WO2011046120A1 - Composition de résine et agent adhésif - Google Patents
Composition de résine et agent adhésif Download PDFInfo
- Publication number
- WO2011046120A1 WO2011046120A1 PCT/JP2010/067895 JP2010067895W WO2011046120A1 WO 2011046120 A1 WO2011046120 A1 WO 2011046120A1 JP 2010067895 W JP2010067895 W JP 2010067895W WO 2011046120 A1 WO2011046120 A1 WO 2011046120A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- adhesive
- meth
- resin composition
- acrylate
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 71
- 239000011342 resin composition Substances 0.000 title claims abstract description 33
- 230000001070 adhesive effect Effects 0.000 claims abstract description 69
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 41
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 17
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 23
- 150000001993 dienes Chemical group 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 5
- 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 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002897 diene group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 12
- -1 2-hydroxypropyl Chemical group 0.000 description 11
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 5
- 150000001925 cycloalkenes Chemical class 0.000 description 5
- 229920001195 polyisoprene Polymers 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 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
- 229920002857 polybutadiene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SYYDEXILBJXXIA-UHFFFAOYSA-N trimethoxy(pent-4-enyl)silane Chemical compound CO[Si](OC)(OC)CCCC=C SYYDEXILBJXXIA-UHFFFAOYSA-N 0.000 description 3
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 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
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-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
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-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
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000006677 Appel reaction Methods 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- WMONOXOCMIPNNU-UHFFFAOYSA-N C=CC(=O)OCCCC(O)COC(=O)C1=CC=CC=C1C(O)=O Chemical compound C=CC(=O)OCCCC(O)COC(=O)C1=CC=CC=C1C(O)=O WMONOXOCMIPNNU-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 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 1
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- 238000010586 diagram Methods 0.000 description 1
- 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 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
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- 230000001678 irradiating effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—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
- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
Definitions
- the present invention relates to an adhesive.
- Cycloolefin polymers are used in applications such as electronic materials, optical lenses and medical materials. Cycloolefin polymers are known as difficult adherends because of their low polarity and lack of many functional groups on the surface. Examples of the adhesive for adhering such a cycloolefin-based resin include a solvent-type adhesive and a hot melt adhesive.
- Patent Document 1 As a method for adhering an olefin resin, there is a method of adhering with an instantaneous adhesive after performing a treatment with a primer as disclosed in Patent Document 1. Moreover, as disclosed in Patent Document 2, an energy ray-curable resin composition containing (meth) acrylate is disclosed.
- a solvent type adhesive uses a solvent. Solvent-type adhesives are harmful to the human body, and it takes time for the solvent to evaporate, so that sufficient adhesive strength itself cannot be obtained.
- the hot melt adhesive requires labor and equipment for melting the adhesive. Also, this adhesive cannot provide sufficient adhesive strength. In the case of using a hot melt adhesive, if the cycloolefin polymer is heated in advance, the adhesive strength is improved, but a new problem that the resin is deformed occurs.
- Patent Document 1 According to the adhesion method disclosed in Patent Document 1, there is a problem that it takes time and effort for primer treatment, and a sufficient adhesion strength cannot be obtained.
- Patent Document 2 discloses an energy ray curable resin composition containing (meth) acrylate. However, there is no description about (meth) acrylate having a dicyclopentenyl group.
- An object of this invention is to provide the adhesive agent for cycloolefin polymers which can express sufficient adhesive strength in a short time with respect to a cycloolefin polymer, for example, and is a solvent-free type and environmentally friendly.
- the present inventor has intensively studied to solve the above-described problems and has arrived at the present invention.
- a resin composition comprising the following components (A) to (E).
- (A) component is a (meth) acrylate having a dicyclopentenyl group
- (B) component is a (meth) acrylate having a hydroxyl group
- (C) component is having a (meth) acryloyl group and is a diene skeleton
- the (meth) acrylate (D) component having a hydrogenated diene-based skeleton is a silane coupling agent (E) component is a photopolymerization initiator.
- the resin composition according to the present invention further comprises (meth) acrylic acid as the component (F).
- the resin composition according to the present invention further contains polyvinyl alcohol as the component (G).
- the component (A) is dicyclopentenyl (meth) acrylate.
- the component (C) has a number average molecular weight of 500 to 50,000.
- the resin composition according to the present invention has a thickness of 0.03 mm, and when cured by irradiation for 15 seconds under conditions of a wavelength of 365 nm and an integrated light quantity of 2000 mJ / cm 2 , the storage elasticity of the cured product.
- the rate is in the range of 0.1 to 100,000 MPa (23 ° C.).
- the present invention is an adhesive comprising the resin composition according to the present invention.
- the adhesive according to the present invention is a cycloolefin polymer adhesive.
- the adhesive according to the present invention is an adhesive for a cycloolefin polymer having a dicyclopentadiene ring structure.
- the present invention is an adhesive body in which adherends are bonded to each other using the adhesive according to the present invention.
- the adherend according to the present invention is at least one member selected from the group consisting of cycloolefin polymer, polycarbonate, cellulose triacetate, polyvinyl alcohol and glass.
- the adhesive according to the present invention is applied to the surface of the adherend so as to have a thickness of 0.0001 to 5 mm, and the adherends are bonded to each other to obtain a wavelength of 200 to 500 nm.
- This is a method for producing an adhesive body comprising curing the adhesive under conditions of an integrated light quantity of 200 to 6000 J / cm 2 and an irradiation time of 1 to 60 seconds.
- the resin composition of the present invention is characterized by high adhesive strength and excellent moisture resistance.
- the component (A) in the present invention is a (meth) acrylate having a dicyclopentenyl group. More specifically, the component (A) is a (meth) acrylate containing one or more dicyclopentenyl groups at the terminal or side chain of the molecule.
- Examples of (A) component (meth) acrylate include dicyclopentenyloxyethyl (meth) acrylate, dicyclopentenyloxypropyl (meth) acrylate, and dicyclopentenyl (meth) acrylate. Of these, dicyclopentenyl (meth) acrylate is preferred.
- the component (B) is a (meth) acrylate containing a hydroxyl group. More specifically, the component (B) is a (meth) acrylate containing one or more hydroxyl groups at the end or side chain of the molecule.
- hydroxyl group-containing (meth) acrylates include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 2-hydroxy-3-phenoxypropyl (meth) acrylate.
- 2-hydroxy-3-phenoxypropyl (meth) acrylate is more preferable from the viewpoint of resin film adhesion.
- the component (C) is a (meth) acrylate having a (meth) acryloyl group and having a diene skeleton or a hydrogenated diene skeleton. More specifically, the component (C) has one or more (meth) acryloyl groups at the terminal or side chain of the molecule, and has a diene skeleton or a hydrogenated diene skeleton.
- (Meth) acrylates preferably (meth) acrylates having one or more (meth) acryloyl groups at the end of the molecule and having a diene skeleton or a hydrogenated diene skeleton. is there. This includes the following components from the viewpoint of imparting flexibility to the resin.
- the main chain skeleton of (meth) acrylate is a diene skeleton or a hydrogenated diene skeleton.
- the diene skeleton or the hydrogenated diene skeleton include one or more skeletons selected from the group consisting of polybutadiene, polyisoprene, a hydrogenated polybutadiene, and a hydrogenated polyisoprene.
- at least one selected from the group consisting of polyisoprene and a hydrogenated product of polyisoprene is preferable, and polyisoprene is more preferable.
- the (meth) acrylate of the component (C) has one or more (meth) acryloyl groups at the terminal or side chain of the main chain skeleton. Among these, those having (meth) acryloyl groups at both ends of the main chain skeleton are preferable.
- the number average molecular weight of the component (C) (meth) acrylate is preferably 500 to 50,000, and more preferably 8000 to 45,000. If the number average molecular weight is 500 or more, the cured product obtained by irradiating the adhesive of the present invention with energy rays has a high hardness, so that it is easy to form an adhesive layer. If the number average molecular weight is 50000 or less, the viscosity of the resulting adhesive is small, so that the workability in mixing during the production process and the workability when using the adhesive in practical applications are good.
- the component (C) (meth) acrylate includes “UC-203” manufactured by Kuraray Co., Ltd. (an esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl methacrylate), “TEAI-” manufactured by Nippon Soda Co., Ltd. 1000 ”(hydrogenated 1,2-polybutadiene terminated urethane methacrylate),“ TE-2000 ”(1,2-polybutadiene terminated urethane methacrylate) manufactured by Nippon Soda Co., Ltd. and derivatives thereof,“ CN-301 ”“ CN-303 ”manufactured by Sartomer "CN-307" (polybutadiene acrylate oligomer).
- Silane coupling agents include ⁇ -chloropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinylpropyltrimethoxysilane, vinyl-tris ( ⁇ -methoxyethoxy) silane, ⁇ - (meta ) Acryloxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N - ⁇ - (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropylmethyldime
- one of the group consisting of ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (meth) acryloxypropyltrimethoxysilane and vinylpropyltrimethoxysilane is preferable.
- a component is a photoinitiator.
- the photopolymerization initiator include an ultraviolet polymerization initiator and a visible light polymerization initiator, both of which are used without limitation.
- examples of the ultraviolet polymerization initiator include benzoin, benzophenone, and acetophenone.
- examples of visible light polymerization initiators include acylphosphine oxide, thioxanthone, metallocene, quinone, and ⁇ -aminoalkylphenone.
- Photopolymerization initiators include benzophenone, 4-phenylbenzophenone, benzoylbenzoic acid, 2,2-diethoxyacetophenone, bisdiethylaminobenzophenone, benzyl, benzoin, benzoyl isopropyl ether, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, thioxanthone 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 1- (4-isopropylphenyl) 2-hydroxy-2-methylpropan-1-one 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-2-methyl-1-phenyl Rupropan-1-one, camphorquinone, 2,4,6-tri
- the resin composition of the present invention contains the components (A) to (E) as essential components.
- the resin composition containing the components (A) to (E) is cured when irradiated with light.
- the cured product has good adhesiveness to the cycloolefin polymer and has a high surface curability during the curing.
- the resin composition of the present invention exhibits high adhesive strength even for general-purpose plastic resins such as polycarbonate, cellulose triacetate, and polyvinyl alcohol, and glass adherends.
- the resin composition in the present invention can contain (meth) acrylic acid as the component (F). This is particularly used from the viewpoint of durability such as moisture resistance.
- the resin composition in the present invention can contain polyvinyl alcohol as the component (G). This includes the following components from the viewpoint of adhesiveness to the polyvinyl alcohol resin.
- the polyvinyl alcohol is not particularly limited as long as it is a polyvinyl alcohol derivative obtained by saponifying polyvinyl acetate.
- the average degree of polymerization of polyvinyl alcohol is preferably from 100 to 5,000, more preferably from 1,000 to 4,000.
- the average degree of saponification of polyvinyl alcohol is preferably 85 to 100 mol%, more preferably 90 to 100 mol%.
- the use amount of the resin composition of the present invention is as follows, from the viewpoint that the adhesiveness of the adhesive to the cycloolefin polymer is particularly high and also has high adhesive strength to other adherends. It is as follows.
- Component (D) is used in an amount of 0.01 to 10 masses per 100 parts by mass of the total amount of component (A), component (B), component (C) and component (F) used as necessary. Part is preferable, 0.1 to 5 parts by weight is more preferable, and typically 0.5 to 1.0 part by weight.
- Component (E) is used in an amount of 0.01 to 30 masses per 100 parts by mass of the total amount of component (A), component (B), component (C) and component (F) used as necessary. Part is preferable, 0.1 to 20 parts by weight is more preferable, and typically 5 to 10 parts by weight.
- Component (F) is used in an amount of 0.1 to 30 parts by mass in 100 parts by mass of the total amount of component (A), component (B), component (C) and component (F) used as necessary.
- the amount is preferably 1 to 20 parts by mass, and typically 10 to 15 parts by mass.
- Component (G) is used in an amount of 0.01 to 50 masses per 100 parts by mass of the total amount of component (A), component (B), component (C) and component (F) used as necessary. Part is preferable, 0.1 to 30 parts by weight is more preferable, and typically 0.5 to 1.0 part by weight.
- the resin composition of the present invention is within the range that does not impair the object of the present invention, and is a graft copolymer, solvent, extender, reinforcing material, plasticizer, thickener, dye, pigment, flame retardant, antioxidant. , And additives such as surfactants can be used.
- the cured product of the resin composition of the present invention preferably has a storage elastic modulus of 0.1 to 100000 MPa (23 ° C.), more preferably has a storage elastic modulus of 10 to 10000 MPa, typically 500 to 5000 MPa. It is.
- the storage elastic modulus of the cured product of the resin composition is 0.1 MPa or more, the cured product is cured and no unreacted component remains.
- the storage elastic modulus is 100000 MPa or less, the cured product does not become too rigid and the adhesive force does not decrease.
- the resin composition of the present invention can be used as an adhesive.
- the adhesive of the present invention exhibits high adhesive strength with respect to one or more selected from the group consisting of, for example, cycloolefin polymer, polycarbonate, cellulose triacetate, polyvinyl alcohol, and glass. In particular, it exhibits high adhesive strength for cycloolefin polymers.
- the cycloolefin polymer of the present invention is a thermoplastic resin having a structural unit derived from a cyclic olefin (cycloolefin) monomer such as norbornene or a polycyclic norbornene monomer.
- cycloolefin polymers include cycloolefin ring-opening polymers, hydrogenated ring-opening copolymers using two or more cycloolefins, chain olefins, aromatic compounds having a vinyl group, and cycloolefins.
- the adhesive according to the present invention is particularly effective for cycloolefin polymers having a dicyclopentadiene ring structure. Moreover, you may introduce
- cycloolefin polymers examples include “Topas” manufactured by Ticona®, Germany, “Arton” manufactured by JSR, “ZEONOR” and “ZEONEX” manufactured by Zeon Japan, Mitsui Chemicals, Inc. “Appel” made by the manufacturer can be mentioned.
- the adhesive bonding method of the present invention is as follows, for example.
- An adhesive is applied to the surface of at least one of the two adherends so as to have a thickness of 0.0001 to 5 mm, typically 0.01 to 0.50 mm.
- irradiation time 1 to 60 seconds, typically 2 to
- a method in which the adhesive is cured under a condition of 30 seconds to adhere the adherend is preferable.
- an antioxidant may be used as the other component.
- a phenol type or a hydroquinone type can be used, and a phenol type is preferably used.
- Antioxidants include ⁇ -naphthoquinone, 2-methoxy-1,4-naphthoquinone, methylhydroquinone, hydroquinone, 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol), catechol, hydroquinone monomethyl ether, mono Tertiary 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 Examples thereof include butyl catechol, 2-butyl-4-hydroxyanisole and 2,6-ditertiary butyl-p-
- the amount of the antioxidant used is 0.01 to 10 parts by mass with respect to 100 parts by mass of the total amount of component (A), component (B), component (C) and component (F) used as necessary. Is preferable, 0.1 to 8 parts by mass is more preferable, and 2.0 to 8.0 parts by mass is more preferable.
- component (A) a (meth) acrylate containing a dicyclopentenyl group, dicyclopentenyl acrylate (“FA-511AS” manufactured by Hitachi Chemical Co., Ltd.)
- component (A) a (meth) acrylate containing a dicyclopentenyl group, dicyclopentenyloxyethyl methacrylate (“FA-512MT” manufactured by Hitachi Chemical Co., Ltd.)
- component (B) Component, 2-hydroxy-3-phenoxypropyl acrylate (“M-5700” manufactured by Toagosei Co., Ltd.) as a (meth) acrylate containing a hydroxyl group
- B) Component, 2-hydroxyethyl methacrylate (“light ester HO” manufactured by Kyoeisha Chemical Co., Ltd.) as a (meth) acrylate containing a hydroxyl group
- C Component, oligomer, “UC-203” (esterified oligomer of maleic anhydride
- Light Ester BZ Lauryl methacrylate (Kyoeisha Chemical Co., Ltd. “Light Ester L”) Antioxidant, (D-1) 2,2-methylene-bis (4-methyl-6-tertiary butylphenol) (“Sumilyzer MDP-S” manufactured by Sumitomo Chemical Co., Ltd.)
- Test piece 12a width 25 mm ⁇ length 100 mm ⁇ thickness 2.0 mm
- a Teflon (registered trademark) tape 10 thickness 80 ⁇ m ⁇ width 25 mm ⁇ length 25 mm having a hole 11 having a size of 0.5 cm 2 in the center was attached to control the adhesive thickness.
- Test pieces 25 mm ⁇ 25 mm ⁇ 0.03 mm are 80 ⁇ m thick ⁇ 11.5 mm wide ⁇ length
- An adhesive was adhered using a 25 mm Teflon (registered trademark) tape as a spacer (adhesion area: 3.125 cm 2 ). After curing, the tensile bond strength was measured using the test piece bonded with an adhesive. Curing conditions followed the method described in [Photocurability].
- a galvanized steel sheet 100 mm ⁇ 25 mm ⁇ 2.0 mm, engineering test service
- the tensile bond strength was measured using the test piece adhered with an adhesive.
- the tensile shear bond strength (unit: MPa) was measured at a tensile rate of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50%.
- Adhesives were prepared by mixing raw materials of the types shown in Table 1 with the compositions shown in Table 1. Various physical properties of the obtained adhesive were measured. The results are shown in Table 1.
- This invention can express sufficient adhesive strength with respect to a cycloolefin polymer, a polycarbonate, polyvinyl alcohol, and glass.
- the present invention has moisture resistance.
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Priority Applications (3)
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JP2011536141A JP5684714B2 (ja) | 2009-10-14 | 2010-10-12 | 樹脂組成物及び接着剤 |
KR1020127012210A KR101696332B1 (ko) | 2009-10-14 | 2010-10-12 | 수지 조성물 및 접착제 |
CN201080046336.1A CN102686622B (zh) | 2009-10-14 | 2010-10-12 | 树脂组合物及粘合剂 |
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JP2009237801 | 2009-10-14 | ||
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WO2011046120A1 true WO2011046120A1 (fr) | 2011-04-21 |
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PCT/JP2010/067895 WO2011046120A1 (fr) | 2009-10-14 | 2010-10-12 | Composition de résine et agent adhésif |
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JP (1) | JP5684714B2 (fr) |
KR (1) | KR101696332B1 (fr) |
CN (1) | CN102686622B (fr) |
TW (1) | TWI492979B (fr) |
WO (1) | WO2011046120A1 (fr) |
Cited By (7)
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JP2011173975A (ja) * | 2010-02-24 | 2011-09-08 | Kuraray Co Ltd | ポリビニルアルコール系重合体フィルム用接着剤 |
WO2012141298A1 (fr) * | 2011-04-13 | 2012-10-18 | 電気化学工業株式会社 | Composition de résine et adhésif |
JP2015108044A (ja) * | 2013-12-03 | 2015-06-11 | 電気化学工業株式会社 | 仮固定用接着剤組成物、それを用いた構造体及び部材の仮固定方法 |
WO2016039277A1 (fr) * | 2014-09-08 | 2016-03-17 | 電気化学工業株式会社 | Composition et procédé de démontage |
EP2927295A4 (fr) * | 2012-11-30 | 2016-08-03 | Lintec Corp | Composition d'agent adhésif, feuille adhésive et dispositif électronique |
JP2016160361A (ja) * | 2015-03-03 | 2016-09-05 | 積水フーラー株式会社 | 紫外線硬化型接着剤組成物 |
WO2021132715A1 (fr) | 2019-12-27 | 2021-07-01 | 三菱ケミカル株式会社 | Structure d'insonorisation |
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Also Published As
Publication number | Publication date |
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TWI492979B (zh) | 2015-07-21 |
KR20120086314A (ko) | 2012-08-02 |
CN102686622A (zh) | 2012-09-19 |
KR101696332B1 (ko) | 2017-01-13 |
JP5684714B2 (ja) | 2015-03-18 |
JPWO2011046120A1 (ja) | 2013-03-07 |
CN102686622B (zh) | 2015-06-17 |
TW201124463A (en) | 2011-07-16 |
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