CN115109544A - Adhesive composition, adhesive layer, and adhesive film - Google Patents
Adhesive composition, adhesive layer, and adhesive film Download PDFInfo
- Publication number
- CN115109544A CN115109544A CN202110294580.XA CN202110294580A CN115109544A CN 115109544 A CN115109544 A CN 115109544A CN 202110294580 A CN202110294580 A CN 202110294580A CN 115109544 A CN115109544 A CN 115109544A
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- Prior art keywords
- meth
- mass
- acrylate
- monomer
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- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 30
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000002313 adhesive film Substances 0.000 title claims abstract description 14
- 239000012790 adhesive layer Substances 0.000 title claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 133
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 129
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 54
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000009477 glass transition Effects 0.000 claims description 12
- -1 n-octyl group Chemical group 0.000 description 55
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 27
- 239000004925 Acrylic resin Substances 0.000 description 19
- 229920000178 Acrylic resin Polymers 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 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 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 150000003926 acrylamides Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 206010057040 Temperature intolerance Diseases 0.000 description 2
- 239000003522 acrylic cement Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000008543 heat sensitivity Effects 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 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 2
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-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
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- IOSXLUZXMXORMX-UHFFFAOYSA-N 1-ethenoxypentane Chemical compound CCCCCOC=C IOSXLUZXMXORMX-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 description 1
- RYZCLQLQLZXPGE-UHFFFAOYSA-N 1-prop-2-enoylpiperidin-2-one Chemical compound C=CC(=O)N1CCCCC1=O RYZCLQLQLZXPGE-UHFFFAOYSA-N 0.000 description 1
- XUZOTORSRZQIJN-UHFFFAOYSA-N 1-prop-2-enoylpiperidin-4-one Chemical compound C=CC(=O)N1CCC(=O)CC1 XUZOTORSRZQIJN-UHFFFAOYSA-N 0.000 description 1
- WLPAQAXAZQUXBG-UHFFFAOYSA-N 1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCC1 WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- SKKHNUKNMQLBTJ-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanyl 2-methylprop-2-enoate Chemical compound C1CC2C(OC(=O)C(=C)C)CC1C2 SKKHNUKNMQLBTJ-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FVWPIHOOWVNTNI-UHFFFAOYSA-N C(CC(C(C=C(F)F)(F)F)(F)F)F Chemical compound C(CC(C(C=C(F)F)(F)F)(F)F)F FVWPIHOOWVNTNI-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- C09J133/24—Homopolymers or copolymers of amides or imides
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention relates to an adhesive composition, an adhesive layer and an adhesive film, the adhesive composition comprising: an acrylic polymer (A), a crosslinking agent (B), and an acrylic polymer (C), the acrylic polymer (A) comprising: units derived from (meth) acrylate monomer (a 1); units derived from a nitrogen-containing monomer (a 2); and a unit derived from at least one selected from the group consisting of a monomer (a3) having an acid group and a monomer (a4) having a hydroxyl group, the acrylic polymer (a) having a weight average molecular weight of 100,000 or more, the acrylic polymer (C) comprising: a unit derived from an alicyclic structure-containing (meth) acrylate monomer (c 1); and units derived from an alkyl (meth) acrylate monomer (c 2).
Description
Technical Field
The invention relates to an adhesive composition, an adhesive layer and an adhesive film.
Background
Acrylic adhesives have been used in various fields since now, and in particular, in recent years, demand for Information Technology (IT) related products such as smart phones is high. These IT-related products are required to have higher performance and higher functions according to their product characteristics.
As an example of an acrylic adhesive used for IT-related products, a heat-sensitive adhesive is required which exhibits strong adhesiveness by heating although IT has slight adhesiveness at normal temperature, and also has sustained adhesiveness after the release of heating. As a specific example thereof, for example, an adhesive containing an acrylic low-molecular weight polymer having a weight average molecular weight of 1,000 to 50,000 has been proposed (for example, see patent document 1). In addition, an adhesive is proposed, comprising: a polymer having a glass transition temperature of less than 0 ℃; and a polymer containing a monomer having a polyorganosiloxane skeleton and a monomer having a glass transition temperature of 40 ℃ or higher as monomer units and having a weight average molecular weight of 10,000 or more and less than 100,000 (see, for example, patent document 2).
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent laid-open No. 2008-222814
[ patent document 2] Japanese patent laid-open No. 2019-123884
Disclosure of Invention
[ problems to be solved by the invention ]
In IT-related products, high optical transparency (film transparency) is required, but in the case of the conventionally known pressure-sensitive adhesives, IT is sometimes difficult to develop micro-adhesiveness at room temperature and strong adhesiveness after heating (hereinafter, micro-adhesiveness at room temperature and strong adhesiveness after heating are sometimes collectively referred to as "high heat-sensitive adhesive force" or the like) while maintaining optical transparency.
The present invention has been made in view of the above circumstances, and an object thereof is to develop a high adhesive force by heat-sensitivity while maintaining optical transparency.
[ means for solving problems ]
The adhesive composition of the present invention comprises: an acrylic polymer (A), a crosslinking agent (B), and an acrylic polymer (C), the acrylic polymer (A) comprising: units derived from (meth) acrylate monomer (a 1); units derived from a nitrogen-containing monomer (a 2); and a unit derived from at least one selected from the group consisting of a monomer (a3) having an acid group and a monomer (a4) having a hydroxyl group, the acrylic polymer (a) having a weight average molecular weight of 100,000 or more, the acrylic polymer (C) comprising: a unit derived from an alicyclic structure-containing (meth) acrylate monomer (c 1); and a unit derived from an alkyl (meth) acrylate monomer (C2), the content of the unit derived from the alicyclic structure-containing (meth) acrylate monomer (C1) being 35% by mass or more and less than 95% by mass in the acrylic polymer (C), the glass transition temperature of the acrylic polymer (C) being 50 ℃ or more, and the weight-average molecular weight of the acrylic polymer (C) being less than 100,000.
[ Effect of the invention ]
By using the adhesive composition of the present invention, high adhesive force can be exhibited by heat-sensitivity while maintaining optical transparency.
Detailed Description
The adhesive composition of the present invention comprises: an acrylic polymer (A), a crosslinking agent (B) and an acrylic polymer (C).
The acrylic polymer (A) comprises: units derived from (meth) acrylate monomer (a 1); units derived from a nitrogen-containing monomer (a 2); and a unit derived from at least one selected from the group consisting of a monomer (a3) having an acid group and a monomer (a4) having a hydroxyl group.
Examples of the (meth) acrylate monomer (a1) include: an alkyl (meth) acrylate monomer having an alkyl group bonded with an ester, a cyclic ether-containing (meth) acrylate monomer, an alicyclic structure-containing (meth) acrylate monomer, an aromatic ring-containing (meth) acrylate monomer, an alkylene oxide structure-containing (meth) acrylate monomer, and the like.
Examples of the alkyl group in the alkyl (meth) acrylate monomer include: a linear alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, a lauryl group, and a stearyl group; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, isohexyl, isoheptyl, isooctyl, 2-ethylhexyl, isononyl, isodecyl, and isostearyl. The number of carbon atoms of the alkyl group is preferably 1 or more, and preferably 20 or less, more preferably 15 or less, and further preferably 12 or less.
Examples of the alkyl (meth) acrylate monomer include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, and the like.
Further, examples of the (meth) acrylate ester monomer (a1) include: cyclic ether-containing (meth) acrylate monomers such as glycidyl (meth) acrylate and tetrahydrofurfuryl (meth) acrylate; alicyclic structure-containing (meth) acrylate monomers such as cyclohexyl (meth) acrylate and isobornyl (meth) acrylate; aromatic ring-containing (meth) acrylate monomers such as phenoxyethyl (meth) acrylate and benzyl (meth) acrylate; and (meth) acrylate monomers containing an alkylene oxide structure, such as 2-methoxyethyl (meth) acrylate, methoxybutyl (meth) acrylate, and methoxypolyethylene glycol (meth) acrylate.
The alkyl (meth) acrylate monomer (a1) includes a low Tg monomer (a1-1) having a homopolymer glass transition temperature (Tg) of less than-15 ℃ and a high Tg monomer (a1-2) having a homopolymer glass transition temperature (Tg) of-15 ℃ or higher.
The low Tg monomer (a1-1) may have a glass transition temperature (Tg) of less than-15 ℃, preferably-20 ℃ or less, more preferably-25 ℃ or less, and the lower limit thereof may be, for example, -100 ℃ or more.
The content of the low Tg monomer (a1-1) in the alkyl (meth) acrylate monomer is preferably 30% by mass or more, more preferably 40% by mass or more, and even more preferably 44% by mass or more, and is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less.
The glass transition temperature of the high Tg monomer (a1-2) is-15 ℃ or higher, preferably-10 ℃ or higher, more preferably-5 ℃ or higher, and the upper limit thereof may be 150 ℃ or lower or 100 ℃ or lower, for example.
The content of the high Tg monomer (a1-2) is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, further preferably 25 parts by mass or more, and preferably 50 parts by mass or less, more preferably 45 parts by mass or less, further preferably 40 parts by mass or less, relative to 100 parts by mass of the low Tg monomer (a 1-1).
The unit derived from the high Tg monomer (a1-2) is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass or more, and preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less in the acrylic polymer (a).
One or more (meth) acrylate monomers (a1) may be used, and alkyl acrylate and alicyclic structure-containing (meth) acrylate monomers are preferred in terms of providing flexibility and cohesive force in a well-balanced manner.
In the acrylic polymer (a), the content of the unit derived from the (meth) acrylate monomer (a1) is preferably 50% by mass or more, more preferably 70% by mass or more, and is preferably 97% by mass or less, more preferably 95% by mass or less.
The nitrogen-containing monomer (a2) is a monomer having a nitrogen atom and a polymerizable double bond in the molecule, preferably a monomer having an amide bond and a polymerizable double bond in the molecule, and examples thereof include: lactam compounds having a vinyl group; (meth) acrylamide monomers; and (meth) acrylate compounds having a functional group containing a nitrogen atom (for example, an amino group, a 1-substituted amino group, a 2-substituted amino group, a nitrile group, etc.).
Examples of the lactam compound having a vinyl group include: n-vinylpyrrolidone, N-vinylcaprolactam, and the like.
The (meth) acrylamide monomer includes: a hydrogen atom or a hydrocarbon group (preferably an aliphatic hydrocarbon group; wherein-CH is contained in the hydrocarbon group) is bonded to the nitrogen atom of the (meth) acrylamide 2 A compound which may be substituted by-CO-, and the hydrogen atom contained in the hydrocarbon group may be substituted by a hydroxyl group), and the like. In addition, when two or more groups (the hydrocarbon group) substitute for the nitrogen atom of the (meth) acrylamide, these groups may be bonded to each other to form a ring including the nitrogen atom.
The number of carbon atoms of the hydrocarbon group (preferably, aliphatic hydrocarbon group) substituted with a nitrogen atom contained in the amide bond is preferably 1 or more, and preferably 10 or less, and more preferably 6 or less.
One or two or more kinds of the (meth) acrylamide monomers (a2) can be used. The (meth) acrylamide monomer may be any of (meth) acrylamide, an N-1 substituted (meth) acrylamide compound, and an N, N-2 substituted (meth) acrylamide compound.
As the (meth) acrylamide compound, one or two or more kinds may be used, and examples thereof include: (meth) acrylamide; n-1 substituted (meth) acrylamide compounds such as N-isopropyl (meth) acrylamide, N- (1, 1-dimethyl-3-oxobutyl) acrylamide, N-methylol (meth) acrylamide, N-methoxymethyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N- (2-hydroxymethyl) acrylamide, and N- (2-hydroxyethyl) acrylamide; n-2 substituted (meth) acrylamide compounds such as N- (meth) acryloylmorpholine, N- (meth) acryloylpiperidone, N- (meth) acryloylpiperidine, N- (meth) acryloylpyrrolidine, N- (meth) acryloyl-4-piperidone, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-diisopropyl (meth) acrylamide, N-methylenebis (meth) acrylamide, and N, N-dimethylaminopropyl (meth) acrylamide.
Among them, the (meth) acrylamide monomer is preferably a monomer containing the monomer represented by the formula (1).
[ solution 1]
[ in the formula (1), R 1 Represents a hydrogen atom or a methyl group; r 2 And R 3 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and-CH contained in the hydrocarbon group 2 -may be substituted by-CO-or-O-, the hydrogen atom contained in said hydrocarbon group may be substituted by a hydroxyl group, R 2 And R 3 May be bonded to each other to form a ring containing a nitrogen atom]
As said R 2 And R 3 The hydrocarbon group represented by (a) may be one or two or more, and examples thereof include: a straight or branched saturated aliphatic hydrocarbon group; straight-chain or branched unsaturated aliphatic hydrocarbon groups, and the like. Among them, a straight-chain or branched saturated aliphatic hydrocarbon group is preferable, and a branched saturated aliphatic hydrocarbon group is more preferable. Preferably R 2 And R 3 Is a hydrogen atom.
The (meth) acrylamide monomer also preferably contains R 2 And R 3 Both of which are the (meth) acrylamide monomers of the hydrocarbon group. In the presence of said compound containing R 2 And R 3 When both are the hydrocarbon group-containing (meth) acrylamide monomers, the content of the unit derived from the monomer is preferably 0.5% by mass or more, more preferably 1% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less in the acrylic polymer (a).
In the nitrogen-containing monomer (a2), the content of the unit derived from the acrylamide monomer is preferably 70% by mass or more, more preferably 80% by mass or more, and still more preferably 90% by mass or more, with the upper limit being 100% by mass.
Examples of the (meth) acrylate compound having a functional group containing a nitrogen atom (for example, an amino group, a 1-substituted amino group, a 2-substituted amino group, a nitrile group, and the like) include: (meth) acrylonitrile, t-butylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, and the like.
In the acrylic polymer (a), the content of the unit derived from the nitrogen-containing monomer (a2) is preferably 0.5% by mass or more, more preferably 1% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less.
The monomer (a3) having an acid group includes a monomer having an acid group and a polymerizable double bond, preferably a monomer having a carboxyl group and a monomer having a sulfo group, and preferably a monomer having a carboxyl group.
As the monomer having a carboxyl group, one or two or more kinds may be used, and examples thereof include: (meth) acrylic acid; carboxyalkyl (meth) acrylates such as carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, and β -carboxyethyl (meth) acrylate; unsaturated carboxylic acids such as itaconic acid, itaconic anhydride, maleic acid, maleic anhydride, fumaric acid, and crotonic acid.
In the monomer (a3) having an acid group, the content of the monomer having a carboxyl group is preferably 80% by mass or more, more preferably 90% by mass or more, and still more preferably 95% by mass or more, with the upper limit being 100% by mass.
In the acrylic polymer (a), the content of the unit derived from the monomer (a3) having an acid group is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less, and still more preferably 12% by mass or less.
Examples of the monomer (a4) having a hydroxyl group include monomers having a hydroxyl group and a polymerizable double bond. Examples of the monomer (a4) having a hydroxyl group include: hydroxyalkyl (meth) acrylates; hydroxyalkyl (meth) acrylamides; polyalkylene glycol (meth) acrylates and the like, preferably hydroxyalkyl (meth) acrylates.
As the monomer having a hydroxyl group (a4), there may be specifically mentioned: hydroxyalkyl (meth) acrylates having an alkyl (alkylene) group having 2 to 10 carbon atoms such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and 8-hydroxyoctyl (meth) acrylate; hydroxyalkyl (meth) acrylamides having an alkyl (alkylene) group having 2 to 8 carbon atoms such as 2-hydroxyethyl (meth) acrylamide, 4-hydroxyethyl (meth) acrylamide, 6-hydroxyhexyl (meth) acrylamide, and 8-hydroxyoctyl (meth) acrylamide; polyalkylene glycol (meth) acrylates such as polyethylene glycol (meth) acrylates, and the like.
The content of the unit derived from the hydroxyl group-containing monomer (a4) in the acrylic monomer (a) is preferably 0.01% by mass or more, more preferably 0.03% by mass or more, further preferably 0.05% by mass or more, and preferably 10% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less.
The total of the units derived from the monomer (a3) having an acid group and the monomer (a4) having a hydroxyl group in the acrylic polymer (a) is 0.5% by mass or more, preferably 1.5% by mass or more, more preferably 2% by mass or more, and preferably 30% by mass or less, more preferably 22% by mass or less, and still more preferably 17% by mass or less.
In the acrylic polymer (a), the total of units derived from the alkyl (meth) acrylate monomer (a1), the nitrogen-containing monomer (a2), the monomer having an acid group (a3), and the monomer having a hydroxyl group (a4) is preferably 70% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, and the upper limit is 100% by mass in the acrylic polymer (a).
The acrylic polymer (a) may have units derived from other monomers (ax) than the alkyl (meth) acrylate monomer (a1), the nitrogen-containing monomer (a2), the monomer having an acid group (a3), and the monomer having a hydroxyl group (a 4).
As the other monomer (ax), one or two or more kinds may be used, and examples thereof include: vinyl ester monomers such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl versatate; vinyl ether monomers such as methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, pentyl vinyl ether, and hexyl vinyl ether; aromatic vinyl monomers such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, ethylvinylbenzene, α -methylstyrene, p-methoxystyrene, p-t-butylstyrene, p-phenylstyrene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, and p-hydroxystyrene; isoprene, chloroprene, butadiene, ethylene, tetrafluoroethylene, vinylidene fluoride, and the like.
The content of the unit derived from another monomer (ax) in the acrylic polymer (a) is preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less, and the lower limit is 0% by mass.
The weight average molecular weight of the acrylic polymer (a) is 100,000 or more, preferably 200,000 or more, more preferably 300,000 or more, and preferably 2,000,000 or less, more preferably 1,800,000 or less, and further preferably 1,500,000 or less.
In the present specification, the number average molecular weight and the weight average molecular weight of the acrylic polymer (a) are converted values measured by Gel Permeation Chromatography (GPC) using polystyrene as a standard sample.
In the pressure-sensitive adhesive composition of the present invention, the content of the acrylic polymer (a) is preferably 15% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, and preferably 99% by mass or less in the nonvolatile content.
In the present specification, the nonvolatile component of the pressure-sensitive adhesive composition means a portion obtained by removing a solvent component optionally contained in the pressure-sensitive adhesive composition.
The acrylic polymer (a) may be produced by copolymerizing the alkyl (meth) acrylate monomer (a1), the nitrogen-containing monomer (a2), the monomer having an acid group (a3), the monomer having a hydroxyl group (a4), and other monomers (ax) used as necessary in the presence of a polymerization initiator.
As the polymerization initiator, for example, one or two or more of thermal polymerization initiators can be used, and there can be mentioned: peroxide initiators such as benzoyl peroxide and lauroyl peroxide; azo initiators such as azobismethylbutyronitrile and azobisisobutyronitrile.
The adhesive composition of the present invention contains a crosslinking agent (B). As the crosslinking agent, one or two or more kinds may be used, and for example, there may be mentioned: isocyanate crosslinking agents, epoxy crosslinking agents, aziridine crosslinking agents, polyvalent metal salt crosslinking agents, metal chelate crosslinking agents, ketone-hydrazide crosslinking agents, oxazoline crosslinking agents, carbodiimide crosslinking agents, silane crosslinking agents, glycidyl (alkoxy) epoxy silane crosslinking agents, and the like.
Among these, isocyanate crosslinking agents, epoxy crosslinking agents, oxazoline crosslinking agents, and carbodiimide crosslinking agents are preferable, isocyanate crosslinking agents, epoxy crosslinking agents, and carbodiimide crosslinking agents are more preferable, and epoxy crosslinking agents are particularly preferable.
The content of the epoxy crosslinking agent in the crosslinking agent (B) is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 80% by mass or more, further preferably 90% by mass or more, and preferably 100% by mass or less.
The content of the crosslinking agent (B) is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more, and is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 1 part by mass or less, relative to 100 parts by mass of the acrylic polymer (a).
The acrylic polymer (C) comprises: a unit derived from an alicyclic structure-containing (meth) acrylate monomer (c 1); and units derived from an alkyl (meth) acrylate monomer (c 2).
The alicyclic structure-containing (meth) acrylate monomer (c1) (hereinafter, may be abbreviated as "(meth) acrylate (c 1)") represents a (meth) acrylate monomer having an alicyclic structure in the molecule. The alicyclic hydrocarbon group may be a monocyclic ring or a bridged ring, and the number of the alicyclic hydrocarbon groups contained in the (meth) acrylate (c1) may be 1 or 2 or more.
Examples of the alicyclic hydrocarbon group contained in the (meth) acrylate (c1) include: monocyclic alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, and cycloheptyl; and bridged alicyclic hydrocarbon groups such as norbornyl, isobornyl, and dicyclopentanyl.
The alicyclic hydrocarbon group contained in the (meth) acrylate (c1) has 3 or more, preferably 5 or more, and preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less carbon atoms.
As the alicyclic structure-containing (meth) acrylate monomer (c1) contained in the (meth) acrylate (c1), specifically, one or two or more kinds can be used, and examples thereof include: a (meth) acrylate monomer having a monocyclic alicyclic structure such as cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, and the like; and (meth) acrylate monomers containing a bridged ring alicyclic structure such as norbornyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentanyl (meth) acrylate.
The content of the unit derived from the (meth) acrylic ester (C1) in the acrylic polymer (C) is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 35% by mass or more, and is preferably 99% by mass or less, more preferably 95% by mass or less, and even more preferably 92% by mass or less.
The alkyl (meth) acrylate monomer (c2) (hereinafter, may be abbreviated as "(meth) acrylate (c 2)") represents a (meth) acrylate monomer having an alkyl group.
Examples of the alkyl group contained in the (meth) acrylic acid ester (c2) include: a linear alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, a lauryl group, and a stearyl group; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, isohexyl, isoheptyl, isooctyl, 2-ethylhexyl, isononyl, isodecyl, and isostearyl.
The alkyl group contained in the (meth) acrylate (c2) preferably has 1 or more carbon atoms, and preferably 20 or less, more preferably 15 or less, and still more preferably 12 or less.
As the (meth) acrylic acid ester (c2), one or two or more kinds may be used, and examples thereof include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, and the like.
The content of the unit derived from the (meth) acrylic acid ester (C2) in the acrylic polymer (C) is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 7% by mass or more, and is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.
The content ratio ((c1)/(c2)) of the unit derived from the (meth) acrylate (c1) to the unit derived from the (meth) acrylate (c2) is preferably 0.1 or more, more preferably 0.5 or more, further preferably 0.7 or more, and preferably 20 or less, more preferably 15 or less, further preferably 12 or less on a mass basis.
The acrylic polymer (C) may contain a unit derived from another monomer (C3) in addition to the unit derived from the alicyclic structure-containing (meth) acrylate monomer (C1) and the alkyl (meth) acrylate monomer (C2).
Examples of the other monomer (c3) include: other (meth) acrylate monomers such as the cyclic ether-containing (meth) acrylate monomer, the aromatic ring-containing (meth) acrylate monomer, and the alkylene oxide structure-containing (meth) acrylate monomer; the nitrogen-containing monomer, and the like.
The content of the other monomer (C3) in the acrylic polymer (C) is preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 12% by mass or less, and the lower limit is 0% by mass.
The glass transition temperature of the acrylic polymer (C) is 50 ℃ or higher, preferably 55 ℃ or higher, more preferably 60 ℃ or higher, and preferably 120 ℃ or lower, more preferably 110 ℃ or lower.
The glass transition temperature Tga (K) of the acrylic polymer (C) can be calculated based on the following Fox formula.
1/Tga＝Σ(Wi/Tgi)
In the Fox formula, Wi represents the content of units derived from the monomers in the acrylic polymer (C), and Tgi (K) represents the glass transition temperature (in absolute temperature) of a homopolymer formed from only the monomers. Details of the Fox formula are described in Physical Society of America (Bulletin of the American Physical Society, Series 2), Vol.1, No.3, page 123 (1956). The glass transition temperature (Tgi) of the homopolymer of each monomer can be, for example, the value described in "coating and paint" (coating Press, 10(No.358), 1982).
The weight average molecular weight of the acrylic polymer (C) is less than 100,000, preferably 80,000 or less, more preferably 60,000 or less, and preferably 1,000 or more, more preferably 1,500 or more, and further preferably 2,500 or more.
In the present specification, the number average molecular weight and the weight average molecular weight of the acrylic polymer (C) represent values converted from polystyrene as a standard sample and measured by Gel Permeation Chromatography (GPC).
In the pressure-sensitive adhesive composition of the present invention, the content of the acrylic polymer (C) is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 7% by mass or more, and preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less in the nonvolatile content.
In the adhesive composition of the present invention, the content of the acrylic polymer (C) is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 7 parts by mass or more, and is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, and even more preferably 20 parts by mass or less, with respect to 100 parts by mass of the acrylic polymer (a).
The acrylic polymer (C) can be produced by copolymerizing the alicyclic structure-containing (meth) acrylate monomer (C1), the alkyl (meth) acrylate monomer (C2), and optionally another monomer (C3) in the presence of a polymerization initiator.
As the polymerization initiator, for example, one or two or more of thermal polymerization initiators can be used, and there can be mentioned: peroxide initiators such as benzoyl peroxide and lauroyl peroxide; azo initiators such as azobismethylbutyronitrile and azobisisobutyronitrile.
The adhesive composition of the present invention preferably comprises a solvent (D). As the solvent (D), one or two or more kinds may be used, and for example, there may be mentioned: aromatic hydrocarbon solvents such as toluene and xylene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone and methyl ethyl ketone; and aliphatic hydrocarbon solvents such as hexane. Among them, the ester solvent is preferably contained.
The content of the ester solvent in the solvent (D) is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 70% by mass or more, and preferably 100% by mass or less.
The content of the solvent (D) in the adhesive composition is preferably 10% by mass or more, more preferably 30% by mass or more, and even more preferably 50% by mass or more, and preferably 90% by mass or less, more preferably 70% by mass or less, and even more preferably 65% by mass or less.
In the pressure-sensitive adhesive composition of the present invention, in order to maintain low yellowing, the content of the adhesion-imparting resin is preferably reduced, and is preferably less than 10 parts by mass, more preferably 8 parts by mass or less, further preferably 3 parts by mass or less, further more preferably 1 part by mass or less, and preferably 0 part by mass, relative to 100 parts by mass of the acrylic polymer.
The adhesive composition of the present invention may also contain a base (ammonia or the like) or an acid for adjusting the pH; a blowing agent; a plasticizer; a softening agent; an antioxidant; fillers such as glass or plastic fibers, balloon beads, and metal powder; colorants such as pigment-dyes; a pH value adjusting agent; a film-forming auxiliary agent; leveling agent; a tackifier; a hydrophobizing agent; defoaming agents; an acid catalyst; acid generators, and the like as additives.
The adhesive layer can be formed by applying the adhesive composition to a support and drying it. The support may be any substrate such as a release sheet or an adhesive sheet.
As the coating method, a knife coater, a reverse coater, a die coater, a lip die coater, a slit die coater, a gravure coater, a curtain coater, or the like can be used.
The thickness of the adhesive layer is preferably 5 μm or more, more preferably 10 μm or more, further preferably 15 μm or more, and preferably 150 μm or less, more preferably 100 μm or less, further preferably 75 μm or less.
The adhesive sheet or adhesive tape of the present invention has the adhesive layer and the substrate. The substrate may be in any shape such as a film, a sheet, a tape, a plate, or a three-dimensional shape, and examples of the material of the substrate include plastics such as polyester resin, polypropylene resin, polyethylene resin, polyimide resin, vinyl chloride resin, and urethane resin; rubber; non-woven fabrics; a metal foil; paper and the like are preferred, and polyester resin is more preferred. The substrate may be a substrate having a smooth surface, or a substrate having irregularities on the surface, such as a fibrous substrate or a foam substrate.
The thickness of the base material is preferably 0.1 μm or more, and preferably 1,000 μm or less.
[ examples ]
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples, and it goes without saying that the present invention can be carried out by appropriately changing the examples within a range that can be adapted to the gist described above and described later, and these are included in the technical scope of the present invention.
[ examples ]
The present invention will be specifically described with reference to examples and comparative examples.
Synthetic example 1: synthesis of acrylic resin (A1) ]
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet, and a thermometer, 200 parts by mass of butyl acrylate (hereinafter, abbreviated as "BA"), 277 parts by mass of 2-ethylhexyl acrylate (hereinafter, abbreviated as "2 EHA"), 400 parts by mass of cyclohexyl acrylate (hereinafter, abbreviated as "CHA"), 50 parts by mass of diacetoneacrylamide (hereinafter, abbreviated as "DAAM"), 70 parts by mass of acrylic acid (hereinafter, abbreviated as "AA"), 3 parts by mass of 4-hydroxybutyl acrylate (hereinafter, abbreviated as "4 HBA"), and 1000 parts by mass of ethyl acetate were charged, and the temperature was raised to 70 ℃ while nitrogen gas was blown under stirring. After 1 hour, 10 parts by mass (5% by mass of solid content) of a2, 2' -azobis (2-methylbutyronitrile) solution obtained by dissolving in ethyl acetate in advance was added. Thereafter, the mixture was held at 70 ℃ for 8 hours under stirring, and then the contents were cooled and filtered through a 200-mesh wire gauze to obtain an acrylic resin (A1) having a nonvolatile content of 50 mass%, a viscosity of 100,000 mPas and a weight-average molecular weight of 90 ten thousand.
[ Synthesis examples 2 to 3]
Acrylic resins (a2) to (A3) were obtained in the same manner as in synthesis example 1, except that the (meth) acrylate monomer (a1), the nitrogen-containing monomer (b), the acid group-containing monomer (c), and the hydroxyl group-containing monomer (d) were changed as shown in table 1.
[ Synthesis example 4: synthesis of acrylic resin (C-1)
395 parts by mass of methyl ethyl ketone (hereinafter, abbreviated as "MEK") was charged into a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, a cooling tube and a nitrogen introduction port, and the temperature was raised to 80 ℃. Then, a mixture containing 220 parts by mass of cyclohexyl methacrylate (hereinafter, abbreviated as "CHMA"), 138 parts by mass of methyl methacrylate (hereinafter, abbreviated as "MMA"), 127 parts by mass of butyl methacrylate (hereinafter, abbreviated as "BMA"), 38 parts by mass of BA, 28 parts by mass of methacrylic acid (hereinafter, abbreviated as "MAA"), 33 parts by mass of MEK and 55 parts by mass of t-butyl peroxy-2-ethylhexanoate (hereinafter, abbreviated as "TBPEH") was dropped into the reaction vessel at the same temperature over 4 hours, and after the dropping, a reaction was carried out at the same temperature for 20 hours to obtain an organic solvent solution of an acrylic resin (C-1) having a nonvolatile component of 55 mass% and a weight average molecular weight of 2,500.
Synthesis examples 5 to 10 and comparative Synthesis examples 1 to 4
Acrylic resins (C-2) to (C-7) and comparative acrylic resins (r-1) to (r-4) were obtained in the same manner as in Synthesis example 4, except that the (meth) acrylate monomer was changed as shown in tables 2 and 3.
[ Table 1]
[ Table 2]
[ Table 3]
[ example 1]
18 parts by mass of the acrylic resin (C-1) obtained in Synthesis example 4 and 0.3 part by mass of an epoxy-based crosslinking agent (Vannatech (Finetcack) hardener EX-50; manufactured by Diesen (DIC) (Strand)) were mixed with stirring so as to become uniform with respect to 100 parts by mass of the acrylic resin (A1) obtained in Synthesis example 1, thereby obtaining an acrylic adhesive composition.
Examples 2 to 13 and comparative examples 1 to 5
As shown in table 4, an acrylic pressure-sensitive adhesive composition was obtained in the same manner as in example 1 except that the acrylic resin (a2) to the acrylic resin (A3) obtained in synthesis example 2 to synthesis example 3 were changed instead of the acrylic resin (a1) obtained in synthesis example 1, and the acrylic resin (C-2) to the acrylic resin (C-7) obtained in synthesis example 5 to synthesis example 10 and the comparative acrylic resin (r-1) to the comparative acrylic resin (r-4) obtained in comparative synthesis example 1 to comparative synthesis example 4 were changed instead of the acrylic resin (C-1) obtained in synthesis example 4.
[ method of processing adhesive film ]
The acrylic pressure-sensitive adhesive composition obtained in example was applied to the surface of a polyethylene terephthalate film (release PET50) whose surface was subjected to release treatment and whose thickness was 50 μm so that the film thickness after drying the solvent was 25 μm, and the solvent was volatilized in a dryer at 80 ℃ for 3 minutes, followed by lamination of a PET50 μm film.
[ measuring method of adhesive Strength ]
The adhesive film produced by the above method was cut into a width of 25mm, and the thus-obtained article was used as a test piece. The adherend was a glass plate and was attached to the adherend by a 2kg roller × 2 reciprocations. After 1 hour of the attachment, 180 degree peel strength was measured at 23 ℃ and 50% RH to obtain adhesive strength.
[ method of measuring adhesive Strength after Heat treatment ]
The adhesive film produced by the above method was cut into a width of 25mm, and the thus-obtained article was used as a test piece. The adherend was a glass plate and was attached to the adherend by a 2kg roller × 2 reciprocations. After the application, the sheet was heated for 5 minutes in a dryer at 120 ℃ and taken out from the dryer, and after 1 hour, the 180-degree peel strength was measured in an environment of 23 ℃ and 50% RH to obtain the post-heat-treatment adhesive strength.
[ method of measuring holding force after Heat treatment ]
The adhesive film produced by the above method was cut into a width of 25mm, and the thus-obtained article was used as a test piece. The stainless steel plate subjected to the mirror finish was attached to the stainless steel plate by 2 reciprocal movements with a 2kg roller having an adhesive area of 25mm × 25 mm. After the adhesion, the test piece was heated for 5 minutes in a dryer at 120 ℃ and taken out from the dryer, and after 1 hour, a load of 1kg was applied to the test piece adhered to the stainless steel plate in a direction (shear direction) of 0 ° to the stainless steel plate in an environment at 70 ℃, and the time until the adhesive film slipped off from the adherend was measured, and the holding time was defined as the holding power after the heat treatment. When the holding time is 24 hours or more, the holding time is 24 hours or more.
[ method of measuring initial color number (b) ]
The adhesive film prepared by the above method was attached to a glass plate, and the thus-obtained article was used as a test piece. The initial color number (b) was measured on the test piece by using a light source C, a visual field of view of 2 degrees, and a "spectrocolorimeter" CM-5000d (Konica Minolta Sensing) (manufactured by Konica Minolta Sensing Co., Ltd.) according to Japanese Industrial Standard (JIS) K7105.
[ method for measuring initial haze and initial light transmittance ]
The adhesive film prepared by the above method was attached to a glass plate, and the thus-obtained article was used as a test piece. The haze and the light transmittance were measured by a haze meter "NDH 5000" (manufactured by Nippon Denshoku industries Co., Ltd.) on the test piece according to JIS K7361-1.
[ measurement methods of color number (b), haze, and light transmittance after Heat treatment ]
The adhesive film prepared by the above method was attached to a glass plate, heated for 5 minutes by a dryer at 120 ℃, and the thus obtained article was used as a test piece, and the color number (b ×) after heat treatment was measured on the test piece in accordance with JIS K7105 in the same manner as the above method. The adhesive film prepared by the above method was attached to a glass plate, and the resultant was heated in a dryer at 120 ℃ for 5 minutes to obtain a test piece, and the haze and the light transmittance were measured by a haze meter "NDH 5000" in accordance with JIS K7361-1 in the same manner as the above method.
In tables 1 to 5, the following compounds are shown for short.
BA: acrylic acid n-butyl ester
2 EHA: 2-ethylhexyl acrylate
CHA: acrylic acid cyclohexyl ester
MA: acrylic acid methyl ester
IBXA: acrylic acid isobornyl ester
DMAA: dimethylacrylamide
DAAM: diacetone acrylamide
AA: acrylic Acid (AA)
HEA: 2-Hydroxyethyl acrylate
4 HBA: acrylic acid 4-hydroxybutyl ester
CHMA: methacrylic acid cyclohexyl ester
MMA: methacrylic acid methyl ester
BMA: methacrylic acid n-butyl ester
MAA: methacrylic acid
TBPEH: peroxy-2-ethylhexanoic acid tert-butyl ester
D-40: van Taike (finetack) hardener D-40 (isocyanate cross-linking agent: manufactured by Diesen (DIC) (Strand))
EX-50: van Taike (Finetack) hardener EX-50 (epoxy cross-linking agent: manufactured by Diesen (DIC))
[ Table 4]
[ Table 5]
[ Table 6]
Examples 1 to 13 are examples of the present invention, and the initial adhesion force shows slight adhesiveness, and after heat treatment, the adhesion force can be improved while maintaining the optical transparency, and high transparency and high adhesion force can be achieved at the same time.
Comparative example 1 is an example in which the total amount of alicyclic alkyl group-containing monomers is less than 35% by mass, and the initial adhesion is high. In comparative example 2, the total content of alicyclic alkyl group-containing monomers was 95 mass% or more, and it was confirmed that the haze after the heat treatment was high and the transparency was insufficient. Comparative examples 3 and 4 are examples in which the acrylic resin for adhesion modification has a Tg of less than 50 ℃ and the initial adhesion is high. Comparative example 5 is an example containing no acrylic resin for adhesion modification, and has high initial adhesion.
Claims (3)
1. An adhesive composition comprising: acrylic polymer A, cross-linking agent B and acrylic polymer C,
the acrylic polymer a comprises: units derived from (meth) acrylate monomer a 1; units derived from a nitrogen-containing monomer a 2; and a unit derived from at least one selected from the group consisting of a monomer a3 having an acid group and a monomer a4 having a hydroxyl group,
the acrylic polymer A has a weight-average molecular weight of 100,000 or more,
the acrylic polymer C comprises: a unit derived from an alicyclic structure-containing (meth) acrylate monomer c 1; and units derived from an alkyl (meth) acrylate monomer c2,
the content of the unit derived from the alicyclic structure-containing (meth) acrylate monomer C1 in the acrylic polymer C is 35% by mass or more and less than 95% by mass,
the acrylic polymer C has a glass transition temperature of 50 ℃ or higher,
the weight average molecular weight of the acrylic polymer C is less than 100,000.
2. An adhesive layer formed from the adhesive composition of claim 1.
3. An adhesive film having the adhesive layer of claim 2.
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