JP5220191B2 - 光学部材用アクリル系組成物、光学部材用保護フィルム、偏光板及び液晶表示装置 - Google Patents
光学部材用アクリル系組成物、光学部材用保護フィルム、偏光板及び液晶表示装置 Download PDFInfo
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- JP5220191B2 JP5220191B2 JP2011516150A JP2011516150A JP5220191B2 JP 5220191 B2 JP5220191 B2 JP 5220191B2 JP 2011516150 A JP2011516150 A JP 2011516150A JP 2011516150 A JP2011516150 A JP 2011516150A JP 5220191 B2 JP5220191 B2 JP 5220191B2
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- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
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- 230000002087 whitening effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Description
本発明のアクリル系共重合体に含まれる光重合性アクリル系重合体は、主鎖と、上記主鎖に結合され、光活性基を提供する光重合性基含有化合物とを含み、これにより、光照射によって開始剤で発生するラジカルによって架橋反応を起こすことができる。
アクリレート(例えば、イソシアネート単量体及びトリメチロールプロパントリ(メタ)アクリレートの反応物などの6官能型アクリレートなどを使用することができるが、これらに限定されるものではない。
窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)80重量部、n−ブチルアクリレート(BA)17重量部及び2−ヒドロキシブチルアクリレート(2−HBA)3.0重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングした後、温度を55℃に維持した。その後、反応器に反応開始剤としてエチルアセテートに50%の濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系共重合体(A)を製造した。
製造例1で製造されたアクリル重合体(A)を、窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に投入し、2−メタクリロイルオキシエチルイソシアネート(2-methacryloyloxyethyl isocyanate)3.3重量部及び適正量の触媒をさらに反応器に投入した。その後、反応器の温度を40℃に維持させた状態で、2時間反応させて光重合性基が導入されたアクリル系重合体(A1)を製造した。
製造例1で使用された反応器に2−エチルヘキシルアクリレート(2−EHA)90重量部、n−ブチルアクリレート(BA)5重量部及び2−ヒドロキシブチルアクリレート(2−HBA)5.0重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングし、反応器の温度を55℃に維持した。その後、反応器に開始剤としてエチルアセテートに50%濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系共重合体(B)を製造した。
製造例3で製造されたアクリル共重合体100重量部、2−メタクリロイルオキシイソシアネート5.5重量部及び適正量の触媒を反応器に投入し、40℃で2時間反応させて光重合性アクリル系共重合体(B1)を製造した。
窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)75重量部、n−ブチルアクリレート(BA)10重量部及び2−ヒドロキシブチルアクリレート(2−HBA)15重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングし、55℃に維持した。その後、反応器に開始剤としてエチルアセテートに50%濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系重合体(C)を製造した。
製造例5で製造されたアクリル重合体100重量部、2−メタクリロイルオキシエチルイソシアネート16.5重量部及び適正量の触媒を反応器に投入し、40℃で2時間反応させて光重合性アクリル系重合体(C1)を製造した。
窒素ガスが還流され、温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)95重量部、n−ブチルアクリレート(BA)4.95重量部及び2−ヒドロキシブチルアクリレート(2−HBA)0.05重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。その後、酸素除去のために窒素ガスを1時間パージングし、55℃に維持した。その後、反応器に開始剤としてエチルアセテートに50%濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系重合体(D)を製造した。
製造例7で製造されたアクリル重合体100重量部、2−メタクリロイルオキシエチルイソシアネート0.055重量部及び適正量の触媒を反応器に投入し、40℃で2時間反応させて光重合性アクリル系重合体(D1)を製造した。
窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)99.5重量部及び2−ヒドロキシブチルアクリレート(2−HBA)0.5重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングした後、温度を55℃に維持した。その後、反応器に反応開始剤としてエチルアセテートに50%の濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系共重合体(E)を製造した。
製造例9で製造されたアクリル重合体(E)を、窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に投入し、2−メタクリロイルオキシエチルイソシアネート(2-methacryloyloxyethyl isocyanate)0.55重量部及び適正量の触媒をさらに反応器に投入した。その後、反応器の温度を40℃に維持させた状態で、2時間反応させて光重合性基が導入されたアクリル系重合体(E1)を製造した。
窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)90.9重量部、n−ブチルアクリレート(BA)9.0重量部及び2−ヒドロキシブチルアクリレート(2−HBA)0.1重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングした後、温度を55℃に維持した。その後、反応器に反応開始剤としてエチルアセテートに50%の濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系共重合体(F)を製造した。
製造例11で製造されたアクリル重合体(F)を、窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に投入し、2−メタクリロイルオキシエチルイソシアネート(2-methacryloyloxyethyl isocyanate)0.11重量部及び適正量の触媒をさらに反応器に投入した。その後、反応器の温度を40℃に維持させた状態で、2時間反応させて光重合性基が導入されたアクリル系重合体(F1)を製造した。
窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に2−エチルヘキシルアクリレート(2−EHA)89.995重量部、n−ブチルアクリレート(BA)10重量部及び2−ヒドロキシブチルアクリレート(2−HBA)0.005重量部を投入し、溶剤としてエチルアセテート(EAc)100重量部を投入した。次に、酸素除去のために窒素ガスを1時間パージングした後、温度を55℃に維持した。その後、反応器に反応開始剤としてエチルアセテートに50%の濃度で希釈させたアゾビスイソブチロニトリル(AIBN)0.05重量部を投入し、8時間反応させてアクリル系共重合体(G)を製造した。
製造例1で製造されたアクリル重合体(G)を、窒素ガスが還流され且つ温度調節が容易な冷却装置を設置した1L反応器に投入し、2−メタクリロイルオキシエチルイソシアネート(2-methacryloyloxyethyl isocyanate)0.0055重量部及び適正量の触媒をさらに反応器に投入した。その後、反応器の温度を40℃に維持させた状態で、2時間反応させて光重合性基が導入されたアクリル系重合体(G1)を製造した。
光重合性アクリル系重合体(A1)100重量部、ポリエチレングリコールの脂肪酸系アルキルエステル及びLiClO4を含む帯電防止剤0.5重量部及び光開始剤として1−ヒドロキシ−シクロヘキシル−フェニルケトン(Irgacure 184、Ciba社製)0.5重量部を混合し、適正濃度に希釈してコーティング液を製造した。次に、コーティング液を厚さが38μmの2軸延伸PETフィルムの一面にコーティングし、乾燥し、厚さを約20μmに制御し、離型フィルムにラミネートした。その後、水銀ランプ(UVB領域、280mJ/cm2)を利用して光重合させて、保護フィルムを製造した。
アクリル系組成物の配合を下記表1及び表2に示されたように実施したことを除いて、実施例1と同一の方法で保護フィルムを製造した(下記表1及び表2で、含量の単位は重量部である)。
実施例及び比較例で製造した保護フィルムが付着された偏光板(200mm×200mm)を高温条件(耐熱条件)(80℃、1,000時間)及び高温高湿条件(耐湿熱条件)(60℃、90%R.H.、1,000時間)条件の下で放置した後、粘着剤面で浮き上がりまたは剥離現象が発生するか否かを観察し、下記基準によって信頼性を評価した。
○:浮き上がりまたは剥離現象無し
△:浮き上がりまたは剥離現象多少ある
×:浮き上がりまたは剥離現象多量発生
実施例及び比較例で製造した保護フィルムを各々40mm×70mmのサイズに切断し、試験片を製造し、JIS K7150及びASTM D1003−95に基づいてヘイズを評価した。具体的に、積分球式光線透過率測定装置を利用して拡散透過率(Td)及び全光線透過率(Ti)を測定し、Tiに対するTdの百分率でヘイズを定義した。その後、試験片を60℃の温度及び90%の相対湿度条件の下で1,000時間放置し、同一の方式でヘイズを測定し、放置前後のヘイズを比較し、白化現象を評価した。
実施例及び比較例で製造した保護フィルムを偏光板の防眩層(AG、日本国DNP社製)面に2Kgのローラーを使用して付着し、23℃の温度及び50%の相対湿度条件で24時間保管した(試料のサイズ:22cm×24cm)。その後、試験片に付着された保護フィルムを40m/分の速度で剥離しながら、偏光板の表面から2cm上部に位置する静電圧測定器(STATIRON−M2)を利用して、偏光板表面で発生する静電圧を測定した。上記と同一の方式で静電圧を10回ずつ測定し、その平均値を数値として下記表2に示した。
実施例及び比較例で製造した保護フィルムを偏光板の防眩層(AG、日本国DNP社製)面にJIS Z 0237に基づいて、2Kgのローラーを利用して付着し、23℃の温度及び65%の相対湿度条件で24時間保管した。その後、引張試験機器を使用して、180゜剥離角度で、0.3m/分及び30.0m/分の剥離速度で剥離強度を測定した。
実施例及び比較例で製造した保護フィルムを偏光板の防眩層(AG、日本DNP社製)面にJIS Z 0237に基づいて2Kgのローラーを使用して付着した。その後、23℃の温度及び65%の相対湿度条件で24時間保管した後、25cm×2.5cmのサイズに切断して試験片を製造した。次に、試験片から保護フィルムの一方を剥離し、他方へ1cm程度を残して、さらに保護フィルムを軽く放して、保護フィルムが再付着される時間を測定する。
○:再付着時間が10秒以下
×:再付着時間が10秒超過
上記のような測定結果を下記表3にまとめて示した。
Claims (19)
- 基材と;該基材上に形成された粘着層とを含み、
前記粘着層は、(メタ)アクリル酸エステル系単量体90重量部〜99.9重量部及び極性単量体0.1重量部〜10重量部を含む単量体混合物の重合体である主鎖と、上記主鎖に結合された光重合性基含有化合物0.06重量部〜16重量部とを含む光重合性アクリル系重合体100重量部と;
帯電防止剤0.01重量部〜9重量部と;
重合開始剤0.01重量部〜9重量部と;を含むアクリル系組成物の硬化物で構成される、光学部材用保護フィルム。 - (メタ)アクリル酸エステル系単量体は、炭素数が1〜14のアルキル基を有するアルキル(メタ)アクリレートであることを特徴とする請求項1に記載の光学部材用保護フィルム。
- 極性単量体が、ヒドロキシ基、カルボキシル基、イソシアネート基、アミノ基またはエポキシ基を含有することを特徴とする請求項1に記載の光学部材用保護フィルム。
- 光重合性基含有化合物が、2−イソシアネートエチル(メタ)アクリレート、1、1−ビス(アクリロイルオキシメチル)エチルイソシアネート、(メタ)アクリロイルオキシエチルイソシアネート、メタ−イソプロペニル−α、α−ジメチルベンジルイソシアネート、メタクリロイルイソシアネート、アリルイソシアネート;アクリロイルモノイソシアネート化合物;(メタ)アクリル酸グリシジル;(メタ)アクリル酸;及び3−メタクリロキシプロピルジメチルクロロシランよりなる群から選択された1つ以上であることを特徴とする請求項1に記載の光学部材用保護フィルム。
- 光重合性アクリル系重合体は、重量平均分子量が20万〜100万であることを特徴とする請求項1に記載の光学部材用保護フィルム。
- 帯電防止剤が、i)アルキレンオキシド含有化合物及び金属塩の混合物;またはii)配位結合性化合物及び金属塩の混合物であることを特徴とする請求項1に記載の光学部材用保護フィルム。
- アルキレンオキシド含有化合物が、ポリアルキレングリコール、ポリアルキレングリコールの脂肪酸系アルキルエステルまたはポリアルキレングリコールのカルボン酸エステルであることを特徴とする請求項6に記載の光学部材用保護フィルム。
- アルキレンオキシド含有化合物は、重量平均分子量が100〜10,000であることを特徴とする請求項6に記載の光学部材用保護フィルム。
- 配位結合性化合物は、オキサレート基含有化合物、ジアミン基含有化合物、多価カルボキシル基含有化合物及びβ−ケトン基含有化合物よりなる群から選択された1つ以上であることを特徴とする請求項6に記載の光学部材用保護フィルム。
- オキサレート基含有化合物が、ジエチルオキサレート、ジメチルオキサレート、ジブチルオキサレート、ジ−tert−ブチルオキサレートまたはビス(4−メチルベンジル)オキサレートであり、ジアミン基含有化合物が、エチレンジアミン、1、2−ジアミノプロパンまたはジアミノブタンであり、多価カルボキシル基含有化合物が、エチレンジアミン−N、N、N’、N’−テトラ酢酸、N、N、N’、N”、N”−ジエチレントリアミンペンタ酢酸、1、4、7、10−テトラアザシクロドデカン−N、N’、N”、N”−テトラ酢酸、1、4、7、10−テトラアザシクロドデカン−N、N’、N”−トリ酢酸、トランス(1、2)−シクロヘキサノジエチレントリアミンペンタ酢酸またはN、N−ビスカルボキシメチルグリシンであり、β−ケトン基含有化合物が、2、4−ペンタジオン、1−ベンゾイルアセトンまたはエチルアセトアセテートであることを特徴とする請求項10に記載の光学部材用保護フィルム。
- 金属塩は、Li+、Na+、K+、Rb+、Cs+、Be2+、Mg2+、Ca2+、Sr2+及びBa2+よりなる群から選択された1つ以上の陽イオン;及びF−、Cl−、Br−、I−、ClO4 −、OH−、CO3 2−、CH3CO2 −、N3 −、HPO4 2−、NO3 −、SO4 2−、CH3(C6H4)SO3 −、CH3C6H4SO3 −、COOH(C6H4)SO3 −、CF3SO2 −、C6H5COO−、CH3COO−、CF3COO−、BF4 −、B(C6H5)4 −、PF6 −、P(C2F5)3F3 −)−、N(SO2CF3)2 −、N(SOC2F5)2 −、N(COC2F5)2 −、N(COC2F5)2 −、N(SO2C4F9)2 −、N(COC4F9)2 −、C(SO2CF3)3 −及びC(SO2CF3)3 −よりなる群から選択された1つ以上の陰イオンを含むことを特徴とする請求項6に記載の光学部材用保護フィルム。
- 重合開始剤は、ベンゾイン系化合物、ヒドロキシケトン系化合物、アミノケトン系化合物またはホスフィンオキシド系化合物であることを特徴とする請求項1に記載の光学部材用保護フィルム。
- アクリル系重合体100重量部に対して0.1重量部〜10重量部の光重合性化合物をさらに含むことを特徴とする請求項1に記載の光学部材用保護フィルム。
- 光重合性化合物が多官能性アクリレート、ウレタンアクリレートオリゴマーまたはエポキシアクリレートオリゴマーであることを特徴とする請求項14に記載の光学部材用保護フィルム。
- 基材は、厚さが5μm〜500μmであることを特徴とする請求項1に記載の光学部材用保護フィルム。
- 粘着層は、厚さが2μm〜100μmであることを特徴とする請求項1に記載の光学部材用保護フィルム。
- 請求項1に記載の保護フィルムが一面または両面に付着された偏光板。
- 請求項18に記載の偏光板が液晶パネルの一面または両面に付着されている液晶表示装置。
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KR101939324B1 (ko) | 2018-09-28 | 2019-01-16 | 효성화학 주식회사 | 내응력(耐應力) 내백화(耐白化) 필름 |
US11426978B2 (en) * | 2018-10-05 | 2022-08-30 | Samsung Display Co., Ltd. | Adhesive member and display device including the same |
KR102526293B1 (ko) | 2019-01-25 | 2023-04-26 | 주식회사 엘지화학 | 표면 보호 필름 및 이를 이용한 유기 발광 전자 장치 제조 방법 |
KR102542899B1 (ko) | 2021-07-20 | 2023-06-15 | 한국화학연구원 | 신규한 n-설포닐 아지리딘 화합물 및 이의 제조방법 |
CN113549411A (zh) * | 2021-08-06 | 2021-10-26 | 深圳力合博汇光敏材料有限公司 | 一种防静电保护膜用的uv固化热熔压敏胶 |
CN114133880A (zh) * | 2021-12-27 | 2022-03-04 | 江西塔益莱高分子材料有限公司 | 一种偏光片用胶粘剂及其制备方法 |
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US5508107A (en) * | 1993-07-28 | 1996-04-16 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive tapes for electronics applications |
EP1431320A1 (en) * | 2002-12-20 | 2004-06-23 | Dainippon Ink And Chemicals, Inc. | Curable liquid compositions containing acrylate groups and beta-dicarbonyl compounds |
JP2005314579A (ja) * | 2004-04-30 | 2005-11-10 | Nitto Denko Corp | 粘着剤組成物、および粘着シート類 |
CN101120070B (zh) * | 2005-02-16 | 2010-12-01 | 日本合成化学工业株式会社 | 光学部件用粘合剂、光学部件用粘合剂的制造方法 |
JP2006309114A (ja) * | 2005-03-30 | 2006-11-09 | Lintec Corp | 偏光板用粘着剤、粘着剤付き偏光板及びその製造方法 |
CN1872933A (zh) * | 2005-03-30 | 2006-12-06 | 琳得科株式会社 | 起偏振片用压敏粘合剂和起偏振片及起偏振片的制备方法 |
DE602006018906D1 (de) * | 2005-05-20 | 2011-01-27 | Nitto Denko Corp | Haftklebemittel, haftklebefolie und oberflächenschutzfilm |
KR100838973B1 (ko) * | 2005-06-08 | 2008-06-17 | 주식회사 엘지화학 | 아크릴계 점착제 조성물 |
KR101198531B1 (ko) * | 2005-06-24 | 2012-11-06 | 토요잉크Sc홀딩스주식회사 | 대전방지 아크릴 점착제 |
JP5259940B2 (ja) * | 2005-09-05 | 2013-08-07 | 日東電工株式会社 | 粘着剤組成物、粘着シートおよび表面保護フィルム |
KR100830814B1 (ko) * | 2005-10-14 | 2008-05-20 | 주식회사 엘지화학 | 아크릴계 점착제 조성물 |
JP2008050590A (ja) * | 2006-07-24 | 2008-03-06 | Nippon Shokubai Co Ltd | 電子線硬化性樹脂組成物、積層体、及び、粘着シート又は粘着フィルム |
JP4493643B2 (ja) * | 2006-12-06 | 2010-06-30 | 日東電工株式会社 | 再剥離型粘着剤組成物、及び粘着テープ又はシート |
JP4994895B2 (ja) * | 2007-03-09 | 2012-08-08 | リンテック株式会社 | 粘着シート |
JP2010523806A (ja) * | 2007-04-13 | 2010-07-15 | スリーエム イノベイティブ プロパティズ カンパニー | 静電気防止性の光学的に透明な感圧性接着剤 |
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- 2009-07-01 US US13/001,773 patent/US20110109849A1/en not_active Abandoned
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CN102083932B (zh) | 2014-08-20 |
CN102083932A (zh) | 2011-06-01 |
WO2010002197A3 (ko) | 2010-04-22 |
TW201014890A (en) | 2010-04-16 |
US20110109849A1 (en) | 2011-05-12 |
KR101114354B1 (ko) | 2012-06-12 |
JP2011526646A (ja) | 2011-10-13 |
WO2010002197A2 (ko) | 2010-01-07 |
TWI471396B (zh) | 2015-02-01 |
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