JP6594208B2 - Composition - Google Patents
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- Publication number
- JP6594208B2 JP6594208B2 JP2015550935A JP2015550935A JP6594208B2 JP 6594208 B2 JP6594208 B2 JP 6594208B2 JP 2015550935 A JP2015550935 A JP 2015550935A JP 2015550935 A JP2015550935 A JP 2015550935A JP 6594208 B2 JP6594208 B2 JP 6594208B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- composition according
- mass
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 75
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 129
- -1 dicarboxylic acid diester Chemical class 0.000 claims description 65
- 239000000853 adhesive Substances 0.000 claims description 51
- 230000001070 adhesive effect Effects 0.000 claims description 50
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000011342 resin composition Substances 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 21
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- 229920006295 polythiol Polymers 0.000 claims description 11
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 7
- 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 claims description 7
- 239000004973 liquid crystal related substance Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 description 35
- 238000012360 testing method Methods 0.000 description 31
- 150000003077 polyols Chemical class 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 239000005062 Polybutadiene Substances 0.000 description 21
- 229920002857 polybutadiene Polymers 0.000 description 21
- 238000001723 curing Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000003573 thiols Chemical class 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
- 230000005484 gravity Effects 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 4
- 229920001195 polyisoprene Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical class CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 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
- 229910001335 Galvanized steel Inorganic materials 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 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
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- MCQNUBHLBYBDRS-UHFFFAOYSA-N dipropan-2-yl nonanedioate Chemical compound CC(C)OC(=O)CCCCCCCC(=O)OC(C)C MCQNUBHLBYBDRS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000008397 galvanized steel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- VBQMTEHUPQSMFY-UHFFFAOYSA-N (2-diethoxyphosphorylphenyl)-(2,4,6-trimethylphenyl)methanone Chemical compound CCOP(=O)(OCC)c1ccccc1C(=O)c1c(C)cc(C)cc1C VBQMTEHUPQSMFY-UHFFFAOYSA-N 0.000 description 1
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- PAEWNKLGPBBWNM-UHFFFAOYSA-N 1,3,5-tris[2-(3-sulfanylbutoxy)ethyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(S)CCOCCN1C(=O)N(CCOCCC(C)S)C(=O)N(CCOCCC(C)S)C1=O PAEWNKLGPBBWNM-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- JKVSAZTYCZKNDX-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCC)=CC=C1N1CCOCC1 JKVSAZTYCZKNDX-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 description 1
- ZZYASVWWDLJXIM-UHFFFAOYSA-N 2,5-di-tert-Butyl-1,4-benzoquinone Chemical compound CC(C)(C)C1=CC(=O)C(C(C)(C)C)=CC1=O ZZYASVWWDLJXIM-UHFFFAOYSA-N 0.000 description 1
- QYXHDJJYVDLECA-UHFFFAOYSA-N 2,5-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)C=C1C1=CC=CC=C1 QYXHDJJYVDLECA-UHFFFAOYSA-N 0.000 description 1
- YWEJNVNVJGORIU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-hydroxy-2-phenylacetate Chemical compound OCCOCCOC(=O)C(O)C1=CC=CC=C1 YWEJNVNVJGORIU-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
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- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 229940105570 ornex Drugs 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- PWGIEBRSWMQVCO-UHFFFAOYSA-N phosphono prop-2-enoate Chemical compound OP(O)(=O)OC(=O)C=C PWGIEBRSWMQVCO-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
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- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- 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
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- 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
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J7/04—Coating
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- 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
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
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- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
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- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
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Description
本発明は、組成物に関する。 The present invention relates to a composition.
ＬＣＤ（液晶ディスプレイ）等の表示体の上に搭載するタッチパネルには、抵抗膜式、静電容量式、電磁誘導式、光学式等がある。これらのタッチパネルの表面に、見た目のデザイン性を良くする化粧板や、タッチする位置を指定するアイコンシートを貼り合わせる場合がある。静電容量式タッチパネルは、透明基板の上に透明電極を形成し、その上に透明板を貼り合わせた構造を有している。 There are a resistive film type, a capacitance type, an electromagnetic induction type, an optical type and the like as a touch panel mounted on a display body such as an LCD (liquid crystal display). There is a case where a decorative board for improving the appearance design and an icon sheet for designating a touch position are pasted on the surface of these touch panels. The capacitive touch panel has a structure in which a transparent electrode is formed on a transparent substrate and a transparent plate is bonded thereon.
従来、化粧板とタッチパネルとの貼り合わせ、アイコンシートとタッチパネルとの貼り合わせ、透明基板と透明板の貼り合わせには、接着剤を用いていた。 Conventionally, an adhesive is used for bonding a decorative plate and a touch panel, bonding an icon sheet and a touch panel, and bonding a transparent substrate and a transparent plate.
これらのアイコンシートやタッチパネルは、表示体の駆動用ＩＣや配線やＬＣＤの枠シール剤を隠し、表示エリアのみを見えるようにし、デザイン性を向上するために、遮光枠を印刷等で被覆する場合がある。この遮光枠があると、遮光枠の下の光硬化性接着剤組成物は遮光枠により光が遮られ、光が当たらずに硬化しないため、接着が不十分となる。 These icon sheets and touch panels cover the shading frame by printing, etc. in order to hide the display element drive IC, wiring, and LCD frame sealant so that only the display area is visible and to improve design. There is. When this light-shielding frame is present, the photocurable adhesive composition under the light-shielding frame is shielded from light by the light-shielding frame, and is not cured without being exposed to light, resulting in insufficient adhesion.
この未硬化による不十分な接着の問題を解決するため、光を斜めや横から照射する等して光の照射角度を調整する方法や、光硬化性接着剤組成物に熱硬化性触媒を添加し、光硬化性に加えて熱硬化性を付与し、光と熱で硬化する方法が実施されていた。 In order to solve the problem of insufficient adhesion due to uncured, a method of adjusting the light irradiation angle by irradiating light obliquely or from the side, etc., or adding a thermosetting catalyst to the photocurable adhesive composition However, a method of imparting thermosetting property in addition to photocuring property and curing with light and heat has been practiced.
しかし、光の照射角度を調整する方法では、遮光枠の幅が広くなると遮光枠の下の光硬化性接着剤組成物の全てを十分に硬化させるのが難しくなり、未硬化部分が残存しやすいという課題があった。光硬化性接着剤組成物に熱硬化性を付与し、光と熱で硬化する方法は、ＬＣＤ、ＥＬディスプレイ、ＬＥＤディスプレイ等の表示パネルを６０〜８０℃に３０〜６０分加温する必要があるため、品質の劣化や商品寿命を短くするおそれがあるという課題があった。 However, in the method of adjusting the light irradiation angle, if the width of the light shielding frame is increased, it becomes difficult to sufficiently cure all of the photocurable adhesive composition under the light shielding frame, and uncured portions are likely to remain. There was a problem. The method of imparting thermosetting to the photocurable adhesive composition and curing with light and heat requires heating display panels such as LCD, EL display, LED display, etc. to 60-80 ° C. for 30-60 minutes. For this reason, there is a problem in that there is a risk of quality deterioration and shortening of the product life.
特許文献１は、（Ａ）ポリイソプレン、ポリブタジエン又はポリウレタンを骨格にもつ（メタ）アクリレートオリゴマー、（Ｂ）柔軟化成分、並びに（Ｃ１）フェノキシエチル（メタ）アクリレート、フェノキシポリエチレングリコール（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、ノニルフェノールＥＯ付加物（メタ）アクリレート、メトキシトリエチレングリコール（メタ）アクリレート及びテトラヒドロフルフリル（メタ）アクリレートから選択した（メタ）アクリレートモノマーを含む光硬化型樹脂組成物が記載されている。 Patent Document 1 describes (A) a (meth) acrylate oligomer having a polyisoprene, polybutadiene or polyurethane as a skeleton, (B) a softening component, and (C1) phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, (Meth) selected from 2-hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, nonylphenol EO adduct (meth) acrylate, methoxytriethylene glycol (meth) acrylate and tetrahydrofurfuryl (meth) acrylate A photocurable resin composition containing an acrylate monomer is described.
近年、ＬＣＤ等の表示体のガラスが薄くなってきている。ガラスが薄くなると外部応力でＬＣＤが変形しやすくなる。薄いガラスを用いたＬＣＤ等の表示体と、アクリル板やポリカーボネート板等の光学機能材料とを、貼り合わせた場合、ガラスとアクリル等の線膨張の違いや、アクリル板やポリカーボネート等のプラスチック成型材の成型時の歪みにより、耐熱試験や耐湿試験において成型歪みの緩和や吸湿／乾燥が起こり、寸法変化や反り等の面精度変化が起きる。特許文献２は、ウレタン系（メタ）アクリレート、ポリブタジエン系（メタ）アクリレート、及びイソプレン系（メタ）アクリレートを成分とする硬化樹脂が記載されている。 In recent years, glass for display bodies such as LCDs has become thinner. When the glass becomes thinner, the LCD is easily deformed by external stress. When a display body such as LCD using thin glass and an optical functional material such as an acrylic plate or polycarbonate plate are bonded together, the difference in linear expansion between glass and acrylic or plastic molding material such as acrylic plate or polycarbonate Due to the strain at the time of molding, relaxation of molding strain and moisture absorption / drying occur in the heat resistance test and moisture resistance test, and surface accuracy changes such as dimensional change and warpage occur. Patent Document 2 describes a cured resin containing urethane (meth) acrylate, polybutadiene (meth) acrylate, and isoprene (meth) acrylate as components.
化粧板とタッチパネルとの貼り合わせ、アイコンシートとタッチパネルとの貼り合わせ、透明基板と透明板との貼り合わせ等といった用途では、使用環境を想定した加温雰囲気での被着体の変形に追随できる程度の柔軟性を有することが望ましいとされている。 In applications such as bonding of decorative plates and touch panels, bonding of icon sheets and touch panels, bonding of transparent substrates and transparent plates, etc., it is possible to follow the deformation of the adherend in a heated atmosphere assuming the use environment. It is desirable to have a degree of flexibility.
一方、使用環境を想定した加温雰囲気での被着体の変形に追随できる程度の柔軟性を有する場合、耐熱試験後の着色や変色、耐湿試験後の強度低下といった課題があることも明らかとなっている。上記課題の解決策として、特許文献４は、ポリイソプレン（メタ）アクリレートオリゴマー、ポリブタジエン（メタ）アクリレートオリゴマー及びポリウレタン（メタ）アクリレートオリゴマーからなる群から選ばれた１種以上のオリゴマーとヒンダードアミンとを含有する光硬化型接着組成物が記載されている。 On the other hand, when it is flexible enough to follow the deformation of the adherend in a heated atmosphere assuming the use environment, it is clear that there are problems such as coloring and discoloration after the heat resistance test, strength reduction after the moisture resistance test It has become. As a solution to the above problem, Patent Document 4 contains at least one oligomer selected from the group consisting of a polyisoprene (meth) acrylate oligomer, a polybutadiene (meth) acrylate oligomer, and a polyurethane (meth) acrylate oligomer, and a hindered amine. A photocurable adhesive composition is described.
特許文献５に（Ａ）特定のイオウ含有（メタ）アクリレート化合物またはこれを含むラジカル反応性組成物、（Ｂ）紫外線吸収剤、（Ｃ）酸化防止剤、及び（Ｄ）重合開始剤を含むことを特徴とする光硬化性組成物が記載されている。 Patent Document 5 contains (A) a specific sulfur-containing (meth) acrylate compound or a radical reactive composition containing the same, (B) an ultraviolet absorber, (C) an antioxidant, and (D) a polymerization initiator. A photocurable composition characterized by: is described.
特許文献６にアクリルポリマー（Ｅ）、不飽和二重結合を有する官能基を２つ以上有するウレタン（メタ）アクリレート（Ａ）、不飽和二重結合を有する官能基を１つ有するモノマー（Ｂ）、光重合開始剤（Ｃ）、チオール基を２つ以上有するポリチオール化合物（Ｄ）を含有する組成物であって、該組成物中におけるウレタン（メタ）アクリレート（Ａ）の重量割合が２重量％〜３０重量％である光硬化型透明接着剤組成物が記載されている。 Patent Document 6 discloses acrylic polymer (E), urethane (meth) acrylate (A) having two or more functional groups having an unsaturated double bond, monomer (B) having one functional group having an unsaturated double bond , A photopolymerization initiator (C), a composition containing a polythiol compound (D) having two or more thiol groups, wherein the weight ratio of urethane (meth) acrylate (A) in the composition is 2% by weight A photocurable transparent adhesive composition of ˜30% by weight is described.
特許文献７に、末端にアリル基を有するアリルエステルオリゴマーであって、その構成成分中に、１０〜８０モル％がイタコン酸から誘導された有機残基を含む脂肪族ジカルボン酸で、残部がイタコン酸以外の不飽和基を含む脂肪族および／または飽和脂肪族および／または芳香族脂肪族ジカルボン酸から誘導された有機残基と、ポリオールから誘導された有機残基を含むアリルエステルオリゴマーを熱硬化性樹脂組成物として使用することが記載されている。 Patent Document 7 discloses an allyl ester oligomer having an allyl group at a terminal, in which 10 to 80 mol% of an aliphatic dicarboxylic acid containing an organic residue derived from itaconic acid is contained, and the rest is itaconic. Thermal curing of allyl ester oligomers containing organic residues derived from aliphatic and / or saturated aliphatic and / or aromatic aliphatic dicarboxylic acids containing unsaturated groups other than acids and organic residues derived from polyols It is described that it is used as an adhesive resin composition.
しかしながら、上記文献記載の従来技術は、以下の点で改善の余地を有していた。
特許文献２の方法は、面精度変化といった変形を抑えようとした場合、接着面が剥がれたり、ＬＣＤが割れたり、ＬＣＤが表示ムラになったりするという問題があった。
特許文献２の課題の解決策として、特許文献３のＵＶ硬化型樹脂が挙げられる。しかし、特許文献３は、イソボルニル（メタ）アクリレートのような剛直な骨格モノマーをベースとした高弾性樹脂であるが故に、高温信頼性試験（耐湿熱性試験）において被着体の膨張収縮に耐えることができず、剥がれを生じてしまう。
また、いずれの文献の技術においても、例えば、タッチパネル等の表示体に使用される化粧板やアイコンシートを貼り合わせる場合、透明基板と透明基板とを貼り合わせる場合、印刷加工された部分を貼り合わせる場合に、被着体正面からでは印刷等の遮光枠により正面から可視光線若しくは紫外線が当たらない箇所を、側面からの可視光線若しくは紫外線により硬化する場合、遮光枠の下の硬化性樹脂組成物の硬化不良を起こすという課題があった。However, the prior art described in the above literature has room for improvement in the following points.
The method of Patent Document 2 has a problem that, when an attempt is made to suppress deformation such as a change in surface accuracy, the adhesive surface is peeled off, the LCD is cracked, or the LCD becomes uneven in display.
As a solution to the problem of Patent Document 2, there is a UV curable resin of Patent Document 3. However, since Patent Document 3 is a highly elastic resin based on a rigid skeleton monomer such as isobornyl (meth) acrylate, it can withstand the expansion and contraction of an adherend in a high temperature reliability test (wet heat resistance test). Can not be peeled off.
Also, in any of the techniques of any document, for example, when a decorative board or icon sheet used for a display body such as a touch panel is bonded, when a transparent substrate and a transparent substrate are bonded, a printed part is bonded. In the case where a portion that is not exposed to visible light or ultraviolet rays from the front side by a light shielding frame such as printing from the front side of the adherend is cured by visible light or ultraviolet rays from the side surface, the curable resin composition under the light shielding frame There was a problem of causing poor curing.
本発明は、上記事情に鑑みてなされたものであり、例えば、タッチパネル等の表示体に使用される化粧板やアイコンシートを貼り合わせる場合、透明基板と透明基板とを貼り合わせる場合、表示体と光学機能材料とを貼り合わせる場合に、好適に用いられる組成物を提供することを目的とする。 The present invention has been made in view of the above circumstances. For example, when a decorative plate and an icon sheet used for a display body such as a touch panel are bonded together, when a transparent substrate and a transparent substrate are bonded together, It aims at providing the composition used suitably when bonding with an optical functional material.
即ち、本発明によれば、下記（Ｐ）、（Ｃ）〜（Ｆ）を含有する組成物が提供される。
（Ｐ）重合性ビニルモノマー
（Ｃ）光重合開始剤
（Ｄ）酸化防止剤
（Ｅ）チオール
（Ｆ）ジカルボン酸ジエステルThat is, according to the present invention, a composition containing the following (P) and (C) to (F) is provided.
(P) polymerizable vinyl monomer (C) photopolymerization initiator (D) antioxidant (E) thiol (F) dicarboxylic acid diester
上記（Ｆ）が式（１）で表されるジカルボン酸ジエステルである該組成物であることが好ましい。 The composition (F) is preferably a dicarboxylic acid diester represented by the formula (1).
上記（Ｅ）チオールがポリチオールであることが好ましい。
上記（Ｐ）重合性ビニルモノマーが、（Ａ）多官能（メタ）アクリレート及び（Ｂ）単官能（メタ）アクリレートを含有する該組成物であることが好ましい。
また、上記（Ａ）多官能（メタ）アクリレートが、ウレタン（メタ）アクリレートである該組成物であることが好ましい。
上記（Ｂ）単官能（メタ）アクリレートが、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートからなる群から選ばれる１種以上を含む該組成物であることが好ましい。
上記（Ｆ）ジカルボン酸ジエステルの含有量は、（Ｐ）重合性ビニルモノマー及び（Ｆ）ジカルボン酸ジエステルの合計１００質量部とした場合に、５〜５０質量部である該組成物であることが好ましい。
また、本発明によれば、該組成物を含む硬化性樹脂組成物が提供される。
また、本発明によれば、該組成物を含む接着剤組成物が提供される。
また、本発明によれば、該接着剤組成物の硬化体が提供される。
また、本発明によれば、該硬化体により被着体が被覆又は接合された複合体が提供される。
該被着体は、トリアセチルセルロース、フッ素系ポリマー、ポリエステル、ポリカーボネート、ポリオレフィン、ガラス、金属からなる群から選ばれる１種以上を含む該複合体であることが好ましい。
また、本発明によれば、該接着剤組成物により被着体を貼り合わせたタッチパネル積層体が提供される。
また、本発明によれば、該接着剤組成物により被着体を貼り合わせた液晶パネル積層体が提供される。
また、本発明によれば、該タッチパネル積層体を用いたディスプレイが提供される。
また、本発明によれば、該液晶パネル積層体を用いたディスプレイが提供される。The (E) thiol is preferably a polythiol.
The (P) polymerizable vinyl monomer is preferably the composition containing (A) polyfunctional (meth) acrylate and (B) monofunctional (meth) acrylate.
Moreover, it is preferable that the said (A) polyfunctional (meth) acrylate is this composition which is urethane (meth) acrylate.
The (B) monofunctional (meth) acrylate is preferably a composition containing one or more selected from the group consisting of hydroxyalkyl (meth) acrylates and alkyl (meth) acrylates.
The content of the (F) dicarboxylic acid diester is 5 to 50 parts by mass when the total of (P) the polymerizable vinyl monomer and (F) dicarboxylic acid diester is 100 parts by mass. preferable.
Moreover, according to this invention, the curable resin composition containing this composition is provided.
Moreover, according to this invention, the adhesive composition containing this composition is provided.
Moreover, according to this invention, the hardening body of this adhesive composition is provided.
Moreover, according to this invention, the composite_body | complex to which the to-be-adhered body was coat | covered or joined by this hardening body is provided.
The adherend is preferably a composite containing at least one selected from the group consisting of triacetylcellulose, fluorine-based polymer, polyester, polycarbonate, polyolefin, glass, and metal.
Moreover, according to this invention, the touch-panel laminated body which bonded together the to-be-adhered body with this adhesive composition is provided.
Moreover, according to this invention, the liquid crystal panel laminated body which bonded together the to-be-adhered body with this adhesive composition is provided.
Moreover, according to this invention, the display using this touch panel laminated body is provided.
Moreover, according to this invention, the display using this liquid crystal panel laminated body is provided.
本発明によれば、深部硬化性に優れた組成物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the composition excellent in deep part sclerosis | hardenability can be provided.
以下、本発明の実施形態を詳細に説明する。
本発明の組成物は、下記（Ｐ）、（Ｃ）〜（Ｆ）を含有する。
（Ｐ）重合性ビニルモノマー
（Ｃ）光重合開始剤
（Ｄ）酸化防止剤
（Ｅ）チオール
（Ｆ）ジカルボン酸ジエステルHereinafter, embodiments of the present invention will be described in detail.
The composition of the present invention contains the following (P) and (C) to (F).
(P) polymerizable vinyl monomer (C) photopolymerization initiator (D) antioxidant (E) thiol (F) dicarboxylic acid diester
この組成によれば、例えば、タッチパネル等の表示体に使用される化粧板やアイコンシートを貼り合わせる場合、透明基板と透明基板とを貼り合わせる場合、印刷加工された部分を貼り合わせる場合に、被着体正面からでは印刷等の遮光枠により正面から可視光線若しくは紫外線が当たらない箇所を、側面からの可視光線若しくは紫外線により硬化する硬化性樹脂組成物を提供することができる。
また、この組成によれば、深部硬化性に優れた組成物を提供できるので、例えば、遮光枠の下の硬化性樹脂組成物の硬化が可能であり、接着剤の硬化不良を抑制する効果を有することができる。According to this composition, for example, when a decorative board or icon sheet used for a display body such as a touch panel is bonded, a transparent substrate and a transparent substrate are bonded, or a printed portion is bonded, It is possible to provide a curable resin composition that cures a portion that is not exposed to visible light or ultraviolet rays from the front side by visible light or ultraviolet rays from the front side due to a light shielding frame such as printing from the front side of the body.
Moreover, according to this composition, since the composition excellent in deep part sclerosis | hardenability can be provided, the hardening of the curable resin composition under a light-shielding frame is possible, for example, The effect which suppresses the hardening defect of an adhesive agent Can have.
本発明の一実施形態において組成物は、上記のように（Ｐ）、（Ｃ）〜（Ｆ）を含有しているので、イソボルニル（メタ）アクリレートのような剛直な骨格のモノマーを使用しなくても、信頼性試験に耐えることが可能である。 In one embodiment of the present invention, since the composition contains (P) and (C) to (F) as described above, a rigid skeleton monomer such as isobornyl (meth) acrylate is not used. However, it is possible to withstand the reliability test.
＜（Ｐ）重合性ビニルモノマー＞
（Ｐ）重合性ビニルモノマーとしては、（メタ）アクリレートが好ましく、（Ａ）多官能（メタ）アクリレート及び（Ｂ）単官能（メタ）アクリレートを含有することがより好ましい。<(P) Polymerizable vinyl monomer>
The (P) polymerizable vinyl monomer is preferably (meth) acrylate, and more preferably contains (A) polyfunctional (meth) acrylate and (B) monofunctional (meth) acrylate.
＜（Ａ）多官能（メタ）アクリレート＞
（Ａ）多官能（メタ）アクリレートとは、（メタ）アクリロイル基を２個以上有する（メタ）アクリレートをいう。多官能（メタ）アクリレートとしては、オリゴマー／ポリマー末端又は側鎖に２個以上（メタ）アクロイル化された多官能（メタ）アクリレートのオリゴマー／ポリマー等が挙げられる。<(A) Polyfunctional (meth) acrylate>
(A) Polyfunctional (meth) acrylate refers to (meth) acrylate having two or more (meth) acryloyl groups. Examples of the polyfunctional (meth) acrylate include oligomers / polymers of polyfunctional (meth) acrylates that are two or more (meth) acryloylated at the oligomer / polymer terminal or side chain.
例えば、多官能（メタ）アクリレートのオリゴマー／ポリマーとしては、
１，２−ポリブタジエン末端ウレタン（メタ）アクリレート（例えば、日本曹達社製「ＴＥＡ−１０００」）や、１，２−ポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物（例えば、１，２−ポリブタジエン骨格中の炭素−炭素結合に水素が付加した水素化ポリブタジエンの両末端に（メタ）アクリロイルオキシ基を有するウレタン（メタ）アクリレートをいう。例えば、日本曹達社製「ＴＥＡＩ−１０００」、ダイセル・オルネクス社製「ＫＲＭ−８７７６」、「ＫＲＭ−８７９２」）や、１，４−ポリブタジエン末端ウレタン（メタ）アクリレート（例えば、大阪有機化学社製「ＢＡＣ−４５」）や、ポリイソプレン末端（メタ）アクリレートや、ポリエステル系ウレタン（メタ）アクリート（例えば、日本合成社製「ＵＶ−２０００Ｂ」、「ＵＶ−３０００Ｂ」、「ＵＶ−７０００Ｂ」、根上工業社製「ＫＨＰ−１１」、「ＫＨＰ−１７」）や、ポリエーテル系ウレタン（メタ）アクリレート（例えば、日本合成社製「ＵＶ−３７００Ｂ」、「ＵＶ−６１００Ｂ」）や、ビスフェノールＡ型エポキシ（メタ）アクリレート等が挙げられる。
なお、ポリブタジエン末端（メタ）ウレタンアクリレートは、分子構造の末端が（メタ）アクリレートである。
上記記載した多官能（メタ）アクリレートのオリゴマー／ポリマーの中では、効果が大きい点で、ウレタン（メタ）アクリレートが好ましい。
また、ウレタン（メタ）アクリレートの中では、ポリブタジエン系ウレタン（メタ）アクリレート、ポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物、ポリエステル系ウレタン（メタ）アクリレート及びポリエーテル系ウレタン（メタ）アクリレートからなる群のうちの１種以上が好ましく、ポリブタジエン系ウレタン（メタ）アクリレート及び／又はポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物がより好ましく、ポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物が最も好ましい。
なお、ポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物の中では、１，２−ポリブタジエン末端ウレタン（メタ）アクリレートの水素添加物が好ましい。ポリブタジエン系ウレタン（メタ）アクリレートの中では、１，４−ポリブタジエン末端ウレタン（メタ）アクリレートが好ましい。 For example, as an oligomer / polymer of polyfunctional (meth) acrylate,
1,2-polybutadiene-terminated urethane (meth) acrylate (for example, “TEA-1000” manufactured by Nippon Soda Co., Ltd.) and hydrogenated products of 1,2-polybutadiene-terminated urethane (meth) acrylate (for example, 1,2-polybutadiene skeleton) This refers to urethane (meth) acrylates having (meth) acryloyloxy groups at both ends of hydrogenated polybutadiene in which hydrogen is added to the carbon-carbon bond, such as “TEAI-1000” manufactured by Nippon Soda Co., Ltd., Daicel Ornex Co., Ltd. "KRM-8776", "KRM-8792"), 1,4-polybutadiene-terminated urethane (meth) acrylate (for example, "BAC-45" manufactured by Osaka Organic Chemical Co., Ltd.), polyisoprene-terminated (meth) acrylate, , Polyester urethane (meth) acrylate (for example, “U” -2000B "," UV-3000B "," UV-7000B "," KHP-11 "," KHP-17 "manufactured by Negami Kogyo Co., Ltd.) and polyether urethane (meth) acrylate (for example," Nippon Gosei Co., Ltd. " UV-3700B "," UV-6100B "), bisphenol A type epoxy (meth) acrylate, and the like.
Polybutadiene-terminated (meth) urethane acrylate has a molecular structure whose end is (meth) acrylate.
Among the polyfunctional (meth) acrylate oligomers / polymers described above, urethane (meth) acrylate is preferred because of its great effect.
Among urethane (meth) acrylates, polybutadiene urethane (meth) acrylate, polybutadiene-terminated urethane (meth) acrylate hydrogenated product, polyester urethane (meth) acrylate and polyether urethane (meth) acrylate 1 or more of these are preferable, a hydrogenated product of polybutadiene-based urethane (meth) acrylate and / or polybutadiene-terminated urethane (meth) acrylate is more preferable, and a hydrogenated product of polybutadiene-terminated urethane (meth) acrylate is most preferable.
Of the hydrogenated products of polybutadiene-terminated urethane (meth) acrylate, hydrogenated products of 1,2-polybutadiene-terminated urethane (meth) acrylate are preferred. Among the polybutadiene-based urethane (meth) acrylates, 1,4-polybutadiene-terminated urethane (meth) acrylate is preferable.
ここで、ウレタン（メタ）アクリレートとは、ポリオール化合物（以後、Ｘで表す）と有機ポリイソシアネート化合物（以後、Ｙで表す）とヒドロキシ（メタ）アクリレート（以後、Ｚで表す）とを反応（例えば、重縮合反応）させることにより得られる、分子内にウレタン結合を有するウレタン（メタ）アクリレートをいう。 Here, the urethane (meth) acrylate is a reaction between a polyol compound (hereinafter represented by X), an organic polyisocyanate compound (hereinafter represented by Y), and a hydroxy (meth) acrylate (hereinafter represented by Z) (for example, , A urethane (meth) acrylate having a urethane bond in the molecule, obtained by a polycondensation reaction).
ポリオール化合物（Ｘ）としては、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、ポリプロピレングリコール、ブチレングリコール、１，４−ブタンジオール、ポリブチレングリコール、１，５−ペンタンジオール、１，６−ヘキサンジオール、１，８−オクタンジオール、１，９−ノナンジオール、３−メチル−１，５−ペンタンジオール、２，４−ジエチル−１，５−ペンタンジオール、２，２−ブチルエチル−１，３−プロパンジオール、ネオペンチルグリコール、シクロヘキサンジメタノール、水素化ビスフェノールＡ、ポリカプロラクトン、トリメチロールエタン、トリメチロールプロパン、ポリトリメチロールプロパン、ペンタエリスリトール、ポリペンタエリスリトール、ソルビトール、マンニトール、グリセリン、ポリグリセリン、ポリテトラメチレングリコール等の多価アルコールや、ポリエチレンオキサイド、ポリプロピレンオキサイド、エチレンオキサイド／プロピレンオキサイドのブロック又はランダム共重合の少なくとも１種の構造を有するポリエーテルポリオール、該多価アルコール又はポリエーテルポリオールと、無水マレイン酸、マレイン酸、フマル酸、無水イタコン酸、イタコン酸、アジピン酸、イソフタル酸等の多塩基酸との縮合物であるポリエステルポリオール、カプロラクトン変性ポリテトラメチレンポリオール等のカプロラクトン変性ポリオール、ポリオレフィン系ポリオール、ポリカーボネート系ポリオール、ポリブタジエンポリオール、ポリイソプレンポリオール、水素化ポリブタジエンポリオール、水素化ポリイソプレンポリオール等のポリジエン系ポリオール、ポリジメチルシロキサンポリオール等のシリコーンポリオール等が挙げられる。
これらの中では、ポリオール化合物（Ｘ）として、ポリブタジエンポリオール、水素化ポリブタジエンポリオール、ポリエーテルポリオール及びポリエステルポリオールからなる群のうちの１種以上を含むことが好ましく、水素化ポリブタジエンポリオールがより好ましい。水素化ポリブタジエンポリオールの中では、式（３）を表される化合物（ｎは正数）が好ましい。
Among these, the polyol compound (X) preferably contains one or more members selected from the group consisting of polybutadiene polyol, hydrogenated polybutadiene polyol, polyether polyol, and polyester polyol, and more preferably hydrogenated polybutadiene polyol. Among the hydrogenated polybutadiene polyols, compounds represented by the formula (3) (n is a positive number) are preferable.
ここで、ポリブタジエン系ウレタン（メタ）アクリレートは、例えば、ポリオール化合物（Ｘ）がポリブタジエンポリオールである。また、ポリエステル系ウレタン（メタ）アクリートは、例えば、ポリオール化合物（Ｘ）がポリエステルポリオールである。また、ポリエーテル系ウレタン（メタ）アクリレートは、例えば、ポリオール化合物（Ｘ）がポリエーテルポリオールである。 Here, in the polybutadiene urethane (meth) acrylate, for example, the polyol compound (X) is a polybutadiene polyol. Further, in the polyester-based urethane (meth) acrylate, for example, the polyol compound (X) is a polyester polyol. Moreover, as for polyether-type urethane (meth) acrylate, polyol compound (X) is a polyether polyol, for example.
有機ポリイソシアネート化合物（Ｙ）としては、格別に限定される必要はないが、例えば芳香族系、脂肪族系、環式脂肪族系、脂環式系等のポリイソシアネートが使用できる。
ポリイソシアネートの中でも、トリレンジイソシアネート（ＴＤＩ）、ジフェニルメタンジイソシアネート（ＭＤＩ）、水添化ジフェニルメタンジイソシアネート（Ｈ−ＭＤＩ）、ポリフェニルメタンポリイソシアネート（クルードＭＤＩ）、変性ジフェニルメタンジイソシアネート（変性ＭＤＩ）、水添化キシリレンジイソシアネート（Ｈ−ＸＤＩ）、キシリレンジイソシアネート（ＸＤＩ）、ヘキサメチレンジイソシアネート（ＨＭＤＩ）、トリメチルヘキサメチレンジイソシアネート（ＴＭＸＤＩ）、テトラメチルキシリレンジイソシアネート（ｍ−ＴＭＸＤＩ）、イソホロンジイソシアネート（ＩＰＤＩ）、ノルボルネンジイソシアネート（ＮＢＤＩ）、１，３−ビス（イソシアナトメチル）シクロヘキサン（Ｈ６ＸＤＩ）等のポリイソシアネートや、これらポリイソシアネートの三量体化合物や、これらポリイソシアネートとポリオールの反応生成物等が好適に用いられる。
以上の中で、有機ポリイソシアネート化合物（Ｙ）としては、水添化キシリレンジイソシアネート（Ｈ−ＸＤＩ）及び／又はイソホロンジイソシアネート（ＩＰＤＩ）が好ましく、イソホロンジイソシアネート（ＩＰＤＩ）がより好ましい。The organic polyisocyanate compound (Y) is not particularly limited, but for example, aromatic, aliphatic, cycloaliphatic, and alicyclic polyisocyanates can be used.
Among polyisocyanates, tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hydrogenated diphenylmethane diisocyanate (H-MDI), polyphenylmethane polyisocyanate (crude MDI), modified diphenylmethane diisocyanate (modified MDI), hydrogenated Xylylene diisocyanate (H-XDI), xylylene diisocyanate (XDI), hexamethylene diisocyanate (HMDI), trimethylhexamethylene diisocyanate (TMXDI), tetramethylxylylene diisocyanate (m-TMXDI), isophorone diisocyanate (IPDI), norbornene diisocyanate (NBDI), 1,3-bis (isocyanatomethyl) cyclohexane (H6XDI) and other poly Isocyanate and, or trimer compounds of these polyisocyanates, reaction products of these polyisocyanates with polyols are preferably used.
Among these, as the organic polyisocyanate compound (Y), hydrogenated xylylene diisocyanate (H-XDI) and / or isophorone diisocyanate (IPDI) is preferable, and isophorone diisocyanate (IPDI) is more preferable.
ヒドロキシ（メタ）アクリレート（Ｚ）としては、例えば、２−ヒドロキシエチル（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−ヒドロキシブチル（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリロイルホスフェート、４−ヒドロキシブチル（メタ）アクリレート、２−（メタ）アクリロイロキシエチル−２−ヒドロキシプロピルフタレート、グリセリンジ（メタ）アクリレート、２−ヒドロキシ−３−（メタ）アクリロイロキシプロピルアクリレート、カプロラクトン変性２−ヒドロキシエチル（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、ジペンタエリスリトールペンタ（メタ）アクリレート、カプロラクトン変性２−ヒドロキシエチル（メタ）アクリレート等が挙げられる。
これらの中で、ヒドロキシ（メタ）アクリレート（Ｚ）としては、ヒドロキシアルキル（メタ）アクリレートが好ましい。ヒドロキシアルキル（メタ）アクリレートの中では、２−ヒドロキシエチル（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−ヒドロキシブチル（メタ）アクリレートからなる群のうちの１種以上を含むことが好ましい。Examples of the hydroxy (meth) acrylate (Z) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxyethyl (meth) acryloyl phosphate, 4-hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycerin di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl acrylate, caprolactone modified 2 -Hydroxyethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone modified 2-hydroxyethyl (meth) acrylate, etc. It is below.
Among these, as hydroxy (meth) acrylate (Z), hydroxyalkyl (meth) acrylate is preferable. Among the hydroxyalkyl (meth) acrylates, it is preferable to include one or more members selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl (meth) acrylate. .
多官能（メタ）アクリレートの重量平均分子量は、特に限定しないが１０００〜６００００が好ましく、１５００〜４００００がより好ましい。重量平均分子量は、下記の条件にて、溶剤としてテトラヒドロフランを用い、ＧＰＣシステム（東ソ−社製ＳＣ−８０１０）等を使用し、市販の標準ポリスチレンで検量線を作成して求めた。 Although the weight average molecular weight of polyfunctional (meth) acrylate is not specifically limited, 1000-60000 are preferable and 1500-40000 are more preferable. The weight average molecular weight was determined by preparing a calibration curve with commercially available standard polystyrene using the GPC system (SC-8010, manufactured by Tosoh Corporation) using tetrahydrofuran as a solvent under the following conditions.
流速：１．０ｍｌ／ｍｉｎ
設定温度：４０℃
カラム構成：東ソー社製「ＴＳＫ ｇｕａｒｄｃｏｌｕｍｎ ＭＰ（×Ｌ）」６．０ｍｍＩＤ×４．０ｃｍ１本、及び東ソー社製「ＴＳＫ−ＧＥＬＭＵＬＴＩＰＯＲＥＨＸＬ−Ｍ」７．８ｍｍＩＤ×３０．０ｃｍ（理論段数１６，０００段）２本、計３本（全体として理論段数３２，０００段）、
サンプル注入量：１００μｌ（試料液濃度１ｍｇ／ｍｌ）
送液圧力：３９ｋｇ／ｃｍ２
検出器：ＲＩ検出器Flow rate: 1.0 ml / min
Set temperature: 40 ° C
Column configuration: “TSK guardcolumn MP (× L)” manufactured by Tosoh Corp. 6.0 mm ID × 4.0 cm 1 and “TSK-GELMULTIPOREHXL-M” 7.8 mm ID × 30.0 cm (16,000 theoretical plates) manufactured by Tosoh Corp. 2, 3 in total (32,000 theoretical plates as a whole)
Sample injection volume: 100 μl (sample solution concentration 1 mg / ml)
Liquid feeding pressure: 39 kg / cm 2
Detector: RI detector
＜（Ｂ）単官能（メタ）アクリレート＞
（Ｂ）単官能（メタ）アクリレートとは、（メタ）アクリロイル基を１個有する（メタ）アクリレートをいう。（Ｂ）単官能（メタ）アクリレートの中では、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートからなる群のうちの１種以上が好ましく、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートを併用することがより好ましい。
なお、本発明の一実施形態において、例えば、イソボルニル（メタ）アクリレートのような剛直な骨格のモノマーを使用しなくてもよい。なぜならば、本発明の一実施形態は、例えば、イソボルニル（メタ）アクリレートを使用しなくとも、耐湿性試験において良好な結果を示すことができる。<(B) Monofunctional (meth) acrylate>
(B) Monofunctional (meth) acrylate refers to (meth) acrylate having one (meth) acryloyl group. (B) Among monofunctional (meth) acrylates, one or more members selected from the group consisting of hydroxyalkyl (meth) acrylates and alkyl (meth) acrylates are preferred, and hydroxyalkyl (meth) acrylates and alkyl (meth) acrylates are preferred. It is more preferable to use together.
In one embodiment of the present invention, for example, a monomer having a rigid skeleton such as isobornyl (meth) acrylate may not be used. This is because one embodiment of the present invention can show good results in a moisture resistance test without using, for example, isobornyl (meth) acrylate.
ヒドロキシアルキル（メタ）アクリレートの中では、式（２）で表される（メタ）アクリレートが好ましい。
式（２）
Ｚ−Ｏ−（Ｒ１−Ｏ−）ｐ−Ｈ
（Ｚは（メタ）アクリロイル基、Ｒ１はアルキレン基、ｐは１〜１０の整数を表す。）
また、式（２）におけるＲ１のアルキレン基の炭素数は１〜８が好ましく、２〜６がより好ましい。Among the hydroxyalkyl (meth) acrylates, (meth) acrylate represented by the formula (2) is preferable.
Formula (2)
Z—O— (R 1 —O—) p —H
(Z represents a (meth) acryloyl group, R 1 represents an alkylene group, and p represents an integer of 1 to 10)
The number of carbon atoms of the alkylene group R 1 in the formula (2) is preferably 1-8, 2-6 is more preferable.
ヒドロキシアルキル（メタ）アクリレートとしては、２−ヒドロキシエチル（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−ヒドロキシブチル（メタ）アクリレート、ジエチレングリコールモノ（メタ）アクリレート及びポリプロピレングリコール（メタ）アクリレート等が挙げられる。これらの中では、接着性や耐湿性の点で、２−ヒドロキシブチル（メタ）アクリレートが好ましい。 As hydroxyalkyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, diethylene glycol mono (meth) acrylate, polypropylene glycol (meth) acrylate, etc. Is mentioned. In these, 2-hydroxybutyl (meth) acrylate is preferable at the point of adhesiveness or moisture resistance.
アルキル（メタ）アクリレートの中では、（メタ）アクリル酸アルキルエステルが好ましい。アルキルエステル中、アルキル基の炭素数は、１〜１６が好ましく、炭素数２〜１４がより好ましく、炭素数４〜１２が最も好ましく、炭素数６〜１０が尚更好ましい。アルキル基は、飽和脂肪族炭化水素基が好ましい。また、アルキル基は、非置換であることが好ましい。
アルキル（メタ）アクリレートとしては、メチル（メタ）アクリレート、エチル（メタ）アクリレート、プロピル（メタ）アクリレート、ブチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ノルマルオクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、デシル（メタ）アクリレート、イソデシル（メタ）アクリレート、ラウリル（メタ）アクリレート、ステアリル（メタ）アクリレート、イソステアリル（メタ）アクリレート等が挙げられる。これらの中では、接着性や耐湿性の点で、オクチル（メタ）アクリレートが好ましく、ノルマルオクチル（メタ）アクリレートがより好ましい。Among alkyl (meth) acrylates, (meth) acrylic acid alkyl esters are preferred. In the alkyl ester, the alkyl group preferably has 1 to 16 carbon atoms, more preferably 2 to 14 carbon atoms, most preferably 4 to 12 carbon atoms, and still more preferably 6 to 10 carbon atoms. The alkyl group is preferably a saturated aliphatic hydrocarbon group. The alkyl group is preferably unsubstituted.
Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, normal octyl (meth) acrylate, and isooctyl (meth) ) Acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, and the like. Among these, octyl (meth) acrylate is preferable and normal octyl (meth) acrylate is more preferable in terms of adhesiveness and moisture resistance.
（Ｐ）重合性ビニルモノマーの含有量は、（Ｐ）及び（Ｆ）の合計量を１００質量部とした場合に、５０〜９５質量部が好ましく、５５〜９０質量部がより好ましく、６０〜８０質量部が最も好ましい。（Ｐ）重合性ビニルモノマーの含有量が５０質量部以上であれば、より良好な硬化性が得られ、９５質量部以下であれば、より接着性の低下を抑制することができる。なお、（Ｐ）重合性ビニルモノマーの含有量は、例えば、50、51、54、55、56、59、60、61、65、69、70、71、75、79、80、81、85、89、90、91、94または、95質量部でもあってもよく、それらいずれか2つの値の範囲内であっても良い。 (P) As for content of a polymerizable vinyl monomer, when the total amount of (P) and (F) is 100 mass parts, 50-95 mass parts is preferable, 55-90 mass parts is more preferable, 60- 80 parts by weight is most preferred. (P) If the content of the polymerizable vinyl monomer is 50 parts by mass or more, better curability can be obtained, and if it is 95 parts by mass or less, a decrease in adhesiveness can be further suppressed. The content of the polymerizable vinyl monomer (P) is, for example, 50, 51, 54, 55, 56, 59, 60, 61, 65, 69, 70, 71, 75, 79, 80, 81, 85, It may be 89, 90, 91, 94, or 95 parts by mass, and may be in the range of any two of them.
（Ｐ）重合性ビニルモノマーが、（Ａ）多官能（メタ）アクリレート及び（Ｂ）単官能（メタ）アクリレートを含有する場合、（Ａ）多官能（メタ）アクリレート及び（Ｂ）単官能（メタ）アクリレートの含有量は、（Ａ）多官能（メタ）アクリレート及び（Ｂ）単官能（メタ）アクリレートの合計１００質量部中、質量比で、（Ａ）：（Ｂ）＝３０〜９５：５〜７０が好ましく、４０〜９０：１０〜６０がより好ましく、５０〜７０：３０〜５０が最も好ましい。 When (P) the polymerizable vinyl monomer contains (A) polyfunctional (meth) acrylate and (B) monofunctional (meth) acrylate, (A) polyfunctional (meth) acrylate and (B) monofunctional (meta ) Acrylate content is (A) :( B) = 30 to 95: 5 in a mass ratio in a total of 100 parts by mass of (A) polyfunctional (meth) acrylate and (B) monofunctional (meth) acrylate. -70 are preferable, 40-90: 10-60 are more preferable, and 50-70: 30-50 are the most preferable.
（Ｂ）単官能（メタ）アクリレートが、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートを併用する場合、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートの含有量は、ヒドロキシアルキル（メタ）アクリレートとアルキル（メタ）アクリレートの合計１００質量部中、質量比で、ヒドロキシアルキル（メタ）アクリレート：アルキル（メタ）アクリレート＝５〜７０：３０〜９５が好ましく、１０〜５０：５０〜９０がより好ましく、２０〜４０：６０〜８０が最も好ましい。 (B) When monofunctional (meth) acrylate uses hydroxyalkyl (meth) acrylate and alkyl (meth) acrylate together, the content of hydroxyalkyl (meth) acrylate and alkyl (meth) acrylate is hydroxyalkyl (meth) In total 100 parts by mass of acrylate and alkyl (meth) acrylate, the mass ratio is preferably hydroxyalkyl (meth) acrylate: alkyl (meth) acrylate = 5-70: 30-95, more preferably 10-50: 50-90. Preferably, 20-40: 60-80 is the most preferable.
＜（Ｃ）光重合開始剤＞
（Ｃ）光重合開始剤は、可視光線や紫外線の活性光線により増感させて樹脂組成物の光硬化を促進するために使用するものである。
光重合開始剤としては、ベンゾフェノン及びその誘導体、ベンジル及びその誘導体、アントラキノン及びその誘導体、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン誘導体、ベンジルジメチルケタール、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−２−メチル−１−フェニル−プロパン−１−オン等のアルキルフェノン誘導体、ジエトキシアセトフェノン、４−ｔ−ブチルトリクロロアセトフェノン等のアセトフェノン誘導体、２−ジメチルアミノエチルベンゾエート、ｐ−ジメチルアミノエチルベンゾエート、ジフェニルジスルフィド、チオキサントン及びその誘導体、カンファーキノン、７，７−ジメチル−２，３−ジオキソビシクロ［２．２．１］ヘプタン−１−カルボン酸、７，７−ジメチル−２，３−ジオキソビシクロ［２．２．１］ヘプタン−１−カルボキシ−２−ブロモエチルエステル、７，７−ジメチル−２，３−ジオキソビシクロ［２．２．１］ヘプタン−１−カルボキシ−２−メチルエステル、７，７−ジメチル−２，３−ジオキソビシクロ［２．２．１］ヘプタン−１−カルボン酸クロライド等のカンファーキノン誘導体、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ン−１−オン、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−アミノアルキルフェノン誘導体、ベンゾイルジフェニルホスフィンオキサイド、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイド、ベンゾイルジエトキシポスフィンオキサイド、２，４，６−トリメチルベンゾイルジメトキシフェニルホスフィンオキサイド、２，４，６−トリメチルベンゾイルジエトキシフェニルホスフィンオキサイド、ビス（２，４，６−トリメチルベンゾイル）−フェニルホスフィンオキサイド等のアシルホスフィンオキサイド誘導体、オキシ−フェニル−アセチックアシッド２−［２−オキソ−２−フェニル−アセトキシ−エトキシ］−エチルエステル及びオキシ−フェニル−アセチックアシッド２−［２−ヒドロキシ−エトキシ］−エチルエステル等が挙げられる。（Ｃ）光重合開始剤は、１種又は２種以上を組み合わせて用いることができる。上記の中では、効果が大きい点で、（Ｃ）光重合開始剤は、アルキルフェノン誘導体とアシルホスフィンオキサイド誘導体からなる群のうちから選ばれる１種以上を含むことが好ましく、アルキルフェノン誘導体とアシルホスフィンオキサイド誘導体を併用することがより好ましい。
アルキルフェノン誘導体とアシルホスフィンオキサイド誘導体を併用した場合、その併用割合は、アシルホスフィンオキサイド誘導体１００質量部に対して、アルキルフェノン誘導体５０〜４００質量部が好ましく、１００〜３００質量部がより好ましく、１５０〜２５０質量部が最も好ましい。
アルキルフェノン誘導体の中では、ベンジルジメチルケタールと１−ヒドロキシシクロヘキシルフェニルケトンからなる群のうちから選ばれる１種以上を含むことが好ましい。また、アシルホスフィンオキサイド誘導体の中では、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイドとビス（２，４，６−トリメチルベンゾイル）−フェニルホスフィンオキサイドからなる群のうちから選ばれる１種以上を含むことが好ましい。<(C) Photopolymerization initiator>
(C) The photopolymerization initiator is used for sensitization with visible light or ultraviolet actinic light to promote photocuring of the resin composition.
Examples of the photopolymerization initiator include benzophenone and derivatives thereof, benzyl and derivatives thereof, anthraquinone and derivatives thereof, benzoin derivatives such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether, benzyl dimethyl ketal, 1- Alkylphenone derivatives such as hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, acetophenone derivatives such as diethoxyacetophenone and 4-t-butyltrichloroacetophenone, 2-dimethylaminoethylbenzoate P-dimethylaminoethyl benzoate, diphenyl disulfide, thioxanthone and its derivatives, camphorquinone, 7,7-dimethyl-2, -Dioxobicyclo [2.2.1] heptane-1-carboxylic acid, 7,7-dimethyl-2,3-dioxobicyclo [2.2.1] heptane-1-carboxy-2-bromoethyl ester, 7,7-dimethyl-2,3-dioxobicyclo [2.2.1] heptane-1-carboxy-2-methyl ester, 7,7-dimethyl-2,3-dioxobicyclo [2.2.1 ] Camphorquinone derivatives such as heptane-1-carboxylic acid chloride, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- Α-aminoalkylphenone derivatives such as (4-morpholinophenyl) -butanone-1, benzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiph Phenylphosphine oxide, benzoyldiethoxyphosphine oxide, 2,4,6-trimethylbenzoyldimethoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyldiethoxyphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl)- Acylphosphine oxide derivatives such as phenylphosphine oxide, oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester and oxy-phenyl-acetic acid 2- [2-hydroxy- Ethoxy] -ethyl ester and the like. (C) A photoinitiator can be used 1 type or in combination of 2 or more types. Among the above, (C) the photopolymerization initiator preferably contains at least one selected from the group consisting of an alkylphenone derivative and an acylphosphine oxide derivative. It is more preferable to use a phosphine oxide derivative in combination.
When the alkylphenone derivative and the acylphosphine oxide derivative are used in combination, the combination ratio is preferably 50 to 400 parts by weight, more preferably 100 to 300 parts by weight, with respect to 100 parts by weight of the acylphosphine oxide derivative. -250 parts by weight is most preferred.
Among the alkylphenone derivatives, it is preferable to include one or more selected from the group consisting of benzyldimethyl ketal and 1-hydroxycyclohexyl phenyl ketone. The acylphosphine oxide derivative includes one or more selected from the group consisting of 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide. It is preferable.
（Ｃ）光重合開始剤の含有量は、（Ｐ）及び（Ｆ）の合計量を１００質量部とした場合に、０．０１〜１０質量部が好ましく、０．０５〜５質量部がより好ましく、０．１〜１質量部が最も好ましい。光重合開始剤の含有量が、０．０１質量部以上であれば、より良好な硬化性が得られ、１０質量部以下であればより良好な深部硬化性が得られる。なお、（Ｃ）光重合開始剤は、例えば、0.01、0.02、0.03、0.04、0.05、0.06、0.09、1、1.01、1.5、1.9、2、3、4、4.5、4.9、5、6、7、8、9または、10質量部でもあってもよく、それらいずれか2つの値の範囲内であっても良い。 (C) As for content of a photoinitiator, when the total amount of (P) and (F) is 100 mass parts, 0.01-10 mass parts is preferable, and 0.05-5 mass parts is more. Preferably, 0.1-1 mass part is the most preferable. If the content of the photopolymerization initiator is 0.01 parts by mass or more, better curability is obtained, and if it is 10 parts by mass or less, better deep part curability is obtained. The (C) photopolymerization initiator is, for example, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.09, 1, 1.01, 1.5, 1.9, 2, 3, 4, 4.5, 4.9, 5, 6, 7 8, 9 or 10 parts by mass, or any of these two values.
＜（Ｄ）酸化防止剤＞
（Ｄ）酸化防止剤は、貯蔵安定性について向上することができる。
酸化防止剤としては、メチルハイドロキノン、ハイドロキノン、２，２−メチレン−ビス（４−メチル−６−ターシャリーブチルフェノール）、６−ｔｅｒｔ−ブチル−４−［３−［（２，４，８，１０−テトラ−ｔｅｒｔ−ブチルジベンゾ［ｄ，ｆ］［１，３，２］ジオキサホスフェピン−６−イル）オキシ］プロピル］−２−メチルフェノール、カテコール、ハイドロキノンモノメチルエーテル、モノターシャリーブチルハイドロキノン、２，５−ジターシャリーブチルハイドロキノン、ｐ−ベンゾキノン、２，５−ジフェニル−ｐ−ベンゾキノン、２，５−ジターシャリーブチル−ｐ−ベンゾキノン、ピクリン酸、クエン酸、フェノチアジン、ターシャリーブチルカテコール、２−ブチル−４−ヒドロキシアニソール及び２，６−ジターシャリーブチル−ｐ−クレゾール等が挙げられる。<(D) Antioxidant>
(D) Antioxidants can improve storage stability.
Antioxidants include methylhydroquinone, hydroquinone, 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol), 6-tert-butyl-4- [3-[(2,4,8,10 -Tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphin-6-yl) oxy] propyl] -2-methylphenol, catechol, hydroquinone monomethyl ether, monotertiary butyl hydroquinone 2,5-ditertiary butyl hydroquinone, p-benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-ditertiary butyl-p-benzoquinone, picric acid, citric acid, phenothiazine, tertiary butyl catechol, 2 -Butyl-4-hydroxyanisole and 2,6-dita Tertiary butyl -p- cresol.
（Ｄ）酸化防止剤の含有量は、（Ｐ）及び（Ｆ）の合計量を１００質量部とした場合に、０．００１〜０．５質量部が好ましく、０．００５〜０．１質量部がより好ましい。酸化防止剤の含有量が、０．００１質量部以上であればより硬化性樹脂組成物の熱による着色や変色が小さく、０．５質量部以下であればより良好な深部硬化性が得られる。なお、（Ｄ）酸化防止剤は、例えば、0.001、0.002、0.003、0.004、0.005、0.006、0.009、0.010、0.011、 0.04、0.05、0.06、0.07、0.08、0.09、0.10、0.20、0.30、0.40、0.45、0.49または、0.5質量部でもあってもよく、それらいずれか2つの値の範囲内であっても良い。 (D) As for content of antioxidant, 0.001-0.5 mass part is preferable when the total amount of (P) and (F) is 100 mass parts, 0.005-0.1 mass Part is more preferred. If the content of the antioxidant is 0.001 part by mass or more, coloring and discoloration due to heat of the curable resin composition is smaller, and if it is 0.5 part by mass or less, better deep curability is obtained. . In addition, (D) antioxidant is, for example, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.009, 0.010, 0.011, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.10, 0.20, 0.30, 0.40, It may be 0.45, 0.49, or 0.5 parts by mass, and may be in the range of any two of them.
＜（Ｅ）チオール＞
（Ｅ）チオールとは、１個以上のチオール基を有する化合物をいう。チオールの中では、深部硬化性の点で、ポリチオールが好ましい。（Ｅ）ポリチオールとは、２個以上のチオール基を有する化合物をいう。ポリチオールとしては、ペンタエリスリトールテトラキス（３−メルカプトブチレート）、ペンタエリスリトールテトラキス（３−メルカプトプロピオネート）、トリメチロールプロパントリス（３−メルカプトプロピオネート）、トリメチロールプロパントリスチオプロピオネート、ペンタエリスリトールテトラキスチオプロピオネート、ジペンタエリスリトールヘキサキス（３−メルカプトプロピオネート）、トリス［（３−メルカプトプロピオニロキシ）−エチル］イソシアヌレート、３−メルカプトブチレート誘導体等が挙げられる。これらのポリチオールは、１種以上を使用できる。<(E) Thiol>
(E) Thiol refers to a compound having one or more thiol groups. Among thiols, polythiol is preferable in terms of deep curability. (E) Polythiol means a compound having two or more thiol groups. Examples of polythiols include pentaerythritol tetrakis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), trimethylolpropane tristhiopropionate, penta Examples include erythritol tetrakisthiopropionate, dipentaerythritol hexakis (3-mercaptopropionate), tris [(3-mercaptopropionyloxy) -ethyl] isocyanurate, and 3-mercaptobutyrate derivatives. One or more of these polythiols can be used.
ポリチオールの中では、３−メルカプトブチレート誘導体が好ましい。３−メルカプトブチレート誘導体としては、１，４−ビス（３−メルカプトブチリルオキシ）ブタン、１，３，５−トリス（３−メルカブトブチルオキシエチル）−１，３，５−トリアジン−２，４，６−（１Ｈ，３Ｈ，５Ｈ）−トリオン、ペンタエリスリトールテトラキス（３−メルカプトブチレート）等が挙げられる。ポリチオールの中では、２級のポリチオールが好ましい。 Of the polythiols, 3-mercaptobutyrate derivatives are preferred. Examples of 3-mercaptobutyrate derivatives include 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2 , 4,6- (1H, 3H, 5H) -trione, pentaerythritol tetrakis (3-mercaptobutyrate), and the like. Of the polythiols, secondary polythiols are preferred.
（Ｅ）チオールの含有量は、（Ｐ）及び（Ｆ）の合計量を１００質量部とした場合０．１〜１０質量部が好ましく、０．５〜５質量部がより好ましい。（Ｅ）チオールの含有量が、（Ｐ）及び（Ｆ）の合計１００質量部に対して、０．１質量部以上であればより良好な深部硬化性が得られ、１０質量部以下であれば硬化性樹脂組成物の熱による着色や変色がより小さくなる。なお、（Ｅ）チオールは、例えば、0.1、0.2、0.3、0.4、0.5、0.6、0.9、1.0、2.0、3.0、4.0、4.5、4.9、5.0、6.0、7.0、8.0、9.0、9.9または、10質量部でもあってもよく、それらいずれか2つの値の範囲内であっても良い。 (E) As for content of thiol, 0.1-10 mass parts is preferable when the total amount of (P) and (F) is 100 mass parts, and 0.5-5 mass parts is more preferable. If the content of (E) thiol is 0.1 parts by mass or more with respect to 100 parts by mass in total of (P) and (F), better deep-part curability can be obtained, and 10 parts by mass or less. For example, coloring and discoloration of the curable resin composition due to heat are further reduced. In addition, (E) thiol is, for example, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.9, 1.0, 2.0, 3.0, 4.0, 4.5, 4.9, 5.0, 6.0, 7.0, 8.0, 9.0, 9.9, or 10 It may be a mass part, and may be in the range of any two of them.
＜（Ｆ）ジカルボン酸ジエステル＞
（Ｆ）ジカルボン酸ジエステルとしては、脂肪族二塩基酸ジエステルが好ましい。脂肪族二塩基酸ジエステルとしては、式（１）で表される化合物が好ましい。<(F) Dicarboxylic acid diester>
(F) As a dicarboxylic acid diester, an aliphatic dibasic acid diester is preferable. As the aliphatic dibasic acid diester, a compound represented by the formula (1) is preferable.
式（１）で表される化合物のＲ１、Ｒ２は、飽和脂肪族炭化水素基が好ましい。また、上記Ｒ１、Ｒ２は、非置換であることが好ましい。上記Ｒ１、Ｒ２は、炭素数２〜１２のアルキル基が好ましく、炭素数４〜１０のアルキル基がより好ましく、炭素数８のアルキル基が最も好ましい。式（１）で表される化合物のＲ３は、飽和脂肪族炭化水素基が好ましい。また上記Ｒ３は、非置換であることが好ましい。上記Ｒ３は、炭素数４〜１０のアルキレン基が好ましく、炭素数７〜８のアルキレン基がより好ましく、炭素数８のアルキレン基が最も好ましい。
（Ｆ）ジカルボン酸ジエステルは、例えば、深部硬化性を良好にし、粘度を調整するために使用される化合物である。（Ｆ）化学式（１）で表されるジカルボン酸ジエステルとして、シュウ酸ジメチル、シュウ酸ジエチル、シュウ酸ジプロピル、シュウ酸ジイソプロピル、シュウ酸ジブチル、シュウ酸ジヘキシル、シュウ酸ジオクチル、マロン酸ジイソプロピル、マロン酸ジブチル、コハク酸ジエチル、コハク酸ジプロピル、コハク酸ジイソプロピル、コハク酸ジブチル、コハク酸ジｔ−ブチル、コハク酸ビス（２−エチルヘキシル）、コハク酸ビス（２−エトキシエチル）、グルタル酸ジエチル、グルタル酸ジブチル、アジピン酸ジメチル、アジピン酸ジエチル、アジピン酸ジプロピル、アジピン酸ジイソプロピル、アジピン酸ジブチル、アジピン酸ジｔ−ブチル、アジピン酸ビス（２−エチルヘキシル）、アジピン酸ジオクチル、ピメリン酸ジメチル、ピメリン酸ジエチル、ピメリン酸ジイソプロピル、ピメリン酸ジブチル、スベリン酸ジメチル、スベリン酸ジエチル、スベリン酸ジプロピル、スベリン酸ジイソプロピル、アゼライン酸ジメチル、アゼライン酸ジエチル、アゼライン酸ジプロピル、アゼライン酸ジイソプロピル、アゼライン酸ジブチル、アゼライン酸ビス（２−エチルヘキシル）、セバシン酸ジメチル、セバシン酸ジエチル、セバシン酸ジプロピル、セバシン酸ジイソプロピル、セバシン酸ジブチル、セバシン酸ビス（２−エチルヘキシル）等が挙げられる。これらのジカルボン酸ジエステルは１種以上を使用できる。（Ｆ）ジカルボン酸ジエステルの中では、セバシン酸ビス（２−エチルヘキシル）が最も好ましい。R 1 and R 2 of the compound represented by the formula (1) are preferably saturated aliphatic hydrocarbon groups. The R 1 and R 2 are preferably unsubstituted. R 1 and R 2 are preferably an alkyl group having 2 to 12 carbon atoms, more preferably an alkyl group having 4 to 10 carbon atoms, and most preferably an alkyl group having 8 carbon atoms. R 3 of the compound represented by the formula (1) is preferably a saturated aliphatic hydrocarbon group. R 3 is preferably unsubstituted. R 3 is preferably an alkylene group having 4 to 10 carbon atoms, more preferably an alkylene group having 7 to 8 carbon atoms, and most preferably an alkylene group having 8 carbon atoms.
(F) Dicarboxylic acid diester is a compound used, for example, to improve the deep-part curability and adjust the viscosity. (F) Dicarboxylic acid diester represented by chemical formula (1) is dimethyl oxalate, diethyl oxalate, dipropyl oxalate, diisopropyl oxalate, dibutyl oxalate, dihexyl oxalate, dioctyl oxalate, diisopropyl malonate, malonic acid Dibutyl, diethyl succinate, dipropyl succinate, diisopropyl succinate, dibutyl succinate, di-t-butyl succinate, bis (2-ethylhexyl) succinate, bis (2-ethoxyethyl) succinate, diethyl glutarate, glutaric acid Dibutyl, dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, dibutyl adipate, di-t-butyl adipate, bis (2-ethylhexyl) adipate, dioctyl adipate, dimethyl pimelate, pi Diethyl phosphate, diisopropyl pimelate, dibutyl pimelate, dimethyl suberate, diethyl suberate, dipropyl suberate, diisopropyl azelate, dimethyl azelate, diethyl azelate, dipropyl azelate, diisopropyl azelate, dibutyl azelate, azelaic acid Examples thereof include bis (2-ethylhexyl), dimethyl sebacate, diethyl sebacate, dipropyl sebacate, diisopropyl sebacate, dibutyl sebacate, bis (2-ethylhexyl) sebacate and the like. One or more of these dicarboxylic acid diesters can be used. Among (F) dicarboxylic acid diesters, bis (2-ethylhexyl) sebacate is most preferred.
（Ｆ）ジカルボン酸ジエステルの含有量は、（Ｐ）及び（Ｆ）の合計量を１００質量部とした場合に、５〜５０質量部が好ましく、１０〜４５質量部がより好ましく、２０〜４０質量部が最も好ましい。（Ｆ）ジカルボン酸ジエステルの含有量は、５質量部以上であればより良好な粘度と深部硬化性が得られ、５０質量部以下であればより良好な深部硬化性が得られる。なお、（Ｆ）ジカルボン酸ジエステルの含有量は、例えば、5、6、7、8、9、10、11、15、20、21、25、29、30、31、35、39、40、41、49または、50質量部でもあってもよく、それらいずれか2つの値の範囲内であっても良い。 The content of (F) dicarboxylic acid diester is preferably 5 to 50 parts by mass, more preferably 10 to 45 parts by mass, when the total amount of (P) and (F) is 100 parts by mass. Part by mass is most preferred. If the content of (F) dicarboxylic acid diester is 5 parts by mass or more, better viscosity and deep part curability are obtained, and if it is 50 parts by mass or less, better deep part curability is obtained. The content of (F) dicarboxylic acid diester is, for example, 5, 6, 7, 8, 9, 10, 11, 15, 20, 21, 25, 29, 30, 31, 35, 39, 40, 41. 49 or 50 parts by mass, or any of these two values.
本発明の一実施形態の組成物は、本発明の目的を損なわない範囲で、一般に使用されているアクリルゴム、ウレタンゴム、アクリロニトリル−ブタジエン−スチレンゴム等の各種エラストマー、極性有機溶媒等の溶剤、増量材、補強材、可塑剤、増粘剤、染料、顔料、難燃剤、シランカップリング剤及び界面活性剤等の添加剤を使用してもよい。 The composition of an embodiment of the present invention is a range of commonly used acrylic rubbers, urethane rubbers, various elastomers such as acrylonitrile-butadiene-styrene rubber, solvents such as polar organic solvents, etc., as long as the object of the present invention is not impaired. Additives such as fillers, reinforcing materials, plasticizers, thickeners, dyes, pigments, flame retardants, silane coupling agents and surfactants may be used.
本発明の一実施形態の組成物にて接着した硬化体は、完全硬化させた後にリワーク（再利用）することが可能である。リワークの方法としては特に制限は無いが、貼り合わされた１種又は２種の被着体間に０．０１〜１００Ｎの荷重を負荷することにより被着体同士を解体し、解体後の被着体を再利用することが可能となる。 The hardened body bonded with the composition of one embodiment of the present invention can be reworked (reused) after being completely cured. The rework method is not particularly limited, but the adherends are disassembled by applying a load of 0.01 to 100 N between the bonded one or two adherends, and the adherend after disassembly is performed. The body can be reused.
本発明の一実施形態の組成物は、例えば、硬化性樹脂組成物であり、また、接着剤組成物として使用できる。本発明の一実施形態の組成物は、例えば、可視光線若しくは紫外線を波長３６５ｎｍにおいて１００ｍＪ／ｃｍ２照射された際に、３ｍｍより大きく、好ましくは４ｍｍ以上の深部硬化が可能な組成物である。本発明の一実施形態の組成物は、例えば、可視光線若しくは紫外線を被着体の正面側より照射した後、可視光線若しくは紫外線が透過しない箇所を被着体の側面側より照射して、被着体を張り合わせることができる接着剤組成物である。
本発明の一実施形態の接着剤組成物は、例えば、可視光線若しくは紫外線を照射することによって、接着剤組成物の硬化体を得ることができる。
本発明の一実施形態の硬化体によって被着体を被覆又は接合された複合体を得えられる。また、被着体は、特に限定しないが、トリアセチルセルロース、フッ素系ポリマー、ポリエステル、ポリカーボネート、ポリオレフィン、ガラス、金属からなる群から選ばれる１種以上を含むことが好ましい。
本発明の一実施形態の接着剤組成物を用いて、公知方法によって、被着体を貼り合わせたタッチパネル積層体を得ることができる。
また、本発明の一実施形態の接着剤組成物を用いて、公知方法によって、被着体を貼り合わせたタッチパネル積層体を得ることができる。また上記タッチパネル積層体を用いてディスプレイを得ることができる。
また、本発明の一実施形態の接着剤組成物を用いて、公知方法によって、被着体を貼り合わせた液晶パネル積層体を得ることができる。また上記液晶パネル積層体を用いてディスプレイを得ることができる。The composition of one embodiment of the present invention is, for example, a curable resin composition, and can be used as an adhesive composition. The composition of one embodiment of the present invention is a composition capable of deep curing, for example, larger than 3 mm, preferably 4 mm or more, when irradiated with 100 mJ / cm 2 of visible light or ultraviolet light at a wavelength of 365 nm. The composition of one embodiment of the present invention, for example, irradiates visible light or ultraviolet light from the front side of the adherend, and then irradiates a portion through which the visible light or ultraviolet light is not transmitted from the side surface of the adherend. It is an adhesive composition capable of pasting a kimono.
The adhesive composition of one embodiment of the present invention can obtain a cured product of the adhesive composition by, for example, irradiation with visible light or ultraviolet light.
The composite_body | complex which coat | covered or joined the adherend with the hardening body of one Embodiment of this invention can be obtained. Moreover, although an adherend is not specifically limited, It is preferable that 1 or more types chosen from the group which consists of a triacetyl cellulose, a fluorine-type polymer, polyester, a polycarbonate, polyolefin, glass, and a metal are included.
Using the adhesive composition of one embodiment of the present invention, a touch panel laminate in which adherends are bonded can be obtained by a known method.
Moreover, the touch panel laminated body which bonded together the to-be-adhered body can be obtained by a well-known method using the adhesive composition of one Embodiment of this invention. A display can be obtained using the touch panel laminate.
Moreover, the liquid crystal panel laminated body which bonded together the to-be-adhered body can be obtained by a well-known method using the adhesive composition of one Embodiment of this invention. A display can be obtained using the liquid crystal panel laminate.
以下に、実験例をあげて、本発明を更に詳細に説明するが、本発明はこれら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 experimental examples, but the present invention is not limited thereto.
（実験例）
特記しない限り、２３℃で、実験した。表１、表２に示す組成の硬化性樹脂組成物を調製し、評価した。結果を表３、表４に示す。(Experimental example)
Unless otherwise stated, experiments were conducted at 23 ° C. Curable resin compositions having the compositions shown in Tables 1 and 2 were prepared and evaluated. The results are shown in Tables 3 and 4.
実験例に記載の硬化性樹脂組成物中の各成分としては、以下の化合物を選択した。 The following compounds were selected as each component in the curable resin composition described in the experimental examples.
但し、表のＫＲＭ−８７７６は、ダイセルサイテック製「ＫＲＭ−８７７６」中に含有するウレタンアクリレートの量を記載した。表のＮＯＡＡは、ダイセルサイテック製「ＫＲＭ−８７７６」中に含有するｎ−オクチルアクリレートの量を記載した。ダイセルサイテック製「ＫＲＭ−８７７６」を使用しない場合等は、大阪有機化学社製のｎ−オクチルアクリレートを使用した。 However, KRM-8776 in the table describes the amount of urethane acrylate contained in “KRM-8776” manufactured by Daicel Cytec. The NOAA in the table describes the amount of n-octyl acrylate contained in “KRM-8777” manufactured by Daicel Cytec. When not using “KRM-8777” manufactured by Daicel Cytec, n-octyl acrylate manufactured by Osaka Organic Chemical Co., Ltd. was used.
＜（Ｐ）重合性ビニルモノマーの（Ａ）多官能（メタ）アクリレート＞
（Ａ）成分の多官能（メタ）アクリレートとして、以下の化合物を選択した。<(P) (A) Polyfunctional (meth) acrylate of polymerizable vinyl monomer>
The following compounds were selected as the polyfunctional (meth) acrylate of component (A).
（Ａ−１）ポリエステル系ウレタンアクリレートオリゴマー（根上工業社製「ＫＨＰ−１１」、構造は以下の通り、ポリオール化合物は、１，４−ブタンジオールとアジピン酸との縮合物であるポリエステルポリオールと、エチレングリコールとアジピン酸との縮合物であるポリエステルポリオールとを有する化合物（１，４−ブタンジオールとアジピン酸との縮合物であるポリエステルポリオール：エチレングリコールとアジピン酸との縮合物であるポリエステルポリオール＝２：３（モル比））、有機ポリイソシアネート化合物はイソホロンジイソシアネート、ヒドロキシ（メタ）アクリレートは２−ヒドロキシエチルアクリレート、ＧＰＣによるポリスチレン換算の重量平均分子量２５０００） (A-1) Polyester urethane acrylate oligomer (“KHP-11” manufactured by Negami Kogyo Co., Ltd., the structure is as follows, the polyol compound is a polyester polyol which is a condensate of 1,4-butanediol and adipic acid, A compound having a polyester polyol which is a condensate of ethylene glycol and adipic acid (polyester polyol which is a condensate of 1,4-butanediol and adipic acid: polyester polyol which is a condensate of ethylene glycol and adipic acid = 2: 3 (molar ratio)), the organic polyisocyanate compound is isophorone diisocyanate, the hydroxy (meth) acrylate is 2-hydroxyethyl acrylate, and the weight average molecular weight in terms of polystyrene by GPC is 25000)
（Ａ−２）ポリエステル系ウレタンアクリレートオリゴマー（日本合成化学社製「ＵＶ−３０００Ｂ」、なお構造は以下の通り、ポリオール化合物は、水素化ポリブタジエンポリオールとアジピン酸との縮合物であるポリエステルポリオール、有機ポリイソシアネート化合物はイソホロンジイソシアネート、ヒドロキシ（メタ）アクリレートは４−ヒドロキシブチルアクリレート、ＧＰＣによるポリスチレン換算の重量平均分子量１５０００、水素化ポリブタジエンポリオールは式（３）で表される化合物（ｎは正数）） (A-2) Polyester urethane acrylate oligomer (“UV-3000B” manufactured by Nippon Synthetic Chemical Co., Ltd., where the structure is as follows, the polyol compound is a polyester polyol which is a condensate of hydrogenated polybutadiene polyol and adipic acid, organic The polyisocyanate compound is isophorone diisocyanate, the hydroxy (meth) acrylate is 4-hydroxybutyl acrylate, the polystyrene equivalent weight average molecular weight 15000 by GPC, the hydrogenated polybutadiene polyol is a compound represented by the formula (3) (n is a positive number))
（Ａ−３）ポリブタジエン系ウレタンアクリレート（ダイセルサイテック製「ＫＲＭ−８７７６」、水素化ポリブタジエン骨格を有するウレタンアクリレートである。なお、構造は以下の通り、ポリオール化合物は水素化ポリブタジエンポリオール、有機ポリイソシアネート化合物はイソホロンジイソシアネート、ヒドロキシ（メタ）アクリレートは２−ヒドロキシエチルアクリレート、ＧＰＣによるポリスチレン換算の重量平均分子量１９０００、水素化ポリブタジエンポリオールは式（３）で表される化合物（ｎは正数）、但し希釈モノマーとしてｎ−オクチルアクリレートを３０質量％含有） (A-3) Polybutadiene-based urethane acrylate ("KRM-8777" manufactured by Daicel Cytec, a urethane acrylate having a hydrogenated polybutadiene skeleton. The structure is as follows. The polyol compound is a hydrogenated polybutadiene polyol, an organic polyisocyanate compound. Is isophorone diisocyanate, hydroxy (meth) acrylate is 2-hydroxyethyl acrylate, polystyrene equivalent weight average molecular weight of 19000, hydrogenated polybutadiene polyol is a compound represented by formula (3) (n is a positive number), but diluting monomer N-octyl acrylate as 30% by mass)
＜（Ｐ）重合性ビニルモノマーの単官能（メタ）アクリレート＞
（Ｂ）成分の単官能（メタ）アクリレートとして、以下の化合物を選択した。
（Ｂ−１）ラウリルアクリレート（大阪有機化学社製「ＬＡ」）
（Ｂ−２）２−ヒドロキシブチルアクリレート（共栄社化学社製「ＨＯＢ−Ａ」）
（Ｂ−３）ｎ−オクチルアクリレート（以下「ＮＯＡＡ」と略す）<(P) Monofunctional (meth) acrylate of polymerizable vinyl monomer>
The following compounds were selected as the monofunctional (meth) acrylate of the component (B).
(B-1) Lauryl acrylate (“LA” manufactured by Osaka Organic Chemical Co., Ltd.)
(B-2) 2-hydroxybutyl acrylate (“HOB-A” manufactured by Kyoeisha Chemical Co., Ltd.)
(B-3) n-octyl acrylate (hereinafter abbreviated as “NOAA”)
＜（Ｃ）光重合開始剤＞
（Ｃ）成分の、光重合開始剤として、以下の化合物を選択した。
（Ｃ−１）１−ヒドロキシシクロヘキシルフェニルケトン（ＢＡＳＦ社製「Ｉｒｇａｃｕｒｅ１８４」、以下「Ｉ−１８４」と略す）
（Ｃ−２）２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイド（ＢＡＳＦ社製「ＬｕｃｉｒｉｎＴＰＯ」、以下「ＴＰＯ」と略す）<(C) Photopolymerization initiator>
The following compounds were selected as the photopolymerization initiator of component (C).
(C-1) 1-hydroxycyclohexyl phenyl ketone ("Irgacure 184" manufactured by BASF, hereinafter abbreviated as "I-184")
(C-2) 2,4,6-trimethylbenzoyldiphenylphosphine oxide ("Lucirin TPO" manufactured by BASF, hereinafter abbreviated as "TPO")
＜（Ｄ）酸化防止剤＞
（Ｄ）成分の酸化防止剤として、以下の化合物を選択した。
（Ｄ−１）６−ｔｅｒｔ−ブチル−４−［３−［（２，４，８，１０−テトラ−ｔｅｒｔ−ブチルジベンゾ［ｄ，ｆ］［１，３，２］ジオキサホスフェピン−６−イル）オキシ］プロピル］−２−メチルフェノール（住友化学工業社製「スミライザーＧＰ」）（以下「ＧＰ」と略す）<(D) Antioxidant>
The following compounds were selected as the antioxidant of component (D).
(D-1) 6-tert-butyl-4- [3-[(2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphine- 6-yl) oxy] propyl] -2-methylphenol (“Sumizer GP” manufactured by Sumitomo Chemical Co., Ltd.) (hereinafter abbreviated as “GP”)
＜（Ｅ）チオール＞
チオール化合物として、以下の化合物を選択した。
（Ｅ−１）ペンタエリスリトールテトラキス（３−メルカプトブチレート）（昭和電工社製「カレンズＭＴ ＰＥ１」）（以下「ＭＴ−ＰＥ１」と略す）
（Ｅ−２）ペンタエリスリトールテトラキス（３−メルカプトプロピオネート）（ＳＣ有機化学製「ＰＢＭＰ」）
（Ｅ−３）１−ドデカンチオール（シグマ・アルドリッチ社製「ＤＤＴ」）<(E) Thiol>
The following compounds were selected as thiol compounds.
(E-1) Pentaerythritol tetrakis (3-mercaptobutyrate) (“Karenz MT PE1” manufactured by Showa Denko KK) (hereinafter abbreviated as “MT-PE1”)
(E-2) Pentaerythritol tetrakis (3-mercaptopropionate) (SC Organic Chemical "PBMP")
(E-3) 1-dodecanethiol ("DDT" manufactured by Sigma-Aldrich)
＜（Ｆ）ジカルボン酸ジエステル＞
（Ｆ）について式（１）で表されるジカルボン酸ジエステルとして、以下の化合物を選択した。
（Ｆ−１）セバシン酸ビス（２−エチルヘキシル）（新日本理化社製「サンソサイザーＤＯＳ」）（以下「ＤＯＳ」と略す）
（Ｆ−２）セバシン酸ジブチル（和光純薬社製）（以下「ＤＢＳ」と略す）
（Ｆ−３）アゼライン酸ビス（２−エチルヘキシル）（和光純薬社製）（以下「ＤＯＺ」と略す）
（Ｆ−４）アジピン酸ビス（２−エチルヘキシル）（和光純薬社製）（以下「ＤＯＡ」と略す）<(F) Dicarboxylic acid diester>
The following compounds were selected as the dicarboxylic acid diester represented by the formula (1) for (F).
(F-1) Bis (2-ethylhexyl) sebacate (manufactured by Shin Nippon Chemical Co., Ltd., “Sunsizer DOS”) (hereinafter abbreviated as “DOS”)
(F-2) Dibutyl sebacate (manufactured by Wako Pure Chemical Industries, Ltd.) (hereinafter abbreviated as “DBS”)
(F-3) Azelaic acid bis (2-ethylhexyl) (manufactured by Wako Pure Chemical Industries, Ltd.) (hereinafter abbreviated as “DOZ”)
(F-4) Bis (2-ethylhexyl) adipate (Wako Pure Chemical Industries, Ltd.) (hereinafter abbreviated as “DOA”)
各種物性は、次のように測定した。 Various physical properties were measured as follows.
〔光硬化性〕
温度２３℃で測定した。光硬化性に関しては、テンパックスガラス（幅２５ｍｍ×長さ２５ｍｍ×厚さ２ｍｍ）の表面に硬化性樹脂組成物を厚み０．１ｍｍになるように塗布した。その後、無電極放電ランプを使用したフュージョン社製硬化装置を用い、波長３６５ｎｍのＵＶ光を積算光量２０００ｍＪ／ｃｍ２の条件にて照射し、硬化させた。
硬化率は、ＦＴ−ＩＲを使用し、以下の式により算出した。炭素と炭素の二重結合の吸収スペクトルは、１６００ｃｍ−１付近のピークを用いた。 [Photocurability]
Measurement was performed at a temperature of 23 ° C. Regarding photocurability, a curable resin composition was applied to a surface of Tempax glass (width 25 mm × length 25 mm × thickness 2 mm) to a thickness of 0.1 mm. Thereafter, using a curing device manufactured by Fusion Corporation using an electrodeless discharge lamp, UV light having a wavelength of 365 nm was irradiated and cured under the condition of an integrated light quantity of 2000 mJ / cm 2 .
The curing rate was calculated by the following formula using FT-IR. The peak near 1600 cm −1 was used for the absorption spectrum of the carbon-carbon double bond.
（硬化率）＝１００−（硬化後の、炭素と炭素の二重結合の吸収スペクトルの強度）／（硬化前の、炭素と炭素の二重結合の吸収スペクトルの強度）×１００（％） (Curing rate) = 100- (Intensity of absorption spectrum of carbon-carbon double bond after curing) / (Intensity of absorption spectrum of carbon-carbon double bond before curing) × 100 (%)
〔硬化収縮率〕
比重瓶に硬化性樹脂組成物を充填し、大気中での質量及び純水中での質量を計測し、液比重を算出した。更に硬化性樹脂組成物を〔光硬化性〕に記載の方法で硬化し、幅２５ｍｍ×長さ２５ｍｍ×厚さ２ｍｍの硬化物を作製し、大気中での質量及び純水中での質量を計測し、硬化物比重を算出した。液比重及び硬化物比重の比率より硬化収縮率を算出した。
硬化収縮率＝（（硬化物比重−液比重）／硬化物比重）×１００（％）[Curing shrinkage]
The specific gravity bottle was filled with the curable resin composition, the mass in the air and the mass in pure water were measured, and the liquid specific gravity was calculated. Furthermore, the curable resin composition is cured by the method described in [Photocurability] to produce a cured product having a width of 25 mm × length of 25 mm × thickness of 2 mm, and the mass in the air and the mass in pure water are measured. It measured and computed hardened | cured material specific gravity. The cure shrinkage was calculated from the ratio of liquid specific gravity and cured product specific gravity.
Curing shrinkage rate = ((cured product specific gravity−liquid specific gravity) / cured product specific gravity) × 100 (%)
〔深部硬化性〕
直径５ｍｍφの穴の開いた長さ２０ｍｍ黒チューブに、硬化性樹脂組成物を充填し、上部からブラックライトにて１ｍＷ／ｃｍ２（３６５ｎｍ）の光を１００秒間照射した（積算光量は１００ｍＪ／ｃｍ２）。その後、黒チューブから硬化物を取り出し、未硬化部分を取り除き、硬化している部分の厚みをマイクロメーターで測定した。[Deep part curability]
A curable resin composition was filled in a black tube having a diameter of 5 mmφ and a length of 20 mm, and 1 mW / cm 2 (365 nm) was irradiated from the top with black light for 100 seconds (the integrated light amount was 100 mJ / cm). 2 ). Then, the hardened | cured material was taken out from the black tube, the uncured part was removed, and the thickness of the hardened part was measured with the micrometer.
〔ポリエチレンテレフタレート（ＰＥＴ）接着性評価（ポリエチレンテレフタレート試験片間の剥離接着強さ）〕
２軸延伸ＰＥＴフィルム（ルミラーＴ６０、平均厚さ１９０μｍ、東レ社製）の試験片（幅５０ｍｍ×長さ１０ｍｍ×厚さ０．１９ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み３０μｍで接着面積を縦４０ｍｍ×横１０ｍｍとして接着させた。光照射による硬化後、接着剤組成物で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射条件は〔光硬化性〕に記載の方法に従った。剥離接着強さ（単位：Ｎ／ｃｍ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度５０ｍｍ／分で測定した。[Polyethylene terephthalate (PET) adhesiveness evaluation (peel adhesion strength between polyethylene terephthalate test pieces)]
Test pieces (width 50 mm × length 10 mm × thickness 0.19 mm) of biaxially stretched PET films (Lumirror T60, average thickness 190 μm, manufactured by Toray Industries, Inc.) are used as the adhesive composition. Then, the adhesive layer was bonded with a thickness of 30 μm and an adhesive area of 40 mm long × 10 mm wide. After curing by light irradiation, by pulling the two end portions of the film that are not in close contact with the test piece bonded with the adhesive composition, the portions where the films are in close contact are peeled off, and the initial 180 ° peeling is performed. The bond strength was measured. The light irradiation conditions followed the method described in [Photocurability]. The peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
〔ガラス接着性評価（耐熱ガラス試験片間の引張接着強さ）〕
耐熱ガラス試験片（幅２５ｍｍ×長さ２５ｍｍ×厚さ２．０ｍｍ）同士を、厚み８０μｍ×幅１１．５ｍｍ×長さ２５ｍｍのテフロン（登録商標）テープをスペーサーとして用い、硬化性樹脂組成物を接着剤組成物として用いて、接着させた（接着面積３ｃｍ２）。光照射条件は〔光硬化性〕に記載の方法に従った。上記条件にて接着剤組成物を硬化させた後、更に、試験片の両面に電気化学工業社製接着剤組成物「Ｇ−５５」を使用し、亜鉛メッキ鋼板（幅１００ｍｍ×長さ２５ｍｍ×厚さ２．０ｍｍ、エンジニアリングテストサービス社製）を接着させた。硬化後、接着剤組成物で接着した該試験片を用いて、亜鉛メッキ鋼板をチャックして、初期の引張剪断接着強さを測定した。引っ張り剪断接着強さ（単位：ＭＰａ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度１０ｍｍ／分で測定した。[Evaluation of glass adhesion (tensile bond strength between heat-resistant glass specimens)]
Heat-resistant glass test pieces (width 25 mm × length 25 mm × thickness 2.0 mm) were used, and a Teflon (registered trademark) tape having a thickness of 80 μm × width 11.5 mm × length 25 mm was used as a spacer. The adhesive composition was used for adhesion (adhesion area 3 cm 2 ). The light irradiation conditions followed the method described in [Photocurability]. After the adhesive composition was cured under the above conditions, an adhesive composition “G-55” manufactured by Denki Kagaku Kogyo Co., Ltd. was used on both sides of the test piece, and a galvanized steel sheet (width 100 mm × length 25 mm × A thickness of 2.0 mm, manufactured by Engineering Test Service Co., Ltd.) was adhered. After the curing, using the test piece bonded with the adhesive composition, the galvanized steel sheet was chucked, and the initial tensile shear bond strength was measured. The tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
〔シクロオレフィンポリマー（ＣＯＰ）接着性評価（シクロオレフィンポリマー試験片間の剥離接着強さ）〕
ＣＯＰフィルム（ＺＥＯＮＯＲ、平均厚さ４０μｍ、日本ゼオン社製）の試験片（幅５０ｍｍ×長さ１０ｍｍ×厚さ０．０４ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み１０μｍで接着面積を縦４０ｍｍ×横１０ｍｍとして接着させた。光照射による硬化後、接着剤で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射条件は〔光硬化性〕に記載の方法に従った。剥離接着強さ（単位：Ｎ／ｃｍ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度５０ｍｍ／分で測定した。[Cycloolefin polymer (COP) adhesion evaluation (peel adhesion strength between cycloolefin polymer specimens)]
Bonding test pieces (width 50 mm x length 10 mm x thickness 0.04 mm) of COP films (ZEONOR, average thickness 40 μm, manufactured by Nippon Zeon Co., Ltd.) using the curable resin composition as an adhesive composition The layers were bonded with a thickness of 10 μm and a bonding area of 40 mm long × 10 mm wide. After curing by light irradiation, by pulling the two non-adhered film end portions of the test piece bonded with an adhesive, the film-adhered portions are peeled off, and the initial 180 ° peel adhesion strength Measured. The light irradiation conditions followed the method described in [Photocurability]. The peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
〔トリアセチルセルロース接着性評価（トリアセチルセルロース試験片間の剥離接着強さ）〕
トリアセチルセルロース（ＴＡＣ）フィルム（平均厚さ４０μｍ、富士フィルム社製）の試験片（幅５０ｍｍ×長さ１０ｍｍ×厚さ０．０４ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み１０μｍで接着面積を縦４０ｍｍ×横１０ｍｍとして接着させた。接着剤組成物で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射による硬化後、接着剤組成物で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射条件は〔光硬化性〕に記載の方法に従った。剥離接着強さ（単位：Ｎ／ｃｍ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度５０ｍｍ／分で測定した。[Evaluation of triacetyl cellulose adhesion (peel adhesion strength between triacetyl cellulose test pieces)]
Using test pieces (width 50 mm × length 10 mm × thickness 0.04 mm) of triacetyl cellulose (TAC) films (average thickness 40 μm, manufactured by Fuji Film Co., Ltd.), and curable resin composition as an adhesive composition. Then, the adhesive layer was bonded with a thickness of 10 μm and an adhesive area of 40 mm long × 10 mm wide. The initial 180 ° peel strength was measured by pulling the two film ends that were not in close contact with the test piece that was adhered with the adhesive composition, thereby peeling the portions where the films were in close contact with each other. . After curing by light irradiation, by pulling the two end portions of the film that are not in close contact with the test piece bonded with the adhesive composition, the portions where the films are in close contact are peeled off, and the initial 180 ° peeling is performed. The bond strength was measured. The light irradiation conditions followed the method described in [Photocurability]. The peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
〔フッ素系ポリマー接着性評価（フッ素ポリマー試験片間の剥離接着強さ）〕
ＰＶＤＦ（Ｐｏｌｙｖｉｎｙｌｉｄｅｎｅ ｆｌｕｏｒｉｄｅ）フィルム（平均厚さ４０μｍ、電気化学工業社製「ＤＸフィルム」）の試験片（幅５０ｍｍ×長さ１０ｍｍ×厚さ０．０４ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み１０μｍで接着面積を縦４０ｍｍ×横１０ｍｍとして接着させた。接着剤組成物で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射による硬化後、接着剤組成物で接着した該試験片の、密着されていない２箇所のフィルム端部を引っ張ることで、フィルム同士が密着された部分を剥離させて、初期の１８０°剥離接着強さを測定した。光照射条件は〔光硬化性〕に記載の方法に従った。剥離接着強さ（単位：Ｎ／ｃｍ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度５０ｍｍ／分で測定した。[Fluoropolymer adhesion evaluation (peel adhesion strength between fluoropolymer specimens)]
Test pieces (width 50 mm × length 10 mm × thickness 0.04 mm) of PVDF (Polyvinylidene fluoride) film (average thickness 40 μm, manufactured by Denki Kagaku Kogyo Co., Ltd.) are bonded to each other with a curable resin composition as an adhesive. Using as a composition, the adhesive layer was bonded with a thickness of 10 μm and a bonding area of 40 mm long × 10 mm wide. The initial 180 ° peel strength was measured by pulling the two film ends that were not in close contact with the test piece that was adhered with the adhesive composition, thereby peeling the portions where the films were in close contact with each other. . After curing by light irradiation, by pulling the two end portions of the film that are not in close contact with the test piece bonded with the adhesive composition, the portions where the films are in close contact with each other are peeled off, and the initial 180 ° peeling is performed. The bond strength was measured. The light irradiation conditions followed the method described in [Photocurability]. The peel adhesion strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
〔ポリカーボネート接着性評価（ポリカーボネート試験片間の引張接着強さ）〕
ポリカーボネート（帝人社製「パンライト」）試験片（幅２５ｍｍ×長さ２５ｍｍ×厚さ２．０ｍｍ）同士を、厚み８０μｍ×幅１２．５ｍｍ×長さ２５ｍｍのテフロン（登録商標）テープをスペーサーとして用い、硬化性樹脂組成物を接着剤組成物として用いて、接着させた（接着面積３ｃｍ２）。光照射条件は〔光硬化性〕に記載の方法に従った。引っ張り剪断接着強さ（単位：ＭＰａ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度１０ｍｍ／分で測定した。[Polycarbonate adhesion evaluation (tensile bond strength between polycarbonate specimens)]
Polycarbonate (“Panlite” manufactured by Teijin Limited) specimens (width 25 mm × length 25 mm × thickness 2.0 mm) and Teflon (registered trademark) tape of thickness 80 μm × width 12.5 mm × length 25 mm as spacers The curable resin composition was used as an adhesive composition and adhered (adhesion area 3 cm 2 ). The light irradiation conditions followed the method described in [Photocurability]. The tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
〔耐湿熱性評価（高温高湿暴露後の耐熱ガラス試験片間の引張接着強さ）〕
テンパックス（登録商標）ガラス（幅２５ｍｍ×長さ２５ｍｍ×厚さ２ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み１００μｍで接着面積を１．０ｃｍ２として接着させ、硬化させた。光照射条件は〔光硬化性〕に記載の方法に従った。硬化後、接着剤組成物で接着した該試験片を、恒温恒湿槽を用いて、温度８５℃、相対湿度８５％の環境下に１０００時間暴露した。暴露後の試験片を用いて、引っ張り剪断接着強さを測定した。引っ張り剪断接着強さ（単位：ＭＰａ）は、引張試験器を用いて温度２３℃、湿度５０％の環境下で引張速度１０ｍｍ／分で測定した。[Heat and heat resistance evaluation (tensile bond strength between heat resistant glass specimens after exposure to high temperature and humidity)]
Tempax (registered trademark) glass (width 25 mm × length 25 mm × thickness 2 mm), using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 100 μm and an adhesive area of 1.0 cm 2 Glued and cured. The light irradiation conditions followed the method described in [Photocurability]. After curing, the test piece bonded with the adhesive composition was exposed to an environment of 85 ° C. and 85% relative humidity for 1000 hours using a constant temperature and humidity chamber. The tensile shear bond strength was measured using the test piece after exposure. The tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
〔耐湿熱性評価（外観観察（面精度変化と黄変度））〕
テンパックス（登録商標）ガラス（幅２５ｍｍ×長さ２５ｍｍ×厚さ２ｍｍ）同士を、硬化性樹脂組成物を接着剤組成物として用いて、接着層の厚み１００μｍで接着面積を１．０ｃｍ２として接着させ、硬化させた。光照射条件は〔光硬化性〕に記載の方法に従った。硬化後、接着剤組成物で接着した該試験片を、恒温恒湿槽を用いて、温度８５℃、相対湿度８５％の環境下に１０００時間暴露した。暴露後、接着剤組成物で接着した該試験片のΔｂ値を、カラー測定装置（ＳＨＩＭＡＤＺＵ社製「ＵＶ−ＶＩＳＩＢＬＥ ＳＰＥＣＴＲＯＰＯＨＯＴＯＭＥＴＥＲ」にて測定し、黄変度とした。暴露後、接着部位の外観を目視で観察し、面精度変化として寸法変化や反り等しているか否かと黄変しているか否かを調べた。[Heat and heat resistance evaluation (appearance observation (change in surface accuracy and degree of yellowing))]
Tempax (registered trademark) glass (width 25 mm × length 25 mm × thickness 2 mm), using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 100 μm and an adhesive area of 1.0 cm 2 Glued and cured. The light irradiation conditions followed the method described in [Photocurability]. After the curing, the test piece bonded with the adhesive composition was exposed to an environment of a temperature of 85 ° C. and a relative humidity of 85% for 1000 hours using a constant temperature and humidity chamber. After the exposure, the Δb value of the test piece bonded with the adhesive composition was measured with a color measuring device (“UV-VISABLE SPECTROPOHOTOMETER” manufactured by SHIMADZU) to determine the degree of yellowing. It was observed visually to check whether the surface accuracy was changed such as dimensional change or warpage and whether it was yellowing.
実験例から、以下のことが判る。本発明の実施例に相当する硬化性樹脂組成物は、深部硬化性に優れている。従って、例えば、光を遮光枠の斜め方向や横方向から照射する場合であっても、遮光枠下の硬化性樹脂組成物を深部まで硬化することが可能である。
さらに本発明の実施例に相当する硬化性樹脂組成物は、遮光枠の下でも、微弱な光（例えば、積算光量１０００〜３０００ｍＪ／ｃｍ２の光）で深部まで硬化することが可能である。
本発明の実施例に相当する硬化性樹脂組成物の実験例は、硬化収縮率が小さいので、耐湿熱性試験後の寸法変化や反り等の面精度変化が見られなかった。実験例６は、（Ｅ）の成分におけるチオール基の数が１個のため、実験例２や実験例３のポリチオールを用いた硬化性樹脂組成物より深部硬化性が小さかった。
本発明の実施例に相当する硬化性樹脂組成物は、耐熱試験後の着色や変色、耐湿試験後の強度低下といった問題が起こらなかった。The following can be seen from the experimental example. The curable resin compositions corresponding to the examples of the present invention are excellent in deep part curability. Therefore, for example, even when light is irradiated from an oblique direction or a lateral direction of the light shielding frame, the curable resin composition under the light shielding frame can be cured to a deep portion.
Furthermore, the curable resin composition corresponding to the example of the present invention can be cured to a deep portion with weak light (for example, light having an integrated light quantity of 1000 to 3000 mJ / cm 2 ) even under a light shielding frame.
In the experimental examples of the curable resin compositions corresponding to the examples of the present invention, since the curing shrinkage rate was small, changes in surface accuracy such as dimensional changes and warping after the wet heat resistance test were not observed. In Experimental Example 6, since the number of thiol groups in the component (E) was one, the deep curable property was smaller than the curable resin composition using the polythiol of Experimental Example 2 or Experimental Example 3.
In the curable resin compositions corresponding to the examples of the present invention, problems such as coloring and discoloration after the heat resistance test and strength reduction after the moisture resistance test did not occur.
Claims (14)
（Ｐ）重合性ビニルモノマー；（Ｃ）光重合開始剤；（Ｄ）酸化防止剤；（Ｅ）チオール；（Ｆ）ジカルボン酸ジエステル、
前記（Ｆ）ジカルボン酸ジエステルが式（１）で表されるジカルボン酸ジエステルであり、
前記（Ｆ）ジカルボン酸ジエステルの含有量は、前記（Ｐ）重合性ビニルモノマー及び（Ｆ）ジカルボン酸ジエステルの合計を１００質量部とした場合に、５〜５０質量部である組成物。 A composition containing the following (P) and (C) to (F) ,
(P) a polymerizable vinyl monomer; (C) a photopolymerization initiator; (D) an antioxidant; (E) a thiol; (F) a dicarboxylic acid diester;
The (F) dicarboxylic acid diester is a dicarboxylic acid diester represented by the formula (1),
The content of the (F) dicarboxylic acid diester is 5 to 50 parts by mass when the total of the (P) polymerizable vinyl monomer and (F) dicarboxylic acid diester is 100 parts by mass .
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| WO2016190361A1 (en) * | 2015-05-26 | 2016-12-01 | デンカ株式会社 | Composition |
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| CN105764930B (en) | 2018-11-16 |
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