMASSORB UV 3346(RTM)、CYASORB UV 3529(RTM)、DASTIB 1082(RTM)、CHIMASSORB 119(RTM)、UVASIL 299(RTM)、UVASIL 125(RTM)、UVASIL 2000(RTM)、UVINUL 5050 H(RTM)、LICHTSCHUTZSTOFF UV 31(RTM)、LUCHEM HA B 18 (RTM)、MARK LA 63(RTM)、MARK LA 68(RTM)、UVASORB HA 88(RTM)、TINUVIN 622(RTM)、HOSTAVIN N30(RTM)及FERRO AM 806(RTM)。
特別佳的是TINUVIN 770(RTM)、TINUVIN 292(RTM)、TINUVIN 123(RTM)、TINUVIN 144(RTM)及TINUVIN 152(RTM)。
本發明的又另一方面是使用式I或II之化合物作為有機材料中之紫外光(UV)與可見光(VIS)吸收劑。
這些化合物的定義及較佳的選擇亦適用於本發明的其它方面。
以下的例子乃用來說明本發明。
a)在15℃下將亞硝基硫酸(40%在硫酸中,14.0克,44.1毫莫耳)緩緩加入正在攪拌中之含有4-氨基-5-溴酞醯亞胺(95%,10.7克,39.9毫莫耳)的醋酸(200毫升)懸浮液。添加的過程中,利用冰浴,使反應混合物的溫度維持在15至17℃之間。添加完成之後(3刻鐘),繼續攪拌2小時。
然後將反應混合物移至一滴液漏斗,並在-15℃下緩緩加至一攪拌中之2-枯基-4-叔辛基苯酚(95%;13.7克,40.1毫莫耳)的甲醇/間-二甲苯(85/15體積比;200ml)溶液,其中含有氫氧化鈉微顆粒(1.8克,45.0毫莫耳)及醋酸鈉(13.1克,159.7毫莫耳)。在添加過程中,利用異丙醇-乾冰浴使反應混合物的溫度維持在-15℃至-9℃之間;利用一電極來測量pH值,並且藉著同時加入氫氧化鈉(30%水溶液,共250毫升)以將pH值維持高於5。添加完成之後(兩小時,初使pH13.7,最終pH5.6),移除冷卻浴,將紅色懸浮液攪拌過夜。加入水(150毫升)及甲苯(250毫升),將水相分離出,再以甲苯(1x250毫升)清洗。將全部有機相以水清洗(2x250毫升),乾燥(用MgSO4),過濾並將溶液蒸發,得到30克的紅色油。加入60克的甲醇,將懸浮液加熱使其迴流。冷卻後(冰浴),化合物1a結晶成紅色固
體,將其濾出,以甲醇清洗再乾燥。得到16.2克(27.4毫莫耳,68.8%)。
熔點:178-179℃
1H-NMR(300MHz,CD2Cl2),δ(ppm):13.14(s,1H),8.34(s,1H),8.18(s,1H),7.92(似d,1H),7.76(似d,1H),7.28-7.24(m,4H),7.20-7.15(m,1H),3.20(s,3H),1.87(s,2H),1.82(s,6H),1.51(s,6H),0.86(s,9H)。
b)將化合物1a(17.2克,29.1毫莫耳)、疊氮化鈉(99%;2.5克,38.1毫莫耳)與1-甲基-2-吡咯烷酮(60毫升)的混合物加熱至120℃。維持該溫度直到不再釋出氮氣(1.5小時)。將黑色溶液冷卻至25℃,然後添加水(100毫升)及甲苯(150毫升)。將水相分離出,再以甲苯(1x50毫升)清洗。將全部有機相以水清洗(3x50毫升),乾燥(用MgSO4),過濾並將溶液蒸發,得到17克的黏性紅色油,靜置後即固化。將粗製的材料溶在熱的甲苯中。加入己烷,令溶液冷卻,化合物1b結晶成黃色固體,將其濾出並乾燥(8克)。將濾液蒸發至乾燥,殘渣從己烷中結晶而出,又得到3.5克。產量為11.5克(21.9毫莫耳,75.3%)。
熔點:198-199℃
1H-NMR(300MHz,CD2Cl2),δ(ppm):10.97(s,1H),8.40-8.39(m,3H),7.76(似d,1H),7.31-7.24(m,4H),7.20-7.15(m,1H),3.25(s,3H),1.91(s,2H),1.83(s,6H),1.54(s,6H),0.86(s,9H)。
a)在室溫下將4-氨基-N-甲基酞醯亞胺(17.8克,10.0毫莫耳)、醋酸鈉(1.64克,20毫莫耳)及醋酸(30克)的混合物攪拌在一起。一滴一滴地加入溴(3.22克,20毫莫耳)的醋酸(10毫升)溶液,同時適當攪拌。在加了大約一半的溴之後形成沈澱。在溴添加完成之後,攪拌仍持續16小時。然後加水(40毫升),過濾以收集產物,用水(10毫升)清洗產物並將其乾燥。
產量:3.18克(95%)。
熔點:216-218℃
1H-NMR(300MHz,DMSO-d6),δ(ppm):7.92(s,1H),6.46(s,寬,2H),2.96(s,3H)。
b)在15℃下將亞硝基硫酸(40%,溶於硫酸中;14.0克,44.1毫莫耳)緩緩加至攪拌中3-氨基-4,6-二溴酞醯亞胺(13.4克,40.0毫莫耳)的醋酸(200毫升)懸浮液。添加的過程中,利用冰浴,使反應混合物的溫度維持在15至17℃之間。添加完成之後(3刻鐘),繼續攪拌1小時。然後將反應混合物移至一滴液漏斗,並在-15℃下緩緩加至一攪拌中之含有2-枯基-4-叔辛基苯酚(95%;13.7克,40.1毫莫耳)的甲醇/間-二甲苯(85/15體積比;200ml)溶液,其中含
有氫氧化鈉微顆粒(1.8克,45.0毫莫耳)及醋酸鈉(13.1克,159.7毫莫耳)。在添加過程中,利用異丙醇-乾冰浴使反應混合物的溫度維持在-15℃至-9℃之間;利用一電極來測量pH值,並且藉著同時加入氫氧化鈉(30%水溶液,共250毫升)以將pH值維持高於5。添加完成之後(兩小時,初使pH13.7,最終pH5.6),移除冷卻浴,將紅色懸浮液攪拌過夜。化合物2a結晶成紅色固體,將其濾出,以異丙醇清洗再乾燥。
產量:16.6克(62%)。
熔點:180℃
1H-NMR(300MHz,CDCl3),δ(ppm):11.70(s,1H),8.14(s,1H),7.78(似d,1H),7.70(似d,1H),7.30-7.28(m,4H),7.21-7.17(m,1H),3.16(s,3H),1.82(s,6H),1.81(s,2H),1.46(s,6H),0.83(s,9H)。
c)將化合物2b(6.70克,10毫莫耳)、疊氮化鈉(99%;0.85克,13毫莫耳)與1-甲基-2-吡咯烷酮(25毫升)的混合物加熱至50℃。維持該溫度直到不再釋出氮氣(2小時)。將黑色溶液冷卻至25℃,然後添加水(25毫升)及醋酸乙酯(50毫升)。將水相分離出,過濾以收集沈澱在醋酸乙酯中的產物。將粗製的原料在熱甲苯(20毫升)中再結晶,將其濾出並乾燥。
產量:1.05克(17.4%)。
熔點:221-225℃(dec.)
1H-NMR(300MHz,CDCl3),δ(ppm):10.89(s,1H),8.41
(s,1H),8.39(似d,1H),7.74(似d,1H),7.29-7.26(m,4H),7.22-7.17(m,1H),3.26(s,3H),1.87(s,2H),1.84(s,6H),1.53(s,6H),0.84(s,9H)。
式3a之中間體化合物及與其類似之化合物亦可用來作為紫外線吸收劑。
a)在25℃下將KOH(53.3克,950毫莫耳)緩緩加至攪拌中之1b(49.8克,94.9毫莫耳)與乙醇/水(體積比1/1,總共200克加40毫升)的混合物。進一步以乙醇(50毫升)稀釋之後,將混合物加熱至80℃,並維持19.75小時。再加KOH(2.65克,47.2毫莫耳),並在80℃下持續攪拌29小時。然後在一迴旋蒸發器中將乙醇蒸發,將所得的橘色懸浮液以水(500毫升)稀釋。緩緩加入HCl(水溶液32% w/w)以將混合物酸化(pH2),將所得的黃色沈澱物濾出。以水(3x100毫升)清洗濾餅,在40℃的真空爐中乾燥,得到3a黃色固體(53.3克)。
熔點:150-175℃(dec.)
HPLC-UV/APCI-MS negative:529.3(M);calcd.for C31H35N3O5:529.3
1H-NMR(300MHz,DMSO-d6),δ(ppm):10.38(s,1H),8.57(br s,2H),7.98(d,J=1.9Hz,1H),7.64(d,J=1.9Hz,1H),7.26-7.18(m,4H),7.14-7.08(m,1H),1.80(s,2H),1.75(s,6H),1.43(s,6H),0.78(s,9H).
b)-d);3d(I):令攪拌中之3a(4.2克,7.9毫莫耳)與甲苯(40克)的混合物進行迴流直到水停止形成(3.75小時;t1),所形成的水藉由一Dean-Stark trap來收集。然後加入苯胺(98%;0.83克,8.7毫莫耳),所得混合物再迴流1.25小時(t2)。在一迴旋蒸發器中將甲苯蒸發,所得殘渣藉由色層
分析(矽膠,己烷/甲苯/醋酸乙酯9/0.5/1)來純化,得到3d(I),為黃色固體(2.4克,51.6%)。
熔點:220-221℃
Anal.calcd.for C37H38N4O3(586.74):C,75.74;H,6.53;N,9.55.Found:C,75.52;H,6.53;N,9.28.
1H-NMR(400MHz,DMSO-d6),δ(ppm):10.26(br s,1H),8.68(s,2H),7.96(d,J=1.8Hz,1H),7.69(d,J=1.8Hz,1H),7.56-7.45(m,5H),7.26-7.20(m,4H),7.14-7.10(m,1H),1.82(s,2H),1.76(s,6H),1.45(s,6H),0.79(s,9H).
b)-d);3d(II):類似於3d(I),從3a(6.35克,12.0毫莫耳)、甲苯(70克)及4-氨基苯甲腈(97%;1.6克,13.1毫莫耳)製備3d(II),迴流分別持續1.1小時(t1)及2.25小時(t2)。所得殘渣藉由色層分析(矽膠,甲苯)來純化,得到3d(II),為黃色固體(4.2克,57.3%)。
熔點:252-253℃
Anal.calcd.for C38H37N5O3(611.75):C,74.61;H,6.10;N,11.45.Found:C,74.04;H,5.83;N,11.37.
1H-NMR(400MHz,DMSO-d6),δ(ppm):10.24(br s,1H),8.72(s,2H),8.05(d,J=8.5Hz,2H),7.95(d,J=1.8Hz,1H),7.76(d,J=8.5Hz,2H),7.69(d,J=1.8Hz,1H),7.26-7.18(m,4H),7.16-7.10(m,1H),1.82(s,2H),1.76(s,6H),1.44(s,6H),0.79(s,9H).
b)-d);3d(III):類似於3d(I),從3a(6.35克,12.0毫莫耳)、
甲苯(70克)及2-氯苯胺(98%;1.7克,13.1毫莫耳)製備3d(III),迴流分別持續1.0小時(t1)及3.25小時(t2)。所得殘渣藉由色層分析(矽膠,甲苯/醋酸乙酯9/1)來純化,得到3d(III),為黃色固體(2.2克,29.5%)。
熔點:179-180℃
Anal.calcd.for C37H37ClN4O3(621.19):C,71.54;H,6.00;Cl,5.71;N,9.02.Found:C,71.04;H,5.90;Cl,5.93;N,8.89.
1H-NMR(300MHz,DMSO-d6),δ(ppm):10.22(s,1H),8.76(s,2H),7.95(d,J=2.1Hz,1H),7.75-7.67(m,3H),7.62-7.53(m,2H),7.27-7.19(m,4H),7.15-7.09(m,1H),1.82(s,2H),1.76(s,6H),1.45(s,6H),0.79(s,9H).
b)-d);3d(IV):類似於3d(I),從3a(6.35克,12.0毫莫耳)、甲苯(70克)及2,6-二異丙基苯胺(90%;2.6克,13.2毫莫耳)製備3d(IV),迴流分別持續1.0小時(t1)及3.0小時(t2)。所得殘渣藉由色層分析(矽膠,甲苯)來純化,得到3d(IV),為黃色固體(3.3克,41.0%)。
熔點:210-211℃
Anal.calcd.for C43H50N4O3(670.90):C,76.98;H,7.51;N,8.35.Found:C,76.70;H,7.47;N,8.29.
1H-NMR(300MHz,CD2Cl2),δ(ppm):11.03(s,1H),8.53(s,2H),8.45(d,J=2.4Hz,1H),7.79(d,J=2.4Hz,1H),7.58-7.53(m,1H),7.39-7.36(m,2H),7.33-7.26(m,4H),7.22-7.16(m,1H),2.78(septet,J=6.8Hz,2H),
1.93(s,2H),1.85(s,6H),1.56(s,6H),1.19(d,J=6.8Hz,12H),0.88(s,9H).
b)-d);3d(V):類似於3d(I),從3a(6.35克,12.0毫莫耳)、甲苯(70克)及乙醇胺(90%;0.81克,13.1毫莫耳)製備3d(V),迴流分別持續1.25小時(t1)及1.5小時(t2)。所得殘渣藉由色層分析(矽膠,甲苯)來純化,得到3d(V),為黃色固體(2.8克,42.1%)。
熔點:161-162℃
Anal.calcd.for C33H38N4O4(554.70):C,71.46;H,6.90;N,10.10.Found:C,71.07;H,6.92;N,10.03.
1H-NMR(300MHz,DMSO-d6),δ(ppm):10.23(s,1H),8.57(s,2H),7.94(d,J=2.2Hz,1H),7.67(d,J=2.2Hz,1H),7.26-7.18(m,4H),7.14-7.08(m,1H),4.88(t,J=5.9Hz,1H),3.72-3.59(m,4H),1.81(s,2H),1.75(s,6H),1.44(s,6H),0.78(s,9H).
b)N,N’-二環己基碳化二亞胺(99%;2.7克,13.0毫莫耳)、3a(6.35克,12.0毫莫耳)與二氯甲烷(40毫升)的混合物在25℃下攪拌一小時。濾出N,N’-二環己基脲,並在一迴旋蒸發器中將二氯甲烷蒸發,得到3b,為黃色固體(5.5克,89.6%)。
熔點:145-160℃(dec.)
HPLC-UV/APCI-MS.negative):511.2(M);calcd.for C31H33N3O4:511.2
1H-NMR(300MHz,CD2Cl2),δ(ppm):10.89(s,1H),8.63
(s,2H),8.44(d,J=2.3Hz,1H),7.81(d,J=2.3Hz,1H),7.31-7.24(m,4H),7.22-7.15(m,1H),1.91(s,2H),1.84(s,6H),1.55(s,6H),0.86(s,9H).
1Viacryl®SC303:丙烯酸酯樹酯(Solutia,原Vianova樹脂)
2Viacryl®SC370:丙烯酸酯樹酯(Solutia,原Vianova樹脂)
3Solvesso ®100:芳香烴,bp.163-180℃(Exxon Corp.)
4Maprenal® MF 650:三聚氰胺樹脂(Solutia,原Vianova樹脂)
5Solvesso ®150:芳香烴,bp.180-203℃(Exxon Corp.)
6Crystal oil 30:脂肪烴,bp.145-200℃(Shell Corp.)
7Baysilone MA:勻染劑(Bayer AG)
Tinuvin 384®,市售紫外線吸收劑,來自於Ciba Specialty Chemicals。
Tinuvin 928®,市售紫外線吸收劑,來自於Ciba Specialty Chemicals。
Tinuvin 400®,市售紫外線吸收劑,來自於Ciba Specialty Chemicals。
Tinuvin 109®,市售紫外線吸收劑,來自於Ciba Specialty Chemicals。
草醯替苯胺是Sanduvor 3206。
例A1及A3的化合物1b及3d(I)-(V)為依據本發明之紫外線吸收劑。
Tinuvin 152®,位阻胺安定劑,來自於Ciba Specialty Chemicals。
此紫外線吸收劑的光學性質依下述評價:將本發明之紫外線吸收劑加入一熱固性壓克力/三聚氰胺透明塗層中(以Viacryl®SC303/Viacryl®SC370/MaprenalMF®650為基礎)濃度為3%,以配方之固體含量為基礎(固體含量:50.4%)。將透明塗層噴在玻璃板上,熟成(130℃/30’)之後得到厚度為20μm的透明塗層的乾燥薄膜。
在將試樣曝光之前,使用UV/VIS光譜儀(Perkin Elmer,Lamda 40)來記錄UV吸收光譜。參考組:未安定之壓克力/三聚氰胺透明塗層。然後,依據SAE J 1960將試樣曝露於Xenon-WOM老化試驗儀(Atlas Corp.)。在曝光後留存的紫外線吸收劑的百分比(在最大λ值測試)乃藉由在規律的曝光時間間隔之後記錄紫外線吸收光譜而監控。測試結果摘於表1。
在一第二實例中,將兩層後續的透明塗層塗覆於彼此之上。第一層透明塗層(透明塗層I)係經過安定,並且依例B1中所詳述者來塗覆。之後將第二層熱固性壓克力/三聚氰胺透明塗層(以Viacryl®SC303/Viacryl®SC370/Maprenal®MF650為基礎)噴在第一透明塗層上,在熟成(130℃/30’)之後,生成厚度40μm的第二透明塗層(透明塗層II)的乾燥膜。第二透明塗層係使用一種紫外線吸收劑組合來安定,其中含有3%Tinuvin 109/1.5%Tinuvin 400及1%Tinuvin152作為
共安定劑(HALS)。參考組:未經安定化的第一透明塗層。如例B1所述,在將試樣曝光之前,使用UV/VIS光譜儀(Perkin Elmer,Lamda 40),來記錄紫外線穿透光譜。然後,依據SAE J 1960,令試樣曝光於Xenon-WOM老化試驗器(Atlas Corp.)。藉由在規律的曝光時間間隔之後記錄穿透光譜來監控穿透值(在396nm測定),作為曝光時間的函數。
如例B1所述製備一熱固性壓克力/三聚氰胺塗層。將此塗料噴灑在電塗覆之鋁板(ED6950A,10x30cm)上,該鋁板係如從ACT實驗室(ACT Laboratories,Inc.,South-field,Michigan 48 075,USA)所購得者,在熟成之後得到一層厚度20μm的乾燥薄膜。然後,依據SAE J 1960令該鋁板曝光於
Xenon-WOM老化試驗器(Atlas Corp.)。在透明塗層下方的電塗層的紫外線防護程度係在規律的曝光時間間隔下監控,作為黃變(yellowing)(依據DIN 6174 b*值)的函數。結果摘於表3。
結果清楚地顯示:
a)在無適當的紫外線防護之下,電塗層有明顯的黃變/紫外光引發之降解
b)使用現有的UV吸收劑包裝(Tinuvin109/Tinuvin 400)對電塗層的保護不足,其切斷的是介於300-385nm的所有紫外光
c)使用在可見光波長區有明顯吸收的UV吸收劑的電塗層有絕佳的保護
如例2中所詳述者,在經過電塗覆的鋁板(ED 6950A,10x30cm)上塗覆兩層後續的透明塗層,該鋁板係如從ACT實驗室(ACT Laboratories,Inc.,South-field,Michigan 48 075,USA)所購得者。參考組:a)兩層透明層都未經過安定化,b)第二透明塗層係以現有的以Tinuvin109/Tinuvin 400為基礎的UV吸收劑包裝來安定,亦即,切斷介於300-385nm的所有紫外光。
然後依據SAE J 1960令試樣曝光於Xenon-WOM老化
試驗器(Atlas Corp.)。透明塗層與光敏性電塗層之間的接著性係在規律的時間間隔下藉由百格試驗(cross hatch)(ISO 2409)及隨後的捲帶試驗而測定。試驗結果摘於表4。
實驗參數如例B1中所列舉者,除了結合使用HALS作為共安定劑來對紫外線吸收劑作測試,亦即,1%TINUVIN®123,以配方的固體含量為基礎。
又一實例中,兩層後續的透明塗層塗覆在彼此之上。第一透明塗層(透明塗層I)係以本發明之紫外線吸收劑與一空間位阻的胺來進行安定,並且依例B1所述來塗覆。隨後將第二熱固性壓克力/三聚氰胺透明塗層(以Viacryl®SC 303/Viacryl®SC 307/Maprenal®MF650為基礎)噴灑在第一透明塗層上,熟成(130℃/30’)之後得到厚度為40μm的第二透明塗層(透明塗層II)的乾燥薄膜。第二透明塗層以3% Tinuvin® 109/1.5% Tinuvin 400®之紫外線吸收劑組合來安定,以及Tinuvin 152®作為共安定劑。參考組是未安定的第一透明塗層。
如例B1中所述,在將試樣曝光之前,使用UV/VIS光譜儀(Perkin Elmer,Lamda 40),來記錄紫外線穿透光譜。然後,依據SAE J 1960,令試樣曝光於Xenon-WOM老化試驗器(Atlas Corp.)。藉由在規律的曝光時間間隔之後記錄穿透
光譜來監控穿透值(在396nm測定),作為曝光時間的函數。測試結果摘於表6:
透明塗層II配方:
Claims (20)
- 一種如式(I)或(II)之化合物,
- 依據申請專利範圍第1項的式(I)或(II)之化合物,其中R1為氫、1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至4碳原子的1至4個烷基取代的該苯基或該苯烷基;或R1為基或基其中L是1至12碳原子的伸烷基、2至12碳原子的亞烷基、亞苄基(benzylidene)、伸對苯基二甲基(p-xylylene)或5至7碳原子的伸環烷基;R2為1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;或R2為-(CH2)m-CO-X1-(Z)p-Y-R15其中X1是-O-,Y是-O-或一直接鍵,Z是C2-C12伸烷基、插入有1至3個氮原子、氧原子或的C4-C12伸烷基,或當Y是一個直接鍵時,Z亦可為一直接鍵;m是2,p是1, R15是氫、C1-C12烷基、或或基R5、R6、R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C18烯基、C2-C6炔基、C5-C12環烷基、苯基、萘基或C7-C15苯烷基;或該直鏈或支鏈C1-C24烷基、直鏈或支鏈C2-C24烯基、C5-C12環烷基、C2-C6炔基可被一或多個-F、-OH、-OR22、-NH2、-NHR22、-N(R22)2、-NHCOR23、NR22COR23、-OCOR24、-COR25、-SO2R26、-PO(R27)n(R28)2-n、-Si(R29)n(R30)3-n、-Si(R22)3、-N+(R22)3A-、-S+(R22)2A-、環氧乙烷基取代;該直鏈或支鏈C1-C24烷基、直鏈或支鏈之未經取代或經取代之C2-C24烯基、C5-C12環烷基或C2-C6炔基亦可嵌插一或多個-O-、-S-、-NH-或-NR22-基;該苯基、萘基或C7-C15苯烷基亦可被一或多個鹵素、-CN-、-CF3、-NO2、-NHR22、-N(R22)2、-SO2R26、-PO(R27)n(R28)2-n、-OH、-OR22、-COR25、-R25所取代;其中n是0、1或2; R22是直鏈或支鏈C1-C18烷基、直鏈或支鏈C2-C18烯基、C5-C10環烷基、苯基、萘基、C7-C15苯烷基,或兩個R22當接到N或Si原子時可與其所連接的原子共同形成吡咯烷、哌啶或嗎啉環;R23是氫、OR22、NHR22、N(R22)2或與R22相同意義,R24是OR22、NHR22、N(R22)2或與R22相同意義,R25是氫、OH、OR22、NHR22或N(R22)2、O-縮水甘油基或與R22相同意義,R26是OH、OR22、NHR22或N(R22)2,R27是NH2、NHR22或N(R22)2,R28是OH或OR22,R29是Cl或OR22,R30是直鏈或支鏈C1-C18烷基;或E1是或基其中R1至R8如上述定義,且Q是直鏈或支鏈C2-C12伸烷基、C5-C10伸環烷基或伸對苯基或下列基團
- 依據申請專利範圍第2項之化合物,其中R1為氫、1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至4碳原子的1至4個烷基取代的該苯基或該苯烷基;R2為1至24碳原子的直鏈或支鏈烷基、2至18碳原子的直鏈或支鏈烯基、5至12碳原子的環烷基、7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;或R2為-(CH2)2-CO-O-(Z)-O-R15其中Z是C2-C12伸烷基、插入有1至3個氧原子的C4-C12伸烷基;R15是氫、C1-C12烷基、或或基R5、R6、R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、直鏈或支鏈C1-C24烷基、C5-C12環烷基、苯 基、C7-C15苯烷基;或該直鏈或支鏈C1-C24烷基或C5-C12環烷基可被一或多個-F、-OH、-OR22、-NH2、-NHR22、-N(R22)2取代;該苯基或C7-C15苯烷基亦可被一或多個鹵素、-CN、-CF3、-OH、-OR22、-COR22、-R22所取代;其中R22是直鏈或支鏈C1-C18烷基、直鏈或支鏈C2-C18烯基、C5-C10環烷基、C6-C16苯基或萘基、C7-C15苯烷基;或E1是或基其中R1至R8如上述定義,且Q是C2-C12伸烷基、C5-C7伸環烷基、伸對苯基或下列基團
- 依據申請專利範圍第3項之化合物,其中R1為氫、1至12碳原子的直鏈或支鏈烷基或7至15碳原子的苯烷基; R2為1至12碳原子的直鏈或支鏈烷基或7至15碳原子的苯烷基、苯基,或在苯環上被1至3個1至4碳原子的烷基取代的該苯基或該苯烷基;R5與R6為氫,或其中一個是Cl或Br;R7及R8獨立地為氫、Cl或Br;X是O或NE1,其中E1是氫、未被取代的或被1至4個OH取代的直鏈或支鏈C1-C6烷基、未被取代的或被F、CF3、CN或Cl取代的苯基,或C7-C9苯烷基。
- 依據申請專利範圍第1項之化合物,其係為式(I)之化合物。
- 依據申請專利範圍第1項之化合物,其為或
- 一種用來製備式(I)或(II)的化合物的方法
- 如申請專利範圍第7項之方法,其中該反應是在一溶劑中進行。
- 如申請專利範圍第7項之方法,其中式III、IV或V的化合物的量相對於式X的疊氮化物的量的莫耳比例是1:1至1:3。
- 如申請專利範圍第7項之方法,其中該反應是在一催化劑的存在下進行。
- 一種對於光引發的降解具有安定性的組成物,包含(a)一受到光引發的降解的有機材料,以及(b)一種如申請專利範圍第1項之式I或II之化合物。
- 依據申請專利範圍第11項之組成物,其尚包含一種空間位阻的胺安定劑及/或一種UV吸收劑,選自於下列所構成之組群中:s-三嗪類(s-triazines)、草醯替苯胺類(oxanilides)、羥基二苯甲酮類(hydroxybenzophenones)、苯甲酸酯類(benzoates)、α-氰基丙烯酸酯類及不同於申請專利範圍第1項中式(I)或(II)的苯并三唑類。
- 依據申請專利範圍第11項之組成物,其中該有機材料是一種記錄材料。
- 依據申請專利範圍第11項之組成物,其中該有機材料是一種天然的、半合成的或合成的聚合物。
- 依據申請專利範圍第14項之組成物,其中該聚合物是一種熱塑性聚合物。
- 依據申請專利範圍第11項之組成物,其中該有機材料是 一塗層。
- 依據申請專利範圍第16項之組成物,其中該塗層是一汽車用塗層。
- 依據申請專利範圍第16項之組成物,其中該塗層是施用在一種對波長大於380nm的電磁輻射敏感的基材上。
- 依據申請專利範圍第11項之組成物,其中式I或II之化合物的存在量,以有機材料的重量為基礎,是0.1%至30重量%。
- 一種如式I或II之化合物的用途,作為塗層中UV(紫外光)及可見光(VIS)的吸收劑。
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US20080157025A1 (en) | 2008-07-03 |
WO2006082145A1 (en) | 2006-08-10 |
BRPI0606893A2 (pt) | 2009-07-21 |
CN101111496A (zh) | 2008-01-23 |
ATE502942T1 (de) | 2011-04-15 |
EP1844049A1 (en) | 2007-10-17 |
JP4975646B2 (ja) | 2012-07-11 |
US7695643B2 (en) | 2010-04-13 |
DE602006020839D1 (de) | 2011-05-05 |
RU2007132974A (ru) | 2009-03-10 |
EP1844049B1 (en) | 2011-03-23 |
KR20070104640A (ko) | 2007-10-26 |
JP2008528657A (ja) | 2008-07-31 |
KR101322194B1 (ko) | 2013-10-30 |
CN101111496B (zh) | 2010-12-29 |
RU2414471C2 (ru) | 2011-03-20 |
TW200633988A (en) | 2006-10-01 |
BRPI0606893B1 (pt) | 2014-10-14 |
MY144674A (en) | 2011-10-31 |
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