JP5979424B2 - 反射防止塗料組成物及び反射防止フィルム - Google Patents
反射防止塗料組成物及び反射防止フィルム Download PDFInfo
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- JP5979424B2 JP5979424B2 JP2012140879A JP2012140879A JP5979424B2 JP 5979424 B2 JP5979424 B2 JP 5979424B2 JP 2012140879 A JP2012140879 A JP 2012140879A JP 2012140879 A JP2012140879 A JP 2012140879A JP 5979424 B2 JP5979424 B2 JP 5979424B2
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Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
ポリ(パーフルオロアルキレンエーテル)鎖とその両末端に重合性不飽和基を有する化合物(A)と、シリコーン鎖を有する重合性不飽和単量体(B)と、反応性官能基(c1)を持つアダマンチル基を有する重合性不飽和単量体(C1)とを必須の単量体成分として共重合させて得られる重合体(P1)に、前記官能基(c1)に対して反応性を有する官能基(d)及び重合性不飽和基を有する化合物(D)を反応させる方法。
ポリ(パーフルオロアルキレンエーテル)鎖とその両末端に重合性不飽和基を有する化合物(A)と、シリコーン鎖を有する重合性不飽和単量体(B)と、反応性官能基(c1)を持つアダマンチル基を有する重合性不飽和単量体(C1)又は反応性官能基(c1)を持たないアダマンチル基を有する重合性不飽和単量体(C2)と、反応性官能基(c3)を有する重合性不飽和単量体(C3)とを必須の単量体成分として共重合させて得られる重合体(P2)に、前記官能基(c1)又は前記官能基(c3)に対して反応性を有する官能基(d)及び重合性不飽和基を有する1種以上の化合物(D)を反応させる方法。
方法1:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸クロライドを脱塩酸反応させて得る方法。
方法2:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸を脱水反応させて得る方法。
方法3:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して2−(メタ)アクリロイルオキシエチルイソシアネートをウレタン化反応させて得る方法。
方法4:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して無水イタコン酸をエステル化反応させて得る方法。
方法5:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対してクロロメチルスチレンを脱塩酸反応させて得る方法。
方法6:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸無水物をエステル化反応させる方法。
方法7:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にカルボキシル基を1つずつ有する化合物に対して4−ヒドロキシブチル(メタ)アクリレートグリシジルエーテルをエステル化反応させて得る方法。
方法8:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にカルボキシル基を1つずつ有する化合物に対してグリシジル(メタ)アクリレートをエステル化反応させて得る方法。
方法9:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にイソシアネート基を1つずつ有する化合物に対して2−ヒドロキシエチル(メタ)アクリレートを反応させて得る方法。
方法10:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にイソシアネート基を1つずつ有する化合物に対して2−ヒドロキシエチル(メタ)アクリルアミドを反応させる方法。
方法11:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にエポキシ基を1つずつ有する化合物に対して(メタ)アクリル酸をエステル化反応させる方法。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
(1)まず基材にハードコート材を塗布・硬化してハードコート層の塗膜を形成する。
(2)上記のハードコート層に本発明の反射防止塗料組成物を塗布・硬化して低屈折率層の塗膜を形成する。この低屈折率層が反射防止フィルムの最表面となる。
なお、上記ハードコート層と低屈折率層との間に、中屈折率層及び/又は高屈折率層を設けても構わない。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、下記構造式(X−1)で表される両末端水酸基含有パーフルオロポリエーテル化合物(X−1)20質量部、溶媒としてジイソプロピルエーテル10質量部、重合禁止剤としてp−メトキシフェノール0.006質量部及び中和剤としてトリエチルアミン3.3質量部を仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらメタクリル酸クロライド3.1質量部を2時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌した後、50℃に昇温して10時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にてメタクリル酸クロライドの消失が確認された。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン69.3質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、合成例1で得られた単量体(A−1−1)74.0質量部、3−ヒドロキシ−1−アダマンチルメタクリレート59.2質量部と下式(Y−1)で表されるポリジメチルシロキサン鎖を有する片末端メタクリロイル基含有単量体37.0質量部と溶媒としてメチルイソブチルケトン100質量部の3種を混合した単量体溶液、ラジカル重合開始剤としてt−ブチルペルオキシ−2−エチルヘキサノエート25.5質量部と溶媒としてメチルイソブチルケトン38.7質量部を混合した開始剤溶液の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了後、105℃で10時間攪拌して、重合体(P1−1)の溶液を得た。
(nの数は平均65である。)
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン65.3質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、合成例1で得られた単量体(A−1−1)74.0質量部、3−ヒドロキシ−1−アダマンチルメタクリレート75.7質量部と(Y−1)で表されるポリジメチルシロキサン鎖を有する片末端メタクリロイル基含有単量体10.7質量部と溶媒としてメチルイソブチルケトン100質量部の3種を混合した単量体溶液、ラジカル重合開始剤としてt−ブチルペルオキシ−2−エチルヘキサノエート24.1質量部と溶媒としてメチルイソブチルケトン30.7質量部を混合した開始剤溶液の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了後、105℃で10時間攪拌して、重合体(P1−2)の溶液を得た。
<反射防止塗料組成物の調製>
中空シリカ微粒子(平均粒子径50nm)を20質量%含有するメチルイソブチルケトン分散液15質量部、ペンタエリスリトールトリアクリレート1.6質量部、光重合開始剤として2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]−フェニル}−2−メチル−プロパン−1−オン(チバ・ジャパン株式会社製「イルガキュア127」)0.1質量部、溶剤としてメチルイソブチルケトン81.8質量部を混合し溶解させて、反射防止塗料組成物のベース組成物を得た。
5官能無黄変型ウレタンアクリレート50質量部、ジペンタエリスリトールヘキサアクリレート50質量部、酢酸ブチル25質量部、光重合開始剤として1−ヒドロキシシクロヘキシルフェニルケトン(チバスペシャリティーケミカルズ社製「イルガキュア184」)5質量部、溶剤としてトルエン54質量部、2−プロパノール28質量部、酢酸エチル28質量部、プロピレングリコールモノメチルエーテル28質量部を混合し溶解させて、ハードコート層用塗料組成物を得た。
黒色の板上に上記で得た反射防止フィルムを置き、反射防止塗料組成物の硬化塗膜の白化の有無を目視で観察し、下記の基準で外観を評価した。評価結果を第1表に示す。
○:白化が生じていないもの。
×:白化が生じているもの。
トライボギア HEIDON 往復磨耗試験機 TYPE:30S(新東科学株式会社製)を用いて、直径27mmの円形の治具にボンスター No,0000(日本スチールウール株式会社製)を取り付けた磨耗試験機(500g/cm2荷重)にて、30往復磨耗させて試験を行った。試験後の塗膜表面に付いた傷の本数を数えて、下記の基準によって耐擦傷性を評価した。
◎:傷の本数が5本未満である。
○:傷の本数が5本以上10本未満である。
△:傷の本数が10本以上50本未満である。
×:傷の本数が50本以上である。
上記で得た反射防止フィルムの反射防止塗料組成物の硬化塗膜の表面に指で指紋を付着させ、ティッシュペーパーで10往復拭き取ったときの拭き取り具合を目視で観察し、下記の基準で指紋汚れ拭き取り性を評価した。
◎:指紋が完全に拭き取れるもの。
○:指紋の付着跡、又は、拭き取り方向に沿って線状の跡が、付着時に比べわずかに残ったもの。
×:指紋の付着跡、又は、拭き取り方向に沿って線状の跡が、付着時の半分以上の濃さで残ったもの。
5℃正反射測定装置を備えた分光光度計(株式会社島津製作所製「UV−3100PC」)を用いて反射率の測定を行った。なお、反射率は波長550nm付近で極小値(最低反射率)となったときの値とした。
上記で得られた反射防止フィルムを、70℃に加温した2.0mol/Lの水酸化カリウム水溶液に1分間浸漬させ、水洗後、100℃で3分間乾燥させて、強アルカリ処理を行った。
実施例1で用いた重合性樹脂(III−1)の20%含有溶液に代えて重合性樹脂(III−2)の40%含有溶液を樹脂分として0.4質量部となるように添加した以外は実施例1と同様に操作して、評価を行った。評価結果を第1表に示す。
比較例1
実施例1で用いた重合性樹脂(III−1)の20%含有溶液に代えて、シリコーンオイル(チッソ株式会社製「サイラプレーンFM−4421」、ポリジメチルシロキサン鎖の両末端に−C3H6OC2H4OHを有するもの)を50質量%含有するメチルイソブチルケトン溶液を0.8質量部(樹脂分として0.4質量部)添加した以外は実施例1と同様に操作して、評価を行った。評価結果を第1表に示す。
実施例1で用いた重合性樹脂(III−1)の20%含有溶液に代えて、FM−0721K(チッソ株式会社製のシリコーンオイル。パーフルオロアルキル基、アダマンチル基を有していないが、重合性不飽和基を片末端に有している。)を50質量%含有するメチルイソブチルケトン溶液を0.8質量部(樹脂分として0.4質量部)添加した以外は実施例1と同様に操作して、評価を行った。評価結果を第1表に示す。
実施例1で用いた重合性樹脂(III−1)の20%含有溶液に代えて、ジメチルシロキサン鎖を有する4官能アクリレート(ビックケミー・ジャパン株式会社製「BYK−UV3570」)を50質量%含有するメチルイソブチルケトン溶液を0.8質量部(樹脂分として0.4質量部)添加した以外は実施例1と同様に操作して、評価を行った。評価結果を第1表に示す。
実施例1で調製した活性エネルギー線硬化性組成物のベース樹脂組成物に、何も添加せずに実施例1と同様に操作して、評価を行った。評価結果を第1表に示す。
Claims (6)
- 低屈折率剤(I)、活性エネルギー線硬化性化合物(II)、及びポリ(パーフルオロアルキレンエーテル)鎖とシリコーン鎖とアダマンチル基と重合性不飽和基とを有する重合性樹脂であって前記活性エネルギー線硬化性化合物(II)以外の重合性樹脂(III)を含有することを特徴とする反射防止塗料組成物。
- 前記シリコーン鎖が分子量2,000〜20,000のものである請求項1記載の反射防止塗料組成物。
- 前記低屈折率剤(I)が中空シリカ微粒子である請求項1記載の反射防止塗料組成物。
- 前記低屈折率剤(I)及び活性エネルギー線硬化性化合物(II)の合計100質量部に対して、前記重合性樹脂(III)を0.1〜20質量部含有する請求項1〜3のいずれか1項記載の反射防止塗料組成物。
- 請求項1〜4のいずれか1項記載の反射防止塗料組成物の硬化塗膜を有することを特徴とする反射防止フィルム。
- 前記硬化塗膜の膜厚が50〜300nmである請求項5記載の反射防止フィルム。
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KR101768929B1 (ko) * | 2010-09-30 | 2017-08-17 | 디아이씨 가부시끼가이샤 | 함불소 중합성 수지, 그것을 사용한 활성 에너지선 경화형 조성물 및 그 경화물 |
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