CN116745380A - Acrylic adhesive, acrylic adhesive composition, adhesive film, and flexible device - Google Patents
Acrylic adhesive, acrylic adhesive composition, adhesive film, and flexible device Download PDFInfo
- Publication number
- CN116745380A CN116745380A CN202180092057.7A CN202180092057A CN116745380A CN 116745380 A CN116745380 A CN 116745380A CN 202180092057 A CN202180092057 A CN 202180092057A CN 116745380 A CN116745380 A CN 116745380A
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- CN
- China
- Prior art keywords
- acrylate
- meth
- acrylic
- weight
- adhesive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003522 acrylic cement Substances 0.000 title claims abstract description 77
- 239000002313 adhesive film Substances 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 238000011084 recovery Methods 0.000 claims abstract description 34
- 230000001070 adhesive effect Effects 0.000 claims abstract description 32
- 239000012790 adhesive layer Substances 0.000 claims abstract description 27
- 239000000853 adhesive Substances 0.000 claims abstract description 16
- 229920001721 polyimide Polymers 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 153
- 239000000178 monomer Substances 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 229920000058 polyacrylate Polymers 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000003860 storage Methods 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 238000005452 bending Methods 0.000 abstract description 66
- 230000000694 effects Effects 0.000 description 76
- 229920005989 resin Polymers 0.000 description 47
- 239000011347 resin Substances 0.000 description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 46
- -1 alkali metal salts Chemical class 0.000 description 46
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 39
- 239000010410 layer Substances 0.000 description 36
- 229920001519 homopolymer Polymers 0.000 description 34
- 239000000758 substrate Substances 0.000 description 30
- 230000009477 glass transition Effects 0.000 description 29
- 239000003431 cross linking reagent Substances 0.000 description 28
- 230000001747 exhibiting effect Effects 0.000 description 28
- 239000010408 film Substances 0.000 description 26
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 24
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 24
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- 238000005259 measurement Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- 150000002148 esters Chemical group 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 15
- 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 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 13
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-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
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 230000033001 locomotion Effects 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
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000009864 tensile test Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000005260 alpha ray Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 230000005250 beta ray Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000002704 decyl 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])* 0.000 description 2
- 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 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 230000005251 gamma ray Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 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 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
- 230000001771 impaired effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002960 margaryl 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])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001196 nonadecyl 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])C([H])([H])[H] 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
- 125000002347 octyl 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])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 125000002958 pentadecyl 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])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 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 2
- 239000010959 steel Substances 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000002889 tridecyl 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])[H] 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 125000002948 undecyl 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])[H] 0.000 description 2
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- SJPFBRJHYRBAGV-UHFFFAOYSA-N n-[[3-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C=C(CN(CC2OC2)CC2OC2)C=CC=1)CC1CO1 SJPFBRJHYRBAGV-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09J7/38—Pressure-sensitive adhesives [PSA]
-
- 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
- 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
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
- G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Provided are an acrylic adhesive which can exhibit both excellent bending properties and excellent recovery properties for bending operations in a low-temperature environment, an acrylic adhesive composition for forming the acrylic adhesive, an adhesive film having an adhesive layer composed of the acrylic adhesive, and a flexible device having the adhesive film. The acrylic adhesive according to the embodiment of the present invention has an adhesive force to a polyimide film of 5.0N/25mm or more at a peeling speed of 300 mm/min and a peeling angle of 180 degrees at 23 ℃, a creep value at-20 ℃ of 70% or more, and a recovery value at-20 ℃ of 70% or more.
Description
Technical Field
The present invention relates to an acrylic adhesive, an acrylic adhesive composition, an adhesive film, and a flexible device.
Background
The adhesive film is used for reinforcement, surface protection, etc. of various shaped members.
For example, when an Integrated Circuit (IC) or a Flexible Printed Circuit (FPC) is bonded to a substrate (for example, a TFT substrate) of a semiconductor element, thermocompression bonding is generally performed using an Anisotropic Conductive Film (ACF). In such thermocompression bonding, an adhesive film may be bonded to the back surface side of the substrate of the semiconductor element in advance to be reinforced (for example, patent document 1).
In addition, as a method for manufacturing a so-called flexible device such as a foldable device or a rollable device, which has been developed in recent years, a peeling layer and a flexible thin film substrate are usually formed on a support substrate such as glass, a TFT substrate is formed on the thin film substrate, and an organic EL layer is further formed thereon. Then, the support substrate is peeled off to manufacture a flexible device, but since the flexible display layer is very thin, the device suffers from defects due to handling or the like. Therefore, an adhesive film may be laminated on the back surface side in advance for reinforcement (for example, patent document 2).
The substrate and the flexible device of the semiconductor element may be repeatedly bent, and if the bending property of the adhesive film attached to the substrate or the like is poor, the recovery after bending may be deteriorated or, at worst, the breakage may occur due to the repeated bending. Specifically, when the adhesive film is attached to a curved portion (for example, a movable curved portion of a folding member or the like), for example, the following problems occur.
In the case where the adhesive film is bent at an angle, a compressive force acts on the inner diameter side of the bend, and therefore, in order to alleviate the force, the adhesive film itself is deformed. Specifically, for example, wrinkles are easily generated.
When the adhesive film is bent at an angle, tensile stress acts on the outer diameter side of the bend. Therefore, when the stress is relaxed, the self-adhesive material floats.
When the adhesive film is bent at an angle, the thickness of the bent portion and the stretched portion of the adhesive film greatly changes, and in this state, wrinkles and lifting easily occur. For example, when the adhesive film is stretched, the thickness of the adhesive film is greatly reduced, and the adhesive film is liable to float from the adherend.
As described above, in the conventional adhesive film, the following of the irregularities of the diagonal portion and the curved portion cannot be sufficiently achieved.
In order to solve the above-described problems, an adhesive film is required to have both of the bending property against bending operation and the recovery property and to be excellent. In particular, the use environments of flexible devices such as foldable devices and crimpable devices, which have been developed in recent years, are various, and there is a need for an adhesive film which can achieve both excellent bending properties against bending motions and excellent recovery properties even in a low-temperature environment where bending properties are difficult to be exhibited.
Prior art literature
Patent literature
Patent document 1: japanese patent No. 5600039
Patent document 2: japanese patent No. 6376271
Disclosure of Invention
Problems to be solved by the invention
The invention aims to provide an acrylic adhesive which can realize excellent bending performance and excellent recovery performance for bending operation under a low-temperature environment, an acrylic adhesive composition for forming the acrylic adhesive, an adhesive film with an adhesive layer formed by the acrylic adhesive, and a flexible device with the adhesive film.
Solution for solving the problem
The acrylic adhesive according to the embodiment of the present invention has an adhesive force to a polyimide film of 5.0N/25mm or more at a peeling speed of 300 mm/min at 23℃and a peeling angle of 180 ℃,
the creep value at-20 ℃ is more than 70%, and the recovery value at-20 ℃ is more than 70%.
In one embodiment, the acrylic adhesive according to the embodiment of the present invention has a gel fraction of 50% or more.
In one embodiment, the acrylic adhesive of the embodiment of the present invention has a storage modulus G' at-20 ℃ of 150kPa or less.
The acrylic adhesive composition of the embodiment of the present invention forms the acrylic adhesive of the embodiment of the present invention,
The acrylic adhesive composition comprises an acrylic polymer (P) having a weight average molecular weight Mw of 120 ten thousand or less.
In one embodiment, the acrylic polymer (P) in the acrylic pressure-sensitive adhesive composition is contained in an amount of 50 wt% or more.
In one embodiment, the acrylic polymer (P) is obtained by polymerizing a monomer component (M) containing at least 1 selected from the group consisting of a monomer (1) represented by the general formula (1) and a monomer (2) represented by the general formula (2).
(in the general formula (1), R 1 Is alkyl with 1-10 carbon atoms, R 2 Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a-COOR group, and R is an alkyl group having 1 to 10 carbon atoms. )
(in the general formula (2), R 3 Is alkylene with 1-10 carbon atoms, R 4 Is alkyl with 1-10 carbon atoms, R 5 Is a hydrogen atom or a methyl group. )
In one embodiment, the monomer component (M) includes an alkyl (meth) acrylate.
The adhesive film according to the embodiment of the present invention has an adhesive layer composed of the acrylic adhesive according to the embodiment of the present invention.
The flexible device according to the embodiment of the present invention includes the adhesive film according to the embodiment of the present invention.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide an acrylic adhesive that exhibits both excellent bending properties and excellent recovery properties for bending operations in a low-temperature environment, an acrylic adhesive composition for forming the acrylic adhesive, an adhesive film having an adhesive layer composed of the acrylic adhesive, and a flexible device having the adhesive film.
Drawings
Fig. 1 is a schematic cross-sectional view showing one embodiment of the flexible device of the present invention, showing one use form of the adhesive film of the embodiment of the present invention.
Detailed Description
In the present specification, the expression "(meth) acrylic acid" means "acrylic acid and/or methacrylic acid", the expression "(meth) acrylic acid ester" means "acrylic acid ester and/or methacrylic acid ester", the expression "(meth) allyl group" means "allyl group and/or methallyl group", and the expression "(meth) acrolein" means "acrolein and/or methacrolein". In the present specification, the expression "acid (salt)" means "acid and/or salt thereof". Examples of the salt include alkali metal salts and alkaline earth metal salts, and specifically, examples thereof include sodium salts and potassium salts.
Acrylic adhesive
The acrylic pressure-sensitive adhesive according to the embodiment of the present invention preferably has an adhesive force to a polyimide film at 23℃at a peeling speed of 300 mm/min and a peeling angle of 180℃of 5.0N/25mm or more, more preferably 5.5N/25mm or more, still more preferably 6.0N/25mm or more, and particularly preferably 6.5N/25mm or more. The upper limit of the adhesive force is usually as large as possible, and is preferably 30N/25mm or less in consideration of balance with other adhesive properties. When the adhesive force is adjusted within the above range, sufficient adhesion to various adherends such as flexible devices including foldable devices and crimpable devices can be exhibited. The measurement of the adhesive force is described later.
The creep value of the acrylic adhesive according to the embodiment of the present invention at-20 ℃ is preferably 70% or more, more preferably 75% or more, still more preferably 80% or more, particularly preferably 85% or more. The upper limit of the creep value is usually preferably 160% or less when considering balance with other adhesive properties. The greater the creep value at-20℃is an index of bending property against bending operation in a low-temperature environment, which means that the more excellent the bending property against bending operation in a low-temperature environment. When the creep value is adjusted to be within the above range, the acrylic adhesive according to the embodiment of the present invention can exhibit excellent bendability to bending operation in a low-temperature environment. The measurement of the creep value will be described later.
The acrylic adhesive according to the embodiment of the present invention preferably has a recovery value at-20 ℃ of 70% or more, more preferably 73% or more, still more preferably 77% or more, and particularly preferably 80% or more. The upper limit of the recovery value is usually as large as possible, and is preferably 95% or less in consideration of balance with other adhesive properties and the like. The recovery value at-20 ℃ is an index of recovery from bending operation at low temperature, and a larger recovery value means that recovery from bending operation is more excellent in a low-temperature environment. When the recovery value is adjusted to be within the above range, the acrylic adhesive according to the embodiment of the present invention can exhibit excellent recovery from bending operation in a low-temperature environment. The measurement of the recovery value will be described later.
The acrylic adhesive according to the embodiment of the present invention is more preferably adjusted to have the creep value at-20 ℃ and the recovery value at-20 ℃ within the above ranges. By adjusting the above, the acrylic pressure-sensitive adhesive according to the embodiment of the present invention can achieve both of more excellent bending property against bending operation and more excellent recovery property under a low-temperature environment. Conventionally, in the design of adhesives, bending property and recovery property against bending operation are often related to each other (track off). The acrylic pressure-sensitive adhesive according to the embodiment of the present invention can satisfactorily achieve both the bending property and the recovery property of bending operation, which have been most of the time, in a low-temperature environment, and can exhibit excellent bending properties in a low-temperature environment.
The gel fraction of the acrylic adhesive according to the embodiment of the present invention is preferably 50% or more, more preferably 55% or more, still more preferably 60% or more, still more preferably 65% or more, particularly preferably 70% or more, and most preferably 75% or more. The upper limit of the gel fraction is 100%. When the gel fraction is adjusted within the above range, the acrylic adhesive according to the embodiment of the present invention can exhibit both excellent bending properties against bending operations and excellent recovery properties in a low-temperature environment. If the gel fraction is too small in the above range, there is a concern that the recovery of bending operation may be lowered particularly in a low-temperature environment. The measurement of the gel fraction is described later.
The storage modulus G' of the acrylic adhesive according to the embodiment of the present invention at-20℃is preferably 150kPa or less, more preferably 140kPa or less, further preferably 130kPa or less, further preferably 120kPa or less, particularly preferably 110kPa or less, and most preferably 100kPa or less. The lower limit of the storage modulus G' is preferably 70kPa or more in consideration of balance with other binder characteristics and the like. When the storage modulus G' is adjusted to be within the above range, the acrylic adhesive according to the embodiment of the present invention can exhibit both excellent bending properties against bending operations and excellent recovery properties in a low-temperature environment. If the storage modulus G' exceeds the above range, there is a concern that the bending property in bending operation may be lowered. The measurement of the storage modulus G' is described later.
The acrylic adhesive according to the embodiment of the present invention is more preferably adjusted to have the gel fraction and the storage modulus G' at-20℃within the above-mentioned ranges. By adjusting the above, the acrylic pressure-sensitive adhesive according to the embodiment of the present invention can exhibit both of more excellent bending property against bending operation and more excellent recovery property under a low-temperature environment.
The acrylic adhesive of the embodiment of the present invention is preferably formed of an acrylic adhesive composition.
The acrylic adhesive can be defined as being formed from an acrylic adhesive composition in this way. This is because: in the case of an acrylic adhesive, since the acrylic adhesive composition causes a crosslinking reaction or the like by heating, ultraviolet irradiation or the like, the acrylic adhesive cannot be directly specified by its structure, and since there is a case where it is almost impractical (impossible or impractical), the acrylic adhesive is appropriately specified as an "object" by defining it as a "formed from the acrylic adhesive composition".
In the case where the acrylic adhesive according to the embodiment of the present invention is formed from the acrylic adhesive composition, any suitable method may be used as a method for forming such an acrylic adhesive within a range that does not impair the effect of the present invention. Examples of the method for forming such an acrylic adhesive include the following: the acrylic pressure-sensitive adhesive composition is applied to an arbitrary suitable substrate, heated and dried as needed, and cured as needed, thereby forming an acrylic pressure-sensitive adhesive on the substrate. Any suitable means may be used as the means for coating as long as the effects of the present invention are not impaired. Examples of such coating means include gravure roll coaters, reverse roll coaters, kiss roll coaters, dip roll coaters, bar coaters, knife coaters, air knife coaters, spray coaters, comma coaters, direct coaters, and roll brush coaters. The acrylic pressure-sensitive adhesive composition may be heated and dried by any suitable means within a range that does not impair the effect of the present invention. Examples of such heating and drying means include heating to about 60 to 180 ℃. Curing of the acrylic adhesive composition may be carried out by any suitable means within a range that does not impair the effects of the present invention. Examples of such curing means include ultraviolet irradiation, laser irradiation, α -ray irradiation, β -ray irradiation, γ -ray irradiation, X-ray irradiation, and electron beam irradiation.
Acrylic adhesive composition
The acrylic adhesive composition according to the embodiment of the present invention is an acrylic adhesive composition forming the acrylic adhesive according to the embodiment of the present invention.
Acrylic Polymer (P)
The acrylic adhesive composition of the embodiment of the present invention includes an acrylic polymer (P). The number of acrylic polymers (P) may be 1 or 2 or more.
The weight average molecular weight Mw of the acrylic polymer (P) is preferably 120 ten thousand or less, more preferably 110 ten thousand or less, further preferably 100 ten thousand or less, further preferably 90 ten thousand or less, particularly preferably 80 ten thousand or less, and most preferably 70 ten thousand or less. The lower limit of the weight average molecular weight Mw is preferably 50 ten thousand or more. When the weight average molecular weight Mw is adjusted to be within the above range, the acrylic adhesive according to the embodiment of the present invention can exhibit both excellent bending properties against bending operations and excellent recovery properties in a low-temperature environment. If the weight average molecular weight Mw exceeds the above range, there is a concern that the bending property in bending operation may be lowered. The measurement of the weight average molecular weight Mw is described later.
The content of the acrylic polymer (P) in the acrylic pressure-sensitive adhesive composition according to the embodiment of the present invention is preferably 50% by weight or more, more preferably 70% by weight or more, still more preferably 90% by weight or more, particularly preferably 95% by weight or more, and most preferably 97% by weight or more. The upper limit of the content ratio is preferably 100% by weight or less. When the content ratio is within the above range, the acrylic pressure-sensitive adhesive according to the embodiment of the present invention can exhibit both excellent bending properties against bending operations and excellent recovery properties in a low-temperature environment. If the content exceeds the above range, the effect of the present invention may not be sufficiently exhibited.
The acrylic polymer (P) is preferably obtained by polymerizing a monomer component (M) containing at least 1 selected from the group consisting of a monomer (1) represented by the general formula (1) and a monomer (2) represented by the general formula (2).
(in the general formula (1), R 1 Is alkyl with 1-10 carbon atoms, R 2 Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a-COOR group, and R is an alkyl group having 1 to 10 carbon atoms. )
(in the general formula (2), R 3 Is alkylene with 1-10 carbon atoms, R 4 Is alkyl with 1-10 carbon atoms, R 5 Is a hydrogen atom or a methyl group. )
The acrylic polymer (P) can be defined as being obtained by polymerizing the monomer component (M) in this way. This is because: the acrylic polymer (P) is formed by polymerization of the monomer component (M), and cannot be determined directly by its structure, and since there is a case where it is almost impractical (impossible or impractical), the acrylic polymer (P) is appropriately determined as an "object" by defining it as "a product obtained by polymerizing the monomer component (M)".
The monomer component (M) contains at least 1 selected from the group consisting of the monomer (1) represented by the general formula (1) and the monomer (2) represented by the general formula (2), and preferably contains both the monomer (1) represented by the general formula (1) and the monomer (2) represented by the general formula (2) in terms of further exhibiting the effects of the present invention.
The number of the monomers (1) represented by the general formula (1) may be 1 or 2 or more.
The monomer (1) represented by the general formula (1) has a structure (C-CH) in which a furan ring structure can be constructed by cyclized polymerization by having 2 polymerizable double bonds at the terminal 2 -O-CH 2 -C) and further having an alkyl ester group (COOR) at least one of the 2 nd carbon atoms from the end of the terminal 2 polymerizable double bonds 1 Radicals), thereby promoting the cyclized polymerization, and can be constructed by the cyclized polymerizationBy introducing alkyl ester groups into the structure of (a) and utilizing these characteristics, the obtained acrylic pressure-sensitive adhesive can exhibit both of more excellent bending properties against bending movements and more excellent recovery properties.
The number of the monomers (2) represented by the general formula (2) may be 1 or 2 or more.
The monomer (2) represented by the general formula (2) has a (meth) acrylate structure (CH) 2 ＝C(R 5 ) COO-) and carbamoyloxy (-O-CO-NH-) and, by utilizing these characteristics, it is possible to obtain an acrylic pressure-sensitive adhesive which exhibits both of a more excellent bending property against bending motion and a more excellent recovery property.
In the monomer (1) represented by the general formula (1), R 1 Is an alkyl group having 1 to 10 carbon atoms, R is an alkyl group having 1 to 10 carbon atoms, from the viewpoint of further exhibiting the effect of the present invention 1 The alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group or an ethyl group, and most preferably a methyl group.
In the monomer (1) represented by the general formula (1), R 2 Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a-COOR group. R is R 2 In the case of an alkyl group having 1 to 10 carbon atoms, R is an amino group which can further exhibit the effect of the present invention 2 The alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably an alkyl group having 1 to 3 carbon atoms. R is R 2 In the case of-COOR group, R is an alkyl group having 1 to 10 carbon atoms, and from the viewpoint of further exhibiting the effect of the present invention, R is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group or an ethyl group, and most preferably a methyl group. From the aspect of further exhibiting the effect of the present invention, R 2 Preferably a hydrogen atom.
In the monomer (2) represented by the general formula (2), R 3 Is an alkylene group having 1 to 10 carbon atoms, R is an alkylene group having 1 to 10 carbon atoms, from the viewpoint of further exhibiting the effect of the present invention 3 Preferably an alkylene group having 1 to 8 carbon atoms, more preferably an alkylene group having 1 to 6 carbon atoms, still more preferably an alkylene group having 1 to 3 carbon atoms, particularly preferably a methylene group (-CH) 2 (-) or ethylene (-CH) 2 CH 2 (-), most preferably ethylene (-CH) 2 CH 2 -)。
In the monomer (2) represented by the general formula (2), R 4 Is an alkyl group having 1 to 10 carbon atoms, R is an alkyl group having 1 to 10 carbon atoms, from the viewpoint of further exhibiting the effect of the present invention 4 The alkyl group is preferably an alkyl group having 2 to 8 carbon atoms, more preferably an alkyl group having 3 to 6 carbon atoms, further preferably an alkyl group having 3 to 5 carbon atoms, particularly preferably a butyl group, and most preferably an n-butyl group.
In the monomer (2) represented by the general formula (2), R 5 Is a hydrogen atom or a methyl group, R is a hydrogen atom or a methyl group, from the aspect of further exhibiting the effect of the present invention 5 Preferably a hydrogen atom.
The content of at least 1 selected from the group consisting of the monomer (1) represented by the general formula (1) and the monomer (2) represented by the general formula (2) in the monomer component (M) is preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight, still more preferably 0.5 to 10% by weight, still more preferably 1.0 to 5.0% by weight, particularly preferably 1.5 to 4.0% by weight, and most preferably 2.0 to 3.5% by weight, in terms of further exhibiting the effects of the present invention.
The content of the monomer (1) represented by the general formula (1) in the monomer component (M) is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight, still more preferably 0.2 to 5.0% by weight, still more preferably 0.3 to 4.0% by weight, particularly preferably 0.4 to 3.0% by weight, and most preferably 0.5 to 2.0% by weight, in order to further exhibit the effect of the present invention.
The content of the monomer (2) represented by the general formula (2) in the monomer component (M) is preferably 0.1 to 20 wt%, more preferably 0.5 to 10 wt%, further preferably 0.8 to 8.0 wt%, further preferably 1.0 to 6.0 wt%, particularly preferably 1.2 to 4.0 wt%, and most preferably 1.5 to 3.0 wt% in terms of further exhibiting the effects of the present invention.
The monomer component (M) preferably contains an alkyl (meth) acrylate. The alkyl group of the ester moiety is preferably an alkyl group having 1 to 16 carbon atoms. The alkyl group of the ester moiety as referred to herein does not include an alkyl group having a polar group such as a hydroxyl group.
The number of alkyl (meth) acrylates may be 1 or 2 or more.
The content of the alkyl (meth) acrylate in the monomer component (M) is preferably 50 to 99% by weight, more preferably 70 to 98% by weight, still more preferably 80 to 97% by weight, particularly preferably 85 to 96% by weight, and most preferably 90 to 95% by weight, in order to further exhibit the effect of the present invention.
As the alkyl (meth) acrylate, any suitable alkyl (meth) acrylate may be used within a range that does not impair the effects of the present invention. As such an alkyl (meth) acrylate, for example, a compound represented by the following formula (1) can be suitably used.
CH 2 ＝C(R 1 )COOR 2 (1)
Here, R in the above formula (1) 1 Is a hydrogen atom or methyl group, R 2 Is an alkyl group having 1 to 20 carbon atoms.
R 2 In view of further exhibiting the effects of the present invention, an alkyl group having 1 to 16 carbon atoms, an alkyl group having 2 to 14 carbon atoms, an alkyl group having 4 to 14 carbon atoms, and an alkyl group having 4 to 12 carbon atoms are preferable.
The alkyl group is preferably a chain alkyl group in view of further exhibiting the effect of the present invention. Here, the term "chain" includes both straight-chain and branched-chain ones.
As R 2 Examples of the alkyl (meth) acrylate which is a chain alkyl group having 1 to 20 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, and propyl (meth) acrylateIsononyl acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, isostearyl (meth) acrylate, nonadecyl (meth) acrylate, eicosyl (meth) acrylate.
In terms of further exhibiting the effects of the present invention, the glass transition temperature Tg of the homopolymer of an alkyl (meth) acrylate which may be contained in the monomer component (M) is preferably-10℃or lower, more preferably-12℃or lower, further preferably-15℃or lower, particularly preferably-18℃or lower, and most preferably-20℃or lower. The lower limit of the glass transition temperature Tg is preferably-80℃or higher. The glass transition temperature Tg of the homopolymer (homo polymer) of the alkyl (meth) acrylate which may be contained in the monomer component (M) can affect the adhesive property and bending property of the acrylic polymer (P). The effect of the present invention can be further exhibited by using, as the alkyl (meth) acrylate that can be contained in the monomer component (M), an alkyl (meth) acrylate whose homopolymer (homo polymer) has a glass transition temperature Tg within the above-mentioned range, whereby the adhesive property and bending property of the acrylic polymer (P) can be appropriately adjusted.
Here, as the glass transition temperature Tg of the homopolymer (homo polymer) of the alkyl (meth) acrylate which can be contained in the monomer component (M), a value described in a known material can be used, and for example, a value described in "Polymer Hand book" (3 rd edition, john wiley & Sons, inc., 1989) can be used. In the case where a plurality of values are described in "Polymer Hand book", a conventional value is used. For the alkyl (meth) acrylate not described in "Polymer Hand book", a catalog value of a monomer manufacturing company was used. As Tg of the homopolymer of alkyl (meth) acrylate, which is not described in the above "Polymer Hand book" and does not provide a catalogue value of a monomer manufacturing company, a value obtained by a measurement method described in japanese patent application laid-open No. 2007-51271 is used.
As a representative example of the glass transition temperature Tg of a homopolymer (homo polymer) of an alkyl (meth) acrylate which may be contained in the monomer component (M), for example, the following is mentioned.
2-ethylhexyl acrylate (2 EHA): -70 DEG C
Lauryl Acrylate (LA): -23 DEG C
n-Butyl Acrylate (BA): -55 DEG C
In terms of further exhibiting the effects of the present invention, the monomer component (M) preferably contains, as the alkyl (meth) acrylate, an alkyl (meth) acrylate (M1) whose homopolymer (homopolymer) has a glass transition temperature Tg in the range of-80℃to-60 ℃. When the monomer component (M) contains the alkyl (meth) acrylate (M1), the content of the alkyl (meth) acrylate (M1) in the monomer component (M) is preferably 40 to 99% by weight, more preferably 45 to 90% by weight, still more preferably 50 to 80% by weight, particularly preferably 55 to 75% by weight, and most preferably 60 to 70% by weight, in order to further exhibit the effect of the present invention.
The glass transition temperature Tg of the homopolymer (homo polymer) of the alkyl (meth) acrylate which may be contained in the monomer component (M) can affect the adhesive property and bending property of the acrylic polymer (P) as described above. The alkyl (meth) acrylate (M1) is used as the alkyl (meth) acrylate that can be contained in the monomer component (M) so that the content ratio in the monomer component (M) falls within the above range, whereby the adhesive property and bending property of the acrylic polymer (P) can be appropriately adjusted, and the effects of the present invention can be further exhibited.
Examples of the alkyl (meth) acrylate (m 1) include 2-ethylhexyl acrylate (2 EHA) (homopolymer) having a glass transition temperature tg= -70 ℃.
In terms of further exhibiting the effects of the present invention, the monomer component (M) preferably contains, as the alkyl (meth) acrylate, an alkyl (meth) acrylate (M2) whose homopolymer (homopolymer) has a glass transition temperature Tg in the range of-40℃to-10 ℃. When the monomer component (M) contains the alkyl (meth) acrylate (M2), the content of the alkyl (meth) acrylate (M2) in the monomer component (M) is preferably 5 to 50% by weight, more preferably 7 to 40% by weight, still more preferably 10 to 30% by weight, particularly preferably 13 to 25% by weight, and most preferably 15 to 22% by weight, in order to further exhibit the effect of the present invention.
The glass transition temperature Tg of the homopolymer (homo polymer) of the alkyl (meth) acrylate which may be contained in the monomer component (M) can affect the adhesive property and bending property of the acrylic polymer (P) as described above. The alkyl (meth) acrylate (M2) is used as the alkyl (meth) acrylate that can be contained in the monomer component (M) so that the content ratio in the monomer component (M) falls within the above range, whereby the adhesive property and bending property of the acrylic polymer (P) can be appropriately adjusted, and the effect of the present invention can be further exhibited.
Examples of the alkyl (meth) acrylate (m 2) include Lauryl Acrylate (LA) (its homopolymer) having a glass transition temperature tg= -23 ℃).
In terms of further exhibiting the effects of the present invention, the monomer component (M) preferably contains, as the alkyl (meth) acrylate, an alkyl (meth) acrylate (M3) whose homopolymer (homopolymer) has a glass transition temperature Tg in the range of more than-60℃and less than-40 ℃. When the monomer component (M) contains the alkyl (meth) acrylate (M3), the content of the alkyl (meth) acrylate (M3) in the monomer component (M) is preferably 0.1 to 30% by weight, more preferably 1 to 20% by weight, still more preferably 3 to 15% by weight, particularly preferably 4 to 13% by weight, and most preferably 5 to 10% by weight, in order to further exhibit the effect of the present invention.
The glass transition temperature Tg of the homopolymer (homo polymer) of the alkyl (meth) acrylate which may be contained in the monomer component (M) can affect the adhesive property and bending property of the acrylic polymer (P) as described above. The alkyl (meth) acrylate (M3) is used as the alkyl (meth) acrylate which can be contained in the monomer component (M) so that the content ratio in the monomer component (M) falls within the above range, whereby the adhesive property and bending property of the acrylic polymer (P) can be appropriately adjusted, and the effect of the present invention can be further exhibited.
The alkyl (meth) acrylate (m 3) mentioned above may be, for example, n-Butyl Acrylate (BA) (its homopolymer) has a glass transition temperature tg= -55 ℃.
From the viewpoint of further exhibiting the effects of the present invention, the monomer component (M) preferably contains at least 1 selected from the group consisting of alkyl (meth) acrylates (M1), alkyl (meth) acrylates (M2), and alkyl (meth) acrylates (M3), more preferably contains at least 2 selected from the group consisting of alkyl (meth) acrylates (M1), alkyl (meth) acrylates (M2), and alkyl (meth) acrylates (M3), and still more preferably contains alkyl (meth) acrylates (M1), alkyl (meth) acrylates (M2), and alkyl (meth) acrylates (M3).
From the viewpoint of further exhibiting the effects of the present invention, the monomer component (M) is typically at least 1 selected from the group consisting of 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate, more preferably at least 2 selected from the group consisting of 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate, and even more preferably 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate.
The monomer component (M) preferably contains a hydroxyl group-containing monomer (M4). The hydroxyl group-containing monomer (m 4) may be 1 or 2 or more.
In terms of further exhibiting the effects of the present invention, the glass transition temperature Tg of the homo-polymer of the hydroxyl group-containing monomer (M4) which may be contained in the monomer component (M) is preferably-10℃or lower, more preferably-15℃or lower, further preferably-20℃or lower, particularly preferably-25℃or lower, most preferably-30℃or lower. The lower limit of the glass transition temperature Tg is preferably-80℃or higher. The glass transition temperature Tg of the homo-polymer of the hydroxyl group-containing monomer (M4) which may be contained in the monomer component (M) can affect the adhesive property and bending property of the acrylic polymer (P). The hydroxyl group-containing monomer (M4) that can be contained in the monomer component (M) can be used to further exhibit the effect of the present invention by appropriately adjusting the adhesive property and bending property of the acrylic polymer (P) by using the hydroxyl group-containing monomer (M4) whose homopolymer (homo polymer) has a glass transition temperature Tg within the above-mentioned range.
Here, as the glass transition temperature Tg of the homo-polymer of the hydroxyl group-containing monomer (M4) that can be contained in the monomer component (M), values described in known materials can be used in the same manner as the aforementioned alkyl (meth) acrylate, and for example, values described in "Polymer Hand book" (3 rd edition, john wiley & Sons, inc., 1989) can be used. In the case where a plurality of values are described in "Polymer Hand book", a conventional value is used. For the hydroxyl group-containing monomer (m 4) not described in the above "Polymer Hand book", a catalog value of the monomer manufacturing company was used. The Tg of the homopolymer of the hydroxyl group-containing monomer (m 4) which is not described in the above-mentioned "Polymer Hand book" and which does not provide a catalogue value of the monomer manufacturing company, was obtained by the measurement method described in JP-A2007-51271.
As a representative example of the glass transition temperature Tg of the homo-polymer of the hydroxyl group-containing monomer (M4) which may be contained in the monomer component (M), for example, the following is mentioned.
2-hydroxyethyl acrylate: -15 DEG C
4-hydroxybutyl acrylate: -40 DEG C
In the case where the monomer component (M) contains the hydroxyl group-containing monomer (M4), the content of the hydroxyl group-containing monomer (M4) in the monomer component (M) is preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight, still more preferably 0.5 to 15% by weight, particularly preferably 1 to 10% by weight, and most preferably 2 to 5% by weight, in order to further exhibit the effects of the present invention.
Examples of the hydroxyl group-containing monomer (m 4) include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate; polypropylene glycol mono (meth) acrylate; n-hydroxyethyl (meth) acrylamide.
In view of further exhibiting the effects of the present invention, the hydroxyl group-containing monomer (m 4) preferably contains a hydroxyalkyl (meth) acrylate, more preferably contains a hydroxyalkyl (meth) acrylate having a linear alkyl group having 2 to 4 carbon atoms in the alkyl moiety. Examples of the hydroxyalkyl (meth) acrylate include 2-hydroxyethyl acrylate (HEA) and 4-hydroxybutyl acrylate (4 HBA), and 4-hydroxybutyl acrylate is preferable in view of further exhibiting the effect of the present invention.
From the viewpoint that the effects of the present invention can be further exhibited, the monomer component (M) preferably contains at least 1 selected from the group consisting of alkyl (meth) acrylate (M1), alkyl (meth) acrylate (M2), and alkyl (meth) acrylate (M3) and contains a hydroxyl-containing monomer (M4), more preferably contains at least 2 selected from the group consisting of alkyl (meth) acrylate (M1), alkyl (meth) acrylate (M2), and alkyl (meth) acrylate (M3) and contains a hydroxyl-containing monomer (M4), and still more preferably, alkyl (meth) acrylate (M1), alkyl (meth) acrylate (M2), and alkyl (meth) acrylate (M3) each contain and contain a hydroxyl-containing monomer (M4).
From the viewpoint of further exhibiting the effects of the present invention, the monomer component (M) is typically preferably at least 1 selected from the group consisting of 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate and contains a hydroxyl-containing monomer (M4), more preferably at least 2 selected from the group consisting of 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate and contains a hydroxyl-containing monomer (M4), and still more preferably 2-ethylhexyl acrylate, lauryl acrylate and n-butyl acrylate all contain and contain a hydroxyl-containing monomer (M4).
The total content of the alkyl (meth) acrylate (M1), the alkyl (meth) acrylate (M2), the alkyl (meth) acrylate (M3), and the hydroxyl group-containing monomer (M4) in the monomer component (M) is preferably 60 to 99% by weight, more preferably 70 to 99% by weight, still more preferably 80 to 99% by weight, particularly preferably 90 to 99% by weight, and most preferably 95 to 98% by weight, from the viewpoint of further exhibiting the effects of the present invention.
The monomer component (M) may further contain monomers other than the monomer (1) represented by the above general formula (1), the monomer (2) represented by the above general formula (2), the above alkyl (meth) acrylate, and the above hydroxyl group-containing monomer (M4) within a range that does not impair the effects of the present invention. The other monomer may be used for the purpose of adjusting the glass transition temperature (Tg) of the acrylic polymer (P), adjusting the adhesive property, and the like. The number of other monomers may be 1 or 2 or more.
Examples of the other monomer include carboxyl group-containing monomers, nitrogen-containing monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, cyano group-containing monomers, acid anhydride group-containing monomers, vinyl esters (for example, vinyl acetate (VAc), vinyl propionate, vinyl laurate), aromatic vinyl compounds, amide group-containing monomers, epoxy group-containing monomers, (meth) acryloylmorpholine, and vinyl ethers.
Examples of the carboxyl group-containing monomer include Acrylic Acid (AA), methacrylic acid (MAA), carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
Examples of the nitrogen-containing monomer include nitrogen-containing vinyl monomers such as N-vinyl-2-pyrrolidone, methyl vinyl pyrrolidone, vinyl pyridine, vinyl piperidone, vinyl pyrimidine, vinyl piperazine, vinyl pyrazine, vinyl pyrrole, vinyl imidazole, vinyl oxazole, vinyl morpholine, (meth) acryloylmorpholine, N-vinylcarboxylic acid amide, and N-vinylcaprolactam; and cyano-containing acrylic monomers such as acrylonitrile and methacrylonitrile. Among these, N-vinyl-2-pyrrolidone is preferable in view of the high effect of improving the adhesive strength due to the improvement of the cohesive force.
The content of the other monomer in the monomer component (M) is preferably 20% by weight or less, more preferably 10% by weight or less, further preferably 5% by weight or less, particularly preferably 3% by weight or less, and most preferably 1% by weight or less.
As a method for obtaining the acrylic polymer (P), for example, various polymerization methods known as a method for synthesizing an acrylic polymer, such as a solution polymerization method, an emulsion polymerization method, a bulk polymerization method, and a suspension polymerization method, can be suitably employed. Among these polymerization methods, a solution polymerization method can be preferably used. As a monomer supply method in the case of performing solution polymerization, a one-time feeding method, a continuous feeding (dropping) method, a batch feeding (dropping) method, or the like, in which the entire amount of the monomer component is supplied at one time, can be suitably employed. The polymerization temperature may be appropriately selected depending on the types of monomers and solvents used, the types of polymerization initiators, and the like, and is preferably 20℃or higher, more preferably 30℃or higher, further preferably 40℃or higher, preferably 170℃or lower, more preferably 160℃or lower, further preferably 140℃or lower. As a method for obtaining the acrylic polymer, photopolymerization by irradiation with light such as UV (typically, in the presence of a photopolymerization initiator), active energy ray irradiation polymerization such as radiation polymerization by irradiation with radiation such as β rays or γ rays, and the like can be used.
The solvent (polymerization solvent) used in the solution polymerization may be appropriately selected from any suitable organic solvents. Examples thereof include aromatic compounds such as toluene (typically aromatic hydrocarbons), acetates such as ethyl acetate, aliphatic or alicyclic hydrocarbons such as hexane and cyclohexane, and the like.
The initiator (polymerization initiator) used in the polymerization may be appropriately selected from any appropriate polymerization initiators depending on the kind of the polymerization method. The polymerization initiator may be 1 or 2 or more.
As the polymerization initiator, for example, examples thereof include 2,2 '-Azobisisobutyronitrile (AIBN), 2' -azobis-2-methylbutyronitrile, dimethyl 2,2 '-azobis (2-methylpropionate), 4' -azobis-4-cyanovaleric acid, azobisisovaleronitrile, azobisisobutyronitrile, azobis-ethyl acetate, azobisisobutyronitrile, azoic acid, azobis-ethyl-acid, azobisisobutyronitrile, and 2,2 '-azobis (2-amidinopropane) dihydrochloride, 2' -azobis [2- (5-methyl-2-imidazolin-2-yl) propane ] dihydrochloride, 2 '-azobis (2-methylpropionamidine) disulfate, 2' -azobis (N, azo initiators such as N '-dimethylene isobutyl amidine) and 2,2' -azobis [ N- (2-carboxyethyl) -2-methylpropionamidine ] hydrate (VA-057, manufactured by Wako pure chemical industries, ltd.); peroxide-based initiators such as potassium persulfate, persulfates such as ammonium persulfate, bis (2-ethylhexyl) peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-sec-butyl peroxydicarbonate, t-butyl peroxyneodecanoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, dilauroyl peroxide, di-n-octanoyl peroxide, 1, 3-tetramethylbutyl peroxy-2-ethylhexanoate, bis (4-methylbenzoyl) peroxide, dibenzoyl peroxide, t-butyl peroxyisobutyrate, 1-bis (t-hexylperoxy) cyclohexane, t-butyl hydroperoxide, hydrogen peroxide, and the like; redox initiators comprising a combination of a persulfate and sodium bisulfite, a combination of a peroxide and sodium ascorbate, and a combination of a peroxide and a reducing agent; substituted ethane initiators such as phenyl-substituted ethane; an aromatic carbonyl compound.
The amount of the polymerization initiator to be used is preferably 0.005 to 1 part by weight, more preferably 0.01 to 1 part by weight, based on 100 parts by weight of the monomer component (M).
Polymerization any suitable other additives may be added within a range that does not impair the effects of the present invention.
Cross-linking Agents
The acrylic adhesive composition of the embodiment of the present invention may include a crosslinking agent. The number of the crosslinking agents may be 1 or 2 or more.
By using a crosslinking agent, an appropriate cohesive force can be imparted to the acrylic adhesive. The crosslinking agent may be contained in the acrylic adhesive in a form after the crosslinking reaction, a form before the crosslinking reaction, a form in which the crosslinking reaction is partially performed, an intermediate or composite form thereof, or the like. The crosslinking agent is typically contained in the acrylic adhesive in a form after the crosslinking reaction.
The content of the crosslinking agent in the acrylic pressure-sensitive adhesive composition is preferably 0.005 to 10 parts by weight, more preferably 0.01 to 7 parts by weight, still more preferably 0.05 to 5 parts by weight, and particularly preferably 0.1 to 1 part by weight, based on 100 parts by weight of the acrylic polymer (P), in order to further exhibit the effect of the present invention.
Examples of the crosslinking agent include isocyanate-based crosslinking agents, epoxy-based crosslinking agents, silicone-based crosslinking agents, oxazoline-based crosslinking agents, aziridine-based crosslinking agents, silane-based crosslinking agents, alkyl etherified melamine-based crosslinking agents, metal chelate-based crosslinking agents, and crosslinking agents such as peroxides, and in terms of further exhibiting the effects of the present invention, isocyanate-based crosslinking agents and epoxy-based crosslinking agents are preferable, and isocyanate-based crosslinking agents are more preferable.
The isocyanate-based crosslinking agent may be a compound having 2 or more isocyanate groups (including an isocyanate-regenerated polar group in which the isocyanate groups are temporarily protected by a blocking agent or by multimerization) in 1 molecule. Examples of the isocyanate-based crosslinking agent include aromatic isocyanates such as toluene diisocyanate and xylene diisocyanate; alicyclic isocyanates such as isophorone diisocyanate; aliphatic isocyanates such as hexamethylene diisocyanate.
Examples of the isocyanate-based crosslinking agent include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; alicyclic isocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate and isophorone diisocyanate; aromatic diisocyanates such as 2, 4-toluene diisocyanate, 4' -diphenylmethane diisocyanate, xylylene diisocyanate, polymethylene polyphenyl isocyanate, and the like; isocyanate adducts such as trimethylolpropane/toluene diisocyanate trimer adducts (for example, trade name Coronatel, manufactured by Tosoh corporation), trimethylolpropane/hexamethylene diisocyanate trimer adducts (for example, trade name: coronate HL, manufactured by Tosoh corporation), and isocyanurate bodies of hexamethylene diisocyanate (for example, trade name: coronate HX, manufactured by Tosoh corporation); trimethylolpropane adduct of xylylene diisocyanate (e.g., manufactured by Mitsui chemical Co., ltd., trade name: TAKENATE D N), trimethylolpropane adduct of xylylene diisocyanate (e.g., manufactured by Mitsui chemical Co., ltd., trade name: TAKENATE D N), trimethylolpropane adduct of isophorone diisocyanate (e.g., manufactured by Mitsui chemical Co., ltd., trade name: TAKENATE D140N), trimethylolpropane adduct of hexamethylene diisocyanate (e.g., manufactured by Mitsui chemical Co., ltd., trade name: TAKENATE D N); polyether polyisocyanates, polyester polyisocyanates, and their adducts with various polyols; polyisocyanates polyfunctional with isocyanurate bonds, biuret bonds, allophanate bonds, and the like. Among these, aromatic isocyanates and alicyclic isocyanates are preferable from the viewpoint of achieving both good balance between deformability and cohesive force.
As the epoxy-based crosslinking agent, a polyfunctional epoxy compound having 2 or more epoxy groups in 1 molecule can be used. Examples of the epoxy-based crosslinking agent include N, N' -tetraglycidyl-m-xylylenediamine, diglycidyl aniline, 1, 3-bis (N, N-diglycidyl aminomethyl) cyclohexane, 1, 6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, sorbitol polyglycidyl ether, glycerol polyglycidyl ether, pentaerythritol polyglycidyl ether, sorbitol polyglycidyl ether, trimethylolpropane polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, triglycidyl-tris (2-hydroxyethyl) isocyanurate, resorcinol diglycidyl ether, bisphenol-S-diglycidyl ether, and epoxy resins having 2 or more epoxy groups in the molecule. Examples of the commercial products of the epoxy crosslinking agent include trade names "tetra C" and "tetra X" manufactured by mitsubishi gas chemical company.
Oligomers
The acrylic adhesive composition of the embodiment of the present invention may contain an oligomer in order to adjust adhesive properties, bending properties, etc. The number of oligomers may be 1 or 2 or more.
The weight average molecular weight Mw of the oligomer is preferably 1000 to 30000, more preferably 1500 to 10000, further preferably 2000 to 8000, particularly preferably 2000 to 5000. By using such an oligomer having a weight average molecular weight Mw, the adhesive properties and bending properties of the acrylic adhesive can be improved.
As the oligomer, an acrylic oligomer is preferable in terms of easy compatibility with an acrylic polymer.
The glass transition temperature Tg of the acrylic oligomer is preferably 20 ℃ or higher, more preferably 40 ℃ or higher, still more preferably 60 ℃ or higher, particularly preferably 80 ℃ or higher, and most preferably 100 ℃ or higher. The upper limit of the glass transition temperature Tg of the acrylic oligomer is preferably 200 ℃ or less, more preferably 180 ℃ or less, and still more preferably 160 ℃ or less.
The glass transition temperature Tg of the acrylic oligomer is a value obtained by Fox equation based on Tg of a homopolymer (homo polymer) of each monomer constituting and weight fraction (copolymerization ratio based on weight) of the monomer. The Fox formula is shown below as a relation between Tg of the copolymer and glass transition temperature Tgi of a homopolymer obtained by homopolymerizing each of the monomers constituting the copolymer.
1/Tg＝Σ(Wi/Tgi)
In the above Fox formula, tg represents the glass transition temperature (unit: K) of the copolymer, wi represents the weight fraction (copolymerization ratio based on weight) of the monomer i of the copolymer, and Tgi represents the glass transition temperature (unit: K) of the homopolymer of the monomer i. As the Tg of the homopolymer, the values described in known materials can be used, and for example, the values described in "Polymer Hand book" (3 rd edition, john Wiley & Sons, inc., 1989) can be used. In the case where a plurality of values are described in "Polymer Hand book", a conventional value is used. For the monomer not described in "Polymer Hand book", a catalog value of a monomer manufacturing company was used. As Tg of the homopolymer of the monomer which is not described in the above "Polymer Hand book" and which does not provide a catalog value of the monomer manufacturing company, a value obtained by a measurement method described in japanese patent application laid-open No. 2007-51271 is used.
The acrylic oligomer contains an alicyclic alkyl (meth) acrylate as a main constituent monomer component. The alicyclic alkyl (meth) acrylate may be 1 or 2 or more.
Examples of the alicyclic alkyl (meth) acrylate include cycloalkyl (meth) acrylates such as cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, and cyclooctyl (meth) acrylate; (meth) acrylic esters having a bicyclic aliphatic hydrocarbon ring such as isobornyl (meth) acrylate; (meth) acrylic esters having an aliphatic hydrocarbon ring having three or more rings, such as dicyclopentanoethyl (meth) acrylate, tricyclopentyl (meth) acrylate, 1-adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, and 2-ethyl-2-adamantyl (meth) acrylate.
The alicyclic alkyl (meth) acrylate is preferably dicyclopentanyl acrylate, dicyclopentanyl methacrylate, cyclohexyl acrylate or cyclohexyl methacrylate, in order to further exhibit the effect of the present invention.
The content of the alicyclic alkyl (meth) acrylate relative to the total amount of the constituent monomer components of the acrylic oligomer is preferably 10 to 99% by weight, more preferably 30 to 98% by weight, still more preferably 40 to 97% by weight, and particularly preferably 50 to 96% by weight, in order to further exhibit the effects of the present invention.
The acrylic oligomer may contain, as a constituent monomer component, a chain alkyl (meth) acrylate having a chain alkyl group, and the number of the chain alkyl (meth) acrylate having a chain alkyl group may be 1 or 2 or more. Here, the term "chain" includes both straight-chain and branched-chain ones.
The chain alkyl (meth) acrylate is preferably a chain alkyl (meth) acrylate having a chain alkyl group of 1 to 20 carbon atoms, and examples thereof include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, and nonadecyl (meth) acrylate.
The chain alkyl (meth) acrylate is preferably methyl methacrylate in view of further exhibiting the effect of the present invention.
The content of the chain alkyl (meth) acrylate relative to the total amount of the constituent monomer components of the acrylic oligomer is preferably 10 to 90% by weight, more preferably 20 to 80% by weight, and even more preferably 30 to 70% by weight, in order to further exhibit the effects of the present invention.
The acrylic oligomer may contain (meth) acrylic acid as a constituent monomer component, and the number of (meth) acrylic acid may be 1 or 2 or more.
As the (meth) acrylic acid, acrylic acid is preferable in that the effect of the present invention can be further exhibited.
The content of (meth) acrylic acid in the total amount of the constituent monomer components of the acrylic oligomer is preferably 0.1 to 20% by weight, more preferably 1 to 10% by weight, and even more preferably 3 to 7% by weight, in order to further exhibit the effect of the present invention.
The oligomer is obtained by polymerizing constituent monomer components by various polymerization methods. In the polymerization of the oligomer, any suitable additive may be used within a range that does not impair the effect of the present invention. Examples of such additives include a polymerization initiator and a chain transfer agent.
The content of the oligomer in the acrylic pressure-sensitive adhesive composition is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, still more preferably 1 to 10 parts by weight, and particularly preferably 1 to 5 parts by weight, based on 100 parts by weight of the acrylic polymer (P), in order to further exhibit the effect of the present invention.
Tackifying resin
The acrylic adhesive composition of the embodiment of the present invention may contain a tackifying resin in order to adjust adhesive properties, bending properties, etc. The number of the tackifying resins may be 1 or 2 or more.
Examples of the tackifying resin include rosin-based tackifying resins, terpene-based tackifying resins, hydrocarbon-based tackifying resins, epoxy-based tackifying resins, polyamide-based tackifying resins, elastomer-based tackifying resins, phenol-based tackifying resins, and ketone-based tackifying resins.
The amount of the tackifier resin used is preferably 5 to 70 parts by weight, more preferably 10 to 60 parts by weight, still more preferably 15 to 50 parts by weight, still more preferably 20 to 45 parts by weight, particularly preferably 25 to 40 parts by weight, and most preferably 25 to 35 parts by weight, based on 100 parts by weight of the acrylic polymer (P), in order to further exhibit the effect of the present invention.
As the tackifying resin, in terms of further exhibiting the effects of the present invention, it is preferable to include a tackifying resin TL having a softening point lower than 105 ℃. The tackifying resin TL can effectively contribute to improvement of deformability in the face direction (shearing direction) of the adhesive layer. The softening point of the tackifying resin used as the tackifying resin TL is preferably 50 to 103 ℃, more preferably 60 to 100 ℃, still more preferably 65 to 95 ℃, particularly preferably 70 to 90 ℃, and most preferably 75 to 85 ℃ in view of obtaining a higher deformability improving effect.
The softening point of the tackifying resin is defined as a value measured based on the softening point test method (ring and ball method) specified in JIS K5902 and JIS K2207. Specifically, the sample was melted rapidly at as low a temperature as possible, taking care to fill the ring placed on a flat metal plate without generating bubbles. After cooling, the portion protruding from the plane containing the upper end of the ring was cut off with a slightly heated knife. Then, a glass container (heating bath) having a diameter of 85mm or more and a height of 127mm or more was placed in a holder (annular base), and glycerin was injected until the depth became 90mm or more. Next, a steel ball (diameter 9.5mm, weight 3.5 g) and a ring filled with the sample were immersed in glycerin so as not to contact each other, and the temperature of glycerin was maintained at 20.+ -. 5 ℃ for 15 minutes. The steel ball is then placed in the center of the surface of the specimen in the ring and placed in a fixed position on the support. Then, the distance from the upper end of the ring to the glycerin surface was kept at 50mm, a thermometer was placed so that the center position of the bulb of water in the thermometer was at the same height as the center of the ring, and the container was heated. The flame of the Bunsen burner used for heating is positioned in the middle of the center and the edge of the bottom of the container, so that the heating is uniform. The proportion of the rise in bath temperature from the start of heating to the time when 40℃was reached was 5.0.+ -. 0.5℃per minute. The sample gradually softened and dropped from the ring, and the temperature at which it eventually contacted the bottom plate was read as the softening point. For the measurement of softening points, 2 or more were simultaneously carried out and the average value thereof was used.
The amount of the tackifier resin TL used is preferably 5 to 50 parts by weight, more preferably 10 to 45 parts by weight, still more preferably 15 to 40 parts by weight, particularly preferably 20 to 35 parts by weight, and most preferably 25 to 32 parts by weight, based on 100 parts by weight of the acrylic polymer (P), in order to further exhibit the effects of the present invention.
As the tackifying resin TL, 1 or 2 or more kinds selected appropriately from those exemplified above, in which the softening point is lower than 105 ℃, can be used. The tackifying resin TL preferably comprises a rosin-based resin.
The rosin-based resin that can be preferably used as the tackifying resin TL includes, for example, rosin esters such as unmodified rosin esters and modified rosin esters. Examples of the modified rosin ester include hydrogenated rosin esters.
The tackifying resin TL preferably contains a hydrogenated rosin ester in terms of further exhibiting the effects of the present invention. The hydrogenated rosin ester preferably has a softening point of less than 105 ℃, more preferably 50 to 100 ℃, still more preferably 60 to 90 ℃, particularly preferably 70 to 85 ℃, and most preferably 75 to 85 ℃ in order to further exhibit the effect of the present invention.
Tackifying resin TL may comprise a non-hydrogenated rosin ester. The term "non-hydrogenated rosin ester" as used herein refers to the concept of the above rosin esters excluding hydrogenated rosin esters. Examples of the non-hydrogenated rosin ester include an unmodified rosin ester, a disproportionated rosin ester, and a polymerized rosin ester.
The non-hydrogenated rosin ester preferably has a softening point of less than 105 ℃, more preferably 50 to 100 ℃, still more preferably 60 to 90 ℃, particularly preferably 70 to 85 ℃, and most preferably 75 to 85 ℃ in order to further exhibit the effect of the present invention.
The tackifying resin TL may contain other tackifying resins in addition to the rosin-based resin. As the other tackifying resin, 1 or 2 or more kinds of tackifying resins selected as appropriate from those exemplified above having a softening point lower than 105 ℃ can be used. The tackifying resin TL may include, for example, rosin-based resins and terpene resins.
The content of the rosin-based resin in the entire tackifying resin TL is preferably more than 50% by weight, more preferably 55% by weight to 100% by weight, still more preferably 60% by weight to 99% by weight, particularly preferably 65% by weight to 97% by weight, and most preferably 75% by weight to 97% by weight, in order to further exhibit the effects of the present invention.
The tackifying resin may be used in combination with the tackifying resin TL having a softening point of 105 ℃ or higher (preferably 105 ℃ to 170 ℃) or higher, in order to further exhibit the effects of the present invention.
As the tackifying resin TH, 1 or 2 or more kinds of tackifying resins having a softening point of 105 ℃ or higher, which are exemplified above, can be suitably selected. The tackifying resin TH may include at least 1 selected from rosin-based tackifying resins (e.g., rosin esters) and terpene-based tackifying resins (e.g., terpene phenol resins).
Other ingredients
The acrylic pressure-sensitive adhesive composition according to the embodiment of the present invention may contain various additives as necessary, which are usual in the field of adhesives such as leveling agents, crosslinking aids, plasticizers, softeners, fillers, antistatic agents, antioxidants, ultraviolet absorbers, antioxidants, light stabilizers, crosslinking catalysts, crosslinking retarders, and the like. As such various additives, conventionally known additives can be used by a conventional method.
Examples of the crosslinking catalyst includeIrons, tetra-n-butyl titanate, tetra-isopropyl titanate, butyltin oxide, dioctyltin dilaurate, and the like. Examples of the crosslinking retarder include compounds that cause keto-enol tautomerism, and concretely include β -diketones such as acetylacetone and 2, 4-hexanedione; acetoacetates such as methyl acetoacetate and ethyl acetoacetate; propionyl acetate esters such as ethyl propionylacetate; isobutyryl acetates such as isobutyryl ethyl acetate; malonates such as methyl malonate and ethyl malonate; etc.
Adhesive film
The pressure-sensitive adhesive film according to the embodiment of the present invention has a pressure-sensitive adhesive layer composed of the acrylic pressure-sensitive adhesive sheet according to the embodiment of the present invention.
The adhesive film according to the embodiment of the present invention may be a film having no substrate and formed only of an adhesive layer, or may be a film having a substrate and an adhesive layer and having a substrate. The adhesive film of the present invention may have any suitable other layer in addition to the base material layer and the adhesive layer within a range that does not impair the effects of the present invention.
The substrate layer may be 1 layer or 2 or more layers. The substrate layer is preferably 1 layer in terms of further exhibiting the effects of the present invention.
The pressure-sensitive adhesive layer may be 1 layer or 2 or more layers. The adhesive layer is preferably 1 layer in terms of further exhibiting the effect of the present invention.
The pressure-sensitive adhesive film according to the embodiment of the present invention may be provided with any suitable release liner on the surface of the pressure-sensitive adhesive layer on the opposite side of the substrate layer for the purpose of protection before use, etc.
Examples of the release liner include a release liner in which the surface of a substrate (liner substrate) such as paper or plastic film is subjected to silicone treatment; and release liners obtained by laminating a polyolefin resin on the surface of a substrate (liner substrate) such as paper or plastic film. Examples of the plastic film as the backing material include polyethylene film, polypropylene film, polybutylene film, polybutadiene film, polymethylpentene film, polyvinyl chloride film, vinyl chloride copolymer film, polyethylene terephthalate film, polybutylene terephthalate film, polyurethane film, and ethylene-vinyl acetate copolymer film.
The thickness of the release liner is preferably 1 μm to 500. Mu.m, more preferably 3 μm to 450. Mu.m, still more preferably 5 μm to 400. Mu.m, particularly preferably 10 μm to 300. Mu.m.
The thickness of the adhesive film according to the embodiment of the present invention is preferably 1 μm to 500. Mu.m, more preferably 5 μm to 200. Mu.m, still more preferably 10 μm to 150. Mu.m, particularly preferably 20 μm to 100. Mu.m, and most preferably 30 μm to 80. Mu.m. When the thickness of the adhesive film according to the embodiment of the present invention is within the above range, the effect of the present invention can be further exhibited.
The adhesive film according to the embodiment of the present invention has a total light transmittance of preferably 20% or more, more preferably 30% or more, still more preferably 40% or more, particularly preferably 50% or more, and most preferably 60% or more.
When the total light transmittance of the adhesive film of the present invention is within the above range, excellent transparency can be further exhibited.
The haze of the adhesive film according to the embodiment of the present invention is preferably 15% or less, more preferably 13% or less, further preferably 10% or less, particularly preferably 8% or less, and most preferably 6% or less. When the haze of the adhesive film of the present invention is within the above range, the adhesive film can further exhibit excellent transparency.
The adhesive film according to the embodiment of the present invention can be preferably used in flexible devices such as foldable devices and crimpable devices because it can exhibit both excellent bending properties against bending motions and excellent recovery properties in a low-temperature environment.
Substrate layer
The thickness of the base material layer is preferably 1 μm to 500. Mu.m, more preferably 5 μm to 300. Mu.m, still more preferably 10 μm to 100. Mu.m, particularly preferably 15 μm to 80. Mu.m, and most preferably 20 μm to 60. Mu.m. When the thickness of the base material layer is within the above range, the effect of the present invention can be further exhibited.
The Young's modulus of the substrate layer at 23℃is preferably 6.0X10 7 Pa or more, more preferably 1.0X10 8 Pa or more, more preferably 5.0X10 8 Pa or more, particularly preferably 8.0X10 8 Pa or more, most preferably 1.0X10 9 Pa or more. The upper limit of the Young's modulus of the base material layer at 23℃is typically preferably 1.0X10 11 Pa or below. When the Young's modulus of the base material layer at 23℃is within the above range, the effect of the present invention can be further exhibited. If the Young's modulus of the base material layer is too low at 23 ℃, there is a concern that the adhesive film may not sufficiently retain the outer diameter side tension with respect to the inner diameter side compression, and the thickness may easily change, and the adhesive film may easily float from the adherend. If the Young's modulus of the base material layer at 23℃is too high, there is a concern that the adhesive film cannot be easily deformed. The method for measuring Young's modulus will be described in detail later.
Any suitable material may be used as the material of the base material layer within a range that does not impair the effects of the present invention. As a material of such a base material layer, a resin material is typically used.
Examples of the resin material as a material of the base layer include acrylic resins such as Polyimide (PI), polyetheretherketone (PEEK), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polymethyl methacrylate (PMMA), polycarbonate, cellulose Triacetate (TAC), polysulfone, polyarylate, polyethylene (PE), polypropylene (PP), ethylene-propylene copolymer, ethylene-vinyl acetate copolymer (EVA), polyamide (nylon), wholly aromatic polyamide (aromatic polyamide), polyvinyl chloride (PVC), polyvinyl acetate, polyphenylene Sulfide (PPs), fluorine resin, and cyclic olefin polymer.
Adhesive layer
The thickness of the pressure-sensitive adhesive layer is preferably 1 μm to 500. Mu.m, more preferably 5 μm to 300. Mu.m, still more preferably 10 μm to 100. Mu.m, particularly preferably 10 μm to 80. Mu.m, and most preferably 10 μm to 60. Mu.m. When the thickness of the adhesive layer is within the above range, the effect of the present invention can be further exhibited.
The pressure-sensitive adhesive layer is formed by forming an acrylic pressure-sensitive adhesive into a layer shape. As a method for forming the adhesive layer, any suitable forming method may be employed within a range that does not impair the effects of the present invention. Examples of such a formation method include the following: the acrylic pressure-sensitive adhesive composition is applied to an arbitrary appropriate substrate, heated and dried as needed, and cured as needed, thereby forming an acrylic pressure-sensitive adhesive layer on the substrate. Any suitable means may be used as the means for coating as long as the effects of the present invention are not impaired. Examples of such coating means include gravure roll coaters, reverse roll coaters, kiss roll coaters, dip roll coaters, bar coaters, knife coaters, air knife coaters, spray coaters, comma coaters, direct coaters, and roll brush coaters. The acrylic pressure-sensitive adhesive composition may be heated and dried by any suitable means within a range that does not impair the effect of the present invention. Examples of such heating and drying means include heating to about 60 to 180 ℃. Curing of the acrylic adhesive composition may be carried out by any suitable means within a range that does not impair the effects of the present invention. Examples of such curing means include ultraviolet irradiation, laser irradiation, α -ray irradiation, β -ray irradiation, γ -ray irradiation, X-ray irradiation, and electron beam irradiation.
Flexible devices
The adhesive film of the present invention can exhibit both excellent bending properties for bending operations and excellent recovery properties in a low-temperature environment, and therefore, can be suitably used for flexible devices such as bendable devices (bendable devices) having movable bending portions, foldable devices (foldable devices), and crimpable devices (crimpable devices).
That is, the flexible device according to the embodiment of the present invention includes the adhesive film according to the embodiment of the present invention. The flexible device of the present invention is provided with the adhesive film of the embodiment of the present invention. The foldable device of the present invention may include any other suitable member as long as it includes the adhesive film of the embodiment of the present invention.
Fig. 1 is a schematic cross-sectional view illustrating an embodiment of a flexible device of the present invention as a representative of one use form of an adhesive film of the embodiment of the present invention. In fig. 1, a foldable device 1000 according to an embodiment of the present invention includes: a cover film 10, an adhesive layer 20, a polarizing plate 30, an adhesive layer 40, a touch sensor 50, an adhesive layer 60, an OLED70, and an adhesive film 100 according to an embodiment of the present invention. The adhesive film 100 according to the embodiment of the present invention is composed of the adhesive layer 80 and the base material layer 90 in fig. 1. The adhesive layers 20, 40, 60 may be adhesive layers containing an adhesive having the same composition as the adhesive layer 80 constituting the adhesive film 100 of the embodiment of the present invention, or may be adhesive layers containing adhesives having different compositions.
Examples
The present invention will be described more specifically with reference to examples and comparative examples. However, the present invention is not limited by them. In the following description, "parts" and "%" are weight basis unless otherwise specified.
The following abbreviations and details of the raw materials used in the production examples, examples and comparative examples are as follows.
2EHA: 2-ethylhexyl acrylate
LA: lauryl acrylate
BA: acrylic acid n-butyl ester
4HBA: acrylic acid 4-hydroxybutyl ester
NVP: n-vinyl-2-pyrrolidone
AOMA (registered trademark): cyclized polymerizable monomer (in general formula (1), R 1 Is methyl, R 2 Is a hydrogen atom. )
V#216: 2-butylcarbamoyloxyethyl acrylate (VISCOAT#216, manufactured by Osaka organic chemical Co., ltd.) (general formula (2), R 3 is-CH 2 CH 2 -、R 4 Is n-butyl, R 5 Is a hydrogen atom. )
MMA: methyl methacrylate
HEA: hydroxy ethyl acrylate
AIBN:2,2' -azobisisobutyronitrile
Irgacure184: photopolymerization initiator (BASF corporation)
Irgacure651: photopolymerization initiator (BASF corporation)
DCPMA: dicyclohexyl methacrylate
C/HX: CORONATE HX (isocyanate-based crosslinking agent manufactured by Tosoh Co., ltd.)
D110N: TAKENATE D110N (isocyanate-based crosslinking agent manufactured by Sanjing chemical Co., ltd.)
HDDA:1, 6-hexanediol diacrylate
Ion: iron catalyst (made by Japanese chemical industry Co., ltd.)
IRGANOX 1010: antioxidant (BASF corporation)
KBM403: silane coupling agent (Xinyue chemical industry Co., ltd.)
< adhesion to polyimide film >
After a separator (MRQ 50T 100J) having a small peeling force was peeled off from the separator of the adhesive film, a polyimide substrate having a thickness of 25 μm (trade name "Upsilex 25RN", manufactured by Yushi Xingzhi Co., ltd.) was bonded to the separator, to prepare an adhesive film with a polyimide substrate. The adhesive film with the polyimide substrate was cut into pieces 25mm wide by 100mm long, and the separator (JT-50 Wa) was peeled off to expose the adhesive, and then a 2kg hand roll was reciprocated 1 time to attach the adhesive film to a polyimide film (trade name "Uilex 50S", manufactured by Yukyi Co., ltd.) to obtain a sample for evaluation.
The obtained sample for evaluation was stored at room temperature for 30 minutes, and then measured by a tensile tester. As a tensile tester, a high-speed mode (AG-50 NXplus) of the trade name "Autograph AG-Xplus HS6000 mm/min", manufactured by Shimadzu corporation, was used. After the test piece for evaluation was set in the tensile testing machine, the tensile test was started. The conditions for the tensile test were set as the peel angle: 180 degrees, peeling speed (stretching speed): 300 mm/min. The load when the adhesive film was peeled off from the polyimide film (Upilex 50S) was measured, and the average load at this time was used as the adhesive force.
< creep value at-20 ℃ and recovery value at-20 >
Taking out only the adhesive layer from the adhesive film, laminating to a thickness of about 1mm, and punching it outCylindrical pellets were prepared and used as a sample for measurement.
The obtained measurement sample was immobilized on a dynamic viscoelasticity measurement device (ARES, manufactured by Rheometrics, inc.)And a fixture for parallel plates. The deformation strain (%) after applying a deformation stress of 10Kpa at-20 ℃ and holding for 600 seconds was set as a value a, the deformation strain after further applying a deformation stress of 0 and holding for 600 seconds was set as B, the a value was set as a creep value at-20 ℃, and the deformation strain (%) was determined to pass [100- { (B value×100)/a value }]The calculated value was taken as a recovery value at-20 ℃.
< gel fraction >
The pressure-sensitive adhesive film was cut out to 50mm×100mm, the pressure-sensitive adhesive layer removed from the pressure-sensitive adhesive film was rolled to an arbitrary size, and a porous polytetrafluoroethylene film (NTF-1122 "manufactured by Nito electric Co., ltd.) having a pore diameter of 0.2 μm and cut out to a size of 100mm×100mm was used as a measurement sample, and the wrapped mouth was bound with kite string. The total weight (A) of the porous polytetrafluoroethylene film and the kite string measured in advance was subtracted from the weight of the sample, and the weight (B) of the measurement sample was calculated. The measurement sample covered with the porous polytetrafluoroethylene film was immersed in about 50mL of ethyl acetate at 23℃for 7 days, and the sol component of the binder was eluted outside the porous polytetrafluoroethylene film. After immersing, a measurement sample covered with a porous polytetrafluoroethylene film was taken out, dried at 130℃for 2 hours, cooled for about 20 minutes, and then the dry weight (the total of the weight of the sample, the porous polytetrafluoroethylene film, and the kite string) was measured (C). The gel fraction of the adhesive was calculated by the following formula.
Gel fraction (%) =100× [ (C-se:Sub>A)/B ]
< storage modulus G' >
The storage modulus G' corresponds to a portion stored as elastic energy when the material is deformed, and is an index indicating the degree of hardness.
Taking out only the adhesive layer from the adhesive film, laminating to a thickness of about 1mm, and punching it outCylindrical pellets were prepared and used as a sample for measurement.
The obtained measurement sample was immobilized on a dynamic viscoelasticity measurement device (ARES, manufactured by Rheometrics, inc.)And (5) calculating the storage modulus G' by using the fixture of the parallel plates. The measurement conditions are as follows.
And (3) measuring: shear mode
Temperature range: -60-210 DEG C
Heating rate: 5 ℃/min
Frequency: 1Hz
< weight average molecular weight Mw >
The weight average molecular weight was measured by Gel Permeation Chromatography (GPC). Specifically, using "Agilent 1260 property" (manufactured by Agilent Technologies, inc.) as a GPC measurement device, a tetrahydrofuran solution containing an amine component was prepared at 0.1% by weight in consideration of the polymer concentration of the sample, allowed to stand for 20 hours, filtered through a 0.45 μm membrane filter, and the filtrate was subjected to GPC measurement.
The measurement was performed under the following conditions, and calculated from standard polystyrene conversion values.
(conditions for molecular weight measurement)
Sample concentration: 0.1% by weight (tetrahydrofuran solution containing an amine component)
Sample injection amount: 100 mu L
Column: trade name "TSK gel GMH-H (S)" (manufactured by Tosoh Co., ltd.)
Eluent: tetrahydrofuran added with amine component
Flow rate: 0.5mL/min
Detector: differential Refractometer (RI)
Column temperature (measurement temperature): 40 DEG C
Standard sample: polystyrene (PS)
Production example 1: production of acrylic Polymer (1)
Into a four-necked flask equipped with a stirring blade, a thermometer, a nitrogen inlet pipe, and a condenser, 2EHA was placed: 66.6 parts by weight, LA:19.0 parts by weight of BA:7.6 parts by weight, 4HBA:3.8 parts by weight, AOMA (registered trademark): 1.0 parts by weight, v#216:1.9 parts by weight of AIBN as a polymerization initiator: 0.1 part by weight of ethyl acetate was charged so that the total concentration thereof became 30% by weight, nitrogen was replaced in the system with slow stirring for 1 hour, the polymerization was carried out for 5 hours while maintaining the liquid temperature in the flask at around 58 ℃, and after completion of the reaction, ethyl acetate was added to adjust the polymer concentration to 28% by weight, thereby obtaining a solution of the acrylic polymer (1). The results are shown in Table 1.
Production examples 2 to 7: production of acrylic polymers (2) to (7)
Solutions of acrylic polymers (2) to (7) were obtained in the same manner as in production example 1 except that the monomer components and various conditions were changed to those described in table 1. The results are shown in Table 1.
Production example 8: production of acrylic oligomer (A)
Dcdma to be used as monomer component: 60 parts by weight of MMA:40 parts by weight of α -thioglycerol as chain transfer agent: 3.5 parts by weight and 100 parts by weight of toluene as a polymerization solvent were mixed and stirred at 70℃for 1 hour under a nitrogen atmosphere. Subsequently, AIBN as a thermal polymerization initiator was charged: 0.2 part by weight, and then reacted at 70℃for 2 hours, and then heated to 80℃for 2 hours to obtain the acrylic oligomer (A). The weight average molecular weight Mw of the acrylic oligomer (A) was 5100 and the glass transition temperature (Tg) was 130 ℃.
[ example 1 ]
Acrylic polymer (1): 100 parts by weight of C/HX as crosslinker: 0.23 part by weight of an acrylic oligomer (A): 2 parts by weight of IRGANOX 1010 as an antioxidant: 0.3 part by weight as catalystIon: 0.01 part by weight of the acrylic pressure-sensitive adhesive composition (1) was mixed and sufficiently stirred, and diluted with ethyl acetate and acetylacetone in an amount of 2% by weight of the solvent component so that the total solid content became 22% by weight, to thereby obtain a coating solution of the acrylic pressure-sensitive adhesive composition (1). The resulting coating solution of the acrylic pressure-sensitive adhesive composition (1) was applied to a silicone-treated surface of a 50 μm thick polyester resin release sheet (product name: JT-50Wa, manufactured by Nito electric Co., ltd.) having been subjected to silicone treatment on one surface so that the thickness thereof after drying became 13. Mu.m, and the surface was dried at a drying temperature of 130℃for 1 minute. Next, a release sheet (product name: MRQ50T100J, manufactured by Mitsubishi chemical Co., ltd.) of a polyester resin having a thickness of 50 μm and one surface subjected to silicone treatment was bonded to the surface of the obtained pressure-sensitive adhesive layer so as to contact the silicone-treated surface, thereby obtaining a pressure-sensitive adhesive film (1). This was aged at 50℃for 3 days, and various evaluations were performed. The results are shown in Table 3.
Examples 2 to 8
Coating solutions of acrylic pressure-sensitive adhesive compositions (2) to (8) and pressure-sensitive adhesive films (2) to (8) were obtained in the same manner as in example 1, except that the raw material compositions and various conditions were changed as shown in table 2. This was aged at 50℃for 3 days, and various evaluations were performed. The results are shown in Table 3.
Comparative examples 1 to 5
Coating solutions of acrylic pressure-sensitive adhesive compositions (C1) to (C5) and pressure-sensitive adhesive films (C1) to (C5) were obtained in the same manner as in example 1, except that the raw material compositions and various conditions were changed to those shown in table 2. This was aged at 50℃for 3 days, and various evaluations were performed. The results are shown in Table 3.
TABLE 1
TABLE 2
TABLE 3
Industrial applicability
The acrylic adhesive and the like according to the embodiments of the present invention can be used for so-called flexible devices and the like such as foldable devices, crimpable devices and the like.
Description of the reference numerals
1000. Foldable device
100. Adhesive film
10. Cover film
20. Adhesive layer
30. Polarizing plate
40. Adhesive layer
50. Contact sensor
60. Adhesive layer
70 OLED
80. Adhesive layer
90. Substrate layer
Claims (9)
1. An acrylic adhesive having an adhesive force to a polyimide film of 5.0N/25mm or more at a peeling speed of 300 mm/min and a peeling angle of 180 DEG at 23 ℃,
The creep value at-20 ℃ is more than 70%, and the recovery value at-20 ℃ is more than 70%.
2. The acrylic adhesive according to claim 1, having a gel fraction of 50% or more.
3. The acrylic adhesive according to claim 1 or 2, which has a storage modulus G' at-20 ℃ of 150kPa or less.
4. An acrylic adhesive composition forming the acrylic adhesive of any one of claims 1 to 3,
the acrylic adhesive composition comprises an acrylic polymer (P) having a weight average molecular weight Mw of 120 ten thousand or less.
5. The acrylic adhesive composition according to claim 4, wherein the acrylic polymer (P) in the acrylic adhesive composition is contained in an amount of 50% by weight or more.
6. The acrylic adhesive composition according to claim 4 or 5, wherein the acrylic polymer (P) is obtained by polymerizing a monomer component (M) comprising at least 1 selected from the group consisting of a monomer (1) represented by the general formula (1) and a monomer (2) represented by the general formula (2),
in the general formula (1), R 1 Is alkyl with 1-10 carbon atoms, R 2 Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a-COOR group, R is an alkyl group having 1 to 10 carbon atoms,
In the general formula (2), R 3 Is alkylene with 1-10 carbon atoms, R 4 Is alkyl with 1-10 carbon atoms, R 5 Is a hydrogen atom or a methyl group.
7. The acrylic adhesive composition according to claim 6, wherein the monomer component (M) comprises an alkyl (meth) acrylate.
8. An adhesive film having an adhesive layer composed of the acrylic adhesive according to any one of claims 1 to 3.
9. A flexible device provided with the adhesive film of claim 8.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021-010277 | 2021-01-26 | ||
| JP2021010277 | 2021-01-26 | ||
| PCT/JP2021/045482 WO2022163165A1 (en) | 2021-01-26 | 2021-12-10 | Acrylic adhesive agent, acrylic adhesive agent composition, adhesive film, and flexible device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116745380A true CN116745380A (en) | 2023-09-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180092057.7A Pending CN116745380A (en) | 2021-01-26 | 2021-12-10 | Acrylic adhesive, acrylic adhesive composition, adhesive film, and flexible device |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2022163165A1 (en) |
| KR (1) | KR20230133896A (en) |
| CN (1) | CN116745380A (en) |
| TW (1) | TW202239927A (en) |
| WO (1) | WO2022163165A1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS593469Y2 (en) | 1979-06-15 | 1984-01-31 | 株式会社山武 | Sealing device for cylinder type proximity switch |
| JPH0214764Y2 (en) | 1986-10-31 | 1990-04-20 | ||
| CN111148811B (en) * | 2017-12-11 | 2021-12-28 | 株式会社Lg化学 | Adhesive composition for foldable display and foldable display comprising the same |
| JP7185479B2 (en) * | 2017-12-28 | 2022-12-07 | 日東電工株式会社 | Resin composition, resin layer, and laminated sheet |
| JP2020204010A (en) * | 2018-11-28 | 2020-12-24 | 日東電工株式会社 | Adhesive film, foldable device and rollable device |
| JP7069068B2 (en) * | 2019-02-27 | 2022-05-17 | リンテック株式会社 | Repeated bending display |
-
2021
- 2021-12-10 JP JP2022578118A patent/JPWO2022163165A1/ja active Pending
- 2021-12-10 WO PCT/JP2021/045482 patent/WO2022163165A1/en active Application Filing
- 2021-12-10 CN CN202180092057.7A patent/CN116745380A/en active Pending
- 2021-12-10 KR KR1020237028639A patent/KR20230133896A/en unknown
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- 2022-01-18 TW TW111102016A patent/TW202239927A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022163165A1 (en) | 2022-08-04 |
| TW202239927A (en) | 2022-10-16 |
| JPWO2022163165A1 (en) | 2022-08-04 |
| KR20230133896A (en) | 2023-09-19 |
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