JPWO2020040209A1 - ハードコート組成物、ハードコート付きポリイミドフィルムおよびその製造方法、ならびに画像表示装置 - Google Patents
ハードコート組成物、ハードコート付きポリイミドフィルムおよびその製造方法、ならびに画像表示装置 Download PDFInfo
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- JPWO2020040209A1 JPWO2020040209A1 JP2020538442A JP2020538442A JPWO2020040209A1 JP WO2020040209 A1 JPWO2020040209 A1 JP WO2020040209A1 JP 2020538442 A JP2020538442 A JP 2020538442A JP 2020538442 A JP2020538442 A JP 2020538442A JP WO2020040209 A1 JPWO2020040209 A1 JP WO2020040209A1
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- hard coat
- polyimide film
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- acid dianhydride
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 104
- 238000004519 manufacturing process Methods 0.000 title claims description 10
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- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 75
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 68
- 230000001678 irradiating effect Effects 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 97
- 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 claims description 95
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- 239000011258 core-shell material Substances 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 36
- 239000011737 fluorine Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 21
- 229910000077 silane Inorganic materials 0.000 claims description 20
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- 125000003118 aryl group Chemical group 0.000 claims description 11
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- 229910044991 metal oxide Inorganic materials 0.000 claims description 8
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- 239000000758 substrate Substances 0.000 description 8
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 7
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 7
- 150000007514 bases Chemical class 0.000 description 7
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002985 plastic film Substances 0.000 description 6
- 229920006255 plastic film Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
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- 239000002612 dispersion medium Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 229920000126 latex Polymers 0.000 description 5
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- JPZRPCNEISCANI-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F JPZRPCNEISCANI-UHFFFAOYSA-N 0.000 description 4
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 4
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- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- 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 4
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- 150000001408 amides Chemical class 0.000 description 2
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Abstract
Description
Y−R1−(Si(OR2)xR3 3−x) …(I)
ポリイミドフィルム1は、全光線透過率が80%以上の透明フィルムである。ポリイミドフィルムの全光線透過率は85%以上が好ましく、88%以上がより好ましく、90%以上がさらに好ましい。ポリイミドフィルムのヘイズは2%以下が好ましく、1%以下がより好ましい。ポリイミドフィルムのヘイズは0.1%以上または0.2%以上であってもよい。
ポリイミドフィルムはポリイミド樹脂を含む。ポリイミド樹脂は、一般に、テトラカルボン酸二無水物(以下、単に「酸二無水物」と記載する場合がある)とジアミンとの縮合により得られるポリアミド酸を脱水環化することにより得られる。すなわち、ポリイミドは、酸二無水物由来構造とジアミン由来構造とを有する。透明ポリイミド樹脂は、好ましくは、酸二無水物およびジアミンの少なくとも一方に、脂環式構造またはフッ素原子を含み、より好ましくは、酸二無水物およびジアミンの両方に、脂環式構造またはフッ素原子を含む。
透明性が高く着色の少ないポリイミドフィルムを得るためには、ポリイミドが、酸二無水物成分として、脂環式酸二無水物および/またはフッ素含有芳香族酸二無水物を含むことが好ましい。
透明ポリイミドは、ジアミン成分として、フッ素含有芳香族ジアミンを含むことが好ましい。
一実施形態において、ポリイミド樹脂は、酸二無水物として、脂環式酸二無水物およびフッ素含有芳香族酸二無水物を含み、ジアミンとして、フッ素含有ジアミンおよびスルホニル基含有ジアミンを含む。
一実施形態において、ポリイミド樹脂は、酸二無水物として上記の一般式(1)で表される酸二無水物(ビス無水トリメリット酸エステル)およびフッ素含有芳香族酸二無水物を含み、ジアミンとしてフッ素含有ジアミンを含む。このポリイミドは、塩化メチレン等の低沸点ハロゲン化アルキルに対して高い溶解性を示し、かつ、ポリイミドフィルムが高い透明性および機械強度を示す傾向がある。
ポリアミド酸は、例えば、有機溶媒中で酸二無水物とジアミンとを反応させることにより得られる。酸二無水物とジアミンは略等モル量(95:100〜105:100のモル比)を用いることが好ましい。酸二無水物の開環を抑制するため、溶媒中にジアミンを溶解させた後、酸二無水物を添加する方法が好ましい。複数種のジアミンや複数種の酸二無水物を添加する場合は、一度に添加してもよく、複数回に分けて添加してもよい。ポリアミド酸溶液は、通常5〜35重量%、好ましくは10〜30重量%の濃度で得られる。
ポリアミド酸の脱水環化によりポリイミドが得られる。ポリイミドフィルムの作製方法としては、支持体上にポリアミド酸溶液を膜状に塗布し、溶媒を乾燥除去するとともにポリアミド酸をイミド化する方法と、ポリイミド酸溶液のイミド化を行い、得られたポリイミド樹脂を溶媒に溶解した溶液を支持体上に膜状に塗布して溶媒を乾燥除去する方法が挙げられる。ポリイミド樹脂の溶媒に対する可溶性が低い場合は、前者の方法が用いられる。可溶性ポリイミドのフィルム化にはいずれの方法も利用できる。残存不純物が少なく透明性の高いポリイミドフィルムを得る観点から、後者の方法が好ましい。
ポリイミドフィルムにハードコート層を形成するためのハードコート組成物は、シロキサン化合物を含有する光硬化性樹脂組成物である。
ハードコート層形成用樹脂組成物に含まれるシロキサン化合物は、光カチオン重合性官能基として脂環式エポキシ基を有する。脂環式エポキシ基としては、3,4−エポキシシクロヘキシル基が好ましい。シロキサン化合物としては、例えばWO2014/204010に記載の光硬化性シロキサン化合物を用いることができる。
Y−R1−(Si(OR2)xR3 3−x) …(I)
R4−(Si(OR2)3 …(II)
ハードコート組成物は、光カチオン重合開始剤を含むことが好ましい。光カチオン重合開始剤は、活性エネルギー線の照射により酸を発生する化合物(光酸発生剤)である。光酸発生剤から生成した酸により、上記のシロキサン化合物の脂環式エポキシ基が反応して、分子間架橋が形成されハードコート材料が硬化する。
ハードコート組成物は、膜特性の調整や、硬化収縮の抑制等を目的として粒子を含んでいてもよい。粒子としては、有機粒子、無機粒子、有機無機複合粒子等を適宜選択して用いればよい。有機粒子の材料としては、ポリ(メタ)アクリル酸アルキルエステル、架橋ポリ(メタ)アクリル酸アルキルエステル、架橋スチレン、ナイロン、シリコーン、架橋シリコーン、架橋ウレタン、架橋ブタジエン等が挙げられる。無機粒子の材料としては、シリカ、チタニア、アルミナ、酸化スズ、ジルコニア、酸化亜鉛、酸化アンチモン等の金属酸化物;窒化珪素、窒化ホウ素等の金属窒素化物;炭酸カルシウム、リン酸水素カルシウム、リン酸カルシウム、リン酸アルミニウム等の金属塩等が挙げられる。有機無機複合フィラーとしては、有機粒子の表面に無機物層を形成したものや、無機粒子の表面に有機物層または有機微粒子を形成したものが挙げられる。
無機粒子をハードコート組成物に配合することにより、硬化膜の表面硬度が向上する傾向がある。特に、金属酸化物粒子を用いた場合に、硬化膜の密着性、耐擦傷性、耐屈曲性等を抑制しつつ、表面硬度が向上する傾向がある。金属酸化物としては、シリカ、チタニア、アルミナ、酸化スズ、ジルコニア、酸化亜鉛、酸化アンチモン等が挙げられる。中でも、有機物による表面修飾が容易であり、分散性に優れることから、シリカ粒子が好ましい。
コアシェルポリマー粒子をハードコート組成物に配合することにより、硬化膜の耐屈曲性が向上する傾向があり、特に、ハードコート層を外側としてハードコートフィルムを屈曲した際のハードコート層の割れや剥がれが抑制される傾向がある。
ハードコート組成物は、反応性希釈剤を含んでいてもよい。組成物に反応性希釈剤を配合することにより、光カチオン重合の反応点(架橋点)の密度が増加するため、硬化速度が高められる場合がある。
ハードコート組成物は、感光性の向上等を目的として光増感剤を含んでいてもよい。光増感剤としては、アントラセン誘導体、ベンゾフェノン誘導体、チオキサントン誘導体、アントラキノン誘導体、ベンゾイン誘導体等が挙げられる。中でも、光誘起電子供与性の観点から、アントラセン誘導体、チオキサントン誘導体、およびベンゾフェノン誘導体が好ましい。
ハードコート組成物は、無溶媒型でもよく、溶媒を含んでいてもよい。溶媒は、ポリイミドフィルムを溶解させないものが好ましい。一方、ポリイミドフィルムを膨潤させる程度の溶解性を有する溶媒を用いることにより、ポリイミドフィルムとハードコート層との密着性が向上する場合がある。溶媒としては、メチルイソブチルケトンやジイソブチルケトン等のケトン類;ブタノールやイソプロピルアルコール等のアルコール類;酢酸ブチルや酢酸イソプロピル等のエステル類;ジエチレングリコールメチルエーテルやプロピレングリコールメチルエーテル等のエーテル類;N,N−ジメチルアセトアミド、N,N−ジメチルホルムアミド、N−メチル−2−ピロリドン等のアミド類;クロロホルム、塩化メチレン等のハロゲン化アルキル類が挙げられる。溶媒の配合量は、上記のシロキサン化合物100重量部に対して500重量部以下が好ましく、300重量部以下がより好ましい。
ハードコート組成物は、無機顔料や有機顔料、可塑剤、分散剤、湿潤剤、増粘剤、消泡剤等の添加剤を含んでいてもよい。また、ハードコート組成物は、上記のシロキサン化合物以外の熱可塑性または熱硬化性の樹脂材料を含んでいてもよい。シロキサン化合物および/またはシロキサン化合物以外の樹脂材料がラジカル重合性を有する場合、ハードコート組成物は、光カチオン重合開始剤に加えて光ラジカル重合開始剤を含んでいてもよい。
ハードコート組成物の調製方法は特に限定されない。例えば、上記の各成分を配合し、ハンドミキサーやスタティックミキサー等による混合、プラネタリーミキサーやディスパー、ロール、ニーダー等による混練等を行ってもよい。これらの操作は、必要に応じて遮光した状態で実施してもよい。
透明ポリイミドフィルム上にハードコート組成物を塗布し、必要に応じて溶媒を乾燥除去した後、活性エネルギー線を照射してハードコート組成物を硬化することにより、ポリイミドフィルム1上にハードコート層2が設けられたハードコート付きポリイミドフィルムが得られる。
上述のように、本発明のハードコート組成物の硬化により形成されるハードコート層は、ポリイミドフィルムとの密着性に優れる。また、ハードコート組成物は、シロキサン化合物が脂環式エポキシ基の重合反応により架橋されたポリマーマトリクスを有するため、ガラスに匹敵する表面硬度を実現し得る。ハードコート付きポリイミドフィルムのハードコート層形成面の鉛筆硬度は3H以上が好ましく、4H以上がより好ましい。さらに、ハードコート層は耐擦傷性にも優れている。
ハードコート付きポリイミドフィルムは、ハードコート層上、またはポリイミドフィルムのハードコート層非形成面には、各種の機能層を設けてもよい。機能層としては、反射防止層、防眩層、帯電防止層、透明電極等が挙げられる。また、ハードコートフィルムには、透明粘着剤層が付設されてもよい。
<ポリイミドフィルム1>
(ポリアミド酸溶液1の調製)
反応容器に、N,N−ジメチルホルムアミド(DMF)を383重量部投入し、窒素雰囲気下で攪拌した。そこに、2,2’−ビス(トリフルオロメチル)ベンジジン:36.3重量部、3,3’−ジアミノジフェニルスルホン:12.0重量部、1,2,3,4−シクロブタンテトラカルボン酸二無水物:15.8重量部、および2,2−ビス(3,4−ジカルボキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン二無水物:35.9重量部を順次添加し、窒素雰囲気下で攪拌してポリアミド酸溶液1を得た。
ポリイミド酸溶液(ポリアミド酸の固形分100重量部)に、イミド化触媒としてピリジン38.4重量部を添加し、攪拌した後、無水酢酸49.5重量部を添加し、120℃で2時間攪拌後、室温まで冷却してポリイミド溶液を得た。溶液を攪拌しながら、1Lのイソプロピルアルコールを滴下して、ポリイミド樹脂を析出させた。その後、濾別したポリイミド樹脂をイソプロピルアルコールで3回洗浄した後、120℃で12時間乾燥させて白色のポリイミド樹脂1(PI−1)の粉体を得た。
ポリイミド樹脂1をメチルエチルケトンに溶解し、固形分濃度17%のポリイミド溶液を得た。コンマコーターを用いて、ポリイミド溶液を無アルカリガラス板上に塗布し、40℃で10分、80℃で30分、150℃で30分、170℃で1時間、大気雰囲気下で乾燥した後、無アルカリガラス板から剥離して、厚み80μmまたは50μmの透明ポリイミドフィルム1を得た。厚み80μmのポリイミドフィルム1の全光線透過率は89.8%であり、厚み50μmのポリイミドフィルム1の全光線透過率は90.0%であった。
(ポリアミド酸溶液2の調製、イミド化およびポリイミド樹脂の析出)
反応容器に、DMFを383重量部投入し、窒素雰囲気下で攪拌した。そこに、2,2’−ビス(トリフルオロメチル)ベンジジン:31.8重量部、および3,3’−ジアミノジフェニルスルホン:10.5重量部を投入し、窒素雰囲気下で撹拌してジアミン溶液を得た。そこに、p−フェニレンビス(トリメリット酸無水物):15.9重量部、2,2−ビス(3,4−ジカルボキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン酸二無水物:37.4重量部、および3,3’,4,4’−ビフェニルテトラカルボン酸二無水物:10.4重量部を加え、窒素雰囲気下で攪拌してポリアミド酸溶液2を得た。得られたポリアミド酸溶液2を用い、上記のポリイミド樹脂1の調製と同様にして、イミド化、ポリイミド樹脂の析出、洗浄および乾燥を行い、白色のポリイミド樹脂2(PI−2)の粉体を得た。
ポリイミド樹脂2を塩化メチレンに溶解し、固形分濃度10%のポリイミド溶液を得た。コンマコーターを用いて、ポリイミド溶液を無アルカリガラス板上に塗布し、40℃で60分、80℃で30分、150℃で30分、170℃で30分、大気雰囲気下で乾燥した後、無アルカリガラス板から剥離して、厚み50μmの透明ポリイミドフィルム2を得た。ポリイミドフィルム2の全光線透過率は89.0%であった。
反応容器に、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ製「SILQUEST A−186」)100重量部、塩化マグネシウム0.12重量部、水11重量部およびプロピレングリコールモノメチルエーテル11重量部を仕込み、130℃で3時間撹拌後、60℃で減圧脱揮して縮合物(シロキサン樹脂)を得た。
厚み80μmの透明ポリイミドフィルム1の表面に、上記のハードコート組成物を乾燥膜厚が10μmとなるようにバーコーターを用いて塗布し、120℃で2分間加熱した。その後、高圧水銀ランプを用いて、波長250〜390nmの積算光量が1000mJ/cm2となるように紫外線を照射してハードコート組成物を硬化させて、ハードコート付きポリイミドフィルム(ハードコートフィルム1)を得た。
ハードコート層の厚みが40μmとなるように塗布厚みを変更したこと以外は実施例1と同様にして、ハードコート付きポリイミドフィルム(ハードコートフィルム2)を得た。
厚み50μmの透明ポリイミドフィルム1を用いたこと以外は実施例2と同様にして、ハードコート付きポリイミドフィルム(ハードコートフィルム3)を得た。
厚み50μmの透明ポリイミドフィルム2を用い、ハードコート樹脂組成物における光酸発生剤の配合量を、シロキサン樹脂100重量部に対して0.2重量部に変更したこと以外は実施例1と同様にして、ハードコート付きポリイミドフィルム(ハードコートフィルム4)を得た。
ハードコート層の厚みが40μmとなるように塗布厚みを変更したこと以外は実施例4と同様にして、ハードコート付きポリイミドフィルム(ハードコートフィルム5)を得た。
基材フィルムとして、ポリイミドフィルムに代えて、厚み50μmのポリエチレンテレフタレート(PET)フィルム(東レ製、L−50T60)、厚み40μmのアクリル系フィルム、厚み50μmのポリエチレンナフタレート(PEN)フィルム(帝人製、Teonex Q51)、および厚み80μmのトリアセチルセルロース(TAC)フィルムを用い、実施例1と同様にして、フィルム表面に厚み10μmのハードコート層を形成した。アクリルフィルムおよびTACフィルムは、それぞれ、アクリル樹脂(クラレ製パラペットHR−G)およびトリアセチルセルロース樹脂(和光純薬製)の塩化メチレン溶液を用いて溶液製膜により作製した。
下記に従って、実施例および比較例で得られたハードコートフィルムを評価した。
ハードコート層に、1mm間隔で100マスの碁盤目状の切り込みを入れ、JIS K5600−5−6:1999に準拠してクロスカット試験を行い、フィルムの表面からハードコート層が剥離したマス目の割合(%)を記録した。数字が小さいほど、ハードコート層の密着性が良好であることを示す。
JIS K5600−5−1:1999に従って、ハードコート層形成面を内側として、タイプ1の試験機を用いて円筒型マンドレル試験を行った。マンドレルの径が小さいほど、耐屈曲性に優れることを示す。
JIS K5600−5−4:1999により、ハードコート層形成面の鉛筆硬度を測定した。
往復磨耗試験機(新東科学製)を用いて、ハードコート層の表面に162g/cm2の荷重をかけてスチールウール#0000を10往復または100往復させた後、傷の有無を目視にて観察した。傷がない場合をOK、傷がある場合をNGとした。
スガ試験機製ヘイズメーターHZ−V3により、JIS K7361−1:1999およびJIS K7136:2000に記載の方法により測定した。
ハードコート樹脂組成物の調製において、シロキサン樹脂100重量部に代えて、シロキサン樹脂と下記の手順で作製したコアシェルポリマー(コアシェルゴム)粒子の分散液を配合した。配合比は表2に示す通りであった(表2におけるコアシェルゴム粒子の量は固形分である)。それ以外はハードコートフィルム1の作製と同様にして、透明ポリイミドフィルムの表面にハードコート組成物を塗布し、加熱乾燥後に紫外線を照射して光硬化を行い、ポリイミドフィルム上に厚み10μmのハードコート層を備えるハードコート付きポリイミドフィルム(ハードコートフィルム6〜9)を得た。
耐圧重合機中に、水200重量部、リン酸三カリウム0.03重量部、リン酸二水素カリウム0.25重量部、エチレンジアミン4酢酸0.002重量部、硫酸第一鉄0.001重量部およびドデシルベンゼンスルホン酸ナトリウム1.5重量部を投入した。攪拌しながら十分に窒素置換を行って酸素を除いた後、ブタジエン75重量部およびスチレン25重量部を系中に投入し、45℃に昇温した。パラメンタンハイドロパーオキサイド0.015重量部、およびナトリウムホルムアルデヒドスルホキシレート(SFS)0.04重量部を順に投入して、重合を開始した。重合開始から4時間後に、パラメンタンハイドロパーオキサイド0.01重量部、エチレンジアミン4酢酸(EDTA)0.0015重量部および硫酸第一鉄0.001重量部を投入した。重合開始から10時間後に減圧下で残存モノマーを脱揮除去し、重合を終了した。得られたスチレン−ブタジエンゴムラテックスの体積平均粒径は100nmであった。
ハードコート樹脂組成物の調製において、シロキサン樹脂100重量部に代えて、シロキサン樹脂90重量部と以下に示す液状アクリル樹脂10重量部を配合した。それ以外はハードコートフィルム1の作製と同様にして、透明ポリイミドフィルムの表面に厚み10μmのハードコート層を備えるハードコート付きポリイミドフィルム(ハードコートフィルム10〜12)を得た。
UG−4010:東亞合成製「ARUFON UG−4010」 側鎖にエポキシ基を有する液状アクリル樹脂(重量平均分子量2900)
UH−2041:東亞合成製「ARUFON UH−2041」 側鎖にOH基を有する液状アクリル樹脂(重量平均分子量2500)
ハードコートフィルム6〜12について、上記と同様の評価を行った。円筒型マンドレル試験による耐屈曲性評価では、ハードコート層形成面を内側として屈曲させる試験(内曲げ)に加えて、ハードコート層形成面を外側として屈曲させる試験(外曲げ)による評価を実施した。ハードコートフィルム3〜9の作製に用いたハードコート組成物の樹脂成分の組成、および評価結果を、ハードコートフィルム1の評価結果とともに表2に示す。
ハードコート樹脂組成物の調製において、シロキサン樹脂100重量部に代えて、シロキサン樹脂と以下に示すシリカ微粒子の分散液とを配合した。配合比は表3に示す通りであった(表3におけるシリカ粒子の量は固形分である)。それ以外はハードコートフィルム1の作製と同様にして、透明ポリイミドフィルムの表面に厚み10μmのハードコート層を備えるハードコート付きポリイミドフィルム(ハードコートフィルム13〜18)を得た。
MEK−EC−2130Y:日産化学製の表面が疎水処理されたコロイダルシリカのコロイド溶液、粒子径:10〜15nm、分散媒:メチルエチルケトン、固形分:30%
MEK−AC−2140Z:日産化学製の表面がメタアクリロイル処理されたコロイダルシリカのコロイド溶液、粒子径:10〜15nm、分散媒:メチルエチルケトン、固形分:40%
PGM−AC−4130Y:日産化学製の表面がメタアクリロイル処理されたコロイダルシリカのコロイド溶液、粒子径:40〜50nm,分散媒:プロピレングリコールモノメチルエーテル、固形分:30%
ハードコートフィルム13〜18について、上記と同様の評価を行った。ハードコートフィルム13〜18の作製に用いたハードコート組成物の樹脂成分の組成、および評価結果を、ハードコートフィルム1の評価結果とともに表3に示す。
2 ハードコート層
10 ハードコートフィルム
Claims (18)
- 透明ポリイミドフィルムの主面上へのハードコート層の形成に用いられるハードコート組成物であって、
脂環式エポキシ基を有するシロキサン化合物を含む、ポリイミドフィルム用ハードコート組成物。 - 前記シロキサン化合物が、下記一般式(I)で表される化合物を含むシラン化合物の縮合物である、請求項1に記載のポリイミドフィルム用ハードコート組成物:
Y−R1−(Si(OR2)xR3 3−x) …(I)
式(I)において、Yは脂環式エポキシ基であり;R1は炭素数1〜10のアルキレン基であり;R2は水素原子または炭素数1〜10のアルキル基であり;R3は、水素原子、炭素数1〜10のアルキル基、炭素数6〜25のアリール基および炭素数7〜12のアラルキル基から選択される1価の炭化水素基であり;xは1〜3の整数である。 - 前記シロキサン化合物の重量平均分子量が500〜20000である、請求項1または2に記載のポリイミドフィルム用ハードコート組成物。
- さらに、光カチオン重合開始剤を含有する、請求項1〜3のいずれか1項に記載のポリイミドフィルム用ハードコート組成物。
- さらに、平均粒子径が5〜1000nmの粒子を含有する、請求項1〜4のいずれか1項に記載のポリイミドフィルム用ハードコート組成物。
- 前記粒子が金属酸化物粒子である、請求項5に記載のポリイミドフィルム用ハードコート組成物。
- 前記金属酸化物粒子が、シリカである請求項6に記載のポリイミドフィルム用ハードコート組成物。
- 前記粒子が、ゴムポリマーのコア層と、前記コア層の表面に設けられたシェル層とを含むコアシェルポリマー粒子である、請求項5に記載のポリイミドフィルム用ハードコート組成物。
- 前記粒子が、表面に、前記シロキサン化合物の脂環式エポキシ基と反応可能な重合性官能基を有する、請求項5〜8のいずれか1項に記載のポリイミドフィルム用ハードコート組成物。
- 前記重合性官能基がエポキシ基である、請求項9に記載のポリイミドフィルム用ハードコート組成物。
- 透明ポリイミドフィルムの主面上に、請求項1〜10のいずれか1項に記載のハードコート組成物の硬化物からなるハードコート層を備え、全光線透過率が80%以上である、ハードコート付きポリイミドフィルム。
- 前記ポリイミドフィルムは、酸二無水物由来構造とジアミン由来構造とを有するポリイミド樹脂を含み、
前記酸二無水物として、脂環式酸二無水物およびフッ素含有芳香族酸二無水物からなる群から選択される1種以上を含み、前記ジアミンとして、フッ素含有ジアミンを含む、請求項11に記載のハードコート付きポリイミドフィルム。 - 前記ポリイミド樹脂は、
前記酸二無水物として、脂環式酸二無水物およびフッ素含有芳香族酸二無水物を、酸二無水物全量100モル%に対して合計70モル%以上含み、
前記ジアミンとして、フルオロアルキル置換ベンジジンおよび3,3’−ジアミノジフェニルスルホンを、ジアミン全量100モル%に対して合計70モル%以上含む、請求項12に記載のハードコート付きポリイミドフィルム。 - 前記ハードコート層の厚みが1〜50μmである、請求項11〜14のいずれか1項に記載のハードコート付きポリイミドフィルム。
- 前記ポリイミドフィルムと前記ハードコート層とが接している、請求項11〜15のいずれか1項に記載のハードコート付きポリイミドフィルム。
- 画像表示パネルの表面に、請求項11〜16のいずれか1項に記載のハードコート付きポリイミドフィルムを備える、表示装置。
- 全光線透過率が80%以上の透明ポリイミドフィルムの主面上に、請求項1〜10のいずれか1項に記載のハードコート組成物を塗布し、
活性エネルギー線を照射して、前記ハードコート組成物を硬化する、ハードコート付きポリイミドフィルムの製造方法。
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