CN116103013A - Active energy ray-curable adhesive composition, cured product, and adhesive sheet - Google Patents
Active energy ray-curable adhesive composition, cured product, and adhesive sheet Download PDFInfo
- Publication number
- CN116103013A CN116103013A CN202211252857.3A CN202211252857A CN116103013A CN 116103013 A CN116103013 A CN 116103013A CN 202211252857 A CN202211252857 A CN 202211252857A CN 116103013 A CN116103013 A CN 116103013A
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- China
- Prior art keywords
- mass
- component
- acrylate
- meth
- adhesive composition
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 73
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000000047 product Substances 0.000 claims abstract description 126
- 239000007787 solid Substances 0.000 claims abstract description 53
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 43
- 229920005862 polyol Polymers 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 150000003077 polyols Chemical class 0.000 claims abstract description 23
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 8
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 8
- 230000009477 glass transition Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims description 26
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000003860 storage Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 7
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 claims description 3
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 3
- 238000005452 bending Methods 0.000 abstract description 28
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- -1 acrylic polyols Chemical class 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000463 material Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
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- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 229920006351 engineering plastic Polymers 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical group 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 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 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
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- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004696 Poly ether ether ketone Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 229920002530 polyetherether ketone Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
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- 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
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 101100112111 Caenorhabditis elegans cand-1 gene Proteins 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
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- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
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- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 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
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003484 crystal nucleating agent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
- 229920005994 diacetyl cellulose Polymers 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AYLRODJJLADBOB-UHFFFAOYSA-N methyl 2,6-diisocyanatohexanoate Chemical compound COC(=O)C(N=C=O)CCCCN=C=O AYLRODJJLADBOB-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- 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
- C09J2467/00—Presence of polyester
- C09J2467/005—Presence of polyester in the release coating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
An object of the present disclosure is to provide an active energy ray-curable adhesive composition, a cured product, and an adhesive sheet having good bending resistance. [ solution ] the present disclosure relates to an active energy ray-curable adhesive composition comprising: (A): (a1) A reaction product of a polyol, (a 2) an aliphatic polyisocyanate and (a 3-1) a hydroxyl group-containing mono (meth) acrylate or (a 3-2) an isocyanate group-containing mono (meth) acrylate, a polyurethane (meth) acrylate having a weight average molecular weight of 40000 or more and 100000 or less, (B): an alkyl mono (meth) acrylate having a glass transition temperature of-50 ℃ or lower, (C): a primary hydroxyl group-containing mono (meth) acrylate, wherein the content of the component (A) in terms of the solid content is 20 to 35 mass% inclusive and the content of the component (B) in terms of the solid content is 40 to 60 mass% inclusive, when the total of the components (A), (B) and (C) is 100 mass%.
Description
Technical Field
The present disclosure relates to an active energy ray-curable adhesive composition, a cured product, and an adhesive sheet.
Background
In recent years, adhesive compositions having characteristics suitable for use in foldable devices (for example, foldable image display devices) have been developed. However, it is known that when a foldable device is bent, a strong load is applied to the respective layers constituting the device, resulting in various problems. For example, when a device is folded, a layer of the adhesive composition (also referred to as "adhesive composition layer" in this disclosure as "cured product") may be peeled off, and thus a cured product which does not peel off even when folded is required.
Patent document 1 discloses an active energy ray-curable adhesive composition containing urethane (meth) acrylate, alkyl mono (meth) acrylate, and primary hydroxyl group-containing mono (meth) acrylate (in the present disclosure, also referred to as "active energy ray-curable adhesive composition" is "adhesive composition").
Prior art literature
Patent literature
Patent document 1: japanese patent application 2020-037689
Disclosure of Invention
Technical problem to be solved by the invention
The bending resistance is not examined in patent document 1.
The purpose of the present disclosure is to provide an active energy ray-curable adhesive composition, a cured product, and an adhesive sheet, each of which has excellent bending resistance.
Technical means for solving the technical problems
As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by a specific active energy ray-curable adhesive composition, a cured product thereof and an adhesive sheet comprising the cured product. Further, the present disclosure is made in order to solve at least part of the above problems, and may be implemented as the following manner or application examples.
Namely, the present disclosure relates to the following items 1 to 6.
(item 1)
An active energy ray-curable adhesive composition comprising
(A) The method comprises the following steps (a1) A reaction product of a polyol, (a 2) an aliphatic polyisocyanate and (a 3-1) a hydroxyl group-containing mono (meth) acrylate or (a 3-2) an isocyanate group-containing mono (meth) acrylate, a urethane (meth) acrylate having a weight average molecular weight of 40000 or more and 100000 or less,
(B) The method comprises the following steps An alkyl mono (meth) acrylate having a glass transition temperature of-50 ℃ or lower,
(C) The method comprises the following steps Mono (meth) acrylates containing a primary hydroxyl group,
wherein the content of the component (A) in terms of solid content is 20 to 35 mass% inclusive, and the content of the component (B) in terms of solid content is 40 to 60 mass% inclusive, when the total of the components (A), (B) and (C) is 100 mass%.
(item 2)
The active energy ray-curable adhesive composition according to item 1, wherein the content of the component (C) in terms of solid content is 10% by mass or more and 30% by mass or less.
(item 3)
The active energy ray-curable adhesive composition according to item 1 or 2, wherein component (B) is at least one selected from the group consisting of 2-ethylhexyl acrylate, n-octyl acrylate, lauryl methacrylate, isononyl acrylate, isodecyl acrylate and n-butyl acrylate.
(item 4)
A cured product of the active energy ray-curable adhesive composition according to any one of items 1 to 3.
(item 5)
The cured product according to item 4, wherein the storage elastic modulus G 'at 25℃and 1 Hz'Is 5.5X10 4 Pa or lower, and a storage elastic modulus G' of 2.5X10 at-20 ℃ and 1Hz 5 Pa or below.
(item 6)
An adhesive sheet, wherein the adhesive sheet has the cured product described in item 4 or 5 on at least one surface of a substrate surface.
Effects of the invention
The active energy ray-curable adhesive composition, cured product and adhesive sheet of the present disclosure have good bending resistance.
Detailed Description
In the present disclosure, numerical ranges of the respective physical characteristic values, contents, and the like can be appropriately set (for example, selected from the values of the upper limit and the lower limit described in the respective items below). Specifically, when the lower limit of the numerical value α is exemplified by A1, A2, A3, etc., and the upper limit of the numerical value α is exemplified by B1, B2, B3, etc., the range of the numerical value α is exemplified by A1 or more, A2 or more, A3 or more, B1 or less, B2 or less, B3 or less, A1 to B1, A1 to B2, A1 to B3, A2 to B1, A2 to B2, A2 to B3, A3 to B1, A3 to B2, A3 to B3, etc. In this disclosure, "to" is used to indicate that numerical values before and after "are included as a lower limit value and an upper limit value. Hereinafter, the constituent elements, the manufacturing method, and the like of the present disclosure will be described in detail.
(A) Composition of the components
(A) The component (a) is a polyurethane (meth) acrylate having a weight average molecular weight of 40000 or more and 100000 or less, which is the reaction product of (a 1) a polyol, (a 2) an aliphatic polyisocyanate, and (a 3-1) a hydroxyl group-containing mono (meth) acrylate or (a 3-2) an isocyanate group-containing mono (meth) acrylate.
(a1) Composition of the components
The cured product of the present disclosure has excellent transparency and bending resistance due to the use of the polyol as the component (a 1). Examples of the component (a 1) include polyether polyols, polyester polyols, polymer polyols, poly (meth) acrylic polyols, polycarbonate polyols, castor oil polyols and polyolefin polyols. In addition, the term (meth) acrylic acid in the present disclosure refers to acrylic acid and/or methacrylic acid.
Examples of the polyether polyol include polyethylene glycol, polypropylene glycol, polytetramethylene ether glycol, polytetramethylene glycol, and the like.
The polyether polyol may be a commercially available product. Examples of the products include polyether glycol (product name "a-di-P", manufactured by ADEKA), polyether triol (product name "a-G", manufactured by ADEKA), polyether tetraol (product name "a-EDP", manufactured by ADEKA), polyethylene glycol (product name "a-1540", manufactured by ADEKA), dipropylene glycol (product name "a-dipropylene glycol", manufactured by da-chemical corporation), polypropylene glycol (product name "a-400", manufactured by da-chemical corporation), polytetramethylene ether glycol (product name "a-PTMG 650", a-PTMG 1000", a-PTMG 2000", a-PTMG 3000", and the like.
The polyester polyol may be a commercially available product. As the above-mentioned products, there may be mentioned the high refractive index level of the mevalsal RX-4800, the product name of the mevalsal RX-4800, the high crystallinity level of the mevalsal OD-X-2523, the product name of the mevalsal OD-X-2547, the product name of the DIC, the transparent level of the mevalsal OD-X-2420, the product name of the mevalsal OD-X-2692, the product name of the DIC, the product name of the high adhesion level of the mevalsal OD-X-2108, the product name of the DIC, the product name of the mevalsal ol 3000, the product name of the polycaprolactone, the product name of the mevalsal OD-X-2420, the product name of the poly-c lactone, the product name of the poly-d 5, the product name of the poly-d 400, and the like.
The polymer polyol may be a commercially available product. Examples of the products include polymer polyols (product name "one", manufactured by Sanyo chemical industry Co., ltd.), and polymer polyols (product name "one" manufactured by Fang Ji, manufactured by AGC, inc.).
The poly (meth) acrylic polyol may be a commercially available product. Examples of the products include acrylic polyols (product name "acrylic polyol #6000", manufactured by large-scale manufacturing company), acrylic polyols (product name "eteac 7315-XS-60", manufactured by small-scale manufacturing company, stock division, inc.), acrylic polyols (product name "acrylic polyol PC #5984", manufactured by large-scale manufacturing company), and the like.
The polycarbonate polyol may be a commercially available product. As a result of the above-mentioned products, examples of the polymer include polycarbonate diol (product name "device", manufactured by mitsubishi chemical company), and product name "power of koku", a product name of koku pen; and (manufactured by tsu corporation), and the product name "schwann fiber and schwann chemical (manufactured by the product name of tsu corporation).
The castor oil based polyol may be a commercially available product. Examples of the products include castor oil polyols (product names "URIC H) and castor oil polyols (product names" castor oil polyol HS CM-025P "," castor oil polyol HS CM-075P ", and national oil).
Examples of the polyolefin polyol include hydroxyl group-containing polybutadiene, hydrogenated hydroxyl group-containing polybutadiene, hydroxyl group-containing polyisoprene, hydrogenated hydroxyl group-containing polyisoprene, hydroxyl group-containing chlorinated polypropylene, hydroxyl group-containing chlorinated polyethylene, and the like.
The polyolefin polyol may be a commercially available product. As the above-mentioned products, polybutadiene diol (product name "Poly bd R-45HT", "Poly bd R-15HT", manufactured by Nissan Kagaku Co., ltd.) (product name "NISSO-PB B-1000", "NISSO-PB B-2000", "NISSO-PB G-1000", "NISSO-PB G-2000", manufactured by Nippon Cadda Co., ltd.), hydrogenated polybutadiene diol (product name "NISSO-PB GI-1000", "NISSO-PB GI-2000", manufactured by Nissan Caddar Co., ltd.), and the like can be mentioned.
(a1) The upper limit of the number average molecular weight of the component may be exemplified by 13000, 12000, 11000, 10000, 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, 1000, 900, 800, etc., and the lower limit may be exemplified by 12000, 11000, 10000, 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, 1000, 900, 800, 700, etc. The number average molecular weight of the component (a 1) is preferably 700 to 13000 from the viewpoint of excellent adhesion and level difference adhesion of the cured product. Since the number average molecular weight of the component (a 1) is less than the lower limit, the cured product tends to be hard, and the cured product tends to be soft beyond the upper limit, and thus the adhesive force and the level difference adhesion tend to be good within the above preferable range. In the present disclosure, the number average molecular weight can be determined by JIS K7252-1: 2016.
(a1) The upper limit of the hydroxyl number of the component (A) is 3.0, 2.8, 2.5, 2.3, 2.0, 1.8, etc., and the lower limit is 2.8, 2.5, 2.3, 2.0, 1.8, 1.5, etc. The hydroxyl number of the component (a 1) is preferably 1.5 to 3.0, more preferably 1.8 to 2.5, from the viewpoint that the cured product has excellent level difference adhesion and processability. In the present disclosure, the hydroxyl number can be determined by JIS K1557-1: 2007. Specifically, the hydroxyl number can be determined by an acetylation method. In the present disclosure, the so-called "level difference conformability" and "workability" have the same meanings as described in japanese patent application 2020-037689.
(a1) The upper limit of the content (solid content conversion) of the component (a 1) in 100 mass% (solid content conversion) of the total amount of the component (a 2) and the component (a 3-1) or the component (a 3-2) is 98 mass%, 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, etc., and the lower limit is 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 1 mass%, etc. In one embodiment, the total amount of the component (a 1), the component (a 2), and the component (a 3-1) or the component (a 3-2) is 100% by mass (in terms of solid content), and the content of the component (a 1) (in terms of solid content) is preferably about 1 to 98% by mass.
(a2) Composition of the components
(a2) The component is aliphatic polyisocyanate. Examples of the component (a 2) include aliphatic diisocyanate, aliphatic triisocyanate, aliphatic tetraisocyanate and the like.
Examples of the component (a 2) include linear aliphatic polyisocyanates, branched aliphatic polyisocyanates, alicyclic aliphatic polyisocyanates, and the like.
Examples of the linear aliphatic diisocyanate include trimethylene diisocyanate, tetramethylene diisocyanate, 1, 5-pentamethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, and the like.
Examples of the branched aliphatic diisocyanate include methyl 2, 6-diisocyanatohexanoate, trimethylhexamethylene diisocyanate, and the like.
Examples of alicyclic aliphatic diisocyanates include dicyclohexylmethane 4,4' -diisocyanate, isophorone diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, 1, 3-bis (i.e., bis) can), cyclohexane-1, 4-diylbis (methylene) diisocyanate, 1-methylcyclohexane-2, 4-diyl diisocyanate, 1, 4-cyclohexane diisocyanate, hydrogenated xylene diisocyanate, hydrogenated toluene diisocyanate, and norbornene diisocyanate.
Examples of the linear aliphatic triisocyanate include lysine triisocyanate and the like.
The component (a 2) is preferably an aliphatic diisocyanate, and more preferably a linear aliphatic diisocyanate and/or a cycloaliphatic diisocyanate, from the viewpoint of excellent durability after the wet heat resistance test and excellent level difference adhesion of the cured product. In the present disclosure, the so-called "durability after wet heat resistance test" is the same as that described in japanese patent application 2020-037689.
(a2) The isocyanate group mole number (NCO (a2) ) Hydroxyl mole number (OH) of component (a 1) (a1) ) Ratio (NCO) (a2) /OH (a1) ) The upper limit of (2) is exemplified by 2.0, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2The lower limits of 1.1, 1.0, 0.9, 0.8, 0.7, 0.6, etc. are exemplified by 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, 1.1, 1.0, 0.9, 0.8, 0.7, 0.6, 0.5, etc. (a2) The isocyanate group mole number (NCO (a2) ) Hydroxyl mole number (OH) of component (a 1) (a1) ) Ratio (NCO) (a2) /OH (a1) ) Preferably about 0.5 to 2.0.
The upper limit of the molecular weight of the component (a 2) in the case of calculation based on the atomic weight may be 1000, 950, 900, 850, 800, 750, 700, 650, 600, 550, 500, 450, 400, 350, 300, 250, 200, 150, 100, 50, 25, etc., and the lower limit may be 950, 900, 850, 800, 750, 700, 650, 600, 550, 500, 450, 400, 350, 300, 250, 200, 150, 100, 50, 25, 10, etc. In one embodiment, the molecular weight of the component (a 2) is preferably 10 to 1000 based on the atomic weight calculation.
(a1) The upper limit of the ratio (mass ratio, in terms of solid content) of the component (a 1) to the component (a 2) is 99/1, 95/5, 90/10, 85/15, 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, 40/60, 35/65, 30/70, 25/75, 20/80, 15/85, 10/90, 5/95, etc., and the lower limit is 95/5, 90/10, 85/15, 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, 40/60, 35/65, 30/70, 25/75, 20/80, 15/85, 10/90, 5/95, 1/99, etc. In one embodiment, the content ratio (mass ratio, solid content conversion) of the component (a 1) to the component (a 2), component (a 1)/component (a 2), is preferably about 1/99 to 99/1.
(a1) The upper limit of the content (solid content conversion) of the component (a 2) in 100 mass% (solid content conversion) of the component (a 2) and the component (a 3-1) is 98 mass%, 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, etc., and the lower limit is 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%, 1 mass%, etc. In one embodiment, the total amount of the component (a 1), the component (a 2), and the component (a 3-1) or the component (a 3-2) is 100% by mass (in terms of solid content), and the content of the component (a 2) (in terms of solid content) is preferably about 1 to 98% by mass.
Component (a 3-1) or component (a 3-2)
The component (a 3-1) is a hydroxyl group-containing mono (meth) acrylate, and the component (a 3-2) is an isocyanate group-containing mono (meth) acrylate. The adhesive composition is excellent in curability because of the use of the component (a 3-1) or the component (a 3-2). When an adhesive composition containing no component (a 3-1) or component (a 3-2) is produced, curing failure occurs, and the cured product becomes too soft at room temperature. When a substrate containing such a cured product is cut, the cured product tends to adhere to the blade surface of the cutting equipment (i.e., workability is deteriorated), so that an adhesive composition containing no component (a 3-1) or component (a 3-2) is not preferable.
Examples of the component (a 3-1) include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxyethyl phthalate, glycerol mono (meth) acrylate, and 2-hydroxy-3-phenoxypropyl (meth) acrylate.
Examples of the component (a 3-2) include 2-isocyanatoethyl (meth) acrylate (2-b) and the like.
The component (a 3-1) or the component (a 3-2) is preferably a hydroxyl group-containing mono (meth) acrylate having 5 to 10 carbon atoms, and more preferably at least one selected from the group consisting of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and hydroxybutyl (meth) acrylate, because the adhesive composition is excellent in curability.
The upper limit of the number of carbon atoms of the component (a 3-1) or the component (a 3-2) is 60, 50, 40, 30, 20, 10, 9, 8, 7, 5, 4, etc., and the lower limit is 50, 40, 30, 20, 10, 9, 8, 7, 5, 4, 3, etc. In one embodiment, the number of carbon atoms in the component (a 3-1) or the component (a 3-2) is preferably about 4 to 60.
The upper limit of the molecular weight of the component (a 3-1) or the component (a 3-2) in the case of calculation based on the atomic weight may be 1000, 950, 900, 850, 800, 750, 700, 650, 600, 550, 500, 450, 400, 350, 300, 250, 200, 150, 100, 50, 25, etc., and the lower limit may be 950, 900, 850, 800, 750, 700, 650, 600, 550, 500, 450, 400, 350, 300, 250, 200, 150, 100, 50, 25, 10, etc. In one embodiment, the molecular weight of the component (a 3-1) or the component (a 3-2) in the case of calculation based on the atomic weight is preferably 10 to 1000.
(a1) The upper limit of the ratio (mass ratio, in terms of solid content) of the component (a 1) or (a 2) to the component (a 3-1) or (a 3-2), the ratio of the component (a 1) or (a 2)/(component a 3-1) or (a 3-2), may be 99.9/0.1, 99.5/0.5, 99/1, 95/5, 90/10, 85/15, 80/20, 75/25, etc., and the lower limit may be 99.5/0.5, 99/1, 95/5, 90/10, 85/15, 80/20, 75/25, 70/30, etc. In one embodiment, the content ratio (mass ratio, in terms of solid content, of the component (a 1) or the component (a 2) to the component (a 3-1) or the component (a 3-2) is preferably about 70/30 to 99.9/0.1.
(a1) The upper limit of the content (solid content conversion) of the component (a 3-1) or the component (a 3-2) in 100 mass% (solid content conversion) is preferably 20 mass%, 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, or the like, and the lower limit is preferably 15 mass%, 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1 mass%, 0.5 mass%, or the like. In one embodiment, the content of the component (a 3-1) or the component (a 3-2) (in terms of solid content) is preferably about 0.1 to 20% by mass, based on 100% by mass of the total of the component (a 1), the component (a 2) and the component (a 3-1) or the component (a 3-2) (in terms of solid content).
Other additives which can be mixed with component (A)
The component (A) may contain various additives as required. The additive may be any of various known additives. The additives may be used singly or in combination of two or more.
Examples of the additives include catalysts, crystal nucleating agents, crystal accelerators, chain transfer agents, and the like.
(A) The component (c) is not particularly limited, and for example, the component (a 1) and the component (a 2) may be reacted to obtain an isocyanate group-terminated urethane prepolymer, and then the isocyanate group-terminated urethane prepolymer may be reacted with the component (a 3-1). The reaction conditions are not particularly limited, and the reaction time is about 1 to 5 hours, with a typical temperature of about 70 to 85 ℃. The ratio of the isocyanate group-terminated urethane prepolymer to the component (a 3-1) is not particularly limited, but the ratio of the number of moles of isocyanate groups (NCO) to the number of moles of hydroxyl groups (OH) of the former (NCO/OH) is usually preferably in the range of about 0.25 to 1.
(A) The component (a) may be obtained by reacting the component (a 1) with the component (a 2) to obtain a hydroxyl-terminated urethane prepolymer, and then reacting the hydroxyl-terminated urethane prepolymer with the component (a 3-2). The reaction conditions are not particularly limited, and the reaction time is about 1 to 5 hours, with a typical temperature of about 70 to 85 ℃. The ratio of the hydroxyl-terminated urethane prepolymer to the component (a 3-2) is not particularly limited, but the ratio (NCO/OH) of the number of moles of isocyanate groups (NCO) to the number of moles of hydroxyl groups (OH) of the former is usually preferably in the range of about 0.5 to 1.
(A) The upper limit of the weight average molecular weight of the component is 100000, 90000, 80000, 70000, 60000, 50000, and the like, and the lower limit is 90000, 80000, 70000, 60000, 50000, 40000, and the like. The weight average molecular weight of the component (a) is 40000 to 100000, preferably 40000 to 90000, from the viewpoint that the cured product has excellent adhesion, level difference adhesion and bending resistance. (A) When the weight average molecular weight of the component is less than the lower limit, the adhesive force of the cured product becomes weak, and the bending resistance tends to be deteriorated; above the upper limit, the viscosity of the adhesive composition increases, and the adhesive composition tends to be difficult to manufacture. In the present disclosure, the weight average molecular weight is a polystyrene equivalent obtained by gel permeation chromatography.
(A) The upper limit of the number of (meth) acryloyl groups in the component (a) may be 15, 10, 8, 6, 4, 2, etc., and the lower limit may be 10, 8, 6, 4, 2, 1, etc. In one embodiment, the number of (meth) acryloyl groups in the component (a) is preferably about 1 to 15.
(A) The upper limit of the (meth) acrylic equivalent weight (g/eq) of the component(s) is 100000, 90000, 80000, 70000, 60000, 50000, 40000, 30000, 20000, 10000, etc., and the lower limit is 90000, 80000, 70000, 60000, 50000, 40000, 30000, 20000, 10000, 5000, etc. In one embodiment, the (meth) acrylic acid equivalent (g/eq) of the component (A) is preferably about 5000 to 100000. In the present disclosure, the (meth) acrylic equivalent weight is expressed as a weight average molecular weight per (meth) acrylic group, and can be calculated from "weight average molecular weight/number of functional groups".
The upper limit of the content (solid content conversion) of the component (a) in 100 mass% (solid content conversion) of the total amount of the component (a), the lower limit of the content (solid content conversion) of the component (B), the upper limit of the content (a) in 35 mass%, 34 mass%, 33 mass%, 32 mass%, 31 mass%, 30 mass%, 29 mass%, 28 mass%, 27 mass%, 26 mass%, 25 mass%, 24 mass%, 23 mass%, 22 mass%, 21 mass%, and the like are exemplified, and the lower limit of the content (a) in the total amount of the component (a), the component (B), the solid content conversion) in the total amount of the component (C) is 34 mass%, 33 mass%, 32 mass%, 31 mass%, 30 mass%, 29 mass%, 28 mass%, 27 mass%, 26 mass%, 25 mass%, 24 mass%, 23 mass%, 22 mass%, 21 mass%, 20 mass% and the like. In one embodiment, the total amount of the component (a), the component (B) and the component (C) is 100% by mass (in terms of solid content), and the content of the component (a) (in terms of solid content) is 20 to 35% by mass. (A) When the content of the component exceeds 35% by mass, the bending resistance is deteriorated, which is not preferable. The smaller the amount of the component (a), the better the bending resistance tends to be. If the content of the component (A) is less than 20% by mass, the curing is poor and the workability is deteriorated, which is not preferable.
(B) Composition of the components
(B) Alkyl mono (meth) acrylates having a glass transition temperature (also referred to herein as "Tg") of less than-50 ℃ of the composition being homopolymers. Since the adhesive composition of the present disclosure contains the component (B), the storage elastic modulus can be reduced, and good bending resistance can be obtained. The "glass transition temperature of the homopolymer" is a value recorded on Wiley-Interscience "polyethylene.
Examples of the component (B) include 2-ethylhexyl acrylate, n-octyl acrylate, lauryl methacrylate, isononyl acrylate, isodecyl acrylate, and n-butyl acrylate.
The component (B) is preferably 2-ethylhexyl acrylate from the viewpoint of excellent adhesion.
(B) The upper limit of the number of carbon atoms of the component (a) is 30, 25, 20, 15, 10, 9, 8, 7, 6, 5, 4, 3, etc., and the lower limit is 25, 20, 15, 10, 9, 8, 7, 6, 5, 4, 3, 2, etc. In one embodiment, the number of carbon atoms of the component (B) is preferably 6 to 15.
(B) The upper limit of Tg of the component is exemplified by-50 ℃, -51 ℃, -52 ℃, -53 ℃, -54 ℃, -55 ℃, -56 ℃, -57 ℃, -58 ℃, -59 ℃, -60 ℃, -61 ℃, -62 ℃, -63 ℃, -64 ℃, -65 ℃, -66 ℃, -67 ℃, -68 ℃, -69 ℃, and the lower limit is exemplified by-51 ℃, -52 ℃, -53 ℃, -54 ℃, -55 ℃, -56 ℃, -57 ℃, -58 ℃, -59 ℃, -60 ℃, -61 ℃, -62 ℃, -63 ℃, -64 ℃, -65 ℃, -66 ℃, -67 ℃, -68 ℃, -69 ℃, and-70 ℃. In one embodiment, the Tg of component (B) is less than-50℃and preferably about-70 to-50 ℃.
(A) The upper limit of the ratio (mass ratio, solid content conversion) of the component (A)/component (B) is exemplified by 50/50, 45/55, 40/60, 35/65, 30/70, 25/75, 20/80, 15/85, etc., and the lower limit is exemplified by 45/55, 40/60, 35/65, 30/70, 25/75, 20/80, 15/85, 10/90, etc. In one embodiment, the content ratio (mass ratio, solid content conversion) of the component (A) to the component (B) is preferably about 10/90 to 50/50.
The upper limit of the content (solid content conversion) of the component (B) in 100 mass% (solid content conversion) of the component (a), the upper limit of the content (solid content conversion) of the component (B) is 60 mass%, 59 mass%, 58 mass%, 57 mass%, 56 mass%, 55 mass%, 54 mass%, 53 mass%, 52 mass%, 51 mass%, 50 mass%, 49 mass%, 48 mass%, 47 mass%, 46 mass%, 45 mass%, 44 mass%, 43 mass%, 42 mass%, 41 mass%, etc., and the lower limit of the content (solid content conversion) of the component (B) is 59 mass%, 58 mass%, 57 mass%, 56 mass%, 55 mass%, 54 mass%, 53 mass%, 52 mass%, 51 mass%, 50 mass%, 49 mass%, 48 mass%, 47 mass%, 46 mass%, 45 mass%, 44 mass%, 43 mass%, 42 mass%, 41 mass%, 40 mass%, etc. In one embodiment, the total amount of the component (a), the component (B) and the component (C) is about 40 to 60 mass% in terms of solid content, based on 100 mass% (in terms of solid content). (B) When the content of the component is less than 40% by mass, the bending resistance is not preferable. (B) When the content of the component exceeds 60 mass%, poor curing and poor workability are caused, which is not preferable.
(C) Composition of the components
(C) The component (C) is mono (methyl) acrylic ester containing primary hydroxyl. The adhesive composition has excellent curability due to the use of the component (C), and the cured product has excellent durability after the wet heat resistance test. When a mono (meth) acrylate containing no hydroxyl group is used as a substitute for the component (C), the durability after the wet heat resistance test and the haze value after the wet heat resistance test are deteriorated. In addition, when a secondary hydroxyl group-containing mono (meth) acrylate is used as a substitute for the component (C), the haze value after the wet heat resistance test becomes poor. In this disclosure, the "haze value after the wet heat resistance test" is the same as that described in Japanese patent application 2020-037689.
Examples of the component (C) include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and cyclohexanedimethanol mono (meth) acrylate.
The component (C) is preferably 2-hydroxyethyl (meth) acrylate and/or 4-hydroxybutyl (meth) acrylate, from the viewpoint that the adhesive composition has excellent curability and the cured product has excellent durability after a wet heat resistance test.
(A) The upper limit of the ratio (mass ratio, solid content conversion) of the component (A)/component (C) is 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, etc., and the lower limit is 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, 40/60, etc. In one embodiment, the content ratio (mass ratio, solid content conversion) of the component (A) to the component (C) is preferably about 40/60 to 80/20.
(B) The upper limit of the ratio (mass ratio, in terms of solid content) of the component (B)/component (C) is 95/5, 90/10, 85/15, 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, etc., and the lower limit is 90/10, 85/15, 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, etc. In one embodiment, the content ratio (mass ratio, solid content conversion) of the component (B) to the component (C) is preferably about 50/50 to 95/5.
The upper limit of the content (solid content conversion) of the component (C) in 100 mass% (solid content conversion) of the total amount of the component (a), the component (B), and the component (C) is exemplified by 30 mass%, 29 mass%, 28 mass%, 27 mass%, 26 mass%, 25 mass%, 24 mass%, 23 mass%, 22 mass%, 21 mass%, 20 mass%, 19 mass%, 18 mass%, 17 mass%, 16 mass%, 15 mass%, 14 mass%, 13 mass%, 12 mass%, 11 mass%, and the like, and the lower limit thereof is exemplified by 29 mass%, 28 mass%, 27 mass%, 26 mass%, 25 mass%, 24 mass%, 23 mass%, 22 mass%, 21 mass%, 20 mass%, 19 mass%, 18 mass%, 17 mass%, 16 mass%, 15 mass%, 14 mass%, 13 mass%, 12 mass%, 11 mass%, 10 mass%, and the like. In one embodiment, the content (in terms of solid content) of the component (C) is preferably about 10 to 30% by mass, based on 100% by mass (in terms of solid content) of the total of the component (a), the component (B) and the component (C).
(D) Composition of the components
The adhesive composition of the present disclosure preferably contains a photo radical polymerization initiator (hereinafter also referred to as "component (D)") because the cured product has excellent curability.
As the component (D), an alkylbenzene type photopolymerization initiator, an acylphosphine oxide type photopolymerization initiator, a hydrogen abstraction type photopolymerization initiator, an oxime ester type photopolymerization initiator, and the like can be mentioned.
Examples of the alkyl benzophenone photopolymerization initiator include benzyl dimethyl ketal (e.g., 2-dimethoxy-1, 2-diphenyl-1-ethanone, etc.), α -hydroxyalkyl phenone (e.g., 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propanone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, etc.), α -aminoalkylphenone (e.g., 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-propanone, etc.), and the like.
Examples of the acylphosphine oxide type photopolymerization initiator include 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide and phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide.
Examples of the hydrogen abstraction photopolymerization initiator include methyl phenylglyoxylate.
Examples of the oxime ester type photopolymerization initiator include 1- [4- (phenylthio) phenyl ] -1, 2-octanedione 2- (O-benzoyl oxime) and 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone 1- (O-acetyl oxime).
The component (D) is preferably an α -hydroxyalkyl benzophenone type photopolymerization initiator and/or an acylphosphine oxide type photopolymerization initiator, from the viewpoint of excellent curability of the adhesive composition.
The upper limit of the content (solid content conversion) of the component (D) in 100 mass% (solid content conversion) of the total amount of the component (a), the component (B), and the component (C) is 10 mass%, 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1.5 mass%, 1 mass%, 0.5 mass%, 0.2 mass%, and the like, and the lower limit thereof is 9 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 4 mass%, 3 mass%, 2 mass%, 1.5 mass%, 1 mass%, 0.5 mass%, 0.2 mass%, 0.1 mass%, and the like. In one embodiment, the content (in terms of solid content) of the component (D) is preferably 0.1% by mass or more and 3% by mass or less, more preferably 0.1% by mass or more and 2% by mass or less, still more preferably 0.1% by mass or more and 1.5% by mass or less, in the total amount of the component (a), (B) and (C) being 100% by mass (in terms of solid content).
Other possible additives
The adhesive composition of the present disclosure may contain various additives as needed. Examples of the additives include surface-modifying agents, surfactants, ultraviolet absorbers, antioxidants, light stabilizers, tackifiers, inorganic fillers, silane coupling agents, colloidal silica, antifoaming agents, wetting agents, rust inhibitors, plasticizers, chain transfer agents, photosensitizers, and the like.
The adhesive composition of the present disclosure may contain (meth) acrylate (E) having a glass transition temperature of a homopolymer exceeding-50 ℃, but the lower the content of the (E) component in the adhesive composition of the present disclosure, the better the bending resistance tends to be. Therefore, when the total of the components (a), (B), (C) and (E) is 100% by mass, the upper limit of the content (mass%) of the component (E) is 13, 10, 8, 6, 4, 2, 1, etc., and the lower limit is 10, 8, 6, 4, 2, 1, 0, etc. When the total of the components (a), (B), (C) and (E) is 100% by mass, the content (mass%) of the component (E) is preferably 13% by mass or less.
The adhesive composition of the present disclosure may contain a tackifier resin having a softening temperature of 100 ℃ or more and 150 ℃ or less as the component (F). In the case where the component (F) is contained in the adhesive composition of the present disclosure, the tackiness of the cured product is improved, but on the other hand, in the case where the content is excessive, the bending resistance of the cured product is adversely affected, and therefore, in the case where the total of the component (a), the component (B) and the component (C) is taken as 100 mass%, the content (mass%) of the component (F) in terms of solid content is preferably less than 1 mass%, and more preferably 0 mass%. Examples of the component (F) include hydroxyl group-containing petroleum resins, disproportionated rosin resins, hydrogenated rosin resins, and the like.
The adhesive composition of the present disclosure may also contain a solvent. Examples of the solvent include ketone solvents, aromatic solvents, alcohol solvents, glycol ether solvents, ester solvents, petroleum solvents, halogenated hydrocarbon solvents, and amide solvents.
Examples of the ketone solvent include methyl ethyl ketone, acetyl acetone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone.
Examples of the aromatic solvent include toluene and xylene.
Examples of the alcohol solvent include methanol, ethanol, n-propanol, isopropanol, butanol, and the like.
Examples of the glycol solvent include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol.
Examples of the glycol ether solvent include ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, and ethylene glycol mono-t-butyl ether.
Examples of the ester solvent include ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, and the like.
Examples of the petroleum solvent include T-SOL 100 (manufactured by ENEOS Co., ltd.), and T-SOL 150 (manufactured by ENEOS Co., ltd.).
Examples of the halogenated alkane solvent include chloroform.
Examples of the amide solvent include dimethylformamide.
The adhesive compositions of the present disclosure may also be used without a solvent. Therefore, the adhesive composition of the present disclosure preferably contains no solvent from the viewpoint of being able to suppress cost and influence on the environment.
The upper limit of the viscosity (mPas/25 ℃) of the adhesive composition of the disclosure may be 10000, 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, 1000, 500, 300, etc., and the lower limit may be 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, 1000, 500, 300, 100, etc. The viscosity (mPas/25 ℃) of the adhesive composition of the present disclosure is preferably 100 or more and 10000 or less, more preferably 300 or more and 8000 or less, still more preferably 500 or more and 7000 or less, from the viewpoint that the adhesive composition has excellent handling properties. The viscosity in the present disclosure is a measured value (5 minutes) by an E-type viscometer (product name "TVE-10", manufactured by UK.K.).
The adhesive composition of the present disclosure is prepared by mixing the (a), (B) and (C) components, and if necessary (D), (E), (F) and other possible additives. The order of mixing is not particularly limited, and may be sequentially mixed, or may be mixed all at once.
Cured product
Products cured by irradiation of the adhesive composition with active energy rays such as ultraviolet rays are also an aspect of the present disclosure. When the adhesive composition contains a solvent, it is conceivable to perform a drying treatment before irradiation with ultraviolet rays. The adhesive composition may be coated on various substrates to form an adhesive composition layer, and the layer may be irradiated with ultraviolet rays to obtain a cured product.
Examples of the ultraviolet light source include an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, and a metal halide lamp. In this apparatus, conditions such as the irradiation intensity of ultraviolet rays, the cumulative light amount, and the conveyance speed in the apparatus are not particularly limited, and the irradiation intensity is usually 80mW/cm 2 Above and 160mW/cm 2 The transport speed is 3 to 50 m/min, and the cumulative light amount is 100mJ/cm 2 Above and 3000mJ/cm 2 The following is given.
Examples of the method for applying the adhesive composition include bar coating, mayer bar coating, air knife coating, gravure coating, reverse gravure coating, offset printing, flexographic printing, screen printing, and the like.
The coating weight is generally 1g/m of dry mass 2 Above and 1000g/m 2 Hereinafter, it is preferably 3g/m 2 Above 500g/m 2 The following ranges.
The thickness of the cured product of the present disclosure is not particularly limited, and from the viewpoint of suitably exhibiting the level difference adhesion and the bubble generation resistance of the cured product, the film thickness after drying is preferably 10 μm or more and 1000 μm or less, and more preferably 25 μm or more and 500 μm or less.
The cured product of the present disclosure preferably has a storage elastic modulus G '(also referred to as "G'" in the present disclosure) of 5.5×10 at 25 ℃ and 1Hz 4 Pa or less, more preferably 1.0X10 4 Pa or more and 5.5X10 4 Pa or less, and more preferably 1.0X10 4 Pa or more and 5.0X10 4 Pa or less, particularly preferably 1.0X10 4 Pa or more and 4.0X10 4 Pa or less, more particularly preferably 1.0X10 4 Pa or more and 3.0X10 4 Pa or less, most preferably 1.0X10 4 Pa or more and 2.5X10 4 Pa or below. Furthermore, the storage elastic modulus G' at-20℃and 1Hz is preferably 2.5X10 5 Pa or less, more preferably 5.0X10 4 Pa or more and 2.5X10 5 Pa or less, more preferably 5.0X10 4 Pa or more and 2.0X10 5 Pa or less, particularly preferably 5.0X10 4 Pa or more and 1.5X10 5 Pa or less, more particularly preferably 5.0X10 4 Pa or more and 1.0X10 5 Pa or less, most preferably 5.0X10 4 Pa or more and 8.0X10 4 Pa or below. With these characteristics, the cured product is considered to have excellent bending resistance at room temperature or in cold weather. In the present disclosure, the storage elastic modulus of the cured product can be determined by JIS K7244-1: 1998. In particular, the storage elastic modulus can be measured as described in the examples.
Molded article
Examples of suitable adhesive compositions include coatings between substrates of various known articles. These articles are not particularly limited, and may be various known articles.
Examples of the article include a body of a home electric appliance such as a television and a remote controller thereof, and a casing and a display of an information terminal such as a mobile phone, a smart phone, a tablet pc, and a personal computer.
The active energy ray curable adhesive composition of the present disclosure is suitable for optical applications, preferably as an Optically Clear Adhesive (OCA). For example, it is applicable to a display panel of a multi-layer structure in a digital display device. Further, since the cured product of the present disclosure is excellent in bending resistance, it is particularly considered to be used for a foldable apparatus.
Substrate for use
Examples of the substrate coated with the adhesive composition of the present disclosure include glass substrates, plastic substrates, paper substrates, cloth substrates, rubber sheet substrates, foam sheet substrates, metal substrates, and the like. Examples of the plastic substrate include thermoplastic plastic substrates and thermosetting plastic substrates. Examples of the thermoplastic base material include general-purpose plastic base materials and engineering plastic base materials. Examples of the general-purpose plastic base material include olefins, polyesters, acrylics, vinyls, and polystyrenes. Examples of the olefins include polyethylene, polypropylene, and norbornene. Examples of polyesters include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene succinate (PBS), polybutylene succinate adipate (PBSA), polybutylene adipate terephthalate (PBAT), polylactic acid (PLA), polyhydroxyalkanoic acid (PHA), and Polycaprolactone (PCL). Examples of the acrylic include polymethyl methacrylate (PMMA). Examples of the vinyl include polyvinyl chloride, polyvinylidene chloride, and polyvinyl alcohol. Examples of the polystyrene include Polystyrene (PS) resin, styrene Acrylonitrile (AS) resin, and styrene butadiene Acrylonitrile (ABS) resin. Examples of the engineering plastic base material include general-purpose engineering plastics and super engineering plastics. Examples of the general-purpose engineering plastic include polycarbonate and polyamide (nylon). As the super engineering plastic, polyether ether ketone (PEEK) and the like can be cited. Examples of the thermosetting plastic base material include polyimide, epoxy resin, melamine resin, and the like. As the other plastic base material, triacetyl cellulose resin and the like can be cited. Examples of the paper base material include japanese paper, kraft paper, cellophane paper, high-quality paper, synthetic paper, surface-coated paper, and the like. The cloth base material may be a woven cloth or a nonwoven cloth obtained by singly or by mixing various fibrous materials. Examples of the rubber sheet base material include natural rubber and butyl rubber. Examples of the foam sheet base material include foamed polyurethane, foamed neoprene, and the like. Examples of the metal substrate include aluminum foil and copper foil. In addition, the substrate may be subjected to a surface treatment (e.g., corona discharge, etc.). In addition, other layers (e.g., easy adhesion layers, anchor layers, etc.) may be disposed between the adhesive composition layers of the present disclosure on one or both sides of the substrate. The substrate is preferably a substrate for optical use. Examples of the optical substrate include polyester films such as polyethylene terephthalate (PET), polybutylene terephthalate, and polyethylene naphthalate (PEN), plastic films such as polyethylene films, polypropylene films, cellophane, diacetyl cellulose films, triacetyl cellulose films, acetyl cellulose butyrate films, polyvinyl chloride films, polyvinylidene chloride films, polyvinyl alcohol films, ethylene-vinyl acetate copolymer films, polystyrene films, polycarbonate films, polymethylpentene films, polysulfone films, polyetheretherketone films, polyethersulfone films, polyetherimide films, polyimide films, fluororesin films, polyamide films, acrylic resin films, norbornene resin films, cycloolefin resin films, glass, tin-doped indium oxide films, ITO films, transparent conductive films, and the like. The thickness of the base material is not particularly limited, but is usually about 30 to 300. Mu.m.
Specifically, as a combination of the cured product of the present disclosure and the optical substrate, the following and the like are exemplified:
(1) Substrate, cured product of the present disclosure, and transparent conductive film (also referred to as "ITO" in the present disclosure)
(2) Substrate, cured product of the present disclosure, liquid crystal display.
Examples
The present disclosure will be further specifically described below by way of examples of production, comparative production, examples, comparative examples, evaluation examples, and comparative evaluation examples, but the present disclosure is not limited to the examples. In the following description, parts and% are based on mass.
The weight average molecular weight (Mw) in the present disclosure is determined by Gel Permeation Chromatography (GPC) under the following conditions.
(GPC measurement conditions)
Model: product name "HLC-8220GPC" (manufactured by Seattle Co., ltd.)
Column: the product name "TSKgel G1000H" and "TSKgel G2000H" (manufactured by Tonka Kogyo Co., ltd.)
Developing solvent: tetrahydrofuran (THF)
Flow rate: 0.6 mL/min
Measuring temperature: 40 DEG C
A detector: differential refraction detector (RI: refractive Index Detector)
Standard substance: monodisperse polystyrene
Sample: a tetrahydrofuran solution having a concentration of 0.2% based on the solid content was prepared from the resin, and 20. Mu.L of the solution was filtered through a microfilter.
In each production example, the NCO measurement method of the urethane prepolymer is as follows.
Measuring device main body: potential difference automatic titration apparatus (product name "AT-400", manufactured by Kyoto electric industry and model Co., ltd.)
Measurement procedure:
1: samples of about 0.500g to 1.000g were weighed in weighing bottles.
2: 10mL of a toluene solution of 0.15mol/L dibutylamine was injected.
3: the weighing bottle with the sample is put into an ultrasonic cleaner to dissolve the sample completely.
4: after confirming complete dissolution of the sample, it was left for 15 minutes (no direct sunlight or high temperature place).
5: after 15 minutes, 100mL of isopropanol was added to the weighing flask. The stirring sheet was placed in a weighing flask.
6: the NCO value was obtained by titration with a 0.1mol/L hydrochloric acid solution (f=1.00).
The sample to be measured is input into an automatic titrator for measurement. If the measurement difference is within 0.30, it is acceptable. If the value is 0.30 or more, the measurement is performed again, and the value is confirmed to be within 0.30. Production example 1: preparation of the component (A-1)
To a reaction apparatus equipped with a condenser, a stirrer and a nitrogen gas pipe, 884 parts of polyethylene glycol having a number average molecular weight of 2000 (product name: d) P-2000 (also referred to as "PPG2000" in the present disclosure), manufactured by ADEKA corporation), 106 parts of isophorone diisocyanate (also referred to as "IPDI" in the present disclosure), 333 parts of 2-ethylhexyl acrylate (also referred to as "2EHA" in the present disclosure), and 0.4 part of stannous octoate were added, and after heating to 80 ℃ and maintaining the temperature for 3 hours, a 2EHA solution of an intermediate isocyanate group-terminated urethane prepolymer was obtained. Then, 10 parts of 4-hydroxybutyl acrylate (also referred to as "4HBA" in the present disclosure) was added, and after completion of the reaction as determined by NCO measurement, a 2EHA solution of urethane acrylate (A-1) (also referred to as "(A-1) component" in the present disclosure) having a weight average molecular weight of 55000, an average number of acryl groups of 2, and an acrylic acid equivalent of 27500 was obtained.
Comparative manufacturing example 1: preparation of the (A-C1) component
In the same reactor as in production example 1, 2000 877 parts of PPG, 110 parts of IPDI and 0.5 part of stannous octoate were added, and the mixture was heated to 80℃and incubated for 3 hours to obtain an intermediate isocyanate group-terminated urethane prepolymer. Then, 13 parts of 2-hydroxyethyl acrylate (also referred to as "HEA" in the present disclosure) was added, and after completion of the reaction as determined by NCO measurement, urethane acrylate (A-C1) (also referred to as "(A-C1) component in the present disclosure) having a weight average molecular weight of 38000, an average number of acryl groups of 2 and an acrylic acid equivalent of 19000 was obtained.
Example 1: preparation of adhesive composition (1)
25 parts of component (A-1), 54 parts of 2-EHA as component (B), 21 parts of 4HBA as component (C) and 0.25 part of 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (product name "JRcure TPO" (also referred to as "TPO" in the present disclosure) as component (D)) were mixed to obtain an adhesive composition (1).
Examples 2 to 4 and comparative examples 1 to 3: adhesive compositions (2) to (4) and adhesive compositions (C1) to (C3)
The procedure of example 1 was conducted in the same manner except that the components were changed as shown in Table 1. Performance evaluation (1): storage elastic modulus (G')
The adhesive compositions (1) to (4) and (C1) to (C3) were applied to a 75 μm thick, heavy-release-treated polyester film (product name "SP-PET-03-75BU", manufactured by Mitsui chemical Fangji Co., ltd.) respectively, the film thickness of the cured product after curing was 100. Mu.m, and a 38 μm thick, light-release-treated polyester film (product name "SP-PET-01-38BU", manufactured by Mitsui chemical Fangji Co., ltd.) was laminated to the adhesive composition-coated layer. Then, the obtained coating film was subjected to a high-pressure mercury lamp (100 mW/cm 2 、900mJ/cm 2 ) Ultraviolet irradiation was performed to prepare a laminate containing a cured product (light-release-treated polyester film/cured product/heavy-release-treated polyester film). Then, a 1 cm. Times.1 cm test piece was cut out from the laminate. Then, the light-release-treated polyester film and the heavy-release-treated polyester film were peeled off from the test piece to obtain cured products (1) to (4) and (C1) to (C3).
The cured products (1) to (4) and (C1) to (C3) were measured by a commercially available measuring apparatus (product name "MCR302", available from the company of the Takara Shuzo), the dynamic viscoelasticity was measured under the following conditions. Then, the storage elastic modulus G 'at-20℃and 1Hz and the storage elastic modulus G' at 25℃and 1Hz were obtained from the measurement results.
(measurement conditions)
The deformation mode is as follows: torsion
Measuring frequency: 1Hz
Deformation: 0.01 to 1 percent of automatic setting
Rate of temperature rise: 3 ℃/min
Measuring temperature: -80-100 DEG C
Shape: parallel plates 8.0mm phi
Performance evaluation (2): bending resistance
The laminate (light peeling-treated polyester film/cured product/heavy peeling-treated polyester film) obtained in the same manner as in the performance evaluation (1) was cut into dimensions of 25mm×150 mm. Then, the cut laminate was peeled off lightly, and a polyester film having a thickness of 50 μm (manufactured by Toyo , product name "コ s" a-4300 ") was attached to the surface of the cured product exposed after the peeling. Then, the heavy release-treated polyester film was peeled off, and a polyester film having a thickness of 50 μm was bonded to the surface of the cured product exposed after the peeling. The laminate was treated in an autoclave at 50℃under 0.5MPa for 20 minutes to prepare a sample for bending test. The two ends of the obtained test piece were fixed to two holding plates of a surface state no-load U-type tensile tester (company, product name "Chamber-FS"). The test was repeated by bending at a radius of curvature (R) =1 mm and a bending speed of 60rpm in an environment having an ambient temperature of-20 ℃ and 25 ℃ and then fully expanding the sheet. Immediately after the completion of the test, the bending portion of the sample for bending test was observed with a magnifying glass, and the bending resistance was evaluated according to the following evaluation criteria.
5: no abnormality was observed at both the bending 15000 times and the bending 100000 times.
4: no abnormality was observed when bending 15000 times, but any one of peeling of the base material, positional displacement of the cured product, bubbles in the cured product, and breakage of the cured product was slightly observed when bending 100000 times.
3: no abnormality was observed when bending 15000 times, but peeling of the base material, positional displacement of the cured product, bubbles in the cured product, and breakage of the cured product were clearly observed when bending 100000 times.
2: when the sheet was bent 15000 times, peeling of the base material, positional displacement of the cured product, bubbles in the cured product, and breakage of the cured product were slightly observed.
1: when the sheet was bent 15000 times, peeling of the base material, positional displacement of the cured product, bubbles in the cured product, and breakage of the cured product were clearly observed.
TABLE 1
The meanings of the terms in Table 1 are as follows.
The values in the tables relating to the contents of the respective components are converted in terms of solid content.
2EHA: 2-ethylhexyl acrylate (product name "2-ethylhexyl acrylate", mitsubishi chemical industry Co., ltd.)
4HBA: 4-hydroxybutyl acrylate (product name "4-HBA", manufactured by Osaka organic chemical industry Co., ltd.)
TPO:2,4, 6-Trimethylbenzoyl-diphenylphosphine oxide (product name "JRcure TPO", new material of Tianjin Jiuzu)
IBXA: isobornyl acrylate (product name "IBXA", manufactured by Osaka organic chemical industries, ltd.)
Claims (6)
1. An active energy ray curable adhesive composition comprising:
(A) The method comprises the following steps (a1) A reaction product of a polyol, (a 2) an aliphatic polyisocyanate and (a 3-1) a hydroxyl group-containing mono (meth) acrylate or (a 3-2) an isocyanate group-containing mono (meth) acrylate, a urethane (meth) acrylate having a weight average molecular weight of 40000 or more and 100000 or less,
(B) The method comprises the following steps An alkyl mono (meth) acrylate having a glass transition temperature of-50 ℃ or lower,
(C) The method comprises the following steps Mono (meth) acrylates containing a primary hydroxyl group,
when the total of the components (A), (B) and (C) is 100% by mass, the content of the component (A) in terms of the solid content is 20% by mass or more and 35% by mass or less, and the content of the component (B) in terms of the solid content is 40% by mass or more and 60% by mass or less.
2. The active energy ray-curable adhesive composition according to claim 1, wherein the solid content of the component (C) is 10 to 30% by mass.
3. The active energy ray-curable adhesive composition according to claim 1 or 2, wherein the component (B) is at least one selected from the group consisting of 2-ethylhexyl acrylate, n-octyl acrylate, lauryl methacrylate, isononyl acrylate, isodecyl acrylate and n-butyl acrylate.
4. An active energy ray-curable adhesive composition according to any one of claims 1 to 3.
5. The cured product according to claim 4, wherein the storage elastic modulus G' at 25℃and 1Hz is 5.5X10% 4 Pa or lower, and a storage elastic modulus G' of 2.5X10 at-20 ℃ and 1Hz 5 Pa or below.
6. An adhesive sheet comprising the cured product according to claim 4 or 5 on at least one surface of a substrate.
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| JP6097132B2 (en) | 2013-04-22 | 2017-03-15 | 昭和電工株式会社 | Photocurable composition for transparent adhesive sheet, adhesive sheet using the same, and use thereof |
| JP6969235B2 (en) | 2016-09-05 | 2021-11-24 | 荒川化学工業株式会社 | UV curable adhesive, cured product, adhesive sheet |
| CN108285745B (en) | 2016-12-20 | 2021-08-13 | 荒川化学工业株式会社 | Ultraviolet-curable adhesive, cured product, and adhesive sheet |
| KR102208594B1 (en) * | 2018-10-30 | 2021-01-28 | 주식회사 엘지화학 | Photosensitive urethane-based resin, adhesive composition comprising the same, and adhesive |
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