JP6931997B2 - Uv硬化性アクリルコポリマー - Google Patents
Uv硬化性アクリルコポリマー Download PDFInfo
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- JP6931997B2 JP6931997B2 JP2016575107A JP2016575107A JP6931997B2 JP 6931997 B2 JP6931997 B2 JP 6931997B2 JP 2016575107 A JP2016575107 A JP 2016575107A JP 2016575107 A JP2016575107 A JP 2016575107A JP 6931997 B2 JP6931997 B2 JP 6931997B2
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- Prior art keywords
- weight
- meth
- acrylate
- monomer
- mixture
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- 229920006243 acrylic copolymer Polymers 0.000 title claims description 57
- 239000000178 monomer Substances 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 107
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 58
- 230000001070 adhesive effect Effects 0.000 claims description 48
- 239000000853 adhesive Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 46
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 28
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 21
- -1 carboxyethyl Chemical group 0.000 claims description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 19
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 11
- 230000009477 glass transition Effects 0.000 claims description 11
- 239000012943 hotmelt Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 239000013557 residual solvent Substances 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims 1
- 150000003440 styrenes Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 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 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical class CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical class CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-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
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- CRJIYMRJTJWVLU-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 3-(5,5-dimethylhexyl)dioxirane-3-carboxylate Chemical compound CC(C)(C)CCCCC1(C(=O)OC(C)(C)CC(C)(C)C)OO1 CRJIYMRJTJWVLU-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- YWEJNVNVJGORIU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-hydroxy-2-phenylacetate Chemical compound OCCOCCOC(=O)C(O)C1=CC=CC=C1 YWEJNVNVJGORIU-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- SKVOYPCECYQZAI-UHFFFAOYSA-N 2-ethylhexyl 2-methylbutan-2-ylperoxy carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)CC SKVOYPCECYQZAI-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- TVWBTVJBDFTVOW-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylperoxy)propane Chemical compound CC(C)COOCC(C)C TVWBTVJBDFTVOW-UHFFFAOYSA-N 0.000 description 1
- UPFQJMVQJWHPOL-UHFFFAOYSA-N 2-methyl-1-phenylpropane-1,2-diol Chemical compound CC(C)(O)C(O)C1=CC=CC=C1 UPFQJMVQJWHPOL-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- RAWISQFSQWIXCW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)CC RAWISQFSQWIXCW-UHFFFAOYSA-N 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
- CARSMBZECAABMO-UHFFFAOYSA-N 3-chloro-2,6-dimethylbenzoic acid Chemical compound CC1=CC=C(Cl)C(C)=C1C(O)=O CARSMBZECAABMO-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 1
- XSHLSPHLMXXQIB-UHFFFAOYSA-N [PH2](OC1=C(C=CC=C1)C(C1=CC=CC=C1)=O)=O Chemical class [PH2](OC1=C(C=CC=C1)C(C1=CC=CC=C1)=O)=O XSHLSPHLMXXQIB-UHFFFAOYSA-N 0.000 description 1
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- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- ZGPBOPXFOJBLIV-UHFFFAOYSA-N butoxycarbonyloxy butyl carbonate Chemical compound CCCCOC(=O)OOC(=O)OCCCC ZGPBOPXFOJBLIV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GEKDHJTUYGMYFB-UHFFFAOYSA-N chromium;pentane-2,4-dione Chemical compound [Cr].CC(=O)CC(C)=O GEKDHJTUYGMYFB-UHFFFAOYSA-N 0.000 description 1
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 description 1
- QNZRVYCYEMYQMD-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu].CC(=O)CC(C)=O QNZRVYCYEMYQMD-UHFFFAOYSA-N 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940057404 di-(4-tert-butylcyclohexyl)peroxydicarbonate Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MBBQAVVBESBLGH-UHFFFAOYSA-N methyl 4-bromo-3-hydroxybutanoate Chemical compound COC(=O)CC(O)CBr MBBQAVVBESBLGH-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XSBOOIFPDDTOMH-UHFFFAOYSA-N pentane-2,4-dione;sodium Chemical compound [Na].CC(=O)CC(C)=O XSBOOIFPDDTOMH-UHFFFAOYSA-N 0.000 description 1
- WATYAKBWIQTPDE-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O WATYAKBWIQTPDE-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 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
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- 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
- C09J133/062—Copolymers with monomers not covered by C09J133/06
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- 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
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- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
- C09J2301/16—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the structure of the carrier layer
- C09J2301/162—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the structure of the carrier layer the carrier being a laminate constituted by plastic layers only
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- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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Landscapes
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- Adhesive Tapes (AREA)
Description
(a)モノマーの混合物を重合させてアクリルコポリマーを形成すること、ここで、該モノマー混合物は、
(i)少なくとも1つの(メタ)アクリル酸エステル単量体40-95重量%、
(ii)少なくとも1つの共重合性モノマー5-60重量%、ここで、該モノマーは、そのホモポリマーのガラス転移温度が-30℃より高いものから選択される、および
(iii)任意に、ヒドロキシル基およびカルボキシル基からなる群から選択される官能基を有する少なくとも1つの共重合可能な官能性モノマー0.5-20重量%
を含む;および
(b)アクリルコポリマーを、触媒の存在下でUV硬化性官能基を含む少なくとも1種のモノマーと反応させて、UV硬化性アクリルコポリマーを形成すること。
i)第3の態様による接着剤組成物を基材上にコーティングして、基材表面上に前記接着剤組成物の層を形成すること;および
ii)接着剤組成物の層にUV光を照射して接着シートを形成すること。
(i)少なくとも1つの(メタ)アクリル酸エステル単量体40-95重量%、
(ii)少なくとも1つの共重合性モノマー5-60重量%、ここで、該モノマーは、そのホモポリマーのガラス転移温度が-30℃より高いものから選択される、および
(iii)任意に、ヒドロキシル基およびカルボキシル基からなる群から選択される官能基を有する少なくとも1つの共重合可能な官能性モノマー0.5-20重量%
を含む。
アクリルコポリマーは、660部の2-エチルヘキシルアクリレート、120部のメタクリル酸、258部のメチルアクリレートおよび400部のエチルアクリレートを共重合することによって、720部のエチルアセテート中で4時間のフルモノマー遅延プロセスによって製造した。並行して、4.77部のAZDN開始剤(VAZO 64)および10.8部のドデシルメルカプタン(連鎖移動剤)を添加した。添加後、混合物を還流温度で2時間維持して完全な転化率を確保した。残留モノマー濃度は、ガスクロマトグラフィーで測定して1%未満であった。
実施例1で調製した。
本明細書のPSA結果のための全てのテープは、接着剤転写によって作製する。未硬化の液体PSA組成物を剥離紙(Loparex Poly Slik 111/120、Apeldoorn、オランダ、ロール番号W03180672)上に引き出す。ブレイブ・インストゥルメンツ社の調節可能なバードアプリケータを使用して、典型的には25−130μmの設定で、最も遅い速度(約1.5m/分)で30cmストロークのGardco自動ドローダウンマシンを用いて100℃でドローダウンを行う。組成物は、200ワット/cmのパワーを有するUV-FusionランプBF9(H-バルブ)を用いて可変速度を有するコンベアベルト上でUV硬化され、その速度は接着剤の厚さに依存する。ランプの出力は、パックを使用してUV-A、BおよびCの線量および放射照度を正しいベルト速度で測定することによって試験する
すべての室温性能試験は、23±2℃、相対湿度50±5%の一定温度/一定湿度管理室で行う。
上記のように調製されたテープは、ステンレス鋼(SST)、ガラスおよび他の材料で作られた試験パネル上に付与することができる。剥離試験は、インストロン(Instron)機でEN 1939に従って付与の20分後に実施する。結果は、25mmあたりのNで報告する。
剪断抵抗は、接着剤の凝集力または内部強度の尺度である。これは、一定の圧力で貼り付けられた表面に平行な方向で、標準平坦面から接着ストリップを引っ張るのに必要な力の量に基づく。これは、一定荷重下でステンレス鋼試験パネルから接着剤被覆シート材料の標準領域を引っ張るのに要する時間として測定する。
SAFTはまた、接着剤の凝集力または内部強度の尺度でもある。この試験は、ASTM D-4498-95にも記載されている同じ構造を使用して剪断試験を修正したものであるが、ここでは一定速度で加熱されたオーブン内に置かれる。試験は、1℃/分の加熱速度で室温から開始して行った。重りが落ちる温度を記録する。重りがまだ210℃で止まる場合、試験は停止され、この値が記録される。
この試験方法は、感圧接着剤の粘着特性を決定することを意図している。この試験方法は、他の表面との接触時に測定可能な強度の結合を迅速に形成する接着剤に適用可能である。これらの方法は、裏張りを有する感圧接着剤のループをステンレス鋼の表面と接触させることを可能にし、適用する唯一の力は感圧知物品自体の重量である。次いで、感圧品を基材から取り出し、感圧品を被着体から除去する力を記録器具によって測定する。ループタック試験は、Finat試験方法No.9に従って、適用の20分後にInstronマシン上で実施する。結果は、25mmあたりのNで報告する。
〔1〕UV硬化性アクリルコポリマーの製造方法であって、
(a)モノマーの混合物を重合させてアクリルコポリマーを形成すること、ここで、該モノマー混合物は、
(i)少なくとも1つの(メタ)アクリレートモノマー40−95重量%、
(ii)そのホモポリマーのガラス転移温度が-30℃より高いものから選択される少なくとも1つの共重合性モノマー5−60重量%、および
(iii)任意に、ヒドロキシル基およびカルボキシル基からなる群から選択される官能基を有する少なくとも1つの共重合可能な官能性モノマー0.5−20重量%
を含み、および
(b)アクリルコポリマーを、触媒の存在下でUV硬化性官能基を含む少なくとも1種のモノマーと反応させて、UV硬化性アクリルコポリマーを形成すること
を含む方法。
〔2〕前記モノマーの混合物は、
(i)少なくとも1つの(メタ)アクリレートモノマー少なくとも約45重量%、好ましくは少なくとも約50重量%;および/または
(ii)少なくとも1つの(メタ)アクリレートモノマー約94重量%以下、好ましくは約80重量%以下、より好ましくは約70重量%以下
を含む、〔1〕に記載の方法。
〔3〕前記少なくとも1種の(メタ)アクリレートモノマーは、
(i)そのホモポリマーのガラス転移温度が約-30℃以下であるものから選択され、および/または
(ii)アルキル(メタ)アクリレートであって、好ましくは、該アルキル(メタ)アクリレートのアルキル基の炭素原子数が3−20の範囲であり、より好ましくは、該アルキル(メタ)アクリレートは、ブチルアクリレート、イソ-オクチルアクリレート、2-エチルヘキシルアクリレート、およびそれらの混合物からなる群から選択される、
〔1〕または〔2〕に記載の方法。
〔4〕前記モノマーの混合物は、
(i)少なくとも1つの共重合性モノマー少なくとも約10重量%、好ましくは少なくとも約20重量%;および/または
(ii)少なくとも1つの共重合性モノマー59重量%以下、好ましくは50重量%以下、より好ましくは40重量%以下
を含む、〔1〕〜〔3〕のいずれかに記載の方法。
〔5〕共重合性モノマーは、アルキル(メタ)アクリレート、ビニルアセテート、スチレン、およびそれらの混合物からなる群から選択され、アルキル(メタ)アクリレートのアルキル基の炭素原子数は好ましくは1−20であり、アルキル(メタ)アクリレートはより好ましくはメチル(メタ)アクリレート、エチル(メタ)アクリレート、tert-ブチル(メタ)アクリレート、およびそれらの混合物からなる群から選択される、〔1〕〜〔4〕のいずれかに記載の方法。
〔6〕前記モノマー混合物は、
(i)少なくとも1つの共重合可能な官能性モノマー少なくとも約1重量%、好ましくは少なくとも約1.5重量%;および/または
(ii)少なくとも1つの共重合可能な官能性モノマー10重量%以下、好ましくは7重量%以下
を含む、〔1〕〜〔5〕のいずれかに記載の方法。
〔7〕〔1〕〜〔6〕のいずれかに記載の方法であって、前記少なくとも1つの共重合可能な官能性モノマーは、ヒドロキシアルキル(メタ)アクリレート、ヒドロキシアルキル(メタ)アクリレートのエトキシル化および/またはプロポキシル化誘導体、それらのラクトン付加物、(メタ)アクリル酸、β-カルボキシエチル(メタ)アクリレート、クロトン酸、マレイン酸、フマル酸、イタコン酸 、アクリル酸、ヒドロキシエチルアクリレート、およびそれらの混合物からなる群から選択され、ここで、ヒドロキシアルキル(メタ)アクリレートのアルキル基の炭素原子数は好ましくは1−20の範囲内であり、ヒドロキシアルキル(メタ)アクリレートは、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレート、ヒドロキシペンチル(メタ)アクリレート、ヒドロキシヘプチル(メタ)アクリレート、ヒドロキシノニル(メタ)アクリレート、ヒドロキシデシル(メタ)アクリレート、それらの異性体、それらのエトキシル化及び/又はプロポキシル化誘導体、それらのラクトンとの付加物;ジエチレングリコールモノ(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、プロピレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、およびそれらの混合物からなる群から選択されることが好ましい、方法。
〔8〕前記モノマーの混合物は、
a)2-エチルヘキシルアクリレート、メタクリル酸、アクリル酸メチルおよびアクリル酸エチル;又は
b)ブチルアクリレート、メタクリル酸、アクリル酸メチルおよびアクリル酸エチル
を含むかまたはそれからなる、請求項1−7のいずれかに記載の方法。
〔9〕〔1〕〜〔8〕のいずれかに記載の方法であって、該方法は、アクリル系モノマー混合物を適切な溶剤中に供給し、アクリル系コポリマーを、UV硬化性基を含む少なくとも1種のモノマーと反応させる前に溶媒を蒸発させる工程をさらに含み、ここで、アクリル系コポリマー中の残留溶剤含有量は好ましくは1重量%未満である、方法。
〔10〕UV硬化性基を含むモノマーは、ビニルおよびエポキシ基を含むモノマー、好ましくはエポキシ官能化アクリレート、より好ましくは(メタ)アクリル酸のグリシジルエステルである、〔1〕〜〔9〕のいずれかに記載の方法。
〔11〕アクリルコポリマーのガラス転移温度は約-60℃−約20℃、好ましくは約-30℃−約10℃の範囲である、〔1〕〜〔10〕のいずれかに記載の方法。
〔12〕〔1〕〜〔11〕のいずれかに記載の方法によって得られるUV硬化性アクリルコポリマー。
〔13〕〔12〕に記載のUV硬化性アクリルコポリマーおよび光開始剤を含む、接着剤組成物、好ましくは感圧接着剤(PSA)またはホットメルト組成物。
〔14〕接着シートの製造方法であって、
i)〔13〕に記載の接着剤組成物を基材上にコーティングして、前記基材表面上に前記接着剤組成物の層を形成すること;および
ii)接着剤組成物の層にUV光を照射して接着シートを形成すること
を含む方法。
〔15〕接着剤、好ましくは感圧接着剤またはホットメルトとしての、〔12〕に記載のUV硬化性アクリルコポリマーの使用。
Claims (13)
- 感圧接着剤またはホットメルトとしてのUV硬化性アクリルコポリマーの製造方法であって、
(a)モノマーの混合物を重合させてアクリルコポリマーを形成すること、ここで、該モノマー混合物は、
(i)そのホモポリマーのガラス転移温度が-30℃以下であるものから選択される少なくとも1つの(メタ)アクリレートモノマー40−94重量%、
(ii)アルキル(メタ)アクリレート、酢酸ビニル、スチレン、およびそれらの混合物からなる群から選択され、そのホモポリマーのガラス転移温度が-30℃より高いものから選択される少なくとも1つの共重合性モノマー5−59.5重量%、および
(iii)ヒドロキシアルキル(メタ)アクリレート、ヒドロキシアルキル(メタ)アクリレートのエトキシル化及び/又はプロポキシル化誘導体、それらのラクトン類との付加物、(メタ)アクリル酸、β−カルボキシエチル(メタ)アクリレート、クロトン酸、マレイン酸、フマル酸、イタコン酸、アクリル酸、メタクリル酸、およびこれらの混合物からなる群から選択される、ヒドロキシル基およびカルボキシル基からなる群から選択される官能基を有する少なくとも1つの共重合可能な官能性モノマー0.5−20重量%
を含み、ここで、該アクリルコポリマー中の残留溶媒含有量は1重量%未満であり、該アクリルコポリマーのガラス転移温度は約-60℃−約20℃の範囲である、
および
(b)アクリルコポリマーを、触媒の存在下でUV硬化性官能基を含む少なくとも1種のモノマーと反応させて、UV硬化性アクリルコポリマーを形成すること
を含む、方法。 - 前記モノマーの混合物は、
(i)少なくとも1つの(メタ)アクリレートモノマー少なくとも約45重量%;および/または
(ii)少なくとも1つの(メタ)アクリレートモノマー約94重量%以下
を含む、請求項1に記載の方法。 - 前記少なくとも1種の(メタ)アクリレートモノマーは、アルキル(メタ)アクリレートである、請求項1または2に記載の方法。
- 前記モノマーの混合物は、
(i)少なくとも1つの共重合性モノマー少なくとも約10重量%;および/または
(ii)少なくとも1つの共重合性モノマー59重量%以下
を含む、請求項1−3のいずれかに記載の方法。 - 共重合性モノマーは、アルキル(メタ)アクリレート、ビニルアセテート、スチレン、およびそれらの混合物からなる群から選択される、請求項1−4のいずれかに記載の方法。
- 前記モノマー混合物は、
(i)少なくとも1つの共重合可能な官能性モノマー少なくとも約1重量%;および/または
(ii)少なくとも1つの共重合可能な官能性モノマー10重量%以下
を含む、請求項1−5のいずれかに記載の方法。 - 請求項1−6のいずれかに記載の方法であって、前記少なくとも1つの共重合可能な官能性モノマーは、ヒドロキシアルキル(メタ)アクリレート、ヒドロキシアルキル(メタ)アクリレートのエトキシル化および/またはプロポキシル化誘導体、それらのラクトン付加物、(メタ)アクリル酸、β-カルボキシエチル(メタ)アクリレート、クロトン酸、マレイン酸、フマル酸、イタコン酸 、アクリル酸、ヒドロキシエチルアクリレート、およびそれらの混合物からなる群から選択される、方法。
- 前記モノマーの混合物は、
a)2-エチルヘキシルアクリレート、メタクリル酸、アクリル酸メチルおよびアクリル酸エチル;又は
b)ブチルアクリレート、メタクリル酸、アクリル酸メチルおよびアクリル酸エチル
を含むかまたはそれからなる、請求項1−7のいずれかに記載の方法。 - UV硬化性基を含むモノマーは、ビニルおよびエポキシ基を含むモノマーである、請求項1−8のいずれかに記載の方法。
- 請求項1−9のいずれかに記載の方法であって、熱及び/又は真空を適用することによって、アクリルコポリマー中の残留溶剤含有量を1重量%未満とする、方法。
- 請求項1−9のいずれかに記載の方法によって得られるUV硬化性アクリルコポリマーからなる感圧接着剤またはホットメルト。
- 請求項11に記載の感圧接着剤またはホットメルトと光開始剤とを含む、感圧接着剤またはホットメルト組成物。
- 接着シートの製造方法であって、
i)請求項12に記載の接着剤組成物を基材上にコーティングして、前記基材表面上に前記接着剤組成物の層を形成すること;および
ii)接着剤組成物の層にUV光を照射して接着シートを形成すること
を含む方法。
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