JP2020125435A - 組成物、その硬化物、および硬化物の製造方法 - Google Patents
組成物、その硬化物、および硬化物の製造方法 Download PDFInfo
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Abstract
Description
本発明の組成物は、カチオン重合性化合物と、芳香族アルコールと、酸発生剤と、を有する。カチオン重合性化合物、芳香族アルコールおよび酸発生剤を併用することで、本発明の組成物は、初期硬化速度、初期密着性およびその後の密着性のバランスに優れた硬化物が得られるものとなる。なお、カチオン重合性化合物、芳香族アルコールおよび酸発生剤を併用することで、上述のような効果を奏する理由については、明確ではないが、以下のように推察される。
カチオン重合性化合物とは、カチオン重合性基を有する化合物であり、活性エネルギー線の照射または加熱により活性化した酸発生剤により高分子化または架橋反応を起こす化合物である。例えば、エポキシ化合物、オキセタン化合物、ビニルエーテル化合物、環状エーテル化合物、環状ラクトン化合物、環状アセタール化合物、環状チオエーテル化合物、スピロオルトエステル化合物、ビニル化合物等が使用でき、これらの1種または2種以上を使用することができる。これらのなかでも、密着力に優れた組成物を得るとの観点から、カチオン重合性化合物は、エポキシ化合物、オキセタン化合物およびビニルエーテル化合物の少なくとも1種を含むことが好ましく、特に、エポキシ化合物を含むことが好ましい。カチオン重合性化合物として、これらの化合物を用いることで、本発明の組成物は、初期硬化速度、初期密着性およびその後の密着性のバランスに優れたものとなる。
脂肪族エポキシ化合物とは、脂肪族エポキシ基を有する化合物である。本発明の組成物においては、脂肪族エポキシ化合物は、後述の脂環式エポキシ化合物や芳香族エポキシ化合物に分類されないエポキシ化合物を指す。また、本発明の組成物において、芳香族エポキシ化合物とは、芳香環を含むエポキシ化合物を意味し、脂環式エポキシ化合物とは、上述のとおり、エポキシシクロアルキル基を有する化合物を意味し、単に脂肪族環を有する化合物は、脂肪族エポキシ基に分類される。また、脂環式エポキシ化合物は、芳香環を含まない化合物である。
脂環式エポキシ化合物は、少なくとも1個のエポキシシクロアルキル基を有する化合物であり、単に脂肪族環を有する化合物は、脂環式エポキシ化合物には該当せず、脂肪族エポキシ基に分類される。エポキシシクロアルキル基は、エポキシ基とシクロアルキル基とが、環構造の一部を共有する構造を有する基である。なお、本発明の組成物においては、エポキシシクロアルキル基および芳香族環の両者を含むものは、脂環式エポキシ化合物に該当するものとする。
であることが好ましく、なかでも、10質量部以上50質量部以下であることが好ましく、特に、15質量部以上35質量部以下であることが好ましい。脂環式エポキシ化合物1の含有量をかかる範囲とすることで、本発明の組成物は、初期硬化速度、初期密着性およびその後の密着性のバランスにより優れた硬化物を形成可能となるからである。
であることが好ましく、なかでも、10質量部以上50質量部以下であることが好ましく、特に、15質量部以上35質量部以下であることが好ましい。脂環式エポキシ化合物2の含有量をかかる範囲とすることで、本発明の組成物は、初期硬化速度、初期密着性およびその後の密着性のバランスにより優れた硬化物を形成可能となるからである。
芳香族エポキシ化合物は、エポキシ基および芳香環を有する化合物を指す。
本発明の組成物においては、オキセタン化合物とは、オキセタン構造を有し、エポキシ構造を含まないものとする。
ビニルエーテル化合物は、ビニルエーテル基を有し、エポキシ基等の環状エーテル基を有しないものである。ビニルエーテル化合物としては、具体的には、ジエチレングリコールモノビニルエーテル、トリエチレングリコールジビニルエーテル、n−ドデシルビニルエーテル、シクロヘキシルビニルエーテル、2−エチルヘキシルビニルエーテル、2−クロロエチルビニルエーテル、エチルビニルエーテル、イソブチルビニルエーテル、トリエチレングリコールビニルエーテル、2−ヒドロキシエチルビニルエーテル、4−ヒドロキシブチルビニルエーテル、1,6−シクロヘキサンジメタノールモノビニルエーテル、エチレングリコールジビニルエーテル、1,4−ブタンジオールジビニルエーテル、1,6−シクロヘキサンジメタノールジビニルエーテル等が挙げられる。
本発明の組成物においては、カチオン重合性化合物として、チイラン化合物、チエタン化合物等のその他の化合物も用いることもできる。このような、カチオン重合性化合物として用いることができるその他の化合物、環状ラクトン化合物、環状アセタール化合物、環状チオエーテル化合物、スピロオルトエステル化合物およびエチレン性不飽和化合物等のビニル化合物等については、特許第6103653号公報等に記載の内容と同様とすることができる。
本発明の組成物において、芳香族アルコールとは、芳香族環を有しているアルコールである。本発明の組成物は、この芳香族アルコールにより、優れた初期硬化速度および初期密着性を発揮することができる。
本発明の組成物に用いられる酸発生剤は、可視光線、紫外線、X線、電子線、高周波のような活性エネルギー線(以下、単に「エネルギー線」とも称する。)照射により酸を発生させることが可能な化合物(以下、単に「光酸発生剤」とも称する。)、または加熱により酸を発生させることが可能な化合物(以下、単に「熱酸発生剤」とも称する。)である。
本発明の組成物は、ラジカル重合性化合物を含有していてもよい。本発明の組成物は、ラジカル重合性化合物を併用することで、硬化性を向上させることができる。ラジカル重合性化合物としては、アクリロイル基、メタクリロイル基、ビニル基等のエチレン性不飽和基を有する化合物を用いることができる。これらラジカル重合性化合物は、エチレン性不飽和基を1つ以上有する化合物を用いることができ、エチレン性不飽和基を1つ有する単官能化合物、エチレン性不飽和基を2以上有する多官能化合物のいずれも用いることができる。
本発明の組成物は、カチオン重合性化合物、芳香族アルコール、および酸発生剤を含むものであるが、本発明の組成物がラジカル重合性化合物を含有する場合、ラジカル重合開始剤を含んでいてもよい。ラジカル重合性化合物の重合が容易となるからである。ラジカル重合開始剤としては、光ラジカル重合開始剤および熱ラジカル重合開始剤のいずれも用いることができるが、硬化速度等に優れる等の観点からは、光ラジカル重合開始剤であることが好ましい。
本発明の組成物は、必要に応じて、上記各成分を溶解または分散可能な溶剤を含んでもよい。溶剤としては、25℃、大気圧下で液状であり、組成物の各成分を分散または溶解可能なものである。また、溶剤は、カチオン重合性化合物、芳香族アルコール、および酸発生剤等と反応しないものである。したがって、例えば、カチオン重合性化合物に分類されるものは、25℃、大気圧下で液状であっても、本発明の組成物においては、溶剤に該当しない。
本発明の組成物は、カチオン重合性化合物、芳香族アルコール、および酸発生剤を必須成分とし、必要に応じて上述のラジカル重合性化合物、ラジカル重合開始剤、溶剤等を有するものであるが、さらに必要に応じてその他の成分を含むものであってもよい。
本発明の組成物の製造方法としては、各成分を均一に混合できる方法であれば特に限定されるものではなく、例えば、公知の混合方法を用いることができる。混合方法については、公知の混合装置を用いる方法を採用でき、例えば、3本ロール、サンドミル、ボールミル等を用いる方法を用いることができる。
本発明の組成物の用途としては、初期硬化速度、初期密着性および密着性が要求される硬化物を形成して使用する用途であれば特に限定されるものではなく、光学フィルム、接着剤、メガネ、撮像用レンズに代表される光学材料、塗料、コーティング剤、ライニング剤、インキ、高屈折材料、水溶性材料、半導体・ディスプレイ・MEMS・医療機器用レジスト、液状レジスト、印刷版、絶縁ワニス、絶縁シート、積層板、プリント基盤、半導体装置用・LEDパッケージ用・液晶注入口用・有機EL用・光素子用・電気絶縁用・電子部品用・分離膜用等の封止剤、成形材料、パテ、ガラス繊維含浸剤、目止め剤、半導体用・太陽電池用等のパッシベーション膜、層間絶縁膜、保護膜、カラーフィルターの保護膜、スペーサー、DNA分離チップ、マイクロリアクター、ナノバイオデバイス、ハードディスク用記録材料、固体撮像素子、発光ダイオード、有機発光デバイス、ルミネセントフィルム、蛍光フィルム、アクチュエーター、ホログラム、プラズモンデバイス、偏光板、偏光フィルム、位相差フィルム、液晶表示装置のバックライトに使用されるプリズムレンズシート、プロジェクションテレビ等のスクリーンに使用されるフレネルレンズシート、レンチキュラーレンズシート等のレンズシートのレンズ部、またはこのようなシートを用いたバックライト等、マイクロレンズ等の光学レンズ、光学素子、光コネクター、光導波路、光学的造形用注型剤等を挙げることができる。本発明の組成物においては、なかでも、用途が、接着剤であることが好ましい。本発明の組成物の特徴を効果的に発揮できるからである。
本発明の硬化物は、本発明の組成物からなるものであり、カチオン重合性化合物に由来する構造単位を含む重合体を有するものである。本発明の硬化物の形状については、用途等に応じて適宜設定することができる。なお、本発明の硬化物の用途等については、「1.組成物」の項に記載の内容と同様とすることができるので、ここでの説明は省略する。また、本発明の組成物については、「A.組成物」の項に記載の内容と同様とすることができるので、ここでの説明は省略する。さらに、本発明の硬化物の製造方法については、カチオン重合性化合物同士を重合し、組成物を硬化できる方法であればよく、例えば、後述する「3.硬化物の製造方法」の項に記載の内容と同様とすることができる。
次に、本発明の硬化物の製造方法について説明する。
本発明の硬化物の製造方法は、本発明の組成物を硬化する硬化工程を有する。本発明の硬化物の製造方法によれば、本発明の組成物が上述の成分を含むものであるため、密着力に優れた硬化物を容易に得ることができる。以下、本発明の硬化物の製造方法に含まれる各工程について説明する。
硬化工程とは、本発明の組成物を硬化する工程である。本工程における本発明の組成物を硬化する方法としては、カチオン重合性化合物に由来する構造単位を含む重合体を形成できる方法であればよい。
本発明の硬化物の製造方法は、必要に応じてその他の工程を有するものであってもよい。このような工程としては、硬化工程後に、硬化物を加熱処理するポストベーク工程、硬化工程前に、本発明の組成物を加熱処理して、本発明の組成物中の溶剤を除去するプリベーク工程、硬化工程前に、本発明の組成物の塗膜を形成する塗膜形成工程、本発明の組成物の硬化物を形成する被接着物への表面処理工程等を挙げることができる。
実施例および比較例で得られた各組成物を、硬化後の厚みが3μmとなるように、一枚のPMMAフィルム(住友化学(株)製テクノロイ125S001)にそれぞれ塗布した後、もう一枚のコロナ放電処理を施したCOP(シクロオレフィンポリマー、日本ゼオン(株)製:品番ゼオノアフィルム14−060)フィルムとラミネーターを用いて貼り合わせ、メタルハライドランプを用いて1000mJ/cm2に相当する光をCOPフィルム越しに照射し、組成物を硬化した。その後、30℃、50%RH、大気圧条件下で24時間静置した後に、2.5cm幅に切り出して評価用サンプルAとし、90°ピール試験を行った。
++:2N以上である。
+:1N以上2N未満である。
−:1N未満である。
30℃、50%RH、大気圧条件下で24時間静置する処置を行わなかった以外は、密着力の評価と同様の手順で評価サンプルを作製した。次いで、この評価サンプルを2.5cm幅に切り出して密着力評価用の評価サンプルBとした。この評価サンプルBを、メタルハライドランプによる光照射完了から10分静置後に、密着力の評価と同様の90°ピール試験を行い、COPフィルムがPMMAフィルムから剥離する際の最大強度を接着力として測定することで得た。評価は下記基準で行った。結果を下記表1〜6に示す。なお、最大強度が大きい程密着力に優れると判断できる。
++:1N以上である。
+:0.5N以上1N未満である。
−:0.5N未満である。
実施例および比較例で得られた各組成物を光化学反応熱熱量計(光DSC、(株)日立ハイテクサイエンス社製DSC−7000X)を用い、光照射時の初期発熱量を測定して硬化性評価とした。試料は各10mg、光照射の条件は、室温(25℃)で365nmの光源を用いて50mWで200mJ照射し、その際に観察される発熱量から初期硬化速度を算出した。初期硬化速度の算出方法は、発熱量を、横軸時間min、縦軸μWでプロットし、UV照射開始時からピークトップまでの傾き(μW/min)を測定することで得た。なお、傾きが大きい程初期硬化速度が速いと判断できる。
++:初期硬化速度(傾き(μW/min))が5×105以上である。
+:初期硬化速度(傾き(μW/min))が4×105以上5×105未満である。
−:初期硬化速度(傾き(μW/min))が4×105未満である。
A2:脂肪族エポキシ化合物(一般式(1)で表される化合物(低分子量化合物))
A3:脂肪族エポキシ化合物(脂肪族エポキシポリマーa(メチルメタクリレート70質量部とグリシジルメタクリレート30質量部との共重合体、重量平均分子量Mw15000)、高分子量化合物))
A4:脂環式エポキシ化合物(セロキサイド2021P(ダイセル社製、一般式(2)で表される化合物、低分子量化合物))
A5:脂環式エポキシ化合物(セロキサイド3000(ダイセル社製、一般式(3)で表される化合物、低分子量化合物))
A6:オキセタン化合物(OXT−221(東亞合成社製、二官能オキセタン化合物))
A7:芳香族エポキシ化合物(1価フェノールのアルキレンオキサイド付加物のモノグリシジルエーテル化物(低分子量化合物))
A8:芳香族エポキシ化合物(ビスフェノールA型エポキシ化合物(低分子量化合物))
A9:4−ヒドロキシブチルビニルエーテル
B1:ベンジルアルコール
B2:4−イソプロピルベンジルアルコール
B3:2−メトキシベンジルアルコール
B4:フェネチルアルコール
B5:フェニルプロパノール
C1:トリプロピレングリコール
C2:ジプロピレングリコール
C3:2,2−ジメチル−1−プロパノール
D1:1,6−ヘキサンジオールアクリレート
D2:4−ヒドロキシブチルアクリレート
E1:ET−2201(増感剤)
F1:東レダウコーニング社製SH−29 Paint additive(レベリング剤)
G1:酸発生剤(芳香族スルホニウム塩、下記2種類の化合物の混合物の50質量%プロピレンカーボネート溶液)
G2:LUNA200(DKSHジャパン社製)
Claims (12)
- カチオン重合性化合物と、芳香族アルコールと、酸発生剤と、を含有することを特徴とする組成物。
- 前記カチオン重合性化合物が、脂肪族エポキシ化合物および脂環式エポキシ化合物のうち少なくとも一方を含む請求項1記載の組成物。
- 前記カチオン重合性化合物が、脂肪族エポキシ化合物および脂環式エポキシ化合物の両者を含む請求項2記載の組成物。
- 前記脂肪族エポキシ化合物および前記脂環式エポキシ化合物の合計量が、前記カチオン重合性化合物100質量部に対して35質量部以上である請求項3記載の組成物。
- 前記カチオン重合性化合物が、ビニルエーテル化合物を含む請求項1〜4のうちいずれか一項記載の組成物。
- 前記芳香族アルコールが、第1級アルコールまたは第2級アルコールである請求項1〜5のうちいずれか一項記載の組成物。
- 前記芳香族アルコールの含有量が、前記カチオン重合性化合物、前記芳香族アルコール、および前記酸発生剤の合計量100質量部中、2質量部以上20質量部以下である請求項1〜6のうちいずれか一項記載の組成物。
- さらに、ラジカル重合性化合物を含む請求項1〜7のうちいずれか一項記載の組成物。
- 前記ラジカル重合性化合物が、水酸基を有するアクリレートまたはメタクリレートである請求項8記載の組成物。
- 接着剤用である請求項1〜9のうちいずれか一項記載の組成物。
- 請求項1〜10のうちいずれか一項記載の組成物からなることを特徴とする硬化物。
- 請求項1〜10のうちいずれか一項記載の組成物を硬化する硬化工程を有することを特徴とする硬化物の製造方法。
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