JP6331013B2 - カチオン硬化性樹脂組成物 - Google Patents
カチオン硬化性樹脂組成物 Download PDFInfo
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- JP6331013B2 JP6331013B2 JP2014105560A JP2014105560A JP6331013B2 JP 6331013 B2 JP6331013 B2 JP 6331013B2 JP 2014105560 A JP2014105560 A JP 2014105560A JP 2014105560 A JP2014105560 A JP 2014105560A JP 6331013 B2 JP6331013 B2 JP 6331013B2
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- 239000011342 resin composition Substances 0.000 title claims description 35
- 125000002091 cationic group Chemical group 0.000 title claims description 29
- -1 3,4-epoxycyclohexyl Compound Chemical class 0.000 claims description 39
- 239000003822 epoxy resin Substances 0.000 claims description 32
- 229920000647 polyepoxide Polymers 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical class C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001723 curing Methods 0.000 claims description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 claims description 4
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims description 3
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 claims description 3
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 claims description 3
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 3
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- HIYIGPVBMDKPCR-UHFFFAOYSA-N 1,1-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1(COC=C)CCCCC1 HIYIGPVBMDKPCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims description 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
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- 238000005259 measurement Methods 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 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 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 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 7
- 238000005979 thermal decomposition reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001924 cycloalkanes Chemical group 0.000 description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 125000005462 imide group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 238000004382 potting Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002848 norbornenes Chemical class 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 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 3
- 239000002245 particle Substances 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- OVJHMJJVXOJMBB-UHFFFAOYSA-N 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)N(CCOC(=O)C=C)C(=O)C21 OVJHMJJVXOJMBB-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- VTESCYNPUGSWKG-UHFFFAOYSA-N (4-tert-butylphenyl)hydrazine;hydrochloride Chemical compound [Cl-].CC(C)(C)C1=CC=C(N[NH3+])C=C1 VTESCYNPUGSWKG-UHFFFAOYSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 1
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 description 1
- IBASEVZORZFIIH-UHFFFAOYSA-N 1-(9h-fluoren-2-yl)ethanone Chemical compound C1=CC=C2C3=CC=C(C(=O)C)C=C3CC2=C1 IBASEVZORZFIIH-UHFFFAOYSA-N 0.000 description 1
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- LSIXBBPOJBJQHN-UHFFFAOYSA-N 2,3-Dimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1C2 LSIXBBPOJBJQHN-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- SNAGVRNJNARVRV-UHFFFAOYSA-N 2-[(3-ethyloxetan-3-yl)methoxymethyl]oxolane Chemical compound C1CCOC1COCC1(CC)COC1 SNAGVRNJNARVRV-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
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- WKXMZIDBVDIVME-UHFFFAOYSA-N 3-[(3-ethyloxetan-3-yl)methoxy]-2,2-bis[(3-ethyloxetan-3-yl)methoxymethyl]propan-1-ol Chemical compound C1OCC1(CC)COCC(CO)(COCC1(CC)COC1)COCC1(CC)COC1 WKXMZIDBVDIVME-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
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- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- PWGAXPBJOGFFMY-UHFFFAOYSA-N 3-ethyl-3-(2-methylpropoxymethoxymethyl)oxetane Chemical compound CC(C)COCOCC1(CC)COC1 PWGAXPBJOGFFMY-UHFFFAOYSA-N 0.000 description 1
- DILMQZOSIJKYHA-UHFFFAOYSA-N 3-ethyl-3-[(2,3,4,5,6-pentabromophenoxy)methyl]oxetane Chemical compound BrC=1C(Br)=C(Br)C(Br)=C(Br)C=1OCC1(CC)COC1 DILMQZOSIJKYHA-UHFFFAOYSA-N 0.000 description 1
- FQUZJULGTSCUDF-UHFFFAOYSA-N 3-ethyl-3-[(2,3,4,5,6-pentachlorophenoxy)methyl]oxetane Chemical compound ClC=1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1OCC1(CC)COC1 FQUZJULGTSCUDF-UHFFFAOYSA-N 0.000 description 1
- LNZCVOLEQJDCJG-UHFFFAOYSA-N 3-ethyl-3-[(2-methylphenoxy)methyl]oxetane Chemical compound C=1C=CC=C(C)C=1OCC1(CC)COC1 LNZCVOLEQJDCJG-UHFFFAOYSA-N 0.000 description 1
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Description
本発明の要旨を次に説明する。
下記の(A)〜(C)成分を含有することを特徴とするカチオン硬化性樹脂組成物
(A)成分:シクロアルカン骨格及び少なくとも1つのグリシジル基を有する化合物
(B)成分:脂環式炭化水素骨格を有する化合物(但し、(A)成分及び環状構造を構成する炭素原子に、(メタ)アクリル基、カルボキシ基、イミド基、スルホ基、シアノ基、ニトロ基からなる群から選択される電子吸引基が直接結合している化合物を除く)
(C)成分:ヨードニウム塩を含有するカチオン開始剤
<(A)成分>
本発明のカチオン硬化性樹脂組成物における(A)成分は、シクロアルカン骨格及び少なくとも1つのグリシジル基を有する化合物であれば特に限定されるものではない。単独、あるいは2種以上を混合して使用することができる。ここで(A)成分のシクロアルカン骨格とは、炭素数3〜12の脂環式炭化水素の構造を意味する。
本発明の(B)成分は、脂環式炭化水素骨格を有する化合物(但し、(A)成分及び環状構造を構成する炭素原子に、(メタ)アクリル基、カルボキシ基、イミド基、スルホ基、シアノ基、ニトロ基、のいずれかから選択される電子吸引基が直接結合している化合物を除く)である。後述する比較例4、5に示すように環状構造を構成する炭素原子に、(メタ)アクリル基、カルボキシ基、イミド基、スルホ基、シアノ基、ニトロ基のいずれかから選択される電子吸引基が直接結合している化合物を用いた場合、低温硬化性が劣ることから好ましくない。なお、上記脂環式炭化水素骨格とは、炭素数3〜12の炭素原子により構成された構造などがあげられる。(B)成分の沸点は特に限定されないが低温硬化性及び作業性の観点から20℃以上が好ましく、更に好ましくは30℃以上であり、特に好ましくは40℃以上である。
本発明の(C)成分は、カチオン開始剤であり、活性エネルギー線の照射又は加熱により酸を発生するヨードニウム塩である。なお、(C)成分の熱分解温度は、組成物の貯蔵安定性の観点から、200℃以上であることが好ましく、より好ましくは220℃以上である。なお、熱分解温度は、(C)成分に対してTG/DTA(熱天秤/示差熱分析)装置を用いて測定した値である。また、本発明の(C)成分は、(A)成分に対して可溶であることから、10μm以下の微細な隙間でも組成物が硬化することができる。
本発明の(D)成分のシランカップリング剤は、(A)〜(C)成分の相溶性を向上させ、より低温硬化性を向上させることができる化合物である。(D)成分としては、例えば、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エトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、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等のグリシジル基含有シランカップリング剤、ビニルトリス(β−メトキシエトキシ)シラン、ビニルトリエトキシシラン、ビニルトリメトキシシラン等のビニル基含有シランカップリング剤、γ−メタクリロキシプロピルトリメトキシシラン等の(メタ)アクリル基含有シランカップリング剤、N−β−(アミノエチル)−γ−アミノプロピルトリメトキシシラン、γ−アミノプロピルトリエトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン等のアミノ基含有シランカップリング剤、その他γ−メルカプトプロピルトリメトキシシラン、γ−クロロプロピルトリメトキシシラン等が挙げられる。これらの中でもグリシジル基含有シランカップリング剤が好ましく用いられ、グリシジル基含有シランカップリング剤の中でも、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トリエトキシシランが好ましい。これらは単独で用いられてもよく、2種以上が併用されてもよい。また、(D)成分の配合量は、特に限定されるものではないが、本発明の(A)成分と(B)成分の合計100質量部に対し0.001〜30質量部であることがあげられる。
組成物を調製するために下記成分を準備した。
<(A)成分>
a1:水添ビスフェノールA型エポキシ樹脂、粘度1900mPas、エポキシ当量205、商品名YX−8000、三菱化学株式会社製
a2:水添ビスフェノールF型エポキシ樹脂、粘度200mPas、エポキシ当量180、商品名YL−6753、三菱化学株式会社製
<(A)成分の比較成分>
a’1:芳香族ビスフェノールA型エポキシ樹脂及び芳香族ビスフェノールF型エポキシ樹脂の混合物、粘度2250mPas、エポキシ当量165、商品名EXA−835LV、DIC株式会社製
<(B)成分>
b1:シクロヘキサン、沸点81℃
b2:シクロペンタン、沸点49℃
b3:2−ノルボルネン、沸点96℃
b4:シクロヘキシルビニルエーテル、沸点147℃
b5:シクロヘキサンジメタノール、沸点283℃
b6:シクロヘキサンジメタノールジビニルエーテル、沸点104℃、商品名CHDVE、日本カーバイド工業株式会社
b7:メチルシクロヘキサン、沸点101℃
<(B)成分の比較成分>
b’1:N−アクリロイルオキシエチルヘキサヒドロフタルイミド(環状構造を構成する炭素原子に電子吸引基であるイミド基が直接結合している脂環式炭化水素骨格を有する化合物)
b’2:シクロヘキシルアクリレート(環状構造を構成する炭素原子に電子吸引基である(メタ)アクリル基が直接結合している脂環式炭化水素骨格を有する化合物)、沸点183℃
<(C)成分>
c1:4−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−フッ素化アルキルフルオロリン酸、熱分解温度247℃
c2:4−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、商品名Photo initiator2074ローディア社製、熱分解温度252℃
<(D)成分>
d1:3−グリシドキシプロピルトリメトキシシラン
表1、2に示す重量割合で、(A)〜(D)成分を加え、遮光環境化で、25℃で攪拌混合し、カチオン硬化性樹脂組成物を調整した。
各カチオン硬化性樹脂組成物の低温硬化性について、示差走査熱量(DSC)を用いて反応開始温度を測定し、その結果を表1、2に示す。なお、DSC測定にはセイコーインスツルメント社製DSC110を用い、窒素雰囲気下昇温速度10℃/minで30〜200℃まで昇温測定した。反応開始温度とは、DSC測定結果のグラフのベースラインとピークの変曲点における接線との交点とした。なお、実施例1、5、6と比較例3〜5の示差走査熱量の測定結果のグラフについて、図1〜6に示す。
実施例1〜12の各カチオン硬化性樹脂組成物0.01gをスライドガラス上に滴下し、カバーグラスを被せてカチオン硬化性組成物が薄膜としてガラスに挟まれた試験片を作成する。次に紫外線照射機により積算光量30kJ/m2の光活性エネルギーを照射後、ガラス同士が接着して手で動かせなくなることを確認する試験を行った。
試験結果は、実施例1〜12の各カチオン硬化性樹脂組成物はすべて接着しており、活性エネルギー線硬化性を有することを確認した。
実施例1において、c1の代わりに、平均粒径3μmの潜在性硬化剤(製品名PN-23J、味の素ファインテクノ株式会社製)を用いた以外は、実施例1と同様にして調製し、比較例6を得た。
2枚のスライドガラスを重ね両端をピンチで固定した後、重なり合う端面が上になるうスライドガラスを垂直に立てる。上部端面中央の重ねあわせ部分に実施例1及び比較例6の硬化性組成物を滴下し、100℃の高温槽に1時間放置する。硬化後のガラスを剥がし、液状の箇所がある場合を「×」、ない場合を「○」とした。
試験結果は、実施例1を用いた場合は「○」であり、比較例6を用いた場合は「×」であった。
Claims (7)
- 下記の(A)〜(D)成分を含有することを特徴とするカチオン硬化性樹脂組成物。
(A)成分:水添ビスフェノールA型エポキシ樹脂、水添ビスフェノールF型エポキシ樹脂、水添ビスフェノールE型エポキシ樹脂、エポキシシクロヘキサン、ピネンオキシド、リモネンジオキシド、ビニルシクロヘキセンジエポキシド、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、ビス(3,4−エポキシシクロヘキシル)アジペート、1,4−シクロヘキサンジメタノールジグリシジルエーテルからなる群のいずれかから選択される化合物
(B)成分:シクロヘキサン、シクロペンタン、2−ノルボルネン、シクロヘキシルビニルエーテル、シクロヘキサンジメタノール、シクロヘキサンジメタノールジビニルエーテル、メチルシクロヘキサンからなる群から少なくとも1以上選択され、(A)成分との混合物が(C)成分を溶解できる脂環式炭化水素骨格を有する化合物
(C)成分:ヨードニウム塩を含有するカチオン開始剤
(D)成分:シランカップリング剤 - (D)成分が、グリシジル基含有シランカップリング剤であることを特徴とする請求項1に記載のカチオン硬化性樹脂組成物。
- (D)成分が、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エトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、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からなる群から少なくとも1以上選択されることを特徴とする請求項1または2のいずれか1項に記載のカチオン硬化性樹脂組成物。
- 前記(A)成分と(B)成分の合計100質量部に対し、(B)成分が0.01〜95質量部、(C)成分が0.001〜30質量部を含有することを特徴とする請求項1〜4のいずれか1項に記載のカチオン硬化性樹脂組成物。
- 熱のみによって硬化するカチオン硬化性樹脂組成物であることを特徴とする請求項1〜5のいずれか1項に記載のカチオン硬化性樹脂組成物。
- 請求項1〜6のいずれか1項に記載のカチオン硬化性樹脂組成物に対して、50〜100℃の温度により硬化することを特徴とする硬化方法。
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