JP2022105415A - Thermal cationic polymerizable resin composition - Google Patents
Thermal cationic polymerizable resin composition Download PDFInfo
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- JP2022105415A JP2022105415A JP2021000194A JP2021000194A JP2022105415A JP 2022105415 A JP2022105415 A JP 2022105415A JP 2021000194 A JP2021000194 A JP 2021000194A JP 2021000194 A JP2021000194 A JP 2021000194A JP 2022105415 A JP2022105415 A JP 2022105415A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 31
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 150000001450 anions Chemical class 0.000 claims abstract description 12
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 12
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 11
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003822 epoxy resin Substances 0.000 claims description 26
- 229920000647 polyepoxide Polymers 0.000 claims description 26
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 238000010943 off-gassing Methods 0.000 abstract 1
- -1 etc.) Chemical compound 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000945 filler Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000003504 photosensitizing agent Substances 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 6
- 239000012766 organic filler Substances 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- 229910021485 fumed silica Inorganic materials 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 4
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000013008 thixotropic agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000004844 aliphatic epoxy resin Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- QKAIFCSOWIMRJG-UHFFFAOYSA-N (4-methylphenyl)-(4-propan-2-ylphenyl)iodanium Chemical compound C1=CC(C(C)C)=CC=C1[I+]C1=CC=C(C)C=C1 QKAIFCSOWIMRJG-UHFFFAOYSA-N 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 2
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- POZBDDCHVAOFSL-UHFFFAOYSA-N S(=O)(OC)[O-].OC1=CC=C(C=C1)[S+](C)C Chemical compound S(=O)(OC)[O-].OC1=CC=C(C=C1)[S+](C)C POZBDDCHVAOFSL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011258 core-shell material Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- CRJIYMRJTJWVLU-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 3-(5,5-dimethylhexyl)dioxirane-3-carboxylate Chemical compound CC(C)(C)CCCCC1(C(=O)OC(C)(C)CC(C)(C)C)OO1 CRJIYMRJTJWVLU-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- LJWZDTGRJUXOCE-UHFFFAOYSA-N 2-(2-ethylhexyl)oxetane Chemical compound CCCCC(CC)CC1CCO1 LJWZDTGRJUXOCE-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- MEVBAGCIOOTPLF-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC(C=C1C=CC=2)=CC=C1C=2OCC1CO1 MEVBAGCIOOTPLF-UHFFFAOYSA-N 0.000 description 1
- XRIRVAYMWUMXBR-UHFFFAOYSA-N 2-hydroperoxypentane Chemical compound CCCC(C)OO XRIRVAYMWUMXBR-UHFFFAOYSA-N 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- RFSCGDQQLKVJEJ-UHFFFAOYSA-N 2-methylbutan-2-yl benzenecarboperoxoate Chemical compound CCC(C)(C)OOC(=O)C1=CC=CC=C1 RFSCGDQQLKVJEJ-UHFFFAOYSA-N 0.000 description 1
- WXDJDZIIPSOZAH-UHFFFAOYSA-N 2-methylpentan-2-yl benzenecarboperoxoate Chemical compound CCCC(C)(C)OOC(=O)C1=CC=CC=C1 WXDJDZIIPSOZAH-UHFFFAOYSA-N 0.000 description 1
- NUIZZJWNNGJSGL-UHFFFAOYSA-N 2-phenylpropan-2-yl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)c1ccccc1 NUIZZJWNNGJSGL-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- OUWCMMDPQFNQHM-UHFFFAOYSA-N 3-ethylbutane-1,2,4-triol Chemical compound CCC(CO)C(O)CO OUWCMMDPQFNQHM-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polyethers (AREA)
- Epoxy Resins (AREA)
Abstract
Description
本発明は熱カチオン重合性樹脂組成物に関する。 The present invention relates to a thermally cationically polymerizable resin composition.
カチオン硬化性樹脂は、その硬化物が機械的強度、耐薬品性、電気絶縁性、接着性などの特性に優れていることから、塗料、電気・電子、土木・建築、接着剤分野などで幅広く利用されている。 Cationic curable resins are widely used in the fields of paints, electrical / electronics, civil engineering / construction, adhesives, etc. because the cured products have excellent properties such as mechanical strength, chemical resistance, electrical insulation, and adhesiveness. It's being used.
一般に、ラジカルレッドクス機構（ヨードニウム塩系の光カチオン重合開始剤と有機過酸化物（熱ラジカル重合開始剤）との組み合わせ）を利用した熱硬化性の樹脂組成物は、低温で硬化可能で、且つ熱硬化のみの場合でも、紫外線硬化及び熱硬化の両方を行った場合と同等の物性を発現することが可能である。このような組成物として、特許文献１～３には、前記したラジカルレッドクス機構及びカチオン硬化性樹脂を含む熱カチオン重合性の組成物が開示されている。 Generally, a thermosetting resin composition using a radical redx mechanism (combination of an iodonium salt-based photocationic polymerization initiator and an organic peroxide (thermal radical polymerization initiator)) can be cured at a low temperature. Moreover, even in the case of only thermosetting, it is possible to exhibit the same physical properties as in the case of performing both ultraviolet curing and thermosetting. As such a composition, Patent Documents 1 to 3 disclose a thermocationically polymerizable composition containing the radical redx mechanism and the cationic curable resin described above.
しかしながら、特許文献１～３に記載された熱カチオン重合性の組成物は、ラジカル発生の機構を利用しているため、酸素阻害を受け易く、表面の硬化性が不十分になることがあった。これにより、硬化が不十分な成分が耐熱試験等でアウトガスとして揮発し、周辺部材を汚染する等の不具合が懸念されていた。 However, since the thermally cationically polymerizable compositions described in Patent Documents 1 to 3 utilize the mechanism of radical generation, they are susceptible to oxygen inhibition and the surface curability may be insufficient. .. As a result, there is a concern that components that are insufficiently cured volatilize as outgas in heat resistance tests and the like, and contaminate peripheral members.
よって、本発明は、表面硬化性に優れ、かつ、アウトガス量が低減された、熱カチオン重合性樹脂組成物を提供することを課題とする。 Therefore, it is an object of the present invention to provide a thermally cationically polymerizable resin composition having excellent surface curability and a reduced amount of outgas.
本発明者等は、上記課題を鑑み鋭意検討を重ねた結果、ラジカルレドックス機構を利用した配合に、熱カチオン開始剤を新たに添加することで、樹脂表面の硬化性を改善することができると共に、アウトガス量を低減することができることを見出した。また、熱カチオン開始剤の添加量を調整することで、ガラス転移温度を高温で維持したまま、表面硬化性を改善することができ、その結果、アウトガス量を低減することができることを見出した。 As a result of diligent studies in view of the above problems, the present inventors can improve the curability of the resin surface by newly adding a thermal cation initiator to the formulation using the radical redox mechanism. , Found that the amount of outgas can be reduced. It was also found that by adjusting the amount of the thermal cation initiator added, the surface curability can be improved while the glass transition temperature is maintained at a high temperature, and as a result, the amount of outgas can be reduced.
本発明は、以下の［１］～［４］に関する。
［１］（Ａ）カチオン硬化性樹脂、
（Ｂ）式：Ａｒ１－Ｉ＋－Ａｒ２・Ｘ－（式中、Ａｒ１及びＡｒ２は、独立して、置換又は非置換のアリール基であり、Ｘ－は、アニオンである）で示されるヨードニウム塩、
（Ｃ）有機過酸化物、及び
（Ｄ）熱カチオン重合開始剤
を含み、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が０．０３重量部以上１．５０重量部以下である、熱カチオン重合性樹脂組成物。
［２］（Ｄ）成分が、スルフォニウム塩である、［１］の熱カチオン重合性樹脂組成物。
［３］（Ｄ）成分のアニオンが、ＳｂＦ６
－、Ｂ（Ｃ６Ｆ５）４
－、又は［Ｐ（ＲＦ）ｎＦ６－ｎ］－（式中、ＲＦは、独立して、炭素原子数１～６の部分又は全フッ素化アルキル基であり、ｎは０～５の整数である）である、［１］又は［２］の熱カチオン重合性樹脂組成物。
［４］（Ａ）成分が、エポキシ樹脂及びオキセタン樹脂からなる群より選択される少なくとも一種である、［１］～［３］のいずれかの熱カチオン重合性樹脂組成物。
The present invention relates to the following [1] to [4].
[1] (A) Cationic curable resin,
Formula (B): Ar 1 −I + −Ar 2 · X − (in the formula, Ar 1 and Ar 2 are independently substituted or unsubstituted aryl groups, and X − is an anion). The iodonium salt shown,
It contains (C) an organic peroxide and (D) a thermal cationic polymerization initiator, and the content of the component (D) is 0.03 part by weight or more and 1.50 parts by weight with respect to 100 parts by weight of the component (A). A thermal cationically polymerizable resin composition which is less than or equal to a portion.
[2] The thermally cationically polymerizable resin composition of [1], wherein the component (D) is a sulfonium salt.
[3] The anion of the component (D) is SbF 6- , B (C 6 F 5 ) 4- , or [P (RF) n F 6-n ] - (in the formula, RF is independent. , A partial or total fluorinated alkyl group having 1 to 6 carbon atoms, where n is an integer of 0 to 5), the thermocationic polymerizable resin composition of [1] or [2].
[4] The thermally cationically polymerizable resin composition according to any one of [1] to [3], wherein the component (A) is at least one selected from the group consisting of an epoxy resin and an oxetane resin.
本発明により、表面硬化性に優れ、かつ、アウトガス量が低減された、熱カチオン重合性樹脂組成物が提供される。 INDUSTRIAL APPLICABILITY According to the present invention, a thermally cationically polymerizable resin composition having excellent surface curability and a reduced amount of outgas is provided.
以下、本発明の実施の形態について詳細に説明する。 Hereinafter, embodiments of the present invention will be described in detail.
［熱カチオン重合性樹脂組成物］
熱カチオン重合性樹脂組成物は、（Ａ）カチオン硬化性樹脂、（Ｂ）式：Ａｒ１－Ｉ＋－Ａｒ２・Ｘ－（式中、Ａｒ１及びＡｒ２は、独立して、置換又は非置換のアリール基であり、Ｘ－は、アニオンである）で示されるヨードニウム塩、（Ｃ）有機過酸化物、及び（Ｄ）熱カチオン重合開始剤を含み、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が０．０３重量部以上１．５０重量部以下である。
[Thermal cationically polymerizable resin composition]
The thermally cationically polymerizable resin composition is (A) a cationically curable resin, (B) formula: Ar 1 −I + −Ar 2 · X − (in the formula, Ar 1 and Ar 2 are independently substituted or substituted. It is an unsubstituted aryl group, and X − is an anion) and contains an iodonium salt (C) an organic peroxide and (D) a thermal cationic polymerization initiator, and 100 parts by weight of the component (A). On the other hand, the content of the component (D) is 0.03 parts by weight or more and 1.50 parts by weight or less.
熱カチオン重合性樹脂組成物は、（Ｄ）成分の含有量が０．０３重量部以上１．５０重量部以下であることから、ガラス転移温度（Ｔｇ）を高温で維持できる。 Since the content of the component (D) in the thermally cationically polymerizable resin composition is 0.03 parts by weight or more and 1.50 parts by weight or less, the glass transition temperature (Tg) can be maintained at a high temperature.
＜（Ａ）カチオン硬化性樹脂＞
カチオン硬化性樹脂としては、分子内に１以上のカチオン重合性基を有する樹脂であれば、特に限定されない。カチオン重合性基としては、エポキシ基、オキセタニル基、ビニルエーテル基等が挙げられる。カチオン硬化性樹脂の具体例としては、エポキシ樹脂、オキセタン樹脂、ポリスチレン系化合物、及びビニルエーテル化合物等が挙げられる。
<(A) Cationic curable resin>
The cationically curable resin is not particularly limited as long as it is a resin having one or more cationically polymerizable groups in the molecule. Examples of the cationically polymerizable group include an epoxy group, an oxetanyl group, a vinyl ether group and the like. Specific examples of the cationically curable resin include epoxy resins, oxetane resins, polystyrene compounds, vinyl ether compounds and the like.
≪エポキシ樹脂≫
エポキシ樹脂としては、芳香族、脂肪族及び脂環式エポキシ樹脂を挙げることができる。
≪Epoxy resin≫
Examples of the epoxy resin include aromatic, aliphatic and alicyclic epoxy resins.
芳香族エポキシ化合物としては、ビスフェノールＡ型エポキシ樹脂（ＤＩＣ社製のＥＰＩＣＬＯＮ８５０、８５０－Ｓ、ＥＸＡ－８５０ＣＲＰ、ＥＸＡ－８０６７等）、ビスフェノールＦ型エポキシ樹脂（ＤＩＣ社製のＥＰＩＣＬＯＮ８３０－Ｓ、ＥＸＡ－８３０ＬＶＰ等）、ビスフェノールＡＤ型エポキシ樹脂、ビスフェノールＳ型エポキシ樹脂、ナフタレン型エポキシ樹脂（ＤＩＣ社製のＥＰＩＣＬＯＮのＨＰ－４０３２Ｄ、ＨＰ－７２００Ｈ等）、フェノールノボラック型エポキシ樹脂（ＤＩＣ社製のＥＰＩＣＬＯＮ Ｎ－７４０、Ｎ－７７０等）、クレゾールノボラック型エポキシ樹脂（ＤＩＣ社製のＥＰＩＣＬＯＮ Ｎ－６６０、Ｎ－６７０、Ｎ－６５５－ＥＸＰ－Ｓ等）、多官能型エポキシ樹脂等が挙げられる。多官能型エポキシ化合物としては、テトラ（ヒドロキシフェニル）アルカンのグリシジルエーテル、テトラヒドロキシベンゾフェノンのグリシジルエーテル、エポキシ化ポリビニルフェノール等が挙げられる。 Examples of the aromatic epoxy compound include bisphenol A type epoxy resin (EPICLON850, 850-S, EXA-850CRP, EXA-8067, etc. manufactured by DIC) and bisphenol F type epoxy resin (EPICLON830-S, EXA-830LVP manufactured by DIC). Etc.), bisphenol AD type epoxy resin, bisphenol S type epoxy resin, naphthalene type epoxy resin (EPICLON HP-4032D, HP-7200H, etc. manufactured by DIC), phenol novolac type epoxy resin (EPICLON N-740 manufactured by DIC). , N-770, etc.), cresol novolac type epoxy resin (EPICLON N-660, N-670, N-655-EXP-S, etc. manufactured by DIC), polyfunctional epoxy resin and the like. Examples of the polyfunctional epoxy compound include glycidyl ether of tetra (hydroxyphenyl) alkane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol.
脂肪族エポキシ樹脂としては、多価アルコール又はそのアルキレンオキシド付加物のポリグリシジルエーテルが挙げられる。脂肪族エポキシ化合物の具体例としては、エチレングリコールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、１，４－ブタンジオールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、１，６－ヘキサンジオールジグリシジルエーテル、グリセリンジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル（共栄社化学社製のエポライト１００ＭＦ）、ポリエチレングリコールジグリシジルエーテル、２，２－ビス（ヒドロキシメチル）－１－ブタノールの１，２－エポキシ－４－（２－オキシラニル）シクロヘキサン付加物（ダイセル社製のＥＨＰＥ３１５０）等が挙げられる。 Examples of the aliphatic epoxy resin include polyhydric alcohol or polyglycidyl ether as an adduct thereof. Specific examples of the aliphatic epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, and 1,6-hexanediol. Diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether (Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.), polyethylene glycol diglycidyl ether, 1,2-bis (hydroxymethyl) -1-butanol 1,2-epoxy Examples thereof include a 4- (2-oxylanyl) cyclohexane adduct (EHPE3150 manufactured by Daicel Co., Ltd.).
脂肪族エポキシ樹脂は、脂環構造を形成する２つの炭素原子と酸素原子とで、エポキシ基が形成された構造を有する樹脂であり、脂環構造を形成する１つの炭素原子に、エポキシ基が結合する脂肪族エポキシ樹脂は含まれない。脂環式エポキシ化合物としては、シクロヘキサン系、シクロヘキシルメチルエステル系、シクロヘキシルメチルエーテル系、スピロ系及びトリシクロデカン系エポキシ化合物が挙げられる。脂環式エポキシ化合物の具体例としては、（３，３’，４，４’－ジエポキシ）ビシクロヘキシル（ダイセル社製のセロキサイド８０１０等）、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（ダイセル社製のセロキサイド２０２１Ｐ等）、１，２：８，９－ジエポキシリモネン、１，２－エポキシ－４－ビニルシクロヘキサン等が挙げられる。 The aliphatic epoxy resin is a resin having a structure in which an epoxy group is formed by two carbon atoms and an oxygen atom forming an alicyclic structure, and one carbon atom forming an alicyclic structure has an epoxy group. Does not include the aliphatic epoxy resin to be bound. Examples of the alicyclic epoxy compound include cyclohexane-based, cyclohexylmethyl ester-based, cyclohexylmethyl ether-based, spiro-based and tricyclodecane-based epoxy compounds. Specific examples of the alicyclic epoxy compound include (3,3', 4,4'-diepoxy) bicyclohexyl (celloxide 8010 manufactured by Daicel, etc.), 3', 4'-epoxycyclohexylmethyl 3,4-epoxy. Cyclohexanecarboxylate (celloxide 2021P manufactured by Daicel, etc.), 1,2: 8,9-diepoxyrimonene, 1,2-epoxy-4-vinylcyclohexane and the like can be mentioned.
≪オキセタン樹脂≫
オキセタン樹脂の具体例としては、３－エチル－３－ヒドロキシメチルオキセタン（オキセタンアルコール）（東亞合成社製のＯＸＴ－１０１等）、２－エチルヘキシルオキセタン（東亞合成社製のＯＸＴ－２１２等）、キシリレンビスオキセタン（ＸＤＯ。東亞合成社製のＯＸＴ－１２１等）、３－エチル－３｛［（３－エチルオキセタン－３－イル）メトキシ］メチル｝オキセタン（東亞合成社製のＯＸＴ－２２１等）、オキセタニルシルセスキオキセタン（東亞合成社製ＯＸＴ－１９１等）、フェノールノボラックオキセタン（東亞合成社製ＰＨＯＸ等）及び３－エチル－３－フェノキシメチルオキセタン（ＰＯＸ。東亞合成社製ＯＸＴ－２１１等）が挙げられる。
≪Oxetane resin≫
Specific examples of the oxetane resin include 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol) (OXT-101 manufactured by Toagosei Co., Ltd.), 2-ethylhexyl oxetane (OXT-212 etc. manufactured by Toagosei Co., Ltd.), and xiri. Lenbis oxetane (XDO, OXT-121, etc. manufactured by Toagosei Co., Ltd.), 3-Ethyl-3 {[(3-ethyloxetane-3-yl) methoxy] methyl} oxetane (OXT-221, etc. manufactured by Toagosei Co., Ltd.) , Oxetane tylsilsesquioxetane (OXT-191 etc. manufactured by Toagosei Co., Ltd.), phenol novolac oxetane (PHOX etc. manufactured by Toagosei Co., Ltd.) and 3-ethyl-3-phenoxymethyloxetane (POX. OXT-211 manufactured by Toagosei Co., Ltd.) Can be mentioned.
≪ビニルエーテル化合物≫
ビニルエーテル化合物の具体例としては、ヒドロキシブチルビニルエーテル（ＩＳＰ社製のＨＢＶＥ等）、１，４－シクロヘキサンジメタノールのビニルエーテル（ＩＳＰ社製のＣＨＶＥ等）、トリエチレングリコールジビニルエーテル（ＩＳＰ社製のＤＶＥ－３等）、ドデシルビニルエーテル（ＩＳＰ社製のＤＤＶＥ等）、及びシクロヘキシルビニルエーテル（ＩＳＰ社製ＣＶＥ等）が挙げられる。
≪Vinyl ether compound≫
Specific examples of the vinyl ether compound include hydroxybutyl vinyl ether (such as HBVE manufactured by ISP), vinyl ether of 1,4-cyclohexanedimethanol (such as CHVE manufactured by ISP), and triethylene glycol divinyl ether (such as DVE-manufactured by ISP). 3 etc.), dodecyl vinyl ether (DDVE etc. manufactured by ISP), and cyclohexyl vinyl ether (CVE etc. manufactured by ISP).
≪好ましいカチオン硬化性樹脂≫
（Ａ）成分は、エポキシ樹脂及びオキセタン樹脂からなる群より選択される少なくとも一種であることが好ましい。
（Ａ）成分は、１種又は２種以上の組み合わせであってよい。
<< Preferred cationic curable resin >>
The component (A) is preferably at least one selected from the group consisting of an epoxy resin and an oxetane resin.
The component (A) may be one kind or a combination of two or more kinds.
＜（Ｂ）式：Ａｒ１－Ｉ＋－Ａｒ２・Ｘ－で示されるヨードニウム塩＞
（Ｂ）成分は、式：Ａｒ１－Ｉ＋－Ａｒ２・Ｘ－（式中、Ａｒ１及びＡｒ２は、独立して、置換又は非置換のアリール基であり、Ｘ－は、アニオンである）で示されるヨードニウム塩（以下、単に「ヨードニウム塩」ともいう。）である。ここで「アリール基」とは、炭素原子数６～１８の芳香族炭化水素基、好ましくは、フェニル基又はナフチル基を意味する。アリール基は、非置換であっても、１つ以上の任意の置換基で置換されていてもよく、そのような置換基として、炭素原子数１～１８の直鎖又は分岐鎖状のアルキル基、炭素原子数１～１８の直鎖又は分岐鎖状のアルコキシ基、炭素原子数２～１８の直鎖又は分岐鎖状のアルコキシカルボニル基、炭素原子数２～１８の直鎖又は分岐鎖状のアシルオキシ基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシル基等を挙げることができる。「アニオン」は、一価のカウンターアニオンであればよいが、非アンチモン系のアニオンであることが好ましく、ＢＦ４
－、ＡｓＦ６
－、又はＢ（Ｃ６Ｆ５）４
－、あるいは［Ｐ（ＲＦ）ｎＦ６－ｎ］－、［Ｃ（ＲＦＳＯ２）３］－、又は［Ｎ（ＲＦＳＯ２）２］－（式中、ＲＦは、独立して、炭素原子数１～６の部分又は全フッ素化アルキル基であり、ｎは０～５の整数である）であることが特に好ましい。
<Equation (B) : Iodonium salt represented by Ar 1 -I + -Ar 2 · X->
The component (B) is the formula: Ar 1 −I + −Ar 2 · X − (in the formula, Ar 1 and Ar 2 are independently substituted or unsubstituted aryl groups, and X − is an anion. (A) is an iodonium salt (hereinafter, also simply referred to as "iodonium salt"). Here, the "aryl group" means an aromatic hydrocarbon group having 6 to 18 carbon atoms, preferably a phenyl group or a naphthyl group. The aryl group may be unsubstituted or substituted with one or more arbitrary substituents, and as such a substituent is a linear or branched alkyl group having 1 to 18 carbon atoms. , A linear or branched alkoxy group having 1 to 18 carbon atoms, a linear or branched alkoxycarbonyl group having 2 to 18 carbon atoms, or a linear or branched alkoxy group having 2 to 18 carbon atoms. Examples thereof include an acyloxy group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group. The "anion" may be a monovalent counter anion, but is preferably a non-antimony anion, and is preferably BF 4- , AsF 6- , or B (C 6 F 5 ) 4- , or [P (. RF) n F 6-n ] - , [ C ( RF SO 2 ) 3 ]-or [N ( RF SO 2 ) 2 ] - (In the formula, RF is independent of the number of carbon atoms. It is particularly preferably a moiety of 1 to 6 or a total fluorinated alkyl group, where n is an integer of 0 to 5).
（Ｂ）成分の具体例としては、ジフェニルヨードニウム・ヘキサフルオロアルセネート、ジ（４－クロロフェニル）ヨードニウム・ヘキサフルオロアルセネート、ジ（４－ブロムフェニル）ヨードニウム・ヘキサフルオロアルセネート、フェニル（４－メトキシフェニル）ヨードニウム・ヘキサフルオロアルセネート、４－メチルフェニル－４－（１－メチルエチル）フェニルヨードニウム・ヘキサフルオロホスフェート、４－メチルフェニル－４－（１－メチルエチル）フェニルヨードニウム・トリ（ペンタフルオロエチル）トリフルオロホスフェート（例えば、サンアプロ社製のＩＫ－１）、４－メチルフェニル－４－（１－メチルエチル）フェニルヨードニウム・テトラキス（ペンタフルオロフェニル）ボレート（例えば、ローディア社製のＰＩ－２０７４）、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・ヘキサフルオロホスフェート（例えば、ＢＡＳＦ社製のＩＲＧＡＣＵＲＥ（登録商標）２５０）、ビス（Ｃ１０～１４－アルキルフェニル）ヨードニウム・ヘキサフルオロホスフェート（例えば、和光純薬工業社製のＷＰＩ－１１３）、４－メチルフェニル－４－（１－メチルエチル）フェニルヨードニウム・ヘキサフルオロアンチモネート（例えば、和光純薬工業製のＷＰＩ－１１６等）等を挙げることができる。このようなヨードニウム塩は、例えばカチオン開始剤として、試薬供給業者から市販されており、容易に入手することができる。 Specific examples of the component (B) include diphenyliodonium / hexafluoroarsenate, di (4-chlorophenyl) iodonium / hexafluoroarsenate, di (4-bromphenyl) iodonium / hexafluoroarsenate, and phenyl (4-methoxy). Phenyl) iodonium hexafluoroarsenate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexafluorophosphate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium tri (pentafluoroethyl) ) Trifluorophosphate (for example, IK-1 manufactured by San-Apro), 4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrakis (pentafluorophenyl) borate (for example, PI-2074 manufactured by Rhodia). , 4-Methylphenyl-4- (2-methylpropyl) phenyliodonium hexafluorophosphate (eg, IRGACURE® 250 manufactured by BASF), Bis (C 10-14 -alkylphenyl) iodonium hexafluorophosphate. (For example, WPI-113 manufactured by Wako Pure Chemical Industries, Ltd.), 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexafluoroantimonate (for example, WPI-116 manufactured by Wako Pure Chemical Industries, Ltd.), etc. Can be mentioned. Such iodonium salts are commercially available from reagent suppliers, for example as cation initiators, and are readily available.
（Ｂ）成分は、１種又は２種以上の組み合わせであってよい。 The component (B) may be one kind or a combination of two or more kinds.
＜（Ｃ）有機過酸化物＞
（Ｃ）有機過酸化物は、パーオキシ基（－Ｏ－Ｏ－）を含む化合物である。有機過酸化物は、ラジカル源である。有機過酸化物から発生したラジカルが、（Ｂ）成分のヨードニウム塩を還元的に分解し、光によらず酸を発生させることにより、カチオン重合を促進させる。有機過酸化物としては、ジアシルパーオキシド類、ヒドロパーオキシド類、ジアルキルパーオキシド類、パーオキシケタール類、パーオキシエステル類、パーオキシカーボネート類等が挙げられる。
<(C) Organic peroxide>
(C) The organic peroxide is a compound containing a peroxy group (—O—O—). Organic peroxides are radical sources. Radicals generated from the organic peroxide reductively decompose the boronium salt of the component (B) to generate an acid regardless of light, thereby promoting cationic polymerization. Examples of the organic peroxide include diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, peroxyesters, peroxycarbonates and the like.
（Ｃ）成分の具体例としては、ジラウロイルパーオキシド、ジベンゾイルパーオキシド、ビス－３，５，５－トリメチルヘキサノイルパーオキシドのようなジアシルパーオキシド類；１，１，３，３－テトラメチルブチルヒドロパーオキシド、クメンヒドロパーオキシド（例えば、化薬アグゾ社製のカヤクメンＨ）、ｔ－ブチルヒドロパーオキシドのようなヒドロパーオキシド類；ジクミルパーオキシド、２，５－ジメチル－２，５－ジ（ｔ－ブチルパーオキシ）ヘキサン、１，３－ビス（ｔ－ブチルパーオキシソプロピル）ベンゼン、ｔ－ブチルクミルパーオキシド、ジ－ｔ－ブチルパーオキシド、２，５－ジメチル－２，５－ジ（ｔ－ブチルパーオキシ）ヘキシン－３のようなジアルキルパーオキシド類；２，２－ビス（４，４－ジ－ｔ－ブチルパーオキシシクロヘキシル）プロパン、１，１－ジ－ｔ－ブチルパーオキシシクロヘキサン、２，２－ジ－ｔ－ブチルペルオキブタンのようなパーオキシケタール類；１，１，３，３－テトラメチルブチルパーオキシネオデカノエート、α－クミルパーオキシネオデカノエート、ｔ－ブチルパーオキシネオデカノエート、ｔ－ブチルパーオキシネオヘプタノエート、ｔ－ブチルパーオキシピバレート、１，１，３，３－テトラメチルブチルパーオキシ－２－エチルヘキサノエート、ｔ－アミルパーオキシ２－エチルヘキサノエート、ｔ－ブチルパーオキシ２－エチルヘキサノエート、ジ－ｔ－ブチルパーオキシヘキサヒドロテレフタレート、ｔ－アミルパーオキシ３，５，５－トリメチルヘキサノエート、ｔ－ブチルパーオキシアセテート、ｔ－ブチルパーオキシベンゾエート、ｔ－ヘキシルパーオキシベンゾエート、ｔ－アミルパーオキシベンゾエートのようなパーオキシエステル類；ジ－２－エチルヘキシルパーオキシジカーボネート、ジイソプロピルパーオキシジカーボネート、ｔ－ブチルパーオキシソプロピルカーボネート、ｔ－ブチルパーオキシ２－エチルヘキシルカーボネート、１，６－ビス（ｔ－ブチルパーオキシカルボニルオキシ）ヘキサンのようなパーオキシカーボネート類等を挙げることができる。このような有機過酸化物は、試薬供給業者から市販されており、容易に入手することができる。 Specific examples of the component (C) include diacyl peroxides such as dilauroyl peroxide, dibenzoyl peroxide, and bis-3,5,5-trimethylhexanoyl peroxide; 1,1,3,3-tetra. Hydroperoxides such as methylbutylhydroperoxide, cumenehydroperoxide (eg, Kayakumen H manufactured by Chemicals Aguso), t-butylhydroperoxide; dicumylperoxide, 2,5-dimethyl-2, 5-Di (t-butylperoxy) hexane, 1,3-bis (t-butylperoxysopropyl) benzene, t-butylcumylperoxide, di-t-butylperoxide, 2,5-dimethyl-2 , 5-Di (t-butylperoxy) hexin-3 and other dialkyl peroxides; 2,2-bis (4,4-di-t-butylperoxycyclohexyl) propane, 1,1-di-t -Peroxyketals such as butylperoxycyclohexane, 2,2-di-t-butylperokibutane; 1,1,3,3-tetramethylbutylperoxyneodecanoate, α-cumylperoxyneo Decanoate, t-butylperoxyneodecanoate, t-butylperoxyneoheptanoate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa Noate, t-amylperoxy2-ethylhexanoate, t-butylperoxy2-ethylhexanoate, di-t-butylperoxyhexahydroterephthalate, t-amylperoxy3,5,5-trimethyl Peroxyesters such as hexanoate, t-butylperoxyacetate, t-butylperoxybenzoate, t-hexylperoxybenzoate, t-amylperoxybenzoate; di-2-ethylhexylperoxydicarbonate, diisopropyl Peroxycarbonates such as peroxydicarbonate, t-butylperoxysopropyl carbonate, t-butylperoxy2-ethylhexyl carbonate, and 1,6-bis (t-butylperoxycarbonyloxy) hexane. Can be done. Such organic peroxides are commercially available from reagent suppliers and are readily available.
（Ｃ）成分は、１種又は２種以上の組み合わせであってよい。 The component (C) may be one kind or a combination of two or more kinds.
＜（Ｄ）熱カチオン重合開始剤＞
（Ｄ）熱カチオン重合開始剤は、加熱によりカチオン重合させる際のカチオン発生源となる成分である。熱カチオン重合開始剤としては、カチオン部分が、芳香族スルフォニウム、芳香族ジアゾニウム、芳香族アンモニウム、チアンスレニウム、チオキサントニウム、又は、（２，４－シクロペンタジエン－１－イル）［（１－メチルエチルベンゼン］－Ｆｅカチオンであり、アニオン部分が、ＳｂＦ６
－、ＢＦ４
－、ＰＦ６
－、Ｂ（Ｃ６Ｆ５）４
－、［Ｐ（ＲＦ）ｎＦ６－ｎ］－（式中、ＲＦは、独立して、炭素原子数１～６の部分又は全フッ素化アルキル基であり、ｎは０～５の整数である）、又は、［ＢＸ４］－（式中、Ｘは少なくとも２つ以上のフッ素原子又はトリフルオロメチル基で置換されたフェニル基である）である、カチオン部分及びアニオン部分で構成されるオニウム塩が挙げられる。熱カチオン重合開始剤は、スルフォニウム塩であることが好ましい。熱カチオン重合開始剤のアニオンが、ＳｂＦ６
－、Ｂ（Ｃ６Ｆ５）４
－、又は［Ｐ（ＲＦ）ｎＦ６－ｎ］－（式中、ＲＦは、独立して、炭素原子数１～６の部分又は全フッ素化アルキル基であり、ｎは０～５の整数である）であることが好ましい。
<(D) Thermal cation polymerization initiator>
(D) The thermal cationic polymerization initiator is a component that becomes a cation generation source when cation polymerization is carried out by heating. As the thermal cation polymerization initiator, the cation moiety is aromatic fluoronium, aromatic diazonium, aromatic ammonium, thianthrenium, thioxanthonium, or (2,4-cyclopentadiene-1-yl) [(1-1-yl). Methylethylbenzene] -Fe cation, and the anion moiety is SbF 6- , BF 4- , PF 6- , B (C 6 F 5 ) 4- , [P (RF) n F 6-n ] - (formula) Among them, RF is independently a partial or total fluorinated alkyl group having 1 to 6 carbon atoms, and n is an integer of 0 to 5) or [BX 4 ] - (X in the formula). Is an onium salt composed of a cation moiety and an anion moiety, which is a phenyl group substituted with at least two or more fluorine atoms or a trifluoromethyl group). The thermal cation polymerization initiator is a sulfonium salt. It is preferable that the anion of the thermal cation polymerization initiator is SbF 6- , B (C 6 F 5 ) 4- , or [P (RF) n F 6-n ] - (in the formula, RF is Independently, it is a partial or total fluorinated alkyl group having 1 to 6 carbon atoms, and n is preferably an integer of 0 to 5).
（Ｄ）成分の市販品としては、サンアプロ社製のＴＡ－６０、ＴＡ－６０Ｂ、ＴＡ－１００、ＴＡ－１２０；ＡＤＥＫＡ社製のアデカオプトンＣＰ－７７、アデカオプトンＣＰ－６６；日本曹達社製のＣＩ－２６３９、ＣＩ－２６２４；キングインダストリーズ社製のＣＸＣ－１６１２、ＣＸＣ－１７３８；三新化学工業社製のサンエイドＳＩ－４５、サンエイドＳＩ－６０、サンエイドＳＩ－８０、サンエイドＳＩ－１００、サンエイドＳＩ－１１０、サンエイドＳＩ－Ｂ３、サンエイドＳＩ－Ｂ３Ａ、サンエイドＳＩ－Ｂ４等が挙げられる。 Commercially available products of the component (D) include TA-60, TA-60B, TA-100, TA-120 manufactured by San-Apro; ADEKA OPTON CP-77 and ADEKA OPTON CP-66 manufactured by ADEKA; CI manufactured by Nippon Soda. -2639, CI-2624; CXC-1612, CXC-1738 manufactured by King Industries; Sun Aid SI-45, Sun Aid SI-60, Sun Aid SI-80, Sun Aid SI-100, Sun Aid SI- manufactured by Sanshin Chemical Industry Co., Ltd. 110, Sun Aid SI-B3, Sun Aid SI-B3A, Sun Aid SI-B4 and the like can be mentioned.
（Ｄ）成分は、１種又は２種以上の組み合わせであってよい。 The component (D) may be one kind or a combination of two or more kinds.
＜（Ｅ）その他の成分＞
熱カチオン重合性樹脂組成物は、本発明の効果を損なわない範囲内であれば、その目的に応じて、その他の成分を含むことができる。その他の成分として、光増感剤、充填剤、カップリング剤（特に、シランカップリング剤）、ポットライフ安定剤、重合禁止剤、溶剤、強化材、着色剤、安定剤、増量剤、粘度調節剤、粘着付与剤、難燃剤、紫外線吸収剤、酸化防止剤、変色防止剤、抗菌剤、防黴剤、老化防止剤、帯電防止剤、可塑剤、滑剤、平滑化剤、発泡剤、離型剤等が挙げられる。
<(E) Other ingredients>
The thermally cationically polymerizable resin composition may contain other components depending on the purpose as long as it does not impair the effects of the present invention. Other ingredients include photosensitizers, fillers, coupling agents (particularly silane coupling agents), pot life stabilizers, polymerization inhibitors, solvents, reinforcing agents, colorants, stabilizers, bulking agents, viscosity regulators. Agents, tackifiers, flame retardants, UV absorbers, antioxidants, discoloration inhibitors, antibacterial agents, fungicides, antioxidants, antistatic agents, plasticizers, lubricants, smoothing agents, foaming agents, mold release Examples include agents.
≪光増感剤≫
光増感剤は、光への感度を高めるための成分である。光増感剤としては、チオキサントン誘導体、カルボニル化合物、有機硫黄化合物、過硫化物、レドックス系化合物、アゾ及びジアゾ化合物、ハロゲン化合物、光還元性色素等が挙げられ、チオキサントン誘導体が好ましい。チオキサントン誘導体の具体例としては、イソプロピルチオキサントン、２，４－ジエチルチオキサントン、２－クロロチオキサントン、２，４－ジエチルチオキサントン、２－クロロチオキサントン、チオキサントンアンモニウム塩等が挙げられ、２，４－ジエチルチオキサントンが好ましい。
光増感剤は、１種又は２種以上の組み合わせであってよい。
≪Photosensitizer≫
The photosensitizer is a component for increasing the sensitivity to light. Examples of the photosensitizer include thioxanthone derivatives, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, photoreducing dyes and the like, and thioxanthone derivatives are preferable. Specific examples of the thioxanthone derivative include isopropylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, thioxanthone ammonium salt and the like, and 2,4-diethylthioxanthone. preferable.
The photosensitizer may be one kind or a combination of two or more kinds.
≪充填剤≫
充填剤は、特に限定されず、公知の無機充填剤及び有機充填剤が挙げられる。
≪Filler≫
The filler is not particularly limited, and examples thereof include known inorganic fillers and organic fillers.
無機充填剤としては、炭酸カルシウム、炭酸マグネシウム、硫酸バリウム、硫酸マグネシウム、珪酸アルミニウム、酸化チタン、アルミナ、酸化亜鉛、二酸化ケイ素（沈降性シリカ、フュームドシリカ（煙霧質シリカ）等）、カオリン、タルク、ガラスビーズ、セリサイト活性白土、水酸化アルミニウム、石綿粉、酸化銅、水酸化銅、酸化鉄、酸化鉛、酸化マグネシウム、酸化スズ、カーボン、マイカ、スメクタイト、カーボンブラック、ベントナイト、窒化アルミニウム、及び窒化ケイ素が挙げられる。密着性の観点から、無機充填剤は、二酸化ケイ素、ガラスビーズ及びタルクであることが好ましく、タルクが特に好ましい。 Examples of the inorganic filler include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, titanium oxide, alumina, zinc oxide, silicon dioxide (precipitated silica, fumed silica (foam silica), etc.), kaolin, and talc. , Glass beads, sericite active white clay, aluminum hydroxide, asbestos powder, copper oxide, copper hydroxide, iron oxide, lead oxide, magnesium oxide, tin oxide, carbon, mica, smectite, carbon black, bentonite, aluminum nitride, and Examples include silicon dioxide. From the viewpoint of adhesion, the inorganic filler is preferably silicon dioxide, glass beads and talc, and talc is particularly preferable.
有機充填剤としては、アクリル粒子、ポリメタクリル酸メチル、ポリスチレン（ポリスチレンビーズ）、これらを構成するモノマー（即ち、メタクリル酸メチル又はスチレン）と他のモノマーとを共重合させて得られる共重合体、ポリエチレン粒子、ポリシロキサン樹脂粒子、ポリアミド粒子、ポリエステル微粒子、ポリウレタン微粒子、及びゴム微粒子（アクリルゴム粒子、イソプレンゴム粒子）が挙げられる。有機充填剤は、コアシェル構造を有していてもよい。密着性の観点から、有機充填剤は、ゴム微粒子であることが好ましく、コアシェル構造を有するゴム微粒子であることが特に好ましい。 Examples of the organic filler include acrylic particles, polymethyl methacrylate, polystyrene (polyester beads), and a copolymer obtained by copolymerizing a monomer (that is, methyl methacrylate or styrene) constituting these with another monomer. Examples thereof include polyethylene particles, polysiloxane resin particles, polyamide particles, polyester fine particles, polyurethane fine particles, and rubber fine particles (acrylic rubber particles, isoprene rubber particles). The organic filler may have a core-shell structure. From the viewpoint of adhesion, the organic filler is preferably rubber fine particles, and particularly preferably rubber fine particles having a core-shell structure.
充填剤が、有機充填剤である場合、有機充填剤の重量平均分子量は、特に限定されないが、５万～４００万であることが好ましく、３０万～３００万であることが特に好ましい。 When the filler is an organic filler, the weight average molecular weight of the organic filler is not particularly limited, but is preferably 50,000 to 4 million, and particularly preferably 300,000 to 3 million.
充填剤の平均粒子径は、特に限定されないが、０．０１μｍ以上１０μｍ未満であることが好ましく、１μｍ～５μｍであることが特に好ましい。充填剤の平均粒子径は、レーザー回折式粒度分布測定装置で測定することができる。 The average particle size of the filler is not particularly limited, but is preferably 0.01 μm or more and less than 10 μm, and particularly preferably 1 μm to 5 μm. The average particle size of the filler can be measured with a laser diffraction type particle size distribution measuring device.
なお、充填剤は、チキソ付与剤として機能する成分であってもよい。チキソ付与剤は、第一の封止用組成物に、塗工性改善等を付与する成分である。チキソ付与剤として機能する充填剤としては、ヒュームドシリカが挙げられる。ヒュームドシリカは、表面処理されていてもよい。無機系のチキソ付与剤の表面処理剤としては、モノアルキルトリアルコキシシラン、ジメチルジクロロシラン、ポリジメチルシロキサン、ヘキサメチルジシラザン等が挙げられる。表面処理された又は未処理のヒュームドシリカは、市販品を用いることができる。
充填剤は、１種単独又は２種以上の組み合わせであってよい。
The filler may be a component that functions as a thixotropic agent. The thixotropic agent is a component that imparts coatability improvement and the like to the first sealing composition. Examples of the filler that functions as a thixotropic agent include fumed silica. The fumed silica may be surface-treated. Examples of the surface treatment agent for the inorganic thixo-imparting agent include monoalkyltrialkoxysilane, dimethyldichlorosilane, polydimethylsiloxane, and hexamethyldisilazane. Commercially available products can be used as the surface-treated or untreated fumed silica.
The filler may be one kind alone or a combination of two or more kinds.
≪シランカップリング剤≫
シランカップリング剤としては、エポキシ基、アルケニル基（例えば、ビニル基）、（メタ）アクリル基、第１級又は第２級アミノ基、メルカプト基、イソシアナト基、ウレイド基及びハロゲン原子からなる群より選択される１種以上の反応性官能基又は前記基で置換されたアルキル基と、１以上のアルコキシ基とを有し、非置換のアルキル基を有していてもよいシラン化合物が挙げられる。なお、前記反応性官能基は、前記反応性官能基で置換されたアルキル基として、シラン化合物のケイ素原子に結合していてもよい。
≪Silane coupling agent≫
The silane coupling agent includes an epoxy group, an alkenyl group (for example, a vinyl group), a (meth) acrylic group, a primary or secondary amino group, a mercapto group, an isocyanato group, a ureido group and a halogen atom. Examples thereof include a silane compound having one or more selected reactive functional groups or an alkyl group substituted with the group and one or more alkoxy groups, which may have an unsubstituted alkyl group. The reactive functional group may be bonded to the silicon atom of the silane compound as an alkyl group substituted with the reactive functional group.
シランカップリング剤の具体例としては、２－（３，４－エポキシシクロヘキシル）エチルトリメトキシシラン、３－グリシドキシプロピルトリメトキシシラン、３－グリシドキシプロピルメチルジエトキシシラン、３－グリシドキシプロピルトリエトキシシラン等のエポキシ基とアルコキシ基とを有し、アルキル基を有していてもよいシラン化合物；ビニルトリメトキシシラン、ｐ－スチリルトリメトキシシラン等のアルケニル基とアルコキシ基とを有し、アルキル基を有していてもよいシラン化合物；３－メタクリロキシプロピルメチルジメトキシシラン、３－メタクリロキシプロピルトリメトキシシラン、３－メタクリロキシプロピルメチルジエトキシシラン、３－メタクリロキシプロピルトリエトキシシラン、３－アクリロキシプロピルトリメトキシシラン等の（メタ）アクリル基とアルコキシ基とを有し、アルキル基を有していてもよいシラン化合物；Ｎ－２－（アミノエチル）－３－アミノプロピルメチルジメトキシシラン、Ｎ－２－（アミノエチル）－３－アミノプロピルトリメトキシシラン、Ｎ－２－（アミノエチル）－３－アミノプロピルトリエトキシシラン、３－アミノプロピルトリメトキシシラン、３－アミノプロピルトリエトキシシラン、３－トリエトキシシリル－Ｎ－（１，３－ジメチル－ブチリデン）プロピルアミン、Ｎ－フェニル－３－アミノプロピルトリメトキシシラン等の第１級又は第２級アミノ基とアルコキシ基とを有し、アルキル基を有していてもよいシラン化合物；３－ウレイドプロピルトリエトキシシラン、３－クロロプロピルトリメトキシシラン、３－メルカプトプロピルメチルジメトキシシラン、３－メルカプトプロピルトリメトキシシラン、ビス（トリエトキシシリルプロピル）テトラスルフィド、３－イソシアナトプロピルトリエトキシシラン等のメルカプト基、イソシアナト基、ウレイド基及びハロゲン原子からなる群より選択される１種以上の基と、１以上のアルコキシ基とを有し、アルキル基を有していてもよいシラン化合物等が挙げられる。
シランカップリング剤は、１種又は２種以上の組み合わせでもよい。
Specific examples of the silane coupling agent include 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycid. A silane compound having an epoxy group such as xypropyltriethoxysilane and an alkoxy group and optionally having an alkyl group; having an alkenyl group such as vinyltrimethoxysilane and p-styryltrimethoxysilane and an alkoxy group. However, a silane compound which may have an alkyl group; 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane. , 3-Acryloxypropyltrimethoxysilane, a silane compound having a (meth) acrylic group and an alkoxy group, and optionally having an alkyl group; N-2- (aminoethyl) -3-aminopropylmethyl Dimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltri Primary or secondary amino groups such as ethoxysilane, 3-triethoxysilyl-N- (1,3-dimethyl-butylidene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and alkoxy groups. Silane compounds having and optionally having an alkyl group; 3-ureidopropyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis (tri). It has one or more groups selected from the group consisting of mercapto groups such as ethoxysilylpropyl) tetrasulfide and 3-isosyanatopropyltriethoxysilane, isocyanato groups, ureido groups and halogen atoms, and one or more alkoxy groups. However, examples thereof include a silane compound which may have an alkyl group.
The silane coupling agent may be used alone or in combination of two or more.
≪その他の（Ｅ）成分≫
重合禁止剤としては、ヒドロキノン、パラメトキシフェノール、ジブチルヒドロキシトルエン等が挙げられる。
ポットライフ安定剤としては、ＳＩ助剤（４－ヒドロキシフェニルジメチルスルホニウムメチルサルファイト）、ヒンダードフェノール系酸化防止剤が挙げられる。
上記した成分以外は、公知の成分から適宜選択できる。
≪Other (E) ingredients≫
Examples of the polymerization inhibitor include hydroquinone, paramethoxyphenol, dibutylhydroxytoluene and the like.
Examples of the pot life stabilizer include SI auxiliaries (4-hydroxyphenyldimethylsulfonium methylsulfite) and hindered phenolic antioxidants.
Other than the above-mentioned components, known components can be appropriately selected.
（Ｅ）成分は、それぞれ、１種又は２種以上の組み合わせであってよい。例えば、（Ｅ）成分は、１種以上の無機充填剤と、１種以上の光増感剤との組み合わせであってもよい。 The component (E) may be one kind or a combination of two or more kinds, respectively. For example, the component (E) may be a combination of one or more kinds of inorganic fillers and one or more kinds of photosensitizers.
＜組成物の調製方法＞
熱カチオン重合性樹脂組成物は、各成分を混合することで製造することができる。なお、（Ｂ）成分～（Ｅ）成分が固体である場合は、各成分（特に、（Ａ）成分）との相溶性の向上のために、溶剤に溶解させて、カチオン重合性樹脂組成物の製造に供されてもよい。
<Preparation method of composition>
The thermally cationically polymerizable resin composition can be produced by mixing each component. When the components (B) to (E) are solid, the cationically polymerizable resin composition is dissolved in a solvent in order to improve the compatibility with each component (particularly, the component (A)). May be used in the production of.
〔硬化方法〕
熱カチオン重合性樹脂組成物は、熱を加えることにより硬化させることができる。また、熱カチオン重合性樹脂組成物は、紫外線等のエネルギー線を照射することにより仮硬化（仮固定）させた後に、熱を加えることによって本硬化（本固定）させてもよい。熱カチオン重合性樹脂組成物を、エネルギー線を照射することにより仮硬化させる場合は、熱カチオン重合性樹脂組成物は、光増感剤を含んでいてもよい。
[Curing method]
The thermally cationically polymerizable resin composition can be cured by applying heat. Further, the heat-cationic polymerizable resin composition may be temporarily cured (temporarily fixed) by irradiating it with energy rays such as ultraviolet rays, and then finally cured (mainly fixed) by applying heat. When the heat-cationically polymerizable resin composition is temporarily cured by irradiating it with energy rays, the heat-cationically polymerizable resin composition may contain a photosensitizer.
＜成分の含有量＞
熱カチオン重合性樹脂組成物における、各成分の含有量は以下の通りであることが好ましい。
（Ａ）成分中のエポキシ樹脂及びオキセタン樹脂の合計の含有量は、（Ａ）成分の１００重量部に対して、６０～１００重量部であることが好ましく、８０～１００重量部であることが特に好ましい。
（Ａ）成分中のオキセタン樹脂の合計の含有量は、エポキシ樹脂の１００重量部に対して、５～５０重量部であることが好ましく、１０～４０重量部であることが特に好ましい。
（Ａ）成分中の脂環式エポキシ樹脂及び芳香族エポキシ樹脂の合計の含有量は、（Ａ）成分中のエポキシ樹脂の１００重量部に対して、６０～１００重量部であることが好ましく、８０～１００重量部であることが特に好ましい。
（Ｂ）成分の含有量は、熱硬化速度の観点から、（Ａ）成分の１００重量部に対して、０．１～１０．０重量部であることが好ましく、０．５～５．０重量部であることが特に好ましい。
（Ｃ）成分の含有量は、熱硬化速度の観点から、（Ａ）成分の１００重量部に対して、１．０～１０．０重量部であることが好ましく、１．５～５．０重量部であることが特に好ましい。
（Ｄ）成分の含有量は、（Ａ）成分の１００重量部に対して、０．０３重量部以上１．５０重量部以下である。（Ｄ）成分の含有量が、（Ａ）成分の１００重量部に対して、０．０３重量部未満である場合、表面硬化性が劣り、かつ、アウトガス量が増加する傾向があり、１．５０重量部超である場合、ガラス転移温度が低温になり、かつ、アウトガス量が増加する傾向がある。
（Ａ）成分～（Ｄ）成分の合計は、熱カチオン重合性樹脂組成物の総量に対して、２０～１００重量部であることが好ましく、３０～１００重量部であることが好ましく、４０～１００重量部であることが特に好ましい。残余は、（Ｅ）成分である。
<Ingredient content>
The content of each component in the thermally cationically polymerizable resin composition is preferably as follows.
The total content of the epoxy resin and the oxetane resin in the component (A) is preferably 60 to 100 parts by weight, preferably 80 to 100 parts by weight, based on 100 parts by weight of the component (A). Especially preferable.
The total content of the oxetane resin in the component (A) is preferably 5 to 50 parts by weight, particularly preferably 10 to 40 parts by weight, based on 100 parts by weight of the epoxy resin.
The total content of the alicyclic epoxy resin and the aromatic epoxy resin in the component (A) is preferably 60 to 100 parts by weight with respect to 100 parts by weight of the epoxy resin in the component (A). It is particularly preferably 80 to 100 parts by weight.
The content of the component (B) is preferably 0.1 to 10.0 parts by weight, preferably 0.5 to 5.0 parts by weight, based on 100 parts by weight of the component (A) from the viewpoint of the heat curing rate. It is particularly preferable to use parts by weight.
The content of the component (C) is preferably 1.0 to 10.0 parts by weight, preferably 1.5 to 5.0 parts by weight, based on 100 parts by weight of the component (A) from the viewpoint of the thermosetting rate. It is particularly preferable to use parts by weight.
The content of the component (D) is 0.03 parts by weight or more and 1.50 parts by weight or less with respect to 100 parts by weight of the component (A). When the content of the component (D) is less than 0.03 part by weight with respect to 100 parts by weight of the component (A), the surface curability tends to be poor and the amount of outgas tends to increase. When it is more than 50 parts by weight, the glass transition temperature tends to be low and the amount of outgas tends to increase.
The total amount of the components (A) to (D) is preferably 20 to 100 parts by weight, preferably 30 to 100 parts by weight, and 40 to 40 parts by weight, based on the total amount of the thermally cationically polymerizable resin composition. It is particularly preferable that the amount is 100 parts by weight. The residue is the component (E).
［用途］
熱カチオン重合性樹脂組成物は、光学部品固定（例えばディスプレイ装置バックライトユニット組立、光ピックアップ組立）、カメラモジュール組立、レンズモジュール組立、光通信用モジュール組立、ハードディスク組立、及び電子部品の保護（例えば、モールド）に用いることができる。
[Use]
The thermocation polymerizable resin composition can be used for fixing optical components (for example, display device backlight unit assembly, optical pickup assembly), camera module assembly, lens module assembly, optical communication module assembly, hard disk assembly, and protection of electronic components (for example). , Mold).
以下に本発明の具体的な実施様態を明らかにするために実施例を示すが、本発明はここに示す実施例のみに限定されるわけではない。 Examples are shown below in order to clarify a specific embodiment of the present invention, but the present invention is not limited to the examples shown here.
実施例及び比較例の各組成物を以下の原材料を使用して製造した。
１．（Ａ）成分：カチオン硬化性樹脂
（１）エポキシ樹脂
クレゾールノボラック型エポキシ樹脂（ＤＩＣ社製、ＥＰＩＣＬＯＮ Ｎ－６５５－ＥＸＰ－Ｓ）
ビスフェノールＡ型エポキシ樹脂（ＤＩＣ社製、ＥＰＩＣＬＯＮ ＥＸＡ－８５０ＣＲＰ）
ビスフェノールＦ型エポキシ樹脂（ＤＩＣ社製、ＥＰＩＣＬＯＮ ＥＸＡ－８３０ＬＶＰ）
脂環式エポキシ樹脂；（３，３’，４，４’－ジエポキシ）ビシクロヘキシル（ダイセル社製、セロキサイド８０１０）
脂環式エポキシ樹脂；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）
（２）オキセタン樹脂
３－エチル－３－フェノキシメチルオキセタン（東亞合成社製、ＯＸＴ－２１１（ＰＯＸ））
キシリレンビスオキセタン（東亞合成社製、ＯＸＴ－１２１（ＸＤＯ））
オキセタニルシルセスキオキセタン（東亞合成社製、ＯＸＴ－１９１）
Each composition of Example and Comparative Example was produced using the following raw materials.
1. 1. (A) Component: Cationic curable resin (1) Epoxy resin Cresol Novolac type epoxy resin (manufactured by DIC, EPICLON N-655-EXP-S)
Bisphenol A type epoxy resin (manufactured by DIC, EPICLON EXA-850CRP)
Bisphenol F type epoxy resin (manufactured by DIC, EPICLON EXA-830LVP)
Alicyclic epoxy resin; (3,3', 4,4'-diepoxy) Bicyclohexyl (manufactured by Daicel, Celoxide 8010)
Alicyclic epoxy resin; 3', 4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (manufactured by Daicel, Celoxide 2021P)
(2) Oxetane Resin 3-Ethyl-3-phenoxymethyloxetane (manufactured by Toagosei Co., Ltd., OXT-211 (POX))
Xylylene bis oxetane (manufactured by Toagosei Co., Ltd., OXT-121 (XDO))
Oxetane sill sesquioxetane (manufactured by Toagosei Co., Ltd., OXT-191)
２．（Ｂ）成分：ヨードニウム塩
４－メチルフェニル－４－（１－メチルエチル）フェニルヨードニウム・テトラキス（ペンタフルオロフェニル）ボレート（ソルベイ（ローディア）社製、ＰＩ－２０７４）。
2. 2. (B) Ingredient: Iodonium salt 4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrakis (pentafluorophenyl) borate (manufactured by Solvay (Rhodia), PI-2074).
３．（Ｃ）成分：有機過酸化物
１，１，３，３－テトラメチルブチルパーオキシ－２－エチルヘキサノエート（日本油脂社製、パーオクタＯ）。
3. 3. (C) Component: Organic peroxide 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (manufactured by NOF Corporation, Perocta O).
４．（Ｄ）成分：熱カチオン重合開始剤
４－ヒドロキシフェニル－メチル－ベンジルスルホニウムトリス（ペンタフルオロエチル）トリフルオロホスフェート（サンアプロ社製、ＴＡ－１００）。
4. (D) Component: Thermal cation polymerization initiator 4-hydroxyphenyl-methyl-benzylsulfonium tris (pentafluoroethyl) trifluorophosphate (manufactured by San-Apro, TA-100).
５．（Ｅ）成分：その他の成分
光増感剤：２，４－ジエチルチオキサントン（日本化薬社製、ＤＥＴＸ－ｓ）
充填剤（フィラー）：シリカ（ＡＧＣ エスアイテック社製、ＮＰ－１００）
充填剤（チキソ付与剤）：ヒュームドシリカ（日本アエロジル社製、ＮＫＣ１３０）
溶剤：４－ブチロラクトン（関東化学社製）
ポットライフ安定剤：４－ヒドロキシフェニルジメチルスルホニウムメチルサルファイト（三新化学社製、ＳＩ助剤）
重合禁止剤）：ジブチルヒドロキシトルエン（関東化学社製、ＢＨＴ）
カップリング剤：３－グリシドキシプロピルトリメトキシシラン（信越化学工業社製、ＫＢＭ４０３）
なお、一部の固体の増感剤、開始剤、添加剤などは樹脂に溶解しにくいものがあるため、予め４－ブチロラクトンに溶解してから樹脂と混合した。
5. (E) Ingredients: Other Ingredients Photosensitizer: 2,4-diethylthioxanthone (manufactured by Nippon Kayaku Co., Ltd., DETX-s)
Filler: Silica (AGC SITEC, NP-100)
Filler (thixotropic agent): fumed silica (manufactured by Aerosil Japan, NKC130)
Solvent: 4-Butyrolactone (manufactured by Kanto Chemical Co., Inc.)
Pot life stabilizer: 4-hydroxyphenyldimethylsulfonium methylsulfite (manufactured by Sanshin Chemical Co., Ltd., SI aid)
Polymerization inhibitor): Dibutylhydroxytoluene (manufactured by Kanto Chemical Co., Inc., BHT)
Coupling agent: 3-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM403)
Since some solid sensitizers, initiators, additives, etc. are difficult to dissolve in the resin, they were previously dissolved in 4-butyrolactone and then mixed with the resin.
実施例１～１３、比較例１～７
〔調製条件〕
熱カチオン重合性樹脂組成物を、表１に記載の配合に基づき、各成分を混合し、室温（２５±３℃。以下同じ。）環境の下、撹拌機で透明になるまで撹拌し、調製した。
Examples 1 to 13, Comparative Examples 1 to 7
[Preparation conditions]
The thermally cationically polymerizable resin composition is prepared by mixing each component based on the formulation shown in Table 1 and stirring the mixture in a room temperature (25 ± 3 ° C.; the same applies hereinafter) environment with a stirrer until it becomes transparent. did.
〔評価条件〕
・表面硬化性
スライドガラス上に樹脂を５０μｍ厚で塗布し、１００℃に加熱したホットプレート上で６０分間熱硬化を行った。室温で１０分間冷却後、指触にて表面硬化性を確認した。
○：硬化、×：表面未硬化(べたつき、タックあり）
[Evaluation conditions]
-A resin was applied to a surface-curable slide glass to a thickness of 50 μm, and thermosetting was performed for 60 minutes on a hot plate heated to 100 ° C. After cooling at room temperature for 10 minutes, the surface curability was confirmed by touch.
○: Hardened, ×: Surface uncured (sticky, tacky)
・アウトガス量
１００μｌのアルミパンに樹脂を１５±２ｍｇ塗布し、１００℃に加熱したホットプレート上で６０分間熱硬化を行った。室温で１０分間冷却後、精密天秤（メトラー・トレド社製、ＸＰ２Ｕ）で秤量した（初期重量）。その後、１５０℃の熱風オーブン（エスペック社製、ＬＣ１１３）で１５時間加熱した。室温で６０分間冷却後、精密天秤で秤量した（加熱後重量）。以下の計算式から重量変化率（%）を求め、アウトガス量とした。
15 ± 2 mg of resin was applied to an aluminum pan having an outgas amount of 100 μl, and thermosetting was performed for 60 minutes on a hot plate heated to 100 ° C. After cooling at room temperature for 10 minutes, the weight was weighed with a precision balance (Mettler Toledo, XP2U) (initial weight). Then, it was heated in a hot air oven (manufactured by Espec Co., LC113) at 150 ° C. for 15 hours. After cooling at room temperature for 60 minutes, the weight was weighed with a precision balance (weight after heating). The weight change rate (%) was calculated from the following formula and used as the outgas amount.
・ガラス転移温度（Ｔｇ）及び貯蔵弾性率
長さ５０ｍｍ、幅１０ｍｍ、厚さ０．５ｍｍの型に注型し、１００℃の熱風オーブン（エスペック社製、ＬＣ１１３）で６０分間熱硬化を行い、硬化物試験片を作製した。得られた硬化物試験片を動的粘弾性測定装置（ＤＭＡ、セイコーインスツル社製、ＤＭＳ６１００）にて、周波数１．０Ｈｚで昇温させながら測定を行った。得られた結果の損失正接ｔａｎδにおけるピークトップ温度をＴｇとした。
Ｔｇと同様の条件で硬化物試験片の作製及び動的粘弾性測定装置（ＤＭＡ、セイコーインスツル社製、ＤＭＳ６１００）による測定を行った。得られた結果において２５℃での貯蔵弾性率の値を抽出した。
-Glass transition temperature (Tg) and storage elastic modulus A mold with a length of 50 mm, a width of 10 mm, and a thickness of 0.5 mm was cast, and heat-cured in a hot air oven (manufactured by Espec Co., LC113) at 100 ° C. for 60 minutes. A cured product test piece was prepared. The obtained cured product test piece was measured with a dynamic viscoelasticity measuring device (DMA, manufactured by Seiko Instruments Inc., DMS6100) while raising the temperature at a frequency of 1.0 Hz. The peak top temperature at the loss tangent tan δ of the obtained result was defined as Tg.
A cured product test piece was prepared and measured by a dynamic viscoelasticity measuring device (DMA, Seiko Instruments Inc., DMS6100) under the same conditions as Tg. In the obtained results, the value of the storage elastic modulus at 25 ° C. was extracted.
結果を以下の表にまとめた。 The results are summarized in the table below.
実施例１～１３の熱カチオン重合性樹脂組成物は、表面硬化性が優れており、かつ、アウトガス量が低減されていた。
特に、実施例１～５の比較により、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が好ましい範囲であると、アウトガス量がより低減されていた。実施例７～１１の比較によっても、同様のことがいえる。
また、実施例１～５と実施例７～１１、及び、実施例６と実施例１２との比較により、熱カチオン重合性樹脂組成物が、更に（Ｅ）成分を含む場合であっても、表面硬化性が優れており、かつ、アウトガス量が低減されていた。
比較例１～６は、（Ｄ）成分を含まないか、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が０．０３重量部未満であるため、表面硬化性が劣っていた。特に、比較例４～６は、アウトガス量が多かった。比較例７は、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が１．５０重量部超であるため、アウトガス量が多かった。そして、実施例１～５と比較例１～３との比較により、（Ｄ）成分以外の組成がほぼ同じであるとき、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量を所定の範囲とすることで、表面硬化性が優れており、かつ、アウトガス量が低減されていた。実施例７～１１と比較例４～６との比較によっても、同様のことがいえる。
The thermally cationically polymerizable resin compositions of Examples 1 to 13 had excellent surface curability and a reduced amount of outgas.
In particular, by comparison of Examples 1 to 5, the amount of outgas was further reduced when the content of the component (D) was in a preferable range with respect to 100 parts by weight of the component (A). The same can be said by comparing Examples 7 to 11.
Further, by comparing Examples 1 to 5 and Examples 7 to 11, and Examples 6 and 12, even when the thermally cationically polymerizable resin composition further contains the component (E), it may be contained. The surface curability was excellent, and the amount of outgas was reduced.
In Comparative Examples 1 to 6, the surface curability is high because the component (D) is not contained or the content of the component (D) is less than 0.03 part by weight with respect to 100 parts by weight of the component (A). It was inferior. In particular, Comparative Examples 4 to 6 had a large amount of outgas. In Comparative Example 7, since the content of the component (D) was more than 1.50 parts by weight with respect to 100 parts by weight of the component (A), the amount of outgas was large. Then, by comparison between Examples 1 to 5 and Comparative Examples 1 to 3, when the compositions other than the component (D) are substantially the same, the component (D) is contained with respect to 100 parts by weight of the component (A). By setting the amount within a predetermined range, the surface curability was excellent and the amount of outgas was reduced. The same can be said by comparing Examples 7 to 11 with Comparative Examples 4 to 6.
Claims (4)
（Ｂ）式：Ａｒ１－Ｉ＋－Ａｒ２・Ｘ－（式中、Ａｒ１及びＡｒ２は、独立して、置換又は非置換のアリール基であり、Ｘ－は、アニオンである）で示されるヨードニウム塩、
（Ｃ）有機過酸化物、及び
（Ｄ）熱カチオン重合開始剤
を含み、（Ａ）成分の１００重量部に対して、（Ｄ）成分の含有量が０．０３重量部以上１．５０重量部以下である、熱カチオン重合性樹脂組成物。 (A) Cationic curable resin,
Formula (B): Ar 1 −I + −Ar 2 · X − (in the formula, Ar 1 and Ar 2 are independently substituted or unsubstituted aryl groups, and X − is an anion). The iodonium salt shown,
It contains (C) an organic peroxide and (D) a thermal cationic polymerization initiator, and the content of the component (D) is 0.03 part by weight or more and 1.50 parts by weight with respect to 100 parts by weight of the component (A). A thermal cationically polymerizable resin composition which is less than or equal to a portion.
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| JP5952732B2 (en) | 2012-12-28 | 2016-07-13 | 協立化学産業株式会社 | Thermally cationic polymerizable composition |
| JP6442333B2 (en) | 2015-03-17 | 2018-12-19 | デクセリアルズ株式会社 | Compound, thermosetting resin composition, and thermosetting sheet |
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