CN117425711A - Adhesive composition and adhesive sheet - Google Patents
Adhesive composition and adhesive sheet Download PDFInfo
- Publication number
- CN117425711A CN117425711A CN202380012036.9A CN202380012036A CN117425711A CN 117425711 A CN117425711 A CN 117425711A CN 202380012036 A CN202380012036 A CN 202380012036A CN 117425711 A CN117425711 A CN 117425711A
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylic polymer
- monomer
- adhesive sheet
- mass
- 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.)
- Pending
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- 239000000853 adhesive Substances 0.000 title claims abstract description 158
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 158
- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 239000000178 monomer Substances 0.000 claims abstract description 222
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 131
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 44
- 230000009477 glass transition Effects 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 239000011347 resin Substances 0.000 claims description 60
- 229920005989 resin Polymers 0.000 claims description 60
- 239000003999 initiator Substances 0.000 claims description 24
- 125000002723 alicyclic group Chemical group 0.000 claims description 21
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 17
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 65
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 64
- -1 2-hydroxypropyl Chemical group 0.000 description 42
- 238000004519 manufacturing process Methods 0.000 description 30
- 239000007787 solid Substances 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 239000004417 polycarbonate Substances 0.000 description 16
- 229920000515 polycarbonate Polymers 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 229920006267 polyester film Polymers 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 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 10
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IAXXETNIOYFMLW-GYSYKLTISA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C(=C)C)C[C@@H]1C2(C)C IAXXETNIOYFMLW-GYSYKLTISA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 230000001186 cumulative effect Effects 0.000 description 9
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 7
- 239000012790 adhesive layer Substances 0.000 description 7
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 7
- 239000005329 float glass Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229940119545 isobornyl methacrylate Drugs 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000005357 flat glass Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 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 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 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 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 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 4
- 239000000758 substrate Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 3
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 3
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 3
- 239000004914 cyclooctane Substances 0.000 description 3
- KYTNZWVKKKJXFS-UHFFFAOYSA-N cycloundecane Chemical compound C1CCCCCCCCCC1 KYTNZWVKKKJXFS-UHFFFAOYSA-N 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 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 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 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 3
- 238000012360 testing method Methods 0.000 description 3
- UGESFXVNLURSNE-UHFFFAOYSA-N (2-prop-2-enoyloxy-1,4-dioxan-2-yl) prop-2-enoate Chemical compound C=CC(=O)OC1(COCCO1)OC(=O)C=C UGESFXVNLURSNE-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 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 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 239000012948 isocyanate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 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
- 150000007974 melamines Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 239000002245 particle Substances 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
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical class 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- 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
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- 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
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- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- 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]
Abstract
The invention aims to provide an adhesive sheet which has excellent adhesion to an adherend even in a high-temperature environment or a damp-heat environment. The present invention relates to an adhesive composition comprising: a (meth) acrylic polymer containing a (meth) acrylic monomer unit having a hydroxyl group and a (meth) acrylic monomer unit having a ring structure; and at least 1 selected from the group consisting of cyclized polymerizable polyfunctional monomers and polyfunctional monomers having a ring structure. The glass transition temperature of the (meth) acrylic polymer is 0 ℃ or lower, and the content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or lower.
Description
Technical Field
The present invention relates to an adhesive composition and an adhesive sheet.
Background
Conventionally, display devices such as a Liquid Crystal Display (LCD) and input devices such as a touch panel used in combination with the display devices have been widely used. In these display devices and input devices, a transparent adhesive sheet is used for application of attaching an optical member, and a transparent adhesive sheet is also used for attachment of a display device and an input device.
When the pressure-sensitive adhesive sheet is used for a display device or the like, the pressure-sensitive adhesive sheet may be stuck to a visually recognizable portion. In this case, the pressure-sensitive adhesive sheet is required to have high transparency and wet heat resistance. For example, patent document 1 discloses an adhesive composition containing an acrylic polymer obtained by polymerizing a monomer containing (a) an alkyl (meth) acrylate monomer having an alkyl group having 10 to 24 carbon atoms and (b) a (meth) acrylate monomer having a substituent capable of forming a cyclic ether structure upon polymerization. In patent document 1, an acrylic polymer has (c) an amide-containing monomer, and thus improvement in wet heat resistance has been studied.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open publication No. 2017-66243
Disclosure of Invention
Problems to be solved by the invention
The pressure-sensitive adhesive sheet to be adhered to an optical member is required to have excellent adhesion in addition to high transparency. In recent years, optical members to which an adhesive sheet is attached are sometimes used under severe environments such as high-temperature and high-humidity environments, and excellent adhesion under such conditions is demanded. However, the pressure-sensitive adhesive sheet obtained in patent document 1 has room for improvement in adhesion to an adherend under a hot and humid environment.
Accordingly, the present inventors have studied for the purpose of providing an adhesive sheet which exhibits excellent adhesion to an adherend even in a high-temperature environment or in a hot and humid environment, in order to solve the problems of the prior art.
Solution for solving the problem
Specifically, the present invention has the following configuration.
[1] An adhesive composition comprising:
a (meth) acrylic polymer containing a (meth) acrylic monomer unit having a hydroxyl group and a (meth) acrylic monomer unit having a ring structure; and
at least 1 selected from the group consisting of cyclized polymerizable polyfunctional monomers and polyfunctional monomers having a ring structure,
The glass transition temperature of the (meth) acrylic polymer is 0 ℃ or lower,
the content of the (meth) acrylic monomer unit having a hydroxyl group in the (meth) acrylic polymer is 20 mass% or more relative to the total mass of the (meth) acrylic polymer,
the content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is 1 mass% or more relative to the total mass of the (meth) acrylic polymer,
the content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or less.
[2] The adhesive composition according to [1], wherein the (meth) acrylic monomer unit having a ring structure is a (meth) acrylic monomer unit having an alicyclic structure.
[3] The adhesive composition according to [1] or [2], which further comprises a resin having a glass transition temperature of 20 ℃ or higher.
[4] The adhesive composition according to any one of [1] to [3], further comprising a polyfunctional monomer which does not have a ring structure and does not undergo cyclization.
[5] The adhesive composition according to any one of [1] to [4], further comprising a monofunctional monomer having a ring structure.
[6] The adhesive composition according to any one of [1] to [5], further comprising a silane coupling agent.
[7] The adhesive composition according to any one of [1] to [6], which further comprises a photopolymerization initiator.
[8] An adhesive sheet formed from the adhesive composition of any one of [1] to [7 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, an adhesive sheet exhibiting excellent adhesion to an adherend even in a high-temperature environment or a hot and humid environment can be obtained.
Drawings
Fig. 1 is a schematic view showing a cross section of an adhesive sheet having a release sheet.
Detailed Description
The present invention will be described in detail below. The following description of technical features is sometimes based on the representative embodiments and specific examples, but the present invention is not limited to such embodiments. In the present specification, the numerical range shown by using "to" refers to a range including numerical values described before and after "to" as a lower limit value and an upper limit value.
In the present specification, "(meth) acrylic" means both or either acrylic or methacrylic. In the present specification, "monomer" and "monomer" have the same meaning, and "polymer" have the same meaning.
(adhesive composition)
The present invention relates to an adhesive composition comprising: a (meth) acrylic polymer containing a (meth) acrylic monomer unit having a hydroxyl group and a (meth) acrylic monomer unit having a ring structure; and at least 1 selected from the group consisting of cyclized polymerizable polyfunctional monomers and polyfunctional monomers having a ring structure. The glass transition temperature of the (meth) acrylic polymer is 0 ℃ or lower, and the content of the (meth) acrylic monomer unit having a hydroxyl group in the (meth) acrylic polymer is 20 mass% or higher relative to the total mass of the (meth) acrylic polymer. The content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is 1 mass% or more relative to the total mass of the (meth) acrylic polymer, and the content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or less.
With the above configuration, the pressure-sensitive adhesive sheet formed from the pressure-sensitive adhesive composition of the present invention exhibits excellent adhesion to an adherend even in a high-temperature environment or in a hot and humid environment. Specifically, when an adhesive sheet formed of the adhesive composition of the present invention was stuck to a polycarbonate sheet or float glass, and after standing in a constant temperature and humidity machine at 95 ℃ for 30 minutes, and a constant load was measured using a weight of 100g, peeling of the adhesive sheet was suppressed, and the adhesive sheet was evaluated to have good adhesion under a high temperature environment. The pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition of the present invention was stuck to a polycarbonate sheet or float glass, and when the pressure-sensitive adhesive sheet was kept in a constant temperature and humidity machine at a temperature of 85 ℃ and a relative humidity of 85% for 60 minutes and then subjected to a constant load measurement using a weight of 100g, peeling of the pressure-sensitive adhesive sheet was suppressed, and the pressure-sensitive adhesive sheet was evaluated as excellent in adhesion under a hot and humid environment.
In addition, the pressure-sensitive adhesive sheet formed from the pressure-sensitive adhesive composition of the present invention is also excellent in outgas resistance. Specifically, even when an adhesive sheet formed from the adhesive composition of the present invention is stuck to an adherend such as a polycarbonate sheet and left to stand for a predetermined time or longer in a high-temperature environment, the occurrence of bubbles and peeling between the adhesive sheet and the adherend is suppressed, and it can be evaluated that the degassing resistance is good.
Further, the adhesive sheet formed from the adhesive composition of the present invention has excellent light resistance (weather resistance). Specifically, when the obtained laminate was set at Super Xenon Weather Meter SX75 manufactured by Suga Test Instruments company and the increase in the b-th value before and after the irradiation of a predetermined light (300 to 400 nm) for 300 hours was suppressed after the both sides of the pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition of the present invention were adhered with glass plates, it was evaluated that the light resistance (weather resistance) was good. In this way, the pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition of the present invention is suppressed in yellowing and exhibits high transparency, and therefore, can be particularly preferably used for optical application adhesion.
(meth) acrylic Polymer
The adhesive composition contains a (meth) acrylic polymer that contains a (meth) acrylic monomer unit having a hydroxyl group and a (meth) acrylic monomer unit having a ring structure, and has a glass transition temperature of 0 ℃ or less. The content of the (meth) acrylic monomer unit having a hydroxyl group in the (meth) acrylic polymer is 20 mass% or more relative to the total mass of the (meth) acrylic polymer, and the content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is 1 mass% or more relative to the total mass of the (meth) acrylic polymer. The content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or less.
Examples of the (meth) acrylic monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, and polyalkylene glycol mono (meth) acrylate. Among them, at least 1 selected from the group consisting of 2-hydroxyethyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate is preferably used.
The content of the (meth) acrylic monomer unit having a hydroxyl group in the (meth) acrylic polymer may be 20 mass% or more, preferably 25 mass% or more, based on the total mass of the (meth) acrylic polymer. The content of the (meth) acrylic monomer unit having a hydroxyl group in the (meth) acrylic polymer is preferably 50 mass% or less relative to the total mass of the (meth) acrylic polymer. When the content of the (meth) acrylic monomer unit having a hydroxyl group is within the above range, the adhesion and the outgas resistance of the adhesive sheet in a high-temperature environment and a hot-humid environment can be more effectively improved.
The (meth) acrylic polymer contains a (meth) acrylic monomer unit having a ring structure. The (meth) acrylic monomer having a ring structure is preferably a (meth) acrylic monomer having an alicyclic or aromatic ring, more preferably a (meth) acrylic monomer having an alicyclic ring. Examples of the alicyclic ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, norbornene, norbornadiene, dicyclopentane, tetrahydrofuran, and tetrahydropyran. The alicyclic ring may have a spiro structure. Examples of the aromatic ring include benzene, naphthalene, anthracene, pyridine, furan, benzofuran, pyrrole, thiophene, imidazole, and oxazole. Of these, the ring structure is preferably an alicyclic ring, and particularly preferably at least 1 selected from cyclohexane, dicyclopentane, isobornane and benzene. The above-mentioned ring structure may further have a substituent. Examples of the substituent include substituents which can be substituted and which are selected from a halogen atom, a haloalkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, a cyano group, an epoxy group, an oxetanyl group, a mercapto group, an amino group, and a (meth) acryloyl group.
Examples of the (meth) acrylic monomer having a ring structure include cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, phenoxyethyl (meth) acrylate, 3-phenoxybenzyl (meth) acrylate, and O-phenylphenoxyethyl (meth) acrylate. The content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is preferably 1 mass% or more, more preferably 3 mass% or more, and still more preferably 5 mass% or more, relative to the total mass of the (meth) acrylic polymer. The content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is preferably 30 mass% or less. When the content of the (meth) acrylic monomer unit having a ring structure is within the above range, the adhesiveness and the outgas resistance of the adhesive sheet can be more effectively improved.
The glass transition temperature of the (meth) acrylic polymer is not more than 0 ℃, preferably not more than-10 ℃, more preferably not more than-20 ℃, and still more preferably not more than-30 ℃. The lower limit of the glass transition temperature of the (meth) acrylic polymer is not particularly limited, but is preferably at least-80 ℃.
The glass transition temperature of the (meth) acrylic polymer can be calculated by the following FOX equation.
1/Tgp＝W1/Tg1+W2/Tg2+···+Wn/Tgn
Tgp is the glass transition temperature of the acrylic polymer, wn is the weight fraction of each monomer, and Tgn is the glass transition temperature when each monomer is made into a homopolymer.
The weight average molecular weight of the (meth) acrylic polymer is preferably more than 10000, more preferably 10 ten thousand or more, and still more preferably 20 ten thousand or more. The weight average molecular weight of the (meth) acrylic polymer is preferably 200 ten thousand or less, more preferably 150 ten thousand or less, and still more preferably 120 ten thousand or less. The weight average molecular weight of the (meth) acrylic polymer means: a standard curve was prepared using standard polystyrene having a known molecular weight, and the standard curve was used to calculate the value obtained by performing measurement by Gel Permeation Chromatography (GPC). As the (meth) acrylic polymer, commercially available ones may be used, or polymers synthesized by a known method may be used.
The (meth) acrylic polymer may contain an alkyl (meth) acrylate unit in addition to the (meth) acrylic monomer unit having a hydroxyl group. Examples of the alkyl (meth) acrylate include alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, and behenyl (meth) acrylate.
When the (meth) acrylic polymer contains an alkyl (meth) acrylate unit, the number of carbon atoms of the alkyl (meth) acrylate is preferably 1 or more, more preferably 2 or more, and still more preferably 3 or more. The number of carbon atoms of the alkyl (meth) acrylate may be 24 or less, may be 20 or less, may be 18 or less, may be 15 or less, may be 12 or less, and may be 9 or less. When the number of carbon atoms of the alkyl (meth) acrylate is within the above range, the adhesion and the outgas resistance of the adhesive sheet can be more effectively improved.
The (meth) acrylic polymer may contain a (meth) acrylic monomer unit having a crosslinkable functional group in addition to a (meth) acrylic monomer unit having a hydroxyl group. Examples of the crosslinkable functional group of the (meth) acrylic monomer having a crosslinkable functional group include an amide group, an amino group, a thiol group, an isocyanate group, an epoxy group, a silanol group, and a carboxylic acid group. The content of the (meth) acrylic monomer unit having a crosslinkable functional group in the (meth) acrylic polymer is preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 3% by mass or less. By setting the content of the (meth) acrylic monomer unit having a crosslinkable functional group in the (meth) acrylic polymer to the above range, the adhesion between the adhesive sheet and the adherend can be more effectively improved.
The content of the (meth) acrylic monomer unit having a carboxylic acid group in the (meth) acrylic polymer may be 0.1 mass% or less and may be 0.01 mass% or less. This means: the (meth) acrylic polymer contains substantially no (meth) acrylic monomer units having carboxylic acid groups. That is, the (meth) acrylic polymer contained in the adhesive composition of the present invention does not contain a (meth) acrylic monomer unit having a carboxylic acid group, and the resulting adhesive composition may be an acid-free adhesive composition.
The (meth) acrylic polymer may have other monomer units as required. The other monomer may be copolymerized with the monomer component, and examples thereof include vinyl acetate, vinyl chloride, and ethyl vinyl ether. The content of the other monomer unit in the (meth) acrylic polymer is preferably 10 mass% or less, more preferably 5 mass% or less.
The content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or less, preferably 0.01 mass% or less. This means: the (meth) acrylic polymer contains substantially no monomer units having nitrogen atoms. By making the (meth) acrylic polymer substantially free of monomer units having nitrogen atoms, the adhesion and light resistance (weather resistance) of the adhesive sheet can be more effectively improved.
The adhesive composition may comprise an acrylic syrup (syrup) a comprising a (meth) acrylic polymer. Here, the acrylic syrup a contains at least a (meth) acrylic polymer and a monomer constituting the (meth) acrylic polymer. Accordingly, the adhesive composition may further contain a monomer constituting the (meth) acrylic polymer in addition to the (meth) acrylic polymer. When the acrylic syrup a contains monomers constituting the (meth) acrylic polymer, these monomers are polymerized in the step of producing the adhesive sheet to form the (meth) acrylic polymer.
< tackifying resin >
The adhesive composition may further comprise a resin having a glass transition temperature of 20 ℃ or higher. In the present invention, a resin having a glass transition temperature of 20 ℃ or higher functions as a tackifying resin (tackifier). By adding the tackifier resin to the adhesive composition in addition to the (meth) acrylic polymer, the compatibility of the components in the adhesive composition is improved, and the adhesive sheet formed from the adhesive composition exhibits more excellent adhesion, outgas resistance, and light resistance (weather resistance).
The glass transition temperature of the resin (tackifying resin) having a glass transition temperature of 20 ℃ or higher is preferably 30 ℃ or higher, more preferably 40 ℃ or higher, and still more preferably 50 ℃ or higher. The glass transition temperature of the tackifier resin is preferably 200℃or lower, more preferably 180℃or lower, and still more preferably 150℃or lower. By setting the glass transition temperature of the tackifier resin to be within the above range, the adhesion of the pressure-sensitive adhesive sheet to an adherend can be improved.
The weight average molecular weight of the tackifier resin is preferably 3000 or more, more preferably 3200 or more, and still more preferably 3500 or more. The weight average molecular weight of the tackifier resin is 10000 or less, more preferably 9000 or less, and still more preferably 8000 or less. The weight average molecular weight of the tackifying resin refers to: a standard curve was prepared using standard polystyrene having a known molecular weight, and the standard curve was used to calculate the value obtained by performing measurement by Gel Permeation Chromatography (GPC). As such a resin, a commercially available product may be used, or a resin synthesized by a known method may be used.
The tackifying resin preferably has substantially no functional groups. In this case, the tackifying resin does not form a crosslinked structure with the (meth) acrylic polymer.
The tackifying resin may comprise monomer units having an alicyclic ring. When the tackifying resin contains a monomer unit having an alicyclic ring, the number of carbon atoms constituting the alicyclic ring is preferably 6 or more. Examples of the alicyclic ring having 6 or more carbon atoms include cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, norbornene, norbornadiene, and dicyclopentane.
As the alicyclic monomer, for example, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and the like can be preferably used.
In the case where the tackifying resin contains a monomer unit having an alicyclic ring, the content of the monomer unit having an alicyclic ring is preferably 5 mass% or more, more preferably 10 mass% or more, relative to the total mass of the tackifying resin. The content of the alicyclic monomer unit is preferably 90 mass% or less, more preferably 80 mass% or less, based on the total mass of the tackifier resin. By setting the content of the monomer unit having an alicyclic ring to the above range, the compatibility between the (meth) acrylic polymer and the tackifying resin can be improved, and the adhesion between the adhesive sheet and the adherend can be more effectively improved.
The tackifying resin may further contain alkyl (meth) acrylate units. Examples of the alkyl (meth) acrylate include alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, and behenyl (meth) acrylate. Among them, the tackifying resin preferably contains methyl (meth) acrylate. The content of the alkyl (meth) acrylate unit is preferably 10 mass% or more, more preferably 15 mass% or more, relative to the total mass of the tackifying resin. The content of the alkyl (meth) acrylate unit is preferably 95 mass% or less, more preferably 90 mass% or less, based on the total mass of the tackifying resin. By setting the content of the alkyl (meth) acrylate unit to the above range, the compatibility between the (meth) acrylic polymer and the tackifying resin can be improved, and the adhesion between the adhesive sheet and the adherend can be more effectively improved.
The tackifying resin may have other monomer units as desired. The other monomer may be copolymerized with the monomer component, and examples thereof include (meth) acrylonitrile, vinyl acetate, vinyl chloride, and ethyl vinyl ether. The content of the other monomer unit in the tackifying resin is preferably 10 mass% or less, more preferably 5 mass% or less.
The content of the tackifying resin in the adhesive composition is preferably 1 part by mass or more, more preferably 1.2 parts by mass or more, and even more preferably 1.5 parts by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The content of the tackifying resin in the adhesive composition is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less, based on 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. In the pressure-sensitive adhesive sheet comprising the pressure-sensitive adhesive composition, the monomer constituting the (meth) acrylic polymer constitutes the (meth) acrylic polymer, and therefore, the content of the tackifying resin is preferably in the above range with respect to 100 parts by mass of the (meth) acrylic polymer. When the content of the tackifier resin is within the above range, the adhesion of the adhesive sheet to the adherend can be improved, and further, the outgas resistance of the adhesive sheet can be more effectively improved.
< Cyclic polymerizable multifunctional monomer/multifunctional monomer having Ring Structure >
The adhesive composition contains at least 1 selected from the group consisting of cyclized polymerizable polyfunctional monomers and polyfunctional monomers having a ring structure. These polyfunctional monomers are polyfunctional monomers having 2 or more reactive double bonds in the molecule, preferably 2 or more and less than 5 reactive double bonds, more preferably 2 or more and less than 4 reactive double bonds. The reactive double bond is preferably a radical polymerizable unsaturated group. It can be considered that: by including at least 1 selected from the group consisting of a cyclized polymerizable polyfunctional monomer and a polyfunctional monomer having a ring structure in the pressure-sensitive adhesive composition, the (meth) acrylic polymer can be crosslinked nonlinearly, whereby a pressure-sensitive adhesive sheet having both flexibility and cohesive force can be produced. As a result, an adhesive sheet exhibiting excellent adhesion to an adherend can be obtained.
The cyclized polymerizable polyfunctional monomer is a polyfunctional monomer that forms a cyclic structure upon polymerization. Among them, the cyclized polymerizable polyfunctional monomer is preferably a polyfunctional monomer which forms a cyclic ether structure upon polymerization. The cyclized polymerizable multifunctional monomer is preferably a multifunctional monomer having at least 2 radically polymerizable unsaturated groups, for example, having a right-end structure in the following structural formula. The cyclized polymerizable polyfunctional monomer forms a cyclic structure (cyclic ether structure) in the main chain when radical polymerization occurs in the presence of a chain transfer agent during polymerization, as shown in the following reaction scheme. The cyclic structure (cyclic ether structure) formed is preferably a 3-to 8-membered ring, more preferably a 5-membered ring or a 6-membered ring.
Wherein R represents a hydrogen atom or a substituent, and the substituent is preferably an organic group having 1 to 30 carbon atoms. Among them, R is preferably a saturated hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, tert-pentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, sec-octyl, tert-octyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, lauryl, tridecyl, myristyl, pentadecyl, cetyl, heptadecyl, stearyl, nonadecyl, eicosyl, hexacosyl, and melissa, and particularly preferably methyl or ethyl.
In the formula, X is preferably a chain transfer agent. Examples of the chain transfer agent include compounds having a mercapto group such as mercapto carboxylic acids, mercapto carboxylic acid esters, alkyl thiols, mercapto alcohols, aromatic thiols, and mercapto isocyanurates.
As the cyclized polymerizable polyfunctional monomer, examples thereof include alpha-allyloxymethyl methacrylate, alpha-allylpropyl methacrylate, isopropyl acrylate, alpha-allylpropyl methacrylate, isopropyl sec-butyl alpha-allyloxy methacrylate, tert-butyl alpha-allyloxy methacrylate, n-pentyl alpha-allyloxy methacrylate, sec-pentyl alpha-allyloxy methacrylate, tert-pentyl alpha-allyloxy methacrylate, n-hexyl alpha-allyloxy methacrylate, sec-hexyl alpha-allyloxy methacrylate, n-heptyl alpha-allyloxy methacrylate, n-octyl alpha-allyloxy methacrylate, sec-octyl alpha-allyloxy methacrylate, tert-octyl alpha-allyloxy methacrylate, 2-ethylhexyl alpha-allyloxy methacrylate, octyl alpha-allyloxy methacrylate, nonyl alpha-allyloxy methacrylate, decyl alpha-allyloxy methacrylate, undecyl alpha-allyloxy methacrylate, and the like. Among them, the cyclized polymerizable polyfunctional monomer is preferably at least 1 selected from the group consisting of α -allyloxymethyl methacrylate, α -allyloxymethyl methacrylate and α -allyloxymethyl methacrylate, more preferably at least 1 selected from the group consisting of α -allyloxymethyl methacrylate and α -allyloxymethyl methacrylate. As the cyclized polymerizable polyfunctional monomer, for example, a monomer described in japanese patent application laid-open No. 2010-16889 can be used.
Further, as the cyclized polymerizable polyfunctional monomer, commercially available ones can be used. Examples of the commercial products include AOMA manufactured by Japanese catalyst Co.
On the other hand, the polyfunctional monomer having a ring structure is a polyfunctional monomer having a ring structure before polymerization. The adhesive composition preferably comprises a polyfunctional monomer having a ring structure.
The ring structure of the polyfunctional monomer having a ring structure is preferably an alicyclic ring, a heterocyclic ring, or an aromatic ring, and more preferably an alicyclic ring or a heterocyclic ring. Examples of the alicyclic ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, norbornene, norbornadiene, dicyclopentane, tetrahydrofuran, and tetrahydropyran. The alicyclic ring may have a spiro structure. Examples of the aromatic ring include benzene, naphthalene, and anthracene. In the case where the ring structure of the polyfunctional monomer having a ring structure is a heterocyclic ring, examples of the heterocyclic ring (including heteroaromatic rings) include pyridine, pyrimidine, purine, furan, benzofuran, pyrrole, thiophene, imidazole, oxazole, ethyleneimine, ethylene oxide, 1, 3-propylene oxide, triazole, and the like. Among them, the heterocyclic ring is preferably a ring containing an oxygen atom or a nitrogen atom, more preferably a ring containing an oxygen atom.
The polyfunctional monomer having a ring structure preferably has a ring structure of 5-membered ring or 6-membered ring.
Examples of the polyfunctional monomer having a ring structure include dioxane diol diacrylate, tricyclodecane dimethanol di (meth) acrylate, alkoxy-modified bisphenol a di (meth) acrylate, caprolactone-modified isocyanurate di (meth) acrylate, tris (2-acryloyloxyethyl) isocyanurate, tris- (2-acryloyloxyethyl) isocyanurate, bis- (2-acryloyloxyethyl) isocyanurate, and tris- (2-acryloyloxyethyl) isocyanurate. Among them, the polyfunctional monomer having a ring structure is preferably a polyfunctional acrylic monomer.
As the polyfunctional monomer having a ring structure, commercially available ones can be used. Examples of the commercial products include A-DOG, A-DCP, A-9300, A-9200YN manufactured by Xinzhou chemical Co., ltd; FA-731A from Hitachi chemical industries, inc.
The cyclized polymerizable polyfunctional monomer and/or the polyfunctional monomer having a ring structure forms a crosslinked structure with the (meth) acrylic polymer in the pressure-sensitive adhesive sheet. The content of the cyclized polymerizable polyfunctional monomer and/or the polyfunctional monomer having a ring structure in the adhesive composition is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The content of the cyclized polymerizable polyfunctional monomer and/or the polyfunctional monomer having a ring structure in the adhesive composition is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The adhesive composition may contain both the cyclized polymerizable multifunctional monomer and the multifunctional monomer having a ring structure, in which case the total content of the cyclized polymerizable multifunctional monomer and the multifunctional monomer having a ring structure is preferably within the above-described range. When the content of the cyclized polymerizable polyfunctional monomer and/or the polyfunctional monomer having a ring structure is within the above range, the adhesion of the pressure-sensitive adhesive sheet can be more effectively improved.
< other multifunctional monomer >
The adhesive composition may further contain a polyfunctional monomer having 2 or more reactive double bonds in the molecule, in addition to the polyfunctional monomer. In this case, the polyfunctional monomer is a polyfunctional monomer having no ring structure and not cyclizing (hereinafter, a polyfunctional monomer having no ring structure and not cyclizing may be referred to as a second polyfunctional monomer). The second polyfunctional monomer preferably has 2 or more and less than 5 reactive double bonds, more preferably 2 or more and less than 4.
Examples of the second polyfunctional monomer include polyethylene glycol diacrylate, polypropylene diacrylate, alkyl diacrylate, polytetramethylene glycol diacrylate, and polypropylene glycol diacrylate. Examples of the monomer having a trifunctional or higher functionality include an alkoxylated trimethylolpropane triacrylate, an alkoxylated glycerol triacrylate, a pentaerythritol acrylate, an alkoxylated pentaerythritol acrylate, an (alkoxylated) ditrimethylolpropane acrylate, an (alkoxylated) dipentaerythritol acrylate, and an (ethoxylated) polyglycerol acrylate.
As the second polyfunctional monomer, commercially available ones can be used. Examples of the commercial products include difunctional monomer A-200 (polyethylene glycol #200 diacrylate) and trifunctional monomer A-TMPT ((alkoxylated) trimethylolpropane acrylate) manufactured by Xinzhou chemical industry Co., ltd; difunctional monomer M240 (polyethylene glycol diacrylate), tetrafunctional monomer M-408 (ditrimethylolpropane tetraacrylate) and the like manufactured by east Asia Synthesis company.
The second polyfunctional monomer forms a crosslinked structure with the (meth) acrylic polymer in the adhesive sheet. The content of the second polyfunctional monomer in the adhesive composition is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomers constituting the (meth) acrylic polymer. The content of the second polyfunctional monomer in the adhesive composition is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. By setting the content of the second polyfunctional monomer to the above range, the hardness of the adhesive sheet can be improved, and the durability, workability, and adhesion of the adhesive sheet can be improved.
(monofunctional monomer)
The adhesive composition may comprise a monofunctional monomer. Monofunctional monomers are monomers having 1 reactive double bond in the molecule.
Examples of the monofunctional monomer include isobornyl (meth) acrylate, isostearyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, and the like. The monofunctional monomer has preferably 3 or more, more preferably 5 or more, still more preferably 7 or more, still more preferably 9 or more, and particularly preferably 10 or more carbon atoms. The monofunctional monomer is preferably a monofunctional monomer having a ring structure, and more preferably isobornyl (meth) acrylate. Examples of the commercial products of the monofunctional monomer include IBXA and IBXMA manufactured by osaka organic chemical industry co.
The content of the monofunctional monomer in the adhesive composition is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The content of the monofunctional monomer in the adhesive composition is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. When the content of the monofunctional monomer is within the above range, the adhesion of the pressure-sensitive adhesive sheet can be more effectively improved.
< crosslinking agent >
The adhesive composition may further contain a crosslinking agent in addition to the above-described polyfunctional monomer. The crosslinking agent may be appropriately selected in consideration of reactivity with the crosslinkable functional group of the (meth) acrylic polymer. The crosslinking agent may be selected from known crosslinking agents such as isocyanate compounds, epoxy compounds, oxazoline compounds, aziridine compounds, metal chelate compounds, and butylated melamine compounds. Among them, the crosslinking agent preferably contains at least 1 selected from the group consisting of isocyanate compounds, epoxy compounds, and metal chelate compounds.
< photopolymerization initiator >
The adhesive composition may further comprise a photopolymerization initiator. The photopolymerization initiator initiates polymerization of the polyfunctional monomer by irradiation of active energy rays. The "active energy ray" herein refers to a ray having energy quanta in an electromagnetic wave or charged particle beam, and examples thereof include ultraviolet rays, electron rays, visible rays, X-rays, ion rays, and the like. Among them, ultraviolet rays or electron beams are preferable from the viewpoint of versatility, and ultraviolet rays are particularly preferable.
Examples of the photopolymerization initiator include, but are not particularly limited to, acetophenone-based photopolymerization initiators such as 2, 2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexyl-phenylketone, 2-hydroxy-2-methyl-1-phenylpropion, 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-methylpropone, and 2-hydroxy-1- (4- (4- (2-hydroxy-2-methylpropanoyl) benzyl) phenyl) -2-methyl-1-propanone; acyl phosphine oxide-based photopolymerization initiators such as 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide and bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide; intramolecular hydrogen abstraction photopolymerization initiators such as methyl benzoylformate and 4-methylbenzophenone; and oil-soluble polymerization initiators such as oxime ester-based photopolymerization initiators and cationic photopolymerization initiators. Among them, the photopolymerization initiator is preferably at least 1 selected from the group consisting of acetophenone-based photopolymerization initiator, acylphosphine oxide-based photopolymerization initiator, and oxime ester-based photopolymerization initiator.
Examples of commercial products of such acetophenone photopolymerization initiators include esacureOne (oligo (2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenylpropion ], a photoinitiator manufactured by IGM RESINS b.v., manufactured by the company), omnirad651 (2, 2-dimethoxy-2-phenylacetophenone, manufactured by IGM RESINS b.v., manufactured by the company), omnirad184 (1-hydroxycyclohexyl-phenylketone, manufactured by IGM RESINS b.v., manufactured by the company), omnirad1173 (2-hydroxy-2-methyl-1-phenylpropion, manufactured by IGM RESINS b.v., manufactured by the company), and commercial products of acylphosphine oxide photopolymerization initiators include Omnirad 819 (bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, manufactured by IGM RESINS b.v., manufactured by the company), omnirad TPO (2, 4, 6-trimethylbenzoyl-diphenylphosphine oxide, manufactured by the company, IGM RESINS b.v., and the like.
The content of the photopolymerization initiator in the adhesive composition is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The content of the photopolymerization initiator in the adhesive composition is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, based on 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. By setting the content of the photopolymerization initiator to the above range, the hardness of the adhesive sheet can be improved, and the durability, workability, and adhesion of the adhesive sheet can be improved.
< silane coupling agent >
The adhesive composition may further comprise a silane coupling agent. By incorporating the silane coupling agent in the pressure-sensitive adhesive composition, the adhesion between the pressure-sensitive adhesive sheet formed of the pressure-sensitive adhesive composition and the adherend can be further improved.
Examples of the silane coupling agent include mercapto silane coupling agents having mercapto groups, epoxy silane coupling agents having epoxy groups, vinyl silane coupling agents having vinyl groups, and isocyanurate silane coupling agents.
As the silane coupling agent, commercially available ones can be used. Examples of the commercial products include KBM-9659, KBM-5103, KBM-502, KBM-503, KBM-402, KBM-403, etc. manufactured by Xinyue chemical industries.
The content of the silane coupling agent in the adhesive composition is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, and still more preferably 0.1 part by mass or more, relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. The content of the silane coupling agent in the adhesive composition is preferably 10 parts by mass or less relative to 100 parts by mass of the total mass of the (meth) acrylic polymer and the monomer constituting the (meth) acrylic polymer. When the content of the silane coupling agent is within the above range, the adhesion of the adhesive sheet can be more effectively improved.
< solvent >
The adhesive composition may comprise a solvent. In this case, the solvent is used for improving the coating suitability of the adhesive composition. Examples of the solvent include hydrocarbons such as hexane, heptane, octane, toluene, xylene, ethylbenzene, cyclohexane, and methylcyclohexane; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, diacetone alcohol, and the like; ethers such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; esters such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, amyl acetate, and ethyl butyrate; polyhydric alcohols such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol monomethyl ether acetate, and derivatives thereof.
< other ingredients >
The adhesive composition may contain other components than the above within a range that does not impair the effects of the present invention. The other component may be a component known as an additive for a pressure-sensitive adhesive. Light stabilizers such as plasticizers, antioxidants, metal corrosion inhibitors, ultraviolet absorbers, and hindered amine compounds can be selected as needed. Dyes and pigments may be added for coloring.
As the plasticizer, for example, a functional group-free acrylic polymer can be used. Examples of the acrylic polymer having no functional group include a polymer composed only of acrylic monomer units having no functional group other than an acrylate group, and a polymer containing acrylic monomer units having no functional group other than an acrylate group and non-acrylic monomer units having no functional group. The acrylic polymer having no functional group is not crosslinked, and therefore, the following property of the acrylic polymer at the time of adhesion to an adherend can be improved without affecting the adhesion.
Examples of the antioxidant include phenol antioxidants, amine antioxidants, lactone antioxidants, phosphorus antioxidants, and sulfur antioxidants. These antioxidants may be used alone or in combination of 1 or more than 2.
The metal corrosion inhibitor is preferably a benzotriazole-based resin, since it is excellent in compatibility with the binder and effect.
Examples of the ultraviolet absorber include benzotriazole-based compounds, benzophenone-based compounds, and triazine-based compounds.
(adhesive sheet)
The present invention also relates to an adhesive sheet obtained by curing the adhesive composition. The pressure-sensitive adhesive sheet of the present invention may be obtained by heat-drying the pressure-sensitive adhesive composition, or may be obtained by photo-curing the pressure-sensitive adhesive composition. Among them, the pressure-sensitive adhesive sheet is preferably obtained by photocuring the pressure-sensitive adhesive composition, and when the pressure-sensitive adhesive sheet of the present invention is formed, the pressure-sensitive adhesive composition is preferably irradiated with an active energy ray to perform a curing reaction. Examples of the active energy ray include ultraviolet rays, electron rays, visible rays, X-rays, and ion rays. Among them, ultraviolet rays or electron beams are preferable from the viewpoint of versatility, and ultraviolet rays are particularly preferable.
The pressure-sensitive adhesive sheet of the present invention is preferably a pressure-sensitive adhesive sheet or a double-sided pressure-sensitive adhesive sheet composed only of a pressure-sensitive adhesive layer. Examples of the double-sided adhesive sheet include a single-layer adhesive sheet composed of an adhesive layer, a multi-layer adhesive sheet in which a plurality of adhesive layers are laminated, and a multi-layer adhesive sheet in which another adhesive layer is laminated between the adhesive layers. The pressure-sensitive adhesive sheet of the present invention may be a multilayer pressure-sensitive adhesive sheet in which a support is laminated between pressure-sensitive adhesive layers. When the double-sided adhesive sheet has a support, a transparent support is preferably used as the support. As the support, a general film used in the optical field similar to the transparent substrate can be used. Such a double-sided pressure-sensitive adhesive sheet is excellent in transparency as a whole, and therefore, can be suitably used for bonding optical members to each other.
The present invention may relate to an adhesive sheet with a release sheet, which includes release sheets on both surfaces of the adhesive sheet. In the case where the release sheet is provided on both surfaces of the adhesive sheet of the present invention, as shown in fig. 1, the release sheet-attached adhesive sheet 10 preferably has release sheets 12a and 12b on both surfaces of the adhesive layer 11.
Examples of the release sheet include: a releasable laminate having a release sheet substrate and a release agent layer provided on one surface of the release sheet substrate; or a polyolefin film such as a polyethylene film or a polypropylene film as a polar substrate.
As the base material for the release sheet in the releasable laminate, a paper or a polymer film can be used. As the release agent constituting the release agent layer, for example, a general-purpose addition-type or condensation-type silicone release agent or a compound containing a long-chain alkyl group can be used. It is particularly preferable to use an addition type silicone release agent having high reactivity.
Specific examples of the silicone-based release agent include BY24-4527 and SD-7220 manufactured BY Tolycorning silicone company; KS-3600, KS-774, X62-2600, etc. manufactured by Xinyue chemical industries, inc. The silicone-based release agent preferably contains a silicone resin having SiO 2 Unit sum (CH) 3 ) 3 SiO 1/2 Units or CH 2 ＝CH(CH 3 )SiO 1/2 A unit of an organosilicon compound. Specific examples of the silicone resin include BY24-843, SD-7292, SHR-1404, etc. manufactured BY Tolydorning silicone company; KS-3800, X92-183, etc. manufactured by Xinyue chemical industries, inc.
As the releasable laminate, a commercially available product can be used. Examples of the heavy separator film A71 as a release-treated polyethylene terephthalate film manufactured by Di DuPont film company and the light separator film A38ST as a release-treated polyethylene terephthalate film manufactured by Di DuPont film company.
The pressure-sensitive adhesive sheet with a release sheet preferably has 1 pair of release sheets having different release forces on both surfaces of the pressure-sensitive adhesive sheet. That is, in order to make the release sheet easily peelable, it is preferable that the release properties of the release sheet 12a and the release sheet 12b are different. If the peelability from one side is different from that from the other side, it is easy to peel only the release sheet on the side having high peelability first. In this case, the peelability of the release sheet 12a and the release sheet 12b may be adjusted according to the adhering method and the adhering order.
The thickness of the pressure-sensitive adhesive sheet is not particularly limited, and is preferably 5 to 1000. Mu.m, more preferably 8 to 500. Mu.m, particularly preferably 10 to 300. Mu.m, depending on the application. When the thickness of the pressure-sensitive adhesive sheet is in the above range, the pressure-sensitive adhesive performance can be maintained and the overflow of the pressure-sensitive adhesive can be suppressed, so that the workability can be improved. Further, by setting the thickness of the adhesive layer to be within the above range, the double-sided adhesive sheet can be easily manufactured.
< method for producing adhesive sheet >
The method for producing an adhesive sheet of the present invention preferably comprises: a step of forming a coating film by applying an adhesive composition to a release sheet; a step of heating the coating film; or a step of irradiating the coating film with active energy rays. In the case where the adhesive composition contains a solvent, it is preferable to include a heat drying step. In the heat drying step, the solvent is removed to form the adhesive layer.
The application of the adhesive composition can be performed using a known application device. Examples of the coating apparatus include blade coaters, air knife coaters, roll coaters, bar coaters, gravure coaters, micro gravure coaters, bar coater, lip coaters, die coaters, curtain coaters, and the like.
In the step of heating the coating film, the coating film is preferably dried under heating conditions. The temperature in the heating step is preferably 70℃or higher, more preferably 80℃or higher, and still more preferably 85℃or higher. The temperature in the heating step is preferably 150℃or lower. The treatment time in the heating step is preferably 10 seconds or longer, more preferably 1 minute or longer, and still more preferably 2 minutes or longer. The treatment time in the heating step is preferably 1 hour or less.
In the step of irradiating the coating film with active energy rays, the cumulative light amount is preferably 100 to 10000mJ/cm 2 The irradiation of active energy rays is more preferably 500 to 5000mJ/cm 2 Is irradiated with active energy rays. In the step of irradiating the coating film with active energy rays, the active energy rays may be irradiated in two stages. For example, the irradiation intensity in the second stage can be increased as compared with that in the first stage. By performing such two-stage irradiation, the molecular weight of the polymer contained in the obtained adhesive sheet can be adjusted, and heat shrinkage and the like of the separator and the like can be suppressed.
< use of adhesive sheet >
The pressure-sensitive adhesive sheet of the present invention is used for adhering an adherend, and the adherend is preferably an optical member. The optical member includes each component in an optical product such as a touch panel and an image display device. Examples of the constituent members of the touch panel include an ITO film having an ITO film provided on a transparent resin film, an ITO glass having an ITO film provided on a surface of a glass plate, a transparent conductive film having a conductive polymer coated on a transparent resin film, a hard coat film, and a fingerprint resistant film. Examples of the constituent members of the image display device include an antireflection film, an alignment film, a polarizing film, a retardation film, and a brightness enhancement film used in a liquid crystal display device. The adhesive sheet of the present invention can be used for attaching modules such as a liquid crystal module and a touch panel module to each other.
Examples of the material used for the optical member include glass, polycarbonate, polyethylene terephthalate, polymethyl methacrylate (PMMA), polyethylene naphthalate, cyclic olefin polymer, cellulose triacetate, polyimide, and cellulose acylate. Among them, the adherend particularly preferably contains at least 1 selected from glass, polycarbonate and PMMA.
In order to improve the adhesion between the optical member and the adhesive sheet, the surface of the optical member may be subjected to corona treatment or plasma treatment.
(laminate)
The present invention may be directed to a laminate comprising the above-described adhesive sheet and an adherend. Here, the adherend is preferably an optical member, and the adherend is preferably at least 1 selected from glass, polycarbonate, and PMMA. The laminate of the present invention is preferably a laminate comprising the adhesive sheet described above and comprising a polycarbonate plate or a PMMA plate. The pressure-sensitive adhesive sheet of the present invention can exhibit excellent adhesion to a polycarbonate sheet, in particular.
Examples
Hereinafter, the features of the present invention will be described in more detail with reference to examples and comparative examples. The materials, amounts, ratios, treatment contents, treatment steps and the like shown in the following examples may be appropriately changed within the scope not departing from the gist of the present invention. Therefore, the scope of the present invention is not limited by the specific examples shown below.
Example 1
< method for producing acrylic Polymer A >
Into a 2L flask equipped with a stirrer, a nitrogen inlet tube, a condenser, and a thermometer, 620g of 2-ethylhexyl acrylate, 290g of 4-hydroxybutyl acrylate, 90g of cyclohexyl methacrylate, and 0.1g of n-dodecylmercaptan were charged, and after nitrogen substitution was performed at a nitrogen flow rate of 300ml/min for 60 minutes, the nitrogen flow rate was reduced to 100ml/min, and the temperature was raised to 65℃by a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In this manner, a slurry a containing the acrylic polymer a having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< method for producing tackifying resin a >
Into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser, and a thermometer, 250g of methyl methacrylate, 250g of isobornyl methacrylate, 20g of n-dodecyl mercaptan, 500g of ethyl acetate, and 200g of methyl ethyl ketone were charged, nitrogen substitution was performed for 60 minutes at a nitrogen flow rate of 300ml/min, and then the nitrogen flow rate was reduced to 100ml/min, and the temperature was raised to 70℃in a water bath, and heating was stopped. AIBN 2g was charged and reacted for 3 hours while controlling the heat release, and subsequently AIBN 3g was additionally charged and reacted for 4 hours, followed by cooling to 30 ℃. As described above, a tackifying resin a having a weight average molecular weight of 6,000 and a glass transition temperature of 95℃was obtained.
< production of adhesive sheet >
The tackifying resin a was dried at 100℃for 5 hours and the solvent was removed. To 100g of the slurry A, 5g of a solvent-removed tackifying resin, 3g of isobornyl acrylate, 1g of a cyclized polymerizable multifunctional monomer (AOMA, manufactured by Japanese catalyst Co., ltd.), and 1g of a multifunctional monomer (New Zhongcun chemical industry Co., ltdPrepared, NK ESTER A-200) 0.3g, a silane coupling agent (KBM-9659, made by Xinyue chemical industries, ltd.) 0.1g, and a photopolymerization initiator (IGF Resins B.V, esacure One) 0.3g were stirred and defoamed to obtain an adhesive composition. The adhesive composition was applied to a polyester film having a thickness of 100 μm and coated with a silicone release agent so as to have a thickness of 175. Mu.m, and laminated with a polyester film having a thickness of 75 μm and coated with a silicone release agent so as to have an illuminance of 5mW/cm 2 The cumulative illuminance was 900mJ/cm 2 The chemical lamp was irradiated so that the illuminance became 200mW/cm 2 The cumulative illuminance was 2000mJ/cm 2 A high-pressure mercury lamp was irradiated, thereby obtaining an adhesive sheet.
Example 2
In the < production of an adhesive sheet >, an adhesive sheet was produced in the same manner as in example 1, except that the addition amount of the cyclized polymerizable polyfunctional monomer (manufactured by the catalyst company of japan, AOMA) was changed to 0.2g and the addition amount of the polyfunctional monomer (manufactured by the chemical industry company of new yo, NK escer a-200) was changed to 0.2 g.
Example 3
In < production of pressure-sensitive adhesive sheet >, a pressure-sensitive adhesive sheet was produced in the same manner as in example 1, except that 0.15g of dioxane diol diacrylate (produced by Xinzhou chemical Co., ltd., A-DOG) was added as a polyfunctional monomer having a ring structure instead of the cyclized polymerizable polyfunctional monomer (produced by Japanese catalyst Co., ltd., AOMA), and the amount of the polyfunctional monomer (produced by Xinzhou chemical Co., ltd., NK ESTER A-200) added was changed to 0.2 g.
Example 4
In < production of pressure-sensitive adhesive sheet >, a pressure-sensitive adhesive sheet was produced in the same manner as in example 1, except that 0.1g of tricyclodecane dimethanol diacrylate (manufactured by Xinzhou chemical Co., ltd., A-DCP) was added as a polyfunctional monomer having a ring structure instead of the cyclized polymerizable polyfunctional monomer (manufactured by Japanese catalyst Co., ltd., AOMA), and the amount of the polyfunctional monomer (manufactured by Xinzhou chemical Co., ltd., NK ESTER A-200) added was changed to 0.2 g.
Example 5
< method for producing acrylic Polymer B >
670g of 2-ethylhexyl acrylate, 240g of 4-hydroxybutyl acrylate, 90g of cyclohexyl methacrylate and 0.1g of n-dodecylmercaptan were put into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser and a thermometer, and after the nitrogen substitution was performed at a nitrogen flow rate of 300ml/min for 60 minutes, the nitrogen flow rate was reduced to 100ml/min, and the temperature was raised to 65℃by heating with a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In this manner, a slurry B containing the acrylic polymer B having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
The tackifying resin a prepared by the same method as in example 1 was dried at 100 ℃ for 5 hours, and the solvent was removed. To 100g of the slurry B, 5g of a tackifying resin from which the solvent was removed, 3g of isobornyl methacrylate, 0.2g of tricyclodecane dimethanol diacrylate (A-DCP, manufactured by Xinzhou chemical Co., ltd.), 0.2g of a polyfunctional monomer (NK ESTER A-200, manufactured by Xinzhou chemical Co., ltd.), 0.1g of a silane coupling agent (KBM-9659, manufactured by Xinyue chemical Co., ltd.), and 0.3g of a photopolymerization initiator (IGM Resins B.V, esacure One) were added, and the mixture was stirred and deaerated to obtain an adhesive composition. The adhesive composition was applied to a polyester film having a thickness of 100 μm and coated with a silicone release agent so as to have a thickness of 175. Mu.m, and laminated with a polyester film having a thickness of 75 μm and coated with a silicone release agent, and then the film was irradiated with an illuminance of 5mW/cm 2 The cumulative illuminance was 900mJ/cm 2 The chemical lamp was irradiated so that the illuminance became 200mW/cm 2 The cumulative illuminance was 2000mJ/cm 2 A high-pressure mercury lamp was irradiated, thereby obtaining an adhesive sheet.
Example 6
< method for producing acrylic Polymer C >
To a 2L flask equipped with a stirrer, a nitrogen inlet tube, a condenser, and a thermometer, 620g of butyl acrylate, 290g of 4-hydroxybutyl acrylate, 90g of cyclohexyl acrylate, and 0.1g of n-dodecyl mercaptan were charged, and after the nitrogen substitution was performed at a nitrogen flow rate of 300ml/min for 60 minutes, the nitrogen flow rate was reduced to 100ml/min, and the temperature was raised to 65℃by heating in a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask at the above monomer ratio, and the solid content was adjusted so that the solid content became 20%. In this manner, a slurry C containing an acrylic polymer C having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
The tackifying resin a prepared by the same method as in example 1 was dried at 100 ℃ for 5 hours, and the solvent was removed. To 100g of the slurry C, 5g of a tackifying resin from which the solvent was removed, 3g of isobornyl methacrylate, 1g of a cyclized polymerizable multifunctional monomer (manufactured by Japanese catalyst Co., ltd., AOMA), 0.3g of a multifunctional monomer (manufactured by Xinzhou Chemie Industrial Co., ltd., NK ESTER A-200), 0.1g of a silane coupling agent (manufactured by Xinyue chemical Co., ltd., KBM-9659) and 0.3g of a photopolymerization initiator (manufactured by IGM Resins B.V Co., esacure One) were added, and the mixture was stirred and defoamed to obtain an adhesive composition. The adhesive composition was applied to a polyester film having a thickness of 100 μm and coated with a silicone release agent so as to have a thickness of 175. Mu.m, and laminated with a polyester film having a thickness of 75 μm and coated with a silicone release agent, and then the film was irradiated with an illuminance of 5mW/cm 2 The cumulative illuminance was 900mJ/cm 2 The chemical lamp was irradiated so that the illuminance became 200mW/cm 2 The cumulative illuminance was 2000mJ/cm 2 A high-pressure mercury lamp was irradiated, thereby obtaining an adhesive sheet.
Comparative example 1
An adhesive sheet was produced in the same manner as in example 1, except that the addition amount of the cyclized polymerizable polyfunctional monomer (manufactured by the catalyst company of japan, AOMA) was changed to 0.5g in < production of adhesive sheet >.
Comparative example 2
In < production of pressure-sensitive adhesive sheet >, a pressure-sensitive adhesive sheet was produced in the same manner as in example 1, except that 0.15g of 1, 6-hexanediol diacrylate (produced by Xinzhou chemical industry Co., ltd., A-HD-N) was added as a polyfunctional monomer instead of the cyclized polymerizable polyfunctional monomer (produced by Japanese catalyst Co., ltd., AOMA), and the amount of the polyfunctional monomer (produced by Xinzhou chemical industry Co., ltd., NK ESTER A-200) added was changed to 0.2 g.
Comparative example 3
In < production of pressure-sensitive adhesive sheet >, a pressure-sensitive adhesive sheet was produced in the same manner as in example 1, except that 0.2g of 1, 10-decanediol diacrylate (A-DOD-N, manufactured by Xinzhou chemical industry Co., ltd.) was added as a polyfunctional monomer instead of the cyclized polymerizable polyfunctional monomer (AOMA, manufactured by Japan catalyst Co., ltd.) and the amount of the polyfunctional monomer (NK ESTER A-200) added was changed to 0.2 g.
Comparative example 4
An adhesive sheet was produced in the same manner as in example 1, except that the cyclized polymerizable polyfunctional monomer (manufactured by Japanese catalyst Co., ltd., AOMA) and the polyfunctional monomer (manufactured by Xinzhou Kogyo Chemie Co., ltd., NK ESTER A-200) were not added to the < production of an adhesive sheet >.
Comparative example 5
< method for producing acrylic Polymer D >
500g of 2-ethylhexyl acrylate, 290g of 4-hydroxybutyl acrylate, 210g of cyclohexyl methacrylate and 0.1g of n-dodecyl mercaptan were put into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser and a thermometer, and after nitrogen substitution was performed for 60 minutes at a nitrogen flow rate of 300ml/min, the nitrogen flow rate was reduced to 100ml/min, and the flask was heated to 65℃by heating with a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask at the above monomer ratio, and the solid content was adjusted so that the solid content became 20%. In the above manner, a slurry D containing the acrylic polymer D having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
Addition of nail to slurry D100 g3g of isobornyl methacrylate, 0.35g of a polyfunctional monomer (NK ESTER A-200, manufactured by Xinzhongcun chemical industry Co., ltd.) and 0.3g of a photopolymerization initiator (IGM Resins B.V, esacure One) were stirred and defoamed to obtain an adhesive composition. The adhesive composition was applied to a polyester film having a thickness of 100 μm and coated with a silicone release agent so as to have a thickness of 175. Mu.m, and laminated with a polyester film having a thickness of 75 μm and coated with a silicone release agent, and then the film was irradiated with an illuminance of 5mW/cm 2 The cumulative illuminance was 900mJ/cm 2 The chemical lamp was irradiated so that the illuminance became 200mW/cm 2 The cumulative illuminance was 2000mJ/cm 2 A high-pressure mercury lamp was irradiated, thereby obtaining an adhesive sheet.
Comparative example 6
< method for producing acrylic Polymer E >
760g of butyl acrylate, 150g of 4-hydroxybutyl acrylate, 90g of cyclohexyl methacrylate and 0.1g of n-dodecyl mercaptan were put into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser and a thermometer, and after nitrogen substitution was performed at a nitrogen flow rate of 300ml/min for 60 minutes, the nitrogen flow rate was reduced to 100ml/min, and the flask was heated to 65℃by heating with a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In the above manner, a slurry E containing the acrylic polymer E having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
An adhesive sheet was produced in the same manner as in example 1, except that the acrylic polymer E was used in < production of adhesive sheet >.
Comparative example 7
< method for producing acrylic Polymer F >
Into a 2L flask equipped with a stirrer, a nitrogen inlet tube, a condenser, and a thermometer, 710g of 2-ethylhexyl acrylate, 290g of 4-hydroxybutyl acrylate, and 0.1g of n-dodecylmercaptan were charged, and after nitrogen substitution was performed for 60 minutes at a nitrogen flow rate of 300ml/min, the nitrogen flow rate was reduced to 100ml/min, and the temperature was raised to 65℃by heating in a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In the above manner, a slurry F containing the acrylic polymer F having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
An adhesive sheet was produced in the same manner as in example 1, except that the acrylic polymer F was used in < production of adhesive sheet >.
Comparative example 8
< method for producing acrylic Polymer G >
520g of 2-ethylhexyl acrylate, 290g of 4-hydroxybutyl acrylate, 90g of cyclohexyl methacrylate, 100g of N-vinyl-2-pyrrolidone and 0.1g of N-dodecyl mercaptan were put into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser and a thermometer, and after nitrogen substitution for 60 minutes at a nitrogen flow rate of 300ml/min, the nitrogen flow rate was reduced to 100ml/min, and the flask was heated to 65℃by heating in a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In this manner, a slurry G containing the acrylic polymer G having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
An adhesive sheet was produced in the same manner as in example 1, except that the acrylic polymer G was used in < production of adhesive sheet >.
Comparative example 9
< method for producing acrylic Polymer H >
520g of 2-ethylhexyl acrylate, 290g of 4-hydroxybutyl acrylate, 90g of cyclohexyl methacrylate, 100g of dimethylacrylamide and 0.1g of n-dodecyl mercaptan were put into a 2L flask equipped with a stirrer, a nitrogen inlet pipe, a condenser and a thermometer, and after the nitrogen substitution was performed at a nitrogen flow rate of 300ml/min for 60 minutes, the nitrogen flow rate was reduced to 100ml/min, and the flask was heated to 65℃by heating in a water bath. AIBN (0.15 g) was charged, allowed to react for 30 minutes while controlling the heat release, and then cooled to room temperature. The additional monomer was charged into the flask so as to be the above-mentioned monomer ratio, and the solid content concentration was adjusted so as to be 20%. In this manner, a slurry H containing the acrylic polymer H having a solid content concentration of 20% by mass and a weight average molecular weight of about 90 ten thousand was obtained.
< production of adhesive sheet >
An adhesive sheet was produced in the same manner as in example 1, except that the acrylic polymer H was used in < production of adhesive sheet >.
(measurement and evaluation)
((calculation of glass transition temperature of (meth) acrylic Polymer)
The glass transition temperature of the acrylic polymer was determined by the following FOX equation.
1/Tgp＝W1/Tg1+W2/Tg2+···+Wn/Tgn
Tgp is the glass transition temperature of the acrylic polymer, wn is the weight fraction of each monomer, and Tgn is the glass transition temperature when each monomer is made into a homopolymer.
(measurement of glass transition temperature of tackifying resin)
For the measurement of the glass transition temperature of the tackifying resin, DSC6200 manufactured by Seiko Instruments inc. The temperature was raised from 0℃to 150℃at a temperature-raising rate of 10℃per minute under an atmosphere of 50ml/min nitrogen flow, with reference to 10mg of alumina, by putting about 10mg of a solvent-removed product of a tackifying resin into an aluminum pot for a sample having a diameter of 5 mm. At this time, the inflection point where the specific heat is changed is read as the glass transition temperature of the tackifying resin.
(measurement of high temperature constant load)
The obtained adhesive sheet was adhered to an easily adhesive polyester film (A4300 manufactured by Toyobo Co., ltd.) having a thickness of 100 μm, and cut so that the adhered portion had a width of 25mm and a length of 50 mm. Then, each of the two films was attached to a polycarbonate sheet (Panlite 1151, manufactured by Di person Co., ltd.) or a float glass (Ping Gangxiao sub-industry Co., ltd.) having a thickness of 1.1mm, and then pressed and bonded 2 times with a 2kg roller. Thereafter, the laminate was treated with an autoclave at a temperature of 30℃and a pressure of 0.5MPa for 30 minutes, and allowed to stand at atmospheric pressure and room temperature for 1 day to obtain an evaluation laminate.
The laminate for evaluation was allowed to stand in a constant temperature and humidity machine at 95℃for 30 minutes, and then set on a table so that the polycarbonate sheet or float glass side became the upper surface. Then, a weight of 100g was hung on the end of the polyester film, and the peeling distance (peeling distance between the polycarbonate sheet or float glass and the adhesive sheet) after 30 minutes was measured, and the evaluation was performed according to the following criteria.
< high temperature constant load (95 ℃), adherend: polycarbonate sheet
A: the stripping distance after 30 minutes is less than 15mm
B: the peeling distance after 30 minutes is more than 15mm and less than 20mm
C: the peeling distance after 30 minutes is more than 20mm
< high temperature constant load (95 ℃), adherend: glass
A: the stripping distance after 30 minutes is less than 5mm
B: the peeling distance after 30 minutes is more than 5mm and less than 10mm
C: the peeling distance after 30 minutes is more than 10mm
(measurement of constant load of damp and heat)
The laminate for evaluation obtained by the above method was allowed to stand in a constant temperature and humidity machine at 85 ℃ and a relative humidity of 85% for 60 minutes, and then was set on a table so that the polycarbonate sheet or the float glass side was the upper surface. Then, a weight of 100g was hung on the end of the polyester film, and the peeling distance (peeling distance between the polycarbonate sheet or float glass and the adhesive sheet) after 30 minutes was measured, and the evaluation was performed according to the following criteria.
< constant load of damp and heat (85 ℃, 85%), adherend: polycarbonate sheet
A: the stripping distance after 30 minutes is less than 15mm
B: the peeling distance after 30 minutes is more than 15mm and less than 20mm
C: the peeling distance after 30 minutes is more than 20mm
< constant load of damp and heat (85 ℃, 85%), adherend: glass
A: the stripping distance after 30 minutes is less than 10mm
B: the peeling distance after 30 minutes is more than 10mm
C: fall within 30 minutes
(degassing resistance)
A polycarbonate (Panlite 1151, manufactured by Di Co., ltd.) having a width of 55mm and a length of 80mm and a thickness of 1mm was stuck on one side of the obtained pressure-sensitive adhesive sheet, and a glass (manufactured by Matsunami Co., ltd.) having a width of 52mm and a length of 76mm and a thickness of 1mm was stuck on the other side, and then the pressure-sensitive adhesive sheet was treated with an autoclave at a temperature of 30℃under a pressure of 0.5MPa for 30 minutes, and allowed to stand at atmospheric pressure and room temperature for 1 day. The obtained laminate for evaluation was put into a dryer at 95℃and taken out after 6 hours, and whether or not bubbles were generated and peeled was evaluated.
A: bubble-free and peeling
C: with bubbles or peeling
(light resistance (weather resistance))
After a glass (manufactured by Matsunami Co., ltd.) having a width of 52mm, a length of 76mm and a thickness of 1mm was stuck on both sides of the obtained adhesive sheet, the sheet was treated with an autoclave at a temperature of 30℃and a pressure of 0.5MPa for 30 minutes, and allowed to stand at atmospheric pressure and room temperature for 1 day. Next, the obtained laminate for evaluation was set in Super Xenon Weather Meter SX75 manufactured by Suga Test Instruments Co., ltd. At a relative humidity of 50%, a black panel temperature of 63℃and an illuminance of 180W/cm 2 Under the conditions of (2) and (3) irradiating the laminate for evaluation with light (300-400 nm) for 300 hours. The chromaticity (b) of the laminate for evaluation was measured using a colorimeter Coloer cut i manufactured by Suga Test Instruments, and evaluated according to the following criteria.
A: the increase in b-value after light irradiation is less than 1.0 compared with the b-value before evaluation
C: an increase in b-value after light irradiation of 1.0 or more compared with b-value before evaluation
TABLE 1
2EHA: 2-ethylhexyl acrylate
BA: butyl acrylate
4HBA: acrylic acid 4-hydroxybutyl ester
CHMA: cyclohexyl methacrylate
CHA: cyclohexyl acrylate
NVP: n-vinyl-2-pyrrolidone
DMAA: dimethylacrylamide
MMA/IBXMA: methyl methacrylate/isobornyl methacrylate.
IBXA: isobornyl acrylate
IBXMA: isobornyl methacrylate
The examples were superior to the comparative examples in adhesion under a high-temperature environment and/or adhesion under a high-temperature and high-humidity environment. In addition, the pressure-sensitive adhesive sheet obtained in examples was also excellent in outgas resistance and light resistance (weather resistance).
Claims (8)
1. An adhesive composition comprising:
a (meth) acrylic polymer containing a (meth) acrylic monomer unit having a hydroxyl group and a (meth) acrylic monomer unit having a ring structure; and
At least 1 selected from the group consisting of cyclized polymerizable polyfunctional monomers and polyfunctional monomers having a ring structure,
the glass transition temperature of the (meth) acrylic polymer is 0 ℃ or lower,
the content of the hydroxyl group-containing (meth) acrylic monomer unit in the (meth) acrylic polymer is 20 mass% or more relative to the total mass of the (meth) acrylic polymer,
the content of the (meth) acrylic monomer unit having a ring structure in the (meth) acrylic polymer is 1 mass% or more relative to the total mass of the (meth) acrylic polymer,
the content of the monomer unit having a nitrogen atom in the (meth) acrylic polymer is 0.1 mass% or less.
2. The adhesive composition according to claim 1, wherein the (meth) acrylic monomer unit having a ring structure is a (meth) acrylic monomer unit having an alicyclic structure.
3. The adhesive composition of claim 1, further comprising a resin having a glass transition temperature of 20 ℃ or higher.
4. The adhesive composition of claim 1, further comprising a multifunctional monomer that does not have a ring structure and does not undergo cyclization.
5. The adhesive composition of claim 1, further comprising a monofunctional monomer having a ring structure.
6. The adhesive composition of claim 1, further comprising a silane coupling agent.
7. The adhesive composition of claim 1, further comprising a photopolymerization initiator.
8. An adhesive sheet formed from the adhesive composition according to any one of claims 1 to 7.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022-059589 | 2022-03-31 | ||
| JP2022059589 | 2022-03-31 | ||
| PCT/JP2023/008568 WO2023189284A1 (en) | 2022-03-31 | 2023-03-07 | Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117425711A true CN117425711A (en) | 2024-01-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202380012036.9A Pending CN117425711A (en) | 2022-03-31 | 2023-03-07 | Adhesive composition and adhesive sheet |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN117425711A (en) |
| TW (1) | TW202340408A (en) |
| WO (1) | WO2023189284A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014081003A1 (en) * | 2012-11-22 | 2014-05-30 | 王子ホールディングス株式会社 | Adhesive composition, adhesive sheet, and laminate |
| CN107077801B (en) * | 2014-10-23 | 2019-10-15 | 琳得科株式会社 | Sticker, adhesive sheet and display body |
| JP2019044024A (en) * | 2017-08-30 | 2019-03-22 | リンテック株式会社 | Adhesive sheet, display body and method for manufacturing display body |
| JP6881500B2 (en) * | 2019-05-16 | 2021-06-02 | 王子ホールディングス株式会社 | Adhesive sheet and laminate |
| JP6705542B1 (en) * | 2019-10-03 | 2020-06-03 | 王子ホールディングス株式会社 | Adhesive sheet |
| JP2021084931A (en) * | 2019-11-26 | 2021-06-03 | 王子ホールディングス株式会社 | Adhesive sheet |
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2023
- 2023-03-07 CN CN202380012036.9A patent/CN117425711A/en active Pending
- 2023-03-07 WO PCT/JP2023/008568 patent/WO2023189284A1/en active Application Filing
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| TW202340408A (en) | 2023-10-16 |
| WO2023189284A1 (en) | 2023-10-05 |
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