CN116891705A - Adhesive composition, laminate, printed wiring board, adhesive film, adhesive layer, image display device, and polarizing plate - Google Patents
Adhesive composition, laminate, printed wiring board, adhesive film, adhesive layer, image display device, and polarizing plate Download PDFInfo
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- CN116891705A CN116891705A CN202310296411.9A CN202310296411A CN116891705A CN 116891705 A CN116891705 A CN 116891705A CN 202310296411 A CN202310296411 A CN 202310296411A CN 116891705 A CN116891705 A CN 116891705A
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- Prior art keywords
- adhesive
- adhesive composition
- acrylate
- component
- biomass
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 94
- 239000000853 adhesive Substances 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000012790 adhesive layer Substances 0.000 title claims description 37
- 239000002313 adhesive film Substances 0.000 title claims description 14
- 239000002028 Biomass Substances 0.000 claims abstract description 49
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 40
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 26
- 239000010408 film Substances 0.000 claims description 25
- 239000012788 optical film Substances 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 13
- 238000002834 transmittance Methods 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 6
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 claims description 5
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 claims description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 5
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 5
- 229940065472 octyl acrylate Drugs 0.000 claims description 5
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 22
- 238000000034 method Methods 0.000 description 19
- -1 Alkyl methacrylates Chemical class 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000004760 accelerator mass spectrometry Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003522 acrylic cement Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000003901 ceryl 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])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
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001802 myricyl 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])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
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])[H] 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000000755 henicosyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002818 heptacosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 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 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 125000002819 montanyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002465 nonacosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002460 pentacosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- C—CHEMISTRY; METALLURGY
- 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
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
-
- 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
- C09J2467/00—Presence of polyester
- C09J2467/005—Presence of polyester in the release coating
-
- 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
- C09J2467/00—Presence of polyester
- C09J2467/006—Presence of polyester in the substrate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
- Polarising Elements (AREA)
Abstract
The invention provides an adhesive composition which uses a material of biological origin and has low dielectric characteristics in a high frequency region. The adhesive composition contains an acrylic copolymer, wherein 30% or more of the total carbon number of the acrylic copolymer is biomass-derived carbon, and the relative dielectric constant at 10GHz is 2.80 or less.
Description
Technical Field
The invention relates to an adhesive composition, a laminate, a printed wiring board, an adhesive film, an adhesive layer for an optical film, an image display device, and a polarizing plate.
Background
In recent years, carbon dioxide emissions caused by the combustion of petroleum-derived products have been regarded as a problem, and the reduction of the amount of fossil resource materials such as petroleum has been sought. Along with this, there has also been an attempt in the field of adhesives to save petroleum resources by using a bio-derived material instead of a petroleum-derived material.
For example, patent document 1 discloses an acrylic adhesive containing an acrylic copolymer. More than 50% of the total carbon number contained in the acrylic adhesive disclosed in patent document 1 is biomass-derived (bio) carbon.
On the other hand, an acrylic adhesive capable of adhering metals such as copper is also used as an adhesive for flexible printed circuit boards (FPC: flexible Printed Circuit).
In recent years, with the increase in the speed of transmission signals represented by the fifth generation mobile communication system (so-called 5G), the increase in the frequency of signals exceeding 6GHz has been advanced. With this, FCP for high-speed transmission is required to have low dielectric characteristics (low dielectric constant, low dielectric loss tangent) in a high-frequency region.
For example, patent document 2 discloses an adhesive composition for a printed wiring board, which has a relative dielectric constant at 10GHz of 3.0 or less and a dielectric loss tangent of 0.008 or less.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2020-105308
Patent document 2: japanese patent No. 6981581
Disclosure of Invention
Technical problem
In consideration of environmental problems, an adhesive having low dielectric characteristics in a high frequency region of 5G is desired.
The present invention has been made in view of the above circumstances, and an object thereof is to provide an adhesive composition which uses a bio-derived material and has low dielectric characteristics in a high frequency region, a laminate using the adhesive composition, a printed wiring board, an adhesive film, an adhesive layer for an optical film, an image display device, and a polarizing plate.
Technical proposal
That is, the present invention adopts the following configuration.
[1] An adhesive composition comprising an acrylic copolymer, wherein 30% or more of the total carbon number of the acrylic copolymer is biomass-derived carbon, and the relative dielectric constant at 10GHz is 2.80 or less.
[2] The adhesive composition according to [1], wherein the acrylic copolymer comprises a component (A1) and a component (A3) as monomer components, the component (A1) is a monomer component represented by the following general formula (1), and the component (A3) is hydroxyalkyl (meth) acrylate.
(in the general formula (1), R 1 Is a hydrogen atom or a methyl group. R is R 2 Is an alkyl group having 1 to 36 carbon atoms. R is R 2 The alkyl group represented is a biomass-derived alkyl group. )
[3] The adhesive composition according to [2], wherein the component (A1) is 1 or 2 kinds selected from the group consisting of isobornyl acrylate, lauryl methacrylate, lauryl acrylate, octyl acrylate, isostearyl acrylate, stearyl methacrylate, and behenyl acrylate.
[4] The adhesive composition according to [1] or [2], which has a haze value of 2.5 or less and a total light transmittance (Total Transmittance) of 97% or more.
[5] A laminate having an adhesive layer formed of the adhesive composition according to [1] or [2 ].
[6] A printed wiring board comprising the laminate according to [5 ].
[7] An adhesive film comprising an adhesive layer formed of the adhesive composition according to any one of [1] to [3] on one or both sides of a resin film.
[8] An adhesive layer for an optical film, which is formed from the adhesive composition of any one of [1] to [3 ].
[9] An image display device wherein the adhesive layer for an optical film of [8] is used for bonding an optical film.
[10] A polarizing plate with an adhesive layer, which uses the adhesive layer for an optical film according to [8 ].
Technical effects
According to the present invention, an adhesive composition using a bio-derived material and having low dielectric characteristics in a high frequency region, a laminate using the adhesive composition, a printed wiring board, an adhesive film, an adhesive layer for an optical film, an image display device, and a polarizing plate can be provided.
Detailed Description
< adhesive composition >
The present embodiment is an adhesive composition containing an acrylic copolymer.
In the present embodiment, the "adhesive" refers to a liquid in which the adhesive composition is dissolved in a solvent.
In the present embodiment, the "adhesive composition" refers to a material which is in a state of a soft solid (viscoelastic body) in a temperature region around room temperature (20 ℃) and has a property of being easily adhered to an adherend by pressure.
Acrylic acid copolymer
The acrylic copolymer is a copolymer having an alkyl (meth) acrylate as a monomer component. When alkyl (meth) acrylate is used as the monomer component, an adhesive composition having high transparency and good adhesive properties can be easily obtained.
In this embodiment, 30% or more of the total carbon number of the acrylic copolymer is biomass-derived carbon.
The high biomass-to-carbon ratio of the acrylic copolymer means that the amount of fossil resource-based materials typified by petroleum and the like used is small.
From the viewpoint of reducing the amount of fossil resource-based material used, a biomass-to-carbon ratio is preferable. In the present embodiment, 35% or more of the total carbon number of the acrylic copolymer may be biomass-derived carbon, and the biomass-derived carbon may be 40% or more, 50% or more, 60% or more, or 70% or more.
The upper limit of the biomass-derived carbon ratio is not particularly limited, and may be 100% or less, 99% or less, 98% or less, 95% or less, 90% or less, or 85% or less.
The upper and lower values of the ratio of biomass-derived carbon may be arbitrarily combined.
As an example of the combination, the upper limit and the lower limit of the ratio of biomass-derived carbon are 30% or more and 100% or less, 35% or more and 99% or less, 40% or more and 98% or less, 50% or more and 95% or less, 60% or more and 90% or less, 70% or more and 85% or less.
Biomass can be measured by measuring the content ratio of the carbon isotope of mass number 14 by accelerator mass spectrometry (Accelerator Mass Spectrometry: AMS method).
In this embodiment, the solvent component contained in the adhesive composition is removed, and the solid content is measured by accelerator mass spectrometry (AMS method), so that the biomass degree of the acrylic copolymer can be measured.
As a result of intensive studies, the present inventors have found that an adhesive composition containing an acrylic copolymer having a high biomass-carbon ratio (30% or more) has dielectric characteristics such that the relative dielectric constant is 2.80 or less in a high frequency band such as 10 GHz.
The reason for this is presumed as follows.
The lower the polarity (the smaller the polarization) the lower the dielectric properties according to Clausius-moslotti's relation. The monomer with high biomass is usually a monomer derived from fatty acid with a large number of carbon atoms in the side chain of the monomer, and is a monomer with low polarity (small polarization). Therefore, the adhesive composition of the present embodiment is presumed to have low dielectric characteristics based on the relational expression of clausius-Mo Suo.
In the present embodiment, the dielectric characteristics of the adhesive composition are relative permittivity and dielectric loss tangent measured at a frequency of 10GHz by a split column dielectric resonator (Split Post Dielectric Resonator) method using, for example, E5071C manufactured by agilent (Agilent Technologies) company as a sample, a single layer sheet of an adhesive resin formed from the adhesive composition.
The alkyl (meth) acrylate is represented by, for example, the following general formula (1).
(in the general formula (1), R 1 Is a hydrogen atom or methyl group, R 2 Is an alkyl group having 1 to 36 carbon atoms. )
The monomer represented by the general formula (1) may be R 1 Alkyl acrylate as hydrogen atom, R may be 1 Alkyl methacrylates which are methyl groups.
R of the general formula (1) 2 Is an alkyl group having 1 to 36 carbon atoms. When the carbon number of the alkyl group is 3 or more, the alkyl group may be linear or branched. In addition, R 2 May be a cyclic alkyl group.
Examples of the linear or branched alkyl group include: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, isostearyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, tetracosyl, triacontyl, hexacosyl, hexatriacontyl, and the like.
Examples of cycloalkyl groups include cyclohexyl and isobornyl.
Component (A1)
In this embodiment, the alkyl (meth) acrylate includes an alkyl (meth) acrylate having a biomass-derived alkyl group at the ester end. Alkyl (meth) acrylates having a biomass-derived alkyl group at the ester end are sometimes described as "(A1) components.
Namely, component (A1) is R in the above general formula (1) 2 The alkyl group represented is a biomass-derived alkyl group. (A1) The component (c) is a component that increases the biomass of the adhesive composition.
Component (A1) is typically an ester of biomass-derived alkanol with biomass-derived or non-biomass-derived (meth) acrylic acid. Examples of biomass-derived alkanols include biomass ethanol (bio ethanol), palm oil, palm kernel oil, coconut oil, and the like derived from plant materials.
In the present embodiment, when the alkyl (meth) acrylate represented by the general formula (1) is the component (A1), R 2 The alkyl group is preferably an alkyl group having 8 or more carbon atoms, more preferably an alkyl group having 10 or more carbon atoms, and particularly preferably an alkyl group having 12 or more carbon atoms.
If R is 2 When the carbon number of (a) is equal to or greater than the lower limit, the number proportion of the biomass-derived carbon atoms in the total carbon number contained in the component (A1) increases, and the biomass-to-carbon ratio increases.
(A1) The component (a) is preferably 1 or 2 selected from the group consisting of isobornyl acrylate, lauryl methacrylate, lauryl acrylate, octyl acrylate, isostearyl acrylate, stearyl methacrylate and behenyl acrylate.
Component (A2)
In this embodiment, the alkyl (meth) acrylate may include an alkyl (meth) acrylate having an alkyl group of non-biomass origin at the ester end. Alkyl (meth) acrylates having an alkyl group of non-biomass origin at the ester end are sometimes described as "(A2) components.
Namely, the component (A2) is as aboveR in the general formula (1) 2 The alkyl groups represented are non-biomass derived alkyl groups.
Although the component (A2) is an arbitrary component, the glass transition point and/or the adhesive strength of the acrylic copolymer can be adjusted by copolymerizing the component (A2).
In the present embodiment, when the alkyl (meth) acrylate represented by the general formula (1) is the component (A2), R 2 Preferably an alkyl group having 7 or less carbon atoms in the longest carbon chain.
In the present embodiment, if R 2 When the carbon number of (2) is equal to or less than the upper limit, the number proportion of biomass-derived carbon atoms in the total carbon number contained in the acrylic copolymer increases, and the biomass-carbon ratio increases.
Specific examples of the component (A2) are 2-ethylhexyl acrylate, n-butyl acrylate or ethyl acrylate.
Component (A3)
In this embodiment, the alkyl (meth) acrylate may include a (meth) acrylate having a hydroxyl group, that is, a hydroxyalkyl (meth) acrylate. Hydroxyalkyl (meth) acrylates are sometimes described as "(A3) components.
(A3) The component (A3) is copolymerized to introduce crosslinking points into the acrylic copolymer.
Specific examples of the component (A3) include at least 1 or more of 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2, 3-dihydroxypropyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and other polyalkylene glycol mono (meth) acrylate.
The acrylic copolymer may be a copolymer of the component (A1) and the component (A3). In this case, the component (A1) may be 1 kind of the above alkyl (meth) acrylate alone or may be used in combination with R 2 2 or more different alkyl (meth) acrylates.
In this case, the proportion of the component (A3) in the acrylic copolymer is preferably 10.0 parts by weight or less, more preferably 7.5 parts by weight or less, further preferably 6.0 parts by weight or less, particularly preferably 5.0 parts by weight or less, and even more preferably 3.0 parts by weight or less, based on the total amount (100 parts by weight) of the component (A1).
The proportion of the component (A3) in the acrylic copolymer may be 0.1 part by weight or more, 1.0 part by weight or more, or 1.5 parts by weight or more based on the total amount (100 parts by weight) of the component (A1).
The proportion of the component (A3) in the acrylic copolymer is, for example, 0.1 to 10.0 parts by weight, 1.0 to 7.5 parts by weight, 1.0 to 6.0 parts by weight, 1.0 to 5.0 parts by weight, 1.5 to 3.0 parts by weight, and the ratio of the component (A3) to the total amount of the component (A1) (100 parts by weight).
The acrylic copolymer may be a copolymer of component (A1), component (A2) and component (A3).
In this case, the proportion of the component (A1) in the total amount (100 parts by weight) of the component (A1) and the component (A2) is preferably 50 parts by weight or more, more preferably 60 parts by weight or more, and still more preferably 70 parts by weight or more.
The proportion of the component (A3) in the acrylic copolymer is preferably 10.0 parts by weight or less, more preferably 7.5 parts by weight or less, further preferably 6.0 parts by weight or less, particularly preferably 5.0 parts by weight or less, and even more preferably 3.0 parts by weight or less, based on the total amount (100 parts by weight) of the component (A1) and the component (A2).
The proportion of the component (A3) in the acrylic copolymer may be 0.1 part by weight or more, 1.0 part by weight or more, or 1.5 parts by weight or more, based on the total amount (100 parts by weight) of the component (A1) and the component (A2).
The proportion of the component (A3) in the acrylic copolymer is, for example, 0.1 to 10.0 parts by weight, 1.0 to 7.5 parts by weight, 1.0 to 6.0 parts by weight, 1.0 to 5.0 parts by weight, 1.5 to 3.0 parts by weight, or the like based on the total amount (100 parts by weight) of the component (A1) and the component (A2).
If the ratio of component (A1) is not less than the lower limit, not less than 30% of the total carbon number of the acrylic copolymer is biomass-derived carbon.
The weight average molecular weight of the acrylic copolymer is not particularly limited, and is preferably 200000 to 5000000, more preferably 300000 to 4000000, and particularly preferably 500000 to 2000000. If the weight average molecular weight of the acrylic copolymer is within this range, the resulting adhesive composition can exhibit excellent adhesion. In the present specification, the weight average molecular weight refers to a polystyrene-equivalent molecular weight obtained by GPC (Gel Permeation Chromatography: gel permeation chromatography).
The acrylic copolymer may be synthesized by polymerizing the monomer of the alkyl (meth) acrylate by radical reaction in the presence of a polymerization initiator by a conventionally known method. The detailed polymerization method is not particularly limited, and conventionally known methods can be used. For example, solution polymerization is preferable.
The adhesive composition of the present embodiment can be produced by mixing the acrylic copolymer with a desired solvent, a crosslinking agent, a tackifier, a silane coupling agent, or the like.
Examples of the crosslinking agent that may be contained in the adhesive composition of the present embodiment are preferably isocyanate compounds having 3 or more functions. Specifically, diisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate, xylylene diisocyanate, and pentamethylene diisocyanate are preferable, and TMP (trimethylol propane) adducts of toluene diisocyanate, isocyanurate bodies of pentamethylene diisocyanate, and the like are particularly preferable.
The haze value of the adhesive composition of the present embodiment is preferably 2.5 or less, more preferably 2.0 or less, and particularly preferably 1.0 or less. The total light transmittance of the adhesive composition is preferably 97% or more.
If the haze value and the total light transmittance of the adhesive composition are in the above ranges, for example, when transparent adherends are bonded to each other, the transparency of the laminate can be improved.
The total light transmittance and haze value of the adhesive composition of the present embodiment can be measured using, for example, a haze meter "NDH4000" manufactured by japan electrochromic, using a single-layer sheet of the adhesive resin formed from the adhesive composition as a sample.
< laminate >
The laminate of the present embodiment is a two-layer laminate of a base material and an adhesive layer in which an adhesive composition is laminated on the base material. In addition, a three-layer laminate in which a base material, an adhesive layer, and a base material are laminated in this order may be used. Here, the adhesive layer refers to a layer of the adhesive composition obtained by applying the adhesive composition of the present embodiment to a substrate and drying the same.
The substrate is preferably 1 or more selected from the group consisting of a modified polyimide resin film, a polyester resin film, a liquid crystal polymer film, a cyclic olefin resin film, a polyphenylene oxide resin film, a polyphenylene sulfide resin film, a polyether ether ketone resin film, a bismaleimide resin film, a triazine resin film, and a benzocyclobutene resin film, for example.
In the laminate of the present embodiment, the thickness of the adhesive layer is, for example, 1 μm or more and 200 μm or less. The thickness of the base material is, for example, 20 μm or more and 200 μm or less.
< printed wiring Board >
The printed wiring board of the present embodiment includes the laminate of the present invention. More specifically, the adhesive composition of the present embodiment includes a laminate in which a metal foil forming a conductive circuit and a resin base material are bonded together as a constituent element. The printed wiring board is, for example, a flexible printed circuit board or a copper-clad circuit board using copper as a metal foil.
Conventionally, as a laminate for a printed wiring board, there is a laminate in which a resin base material and a metal base material are laminated via an adhesive layer. The adhesive composition of the present invention is a biomass material having low dielectric characteristics in a high frequency region. Therefore, the binder derived from fossil raw materials conventionally used for printed wiring boards can be replaced with a biomass material.
< adhesive film >
The adhesive film of the present embodiment includes an adhesive layer formed of the adhesive composition of the present embodiment described above on one or both sides of the resin film.
< adhesive layer for optical film >
The adhesive layer for an optical film of the present embodiment can be formed by applying the adhesive composition of the present embodiment to a substrate and/or a release film, and then crosslinking the adhesive composition. The gel fraction of the crosslinked adhesive layer for an optical film is preferably 60 to 90%.
When the adhesive layer for an optical film of the present embodiment is used for bonding between layers of an optical member or the like, a thin adhesive layer is preferable. The thickness of the adhesive layer for an optical film is preferably 5 to 25. Mu.m.
< image display device >
The present embodiment is an image display device in which the adhesive layer for an optical film of the present embodiment is used for bonding an optical film.
The adhesive layer for an optical film according to the present embodiment can be used for bonding glass plates and the like of an image display device.
The image display device of the present embodiment includes, but is not limited to, a liquid crystal display device (liquid crystal panel), an organic EL display device (liquid crystal panel), a touch panel, and electronic paper.
< polarizing plate >
The present embodiment is a polarizing plate, and the adhesive layer for an optical film of the present embodiment is used for bonding an optical film.
The adhesive layer for an optical film of the present embodiment has sufficient transparency, and is therefore suitable for bonding a polarizing plate.
Examples (example)
Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
< preparation of adhesive composition >
Example 1
(1) Production of acrylic acid copolymer
Nitrogen was introduced into a reaction apparatus equipped with a stirrer, a thermometer, a reflux condenser and a nitrogen inlet tube, and the air in the reaction apparatus was replaced with nitrogen. Then, 50 parts by weight of isobornyl acrylate, 50 parts by weight of 2-ethylhexyl acrylate, 1.0 part by weight of 4-hydroxybutyl (meth) acrylate, and a solvent (ethyl acetate) were added together in the reaction apparatus. Then, 0.1 part by weight of azobisisobutyronitrile was added dropwise thereto as a polymerization initiator for 2 hours, and reacted at 65℃for 6 hours to obtain an acrylic copolymer solution.
The weight average molecular weight (Mw) and the molecular weight dispersity (Mw/Mn) of the acrylic copolymer as measured by GPC based on standard polystyrene are shown in Table 1.
(2) Production of adhesive composition
To 100 parts by weight of the obtained acrylic copolymer, 0.5 parts by mass of a crosslinking agent (corning (registered trademark) L45E) was added and mixed with stirring to obtain an adhesive composition of example 1.
(3) Production of adhesive sheet
The adhesive composition was applied to a release film comprising a polyethylene terephthalate (PET) film obtained by coating with a silicone resin, and then dried at 90 ℃.
Examples 2 to 11 and comparative examples 1 to 2
Adhesive compositions of examples 2 to 11 and comparative examples 1 to 2 shown in table 1 below were prepared by the same method as in example 1.
[ Table 1]
The symbols in table 1 represent the following materials. [] The numerical values in the above are the blending amounts (parts by weight).
IBOA: isobornyl acrylate
LMA: lauryl methacrylate
LA: lauryl acrylate
OCA: octyl acrylate
ISTA: isostearyl acrylate
SA: stearyl acrylate
SMA: stearyl methacrylate
THFA: tetrahydrofuran acrylate
BHA: behenyl acrylate
2EHA: 2-ethylhexyl acrylate
4HBA: acrylic acid 4-hydroxybutyl ester
[ measurement of Biomass degree ]
The biomass degree shown in table 1 is a value calculated by the following method.
The biomass content of the acrylic copolymer contained in the adhesive composition was measured by measuring the content of the carbon isotope of mass number 14 by accelerator mass spectrometry (AMS method) measured in accordance with ASTM D6866.
Specifically, the adhesive sheet obtained in the above "(3) production of adhesive sheet" was measured for the biomass content of the acrylic copolymer contained in the adhesive composition by measuring the content of the carbon isotope of the mass number 14 by the accelerator mass spectrometry (AMS method) measured in accordance with ASTM D6866.
The adhesive sheet obtained in the above "(3) production of an adhesive sheet" corresponds to a solid component excluding the solvent component of the adhesive composition, and therefore the biomass level of the adhesive sheet can be regarded as the biomass level of the acrylic copolymer contained in the adhesive composition.
[ measurement of dielectric Properties ]
The adhesive sheet obtained in the above "(3) production of an adhesive sheet" was laminated on both sides with a release film composed of a polyethylene terephthalate (PET) film obtained by coating with a silicone resin, to obtain a laminate sheet having a three-layer structure of a release film a, an adhesive layer C and a release film B.
Dielectric characteristics of the obtained three-layer laminated sheet were measured.
The dielectric properties of the individual release film monolayers on both sides and thus the dielectric properties of the laminate were measured.
The dielectric characteristics of the adhesive composition alone were calculated from the thickness information of each layer using the complex dielectric constant values obtained from the measurement results of the single layer and the laminated sheet of the release film.
Specifically, the method is described below.
The thickness of the release film A was tA (μm), and the complex dielectric constant was εA.
The thickness of the release film B was tB (μm), and the complex dielectric constant was εB.
The thickness of the adhesive layer C was set to tC (μm), and the complex dielectric constant was set to εC.
In this case, the relationship of complex dielectric constants (εTotal) of the laminated sheets of the entire three-layer structure is represented by the following formula.
The complex dielectric constant εC of the adhesive composition monomer was calculated according to the following formula.
εTotal×(tA+tB+tC)＝εA×tA+εB×tB+εC×tC
Regarding the dielectric characteristics, the relative permittivity and dielectric loss tangent were measured for a frequency of 10GHz by a split column dielectric resonator method using E5071C manufactured by agilent corporation. The results are shown in Table 2.
[ method for measuring total light transmittance ]
The adhesive sheet obtained in the above "(3) production of adhesive sheet" was measured for total light transmittance (%) by using N3 in accordance with JIS K7361-1 (test method for total light transmittance of plastic-transparent material-part 1: single beam method) using a haze meter (trade name: NDH 4000) manufactured by Nippon Denshoku Co., ltd. And the average value thereof was taken as the total light transmittance.
[ method for measuring haze value ]
The adhesive sheet obtained in the above "(3) production of adhesive sheet" was measured for haze value (%) using N3 in accordance with JIS K7136 (method for obtaining haze of plastic-transparent material) using a haze meter (trade name: NDH 4000) manufactured by japan electrochromic co.
[ measurement of adhesive Strength ]
The adhesive sheet obtained in the above "(3) production of adhesive sheet" was transferred onto one side of a substrate of a polyester film having a thickness of 50 μm, to obtain an adhesive film (optical film with an adhesive layer) to be a sample. The obtained adhesive film was bonded to the surface of a stainless steel foil having a thickness of 2mm by a pressure-bonding roller, and the film was subjected to an atmosphere of 23 ℃ x 50% rh for 20 minutes. As a method for measuring the adhesive force when the adhesive film is peeled from the surface of the stainless steel foil, the peel strength of the adhesive film was measured by a tensile tester according to JIS Z0237 (adhesive tape, adhesive sheet test method), and the peel strength when peeled at a speed of 300mm/min in the 180 ° direction was taken as the adhesive force (N/25 mm) of the adhesive layer of the adhesive film.
[ Table 2]
Comparative example 1, in which biomass-derived carbon was 0%, and comparative example 2, in which biomass-derived carbon was less than 30%, had a relative dielectric constant exceeding 2.80.
On the other hand, examples 1 to 11 in which carbon derived from biomass was 30% or more of the total carbon number of the acrylic copolymer were confirmed to have a relative dielectric constant of 2.80 or less and low dielectric characteristics in the high frequency region.
The relative permittivity of example 5, which had a biomass content of 78.0% at the highest, was the lowest, and it can be seen that the higher the biomass content, the lower the relative permittivity tended.
It was confirmed that examples 1 to 11 exhibited high total light transmittance and haze values to the same extent as comparative example 1, which did not originate from biomass.
It was confirmed that examples 1 to 11 can arbitrarily cope with the adhesive strength range from weak (0.4N/25 mm) to strong (16.5N/25 mm).
Examples 12 to 25 and comparative examples 3 to 4
Adhesive compositions of examples 12 to 25 and comparative examples 3 to 4 shown in Table 3 below were prepared in the same manner as in example 1.
[ Table 3]
In table 3, each symbol represents the following material. [] The numerical values in the above are the blending amounts (parts by weight).
IBOA: isobornyl acrylate
LMA: lauryl methacrylate
LA: lauryl acrylate
OCA: octyl acrylate
ISTA: isostearyl acrylate
SA: stearyl acrylate
SMA: stearyl methacrylate
THFA: tetrahydrofuran acrylate
BHA: behenyl acrylate
2EHA: 2-ethylhexyl acrylate
4HBA: acrylic acid 4-hydroxybutyl ester
EA: acrylic acid ethyl ester
BA: butyl acrylate
The biomass degree values shown in table 3 are values measured by the method described in [ measurement of biomass degree ] above.
The adhesive compositions of examples 12 to 25 and comparative examples 3 to 4 were measured for relative permittivity, dielectric loss tangent, total light transmittance, haze value and adhesive strength by the methods described in [ measurement of dielectric characteristics ], [ measurement of total light transmittance ], [ measurement of haze value ], and [ measurement of adhesive strength ]. The results are shown in Table 4.
[ Table 4]
Comparative example 4, in which biomass-derived carbon was 0%, had a relative dielectric constant exceeding 2.80. In addition, comparative example 3, in which biomass-derived carbon was 41.0%, had a relative dielectric constant exceeding 2.80.
On the other hand, in examples 12 to 25 in which 30% or more of the total carbon number of the acrylic copolymer was biomass-derived carbon, it was confirmed that the relative dielectric constant was all 2.80 or less and that the low dielectric characteristics were exhibited in the high frequency region.
It was confirmed that examples 12 to 25 can arbitrarily cope with the adhesive strength range from weak (0.2N/25 mm) to strong (18.4N/25 mm).
Claims (10)
1. An adhesive composition comprising an acrylic copolymer,
more than 30% of the total carbon number of the acrylic copolymer is biomass-derived carbon,
the relative dielectric constant of the adhesive composition at 10GHz is 2.80 or less.
2. The adhesive composition according to claim 1, wherein the acrylic copolymer has a component (A1) and a component (A3) as monomer components,
the component (A1) is a monomer component represented by the following general formula (1),
the component (A3) is hydroxyalkyl (meth) acrylate,
in the general formula (1), R 1 Is a hydrogen atom or methyl group, R 2 Is C1-36 alkyl, R 2 The alkyl group represented is a biomass-derived alkyl group.
3. The adhesive composition according to claim 2, wherein the component (A1) is 1 or 2 selected from the group consisting of isobornyl acrylate, lauryl methacrylate, lauryl acrylate, octyl acrylate, isostearyl acrylate, stearyl methacrylate and behenyl acrylate.
4. The adhesive composition according to claim 1 or 2, wherein the adhesive composition has a haze value of 2.5 or less and a total light transmittance of 97% or more.
5. A laminate comprising an adhesive layer formed from the adhesive composition according to claim 1 or 2.
6. A printed wiring board comprising the laminate according to claim 5.
7. An adhesive film comprising an adhesive layer formed of the adhesive composition according to claim 1 or 2 on one or both sides of a resin film.
8. An adhesive layer for an optical film, characterized by being formed of the adhesive composition according to claim 1 or 2.
9. An image display device, wherein the adhesive layer for an optical film according to claim 8 is used for bonding an optical film.
10. A polarizing plate with an adhesive layer, wherein the adhesive layer for an optical film according to claim 8 is used.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022053518 | 2022-03-29 | ||
| JP2022-053518 | 2022-03-29 | ||
| JP2023004571A JP2023147185A (en) | 2022-03-29 | 2023-01-16 | Adhesive composition, laminate, printed wiring board, adhesive film, adhesive layer for optical films, image display device and polarizing plate |
| JP2023-004571 | 2023-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116891705A true CN116891705A (en) | 2023-10-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310296411.9A Pending CN116891705A (en) | 2022-03-29 | 2023-03-24 | Adhesive composition, laminate, printed wiring board, adhesive film, adhesive layer, image display device, and polarizing plate |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2023147185A (en) |
| KR (1) | KR20230140395A (en) |
| CN (1) | CN116891705A (en) |
| TW (1) | TW202402999A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7386609B2 (en) | 2018-12-27 | 2023-11-27 | 日東電工株式会社 | adhesive composition |
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- 2023-01-16 JP JP2023004571A patent/JP2023147185A/en active Pending
- 2023-03-23 KR KR1020230037742A patent/KR20230140395A/en unknown
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| JP2023147185A (en) | 2023-10-12 |
| KR20230140395A (en) | 2023-10-06 |
| TW202402999A (en) | 2024-01-16 |
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