JP6273879B2 - 活性エネルギー線重合性樹脂組成物及び積層体 - Google Patents
活性エネルギー線重合性樹脂組成物及び積層体 Download PDFInfo
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- JP6273879B2 JP6273879B2 JP2014024739A JP2014024739A JP6273879B2 JP 6273879 B2 JP6273879 B2 JP 6273879B2 JP 2014024739 A JP2014024739 A JP 2014024739A JP 2014024739 A JP2014024739 A JP 2014024739A JP 6273879 B2 JP6273879 B2 JP 6273879B2
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- meth
- vinyl
- acrylate
- acid
- ether
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- 150000001875 compounds Chemical class 0.000 claims description 182
- 239000000853 adhesive Substances 0.000 claims description 52
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 229920005989 resin Polymers 0.000 claims description 34
- 239000011347 resin Substances 0.000 claims description 34
- 239000000758 substrate Substances 0.000 claims description 29
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- 239000013522 chelant Substances 0.000 claims description 24
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- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 22
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- 238000006116 polymerization reaction Methods 0.000 claims description 17
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- 125000004122 cyclic group Chemical group 0.000 claims description 14
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- 125000001033 ether group Chemical group 0.000 claims description 10
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- 239000010408 film Substances 0.000 description 162
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 91
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- 230000003287 optical effect Effects 0.000 description 25
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- 206010040844 Skin exfoliation Diseases 0.000 description 21
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- 229910052757 nitrogen Inorganic materials 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
- 229960000834 vinyl ether Drugs 0.000 description 14
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- 125000001931 aliphatic group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
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- 238000000034 method Methods 0.000 description 11
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
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- 229930185605 Bisphenol Natural products 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 125000002091 cationic group Chemical group 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- 229910052719 titanium Inorganic materials 0.000 description 9
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 229910052726 zirconium Inorganic materials 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
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- 239000005977 Ethylene Substances 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
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- 229920000728 polyester Polymers 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 8
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- 230000000694 effects Effects 0.000 description 7
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
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- 125000000623 heterocyclic group Chemical group 0.000 description 6
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- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- NPWJBNPQTPEEGC-UHFFFAOYSA-N tetradecyl 4-ethenylbenzoate Chemical compound C(CCCCCCCCCCCCC)OC(C1=CC=C(C=C1)C=C)=O NPWJBNPQTPEEGC-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LWLOKSXSAUHTJO-IMJSIDKUSA-N trans-2,3-butylene carbonate Chemical compound C[C@@H]1OC(=O)O[C@H]1C LWLOKSXSAUHTJO-IMJSIDKUSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- NELVVTIEGZVCKM-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CCCNC(=O)C=C.C[N+](C)(C)CCCNC(=O)C=C NELVVTIEGZVCKM-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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Landscapes
- Polarising Elements (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
Description
高温環境下では接着性が弱いとPVA系偏光子と保護フィルムの熱収縮率の違いにより、PVA系偏光子と保護フィルムとが剥がれる問題が発生することがあるが、前記カチオン重合性紫外線硬化型接着剤により形成した偏光板では過酷な環境下における耐久性を満足することはできていなかった。
更に近年、偏光子や保護フィルムの薄膜化が進んでおり、(メタ)アクリロイル基を有する化合物に係る硬化性成分を含有する活性エネルギー線硬化型接着剤により偏光板を形成した場合、接着剤の硬化収縮が大きいため偏光板にシワや凹凸が発生することがある。
金属キレート化合物(C)と、
活性エネルギー線重合開始剤(D)とを含有し、
前記化合物(A)が、アルコキシ基、エーテル基、ヒドロキシル基及びケト基(ただし、α,β−不飽和二重結合基に直接結合しているアルコキシ基、エーテル基、ヒドロキシル基及びケト基を除く)からなる群から選択される1以上の官能基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)と
化合物(A)が、1以上の環状構造を有するα,β−エチレン性不飽和二重結合基含有化合物(a2)とを含むことを特徴とする偏光板の保護フィルムを貼着するための接着剤である活性エネルギー線重合性樹脂組成物に関する。
該基材(G)の少なくとも一方の主面に、上記活性エネルギー線重合性樹脂組成物からなる樹脂層が設けられた偏光板に関する。
該光学フィルムの少なくとも一方の主面に設けられた上記活性エネルギー線重合性樹脂組成物からなる樹脂層とを有する光学素子用積層体に関する。
<活性エネルギー線重合性樹脂組成物>
本発明の活性エネルギー線重合性組成物はα,β−エチレン性不飽和二重結合基含有化合物(A)および/またはカチオン重合性化合物(ただしα,β−エチレン性不飽和二重結合基とカチオン重合性重合基の両方を含む化合物を除く)(B)と、金属キレート化合物(C)と活性エネルギー線開始剤(D)を必須成分とする活性エネルギー線重合性樹脂組成物であることを特徴とする。
(A)成分:
α,β−エチレン性不飽和二重結合基含有化合物(A)は、1個以上のα,β−不飽和二重結合基を含有する化合物であれば、特に制限はなく、使用できるが、その構造中にアルコキシ基、エーテル基、ヒドロキシル基及びケト基(ただし、α,β−不飽和二重結合基に直接結合しているカルボニル基を除く)からなる群から選択される1以上の官能基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)を含有することが好ましい。
化合物(a1)がアルコキシ基、エーテル基、ヒドロキシ基、ケト基からなる群から選択される1以上の官能基を有することにより金属キレート化合物(C)との間での配位結合や共有結合といった相互作用が働き、後述の基材(G)との密着性向上に大きな効果を示す。また、活性エネルギー線硬化樹脂組成物の凝集力や架橋度を向上させることができ、該基材(G)の少なくとも一方の主面に設けられた上記活性エネルギー線重合性樹脂組成物からなる樹脂層とを有する積層体としての耐熱性、耐湿熱性、熱的寸法安定性向上に大きな効果を示す。
(メタ)アクリル酸のラウロキシ -ポリエチレングリコール、オクトキシポリエチレングリコール、ステアロキシ等のアルキル末端ポチエチレングリコール類との脱水縮合で得られる化合物等が挙げられるが、特にこれらに限定されるものではない。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
例えば、N−ヒドロキシエチル(メタ)アクリルアミド〔N−ヒドロキシエチルアクリルアミドとN−ヒドロキシエチルメタクリルアミドとを併せて「N−ヒドロキシエチル(メタ)アクリルアミド」と表記する。以下同様。〕、N−ヒドロキシプロピル(メタ)アクリルアミド、N−ヒドロキシブチル(メタ)アクリルアミド、N−ヒドロキシヘキシル(メタ)アクリルアミド、N−ヒドロキシオクチル(メタ)アクリルアミド等の水酸基含有の(メタ)アクリルアミド類;
化合物(a1−2)としては、金属器レート化合物(C)の相互作用と後述の基材(G)との密着性の面より、(メタ)アクリル酸、モノ(メタ)アクリル酸ω−カルボキシポリカプロラクトンエステルであるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
芳香脂肪族ポリイソシアネートとしては、ω,ω’−ジイソシアネート−1,3−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジエチルベンゼン、1,4−テトラメチルキシリレンジイソシアネート、1,3−テトラメチルキシリレンジイソシアネート等を挙げることができる。
フェニレンジアミン、キシリレンジアミン、2,4−トリレンジアミン、2,6−トリレンジアミン、ジエチルトルエンジアミン,3,3’−ジクロロ−4,4’−ジアミノジフェニルメタン、4,4’−ビス−(sec−ブチル)ジフェニルメタン等の芳香族ジアミン;
トリメチルシリルジメチルアミン等の単官能のシリルアミノ基を保有するシリルアミン類;
1,1,3,3−テトラメチルジシラザン等の2官能のシリルアミノ基を保有するシリルアミン類が使用できる。
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類;
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等が挙げられる。
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;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
化合物(a1)が1重量部より少ないと、後述の金属キレート化合物(C)の溶解性を低下させるだけで無く、後述の基材(G)との密着性が低下する。化合物(a1)が60重量部より多いと、耐水性が劣るため好ましくない。化合物(a2)が1重量部より少ないと、塗膜の耐熱性や耐湿熱性が低下する。化合物(a2)が45重量部より多いと、塗膜の柔軟性が失われ、脆くなったりするため好ましくない。
カチオン重合性化合物(B)はカチオンにより重合する化合物を全て含んでいる。カチオン重合性化合物(B)としては活性エネルギー線による反応性の観点から、環状ヘテロ化合物やビニルエーテル化合物が好ましく、3員環エーテルであるオキシラン化合物(b2)が特に好ましい。オキシラン化合物が反応するとヒドロキシル基が発生し、金属キレート化合物との相互作用が働き、後述の基材(G)との密着性向上に大きな効果を示す。また、活性エネルギー線硬化樹脂組成物の凝集力や架橋度を向上させることができ、該基材(G)の少なくとも一方の主面に設けられた上記活性エネルギー線重合性樹脂組成物からなる樹脂層とを有する積層体としての耐熱性、耐湿熱性、熱的寸法安定性向上に大きな効果を示す。
ここに例示したオキシラン化合物は、それぞれ単独で使用してもよいし、また複数のオキシラン化合物を混合して使用してもよい。
等の環状化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合し得る芳香環が挙げられる。
オキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−2−オン、7−[2−(2−オキソ−4−メチル−1,3−ジオキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−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、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、4,5−ジクロロ−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−(フェニルチオメチル)−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、4,4,5,5−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−(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;
化合物(b1)が1重量部より少ないと、後述の無機ホウ素系化合物(C)の溶解性を低下させるだけで無く、後述の基材(G)との密着性が低下する。化合物(b1)が60重量部より多いと、耐水性が劣るため好ましくない。
金属キレート化合物(C)は、α,β−エチレン性不飽和二重結合基含有化合物(A)やカチオン重合性化合物(B)と相互作用して水や有機溶剤を含まずとも安定で均一な活性エネルギー線重合性樹脂組成物の液を形成できることを可能とし、当該組成物の液を活性エネルギー線で硬化後は、化合物(A)及び/又は化合物(B)と配位結合や共有結合を介して結合した塗膜を形成する。また、後述の基材(G)の表面官能基と結合を形成して密着性を良くするだけでなく、抜き打ち加工性や耐熱性、耐湿熱性を向上させる。化合物(C)は単独又は混合して使用可能である。
化合物(C)が0.1重量%部未満であると所望の接着力発現に至らず、10重量%以上であると、時間の経過で析出したり、樹脂成分が減ることで密着力が低下するなどの問題が生じる場合がある。
活性エネルギー線重合開始剤(D)としては例えば活性エネルギー線ラジカル重合開始剤(d1)や活性エネルギー線カチオン開始剤(d2)を使うことができる。本発明の樹脂組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。そのため樹脂組成物には、活性エネルギー線重合開始剤(D)を含む必要がある。活性エネルギー線重合開始剤(D)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましい。
具体例として、例えば、以下が挙げられる。2,2−ジメトキシ−2−フェニルアセトフェノン、アセトフェノン、ベンゾフェノン、キサントフルオレノン、ベンズアルデヒド、アントラキノン、3−メチルアセトフェノン、4−クロロベンゾフェノン、4,4’−ジアミノベンゾフェノン、ベンゾインプロピルエーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4−チオキサントン、カンファーキノン、及び2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン等。
また、市販品としては、例えば、以下が挙げられる。イルガキュアー184,907,651,1700,1800,819,369,及び261(BASF社製)、DAROCUR−TPO(BASF社製、2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド)、ダロキュア−1173(メルク社製)、エザキュアーKIP150,及びTZT(日本シイベルヘグナー社製)、カヤキュアBMS,及びカヤキュアDMBI(日本化薬社製)等。
また、分子内に少なくとも1個の(メタ)アクリロイル基を有する光重合開始剤を使用することもできる。
本発明では、上記成分(D)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。本発明では、上記成分(D)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。
本発明の樹脂組成物は、本発明による効果を損なわない範囲であれば、各種添加剤を適宜配合することも可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩、及び染顔料等の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、シランカップリング剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、酸化防止剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、及び消泡剤等の、独立した充填剤としてではなく、ポリマーブレンド又はポリマーアロイとして、樹脂組成物中に、溶解、半溶解又はミクロ分散させることも可能である。
(I)第1の透明フィルム(第1の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第1の重合性接着層を形成する。また、第2の透明フィルム(第2の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第2の重合性接着層を形成する。次いで、ポリビニルアルコール系偏光子の両主面に、上記第1の重合性接着層と第2の重合性接着層とを、同時に/又は順番に、重ね合わせる。次いで、得られた積層体に活性エネルギー線を照射し、第1及び第2の接着層を重合硬化させる。
実施例によって限定されるものではない。また、下記実施例及び比較例に記載の、「部」及び「%」は、それぞれ「重量部」および「重量%」を表す。
ただし、配合例3、4、22〜38、41、42に基づく、実施例1、3、20〜36は参考例である。
<活性エネルギー線重合性樹脂組成物の調整>
[配合例1〜61]
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、表1〜表3に示す比率(重量部)で仕込み、ディスパーにて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す活性エネルギー線重合性樹脂組成物をそれぞれ得た。
2MTA:アクリル酸2−メトキシエチル
ALE200:アクリル酸ラウロキシ-ポリエチレングリコール(n=4)
MCMA:アクリル酸(メトキシカルボニル)メチル
4HBA:アクリル酸4−ヒドロキシブチル
2HEA:アクリル酸2−ヒドロキシエチル
AA:アクリル酸
UV3000B:日本合成化学工業社製 ポリウレタン系オリゴマー(ウレタンアクリレート)
Ebecryl600:ダイセルサイテック社製ポリエポキシ系オリゴマー(エポキシアクリレート)
DCPA:アクリル酸ジシクロペンタニル
IBXA:アクリル酸イソボルニル
CHDMMA:アクリル酸1,4−シクロヘキサンジメタノール
nBA:アクリル酸ブチル
NPGDA:ジアクリル酸ネオペンチルグリコール
JER828:2,2'−(ジメチルメチレン)ビス[(p−フェニレン)オキシメチレン]ビスオキシラン (三菱化学社製)
CEP−01:1,3−フェニレンビス(メチレン)ビス(7−オキサビシクロ[4.1.0]ヘプタン−3−カルボキシレイト)
2021P:3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート (ダイセル社製 セロキサイド2021P)
EGDG:エチレングリコールジグリシジルエーテル
GCDG:グリセリンジグリシジルエーテル
OXT−101:3−エチル−3−ヒドロキシメチルオキセタン(東亞合成社製 アロンオキセタンOXT−101)
GC:グリセリンカーボネート
DEGVE:ジエチレングリコールモノビニルエーテル
TC100:チタンアセチルアセトネート(マツモトファインケミカル社製)
TC400:チタントリエタノールアミネート(マツモトファインケミカル社製)
ZC150:ジルコニウムテトラアセチルアセトネート(マツモトファインケミカル社製)
ALM:アルミニウムアルキルアセトアセテート・ジイソプロピレート(川研ファインケミカル社製)
TPO:2,4,6−トリメチルベンゾイル-ジフェニル-フォスフィンオキサイト゛(BASF社製,DAROCUR TPO)
CPI110P:トリアリールスルホニウム塩タイプの光酸発生剤(サンアプロ社製)
各配合例で得られた樹脂組成物の外観を観察し、目視にて評価した。
各配合例で得られた樹脂組成物を23℃の雰囲気下でE型粘度計(東機産業社製 TV−22)にて、約1.2mlを測定用試料とし、回転速度0.5〜100rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
[実施例1〜64][比較例1〜6]
透明フィルム(1)、(2)として、表5に示すフィルムを使用し、以下の方法で積層体を作成した。
透明フィルム(1)、(2)の表面に300W・min/m2 の放電量でコロナ処理を行い、表面処理後1時間以内に、表1〜表3に示す活性エネルギー線重合性接着剤をワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、活性エネルギー線重合性接着層を形成し、前記活性エネルギー線重合性接着層との間にポリビニルアルコール系偏光子を挟み、透明フィルム(1)/接着層/PVA系偏光子/接着層/透明フィルム(2)からなる積層体を得た。透明フィルム(1)がブリキ板に接するように、この積層体の四方をセロハンテープで固定し、ブリキ板に固定した。
接着力は、JIS K6 854−4 接着剤−剥離接着強さ試験方法−第4部:浮動ローラー法に準拠して測定した。
即ち、得られた偏光板を、25mm×150mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを両面粘着テープ(トーヨーケム社製DF8712S)を使用して、ラミネータを用いて金属板上に貼り付けて、偏光板と金属板との測定用の積層体を得た。測定用の積層体の偏光板には、保護フィルムと偏光子の間に予め剥離のキッカケを設けておき、この測定用の積層体を23℃、相対湿度50%の条件下で、300mm/分の速度で引き剥がし、剥離力とした。この際、ポリビニルアルコール系偏光子と保護フィルム(1)、及びポリビニルアルコール系偏光子と保護フィルム(2)との双方の剥離力を測定した。この剥離力を接着力として4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:剥離不可、あるいは偏光板破壊
○:剥離力が2.0(N/25mm)以上〜5.0(N/25mm)未満。
△:剥離力が1.0(N/25mm)以上〜2.0(N/25mm)未満。
×:剥離力が1.0(N/25mm)未満。
コロナ処理を施していない日本ゼオン社製のポリノルボルネン系フィルム(商品名「ゼオノア ZF−14:100μm」に、活性エネルギー線重合性接着剤を、ワイヤーバーコーターを用いて膜厚20〜25μmとなるように塗工し、活性エネルギー線重合性接着層を形成した。さらに活性エネルギー線重合性接着層の上にコロナ処理を施していないゼオノア ZF−14を重ね、3層からなる積層体を得た後、活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の活性エネルギー線を照射し活性エネルギー線重合性接着層を重合硬化させた。3層からなる積層体のゼオノア ZF−14を剥離し接着剤層を得た。
接着剤層の重量を測定した後(重量1)を金属メッシュと金属メッシュの間に挟み接着剤層同士が重ならないようにし、メチルエチルケトン(MEK)中で3時間還流した。さらに80℃−30分乾燥し、接着剤層の重量を測定した(重量2)。下記式よりゲル分率を求め、3段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
ゲル分率(%)={1−(重量1−重量2)/重量1)}×100
(評価基準)
○:ゲル分率が90%以上
△:ゲル分率が80%以上〜90%未満
×:ゲル分率が80%未満
ダンベル社製の100mm×100mmの刃を用い、作製した偏光板を保護フィルム(1)側から打ち抜いた。
打ち抜いた偏光板の、周辺の剥離距離を定規で測定し、以下の4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0mm
○:1mm以下
△:1〜3mm
×:3mm以上
上記偏光板小片を80℃−dryと60℃−90RH%の恒温恒湿機中に放置し、60時間後の延伸方向の縮み量を測定し、元の長さ(100mm)に対する縮み量の割合を収縮率とし求め、以下の3段階で評価をした。
なお、「dry」とは、湿度調整機能付のオーブンで、温度のみコントロールし、湿度のコントロールを行わなかった場合の試験条件である。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
○:収縮率が0.2%以下
△:収縮率が0.2%より大きくて0.4%以下
×:収縮率が0.4%を超える。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、80℃−dry、及び100℃dryの条件下で、それぞれ1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:100℃−dryの条件下でも剥がれが全く無し。
○:80℃−dry条件下で剥がれが全く無し。
△:80℃−dry条件下で1mm未満の剥がれあり。
×:80℃−dry条件下で1mm以上の剥がれあり。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、60℃−90%RHの条件下、及び85℃−85%RHの条件下で1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:85℃−85%RHの条件下でも剥がれが全く無し。
○:60℃−90%RHの条件下で剥がれが全く無し。
△:60℃−90%RHの条件下で1mm未満の剥がれあり。
×:60℃−90%RHの条件下で1mm以上の剥がれあり。
[実施例66〜135][比較例7〜12]
表1〜表3に示した樹脂組成物を活性エネルギー線重合性コート剤として使用し、光学フィルムとして、表6に示すフィルムを使用し、以下の方法で積層体を作成した。
光学フィルム表面を300W・min/m2の放電量でコロナ処理を行い、表面処理後1時間以内に、配合例に示す樹脂組成物を活性エネルギー線重合性コート剤として、ワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、コート剤層を形成した。光学フィルムがブリキ板に接するように、この積層体の四方をセロハンテープで、ブリキ板に固定した。
UV照射装置(東芝社製 高圧水銀灯)内を乾燥窒素で置換後、波長365nmの最大照度300mW/cm2、積算光量300mJ/cm2の紫外線をコート剤層側から照射して、コート剤層を有する積層体を作製した。
JIS K5400に従い、碁盤目剥離試験を実施した。100マス中の剥離したマス数を4段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0マス
○:1〜10マス
△:11〜30マス
×:31マス以上
各実施例と比較例で得られた積層体を、50mm×40mmの大きさに裁断し、80℃−dryの条件下で1000時間暴露した。暴露後積層体の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
○:剥がれが全く無し
△:1mm未満の剥がれあり
×:1mm以上の剥がれあり
尚、例示フィルムの表記として、
TAC80:富士フィルム社製 ポリトリアセチルセルロース系フィルム(紫外線吸収剤含有、膜厚80μm)、
TAC50:富士フィルムビジネスサプライ社製 ポリトリアセチルセルロース系フィルム(紫外線吸収剤を含有していない、膜厚50μm)、
ZF−14:日本ゼオン社製 ポリノルボルネン系フィルム(紫外線吸収剤を含有していない、膜厚100μm)、
HBD−002:三菱レーヨン社製ポリアクリル系フィルム(紫外線吸収剤を含有していない、膜厚50μm)、
R−140:カネカ社製 ポリカーボネート系フィルム(紫外線吸収剤を含有しない、膜厚43μm)、
エンプレットS:ユニチカ社製 ポリエステル系フィルム(紫外線吸収剤を含有する、膜厚50μm)、
TUX−HZ:東セロ社製 ポリエチレン系フィルム(紫外線吸収剤を含有する、50μm)
を示す。
また、本発明の樹脂組成物をコート剤として用いた場合は、表5と同様の傾向であり、表6に示す様に実施例69〜77、79〜84、88〜92、94〜100、103〜107、109〜135では、密着性、及び耐熱性とも優れ、特に問題無い。また、実施例66〜68、78、85〜87、93、100〜102、108は、密着性、および耐熱性のレベルが低いが、使用することが可能である。これに対して比較例7〜12では、特に密着性、あるいは耐熱性に劣ることがわかる。
Claims (5)
- α,β−エチレン性不飽和二重結合基含有化合物(A)と、
金属キレート化合物(C)と、
活性エネルギー線重合開始剤(D)とを含有し、
前記化合物(A)が、アルコキシ基、エーテル基、ヒドロキシル基及びケト基(ただし、α,β−不飽和二重結合基に直接結合しているアルコキシ基、エーテル基、ヒドロキシル基及びケト基を除く)からなる群から選択される1以上の官能基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)と
化合物(A)が、1以上の環状構造を有するα,β−エチレン性不飽和二重結合基含有化合物(a2)とを含むことを特徴とする偏光板の保護フィルムを貼着するための接着剤である活性エネルギー線重合性樹脂組成物。 - 活性エネルギー線重合組成物全量中、
化合物(C)を0.1〜10重量%、
活性エネルギー線重合開始剤(D)0.01〜20重量%含有することを特徴とする請求項1記載の活性エネルギー線重合性樹脂組成物。 - 基材(G)である保護フィルム、偏光子、及び、保護フィルムと偏光子とを接着する樹脂層を含んでなる偏光板であって、
該基材(G)の少なくとも一方の主面に、請求項1または2いずれか記載の樹脂組成物からなる樹脂層が設けられた偏光板。
- 基材(G)が、透明フィルム(H)であることを特徴とする請求項3記載の偏光板。
- 前記、透明フィルム(H)が、ポリアセチルセルロース系フィルム、ポリノルボルネン系フィルム、ポリプロピレン系フィルム、ポリアクリル系フィルム、ポリカーボネート系フィルム、ポリエステル系フィルム、ポリビニルアルコール系フィルム及びポリイミド系フィルムからなる群から選択される少なくとも1種であることを特徴とする請求項4記載の偏光板。
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