JP2013129785A - 感圧式接着剤組成物、及びそれを用いてなる感圧式接着剤フィルム - Google Patents
感圧式接着剤組成物、及びそれを用いてなる感圧式接着剤フィルム Download PDFInfo
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- JP2013129785A JP2013129785A JP2011281439A JP2011281439A JP2013129785A JP 2013129785 A JP2013129785 A JP 2013129785A JP 2011281439 A JP2011281439 A JP 2011281439A JP 2011281439 A JP2011281439 A JP 2011281439A JP 2013129785 A JP2013129785 A JP 2013129785A
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- Prior art keywords
- group
- meth
- sensitive adhesive
- substituent
- methyl
- 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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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 177
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- -1 salt compound Chemical class 0.000 claims abstract description 430
- 229920001577 copolymer Polymers 0.000 claims abstract description 98
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 81
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 50
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 44
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 33
- 125000000524 functional group Chemical group 0.000 claims abstract description 32
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 31
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 24
- 150000008040 ionic compounds Chemical class 0.000 claims abstract description 20
- 229910052751 metal Chemical class 0.000 claims abstract description 16
- 239000002184 metal Chemical class 0.000 claims abstract description 16
- 230000009477 glass transition Effects 0.000 claims abstract description 9
- 125000005647 linker group Chemical group 0.000 claims description 125
- 125000001424 substituent group Chemical group 0.000 claims description 110
- 239000000178 monomer Substances 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 230000003287 optical effect Effects 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 239000010410 layer Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000011521 glass Substances 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 20
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 210000002858 crystal cell Anatomy 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000013522 chelant Substances 0.000 claims description 7
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 6
- 150000002012 dioxanes Chemical class 0.000 claims description 5
- 150000004862 dioxolanes Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 150000004901 trioxanes Chemical class 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000005499 phosphonyl group Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract description 7
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 159
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 156
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 88
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- 230000015572 biosynthetic process Effects 0.000 description 64
- 238000003786 synthesis reaction Methods 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 62
- 239000002253 acid Substances 0.000 description 60
- 239000000243 solution Substances 0.000 description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 53
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 42
- 238000007792 addition Methods 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 35
- 229920002554 vinyl polymer Polymers 0.000 description 30
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 27
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 26
- 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 25
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 238000000034 method Methods 0.000 description 25
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 20
- 125000002947 alkylene group Chemical group 0.000 description 20
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000012790 adhesive layer Substances 0.000 description 19
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 15
- 239000002216 antistatic agent Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 14
- 239000012788 optical film Substances 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 239000000853 adhesive Substances 0.000 description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 11
- 230000001476 alcoholic effect Effects 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 238000007667 floating Methods 0.000 description 11
- 238000005187 foaming Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 10
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000007789 sealing Methods 0.000 description 9
- 230000003068 static effect Effects 0.000 description 9
- 229920002284 Cellulose triacetate Polymers 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 8
- 230000005611 electricity Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 125000005587 carbonate group Chemical group 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 229940070710 valerate Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
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- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 6
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 6
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- 125000004018 acid anhydride group Chemical group 0.000 description 5
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 238000004132 cross linking Methods 0.000 description 5
- 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 5
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
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- 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 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
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Abstract
【解決手段】官能基として水酸基及び/又はカルボキシル基を有し、更に側鎖に二個以上の酸素原子を有する四員環以上の環状化合物を開環付加してなるガラス転移温度が−60〜0℃の共重合体(A)と、共重合体(A)中の官能基と反応し得る官能基を有する架橋剤(B)と、特定構造を有するアンモニウム塩または金属塩系化合物であるイオン性化合物(C)を含有することを特徴とする感圧式接着剤組成物。
【選択図】 なし
Description
また、FPDは、表示装置として利用するだけではなく、その表面にタッチパネルの機能を設けて、入力装置として利用されることもある。タッチパネルにも、保護フィルム、反射防止フィルムやITO蒸着樹脂フィルムなどが使用されている。
このようなフィルムは、感圧式接着剤を介して被着体に貼着して表示装置に使用されている。表示装置に用いられる感圧式接着剤は、まず透明性に優れることが要求されるので、アクリル系樹脂を主剤とする感圧式接着剤が一般に使用されている。
しかし、貼着後の積層体は、一般に、接着性向上のために高温下で一定時間保管した後に検査されるので、その間に剥離強度が高くなって偏光フィルムを剥ぎ取り難くなるばかりでなく、偏光フィルムの再剥離性が低下して剥がした後、ガラス面に糊残りや曇り等の汚染が生じる場合があった。
そこで感圧式接着剤の分子量や感圧式接着剤の架橋度を調整し、接着力を高くすることによって、偏光フィルムの寸法変化に抗して、過酷な環境下でも発泡、浮き、剥がれが生じないようにする試みがなされた。
しかし、リワークする際に生じる静電気により液晶や電子回路にトラブルを起こす場合がある。また、上記のように剥離フィルムを剥離する際に生じる静電気により、偏光フィルムが帯電し液晶セル用のガラス面に貼り付ける場合にも、同様なトラブルが発生することが指摘されている。さらには、静電気の存在は、埃やクズを吸引してしまい、異物による欠点を引き起こす問題も有しており、早期の解決が望まれていた。
例えば、積層される部材に対して制電性能を付与するためには、樹脂には制電剤による処理が行われていることが多い。制電剤の利用のされ方によって、表面処理と内部処理に大別される。
また、電子顕微鏡でなければ確認できない10μm以下の気泡が、中央部に1m2あたり10個程度発生してしまう。
さらに、20インチ以上の表示装置では、見やすさの観点から光源の輝度を高く設定しなければならない。特許文献7に記載される感圧式接着剤を用いてなる感圧式接着光学フィルムは、20インチ未満の表示装置では白抜けは問題視されなかった。しかし、20インチ以上で使用される高輝度の光源を用いた表示装置では白抜けが目立ってしまうという問題も生じた。
また、耐熱性向上のため、アセトアセチル基を有する単量体を共重合した感圧式接着剤(特許文献11)が知られている。
従って、一般的な感圧式接着剤を提供する際には、制電性能の補助効果を示すものの、特許文献9、10に記載される感圧式接着剤を用いた感圧式接着光学フィルムは、被着体に貼着後、高温下または高温高湿条件下、低温から高温までのヒートサイクル等に長期間曝されたり、重合中、分解で生じたりした、ポリエーテル系オリゴマーにより、ポリエーテルポリオール(特許文献7)を配合した場合と同様、光学フィルムの周辺端部に極めて小さい気泡がスジ状に連なった状態で発生してしまう。
さらに、アルキレンオキサイドの付加したアクリル酸系単量体を共重合しただけでは、制電効果を得ることは出来ない。そのため、このようなアルキレンオキサイドの付加したアクリル酸系共重合体に制電剤を加える場合がある。この場合、制電剤が被着体側の界面に移行して、感圧式接着光学フィルムを剥離した際には制電性能の向上は認められるが、被着体に貼着後、高温下または高温高湿条件下では、制電剤の界面移行により、浮き・ハガレが起こるなど、耐熱、耐湿熱性が著しく低下することが知られている。
さらには、制電性能のみならず、透明性や樹脂、溶剤への溶解性(相溶性)、並びに耐湿熱性を併せ持つ感圧式接着剤が望まれていた。
すなわち、第1の発明は、官能基として水酸基及び/又はカルボキシル基を有し、更に側鎖に二個以上の酸素原子を有する四員環以上の環状化合物を開環付加してなるガラス転移温度が−60〜0℃の共重合体(A)と、共重合体(A)中の官能基と反応し得る官能基を有する架橋剤(B)と、下記一般式(1)、(2)または(3)から選ばれるイオン性化合物(C)とを含有することを特徴とする感圧式接着剤組成物に関する。
〔一般式(3)中R5〜R8は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルケニル基、置換基を有してもよいアルキニル基、置換基を有してもよいアリール基、又は、置換基を有してもよい複素環基を表し、隣り合う置換基同士で環を形成してもよい。
R9は、置換基を有してもよいアルキレン結合基、置換基と二重結合を有してもよいアルキレン結合基、置換基と三重結合を有してもよいアルキレン結合基、置換基を有してもよいアリーレン結合基、置換基を有してもよい複素環結合基、又は、エーテル結合基、エステル結合基、チオエーテル結合基、ジチオール結合基、カルボニル結合基、スルフィニル結合基、スルホニル結合基、ホスホニル結合基、アミノ結合基、イミノ結合基、もしくはシリル結合基を表す。
R10は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、ハロゲン基を表す。
R11は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、−R9R10を表す。〕
また、第5の発明は、環状ホルマール(f−1)が、ジオキソラン類、ジオキサン類、トリオキサン類から選ばれる少なくとも1種であることを特徴とする第4の発明の感圧式接着剤組成物に関する。
また、第7の発明は、共重合体(A)100重量部に対して、イオン性化合物(C)を0.01〜10重量部含むことを特徴とする第1〜6の発明いずれかの感圧式接着剤組成物に関する。
また、第9の発明は、架橋剤(B)がエポキシ化合物(b2)、アジリジン化合物(b3)、カルボジイミド化合物(b4)、オキサゾリン化合物(b5)、もしくは金属キレート化合物(b6)のいずれかであることを特徴とする第1〜7の発明いずれかの感圧式接着剤組成物に関する。
また、第10の発明は、第1〜9の発明のいずれかに記載の感圧式接着剤組成物から形成される感圧式接着剤層上に光学部材が積層されてなる積層体に関する。
本発明に用いられる感圧式接着剤組成物は、官能基として水酸基及び/又はカルボキシル基を有し、更に側鎖に二個以上の酸素原子を有する四員環以上の環状化合物を開環付加してなるガラス転移温度が−60〜0℃の共重合体(A)と、共重合体(A)中の官能基と反応し得る官能基を有する架橋剤(B)、及びイオン性化合物(C)を含有することを特徴とする感圧式接着剤組成物である。
2−(2'−ヒドロキシ−5'−(メタ)アクリロイルオキシプロピルフェニル)−5−クロロ−2H−ベンゾトリアゾール、2−(2'−ヒドロキシ−3'−tert−ブチル−5'−(メタ)アクリロイルオキシエチルフェニル)−2H−ベンゾトリアゾール、2−(2'−ヒドロキシ−3'−tert−ブチル−5'−(メタ)アクリロイルオキシエチルフェニル)−5−クロロ−2 H−ベンゾトリアゾール等の水酸基含有ベンゾトリアゾール系(メタ)アクリル酸エステル類;
等のアルコキシシリル基含有(メタ)アクリル酸エステル類;
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
4−ビニル安息香酸メチルポリ(エチレンオキサイド)、4−ビニル安息香酸エチルポリ(エチレンオキサイド)、4−イソプロペニル安息香酸メチルポリ(プロピレンオキサイド)、4−イソプロペニル安息香酸エチルポリ(プロピレンオキサイド)などのポリアルキレンオキサイド部位を有するビニル安息香酸エステル系またはイソプロペニル安息香酸エステル系単量体;
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
例えば、4−アクリロイルモルホリン、N−ビニル−2−ピロリドン、N−ビニル−ε−カプロラクタムなどの環状アミド基含有(メタ)アクリルアミド類;
例えば、2−ビニルピリジン、4−ビニルピリジン、2−ビニルピペラジン、N−ビニルイミダゾール、4−ビニルピペラジン、2,4−ジアミノ−6−ビニル−s−トリアジンなどの窒素原子含有複素環ビニル系単量体;
例えば、ギ酸ビニル、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、カプリン酸ビニル、ラウリン酸ビニル、バーサチック酸ビニル、ピバリン酸ビニル、パルミチン酸ビニル、ステアリン酸ビニル等のカルボン酸のビニルエステル類;
例えば、グリシジルシンナマート、アリルグリシジルエーテル、ビニルシクロヘキセンモノオキシラン、1,3−ブタジエンモノオキシラン等のグリシジル基含有ビニルエステル類;
例えば、アレン、1,2−ブタジエン、1,3−ブタジエン、2−メチル−1,3−ブタジエン、2−クロロ−1,3−ブタジエンなどのジエン類;
例えば、cis−コハク酸ジアリル、2−メチリデンコハク酸ジアリル、(E)−ブタ−2−エン酸ビニル、(Z)−オクタデカ−9−エン酸ビニル、(9Z,12Z,15Z)−オクタデカ−9,12,15−トリエン酸ビニル等の多官能の不飽和結合を含有するエチレン性不飽和単量体類;
の前駆体(AP)は、定法に従い、重合開始剤を用いて、塊状重合、溶液重合、乳化重合、懸濁重合などの方法により合成される。好ましくは溶液重合で合成される。
トリメチレンスルホキシラート、1,3,5‐ジオキサチアン、2‐クロロ‐4‐メチル‐1,3,2‐ジオキサホスホラン、2‐スルフィド、2‐クロロ‐1,3,2‐ジオキサルセナン、2‐ブロモ‐1,3,2‐ジオキサルセナン、2‐クロロ‐1,3,2‐ジオキサホスホリナン2‐スルフィド、2‐チオラト‐1,3,2‐ジオキサホスホリナン2‐セレニド等の2個の酸素原子以外に、更に他の原子を有するジオキサン誘導体類が挙げられる。
5‐(フェニルチオ)‐1,3‐ジオキソラン‐2‐オン、5‐(ベンジルオキシ)‐1,3‐ジオキソラン‐2‐オン、4‐(イソブトキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(4‐ノニルベンジルオキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(4‐クロロフェニルチオメチル)‐1,3‐ジオキソラン‐2‐オン、4‐[3‐(クロロメチル)フェニル]‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(クロロメチル)フェニル]‐1,3‐ジオキソラン‐2‐オン、4,4‐ジプロピル‐5‐[1‐(4‐メトキシフェノキシ)エテニル]‐1,3‐ジオキソラン‐2‐オン、4,4‐ジペンチル‐5‐[1‐(4‐メトキシフェノキシ)エテニル]‐1,3‐ジオキソラン‐2‐オン、4,4‐ジイソプロピル‐5‐[1‐(4‐メトキシフェノキシ)エテニル]‐1,3‐ジオキソラン‐2‐オン、4,4‐ジフェネチル‐5‐[1‐(4‐メトキシフェノキシ)エテニル]‐1,3‐ジオキソラン‐2‐オン、4,4‐ビス(2‐シクロヘキシルエチル)‐5‐[1‐(4‐メトキシフェノキシ)エテニル]‐1,3‐ジオキソラン‐2‐オン、4‐[1‐(フェニルチオ)シクロヘキシル]‐1,3‐ジオキソラン‐2‐オン、4‐(3‐メトキシ‐4‐エトキシフェニル)‐5‐(ヒドロキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(フェノキシカルボニルオキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐ベンジリデン‐5,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、4‐[(2‐ナフチル)メチレン]‐5,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、4‐(4‐クロロベンジリデン)‐5,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(トリフルオロメチル)ベンジリデン]‐5,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、5‐メチル‐5‐フェニル‐4‐(3‐フェニルプロピリデン)‐1,3‐ジオキソラン‐2‐オン、5,5‐ジメチル‐4‐(3‐フェニルプロピリデン)‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(クロロカルボニルオキシ)ブチル]‐1,3‐ジオキソラン‐2‐オン、4‐クロロ‐1,3‐ジオキソラン‐2‐オン、4‐クロロ‐4,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、4‐(クロロカルボニルオキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(p‐クロロフェノキシメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(クロロメチル)‐1,3‐ジオキソラン‐2‐オン、フルオロエチレンカーボネート、4‐フルオロ‐5‐メチル‐1,3‐ジオキソラン‐2‐オン、4‐(フルオロメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(2,2,3,3,4,4,5,5,5‐ノナフルオロペンチル)‐1,3‐ジオキソラン‐2‐オン、4,5‐ジフルオロ‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐メチル‐1,3‐ジオキソラン‐2‐オン、4,4‐ジフルオロ‐1,3‐ジオキソラン‐2‐オン、4,5‐ジクロロ‐1,3‐ジオキソラン‐2‐オン、4‐(α,α‐ジフルオロベンジル)‐1,3‐ジオキソラン‐2‐オン、4‐[(テトラヒドロフラン‐3‐イル)ジフルオロメチル]‐1,3‐ジオキソラン‐2‐オン、(4S,5R)‐4,5‐ジフェニル‐1,3‐ジオキソラン‐2‐オン、4α,5α‐ジメチル‐1,3‐ジオキソラン‐2‐オン、(4R,5R)‐4,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、(4S,5S)‐4,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、(4S)‐4β‐メチル‐1,3‐ジオキソラン‐2‐オン、(R)‐4‐メチル‐1,3‐ジオキソラン‐2‐オン、(S)‐5‐エチル‐1,3‐ジオキソラン‐2‐オン、4‐[(トリフェニルシリル)メチル]‐5,5‐ジメチル‐1,3‐ジオキソラン‐2‐オン、4‐[9‐(3‐チエニル)ノニル]‐1,3‐ジオキソラン‐2‐オン、4‐(メチルアミノメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(4‐クロロフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐(フェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐(4‐メトキシフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐(4‐ブロモフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐[(4‐メトキシフェニル)チオ]‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐(4‐ブロモフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐(フェニルチオフルオロメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(フェニルチオジフルオロメチル)‐1,3‐ジオキソラン‐2‐オン、4‐(フェニルチオメチル)‐1,3‐ジオキソラン‐2‐オン、4‐[ジフルオロ(フェニルスルホニル)メチル]‐1,3‐ジオキソラン‐2‐オン、4‐[ジフルオロ(フェニルスルフィニル)メチル]‐1,3‐ジオキソラン‐2‐オン、4,4′‐[スルホニルビス(p‐フェニレンオキシメチレン)]ビス(1,3‐ジオキソラン‐2‐オン)、4‐(4‐メチルフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐(4‐メチルフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐[[4‐(フルオロメチル)フェニル]チオ]‐1,3‐ジオキソラン‐2‐オン、4,4,5,5‐テトラメチル‐2‐(フェニルスルホニルオキシイミノ)‐1,3‐ジオキソラン、2‐(4‐ニトロフェノキシ)‐4‐メチル‐2‐ホスファ(V)‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐(フェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐フルオロ‐4‐(4‐クロロフェニルチオ)‐1,3‐ジオキソラン‐2‐オン、4‐(グリシジルオキシメチル)‐1,3‐ジオキソラン‐2‐オン、グリシジルカルバミド酸(2‐オキソ‐1,3‐ジオキソラン‐4‐イル)メチル、4‐(ノルボルナ‐5‐エン‐2‐イル)‐1,3‐ジオキソラン‐2‐オン、4‐[2‐(2‐ナフチル)エチル]‐5‐メトキシ‐1,3‐ジオキソラン‐2‐オン、4‐[2‐(1‐ナフチル)エチル]‐5‐メトキシ‐1,3‐ジオキソラン‐2‐オン、4,4‐ジメチル‐5‐(3‐チエニルメチレン)‐1,3‐ジオキソラン‐2‐オン、4‐[2‐[ジメチル(トリメチルシリルオキシ)シリル]エチル]‐1,3‐ジオキソラン‐2‐オン、4‐[2‐[(メチル)ビス(トリメチルシリルオキシ)シリル]エチル]‐1,3‐ジオキソラン‐2‐オン、4‐[2‐(トリメチルシリル)エチル]‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(グリシジルカルバモイルオキシ)ブチル]‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(2‐オキソ‐1,3‐ジオキソラン‐4‐イルメチルカルバモイルオキシ)ブチル]‐1,3‐ジオキソラン‐2‐オン、4‐[4‐(グリシジルカルバモイルオキシ)ブチル]‐1,3‐ジオキソラン‐2‐オン、4‐(2‐オキソ‐1,3‐ジオキソラン‐4‐イルメチルカルバモイルオキシメチル)‐1,3‐ジオキソラン‐2‐オンなどの5員環カーボネート類;
[製造法1]
あるいは、予め(a1)及び/又は(a2)、及び必要に応じて(a3)で示されるエチレン性不飽和単量体を共重合することにより共重合体(A)の前駆体(AP)を得た(工程1)のち、前駆体(AP)に含有されている水酸基及び/又はカルボキシル基に、環状エステル(f)を開環付加反応させることにより共重合体(A)を得る(工程2)方法と、
[製造法2]
あるいは、予め(a1)及び/又は(a2)、及び必要に応じて(a3)で示されるエチレン性不飽和単量体に環状エステル(f)を共存させて、エチレン性不飽和単量体を共重合するとともに、環状エステル(f)の開環付加反応を同時におこなうことにより、共重合体(A)を得る(工程3)方法、
のいずれかの方法により、共重合体(A)に有酸素結合基を導入することができる。
また、共重合体(A)中の官能基がカルボキシル基のみの場合における開環付加反応は、後述の触媒によって、環状化合物の酸素原子に求電子付加してカルボカチオンが生成し、共重合体(A)中のカルボキシル基が開始点となって開環付加し、末端に新たなカルボキシル基を生成する。同様にして環状化合物(f)が開環付加してカチオン重合するが、水酸基への反応性の方が著しく速いため、含有している水分が開始点となって、カチオン重合するのが一般的である。
水酸化マグネシウム、水酸化カルシウム、水酸化ストロンチウム、水酸化バリウム等のアルカリ土類金属水酸化物類;
を挙げることができる。
有機チタン化合物類としては、例えば、ジブチルチタニウムジクロライド、テトラブチルチタネート、テトラブトキシチタネート、テトラエチルチタネート、テトライソプロピルチタネート、ブトキシチタニウムトリクロライド等を挙げることができる。
有機鉄化合物類としては、例えば、2−エチルヘキサン酸鉄、鉄アセチルアセトネートなどを挙げることができる。
有機コバルト化合物類としては、例えば、酢酸コバルト、安息香酸コバルト、2−エチルヘキサン酸コバルト等を挙げることができる。
金属ハロゲン化物類としては、例えば、塩化第一錫、臭化第一錫、ヨウ化第一錫等を挙げることができる。
トシル酸類としては、例えば、p−トルエンスルホン酸、ベンゼンスルホン酸、キシレンスルホン酸、エチルベンゼンスルホン酸、クロロベンゼンスルホン酸等が挙げられ、これらのアルカリ金属塩、アンモニウム塩、アミン塩、及び水和物も含まれる。
一方、共重合体(A)の官能基がカルボキシル基の場合、その酸価は0.01〜50mgKOH/gが好ましく、0.1〜30mgKOH/gがより好ましい。そして水酸基と反応しうる架橋剤(B)を用いた場合は0.1〜10mgKOH/gが好ましい。上記それぞれの数値範囲外のときは、感圧式接着剤として用いた場合の耐湿熱性が低下する恐れがある。
ヒドロシラン類としては、例えば、トリメチルシラン、トリエチルシラン、トリプロピルシラン、トリブチルシラン、トリヘキシルシラン、ジエチルメチルシラン、ブチルジメチルシラン、ジメチルフェニルシラン、トリフェニルシラン、メチルフェニルエテニルシラン、ペンタメチルジシロキサン、アリルジメチルシラン、トリス(トリメチルシロキシ)シラン、1,1,1,3,5,5,5−ヘプタメチルトリシロキサン、1,1,1,3,5,7,7,7−オクタメチルテトラシロキサン、1,3,5,7,9−オクタフェニルシクロテトラシロキサン等の単官能のSi−H基を有するヒドロシラン類が挙げられる。
テトラヒドロフラン−2,5−ジオンの誘導体(メチルテトラヒドロフラン−2,5−ジオン、2,2−ジメチルテトラヒドロフラン−2,5−ジオン、ブチルテトラヒドロフラン−2,5−ジオン、イソブチルテトラヒドロフラン−2,5−ジオン、ヘキシル無水コハク酸、オクチル無水コハク酸、ドデセニルテトラヒドロフラン−2,5−ジオン、フェニルテトラヒドロフラン−2,5−ジオン等)、テトラヒドロピラン−2,6−ジオンの誘導体(テトラヒドロピラン−2,6−ジオン、3−アリルテトラヒドロピラン−2,6−ジオン、2,4−ジメチルテトラヒドロピラン−2,6−ジオン、2,4−ジエチルテトラヒドロピラン−2,6−ジオン、ブチルテトラヒドロピラン−2,6−ジオン、ヘキシルテトラヒドロピラン−2,6−ジオン等)、2,5−ジヒドロフラン−2,5−ジオンの誘導体(2−メチル2,5−ジヒドロフラン−2,5−ジオン、2,3−ジメチル2,5−ジヒドロフラン−2,5−ジオン、ブチル2,5−ジヒドロフラン−2,5−ジオン、ペンチル2,5−ジヒドロフラン−2,5−ジオン、ヘキシル2,5−ジヒドロフラン−2,5−ジオン、オクチル2,5−ジヒドロフラン−2,5−ジオン、デシル2,5−ジヒドロフラン−2,5−ジオン、ドデシル2,5−ジヒドロフラン−2,5−ジオン、2,3−ジクロロ2,5−ジヒドロフラン−2,5−ジオン、フェニル2,5−ジヒドロフラン−2,5−ジオン、2,3−ジフェニル2,5−ジヒドロフラン−2,5−ジオン等)などの無水物誘導体も利用できる。
また共重合体(A)の官能基がカルボキシル基の場合、封止化合物(D)は、アミン化合物(d4)を用いることが好ましい。
ところで、感圧式接着剤の場合、主成分たる共重合体(A)に対し、後述の架橋剤(B)は、少量配合することが一般的である。このような感圧式接着剤から形成される接着剤層は、架橋状態が緩い(換言すると疎)なので、緻密に架橋される硬化塗膜とは異なり、接着剤層のTgは、架橋前の共重合体(A)のTgにほぼ等しい。従って、感圧式接着剤から形成される感圧式接着剤層のTgが0℃以下、好ましくは−5℃以下となるように、各種エチレン性不飽和単量体や、あるいは環状化合物(f)の種類、量を選択すればよい。
一方、共重合体(A)に対し、後述の架橋剤(B)を多量配合して得られる、いわゆる架橋性IPN構造を形成した接着剤層は、架橋後のTgが架橋前と大幅に異なるため、DSC測定(示差走査熱量測定)や動的粘弾性測定により求めることが好ましい。
共重合体(A)のMwが500,000未満の場合は、光学用感圧式接着フィルムをガラス等の液晶用セル部材に貼着した後、感圧式接着剤層の凝集破壊が起こりやすくなる場合がある。
本発明において、共重合体(A)に架橋剤(B)を含有させることで、感圧式接着剤が得られる。
本発明の架橋剤(B)とは、上述したように、感圧式接着剤組成物の架橋構造を形成するため、さらに架橋構造に加えて架橋性IPN構造を形成するために使用され、より具体的には、共重合体(A)の水酸基及び/又はカルボキシル基と反応しうる化合物である。
共重合体(A)中の官能基がカルボキシル基の場合、架橋剤(B)の官能基としてはイソシアネート基、オキシラン基、アミノ基、アジリジル基、オキサゾリン基、金属キレート基が挙げられ、共重合体(A)中の官能基が水酸基の場合は、架橋剤(B)の官能基としてはイソシアネート基、N−ヒドロキシメチル基が挙げられる。
特に、イソシアネート基を有するポリイソシアネート化合物(b1)は、架橋反応後の感圧式接着剤の接着性や被覆層への密着性に優れていることから好ましく用いられる。
錫系化合物としては、ジブチル錫ジクロライド、ジブチル錫オキサイド、ジブチル錫ジブロマイド、ジブチル錫ジマレエート、ジブチル錫ジラウレート(別名:DBTDL)、ジブチル錫ジアセテート、ジブチル錫スルファイド、トリブチル錫スルファイド、トリブチル錫オキサイド、トリブチル錫アセテート、トリエチル錫エトキサイド、トリブチル錫エトキサイド、ジオクチル錫オキサイド、トリブチル錫クロライド、トリブチル錫トリクロロアセテート、2−エチルヘキサン酸錫等が挙げられる。
非錫系化合物としては、例えばジブチルチタニウムジクロライド、テトラブチルチタネート、ブトキシチタニウムトリクロライドなどのチタン系、オレイン酸鉛、2−エチルヘキサン酸鉛、安息香酸鉛、ナフテン酸鉛などの鉛系、2−エチルヘキサン酸鉄、鉄2,4−ペンタジオネートなどの鉄系、安息香酸酸コバルト、2−エチルヘキサン酸コバルトなどのコバルト系、ナフテン酸亜鉛、2−エチルヘキサン酸亜鉛などの亜鉛系、ナフテン酸ジルコニウムなどが挙げられる。
上記触媒の中で、ジブチル錫ジラウレート(別名:DBTDL)、2−エチルヘキサン酸錫等が反応性や衛生性の点で好ましい。
このような化合物としては、以下のジイソシアネートを脱炭酸縮合反応させたものが挙げられる。
ジイソシアネートとしては、4,4’−ジフェニルメタンジイソシアネート、3,3’−ジメトキシ−4,4’−ジフェニルメタンジイソシアネート、3,3’−ジメチル−4,4’−ジフェニルメタンジイソシアネート、4,4’−ジフェニルエーテルジイソシアネート、3,3’−ジメチル−4,4’−ジフェニルエーテルジイソシアネート、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、1−メトキシフェニル−2,4−ジイソシアネート、イソホロンジイソシアネート、4,4’−ジシクロヘキシルメタンジイソシアネート、テトラメチルキシリレンジイソシアネートの内の一種、またはこれらの混合物を使用することができる。
本発明に用いられる下記一般式(1)で表されるアンモニウム塩系の化合物(C1)、下記一般式(2)で表されるアルカリ金属塩系の化合物(C2)、及び下記一般式(3)で表されるアンモニウム塩系の化合物(C3)について説明する。
R9は、置換基を有してもよいアルキレン結合基、置換基と二重結合を有してもよいアルキレン結合基、置換基と三重結合を有してもよいアルキレン結合基、置換基を有してもよいアリーレン結合基、置換基を有してもよい複素環結合基、又は、エーテル結合基、エステル結合基、チオエーテル結合基、ジチオール結合基、カルボニル結合基、スルフィニル結合基、スルホニル結合基、ホスホニル結合基、アミノ結合基、イミノ結合基、もしくはシリル結合基を表す。
R10は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、ハロゲン基を表す。
R11は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、−R9R10を表す。〕
置換基を有してもよいアルキニル基としては、炭素数2〜10のアルキニル基が好ましく、例えば、エチニル基、プロピニル基、プロパルギル基等が挙げられる。
置換基と三重結合を有してもよいアルキレン結合基としては、1つ以上の三重結合を有する炭素数2〜10のアルキレン結合基が挙げられる。
R5〜R8は、化合物の安定性面から考慮して、置換基を有してもよいアルキル基が好ましい。
例えば、アセトン、酢酸エチル、シクロヘキサン、トルエン、メチルエチルケトン、イソプロピルアルコール、その他の炭化水素系溶媒等の有機溶媒や、水をさらに添加して、感圧式接着剤組成物の粘度を調整することもできるし、感圧式接着剤組成物を加熱して粘度を低下させることもできる。
さらに、多数の有酸素結合基が存在しているため、この有酸素結合の不対電子も多数存在したペンダントしたような状態を呈し、液晶セル用ガラス等の被着体界面近傍の配向するため、不対電子間の距離が短くなり、この不対電子を通してネットワークを形成し、導電パスが形成される。ここで、感圧式接着剤フィルムに積層されている剥離フィルムを剥がして被着体の貼着する場合や、一度貼着された偏光フィルム等を被着体から剥がしたり、また新しい偏光フィルム等が貼り直されたりするリワークの場合に帯電するが、これらの剥離や貼着に伴う圧力変化のため、上記のイオン性化合物(C)等の制電剤と有酸素結合基との疑似配位結合が壊れ、被着体界面付近の有酸素結合基に由来する導電パス上で速やかにイオン伝導が起こりやすくなるため、帯電防止性能が向上する。また以上の理由により、従来よりも過酷な条件下における耐熱性及び耐湿熱性をも向上することができるため、光学部材用として好ましく使用することができる。
本発明の光学用感圧式接着剤フィルムは、以下のようにして得ることができる。
剥離性フィルムの剥離処理面に感圧式接着剤組成物を塗工、乾燥し、フィルム状基材である光学フィルムを感圧式接着剤層の表面に積層したり、フィルム状基材である光学フィルムに感圧式接着剤組成物を塗工、乾燥し、感圧式接着剤層の表面に剥離性フィルムの剥離処理面を積層したりすることによって、光学用感圧式接着剤フィルムを得ることができる。共重合体(A)と架橋剤(B)との架橋反応は、感圧式接着剤組成物の乾燥時、及び形成された感圧式接着剤層表面にフィルム状の光学フィルムや剥離性フィルムを積層する際、さらには積層した後に進行する。
感圧式接着剤組成物は、感圧式接着剤フィルムを形成するために用いられる。
感圧式接着剤フィルムの基本的積層構成は、フィルム状基材/感圧式接着剤層/剥離性フィルムのような片面感圧式接着剤フィルム、あるいは剥離性フィルム/感圧式接着剤層/フィルム状基材/感圧式接着剤層/剥離性フィルムのような両面感圧式接着剤フィルムである。使用時に、剥離性フィルムが剥がされ、感圧式接着剤層が被着体に貼付される。感圧式接着剤組成物は、貼着の際、被着体に感圧式接着剤層が触れるその瞬間に感圧式接着剤層がタックを有すのみならず、感圧式接着剤組成物以外の接着剤(以下、単に接着剤という)とは異なり、貼着中も完全に固化することなく、タックと適度な固さを有しつつ、貼着状態を維持するための凝集力を有することが必要である。凝集力は分子量に大きく依存する。
偏光フィルムは、偏光板とも呼ばれ、ポリビニルアルコール系偏光子の両面を2枚のトリアセチルセルロース系保護フィルム(以下、「TACフィルム」という)や2枚のシクロオレフィ系フィルムやアクリル系フィルムで挟んだ多層構造フィルムである。
感圧式接着剤層の厚さは、0.1μm〜200μmであることが好ましく、0.1μm〜100μmであることがより好ましい。0.1μm未満では十分な接着力が得られないことがあり、200μmを超えても接着力等の特性はそれ以上向上しない場合が多い。
乾燥方法には特に制限はなく、熱風乾燥、赤外線や減圧法を利用したものが挙げられる。乾燥条件としては感圧式接着剤組成物の架橋形態、膜厚や選択した溶剤にもよるが、通常60〜180℃程度の熱風加熱でよい。
本発明の積層体は、例えば、偏光フィルム、位相差フィルム、楕円偏光フィルム、反射防止フィルム、輝度向上フィルム等の各種光学特性を持つ、いわゆるシート(フィルムともいう)状の光学部材の片方の面に、本発明の感圧式接着剤から形成される感圧式接着剤層を積層し、さらに、その上層に剥離性フィルムを積層して、まず、上述の光学用感圧式接着剤フィルムを形成する。
(ア)剥離性フィルムの剥離処理面に感圧式接着剤を塗工、乾燥し、フィルム状の光学部材を接着層の表面に積層したり、
(イ)フィルム状の光学部材に、直接、感圧式接着剤を塗工、乾燥し、接着層の表面に剥離性フィルムの剥離処理面を積層したりすることによって得ることができる。
共重合体(A)と架橋剤(B)との反応は、感圧式接着剤組成物を乾燥する際、及び感圧式接着剤層表面にフィルム状の光学部材や剥離性フィルムを積層する際及び積層した後に進行する。
なお、本発明の光学用感圧式接着剤フィルムは、上記態様に限定されるものではなく、光学部材の両方の面に感圧式接着剤層が設けられていてもよい。
また、必ずしも剥離性フィルムを使用する必要はない。
そして、光学用感圧式接着剤フィルムの接着剤層の表面を覆っていた剥離性フィルムを剥がし、フィルム部材やガラス部材に貼着することによって光学用途に使用可能な積層体として使用することができる。
特に、本発明の光学用感圧式接着剤フィルムを液晶セル用ガラス部材に貼着することによって、光学部材/感圧式接着剤層/ガラス部材という構成の光学用ガラス積層体を得たものを液晶セル用部材という。
(合成例1)
反応槽、攪拌機、温度計、還流冷却器、空気導入管を備えた重合反応装置の反応槽に、下記、エチレン性不飽和単量体、環状エステル(f)、触媒及び有機溶剤をそれぞれ下記の比率で仕込んだ。
アクリル酸2−ヒドロキシエチル(a1) 22.7部
ピリジン 16.7部
トルエン 90.0部
[滴下装置]
メチルクロロフォーメイト 17.3部
合成例1で用いたメチルクロロフォーメイト17.3gの代わりにブチルクロロフォーメイト25.0gを用いた以外は上記合成方法と同様にして、アクリル酸エチル−ブチルカーボネートを得た。得られた生成物の収率は分子量測定により82%であった。
(合成例3)
反応槽、攪拌機、温度計、還流冷却器、滴下装置、空気導入管を備えた重合反応装置の反応槽及び滴下装置に、下記、エチレン性不飽和単量体、開始剤及び有機溶剤をそれぞれ下記の比率で仕込んだ。
アクリル酸n−ブチル(a3) 49部
アクリル酸(a2) 1部
酢酸メチル 30部
2,2’−アゾビスイソブチロニトリル 0.05部
[滴下装置]
アクリル酸n−ブチル(a3) 29部
アクリル酸(a2) 1部
合成例1で作成したエチレン性不飽和単量体 20部
酢酸エチル 36部
2,2’−アゾビスイソブチロニトリル 0.05部
合成例3で用いたエチレン性不飽和単量体(a2)をアクリル酸2−ヒドロキシエチル(a1)に変更した以外は合成例2と同様にして反応を行って、EAcで濃度を約40%に調整し、若干粘度上昇が認められたが、透明な溶液を得た。
合成例3で用いた、合成例1で作成したアクリル酸エチル−メチルカーボネートを合成例2で作製したアクリル酸エチル−ブチルカーボネートに変更した以外は合成例3と同様にして反応を行って、EAcで濃度を約40%に調整し、若干粘度上昇が認められたが、透明な溶液を得た。
<共重合体(A)の前駆体(AP)製造(工程1)>
(合成例6)
反応槽、攪拌機、温度計、還流冷却器、滴下装置、空気導入管を備えた重合反応装置の反応槽及び滴下装置に、下記、エチレン性不飽和単量体、開始剤及び有機溶剤をそれぞれ下記の比率で仕込んだ。
アクリル酸n−ブチル(a3) 49部
アクリル酸2−ヒドロキシエチル(a1) 10部
アクリル酸(a2) 1部
酢酸メチル 30部
2,2’−アゾビスイソブチロニトリル 0.05部
[滴下装置]
アクリル酸n−ブチル(a3) 29部
アクリル酸(a2) 1部
アクリル酸2−ヒドロキシエチル(a1) 10部
酢酸エチル 36部
2,2’−アゾビスイソブチロニトリル 0.05部
合成例6で用いたエチレン性不飽和単量体を下記のように変更して仕込んだ。
アクリル酸n−ブチル(a3) 43部
アクリル酸2−ヒドロキシエチル(a1) 10部
アクリル酸メチル(a3) 5部
メタクリル酸メチル(a3) 2部
酢酸メチル 30部
2,2’−アゾビスイソブチロニトリル 0.05部
[滴下装置]
アクリル酸n−ブチル(a3) 30部
アクリル酸2−ヒドロキシエチル(a1) 10部
酢酸エチル 36部
2,2’−アゾビスイソブチロニトリル 0.05部
合成例6で用いたエチレン性不飽和単量体を下記のように変更して仕込んだ。
アクリル酸n−ブチル(a3) 40部
アクリル酸(a2) 5部
アクリル酸メチル(a3) 5部
酢酸メチル 30部
2,2’−アゾビスイソブチロニトリル 0.05部
[滴下装置]
アクリル酸n−ブチル(a3) 45部
アクリル酸(a2) 5部
酢酸エチル 36部
2,2’−アゾビスイソブチロニトリル 0.05部
(合成例9)
攪拌機、温度計、還流冷却器、滴下装置及び窒素導入管を取り付けた重合反応装置を用意し、反応槽及び滴下装置に、前駆体(AP)溶液、環状化合物(f)、触媒及び有機溶剤を各々下記の比率で仕込んだ。
合成例6で得られた前駆体(AP)溶液 200部
[滴下装置]
エチレンカーボネート(f2) 44部
p−トルエンスルホン酸(触媒) 0.5部
酢酸エチル 30部
次いで、これに滴下装置より環状化合物(f)混合物を1時間かけて等速で滴下した。さらに、攪拌しながら12時間反応・熟成した後、酢酸エチル加えて室温まで冷却して反応を終了し、共重合体(A)を含む透明な溶液を得た。
合成例9で用いた環状化合物であるエチレンカーボネート(f2)44部を、プロピレンカーボネート51部(合成例10)、グリセリンカーボネート59部(合成例11)、1,3−ジオキソラン37部(合成例12)、1,3−ジオキサン44部(合成例13)、1,3,5−トリオキサン45部(合成例14)にそれぞれ変更した以外は合成例9と同様にして反応を行って、EAcで濃度を約40%に調整し、透明な溶液を得た。
合成例9で用いた前駆体(AP)溶液200部を、合成例7で得られた前駆体(AP)溶液(合成例15)、合成例8で得られた前駆体(AP)溶液(合成例16)にそれぞれ変更した以外は合成例9と同様にして反応を行って、EAcで濃度を約40%に調整し、透明な溶液を得た。
(合成例17)
攪拌機、温度計、還流冷却器、滴下装置及び窒素導入管を取り付けた反応装置を用意し、反応槽及び滴下装置に、合成例12で得た共重合体(A)を含む樹脂溶液、モノイソシアネート化合物(d3)及び有機溶剤をそれぞれ下記の比率で仕込んだ。
合成例9で得た共重合体(A)溶液 200部
[滴下装置]
p−トルエンスルホニルイソシアネート(d3) 3部
酢酸エチル 10部
合成例17において用いたモノイソシアネート化合物(d3)をシラン化合物(d1)としてトリメチルシラノール2部に変更したこと以外は合成例17と同様にして酢酸エチルを加えて調製を行って、水酸基価を調整した共重合体(A’)を含む、濃度約40%の透明な溶液を得た。
合成例17において用いたモノイソシアネート化合物(d3)を酸無水物基含有化合物(d2)として無水マレイン酸2.5部に変更したこと以外は合成例17と同様にして酢酸エチルを加えて調製を行って、水酸基価を調整した共重合体(A’)を含む、濃度約40%の透明な溶液を得た。
合成例17で得られた樹脂溶液にアミン化合物(d4)としてエチルアミン3部を加えて、合成例17と同様にして反応を行って、酢酸エチルを加えて調製を行って、酸価を調整した共重合体(A’)を含む、濃度約40%の透明な溶液を得た。
(合成例21)
反応槽、攪拌機、温度計、還流冷却器、滴下装置、空気導入管を備えた重合反応装置の反応槽及び滴下装置に、下記、エチレン性不飽和単量体、環状エステル、開始剤、触媒及び有機溶剤をそれぞれ下記の比率で仕込んだ。
アクリル酸n−ブチル(a5) 49部
アクリル酸2−ヒドロキシエチル(a1) 10部
アクリル酸(a2) 1部
酢酸メチル 30部
2,2’−アゾビスイソブチロニトリル 0.05部
[滴下装置]
アクリル酸n−ブチル(a5) 29部
アクリル酸(a2) 1部
アクリル酸2−ヒドロキシエチル(a1) 10部
酢酸エチル 43部
エチレンカーボネート(f) 44部
2,2’−アゾビスイソブチロニトリル 0.1部
p−トルエンスルホン酸(触媒) 0.6部
次いで、これに滴下装置より環状エステル(f)を含む混合物を2時間かけて等速で滴下した。さらに、攪拌しながら10時間反応・熟成した後、酢酸エチルで約40%に調整して、室温まで冷却して反応を終了し、共重合体(A)を含む透明な溶液を得た。
(合成例22)
攪拌機、温度計、還流冷却器、滴下装置及び窒素導入管を取り付けた反応装置を用意し、反応槽及び滴下装置に、合成例18で得た共重合体(A)を含む樹脂溶液、モノイソシアネート化合物(d3)及び有機溶剤をそれぞれ下記の比率で
仕込んだ。
合成例21で得た共重合体(A)溶液 200部
[滴下装置]
フェニルイソシアネート (d3) 3部
酢酸エチル 10部
(合成例23〜114)
特開2009−84541号公報に従って表1〜6記載のアンモニウム塩系の化合物(C1−1)〜(C1−92)を合成した。
(合成例115〜124)
定法に従い、表7記載のアンモニウム塩系の化合物(C2−1)〜(C2−10)を合成した。
(合成例125〜230)
米国特許第6,372,829号明細書に従って表8〜14記載のアンモニウム塩系の化合物(C3−1)〜(C3−106)を合成した。
エチレン性不飽和単量体の外観を目視にて評価した。
《収率》
エチレン性不飽和単量体(a4)の重量平均分子量(Mw)の測定で収率を確認した。Mwは昭和電工社製GPC(ゲルパーミエーションクロマトグラフィー)「ShodexGPC System−21」を用いた。GPCは溶媒に溶解した物質をその分子サイズの差によって分離定量する液体クロマトグラフィーであり、重量平均分子量(Mw)の決定はポリスチレン換算で行った。
共栓三角フラスコ中に試料をそれぞれ精密に約1g量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。酸価(mgKOH/g)は次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
HEA:アクリル酸2−ヒドロキシエチル、EC:エチレンカーボネート、ND:検出せず。
共重合体(A)の溶液、及び水酸基価を調整した共重合体(A’)の溶液の外観を目視にて評価した。
《不揮発分濃度(NV)の測定》
共重合体(A)の溶液の溶液、及び水酸基価を調整した共重合体(A’)の溶液、約1gを金属容器に秤量し、150℃オーブンにて20分間乾燥して、残分を秤量して残率計算をし、不揮発分濃度(%)とした。
共重合体(A)の溶液、及び水酸基価を調整した共重合体(A’)の溶液を23℃の雰囲気下でB型粘度計(東京計器社製)にて、#3のローターを使用して12rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
《重量平均分子量(Mw)の測定》
共重合体(A)、及び水酸基価を調整した共重合体(A’)の重量平均分子量(Mw)の測定は昭和電工社製GPC(ゲルパーミエーションクロマトグラフィー)「ShodexGPC System−21」を用いた。GPCは溶媒に溶解した物質をその分子サイズの差によって分離定量する液体クロマトグラフィーであり、重量平均分子量(Mw)の決定はポリスチレン換算で行った。
共栓三角フラスコ中に試料、約1gを精密に量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
乾燥状態の樹脂の値として、酸価(mgKOH/g)を次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}/(不揮発分濃度/100)
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
共栓三角フラスコ中に試料、約1gを精密に量り採り、トルエン/エタノール(容量比:トルエン/エタノール=2/1)混合液100mlを加えて溶解する。更にアセチル化剤(無水エタン酸25gをピリジンで溶解し、容量100mlとした溶液)を正確に5ml加え、約1時間攪拌した。これに、フェノールフタレイン試液を指示薬として加え、30秒間持続する。その後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定する。
水酸基価は次式により求めた。水酸基価は樹脂の乾燥状態の数値とした(単位:mgKOH/g)。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
ロボットDSC(示差走査熱量計、セイコーインスツルメンツ社製「RDC220」)に「SSC5200ディスクステーション」(セイコーインスツルメンツ社製)を接続して、測定に使用した。
各合成例で得られた共重合体(A)の溶液、及び水酸基価を調整した共重合体(A’)の溶液を、剥離処理されたポリエステルフィルムに塗工・乾燥し、乾燥した樹脂を約10mgかきとり、試料としてアルミニウムパンに入れ、秤量して示差走査熱量計にセットし、試料を入れない同タイプのアルミニウムパンをリファレンスとして、100℃の温度で5分間加熱した後、液体窒素を用いて−120℃まで急冷処理した。その後10℃/分で昇温し、昇温中に得られたDSCチャートからガラス転移温度(Tg、単位:℃)を決定した。
BA:アクリル酸n−ブチル、MA:アクリル酸メチル、AA:アクリル酸、HEA:アクリル酸2−ヒドロキシエチル、MMA:メタクリル酸メチル、EC:エチレンカーボネート、PC:プロピレンカーボネート、GC:グリセリンカーボネート、OXO:1,3−ジオキソラン、DOX:1,3−ジオキサン、TOX:1,3,5−トリオキサン、PTSI:p−トルエンスルホニルイソシアネート、PhNCO:フェニルイソシアネート、TMS:トリメチルシラノール、EA:エチルアミン、MAnh:無水マレイン酸、EAc:酢酸エチル、AIBN:2,2’−アゾビスイソブチロニトリル、PTS:p−トルエンスルホン酸。
合成例9で得られた共重合体(A)の溶液100部に対して、アンモニウム塩系の化合物(C1)を0.5部、更に架橋剤(B)として、TDI/TMP(トルレンジイソシネートのトリメチロールプロパンアダクト体)5部、および塗工粘度が2000〜3000mPa・sとなるようにTolを加え加えてよく撹拌して、感圧式接着剤組成物を得た。
これを剥離処理されたポリエステルフィルム(以下、「剥離性フィルム」という。)上に乾燥後の厚みが25μmになるように塗工し、100℃で2分間乾燥させ、感圧式接着剤層を形成した。
乾燥後、感圧式接着剤層に、ポリビニルアルコール(PVA)系偏光子の両面をトリアセチルセルロース(TAC)系保護フィルムで挟んだ多層構造の偏光フィルムの片面を貼り合せ、「剥離性フィルム/感圧式接着剤層/TACフィルム/PVA/TACフィルム」なる構成の積層フィルムを得た。
次いで、得られた積層フィルムを温度23℃相対湿度50%の条件で1週間熟成(暗反応)させて、感圧式接着剤層の反応を進行させ、光学用感圧式接着剤フィルムを得た。
実施例1で使用した、合成例9で得られた共重合体(A)溶液の代わりに、合成例3〜8で作成した樹脂溶液を使用したこと以外は実施例1と同様にして、光学用感圧式接着フィルムを得た。
実施例1で使用した、合成例9で作成した共重合体(A)の溶液の代わりに、合成例10〜22で得られた共重合体(A)の溶液をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
実施例1で使用したイオン性化合物(C)の代わりに、(C1−26)(実施例15)、(C1−64)(実施例16)、(C−89)(実施例17)をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
実施例1で使用したイオン性化合物(C)の代わりに、合成例133〜139で得られた(C3−39)(実施例18)、(C3−83)(実施例19)、(C3−84)(実施例20)をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
(実施例21〜22)
実施例1で使用した架橋剤(B)のTDI/TMPの代わりに、実施例21ではXDI/TMP(キシリレンジイソシネートのトリメチロールプロパンアダクト体)を、実施例22ではHMDI/ビュレット(ヘキサメチレンジイソシアネートのビュレットアダクト体)を、それぞれ5部添加したこと以外は、実施例1と同様にして、感圧式接着剤フィルムを作製した。
実施例1で使用した架橋剤(B)のTDI/TMPの代わりに、、実施例23ではHBAP(2,2’−ビスヒドロキシメチルブタノールトリス[3−(1−アジリジニル)プロピオネート])0.1部、実施例24ではTGMXDA(N,N,N’,N’−テトラグリシジル−m−キシリレンジアミン)5部、実施例25ではV−05(カルボジイミド化合物である「カルボジライトV−05」:日清紡績株式会社製)5部、実施例26ではAlキレート(アルミニウムトリス(2,4−ペンタジオネート))1部を、それぞれ1部添加したこと以外は、実施例1と同様にして、光学用感圧式接着フィルムを作製した。尚、実施例26では溶剤をメチルエチルケトンからイソプロピルアルコール(IPA)に変更して使用した。
実施例14で使用した架橋剤(B)のTDI/TMPの代わりに、実施例27ではXDI/TMP(キシリレンジイソシネートのトリメチロールプロパンアダクト体)を、実施例28ではHMDI/ビュレット(ヘキサメチレンジイソシアネートのビュレットアダクト体)を、それぞれ5部添加したこと以外は、実施例1と同様にして、感圧式接着剤フィルムを作製した。
実施例14で使用した架橋剤(B)のTDI/TMPの代わりに、、実施例29ではHBAP(2,2’−ビスヒドロキシメチルブタノールトリス[3−(1−アジリジニル)プロピオネート])0.1部、実施例30ではTGMXDA(N,N,N’,N’−テトラグリシジル−m−キシリレンジアミン)5部、実施例31ではV−05(カルボジイミド化合物である「カルボジライトV−05」:日清紡績株式会社製)5部、実施例32ではAlキレート(アルミニウムトリス(2,4−ペンタジオネート))1部を、それぞれ1部添加したこと以外は、実施例1と同様にして、光学用感圧式接着剤フィルムを作製した。尚、実施例32では溶剤をメチルエチルケトンからイソプロピルアルコール(IPA)に変更して使用した。
実施例1で使用したイオン性化合物(C)の代わりに、(C1−1)〜(C1−3)および(C1−5)〜(C1−92)をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
実施例1で使用したイオン性化合物(C)の代わりに、(C2−1)〜(C2−10)をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
実施例1で使用したイオン性化合物(C)の代わりに、(C3−1)〜(C3−106)をそれぞれ使用した以外は実施例1と同様にして、光学用感圧式接着フィルムを作製した。
得られた感圧式接着剤組成物について、架橋剤(B)添加後、25℃における粘度を1時間おきに10時間後まで、B型粘度計(東京計器社製)を用い、12rpm、1分間回転の条件で測定し、可使時間(ポットライフ)を3段階で評価した。
○:「8時間までの粘度上昇率が2倍未満。全く問題なし。」
△:「5時間までの粘度上昇率が2倍未満。実用上使用可。」
×:「5時間未満でゲル化。実用上問題あり。」
得られた感圧式接着剤組成物を、剥離性フィルムにコンマコーターにて速度2m/minで塗工し、100℃オーブンにて乾燥し、厚みが25μmの感圧式接着剤層を形成し、接着剤層の表面に厚さ50μmのポリエステルフィルムを貼り合わせ、感圧式接着剤フィルムを作製した。そして剥離フィルムを剥がした後の接着剤層表面(塗工面)の状態について目視にて観察し、3段階で評価した。
○:「平滑な塗工面が得られた。全く問題なし。」
△:「塗工面の端部に若干のハジキや発泡が認められるが、実用上問題無し。」
×:「塗工面にハジキ、発泡やスジ引きが認められ、実用上問題あり。」
各実施例、比較例で得られた感圧式接着剤組成物を、剥離性フィルムにコンマコーターにて速度2m/minで塗工し、100℃オーブンにて乾燥し、厚みが25μmの感圧式接着剤層を形成し、接着剤層の表面に剥離性フィルムを貼り合わせ、剥離性フィルムに狭持された感圧式接着剤フィルムを作製した。
これを温度23℃、相対湿度50%の条件で1週間熟成させた後、両方の剥離性フィルムを取り除き、感圧式接着剤層単体の外観を目視判定するとともに、HAZEを「NDH−300A」[日本電色工業(株)社製]で測定した。
○:実用上全く問題がなく、非常に良好である。HAZE:0.5未満。
△:曇り等は認められない、かつHAZE:0.5以上2未満、実用上問題無く使用できる。
×:若干曇りが認められる、またはHAZE:2以上。実用上問題がある。
各実施例、比較例で得られた光学用感圧式接着剤フィルムを25mm×150mmの大きさに裁断し、剥離性フィルムを剥がし、厚さ1.1mmのフロートガラス板にラミネータを用いて貼り付け、50℃で5気圧の条件のオートクレーブ内に20分保持させて、偏光フィルムとガラス板との積層体を得た。
この積層体を23℃、相対湿度50%で1週間放置した後に、180度方向に300mm/分の速度で引き剥がし、剥離後のガラス表面の曇りを目視で観察し、3段階で評価した。
○:曇りがなく、実用上全く問題がない、非常に良好である。
△:若干曇りが認められるが、実用上問題なく、良好である。
×:全面的に感圧式接着剤組成物の転着が認められ、実用不可である。
各実施例、比較例で得られた光学用感圧式接着剤フィルムを150mm×80mmの大きさに裁断し、剥離性フィルムを剥がし、厚さ1.1mmのフロートガラス板の両面に、それぞれの偏光フィルムの吸収軸が直交するようにラミネータを用いて貼着した。続いて、この偏光フィルムが貼り付けられたガラス板を50℃で5気圧の条件のオートクレーブ内に20分保持させて、偏光フィルムとガラス板との積層体の液晶セル用部材を得た。
耐熱性の評価として、上記積層物を95℃で1000時間放置した後の浮きハガレ、および積層物に光を透過させたときの光漏れ(白抜け)を目視で観察した。
また、耐湿熱性の評価として、上記積層体を80℃、相対湿度90%で1000時間放置した後の浮きハガレ、および積層体に光を透過させたときの光漏れ(白抜け)を目視で観察した。
耐熱性、耐湿熱性について、下記の4段階の評価基準に基づいて評価をおこなった。
◎:浮きハガレ・発泡・白ぬけ・ズレが全く認められず、実用上全く問題なし、非常に良好である。
○:浮きハガレ・発泡・白ぬけが全く認められず、ズレが0.2mm未満で、実用上全く問題なし。
△:若干浮きハガレ・発泡・白ぬけが認められるが、ズレが0.2〜0.5mm未満で、実用上問題がなく、良好である
×:全面的に浮きハガレ・発泡・白ぬけがあり、実用不可である。
感圧式接着剤フィルムの剥離フィルムを剥がし、露出した接着剤層表面の表面抵抗値を、23℃−35、45、55%RHの各条件下で、表面抵抗値測定装置(三菱化学株式会社製:MCT−HT450)を用いて測定し(単位:Ω/□)、初期値と経時値の制電性能評価とした。
(初期値評価)
剥離性フィルムにコンマコーターにて速度2m/minで塗工し、100℃オーブンにて乾燥し、厚みが25μmの感圧式接着剤層を形成し、接着剤層の表面に厚さ50μmのポリエステルフィルムを貼り合わせ、感圧式接着剤フィルムを作製した。温度23℃、相対湿度50%の条件で1週間熟成させた後に上記の方法にて制電性能を評価し、初期値とした。
(経時値評価)
上記、1週間熟成させた感圧式接着剤フィルムを温度60℃、相対湿度95%の条件下で7日間放置し、次に温度23℃、相対湿度50%の条件下で24時間おいて、上記の方法にて制電性能を評価し、経時値とした。
○:「表面抵抗値が1.0×1010未満。」
△:「表面抵抗値が1.0×1010以上、1.0×1011未満。」
×:「表面抵抗値が2.0×1011以上。」
感圧式接着剤フィルムの剥離フィルムを剥がし、露出した接着剤層をテフロン(登録商標)のシート(厚さ1mm)に温度23℃、相対湿度50%の条件にて貼着し、ハンドロールで圧着した。圧着から24時間経過後、ガラス板上で、静電気除去機(キーエンス社製「SJ−F010」)で除電した後に、感圧式接着剤フィルムをテフロン(登録商標)のシートから剥離して、テフロン(登録商標)のシート表面の静電気を静電気測定器(シシド静電気株式会社製「STATION DZ3」)で10箇所測定して絶対値が最大の値を剥離帯電(単位:kV)とした。
○:「剥離耐電圧が±0.1kV未満。」
△:「剥離耐電圧が±0.1kV以上、±0.5kV未満。」
×:「剥離耐電圧が±0.5kV以上。」
TDI/TMP:トルレンジイソシネートのトリメチロールプロパンアダクト体、XDI/TMP:キシリレンジイソシネートのトリメチロールプロパンアダクト体、HMDI/ビュレット:ヘキサメチレンジイソシアネートのビュレットアダクト体、HBAP:2,2’−ビスヒドロキシメチルブタノールトリス[3−(1−アジリジニル)プロピオネート]、TGMXDA:N,N,N’,N’−テトラグリシジル−m−キシリレンジアミン、V−05:カルボジイミド化合物である「カルボジライトV−05」、Alキレート:アルミニウムトリス(2,4−ペンタジオネート)、IPA:イソプロピルアルコール、Tol:トルエン。
これに対して、カーボネート基を有するエチレン性不飽和単量体成分を共重合した比較例1〜3では、重合安定性があまり良くないため、塗工性に悪影響を及ぼすため、耐久性に劣り、更に期待したほどの制電性能が得られない。また、側鎖にカーボネート基を含まない比較例3〜6では、導電パスが形成されないため、制電性能を殆ど示さないことが認められ、ガラス板に貼着後、高温下にもしくは高温高湿度下に長期間おかれると、制電剤のマイグレーションと思われる発泡や浮き剥がれ等が発生し、耐久性に劣ることも認められる。
Claims (11)
- 官能基として水酸基及び/又はカルボキシル基を有し、更に側鎖に二個以上の酸素原子を有する四員環以上の環状化合物(f)を開環付加してなるガラス転移温度が−60〜0℃の共重合体(A)と、共重合体(A)中の官能基と反応し得る官能基を有する架橋剤(B)と、下記一般式(1)、(2)または(3)から選ばれるイオン性化合物(C)とを含有することを特徴とする感圧式接着剤組成物。
一般式(1)
〔一般式(1)中R1〜R8は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルケニル基、置換基を有してもよいアルキニル基、置換基を有してもよいアリール基、又は、置換基を有してもよい複素環基を表し、R5〜R8は、隣り合う置換基同士で環を形成してもよい。〕
一般式(2)
〔一般式(2)中R1〜R4は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルケニル基、置換基を有してもよいアルキニル基、置換基を有してもよいアリール基、又は、置換基を有してもよい複素環基を表し、A+は、アルカリ金属イオンを表す。〕
一般式(3)
〔一般式(3)中R5〜R8は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルケニル基、置換基を有してもよいアルキニル基、置換基を有してもよいアリール基、又は、置換基を有してもよい複素環基を表し、隣り合う置換基同士で環を形成してもよい。
R9は、置換基を有してもよいアルキレン結合基、置換基と二重結合を有してもよいアルキレン結合基、置換基と三重結合を有してもよいアルキレン結合基、置換基を有してもよいアリーレン結合基、置換基を有してもよい複素環結合基、又は、エーテル結合基、エステル結合基、チオエーテル結合基、ジチオール結合基、カルボニル結合基、スルフィニル結合基、スルホニル結合基、ホスホニル結合基、アミノ結合基、イミノ結合基、もしくはシリル結合基を表す。
R10は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、ハロゲン基を表す。
R11は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、又は、−R9R10を表す。〕 - 共重合体(A)は、官能基として水酸基を有するエチレン性不飽和単量体(a1)及び/又はカルボキシル基を有するエチレン性不飽和単量体(a2)、更に必要に応じて(a1)、(a2)以外のエチレン性不飽和単量体(a3)を共重合して得られる共重合体(A)であって、さらに、共重合体(A)の前駆体(AP)100重量部に対して、(a1)及び/又は(a2)を1〜40重量部含有するものであることを特徴とする、請求項1記載の感圧式接着剤組成物。
- 共重合体(A)の側鎖に二個以上の酸素原子を有する四員環以上の環状化合物を開環付加してなる結合基は、(水酸基及び/又はカルボキシル基を有する、)共重合体(A)の前駆体(AP)中の水酸基及び/又はカルボキシル基と、二個以上の酸素原子を有する四員環以上の環状化合物(f)との反応により生成するものであることを特徴とする、請求項1または2記載の感圧式接着剤組成物。
- 二個以上の酸素原子を有する四員環以上の環状化合物(f)が、環状ホルマール(f−1)及び/又は、環状カーボネート(f−2)であることを特徴とする請求項3記載の感圧式接着剤組成物。
- 環状ホルマール(f−1)が、ジオキソラン類、ジオキサン類、トリオキサン類から選ばれる少なくとも1種であることを特徴とする請求項4記載の感圧式接着剤組成物。
- 共重合体(A)が、共重合体(A)の前駆体(AP)100重量部に対して、二個以上の酸素原子を有する四員環以上の環状化合物(f)1〜150重量部を用いてなることを特徴とする請求項4または5記載の感圧式接着剤組成物。
- 共重合体(A)100重量部に対して、イオン性化合物(C)を0.01〜10重量部含むことを特徴とする請求項1〜6いずれか記載の感圧式接着剤組成物。
- 架橋剤(B)がポリイソシアネート化合物(b1)であることを特徴とする請求項1〜7いずれか記載の感圧式接着剤組成物。
- 架橋剤(B)がエポキシ化合物(b2)、アジリジン化合物(b3)、カルボジイミド化合物(b4)、オキサゾリン化合物(b5)、もしくは金属キレート化合物(b6)のいずれかであることを特徴とする請求項1〜7いずれか記載の感圧式接着剤組成物。
- 請求項1〜9いずれかに記載の感圧式接着剤組成物から形成される感圧式接着剤層上に光学部材が積層されてなる積層体。
- 液晶セル用ガラス部材、請求項1〜9いずれかに記載の感圧式接着剤組成物から形成される感圧式接着剤層、及び光学部材が順次積層されてなる液晶セル用部材。
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KR102125020B1 (ko) * | 2018-09-05 | 2020-06-19 | (주)이녹스첨단소재 | 디스플레이용 점착시트 및 이를 포함하는 디스플레이 |
JP2020070313A (ja) * | 2018-10-29 | 2020-05-07 | リンテック株式会社 | 飛散防止粘着シート |
JP7026663B2 (ja) | 2018-10-29 | 2022-02-28 | イノックス・アドバンスト・マテリアルズ・カンパニー・リミテッド | ディスプレイ用粘着シートおよびこれを含むディスプレイ |
JP2020070441A (ja) * | 2018-10-29 | 2020-05-07 | イノックス アドバンスド マテリアルズ カンパニー リミテッド | ディスプレイ用粘着シートおよびこれを含むディスプレイ |
CN111100575A (zh) * | 2018-10-29 | 2020-05-05 | 利诺士尖端材料有限公司 | 显示器用粘结片及包括其的显示器 |
CN111100585A (zh) * | 2018-10-29 | 2020-05-05 | 琳得科株式会社 | 飞散防止粘着片 |
CN111100585B (zh) * | 2018-10-29 | 2023-04-07 | 琳得科株式会社 | 飞散防止粘着片 |
JP7388814B2 (ja) | 2018-10-29 | 2023-11-29 | リンテック株式会社 | 飛散防止粘着シート |
CN111117510A (zh) * | 2018-10-30 | 2020-05-08 | 利诺士尖端材料有限公司 | 显示器用粘结片及包括其的显示器 |
CN111117510B (zh) * | 2018-10-30 | 2022-08-02 | 利诺士尖端材料有限公司 | 显示器用粘结片及包括其的显示器 |
JP2021178979A (ja) * | 2020-05-07 | 2021-11-18 | 藤森工業株式会社 | 粘着フィルム |
JP7132407B2 (ja) | 2020-05-07 | 2022-09-06 | 藤森工業株式会社 | 粘着フィルム |
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