CN116075568B - Color-changeable adhesive sheet - Google Patents
Color-changeable adhesive sheet Download PDFInfo
- Publication number
- CN116075568B CN116075568B CN202180061843.0A CN202180061843A CN116075568B CN 116075568 B CN116075568 B CN 116075568B CN 202180061843 A CN202180061843 A CN 202180061843A CN 116075568 B CN116075568 B CN 116075568B
- Authority
- CN
- China
- Prior art keywords
- color
- meth
- mass
- adhesive layer
- adhesive sheet
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000853 adhesive Substances 0.000 title claims abstract description 101
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 101
- 239000012790 adhesive layer Substances 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000003593 chromogenic compound Substances 0.000 claims abstract description 8
- 238000012360 testing method Methods 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 17
- 239000011521 glass Substances 0.000 claims description 13
- 238000013329 compounding Methods 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000000178 monomer Substances 0.000 description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 62
- 230000008859 change Effects 0.000 description 57
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 45
- 239000010410 layer Substances 0.000 description 41
- -1 2-ethylhexyl Chemical group 0.000 description 36
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 29
- 229920000058 polyacrylate Polymers 0.000 description 24
- 239000003431 cross linking reagent Substances 0.000 description 23
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 20
- 229920005601 base polymer Polymers 0.000 description 19
- 238000004132 cross linking Methods 0.000 description 19
- 238000002834 transmittance Methods 0.000 description 17
- 239000004020 conductor Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000006103 coloring component Substances 0.000 description 14
- 238000009792 diffusion process Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 239000003505 polymerization initiator Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000002985 plastic film Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- FKAWETHEYBZGSR-UHFFFAOYSA-N 3-methylidenepyrrolidine-2,5-dione Chemical compound C=C1CC(=O)NC1=O FKAWETHEYBZGSR-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229920002457 flexible plastic Polymers 0.000 description 2
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011295 pitch Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- VIVYBCKORJTEEV-UHFFFAOYSA-L zinc;2-carboxyphenolate;trihydrate Chemical compound O.O.O.[Zn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O VIVYBCKORJTEEV-UHFFFAOYSA-L 0.000 description 2
- AURYLBASVGNSON-UHFFFAOYSA-N (2,5-dioxopyrrolidin-3-ylidene)methyl prop-2-enoate Chemical compound C=CC(=O)OC=C1CC(=O)NC1=O AURYLBASVGNSON-UHFFFAOYSA-N 0.000 description 1
- RQHGZNBWBKINOY-PLNGDYQASA-N (z)-4-tert-butylperoxy-4-oxobut-2-enoic acid Chemical compound CC(C)(C)OOC(=O)\C=C/C(O)=O RQHGZNBWBKINOY-PLNGDYQASA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- HASUCEDGKYJBDC-UHFFFAOYSA-N 1-[3-[[bis(oxiran-2-ylmethyl)amino]methyl]cyclohexyl]-n,n-bis(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC1CC(CN(CC2OC2)CC2OC2)CCC1)CC1CO1 HASUCEDGKYJBDC-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- DCRYNQTXGUTACA-UHFFFAOYSA-N 1-ethenylpiperazine Chemical compound C=CN1CCNCC1 DCRYNQTXGUTACA-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- NWHSSMRWECHZEP-UHFFFAOYSA-N 1-ethenylpyrazole Chemical compound C=CN1C=CC=N1 NWHSSMRWECHZEP-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 description 1
- DGPVNNMFVYYVDF-UHFFFAOYSA-N 1-prop-2-enoylpyrrolidin-2-one Chemical compound C=CC(=O)N1CCCC1=O DGPVNNMFVYYVDF-UHFFFAOYSA-N 0.000 description 1
- NQDOCLXQTQYUDH-UHFFFAOYSA-N 1-propan-2-ylpyrrole-2,5-dione Chemical compound CC(C)N1C(=O)C=CC1=O NQDOCLXQTQYUDH-UHFFFAOYSA-N 0.000 description 1
- WLPAQAXAZQUXBG-UHFFFAOYSA-N 1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCC1 WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 description 1
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 description 1
- HUOKHAMXPNSWBJ-UHFFFAOYSA-N 2'-chloro-6'-(diethylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(C)C=C1OC1=CC(N(CC)CC)=CC=C21 HUOKHAMXPNSWBJ-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- NFHVQKQXNHFCKH-UHFFFAOYSA-N 2-ethenyl-3h-1,2-oxazole Chemical compound C=CN1CC=CO1 NFHVQKQXNHFCKH-UHFFFAOYSA-N 0.000 description 1
- QERTUMILBWNEJM-UHFFFAOYSA-N 2-ethenyl-3h-1,2-thiazole Chemical compound C=CN1CC=CS1 QERTUMILBWNEJM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-UHFFFAOYSA-N 0.000 description 1
- JCGIDGTXJZXFNJ-UHFFFAOYSA-N 2-methylpropanimidamide;sulfo hydrogen sulfate Chemical compound CC(C)C(N)=N.OS(=O)(=O)OS(O)(=O)=O JCGIDGTXJZXFNJ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- AAYRWMCIKCRHIN-UHFFFAOYSA-N propane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CCCS(O)(=O)=O AAYRWMCIKCRHIN-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The adhesive sheet S includes an adhesive layer 10 that changes color due to an external stimulus. The adhesive layer 10 comprises an adhesive composition. The adhesive composition comprises: a chromogenic compound that develops color by reaction with an acid, an acid generator, and a metal complex.
Description
Technical Field
The present invention relates to a color-changeable adhesive sheet.
Background
Display panels such as organic EL panels have a laminated structure including a pixel panel and a protective member. In the manufacturing process of such a display panel, for example, a transparent adhesive sheet is used for bonding elements included in the laminated structure to each other.
As a transparent adhesive sheet to be disposed on the light emission side (image display side) of a pixel panel in a display panel, an adhesive sheet in which a colored portion for imparting design, shielding, antireflection, and the like to a predetermined portion of the same sheet is formed in advance has been proposed. Such an adhesive sheet is described in patent document 1, for example. Specifically, patent document 1 describes an adhesive sheet having a colored portion containing a carbon black pigment.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2017-203810
Disclosure of Invention
Problems to be solved by the invention
However, in the case of using an adhesive sheet having a colored portion formed in advance in the manufacturing process of a display panel, it is not possible to appropriately check the presence or absence of foreign matter and air bubbles between an adherend and the colored portion of the adhesive sheet after the adhesive sheet is bonded to the adherend. In the bonding of an adhesive sheet in the process of manufacturing a display panel, it is required that the presence or absence of foreign matter and air bubbles between an adherend and the adhesive sheet after bonding can be appropriately checked.
On the other hand, from the viewpoint of ensuring the function of the colored portion of the pressure-sensitive adhesive sheet for display panels, it is required to suppress the diffusion of the coloring component in the colored portion with time.
The present invention provides: the color-changeable adhesive sheet is capable of locally changing the color of the adhesive layer after being adhered to an adherend, and is suitable for inhibiting the diffusion of coloring components in the color-changing portion.
Solution for solving the problem
The present invention [1] is a color-changeable adhesive sheet comprising an adhesive layer that changes color due to an external stimulus, wherein the adhesive layer comprises an adhesive composition comprising: a chromogenic compound that develops color by reaction with an acid, an acid generator, and a metal complex.
The invention [2] comprises the color-changeable adhesive sheet according to [1], wherein the compounding ratio of the metal complex is 10 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the color-developing compound.
The invention [3] comprises the color-changeable adhesive sheet according to the above [1] or [2], wherein the color-developed compound is capable of coordinating with the metal complex.
The invention [4] comprises the variable color adhesive sheet according to any one of [1] to [3], wherein the color-developing compound is a leuco dye and the metal complex is a zinc complex.
The invention [5] comprises the variable color adhesive sheet according to any one of [1] to [4], wherein the adhesive layer has a thickness of 10 μm or more and 300 μm or less.
The invention [6] comprises the variable color adhesive sheet according to any one of [1] to [5], further comprising a base material disposed on one side in the thickness direction of the adhesive layer.
The invention [7] comprises the variable color adhesive sheet according to any one of [1] to [6], wherein the adhesive layer is adhered to a glass plate, and the adhesive force to the glass plate is 1.0N/25mm or more and 50N/25mm or less in a peeling test under peeling conditions of 23 ℃ at a peeling angle of 180 DEG and a peeling speed of 300 mm/min.
ADVANTAGEOUS EFFECTS OF INVENTION
The color-changeable adhesive sheet of the present invention is provided with an adhesive layer that changes color due to an external stimulus. Therefore, after the color-changeable adhesive sheet is attached to the adherend, an external stimulus is applied to the portion of the adhesive layer to be color-changed, and the adhesive layer can be locally color-changed. In such a color-changeable pressure-sensitive adhesive sheet, after lamination and before formation of the color-changeable portion of the pressure-sensitive adhesive layer, the presence or absence of foreign matter and bubbles between the color-changeable pressure-sensitive adhesive sheet and the adherend can be checked.
In addition, the adhesive layer contains an adhesive composition containing a metal complex. Therefore, the diffusion of the coloring component in the color change portion can be suppressed.
Drawings
Fig. 1 is a schematic cross-sectional view of an embodiment of the color-changeable adhesive sheet of the present invention.
Fig. 2 is a schematic cross-sectional view of a modification of the color-changeable adhesive sheet of the present invention (when the adhesive sheet is a single-sided adhesive sheet with a base material).
Fig. 3 shows an example of a method of using the color-changeable adhesive sheet of the present invention. Fig. 3A shows a process of preparing a variable color adhesive sheet and an adherend. Fig. 3B shows a process of joining members to each other by means of a variable color adhesive sheet. Fig. 3C shows a process of forming a color change portion in the adhesive layer of the color-changeable adhesive sheet.
Fig. 4 is an explanatory view showing an example of a method of using the color-changeable adhesive sheet of the present invention, and fig. 4A is an explanatory view when color-changeable portions are provided in a pattern shape corresponding to the (i.e., opposite) pattern shape of the conductor layer. Fig. 4B is an explanatory diagram showing that the color change portion oozes out due to diffusion of the coloring component in the color change portion, so that the visibility of the display panel is reduced. Fig. 4C is an explanatory diagram showing that the color change portion becomes small due to diffusion of the coloring component in the color change portion, and external light reflection in the conductor layer cannot be suppressed.
Detailed Description
1. Color-changeable adhesive sheet
As shown in fig. 1, the adhesive sheet S includes an adhesive layer 10. The pressure-sensitive adhesive sheet S has a sheet shape of a predetermined thickness, and extends in a direction (plane direction) orthogonal to the thickness direction. The pressure-sensitive adhesive sheet S is used, for example, as a transparent pressure-sensitive adhesive sheet disposed on the image display side of a pixel panel (for example, a laminated structure including the pixel panel and a protective member) in a display panel.
The adhesive layer 10 is a pressure-sensitive adhesive layer having transparency (visible light transmittance) formed of an adhesive composition.
The adhesive composition comprises: a base polymer, a chromogenic compound that develops color by reaction with an acid, an acid generator, and a metal complex.
The base polymer is an adhesive component for exhibiting adhesiveness in the adhesive layer 10. The base polymer exhibits rubber elasticity in the room temperature range. Examples of the base polymer include acrylic polymers, rubber polymers, polyester polymers, urethane polymers, polyether polymers, silicone polymers, polyamide polymers, and fluoropolymers. From the viewpoint of ensuring good transparency and adhesion in the adhesive layer 10, an acrylic polymer is preferably used as the base polymer.
The content ratio of the base polymer in the pressure-sensitive adhesive layer 10 is, for example, 50 mass% or more, preferably 60 mass% or more, and more preferably 70 mass% or more, from the viewpoint of appropriately exhibiting the function of the base polymer in the pressure-sensitive adhesive layer 10.
The acrylic polymer is, for example, a polymer obtained by polymerizing a monomer component containing an alkyl (meth) acrylate in a proportion of 50 mass% or more. "(meth) acrylic" refers to acrylic and/or methacrylic.
Examples of the alkyl (meth) acrylate include alkyl (meth) acrylates having a linear or branched alkyl group having 1 to 20 carbon atoms. Examples of such alkyl (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isopropyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, neopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, isotridecyl (meth) acrylate, tetradecyl (meth) acrylate, isotetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate and eicosanyl (meth) acrylate. The alkyl (meth) acrylate may be used alone or in combination of two or more. As the alkyl (meth) acrylate, an alkyl acrylate having an alkyl group of 1 to 12 carbon atoms is preferably used, more preferably an alkyl acrylate having an alkyl group of 2 to 12 carbon atoms in combination with methyl acrylate, still more preferably a methyl acrylate and 2-ethylhexyl acrylate in combination.
The proportion of the alkyl (meth) acrylate in the monomer component is, for example, 50 mass% or more, preferably 60 mass% or more, and more preferably 70 mass% or more, from the viewpoint of appropriately exhibiting basic characteristics such as adhesiveness in the adhesive layer 10. The same ratio is, for example, 99 mass% or less.
The monomer component may comprise a copolymerizable monomer copolymerizable with the alkyl (meth) acrylate. Examples of the copolymerizable monomer include monomers having a polar group (polar group-containing monomers). The polar group-containing monomer is advantageous for introducing the crosslinking point into the acrylic polymer and for ensuring the modification of the acrylic polymer such as the aggregation force of the acrylic polymer.
Examples of the polar group-containing monomer include a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and a carboxyl group-containing monomer. The copolymerizable monomer preferably contains at least one selected from the group consisting of a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and a carboxyl group-containing monomer. More preferably, the copolymerizable monomer contains a hydroxyl group-containing monomer and/or a monomer having a nitrogen atom-containing ring.
Examples of the hydroxyl group-containing monomer include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate and (4-hydroxymethylcyclohexyl) methyl (meth) acrylate. As the hydroxyl group-containing monomer, 2-hydroxyethyl (meth) acrylate is preferably used, and 2-hydroxyethyl acrylate is more preferably used.
The proportion of the hydroxyl group-containing monomer in the monomer component is, for example, 1% by mass or more, preferably 3% by mass or more, and more preferably 5% by mass or more from the viewpoint of introducing the crosslinked structure into the acrylic polymer and securing the aggregation force in the adhesive layer 10. The same ratio is, for example, 30 mass% or less, preferably 20 mass% or less, from the viewpoints of adjustment of the viscosity of a polymerization reaction solution at the time of polymerization of an acrylic polymer and adjustment of the polarity of the acrylic polymer (concerning compatibility of various additive components in the adhesive layer 10 with the acrylic polymer).
Examples of the monomer having a nitrogen atom-containing ring include N-vinyl-2-pyrrolidone, N-methyl vinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyridine, N-vinylpiperazine, N-vinylpyrzine, N-vinylpyrrolidone, N-vinylimidazole, N-vinyloxazole, N- (meth) acryl-2-pyrrolidone, N- (meth) acryl piperidine, N- (meth) acryl pyrrolidine, N-vinylmorpholine, N-vinyl-3-morpholone, N-vinyl-2-caprolactam, N-vinyl-1, 3-oxazin-2-one, N-vinyl-3, 5-morpholinedione, N-vinylpyrazole, N-vinylisoxazole, N-vinylthiazole and N-vinylisothiazole. As the monomer having a nitrogen atom-containing ring, N-vinyl-2-pyrrolidone is preferably used.
The proportion of the monomer having a nitrogen atom-containing ring in the monomer component is, for example, 1% by mass or more, preferably 3% by mass or more, and more preferably 5% by mass or more, from the viewpoints of securing the aggregation force in the pressure-sensitive adhesive layer 10 and securing the adhesion force to the adherend in the pressure-sensitive adhesive layer 10. The same ratio is, for example, 30 mass% or less, preferably 20 mass% or less, from the viewpoints of adjustment of the glass transition temperature of the acrylic polymer and adjustment of the polarity of the acrylic polymer (concerning compatibility of various additive components in the adhesive layer 10 with the acrylic polymer).
Examples of the carboxyl group-containing monomer include acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
The ratio of the carboxyl group-containing monomer in the monomer component is, for example, 1% by mass or more, preferably 3% by mass or more, and more preferably 5% by mass or more, from the viewpoints of introduction of the crosslinked structure into the acrylic polymer, securing of the aggregation force in the adhesive layer 10, and securing of the adhesion force to the adherend in the adhesive layer 10. The same ratio is, for example, 30 mass% or less, preferably 20 mass% or less, from the viewpoints of adjustment of the glass transition temperature of the acrylic polymer and avoidance of corrosion risk of the adherend by acid.
The monomer component may comprise other copolymerizable monomers. Examples of the other copolymerizable monomer include acid anhydride monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, epoxy group-containing monomers, cyano group-containing monomers, amide group-containing monomers, monomers having a succinimide skeleton, maleimides, itaconimides, alkoxy group-containing monomers, vinyl esters, vinyl ethers, and aromatic vinyl compounds.
Examples of the acid anhydride monomer include maleic anhydride and itaconic anhydride.
Examples of the sulfonic acid group-containing monomer include styrene sulfonic acid, allyl sulfonic acid, sodium vinylsulfonate, 2- (meth) acrylamide-2-methylpropanesulfonic acid, (meth) acrylamide propane sulfonic acid, sulfopropyl (meth) acrylate, and (meth) acryloxynaphthalene sulfonic acid.
Examples of the phosphate group-containing monomer include 2-hydroxyethyl acryloyl phosphate.
Examples of the epoxy group-containing monomer include epoxy group-containing acrylates such as glycidyl (meth) acrylate and 2-ethyl glycidyl (meth) acrylate, allyl glycidyl ether, and glycidyl (meth) acrylate.
Examples of the cyano group-containing monomer include acrylonitrile and methacrylonitrile.
Examples of the amide group-containing monomer include N-vinylcarboxylic acid amide, N-hydroxyalkyl (meth) acrylamide, N-alkoxyalkyl (meth) acrylamide, N-dimethylaminopropyl (meth) acrylamide, and N- (meth) acryloylmorpholine.
Examples of the N-vinylcarboxylic acid amides include (meth) acrylamide, N-dialkyl (meth) acrylamide, N-alkyl (meth) acrylamide, and N-vinylacetamide.
Examples of the N, N-dialkyl (meth) acrylamides include N, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-dipropyl (meth) acrylamide, N-diisopropyl (meth) acrylamide, N-di (N-butyl) (meth) acrylamide and N, N-di (t-butyl) (meth) acrylamide.
Examples of the N-alkyl (meth) acrylamide include N-ethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butyl (meth) acrylamide, and N-N-butyl (meth) acrylamide.
Examples of the N-hydroxyalkyl (meth) acrylamide include N- (2-hydroxyethyl) (meth) acrylamide, N- (2-hydroxypropyl) (meth) acrylamide, N- (1-hydroxypropyl) (meth) acrylamide, N- (3-hydroxypropyl) (meth) acrylamide, N- (2-hydroxybutyl) (meth) acrylamide, N- (3-hydroxybutyl) (meth) acrylamide, and N- (4-hydroxybutyl) (meth) acrylamide. Examples of the N-alkoxyalkyl (meth) acrylamide include N-methoxymethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, and N-butoxymethyl (meth) acrylamide.
Examples of the monomer having a succinimide skeleton include N- (meth) acryloyloxymethylene succinimide, N- (meth) acryl-6-oxyhexamethylene succinimide, and N- (meth) acryl-8-oxyhexamethylene succinimide.
Examples of the maleimides include N-cyclohexylmaleimide, N-isopropylmaleimide, N-laurylmaleimide and N-phenylmaleimide.
Examples of the itaconimides include N-methyl itaconimide, N-ethyl itaconimide, N-butyl itaconimide, N-octyl itaconimide, N-2-ethylhexyl itaconimide, N-cyclohexyl itaconimide and N-month Gui Jiyi itaconimide.
Examples of the alkoxy group-containing monomer include alkoxyalkyl (meth) acrylates and alkoxyalkyleneglycol (meth) acrylates. Examples of the alkoxyalkyl (meth) acrylate include 2-methoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, propoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, and ethoxypropyl (meth) acrylate. Examples of the alkoxyalkylene glycol (meth) acrylate include methoxyethylene glycol (meth) acrylate and methoxypolypropylene glycol (meth) acrylate.
Examples of vinyl esters include vinyl acetate and vinyl propionate.
Examples of vinyl ethers include methyl vinyl ether and ethyl vinyl ether.
Examples of the aromatic vinyl compound include styrene, α -methylstyrene and vinyltoluene. Examples of the olefins include ethylene, butadiene, isoprene and isobutylene.
The copolymerizable monomer may be used alone or in combination of two or more.
The acrylic polymer can be formed by polymerizing the above monomer components. Examples of the polymerization method include solution polymerization, bulk polymerization and emulsion polymerization, and preferably include solution polymerization. In solution polymerization, for example, a reaction solution is prepared by compounding a monomer component and a polymerization initiator in a solvent, and then the reaction solution is heated. Then, the polymerization reaction of the monomer components in the reaction solution is performed, whereby an acrylic polymer solution containing an acrylic polymer can be obtained.
As the polymerization initiator, for example, a thermal polymerization initiator is used. The amount of the polymerization initiator to be used is, for example, 0.05 parts by mass or more based on 100 parts by mass of the monomer component. The same amount is, for example, 1 part by mass or less.
Examples of the thermal polymerization initiator include azo-based polymerization initiators and peroxide-based polymerization initiators. Examples of the azo-based polymerization initiator include 2,2' -azobisisobutyronitrile, 2' -azobis-2-methylbutyronitrile, dimethyl 2,2' -azobis (2-methylpropionate), 4' -azobis-4-cyanovaleric acid, azobisisovaleronitrile, 2' -azobis (2-amidinopropane) dihydrochloride, 2' -azobis [2- (5-methyl-2-imidazolin-2-yl) propane ] dihydrochloride, 2' -azobis (2-methylpropionamidine) disulfate and 2,2' -azobis (N, N ' -dimethyleneisobutyl amidine) dihydrochloride. Examples of the peroxide-based polymerization initiator include dibenzoyl peroxide, t-butyl peroxymaleate, and lauroyl peroxide.
The weight average molecular weight of the acrylic polymer is 100000 or more, preferably 300000 or more, more preferably 500000 or more from the viewpoint of securing the aggregation force in the adhesive layer 10. The same weight average molecular weight is, for example, 5000000 or less, preferably 3000000 or less, more preferably 2000000 or less. The weight average molecular weight of the acrylic polymer was measured by Gel Permeation Chromatography (GPC), and calculated from polystyrene conversion.
The glass transition temperature (Tg) of the base polymer is, for example, 0℃or lower, preferably-10℃or lower, more preferably-20℃or lower. The same glass transition temperature is, for example, -80 ℃ or higher.
For the glass transition temperature (Tg) of the polymer, a glass transition temperature (theoretical value) obtained based on the following Fox formula can be used. The Fox formula is a relation between the glass transition temperature Tg of the polymer and the glass transition temperature Tgi of the homopolymer of the monomers constituting the polymer. In the following Fox formula, tg represents the glass transition temperature (. Degree. C.) of the polymer, wi represents the weight fraction of the monomer i constituting the polymer, tgi represents the glass transition temperature (. Degree. C.) of the homopolymer formed from the monomer i. As the glass transition temperature of the homopolymer, literature values such as "Polymer Handbook" (4 th edition, john Wiley & Sons, inc., 1999) and "synthetic resin for New Polymer library 7 paint" are used (Santa Clara, north Korea, polymer journal, 1995) to list the glass transition temperatures of various homopolymers. On the other hand, the glass transition temperature of the homopolymer of the monomer can be obtained by a method specifically described in JP-A2007-51271.
Fox 1/(273+tg) =Σ [ Wi/(273+tgi) ]
Examples of the color-developing compound (color-developing compound) that develops color by reaction with an acid include leuco dyes, triarylmethane-based pigments, diphenylmethane-based pigments, fluoran-based pigments, spiropyran-based pigments, and rhodamine-based pigments. The color former may be used alone or in combination of two or more.
Examples of leuco dyes include 2 '-anilino-6' - (N-ethyl-N-isopentylamino) -3 '-methyl spiro [ tetrachlorophthalide-3, 9' - [9H ] xanthene ], 3-dibutylamino-6-methyl-7-anilinofluoran, 3-dipropylamino-6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7-anilinofluoran, 3-dimethylamino-6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7-dimethylaminofluoran and 3- (4-diethylamino-2-ethoxyphenyl) -3- (1-ethyl-2-methylindol-3-yl) -4-azaphthalide.
Examples of the triarylmethane-based dye include p, p', p "-tris (dimethylamino) triphenylmethane. Examples of the diphenylmethane-series dye include 4, 4-bis-dimethylaminophenyl benzhydryl benzyl ether. Examples of the fluoran-based coloring matter include 3-diethylamino-6-methyl-7-chlorofluoran. Examples of the spiropyran-based pigment include 3-methyl spiropyran. Examples of rhodamine pigments include rhodamine-B-anilinopactam.
In the pressure-sensitive adhesive layer 10, a leuco dye is preferably used as the color-developing compound, and more preferably 2 '-anilino-6' - (N-ethyl-N-isopentylamino) -3 '-methyl spiro [ tetrachlorophthalein-3, 9' - [9H ] xanthene ] is used.
In addition, it is preferable that the chromogenic compound after chromogenic is capable of coordinating with the metal complex. The color-developing compound after color development may be coordinated to the metal complex, and the diffusion of the coloring component (color-developing compound) in the color-changing portion 11 may be suppressed.
The amount of the color former compound to be blended is, for example, 0.5 parts by mass or more, preferably 1 part by mass or more relative to 100 parts by mass of the base polymer. The same amount is, for example, 10 parts by mass or less, preferably 7 parts by mass or less, and more preferably 5 parts by mass or less.
As the acid generator, a photoacid generator that generates an acid by irradiation with active energy rays is preferably used. In this case, the portion of the adhesive layer 10 that is irradiated with active energy rays as external stimulus can be discolored. Specifically, in the portion of the pressure-sensitive adhesive layer 10 irradiated with the active energy ray, an acid is generated by the photoacid generator, and the color-developing compound develops color by the acid. The portion of the pressure-sensitive adhesive layer 10 irradiated with the active energy ray is colored black, for example, according to the color development of the color-developing compound. The kind of the active energy ray as the external stimulus is determined according to the kind of the photoacid generator (specifically, the wavelength of the active energy ray of the photoacid generator generating the acid). Examples of the active energy ray include ultraviolet rays, visible rays, infrared rays, X rays, α rays, β rays, and γ rays. From the viewpoints of versatility of the apparatus to be used and ease of handling, ultraviolet rays are preferable as active energy rays.
Examples of the photoacid generator include onium compounds that generate acid by ultraviolet irradiation. The onium compound is provided, for example, in the form of an onium salt of an onium cation and an anion. Examples of onium cations include iodonium and sulfonium. Examples of the anions include Cl - 、Br - 、I - 、ZnCl 3 - 、HSO 3 - 、BF 4 - 、PF 6 - 、AsF 6 - 、SbF 6 - 、CH 3 SO 3 - 、CF 3 SO 3 - 、C 4 F 9 HSO 3 - 、(C 6 F 5 ) 4 B - And (C) 4 H 9 ) 4 B - . The photoacid generator may be used alone or in combination of two or more. As photoacid generator, sulfonium and C are preferably mentioned 4 F 9 HSO 3 - The onium salt (onium compound) formed.
The compounding amount of the acid generator is, for example, 1 part by mass or more, preferably 2 parts by mass or more, more preferably 5 parts by mass or more, and still more preferably 6 parts by mass or more relative to 100 parts by mass of the base polymer. The same amount is, for example, 20 parts by mass or less, preferably 15 parts by mass or less, more preferably 10 parts by mass or less.
The amount of the acid generator to be blended is, for example, 100 parts by mass or more, preferably 200 parts by mass or more, more preferably 300 parts by mass or more, and still more preferably 330 parts by mass or more, based on 100 parts by mass of the color former. The same amount is, for example, 1000 parts by mass or less, preferably 700 parts by mass or less, and more preferably 500 parts by mass or less.
The metal complex is compounded to inhibit diffusion of the coloring component (color former) in the color-changing portion 11.
Specifically, the metal complex is coordinated to the chromogenic compound after the coloration. Thereby the volume of the color former becomes large. This can suppress the color component (color former) in the color-changing portion 11 from diffusing with time.
The metal complex is obtained by coordinating a ligand to a metal ion.
Examples of the metal constituting the metal ion include alkali metals of group 1, alkaline earth metals of group 2, and transition metals of groups 3 to 12 according to the periodic table (IUPAC Periodic Table of the Elements (version date 19 febrary 2010). The same applies hereinafter). The metal is preferably an alkaline earth metal of group 2 or a transition metal of groups 3 to 12, and Mg (magnesium) is exemplified from the viewpoint of strong coordination of the leuco dye to the carboxyl group of the color former, and Zn (zinc) is exemplified from the viewpoint of contribution of amphoteric counter ion formed with the leuco dye based on a metal complex. That is, as the metal complex, a zinc-based complex in which the metal constituting the metal ion is zinc is preferable.
Examples of the ligand include a monodentate ligand and a bidentate ligand. Examples of the monodentate ligand include hydroxyl (OH) - ) Halogen (e.g. chlorine (Cl) - ) Cyano (CN) - ). Examples of bidentate ligands include ethylenediamine, bipyridine, phenanthroline, and salicylic acid.
Among such metal complexes, bidentate ligands are preferable, and water Yang Suanxin (specifically, zinc salicylate trihydrate) is more preferable from the viewpoint of contribution of amphoteric counter ions.
The metal complex may be used alone or in combination of two or more.
The amount of the metal complex to be compounded is, for example, 0.1 part by mass or more, preferably 0.2 part by mass or more, more preferably 0.5 part by mass or more, and still more preferably 0.8 part by mass or more relative to 100 parts by mass of the base polymer. The same amount is, for example, 5 parts by mass or less, preferably 2 parts by mass or less.
The amount of the metal complex to be blended is, for example, 10 parts by mass or more, preferably 20 parts by mass or more, and more preferably 40 parts by mass or more, with respect to 100 parts by mass of the color former, from the viewpoint of suppressing the color former (color former) in the color-changing portion 11 from diffusing with time. The same amount of the coloring component (color-forming compound) to be blended is, for example, 100 parts by mass or less, preferably 80 parts by mass or less, from the viewpoint of suppressing the diffusion of the coloring component (color-forming compound) in the color-changing portion 11 with time.
The adhesive composition may contain a crosslinking agent from the viewpoint of introducing a crosslinked structure into the base polymer. Examples of the crosslinking agent include isocyanate crosslinking agents, epoxy crosslinking agents, oxazoline crosslinking agents, aziridine crosslinking agents, carbodiimide crosslinking agents, and metal chelate crosslinking agents. The crosslinking agent may be used alone, or two or more thereof may be used in combination.
Examples of the isocyanate crosslinking agent include toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylene diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, and polymethylene polyphenyl isocyanate. Further, as the isocyanate crosslinking agent, derivatives of these isocyanates can be mentioned. Examples of the isocyanate derivative include isocyanurate modified products and polyol modified products. Examples of the commercial products of the isocyanate crosslinking agent include CORONATE L (trimethylolpropane adduct of toluene diisocyanate, manufactured by eastern corporation), CORONATE HL (trimethylolpropane adduct of hexamethylene diisocyanate, manufactured by eastern corporation), CORONATE HX (isocyanurate body of hexamethylene diisocyanate, manufactured by eastern corporation), and TAKENATE D N (trimethylolpropane adduct of xylene diisocyanate, manufactured by three-well chemistry).
Examples of the epoxy crosslinking agent include bisphenol a, epichlorohydrin type epoxy resins, ethylene glycidyl ether, polyethylene glycol diglycidyl ether, glycerol triglycidyl ether, 1, 6-hexanediol glycidyl ether, trimethylolpropane triglycidyl ether, diglycidyl aniline, diamine glycidyl amine, N' -tetraglycidyl-m-xylylenediamine, and 1, 3-bis (N, N-diglycidyl aminomethyl) cyclohexane.
The crosslinking agent is preferably an isocyanate crosslinking agent, and more preferably a trimethylolpropane adduct of xylene diisocyanate.
The amount of the crosslinking agent to be blended is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, and more preferably 0.07 parts by mass or more, relative to 100 parts by mass of the base polymer, from the viewpoint of securing the aggregation power of the adhesive layer 10. From the viewpoint of ensuring good tackiness in the pressure-sensitive adhesive layer 10, the amount of the crosslinking agent blended per 100 parts by mass of the base polymer is, for example, 10 parts by mass or less, preferably 5 parts by mass or less, and more preferably 3 parts by mass or less.
When a crosslinking structure is introduced into the base polymer, a crosslinking catalyst may be used in order to allow the crosslinking reaction to proceed efficiently. Examples of the crosslinking catalyst include metal-based crosslinking catalysts.
Examples of the metal-based crosslinking catalyst include dibutyltin dilaurate, tetra-n-butyl titanate, tetraisopropyl titanate, iron acetylacetonate, and butyltin oxide. The crosslinking catalyst is preferably dibutyltin dilaurate. The amount of the crosslinking catalyst used is, for example, 0.0001 parts by mass or more based on 100 parts by mass of the base polymer. The same amount is, for example, 1 part by mass or less.
In the case where an isocyanate crosslinking agent (specifically, trimethylolpropane adduct of xylene diisocyanate) is compounded as the crosslinking agent and a metal-based crosslinking catalyst (specifically, dibutyltin dilaurate) is compounded as the crosslinking catalyst, acetylacetone is preferably compounded in the adhesive composition.
If acetylacetone is compounded, then acetylacetone coordinates to dibutyltin dilaurate. Thus, the progress of the crosslinking reaction can be suppressed before the adhesive composition is applied to the release film (or the substrate 20) to form a coating film. Further, as will be described in detail later, the heat drying is performed at the time of forming the coating film, so that acetylacetone can be removed and the crosslinking reaction can be performed.
The amount of acetylacetone used is, for example, 100 parts by mass or more, preferably 10000 parts by mass or more, relative to 100 parts by mass of the crosslinking catalyst. The same amount is, for example, 50000 parts by mass or less.
The adhesive composition may contain other components as needed. Examples of the other component include a polymerizable compound and a cured product thereof, a photopolymerization initiator, a silane coupling agent, a thickener, a plasticizer, a softener, an antioxidant, a surfactant, and an antistatic agent.
Examples of the polymerizable compound include a monomer (monofunctional monomer) having one polymerizable functional group (ethylenically unsaturated double bond) and a monomer (polyfunctional monomer) having a plurality of polymerizable functional groups. Examples of the monofunctional monomer include monofunctional (meth) acrylates. Examples of the polyfunctional monomer include polyfunctional (meth) acrylates.
In the case where the adhesive composition contains a polymerizable compound, it is preferable that the adhesive composition further contains a photopolymerization initiator.
The adhesive composition is obtained by blending the base polymer, the color-developing compound that develops color by reaction with an acid, the acid generator, the metal complex, the crosslinking agent blended as needed, the crosslinking catalyst blended as needed, the acetylacetone blended as needed, and the other components blended as needed in the above-mentioned proportions.
The adhesive sheet S can be produced, for example, as follows: the adhesive composition is applied to a release film (release film 1) to form a coating film, and then the coating film is dried to produce the adhesive composition (in fig. 1, an adhesive sheet S is disposed on a release film L shown by a virtual line).
Examples of the release film include a flexible plastic film. Examples of the plastic film include polyethylene terephthalate film, polyethylene film, polypropylene film and polyester film. The thickness of the release film is, for example, 3 μm or more. The same thickness is, for example, 200 μm or less. The surface of the release film is preferably subjected to a mold release treatment.
Examples of the method for applying the adhesive composition include roll coating, kiss roll coating, gravure coating, reverse roll coating, roll brush, spray coating, dip roll coating, bar coating, blade coating, air knife coating, curtain coating, lip coating, and die coating. The drying temperature of the coating film is, for example, 50℃or higher. The same drying temperature is, for example, 200℃or lower. The drying time is, for example, 5 seconds or longer. The same drying time is, for example, 20 minutes or less.
When the adhesive composition contains a crosslinking agent, the crosslinking reaction proceeds simultaneously with the drying or by the subsequent aging. Curing conditions are appropriately set according to the type of the crosslinking agent. The curing temperature is, for example, 20℃or higher. The same curing temperature is, for example, 160℃or lower. The curing time is, for example, 1 minute or more. The same aging time is, for example, 7 days or less.
In the case where the adhesive composition contains acetylacetone (in other words, in the case where acetylacetone is coordinated to dibutyltin dilaurate), the acetylacetone coordinated to dibutyltin dilaurate is removed during drying. Thereby, the crosslinking reaction can be performed.
In addition, a release film (release film 2) may be further laminated on the adhesive layer 10 on the release film 1 before or after curing. The 2 nd release film is, for example, a flexible plastic film subjected to a surface release treatment. As the 2 nd release film, the same films as those described above with respect to the 1 st release film can be used.
As described above, the pressure-sensitive adhesive sheet S having the pressure-sensitive adhesive surface protected by the release film can be produced. When the pressure-sensitive adhesive sheet S is used, each release film is peeled from the pressure-sensitive adhesive sheet S as necessary.
The thickness of the pressure-sensitive adhesive layer 10 is, for example, 10 μm or more, preferably 15 μm or more, from the viewpoint of securing sufficient adhesion to an adherend. From the viewpoint of the handleability of the adhesive sheet S, the thickness of the adhesive layer 10 is, for example, 300 μm or less, preferably 100 μm or less, and more preferably 50 μm or less.
The haze of the pressure-sensitive adhesive layer 10 is, for example, 3% or less, preferably 2% or less, and more preferably 1% or less. Such a configuration is suitable for checking the presence or absence of foreign matter and air bubbles between the adhesive sheet S and the adherend after the adhesive sheet S is bonded to the adherend. The haze of the pressure-sensitive adhesive layer 10 can be measured by using a haze meter in accordance with JIS K7136 (year 2000). Examples of the haze meter include "NDH2000" manufactured by Nippon electric color industry Co., ltd., and "HM-150" manufactured by Toku Kogyo Co., ltd.
The average transmittance of the adhesive layer 10 at a wavelength of 400 to 700nm (average transmittance before external stimulus is applied to the adhesive layer 10) is, for example, 80% or more, preferably 85% or more, and more preferably 90% or more. Such a configuration is suitable for checking the presence or absence of foreign matter and air bubbles between the adhesive sheet S and the adherend after the adhesive sheet S is bonded to the adherend.
In the pressure-sensitive adhesive sheet S, after the pressure-sensitive adhesive layer 10 is applied to a glass plate, the pressure-sensitive adhesive force to the glass plate in a peeling test under peeling conditions of 23℃at a peeling angle of 180℃and a peeling speed of 300 mm/min is, for example, 1.0N/25mm or more, preferably 5.0N/25mm or more. The same adhesive force is preferably 50N/25mm or less, more preferably 40N/25mm or less, and still more preferably 20N/25mm or less.
For the adhesive layer 10, the shear storage modulus at 25℃shown in the dynamic viscoelasticity measurement at a frequency of 1Hz and a heating rate of 5 ℃/min is preferably 0.1X10 5 Pa or more, more preferably 0.5X10 5 Pa or more, more preferably 1X 10 5 Pa or more. The shear storage modulus is preferably 10X 10 5 Pa or less, more preferably 5×10 5 Pa or less, more preferably 3×10 5 Pa or below.
As shown in fig. 2, the pressure-sensitive adhesive sheet S may be a single-sided pressure-sensitive adhesive sheet with a base material including a base material 20 in addition to the pressure-sensitive adhesive layer 10. In this case, the pressure-sensitive adhesive sheet S specifically includes the pressure-sensitive adhesive layer 10 and the base material 20 disposed on one side in the thickness direction D. The substrate 20 is preferably in contact with one surface of the adhesive layer 10 in the thickness direction D.
The base material 20 is an element functioning as a transparent support. The base material 20 is, for example, a plastic film having flexibility. Examples of the constituent material of the plastic film include polyolefin, polyester, polyamide, polyimide, polyvinyl chloride, polyvinylidene chloride, cellulose, polystyrene, and polycarbonate. Examples of the polyolefin include polyethylene, polypropylene, poly-1-butene, poly-4-methyl-1-pentene, ethylene/propylene copolymer, ethylene/1-butene copolymer, ethylene/vinyl acetate copolymer, ethylene/ethyl acrylate copolymer and ethylene/vinyl alcohol copolymer. Examples of the polyester include polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate. Examples of the polyamide include polyamide 6,6 and partially aromatic polyamide. In the base material 20, from the viewpoint of both the transparency and the mechanical strength, the plastic material of the base material 20 is preferably polyester, more preferably polyethylene terephthalate.
The substrate 20 has transparency. The haze of the substrate 20 is, for example, 3% or less, preferably 2% or less, and more preferably 1% or less. The haze of the substrate 20 can be measured by using a haze meter according to JIS K7136 (year 2000).
The surface of the substrate 20 on the side of the adhesive layer 10 may be subjected to a physical treatment, a chemical treatment, or a primer treatment for improving the adhesion to the adhesive layer 10. Examples of the physical treatment include corona treatment and plasma treatment. Examples of the chemical treatment include an acid treatment and an alkali treatment.
From the viewpoint of securing strength for the base material 20 to function as a support, the thickness of the base material 20 is, for example, 5 μm or more, preferably 10 μm or more, and more preferably 20 μm or more. In addition, from the viewpoint of achieving moderate flexibility in the adhesive sheet S, the thickness of the base material 20 is, for example, 200 μm or less, preferably 150 μm or less, and more preferably 100 μm or less.
The pressure-sensitive adhesive sheet S shown in fig. 2 can be produced in the same manner as the production method described above, except that the base material 20 is used instead of the 1 st release film, for example.
Fig. 3 shows an example of a method of using the adhesive sheet S. The method comprises the following steps: a preparation process, a bonding process and a color change part forming process.
First, in the preparation step, as shown in fig. 3A, the adhesive sheet S, the 1 st member 31, and the 2 nd member 32 are prepared. The 1 st member 31 is, for example, a display panel. The 1 st member 31 may be other electronic devices and optical devices. The 2 nd member 32 is, for example, a transparent substrate. Examples of the transparent substrate include a transparent plastic substrate and a transparent glass substrate.
Next, in the joining step, as shown in fig. 3B, the 1 st member 31 and the 2 nd member 32 are joined by the adhesive sheet S. Thus, a laminate W was obtained. In the laminate W, the adhesive sheet S is disposed so as to be in surface contact with one surface of the 1 st member 31 in the thickness direction, and the 2 nd member 32 is disposed so as to be in surface contact with one surface of the adhesive sheet S in the thickness direction.
After the bonding step, the presence or absence of foreign matter and air bubbles between the members 31, 32 and the adhesive sheet S is checked as necessary.
Next, in the color change step, as shown in fig. 3C, an external stimulus is applied to the adhesive layer 10 in the laminate W, and a color change portion 11 is formed in the adhesive layer 10. Specifically, from the transparent 2 nd member 32 side, active energy rays as external stimuli are irradiated to the adhesive layer 10 through a mask pattern (not shown) for masking a predetermined region in the adhesive layer 10. Thereby, the portions of the adhesive layer 10 not masked by the mask pattern are discolored.
In this step, an acid is generated from the photoacid generator in the portion of the pressure-sensitive adhesive layer 10 irradiated with the active energy ray, and the color-developing compound develops color by reacting with the acid. Thereby, the color change portion 11 is formed in the adhesive layer 10.
The pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S contains a color-developing compound as described above. Therefore, after the adhesive sheet S is attached to the adherend (in this embodiment, the members 31 and 32), external stimulus is applied to the portion of the adhesive layer 10 to be discolored, whereby the adhesive layer 10 can be locally discolored. In the adhesive sheet S which can be bonded to an adherend and in which the color change portion 11 can be formed in the adhesive layer 10, the presence or absence of foreign matter and air bubbles between the adhesive sheet S and the adherend can be checked after bonding and before forming the color change portion 11 of the adhesive layer 10.
In addition, as described above, the adhesive layer 10 contains the adhesive composition containing the metal complex. Therefore, the diffusion of the coloring component (color former) in the color-changing portion 11 can be suppressed.
In detail, the metal complex is coordinated with the color former after color development, whereby the color former can suppress the diffusion of the coloring component (color former) in the color-change portion 11 with time.
The degree of diffusion of the coloring component (color-developing compound) in the color-change portion 11 can be determined by measuring the 1 st color-change width W1, the 2 nd color-change width W2, and the 3 rd color-change width W3.
The 1 st color change width W1 is determined as follows: the adhesive layer 10 was subjected to linear external stimulus, and the width of the color change region formed in the adhesive layer 10 was measured to obtain the result.
The 2 nd color change width W2 was obtained as follows: the width of the color change region after formation in the adhesive layer 10 and further heat treatment at 85 ℃ for 120 hours was measured by applying an external stimulus to the adhesive layer 10 in a linear shape.
The 3 rd color change width W3 is determined as follows: the width of the color change region after forming in the adhesive layer 10 and further heat-treating the adhesive layer 10 at 85 ℃ for 240 hours was measured by applying an external stimulus to the adhesive layer 10 in a linear shape.
Then, in the adhesive layer 10, the 1 st color change width W1 and the 2 nd color change width W2 preferably satisfy the following formula (1).
0.5<W2/W1<2 (1)
In the pressure-sensitive adhesive layer 10, the 1 st color-change width W1 and the 3 rd color-change width W3 preferably satisfy the following formula (2).
0.5<W3/W1<2 (2)
The average transmittance T1 and the average transmittance T2 preferably satisfy the following expression (3), and preferably satisfy the following expression (4).
0.5<T2/T1<3 (3)
0.5<T2/T1<2 (4)
If the above formula (3) or the above formula (4) is satisfied, the weather resistance is excellent.
The average transmittance T1 can be obtained by the weather resistance test described later.
The average transmittance T1 is, for example, 10% or more, preferably 15% or more. The same average transmittance T1 is, for example, 40% or less, preferably 30% or less.
The average transmittance T2 can be obtained by the weather resistance test described later.
The average transmittance T2 is, for example, 15% or more, preferably 24% or more. The same average transmittance T2 is, for example, 50% or less, preferably 40% or less.
From the viewpoint of weather resistance, the color difference measured according to the weather resistance test described later is, for example, 30 or less, preferably 28 or less, more preferably 25 or less, and still more preferably 20 or less.
As an example of a method of using the adhesive sheet S, the adhesive sheet S may be disposed on the light emission side (image display side) of a pixel panel in a display panel.
As shown in fig. 4A in detail, in the case where the 1 st member 31 is a display panel, the color change portions 11 are provided in a pattern shape corresponding to (i.e., facing) the conductor layer 33 as the metal wiring formed on the pixel panel provided in the display panel. Thereby, external light reflection in the conductor layer can be suppressed.
The width of the conductor layer is, for example, 10 μm or more. The same width is, for example, 300 μm or less.
The conductor layers are preferably formed at fine pitches. The distance between the conductor layers 33 is, for example, 10 μm or more. The same interval is 100000 μm or less, for example.
The line width of the color change portion 11 corresponds to the width of the conductor layer. Specifically, the line width of the color change portion 11 is, for example, 10 μm or more. The same line width is, for example, 300 μm or less. The interval between the color-changing portions 11 is, for example, 10 μm or more. The same interval is 100000 μm or less, for example.
On the other hand, in the color change portion 11, the coloring component (specifically, the color-forming compound) diffuses with time. Due to such diffusion, as shown in fig. 4B, bleeding of the color-changing portion 11 occurs, and the color-changing portion 11 erodes the visible portion. In detail, the interval between the color change portions 11 corresponding to the respective conductor layers 33 becomes narrow. Thereby, the visibility of the display panel is reduced.
In addition, the color change portion 11 may be reduced in size due to such diffusion. Thus, as shown in fig. 4C, the color change portion 11 becomes smaller than the pattern shape corresponding to the conductor layer 33, and external light reflection in the conductor layer 33 cannot be suppressed.
Particularly in the case where the conductor layers 33 are provided at a fine pitch, the color-changing portions 11 corresponding to the conductor layers 33 are spaced apart from each other more narrowly than originally. Therefore, the above erosion must be sufficiently suppressed.
On the other hand, in the adhesive sheet S, the adhesive layer 10 contains an adhesive composition containing a metal complex. Therefore, the diffusion of the coloring component (color former) in the color-changing portion 11 can be suppressed. Accordingly, the visibility of the display panel provided with the conductor layer 33 can be improved. In addition, external light reflection in the conductor layer 33 can be suppressed.
In the above description, the shape of the color change portion 11 is linear, but the shape of the color change portion 11 is not particularly limited. Specifically, examples of the shape of the color change portion 11 include a linear shape, a dot shape, a rectangular shape, a circular shape, an elliptical shape, and an indefinite shape.
Examples
The present invention will be specifically described with reference to examples, but the present invention is not limited to the examples. Specific numerical values such as the compounding amount (content), physical property value, and parameter described below may be replaced with upper limits (as numerical values defined as "below" or "lower" or as numerical values defined as "above" or "exceeding") or lower limits (as numerical values defined as "above" or "lower") of the compounding amount (content), physical property value, and parameter described in the above-described "specific embodiment".
< preparation of base Polymer >
Production example 1
In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser and a nitrogen inlet tube, a mixture containing 63 parts by mass of 2-ethylhexyl acrylate (2 EHA), 9 parts by mass of Methyl Methacrylate (MMA), 13 parts by mass of 2-hydroxyethyl acrylate (HEA), 15 parts by mass of N-vinyl-2-pyrrolidone (NVP), 0.2 part by mass of 2,2' -Azobisisobutyronitrile (AIBN) as a polymerization initiator and 233 parts by mass of ethyl acetate as a solvent was stirred at 60 ℃ under a nitrogen atmosphere for 7 hours (polymerization reaction). Thus, a polymer solution containing an acrylic polymer was obtained. The weight average molecular weight (Mw) of the acrylic polymer in the polymer solution was 120 ten thousand.
< preparation of adhesive composition >
Example 1
The following components were uniformly mixed with respect to 100 parts by mass of the acrylic polymer (base polymer) in the above polymer solution containing the acrylic polymer of production example 1 to prepare an adhesive composition.
A chromogenic compound that develops color by reaction with an acid: leuco dye, 2 '-anilino-6' - (N-ethyl-N-isopentylamino) -3 '-methyl spirocyclic [ tetrachlorophthalein-3, 9' - [9H ] xanthene ] (trade name: S-205, manufactured by mountain chemical industry Co., ltd.) 2.00 parts by mass
Acid generator: photoacid generator, sulfonium and (C) 6 F 5 ) 4 B - 7.00 parts by mass of an onium salt (trade name: CPI-310B, san-Apro Ltd.)
Metal complex: zinc salicylate trihydrate (Fuji film and Guangdong Kagaku Co., ltd.) 0.38 parts by mass
Crosslinking agent: TAKENATE D110N (75% ethyl acetate solution of trimethylolpropane adduct of xylene diisocyanate, sanjing chemical Co., ltd.) 0.25 parts by mass (solid content conversion)
Crosslinking catalyst: 0.01 part by mass (in terms of solid content) of dibutyltin dilaurate (1% by mass ethyl acetate solution)
Acetylacetone: 3.00 parts by mass
< formation of adhesive layer >)
The pressure-sensitive adhesive composition was applied to a release film (polyester film, thickness 38 μm, mitsubishi resin Co., ltd., MRF#38) having one side as a release surface to form a coating film. Subsequently, the coating film was dried at 132℃for 3 minutes to form an adhesive layer having a thickness of 25. Mu.m. A release film (polyester film, thickness 38 μm, mitsubishi resin Co., ltd., MRF#38) having a thickness 38 μm, which was a release surface of one side of the polyester film, was bonded to the pressure-sensitive adhesive layer. Then, the adhesive layer was cured at 60℃for 1 day, and the crosslinking reaction was allowed to proceed.
As described above, the adhesive sheet of example 1 was produced. The composition of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive sheet of example 1 is shown in table 1 (the same applies to examples and comparative examples described later) in terms of parts by mass.
Example 2, example 3 and comparative example 1
An adhesive sheet was produced in the same manner as the adhesive sheet of example 1.
Wherein the composition of the adhesive composition was changed according to table 1.
< evaluation >
1. Weather resistance test
(production of samples for weather resistance test)
One surface of Eagle glass (thickness 0.55mm, manufactured by Song Nitro Co., ltd.) was laminated in this order to form an adhesive layer of 25 μm, UVA-TAC 32 μm, UVA-OCA100 μm and UVA-TAC 32 μm in each example and each comparative example. In the laminate of each example and each comparative example, the sample was irradiated with ultraviolet light. Specifically, for the adhesive sheet (adhesive layer) in the sample, ultraviolet rays were irradiated from the Eagle glass side through the same glass in an environment of 23 ℃ and 50% relative humidity (by this UV irradiation, the leuco dye in the adhesive layer was reacted with the photoacid generator). In the UV irradiation, a UV-LED lamp having a wavelength of 365nm in a UV-LED irradiation apparatus (model "QEL-350-RU 6W-CW-MY") manufactured by Quarktec Technology Co., ltd was used as a light source so that the cumulative irradiation light amount was 8000mJ/cm 2 (accumulated amount of irradiation light in the wavelength range of 320 to 390 nm). As described above, a sample for weather resistance test was prepared.
The UVA-TAC is provided with: TAC film (KC 2UA, manufactured by KONICA MINOLTA Co., ltd.) and film of hard coat layer (thickness: 7 μm) was formed on one side of KC2UA (thickness: 25 μm) by hard coat treatment), thereby obtaining (thickness: 32 μm)
UVA-OCA: adhesive tape having ultraviolet absorbing function, trade name "CS9934U", 100 μm thick, manufactured by Nito Denko K.K.)
(weather resistance test)
Average transmittance, L, a, and b values were measured in the samples for the weather resistance test of each example and each comparative example.
Specifically, the sample for weather resistance test was set in a transmittance measuring device (U4150 spectrophotometer, manufactured by Hitachi High-Tech Co., ltd.) so as to emit light from the Eagle glass side. Then, the average transmittance, L, a, and b values at wavelengths of 400nm to 700nm were measured, respectively.
Specifically, the average transmittance (T1) at a wavelength of 400nm to 700nm, the L (L1) for the sample for the weather resistance test, the a (a 1) for the sample for the weather resistance test, and the b (b 1) for the sample for the weather resistance test were measured, respectively.
Subsequently, a super xenon lamp weatherometer SX75 manufactured by Suga Test Instruments co., ltd was used as a sample for weatherometer, and a super xenon lamp having an illuminance of 120W in a wavelength range of 300 to 400nm was irradiated for 24 hours. Thus, a sample for a weather resistance test after 24 hours of irradiation was obtained.
Next, according to the same procedure as described above, the average transmittance, L, a, and b values of the samples for the weather resistance test after 24 hours of irradiation were measured.
Specifically, the average transmittance (T2) at a wavelength of 400nm to 700nm of the sample for the weathering test after 24 hours of irradiation, L (L2) of the sample for the weathering test after 24 hours of irradiation, a (a 2) of the sample for the weathering test after 24 hours of irradiation, and b (b 2) of the sample for the weathering test after 24 hours of irradiation were measured, respectively.
Then, based on the following equation (7), a color difference (Δe) is calculated.
ΔE＝((L2*-L1*) 2 +(a2*-a1*) 2 +(b2*-b1*) 2 ) 1/2 (7)
The results of T1, T2 and color difference (ΔE) are shown in Table 1.
2. Durability test
A line-shaped color change portion is formed in an adhesive layer of an adhesive sheet by irradiating the adhesive layer with ultraviolet light through a photomask having a line-shaped opening. The photomask was formed of a dry film photoresist disposed on the side surface of the base film in the adhesive sheet, and the line width of the opening of the photomask was 200 μm. In ultraviolet irradiation, a UV-LED lamp with a wavelength of 365nm in a UV-LED irradiation apparatus (model "QEL-350-RU 6W-CW-MY") manufactured by Quarktec Technology co., ltd was used as a light source, and an adhesive layer was faced through a photomask and a substrate film Irradiating with ultraviolet rays to give an accumulated irradiation light quantity of 2000mJ/cm 2 (accumulated amount of irradiation light in the wavelength range of 320 to 390 nm).
Next, the line width of the linear color change portion formed in the pressure-sensitive adhesive layer was measured (measurement of the 1 st color change width W1). Specifically, first, a linear color change portion formed in the adhesive layer was observed with a digital microscope (trade name "VHX-900", manufactured by KEYENCE corporation), and a region including a part of the color change portion and the vicinity thereof was photographed at a magnification of 50 times. Then, the captured image is binarized by image analysis software. Next, in the binarized image, the line width of the linear color change portion (1 st color change width W1) was measured.
Next, the pressure-sensitive adhesive sheet having the linear color-change portions formed in the pressure-sensitive adhesive layer was subjected to heat treatment at 85 ℃ for 120 hours (durability test 1).
Next, the line width of the linear color change portion in the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet was measured (measurement of the 2 nd color change width W2). The specific measurement method is the same as the measurement method described above concerning the measurement of the 1 st color change width W1. Table 1 shows the 1 st color change width W1 of the linear color change portion before the 1 st durability test, the 2 nd color change width W2 of the linear color change portion after the 1 st durability test, and the rate of increase (W2/W1) of the 2 nd color change width W2 with respect to the 1 st color change width W1.
Further, the degree of oozing inhibition of the linear color change portion formed was examined in the same manner as described above, except that the 2 nd durability test was performed instead of the 1 st durability test for the adhesive layers of the adhesive sheets of examples 1 to 3 and comparative example 1. In the durability test 2, the adhesive sheet having the linear color change portion formed in the adhesive layer was subjected to heat treatment at 85℃for 240 hours. Table 1 shows the 1 st color change width W1 of the linear color change portion before the 2 nd durability test, the 3 rd color change width W3 of the linear color change portion after the 2 nd durability test, and the rate of increase of the 3 rd color change width W3 relative to the 1 st color change width W1 (3 rd color change width W3/1 st color change width W1).
3. Peel test
The adhesive layers of each example and each comparative example were attached to a glass plate. After that, the adhesion to the glass plate was measured based on the following conditions. The results are shown in Table 1.
(measurement conditions)
Temperature: 23 DEG C
Peel angle: 180 degree
Peeling speed: 300 mm/min
TABLE 1
TABLE 1
The color of the adhesive layer changes to red.
The present invention is provided as an exemplary embodiment of the present invention, but it is merely an example and is not to be construed as limiting. Variations of the present invention that are obvious to those skilled in the art are encompassed in the appended claims.
Industrial applicability
The color-changeable adhesive sheet of the present invention is suitably used in the manufacturing process of display panels.
Description of the reference numerals
S adhesive sheet (variable color adhesive sheet)
10. Adhesive layer
11. Color change portion
20. Substrate material
31. 1 st component
32. Component 2
33. Conductor layer
Claims (6)
1. A color-changeable adhesive sheet comprising an adhesive layer which changes color due to an external stimulus,
the adhesive layer comprises an adhesive composition,
the adhesive composition comprises: a chromogenic compound that develops color by reaction with an acid, an acid generator and a metal complex,
the chromogenic compound after chromogenic is capable of coordinating with the metal complex.
2. The color-changeable adhesive sheet according to claim 1, wherein the compounding ratio of the metal complex is 10 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the color-developing compound.
3. The color-changeable adhesive sheet according to claim 1, wherein,
the color-developing compound is a leuco dye,
the metal complex is a zinc complex.
4. The variable color adhesive sheet according to claim 1, wherein the adhesive layer has a thickness of 10 μm or more and 300 μm or less.
5. The color-changeable adhesive sheet according to claim 1, further comprising a base material disposed on one side in the thickness direction of the adhesive layer.
6. The color-changeable adhesive sheet according to claim 1, wherein the adhesive layer, after being attached to a glass plate, exhibits an adhesive force of 1.0N/25mm or more and 50N/25mm or less to the glass plate in a peeling test under peeling conditions of 23 ℃ at a peeling angle of 180 ° and a peeling speed of 300 mm/min.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020152234A JP2022046282A (en) | 2020-09-10 | 2020-09-10 | Color-changeable adhesive sheet |
| JP2020-152234 | 2020-09-10 | ||
| PCT/JP2021/031866 WO2022054634A1 (en) | 2020-09-10 | 2021-08-31 | Color-changeable adhesive sheet |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116075568A CN116075568A (en) | 2023-05-05 |
| CN116075568B true CN116075568B (en) | 2024-02-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180061843.0A Active CN116075568B (en) | 2020-09-10 | 2021-08-31 | Color-changeable adhesive sheet |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2022046282A (en) |
| KR (1) | KR102572376B1 (en) |
| CN (1) | CN116075568B (en) |
| TW (1) | TW202223034A (en) |
| WO (1) | WO2022054634A1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62153377A (en) * | 1985-12-27 | 1987-07-08 | F S K Kk | Pressure-sensitive adhesive sheet |
| JPH02107681A (en) * | 1988-10-18 | 1990-04-19 | Tomoegawa Paper Co Ltd | Photo-sensitive tacky adhesive sheet |
| JP2007326960A (en) * | 2006-06-08 | 2007-12-20 | Tombow Pencil Co Ltd | Pressure-sensitive transfer adhesive tape and coating film-transferring tool |
| WO2016129568A1 (en) * | 2015-02-09 | 2016-08-18 | 株式会社スリーボンド | Method for curing photocurable resin composition and cured product |
| JP2016196541A (en) * | 2015-04-02 | 2016-11-24 | 山本化成株式会社 | Liquid resin composition for active ray-curable adhesive |
| WO2019035411A1 (en) * | 2017-08-18 | 2019-02-21 | 積水化学工業株式会社 | Moisture curable resin composition, adhesive for electronic components, and adhesive for display elements |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106715477B (en) * | 2014-09-29 | 2018-10-12 | 三键有限公司 | Photocurable resin composition |
| JP2017203810A (en) | 2016-05-09 | 2017-11-16 | 日本化薬株式会社 | Light absorption layer contained in color filter for organic electroluminescence display and sheet using the same |
| WO2020189390A1 (en) * | 2019-03-15 | 2020-09-24 | 日東電工株式会社 | Adhesive agent composition, adhesive agent layer, and adhesive sheet |
| WO2021075401A1 (en) * | 2019-10-18 | 2021-04-22 | 日東電工株式会社 | Adhesive sheet and intermediate laminate |
-
2020
- 2020-09-10 JP JP2020152234A patent/JP2022046282A/en not_active Withdrawn
-
2021
- 2021-08-31 WO PCT/JP2021/031866 patent/WO2022054634A1/en active Application Filing
- 2021-08-31 KR KR1020237007100A patent/KR102572376B1/en active IP Right Grant
- 2021-08-31 CN CN202180061843.0A patent/CN116075568B/en active Active
- 2021-09-10 TW TW110133729A patent/TW202223034A/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62153377A (en) * | 1985-12-27 | 1987-07-08 | F S K Kk | Pressure-sensitive adhesive sheet |
| JPH02107681A (en) * | 1988-10-18 | 1990-04-19 | Tomoegawa Paper Co Ltd | Photo-sensitive tacky adhesive sheet |
| JP2007326960A (en) * | 2006-06-08 | 2007-12-20 | Tombow Pencil Co Ltd | Pressure-sensitive transfer adhesive tape and coating film-transferring tool |
| WO2016129568A1 (en) * | 2015-02-09 | 2016-08-18 | 株式会社スリーボンド | Method for curing photocurable resin composition and cured product |
| JP2016196541A (en) * | 2015-04-02 | 2016-11-24 | 山本化成株式会社 | Liquid resin composition for active ray-curable adhesive |
| WO2019035411A1 (en) * | 2017-08-18 | 2019-02-21 | 積水化学工業株式会社 | Moisture curable resin composition, adhesive for electronic components, and adhesive for display elements |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2022046282A (en) | 2022-03-23 |
| CN116075568A (en) | 2023-05-05 |
| WO2022054634A1 (en) | 2022-03-17 |
| KR20230037674A (en) | 2023-03-16 |
| KR102572376B1 (en) | 2023-08-29 |
| TW202223034A (en) | 2022-06-16 |
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