JPWO2020045358A1 - Composition, adhesive containing it, cured product thereof and method for producing the same - Google Patents
Composition, adhesive containing it, cured product thereof and method for producing the same Download PDFInfo
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- JPWO2020045358A1 JPWO2020045358A1 JP2020539448A JP2020539448A JPWO2020045358A1 JP WO2020045358 A1 JPWO2020045358 A1 JP WO2020045358A1 JP 2020539448 A JP2020539448 A JP 2020539448A JP 2020539448 A JP2020539448 A JP 2020539448A JP WO2020045358 A1 JPWO2020045358 A1 JP WO2020045358A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 159
- 239000000853 adhesive Substances 0.000 title claims abstract description 127
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 127
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 239000003999 initiator Substances 0.000 claims description 38
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 14
- 125000003566 oxetanyl group Chemical group 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 230000001678 irradiating effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 46
- -1 curing speed Substances 0.000 description 137
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 63
- 238000001723 curing Methods 0.000 description 55
- 239000004593 Epoxy Substances 0.000 description 39
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 239000000126 substance Substances 0.000 description 20
- 239000010408 film Substances 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 16
- 238000011156 evaluation Methods 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 150000001450 anions Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 150000002605 large molecules Chemical class 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 150000003384 small molecules Chemical class 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 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 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 0 CS(c1ccc(*)cc1)(c1ccc(*)cc1)c(cc1)ccc1Sc(cc1)ccc1[S+]c(cc1)ccc1OCCO Chemical compound CS(c1ccc(*)cc1)(c1ccc(*)cc1)c(cc1)ccc1Sc(cc1)ccc1[S+]c(cc1)ccc1OCCO 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 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 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000002985 plastic film Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229940052303 ethers for general anesthesia Drugs 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 4
- 229920006255 plastic film Polymers 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 150000002921 oxetanes Chemical class 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
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 2
- UWFHYGTWXNRUDH-UHFFFAOYSA-N 3-ethyl-3-[4-[(3-ethyloxetan-3-yl)methoxy]butoxymethyl]oxetane Chemical compound C1OCC1(CC)COCCCCOCC1(CC)COC1 UWFHYGTWXNRUDH-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
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
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- 229910052711 selenium Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GJOGTGLNIWPDPF-UHFFFAOYSA-N trifluoromethyl hydrogen sulfite Chemical compound OS(=O)OC(F)(F)F GJOGTGLNIWPDPF-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Polyethers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
硬化速度および耐水性に優れ、かつ、接着力に優れた硬化物が得られる組成物、これを含有する接着剤、その硬化物およびその製造方法を提供する。ラジカル重合性成分(A)およびカチオン重合性成分(B)を含有する組成物であり、ラジカル重合性成分(A)が、架橋縮合環を有するラジカル重合性化合物(A1)をラジカル重合性成分(A)100質量部中に70〜100質量部含有し、カチオン重合性成分(B)が、架橋縮合環を有するカチオン重合性化合物(B1)をカチオン重合性成分(B)100質量部中に10〜50質量部含有する。Provided are a composition capable of obtaining a cured product having excellent curing speed and water resistance and excellent adhesive strength, an adhesive containing the same, a cured product thereof, and a method for producing the same. A composition containing a radically polymerizable component (A) and a cationically polymerizable component (B), wherein the radically polymerizable component (A) is a radically polymerizable component (A1) having a crosslinked condensed ring. A) The cationically polymerizable component (B) contains 70 to 100 parts by mass in 100 parts by mass, and the cationically polymerizable compound (B1) having a crosslinked condensed ring is 10 in 100 parts by mass of the cationically polymerizable component (B). Contains ~ 50 parts by mass.
Description
本発明は、組成物、これを含有する接着剤、その硬化物およびその製造方法に関し、詳しくは、硬化速度および耐水性に優れ、かつ、接着力に優れた硬化物が得られる組成物、これを含有する接着剤、その硬化物およびその製造方法に関する。 The present invention relates to a composition, an adhesive containing the same, a cured product thereof, and a method for producing the same. The present invention relates to an adhesive containing the above, a cured product thereof, and a method for producing the same.
カチオン硬化性組成物は、インキ、塗料、各種コーティング剤、接着剤、光学部材等の分野において用いられている。このような、硬化性組成物の改良に関して、種々の報告がなされている。 Cathodic curable compositions are used in the fields of inks, paints, various coating agents, adhesives, optical members and the like. Various reports have been made on such improvements in the curable composition.
例えば、特許文献1では、低粘度で、硬化性に優れ、各種プラスチックフィルムまたはシートへの接着力および無色透明性にも優れたプラスチックフィルム等用活性エネルギー線硬化型接着剤組成物が提案されている。また、特許文献2では、低粘度で、硬化性に優れ、塗工・硬化時の雰囲気湿度が高くとも各種プラスチックフィルム等への接着力に優れ、無色透明性にも優れたプラスチックフィルム等用活性エネルギー線硬化型接着剤組成物が提案されている。さらに、特許文献3では、塗工環境の湿度が高くても、硬化性に優れ、一定時間経過後の接着力、耐久性および耐湿熱試験終了後の接着力が良好であり、低粘度である光硬化性接着剤が提案されている。さらにまた、特許文献4では、ジシクロペンタジエン骨格を有するジアクリレートとジシクロペンタジエン骨格を有するジグリシジルエーテルを有する光および熱硬化性樹脂組成物を適用して、硬化性樹脂組成物層を形成する工程と、さらに硬化性樹脂組成物層に活性エネルギー線を照射する工程を有する積層体の製造方法が提案されている。 For example, Patent Document 1 proposes an active energy ray-curable adhesive composition for plastic films and the like, which has a low viscosity, is excellent in curability, and has excellent adhesive strength to various plastic films or sheets and colorless transparency. There is. Further, in Patent Document 2, the activity for plastic films, etc., which has low viscosity, is excellent in curability, is excellent in adhesive strength to various plastic films, etc. even if the atmospheric humidity at the time of coating and curing is high, and is also excellent in colorless transparency. Energy ray-curable adhesive compositions have been proposed. Further, in Patent Document 3, even if the humidity of the coating environment is high, the curability is excellent, the adhesive strength after a lapse of a certain period of time, the durability and the adhesive strength after the end of the moisture resistance heat test are good, and the viscosity is low. Photocurable adhesives have been proposed. Furthermore, in Patent Document 4, a light and thermosetting resin composition having a diacrylate having a dicyclopentadiene skeleton and a diglycidyl ether having a dicyclopentadiene skeleton is applied to form a curable resin composition layer. A method for producing a laminate having a step and a step of irradiating the curable resin composition layer with active energy rays has been proposed.
しかしながら、特許文献1〜4で提案されているカチオン硬化性組成物では、十分な硬化性が得られず、得られる硬化物の耐水性が十分ではないという問題がある。例えば、接着剤として用いた場合に、硬化速度が不十分な場合や、十分な接着力および耐水性が得られない場合がある。 However, the cationically curable compositions proposed in Patent Documents 1 to 4 have a problem that sufficient curability cannot be obtained and the water resistance of the obtained cured product is not sufficient. For example, when used as an adhesive, the curing rate may be insufficient, or sufficient adhesive strength and water resistance may not be obtained.
そこで、本発明は、上記問題点に鑑みてなされたものであり、本発明の目的は、硬化速度および耐水性に優れ、かつ、接着力に優れた硬化物が得られる組成物、これを含有する接着剤、その硬化物およびその製造方法を提供することにある。 Therefore, the present invention has been made in view of the above problems, and an object of the present invention is to include a composition capable of obtaining a cured product having excellent curing speed and water resistance and excellent adhesive strength. It is an object of the present invention to provide an adhesive, a cured product thereof, and a method for producing the same.
本発明者等は、上記課題を解消するために鋭意検討した結果、上記の目的を達成したものである。以下に、本発明について、詳細に説明する。 The present inventors have achieved the above object as a result of diligent studies to solve the above problems. Hereinafter, the present invention will be described in detail.
すなわち、本発明の組成物は、ラジカル重合性成分(A)およびカチオン重合性成分(B)を含有する組成物において、 前記ラジカル重合性成分(A)が、架橋縮合環を有するラジカル重合性化合物(A1)をラジカル重合性成分(A)100質量部中に70〜100質量部含有し、
前記カチオン重合性成分(B)が、架橋縮合環を有するカチオン重合性化合物(B1)をカチオン重合性成分(B)100質量部中に10〜50質量部含有することを特徴とするものである。That is, the composition of the present invention is a composition containing a radically polymerizable component (A) and a cationically polymerizable component (B), wherein the radically polymerizable component (A) is a radically polymerizable compound having a crosslinked condensed ring. 70 to 100 parts by mass of (A1) is contained in 100 parts by mass of the radically polymerizable component (A).
The cationically polymerizable component (B) is characterized by containing 10 to 50 parts by mass of the cationically polymerizable compound (B1) having a crosslinked condensed ring in 100 parts by mass of the cationically polymerizable component (B). ..
本発明の組成物においては、さらに、ラジカル重合性開始剤(C)およびカチオン重合性開始剤(D)を含有し、
前記ラジカル重合性成分(A)、前記カチオン重合性成分(B)、前記ラジカル重合性開始剤(C)および前記カチオン重合性開始剤(D)の総量100質量部中に、前記ラジカル重合性成分(A)40〜60質量部、前記カチオン重合性成分(B)30〜50質量部、前記ラジカル重合性開始剤(C)1〜10質量部および前記カチオン重合性開始剤(D)1〜10質量部を含有することが好ましい。かかる組成物は、初期硬化性に優れている。The composition of the present invention further contains a radically polymerizable initiator (C) and a cationically polymerizable initiator (D).
The radically polymerizable component in 100 parts by mass of the total amount of the radically polymerizable component (A), the cationically polymerizable component (B), the radically polymerizable initiator (C) and the cationically polymerizable initiator (D). (A) 40 to 60 parts by mass, the cationically polymerizable component (B) 30 to 50 parts by mass, the radically polymerizable initiator (C) 1 to 10 parts by mass, and the cationically polymerizable initiator (D) 1 to 10 parts. It preferably contains parts by mass. Such a composition is excellent in initial curability.
また、本発明の組成物においては、前記ラジカル重合性化合物(A1)および前記カチオン重合性化合物(B1)に含まれる架橋縮合環が、下記式(I)で表される構造を有する架橋縮合環であることが好ましい。かかる組成物は、得られる硬化物が耐水性に優れている。
Further, in the composition of the present invention, the crosslinked condensed ring contained in the radically polymerizable compound (A1) and the cationically polymerizable compound (B1) has a structure represented by the following formula (I). Is preferable. In such a composition, the obtained cured product has excellent water resistance.
さらに、本発明の組成物においては、前記カチオン重合性成分(B)として、架橋縮合環を有さない重量平均分子量1,000以上30,000未満のカチオン重合性化合物(B2)を含有することが好ましい。かかる組成物からは、耐水性に優れる硬化物が得られる。 Further, in the composition of the present invention, as the cationically polymerizable component (B), a cationically polymerizable compound (B2) having no crosslinked condensed ring and having a weight average molecular weight of 1,000 or more and less than 30,000 is contained. Is preferable. From such a composition, a cured product having excellent water resistance can be obtained.
さらにまた、本発明の組成物においては、前記カチオン重合性成分(B)として、架橋縮合環を有さない重量平均分子量200以上1,000未満のカチオン重合性化合物(B3)を含有することが好ましい。かかる組成物からは、塗工性および耐水性に優れる硬化物が得られる。 Furthermore, the composition of the present invention may contain, as the cationically polymerizable component (B), a cationically polymerizable compound (B3) having a weight average molecular weight of 200 or more and less than 1,000, which does not have a crosslinked condensed ring. preferable. From such a composition, a cured product having excellent coatability and water resistance can be obtained.
また、本発明の組成物においては、前記カチオン重合性化合物(B3)が、オキセタニル基を有する化合物を含むことが好ましい。かかる組成物からは、耐水性に優れる硬化物が得られる。 Further, in the composition of the present invention, it is preferable that the cationically polymerizable compound (B3) contains a compound having an oxetanyl group. From such a composition, a cured product having excellent water resistance can be obtained.
さらに、本発明の組成物においては、前記ラジカル重合性成分(A)として、カチオン重合性基を有し、イソシアヌレート環および架橋縮合環を有さないラジカル重合性化合物(A2)を含有することが好ましい。かかる組成物は、塗工性および初期接着性に優れている。 Further, in the composition of the present invention, the radically polymerizable component (A) contains a radically polymerizable compound (A2) having a cationically polymerizable group and not having an isocyanurate ring and a crosslinked condensed ring. Is preferable. Such a composition is excellent in coatability and initial adhesiveness.
さらにまた、本発明の組成物においては、前記ラジカル重合性成分(A)として、イソシアヌレート環を含有し、架橋縮合環を有さないラジカル重合性化合物(A3)を含有することが好ましい。かかる組成物からは、耐水性に優れる硬化物が得られる。 Furthermore, in the composition of the present invention, it is preferable that the radically polymerizable component (A) contains an isocyanurate ring and a radically polymerizable compound (A3) having no crosslinked condensed ring. From such a composition, a cured product having excellent water resistance can be obtained.
本発明の接着剤は、本発明の組成物を含むことを特徴とするものである。本発明の組成物を含有することで、硬化速度に優れ、かつ、接着力および耐水性に優れた硬化物が得られる接着剤となる。 The adhesive of the present invention is characterized by containing the composition of the present invention. By containing the composition of the present invention, it becomes an adhesive capable of obtaining a cured product having excellent curing speed and excellent adhesive strength and water resistance.
本発明の硬化物は、本発明の組成物の硬化物であることを特徴とするものである。本発明の組成物を用いることで接着力および耐水性に優れた硬化物となる。 The cured product of the present invention is characterized by being a cured product of the composition of the present invention. By using the composition of the present invention, a cured product having excellent adhesive strength and water resistance can be obtained.
本発明の硬化物の製造方法は、本発明の組成物に対して、活性エネルギー線を照射または加熱する工程を含むことを特徴とするものである。本発明の組成物は、上記成分を含むものであるため、接着力および耐水性に優れた硬化物を容易に得ることができる。 The method for producing a cured product of the present invention is characterized by including a step of irradiating or heating the composition of the present invention with active energy rays. Since the composition of the present invention contains the above components, a cured product having excellent adhesive strength and water resistance can be easily obtained.
本発明によれば、硬化速度および耐水性に優れ、かつ、接着力に優れた硬化物が得られる組成物、これを含有する接着剤、その硬化物およびその製造方法を提供することができる。 According to the present invention, it is possible to provide a composition capable of obtaining a cured product having excellent curing speed and water resistance and excellent adhesive strength, an adhesive containing the same, a cured product thereof, and a method for producing the same.
以下、本発明の組成物、これを含有する接着剤、その硬化物およびその製造方法について、詳細に説明する。 Hereinafter, the composition of the present invention, an adhesive containing the same, a cured product thereof, and a method for producing the same will be described in detail.
<組成物>
まず、本発明の組成物について説明する。本発明の組成物は、ラジカル重合性成分(A)(以下、「成分(A)」とも称す)およびカチオン重合性成分(B)(以下、「成分(B)」とも称す)を含有する組成物である。本発明の組成物においては、架橋縮合環を有するラジカル重合性化合物(A1)(以下、「化合物(A1)」とも称す」を、成分(A)100質量部中に70〜100質量部含有し、架橋縮合環を有するカチオン重合性化合物(B1)(以下、「化合物(B1)」とも称す)を、成分(B)100質量部中に10〜50部含有する。すなわち、化合物(A1)と化合物(B1)を上記の通り適切な割合で含有することにより、硬化速度に優れ、かつ、接着力および耐水性に優れた硬化物が得られる。<Composition>
First, the composition of the present invention will be described. The composition of the present invention contains a radically polymerizable component (A) (hereinafter, also referred to as “component (A)”) and a cationically polymerizable component (B) (hereinafter, also referred to as “component (B)”). It is a thing. In the composition of the present invention, 70 to 100 parts by mass of a radically polymerizable compound (A1) having a crosslinked condensed ring (hereinafter, also referred to as “compound (A1)”” is contained in 100 parts by mass of the component (A). , A cationically polymerizable compound (B1) having a crosslinked condensed ring (hereinafter, also referred to as “compound (B1)”) is contained in 100 parts by mass of the component (B) in an amount of 10 to 50 parts, that is, with the compound (A1). By containing the compound (B1) in an appropriate ratio as described above, a cured product having excellent curing rate and excellent adhesive strength and water resistance can be obtained.
本発明の組成物においては、化合物(A1)、化合物(B1)に加えてラジカル重合性開始剤(C)(以下、「成分(C)」とも称す)およびカチオン重合性開始剤(D)(以下、「成分(D)」とも称す)を含有すると、硬化性が高い組成物が得られることから好ましい。本発明の組成物中の成分(A)、成分(B)、成分(C)および成分(D)の好ましい割合は、成分(A)、成分(B)、成分(C)および成分(D)の総量100質量部中に、それぞれ成分(A)40〜60質量部、成分(B)30〜50質量部、成分(C)1〜10質量部および成分(D)1〜10質量部である。かかる割合とすることで、硬化速度に優れ、かつ、接着力および耐水性に優れた硬化物が得られる組成物を得ることできる。 In the composition of the present invention, in addition to the compound (A1) and the compound (B1), a radical polymerizable initiator (C) (hereinafter, also referred to as “component (C)”) and a cationically polymerizable initiator (D) ( Hereinafter, it is also referred to as “component (D)”), which is preferable because a highly curable composition can be obtained. The preferable ratios of the component (A), the component (B), the component (C) and the component (D) in the composition of the present invention are the component (A), the component (B), the component (C) and the component (D). 40 to 60 parts by mass of component (A), 30 to 50 parts by mass of component (B), 1 to 10 parts by mass of component (C), and 1 to 10 parts by mass of component (D), respectively. .. With such a ratio, it is possible to obtain a composition capable of obtaining a cured product having excellent curing speed and excellent adhesive strength and water resistance.
また、本発明の組成物において、成分(A)と成分(B)の割合としては、成分(A)100質量部に対して成分(B)が50〜130質量部の場合が好ましい。成分(A)と成分(B)の割合が上記の範囲である場合、接着力と耐水性に優れた硬化物が得られることから好ましい。以下、各成分について、詳細に説明する。 Further, in the composition of the present invention, the ratio of the component (A) to the component (B) is preferably 50 to 130 parts by mass with respect to 100 parts by mass of the component (A). When the ratio of the component (A) to the component (B) is in the above range, a cured product having excellent adhesive strength and water resistance can be obtained, which is preferable. Hereinafter, each component will be described in detail.
<ラジカル重合性成分(A)>
成分(A)は、ラジカル重合性基を有する化合物である。このラジカル重合性基とは、ラジカルの存在下で重合が可能な基を意味し、例えば、アクリル基、メタクリル基、ビニル基およびチオール基等が挙げられる。成分(A)は、化合物(A1)、カチオン重合性基を有し、イソシアヌレート環および架橋縮合環を有さないラジカル重合性化合物(A2)(以下、「化合物(A2)」とも称す)、イソシアヌレート環を有し、架橋縮合環を有さないラジカル重合性化合物(A3)(以下、「化合物(A3)」とも称す)および化合物(A1)〜化合物(A3)に属さないその他のラジカル重合性化合物から構成される。なお、単独または2種以上の、これらの化合物を混合して使用することができる。<Radical polymerizable component (A)>
The component (A) is a compound having a radically polymerizable group. The radically polymerizable group means a group capable of polymerization in the presence of a radical, and examples thereof include an acrylic group, a methacryl group, a vinyl group and a thiol group. The component (A) is a compound (A1), a radically polymerizable compound (A2) having a cationically polymerizable group and not having an isocyanurate ring and a crosslinked condensed ring (hereinafter, also referred to as “compound (A2)”). A radically polymerizable compound (A3) having an isocyanurate ring and no crosslinked condensed ring (hereinafter, also referred to as “compound (A3)”) and other radical polymerizations not belonging to compounds (A1) to (A3). It is composed of sex compounds. In addition, these compounds may be used alone or in mixture of two or more kinds.
成分(A)は、本発明の組成物の塗工容易性、硬化速度等の観点からは、低分子量化合物を含むことが好ましい。また、低分子量化合物は、組成物中への分散性または溶解性等に優れるため、透明性に優れた硬化物を得ることができるからである。一方、ラジカル重合性化合物は、本発明の組成物の接着力等の観点からは、高分子量化合物を含むことが好ましい。組成物の塗工容易性、硬化速度、接着力のバランスの観点から、ラジカル重合性化合物は、低分子量化合物および高分子量化合物の両者を含むことが好ましい。さらに、高分子量化合物は、低分子量化合物と共に用いられることで、本発明の組成物中への分散または溶解性を向上でき、透明性に優れた硬化物を得ることができる。 The component (A) preferably contains a low molecular weight compound from the viewpoint of ease of coating, curing rate, and the like of the composition of the present invention. Further, since the low molecular weight compound is excellent in dispersibility or solubility in the composition, a cured product having excellent transparency can be obtained. On the other hand, the radically polymerizable compound preferably contains a high molecular weight compound from the viewpoint of adhesive strength and the like of the composition of the present invention. From the viewpoint of the balance between ease of coating, curing speed, and adhesive strength of the composition, the radically polymerizable compound preferably contains both a low molecular weight compound and a high molecular weight compound. Further, when the high molecular weight compound is used together with the low molecular weight compound, the dispersion or solubility in the composition of the present invention can be improved, and a cured product having excellent transparency can be obtained.
低分子量化合物の分子量としては、所望の塗工性等が得られるものであればよく、例えば、1,000以下とすることができ、50以上500以下であることが好ましく、なかでも50以上300以下であることが好ましい。高分子量化合物の分子量は、所望の接着容易性等が得られるものであればよく、例えば、1,000より大きいものとすることができ、1,000以上50,000以下であることが好ましく、なかでも、5,000以上20,000以下であることが好ましい。なお、以下、分子量は、化合物が重合体である場合には、重量平均分子量(Mw)を示すものである。 The molecular weight of the low molecular weight compound may be any as long as it can obtain desired coatability, for example, 1,000 or less, preferably 50 or more and 500 or less, and more than 50 or 300. The following is preferable. The molecular weight of the high molecular weight compound may be any as long as it can obtain desired adhesive ease, for example, it can be larger than 1,000, and preferably 1,000 or more and 50,000 or less. Above all, it is preferably 5,000 or more and 20,000 or less. Hereinafter, the molecular weight indicates the weight average molecular weight (Mw) when the compound is a polymer.
ここで、重量平均分子量は、ゲル・パーミエーション・クロマトグラフィー(GPC)により、標準ポリスチレン換算値として求めることができる。重量平均分子量Mwは、例えば、日本分光(株)製のGPC(LC−2000plusシリーズ)を用い、溶出溶剤をテトラヒドロフランとし、校正曲線用ポリスチレンスタンダードをMw1,110,000、707,000、397,000、189,000、98,900、37,200、13,700、9,490、5,430、3,120、1,010、589(東ソー(株)社製 TSKgel標準ポリスチレン)とし、測定カラムをKF−804、KF−803、KF−802(昭和電工(株)製)として測定して得ることができる。また、測定温度は40℃とすることができ、流速は1.0mL/分とすることができる。 Here, the weight average molecular weight can be determined as a standard polystyrene-equivalent value by gel permeation chromatography (GPC). For the weight average molecular weight Mw, for example, GPC (LC-2000plus series) manufactured by JASCO Corporation is used, the elution solvent is tetrahydrofuran, and the polystyrene standard for calibration curve is Mw1, 110,000, 707,000, 397,000. , 189,000, 98,900, 37,200, 13,700, 9,490, 5,430, 3,120, 1,010,589 (TSKgel standard polystyrene manufactured by Showa Denko Corporation), and the measurement column was It can be obtained by measuring as KF-804, KF-803, KF-802 (manufactured by Showa Denko Corporation). The measurement temperature can be 40 ° C. and the flow velocity can be 1.0 mL / min.
本発明の組成物に含有される成分(A)の含有量は、組成物100質量部に対して耐水性に優れることから、40〜60質量部が好ましく、特に好ましくは、45〜55質量部である。 The content of the component (A) contained in the composition of the present invention is preferably 40 to 60 parts by mass, particularly preferably 45 to 55 parts by mass, because it is excellent in water resistance with respect to 100 parts by mass of the composition. Is.
<化合物(A1)>
化合物(A1)は、架橋縮合環を有するラジカル重合性化合物である。化合物(A1)が有する架橋縮合環とは、3個以上の炭素原子を共有する縮合環を意味し、一般式(I)で表される構造を有する架橋縮合環が含まれていることが好ましい。<Compound (A1)>
Compound (A1) is a radically polymerizable compound having a crosslinked condensed ring. The crosslinked condensed ring contained in the compound (A1) means a condensed ring sharing three or more carbon atoms, and preferably contains a crosslinked condensed ring having a structure represented by the general formula (I). ..
このような構造の架橋縮合環としては、例えば下記に示す架橋縮合環が挙げられる。 Examples of the crosslinked condensed ring having such a structure include the crosslinked condensed ring shown below.
例示した架橋縮合環の中でも、架橋縮合環No.6、No.7およびNo.8を有する化合物(A1)を含有する接着剤は、高い接着力および耐水性を有することから、好ましい。架橋縮合環No.6は、構造が安定で生産性が高いことから特に好ましい。 Among the crosslinked condensed rings exemplified, the crosslinked condensed ring No. 6, No. 7 and No. An adhesive containing the compound (A1) having 8 is preferable because it has high adhesive strength and water resistance. Crosslinked fused ring No. 6 is particularly preferable because it has a stable structure and high productivity.
ラジカル重合性基の数が、1〜4個の化合物(A1)は、接着力と塗工性のバランスが良いことから好ましく、ラジカル重合性基の数が、1〜3個の化合物(A1)は、特に好ましい。 A compound (A1) having 1 to 4 radically polymerizable groups is preferable because it has a good balance between adhesive strength and coatability, and a compound (A1) having 1 to 3 radically polymerizable groups is preferable. Is particularly preferred.
化合物(A1)としては、例えば、トリシクロデカンジメタノールジ(メタ)アクリレート、ジシクロペンタニルオキシエチル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレ−ト、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ノルボルニル(メタ)アクリレート、ジメチロールジシクロペンタンジ(メタ)アクリレート、ジメチロール−トリシクロデカンジ(メタ)アクリレート、アダマンタン(メタ)アクリレート、2−イソプロピル−2−アダマンチル(メタ)アクリレート等が挙げられる。 Examples of the compound (A1) include tricyclodecanedimethanol di (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylicate, and dicyclopentanyl (meth) acrylate. Dicyclopentenyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, norbornyl (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, dimethylol-tricyclodecanedi (meth) acrylate, adamantan (meth) acrylate, Examples thereof include 2-isopropyl-2-adamantyl (meth) acrylate.
化合物(A1)としては、市販品を用いることもできる。市販品としては、例えば、カヤラッドR−684(以上、日本化薬製);A−DCPおよびDCP(以上、新中村化学工業製);FA−511AS、FA−512AS、FA−513AS、FA−512M、FA−512MT、FA−513M(以上、日立化成製)が挙げられる。 As the compound (A1), a commercially available product can also be used. Examples of commercially available products include Kayarad R-684 (above, manufactured by Nippon Kayaku); A-DCP and DCP (above, manufactured by Shin Nakamura Chemical Industry Co., Ltd.); FA-511AS, FA-512AS, FA-513AS, FA-512M. , FA-512MT, FA-513M (all manufactured by Hitachi Chemical).
<化合物(A2)>
化合物(A2)としては、カチオン重合性基を有し、イソシアヌレート環および架橋縮合環を有さないラジカル重合性化合物であればよく、特に制限されない。<Compound (A2)>
The compound (A2) is not particularly limited as long as it is a radically polymerizable compound having a cationically polymerizable group and not having an isocyanurate ring and a crosslinked condensed ring.
カチオン重合性基とは、酸の存在下で重合が可能な基を意味し、例えば、水酸基、エポキシ基、脂環式エポキシ基、オキセタニル基およびビニルエーテル基等が挙げられる。化合物(A2)の有するカチオン重合性基としては、基材密着性の観点からは水酸基が好ましい。初期硬化性および接着力の観点からは、エポキシ基が好ましい。 The cationically polymerizable group means a group that can be polymerized in the presence of an acid, and examples thereof include a hydroxyl group, an epoxy group, an alicyclic epoxy group, an oxetanyl group and a vinyl ether group. As the cationically polymerizable group of the compound (A2), a hydroxyl group is preferable from the viewpoint of substrate adhesion. Epoxy groups are preferred from the standpoint of initial curability and adhesive strength.
化合物(A2)としては、例えば、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシ−3−アクリロイロキシプロピル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート等の水酸基含有アクリル酸エステル;N−2−ヒドロキシエチル(メタ)アクリルアミド、N−ビニルホルムアミド等の水酸基含有アクリルアミド;ビニルフェノール、アリルアルコール、クロチルアルコール等のビニルアルコール;、水酸基含有ビニルモノマー、エポキシ化合物に(メタ)アクリル酸を反応させた、エチレングリコールジグリシジルエーテルのエポキシ(メタ)アクリレート、ジエチレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、トリエチレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、ポリエチレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、プロピレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、トリプロピレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、ポリプロピレングリコールジグリシジルエーテルのモノ(メタ)アクリレート、ネオペンチルグリコールジグリシジルエーテルのモノ(メタ)アクリレート等のエポキシ(メタ)アクリレート;、(メタ)アクリル酸グリシジル、および下記化合物(A2)No.1〜No.4、(3−エチルオキセタン−3−イル)メチルアクリレート等が挙げられる。 Examples of the compound (A2) include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxy-3-acryloyloxy. Hydroxyl-containing acrylic acid esters such as propyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol tri (meth) acrylate; N-2-hydroxyethyl (meth) acrylamide, Hydroxide-containing acrylamide such as N-vinylformamide; Vinyl alcohol such as vinylphenol, allyl alcohol, and crotyl alcohol; Epoxy of ethylene glycol diglycidyl ether obtained by reacting hydroxyl group-containing vinyl monomer and epoxy compound with (meth) acrylic acid Mono (meth) acrylate, mono (meth) acrylate of diethylene glycol diglycidyl ether, mono (meth) acrylate of triethylene glycol diglycidyl ether, mono (meth) acrylate of polyethylene glycol diglycidyl ether, mono (meth) acrylate of propylene glycol diglycidyl ether. ) Acrylate, mono (meth) acrylate of tripropylene glycol diglycidyl ether, mono (meth) acrylate of polypropylene glycol diglycidyl ether, mono (meth) acrylate of neopentyl glycol diglycidyl ether; Meta) glycidyl acrylate, and the following compound (A2) No. 1-No. 4, (3-ethyloxetane-3-yl) methyl acrylate and the like can be mentioned.
化合物(A2)のラジカル重合性基としては、硬化性が優れるとの観点から、ラジカル重合性基としては、アクリル基が好ましい。また、粘度が低く塗工性に優れるとの観点から、ラジカル重合性基を1つまたは2つ有することが好ましい。 As the radically polymerizable group of the compound (A2), an acrylic group is preferable as the radically polymerizable group from the viewpoint of excellent curability. Further, from the viewpoint of low viscosity and excellent coatability, it is preferable to have one or two radically polymerizable groups.
ラジカル重合性化合物(A2)がラジカル重合性成分(A)に含有される場合、ラジカル重合性化合物(A2)の好ましい含有量は、接着性、耐水性および流動性に優れることから、ラジカル重合性成分(A)100質量部中に0〜20質量部が好ましく、特に好ましくは、5〜10質量部である。 When the radically polymerizable compound (A2) is contained in the radically polymerizable component (A), the preferable content of the radically polymerizable compound (A2) is excellent in adhesiveness, water resistance and fluidity, and thus radically polymerizable. The amount is preferably 0 to 20 parts by mass, particularly preferably 5 to 10 parts by mass in 100 parts by mass of the component (A).
<化合物(A3)>
化合物(A3)としては、イソシアヌレート環を含有し、架橋縮合環を有さないラジカル重合性化合物であればよく、特に制限されない。<Compound (A3)>
The compound (A3) is not particularly limited as long as it is a radically polymerizable compound containing an isocyanurate ring and not having a crosslinked condensed ring.
化合物(A3)としては、例えば、ε−カプロラクトン変性トリス[2−(メタ)アクリロキシエチル]イソシアヌレート、トリ[(メタ)アクリロイルエチル]イソシアヌレート、トリス[3−(メタ)アクリロキシプロピル]イソシアヌレート等のトリス[(メタ)アクリロキシアルキル]イソシアヌレート、およびジ[(メタ)アクリロイルエチル]−2−ヒドロキシエチルイソシアヌレート、モノアリルイソシアヌレート、ジアリルイソシアヌレート、トリアリルイソシアヌレートおよび下記化合物(A3)No.1等が挙げられる。 Examples of the compound (A3) include ε-caprolactone-modified tris [2- (meth) acryloxyethyl] isocyanurate, tri [(meth) acryloylethyl] isocyanurate, and tris [3- (meth) acryloxypropyl] isocyanate. Tris [(meth) acryloxyalkyl] isocyanurate such as nurate, and di [(meth) acryloyl ethyl] -2-hydroxyethyl isocyanurate, monoallyl isocyanurate, diallyl isocyanurate, triallyl isocyanurate and the following compounds (A3) ) No. 1st grade can be mentioned.
化合物(A3)としては、市販品を用いることもできる。市販品としては、例えば、アロニックスM−215、M−315(以上、東亞合成);NKエステルA−9300、A−9300−1CL、A−9300−3CL(以上、新中村化学工業製);タイク(三菱ケミカル製)等が挙げられる。 As the compound (A3), a commercially available product can also be used. Examples of commercially available products include Aronix M-215 and M-315 (above, Toagosei); NK Ester A-9300, A-9300-1CL, A-9300-3CL (above, manufactured by Shin Nakamura Chemical Industry Co., Ltd.); (Made by Mitsubishi Chemical) and the like.
化合物(A3)のラジカル重合性基としては、硬化性が優れるとの観点から、アクリル基が好ましい。また、硬化性が優れるとの観点から、複数のラジカル重合性基を有することが好ましく、特に2〜3個が好ましい。 As the radically polymerizable group of compound (A3), an acrylic group is preferable from the viewpoint of excellent curability. Further, from the viewpoint of excellent curability, it is preferable to have a plurality of radically polymerizable groups, and particularly 2 to 3 are preferable.
ラジカル重合性化合物(A3)がラジカル重合性成分(A)に含有される場合、ラジカル重合性化合物(A3)の好ましい含有量は、耐水性および流動性に優れることからラジカル重合性成分(A)100質量部中に0〜20質量部が好ましく、特に好ましくは、5〜10質量部である。 When the radically polymerizable compound (A3) is contained in the radically polymerizable component (A), the preferable content of the radically polymerizable compound (A3) is excellent in water resistance and fluidity, so that the radically polymerizable component (A) It is preferably 0 to 20 parts by mass, particularly preferably 5 to 10 parts by mass in 100 parts by mass.
<その他のラジカル重合性化合物>
その他のラジカル重合性化合物としては、例えば、エチレン、プロピレン、ブチレン、イソブチレン、塩化ビニル、塩化ビニリデン、フッ化ビニリデン、テトラフルオロエチレン等の不飽和脂肪族炭化水素;(メタ)アクリル酸、α−クロルアクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸、コハク酸モノ[2−(メタ)アクリロイロキシエチル]、フタル酸モノ[2−(メタ)アクリロイロキシエチル]、ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート;1個のカルボキシル基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート等の不飽和多塩基酸;(メタ)(メタ)アクリル酸メチル、(メタ)アクリル酸ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸−t−ブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸イソオクチル、(メタ)アクリル酸イソノニル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸ジメチルアミノメチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸アミノプロピル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸エトキシエチル、(メタ)アクリル酸ポリ(エトキシ)エチル、(メタ)アクリル酸ブトキシエトキシエチル、(メタ)アクリル酸エチルヘキシル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸テトラヒドロフリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸アリル、(メタ)アクリル酸ベンジル、1,10−デカンジオールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ポリエステル(メタ)アクリレートオリゴマー等の不飽和一塩基酸および多価アルコールまたは多価フェノールのエステル;(メタ)アクリル酸亜鉛、(メタ)アクリル酸マグネシウム等の不飽和多塩基酸の金属塩;マレイン酸無水物、イタコン酸無水物、シトラコン酸無水物、メチルテトラヒドロ無水フタル酸、テトラヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸−無水マレイン酸付加物、ドデセニル無水コハク酸、無水メチルハイミック酸等の不飽和多塩基酸の酸無水物;(メタ)アクリルアミド、メチレンビス−(メタ)アクリルアミド、ジエチレントリアミントリス(メタ)アクリルアミド、キシリレンビス(メタ)アクリルアミド、α−クロロアクリルアミド等の不飽和一塩基酸および多価アミンのアミド;アクロレイン等の不飽和アルデヒド;(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデン、シアン化アリル等の不飽和ニトリル;スチレン、4−メチルスチレン、4−エチルスチレン、4−メトキシスチレン、4−ヒドロキシスチレン、4−クロロスチレン、ジビニルベンゼン、ビニルトルエン、ビニル安息香酸、ビニルスルホン酸、4−ビニルベンゼンスルホン酸、ビニルベンジルメチルエーテル、ビニルベンジルグリシジルエーテル等の不飽和芳香族化合物;メチルビニルケトン等の不飽和ケトン;ビニルアミン、アリルアミン、N−ビニルピロリドン、ビニルピペリジン等の不飽和アミン化合物;ビニルメチルエーテル、ビニルエチルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル、アリルグリシジルエーテル等のビニルエーテル;マレイミド、N−フェニルマレイミド、N−シクロヘキシルマレイミド等の不飽和イミド類;インデン、1−メチルインデン等のインデン類;1,3−ブタジエン、イソプレン、クロロプレン等の脂肪族共役ジエン類;ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート、ポリシロキサン等の重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー類;ビニルクロリド、ビニリデンクロリド、ジビニルスクシナート、ジアリルフタラート、トリアリルホスファート、トリアリルイソシアヌラート、ビニルチオエーテル、ビニルイミダゾール、ビニルオキサゾリン、ビニルカルバゾール、ビニルピロリドンおよびビニルピリジンおよびポリイソシアネート化合物のビニルウレタン化合物等が挙げられる。<Other radically polymerizable compounds>
Other radically polymerizable compounds include, for example, unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene; (meth) acrylic acid, α-chlor. Acrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allylacetic acid, cinnamic acid, sorbic acid, mesaconic acid, mono-succinic acid [2- (meth) acryloy Roxyethyl], mono (2- (meth) acrylicyloxyethyl] phthalate, ω-carboxypolycaprolactone mono (meth) acrylate, and other mono (meth) acrylates of polymers having carboxy groups and hydroxyl groups at both ends; Unsaturated polybasic acids such as polyfunctional (meth) acrylates having one carboxyl group and two or more (meth) acryloyl groups; methyl (meth) (meth) acrylate, butyl (meth) acrylate, (meth). ) Isobutyl acrylate, -t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, (meth) acrylate Stearyl, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, aminopropyl (meth) acrylate, dimethylamino (meth) acrylate Propyl, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, ethylhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, (meth) acrylate Tetrahydrofuryl, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, 1,10-decanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate , Triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, Trimethylol ethanetri (meth) acrylate, trimethylol propanthry (meth) acrylate, dipentaerythri Unsaturated monobasic acids such as tallhexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, polyester (meth) acrylate oligomers and esters of polyhydric alcohols or phenols; zinc (meth) acrylate, (meth) acrylic acid. Metallic salts of unsaturated polybasic acids such as magnesium; maleic acid anhydride, itaconic acid anhydride, citraconic acid anhydride, methyltetrahydroanophthalic acid, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2, 5-Dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecenyl succinic anhydride, methylhymic acid anhydride, etc. Acid anhydrides of unsaturated polybasic acids; unsaturated monobasic acids and polyvalent amines such as (meth) acrylamide, methylenebis- (meth) acrylamide, diethylenetriaminetris (meth) acrylamide, xylylenebis (meth) acrylamide, α-chloroacrylamide Amid; unsaturated aldehydes such as achlorine; unsaturated nitriles such as (meth) acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, Unsaturated aromatic compounds such as 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinyl benzoic acid, vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzylmethyl ether, vinylbenzylglycidyl ether; methylvinyl Unsaturated ketones such as ketones; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone, vinylpiperidin; vinyl ethers such as vinylmethyl ether, vinylethyl ether, n-butylvinyl ether, isobutylvinyl ether, allylglycidyl ether; maleimide, Unsaturated imides such as N-phenylmaleimide and N-cyclohexylmaleimide; indens such as inden and 1-methylinden; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; polystyrene, polymethyl (meth) Macromonomonics having a mono (meth) acryloyl group at the end of a polymer molecular chain such as acrylate, poly-n-butyl (meth) acrylate, polysiloxane; vinyl chloride, vinylidene chloride, etc. Examples thereof include divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone and vinyl urethane compounds of vinyl pyridine and polyisocyanate compounds.
その他のラジカル重合性化合物としては、市販品を用いることもできる。市販品としては、例えば、カヤラッドDPHA、DPEA−12、PEG400DA、THE−330、RP−1040、NPGDA、PET30(以上、日本化薬製);NKエステルA−DOD−N、A−DPH、A−TMPT、A−HD−N、TMPT、NPGおよびHD−N(以上、新中村化学工業製);SPC−1000、SPC−3000(以上、昭和電工製);NKオリゴ U−4HA、U−4H、U−6HA、U−15HA、U−108A、U−1084A、U−200AX、U−122A、U−340A、U−324A、UA−53H、UA−100、AH−600(以上、新中村化学工業(株)製)、UA−306H、AI−600、UA−101T、UA−101I、UA−306T、UA−306I(以上、共栄社化学(株)製)、アートレジン UN−9200A、UN−3320HA、UN−3320HB、UN−3320HC、UN−3320HS、SH−380G、SH−500、SH−9832、UN−901T、UN−904、UN−905、UN−906、UN−906S、UN−907、UN−952、UN−953、UN−954、H−91、H−135(以上、根上工業(株)製)、サートマー CN968、CN975、CN989、CN9001、CN9010、CN9025、CN9029、CN9165、CN2260(以上、サートマー社製)、EBECRYL 8810(ダイセル社製)等が挙げられる。 As the other radically polymerizable compound, a commercially available product can also be used. Commercially available products include, for example, Kayarad DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30 (all manufactured by Nippon Kayaku); NK ester A-DOD-N, A-DPH, A- TMPT, A-HD-N, TMPT, NPG and HD-N (above, manufactured by Shin Nakamura Chemical Industry Co., Ltd.); SPC-1000, SPC-3000 (above, manufactured by Showa Denko); NK Oligo U-4HA, U-4H, U-6HA, U-15HA, U-108A, U-1084A, U-200AX, U-122A, U-340A, U-324A, UA-53H, UA-100, AH-600 (above, Shin Nakamura Chemical Industry) UA-306H, AI-600, UA-101T, UA-101I, UA-306T, UA-306I (all manufactured by Kyoeisha Chemical Industry Co., Ltd.), Art Resin UN-9200A, UN-3320HA, UN-3320HB, UN-3320HC, UN-3320HS, SH-380G, SH-500, SH-9832, UN-901T, UN-904, UN-905, UN-906, UN-906S, UN-907, UN- 952, UN-953, UN-954, H-91, H-135 (above, manufactured by Negami Kogyo Co., Ltd.), Sartmer CN968, CN975, CN989, CN9001, CN9010, CN9025, CN9029, CN9165, CN2260 (above, Sartmer) EBECRYL 8810 (manufactured by Daicel) and the like.
<カチオン重合性成分(B)>
本発明の組成物に含まれるカチオン重合性成分(B)は、カチオン重合性基を有し、ラジカル重合性基を有さない化合物である。成分(B)は、化合物(B1)、カチオン重合性基を有し、架橋縮合環を有さない重量平均分子量1,000以上30,000未満のカチオン重合性化合物(B2)(以下、「化合物(B2)」とも称す)、架橋縮合環を有さない重量平均分子量200以上1,000未満のカチオン重合性化合物(B3)(以下、「化合物(B3)」とも称す)および化合物(B1)〜化合物(B3)に属さないその他のカチオン重合性化合物から構成される。なお、本発明の組成物では、単独または2種以上の成分(B)を混合して使用することができる。また、分子量は、化合物が重合体である場合には、重量平均分子量(Mw)を示すものである。<Cation-polymerizable component (B)>
The cationically polymerizable component (B) contained in the composition of the present invention is a compound having a cationically polymerizable group and not having a radically polymerizable group. The component (B) is a compound (B1), a cationically polymerizable compound (B2) having a cationically polymerizable group and having no crosslinked condensed ring and having a weight average molecular weight of 1,000 or more and less than 30,000 (hereinafter, "compound"). (B2) ”), a cationically polymerizable compound (B3) having no crosslinked condensed ring and having a weight average molecular weight of 200 or more and less than 1,000 (hereinafter, also referred to as“ compound (B3) ”) and compound (B1) to It is composed of other cationically polymerizable compounds that do not belong to compound (B3). In the composition of the present invention, it can be used alone or in combination of two or more kinds of components (B). Further, the molecular weight indicates the weight average molecular weight (Mw) when the compound is a polymer.
本発明の組成物に含有される成分(B)の含有量は、組成物100質量部に対して耐水性に優れることから30〜50質量部が好ましく、特に好ましくは、40〜50質量部である。 The content of the component (B) contained in the composition of the present invention is preferably 30 to 50 parts by mass, particularly preferably 40 to 50 parts by mass, because it is excellent in water resistance with respect to 100 parts by mass of the composition. be.
成分(B)は、本発明の組成物の塗工容易性、硬化速度等の観点からは、低分子量化合物を含むことが好ましい。また、低分子量化合物は、組成物中への分散性または溶解性等に優れるため、透明性に優れた硬化物を得ることができるからである。一方、カチオン重合性化合物は、本発明の組成物の接着力等の観点からは、高分子量化合物を含むことが好ましい。また、カチオン重合性化合物は、組成物の塗工容易性、硬化速度、接着力のバランスの観点からは、低分子量化合物および高分子量化合物の両者を含むことが好ましい。また、高分子量化合物は、低分子量化合物と共に用いられることで、本発明の組成物中への分散または溶解性を向上でき、透明性に優れた硬化物を得ることができるからである。 The component (B) preferably contains a low molecular weight compound from the viewpoint of ease of coating, curing rate, and the like of the composition of the present invention. Further, since the low molecular weight compound is excellent in dispersibility or solubility in the composition, a cured product having excellent transparency can be obtained. On the other hand, the cationically polymerizable compound preferably contains a high molecular weight compound from the viewpoint of adhesive strength and the like of the composition of the present invention. Further, the cationically polymerizable compound preferably contains both a low molecular weight compound and a high molecular weight compound from the viewpoint of the balance of ease of coating, curing speed and adhesive strength of the composition. Further, when the high molecular weight compound is used together with the low molecular weight compound, the dispersion or solubility in the composition of the present invention can be improved, and a cured product having excellent transparency can be obtained.
高分子量化合物の含有量は、所望の硬化速度および接着力が得られるものであれば特に限定されるものではなく、例えば、接着力および透明性等のバランスの観点から、適宜調整されるものである。高分子量化合物の含有量は、具体的には、本発明の組成物の固形分100質量部中に0質量部以上20質量部以下とすることができ、2質量部以上15質量部以下であることが好ましく、なかでも、3質量部以上10質量部以下であることが好ましい。含有量がかかる範囲内であることで、本発明の組成物は、硬化速度および接着力に優れたものとなるからであり、特に接着力に優れると共に透明性に優れた硬化物を形成可能となるからである。 The content of the high molecular weight compound is not particularly limited as long as it can obtain a desired curing rate and adhesive strength, and is appropriately adjusted from the viewpoint of balance of adhesive strength and transparency, for example. be. Specifically, the content of the high molecular weight compound can be 0 parts by mass or more and 20 parts by mass or less in 100 parts by mass of the solid content of the composition of the present invention, and is 2 parts by mass or more and 15 parts by mass or less. It is preferable that the amount is 3 parts by mass or more and 10 parts by mass or less. This is because the composition of the present invention has excellent curing speed and adhesive strength when the content is within such a range, and it is possible to form a cured product having particularly excellent adhesive strength and excellent transparency. Because it becomes.
<化合物(B1)>
化合物(B1)は、架橋縮合環を有するカチオン重合性化合物である。架橋縮合環の中でも耐水性に優れることから、上記一般式(I)で表される構造を有する架橋縮合環が好ましく、特に上記架橋縮合環No.6、No.7およびNo.8を有する化合物(B1)を含有する接着剤は高い接着力および耐水性を有することから、好ましい。架橋縮合環No.6は、構造が安定で生産性が高いことから特に好ましい。<Compound (B1)>
Compound (B1) is a cationically polymerizable compound having a crosslinked condensed ring. Among the crosslinked condensed rings, the crosslinked condensed ring having the structure represented by the above general formula (I) is preferable because it is excellent in water resistance, and the above crosslinked condensed ring No. 6, No. 7 and No. An adhesive containing the compound (B1) having 8 is preferable because it has high adhesive strength and water resistance. Crosslinked fused ring No. 6 is particularly preferable because it has a stable structure and high productivity.
化合物(B1)としては、例えば、下記化合物(B1)No.1〜No.22等が挙げられる。 Examples of the compound (B1) include the following compound (B1) No. 1-No. 22 and the like can be mentioned.
化合物(B1)としては、市販品を用いることもできる。市販品としては、例えば、アデカレジンEP−4088L、4088S(以上、ADEKA製);XD−1000(日本化薬製)HP−7200(DIC製)等が挙げられる。 As the compound (B1), a commercially available product can also be used. Examples of commercially available products include ADEKA REGIN EP-4088L and 4088S (all manufactured by ADEKA); XD-1000 (manufactured by Nippon Kayaku) HP-7200 (manufactured by DIC) and the like.
化合物(B1)のカチオン重合性基としては、硬化性が高く、接着力に優れるとの観点からは、エポキシ基が好ましく、特にグリシジルエーテル基が好ましい。また、硬化性が優れること観点から、複数のカチオン重合性基を有することが好ましく、特に2〜3個が好ましい。 As the cationically polymerizable group of the compound (B1), an epoxy group is preferable, and a glycidyl ether group is particularly preferable, from the viewpoint of high curability and excellent adhesive strength. Further, from the viewpoint of excellent curability, it is preferable to have a plurality of cationically polymerizable groups, and particularly 2 to 3 are preferable.
<化合物(B2)>
化合物(B2)は、架橋縮合環を有さない重量平均分子量1,000以上30,000未満のカチオン重合性化合物であればよく、特に制限されない。重量平均分子量は、上述の測定方法によって測定できる。化合物(B2)を含有する組成物は、耐水性が向上することから好ましい。<Compound (B2)>
The compound (B2) is not particularly limited as long as it is a cationically polymerizable compound having no crosslinked condensed ring and having a weight average molecular weight of 1,000 or more and less than 30,000. The weight average molecular weight can be measured by the above-mentioned measuring method. A composition containing the compound (B2) is preferable because it improves water resistance.
化合物(B2)としては、例えば、グリシジルメタクリレートの重合物およびグリシジルメタクリレートとメチルメタクリレートの共重合物等のグリシジルメタクリレートの共重合物、並びにそれらの一部を変性したものが挙げられ、グリシジルメタクリレートとしては、グリシジルメタクリレート、2−メチルグリシジルメタクリレート、4−ヒドロキシブチルメタクリレート、ビスフェノールAのジグリシジルエーテル、ビスフェノールFのジグリシジルエーテル等を挙げることができる。また、これ以外にも、ノボラック型エポキシ樹脂、2−ヒドロキシエチルビニルエーテル、トリエチレングリコールビニルモノエーテル、テトラエチレングリコールジビニルエーテル、トリメチロールプロパントリビニルエーテル等の重合体およびこれらの共重合体等が挙げられる。 Examples of the compound (B2) include a polymer of glycidyl methacrylate, a copolymer of glycidyl methacrylate such as a copolymer of glycidyl methacrylate and methyl methacrylate, and a partially modified product thereof. Examples of the compound (B2) include glycidyl methacrylate. , Glycidyl methacrylate, 2-methylglycidyl methacrylate, 4-hydroxybutyl methacrylate, diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F and the like. In addition to this, polymers such as novolak type epoxy resin, 2-hydroxyethyl vinyl ether, triethylene glycol vinyl monoether, tetraethylene glycol divinyl ether, and trimethyl propantrivinyl ether, and copolymers thereof and the like can be mentioned. ..
化合物(B2)としては、市販品を用いることもできる。市販品としては、例えば、G−0130M(以上、日油製)、EOCN−104S(日本化薬製)等が挙げられる。 As the compound (B2), a commercially available product can also be used. Examples of commercially available products include G-0130M (manufactured by NOF Corporation) and EOCN-104S (manufactured by Nippon Kayaku).
化合物(B2)としては、エポキシ当量が1,000以下の場合、硬化性に優れることから好ましく、エポキシ当量が200〜600が特に好ましい。 As the compound (B2), when the epoxy equivalent is 1,000 or less, it is preferable because it is excellent in curability, and the epoxy equivalent is particularly preferably 200 to 600.
また、化合物(B2)の有するカチオン重合性基としては、硬化性が高く、接着力が高い組成物が得られることから、エポキシ基が好ましく、特にグリシジルエーテル基が好ましい。 Further, as the cationically polymerizable group of the compound (B2), an epoxy group is preferable, and a glycidyl ether group is particularly preferable, because a composition having high curability and high adhesive strength can be obtained.
カチオン重合性成分(B)に含有されていてもよいカチオン重合性化合物(B2)の好ましい含有量は、耐水性および流動性に優れることからカチオン重合性成分(B)100質量部中に0〜30質量部であり、特に好ましくは、5〜20質量部である。 The preferable content of the cationically polymerizable compound (B2) which may be contained in the cationically polymerizable component (B) is 0 to 0 in 100 parts by mass of the cationically polymerizable component (B) because of its excellent water resistance and fluidity. It is 30 parts by mass, and particularly preferably 5 to 20 parts by mass.
<化合物(B3)>
化合物(B3)は、架橋縮合環を有さない重量平均分子量200以上1,000未満のカチオン重合性化合物であればよく、特に限定されない。化合物(B3)を含有する組成物は、接着力と塗布性を両立できることから好ましい。化合物(B3)としては、例えば芳香族エポキシ化合物、脂環式エポキシ化合物、脂肪族エポキシ化合物、オキセタン化合物等が挙げられる。ただし、エポキシ基とオキセタニル基を同一分子内に有する化合物は、オキセタン化合物に分類される。<Compound (B3)>
The compound (B3) is not particularly limited as long as it is a cationically polymerizable compound having no crosslinked condensed ring and having a weight average molecular weight of 200 or more and less than 1,000. A composition containing the compound (B3) is preferable because it can achieve both adhesive strength and coatability. Examples of the compound (B3) include aromatic epoxy compounds, alicyclic epoxy compounds, aliphatic epoxy compounds, and oxetane compounds. However, a compound having an epoxy group and an oxetanyl group in the same molecule is classified as an oxetane compound.
エポキシ当量が500以下の化合物(B3)を含有する組成物は、硬化性に優れることから好ましく、エポキシ当量が200以下の化合物(B3)を含有する組成物が、特に好ましい。 A composition containing a compound (B3) having an epoxy equivalent of 500 or less is preferable because it has excellent curability, and a composition containing a compound (B3) having an epoxy equivalent of 200 or less is particularly preferable.
化合物(B3)の有するカチオン重合性基としては、硬化性が高く、接着力が高い組成物が得られることから、エポキシ基が好ましく、特にグリシジルエーテル基が好ましい。また、化合物(B3)としては、耐水性に優れた組成物が得られるため、オキセタニル基を有する化合物も好ましい。 As the cationically polymerizable group of the compound (B3), an epoxy group is preferable, and a glycidyl ether group is particularly preferable, because a composition having high curability and high adhesive strength can be obtained. Further, as the compound (B3), a compound having an oxetanyl group is also preferable because a composition having excellent water resistance can be obtained.
カチオン重合性化合物(B3)がカチオン重合性成分(B)に含有される場合、好ましい含有量は、耐水性および流動性に優れることからカチオン重合性成分(B)100質量部中に0〜90質量部が好ましく、特に好ましくは、35〜80質量部である。 When the cationically polymerizable compound (B3) is contained in the cationically polymerizable component (B), the preferable content is 0 to 90 in 100 parts by mass of the cationically polymerizable component (B) because of its excellent water resistance and fluidity. It is preferably parts by mass, particularly preferably 35 to 80 parts by mass.
カチオン重合性基を1〜3つ含む化合物(B3)を含有する組成物は、接着力と塗布性を両立できることから好ましく、特にカチオン重合性基を1〜2つ含む化合物(B3)が特に好ましい。 A composition containing a compound (B3) containing 1 to 3 cationically polymerizable groups is preferable because it can achieve both adhesive strength and coatability, and a compound (B3) containing 1 to 2 cationically polymerizable groups is particularly preferable. ..
化合物(B3)としての脂環式エポキシ化合物とは、脂環式エポキシ基(3,4−エポキシシクロヘキシル基)を有し、架橋縮合環を有さない重量平均分子量200以上1,000未満のカチオン重合性化合物を意味する。化合物(B3)として脂環式エポキシ化合物を用いることで、初期硬化性が向上することから好ましい。 The alicyclic epoxy compound as the compound (B3) is a cation having an alicyclic epoxy group (3,4-epoxycyclohexyl group) and having no crosslinked condensed ring and having a weight average molecular weight of 200 or more and less than 1,000. It means a polymerizable compound. It is preferable to use an alicyclic epoxy compound as the compound (B3) because the initial curability is improved.
脂環式エポキシ化合物としては、例えば、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シルカルボキシレート、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、3,4−エポキシ−1−メチルシクロヘキシル−3,4−エポキシ−1−メチルヘキサンカルボキシレート、6−メチル−3,4−エポキシシクロヘキシルメチル−6−メチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−3−メチルシクロヘキシルメチル−3,4−エポキシ−3−メチルシクロヘキサンカルボキシレート、3,4−エポキシ−5−メチルシクロヘキシルメチル−3,4−エポキシ−5−メチル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メチル)アジペート、3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、メチレンビス(3,4−エポキシシクロヘキサン)、プロパン−2,2−ジイル−ビス(3,4−エポキシシクロヘキサン)、2,2−ビス(3,4−エポキシシクロヘキシル)プロパン、ジシクロペンタジエンジエポキサイド、エチレンビス(3,4−エポキシシクロヘキサンカルボキシレート)、エポキシヘキサヒドロフタル酸ジオクチル、エポキシヘキサヒドロフタル酸ジ−2−エチルヘキシル、1−エポキシエチル−3,4−エポキシシクロヘキサン、1,2−エポキシ−2−エポキシエチルシクロヘキサン、7−オキサビシクロ[4.1.0]ヘプタン,ポリ[オキシ−(1−オキソ−1,6−ヘキサンジイル)]誘導体、ヘキサン二酸ビス[(7−オキサビシクロ[4.1.0]ヘプタン−3−イル)メチル]、α−ピネンオキシド、リモネンジオキシドが挙げられる。 Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexylcarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, and 3,4-epoxy-. 1-Methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3 -Methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexanemethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis (3,4-epoxy) Cyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2- Bis (3,4-epoxycyclohexyl) propane, dicyclopentadienediepoxiside, ethylenebis (3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1- Epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 7-oxabicyclo [4.1.0] heptane, poly [oxy- (1-oxo-1,6-hexanediyl) )] Derivatives, bis hexanediate [(7-oxabicyclo [4.1.0] heptane-3-yl) methyl], α-pinene oxide, limonendioxide can be mentioned.
脂環式エポキシ化合物としては、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または3,4−エポキシ−1−メチルシクロヘキシル−3,4−エポキシ−1−メチルヘキサンカルボキシレートおよび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シルカルボキシレートが、接着力向上の観点から好ましい。 As the alicyclic epoxy compound, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate or 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate and 3 , 4-Epoxycyclohexylmethyl-3,4-Epoxycyclohexylcarboxylate is preferable from the viewpoint of improving adhesive strength.
脂環式エポキシ化合物としては、市販品のものを用いることができ、例えば、セロキサイド2021P、セロキサイド2081、セロキサイド2000、セロキサイド3000、サイクロマーM100(ダイセル社製);CYRACURE UVR−6128(ダウ・ケミカル社製)等が挙げられる。 As the alicyclic epoxy compound, a commercially available product can be used, for example, celoxide 2021P, celoxide 2081, celoxide 2000, celoxide 3000, cyclomer M100 (manufactured by Daicel); CYRACURE UVR-6128 (Dow Chemical). Made) and the like.
脂環式エポキシ化合物の含有量としては、所望の硬化速度および接着力を得られればよく、例えば、化合物(B)100質量部中に0質量部以上50質量部以下とすることができ、なかでも、1質量部以上20質量部以下であることが好ましい。含有量がかかる範囲であることで、本発明の組成物は、硬化速度および接着力に優れたものとなる。 The content of the alicyclic epoxy compound may be such that a desired curing rate and adhesive strength can be obtained, and for example, it can be 0 parts by mass or more and 50 parts by mass or less in 100 parts by mass of the compound (B). However, it is preferably 1 part by mass or more and 20 parts by mass or less. The composition of the present invention is excellent in curing speed and adhesive strength when the content is in such a range.
化合物(B3)としての脂肪族エポキシ化合物とは、脂環式エポキシ化合物や後述の芳香族エポキシ化合物に分類されない架橋縮合環を有さない重量平均分子量200以上1,000未満のカチオン重合性化合物を指し、脂肪族環および芳香族環を含まないものを意味する。 The aliphatic epoxy compound as the compound (B3) is a cationically polymerizable compound having a weight average molecular weight of 200 or more and less than 1,000, which does not have a crosslinked condensed ring which is not classified into an alicyclic epoxy compound or an aromatic epoxy compound described later. Refers to one that does not contain an aliphatic ring and an aromatic ring.
脂肪族エポキシ化合物の具体例としては、脂肪族アルコールのグリシジルエーテル化物、アルキルカルボン酸のグリシジルエステル等の単官能エポキシ化合物や、脂肪族多価アルコールまたはそのアルキレンオキサイド付加物のポリグリシジルエーテル化物、脂肪族長鎖多塩基酸のポリグリシジルエステル等の多官能エポキシ化合物が挙げられる。 Specific examples of the aliphatic epoxy compound include monofunctional epoxy compounds such as glycidyl etherified products of aliphatic alcohols and glycidyl esters of alkylcarboxylic acids, polyglycidyl etherified products of aliphatic polyhydric alcohols or alkylene oxide adducts thereof, and fats. Examples thereof include polyfunctional epoxy compounds such as polyglycidyl esters of long-chain polybasic acids.
脂肪族エポキシ化合物の代表的な化合物としては、1,4−ブタンジオールジグリシジレート、アリルグリシジルエーテル、ブチルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、C12〜13混合アルキル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、1,6−ヘキサンジオールジグリシジルエーテル、水素添加ビスフェノールAジグリシジルエーテル、グリセリントリ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、ソルビトールテトラグリシジルエーテル、ジペンタエリスリトールヘキサグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル等の多価アルコールのグリシジルエーテル、またプロピレングリコール、トリメチロールプロパン、グリセリン等の脂肪族多価アルコールに1種または2種以上のアルキレンオキサイドを付加することによって得られるポリエーテルポリオールのポリグリシジルエーテル化物、脂肪族長鎖二塩基酸のジグリシジルエステルが挙げられる。更に、脂肪族高級アルコールのモノグリシジルエーテルや高級脂肪酸のグリシジルエステル、エポキシ化大豆油、エポキシステアリン酸オクチル、エポキシステアリン酸ブチル、エポキシ化大豆油、エポキシ化ポリブタジエン等が挙げられる。 Typical compounds of aliphatic epoxy compounds include 1,4-butanediol diglycidylate, allylglycidyl ether, butylglycidyl ether, 2-ethylhexyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, and 1,4-butanediol. Diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, glycerin triglycidyl ether, trimethylpropantriglycidyl ether, sorbitol tetraglycidyl ether, dipentaerythritol hexaglycidyl ether, polyethylene glycol diglycidyl Poly obtained by adding one or more alkylene oxides to glycidyl ether, which is a polyhydric alcohol such as ether or polypropylene glycol diglycidyl ether, or aliphatic polyhydric alcohol such as propylene glycol, trimethylolpropane, or glycerin. Examples thereof include polyglycidyl ethers of ether polyols and diglycidyl esters of aliphatic long-chain dibasic acids. Further, monoglycidyl ether of an aliphatic higher alcohol, glycidyl ester of a higher fatty acid, epoxidized soybean oil, octyl epoxide stearate, butyl epoxy stearate, epoxidized soybean oil, epoxidized polybutadiene and the like can be mentioned.
脂肪族エポキシ化合物としては、脂肪族アルコールのグリシジルエーテル化物あるいは脂肪族多価アルコールまたはそのアルキレンオキサイド付加物のポリグリシジルエーテル化物が、粘度、塗工性および反応性が向上するので好ましく、さらに、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または1,6−ヘキサンジオールジグリシジルエーテルが好ましい。 As the aliphatic epoxy compound, a glycidyl etherified product of an aliphatic alcohol or a polyglycidyl etherified product of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof is preferable because it improves viscosity, coatability and reactivity, and further, ethylene is preferable. Glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether or 1,6-hexanediol diglycidyl ether are preferred.
脂肪族エポキシ化合物としては、市販品のものを用いることができ、例えば、デナコールEX−121、デナコールEX−171、デナコールEX−192、デナコールEX−211、デナコールEX−212、デナコールEX−313、デナコールEX−314、デナコールEX−321、デナコールEX−411、デナコールEX−421、デナコールEX−512、デナコールEX−521、デナコールEX−611、デナコールEX−612、デナコールEX−614、デナコールEX−622、デナコールEX−810、デナコールEX−811、デナコールEX−850、デナコールEX−851、デナコールEX−821、デナコールEX−830、デナコールEX−832、デナコールEX−841、デナコールEX−861、デナコールEX−911、デナコールEX−941、デナコールEX−920、デナコールEX−931(以上、ナガセケムテックス製);エポライトM−1230、エポライト40E、エポライト100E、エポライト200E、エポライト400E、エポライト70P、エポライト200P、エポライト400P、エポライト1500NP、エポライト1600、エポライト80MF、エポライト100MF(以上、共栄社化学製)、アデカグリシロールED−503、アデカグリシロールED−503G、アデカグリシロールED−506、アデカグリシロールED−523T、アデカレジンEP−4088S、KRM−523P、KRM−408、KRM−140(以上、ADEKA製);2EH(四日市合成製)等が挙げられる。 As the aliphatic epoxy compound, commercially available products can be used, for example, Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-221, Denacol EX-212, Denacol EX-313, Denacol. EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX-512, Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-622, Denacol EX-810, Denacol EX-811, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, Denacol EX-911, Denacol EX-941, Denacol EX-920, Denacol EX-931 (all manufactured by Nagase ChemteX); Epolite M-1230, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 400E, Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP , Epolite 1600, Epolite 80MF, Epolite 100MF (Kyoeisha Chemical Co., Ltd.), Adeka Glycyrrol ED-503, Adeka Glycyllol ED-503G, Adeka Glycyrrol ED-506, Adeka Glycyrrol ED-523T, Adeka Resin EP-4088S, Examples thereof include KRM-523P, KRM-408, and KRM-140 (all manufactured by ADEKA); 2EH (manufactured by Yokkaichi Chemical Co., Ltd.).
脂肪族エポキシ化合物の含有量としては、所望の硬化速度および接着力を得られればよく、例えば、化合物(B)100質量部中に0質量部以上90質量部以下とすることができ、なかでも、30質量部以上80質量部以下であることが好ましい。含有量がかかる範囲であることで、本発明の組成物は、硬化速度および接着力に優れたものとなる。 The content of the aliphatic epoxy compound may be such that a desired curing rate and adhesive strength can be obtained, and for example, it can be 0 parts by mass or more and 90 parts by mass or less in 100 parts by mass of the compound (B). , 30 parts by mass or more and preferably 80 parts by mass or less. The composition of the present invention is excellent in curing speed and adhesive strength when the content is in such a range.
化合物(B3)としての芳香族エポキシ化合物は、脂環式エポキシ化合物に分類されず架橋縮合環を有さない重量平均分子量200以上1,000未満の芳香環を含有するエポキシ化合物を意味する。 The aromatic epoxy compound as the compound (B3) means an epoxy compound containing an aromatic ring having a weight average molecular weight of 200 or more and less than 1,000, which is not classified as an alicyclic epoxy compound and does not have a crosslinked condensed ring.
芳香族エポキシ化合物の具体例としては、フェノール、クレゾール、ブチルフェノール等、少なくとも1個の芳香族環を有する1価フェノールまたは、そのアルキレンオキサイド付加物のモノ/ポリグリシジルエーテル化物、例えばビスフェノールA、ビスフェノールF、またはこれらに更にアルキレンオキサイドを付加した化合物のグリシジルエーテル化物やフェノールノボラック型エポキシ化合物;レゾルシノールやハイドロキノン、カテコール等の2個以上のフェノール性水酸基を有する芳香族化合物のグリシジルエーテル;ベンゼンジメタノールやベンゼンジエタノール、ベンゼンジブタノール等のアルコール性水酸基を2個以上有する芳香族化合物のポリグリシジルエーテル化物;フタル酸、テレフタル酸、トリメリット酸等の2個以上のカルボン酸を有する多塩基酸芳香族化合物のポリグリシジルエステル、安息香酸やトルイル酸、ナフトエ酸等の安息香酸類のポリグリシジルエステル、安息香酸のグリシジルエステル、スチレンオキサイドまたはジビニルベンゼンのエポキシ化物等が挙げられる。中でも、フェノール類のポリグリシジルエーテル、アルコール性水酸基を2個以上有する芳香族化合物のポリグリシジルエーテル化物、多価フェノール類のポリグリシジルエーテル化物、安息香酸類のポリグリシジルエステル、多塩基酸類のポリグリシジルエステルの群から選ばれる少なくとも一種を含有することが、本発明の組成物の低粘度化の観点から好ましい。芳香族エポキシ化合物としては、ビスフェノールA型エポキシ化合物、ビスフェノールF型エポキシ化合物、ビスフェノールE型エポキシ化合物、フェノールノボラック型エポキシ化合物が、接着力に優れるため好ましい。 Specific examples of the aromatic epoxy compound include monovalent phenol having at least one aromatic ring such as phenol, cresol, and butylphenol, or a mono / polyglycidyl etherified product of an alkylene oxide adduct thereof, such as bisphenol A and bisphenol F. , Or glycidyl ethers of compounds to which alkylene oxide is further added; glycidyl ethers of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, and catechol; benzenedimethanol and benzene. Polyglycidyl etherified compounds of aromatic compounds having two or more alcoholic hydroxyl groups such as diethanol and benzenedibutanol; polybasic acid aromatic compounds having two or more carboxylic acids such as phthalic acid, terephthalic acid and trimellitic acid. Examples thereof include polyglycidyl esters, polyglycidyl esters of benzoic acids such as benzoic acid, toluic acid, and naphthoic acid, glycidyl esters of benzoic acid, and epoxidized compounds of styrene oxide or divinylbenzene. Among them, polyglycidyl ethers of phenols, polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, polyglycidyl ethers of polyhydric phenols, polyglycidyl esters of benzoic acids, and polyglycidyl esters of polybasic acids. It is preferable to contain at least one selected from the above group from the viewpoint of reducing the viscosity of the composition of the present invention. As the aromatic epoxy compound, a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol E type epoxy compound, and a phenol novolac type epoxy compound are preferable because they have excellent adhesive strength.
芳香族エポキシ化合物としては、市販品のものを用いることができ、例えば、デナコールEX−145、デナコールEX−146、デナコールEX−147、デナコールEX−201、デナコールEX−203、デナコールEX−711、デナコールEX−721、オンコートEX−1020、オンコートEX−1030、オンコートEX−1040、オンコートEX−1050、オンコートEX−1051、オンコートEX−1010、オンコートEX−1011、オンコート1012(ナガセケムテックス社製);オグソールPG−100、オグソールEG−200、オグソールEG−210、オグソールEG−250(大阪ガスケミカル社製);HP4032、HP4032D、HP4700(DIC社製);ESN−475V(新日鉄住金化学社製);エピコートYX8800(三菱化学社製);マープルーフG−0105SA、マープルーフG−0130SP(日油社製);エピクロンN−665、エピクロンHP−7200(DIC社製);EOCN−1020、EOCN−102S、EOCN−103S、EOCN−104S、XD−1000、NC−3000、EPPN−501H、EPPN−501HY、EPPN−502H、NC−7000L(日本化薬社製);アデカレジンEP−4000、アデカレジンEP−4005、アデカレジンEP−4100、アデカレジンEP−4901、アデカレジンEP−3300E、アデカレジンEP−3950S、KRM−430、KRM−501(ADEKA社製);TECHMORE VG−3101L(プリンテック社製)等が挙げられる。 As the aromatic epoxy compound, commercially available products can be used, for example, Denacol EX-145, Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711, Denacol. EX-721, On-Coat EX-1020, On-Coat EX-1030, On-Coat EX-1040, On-Coat EX-1050, On-Coat EX-1051, On-Coat EX-1010, On-Coat EX-1011, On-Coat 1012 ( Nagase ChemteX Co., Ltd.); Ogsol PG-100, Ogsol EG-200, Ogsol EG-210, Ogsol EG-250 (manufactured by Osaka Gas Chemical Co., Ltd.); HP4032, HP4032D, HP4700 (manufactured by DIC); ESN-475V (Nippon Steel) Sumikin Chemical Co., Ltd.); Epicoat YX8800 (Mitsubishi Chemical Co., Ltd.); Marproof G-0105SA, Marproof G-0130SP (Nippon Kayaku Co., Ltd.); Epicron N-665, Epicron HP-7200 (DIC); EOCN- 1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); Adeka Resin EP-4000, Adeka Resin EP-4005, Adeka Resin EP-4100, Adeka Resin EP-4901, Adeka Resin EP-3300E, Adeka Resin EP-3950S, KRM-430, KRM-501 (manufactured by ADEKA); TECHMORE VG-3101L (manufactured by DIC), etc. Can be mentioned.
芳香族エポキシ化合物の含有量としては、所望の硬化速度および接着力を得られればよく、例えば、化合物(B)100質量部中に0質量部以上90質量部以下とすることができ、なかでも、10質量部以上50質量部以下であることが好ましい。含有量がかかる範囲であることで、本発明の組成物は、硬化速度および接着力に優れたものとなる。 The content of the aromatic epoxy compound may be such that a desired curing rate and adhesive strength can be obtained, and for example, it can be 0 parts by mass or more and 90 parts by mass or less in 100 parts by mass of the compound (B). It is preferably 10 parts by mass or more and 50 parts by mass or less. The composition of the present invention is excellent in curing speed and adhesive strength when the content is in such a range.
化合物(B3)としてのオキセタン化合物とは、オキセタニル基を有し、架橋縮合環を有さない重量平均分子量200以上1,000未満のオキセタン化合物を意味する。 The oxetane compound as the compound (B3) means an oxetane compound having an oxetanyl group and having no crosslinked condensed ring and having a weight average molecular weight of 200 or more and less than 1,000.
硬化性および塗布性のバランスに優れることから、オキセタニル基を1〜3含有するオキセタン化合物が好ましく、オキセタニル基を2つ含有するオキセタン化合物が特に好ましい。 An oxetane compound containing 1 to 3 oxetanyl groups is preferable, and an oxetane compound containing 2 oxetanyl groups is particularly preferable, because the balance between curability and coatability is excellent.
オキセタン化合物としては、3,3’−[オキシビス(メチレン)]ビス(3−エチルオキセタン)、(3,7−ビス(3−オキセタニル)−5−オキサ−ノナン、1,4−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]ベンゼン、1,2−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]エタン、1,3−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]プロパン、エチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、トリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、テトラエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル、1,4−ビス(3−エチル−3−オキセタニルメトキシ)ブタン、1,6−ビス(3−エチル−3−オキセタニルメトキシ)ヘキサン、3−エチル−3−(3−エチル−3−オキセタニルメチルオキシメチル)オキセタン、キシリレンビスオキセタン等の二官能オキセタン化合物、3−エチル−3−[(フェノキシ)メチル]オキセタン、3−エチル−3−(ヘキシロキシメチル)オキセタン、3−エチル−3−(2−エチルヘキシロキシメチル)オキセタン、3−エチル−3−(ヒドロキシメチル)オキセタン、3−エチル−3−(クロロメチル)オキセタン等の一官能オキセタン化合物等が挙げられ、一官能脂肪族オキセタン化合物が、粘度および反応性の点から好ましい。これらは1種単独あるいは2種以上を組み合わせて用いることができる。 Examples of the oxetane compound include 3,3'-[oxybis (methylene)] bis (3-ethyloxetane), (3,7-bis (3-oxetanyl) -5-oxa-nonane, and 1,4-bis [(3). -Ethyl-3-oxetanylmethoxy) methyl] benzene, 1,2-bis [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl-3-oxetanylmethoxy) methyl] Propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, triethylene glycolbis (3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycolbis (3-ethyl-3-oxetanylmethyl) ether, 1 , 4-bis (3-ethyl-3-oxetanylmethoxy) butane, 1,6-bis (3-ethyl-3-oxetanylmethoxy) hexane, 3-ethyl-3- (3-ethyl-3-oxetanylmethyloxymethyl) ) Bifunctional oxetane compounds such as oxetane and xylylene bis oxetane, 3-ethyl-3-[(phenoxy) methyl] oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (2-) Examples thereof include monofunctional oxetane compounds such as ethylhexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl) oxetane, and 3-ethyl-3- (chloromethyl) oxetane. And, it is preferable from the viewpoint of reactivity. These can be used individually by 1 type or in combination of 2 or more types.
オキセタン化合物としては、カチオン重合性モノマーを主成分とする市販品のものを用いることができ、例えば、アロンオキセタンOXT−121、OXT−221、EXOH、POX、OXA、OXT−101、OXT−211、OXT−212、OXT−221(東亞合成社製)、エタナコールOXBP、OXTP(宇部興産社製)等が挙げられる。 As the oxetane compound, a commercially available product containing a cationically polymerizable monomer as a main component can be used. For example, Aron oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-221, Examples thereof include OXT-212, OXT-221 (manufactured by Toagosei Co., Ltd.), Ethanacole OXBP, and OXTP (manufactured by Ube Industries, Ltd.).
オキセタン化合物の含有量としては、所望の硬化速度および接着力を得られるものであればよく、例えば、化合物(B)100質量部中に0質量部以上50質量部以下とすることができ、なかでも、5質量部以上30質量部以下であることが好ましい。含有量がかかる範囲であることで、本発明の組成物は、塗工性および硬化速度に優れたものとなる。 The content of the oxetane compound may be any as long as it can obtain a desired curing rate and adhesive strength. For example, the content of the oxetane compound can be 0 parts by mass or more and 50 parts by mass or less in 100 parts by mass of the compound (B). However, it is preferably 5 parts by mass or more and 30 parts by mass or less. The composition of the present invention is excellent in coatability and curing speed when the content is in such a range.
<ラジカル重合性開始剤(C)>
本発明の組成物に用いられる成分(C)としては、従来既知のラジカル重合性開始剤を用いることが可能である。<Radical Polymerization Initiator (C)>
As the component (C) used in the composition of the present invention, a conventionally known radical polymerizable initiator can be used.
成分(C)とは、光ラジカル重合性開始剤と熱ラジカル重合性開始剤である。反応性が高いことから光ラジカル重合性開始剤がより好ましい。 The component (C) is a photoradical polymerizable initiator and a thermal radical polymerizable initiator. Photoradical polymerization initiators are more preferred because of their high reactivity.
成分(C)としては、光照射によりラジカルを発生するものであれば特に制限されず従来既知の化合物を用いることが可能であり、例えば、アセトフェノン系化合物、ベンジル系化合物、ベンゾフェノン系化合物、チオキサントン系化合物およびオキシムエステル系化合物等を好ましいものとして例示することができる。 The component (C) is not particularly limited as long as it generates radicals by light irradiation, and conventionally known compounds can be used. For example, acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds can be used. Compounds, oxime ester compounds and the like can be exemplified as preferable ones.
アセトフェノン系化合物としては例えば、ベンゾイン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4’−イソプロピル−2−ヒドロキシ−2−メチルプロピオフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、2−ヒドロキシメチル−2−メチルプロピオフェノンおよび1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン等のα−ヒドロキシアセトフェノン系化合物;ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン−n−ブチルエーテル、ベンゾインイソブチルエーテルジエトキシアセトフェノンおよび2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン等のα−アルコキシアセトフェノン系化合物;p−ジメチルアミノアセトフェノン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパノン−1、および2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1等のα−アミノアセトフェノン系化合物;p−ターシャリブチルジクロロアセトフェノン、p−ターシャリブチルトリクロロアセトフェノン、p−アジドベンザルアセトフェノン、が挙げられる。 Examples of acetophenone compounds include benzoin, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexylphenylketone, 2 Α-Hydroxyacetophenone compounds such as −hydroxymethyl-2-methylpropiophenone and 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one; Α-alkoxyacetophenone compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether diethoxyacetophenone and 2,2-dimethoxy-1,2-diphenylethane-1-one; p-dimethylaminoacetophenone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone Examples thereof include α-aminoacetophenone compounds such as -1, p-tershalibutyldichloroacetophenone, p-tershaributyltrichloroacetophenone, and p-azidobenzalacetophenone.
本発明の組成物においては、得られる硬化物が透明性に優れることからアセトフェノン系化合物が好ましく、特にα−ヒドロキシアセトフェノン系化合物が特に好ましい。 In the composition of the present invention, an acetophenone-based compound is preferable, and an α-hydroxyacetophenone-based compound is particularly preferable because the obtained cured product is excellent in transparency.
ベンジル系化合物としては、ベンジル等が挙げられる。 Examples of the benzyl compound include benzyl and the like.
ベンゾフェノン系化合物としては、例えば、ベンゾフェノン、o−ベンゾイル安息香酸メチル、ミヒラーケトン、4,4’−ビスジエチルアミノベンゾフェノン、4,4’−ジクロロベンゾフェノンおよび4−ベンゾイル−4’−メチルジフェニルスルフィド等が挙げられる。 Examples of benzophenone compounds include benzophenone, methyl o-benzoyl benzoate, Michler ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 4-benzoyl-4'-methyldiphenylsulfide and the like. ..
チオキサントン系化合物としては、チオキサントン、2−メチルチオキサントン、2−エチルチオキサントン、2−クロロチオキサントン、2−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等が挙げられる。 Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, 2,4-diethylthioxanthone and the like.
オキシムエステル系化合物とは、オキシムエステル基を有する化合物を意味し、光ラジカル重合性開始剤の中でも感度が良好であることから、好ましい。 The oxime ester-based compound means a compound having an oxime ester group, and is preferable because it has good sensitivity among photoradical polymerizable initiators.
好ましいオキシムエステル系化合物としては、例えば下記に示す化合物No.C1〜No.C14が挙げられる。 Preferred oxime ester compounds include, for example, the compound No. 1 shown below. C1-No. C14 can be mentioned.
その他のラジカル重合性開始剤としては、2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド等のホスフィンオキサイド系化合物およびビス(シクロペンタジエニル)−ビス[2,6−ジフルオロ−3−(ピル−1−イル)]チタニウム等のチタノセン系化合物等が挙げられる。 Other radical polymerization initiators include phosphine oxide compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pill-). 1-yl)] Examples thereof include titanosen-based compounds such as titanium.
市販のラジカル開始剤としては、アデカオプトマーN−1414、N−1717、N−1919、アデカアークルズNCI−831、NCI−930(以上、ADEKA製);IRGACURE184、IRGACURE369、IRGACURE651、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02、IRGACURE784(以上、BASF製);TR−PBG−304、TR−PBG−305、TR−PBG−309およびTR−PBG−314(以上、Tronly製)等が挙げられる。 Commercially available radical initiators include ADEKA PUTMER N-1414, N-1717, N-1919, ADEKA ARCLUS NCI-831, NCI-930 (all manufactured by ADEKA); IRGACURE184, IRGACURE369, IRGACURE651, IRGACURE907, IRGACURE ORE. 01, IRGACURE OXE 02, IRGACURE784 (above, manufactured by BASF); TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-314 (above, manufactured by Trony) and the like.
熱ラジカル重合性開始剤としては、加熱によりラジカルを発生するものであれば特に制限されず従来既知の化合物を用いることが可能であり、例えば、アゾ系化合物、過酸化物および過硫酸塩等を好ましいものとして例示することができる。 The thermal radical polymerization initiator is not particularly limited as long as it generates radicals by heating, and conventionally known compounds can be used. For example, azo compounds, peroxides, persulfates and the like can be used. It can be exemplified as a preferable one.
アゾ系化合物としては、2,2’−アゾビスイソブチロニトリル、2,2’−アゾビス(メチルイソブチレ−ト)、2,2’−アゾビス−2,4−ジメチルバレロニトリル、1,1’−アゾビス(1−アセトキシ−1−フェニルエタン)等が挙げられる。 Examples of azo compounds include 2,2'-azobisisobutyronitrile, 2,2'-azobis (methylisobutyrate), 2,2'-azobis-2,4-dimethylvaleronitrile, and 1,1'-. Azobis (1-acetoxy-1-phenylethane) and the like can be mentioned.
過酸化物としては、ベンゾイルパーオキサイド、ジ−t−ブチルベンゾイルパーオキサイド、t−ブチルパーオキシピバレートおよびジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート等が挙げられる。 Examples of the peroxide include benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate and di (4-t-butylcyclohexyl) peroxydicarbonate.
過硫酸塩としては、過硫酸アンモニウム、過硫酸ナトリウムおよび過硫酸カリウム等の過硫酸塩等が挙げられる。 Examples of the persulfate include persulfates such as ammonium persulfate, sodium persulfate and potassium persulfate.
本発明の組成物においては、成分(C)は、これまでに例示した一種または二種以上を混合して用いることができる。 In the composition of the present invention, the component (C) can be used as one or a mixture of two or more of the above-exemplified types.
本発明の組成物において、成分(C)の含有量は、特に限定されるものではないが、成分(A)〜(D)の総量100質量部中、1〜10質量部が好ましく、また、成分(A)100質量部に対して硬化性が良好なことから好ましくは、1〜10質量部であり、さらに好ましくは3〜8質量部である。成分(C)の含有量が、上記の範囲内の場合、硬化性が良好で重合性開始剤の析出を伴わない保存安定性に優れる重合性組成物が得られるので好ましい。 In the composition of the present invention, the content of the component (C) is not particularly limited, but is preferably 1 to 10 parts by mass based on 100 parts by mass of the total amount of the components (A) to (D). Since the curability is good with respect to 100 parts by mass of the component (A), it is preferably 1 to 10 parts by mass, and more preferably 3 to 8 parts by mass. When the content of the component (C) is within the above range, a polymerizable composition having good curability and excellent storage stability without precipitation of the polymerizable initiator can be obtained, which is preferable.
<カチオン重合性開始剤(D)>
本発明の組成物に用いられる成分(D)は、可視光線、紫外線、X線、電子線、高周波のような活性エネルギー線(以下、単に「活性エネルギー線」とも称する。)照射により酸を発生させることが可能な化合物(以下、「光カチオン重合性開始剤」とも称する。)、または加熱により酸を発生させることが可能な化合物(以下、「熱カチオン重合性開始剤」とも称する。)である。<Cationic polymerizable initiator (D)>
The component (D) used in the composition of the present invention generates an acid by irradiation with active energy rays (hereinafter, also simply referred to as "active energy rays") such as visible light, ultraviolet rays, X-rays, electron beams, and high frequencies. A compound capable of generating an acid (hereinafter, also referred to as a “photocationic polymerizable initiator”) or a compound capable of generating an acid by heating (hereinafter, also referred to as a “thermocationic polymerizable initiator”). be.
本発明の組成物においては、成分(D)は、芳香環を有し、芳香環の数が3以上である。芳香環としては、ベンゼン環、ナフタレン環、アントラセン環等の環構造を形成する原子が全て炭素原子である芳香族炭化水素環、フラン環、ベンゾフラン環、ジベンゾフラン環、チオフェン環等の環構造を形成する原子に炭素原子以外の原子を含む芳香族複素環を挙げることができる。 In the composition of the present invention, the component (D) has an aromatic ring, and the number of aromatic rings is 3 or more. As the aromatic ring, an aromatic hydrocarbon ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a thiophene ring or the like in which all the atoms forming the ring structure such as a benzene ring, a naphthalene ring and an anthracene ring are carbon atoms are formed. Aromatic heterocycles containing atoms other than carbon atoms can be mentioned.
本発明の組成物においては、成分(D)の種類としては、光カチオン重合性開始剤および熱カチオン重合性開始剤のいずれも用いることができるが、感度の観点からは、光カチオン重合性開始剤であることが好ましい。 In the composition of the present invention, either a photocationic polymerizable initiator or a thermocationic polymerizable initiator can be used as the type of the component (D), but from the viewpoint of sensitivity, the photocationic polymerizable initiator is used. It is preferably an agent.
光カチオン重合性開始剤としては、オニウム塩である複塩またはその誘導体、あるいはオキシムスルホネート化合物、ハロゲン含有化合物、ジアゾケトン化合物、スルホン化合物、スルホン酸化合物、ジアゾメタン化合物、ニトロベンジル化合物、ベンゾイントシレート化合物、鉄アレーン錯体、アセトフェノン誘導体化合物等を用いることができ、これらは単独でまたは2種以上を混合して使用することができる。 Examples of the photocationic polymerizable initiator include a compound salt which is an onium salt or a derivative thereof, an oxime sulfonate compound, a halogen-containing compound, a diazoketone compound, a sulfo compound, a sulfonic acid compound, a diazomethane compound, a nitrobenzyl compound, and a benzointosilate compound. Iron arene complexes, acetophenone derivative compounds and the like can be used, and these can be used alone or in admixture of two or more.
本発明の組成物においては、なかでも、光カチオン重合性開始剤が、オニウム塩である複塩またはその誘導体であることが好ましい。かかる光カチオン重合性開始剤であることで、本発明の組成物は、硬化速度および接着力に優れたものとなるからである。 In the composition of the present invention, the photocationic polymerizable initiator is preferably a double salt which is an onium salt or a derivative thereof. This is because the composition of the present invention is excellent in curing speed and adhesive strength by being such a photocationic polymerizable initiator.
オニウム塩である複塩またはその誘導体のうち、芳香環の数が3以上である化合物としては、下記一般式(1)で表される陽イオンと陰イオンの塩を挙げることができる。 Among the double salt which is an onium salt or a derivative thereof, examples of the compound having 3 or more aromatic rings include salts of cations and anions represented by the following general formula (1).
[A]m+[B]m− (1)[A] m + [B] m- (1)
ここで陽イオン[A]m+はオニウムであることが好ましく、その構造は、例えば、下記一般式(2)で表すことができる。Here, the cation [A] m + is preferably onium, and its structure can be represented by, for example, the following general formula (2).
[(R10)aQ]m+ (2)[(R 10 ) a Q] m + (2)
ここで、R10は炭素原子数が1〜60であり、炭素原子以外の原子をいくつ含んでいても構わない有機基である。
aは1〜5の整数である。
a個のR10は各々独立で、同一でも異なっていても構わない。
a個のR10は、少なくとも1つが、芳香環を有する上記有機基であり、a個のR10中に含まれる芳香環の数が3以上である。QはS,N,Se,Te,P,As,Sb,Bi,O,I,Br,Cl,F,N=Nからなる群から選ばれる原子あるいは原子団である。また、陽イオン[A]m+中のQの原子価をqとしたとき、m=a−qなる関係が成り立つことが必要である。ただし、N=Nは原子価0として扱う。Here, R 10 is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms.
a is an integer of 1-5.
The a R 10s are independent of each other and may be the same or different.
The a number of R 10s is the organic group having at least one aromatic ring, and the number of aromatic rings contained in the a number of R 10s is 3 or more. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N = N. Further, when the valence of Q in the cation [A] m + is q, it is necessary that the relationship m = a−q is established. However, N = N is treated as having a valence of 0.
また、陰イオン[B]m−は、ハロゲン化物錯体であることが好ましく、その構造は、例えば、下記一般式(3)で表すことができる。Further, the anion [B] m- is preferably a halide complex, and its structure can be represented by, for example, the following general formula (3).
[LXb]m− (3)[LX b ] m- (3)
ここで、Lはハロゲン化物錯体の中心原子である金属または半金属(Metalloid)であり、B,P,As,Sb,Fe,Sn,Bi,Al,Ca,In,Ti,Zn,Sc,V,Cr,Mn,Co等である。Xはハロゲン原子である。bは3〜7の整数である。また、陰イオン[B]m−中のLの原子価をpとしたとき、m=b−pなる関係が成り立つことが必要である。Here, L is a metal or metalloid that is the central atom of the halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V. , Cr, Mn, Co and the like. X is a halogen atom. b is an integer of 3 to 7. Further, when the valence of L in the anion [B] m- is p, it is necessary that the relationship m = bp is established.
一般式(3)の陰イオン[LXb]m−の具体例としては、テトラキス(ペンタフルオロフェニル)ボレート[(C6F5)4B]−、テトラフルオロボレート(BF4)−、ヘキサフルオロホスフェート(PF6)−、ヘキサフルオロアンチモネート(SbF6)−、ヘキサフルオロアルセネート(AsF6)−、ヘキサクロロアンチモネート(SbCl6)−、トリス(ペンタフルオロメチル)トリフルオロリン酸イオン(FAPアニオン)等を挙げることができる。 Specific examples of the anion [LX b ] m- of the general formula (3) include tetrakis (pentafluorophenyl) borate [(C 6 F 5 ) 4 B] − , tetrafluoroborate (BF 4 ) − , and hexafluoro. Phosphate (PF 6 ) - , Hexafluoroantimonate (SbF 6 ) - , Hexafluoroarsenate (AsF 6 ) - , Hexachloroantimonate (SbCl 6 ) - , Tris (pentafluoromethyl) trifluorophosphate ion (FAP anion) And so on.
また、陰イオン[B]m−は、下記一般式(4)で表される構造のものも好ましく用いることができる。Further, as the anion [B] m− , one having a structure represented by the following general formula (4) can also be preferably used.
[LXb−1(OH)]m− (4)[LX b-1 (OH)] m- (4)
ここで、L,X,bは上記と同様である。また、その他用いることのできる陰イオンとしては、過塩素酸イオン(ClO4)−、トリフルオロメチル亜硫酸イオン(CF3SO3)−、フルオロスルホン酸イオン(FSO3)−、トルエンスルホン酸陰イオン、トリニトロベンゼンスルホン酸陰イオン、カンファースルフォネート、ノナフロロブタンスルフォネート、ヘキサデカフロロオクタンスルフォネート、テトラアリールボレート、テトラキス(ペンタフルオロフェニル)ボレート等を挙げることができる。Here, L, X, and b are the same as described above. Other anions that can be used include perchlorate ion (ClO 4 ) − , trifluoromethyl sulfite ion (CF 3 SO 3 ) − , fluorosulfonic acid ion (FSO 3 ) − , and toluene sulfonic acid anion. , Trinitrobenzene sulfonic acid anion, camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctanesulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
本発明の組成物では、このようなオニウム塩の中でも、下記群Iまたは群IIで表されるスルホニウムカチオンとヘキサフルオロアンチモンイオン、テトラキス(ペンタフルオロフェニル)ボレートイオン等のスルホニウム塩を使用することが特に有効である。これらの中から、その1種を単独で、または2種以上を混合して使用することができる。 In the composition of the present invention, among such onium salts, sulfonium cations represented by the following group I or group II and sulfonium salts such as hexafluoroantimon ion and tetrakis (pentafluorophenyl) borate ion can be used. Especially effective. From these, one of them can be used alone, or two or more of them can be mixed and used.
これらの中でも、実用面と光感度の観点から、芳香族ヨードニウム塩、芳香族スルホニウム塩を用いることが好ましく、特に、芳香族スルホニウム塩であることが好ましく、下記一般式(5)で表される芳香族スルホニウム塩が、感度の点からさらに好ましい。また、光カチオン重合性開始剤が芳香族スルホニウム塩であることで、本発明の組成物は、硬化速度および接着力に優れたものとなるからである。 Among these, from the viewpoint of practical use and photosensitivity, it is preferable to use an aromatic iodonium salt or an aromatic sulfonium salt, and in particular, an aromatic sulfonium salt is preferable, and it is represented by the following general formula (5). Aromatic sulfonium salts are more preferred in terms of sensitivity. Further, since the photocationic polymerizable initiator is an aromatic sulfonium salt, the composition of the present invention has excellent curing speed and adhesive strength.
ここで、一般式(5)中、R121、R122、R123、R124、R125、R126、R127、R128、R129およびR130は、それぞれ独立に、水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基または炭素原子数2〜10のエステル基を表し、
R131、R132、R133およびR134は、それぞれ独立に、水素原子、ハロゲン原子または炭素原子数1〜10のアルキル基を表し、
R135は、水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基または下記化学式(A)〜(C)より選択されるいずれかの置換基を表し、Anq−はq価の陰イオンを表し、pは電荷を中性にする係数を表す。Here, in the general formula (5), R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 and R 130 are independently hydrogen atoms and halogen atoms, respectively. , An alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms.
R 131 , R 132 , R 133 and R 134 each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms.
R 135 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituent selected from the following chemical formulas (A) to (C), and An q − is a q-valent anion. Represents, and p represents the coefficient for neutralizing the charge.
化学式(A)〜(C)中、R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R245、R246、R247、R248およびR249は、それぞれ独立に、水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基または炭素原子数2〜10のエステル基を表し、
R240、R241、R242、R243およびR244は、それぞれ独立に、水素原子、ハロゲン原子または炭素原子数1〜10のアルキル基を表し、*は、一般式(5)中のSとの結合位置を表す。In the chemical formulas (A) to (C), R221 , R222 , R223 , R224 , R225 , R226 , R227 , R228 , R229 , R230 , R231 , R232 , R233 , R 234 , R 236 , R 237 , R 238 , R 239 , R 245 , R 246 , R 247 , R 248 and R 249 are independently hydrogen atoms, halogen atoms, and alkyl groups having 1 to 10 carbon atoms. Represents an alkoxy group having 1 to 10 carbon atoms or an ester group having 2 to 10 carbon atoms.
R 240 , R 241 and R 242 , R 243 and R 244 each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms, and * represents S in the general formula (5). Represents the connection position of.
一般式(5)で表される化合物において、R121、R122、R123、R124、R125、R126、R127、R128、R129、R130、R131、R132、R133、R134、R135、R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R240、R241、R242、R243、R244、R245、R246、R247、R248およびR249で表されるハロゲン原子としては、フッ素、塩素、臭素、ヨウ素等が挙げられる。Among the compounds represented by the general formula (5), R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133. , R 134 , R 135 , R 221 , R 222 , R 223 , R 224 , R 225 , R 226 , R 227 , R 228 , R 229 , R 230 , R 231 , R 232 , R 233 , R 234 , R 236, the halogen atom represented by R 237, R 238, R 239 , R 240, R 241, R 242, R 243, R 244, R 245, R 246, R 247, R 248 and R 249, fluorine , Chlorine, bromine, iodine and the like.
R121、R122、R123、R124、R125、R126、R127、R128、R129、R130、R131、R132、R133、R134、R135、R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R240、R241、R242、R243、R244、R245、R246、R247、R248およびR249で表される炭素原子数1〜10のアルキル基としては、メチル、エチル、プロピル、イソプロピル、ブチル、s−ブチル、t−ブチル、イソブチル、アミル、イソアミル、t−アミル、ヘキシル、シクロヘキシル、ヘプチル、オクチル、ノニル、エチルオクチル、2−メトキシエチル、3−メトキシプロピル、4−メトキシブチル、2−ブトキシエチル、メトキシエトキシエチル、メトキシエトキシエトキシエチル、3−メトキシブチル、2−メチルチオエチル、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、ブロモメチル、ジブロモメチル、トリブロモメチル、ジフルオロエチル、トリクロロエチル、ジクロロジフルオロエチル、ペンタフルオロエチル、ヘプタフルオロプロピル、ノナフルオロブチル、デカフルオロペンチル、トリデカフルオロヘキシル、ペンタデカフルオロヘプチル、ヘプタデカフルオロオクチル、メトキシメチル、1,2−エポキシエチル、メトキシエチル、メトキシエトキシメチル、メチルチオメチル、エトキシエチル、ブトキシメチル、t−ブチルチオメチル、4−ペンテニルオキシメチル、トリクロロエトキシメチル、ビス(2−クロロエトキシ)メチル、メトキシシクロヘキシル、1−(2−クロロエトキシ)エチル、1−メチル−1−メトキシエチル、エチルジチオエチル、トリメチルシリルエチル、t−ブチルジメチルシリルオキシメチル、2−(トリメチルシリル)エトキシメチル、t−ブトキシカルボニルメチル、エチルオキシカルボニルメチル、エチルカルボニルメチル、t−ブトキシカルボニルメチル、アクリロイルオキシエチル、メタクリロイルオキシエチル、2−メチル−2−アダマンチルオキシカルボニルメチル、アセチルエチル、2−メトキシ−1−プロペニル、ヒドロキシメチル、2−ヒドロキシエチル、1−ヒドロキシエチル、2−ヒドロキシプロピル、3−ヒドロキシプロピル、3−ヒドロキシブチル、4−ヒドロキシブチル、1,2−ジヒドロキシエチル等が挙げられる。R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 135 , R 221 and R 222. , R 223 , R 224 , R 225 , R 226 , R 227 , R 228 , R 229 , R 230 , R 231 and R 232 , R 233 , R 234 , R 236 , R 237 , R 238 , R 239 , R As alkyl groups having 1 to 10 carbon atoms represented by 240, R 241 , R 242 , R 243 , R 244 , R 245 , R 246 , R 247 , R 248 and R 249, methyl, ethyl, propyl, etc. Isopropyl, butyl, s-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyloctyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-Butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromo Methyl, difluoroethyl, trichloroethyl, dichlorodifluoroethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, decafluoropentyl, tridecafluorohexyl, pentadecafluoroheptyl, heptadecafluorooctyl, methoxymethyl, 1,2- Epoxyethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, ethoxyethyl, butoxymethyl, t-butylthiomethyl, 4-pentenyloxymethyl, trichloroethoxymethyl, bis (2-chloroethoxy) methyl, methoxycyclohexyl, 1-( 2-Chloroethoxy) ethyl, 1-methyl-1-methoxyethyl, ethyldithioethyl, trimethylsilylethyl, t-butyldimethylsilyloxymethyl, 2- (trimethylsilyl) ethoxymethyl, t-butoxycarbonylmethyl, ethyloxycarbonylmethyl, Ethylcarbonylmethyl, t-butoxycarbonylmethyl, acryloyloxyethyl, methacrylo Iloxyethyl, 2-methyl-2-adamantyloxycarbonylmethyl, acetylethyl, 2-methoxy-1-propenyl, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3 -Hydroxybutyl, 4-hydroxybutyl, 1,2-dihydroxyethyl and the like can be mentioned.
R121、R122、R123、R124、R125、R126、R127、R128、R129、R130、R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R245、R246、R247、R248およびR249で表される炭素原子数1〜10のアルコキシ基としては、メトキシ、エトキシ、プロピルオキシ、イソプロピルオキシ、ブチルオキシ、s−ブチルオキシ、t−ブチルオキシ、イソブチルオキシ、ペンチルオキシ、イソアミルオキシ、t−アミルオキシ、ヘキシルオキシ、シクロヘキシルオキシ、シクロヘキシルメチルオキシ、テトラヒドロフラニルオキシ、テトラヒドロピラニルオキシ、2−メトキシエチルオキシ、3−メトキシプロピルオキシ、4−メトキシブチルオキシ、2−ブトキシエチルオキシ、メトキシエトキシエチルオキシ、メトキシエトキシエトキシエチルオキシ、3−メトキシブチルオキシ、2−メチルチオエチルオキシ、トリフルオロメチルオキシ等が挙げられる。R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 221 , R 222 , R 223 , R 224 , R 225 , R 226 , R 227. , R 228 , R 229 , R 230 , R 231 and R 232 , R 233 , R 234 , R 236 , R 237 , R 238 , R 239 , R 245 , R 246 , R 247 , R 248 and R 249 . Alkoxy groups having 1 to 10 carbon atoms include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, and hexyloxy. Cyclohexyloxy, Cyclohexylmethyloxy, Tetrahydrofuranyloxy, Tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxyethoxyethoxyethyloxy , 3-methoxybutyloxy, 2-methylthioethyloxy, trifluoromethyloxy and the like.
R121、R122、R123、R124、R125、R126、R127、R128、R129、R130、R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R245、R246、R247、R248およびR249で表される炭素原子数2〜10のエステル基としては、メトキシカルボニル、エトキシカルボニル、イソプロピルオキシカルボニル、フェノキシカルボニル、アセトキシ、プロピオニルオキシ、ブチリルオキシ、クロロアセチルオキシ、ジクロロアセチルオキシ、トリクロロアセチルオキシ、トリフルオロアセチルオキシ、t−ブチルカルボニルオキシ、メトキシアセチルオキシ、ベンゾイルオキシ等が挙げられる。R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 221 , R 222 , R 223 , R 224 , R 225 , R 226 , R 227. , R 228 , R 229 , R 230 , R 231 and R 232 , R 233 , R 234 , R 236 , R 237 , R 238 , R 239 , R 245 , R 246 , R 247 , R 248 and R 249 . Examples of the ester group having 2 to 10 carbon atoms include methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarbonyl, acetoxy, propionyloxy, butyloxy, chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy and trifluoroacetyloxy. , T-Butylcarbonyloxy, methoxyacetyloxy, benzoyloxy and the like.
一般式(5)中のpAnq−で表されるq価のアニオンとしては、上述の陰イオン[B]m−として挙げたもののうち、所定の価数のアニオンを用いることができる。 As the q-valent anion represented by pAn q- in the general formula (5), an anion having a predetermined valence among those listed as the above-mentioned anion [B] m- can be used.
本発明の組成物においては、R135が、化学式(A)〜(C)より選択されるものであることが好ましく、なかでも、化学式(A)または(C)より選択されるものであることが好ましい。R135が上述の構造を有することにより、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。本発明の組成物においては、成分(D)の分散安定性の観点からは、R135が化学式(C)であるものであることが好ましい。一方、硬化速度および接着力により優れたものとする観点からは、R135が化学式(A)であるものであることが好ましい。本発明の組成物においては、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとする観点からは、成分(D)は、R135が化学式(A)であるものと、化学式(C)であるものとの両者を含むことが好ましい。In the composition of the present invention, R 135 is preferably selected from the chemical formulas (A) to (C), and above all, it is selected from the chemical formulas (A) or (C). Is preferable. This is because the R 135 having the above-mentioned structure has an excellent balance between the dispersion stability of the component (D), the curing speed, and the adhesive force. In the composition of the present invention, it is preferable that R135 has the chemical formula (C) from the viewpoint of the dispersion stability of the component (D). On the other hand, from the viewpoint of making the curing speed and the adhesive strength more excellent, it is preferable that R 135 has the chemical formula (A). In the composition of the present invention, R 135 is the chemical formula (A) of the component (D) from the viewpoint of excellent balance between the dispersion stability of the component (D), the curing rate and the adhesive force. It is preferable to include both those having a chemical formula (C) and those having a chemical formula (C).
成分(D)は、R135が化学式(A)であるものと、化学式(C)であるものとの両者を含む場合、R135が化学式(A)であるものの含有量は、化学式(C)であるもの100質量部に対して、10質量部以上200質量部以下とすることができ、なかでも、50質量部以上、200質量部以下であることが好ましく、80質量部以上120質量部以下であることが好ましい。かかる範囲の含有量であることで、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。Component (D), if it contains both as R 135 is as a chemical formula (A), Formula (C), the content of those R 135 is a chemical formula (A), formula (C) It can be 10 parts by mass or more and 200 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less, and 80 parts by mass or more and 120 parts by mass or less. Is preferable. This is because the content in such a range makes the balance between the dispersion stability of the component (D), the curing speed and the adhesive force excellent.
R121、R122、R123、R124、R125、R126、R127、R128、R129、R130、R131、R132、R133およびR134は、水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基または炭素原子数2〜10のエステル基であるが、なかでも、水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基であることが好ましく、特に、水素原子であることが好ましい。上述の官能基であることで、本発明の組成物は、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。また、上記カチオン重合性開始剤が合成容易なものとなるからである。R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 and R 134 are hydrogen atoms, halogen atoms, and carbon. It is an alkyl group having 1 to 10 atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 10 carbon atoms. , An alkoxy group having 1 to 10 carbon atoms is preferable, and a hydrogen atom is particularly preferable. This is because the above-mentioned functional group makes the composition of the present invention excellent in balance between the dispersion stability of the component (D), the curing speed and the adhesive force. In addition, the cationically polymerizable initiator can be easily synthesized.
R221、R222、R223、R224、R225、R226、R227、R228、R229、R230、R231、R232、R233、R234、R236、R237、R238、R239、R240、R241、R242、R243、R244、R245、R246、R247、R248およびR249は水素原子、ハロゲン原子、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基であることが好ましく、特に、水素原子であることが好ましい。上述の官能基であることで、本発明の組成物は、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。また、上記カチオン重合性開始剤が合成容易なものとなるからである。 R221 , R222 , R223 , R224 , R225 , R226 , R227 , R228 , R229 , R230 , R231 , R232 , R233 , R234 , R236 , R237 , R238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 , R 245 , R 246 , R 247 , R 248 and R 249 are hydrogen atoms, halogen atoms, alkyl groups with 1 to 10 carbon atoms, It is preferably an alkoxy group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom. This is because the above-mentioned functional group makes the composition of the present invention excellent in balance between the dispersion stability of the component (D), the curing speed and the adhesive force. In addition, the cationically polymerizable initiator can be easily synthesized.
本発明の組成物においては、成分(D)の含有量としては、所望の硬化速度および接着力を得られるものであればよく、例えば、本発明の組成物の固形分100質量部中に、0.1質量部以上10質量部以下であることが好ましく、なかでも、0.5質量部以上8質量部以下であることが好ましく、特に、1.0質量部以上7質量部以下であることが好ましく、なかでも特に1.5質量部以上6質量部以下であることが好ましく、なかでも特に、2.0質量部以上5質量部以下であることが好ましい。かかる範囲の含有量であることで、本発明の組成物は、成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなる。なお、本発明の組成物の固形分とは、溶剤以外の全ての成分を含むものである。 In the composition of the present invention, the content of the component (D) may be such that a desired curing rate and adhesive strength can be obtained. For example, in 100 parts by mass of the solid content of the composition of the present invention, It is preferably 0.1 part by mass or more and 10 parts by mass or less, particularly preferably 0.5 part by mass or more and 8 parts by mass or less, and particularly 1.0 part by mass or more and 7 parts by mass or less. It is preferable that the amount is 1.5 parts by mass or more and 6 parts by mass or less, and particularly preferably 2.0 parts by mass or more and 5 parts by mass or less. When the content is in such a range, the composition of the present invention has an excellent balance between the dispersion stability of the component (D), the curing rate and the adhesive force. The solid content of the composition of the present invention includes all components other than the solvent.
カチオン重合性開始剤(D)の市販品としては、例えば、「CPI−100P」、「CPI−101A」(以上、サンアプロ株式会社製)、;「IRGACURE 250」(BASF SE社製)、「アデカオプトマーSP−172」、「アデカオプトマーSP−170」、「アデカオプトマーSP−152」、「アデカオプトマーSP−150」(以上、株式会社ADEKA製)、;「サンエイド SI−60L」、「サンエイド SI−80L」、「サンエイド SI−100L」、「サンエイド SI−150L」(以上、三新化学工業株式会社製)等が挙げられる。 Commercially available products of the cationically polymerizable initiator (D) include, for example, "CPI-100P", "CPI-101A" (all manufactured by San-Apro Co., Ltd.); "IRGACURE 250" (manufactured by BASF SE Corporation), "ADEKA CORPORATION". Optomer SP-172 "," ADEKA PTMER SP-170 "," ADEKA OPTMER SP-152 "," ADEKA PTMER SP-150 "(all manufactured by ADEKA CORPORATION);" Sun Aid SI-60L ", Examples thereof include "Sun Aid SI-80L", "Sun Aid SI-100L", and "Sun Aid SI-150L" (all manufactured by Sanshin Chemical Industry Co., Ltd.).
本発明の組成物は、硬化速度および接着力に優れたものとの観点から、成分(D)の含有量としては、成分(A)〜(D)の総量100質量部中、1〜10質量部が好ましく、また、成分(B)100質量部に対して、1質量部以上8質量部以下であることが好ましく、特に、1.5質量部以上7質量部以下であることが好ましく、なかでも特に2.0質量部以上6質量部以下であることが好ましく、なかでも特に、3.0質量部以上5質量部以下であることが好ましい。 From the viewpoint of excellent curing speed and adhesive strength, the composition of the present invention contains 1 to 10 parts by mass of the component (D) in 100 parts by mass of the total amount of the components (A) to (D). The amount is preferably 1 part by mass or more and 8 parts by mass or less, and particularly preferably 1.5 parts by mass or more and 7 parts by mass or less with respect to 100 parts by mass of the component (B). However, it is particularly preferably 2.0 parts by mass or more and 6 parts by mass or less, and particularly preferably 3.0 parts by mass or more and 5 parts by mass or less.
<溶剤>
本発明の組成物には溶剤を用いてもよく、溶剤は、組成物中の各成分を分散または溶解可能なものであり、常温常圧下で液体の化合物である。なお、溶剤としては、アクリル基、メタクリル基、ビニル基、エポキシ基、オキセタン基を有する化合物を含まないものを用いることができる。<Solvent>
A solvent may be used in the composition of the present invention, and the solvent is a compound capable of dispersing or dissolving each component in the composition and is a liquid compound under normal temperature and pressure. As the solvent, a solvent that does not contain a compound having an acrylic group, a methacrylic group, a vinyl group, an epoxy group, or an oxetane group can be used.
このような溶剤としては、水、有機溶剤のいずれも用いることができるが、有機溶剤を好ましく用いることができる。有機溶剤の含有量としては、所望の硬化速度および接着力が得られるものであればよく、溶剤100質量部中に80質量部以上であることが好ましく、90質量部以上であることが好ましく、なかでも95質量部以上であることが好ましく、特に、100質量部、すなわち、溶剤として有機溶剤のみを含むことが好ましい。含有量がかかる範囲であることで、本発明の組成物は、成分(C)および成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。 As such a solvent, either water or an organic solvent can be used, but an organic solvent can be preferably used. The content of the organic solvent may be any as long as it can obtain a desired curing rate and adhesive strength, and is preferably 80 parts by mass or more, preferably 90 parts by mass or more in 100 parts by mass of the solvent. Among them, it is preferably 95 parts by mass or more, and particularly preferably 100 parts by mass, that is, it contains only an organic solvent as a solvent. This is because the composition of the present invention has an excellent balance between the dispersion stability of the component (C) and the component (D), the curing speed, and the adhesive force when the content is within such a range.
有機溶剤としては、プロピレンカーボネート、エチレンカーボネート、1,2−ブチレンカーボネート、ジメチルカーボネートおよびジエチルカーボネート等のカーボネート類;アセトン、メチルエチルケトン、シクロヘキサノン、メチルイソアミルケトン、2−ヘプタノン等のケトン類;エチレングリコール、エチレングリコールモノアセテート、ジエチレングリコール、ジエチレングリコールモノアセテート、プロピレングリコール、プロピレングリコールモノアセテート、ジプロピレングリコールおよびジプロピレングリコールモノアセテートのモノメチルエーテル、モノエチルエーテル、モノプロピルエーテル、モノブチルエーテルまたはモノフェニルエーテル等の多価アルコール類およびその誘導体;ジオキサンのような環式エーテル類;蟻酸エチル、乳酸メチル、乳酸エチル、酢酸メチル、酢酸エチル、酢酸ブチル、ピルビン酸メチル、アセト酢酸メチル、アセト酢酸エチル、ピルビン酸エチル、エトキシ酢酸エチル、メトキシプロピオン酸メチル、エトキシプロピオン酸エチル、2−ヒドロキシプロピオン酸メチル、2−ヒドロキシプロピオン酸エチル、2−ヒドロキシ−2−メチルプロピオン酸エチル、2−ヒドロキシ−3−メチルブタン酸メチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート等のエステル類;トルエン、キシレン等の芳香族炭化水素類;γ−カプロラクトン、δ−カプロラクトン、ε−カプロラクトン、ジメチル−ε−カプロラクトン、δ−バレロラクトン、γ−バレロラクトン、およびγ−ブチロラクトン等のラクトン類等が挙げられ、これらの溶媒は1種または2種以上の混合溶媒として使用することができる。有機溶剤の中でも、多価アルコール類の誘導体、ラクトン類、カーボネート類であることが好ましく、特に、カーボネート類であることが好ましく、なかでも特に、プロピレンカーボネートであることが好ましい。これらの有機溶剤を用いることで、本発明の組成物は、成分(C)および成分(D)の分散安定性と硬化速度および接着力とのバランスに優れたものとなるからである。 Examples of the organic solvent include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate and diethyl carbonate; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone and 2-heptanone; ethylene glycol and ethylene. Polyhydric alcohols such as glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol and dipropylene glycol monoacetate monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether or monophenyl ether. Classes and derivatives thereof; cyclic ethers such as dioxane; ethyl acetate, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl pyruvate, ethoxyacetate Ethyl, methyl methoxypropionate, ethyl ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxy Esters such as butyl acetate and 3-methyl-3-methoxybutyl acetate; aromatic hydrocarbons such as toluene and xylene; γ-caprolactone, δ-caprolactone, ε-caprolactone, dimethyl-ε-caprolactone, δ-valerolactone , Γ-Valerolactone, lactones such as γ-butyrolactone, and the like, and these solvents can be used as one or more mixed solvents. Among the organic solvents, derivatives of polyhydric alcohols, lactones and carbonates are preferable, carbonates are particularly preferable, and propylene carbonate is particularly preferable. This is because the composition of the present invention has an excellent balance between the dispersion stability of the component (C) and the component (D), the curing speed, and the adhesive force by using these organic solvents.
有機溶剤の分子量としては、成分(A)〜成分(D)の溶解性または分散安定性と硬化速度および接着力とのバランスに優れたものとなる観点からは、50以上300以下であることが好ましく、なかでも、80以上200以下であることが好ましく、90以上150以下であることが好ましい。 The molecular weight of the organic solvent is 50 or more and 300 or less from the viewpoint of excellent balance between the solubility or dispersion stability of the components (A) to (D), the curing rate and the adhesive force. It is preferable that it is 80 or more and 200 or less, and 90 or more and 150 or less.
有機溶剤の沸点としては、硬化物からの揮散の少ないものとする観点からは、100℃以上350℃以下であることが好ましく、なかでも、130℃以上300℃以下であることが好ましく、特に、200℃以上300℃以下であることが好ましく、中でも特に200℃以上250℃以下であることが好ましい。なお、沸点は、大気圧下における値を表すものである。 The boiling point of the organic solvent is preferably 100 ° C. or higher and 350 ° C. or lower, particularly preferably 130 ° C. or higher and 300 ° C. or lower, from the viewpoint of reducing volatilization from the cured product. It is preferably 200 ° C. or higher and 300 ° C. or lower, and particularly preferably 200 ° C. or higher and 250 ° C. or lower. The boiling point represents a value under atmospheric pressure.
<その他の成分>
本発明の組成物は、上記の成分以外も必要に応じてその他の成分を含むことができる。その他の成分は、必要に応じて、無機フィラー、有機フィラー、顔料、シランカップリング剤、染料等の着色剤、光増感剤、消泡剤、増粘剤、チクソ剤、界面活性剤、レベリング剤、難燃剤、可塑剤、安定剤、重合禁止剤、紫外線吸収剤、酸化防止剤、静電防止剤、流動調整剤および接着促進剤等の各種樹脂添加物等を含むことができる。その他の成分の合計の含有量は、本発明の組成物の固形分中に30質量%以下が好ましい。<Other ingredients>
The composition of the present invention may contain other components other than the above components, if necessary. Other ingredients include inorganic fillers, organic fillers, pigments, silane coupling agents, colorants such as dyes, photosensitizers, defoamers, thickeners, thixogens, surfactants, and leveling, as required. It can contain various resin additives such as agents, flame retardants, plasticizers, stabilizers, polymerization inhibitors, ultraviolet absorbers, antioxidants, antioxidants, flow modifiers and adhesion promoters. The total content of the other components is preferably 30% by mass or less in the solid content of the composition of the present invention.
本発明の組成物の製造方法としては、上記各成分を均一に混合できる方法であれば特に限定されるものではなく、例えば、成分(A)および成分(B)に対して、成分(C)、成分(D)および溶剤を添加して混合する方法を挙げることができる。なお、混合方法については、公知の混合装置を用いる方法を採用でき、例えば、3本ロール、サンドミル、ボールミル等を用いる方法を挙げることができる。 The method for producing the composition of the present invention is not particularly limited as long as each of the above components can be uniformly mixed. For example, the component (C) is compared with the component (A) and the component (B). , The method of adding the component (D) and the solvent and mixing them. As a mixing method, a method using a known mixing device can be adopted, and examples thereof include a method using a three-roll, sand mill, ball mill and the like.
本発明の組成物の硬化方法としては、成分(C)および成分(D)の種類に応じて適宜設定されるものである。硬化方法としては、成分(C)および成分(D)が光ラジカル重合開始剤および光カチオン重合性開始剤である場合には、本発明の組成物に対して、活性エネルギー線を照射する活性エネルギー線照射処理を行う方法を用いることができる。 The curing method of the composition of the present invention is appropriately set according to the types of the component (C) and the component (D). As a curing method, when the component (C) and the component (D) are a photoradical polymerization initiator and a photocationic polymerizable initiator, the composition of the present invention is irradiated with active energy rays. A method of performing a radical irradiation treatment can be used.
活性エネルギー線としては、可視光線、紫外線、電子線、X線、放射線、高周波等を挙げることができ、紫外線が経済的に最も好ましい。紫外線の光源としては、紫外線レーザー、水銀ランプ、キセノンレーザ、メタルハライドランプ等が挙げられる。また、本発明の組成物はLED光源を照射により硬化させることが可能である。LED光源からの活性エネルギー線としては、紫外線が挙げられる。LED光源からの活性エネルギー線の波長としては、350nm〜405nmが挙げられる。本発明の組成物は、カチオン重合性開始剤が光カチオン重合性開始剤である場合には、活性エネルギー線照射により通常は0.1秒〜数分後に指触乾燥状態或いは溶媒不溶性の状態に硬化することができる。活性エネルギー線および活性エネルギー線への暴露時間としては、国際公開2013/172145号公報等に記載の内容と同様とすることができる。 Examples of the active energy ray include visible light, ultraviolet light, electron beam, X-ray, radiation, high frequency, and the like, and ultraviolet light is most economically preferable. Examples of the ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp. Further, the composition of the present invention can be cured by irradiating an LED light source. Examples of the active energy ray from the LED light source include ultraviolet rays. Examples of the wavelength of the active energy ray from the LED light source include 350 nm to 405 nm. When the cationically polymerizable initiator is a photocationic polymerizable initiator, the composition of the present invention usually becomes dry to the touch or solvent-insoluble after 0.1 seconds to several minutes by irradiation with active energy rays. Can be cured. The exposure time to the active energy rays and the active energy rays can be the same as that described in International Publication No. 2013/172145.
本発明の組成物の硬化方法としては、成分(C)が熱ラジカル重合性開始剤である場合、または成分(D)が熱カチオン重合性開始剤である場合には、本発明の組成物に対して、加熱処理を行う方法を用いることができる。本発明の組成物を加熱により硬化させる場合の条件は、70℃〜250℃で1〜100分とすることができる。プレベイク(PAB;Pre applied bake)した後、加圧して、ポストベイク(PEB;Post exposure bake)してもよいし、異なる数段階の温度でベイクしてもよい。加熱条件は各成分の種類および配合割合によって異なるが、例えば、70℃〜180℃で、オーブンなら5分間〜15分間、ホットプレートなら1〜5分間とすることができる。その後、塗膜を硬化させるために180℃〜250℃、好ましくは200℃〜250℃で、オーブンなら30分間〜90分間、ホットプレートなら5分間〜30分間加熱処理することによって硬化膜を得ることができる。 As a method for curing the composition of the present invention, when the component (C) is a thermal radical polymerizable initiator, or when the component (D) is a thermal cationic polymerizable initiator, the composition of the present invention can be used. On the other hand, a method of performing heat treatment can be used. The conditions for curing the composition of the present invention by heating can be 70 ° C. to 250 ° C. for 1 to 100 minutes. It may be pre-baked (PAB) and then pressurized to post-bake (PEB), or it may be baked at several different temperatures. The heating conditions vary depending on the type and blending ratio of each component, but can be, for example, 70 ° C. to 180 ° C., 5 minutes to 15 minutes for an oven, and 1 to 5 minutes for a hot plate. Then, a cured film is obtained by heat-treating the coating film at 180 ° C. to 250 ° C., preferably 200 ° C. to 250 ° C. for 30 minutes to 90 minutes in an oven and 5 minutes to 30 minutes in a hot plate. Can be done.
本発明の組成物の用途としては、硬化物を形成して使用する用途であれば特に限定されるものではなく、光学フィルム、接着剤、メガネ、撮像用レンズに代表される光学材料、塗料、コーティング剤、ライニング剤、インキ、高屈折材料、水溶性材料、半導体・ディスプレイ・MEMS・医療機器用レジスト、液状レジスト、印刷版、絶縁ワニス、絶縁シート、積層板、プリント基盤、半導体装置用・LEDパッケージ用・液晶注入口用・有機EL用・光素子用・電気絶縁用・電子部品用・分離膜用等の封止剤、成形材料、パテ、ガラス繊維含浸剤、目止め剤、半導体用・太陽電池用等のパッシベーション膜、層間絶縁膜、保護膜、カラーフィルターの保護膜、スペーサー、DNA分離チップ、マイクロリアクター、ナノバイオデバイス、ハードディスク用記録材料、固体撮像素子、発光ダイオード、有機発光デバイス、ルミネセントフィルム、蛍光フィルム、アクチュエーター、ホログラム、プラズモンデバイス、偏光板、偏光フィルム、位相差フィルム、液晶表示装置のバックライトに使用されるプリズムレンズシート、プロジェクションテレビ等のスクリーンに使用されるフレネルレンズシート、レンチキュラーレンズシート等のレンズシートのレンズ部、またはこのようなシートを用いたバックライト等、マイクロレンズ等の光学レンズ、光学素子、光コネクター、光導波路、光学的造形用注型剤等を挙げることができる。 The use of the composition of the present invention is not particularly limited as long as it is used by forming a cured product, and is an optical film, an adhesive, glasses, an optical material typified by an imaging lens, a paint, and the like. Coating agents, lining agents, inks, highly refracting materials, water-soluble materials, semiconductors / displays / MEMS / medical device resists, liquid resists, printing plates, insulating varnishes, insulating sheets, laminates, printed substrates, semiconductor device / LEDs Sealants, molding materials, putties, glass fiber impregnants, sealants, semiconductors, etc. for packages, liquid crystal inlets, organic EL, optical elements, electrical insulation, electronic parts, separation films, etc. Passion film for solar cells, interlayer insulation film, protective film, protective film for color filter, spacer, DNA separation chip, microreactor, nanobiodevice, recording material for hard disk, solid-state imaging device, light emitting diode, organic light emitting device, lumine Cent film, fluorescent film, actuator, hologram, plasmon device, polarizing plate, polarizing film, retardation film, prism lens sheet used for backlight of liquid crystal display, Frenel lens sheet used for screen of projection TV, etc. Examples include the lens portion of a lens sheet such as a lenticular lens sheet, a backlight using such a sheet, an optical lens such as a microlens, an optical element, an optical connector, an optical waveguide, a casting agent for optical modeling, and the like. Can be done.
本発明の組成物は、硬化速度および接着力に優れているとの効果をより効果的に発揮できる観点から、接着剤に用いられることが好ましい。接着剤の具体的な用途としては、メガネや撮像用レンズに代表される光学材料、積層板やプリント基盤に代表される電子材料用途、ヘッドアップディスプレイやカーナビゲーションに代表される車載用機器および有機ELや液晶に代表されるディスプレイパネル等の各種の用途に使用することができる。なかでも、透明性が要求される用途に用いられることが好ましく、特に、光学材料、車載用機器、ディスプレイパネル等の用途に用いられることが好ましい。 The composition of the present invention is preferably used as an adhesive from the viewpoint of being able to more effectively exert the effects of being excellent in curing speed and adhesive strength. Specific applications of adhesives include optical materials such as eyeglasses and imaging lenses, electronic materials such as laminates and printed substrates, in-vehicle devices such as head-up displays and car navigation systems, and organic materials. It can be used for various purposes such as display panels typified by EL and liquid crystal. Of these, it is preferably used in applications that require transparency, and in particular, it is preferably used in applications such as optical materials, in-vehicle devices, and display panels.
本発明の組成物を接着剤として用いる場合、本発明の接着剤により接着される被着体は、無機材料、有機材料のいずれも用いることができる。 When the composition of the present invention is used as an adhesive, either an inorganic material or an organic material can be used as the adherend to be adhered by the adhesive of the present invention.
有機材料としては、例えば、ジアセチルセルロース、トリアセチルセルロース(TAC)、プロピオニルセルロース、ブチリルセルロース、アセチルプロピオニルセルロース、ニトロセルロース等のセルロースエステル;ポリアミド;ポリイミド;ポリウレタン;エポキシ化合物;ポリカーボネート;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレート、ポリ−1,4−シクロヘキサンジメチレンテレフタレート、ポリエチレン−1,2−ジフェノキシエタン−4,4’−ジカルボキシレート、ポリブチレンテレフタレート等のポリエステル;ポリスチレン;ポリエチレン、ポリプロピレン、ポリメチルペンテン、ポリテトラフルオロエチレン、シクロオレフィンポリマー等のポリオレフィン;ポリビニルアルコール、ポリ酢酸ビニル、ポリ塩化ビニル、ポリフッ化ビニル等のビニル化合物;ポリメチルメタクリレート、ポリアクリル酸エステル等のアクリル系樹脂;ポリカーボネート;ポリスルホン;ポリエーテルスルホン;ポリエーテルケトン;ポリエーテルイミド;ポリオキシエチレン、ノルボルネン樹脂等の高分子材料が挙げられる。また、無機材料としては、例えば、ソーダガラスおよび石英ガラス等のガラス、金属、金属酸化物等を挙げることができる。 Examples of the organic material include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetyl propionyl cellulose, and nitro cellulose; polyamide; polyimide; polyurethane; epoxy compounds; polycarbonate; polyethylene terephthalate, polyethylene. Polyesters such as naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyetane-4,4'-dicarboxylate, polybutylene terephthalate; polystyrene; polyethylene, polypropylene, Polyethylenes such as polymethylpentene, polytetrafluoroethylene and cycloolefin polymers; vinyl compounds such as polyvinyl alcohol, polyvinyl acetate, polyvinyl chloride and polyvinyl fluoride; acrylic resins such as polymethylmethacrylate and polyacrylic acid esters; polycarbonates Polycarbonate; polyether sulfone; polyether ketone; polyetherimide; polymer materials such as polyoxyethylene and norbornene resin can be mentioned. Examples of the inorganic material include glass such as soda glass and quartz glass, metals, metal oxides, and the like.
<接着剤>
次に、本発明の接着剤について説明する。
本発明の接着剤は、本発明の組成物を含むものである。本発明の組成物を含むものであることで、本発明の接着剤は、硬化速度、接着力および耐水性に優れている。<Adhesive>
Next, the adhesive of the present invention will be described.
The adhesive of the present invention contains the composition of the present invention. By including the composition of the present invention, the adhesive of the present invention is excellent in curing speed, adhesive strength and water resistance.
本発明の接着剤は、本発明の組成物を用いて製造することができる。本発明の接着剤は、本発明の組成物のみからなるものであってもよく、本発明の組成物と、接着剤を製造する際に用いられることが知られている各種の添加剤等を公知の混合装置を用いて混合することで製造することができる。なお、本発明の組成物および接着剤の用途については、組成物の項に記載の内容と同様とすることができるので、ここでの説明は省略する。 The adhesive of the present invention can be produced using the composition of the present invention. The adhesive of the present invention may consist only of the composition of the present invention, and the composition of the present invention and various additives known to be used in producing the adhesive may be used. It can be produced by mixing using a known mixing device. The uses of the composition and the adhesive of the present invention can be the same as those described in the section of the composition, and thus the description thereof will be omitted here.
本発明の接着剤が、2つの部材を接着する接着剤として用いられる場合、本発明の接着剤の硬化後の厚みとしては、本発明の接着剤の用途等に応じて適宜設定されるものであるが、例えば、0.5μm以上10μm以下とすることができる。 When the adhesive of the present invention is used as an adhesive for adhering two members, the thickness of the adhesive of the present invention after curing is appropriately set according to the use of the adhesive of the present invention and the like. However, for example, it can be 0.5 μm or more and 10 μm or less.
<硬化物>
次に、本発明の硬化物について説明する。
本発明の硬化物は、本発明の組成物の硬化物である。本発明の硬化物は、例えば、硬化速度および接着力に優れた接着層として用いることができる。なお、本発明の組成物については、「組成物」の項に記載の内容と同様とすることができるので、ここでの説明は省略する。<Cured product>
Next, the cured product of the present invention will be described.
The cured product of the present invention is a cured product of the composition of the present invention. The cured product of the present invention can be used, for example, as an adhesive layer having excellent curing speed and adhesive strength. The composition of the present invention can be the same as that described in the section "Composition", and thus the description thereof will be omitted here.
本発明の硬化物は、本発明の組成物の硬化物であり、本発明の組成物の重合物を含むものである。すなわち、本発明の硬化物は、架橋縮合環を有する。 The cured product of the present invention is a cured product of the composition of the present invention and contains a polymer of the composition of the present invention. That is, the cured product of the present invention has a crosslinked condensed ring.
本発明の硬化物の平面視形状、厚み等については、硬化物の用途等に応じて適宜設定することができる。 The plan-view shape, thickness, etc. of the cured product of the present invention can be appropriately set according to the intended use of the cured product.
本発明の硬化物は、本発明の組成物を所望の形状となるように形成し、硬化させたものであり、製造方法については特に限定されるものではない。このような製造方法としては、例えば、後述する硬化物の製造方法の項に記載の内容と同様とすることができるため、ここでの説明は省略する。 The cured product of the present invention is obtained by forming the composition of the present invention into a desired shape and curing the composition, and the production method is not particularly limited. As such a manufacturing method, for example, the same contents as described in the section of the method for manufacturing a cured product described later can be used, and thus the description thereof will be omitted here.
本発明の硬化物の用途等については、組成物の項に記載の内容と同様とすることができる。 The uses and the like of the cured product of the present invention can be the same as those described in the section of composition.
<硬化物の製造方法>
次に、本発明の硬化物の製造方法について説明する。
本発明の硬化物の製造方法は、本発明の組成物を硬化する硬化工程を有する。本発明の硬化物の製造方法によれば、硬化工程が本発明の組成物を用いるものであるため、硬化速度および接着力を有する硬化物を得ることができる。以下、本発明の硬化物の製造方法の各工程について詳細に説明する。<Manufacturing method of cured product>
Next, a method for producing a cured product of the present invention will be described.
The method for producing a cured product of the present invention includes a curing step of curing the composition of the present invention. According to the method for producing a cured product of the present invention, since the curing step uses the composition of the present invention, a cured product having a curing speed and adhesive strength can be obtained. Hereinafter, each step of the method for producing a cured product of the present invention will be described in detail.
1.硬化工程
硬化工程は、本発明の組成物を硬化する工程であり、活性エネルギー線を照射または加熱する工程を含む。このような硬化方法については、「A.組成物」の項に記載の内容と同様とすることができる。1. 1. Curing Step The curing step is a step of curing the composition of the present invention, and includes a step of irradiating or heating active energy rays. Such a curing method can be the same as the content described in the section of "A. Composition".
2.その他の工程
本発明の硬化物の製造方法は、必要に応じてその他の工程を有するものであってもよい。このような工程としては、本発明の組成物を硬化する工程の前に、本発明の組成物を塗布する工程等を挙げることができる。本発明の組成物を塗布する方法としては、スピンコーター、ロールコーター、バーコーター、ダイコーター、カーテンコーター、各種の印刷、浸漬等の公知の方法を用いることができる。塗布する工程は、本発明の組成物を基材上に塗布することができる。2. Other Steps The method for producing a cured product of the present invention may have other steps, if necessary. Examples of such a step include a step of applying the composition of the present invention before the step of curing the composition of the present invention. As a method for applying the composition of the present invention, known methods such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing, and immersion can be used. In the coating step, the composition of the present invention can be applied onto the substrate.
基材としては、硬化物の用途等に応じて適宜設定することができ、ソーダガラス、石英ガラス、半導体基板、金属、紙、プラスチック等を含むものを挙げることができる。また、硬化物は、基材上で形成された後、基材から剥離して用いても、基材から他の被着体に転写して用いてもよい。 The base material can be appropriately set according to the intended use of the cured product, and examples thereof include soda glass, quartz glass, semiconductor substrates, metals, paper, plastics, and the like. Further, the cured product may be formed on the base material and then peeled off from the base material, or may be transferred from the base material to another adherend and used.
本発明の製造方法により製造される硬化物および用途等については、硬化物の項に記載の内容と同様とすることができる。 The cured product produced by the production method of the present invention, its use, and the like can be the same as those described in the section of the cured product.
本発明の組成物、これを含有する接着剤、その硬化物およびその製造方法は、上記実施形態に限定されるものではない。上記実施形態は、例示であり、本発明の特許請求の範囲に記載された技術的思想と実質的に同一な構成を有し、同様な作用効果を奏するものは、いかなるものであっても本発明の技術的範囲に包含される。 The composition of the present invention, an adhesive containing the same, a cured product thereof, and a method for producing the same are not limited to the above-mentioned embodiments. The above embodiment is an example, and any one having substantially the same configuration as the technical idea described in the claims of the present invention and exhibiting the same effect and effect is the present invention. It is included in the technical scope of the invention.
以下、本発明を、実施例等を挙げてさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to Examples and the like, but the present invention is not limited to these Examples.
[実施例1〜28および比較例1〜7]
下記表1〜表5に記載の配合に従って、各成分を配合して組成物を得た。各成分は以下の材料を用いた。なお、表中の配合量は、各成分の質量部を表す。[Examples 1-28 and Comparative Examples 1-7]
Each component was blended according to the blending shown in Tables 1 to 5 below to obtain a composition. The following materials were used for each component. The blending amount in the table represents the mass part of each component.
成分(A)
A1−1:トリシクロデカンジメタノールジアクリレート
A1−2:ジシクロペンタニルアクリレ−ト
A2−1:4−n−ヒドロキシブチルアクリレート
A2−2:化合物(A2)No.1
A3−1:トリ(アクリロイルエチル)イソシアヌレート
A3−2:ε−カプロラクトン変性トリス(2−アクリロキシエチル)
イソシアヌレート
A4−1:1,6−ヘキサンジオールジアクリレート
A4−2:1,10−デカンジオールジアクリレートIngredient (A)
A1-1: Tricyclodecanedimethanol diacrylate A1-2: Dicyclopentanylacrylate A2-1: 4-n-hydroxybutyl acrylate A2-2: Compound (A2) No. 1
A3-1: Tri (acryloyl ethyl) isocyanurate A3-2: ε-caprolactone-modified tris (2-acryloyl ethyl)
Isocyanurate A4-1: 1,6-hexanediol diacrylate A4-2: 1,10-decanediol diacrylate
成分(B)
B1−1:化合物(B1)No.1
B1−2:化合物(B1)No.2
B2−1:グリシジルメタクリレートとメチルメタクリレートの共重合物
(重量平均分子量8,000、エポキシ当量500〜600g/
eq.)
B2−2:グリシジルメタクリレートとメチルメタクリレートの共重合物
(重量平均分子量15,000、エポキシ当量500〜600g/
eq.)
B3−1:1,4−ブタンジオールジグリシジレート
B3−2:3,4−エポキシシクロヘキシルメチル−3,4−エポキシ
シクロヘキシルカルボキシレート
B3−3:トリメチロールプロパントリグリシジルエーテル
B3−4:3,3’−[オキシビス(メチレン)]ビス(3−エチルオキセ
タン)
B3−5:ビスフェノールAのジグリシジエーテルIngredient (B)
B1-1: Compound (B1) No. 1
B1-2: Compound (B1) No. 2
B2-1: Copolymer of glycidyl methacrylate and methyl methacrylate (weight average molecular weight 8,000, epoxy equivalent 500-600 g /
eq. )
B2-2: Copolymer of glycidyl methacrylate and methyl methacrylate (weight average molecular weight 15,000, epoxy equivalent 500-600 g /
eq. )
B3-1: 1,4-butanediol diglycidylate B3-2: 3,4-epoxycyclohexylmethyl-3,4-epoxy
Cyclohexylcarboxylate B3-3: Trimethylolpropane Triglycidyl ether B3-4: 3,3'-[oxybis (methylene)] bis (3-ethyloxe)
Tan)
B3-5: Diglycidiether of bisphenol A
成分(C)
C−1:1−ヒドロキシシクロヘキシルフェニルケトンIngredient (C)
C-1: 1-Hydroxycyclohexylphenyl ketone
成分(D)
D−1:CPI−100P(サンアプロ株式製)Ingredient (D)
D-1: CPI-100P (manufactured by Sun Appro Co., Ltd.)
添加剤
E−1:レベリング剤(東レ・ダウコーニング社製SH−29PA)Additive E-1: Leveling agent (SH-29PA manufactured by Toray Dow Corning)
[評価]
得られた各組成物につき、粘度、初期硬化性、接着力および耐水性を、下記の手順に従って評価した。[evaluation]
For each of the obtained compositions, the viscosity, initial curability, adhesive strength and water resistance were evaluated according to the following procedure.
(粘度)
得られた各組成物を、それぞれ25℃においてE型粘度計で粘度を測定した。粘度が30〜80mPa・sの組成物は塗工性に優れることから好ましく、40〜70mPa・sの組成物は、特に好ましい。(viscosity)
The viscosity of each of the obtained compositions was measured with an E-type viscometer at 25 ° C. A composition having a viscosity of 30 to 80 mPa · s is preferable because it is excellent in coatability, and a composition having a viscosity of 40 to 70 mPa · s is particularly preferable.
(評価用サンプルの作製方法)
得られた各組成物を、硬化後の厚みが3μmとなるように、一枚のPMMAフィルム(住友化学(株)製テクノロイ125S001)にそれぞれ塗布した後、もう一枚のコロナ放電処理を施したCOP(シクロオレフィンポリマー、日本ゼオン(株)製:品番ゼオノアフィルム14−060)フィルムとラミネーターを用いて貼り合わせ、無電極紫外光ランプを用いて1,000mJ/cm2に相当する光をCOPフィルム越しに照射して評価用サンプルを得た。(Method of preparing sample for evaluation)
Each of the obtained compositions was applied to one PMMA film (Technoloy 125S001 manufactured by Sumitomo Chemical Co., Ltd.) so that the thickness after curing was 3 μm, and then another corona discharge treatment was performed. COP (Cycloolefin Polymer, manufactured by Nippon Zeon Co., Ltd .: Part No. Zeonoa Film 14-060) A film and a laminator are used to bond them together, and a non-electrode ultraviolet light lamp is used to emit light equivalent to 1,000 mJ / cm 2 to the COP film. A sample for evaluation was obtained by irradiating through.
得られた評価用サンプルの90°ピール試験を行い、下記基準で評価を行った。結果を下記表1〜表5に併記する。なお、90°ピール試験は、25℃条件下、評価用サンプルを、引っ張り試験機FTN1−13A(アイコーエンジニアリング社製)でPMMAフィルムを90°方向に引っ張って剥がし、PMMAフィルムがCOPフィルムから剥離する際の最大強度を接着力として測定した。 The obtained evaluation sample was subjected to a 90 ° peel test and evaluated according to the following criteria. The results are also shown in Tables 1 to 5 below. In the 90 ° peel test, the evaluation sample is peeled off by pulling the PMMA film in the 90 ° direction with a tensile tester FTN1-13A (manufactured by Aiko Engineering Co., Ltd.) under 25 ° C. conditions, and the PMMA film is peeled off from the COP film. The maximum strength of the film was measured as the adhesive force.
(初期硬化性)
得られた評価用サンプルについて30℃、50%RH、大気圧条件下で露光から3分静置した後に、2.0cm幅に切り出して評価用サンプルを得た。この評価用サンプルを用いて90°ピール試験を行い、下記基準で評価を行った。結果を下記表1〜表5に併記する。(Initial curability)
The obtained evaluation sample was allowed to stand for 3 minutes from exposure under the conditions of 30 ° C., 50% RH, and atmospheric pressure, and then cut into a width of 2.0 cm to obtain an evaluation sample. A 90 ° peel test was performed using this evaluation sample, and evaluation was performed according to the following criteria. The results are also shown in Tables 1 to 5 below.
A:接着力が0.6N/20mm以上
B:接着力が0.4N/20mm以上、0.6N/20mm未満
C:接着力が0.4N/20mm未満
評価がA、Bの物は接着剤として好ましく使用でき、評価がAの物が特に好ましい。評価がCのものは、使用できる用途が限定されるため好ましくない。A: Adhesive strength is 0.6N / 20mm or more B: Adhesive strength is 0.4N / 20mm or more, less than 0.6N / 20mm C: Adhesive strength is less than 0.4N / 20mm It can be preferably used as a product, and a product having an evaluation of A is particularly preferable. Those with an evaluation of C are not preferable because the applications that can be used are limited.
(接着力)
得られた評価用サンプルについて30℃、50%RH、大気圧条件下で露光から12時間後に、2.0cm幅に切り出して接着力評価用サンプルを得た。得られたサンプルについて、上記の条件で90°ピール試験を行い接着力を測定し、下記の基準で評価を行った。(Adhesive strength)
The obtained evaluation sample was cut into a width of 2.0 cm 12 hours after exposure under the conditions of 30 ° C., 50% RH, and atmospheric pressure to obtain an adhesive strength evaluation sample. The obtained sample was subjected to a 90 ° peel test under the above conditions to measure the adhesive strength, and evaluated according to the following criteria.
A:接着力が2.5N/20mm以上
B:接着力が1.5N/20mm以上2.5N/20mm未満
C:接着力が1.0N/20mm以上1.5N/20mm未満
D:接着力が1.0N/20mm未満
接着力がAまたはBの物は接着剤として使用でき、特にAのものが好ましい。接着力がC、Dのものは、接着剤として好ましくない。A: Adhesive strength is 2.5N / 20mm or more B: Adhesive strength is 1.5N / 20mm or more and less than 2.5N / 20mm C: Adhesive strength is 1.0N / 20mm or more and less than 1.5N / 20mm D: Adhesive strength Those having an adhesive strength of less than 1.0 N / 20 mm and having an adhesive strength of A or B can be used as an adhesive, and those having an adhesive strength of A are particularly preferable. Adhesive strengths C and D are not preferable as adhesives.
(耐水性)
耐水性については温水後接着力により評価した。得られた評価用サンプルについて30℃、50%RH、大気圧条件下で露光から12時間後に、60℃の温水に48時間浸漬した後、温水から取り出して乾燥させたのち、2.0cm幅に切り出して温水後接着力評価用サンプルを得た。得られたサンプルについて、上記の方法で90°ピール試験を行い、温水後接着力を測定し、下記の基準で評価を行った。(water resistant)
The water resistance was evaluated by the adhesive strength after warm water. The obtained evaluation sample was immersed in warm water at 60 ° C. for 48 hours 12 hours after exposure under the conditions of 30 ° C., 50% RH, and atmospheric pressure, removed from the warm water, dried, and then expanded to a width of 2.0 cm. It was cut out to obtain a sample for evaluation of adhesive strength after warm water. The obtained sample was subjected to a 90 ° peel test by the above method, the adhesive strength after warm water was measured, and the evaluation was performed according to the following criteria.
A:温水後接着力が2.5N/20mm以上
B:温水後接着力が1.5N/20mm以上2.5N/20mm未満
C:温水後接着力が1.0N/20mm以上1.5N/20mm未満
D:温水後接着力が1.0N/20mm未満
温水後接着力がA、BまたはCの物は耐水性に優れた接着剤として使用でき、AまたはBのものが好ましく、特にAのものが好ましい。温水後接着力がDのものは、耐水性が求められる用途の接着剤として好ましくない。 A: Adhesive strength after warm water is 2.5N / 20mm or more B: Adhesive strength after warm water is 1.5N / 20mm or more and less than 2.5N / 20mm C: Adhesive strength after warm water is 1.0N / 20mm or more 1.5N / 20mm Less than D: Adhesive strength after warm water is less than 1.0 N / 20 mm Those with adhesive strength after warm water A, B or C can be used as an adhesive with excellent water resistance, and those with A or B are preferable, especially those with A. Is preferable. An adhesive having an adhesive strength of D after warm water is not preferable as an adhesive for applications requiring water resistance.
表1〜5より実施例の組成物は、塗工性、初期硬化性、接着力および耐水性に優れることが確認できた。よって本発明の組成物は、接着剤として有用である。 From Tables 1 to 5, it was confirmed that the compositions of Examples were excellent in coatability, initial curability, adhesive strength and water resistance. Therefore, the composition of the present invention is useful as an adhesive.
Claims (11)
前記ラジカル重合性成分(A)が、架橋縮合環を有するラジカル重合性化合物(A1)をラジカル重合性成分(A)100質量部中に70〜100質量部含有し、
前記カチオン重合性成分(B)が、架橋縮合環を有するカチオン重合性化合物(B1)をカチオン重合性成分(B)100質量部中に10〜50質量部含有することを特徴とする組成物。In the composition containing the radically polymerizable component (A) and the cationically polymerizable component (B),
The radically polymerizable component (A) contains 70 to 100 parts by mass of the radically polymerizable compound (A1) having a crosslinked condensed ring in 100 parts by mass of the radically polymerizable component (A).
A composition, wherein the cationically polymerizable component (B) contains 10 to 50 parts by mass of a cationically polymerizable compound (B1) having a crosslinked condensed ring in 100 parts by mass of the cationically polymerizable component (B).
前記ラジカル重合性成分(A)、前記カチオン重合性成分(B)、前記ラジカル重合性開始剤(C)および前記カチオン重合性開始剤(D)の総量100質量部中に、前記ラジカル重合性成分(A)40〜60質量部、前記カチオン重合性成分(B)30〜50質量部、前記ラジカル重合性開始剤(C)1〜10質量部および前記カチオン重合性開始剤(D)1〜10質量部を含有する請求項1記載の組成物。Further, it contains a radically polymerizable initiator (C) and a cationically polymerizable initiator (D).
The radically polymerizable component in 100 parts by mass of the total amount of the radically polymerizable component (A), the cationically polymerizable component (B), the radically polymerizable initiator (C) and the cationically polymerizable initiator (D). (A) 40 to 60 parts by mass, the cationically polymerizable component (B) 30 to 50 parts by mass, the radically polymerizable initiator (C) 1 to 10 parts by mass, and the cationically polymerizable initiator (D) 1 to 10 parts. The composition according to claim 1, which contains a part by mass.
The composition according to claim 1 or 2, wherein the crosslinked condensed ring contained in the radically polymerizable compound (A1) and the cationically polymerizable compound (B1) is a crosslinked condensed ring having a structure represented by the following formula (I). thing.
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JP2017149135A (en) * | 2016-02-25 | 2017-08-31 | 協立化学産業株式会社 | Method for producing layered body |
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