JP6432225B2 - 粘着剤および粘着シート - Google Patents
粘着剤および粘着シート Download PDFInfo
- Publication number
- JP6432225B2 JP6432225B2 JP2014179830A JP2014179830A JP6432225B2 JP 6432225 B2 JP6432225 B2 JP 6432225B2 JP 2014179830 A JP2014179830 A JP 2014179830A JP 2014179830 A JP2014179830 A JP 2014179830A JP 6432225 B2 JP6432225 B2 JP 6432225B2
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- JP
- Japan
- Prior art keywords
- sensitive adhesive
- pressure
- meth
- weight
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000001070 adhesive effect Effects 0.000 title claims description 50
- 239000000853 adhesive Substances 0.000 title claims description 49
- -1 isocyanate compound Chemical class 0.000 claims description 108
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 83
- 239000000178 monomer Substances 0.000 claims description 56
- 239000012948 isocyanate Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229920000058 polyacrylate Polymers 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims description 8
- 239000012790 adhesive layer Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 150000003335 secondary amines Chemical class 0.000 description 26
- 239000010410 layer Substances 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 229920005672 polyolefin resin Polymers 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 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 10
- 239000010408 film Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate 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
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 239000013638 trimer Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 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 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011162 core material Substances 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
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- 229920002554 vinyl polymer Polymers 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- XHCSLCUESAXELX-UHFFFAOYSA-N 2-hex-5-enyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound C(O)C(CCCCC=C)(CO)CO XHCSLCUESAXELX-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
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- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920003050 poly-cycloolefin Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
Description
アクリル系重合体(A)がカルボキシル基含有モノマー0.3〜15重量%を含むモノマー混合物をラジカル重合してなる重合体、
イソシアネート化合物(B)が、3官能以上のイソシアネート化合物(b1)中のイソシアネート基100モルに対して、単官能アルコール(b2)及び第2級アミン(b3)のうち少なくともいずれか一方を合計5モル以上40モル未満反応してなる化合物であることを特徴とする。
アクリル系重合体(A)がカルボキシル基含有モノマー0.3〜15重量%を含むモノマー混合物をラジカル重合してなる重合体、
イソシアネート化合物(B)が、3官能のイソシアネート化合物(b1)中のイソシアネート基100モルに対して、単官能アルコール(b2)及び第2級アミン(b3)のうち少なくともいずれか一方を合計5モル以上40モル未満反応してなる化合物であることを特徴とする。
本発明の粘着剤は、塗工により粘着剤層を形成し、粘着シートとして使用することが好ましい。
ラジカル重合開始剤は、単独または2種以上を併用できる。
イソシアネート化合物(B)は、3官能以上のイソシアネート化合物(b1)と単官能アルコール(b2)との反応によりウレタン結合が、同じく第2級アミン(b3)との反応によりウレア結合がそれぞれ導入される。ウレタン結合またはウレタン結合の存在により粘着剤の凝集力が向上する。
トリメチロールブテン、トリメチロールヘプテン、トリメチロールペンテン、トリメチロールヘキセン、トリメチロールヘプテン、トリメチロールオクテン、トリメチロールデセン、トリメチロールドデセン、トリメチロールトリデセン、トリメチロールペンタデセン、トリメチロールヘキサデセン、トリメトロールヘプタデセン、トリメチロールオクタデセン、1,2,6−ブタントリオール、1,2,4−ブタントリオール、およびグリセリン等の3官能ポリオール;
ペンタエリスリトール、ジペンタエリスリトール、ソルビトール、およびキシリトール等の4官能以上のポリオール;
トリエチレンテトラミン、ジエチレントリアミン、およびトリアミノプロパン等のポリアミン;
ペンタエリスリトールテトラキス(3−メルカプトブチレート)等のポリチオールが挙げられる。
3官能以上のイソシアネート化合物(b1)は、単独または2種以上を併用できる。
単官能アルコール(b2)は、単独または2種以上を併用できる。
第2級アミン(b3)は、単独または2種以上を併用できる。
架橋剤は、単独または2種以上を併用できる。
ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリイソプロポキシシラン、ビニルトリブトキシシラン、ビニルメチルジメトキシシラン、およびビニルメチルジエトキシシラン等のビニル基を有するアルコキシシラン化合物;
3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、3−アミノプロピルトリプロポキシシラン、3−アミノプロピルメチルジメトキシシラン、3−アミノプロピルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジエトキシシラン、およびN−フェニル−3−アミノプロピルトリメトキシシラン等のアミノ基を有するアルコキシシラン化合物;
3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、3−メルカプトプロピルトリプロポキシシラン、3−メルカプトプロピルメチルジメトキシシラン、3−メルカプトプロピルメチルジエトキシシランなどのメルカプト基を有するアルコキシシラン化合物;
3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−グリシドキシプロピルトリプロポキシシラン、3−グリシドキシプロピルトリブトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン、および2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン等のエポキシ基を有するアルコキシシラン化合物;
テトラメトキシシラン、テトラエトキシシラン、テトラプロポキシシラン、およびテトラブトキシシラン等のテトラアルコキシシラン化合物;
3−クロロプロピルトリメトキシシラン、n−ヘキシルトリメトキシシラン、n−ヘキシルトリエトキシシラン、n−デシルトリメトキシシラン、n−デシルトリエトキシシラン、スチリルトリメトキシシラン、フェニルトリメトキシシラン、ジフェニルジメトキシシラン、3−トリエトキシシリル−N−(1,3−ジメチルブチリデン)プロピルアミン、1,3,5−トリス(3−トリメトキシシリルプロピル)イソシアヌレート、3−イソシアネートプロピルトリメトキシシラン、3−イソシアネートプロピルトリエトキシシラン、ヘキサメチルジシラザン、および分子内にアルコキシシリル基を有するシリコーンレジン等が挙げられる。
数式(1) ゲル分率(重量%)=(G2/G1)×100
G1:酢酸エチルで抽出する前の粘着剤層の重量
G2:酢酸エチルで抽出・乾燥した後の粘着剤層の重量
(合成例1−1)
撹拌機、温度計、還流冷却管、滴下装置、窒素導入管を備えた反応容器(以下、単に「反応容器」と記述する。)に窒素雰囲気下、アクリル酸ブチル95部、アクリル酸5部、酢酸エチル80部、2,2'−アゾビスイソブチロニトリル(以下「AIBN」と記述する。)0.015部を仕込んだ。撹拌しながら加熱を行い重合反応の開始を確認して還流温度で2時間反応した。次いで、AIBN 0.03部を反応溶液に添加し6時間反応を継続した。その後、反応容器を冷却し酢酸エチル120部を加え、不揮発分32.8%、重量平均分子量が109万のアクリル系重合体溶液を得た。
反応容器に窒素雰囲気下、アクリル酸ブチル90部、アクリル酸10部、酢酸エチル150部、AIBN 0.03部を仕込んだ。撹拌しながら加熱を行い重合反応の開始を確認して還流温度で2時間反応した。次いで、AIBN 0.03部を反応溶液に添加し6時間反応を継続した。その後、反応容器を冷却し酢酸エチル50部を加え、不揮発分33.0%、重量平均分子量が79万のアクリル系重合体溶液を得た。
モノマーの種類及び配合量を表1の記載に従った他は、合成例1−2と同様に行うことで合成例1−2〜1−10の重合体を得た。
各重合体溶液の外観を目視で評価した。
重量平均分子量の測定は島津製作所製GPC「LC−GPCシステム」を用いた。GPCは溶媒(THF;テトラヒドロフラン)に溶解した物質をその分子サイズの差によって分離定量する液体クロマトグラフィーであり、重量平均分子量の決定はポリスチレン換算で行った。
装置名 : 島津製作所社製、LC−GPCシステム「Prominence」
カラム : 東ソー社製GMHXL 4本、東ソー社製HXL-H 1本を直列に連結した。
移動相溶媒 : テトラヒドロフラン
流量 : 1.0ml/min
カラム温度 : 40℃
BA : アクリル酸ブチル
2EHA : アクリル酸2−エチルヘキシル
AA : アクリル酸
HEA : アクリル酸2−ヒドロキシエチル
(合成例2−1)
反応容器に窒素雰囲気下、コロネートL(TDI(トリレンジイソシアネート)のTMP(トリメチロールプロパン)アダクト体、日本ポリウレタン工業社製)75部、2−エチルヘキシルアルコール10部を仕込んだ。この反応容器を攪拌しながら80℃に加熱し、更に4時間反応させた。反応溶液のNCO価を測定し、NCO価を確認して、反応容器を冷却し反応を終了した。このイソシアネート化合物溶液は淡黄色透明な粘稠の液体であった。その結果を表2に示す。なお合成例の配合部数は不揮発分換算である。
表2の重量比率に従って各原料を仕込み、合成例2−1と同様の方法でイソシアネート化合物(B)を合成した。その結果を表2に示す。
共栓三角フラスコ中に試料を精密に量り採り、クロロベンゼン25ml、ジ−n−ブチルアミン/オルトジクロロベンゼン(重量比:ジ−n−ブチルアミン/オルトジクロロベンゼン=1/24.8)混合液10mlを加えて溶解する。これに、メタノール80g、ブロムフェノールブルー試薬を指示薬として加え、0.1Nアルコール性塩酸溶液で滴定した。溶液が黄緑色を呈し、30秒間保持するまで滴定を続けた。NCO価は次式により求めた。
ただし、W:試料の採取量(g)
B:試料滴定に要した0.1Nアルコール性塩酸溶液の消費量(ml)
C:空試験の滴定に要した0.1Nアルコール性塩酸溶液の消費量(ml)
F:0.1Nアルコール性塩酸溶液の力価
TDI/TMP : トリレンジイソシアネートのトリメチロールプロパンアダクト体(NCO価=13.2、不揮発分=75%)
IPDI/TMP : イソホロンジイソシアネートのトリメチロールプロパンアダクト体(NCO価=10.5、不揮発分=75%)
IPDI/ヌレート : イソホロンジイソシアネートのイソシアヌレート3量体(NCO価=11.8、不揮発分=70%)
合成例1−1で得られたアクリル系重合体溶液中のアクリル系重合体100部に対して、合成例2−1で得られたイソシアネート化合物2部、粘着付与剤としてA−100を25部配合し、更に溶剤として酢酸エチルを加えて不揮発分を30%に調整して粘着剤を得た。
前記粘着剤を、厚さ38μmの剥離性シート(ポリエチレンテレフタレート製)上に、乾燥後の厚さが25μmになるようにコンマコーターで塗工を行い、100℃で2分間乾燥することで粘着剤層を形成した。次いで、この粘着剤層に、厚さ50μmの基材(ポリエチレンテレフタレート製、以下、PETシートという)を貼り合せ、温度23℃相対湿度50%の条件で1週間熟成することで「剥離性シート/粘着剤層/PETシート」という構成の粘着シートを得た。なお実施例および比較例の配合部数は不揮発分比である。
原料を表3、4の配合に従って変更した以外は実施例1と同様に行うことで実施例2〜17および比較例1〜10の粘着シートを得た。
ただし、実施例14は参考例である。
得られた粘着シートを幅25mm・縦150mmの大きさに準備した。23℃、相対湿度50%雰囲気下、前記粘着シートから剥離性シートを剥がして露出した粘着剤層をポリプロピレン(PP)板に貼り付け、2kgロールで1往復圧着した24時間放置した後に引張試験機を用いて180度方向に300mm/分の速度で引き剥がす180°ピール試験において粘着力を測定し、下記の評価基準に基づいて評価を行った。(JIS Z0237:2000に準拠)
◎:「粘着力が14N以上であり、非常に良好。」
○:「粘着力が10N以上14N未満であり、良好。」
×:「粘着力が10N未満であり、実用不可。」
上記同様にステンレス(SUS)板に対して粘着力を測定し、下記の評価基準に基づいて評価を行った。
◎:「粘着力が16N以上であり、非常に良好。」
○:「粘着力が12N以上16N未満であり、良好。」
×:「粘着力が12N未満であり、実用不可。」
得られた粘着シートを幅25mm・縦150mmの大きさに準備した。JIS Z0237:2000に準拠して前記粘着シートから剥離性シートを剥がして、研磨した幅30mm・縦150mmのステンレス板の下端部幅25mm・横25mmの部分に粘着剤層を貼着し、2kgロールで1往復圧着した後、40℃雰囲気で1kgの荷重をかけ、7万秒放置することで保持力を測定した。評価は、粘着シート貼付面上端部が下にずれた長さを測定した。
評価基準
○:「ずれた長さが0.5mm未満である。良好。」
×:「ずれた長さが0.5mm以上である。実用不可。」
A.塗液安定性
ポットライフを判定するため塗液安定性を評価した。得られた粘着剤の配合10分後の粘度をB型粘度計にて測定した(粘着剤温度は23℃に調整)。さらにこの粘着剤を23℃、相対湿度50%雰囲気で8時間放置した後、再度B型粘度計にて粘度を測定した(粘着剤温度は23℃に調整)。また、8時間放置した後の粘着剤の外観を目視にて観察した。
なお、評価は、上記配合10分後の粘着剤の粘度、配合8時間後の粘着剤粘度、粘着剤外観から下記3段階の評価基準に基づいて行った。
○:「(配合8時間後の粘着剤の粘度)/(配合10分後の粘着剤の粘度)が1.2未満かつ、 粘着剤が透明。良好。」
△:「(配合8時間後の粘着剤の粘度)/(配合10分後の粘着剤の粘度)が1.2以上〜2. 0未満、または、粘着剤にわずかに濁りが発生し、実用不可。」
×:「(配合8時間後の粘着剤の粘度)/(配合10分後の粘着剤の粘度)が2以上、または、 粘着剤全体に濁りが発生し、実用不可。」
上記塗液安定性評価で8時間放置した後の粘着剤を塗工して粘着シートを得た。得られた粘着シ ートの粘着剤層の透明性を目視にて評価した。粘着剤層の外観に関しては、下記の3段階の評価 基準に基づいて評価を行った。
○:「塗膜は透明で実用上問題がない」
△:「塗膜はわずかに白化しており、実用上問題がある」
×:「塗膜全面が白化しており、実用不可である」
A−100 : スーパーエステルA−100(ロジン誘導体、荒川化学社製)
A−75 : スーパーエステルA−75(ロジン誘導体、荒川化学社製)
Claims (4)
- アクリル系重合体(A)100重量部に対して、イソシアネート化合物(B)0.5重量部以上5重量部未満を含み、
前記アクリル系重合体(A)がカルボキシル基含有モノマー0.3〜15重量%を含むモノマー混合物をラジカル重合してなる重合体であり、
前記イソシアネート化合物(B)が、3官能以上のイソシアネート化合物(b1)中のイソシアネート基100モルに対して、単官能アルコール(b2)及び第2級アミン(b3)のうち少なくともいずれか一方を合計5モル以上40モル未満反応してなる化合物であり、
かつ、粘着付与樹脂を含有することを特徴とする、粘着剤。 - 前記単官能アルコール(b2)が、炭素数4〜25のアルキル基を有する脂肪族アルコールであることを特徴とする、請求項1記載の粘着剤。
- 前記第2級アミン(b3)が、炭素数4〜25のアルキル基を分子内に1個以上有する脂肪族第2級アミンであることを特徴とする、請求項1または2記載の粘着剤。
- 基材および請求項1〜3いずれか1項に記載の粘着剤から形成してなる粘着剤層を備えた、粘着シート。
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