WO2018173979A1 - Composition adhésive sensible à la pression et feuille adhésive sensible à la pression - Google Patents
Composition adhésive sensible à la pression et feuille adhésive sensible à la pression Download PDFInfo
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- WO2018173979A1 WO2018173979A1 PCT/JP2018/010632 JP2018010632W WO2018173979A1 WO 2018173979 A1 WO2018173979 A1 WO 2018173979A1 JP 2018010632 W JP2018010632 W JP 2018010632W WO 2018173979 A1 WO2018173979 A1 WO 2018173979A1
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- WIPO (PCT)
- Prior art keywords
- pressure
- sensitive adhesive
- group
- carbon atoms
- adhesive composition
- Prior art date
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 243
- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims abstract description 87
- 239000010410 layer Substances 0.000 claims abstract description 68
- 239000000853 adhesive Substances 0.000 claims description 97
- 230000001070 adhesive effect Effects 0.000 claims description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 79
- -1 carbamoyloxy group Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 25
- 125000004423 acyloxy group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 229940125898 compound 5 Drugs 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical group O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 description 50
- 239000012790 adhesive layer Substances 0.000 description 33
- 238000011156 evaluation Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 229920000459 Nitrile rubber Polymers 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229920002799 BoPET Polymers 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 229920006243 acrylic copolymer Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052609 olivine Inorganic materials 0.000 description 4
- 239000010450 olivine Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 125000006841 cyclic skeleton Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000000411 transmission spectrum Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006608 n-octyloxy group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 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
- 125000004149 thio group Chemical group *S* 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940126001 AT-527 Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002042 Silver nanowire Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- YRXGUZPUZBCGST-UHFFFAOYSA-N [2-(hydroxymethoxy)phenyl]-phenylmethanone Chemical compound OCOC1=CC=CC=C1C(=O)C1=CC=CC=C1 YRXGUZPUZBCGST-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Definitions
- This disclosure relates to an adhesive composition and an adhesive sheet.
- blue light for example, light in a wavelength region of 380 nm to 500 nm
- ultraviolet rays for example, light in a wavelength region of 300 nm to 400 nm
- attempts have been made to impart a function of blocking ultraviolet rays and / or blue light in display sheets and window films.
- Japanese Patent Application Laid-Open No. 2016-130276 discloses a screen protection film having a base material and a pressure-sensitive adhesive layer provided on the base material as a film having excellent ultraviolet absorbing ability, A hard coat layer is provided on the surface opposite to the pressure-sensitive adhesive layer, the pressure-sensitive adhesive layer contains an acrylic copolymer and a triazine ultraviolet absorber, and the acrylic copolymer is methyl.
- the acrylate monomer unit is contained in an amount of 1 to 20% by mass based on the solid content of the acrylic copolymer, and the pressure-sensitive adhesive layer contains the triazine-based ultraviolet absorber in 100 parts by mass of the acrylic copolymer. 10 to 20 parts by mass, using a image clarity measuring device in accordance with JIS K7374: 2007, and placing it on the sample table with the adhesive layer of the screen protection film facing the light source, A screen protection film having a image clarity of 80 to 100% measured at a base angle of 45 degrees, a transmission mode, and a comb width of 0.125 mm is known (see, for example, JP-A-2016-130276).
- a film containing an ultraviolet absorber in the adhesive layer at least one hindered phenolic antioxidant selected from the group consisting of an adhesive, an ultraviolet absorber, a triazine skeleton, a thio skeleton, and a cresol skeleton
- a pressure-sensitive adhesive film having a pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive composition comprising see, for example, JP-A-2014-193939).
- the ultraviolet absorber is generally a compound having a cyclic skeleton.
- the compound having a cyclic skeleton has high rigidity, in the pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition containing the ultraviolet absorber, the cohesive energy may increase and the pressure-sensitive adhesive force may decrease.
- the adhesive sheet is required to have excellent adhesive strength, it is not desirable that the adhesive strength of the adhesive layer is reduced by the ultraviolet absorber.
- One embodiment of the present invention provides a pressure-sensitive adhesive composition that has a function of blocking ultraviolet light and blue light, is capable of forming a pressure-sensitive adhesive layer that has an excellent pressure-sensitive adhesive force, and is capable of forming a pressure-sensitive adhesive layer. About that. Another embodiment of this invention is related with providing the adhesive sheet which has an adhesive layer containing the said adhesive composition.
- Means for solving the above problems include the following aspects.
- a pressure-sensitive adhesive composition comprising a pressure-sensitive adhesive and an ultraviolet absorber having at least one of —S— and —SO 2 — in the molecule.
- X 1 and X 2 each independently represent an oxygen atom, a sulfur atom, or NR 17 , and at least one of X 1 and X 2 represents a sulfur atom.
- R 17 represents a hydrogen atom or a monovalent substituent.
- R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are each independently a hydrogen atom, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or a carbon number.
- R 21 , R 22 , and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an acyloxy group having 2 to 30 carbon atoms. Or a carbamoyloxy group having 1 to 30 carbon atoms.
- At least one of R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 in the formula (1) represents a linear alkyl group having 4 to 12 carbon atoms, according to ⁇ 4>.
- ⁇ 6> The pressure-sensitive adhesive composition according to ⁇ 4> or ⁇ 5>, wherein at least one of R 21 , R 22 , and R 23 in formula (2) represents a linear alkyl group having 4 to 12 carbon atoms.
- the ultraviolet absorber includes at least one compound selected from the group consisting of Compound 1, Compound 2, Compound 3, and Compound 5 represented by the following structural formula: The pressure-sensitive adhesive composition according to any one of the above.
- the content of the ultraviolet absorber is any one of ⁇ 1> to ⁇ 8>, which is 0.5% by mass or more and 10% by mass or less with respect to the total solid content of the pressure-sensitive adhesive composition.
- Adhesive composition ⁇ 10> The pressure-sensitive adhesive according to any one of ⁇ 1> to ⁇ 9>, wherein the content of the ultraviolet absorber is 1% by mass to 5% by mass with respect to the total solid content of the pressure-sensitive adhesive composition.
- Agent composition is any one of ⁇ 1> to ⁇ 8>, which is 0.5% by mass or more and 10% by mass or less with respect to the total solid content of the pressure-sensitive adhesive composition.
- a pressure-sensitive adhesive composition that has a function of blocking ultraviolet light and blue light, is capable of forming a pressure-sensitive adhesive layer having an excellent pressure-sensitive adhesive force, with a decrease in the pressure-sensitive adhesive force caused by an ultraviolet absorber.
- a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition is provided.
- a numerical range indicated by using “to” means a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively.
- an upper limit value or a lower limit value described in a numerical range may be replaced with an upper limit value or a lower limit value in another numerical range.
- the upper limit value or the lower limit value described in a certain numerical range may be replaced with the values shown in the examples.
- a combination of two or more preferred embodiments is a more preferred embodiment.
- the content or content rate of each component means the total content or content rate of the plurality of types of substances unless there is a specific case when there are a plurality of types of substances corresponding to the respective components.
- “ultraviolet light” means light in the wavelength region of 300 nm to 400 nm.
- “blue light” means light in the wavelength region of 380 nm to 500 nm.
- blocking ultraviolet rays includes not only completely blocking ultraviolet rays but also blocking at least part of ultraviolet rays and reducing the transmittance of ultraviolet rays through an adhesive layer. To do. The same applies to “blocking of blue light”.
- the pressure-sensitive adhesive composition of the present disclosure includes a pressure-sensitive adhesive and an ultraviolet absorber having at least one of —S— and —SO 2 — in the molecule (hereinafter also referred to as “specific ultraviolet absorber”). Including. According to the pressure-sensitive adhesive composition of the present disclosure, a pressure-sensitive adhesive layer that has an ultraviolet and blue light blocking function, suppresses a decrease in the pressure-sensitive adhesive force due to the ultraviolet absorber, and has an excellent pressure-sensitive adhesive force can be formed. The reason why the pressure-sensitive adhesive composition of the present disclosure can exhibit such an effect is not clear, but the present inventor presumes as follows.
- an ultraviolet absorber is a compound having a cyclic skeleton, and therefore has high rigidity.
- cohesive energy increases and adhesive strength decreases. There is a case.
- the pressure-sensitive adhesive composition of the present disclosure includes a pressure-sensitive adhesive and an ultraviolet absorber having a structure of at least one of —S— and —SO 2 — in the molecule (that is, a specific ultraviolet absorber).
- an ultraviolet absorber having a structure of at least one of —S— and —SO 2 — in the molecule (that is, a specific ultraviolet absorber).
- the pressure-sensitive adhesive composition of the present disclosure includes a pressure-sensitive adhesive and a specific ultraviolet absorber, so that when the pressure-sensitive adhesive layer is formed as a pressure-sensitive adhesive layer, the pressure-sensitive adhesive force is not lowered, but rather improved, and ultraviolet and blue light It is also possible to provide a blocking function.
- the screen protective film described in JP-A-2016-130276 and the pressure-sensitive adhesive film described in JP-A-2014-193939 contain an ultraviolet absorber in the pressure-sensitive adhesive layer. Is not an ultraviolet absorber having a —S— structure and / or a —SO 2 — structure in the molecule. Therefore, it is considered that the screen protective film described in Japanese Patent Application Laid-Open No. 2016-130276 and the adhesive film described in Japanese Patent Application Laid-Open No. 2014-19393939 have a decrease in adhesive force due to containing an ultraviolet absorber. In addition, Japanese Patent Application Laid-Open No. 2016-130276 and Japanese Patent Application Laid-Open No. 2014-193939 do not pay any attention to the influence of the ultraviolet absorber on the adhesive force of the adhesive layer.
- the pressure-sensitive adhesive composition of the present disclosure includes a pressure-sensitive adhesive.
- the pressure-sensitive adhesive can contribute to the expression of the pressure-sensitive adhesive force of the pressure-sensitive adhesive layer formed by the pressure-sensitive adhesive composition.
- the pressure-sensitive adhesive contained in the pressure-sensitive adhesive composition of the present disclosure is not particularly limited.
- the form of the pressure-sensitive adhesive may be a solvent-based pressure-sensitive adhesive, a solventless pressure-sensitive adhesive, a water-dispersed pressure-sensitive adhesive, or a solid pressure-sensitive adhesive.
- Examples of the pressure-sensitive adhesive include acrylic pressure-sensitive adhesives, urethane-based pressure-sensitive adhesives, silicone-based pressure-sensitive adhesives, and rubber-based pressure-sensitive adhesives.
- a commercial item can be used as an adhesive.
- acrylic adhesives include ARONTAC (registered trademark, the same shall apply hereinafter) HV-C3050, ARONTAC HV-C9500, ARONTAC HV-C9506, ARONTAC HV-C3006, ARONTAC HV-C6320 from Toagosei Co., Ltd.
- Nipol registered trademark, the same shall apply hereinafter
- Examples of commercially available urethane-based pressure-sensitive adhesives include Toyochem Co., Ltd.'s olivine (registered trademark, hereinafter the same) SP-205, olivine SH-109, olivine SH-101, olivine SH-101M, and the like.
- Examples of commercially available silicone pressure-sensitive adhesives include SD4584, SD4585, SD4560, SD4570, SD4580, and SD4587 from Toray Dow Corning Co., Ltd.
- Examples of commercially available rubber-based pressure-sensitive adhesives include Nipol LX430, Nipol KX415, Nipol SX1105A manufactured by Nippon Zeon Co., Ltd., and Oribain BPS5079-1 manufactured by Toyochem Co., Ltd.
- the pressure-sensitive adhesive composition of the present disclosure may contain only one type of pressure-sensitive adhesive, or may contain two or more types.
- the content rate of the solid content of the pressure-sensitive adhesive in the pressure-sensitive adhesive composition of the present disclosure is not particularly limited. % Or less, 60 mass% or more and 98 mass% or less are more preferable, and 70 mass% or more and 97 mass% or less are still more preferable.
- the “solid content of the pressure-sensitive adhesive” in the present disclosure means a residue obtained by removing the solvent and water from the components constituting the pressure-sensitive adhesive.
- the “total solid content of the pressure-sensitive adhesive composition” means the total amount of the residue obtained by removing the solvent and water from the components constituting the pressure-sensitive adhesive composition.
- the pressure-sensitive adhesive composition of the present disclosure includes an ultraviolet absorber having at least one of —S— and —SO 2 — in the molecule (that is, a specific ultraviolet absorber).
- the specific ultraviolet light absorber can contribute not only to imparting ultraviolet and blue light blocking functions to the pressure-sensitive adhesive layer, but also to improving the pressure-sensitive adhesive strength of the pressure-sensitive adhesive layer.
- the specific ultraviolet absorber may have only the —S— structure in the molecule, may have only the —SO 2 — structure, and has both the —S— structure and the —SO 2 — structure. You may have.
- the specific ultraviolet absorber preferably has a cyclic structure in the molecule from the viewpoint that, for example, a more excellent ultraviolet blocking function and blue light blocking function can be imparted to the pressure-sensitive adhesive layer. And at least one cyclic structure selected from 3,5-pyrazolidinedione rings is more preferable.
- the specific ultraviolet absorber can impart, for example, a more excellent ultraviolet blocking function and blue light blocking function to the adhesive layer, and can further improve the adhesive strength of the adhesive layer. From the viewpoint, it is preferable to include at least one compound selected from the compound represented by the following formula (1) and the compound represented by the formula (2).
- X 1 and X 2 in Formula (1) each independently represent an oxygen atom, a sulfur atom, or NR 17 , and at least one of X 1 and X 2 represents a sulfur atom, from the viewpoint of improving heat resistance, It is preferable that both X 1 and X 2 represent a sulfur atom.
- R 17 represents a hydrogen atom or a monovalent substituent, and preferably represents a hydrogen atom.
- the monovalent substituent represented by R 17 is preferably an alkyl group, an alkoxy group, an acyloxy group, or a carbamoyloxy group.
- R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 in formula (1) are each independently a hydrogen atom, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, or an alkyl group having 1 to 30 carbon atoms.
- An alkoxy group, an acyloxy group having 2 to 30 carbon atoms, or a carbamoyloxy group having 1 to 30 carbon atoms is represented.
- the alkyl group represented by R 11 to R 16 may further have a monovalent substituent, and may be linear, branched or cyclic.
- the alkyl group has 1 to 30 carbon atoms, preferably 4 to 12 carbon atoms, and more preferably 4 to 8 carbon atoms. Note that these carbon numbers do not include the carbon number of the substituent when the alkyl group further has a substituent. The substituent will be described later.
- alkyl group having 1 to 30 carbon atoms examples include methyl group, ethyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-octyl group, i-octyl group, 2 -Ethylhexyl group, n-nonyl group, i-nonyl group, n-decyl group, n-dodecyl group, stearyl group, lauryl group, cyclohexyl group and the like.
- the alkoxy group having 1 to 30 carbon atoms represented by R 11 to R 16 is represented as —OR A1 (R A1 is an alkyl group), and R A1 has the same meaning as the alkyl group represented by R 11 to R 16. It is.
- R A1 is an alkyl group
- R A1 has the same meaning as the alkyl group represented by R 11 to R 16. It is.
- Examples of the alkoxy group having 1 to 30 carbon atoms include methoxy group, ethoxy group, propoxy group, n-octyloxy group, methoxyethoxy group, hydroxyethoxy group, 3-carboxypropoxy group and the like.
- the acyloxy group having 2 to 30 carbon atoms represented by R 11 to R 16 may further have a monovalent substituent.
- the acyloxy group has 2 to 30 carbon atoms, preferably 3 to 12, more preferably 4 to 10, still more preferably 4 to 8. These carbon numbers do not include the carbon number of the substituent when the acyloxy group further has a substituent.
- Examples of the acyloxy group having 2 to 30 carbon atoms include 2-ethylhexanoyloxy group, n-octanoyloxy group, formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy group, p-methoxy group A phenylcarbonyloxy group etc. are mentioned.
- the carbamoyloxy group having 1 to 30 carbon atoms represented by R 11 to R 16 may further have a monovalent substituent.
- the carbamoyloxy group has 1 to 30 carbon atoms, preferably 4 to 10 carbon atoms. These carbon numbers do not include the carbon number of the substituent when the carbamoyloxy group further has a substituent.
- Examples of the carbamoyloxy group having 1 to 30 carbon atoms include N-methylcarbamoyloxy group, N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N, N-di- Examples thereof include an n-octylaminocarbonyloxy group and a Nn-octylcarbamoyloxy group.
- At least one of R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 in formula (1) are preferably represented a linear alkyl group having 4 to 12 carbon atoms.
- R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 in Formula (1) is a linear alkyl group having 4 to 12 carbon atoms.
- both X 1 and X 2 are sulfur atoms
- R 11 is an alkyl group having 1 to 30 carbon atoms
- R 12 is an alkyl group having 1 to 30 carbon atoms.
- An embodiment in which the alkyl group is R 13 is an acyloxy group having 3 to 12 carbon atoms
- R 14 is a hydrogen atom
- R 15 is a hydrogen atom
- R 16 is an acyloxy group having 3 to 12 carbon atoms.
- both X 1 and X 2 are sulfur atoms
- R 11 is an alkyl group having 4 to 12 carbon atoms
- R 12 is an alkyl group having 4 to 12 carbon atoms
- R 13 is 4 to 12 carbon atoms.
- an acyloxy group of 10 More preferred is an acyloxy group of 10; R 14 is a hydrogen atom; R 15 is a hydrogen atom; and R 16 is an acyloxy group having 4 to 10 carbon atoms, and both X 1 and X 2 are sulfur.
- An atom, and R 11 is an alkyl having 4 to 8 carbon atoms.
- a kill group, R 12 is an alkyl group having 4 to 8 carbon atoms, R 13 is an acyloxy group having 4 to 8 carbon atoms, R 14 is a hydrogen atom, R 15 is a hydrogen atom,
- An embodiment in which 16 is an acyloxy group having 4 to 8 carbon atoms is further preferred. According to such an aspect, a more excellent ultraviolet blocking function and blue light blocking function can be imparted to the pressure-sensitive adhesive layer. Moreover, the adhesive force of an adhesive layer can be improved more.
- R 21 , R 22 and R 23 in formula (2) are each independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an acyloxy group having 2 to 30 carbon atoms, Alternatively, it represents a carbamoyloxy group having 1 to 30 carbon atoms.
- the alkyl group represented by R 21 to R 23 may further have a monovalent substituent, and may be linear, branched or cyclic.
- the alkyl group has 1 to 30 carbon atoms, and preferably 1 to 12 carbon atoms. Note that these carbon numbers do not include the carbon number of the substituent when the alkyl group further has a substituent.
- alkyl group having 1 to 30 carbon atoms examples include methyl group, ethyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-octyl group, i-octyl group, 2 -Ethylhexyl group, n-nonyl group, i-nonyl group, n-decyl group, n-dodecyl group, stearyl group, lauryl group, cyclohexyl group and the like.
- the alkoxy group having 1 to 30 carbon atoms represented by R 21 to R 23 is represented as —OR A2 (R A2 is an alkyl group), and R A2 has the same meaning as the alkyl group represented by R 21 to R 23. It is.
- R A2 is an alkyl group
- R A2 has the same meaning as the alkyl group represented by R 21 to R 23. It is.
- Examples of the alkoxy group having 1 to 30 carbon atoms include methoxy group, ethoxy group, propoxy group, n-octyloxy group, methoxyethoxy group, hydroxyethoxy group, 3-carboxypropoxy group and the like.
- the acyloxy group having 2 to 30 carbon atoms represented by R 21 to R 23 may further have a monovalent substituent.
- the acyloxy group has 2 to 30 carbon atoms, preferably 4 to 10 carbon atoms. These carbon numbers do not include the carbon number of the substituent when the acyloxy group further has a substituent.
- Examples of the acyloxy group having 2 to 30 carbon atoms include 2-ethylhexanoyloxy group, n-octanoyloxy group, formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy group, p-methoxy group A phenylcarbonyloxy group etc. are mentioned.
- the carbamoyloxy group having 1 to 30 carbon atoms represented by R 21 to R 23 may further have a monovalent substituent.
- the carbamoyloxy group has 1 to 30 carbon atoms, preferably 4 to 10 carbon atoms. These carbon numbers do not include the carbon number of the substituent when the carbamoyloxy group further has a substituent.
- Examples of the carbamoyloxy group having 1 to 30 carbon atoms include N-methylcarbamoyloxy group, N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N, N-di- Examples thereof include an n-octylaminocarbonyloxy group and a Nn-octylcarbamoyloxy group.
- At least one of R 21 , R 22 , and R 23 in Formula (2) has 4 to 12 carbon atoms. It preferably represents a linear alkyl group, and more preferably represents a linear alkyl group having 8 to 12 carbon atoms.
- R 21 , R 22 , and R 23 in formula (2) is a linear alkyl group having 4 to 12 carbon atoms, a flexible portion is formed in the structure of the ultraviolet absorber, and thus the formed adhesive The tenacity of the agent layer is improved and the adhesive strength is further increased.
- R 21 is an alkyl group
- R 22 is an alkyl group
- R 23 is an alkyl group
- R 21 has 1 to 4 carbon atoms. More preferred is an alkyl group, R 22 is an alkyl group having 1 to 4 carbon atoms, R 23 is an alkyl group having 4 to 12 carbon atoms, and R 21 is an alkyl group having 1 to 4 carbon atoms. More preferably, R 22 is an alkyl group having 1 to 4 carbon atoms, and R 23 is an alkyl group having 8 to 12 carbon atoms.
- a more excellent ultraviolet blocking function and blue light blocking function can be imparted to the pressure-sensitive adhesive layer.
- the adhesive force of an adhesive layer can be improved more.
- the substituent that the alkyl group, acyloxy group, and carbamoyloxy group in Formula (1) and Formula (2) may have can be arbitrarily selected from the following substituent group.
- Substituent group halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyl Oxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto Group, alkylthio group, arylthio group, heterocyclic thio group
- Specific examples of the specific ultraviolet absorber are shown below. However, the specific ultraviolet absorber is not limited to these compounds.
- the following compound 1, compound 2, and compound 5 are specific examples of the compound represented by formula (1), and the following compound 3 and compound 6 are specific examples of the compound represented by formula (2). It is an example.
- the specific ultraviolet light absorber Preferably contains at least one compound selected from the group consisting of Compound 1, Compound 2, Compound 3, and Compound 5. Since all of Compound 1, Compound 2, Compound 3, and Compound 5 have a linear alkyl group having 4 or more carbon atoms, a flexible portion is generated in the structure. Thereby, in the adhesive layer formed of the adhesive composition containing at least one compound selected from the group consisting of Compound 1, Compound 2, Compound 3, and Compound 5, a linear alkyl group having 4 or more carbon atoms is added.
- the tenacity is improved, and thus the pressure-sensitive adhesive strength is further increased.
- the specific ultraviolet absorber contained in the pressure-sensitive adhesive composition of the present disclosure is at least one compound selected from the group consisting of Compound 1, Compound 2, Compound 3, and Compound 5, The yellowishness of the pressure-sensitive adhesive layer that may be caused is further suppressed.
- compound 4 is preferably included. Since compound 4 has absorption in the region on the long wavelength side due to its skeletal structure, an excellent blue light blocking function can be imparted to the pressure-sensitive adhesive layer.
- a commercial item can be used as a specific ultraviolet absorber.
- specific ultraviolet absorbers include Tinuvin (registered trademark) PS, 99-2, 326, 384-2, 900, 928, 1130, 400, 405, 460, 477, 479, etc., manufactured by BASF Japan. Can be mentioned.
- the pressure-sensitive adhesive composition of the present disclosure may contain only one type of specific ultraviolet absorber, or may contain two or more types.
- the content rate of the specific ultraviolet absorber in the adhesive composition of this indication is not restrict
- the content of the specific ultraviolet absorber in the pressure-sensitive adhesive composition of the present disclosure is 0.5% by mass or more with respect to the total solid content of the pressure-sensitive adhesive composition, more excellent ultraviolet light with respect to the pressure-sensitive adhesive layer A blocking function and a blue light blocking function can be provided. Moreover, the adhesive force of an adhesive layer can be improved more.
- the adhesive force of the adhesive layer by an ultraviolet absorber as the content rate of the specific ultraviolet absorber in the adhesive composition of this indication is 10 mass% or less with respect to the total solid of an adhesive composition. Is further suppressed. Moreover, yellowishness that can be caused by the ultraviolet absorber is further suppressed.
- the ratio of the solid content of the specific ultraviolet absorber to the solid content of the adhesive in the pressure-sensitive adhesive composition of the present disclosure (hereinafter also referred to as “solid content of the specific ultraviolet absorber / solid content of the adhesive”) is, for example, 1
- the mass% is preferably 20% by mass or less, more preferably 2% by mass or more and 10% by mass or less, and further preferably 4% by mass or more and 10% by mass or less.
- the pressure-sensitive adhesive force of the pressure-sensitive adhesive layer can be further improved.
- the solid content of the specific ultraviolet absorber / the solid content of the adhesive in the pressure-sensitive adhesive composition of the present disclosure is 20% by mass or less, a decrease in the adhesive strength of the pressure-sensitive adhesive layer due to the ultraviolet absorber is further suppressed.
- the pressure-sensitive adhesive composition of the present disclosure may contain components other than the components described above (so-called other components) as necessary within a range not impairing the effects of the present disclosure.
- other components include a solvent, an antioxidant, a crosslinking agent, a surfactant, a filler, a colorant, a light stabilizer, a thickener, and a polymerization initiator.
- the pressure-sensitive adhesive composition of the present disclosure preferably contains a solvent from the viewpoint of improving applicability.
- the “solvent” used herein includes a solvent for dilution used for dilution and a solvent contained in a commercially available adhesive.
- Solvents include hexane, heptane, octane, toluene, xylene, ethylbenzene, cyclohexane, methylcyclohexane and other hydrocarbons; dichloromethane, trichloroethane, trichloroethylene, tetrachloroethylene, dichloropropane and other halogenated hydrocarbons; methanol, ethanol, propanol, Alcohols such as isopropyl alcohol, butanol, isobutyl alcohol, diacetone alcohol; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; methyl acetate, acetic acid Esters such as ethyl, butyl
- the content of the solvent in the pressure-sensitive adhesive composition is, for example, from 30% by mass to 80% by mass with respect to the total amount of the pressure-sensitive adhesive composition from the viewpoint of improving coatability. %, More preferably 40% to 70% by weight, and still more preferably 40% to 60% by weight.
- the pressure-sensitive adhesive sheet of the present disclosure has a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition of the present disclosure described above. Since the pressure-sensitive adhesive sheet of the present disclosure has a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition of the present disclosure, the pressure-sensitive adhesive sheet has an excellent ultraviolet and blue light blocking function. In addition, the pressure-sensitive adhesive sheet of the present disclosure has an excellent pressure-sensitive adhesive force with a decrease in pressure-sensitive adhesive force caused by the ultraviolet absorber.
- the pressure-sensitive adhesive sheet of the present disclosure may be a pressure-sensitive adhesive sheet having no base material (non-base material type), or a pressure-sensitive adhesive sheet having a base material (substrate-type).
- the substrate is not particularly limited, and examples thereof include resin films such as polyethylene terephthalate (PET), polyethylene, polystyrene, polypropylene, polycarbonate, polyvinyl acetal, and acrylic resin.
- PET polyethylene terephthalate
- the substrate is preferably transparent.
- the thickness of the substrate is not particularly limited, and is preferably 15 ⁇ m to 1000 ⁇ m from the viewpoint of durability, for example.
- the exposed surface of the pressure-sensitive adhesive layer may be protected by a release film.
- a release film will not be restrict
- the resin film for example, PET film
- the peeling processing agent for example, silicone
- the release film protects the surface of the pressure-sensitive adhesive layer until the pressure-sensitive adhesive sheet is used, and is peeled off during use.
- the thickness of the pressure-sensitive adhesive layer is not particularly limited, and can be appropriately set according to the use, required performance, and the like.
- the thickness of the pressure-sensitive adhesive layer is preferably set in the range of 10 ⁇ m to 50 ⁇ m.
- the pressure-sensitive adhesive sheet of the present disclosure has an excellent blue light blocking function and has a superior pressure-sensitive adhesive strength reduction due to the inclusion of an ultraviolet absorber. Therefore, the pressure-sensitive adhesive sheet is suitably used, for example, as a display sheet. be able to.
- the adhesive sheet of this indication may have functional layers, such as a hard-coat layer, for example.
- the adhesive sheet of this indication is further excellent in the blocking
- the adhesive sheet of this indication may have functional layers, such as a heat insulation layer, for example.
- the pressure-sensitive adhesive sheet of the present disclosure By using the pressure-sensitive adhesive sheet of the present disclosure for application to an adherend having a polar group, the effect of improving the pressure-sensitive adhesive force is more remarkably exhibited.
- the adherend having a polar group include glass, metal, metal oxide, inorganic oxide, epoxy resin, urethane resin, imide resin, and amide resin.
- the polar group in which the sulfur atom of the ultraviolet absorber having a —S— structure and / or —SO 2 — structure in the molecule that is, the specific ultraviolet absorber
- the adhesive strength of the pressure-sensitive adhesive layer may be improved because of the interaction with the pressure-sensitive adhesive layer.
- the method for producing the pressure-sensitive adhesive sheet of the present disclosure is not particularly limited as long as the pressure-sensitive adhesive sheet of the present disclosure described above can be produced.
- the pressure-sensitive adhesive sheet of the present disclosure can be produced, for example, by the following method.
- the pressure-sensitive adhesive sheet of the present disclosure is formed by applying the pressure-sensitive adhesive composition to the release-treated surface of the release film and forming a coating film of the pressure-sensitive adhesive composition, and then forming the coating.
- An adhesive layer can be formed and produced by drying the film. If necessary, another release film may be overlaid on the formed pressure-sensitive adhesive layer so that the release treatment surface is in contact therewith.
- the pressure-sensitive adhesive sheet of the present disclosure is obtained by applying a pressure-sensitive adhesive composition to one side of a base material, forming a pressure-sensitive adhesive composition coating film, and then forming the formed coating film.
- the pressure-sensitive adhesive layer can be formed and produced by drying. If necessary, a release film may be overlaid on the formed pressure-sensitive adhesive layer so that the release treatment surface is in contact therewith.
- the method of applying the pressure-sensitive adhesive composition to the release film or the substrate is not particularly limited, and examples thereof include a blade coater, a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, and a spray.
- a blade coater a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, and a spray.
- the well-known coating method using a coater etc. is mentioned.
- Example 1 to Example 39 By stirring and mixing the components constituting the pressure-sensitive adhesive composition described in Tables 1 to 3 below using a stirrer equipped with a stirring blade [Three-One Motor (registered trademark), Shinto Kagaku Co., Ltd.] A pressure-sensitive adhesive composition was obtained.
- the numerical values described in the column of each component in Tables 1 to 4 indicate the content (unit: part by mass) of the component, and “-” means that the component is not contained.
- the numerical values of the pressure-sensitive adhesive content in Tables 1 to 4 are solid content conversion values.
- ⁇ Ultraviolet absorber> Compound 1 to compound 7 (compound 1 to compound 7 described above)
- Compound 8 [trade name: Tinuvin 326, triazole ultraviolet absorber, BASF Japan Ltd.]
- Compound 9 [trade name: Tinuvin 405, triazine ultraviolet absorber, BASF Japan Ltd.]
- Compound 10 [trade name: Tinuvin 477, triazine ultraviolet absorber, BASF Japan Ltd.]
- Compound 11 [hydroxymethoxybenzophenone sulfonic acid] ⁇ Solvent> ⁇ Methyl ethyl ketone (abbreviation: MEK)
- an evaluation pressure-sensitive adhesive sheet was produced as follows. Blade coater on a polyethylene terephthalate (PET) film (trade name: Cosmo Shine (registered trademark) A4300, thickness: 100 ⁇ m, Toyobo Co., Ltd.) as a substrate so that the film thickness after drying is 20 ⁇ m. A pressure-sensitive adhesive composition was applied to form a coating film of the pressure-sensitive adhesive composition. Next, the formed coating film was dried at 120 ° C. for 120 seconds to obtain an evaluation pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer (thickness: 20 ⁇ m) on the substrate.
- PET polyethylene terephthalate
- Adhesive strength was measured in accordance with Japanese Industrial Standard JIS Z0237: 2009.
- the evaluation pressure-sensitive adhesive sheet obtained above was cut into a size of 0.025 m ⁇ 0.1 m to prepare two pressure-sensitive adhesive sheet pieces for pressure-sensitive adhesive strength evaluation.
- the prepared pressure-sensitive adhesive sheet for evaluating the adhesive strength one of them is an environment of 23 ° C. and 50% relative humidity using a dedicated rubber roll [product name: tape pressing roll (manual type), Imoto Seisakusho Co., Ltd.] Underneath, the pressure-sensitive adhesive layer was pressed and bonded to a glass plate (thickness: 10 mm) placed on a table with a load of 1 kg to prepare a test piece A.
- the other sheet was used at 23 ° C. and relative humidity 50 using a dedicated rubber roll [product name: tape crimping roll (manual type), Imoto Seisakusho Co., Ltd.].
- the pressure-sensitive adhesive layer was pressure-bonded and bonded to a SUS (stainless steel) 304 plate (thickness: 10 mm) placed on a table with a load of 1 kg to prepare a test piece B.
- the adhesive strength (unit: N / 25 mm) when the adhesive strength evaluation adhesive sheet was peeled 180 ° in the long side (0.1 m) direction from the glass plate and the SUS304 plate, respectively.
- the electric horizontal type digital force gauge stand [Product name: FGS-50XB, Nidec Symposium] with a digital force gauge [Product name: FGP-5, Nidec Symposium]
- the substrate that is, PET film
- the pressure-sensitive adhesive layer were combined and sandwiched between jigs, and the measurement was performed under the condition of a peeling rate of 100 mm / min.
- the pressure-sensitive adhesive layer formed by the pressure-sensitive adhesive composition containing the ultraviolet absorber is used to determine how much the pressure-sensitive adhesive force of the pressure-sensitive adhesive layer is changed by the pressure-sensitive adhesive composition containing the ultraviolet absorber. It confirmed by comparing force and the adhesive force of the adhesive layer formed with the adhesive composition which does not contain a ultraviolet absorber.
- Example 1 Example 5, Example 9, Example 13, Example 17, Example 21, Example 25, Examples 29 to 39, Comparative Example 1, Comparative Example 5, Comparative Example 9, And the change (unit: N / 25mm) of the adhesive force by the ultraviolet absorber of each adhesive layer formed with the adhesive composition of Comparative Example 13 is the adhesive layer formed with the adhesive composition of Reference Example 1.
- Example 2 Example 6, Example 10, Example 14, Example 18, Example 22, Example 26, Comparative Example 2, Comparative Example 6, Comparative Example 10, and Comparative Example 14
- the change in the adhesive strength (unit: N / 25 mm) of each formed adhesive layer by the ultraviolet absorber was calculated based on the adhesive strength of the adhesive layer formed by the adhesive composition of Reference Example 2.
- the change (unit: N / 25 mm) of the adhesive strength of each formed adhesive layer by the ultraviolet absorber was calculated based on the adhesive strength of the adhesive layer formed by the adhesive composition of Reference Example 3.
- the change (unit: N / 25 mm) of the adhesive strength of each formed adhesive layer by the ultraviolet absorber was calculated based on the adhesive strength of the adhesive layer formed by the adhesive composition of Reference Example 4.
- a positive value for the change in adhesive strength means that the adhesive strength of the adhesive layer has been improved by the UV absorber, and a negative value for the change in adhesive strength means that the UV absorption It means that the adhesive strength of the pressure-sensitive adhesive layer was lowered by the agent.
- the results are shown in Tables 5-8.
- the integral value of the spectrum area in the adhesive sheet (that is, the adhesive sheet piece for optical property evaluation of Examples and Comparative Examples) having an adhesive layer formed of an adhesive composition containing an ultraviolet absorber
- From the integral value of the spectrum area in the pressure-sensitive adhesive sheet (that is, the pressure-sensitive adhesive sheet piece for optical property evaluation of the reference example) having a pressure-sensitive adhesive layer formed by a pressure-sensitive adhesive composition not containing the UV, it was decreased by including the ultraviolet absorber.
- the ratio of the integral value of the spectral area (that is, the ultraviolet blocking rate) was calculated, and the ultraviolet blocking function of the adhesive layer was evaluated.
- the evaluation criteria are shown below. In the following evaluation criteria, “S” indicates the most excellent ultraviolet blocking function, and if “S” or “A”, there is no practical problem.
- the ultraviolet blocking rate is 70% or more.
- Blue light blocking rate based on ISO 12312-1: 2013 standard is 50% or more.
- the prepared pressure-sensitive adhesive sheet piece for optical property evaluation was placed on white paper.
- the pressure-sensitive adhesive sheet piece for optical property evaluation on paper was visually observed, and whether or not the pressure-sensitive adhesive sheet piece for optical property evaluation had a yellowish color was evaluated according to the following evaluation criteria.
- the pressure-sensitive adhesive compositions of Examples 1 to 39 including pressure-sensitive adhesives and ultraviolet absorbers having at least one of —S— and —SO 2 — structures in the molecule.
- the pressure-sensitive adhesive layer formed of the product had a function of blocking ultraviolet rays and blue light, and was excellent in adhesive strength. Further, it is clear that the adhesive layers formed from the adhesive compositions of Examples 1 to 39 are improved in adhesive strength by containing an ultraviolet absorber in comparison with Reference Examples 1 to 4. It became.
- a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive compositions of Comparative Examples 1 to 16 containing a pressure-sensitive adhesive and an ultraviolet absorber having neither of the structures of —S— or —SO 2 — in the molecule Although it has an ultraviolet blocking function, it has been observed that the adhesive strength tends to decrease when it contains an ultraviolet absorber.
- a PET film (trade name: KB film N10, thickness: 100 ⁇ m, Kimoto Co., Ltd.) having a hard coat layer on one side was prepared.
- the pressure-sensitive adhesive composition of Example 1 was applied using a blade coater so that the film thickness after drying was 20 ⁇ m.
- the coating film was formed.
- the formed coating film was dried at 120 ° C. for 120 seconds to prepare a pressure-sensitive adhesive sheet (that is, a pressure-sensitive adhesive sheet for display sheet) as a display sheet having a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m.
- the produced pressure-sensitive adhesive sheet for display sheet had a function of blocking ultraviolet light and blue light, and was excellent in adhesive strength.
- a PET film (thickness: 100 ⁇ m) having a heat insulating layer containing silver nanowires described in paragraph [0117] of JP-A-2016-33629 was prepared.
- the pressure-sensitive adhesive composition of Example 1 was applied to the surface of the PET film opposite to the heat insulating layer using a blade coater so that the film thickness after drying was 20 ⁇ m.
- a coating film was formed.
- the formed coating film was dried at 120 ° C. for 120 seconds to prepare a pressure-sensitive adhesive sheet (that is, a pressure-sensitive adhesive sheet for window film) as a window film having a pressure-sensitive adhesive layer having a thickness of 20 ⁇ m.
- the produced adhesive sheet for window films had a function of blocking ultraviolet light and blue light, and was excellent in adhesive strength.
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Abstract
L'invention concerne une composition adhésive sensible à la pression qui comprend un adhésif sensible à la pression et un absorbeur d'ultraviolets ayant la structure – S- et/ou la structure – SO2- dans la molécule ; et une feuille adhésive sensible à la pression comprenant une couche adhésive sensible à la pression comprenant la composition adhésive sensible à la pression.
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JP2019507647A JPWO2018173979A1 (ja) | 2017-03-21 | 2018-03-16 | 粘着剤組成物及び粘着シート |
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JP2017054562 | 2017-03-21 | ||
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PCT/JP2018/010632 WO2018173979A1 (fr) | 2017-03-21 | 2018-03-16 | Composition adhésive sensible à la pression et feuille adhésive sensible à la pression |
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JPWO2020261886A1 (fr) * | 2019-06-28 | 2020-12-30 | ||
WO2021006097A1 (fr) * | 2019-07-09 | 2021-01-14 | 富士フイルム株式会社 | Feuille adhésive, corps multicouche, dispositif d'affichage et dispositif d'affichage électroluminescent organique |
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WO2020261886A1 (fr) * | 2019-06-28 | 2020-12-30 | 富士フイルム株式会社 | Absorbeur de rayons ultraviolets, composition absorbant les rayons ultraviolets, film, stratifié et nouveau composé absorbant les rayons ultraviolets |
CN113993856A (zh) * | 2019-06-28 | 2022-01-28 | 富士胶片株式会社 | 紫外线吸收剂、紫外线吸收组合物、紫外线吸收膜、层叠体及新型化合物 |
JP7279162B2 (ja) | 2019-06-28 | 2023-05-22 | 富士フイルム株式会社 | 紫外線吸収剤、紫外線吸収組成物、紫外線吸収膜、積層体及び新規化合物 |
US12173188B2 (en) | 2019-06-28 | 2024-12-24 | Fujifilm Corporation | Ultraviolet absorbing agent, ultraviolet absorbing composition, ultraviolet absorbing film, laminate, and novel compound |
WO2021006097A1 (fr) * | 2019-07-09 | 2021-01-14 | 富士フイルム株式会社 | Feuille adhésive, corps multicouche, dispositif d'affichage et dispositif d'affichage électroluminescent organique |
JPWO2021006097A1 (fr) * | 2019-07-09 | 2021-01-14 | ||
KR20220016186A (ko) * | 2019-07-09 | 2022-02-08 | 후지필름 가부시키가이샤 | 점착제 시트, 적층체, 표시 장치, 유기 일렉트로 루미네선스 표시 장치 |
CN114096632A (zh) * | 2019-07-09 | 2022-02-25 | 富士胶片株式会社 | 粘合剂片、层叠体、显示装置及有机电致发光显示装置 |
JP7291786B2 (ja) | 2019-07-09 | 2023-06-15 | 富士フイルム株式会社 | 粘着剤シート、積層体、表示装置、有機エレクトロルミネッセンス表示装置 |
CN114096632B (zh) * | 2019-07-09 | 2023-06-27 | 富士胶片株式会社 | 粘合剂片、层叠体、显示装置及有机电致发光显示装置 |
KR102594786B1 (ko) * | 2019-07-09 | 2023-10-26 | 후지필름 가부시키가이샤 | 점착제 시트, 적층체, 표시 장치, 유기 일렉트로 루미네선스 표시 장치 |
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