JP2018177952A - 硬化性組成物、硬化物及びハードコートフィルム - Google Patents
硬化性組成物、硬化物及びハードコートフィルム Download PDFInfo
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- JP2018177952A JP2018177952A JP2017079167A JP2017079167A JP2018177952A JP 2018177952 A JP2018177952 A JP 2018177952A JP 2017079167 A JP2017079167 A JP 2017079167A JP 2017079167 A JP2017079167 A JP 2017079167A JP 2018177952 A JP2018177952 A JP 2018177952A
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Landscapes
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Abstract
Description
ポリオルガノシルセスキオキサン:下記式(1)で表される構成単位を有し、下記式(I)で表される構成単位と、下記式(II)で表される構成単位のモル比[式(I)で表される構成単位/式(II)で表される構成単位]が5以上であり、シロキサン構成単位の全量(100モル%)に対する、下記式(1)で表される構成単位、及び下記式(4)で表される構成単位の割合が55〜100モル%であり、数平均分子量が1000〜3000、分子量分散度(重量平均分子量/数平均分子量)が1.0〜3.0である
本発明の硬化性組成物は、下記のポリオルガノシルセスキオキサン及び表面に(メタ)アクリロイル基を含む基を有するシリカ粒子を必須成分として含む硬化性組成物である。本発明の硬化性組成物は、特にハードコート層形成用硬化性組成物であることが好ましい。後述のように、硬化性組成物は、さらに、光カチオン重合開始剤、及びポリオルガノシルセスキオキサン以外のカチオン硬化性化合物等のその他の成分を含んでいてもよい。
前記ポリオルガノシルセスキオキサン(シルセスキオキサン)は、下記式(1)で表される構成単位を有し、下記式(I)で表される構成単位(「T3体」と称する場合がある)と、下記式(II)で表される構成単位(「T2体」と称する場合がある)のモル比[式(I)で表される構成単位/式(II)で表される構成単位;「T3体/T2体」と記載する場合がある]が5以上であり、シロキサン構成単位の全量(100モル%)に対する下記式(1)で表される構成単位及び後述の式(4)で表される構成単位の割合(総量)が55〜100モル%であり、数平均分子量が1000〜3000、分子量分散度[重量平均分子量/数平均分子量]が1.0〜3.0であることを特徴とする。
測定装置:商品名「JNM−ECA500NMR」(日本電子(株)製)
溶媒:重クロロホルム
積算回数:1800回
測定温度:25℃
測定装置:商品名「FT−720」((株)堀場製作所製)
測定方法:透過法
分解能:4cm-1
測定波数域:400〜4000cm-1
積算回数:16回
測定装置:商品名「LC−20AD」((株)島津製作所製)
カラム:Shodex KF−801×2本、KF−802、及びKF−803(昭和電工(株)製)
測定温度:40℃
溶離液:THF、試料濃度0.1〜0.2重量%
流量:1mL/分
検出器:UV−VIS検出器(商品名「SPD−20A」、(株)島津製作所製)
分子量:標準ポリスチレン換算
本発明の硬化性組成物は、必須の成分として表面に(メタ)アクリロイル基を含む基を有するシリカ粒子を含む。前記シリカ粒子は、シリカ粒子の表面に無数の水酸基(Si−OH基)が存在し、硬化時に当該水酸基と前記ポリオルガノシルセスキオキサンとが反応することで、ポリオルガノシルセスキオキサンの硬化後の架橋密度が向上する。また、硬化時に複数の前記シリカ粒子における(メタ)アクリロイル基どうしが結合することで、硬化後の架橋密度が向上する。このように硬化後の架橋密度が向上することで、硬化物(特に、ハードコート層)における耐擦傷性やリコート性が向上する。さらに、前記シリカ粒子は、表面に(メタ)アクリロイル基を有することで、硬化性組成物における安定性を付与できると考えられる。前記の安定性とは、硬化前の硬化性組成物の調製段階において、前記シリカ粒子とポリオルガノシルセスキオキサンとが反応して、硬化性組成物の粘度が著しく上昇(ゲル化)したり、固化したりしないことを言う。(メタ)アクリロイル基を含む基などの官能基を表面に有さない通常のシリカ粒子(SiO2粒子)を用いた場合、シリカ粒子どうしが凝集し、硬化性組成物がゲル化するおそれがある。前記シリカ粒子は、(メタ)アクリロイル基以外の官能基(例えば、シリコーン変性基)を有していてもよい。なお、(メタ)アクリロイル基は、アクリロイル基(アクリル基)及びメタアクリロイル基(メタクリル基)の総称である。
前記硬化性組成物は、タックフリーとなるまでの硬化時間が短縮できる点で、硬化触媒として光カチオン重合開始剤を含むことが好ましい。
本発明の硬化性組成物におけるカチオン硬化性化合物(ポリオルガノシルセスキオキサン等)の重合反応を進行させることにより、硬化性組成物を硬化させることができ、硬化物を得ることができる。本発明の硬化物は、前記硬化性組成物を用いているため、表面の平滑性などの外観及び加工性が良く、リコート性を有する。
本発明のハードコートフィルムは、基材と、当該基材の少なくとも一方の表面に形成されたハードコート層とを有するハードコートフィルムであって、前記ハードコート層が、本発明の硬化性組成物の硬化物層であることを特徴とする。なお、本発明のハードコートフィルムにおける前記ハードコート層は、上記基材の一方の表面(片面)のみに形成されていてもよいし、両方の表面(両面)に形成されていてもよい。
本発明のハードコートフィルムは、公知乃至慣用のハードコートフィルムの製造方法に準じて製造することができ、その製造方法は特に限定されないが、例えば、上記基材の少なくとも一方の表面に前記硬化性組成物(特に、ハードコート層形成用硬化性組成物)を塗布し、上述のハードコート層と同様に、硬化性組成物を硬化させることにより製造できる。硬化性組成物を硬化させる際の条件は、特に限定されず、上述のハードコート層を形成する際の条件から適宜選択可能である。
温度計、攪拌装置、還流冷却器、及び窒素導入管を取り付けた300ミリリットルのフラスコ(反応容器)に、窒素気流下で2−(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(以下、「EMS」と称する)161.5ミリモル(39.79g)、フェニルトリメトキシシラン(以下、「PMS」と称する)9ミリモル(1.69g)、及びアセトン165.9gを仕込み、50℃に昇温した。このようにして得られた混合物に、5%炭酸カリウム水溶液4.70g(炭酸カリウムとして1.7ミリモル)を5分で滴下した後、水1700ミリモル(30.60g)を20分かけて滴下した。なお、滴下の間、著しい温度上昇は起こらなかった。その後、50℃のまま、重縮合反応を窒素気流下で4時間行った。
重縮合反応後の反応溶液中の生成物を分析したところ、数平均分子量は1911であり、分子量分散度は1.47であった。上記生成物の29Si−NMRスペクトルから算出されるT2体とT3体の割合[T3体/T2体]は10.3であった。
その後、反応溶液を冷却し、下層液が中性になるまで水洗を行い、上層液を分取した後、1mmHg、40℃の条件で上層液から溶媒を留去し、無色透明の液状の生成物(エポキシ基含有ポリオルガノシルセスキオキサン)を得た。上記生成物のTd5は370℃であった。
(ハードコートフィルムの作製)
合成例1で得られた硬化性樹脂A(ポリオルガノシルセスキオキサン)61.6重量部、脂環エポキシ基を有する化合物(商品名「EHPE3150」(株)ダイセル製)6.9重量部、メチルイソブチルケトン(MIBK)(関東化学(株)製)30重量部、光カチオン重合開始剤(商品名「CPI−210S」、サンアプロ(株)製)1重量部、及び表面に(メタ)アクリロイル基を含む基を有するシリカ粒子(商品名「NanoBYK 3651」、ビックケミー・ジャパン(株)製)0.5重量部の混合溶液を調製し、これを硬化性組成物とした。
上記で得られた硬化性組成物を、PEN(ポリエチレンナフタレート)フィルム(商品名「テオネックス」(登録商標)、帝人デュポンフィルム(株)製、厚み50μm)上に、硬化後のハードコート層の厚みが40μmとなるようにワイヤーバー#44を使用して流延塗布した後、80℃のオーブン内で1分間放置(プレベイク)し、次いで5秒間紫外線を照射した(紫外線照射量:400mJ/cm2)。最後に150℃で30分間熱処理(エージング)することによって、ハードコート層を有するハードコートフィルム(ハードコート層/基材)を作製した。
硬化性組成物の組成を表1に示すように変更したこと以外は実施例1と同様にして、組成物を調製し、ハードコート層を有するハードコートフィルムを作製した。表1の硬化性組成物の表面に(メタ)アクリロイル基を含む基を有するシリカ粒子における、「NanoBYK 3652」は、商品名「NanoBYK 3652」(ビックケミー・ジャパン(株)製)である。表1の硬化性組成物の表面に(メタ)アクリロイル基を含む基を有するシリカ粒子における、「BYK−LPX 22699」は、商品名「BYK−LPX 22699」(ビックケミー・ジャパン(株)製)である。また、表1の硬化性組成物のレベリング剤における「BYK−370」は、シリコーン系レベリング剤であり、商品名「BYK−370」(ビックケミー・ジャパン(株)製)である。また、表1の硬化性組成物のレベリング剤における「サーフロン S−243」は、フッ素系レベリング剤であり、商品名「サーフロン S−243」(DIC(株)製)である。シリカ粒子における「MEK−ST」は、商品名「MEK−ST」(日産化学工業(株)製)であり、(メタ)アクリロイル基を含む基を有さないシリカ粒子である。なお、表1に記載の硬化性組成物の原料の配合量の単位は、重量部である。
上記で得た実施例1〜3、及び比較例1〜3のハードコートフィルムについて、以下の方法により各種評価を行った。結果を表1に示す。比較例4は、硬化性組成物がゲル化し、ハードコートフィルムを作製することができなかったため、評価を行わなかった。
以下の方法で実施例1〜3、及び比較例1〜3のハードコートフィルムのハードコート層上に機能層を形成したハードコートフィルムについて密着性試験を行った。
この機能層形成用硬化性組成物を、ハードコートフィルムのハードコート層上に、硬化後の機能層の厚みが5μmとなるようにワイヤーバー#14を使用して流延塗布した後、70℃のオーブン内で1分間放置(プレベイク)し、次いで5秒間紫外線を照射した(紫外線照射量:120mJ/cm2)。これにより機能層を形成したハードコートフィルム(機能層/ハードコート層/基材)を作製した。
○(密着性が良好):100マス中1マスも剥がれがない
×(密着性が不良):100マス中1マス以上の剥がれがある
ハードコートフィルムの表面(ハードコート層の表面)を蛍光灯の下で目視することにより、外観を評価した。
○(外観が良好):表面に歪みや凹凸がほとんどない
△(外観がやや不良):表面に歪みや凹凸が少し見られる
×(外観が不良):表面に歪みや凹凸が見られる
上記で得たハードコートフィルムにおける表面(ハードコート層の表面)の鉛筆硬度を、JIS K5600−5−4に準じて評価した。なお、荷重は750gで行った。
Claims (9)
- 下記ポリオルガノシルセスキオキサンと、表面に(メタ)アクリロイル基を含む基を有するシリカ粒子とを含む硬化性組成物。
ポリオルガノシルセスキオキサン:下記式(1)で表される構成単位を有し、下記式(I)で表される構成単位と、下記式(II)で表される構成単位のモル比[式(I)で表される構成単位/式(II)で表される構成単位]が5以上であり、シロキサン構成単位の全量(100モル%)に対する、下記式(1)で表される構成単位、及び下記式(4)で表される構成単位の割合が55〜100モル%であり、数平均分子量が1000〜3000、分子量分散度(重量平均分子量/数平均分子量)が1.0〜3.0である
- 前記ポリオルガノシルセスキオキサンは、R2が、置換若しくは無置換のアリール基である請求項2又は3に記載の硬化性組成物。
- 前記ポリオルガノシルセスキオキサン以外のエポキシ化合物を含む請求項1〜4のいずれか1項に記載の硬化性組成物。
- 光カチオン重合開始剤を含む請求項1〜5のいずれか1項に記載の硬化性組成物。
- ハードコート層形成用硬化性組成物である請求項1〜6のいずれか1項に記載の硬化性組成物。
- 請求項1〜7のいずれか1項に記載の硬化性組成物の硬化物。
- 基材と、当該基材の少なくとも一方の表面に形成されたハードコート層とを有するハードコートフィルムであって、前記ハードコート層が、請求項1〜7のいずれか1項に記載の硬化性組成物の硬化物層であることを特徴とするハードコートフィルム。
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CN115298275A (zh) * | 2020-03-27 | 2022-11-04 | 富士胶片株式会社 | 硬涂层形成用组合物、硬涂膜、硬涂膜的制造方法及具备硬涂膜的物品 |
CN115298275B (zh) * | 2020-03-27 | 2024-03-15 | 富士胶片株式会社 | 硬涂层形成用组合物、硬涂膜、硬涂膜的制造方法及具备硬涂膜的物品 |
WO2023054563A1 (ja) * | 2021-09-30 | 2023-04-06 | 積水化学工業株式会社 | 硬化性樹脂組成物、コーティング層、及び、フィルム |
WO2023054561A1 (ja) * | 2021-09-30 | 2023-04-06 | 積水化学工業株式会社 | 硬化性樹脂組成物、コーティング層、及び、フィルム |
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