JP5765938B2 - 有機金属化合物を主成分とする光潜伏性触媒 - Google Patents

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Publication number

JP5765938B2

JP5765938B2 JP2010529346A JP2010529346A JP5765938B2 JP 5765938 B2 JP5765938 B2 JP 5765938B2 JP 2010529346 A JP2010529346 A JP 2010529346A JP 2010529346 A JP2010529346 A JP 2010529346A JP 5765938 B2 JP5765938 B2 JP 5765938B2

Authority

JP

Japan

Prior art keywords

alkyl

phenyl

substituted

hydrogen

alkoxy

Prior art date

2007-10-17

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 - Fee Related

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• 239000003054 catalyst Substances 0.000 title claims description 76
• 150000002902 organometallic compounds Chemical class 0.000 title description 4
• 239000000203 mixture Substances 0.000 claims description 180
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 178
• 125000000217 alkyl group Chemical group 0.000 claims description 149
• -1 diphenylamino Chemical group 0.000 claims description 144
• 239000001257 hydrogen Substances 0.000 claims description 134
• 229910052739 hydrogen Inorganic materials 0.000 claims description 134
• 150000001875 compounds Chemical class 0.000 claims description 103
• 150000002431 hydrogen Chemical class 0.000 claims description 86
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 150000002367 halogens Chemical class 0.000 claims description 63
• 229910052751 metal Inorganic materials 0.000 claims description 52
• 239000002184 metal Substances 0.000 claims description 52
• 238000000034 method Methods 0.000 claims description 52
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 46
• 125000001624 naphthyl group Chemical group 0.000 claims description 46
• 229920005862 polyol Polymers 0.000 claims description 42
• 239000003973 paint Substances 0.000 claims description 37
• 150000003077 polyols Chemical class 0.000 claims description 37
• 239000012948 isocyanate Substances 0.000 claims description 36
• 150000002513 isocyanates Chemical class 0.000 claims description 36
• 239000000758 substrate Substances 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 28
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 26
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
• 238000004132 cross linking Methods 0.000 claims description 21
• 229910052726 zirconium Inorganic materials 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 239000000463 material Substances 0.000 claims description 20
• 239000004814 polyurethane Substances 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 229910052718 tin Inorganic materials 0.000 claims description 20
• 125000005561 phenanthryl group Chemical group 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 239000000853 adhesive Substances 0.000 claims description 17
• 230000001070 adhesive effect Effects 0.000 claims description 17
• 238000010438 heat treatment Methods 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 15
• 239000000654 additive Substances 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 229910052719 titanium Inorganic materials 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 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 14
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 238000007639 printing Methods 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 150000008366 benzophenones Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 230000005670 electromagnetic radiation Effects 0.000 claims description 7
• 239000006260 foam Substances 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 150000002540 isothiocyanates Chemical class 0.000 claims description 7
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
• 101150065749 Churc1 gene Proteins 0.000 claims description 6
• 102100038239 Protein Churchill Human genes 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 238000004382 potting Methods 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
• 239000012778 molding material Substances 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 239000003566 sealing material Substances 0.000 claims description 3
• 230000015572 biosynthetic process Effects 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 5
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
• 230000001678 irradiating effect Effects 0.000 claims 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 70
• 239000000047 product Substances 0.000 description 57
• 239000000243 solution Substances 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 238000004519 manufacturing process Methods 0.000 description 46
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 44
• 239000007787 solid Substances 0.000 description 40
• 238000002844 melting Methods 0.000 description 37
• 230000008018 melting Effects 0.000 description 37
• 229910052786 argon Inorganic materials 0.000 description 35
• 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 33
• 238000000576 coating method Methods 0.000 description 33
• 238000002360 preparation method Methods 0.000 description 30
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
• 239000008199 coating composition Substances 0.000 description 24
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
• 239000005056 polyisocyanate Substances 0.000 description 21
• 229920001228 polyisocyanate Polymers 0.000 description 21
• 239000000843 powder Substances 0.000 description 21
• 239000011248 coating agent Substances 0.000 description 20
• 238000009472 formulation Methods 0.000 description 19
• 239000000178 monomer Substances 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
• 238000001723 curing Methods 0.000 description 17
• 230000005855 radiation Effects 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• 229910052782 aluminium Inorganic materials 0.000 description 16
• 229920002635 polyurethane Polymers 0.000 description 16
• 239000012965 benzophenone Substances 0.000 description 15
• 239000000049 pigment Substances 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 125000002524 organometallic group Chemical group 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• 125000004429 atom Chemical group 0.000 description 13
• 239000013078 crystal Substances 0.000 description 13
• 229920000642 polymer Polymers 0.000 description 13
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• 239000011347 resin Substances 0.000 description 13
• 239000010936 titanium Substances 0.000 description 13
• NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 12
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• 125000002252 acyl group Chemical group 0.000 description 11
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• 238000004821 distillation Methods 0.000 description 11
• 239000003446 ligand Substances 0.000 description 11
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• 239000005058 Isophorone diisocyanate Substances 0.000 description 10
• 239000007983 Tris buffer Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
• NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 10
• ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 10
• CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 9
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• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 239000000976 ink Substances 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
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• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
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