JP6459394B2 - 光重合増感剤組成物とそれを含む光重合性組成物 - Google Patents
光重合増感剤組成物とそれを含む光重合性組成物 Download PDFInfo
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- JP6459394B2 JP6459394B2 JP2014219798A JP2014219798A JP6459394B2 JP 6459394 B2 JP6459394 B2 JP 6459394B2 JP 2014219798 A JP2014219798 A JP 2014219798A JP 2014219798 A JP2014219798 A JP 2014219798A JP 6459394 B2 JP6459394 B2 JP 6459394B2
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- anthracene
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- ether
- compound
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- 239000000203 mixture Substances 0.000 title claims description 99
- -1 anthracene compound Chemical class 0.000 claims description 154
- 150000001875 compounds Chemical class 0.000 claims description 154
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 100
- 239000003999 initiator Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000003505 polymerization initiator Substances 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 230000001678 irradiating effect Effects 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000008033 biological extinction Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- 239000011248 coating agent Substances 0.000 description 28
- 238000006116 polymerization reaction Methods 0.000 description 28
- 238000000576 coating method Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 17
- 238000002156 mixing Methods 0.000 description 13
- 239000001294 propane Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 11
- QPCMKVGYDGXROK-UHFFFAOYSA-N (10-octanoyloxyanthracen-9-yl) octanoate Chemical compound C(CCCCCCC)(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(CCCCCCC)=O QPCMKVGYDGXROK-UHFFFAOYSA-N 0.000 description 9
- 238000004040 coloring Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 6
- UOPZCYRGLJQIHQ-UHFFFAOYSA-N 1-(2-acetyloxypropoxy)propan-2-yl acetate Chemical compound CC(=O)OC(C)COCC(C)OC(C)=O UOPZCYRGLJQIHQ-UHFFFAOYSA-N 0.000 description 6
- KWDCKLXGUZOEGM-UHFFFAOYSA-N 1-methoxy-3-(3-methoxypropoxy)propane Chemical compound COCCCOCCCOC KWDCKLXGUZOEGM-UHFFFAOYSA-N 0.000 description 6
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 6
- JZKVBTRQEQWFCU-UHFFFAOYSA-N 3-(3-acetyloxypropoxy)propyl acetate Chemical compound CC(=O)OCCCOCCCOC(C)=O JZKVBTRQEQWFCU-UHFFFAOYSA-N 0.000 description 6
- KEPGNQLKWDULGD-UHFFFAOYSA-N 3-(3-prop-2-enoyloxypropoxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCCCOC(=O)C=C KEPGNQLKWDULGD-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 229940028820 didecyl ether Drugs 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229960000834 vinyl ether Drugs 0.000 description 6
- DFMJWQFCLBTBHC-UHFFFAOYSA-N (10-butoxycarbonyloxyanthracen-9-yl) butyl carbonate Chemical compound C(CCC)OC(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(=O)OCCCC DFMJWQFCLBTBHC-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- LAJCSHRWLHTXHK-UHFFFAOYSA-N (10-propoxycarbonyloxyanthracen-9-yl) propyl carbonate Chemical compound C(CC)OC(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(=O)OCCC LAJCSHRWLHTXHK-UHFFFAOYSA-N 0.000 description 4
- RNJVAUBBYGWVBF-UHFFFAOYSA-N 1-(2-prop-2-enoyloxypropoxy)propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COCC(C)OC(=O)C=C RNJVAUBBYGWVBF-UHFFFAOYSA-N 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- GDFQRDTZOFMSSM-UHFFFAOYSA-N (10-methoxycarbonyloxyanthracen-9-yl) methyl carbonate Chemical compound C1=CC=C2C(OC(=O)OC)=C(C=CC=C3)C3=C(OC(=O)OC)C2=C1 GDFQRDTZOFMSSM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KHEDNBRORNZTNH-UHFFFAOYSA-N [10-(2-ethylhexanoyloxy)anthracen-9-yl] 2-ethylhexanoate Chemical compound C(C)C(C(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(C(CCCC)CC)=O)CCCC KHEDNBRORNZTNH-UHFFFAOYSA-N 0.000 description 3
- GROQZUISBOBUSK-UHFFFAOYSA-N [10-(2-ethylhexoxycarbonyloxy)anthracen-9-yl] 2-ethylhexyl carbonate Chemical compound C(C)C(COC(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(=O)OCC(CCCC)CC)CCCC GROQZUISBOBUSK-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 150000008648 triflates Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OBKAPNBVQRIESX-UHFFFAOYSA-N (1,5-diethyl-10-pentoxycarbonyloxyanthracen-9-yl) pentyl carbonate Chemical compound C(C)C1=CC=CC2=C(C3=C(C=CC=C3C(=C12)OC(=O)OCCCCC)CC)OC(=O)OCCCCC OBKAPNBVQRIESX-UHFFFAOYSA-N 0.000 description 2
- FYPMMVCUYHHMDL-UHFFFAOYSA-N (1,5-dimethyl-10-pentoxycarbonyloxyanthracen-9-yl) pentyl carbonate Chemical compound CC1=CC=CC2=C(C3=C(C=CC=C3C(=C12)OC(=O)OCCCCC)C)OC(=O)OCCCCC FYPMMVCUYHHMDL-UHFFFAOYSA-N 0.000 description 2
- YHYQARHERJNHGZ-UHFFFAOYSA-N (1,5-dimethyl-10-propoxycarbonyloxyanthracen-9-yl) propyl carbonate Chemical compound CC1=CC=CC2=C(C3=C(C=CC=C3C(=C12)OC(=O)OCCC)C)OC(=O)OCCC YHYQARHERJNHGZ-UHFFFAOYSA-N 0.000 description 2
- NUMNPTVZWVXURK-UHFFFAOYSA-N (1-ethyl-10-pentoxycarbonyloxyanthracen-9-yl) pentyl carbonate Chemical compound C(C)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)OC(=O)OCCCCC)OC(=O)OCCCCC NUMNPTVZWVXURK-UHFFFAOYSA-N 0.000 description 2
- ACKUVGREPZUNCR-UHFFFAOYSA-N (1-methyl-10-pentoxycarbonyloxyanthracen-9-yl) pentyl carbonate Chemical compound CC1=CC=CC2=C(C3=CC=CC=C3C(=C12)OC(=O)OCCCCC)OC(=O)OCCCCC ACKUVGREPZUNCR-UHFFFAOYSA-N 0.000 description 2
- NZCXMLLQAOKFQK-UHFFFAOYSA-N (1-methyl-10-propoxycarbonyloxyanthracen-9-yl) propyl carbonate Chemical compound CC1=CC=CC2=C(C3=CC=CC=C3C(=C12)OC(=O)OCCC)OC(=O)OCCC NZCXMLLQAOKFQK-UHFFFAOYSA-N 0.000 description 2
- CTOSPCGRZKPFTA-UHFFFAOYSA-N (10-butanoyloxyanthracen-9-yl) butanoate Chemical compound C(CCC)(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC12)OC(CCC)=O CTOSPCGRZKPFTA-UHFFFAOYSA-N 0.000 description 2
- XBQLWGMSQVDUCP-UHFFFAOYSA-N (10-butoxycarbonyloxy-1,5-diethylanthracen-9-yl) butyl carbonate Chemical compound C(C)C1=CC=CC2=C(C3=C(C=CC=C3C(=C12)OC(=O)OCCCC)CC)OC(=O)OCCCC XBQLWGMSQVDUCP-UHFFFAOYSA-N 0.000 description 2
- GMUROYPGSBKELF-UHFFFAOYSA-N (10-butoxycarbonyloxy-1,5-dimethylanthracen-9-yl) butyl carbonate Chemical compound CCCCOC(=O)Oc1c2cccc(C)c2c(OC(=O)OCCCC)c2cccc(C)c12 GMUROYPGSBKELF-UHFFFAOYSA-N 0.000 description 2
- BURWNARUFSPNIO-UHFFFAOYSA-N (10-butoxycarbonyloxy-1-ethylanthracen-9-yl) butyl carbonate Chemical compound C(C)C1=CC=CC2=C(C3=CC=CC=C3C(=C12)OC(=O)OCCCC)OC(=O)OCCCC BURWNARUFSPNIO-UHFFFAOYSA-N 0.000 description 2
- CVUDLOPTZQZAKG-UHFFFAOYSA-N (10-butoxycarbonyloxy-1-methylanthracen-9-yl) butyl carbonate Chemical compound CC1=CC=CC2=C(C3=CC=CC=C3C(=C12)OC(=O)OCCCC)OC(=O)OCCCC CVUDLOPTZQZAKG-UHFFFAOYSA-N 0.000 description 2
- WGEAIXAVTXYFAI-UHFFFAOYSA-N (10-butoxycarbonyloxy-2,3-diethylanthracen-9-yl) butyl carbonate Chemical compound C(C)C1=CC2=C(C3=CC=CC=C3C(=C2C=C1CC)OC(=O)OCCCC)OC(=O)OCCCC WGEAIXAVTXYFAI-UHFFFAOYSA-N 0.000 description 2
- VGAUINDVHNFOMK-UHFFFAOYSA-N (10-butoxycarbonyloxy-2,3-dimethylanthracen-9-yl) butyl carbonate Chemical compound CC1=CC2=C(C3=CC=CC=C3C(=C2C=C1C)OC(=O)OCCCC)OC(=O)OCCCC VGAUINDVHNFOMK-UHFFFAOYSA-N 0.000 description 2
- DZIIIOIUDDUCEM-UHFFFAOYSA-N (10-butoxycarbonyloxy-2,6-diethylanthracen-9-yl) butyl carbonate Chemical compound C(C)C1=CC2=C(C3=CC=C(C=C3C(=C2C=C1)OC(=O)OCCCC)CC)OC(=O)OCCCC DZIIIOIUDDUCEM-UHFFFAOYSA-N 0.000 description 2
- UPKKYKXTCQXBRG-UHFFFAOYSA-N (10-butoxycarbonyloxy-2,6-dimethylanthracen-9-yl) butyl carbonate Chemical compound CC1=CC2=C(C3=CC=C(C=C3C(=C2C=C1)OC(=O)OCCCC)C)OC(=O)OCCCC UPKKYKXTCQXBRG-UHFFFAOYSA-N 0.000 description 2
- QMLVEJFOUZCQQS-UHFFFAOYSA-N (10-butoxycarbonyloxy-2-ethylanthracen-9-yl) butyl carbonate Chemical compound C(C)C1=CC2=C(C3=CC=CC=C3C(=C2C=C1)OC(=O)OCCCC)OC(=O)OCCCC QMLVEJFOUZCQQS-UHFFFAOYSA-N 0.000 description 2
- MMQHMWYEEWVGII-UHFFFAOYSA-N (10-ethoxycarbonyloxyanthracen-9-yl) ethyl carbonate Chemical compound C(C)OC(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC12)OC(=O)OCC MMQHMWYEEWVGII-UHFFFAOYSA-N 0.000 description 2
- HDXJWZHGDQGINF-UHFFFAOYSA-N (10-hexanoyloxyanthracen-9-yl) hexanoate Chemical compound C(CCCCC)(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(CCCCC)=O HDXJWZHGDQGINF-UHFFFAOYSA-N 0.000 description 2
- YPESPOJYFDMJPO-UHFFFAOYSA-N (10-nonanoyloxyanthracen-9-yl) nonanoate Chemical compound C(CCCCCCCC)(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC=12)OC(CCCCCCCC)=O YPESPOJYFDMJPO-UHFFFAOYSA-N 0.000 description 2
- ICDVRRFJYKMRAK-UHFFFAOYSA-N (10-propanoyloxyanthracen-9-yl) propanoate Chemical compound C(CC)(=O)OC=1C2=CC=CC=C2C(=C2C=CC=CC12)OC(CC)=O ICDVRRFJYKMRAK-UHFFFAOYSA-N 0.000 description 2
- KHTNKEAKUIDVLR-UHFFFAOYSA-N (2,3-diethyl-10-pentoxycarbonyloxyanthracen-9-yl) pentyl carbonate Chemical compound C(C)C1=CC2=C(C3=CC=CC=C3C(=C2C=C1CC)OC(=O)OCCCCC)OC(=O)OCCCCC KHTNKEAKUIDVLR-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
Description
本発明における化合物(A)は、一般式(1)に記載の構造を有するアントラセン化合物である。
本発明における化合物(B)としては、化合物に400nm〜500nmの波長範囲の光を照射したときの光の吸収における吸光係数の最大値を比較したとき、一般式(1)で表わされる化合物より該最大値が大きい化合物を用いる。
本発明に用いられる光重合性化合物としては、光カチオン重合する光カチオン重合性化合物であってもよく、光ラジカル重合する光ラジカル重合性化合物であってもよく、更には、それらの両方を含む光ハイブリッド重合性化合物であってもよい。
本発明に用いられる光カチオン重合性化合物は、ブレンステッド酸あるいはルイス酸等の酸によってカチオン重合する化合物である。例えば、エポキシ環、オキセタン環、テトラヒドロフラン環、テトラヒドロピラン環、ジオキソラン環、ジチアン環、トリチアン環、ジチオラン環等を含む環状エーテル類や環状チオエーテル類、チオエーテル類、ビニルエーテル類、ラクトン等を挙げることができる。
本発明で用いられる光ラジカル重合性化合物は、分子中にラジカルと反応しうる官能基(ラジカル重合性官能基)を有していれば特に限定されない。通常このような官能基として(メタ)アクリル基、ビニル基等の不飽和結合を含む官能基が挙げられ、これらを有する化合物としては以下のようなものが挙げられる。ラジカル重合性官能基は化合物中に少なくとも1つ含まれている必要があり、2以上含まれていても良い。
本発明で用いられる光カチオン重合開始剤は光照射により光カチオン重合性化合物に対する重合開始種を発生するものが用いられる。特に光照射によってブレンステッド酸又はルイス酸等を発生する光酸発生剤が好適に用いられる。
本発明で用いられる、光ラジカル重合開始剤は光照射により分解しラジカルを発生する化合物、または光照射により開始剤自体が励起し他の化合物と反応しラジカルを発生するような化合物等光照射によりラジカル開始種を発生するような化合物が選ばれる。
本発明に係る光重合性組成物には上記光カチオン重合性化合物、光ラジカル重合性化合物いずれについてもその分子中にカルボキシル基、フェノール性水酸基、スルホン酸基等のアルカリ可溶となる置換基を有する光重合性化合物も用いることができる。それらアルカリ可溶となる重合性化合物を用いる場合はこれらを含む光重合性組成物を、パタンを有するマスクを介して光照射し重合、硬化させたのちアルカリ現像により、マスクされた部分の未重合の光重合性組成物が取り除かれ、パタンを形成することが可能となる。
本発明に係る光重合性組成物は、式(1)に示される9,10−ビス(置換アシルオキシ)アントラセン化合物又は9,10−ビス(置換カルボニルオキシ)アントラセン化合物及び式(2)に示される化合物又はチオキサントン誘導体からなる光重合増感剤組成物、上述した光重合性化合物並びに光重合開始剤を混合して得ることができる。
本発明の光重合性組成物は光照射することにより重合、硬化させることができる。本発明に係る光重合性組成物は種々の方法で重合、硬化させることが可能である。例えば、適当な基材上に塗布したもの、該光重合性組成物を、スペーサを配したガラス板等にはさみこんだもの等に光を照射して塗膜やフィルム、シートを得ることができる。また、光を透過するような型に該光重合性組成物を流涎したもの等に光を照射することにより重合、硬化した成型物が得られる。また該光重合性組成物を塗布しその後適当なパタンを有するマスクを介して光を照射することにより、パターンに応じた重合、硬化を行うこともできる。
本発明における光照射の際に用いられる光源としては、波長が300〜500nmの波長の光を含む光源を使用することが好ましい。複数の波長成分を含む光源でもよいし、またLEDやレーザ光を用いるもので所謂単色光を発する光源でも構わない。具体的には高圧水銀ランプ、超高圧水銀メタルハライドランプ、ガリウムドープドランプ、マイクロ波励起方式UVランプ(例えばフュージョン(株)製のHバルブ、Dバルブ、Vバルブ)、365nm、375nm、395nm、405nm、436nm等の波長の光を発するLEDランプ又はレーザ光等が挙げられる。太陽光や白熱灯や蛍光灯等の照明器具の光の使用も可能である。
本発明に係る光重合性組成物は光照射によって反応、重合、硬化させることができるコーティング剤、塗料、インク、成型材等に用いることができる。具体的には金属や樹脂、ガラス、紙、木材等の基材上に塗布する塗料、ハードコート剤、汚れ防止膜、反射防止膜、衝撃緩衝膜、オーバーコート剤等のコーティング剤や保護膜材料、光硬化型の接着剤、粘着剤、光崩壊・分解型の塗料、塗膜、成型物、さらにホログラム材料等の光記録媒体又は光記録媒体向け材料、光造形用樹脂、3Dプリンタ用インク(樹脂)、電子回路や半導体製造用レジスト、液晶ディスプレイ、有機ELディスプレイ等のディスプレイ向けカラーフィルター用レジスト、ブラックマトリックス用レジスト、ドライフィルムレジスト等の電子材料向けレジスト、層間絶縁膜、保護膜、光取り出し膜、封止剤、シール材、スクリーン印刷・オフセット印刷・グラビア印刷等の印刷用インク、インクジェットプリンタ向けの光硬化型インク、レーザパタニング用組成物、レンズ、レンズアレイ、光導波路、導光板、光拡散板、回折素子、光学用接着剤等の光学部材、ナノインプリンティング用材料等の種々の用途への適用が可能である。本発明の光重合増感剤組成物及び光重合性組成物はその重合物、硬化物の着色が抑制されうることから特に、LCDや有機ELディスプレイのような映像関連デバイスやタッチパネル、レンズ等光学素子に用いるOCA(Optically Clear Adhesive)やOCR(Optical Clear Resin)などをはじめとする接着剤、粘着剤、コーティング剤などに好適に用いられる。
100重量部の3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート(ダイセル社製、セロキサイド2021P)と2重量部の光カチオン開始剤(ジフェニル−4−フェニルチオフェニルスルホニウムヘキサフルオロホスフェート、CPI−100P(サンアプロ社製))、1重量部の9,10−ビス(n−オクタノイルオキシ)アントラセン及び0.01重量部のアントラセン−9,10−ジブチルエーテルを室温で混合、溶解し光重合性組成物を調製した。この光重合性組成物を厚さ50μmのTAC(三酢酸セルロース)フィルム上にバーコータ(No.8)で塗布し膜厚およそ12μmの塗膜を形成した。その後、中心波長395nmのLED光(50mW/cm2)を照射し塗膜の表面べとつきがなくなるまでの照射時間(タックフリータイム)を測定したところ、140秒であった。またこの時の硬化塗膜の黄色度(YI)を測定したところYI=0.90であった。
実施例1のアントラセン−9,10−ジブチルエーテルの使用量を0.05重量部に変えた以外は実施例1と同様に塗膜の硬化を行ったところ、その時のタックフリータイムは125秒であった。また、この時の硬化塗膜の黄色度(YI)を測定したところYI=1.11であった。
実施例1のアントラセン−9,10−ジブチルエーテルの使用量を0.1重量部に変えた以外は実施例1と同様に塗膜の硬化を行ったところ、その時のタックフリータイムは105秒であった。また、この時の硬化塗膜の黄色度(YI)を測定したところYI=1.05であった。
100重量部の3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート(ダイセル社製、セロキサイド2021P)と2重量部の光カチオン開始剤(4−メチルフェニル)[4−(2−メチルプロピル)フェニル]ヨードニウムヘキサフルオロフォスフェート、イルガキュア250(ビー・エー・エス・エフ社製、「イルガキュア」はビー・エー・エス・エフ社の登録商標)、1重量部の9,10−ビス(n−オクタノイルオキシ)アントラセン及び0.1重量部のジエチルチオキサントンを室温で混合、溶解し光重合性組成物を調製した。この光重合性組成物を厚さ50μmのTAC(三酢酸セルロース)フィルム上にバーコータ(No.8)で塗布し膜厚およそ12μmの塗膜を形成した。その後、中心波長395nmのLED光(50mW/cm2)を照射し塗膜の表面べとつきがなくなるまでの照射時間(タックフリータイム)を測定したところ、12秒であった。またこの時の硬化塗膜の黄色度(YI)を測定したところYI=0.57であった。
100重量部の3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート(ダイセル社製、セロキサイド2021P)と2重量部の光カチオン開始剤(ジフェニル−4−フェニルチオフェニルスルホニウムヘキサフルオロホスフェート、CPI−100P(サンアプロ社製))、1重量部のアントラセン−9,10−ジブチルエーテルを室温で混合、溶解し光重合性組成物を調製した。このようにして得られた光重合性組成物を実施例1と同様に硬化させたところ、その時のタックフリータイムは90秒であった。また、この時の硬化塗膜の黄色度(YI)を測定したところYI=2.59であった。
比較例1のアントラセン−9,10−ジブチルエーテルに代えて9,10−ビス(n−オクタノイルオキシ)アントラセンを用いた光重合性組成物を使用した以外は実施例1と同様に塗膜の硬化を行ったところ、その時のタックフリータイムは145秒であった。また、この時の硬化塗膜の黄色度(YI)を測定したところYI=0.95であった。
100重量部の3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート(ダイセル社製、セロキサイド2021P)と2重量部の光カチオン開始剤(4−メチルフェニル)[4−(2−メチルプロピル)フェニル]ヨードニウムヘキサフルオロフォスフェート、イルガキュア250(ビー・エー・エス・エフ社製、「イルガキュア」はビー・エー・エス・エフ社の登録商標)、1重量部の9,10−ビス(n−オクタノイルオキシ)アントラセンを室温で混合、溶解し光重合性組成物を調製した。この光重合性組成物を厚さ50μmのTAC(三酢酸セルロース)フィルム上にバーコータ(No.8)で塗布し膜厚およそ12μmの塗膜を形成した。その後、中心波長395nmのLED光(50mW/cm2)を照射し塗膜の表面べとつきがなくなるまでの照射時間(タックフリータイム)を測定したところ、21秒であった。またこの時の硬化塗膜の黄色度(YI)を測定したところYI=0.60であった。
100重量部の3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート(ダイセル社製、セロキサイド2021P)と2重量部の光カチオン開始剤(4−メチルフェニル)[4−(2−メチルプロピル)フェニル]ヨードニウムヘキサフルオロフォスフェート、イルガキュア250(ビー・エー・エス・エフ社製、「イルガキュア」はビー・エー・エス・エフ社の登録商標)、1重量部のジエチルチオキサントンを室温で混合、溶解し光重合性組成物を調製した。この光重合性組成物を厚さ50μmのTAC(三酢酸セルロース)フィルム上にバーコータ(No.8)で塗布し膜厚およそ12μmの塗膜を形成した。その後、中心波長395nmのLED光(50mW/cm2)を照射し塗膜の表面べとつきがなくなるまでの照射時間(タックフリータイム)を測定したところ、8秒であった。またこの時の硬化塗膜の黄色度(YI)を測定したところYI=2.62であった。
Claims (9)
- (A)一般式(1)で示されるアントラセン化合物及び(B)波長400nm以上500nm以下の波長領域における吸光係数の最大値が(A)の化合物の波長400nm以上500nm以下の波長領域における吸光係数の最大値より大きい値を持つ化合物、を含む光重合増感剤組成物であり、化合物(B)がチオキサントン誘導体又は一般式(2)で表わされるアントラセン化合物であることを特徴とする光重合増感剤組成物。
(一般式(1)において、R 1 は炭素数1から20のアルキル基、炭素数6から20のアリール基、炭素数1から20のアルコキシ基又は炭素数6から20のアリールオキシ基を示し、X 1 、Y 1 は同一であっても異なっていてもよく、水素原子又は炭素数1から8のアルキル基を示す。)
(一般式(2)において、R2は置換基を有してもよい炭素数1から12までの直鎖状または分岐状のアルキル基を表わし、二つのR2は互いに異なっていても良いし、同一のものでもよい。有してもよい置換基としては、水酸基、アリール基、ビニル基、アルコキシ基、アリールオキシ基、ハロゲン原子、アセトキシ基、(メタ)アクリルオキシ基、グリシジル基のいずれかである。また、式(2)中、X2、Y2は同一であっても異なっていても良い水素原子、アルキル基、水酸基、アルコキシ基、アリールオキシ基、アルキルチオ基、アリールチオ基、カルボキシル基、スルホン酸基のいずれかを示す。) - 化合物(B)の割合が化合物(A)に対して0.001重量%から100重量%の範囲であることを特徴とする請求項1に記載の光重合増感剤組成物。
- 請求項1又は2に記載の光重合増感剤組成物に加え、(C)光重合開始剤及び(D)光重合性化合物を含むことを特徴とする光重合性組成物。
- 光重合開始剤(C)が光カチオン重合開始剤、光重合性化合物(D)が光カチオン重合性化合物であることを特徴とする請求項3記載の光重合性組成物。
- 光重合開始剤(C)が光ラジカル重合開始剤、光重合性化合物(D)が光ラジカル重合性化合物であることを特徴とする請求項3記載の光重合性組成物。
- 光重合性化合物(D)が光ラジカル重合性化合物及び光カチオン重合性化合物両者を含むものであることを特徴とする請求項3記載の光重合性組成物。
- 請求項3乃至請求項6のいずれか一項に記載の光重合性組成物にエネルギー線を照射することにより得られた重合物。
- 請求項3乃至請求項6のいずれか一項に記載の光重合性組成物にエネルギー線を照射することにより重合物を得る重合物の製造方法。
- 照射するエネルギー線が300nm〜500nmの波長範囲の光を含有することを特徴とする、請求項8記載の重合物の製造方法。
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JP6299235B2 (ja) * | 2013-01-25 | 2018-03-28 | 川崎化成工業株式会社 | 9,10−ビス(長鎖アシルオキシ)アントラセン化合物、その製造法及びその用途 |
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