CN108603084B - Adhesive and adhesive sheet - Google Patents
Adhesive and adhesive sheet Download PDFInfo
- Publication number
- CN108603084B CN108603084B CN201780008321.8A CN201780008321A CN108603084B CN 108603084 B CN108603084 B CN 108603084B CN 201780008321 A CN201780008321 A CN 201780008321A CN 108603084 B CN108603084 B CN 108603084B
- Authority
- CN
- China
- Prior art keywords
- adhesive
- meth
- acrylate
- weight
- acrylic polymer
- 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.)
- Active
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- 239000000853 adhesive Substances 0.000 title claims abstract description 118
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 115
- 239000000178 monomer Substances 0.000 claims abstract description 52
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000011347 resin Substances 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 150000003573 thiols Chemical class 0.000 claims abstract description 7
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 239000012790 adhesive layer Substances 0.000 claims description 20
- 229920000098 polyolefin Polymers 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000576 coating method Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 14
- 239000007788 liquid Substances 0.000 abstract description 6
- -1 acrylate ester Chemical class 0.000 description 51
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 239000004743 Polypropylene Substances 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- 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 13
- 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 13
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 13
- 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 13
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- 125000005442 diisocyanate group Chemical group 0.000 description 10
- 239000004848 polyfunctional curative Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920001083 polybutene Polymers 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000010734 process oil Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000008096 xylene Substances 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 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 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- MADOXCFISYCULS-UHFFFAOYSA-N octyl 2-sulfanylacetate Chemical compound CCCCCCCCOC(=O)CS MADOXCFISYCULS-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- GCYUJISWSVALJD-UHFFFAOYSA-N 1,1-diethylcyclohexane Chemical compound CCC1(CC)CCCCC1 GCYUJISWSVALJD-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-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
- 229940035024 thioglycerol Drugs 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- 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
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
Abstract
The invention aims to provide an adhesive and an adhesive sheet which satisfy high nonvolatile content, pot life and coating property and can be used as a one-liquid hardening type adhesive with good heat resistance. The adhesive comprises an acrylic polymer (A) obtained by polymerizing a monomer mixture containing 6-18% by mass of an acidic group-containing monomer (a1) and 15-94% by weight of 2-ethylhexyl acrylate in the presence of a chain transfer compound, the chain transfer compound comprising one selected from the group consisting of methyl ethyl ketone, thiol, and an adhesion-imparting resin, and having a nonvolatile content concentration of 52-75% by mass, a chelate-type curing agent (B), an organic solvent (C) (wherein the alcohol (D) is excluded), an alcohol (D), and a keto-enol tautomer-forming compound (E).
Description
Technical Field
The present invention relates to a solvent-based adhesive and an adhesive sheet.
Background
The adhesive is widely used because it is used for an adhesive label or an adhesive sheet. The adhesive is generally a solvent-based adhesive or a water-based adhesive, and among them, there is an increasing demand for a water-based adhesive which is inexpensive and has little discharge of a solvent. On the other hand, solvent-based adhesives are widely used in applications where water-based adhesives are insufficient in water resistance, heat resistance, and the like. However, in the market, there is a strong demand for a solvent-based adhesive that reduces costs and environmental loads. Therefore, a method of reducing the amount of solvent volatilized when coating and drying the adhesive and suppressing the heat energy for drying by increasing the nonvolatile component of the solvent-based adhesive has been studied. In addition, a 2-liquid curing type in which a curing agent is prepared immediately before coating is often used for a general solvent-based adhesive because of a problem of pot life, and a method of reducing the cost of an adhesive sheet and reducing the environmental load such as a method of reducing a preparation step at a coating site by preparing an adhesive having a long pot life in which a curing agent is prepared in advance (hereinafter, referred to as a one-liquid curing type) has been studied.
However, in the case of a solvent-based adhesive, if the amount of the organic solvent contained is simply reduced, the nonvolatile content is relatively increased, and the viscosity of the adhesive is increased. Therefore, the fluidity of the adhesive is lowered, and the surface of the adhesive layer formed by coating becomes uneven, thereby causing a problem that the adhesiveness to the adherend is lowered.
Accordingly, patent document 1 discloses an adhesive containing an acrylic polymer having a weight average molecular weight of 5 to 30 ten thousand and an organic solvent (B) having a chain transfer constant of vinyl acetate in the organic solvent of 250 or more at 60 ℃, wherein the solid content concentration is 60% or more and the viscosity is 20,000mPa · s/25 ℃ or less.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2011-246700
Disclosure of Invention
Problems to be solved by the invention
However, since the conventional adhesive can provide an adhesive layer having low surface smoothness and the like, and has low coatability, and in addition, the weight average molecular weight is set to be too low, there is a problem in heat resistance that when the adhesive sheet is used in a high-temperature environment, the adhesive layer is broken by aggregation and the adhesive sheet is peeled from an adherend.
The invention aims to provide an adhesive and an adhesive sheet which satisfy high nonvolatile content, pot life and coating property and can be used as a one-liquid hardening type adhesive with good heat resistance.
Means for solving the problems
The adhesive of the present invention comprises at least one of an acrylic polymer (A) obtained by polymerizing a monomer mixture containing 6 to 18% by mass of an acidic group-containing monomer (a1) and 15 to 94% by weight of 2-ethylhexyl acrylate in the presence of a chain transfer compound, a chelate-type curing agent (B), an organic solvent (C) (wherein the alcohol (D) is excluded), an alcohol (D), and a keto-enol tautomer-forming compound (E),
the chain transfer compound contains one selected from the group consisting of methyl ethyl ketone, thiol, and a tackiness imparting resin, and the nonvolatile content concentration is 52 to 75% by mass.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, an adhesive and an adhesive sheet which satisfy high nonvolatile content, pot life and coatability and which can be used as a one-pack type adhesive having excellent heat resistance can be provided.
Detailed Description
Before describing the present invention in detail, terms are defined. Sheets, films and tapes are synonymous. The (meth) acrylic acid includes acrylic acid and methacrylic acid. The (meth) acrylate includes acrylates and methacrylates. The monomer is a monomer having an ethylenically unsaturated double bond. The adherend is an object to which an adhesive sheet is attached.
The adhesive of the present invention comprises at least one of an acrylic polymer (A) obtained by polymerizing a monomer mixture containing 6 to 18% by mass of an acidic group-containing monomer (a1) and 15 to 94% by weight of 2-ethylhexyl acrylate in the presence of a chain transfer compound, a chelate-type curing agent (B), an organic solvent (C) (wherein the alcohol (D) is excluded), an alcohol (D), and a keto-enol tautomer-forming compound (E),
the chain transfer compound contains one selected from the group consisting of methyl ethyl ketone, thiol, and a tackiness imparting resin, and the nonvolatile content concentration is 52 to 75% by mass.
The adhesive of the present invention can expand the molecular weight distribution of the acrylic polymer (a) by using a suitable amount of 2-ethylhexyl acrylate having a low reaction rate, and can improve the nonvolatile content, the pot life and the coatability by using the chelate-type curing agent (B), the alcohol (D) and any of the keto-enol tautomer forming compounds (E). In addition, the heat resistance of the adhesive can be improved by using an appropriate amount of the combination of the acidic group-containing monomer (a1) and the chelate-type curing agent (B).
The adhesive of the present invention is preferably used by forming an adhesive layer by coating and processing the adhesive layer into an adhesive sheet having a substrate. The adhesive of the present invention is not only an adhesive sheet, but also does not prevent the use in the form of a liquid as it is, such as a so-called "paste". In addition, the pressure-sensitive adhesive sheet can be used as a so-called casting pressure-sensitive adhesive sheet which is composed of only an adhesive layer without using a base material.
In the present invention, the acrylic polymer (a) is a polymer obtained by solution polymerization of a monomer mixture. The solution polymerization may be carried out by a known polymerization method. In addition, the monomer mixture is preferably subjected to solution polymerization in the presence of a chain transfer compound.
The monomer mixture contains 6 to 18 mass% of the acidic group-containing monomer (a1) and 15 to 94 mass% of 2-ethylhexyl acrylate as essential monomers, and contains monomers other than these monomers as arbitrary monomers.
The acid group-containing monomer (a1) contributes to crosslinking in the curing reaction between the acrylic polymer (a) and the chelate-type curing agent (B), and the cohesive force of the adhesive layer is increased by the crosslinking.
Examples of the acidic group-containing monomer (a1) include: (meth) acrylic acid, 2-carboxyethyl (meth) acrylate, dimer (meth) acrylic acid, crotonic acid, maleic anhydride, fumaric acid, citraconic acid, glutaconic acid, itaconic acid, acrylamide N-glycolic acid, cinnamic acid, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxyethyl succinate, and the like. Among these monomers, (meth) acrylic acid is preferred.
The acidic group-containing monomer (a1) is contained in an amount of preferably 6 to 18% by weight, more preferably 8 to 16% by weight, and still more preferably 10 to 15% by weight, based on 100% by weight of the monomer mixture. When the acid group-containing monomer (a1) is contained in an amount of 6% by weight or more, good heat resistance can be obtained. Further, when the content is 18% by weight or less, good coatability and good pot life can be obtained.
2-ethylhexyl acrylate has a low polymerization rate in radical polymerization, and tends to expand the molecular weight distribution of the acrylic polymer (A). This can suppress the viscosity of the adhesive, and therefore, when the nonvolatile content concentration of the adhesive is set high, good application properties can be obtained.
The 2-ethylhexyl acrylate is preferably contained in an amount of 15 to 94% by weight, more preferably 30 to 90% by weight, still more preferably 40 to 80% by weight, and particularly preferably 45 to 60% by weight, based on 100% by weight of the monomer mixture.
When 2-ethylhexyl acrylate is contained in an appropriate amount, heat resistance and coatability are improved.
In the present invention, the optional monomer is preferably a (meth) acrylate monomer other than 2-ethylhexyl acrylate, an amide group-containing monomer, an amino group-containing monomer, an epoxy group-containing monomer, an aromatic ring-containing monomer, an alicyclic hydrocarbon group-containing monomer, a vinyl ester, an alkoxy (meth) acrylate, a hydroxyl group-containing monomer, or the like.
Examples of the (meth) acrylate ester monomer include: methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-dodecyl (meth) acrylate, n-tridecyl (meth) acrylate, n-tetradecyl (meth) acrylate, and the like. Among these monomers, mention may be made of: (meth) acrylate having an alkyl chain of 1 to 2 carbon atoms (methyl (meth) acrylate, ethyl (meth) acrylate), n-butyl acrylate, 2-ethylhexyl acrylate, and the like. Furthermore, the (meth) acrylic monomer does not contain an alkoxy (meth) acrylate.
Examples of amide group-containing monomers include: (meth) acrylamide, N-methyl (meth) acrylamide, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N' -methylenebisacrylamide, N-methylol (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, N-vinylpyrrolidinone, diacetone acrylamide, N-dimethylaminopropyl (meth) acrylamide, (meth) acryloylmorpholine and the like.
Examples of the amino group-containing monomer include: n, N-dimethylaminoethyl (meth) acrylate, N-dimethylaminopropyl (meth) acrylate, and the like.
Examples of epoxy group-containing monomers include: glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, allyl glycidyl ether, and the like.
Examples of the aromatic ring-containing monomer include: phenyl acrylate, phenoxyethyl (meth) acrylate, benzyl (meth) acrylate, biphenyl (meth) acrylate, styrene, vinyltoluene, alpha-methylstyrene, and the like.
Examples of the alicyclic hydrocarbon group-containing monomer include: cyclohexyl (meth) acrylate, dicyclopentyl (meth) acrylate, isobornyl (meth) acrylate, and the like.
Examples of vinyl esters include: vinyl acetate, vinyl propionate, vinyl laurate, and the like.
Examples of the alkoxy (meth) acrylates include: 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 2-methoxybutyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and the like.
Examples of the hydroxyl group-containing monomer include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, 4-hydroxymethylcyclohexyl) methyl acrylate, N-methylol (meth) acrylamide, vinyl alcohol, allyl alcohol, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether and the like.
Among the arbitrary monomers, the use of a hydroxyl group-containing monomer is preferable because the cohesive force of the adhesive agent layer increases and the heat resistance improves. The hydroxyl group-containing monomer is more preferably 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate.
The hydroxyl group-containing monomer is preferably contained in an amount of 0.05 to 3 wt%, more preferably 0.1 to 2 wt%, and still more preferably 0.2 to 1.5 wt% based on 100 wt% of the monomer mixture.
Any of the monomers may be used alone or in combination of two or more.
The solution polymerization uses a radical polymerizable polymerization initiator. The polymerization initiator is preferably an azo compound, a peroxide, or the like. Examples of azo compounds include: 2, 2 '-azobis (2-methylisobutyronitrile), 2' -azobisisobutyronitrile, and the like. The peroxide is preferably t-butylperoxy-2-ethylhexanoate, benzoyl peroxide, di-t-butylperoxide, 1-bis (t-butylperoxy) -3, 3, 5-trimethylcyclohexane, or the like.
The polymerization initiator may be used alone or in combination of two or more.
The polymerization initiator is preferably used in an amount of 0.03 to 1.5 parts by weight, more preferably 0.1 to 1 part by weight, based on 100 parts by weight of the monomer mixture. When a proper amount of the polymerization initiator is used, the polymerization average molecular weight can be easily adjusted, and the adhesive properties can be adjusted.
The temperature of the solution polymerization may be suitably adjusted, but is usually about 70 ℃ to 100 ℃.
For solution polymerization, a chain transfer agent may be used in order to adjust the molecular weight or molecular weight dispersity. The chain transfer agent is preferably a compound having a chain transfer constant of 250 or more with respect to vinyl acetate at 60 ℃ (hereinafter, also referred to as a chain transfer compound). When a chain transfer agent is used, an acrylic polymer having a high molecular weight and a low viscosity is easily obtained, and thus the fluidity of the adhesive is improved, and thus the coatability is further improved. The chain transfer constant is more preferably 300 or more, and still more preferably 400 or more. On the other hand, the upper limit of the chain transfer constant is not limited, but is about 1000, since the molecular weight can be adjusted by a small amount when the amount is reduced. The molecular weight is a weight average molecular weight unless otherwise specified.
The chain transfer compound is preferably a ketone, thiol, adhesion-imparting resin, or the like.
Examples of ketones are: acetone, methyl ethyl ketone, hexanone, cyclohexanone methyl ethyl ketone, and the like. Of these ketones, Methyl Ethyl Ketone (MEK) is preferred. Further, with respect to the chain transfer constants for vinyl acetate at 60 ℃, methyl ethyl ketone was 738, toluene was 208.9, acetone was 117, and ethyl acetate was 33. These values are based on J.Brandreu (J.brandrup), Polymer Handbook (Polymer Handbook), p.II-91, interdiscipline (Interscience), written by E.H. Immergut (E.H. Immergut).
Examples of thiols include: mercaptoethanol, thioglycerol, thioglycolic acid, 3-mercaptopropionic acid, thiomalic acid, 2-mercaptoethanesulfonic acid, butanethiol, octanethiol, decanethiol, dodecanethiol, hexadecanethiol, octadecanethiol, cyclohexylthiol, thiophenol, octyl thioglycolate, octyl 3-mercaptopropionate, and the like. Among these thiols, octyl thioglycolate is preferable.
The weight average molecular weight of the acrylic polymer (a) used in the present invention is arbitrarily set as long as the above-mentioned problem can be solved, and is preferably 30 to 90 ten thousand, more preferably 40 to 80 ten thousand, and further preferably 50 to 70 ten thousand. When the weight average molecular weight is set in an appropriate range, both heat resistance and coatability can be easily achieved. The weight average molecular weight is a molecular weight in terms of polystyrene measured by Gel Permeation Chromatography (GPC).
The acrylic polymer (A) preferably has a molecular weight dispersion degree (molecular weight distribution) of 3 to 12, more preferably 3 to 10, and even more preferably 3 to 8. By setting the molecular weight dispersion degree to 3 to 12, the viscosity of the acrylic polymer (A) is reduced, so that both coatability and heat resistance are easily achieved. Further, the molecular weight dispersity is a value obtained by dividing a weight average molecular weight by a number average molecular weight.
The adhesive of the present invention is characterized by comprising a chelate-type hardener (B), an alcohol (D) and/or a keto-enol tautomer forming compound (E) in addition to the acrylic polymer (a), the organic solvent (C). By adding the alcohol (D) or the compound (E) having a reaction delaying effect to the chelate-type curing agent (B) which reacts with the acrylic polymer (a), a good pot life can be maintained without causing a curing reaction in a solution, and further, the alcohol or the compound (E) volatilizes at the time of drying, whereby the curing reaction is accelerated and good heat resistance is exhibited in the case of an adhesive after application and drying.
In the present invention, the chelate-type curing agent (B) is a compound containing a polyvalent metal and a ligand. Examples of polyvalent metals include: nickel, aluminum, chromium, iron, titanium, zinc, cobalt, manganese, zirconium, and the like. Examples of the ligand include acetylacetone and acetoacetate.
The chelate-type hardener (B) may be a compound part in which a polyvalent metal and a ligand are arbitrarily combined, and is preferably a compound in which aluminum is combined with a polyvalent metal and acetylacetone or acetoacetate is combined with a ligand.
The chelate-type curing agent (B) may be used alone or in combination of two or more.
The chelate-type curing agent (B) is preferably blended in an amount of 0.1 to 1.5 parts by weight, more preferably 0.2 to 1.2 parts by weight, and still more preferably 0.3 to 1.0 part by weight, based on 100 parts by weight of the acrylic polymer (a). When the chelate type curing agent (B) is added in an amount of 0.1 part by weight or more, the cohesive force and heat resistance are further improved. Further, when 1.5 parts by weight or less is used, the adhesion between the base material and the adhesive agent layer is further improved.
The adhesive of the present invention may further be used in combination with other hardeners. The other hardener is preferably, for example, an isocyanate hardener, an epoxy hardener, an aziridine hardener, or the like.
The isocyanate curing agent is preferably a diisocyanate or a polyisocyanate having a trifunctional or higher isocyanate group which is modified with a diisocyanate.
The diisocyanate is preferably an aromatic diisocyanate, an aliphatic diisocyanate or an alicyclic diisocyanate.
Examples of the aromatic diisocyanate include: 1, 5-naphthylene diisocyanate, 4 ' -diphenylmethane diisocyanate, 4 ' -diphenyldimethylmethane diisocyanate, 4 ' -dibenzyl isocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1, 3-phenylene diisocyanate, 1, 4-phenylene diisocyanate, toluene diisocyanate, and the like.
Examples of the aliphatic diisocyanate include: butane-1, 4-diisocyanate, hexamethylene diisocyanate, isopropylidene diisocyanate, methylene diisocyanate, 2, 4-trimethylhexamethylene diisocyanate, xylene diisocyanate, m-tetramethylxylene diisocyanate, dimer diisocyanate which converts the carboxyl group of dimer acid to an isocyanate group, and the like.
Examples of the alicyclic diisocyanate include: cyclohexane-1, 4-diisocyanate, isophorone diisocyanate, lysine diisocyanate, dicyclohexylmethane-4, 4' -diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, methylcyclohexane diisocyanate, norbornane diisocyanate, and the like.
The polyisocyanate is preferably a so-called adduct in which a diisocyanate is modified with a trifunctional polyol component, a biuret product in which a diisocyanate reacts with water, or a trimer (isocyanurate product) having an isocyanurate ring formed of three molecules of a diisocyanate.
Examples of polyisocyanates include: trimethylolpropane adduct of toluene diisocyanate, biuret product of hexamethylene diisocyanate, allophanate product of hexamethylene diisocyanate, and isocyanurate product of isophorone diisocyanate.
Examples of epoxy hardeners include: 1, 3-bis (N, N ' -diglycidylaminomethyl) cyclohexane, N, N, N ', N ' -tetraglycidyl-m-xylylenediamine, ethylene glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, diglycidylaniline, diglycidylamine and the like.
Examples of aziridine hardeners include: diphenylmethane-4, 4' -bis (1-aziridinecarboxamido), trimethylolpropane tri- β -aziridinylpropionate, tetramethylolmethane tri- β -aziridinylpropionate, toluene-2, 4-bis (1-aziridinecarboxamido), triethylenemelamine, bis-isophthaloyl-1- (2-methylaziridine), tri-1- (2-methylaziridine) phosphine, trimethylolpropane tri- β - (2-methylaziridine) propionate, and the like.
The other curing agent may be blended in an amount of about 0.05 to 5.0 parts by weight based on 100 parts by weight of the acrylic polymer (A).
The organic solvent (C) is used as a solvent for solution polymerization or a diluting solvent for adjusting the viscosity of the adhesive. The organic solvent (C) can be selected from the viewpoints of leveling property and drying property at the time of coating, and influence on the environment and human body. The organic solvent (C) is preferably an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, ester, ketone, or the like. Further, the organic solvent (C) of the present invention does not contain an alcohol.
Examples of the aliphatic hydrocarbon include n-hexane and n-heptane.
Examples of alicyclic hydrocarbons include: known compounds such as cyclopentane, cyclohexane, methylcyclohexane, dimethylcyclohexane, trimethylcyclohexane, ethylcyclohexane, diethylcyclohexane, decahydronaphthalene, bicycloheptane, tricyclodecane, hexahydroindanocyclohexane, cyclooctane, α -pinene, terpinolene, and limonene.
Examples of the aromatic hydrocarbon include: toluene, xylene, benzene, solvent oil, etc.
Examples of esters include: ethyl acetate, butyl acetate, and the like.
Examples of ketones are: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and the like.
Among these, the organic solvent (C) is preferably ethyl acetate, methyl ethyl ketone, or toluene, in terms of drying property, solubility, and chain transfer effect during solution polymerization.
The adhesive of the present invention comprises at least one of an alcohol (D) and a keto-enol tautomer-forming compound (E). When these compounds are formulated, they act on the chelate-type curing agent (B) to greatly increase the pot life of the adhesive.
Examples of the alcohol (D) include: methanol, ethanol, 1-propanol, isopropanol, 1-butanol, isobutanol, t-butanol, 1-pentanol, isopentanol, 1-hexanol, 4-methyl-2-pentanol, 1-heptanol, 1-octanol, isooctanol, 2-ethylhexanol, 1-nonanol, isononanol, 1-decanol, 1-dodecanol, 1-myristyl alcohol, cetyl alcohol, 1-stearyl alcohol, isostearyl alcohol, 2-octyldecanol, 2-octyldodecanol, 2-hexyldecanol, behenyl alcohol, oleyl alcohol, and the like. Among these alcohols, methanol, ethanol, 1-propanol and isopropanol are preferable in terms of volatility during drying, compatibility with the chelate-type curing agent and pot life.
The alcohol (D) is preferably contained in the adhesive in an amount of 2 to 40% by weight, more preferably 5 to 30% by weight. By including 2% by weight or more of the alcohol (D), the pot life is further improved. Further, by containing 40% by weight or less, the coating property is further improved, and the adjustment of the molecular weight of the acrylic polymer (a) becomes easy. The alcohol (D) may be used as a solvent in solution polymerization.
The keto-enol tautomer forming compound (E) is a compound that can form a keto-enol tautomer, and is preferably acetylacetone, an acetoacetate ester, a malonate ester, or the like.
Examples of the acetoacetic ester include: methyl acetoacetate, ethyl acetoacetate, isopropyl acetoacetate, butyl acetoacetate, isobutyl acetoacetate, t-butyl acetoacetate, and the like.
Malonic esters are listed, for example: dimethyl malonate, diethyl malonate, dibutyl malonate and the like.
Among these, the keto-enol tautomer-forming compound (E) is preferably acetylacetone from the viewpoint of ease of volatilization upon drying.
The keto-enol tautomer forming compound (E) is preferably contained in the adhesive in an amount of 0.05 to 5 wt%, more preferably 0.1 to 3 wt%, and still more preferably 0.2 to 2 wt%. If 0.05% by weight or more of the keto-enol tautomer-forming compound (E) is contained, the pot life is further improved. When the content is 5% by weight or less, the cohesive force of the adhesive agent layer is further improved.
The alcohol (D) and the keto-enol tautomer-forming compound (E) both inhibit the reaction of the chelate-type hardener (B), and therefore can be used alone or in combination. Further, in the case of using them together, the amount of blending can be suppressed as compared with the case of using them individually.
The adhesive of the present invention may further comprise a polyolefin. By containing polyolefin, the cohesive force of the adhesive is further improved, and the adhesive force to a low-polarity adherend made of polyolefin can be improved.
Polyolefins can be classified into chlorinated polyolefins (hereinafter, chlorinated polyolefins) and non-chlorinated polyolefins (hereinafter, non-chlorinated polyolefins). Examples of chlorinated polyolefins include: chlorinated polypropylene, acid-modified chlorinated polypropylene, acrylic acid-modified chlorinated polypropylene, chlorinated polyethylene, chlorinated ethylene-vinyl acetate copolymer, and the like. Among these, chlorinated polypropylene, acid-modified chlorinated polypropylene, and acrylic acid-modified chlorinated polypropylene are preferable, and chlorinated polypropylene is more preferable, in terms of excellent solubility and high adhesion to a polyolefin adherend.
The chlorinated polyolefin preferably has a chlorine content of 20% to 45% inclusive, more preferably 28% to 45% inclusive, in view of its high effect of improving the adhesive force to a low-polarity adherend made of polyolefin.
Examples of the non-chlorinated polyolefin include: polyethylene, polypropylene, an α -olefin-propylene copolymer, an ethylene-vinyl acetate copolymer, polybutene, maleated polybutene, polybutadiene and its hydride, polyisoprene and its hydride, maleated polybutadiene, maleated polyisoprene, polybutadiene polyol and its hydride, polyisoprene polyol and its hydride, lubricating oil such as process oil or mobile paraffin, and the like. Among these, α -olefin-polypropylene copolymers, polybutene, and lubricating oils are preferable in terms of excellent solubility and high adhesion to the polyolefin adherend. The lubricating oil is preferably a paraffin-based lubricating oil, a naphthene-based lubricating oil, or the like.
The polyolefin usable in the adhesive of the present invention is preferably a non-chlorinated polyolefin, and particularly preferably polybutene or a lubricating oil, from the viewpoint of excellent transparency of the adhesive.
The weight average molecular weight of the polyolefin is preferably 10 ten thousand or less, more preferably 5 ten thousand or less, in order to maintain compatibility with the acrylic polymer (a). The lower limit of the weight average molecular weight of the polyolefin is not particularly limited, but is preferably 200 or more.
The adhesive of the present invention may further comprise an adhesion-imparting resin. The adhesion-imparting resin may be prepared by any method such as a method used in solution polymerization or a method of blending the resin in the acrylic polymer (a). When the adhesion-imparting resin is used in solution polymerization, it functions as a chain transfer agent and the molecular weight of the acrylic polymer (a) can be easily adjusted. Further, when the acrylic polymer (A) is blended, the adhesive force can be further improved.
The softening point of the adhesion-imparting resin is preferably 80 ℃ or higher, more preferably 90 ℃ or higher, and still more preferably 100 ℃ or higher. The upper limit of the softening point is preferably 170 ℃, more preferably 160 ℃, and still more preferably 155 ℃. The softening point of the adhesion-imparting resin is 80 to 170 ℃, and the adhesion and heat resistance can be easily achieved at a high level. The softening point is a softening temperature measured by a dry-bulb method defined in Japanese Industrial Standards (JIS) K5902.
Examples of the adhesion-imparting resin include: rosin-based resins, polymerized rosin-based resins, rosin ester-based resins, polymerized rosin ester-based resins, terpene-phenol-based resins, benzofuran-based resins, coumarone-indene-based resins, styrene-based resins, xylene-based resins, phenol-based resins, petroleum-based resins, and the like. Among these, rosin-based resins, polymerized rosin-based resins, rosin ester-based resins, and polymerized rosin ester-based resins are preferable, and rosin ester-based resins and polymerized rosin ester-based resins are more preferable, from the viewpoint that compatibility with an acrylic polymer is good and adhesion performance can be further improved.
The adhesion-imparting resin may be used alone or in combination of two or more.
The adhesion-imparting resin is used preferably in an amount of 10 to 40 parts by weight, more preferably 15 to 35 parts by weight, based on 100 parts by weight of the acrylic polymer (a). When the adhesion-imparting resin is used in an amount of 10 to 40 parts by weight, the adhesion and cohesive forces can be maintained at a high level, and therefore, heat resistance can be easily obtained.
The adhesive of the present invention may further contain a flame retardant aid, a heat resistant stabilizer, a weather resistant stabilizer, an anti-aging agent, an ultraviolet absorber, a leveling agent, an antistatic agent, a slip aid, an anti-blocking agent, an antifogging agent, a lubricant, a dye, a wax, an emulsion, a magnetic substance, and a dielectric property adjuster as optional components.
The adhesive of the present invention has a nonvolatile content concentration of 52 to 75 wt%, preferably 55 to 70 wt%, and more preferably 55 to 65 wt%. By setting the nonvolatile content of the adhesive to a high concentration, the content of the organic solvent (C) can be relatively suppressed, and therefore, the drying cost at the time of coating and the load on the environment and human body can be suppressed.
The adhesive of the present invention preferably has a viscosity at 25 ℃ of 2000 to 20000 mPas, more preferably 2000 to 15000 mPas, and still more preferably 2000 to 10000 mPas. By setting the viscosity of the adhesive within an appropriate range, an adhesive layer having improved coatability and a smooth surface can be easily obtained. The viscosity was measured 1 minute after the start of rotation at 12rpm with a #3 spindle using a BL type viscometer at 25 ℃.
The adhesive sheet of the present invention preferably includes a substrate and an adhesive layer formed of an adhesive.
The adhesive layer is generally formed by applying an adhesive to a substrate, or by applying an adhesive to a release sheet and transferring the formed adhesive layer to a substrate. Further, a release sheet is generally bonded to the surface of the adhesive layer not in contact with the substrate and stored.
The substrate is preferably paper, plastic, cloth. The form of the substrate is preferably a sheet, a plate or a foam.
Examples of the raw material of the substrate include: polyolefins such as Polyethylene and Polypropylene (PP), polyesters such as polyethylene terephthalate (PET), plastics such as polystyrene, polyvinyl chloride, polycarbonate and cellophane, paper such as high-quality paper, kraft paper and crepe paper, cloth such as woven cloth and nonwoven cloth, elastomers such as ethylene propylene diene rubber, chloroprene rubber and isoprene rubber, and skins.
The thickness of the substrate is usually about 25 μm to 10000. mu.m.
The adhesive can be applied by a known coating method such as spin coating, spray coating, bar coating, knife coating, roll knife coating, die coating, or gravure coating. It is also preferable to perform a drying step at the time of coating. The drying step may be performed by a known apparatus such as a hot air oven, an electric oven, or an infrared heater.
In consideration of the balance between cost and adhesive performance, the thickness of the adhesive layer is usually about 20 to 300 μm, and more preferably about 20 to 100 μm.
The adhesive sheet of the present invention is used for various applications such as fixing of a roof panel, a floor panel, an interior and exterior panel of a vehicle, shielding for vehicle painting or surface treatment, product protection at shipment, fixing of interior and exterior members of a building, curing protection of concrete, fixing of members of household electric appliances, advertisement posting in vending machines, fixing of speaker nets of Liquid Crystal Displays (LCD), light-collecting rings, fixing of decorative plates, packaging, bundling, and temporary fixing.
[ examples ]
The present invention will be described more specifically with reference to examples, but the present invention is not limited to the examples. In the examples, "part(s)" means "part(s) by weight" and "%" means "% by weight".
"example 1"
Using a polymerization apparatus equipped with a stirrer, a thermometer, a dropping tube, and a reflux condenser, a reaction tank was charged with a half of a raw material mixture prepared from 66 parts of butyl acrylate, 20 parts of 2-ethylhexyl acrylate, 5.0 parts of methyl acrylate, 3.0 parts of methyl methacrylate, 6.0 parts of acrylic acid, 5 parts of methyl ethyl ketone, 65 parts of ethyl acetate, and 0.1 part of benzoyl peroxide under a nitrogen atmosphere. In addition, the remaining half of the raw material mixture was charged into the dropping layer. Then, the heating of the reaction tank was started. After confirming the start of the polymerization reaction, the raw material mixture was dropped from the dropping tube over 1 hour. After the end of the dropwise addition, the solution polymerization was further continued under reflux for 7 hours. After the completion of the reaction, the reaction mixture was cooled to obtain an acrylic polymer solution containing 58.8% of nonvolatile components. The weight average molecular weight of the acrylic polymer solution thus obtained was 100 ten thousand, and the degree of dispersion of the molecular weight was 3.8. Further, 20.0 parts of an adhesion-imparting resin (penel (Pencel) D-125 manufactured by seikagawa chemical corporation), 5.0 parts of isopropyl alcohol as a diluting solvent, 10.0 parts of ethyl acetate, 0.5 parts of acetylacetone as a keto-enol tautomer forming compound, and 0.4 parts of aluminum triacetylacetonate as a chelate-type curing agent were added to 100 parts of nonvolatile components of the acrylic polymer solution, and the mixture was sufficiently stirred to obtain an adhesive. The adhesive had a nonvolatile content of 58.5% and a viscosity of 22000 mPas.
"example 2 to example 18"
Adhesives of examples 2 to 18 were obtained in the same manner as in example 1, except that the raw materials and blending amounts of example 1 were changed as shown in tables 1 and 2.
Comparative example 1 "
Using a polymerization apparatus equipped with a stirrer, a thermometer, a dropping tube, and a reflux condenser, a reaction tank was charged with half of a raw material mixture prepared from 45 parts of butyl acrylate, 10 parts of 2-ethylhexyl acrylate, 10 parts of isobutyl acrylate, 10 parts of ethyl acrylate, 25 parts of acrylic acid, 20 parts of methyl ethyl ketone, 80 parts of ethyl acetate, and 0.1 part of benzoyl peroxide under a nitrogen atmosphere. In addition, the remaining half of the raw material mixture was charged into the dropping layer. Then, the heating of the reaction tank was started. After confirming the start of the polymerization reaction, the raw material mixture was dropped from the dropping tube over 1 hour. After the end of the dropwise addition, the solution polymerization was further continued under reflux for 7 hours. After the completion of the reaction, the reaction mixture was cooled to obtain an acrylic polymer solution containing 50% of nonvolatile components. The weight average molecular weight of the acrylic polymer solution thus obtained was 88 ten thousand, and the degree of molecular weight dispersion was 9.5. To 100 parts of nonvolatile components of the acrylic polymer solution were added 20.0 parts of a tackiness imparting resin (peruvi (penel) D-125), 20 parts of methanol as a diluent solvent, 20 parts of methyl ethyl ketone, 0.5 part of acetylacetone as a ketone-enol tautomer forming compound, and 0.4 part of aluminum triacetylacetonate as a chelate-type curing agent, followed by sufficient stirring to obtain a tacky adhesive. The adhesive had a nonvolatile content of 46.1% and a viscosity of 8000 mPas.
Comparative examples 2 to 6 "
Adhesives of comparative examples 2 to 6 were obtained in the same manner as in comparative example 1, except that the raw materials and the amounts of blending in comparative example 1 were changed as shown in table 2.
< nonvolatile fraction >
The nonvolatile content was determined from the weight ratio of the nonvolatile content before and after drying in an electric oven at 150 ℃ to 20 minutes.
< viscosity >
The viscosity was measured at 25 ℃ for 1 minute from the start of rotation at 12rpm using a BL type viscometer using a #3 spindle.
< weight average molecular weight >
The weight average molecular weight (Mw) was determined by GPC under the following conditions.
GPC apparatus: shimadzu excellence (SHIMADZU science) model LC-20AD (made by Shimadzu corporation)
Pipe column: 2 Tosoh (TOSOH) TSK-GEL alpha-M7.8X 300 (manufactured by Tosoh corporation)
Solvent: 10mM LiBr (lithium bromide) dimethylformamide solution
Flow rate: 0.5ml/min
Temperature: 40 deg.C
Sample concentration: 0.2 wt.%
Sample injection amount: 100 μ l
A detector: refractive Index (Refractive Index) (wavelength 254nm), type RID-10A
< pot life >
The obtained adhesive was stored at 50 ℃ for 1 month, and then the viscosity was measured to calculate the viscosity increase rate.
Viscosity increase rate (%) - (viscosity after 50 to 1 month/viscosity immediately after blending) × 100
Very good: the viscosity increase rate is less than 10%. Is excellent in
O: the viscosity increase rate is 10% or more and less than 20%. Good effect
And (delta): the viscosity increase rate is 20% or more and less than 30%. It is practical.
X: the viscosity increase rate is more than 30%. It is not practical.
< coatability >
The coatability was evaluated by visual observation of the surface of an adhesive layer formed by coating the obtained adhesive using a notched wheel coater at a coating speed of 30m/min to a dry thickness of 50 μm. The evaluation criteria are as follows.
O: a coated surface having a smooth surface can be obtained. Is good.
And (delta): the coated surface was not smooth. But is practical.
X: producing a stripe or depression of the roller on the coated side. It is not practical.
[ preparation of adhesive sheet ]
The obtained adhesive was coated on a commercially available release sheet using a notch wheel coater so that the dry thickness became 50 μm, dried in an electric oven for 100 to 2 minutes, and a polyethylene terephthalate (PET) film having a thickness of 50 μm was attached to the adhesive layer after removing the solvent to obtain an adhesive sheet. After curing was completed by curing in a constant temperature and humidity chamber in an environment of 23 to 50% RH for 7 days, the following physical properties were evaluated.
< adhesion >
The adhesive sheet thus obtained was cut into a size of 25mm in width and 100mm in length to prepare a sample. Subsequently, the release sheet was peeled from the sample in an environment of 23 to 50% RH based on JIS Z0237, and the exposed adhesive layer was attached to a polished stainless steel (SUS) plate, subjected to pressure contact to 1 round trip with a 2kg roller, and then the adhesive force (N/25mm) was measured under conditions of a peel speed of 300mm/min and a peel angle of 180 ° using a tensile tester 24 hours after the attachment. Adhesion to polypropylene panels was likewise determined.
"relative to SUS plate"
O: the adhesive force is more than 20N/25 mm. Good effect
And (delta): the adhesive force is more than 15N/25mm and less than 20N/25 mm. It is practical.
X: less than 15N/25 mm. It is not practical.
Relative to PP plate "
Very good: the adhesive force is more than 10N/25 mm. Is excellent.
O: the adhesive force is more than 5N/25mm and less than 10N/25 mm. Good effect
And (delta): the adhesive force is more than 3N/25mm and less than 5N/25 mm. It is practical.
X: less than 3N/25 mm. It is not practical.
< holding force >
The adhesive sheet thus obtained was cut into a size of 25mm in width and 100mm in length to prepare a sample. Then, the release sheet was peeled from the sample in an environment of 23 to 50% RH in accordance with JIS Z0237, and the exposed portion of the adhesive agent layer having a width of 25mm and a length of 25mm at the tip end was stuck to a polished stainless steel (SUS) plate, and after 1 time of reciprocal pressure bonding with a 2kg roller, a load of 1kg was applied in an environment of 80 ℃, and the plate was held for 7 ten thousand seconds. For the evaluation, the number of seconds of the sample falling from the SUS plate was indicated. The number of mm in which the adhesive layer and the leading end portion of the SUS plate were deviated downward by the load was indicated when the sample was not dropped. Evaluation criteria are shown below.
Very good: the deflection of the sample is excellent below 2mm
O: the deflection of the sample is preferably 2mm or more and less than 5mm
And (delta): the deflection of the sample was 5mm or more and there was no problem in practical use without dropping
X: the sample can not fall down practically
< anchorage >
The adhesiveness between the adhesive layer and the foam base material was evaluated as anchorage. The adhesive sheet thus obtained was cut into a size of 25mm in width and 100mm in length to prepare a sample. Then, a foam sheet (width 30mm, length 130mm, thickness 10mm, ECS manufactured by inoac) lined with an SUS plate was adhered to a double-sided tape in an environment of 23 to 50% RH for 1 time reciprocal pressure bonding with a 2kg roller, and then the adhesive force (N/25mm) was measured under conditions of a peeling speed of 300mm/min and a peeling angle of 180 ° after 24 hours of adhesion using a tensile tester.
Very good: the adhesive force is more than 5N/25 mm. Is excellent. The substrate breaks.
O: the adhesive force is more than 2N/25mm and less than 5N/25 mm. With fracture of the substrate. Good effect
And (delta): the adhesive force is more than 1N/25mm and less than 2N/25 mm. It is practical.
X: less than 1N/25 mm. It is not practical.
< transparency >
The transparency of the adhesive layer of the obtained adhesive sheet was visually evaluated. Evaluation criteria are shown below.
O: is colorless and transparent. Is good.
And (delta): slight whitening and coloration. It is practical.
X: there was severe whitening and agglomeration. It is not practical.
The abbreviations in tables 1 and 2 have the following meanings.
BA: acrylic acid butyl ester
2 EHA: 2-ethylhexyl acrylate
IBA: acrylic acid isobutyl ester
IBMA: methacrylic acid isobutyl ester
MA: acrylic acid methyl ester
MMA: methacrylic acid methyl ester
EA: acrylic acid ethyl ester
Vac: vinyl Acetate (VAE)
AA: acrylic acid
MAA: methacrylic acid
HEA: 2-Hydroxyethyl acrylate
4 HBA: acrylic acid 4-hydroxybutyl ester
MEK: methyl ethyl ketone
IPA: isopropanol (I-propanol)
Percelu (Pencel) D-125: rosin ester based tackifier resin manufactured by Mitsukawa chemical Co Ltd
Peruvian (Pencel) AZ: rosin ester based tackifier resin manufactured by Mitsukawa chemical Co Ltd
Super Ester (Super Ester) S-100: rosin ester based tackifier resin manufactured by Mitsukawa chemical Co Ltd
Urastene (Ultrathene) 725: tosoh corporation for ethylene-vinyl acetate copolymers
Saperculon (Supercron) 930: the weight-average molecular weight of the chlorinated polypropylene manufactured by Japan paper-making company is about 7 ten thousand, and the chlorine content is 21%
Saperculon (Supercron) 390: the weight-average molecular weight of the chlorinated polypropylene manufactured by Japan paper-making company is about 2 ten thousand, and the chlorine content is 36%
Suppacoulom (Supercron) 370M: the weight average molecular weight of the chlorinated polypropylene manufactured by Japan paper-making company is about 1 ten thousand, and the chlorine content is 30%
Saperculon (Supercron) 814B: the chlorinated polypropylene produced by Japan paper-making company has a weight-average molecular weight of about 1.5 ten thousand and a chlorine content of 41%
PB 300: dalin (DAELIM) Inc. liquid polybutene having a weight average molecular weight of about 300
Super oil (super oil) M32: the weight average molecular weight of the paraffin-based lubricating oil manufactured by JX energy GmbH is about 400
Tina Process oil (Diana Process oil) NP-24: naphthenic lubricating oils manufactured by Shikino Limited company have a weight average molecular weight of about 300
Aluminum chelate compound a: preparation of aluminum tris (acetylacetonate) by Chuanjia Fine Chemicals
TDI-TMP solution: trimethylolpropane adduct of toluene diisocyanate (nonvolatile content 375%)
From the results in tables 3 and 4, the adhesives of examples 1 to 18 all had good pot lives and were excellent in adhesion and heat resistance. The heat resistance was determined from the results of the holding force.
Claims (6)
1. An adhesive comprising an acrylic polymer (A) obtained by polymerizing a monomer mixture containing 6 to 18% by mass of an acidic group-containing monomer (a1) and 15 to 94% by weight of 2-ethylhexyl acrylate in the presence of a chain transfer compound, a chelate-type curing agent (B), and an organic solvent (C),
the adhesive further comprises at least one of an alcohol (D) and a keto-enol tautomer forming compound (E),
and the adhesive further comprises a polyolefin,
the organic solvent (C) does not contain the alcohol (D),
the chain transfer compound contains one selected from the group consisting of methyl ethyl ketone, thiol, and a tackiness imparting resin, and the nonvolatile content concentration is 52 to 75% by mass.
2. The adhesive of claim 1, wherein the monomer mixture further comprises a hydroxyl-containing monomer.
3. The adhesive according to claim 1 or 2, wherein the weight average molecular weight of the acrylic polymer (a) is 30 to 90 ten thousand.
4. The adhesive according to claim 1 or 2, wherein the acrylic polymer (A) has a molecular weight dispersity of 3 to 12.
5. The adhesive according to claim 1 or 2, wherein the adhesive has a viscosity of 2000 to 20000 mPa-s at 25 ℃.
6. An adhesive sheet, comprising: a substrate, and an adhesive layer which is a cured product of the adhesive according to any one of claims 1 to 5.
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| JP2016018152 | 2016-02-02 | ||
| JP2016-018152 | 2016-02-02 | ||
| JP2016206792A JP6108023B1 (en) | 2016-02-02 | 2016-10-21 | Adhesive and adhesive sheet |
| JP2016-206792 | 2016-10-21 | ||
| PCT/JP2017/002304 WO2017135102A1 (en) | 2016-02-02 | 2017-01-24 | Adhesive agent and adhesive sheet |
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| JP7175622B2 (en) * | 2017-10-06 | 2022-11-21 | 日東電工株式会社 | Acrylic pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet |
| JP7063689B2 (en) * | 2017-10-06 | 2022-05-09 | 日東電工株式会社 | Acrylic adhesive composition and adhesive sheet |
| CN109628026B (en) * | 2017-10-06 | 2022-09-23 | 日东电工株式会社 | Acrylic pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet |
| JP7063690B2 (en) * | 2017-10-06 | 2022-05-09 | 日東電工株式会社 | Adhesive sheet |
| CN109628025A (en) * | 2017-10-06 | 2019-04-16 | 日东电工株式会社 | Acrylic pressure-sensitive adhesive compositions and bonding sheet |
| EP3498797B1 (en) | 2017-12-15 | 2021-08-11 | Henkel AG & Co. KGaA | Adhesive tape for bonding textile materials |
| JP7067188B2 (en) * | 2018-03-28 | 2022-05-16 | 東洋インキＳｃホールディングス株式会社 | Adhesive composition and adhesive sheet |
| US20220006137A1 (en) * | 2018-11-16 | 2022-01-06 | 3M Innovative Properties Company | Curable compositions, articles therefrom, and methods of making and using same |
| JP7338444B2 (en) | 2019-12-17 | 2023-09-05 | 東洋インキＳｃホールディングス株式会社 | Adhesives and adhesive sheets |
| WO2021124857A1 (en) * | 2019-12-20 | 2021-06-24 | 株式会社アイセロ | Thermoplastic adhesive composition |
| KR102178754B1 (en) * | 2020-03-06 | 2020-11-13 | 차동화 | Crack repair composition |
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| CA2017996C (en) * | 1989-06-09 | 1997-06-10 | Eli Levine | Adhesive |
| JPH10158618A (en) * | 1996-11-27 | 1998-06-16 | Nippon Synthetic Chem Ind Co Ltd:The | Pressure-sensitive adhesive composition |
| JP5540219B2 (en) * | 2009-09-15 | 2014-07-02 | 綜研化学株式会社 | Adhesive composition |
| CN102858872B (en) * | 2010-04-27 | 2016-06-29 | 日本合成化学工业株式会社 | Acrylic resin solution, adhesive composition, binding agent, bonding sheet, optical component with adhesive phase |
| JP2013203791A (en) * | 2012-03-27 | 2013-10-07 | Toyo Ink Sc Holdings Co Ltd | Adhesive and adhesive processed product |
| JP5901399B2 (en) * | 2012-04-05 | 2016-04-06 | 藤森工業株式会社 | Adhesive composition and surface protective film |
| JP5651158B2 (en) * | 2012-11-30 | 2015-01-07 | 綜研化学株式会社 | Adhesive composition |
| JP6062811B2 (en) * | 2013-06-15 | 2017-01-18 | 日東電工株式会社 | Adhesive composition, adhesive layer and adhesive sheet |
| JP6241260B2 (en) * | 2013-12-20 | 2017-12-06 | 東洋インキＳｃホールディングス株式会社 | Removable water-based pressure-sensitive adhesive and pressure-sensitive adhesive sheet |
| JP6403186B2 (en) * | 2014-05-20 | 2018-10-10 | 日東電工株式会社 | Pressure-sensitive adhesive layer, pressure-sensitive adhesive sheet, and method for producing pressure-sensitive adhesive layer |
| JP6342229B2 (en) * | 2014-06-13 | 2018-06-13 | 日東電工株式会社 | Adhesive composition, adhesive sheet, and optical member |
| JP2016011363A (en) * | 2014-06-27 | 2016-01-21 | 日東電工株式会社 | Adhesive composition, adhesive sheet and optical member |
| JP6419467B2 (en) * | 2014-06-27 | 2018-11-07 | 日東電工株式会社 | Adhesive composition, adhesive sheet, and optical member |
| JP6390376B2 (en) * | 2014-11-25 | 2018-09-19 | 東洋インキＳｃホールディングス株式会社 | Adhesive and adhesive sheet |
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| CN108603084A (en) | 2018-09-28 |
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