JP6842977B2 - 積層体 - Google Patents
積層体 Download PDFInfo
- Publication number
- JP6842977B2 JP6842977B2 JP2017079165A JP2017079165A JP6842977B2 JP 6842977 B2 JP6842977 B2 JP 6842977B2 JP 2017079165 A JP2017079165 A JP 2017079165A JP 2017079165 A JP2017079165 A JP 2017079165A JP 6842977 B2 JP6842977 B2 JP 6842977B2
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- hard coat
- coat layer
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- 0 **1ON1N=C Chemical compound **1ON1N=C 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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Description
前記ハードコート層は、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の硬化物層である積層体を提供する。
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
図1は、本発明の積層体の態様の一例を示す断面概念図である。図1において、積層体1は、ハードコート層2と、当該ハードコート層2と接する機能層3とを有する二層以上で構成される積層部4と、当該ハードコート層2と接する基材5とを有し、当該機能層3が積層体1の最表面である積層体である。前記ハードコート層2は、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、後記のハードコート層形成用硬化性組成物の硬化物層である。
本発明におけるハードコート層は、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必須成分として含む、ハードコート層形成用硬化性組成物の硬化物層である。本発明の積層体は、前記ハードコート層を有することで、表面の平滑性(厚みの均一性)などの外観が良く、表面硬度が高く、リコート性を有する。
ハードコート層形成用硬化性組成物は、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。後述のように、ハードコート層形成用硬化性組成物は、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
本発明において表面に(メタ)アクリロイル基を含む基を有するシリカ粒子は、リコート性を付与し、耐擦傷性や表面硬度をより向上させる性質を有する。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。さらに、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、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。また、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。
前記ハードコート層形成用硬化性組成物は、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。
機能層は、例えば、耐擦傷性、耐摩耗性、防汚性(耐汚染性)、防指紋性、反射防止性(低反射性)等の機能を有する機能層である。機能層は、携帯電話やスマートフォンなどの表示装置におけるハードコート層において用いられる上記で挙げた機能を有する一般的な公知乃至慣用の機能層である。機能層を構成する材料としては、例えば、アクリル系材料、フッ素系材料、シリコーン系材料が挙げられる。
前記基材としては、プラスチック基材、金属基材、セラミックス基材、半導体基材、ガラス基材、紙基材、木基材(木製基材)、表面が塗装表面である基材等の公知乃至慣用の基材を用いることができ、特に限定されない。中でも、プラスチック基材が好ましい。前記基材は、単層の構成を有していてもよいし、多層(積層)の構成を有していてもよく、その構成(構造)は特に限定されない。
本発明の積層体は、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ハードコート層形成用硬化性組成物を塗布し、必要に応じて溶剤を乾燥によって除去した後、該硬化性組成物(硬化性組成物層)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、例えば、上述の硬化物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。
(ハードコート層の作製)
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、及びシリカ粒子の表面にアクリル官能基を有するレベリング剤(商品名「BYK−LPX 22699」、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、これをハードコート層形成用硬化性組成物とした。
上記で得られたハードコート層形成用硬化性組成物を、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20μm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基材(ハードコート層/基材)を作製した。
本実施例において、ハードコート層へのコロナ処理は、以下の条件で行った。なお、コロナ処理後の表面濡れ性は、42dyne以上となるようにした。
コロナ処理環境: 室温、空気雰囲気下
高周波電源の出力: 0.2kW
フィルム(ハードコート層を有する基材)とコロナ発生場所の間隔: 2mm
処理回数: 4回
アクリレートモノマー(商品名「UA−1100H」、新中村化学(株)製)28.4重量部、環化重合性モノマー(商品名「FX−AO−MA」、日本触媒(株)製)0.3重量部、CAP(セルロースアセテートプロピオネート)、商品名「CAP−482−20」、イーストマンケミカルジャパン(株)製)0.3重量部、フッ素系アクリレート添加剤(商品名「KY−1203」、信越化学工業(株)製)0.1重量部、フッ素系添加剤(商品名「メガファック RS−55」、DIC製)0.1重量部、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(商品名「イルガキュア 184」、BASF製)0.6重量部、及び光重合開始剤として2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン−1−オン(商品名「イルガキュア 907」、BASF製)0.3重量部を、メチルエチルケトン(MEK)30重量部に溶解させてこれを機能層形成用硬化性組成物とした。
この機能層形成用硬化性組成物を、上記で得た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)。これにより積層体(機能層/ハードコート層/基材)を作製した。
ハードコート層形成用硬化性組成物の組成、及びハードコート層の厚みを表1に示すように変更したこと以外は実施例1と同様にしてハードコート層形成用硬化性組成物を調製してハードコート層を作製し、さらに実施例1と同様にしてハードコート層上に機能層を積層させて積層体を作製した。ハードコート層へのコロナ処理の有無は、表1のとおりである。表1のハードコート層形成用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、フッ素化合物のエチレンオキサイド付加物、商品名「サーフロン S−243」(AGCセイミケミカル(株)製)である。また、表1のハードコート層形成用硬化性組成物のシリコーンアクリレートにおける「KRM8479」は、商品名「KRM8479」(ダイセル・オルネクス(株)社製)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1〜6の積層体について、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7は、硬化性組成物がゲル化したためハードコート層を作製することができなかった。よって、比較例7については評価を行わなかった。
積層体の密着性(機能層とハードコート層の密着性)は、JIS K5400−8.5に従って、クロスカット後の碁盤目テープ試験によって評価した。評価は、積層体の表面の任意の箇所に、カッターナイフで100マスの切り込みを入れてテープ試験を行い、テープ試験により剥がれなかったマスの数により下記のとおり評価を行った。なお、表1では、例えば100マス中100マス剥がれなかった場合、(100/100)と記載した。
○(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
積層体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ない
×(外観が不良):表面に歪みや凹凸が見られる
上記で得られた積層体の機能層表面の水接触角(液滴法)を測定し、以下の基準で防汚性を評価した。
○(防汚性が良い):水接触角が90°以上
×(防汚性が悪い):水接触角が90°未満
上記で得た積層体における表面の鉛筆硬度を、JIS K5600−5−4に準じて評価した。なお、荷重は750gで行った。
上記で得た積層体の表面に対し、荷重1000g/cm2にて表1に記載の所定の回数、#0000スチールウールを往復させた。100回毎に下記の基準にて表面に付いた傷の有無を確認し、耐擦傷性を評価した。
OK:所定の回数にて傷が見られない
NG:所定の回数にて傷が見られる
2 ハードコート層
3 機能層
4 積層部
5 基材
Claims (9)
- ハードコート層と、当該ハードコート層と接する機能層とを有する、2層以上で構成される積層部と、当該ハードコート層と接する基材とを有し、当該機能層が積層体の最表面である積層体であって、
前記ハードコート層は、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の硬化物層であり、
前記機能層は、紫外線硬化系化合物を含む硬化性組成物の硬化物層である、積層体。
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に記載の積層体。
- 前記ハードコート層に係る硬化性組成物は、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項に記載の積層体。
- 前記ハードコート層に係る硬化性組成物は、光カチオン重合開始剤を含む請求項1〜5のいずれか1項に記載の積層体。
- 前記ハードコート層の厚みは、1〜100μmである請求項1〜6のいずれか1項に記載の積層体。
- 前記機能層の厚みは、0.1〜50μmである請求項1〜7のいずれか1項に記載の積層体。
- 総厚みは、10〜1000μmである請求項1〜8のいずれか1項に記載の積層体。
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WO2020175337A1 (ja) * | 2019-02-27 | 2020-09-03 | 富士フイルム株式会社 | 積層体、積層体を備えた物品、及び画像表示装置 |
CN118522220A (zh) * | 2019-06-26 | 2024-08-20 | 应用材料公司 | 可折叠显示器的柔性多层覆盖透镜堆叠 |
JP2023019888A (ja) * | 2021-07-30 | 2023-02-09 | デクセリアルズ株式会社 | 積層体、屋外用積層体、及びハードコート層形成材料 |
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JPS5699263A (en) * | 1980-01-10 | 1981-08-10 | Nippon Sheet Glass Co Ltd | Coating composition |
US7297731B2 (en) * | 2003-03-11 | 2007-11-20 | 3M Innovative Properties Company | Coating dispersions for optical fibers |
JP2005133026A (ja) * | 2003-10-31 | 2005-05-26 | Lintec Corp | コーティング用組成物、ハードコートフィルムおよび光ディスク |
JP5092440B2 (ja) * | 2007-02-16 | 2012-12-05 | Jsr株式会社 | 硬化性組成物、その硬化膜及び積層体 |
JP2009138059A (ja) * | 2007-12-04 | 2009-06-25 | Canon Inc | 成形用材料、それを用いた成形品およびその製造方法 |
JP2009206197A (ja) * | 2008-02-26 | 2009-09-10 | Fujifilm Corp | ナノインプリント用硬化性組成物、硬化物およびその製造方法 |
JP5066484B2 (ja) | 2008-05-22 | 2012-11-07 | シーアイ化成株式会社 | 積層体及びその製造方法 |
KR101585269B1 (ko) * | 2010-02-10 | 2016-01-14 | (주)엘지하우시스 | 하드코팅 형성용 수지 조성물 |
JP5470166B2 (ja) * | 2010-06-11 | 2014-04-16 | 東亞合成株式会社 | 硬化型コーティング剤組成物 |
JP6057320B2 (ja) * | 2011-07-13 | 2017-01-11 | 関西ペイント株式会社 | 積層体及び積層体の製造方法 |
JP2014191173A (ja) * | 2013-03-27 | 2014-10-06 | Daicel Corp | ハードコートフィルム及びその製造方法 |
JP6219250B2 (ja) * | 2013-12-13 | 2017-10-25 | 株式会社ダイセル | ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物 |
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US20200062996A1 (en) | 2020-02-27 |
CN110546001B (zh) | 2022-05-03 |
KR20190138652A (ko) | 2019-12-13 |
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WO2018189946A1 (ja) | 2018-10-18 |
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