JP2015108099A - 活性エネルギー線重合性樹脂組成物及び積層体 - Google Patents
活性エネルギー線重合性樹脂組成物及び積層体 Download PDFInfo
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- JP2015108099A JP2015108099A JP2013252460A JP2013252460A JP2015108099A JP 2015108099 A JP2015108099 A JP 2015108099A JP 2013252460 A JP2013252460 A JP 2013252460A JP 2013252460 A JP2013252460 A JP 2013252460A JP 2015108099 A JP2015108099 A JP 2015108099A
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- meth
- vinyl
- acrylate
- acid
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Abstract
優れた耐熱性等を有する新規な活性エネルギー線重合性樹脂組成物であって、各種光学フィルムの貼り合わせにおいて、概活性エネルギー線重合性樹脂組成物を使用した接着剤、及び/またはコート剤を使用する事によって、各種光学フィルムの種類を問わず、簡便かつ強固に接着や密着ができ、低露光量での重合硬化性に優れ、有機溶剤を実質的に含まない高耐久性の光学素子用積層体を提供することを目的とする。
【解決手段】
分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)と、分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)とを必須成分とする活性エネルギー線重合性樹脂組成物。
【選択図】なし
Description
分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)と、
を必須成分とする活性エネルギー線重合性樹脂組成物に関する。
化合物(A)を0.5〜95重量%、
化合物(B)を5〜99.5重量%、
含有することを特徴とする上記活性エネルギー線重合性樹脂組成物に関する。
分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)と、
を必須成分とする光学素子用活性エネルギー線重合性樹脂組成物に関する。
<活性エネルギー線重合性樹脂組成物>
本発明の活性エネルギー線重合性樹脂組成物は、少なくとも、分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)と、分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)とを必須成分として含むことを特徴とする。
(A)成分:
本発明の樹脂組成物において、分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)とは、少なくともα,β−不飽和二重結合基を有するモノマーの重合体及び/又は各種化合物に、B原子を有する化合物を反応させて得られる化合物であって、分子内に、1個以上のα,β−不飽和二重結合基を有する。上記化合物(A)は、α,β−不飽和二重結合基の他に、各種官能基を有してもよい。本発明の一実施形態において、上記化合物(A)は、B原子を有する化合物としての硼素系化合物(a1)と後述の水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(b1)とを反応させて生成した化合物であって、α,β−エチレン性不飽和二重結合基を有する化合物である。これらの反応は、Boronic acids - Preparation and applications in organic synthesis and medicine 2005 Dennis G. Hall に記載されているような一般的な反応によって得られる。
例えば、ホウ酸とアルコールまたはフェノールとの反応により得られるもの、例えば、ホウ酸トリメチル、ホウ酸トリエチル、ホウ酸トリ−n−プロピル、ホウ酸トリ−n−ブチル、ホウ酸トリフェニル、ホウ酸トリイソプロピル、ホウ酸トリ−t−アミル、ホウ酸トリフェニル、トリメトキシボロキシン、ホウ酸トリ−2−シクロヘキシルシクロヘキシル、ホウ酸トリエタノールアミン、ホウ酸トリイソプロピルアミン、ホウ酸マンニトール、ホウ酸グリセロール、およびホウ酸トリイソプロパノールアミンなどのホウ酸エステル類が挙げられる。
また、本発明の硼素系化合物(a1)には、ボロン酸の誘導体も含まれる。例えば、メチルボロン酸、エチルボロン酸、ブチルボロン酸、シクロヘキシルボロン酸などの、アルキルまたはアルケニルボロン酸;
例えば、フェニルボロン酸、ナフタレンボロン酸、アントラセンボロン酸などの、アリールボロン酸、1,4−ベンゼンジボロン酸またはこれらのアリール基に任意の置換基を有する、置換型アリールボロン酸が挙げられる。
本発明に使用される硼素系化合物(a1)の使用量としては、少なくとも、分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)の総量を100重量%としたときに、0.1重量%以上、50重量%以下であることが好ましい。0.1重量%未満であると、B原子の含有量が低下し、水素結合を形成することが困難となるため、所望の接着力発現に至らない。50重量%以上であると、時間の経過で析出してきたり、液としての粘度が上がりすぎてゲル化したりするなどの問題が生じる場合がある。特に好ましくは0.5重量%以上、40重量%以下である。
この目的に適切な重合体には、種々の活性水素含有重合体のいずれかを挙げられ、これには、例えば、アクリル重合体、ポリエステル重合体、ポリウレタン重合体、ポリエーテル重合体の少なくとも1種から選択される。
当該樹脂組成物をを活性エネルギー線で硬化後は、化合物(A)のα,β−エチレン性不飽和二重結合基による活性エネルギー線重合反応だけでなく、未反応のB−O−H結合が残存すれば、含有のB原子由来の水素結合性能により、後述の化合物(b1)由来の水酸基と結合した塗膜を形成する。また、後述の基材(G)の表面官能基と結合を形成して密着性を良くする効果がある。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上述の必須成分に加えて、分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)を含有することが重要である。特に、1個以上のα,β−不飽和二重結合基を含有する化合物であれば、特に制限はなく、使用できるが、その構造中に1個以上の水酸基を含有するα,β−エチレン性不飽和二重結合基含有化合物(b1)を含有することが好ましい。化合物(b1)には、水酸基を有し、環状構造を有しない化合物(b1−1)と、水酸基を有し、環状構造を有する化合物(b1−2)に分けられるが、いずれも水酸基を有することによって、後述の基材(G)との密着性向上に大きな効果を示す。
更に、耐熱性、あるいは耐湿熱性等の耐久性向上の点で、分子内に水酸基を有せず、かつ、1個以上の環状構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2)を含有することが好ましい。また、(b1),(b2)以外のα,β−エチレン性不飽和二重結合基含化合物(b3)も含有することができる。
なお、本願では、「(メタ)アクリロイル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、「(メタ)アクリロイルオキシ」、及び「(メタ)アリル」と表記した場合には、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタクリロイル」、「アクリル酸及び/又はメタクリル酸」、「アクリレート及び/又はメタクリレート」、「アクリロイルオキシ及び/又はメタクリロイルオキシ」、及び「アリル及び/又はメタリル」を表すものとする。
例えば、N−ヒドロキシエチル(メタ)アクリルアミド、N−ヒドロキシプロピル(メタ)アクリルアミド、N−ヒドロキシブチル(メタ)アクリルアミド、N−ヒドロキシヘキシル(メタ)アクリルアミド、N−ヒドロキシオクチル(メタ)アクリルアミド等の水酸基含有の(メタ)アクリルアミド類;
化合物(B)としては、基材との密着性の面より、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸4−ヒドロキシブチル、ε−カプロラクトン1〜2mol付加(メタ)アクリル酸2−ヒドロキシエチル等の炭素数2〜18であるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
化合物(b1−2)としては、その構造中に水酸基と環状構造の双方を有するものであれば特に制限はなく、例えば、(メタ)アクリル酸1,2−シクロヘキサンジメタノール、(メタ)アクリル酸1,3−シクロヘキサンジメタノール、(メタ)アクリル酸1,4−シクロヘキサンジメタノール、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシメチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシエチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシプロピル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシブチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシデシル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシオクタデシル、(メタ)アクリル酸モノヒドロキシエチルフタレート、(メタ)アクリル酸2−(4−ベンゾイル−3−ヒドロキシフェノキシ)エチル等の水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類;
4−ビニル安息香酸メチルポリ(エチレンオキサイド)、4−ビニル安息香酸エチルポリ(エチレンオキサイド)、4−イソプロペニル安息香酸メチルポリ(プロピレンオキサイド)、4−イソプロペニル安息香酸エチルポリ(プロピレンオキサイド)などのポリアルキレンオキサイド部位を有するビニル安息香酸エステル系またはイソプロペニル安息香酸エステル系単量体類;
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類等が挙げられる。
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
化合物(b1)が1重量部より少ないと、後述の基材(G)との密着性が低下する。化合物(b1)が45重量部より多いと、耐水性が劣るため好ましくない。化合物(b2)が1重量部より少ないと、塗膜の耐熱性や耐湿熱性が低下する。化合物(b2)が45重量部より多いと、塗膜の柔軟性が失われ、脆くなったりするため好ましくない。
化合物(A)が0.5重量%以上であると、十分な凝集力が得られ易く耐熱性や耐湿熱性の向上効果が期待できる。一方、化合物(A)が95重量%以下であると、樹脂組成物をコート剤、あるいは接着剤として用いた場合に、基材(G)に対する密着性や接着性が向上するので好ましい。
本発明の樹脂組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。しかし、上記樹脂組成物は、成分(A)と(B)の必須成分に加えて、必要に応じて、活性エネルギー線重合開始剤(E)を含んでもよい。活性エネルギー線重合開始剤(E)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましく、紫外線の照射によって重合反応を進行させる場合、樹脂組成物は、活性エネルギー線重合開始剤(E)を含むことが好ましい。
具体例として、例えば、以下が挙げられる。2,2−ジメトキシ−2−フェニルアセトフェノン、アセトフェノン、ベンゾフェノン、キサントフルオレノン、ベンズアルデヒド、アントラキノン、3−メチルアセトフェノン、4−クロロベンゾフェノン、4,4’−ジアミノベンゾフェノン、ベンゾインプロピルエーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4−チオキサントン、カンファーキノン、及び2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン等。
また、市販品としては、例えば、以下が挙げられる。イルガキュアー184,907,651,1700,1800,819,369,及び261(BASF社製)、DAROCUR−TPO(BASF社製、2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド)、ダロキュア−1173(メルク社製)、エザキュアーKIP150,及びTZT(日本シイベルヘグナー社製)、カヤキュアBMS,及びカヤキュアDMBI(日本化薬社製)等。
また、分子内に少なくとも1個の(メタ)アクリロイル基を有する光重合開始剤を使用することもできる。
また、ヘテロ環状構造を有するα,β−エチレン性不飽和二重結合基含有化合物(b2−2)として、(メタ)アクリル酸グリシジル、4−(グリシジルオキシ)ブチル(メタ)アクリレート、(メタ)アクリル酸(3−メチル−3−オキセタニル)メチル、(メタ)アクリル酸−3,4−エポキシシクロヘキシルメチルなどの3員環または4員環の酸素原子を有するヘテロ環含有(メタ)アクリル酸エステル類や後述のカチオン重合性化合物(D)を使用した場合には、活性エネルギー線重合開始剤として、必要に応じて公知の光酸発生剤を含有することが好ましい。光酸発生剤としては、例えば、UVACURE1590(ダイセル・サイテック社製)、CPI−110P(サンアプロ社製)、などのスルホニウム塩やIRGACURE250(チバ・スペシャルティ・ケミカルズ社製)、WPI−113(和光純薬社製)、Rp−2074(ローディア・ジャパン社製)等のヨードニウム塩などに例示されるものが挙げられ、併用使用する事で、重合架橋が進み、熱や湿度に対する耐久性に優れる接着層を形成するため好ましい。
また、分子内に少なくとも1個の(メタ)アクリロイル基を有する活性エネルギー線重合開始剤を使用することもできる。
本発明では、上記成分(E)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。本発明では、上記成分(E)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、オリゴマー(C)を含んでもよい。オリゴマー(C)を使用することによって、樹脂組成物をコート剤又は接着剤として使用した時に、基材に対する接着性及び密着性をより向上させることができる。また樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
ポリエステル系オリゴマー(c1)としては、主鎖骨格に多塩基酸と多価アルコールを重縮合して得られるポリエステルの末端あるいはポリエステル鎖中の水酸基と(メタ)アクリル酸、マレイン酸などの分子内に1個以上のカルボキシル基を有するα,β−エチレン性不飽和二重結合基含有化合物とのエステル化によって得られる化合物、あるいはポリエステルの末端あるいはポリエステル鎖中のカルボキシル基と(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピルなどの前述の化合物(b1)とのエステル化によって得られる化合物である。その他、酸無水物と(メタ)アクリル酸グリシジルと少なくとも1個の水酸基を有する化合物とから得られるポリエステルオリゴマー等もポリエステルオリゴマー(c1)として使用可能である。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
ポリウレタン系オリゴマー(c2)は、少なくとも1個以上のイソシアネート基を有する化合物と前記化合物(b1)を反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と上述の多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(b1)を反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、更に少なくとも1個以上のアミノ基を有する化合物とを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(b1)とを反応させて得られる化合物である。また、イソシアネート基とアミノ基とを反応させて得られるウレア結合基を含有したものもポリウレタン系オリゴマー(d2)に含む。
フェニレンジアミン、キシリレンジアミン、2,4−トリレンジアミン、2,6−トリレンジアミン、ジエチルトルエンジアミン,3,3’−ジクロロ−4,4’−ジアミノジフェニルメタン、4,4’−ビス−(sec−ブチル)ジフェニルメタン等の芳香族ジアミン;
トリメチルシリルジメチルアミン等の単官能のシリルアミノ基を保有するシリルアミン類;
1,1,3,3−テトラメチルジシラザン等の2官能のシリルアミノ基を保有するシリルアミン類が使用できる。
ポリエポキシ系オリゴマー(c3)は、グリシジル基を有する化合物とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有するα,β−不飽和二重結合基含有化合物との反応により得られる化合物であり、実質的にグリシジル基を有さず、かつα,β−不飽和二重結合基含有化合物を有する化合物である。代表例としてビスフェノール型、エポキシ化油型、フェノールノボラック型、脂環型が挙げられる。ビスフェノール型ポリエポキシ系オリゴマーとしては、ビスフェノール類とエピクロルヒドリンとを反応させて得られるビスフェノール型ジグリシジルエーテルと(メタ)アクリル酸などの分子内に1個以上のカルボキシル基を有するα,β−不飽和二重結合基含有化合物とを反応して得られるものである。
本発明では、オリゴマー(C)として、アクリル系オリゴマー(c4)を使用することもできる。使用可能な化合物の具体例として、α,β−不飽和二重結合基を有する変性ポリエーテル、アミン変性されたα,β−不飽和二重結合基含有化合物、並びに、アルキッド樹脂、スピロアセタール樹脂、ポリブタジエン樹脂、ポリチオールポリエン樹脂及び多価アルコール等の各種化合物にα,β−不飽和二重結合基を付加させた変性α,β−不飽和二重結合基含有化合物、からなる群より選択される1以上の化合物の、オリゴマーまたはプレポリマーを使用することができる。
なお、数平均分子量(Mn)、重量平均分子量(Mw)、酸価(AV)及び水酸基価(OHV)の測定方法については後述する。
本発明の樹脂組成物の一実施形態において、樹脂組成物は、上記必須成分に加えて、カチオン重合性化合物(D)を含んでもよい。カチオン重合性化合物(D)を使用することによって、樹脂組成物をコート剤又は接着剤として使用した時に、活性エネルギー線照射による異種重合硬化が可能なるため、硬化塗膜が相分離構造を形成し、弾性と応力緩和性やクリープ特性を制御しやすいため、基材に対する接着性又は密着性をより向上させることができる。また樹脂層の耐熱性又は耐湿熱性を向上させることが容易となる。
カチオン重合性化合物(D)としては活性エネルギー線による反応性の観点から、環状ヘテロ化合物や上述の化合物(B)中に例示されるビニルエーテル類が好ましく、環状ヘテロ化合物のうち、3員環状エーテル基を1つ以上有するオキシラン化合物(d1)が特に好ましく用いられる。
三員環状の環状エーテル基としては、例えば、オキシラン、メチルオキシラン、フェニルオキシラン、1,2−ジフェニルオキシラン、メチリデンオキシラン、オキシラニルメチル、オキシラニルメタノール、オキシランカルボン酸、(クロロメチル)オキシラン、(ブロモメチル)オキシラン、オキシラニルアセトニトリル等の脂肪族系環状エーテル基;
例えば、3,4−オキシランシクロヘキシルメチル 3,4−オキシランシクロヘキサンカルボキシレート、3,4−オキシラン−6−メチルシクロヘキシルメチル 3,4−オキシラン−6−メチルシクロヘキサンカルボキシレート、エチレンビス(3,4−オキシランシクロヘキサンカルボキシレート)、ビス(3,4−オキシランシクロヘキシルメチル)アジペート、ビス(3,4−オキシラン−6−メチルシクロヘキシルメチル) アジペート、ジエチレングリコールビス(3,4−オキシランシクロヘキシルメチルエーテル)、エチレングリコールビス(3,4−オキシランシクロヘキシルメチルエーテル)、2,3,14,15−ジオキシラン−7,11,18,21−テトラオキサトリスピロ−[5.2.2.5.2.2]ヘンイコサン(また、3,4−オキシランシクロヘキサンスピロ−2’,6’−ジオキサンスピロ−3’’,5’’−ジオキサンスピロ−3’’’,4’’’−オキシランシクロヘキサンとも命名できる化合物)、4−(3,4−オキシランシクロヘキシル)−2,6−ジオキサ−8,9−オキシランスピロ[5.5]ウンデカン、4−ビニルシクロヘキセンジオキサイド、ビス−2,3−オキシランシクロペンチルエーテル、及びジシクロペンタジエンジオキサイド等の脂環式環に結合した三員環状の環状エーテル基が挙げられる。これら三員環状の環状エーテル基含有化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合した化合物となり、オキシラン化合物(d1)となりうる。
ここに例示したオキシラン化合物は、それぞれ単独で使用してもよいし、また複数のオキシラン化合物を混合して使用してもよい。
等の環状化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合し得る芳香環が挙げられる。
工業的には、プロピオラクトン、ブチロラクトン、バレロラクトン、カプロラクトン、1,3−ジオキソラン、1,2−ジオキサン、1,3−ジオキサン、1,4−ジオキサン、1,3,5−トリオキサン、エチレンカーボネート、プロピレンカーボネート、グリセリンカーボネート等が反応性の点で好ましく用いられる。
このように、本発明の樹脂組成物に、カチオン重合性化合物(D)を併用することによって、活性エネルギー線を照射して重合硬化した塗膜の硬化収縮を抑制しやすいため、硬化収縮が大きいことに起因する積層体の外観不良も改善することが可能となる。
本発明の樹脂組成物は、本発明による効果を損なわない範囲であれば、各種添加剤を適宜配合することも可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩、及び染顔料等の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、シランカップリング剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、酸化防止剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、及び消泡剤等の、独立した充填剤としてではなく、ポリマーブレンド又はポリマーアロイとして、樹脂組成物中に、溶解、半溶解又はミクロ分散させることも可能である。
(I)第1の透明フィルム(第1の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第1の重合性接着層を形成する。また、第2の透明フィルム(第2の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第2の重合性接着層を形成する。次いで、ポリビニルアルコール系偏光子の両主面に、上記第1の重合性接着層と第2の重合性接着層とを、同時に/又は順番に、重ね合わせる。次いで、得られた積層体に活性エネルギー線を照射し、第1及び第2の接着層を重合硬化させる。
(合成例1〜15);製造方法1
反応槽(500ml)、攪拌機、温度計、還流冷却器、窒素導入環及び空気導入管を備えた重合反応装置の反応槽に、重合禁止剤0.01gとモレキュラーシーブ200gを加え、下記、硼素系化合物(a1)、及び化合物(b1)をそれぞれ表1に示す比率で仕込んだ。次に、反応槽内の空気を窒素ガスで置換した後、攪拌しながら酸素濃度が10%程度になるように空気を導入し、60℃まで昇温し、発生する水素ガスを系外に放出しながら3時間攪拌反応した。次に、60℃、5〜10Torrの条件で減圧蒸留を行い、未反応の化合物(b1)を除去した。その後、常温まで冷却し、表1に示す化合物(A)を得た。1H−NMR測定を行い、目的物が生成していることを確認した。尚、合成例2,3,7及び8で得られた生成物は各置換体の混合物であった。
反応槽(500ml)、攪拌機、温度計、還流冷却器、窒素導入環及び空気導入管を備えた重合反応装置の反応槽に、重合禁止剤0.01gとモレキュラーシーブ200gを加え、ホウ酸エステル(a1)、及び化合物(b1)をそれぞれ表1に示す比率で仕込んだ。次に、反応槽内の空気を窒素ガスで置換した後、攪拌しながら酸素濃度が10%程度になるように空気を導入し、攪拌しながら90℃まで昇温し、反応を開始した。副生成物であるアルコールを系外に留去しながら12時間反応した次に、90℃、5〜10Torrの条件で減圧蒸留を行い、未反応の化合物(b1)を除去した。その後、常温まで冷却し、表1に示す化合物(A)を得た。1H−NMR測定を行い、目的物が生成していることを確認した。
・成分(a)
H3BO3:オルトホウ酸、BDBO:1,4−ベンゼンジボロン酸、TIPB:ホウ酸トリイソプロピル
・成分(b1−1)
2HEA:アクリル酸2−ヒドロキシエチル、4HBA:アクリル酸4−ヒドロキシブチル、DEGA:アクリル酸ジエチレングリコール、FA2D:2−(アクリロイルオキシ)エチル6−ヒドロキシヘキサノネート
・成分(b1−2)
CHDMA:アクリル酸1,4−シクロヘキサンジメタノール、HPPA:アクリル酸2−ヒドロキシ−3−フェノキシプロピル
本発明では、上述の成分に限定されることなく、各種特性に優れた化合物(A)を合成することができる。
各合成例で得られた化合物(A)の外観を観察し、目視にて評価した。
各合成例で得られた化合物(A)の約1.2mlを測定用試料として使用した。23℃の雰囲気下で、E型粘度計(東機産業社製 TV−22)を使用し、回転速度0.5〜100rpmで、1分間回転の条件で測定を行い、溶液粘度(mPa・s)を求めた。
各合成例で得られた化合物(A)の仕込み数量と仕上がり数量を秤量し、以下の計算方法で収率を計算し、%で表示した。
収率(%)=100x仕上がり数量(g)/仕込み数量(g)
各合成例で得られた化合物(A)約5mgを重クロロホルム0.6gに溶解し、室温条件にて、積算回数10秒x64回の条件で、NMR測定を行った。測定はすべて、日本電子社製、JNM−LA400を用いて1H−NMR測定をおこなった。また、反応はすべて、合成例1〜15では有化合物(b1)のアルコール性OHのプロトン、3.65ppmピークの消失で確認した。更に、合成例16,17では、B−O−Cのイソプロピル基の由来の炭素原子に結合したプロトン1.19ppmピーク消失で確認した。
硼素系化合物(a)の、水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(b1)による反応置換数において、複製する各置換体の生成比率を算出するため、前記した1H−NMRを用いて判断した。B−O−Hのプロトンピーク(2.0ppm)とB−O−CHのプロトンピーク(3.82〜4.32ppm)の積分値比率を求め、比率を計算した。
[配合例1〜49]
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)、分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)、オリゴマー(C)、カチオン重合性化合物(D)、活性エネルギー線重合開始剤(E)、及び各種添加剤(F)を表2に示す比率で仕込み、エアモーターにて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す活性エネルギー線重合性樹脂組成物を得た。
・成分(a)
表1を参照。
・成分(b1−1)
4HBA:アクリル酸4−ヒドロキシブチル、2HEA:アクリル酸2−ヒドロキシエチル
・成分(b1−2)
CHDMA:アクリル酸1,4−シクロヘキサンジメタノール、HPPA:アクリル酸2−ヒドロキシ−3−フェノキシプロピル
・成分(b2−1)
IBXA:アクリル酸イソボルニル、DCPA:アクリル酸ジシクロペンタニル、ADCP:ジアクリル酸ジシクロペンタニル
・成分(b2−2)
ACMO:4−アクリロイルモルホリン、GMA:メクリル酸グリシジル
・成分(b3)
NPGDA:ジアクリル酸ネオペンチルグリコール、BA:アクリル酸ブチル
・成分(c1)
Ebecryl 885:ダイセルサイテック社製 ポリエステルアクリレート
・成分(c2)
紫光UV3000B:日本合成化学工業社製 ポリウレタン系オリゴマー(ウレタンアクリレート)
・成分(d1−1)
CEP01:1,3−フェニレンビス(メチレン)ビス(7−オキサビシクロ[4.1.0]ヘプタン−3−カルボキシレイト)、JER828:ビスフェノールA型オキシラン樹脂(三菱化学社製)
・成分(d1)
2021P:3,4−オキシランシクロヘキシルメチル−3,4−オキシランシクロヘキサンカルボキシレート(ダイセル化学工業社製)
・成分(d2)
DOME:ジ(1−エチル−3−オキセタニル)メチルエーテル
・成分(d3)
GC:グリセリンカーボネート
・成分(E)
TPO:2,4,6−トリメチルベンゾイル-ジフェニル-フォスフィンオキサイト゛(BASF社製,DAROCUR TPO)、CPI−110P:p-フェニルチオフェニルジフェニルスルホニウムPF6塩
本発明では、上述の成分に限定されることなく、各種特性に優れた活性エネルギー線重合性樹脂組成物を提供することができる。
各配合例で得られた化合物(A)の外観を観察し、目視にて評価した。
上述したように、各配合例で得られた樹脂組成物を23℃の雰囲気下でE型粘度計(東機産業社製 TV−22)にて、約1.2mlを測定用試料とし、回転速度0.5〜100rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
数平均分子量(Mn)と重量平均分子量(Mw)の測定は、昭和電工社製GPC(ゲルパーミエーションクロマトグラフィー)「ShodexGPC System−21」を用いた。GPCは溶媒に溶解した物質をその分子サイズの差によって分離定量する液体クロマトグラフィーであり、溶媒としてはテトロヒドロフラン、数平均分子量(Mn)と重量平均分子量(Mn)の決定はポリスチレン換算で行った。
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容量比:トルエン/エタノール=2/1)混合液100mlを加えて溶解する。更にアセチル化剤(無水酢酸25gをピリジンで溶解し、容量100mlとした溶液)を正確に5ml加え、約1時間攪拌した。これに、フェノールフタレイン試液を指示薬として加え、30秒間持続する。その後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定する。
水酸基価は次式により求めた。水酸基価は樹脂の乾燥状態の数値とした(単位:mgKOH/g)。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
乾燥状態の樹脂の値として、酸価(mgKOH/g)を次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}/(不揮発分濃度/100)
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
ロボットDSC(示差走査熱量計、セイコーインスツルメンツ社製「RDC220」)に「SSC5200ディスクステーション」(セイコーインスツルメンツ社製)を接続して、測定に使用した。
試料約10mgをアルミニウムパンに入れ、秤量して示差走査熱量計にセットし、試料を入れない同タイプのアルミニウムパンをリファレンスとして、100℃の温度で5分間加熱した後、液体窒素を用いて−120℃まで急冷処理した。その後10℃/分で昇温し、昇温中に得られたDSCチャートからガラス転移温度(Tg、単位:℃)を決定した。
[実施例1〜51][比較例1〜9]
表2及び3に示した樹脂組成物を活性エネルギー線重合性接着剤として使用して、以下の積層体を作成した。
透明フィルム(H)である保護フィルム(1)として、日本ゼオン社製 紫外線吸収剤を含有しないポリノルボルネン系フィルム:商品名「ZF−14」(厚み100μm)を用い、保護フィルム(2)として、三菱レイヨン社製 紫外線吸収剤を含有しないポリアクリル系フィルム:商品名「HDB−002」(厚み50μm)を使用し、それぞれその表面に300W・min/m2 の放電量でコロナ処理を行い、表面処理後1時間以内に、配合例に示す接着剤をワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、接着層を形成し、接着層との間に上記のポリビニルアルコール系偏光子を挟み、保護フィルム(1)/接着層/PVA系偏光子/接着層/保護フィルム(2)からなる積層体を得た。
保護フィルム(1)がブリキ板に接するように、この積層体の四方をセロハンテープで固定し、ブリキ板に固定した。
活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の紫外線を保護フィルム(2)側から照射して、偏光板を作製した。
接着力は、JIS K6 854−4 接着剤−剥離接着強さ試験方法−第4部:浮動ローラー法に準拠して測定した。
即ち、得られた偏光板を、25mm×150mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを両面粘着テープ(トーヨーケム社製DF8712S)を使用して、ラミネータを用いて金属板上に貼り付けて、偏光板と金属板との測定用の積層体を得た。測定用の積層体の偏光板には、保護フィルムと偏光子の間に予め剥離のキッカケを設けておき、この測定用の積層体を23℃、相対湿度50%の条件下で、300mm/分の速度で引き剥がし、剥離力とした。この際、ポリビニルアルコール系偏光子と保護フィルム(1)、及びポリビニルアルコール系偏光子と保護フィルム(2)との双方の剥離力を測定した。この剥離力を接着力として4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:剥離不可、あるいは偏光板破壊
○:剥離力が2.0(N/25mm)以上〜5.0(N/25mm)未満。
△:剥離力が1.0(N/25mm)以上〜2.0(N/25mm)未満。
×:剥離力が1.0(N/25mm)未満。
コロナ処理を施していない日本ゼオン社製のポリノルボルネン系フィルム(商品名「ゼオノア ZF−14:100μm」に、活性エネルギー線重合性接着剤を、ワイヤーバーコーターを用いて膜厚20〜25μmとなるように塗工し、接着層を形成した。さらに接着層の上にコロナ処理を施していないゼオノア ZF−14を重ね、3層からなる積層体を得た後、活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の活性エネルギー線を照射し接着層を重合硬化させた。3層からなる積層体のゼオノア ZF−14を剥離し接着剤層を得た。
接着剤層の重量を測定した後(重量1)を金属メッシュと金属メッシュの間に挟み接着剤層同士が重ならないようにし、メチルエチルケトン(MEK)中で3時間還流した。さらに80℃−30分乾燥し、接着剤層の重量を測定した(重量2)。下記式よりゲル分率を求め、3段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
ゲル分率(%)={1−(重量1−重量2)/重量1)}×100
(評価基準)
○:ゲル分率が90%以上
△:ゲル分率が80%以上〜90%未満
×:ゲル分率が80%未満
ダンベル社製の100mm×100mmの刃を用い、作製した偏光板を保護フィルム(1)側から打ち抜いた。
打ち抜いた偏光板の、周辺の剥離距離を定規で測定し、以下の4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0mm
○:1mm以下
△:1〜3mm
×:3mm以上
上記偏光板小片を60℃−dryと60℃−90RH%の恒温恒湿機中に放置し、60時間後の延伸方向の縮み量を測定し、元の長さ(100mm)に対する縮み量の割合を収縮率とし求め、以下の3段階で評価をした。
なお、「dry」とは、湿度調整機能付のオーブンで、温度のみコントロールし、湿度のコントロールを行わなかった場合の試験条件である。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
○:収縮率が0.2%以下
△:収縮率が0.2%より大きくて0.4%以下
×:収縮率が0.4%を超える。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、80℃−dry、及び100℃dryの条件下で、それぞれ1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:100℃−dryの条件下でも剥がれが全く無し。
○:80℃−dry条件下で剥がれが全く無し。
△:80℃−dry条件下で1mm未満の剥がれあり。
×:80℃−dry条件下で1mm以上の剥がれあり。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、60℃−90%RHの条件下、及び85℃−85%RHの条件下で1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:85℃−85%RHの条件下でも剥がれが全く無し。
○:60℃−90%RHの条件下で剥がれが全く無し。
△:60℃−90%RHの条件下で1mm未満の剥がれあり。
×:60℃−90%RHの条件下で1mm以上の剥がれあり。
ZF−14:日本ゼオン社製ポリノルボルネン系フィルム、HBD−002:三菱レイヨン社製アクリル系フィルム。
[実施例101〜151][比較例11〜19]
表1及び2に示した樹脂組成物を活性エネルギー線重合性コート剤として使用し、以下の積層体を作成した。
光学フィルムとして、富士フィルム社製の紫外線吸収剤含有ポリトリアセチルセルロース系フィルム:商品名「フジタック:80μm」を用いた。光学フィルム表面を300W・min/m2の放電量でコロナ処理を行い、表面処理後1時間以内に、配合例に示す樹脂組成物を活性エネルギー線重合性コート剤として、ワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、コート剤層を形成した。
光学フィルムがブリキ板に接するように、この積層体の四方をセロハンテープで、ブリキ板に固定した。
UV照射装置(東芝社製 高圧水銀灯)内を乾燥窒素で置換後、波長365nmの最大照度300mW/cm2、積算光量300mJ/cm2の紫外線をコート剤層側から照射して、コート剤層を有する積層体を作製した。
JIS K5400に従い、碁盤目剥離試験を実施した。100マス中の剥離したマス数を4段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0マス
○:1〜10マス
△:11〜30マス
×:31マス以上
各実施例と比較例で得られた積層体を、50mm×40mmの大きさに裁断し、80℃−dryの条件下で1000時間暴露した。暴露後積層体の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
○:剥がれが全く無し
△:1mm未満の剥がれあり
×:1mm以上の剥がれあり
また、本発明の樹脂組成物をコート剤として用いた場合は、表4と同様の傾向であり、表5に示す様に実施例106〜159では、密着性、及び耐熱性とも優れ、特に問題無い。また、実施例101〜105は、密着性、および耐熱性のレベルが低いが、使用することが可能である。これに対して比較例11〜19では、特に密着性、あるいは耐熱性に劣ることがわかる。
Claims (11)
- 分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)と、
分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)と、
を必須成分とする活性エネルギー線重合性樹脂組成物。 - 活性エネルギー線重合性組成物全量中、
化合物(A)を0.5〜95重量%、
化合物(B)を5〜99.5重量%、
含有することを特徴とする請求項1記載の活性エネルギー線重合性樹脂組成物。 - 化合物(A)は硼素系化合物(a1)と水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(b1)とを反応させて得られた化合物であることを特徴とする請求項1又は2記載の樹脂組成物。
- 硼素系化合物(a1)は、B−O−H結合を1つ以上有することを特徴とする請求項1〜3いずれか記載の活性エネルギー線重合性樹脂組成物。
- 化合物(B)が、水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(b1)を含むことを特徴とする請求項1〜4いずれか記載の活性エネルギー線重合性樹脂組成物。
- 前記、化合物(B)が、1個以上の環状構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2)を含む、請求項1〜5いずれか記載の活性エネルギー線重合性樹脂組成物。
- 分子内に1個以上のB原子を有するα,β−エチレン性不飽和二重結合基含有化合物(A)と、
分子内にB原子を有しないα,β−エチレン性不飽和二重結合基含有化合物(B)と、
を必須成分とする光学素子用活性エネルギー線重合性樹脂組成物。 - 基材(G)と、該基材(G)の少なくとも一方の主面に設けられた、請求項1〜7のいずれか1項に記載の樹脂組成物からなる樹脂層とを有することを特徴とする積層体。
- 基材(G)が、透明フィルム(H)であることを特徴とする請求項8記載の積層体。
- 透明フィルム(H)が、ポリアセチルセルロース系フィルム、ポリノルボルネン系フィルム、ポリプロピレン系フィルム、ポリアクリル系フィルム、ポリカーボネート系フィルム、ポリエステル系フィルム、ポリビニルアルコール系フィルム、及びポリイミド系フィルムからなる群から選択される少なくとも1種であることを特徴とする請求項9に記載の積層体。
- 光学フィルムと、該光学フィルムの少なくとも一方の主面に設けられた、請求項1〜6のいずれか記載の樹脂組成物からなる樹脂層とを有することを特徴とする光学素子用積層体。
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