JP2016053101A - 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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- JP2016053101A JP2016053101A JP2014178465A JP2014178465A JP2016053101A JP 2016053101 A JP2016053101 A JP 2016053101A JP 2014178465 A JP2014178465 A JP 2014178465A JP 2014178465 A JP2014178465 A JP 2014178465A JP 2016053101 A JP2016053101 A JP 2016053101A
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Abstract
Description
分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)と、
分子中にカルボキシル基を含有しないα,β−不飽和二重結合基含有化合物(C)とを
含有する活性エネルギー線重合性樹脂組成物に関する。
ただし、化合物(B)および化合物(C)は、化合物(A)以外の化合物である。
化合物(A)を0.5〜30重量%、
化合物(B)を0.5〜20重量%、
化合物(C)を50〜99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。
該光学フィルムの少なくとも一方の主面に設けられた上記樹脂組成物からなる樹脂層とを有する光学素子用積層体に関する。
<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、分子中に1個以上のオキサゾリン環を有する化合物(A)と、
分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)と、分子中にカルボキシル基を含有しないα,β−不飽和二重結合基含有化合物(C)と、を必須成分として含むことを特徴とした
活性エネルギー線重合性樹脂組成物。
ただし、化合物(B)および化合物(C)は、分子中に1個以上のオキサゾリン環を有するα,β−不飽和二重結合基含有化合物(A)以外の化合物である。
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。
(A)成分:
本発明の活性エネルギー線重合性樹脂組成物(以下樹脂組成物と称す。)における分子中に1個以上のオキサゾリン環を有する化合物(A)としては、分子中に1個以上のオキサゾリン環を有するα,β−不飽和二重結合基含有化合物(a1)であるか、または、分子中に1個以上のオキサゾリン環を有するα,β−不飽和二重結合基含有化合物(a1)および後述のα,β−不飽和二重結合基含有化合物(C')を含んで重合してなる共重合体樹脂(ac)が挙げられる。ここで、化合物(a1)は分子中にオキサゾリン環とα,β−不飽和二重結合基がそれぞれ1個以上含有する化合物である。オキサゾリン環は酸素原子と窒素原子をそれぞれ一つ含むヘテロ5員環であり、活性水素の存在で容易に開環する環構造である。このため、化合物(a1)由来のオキサゾリン環が1個以上存在するので、活性エネルギー線照射により、後述の分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)との間で相互作用し、化合物(A)が擬似的にα,β−不飽和二重結合基を複数有する多官能単量体や感光性樹脂の如く挙動するため、より緻密な3次元網目構造の反応硬化物を形成することができ、耐久性に優れた積層体を製造することができる。
なお共重合体樹脂(ac)の構成成分である各α,β−不飽和二重結合基含有化合物から形成され得るホモポリマーのTgが既知であれば、各ホモポリマーのTgと各α,β−不飽和二重結合基含有化合物の構成比とに基づいて、樹脂(ac)のTgを理論的に求めることも可能である。。
<FOX式>1/Tg=W1/Tg1+W2/Tg2+…+Wi/Tgi+…+Wn/Tgn
〔上記FOX式は、n種の単量体からなる重合体を構成する各α,β−不飽和二重結合基含有化合物のホモポリマーのガラス転移温度をTgi(K)とし、各α,β−不飽和二重結合基含有化合物の質量分率を、Wiとしており、(W1+W2+…+Wi+…Wn=1)である。〕
本発明における樹脂(ac)は、上記したような種々のα,β−不飽和二重結合基含有化合物(a1)及び(C')の合計100重量部に対して、0.001〜20重量部の重合開始剤を用いて塊状重合、溶液重合、乳化重合、あるいは懸濁重合などの方法により合成される。好ましくは溶液重合や塊状重合で合成される。
分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)について説明する。本発明において、上記化合物(B)とは、分子内に少なくとも1個のカルボキシル基を有し、かつ少なくとも1個のα,β−不飽和二重結合基を含有する化合物である。上記化合物(B)におけるカルボキシル基は、前述の、化合物(a1)中のオキサゾリン環と開環付加反応等の相互作用を示す。その結果、上記相互作用において、α,β−不飽和二重結合基が複数存在する多官能のα,β−不飽和二重結合基含有化合物が形成されるため、重合硬化物の架橋密度が大きく向上することになる。
分子内にカルボキシル基を有しないα,β−不飽和二重結合基含有化合物(C)について説明する。本発明において、上記化合物(C)は、分子中にカルボキシル基、及びオキサゾリン環を有しないα,β−不飽和二重結合基を含有する化合物のモノマーであり、重合硬化物のガラス転移点(Tg)を向上させて高凝集力を発現させたり、耐熱性や耐水性等の耐性の良好な樹脂硬化物を形成することが可能となるものである。
化合物(c1−1)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(c1−2)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;
本発明において、上記化合物(c2)は、分子内にカルボキシル基、及び水酸基を有しないα,β−不飽和二重結合基を含有する化合物であり、樹脂組成物に上記成分(c2)を含有することによって、前記化合物(a1)、あるいは共重合体樹脂(ac)との共重合反応の効率化及び高感度化を図ることが容易である。また、上記樹脂(X)を容易に低粘度化できるとともに、塗工時の作業性を向上させることが容易となる。また、塗工物のガラス転移点(Tg)を向上させて高凝集力を発現させたり、耐熱性や耐水性等の耐性の良好な硬化層を形成することが可能となるものである。特に限定するものではなく、成分(c2)として使用可能な化合物としては、以下が挙げられる。
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;
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;
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。
例えば、メチルビニルエーテル、エチルビニルエーテル、2−クロロビニルエーテル、n−プロピルビニルエーテル、アリルビニルエーテル、イソプロピルビニルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル、イソブチルビニルエーテル、tert−ブチルビニルエーテル、n−ペンチルビニルエーテル、イソペンチルビニルエーテル、tert−ペンチルビニルエーテル、n−ヘキシルビニルエーテル、イソヘキシルビニルエーテル、2−エチルブチルビニルエーテル、2−エチルヘキシルビニルエーテル、n−ヘプチルビニルエーテル、n−オクチルビニルエーテル、イソオクチルビニルエーテル、ノニルビニルエーテル、デシルビニルエーテル、ドデシルビニルエーテル、ヘキサンデシルビニルエーテル、オクタデシルビニルエーテル、エトキシメチルビニルエーテル、2−メトキシエチルビニルエーテル、2−エトキシエチルビニルエーテル、2−ブトキシエチルビニルエーテル、アセトキシメチルビニルエーテル、2−アセトキシエチルビニルエーテル、3−アセトキシプロピルビニルエーテル、4−アセトキシブチルビニルエーテル、4−エトキシブチルビニルエーテル、2−(2−メトキシエトキシ)エチルビニルエーテル、3−ヒドロキシプロピルビニルエーテル、4−ヒドロキシブチルビニルエーテル、5−ヒドロキシペンチルビニルエーテル、6−ヒドロキシヘキシルビニルエーテル、ジエチレングリコールメチルビニルエーテル、ジエチレングリコールエチルビニルエーテル、ジエチレングリコールブチルビニルエーテルなどの脂肪族ビニルエーテル類;
化合物(A)および化合物(B)が、それぞれ0.5重量%以上であれば、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30重量%以下、または化合物(B)が20重量%以下であれば、樹脂組成物をコート剤や接着剤として用いた場合に、硬化塗膜の硬化収縮が低減でき、加工性が向上するので好ましい。
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(D)を含んでもよい。オリゴマー(D)を使用することによって、樹脂組成物をコート剤や接着剤として使用した時、造形性及び硬化収縮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(d1)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(c1)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(d1)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(d2)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(c1)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ポリオール類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(c1)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ポリオール類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(c1)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。
ポリエポキシ系オリゴマー(d3)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(D)として、アクリル系オリゴマー(d4)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。
しかし、本発明は、上記成分(d2)以外のオリゴマー成分を使用した場合についても、その他の構成成分を適切に配合することによって、所望とする特性を容易に得ることができる。
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)、(B)、及び(C)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。
例えば、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−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−オン等が挙げられる。市販品としては、例えば、イルガキュアー184,907,651,1700,1800,819,369,261、DAROCUR−TPO(BASF社製 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ド)、ダロキュアー1173(メルク社製)、エザキュアーKIP150、TZT(日本シイベルヘグナー社製)、カヤキュアBMS、カヤキュアDMBI(日本化薬社製)等が挙げられる。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ラジカル重合開始剤を、本発明のラジカル重合開始剤(e1)として用いることができる。
げられる。
上記、増感剤の中でチオキサントン誘導体としては、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジクロロチオキサントン、2−イソプロピルチオキサントン、4−イソプロピルチオキサントン、1−クロロ−4−プロポキシチオキサントン等を挙げることができ、ベンゾフェノン類としては、ベンゾフェノン、4−メチルベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4,4'−ジメチルベンゾフェノン、4,4'−ジメトキシベンゾフェノン、4,4'−ビス(ジエチルアミノ)ベンゾフェノン等を挙げることができ、クマリン類としては、クマリン1、クマリン338、クマリン102等を挙げることができ、ケトクマリン類としては、3,3'−カルボニルビス(7−ジエチルアミノクマリン)等を挙げることができるが、これらに限定されるものではない。
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(F)を含んでもよい。カチオン重合性化合物(F)を使用することによって、樹脂組成物をコーティング剤や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、硬化物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、適度な弾性や可撓性維持と硬化収縮抑制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。
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(F)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コート剤や接着剤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硬化塗膜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、その他の成分として各種添加剤(Q)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、酸素除去剤、還元剤、連鎖移動剤、重合促進剤、カブリ防止剤、退色防止剤、ハレーション防止剤、蛍光増白剤、界面活性剤、着色剤、増量剤、発泡剤、消泡剤、防カビ剤、熱重合防止剤、帯電防止剤、磁性体やその他種々の特性を付与する添加剤等の、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。
本発明の活性エネルギー線重合性樹脂組成物は、上記、分子中に1個以上のオキサゾリン環を有する化合物(A)、分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)、及び分子中にカルボキシル基を含有しないα,β−不飽和二重結合基含有化合物(C)を必須成分とし、更に、必要に応じて、オリゴマー(D)、光重合開始剤(E)、カチオン重合性化合物(F)、及びその他の成分(Q)を配合後、均一に混合することによって製造することができる。攪拌・混合する際には、減圧装置を備えた1軸または多軸エクストルーダー、ニーダー、ディソルバーのような汎用の機器を使用し攪拌・混合することにより調製してもよい。攪拌・混合する際の温度は、通常、10〜60℃に設定されるのが好ましい。調製時の設定温度が10℃未満では、粘度が高すぎて均一な撹拌・混合作業が困難になる場合があり、逆に、調製時の温度が60℃を超えると、熱による硬化反応が起きる場合があり、正常な樹脂組成物が得られない場合があるので、好ましくない。
なお、本発明における活性エネルギー線重合性樹脂組成物は、実質的に有機溶剤を含まないことが好ましいが、機溶剤を含有することも可能である。 例えば、メタノール、エタノール、イソプロピルアルコール、アセトン、メチルエチルケトン、メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢酸ブチル、シクロヘキサン、トルエン、キシレンその他の炭化水素系溶媒等の有機溶媒や、水をさらに添加して、樹脂組成物の粘度を調整することもできるし、樹脂組成物を加熱して粘度を低下させることもできる。
本発明の樹脂組成物は、好ましくは、コート剤又は接着剤の用途で使用される。代表的に、樹脂組成物は、常法にしたがい適当な方法で、基材の片面、または両面に塗工され、次いで重合硬化されることによって、樹脂層を形成する。したがって、本発明の一実施形態は、後述の基材(G)と、該基材(G)の少なくとも一方の主面に設けられた、樹脂組成物からなる樹脂層とを有する、積層体に関する。本実施形態において、樹脂層の膜厚は、積層体の用途に応じて設定される。
本発明の活性エネルギー線重合性樹脂組成物の活性エネルギー線による重合反応は、前記した基材(G)のうち、フィルム状基材である透明フィルム、及び該透明フィルムの少なくとも一方の面に位置する活性エネルギー線重合性樹脂組成物層とを具備する、積層体の形成に使用されることが好ましい。
本発明において、透明フィルムの積層体は、以下のようにして得ることができる。
プリズムシートとは、ディスプレイに使用され、正面方向の輝度を向上させるために、液晶パネルのバックライトの導光板上面に設置されるシートで、前方への集光効果を持たせ、正面輝度を向上させるレンズシートと呼ばれる光学フィルム(I)である。
上記、プリズムシートは、一般的に、ポリエステル系樹脂のベースフィルムの上に、アクリル系樹脂のプリズム部(レンズ部)が微細に積層された構造を有し、照度分布,輝度分布,出射角度特性などを考慮して正面輝度の向上のために2枚のプリズムシートを光学軸が互いに異なるように積層(ほぼ直交)して使用される。この際、プリズムピッチ,プリズム深さ,プリズムの材質、光学軸角度により、正面輝度が変化するため、接着剤等で積層固定されて使用されて、これをさらに導光板等の他の光学フィルムに積層されて光学素子用積層体として使用される。
[合成例1〜14]
反応槽、滴下装置、攪拌機、温度計、還流冷却器、窒素導入管を備えた重合反応装置の反応槽に、分子中に1個以上のオキサゾリン環を有するα,β−不飽和二重結合基含有化合物(a1)、α,β−不飽和二重結合基含有化合物(a2)、重合開始剤及び有機溶剤(酢酸エチル)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、攪拌しながら空気雰囲気下中、80℃まで昇温し、滴下装置から表1記載の混合物を滴下開始した。2時間かけて滴下を行った後、さらに攪拌しながら6時間熟成後、酢酸エチルを加えて冷却を行い、樹脂(A)を含む樹脂溶液を得た。
次に、得られた樹脂溶液について、減圧濃縮を施し、得られた粗生成物をメタノール中で再沈殿させた。さらにメタノールで2回、粗生成物を洗浄し、減圧乾燥させた。再度、得られた粗生成物をトルエンに溶かし、ヘキサン500mlに加えて再沈殿により精製し、減圧乾燥を行い、無溶剤の樹脂(A)を得た。
各合成例で得られた樹脂溶液の液体外観を目視にて評価した。
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る。試料をテトラヒドロフランに溶解して、テトラヒドロフランを展開溶剤として流速を0.6ml/min、カラム温度を40℃の条件にて、測定した。標準物質としての単分散分子量のポリスチレンを使用した検量線を作成し、共重合体(A)および共重合体(B)の分子量をポリスチレン換算の数平均分子量(Mn)、重量平均分子量(Mw)を測定した。
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。
樹脂溶液を、剥離処理されたポリエステルフィルムに塗工し、活性エネルギー線を照射し、重合硬化させたものを約10mgかきとり、試料として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。
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
共栓三角フラスコ中に試料、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)
・成分(a1)
OEA:アクリル酸2−(4−オキサゾリン−3−イル)エチル、IPOZO:2−イソプロペニル−2−オキサゾリン、VOZO:2−ビニル−2−オキサゾリン
・成分(c1−1)
HEA:アクリル酸2−ヒドロキシエチル、HEMA:メタクリル酸2−ヒドロキシエチル
・成分(c1−2)
CHDMA:アクリル酸1,4−シクロヘキサンジメタノール
・成分(c2)
BzMA:メタクリル酸ベンジル、MMA:メタクリル酸メチル、DMAA:N,N−ジメチルアクリルアミド、St:スチレン
・開始剤
AIBN:アゾイソブチロニトリル
・溶媒
EAc:酢酸エチルを示す。
「配合例1〜45]
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、分子中に1個以上のオキサゾリン環を有する化合物(A)、分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)、分子中にカルボキシル基を含有しないα,β−不飽和二重結合基含有化合物(C)オリゴマー(D)、光重合開始剤(E)、カチオン重合性化合物(F)、触媒(P)、及びその他の成分(Q)を表2に示す比率で仕込み、にて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す樹脂組成物を得た。
・成分(A)
VOZO:2−ビニル−2−オキサゾリン、IPOZO:2−イソプロペニル−2−オキサゾリン、合成例:合成例1〜12。表1参照。
・成分(B)
AA:アクリル酸、OHPA:2−アクリロイルオキシエチルヘキサヒドロフタレート
・成分(C)
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、CHDMA:アクリル酸1,4−シクロヘキサンジメタノール、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、GMA:メクリル酸グリシジル
・成分(D)
811:Ebecryl811(ダイセルサイテック社製 ポリエステル系オリゴマー(ポリエステルアクリレート))、
3000B: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))、
600:Ebecryl600(ダイセルサイテック社製 ポリエポキシ系オリゴマー(エポキシアクリレート))
・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
・成分(F)
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 (ダイセル社製)、DOME:ジ(1−エチル−3−オキセタニル)メチルエーテル、GC:グリセリンカーボネート
・成分(Q)
A−174:タナック社製シランカップリング剤、DEX−S:日本化薬社製 チオキサントン系増感剤、AO−50:アデカ社製 酸化防止剤を示す。
[実施例1〜38][比較例1〜6]
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樹脂組成物を接着剤として使用して、以下の積層体を作成した。
プリズムシートとして、日本特殊光学樹脂社製プリズムシート:商品名「LPV90−1.0」を2枚使用し、第1のプリズムシートの背面(凸部のレンズ面ではない面)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1μmとなるように塗工し、接着剤層を形成した。次に第2のプリズムシートの正面(凸部のレンズ面)を、光学軸が互いに異なるようほぼ直交に積層し、第1のプリズムシートの背面/接着剤層/第2のプリズムシートの正面からなる積層体を得た。
第1のプリズムシートの正面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の紫外線を第2のプリズムシートの背面側から照射して、固定化したプリズムシートの積層体を作製した。
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、得られた積層体(固定化したプリズムシートの積層体)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、固定化したプリズムシートの積層体と金属板との測定用の積層体を得た。測定用の積層体には、2枚のプリズムシート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)
◎:剥離力が5.0(N/25mm)以上、剥離不可、あるいはプリズムシート破壊
○:剥離力が1.0(N/25mm)以上〜5.0(N/25mm)未満。
△:剥離力が0.5(N/25mm)以上〜1.0(N/25mm)未満。
×:剥離力が0.5(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樹脂組成物を、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、樹脂組成物層を形成した。さらに樹脂組成物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樹脂組成物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を剥離し樹脂組成物層を得た。
樹脂組成物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樹脂組成物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、樹脂組成物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、作製した固定化したプリズムシートの積層体を第2のプリズムシートの背面側から打ち抜いた。
打ち抜いた固定化したプリズムシートの積層体の、周辺の剥離距離を定規で測定し、以下の3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、浮き、剥がれ無し
△:0〜0.5mm
×:0.5mm以上
上記固定化したプリズムシートの積層体小片を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。
上記固定化したプリズムシートの積層体を、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、上記固定化したプリズムシートの積層体の端部の剥がれの有無を目視にて、以下の4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0.5mm未満の剥がれあり。
×:80℃−dry条件下で0.5mm以上の剥がれあり。
上記固定化したプリズムシートの積層体を、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、上記固定化したプリズムシートの積層体の端部の剥がれの有無を目視にて、以下の4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0.5mm未満の剥がれあり。
×:60℃−90%RHの条件下で0.5mm以上の剥がれあり。
[実施例101〜154][比較例11〜16]
表1及び表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2μm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
これに対して比較例1〜6では、剥離強度、ゲル分率、打ち抜き加工性、収縮率、耐熱性、耐湿熱性のいずれにも難があり、使用困難であることがわかる。
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3と同様の傾向であり、表4に示す様に実施例101〜105、110、111、114〜121、127〜142、145〜149、151〜154では、密着性、耐熱性及び柔軟性とも優れ、特に問題無い。また、実施例106〜109、112、113、123〜126、143、150では、密着性、および耐熱性のいずれかのレベルが低いが、使用することが可能である。これに対して比較例111〜116では、密着性、および耐熱性のいずれかに難があり、使用困難であることがわかる。
Claims (10)
- 分子中に1個以上のオキサゾリン環を有する化合物(A)と、
分子中に1個以上のカルボキシル基を含有するα,β−不飽和二重結合基含有化合物(B)と、
分子中にカルボキシル基を含有しないα,β−不飽和二重結合基含有化合物(C)とを
含有する活性エネルギー線重合性樹脂組成物。
ただし、化合物(B)および化合物(C)は、化合物(A)以外の化合物である。 - 活性エネルギー線重合性組成物全量中、
化合物(A)を0.5〜30重量%、
化合物(B)を0.5〜20重量%、
化合物(C)を50〜99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(C)が、水酸基を有するα,β−不飽和二重結合基含有化合物(c1)を含有することを特徴とする請求項1または2記載の活性エネルギー線重合性樹脂組成物。
- 化合物(A)が、分子中に1個以上のオキサゾリン環を有するα,β−不飽和二重結合基含有化合物(a1)であることを特徴とする請求項1〜3のいずれかに記載の活性エネルギー線重合性樹脂組成物。
- 化合物(A)が、化合物(a1)と、化合物(C´)とを共重合してなる共重合体樹脂(ac)を含有することを特徴とする請求項1〜4のいずれかに記載の活性エネルギー線重合性樹脂組成物。
- 化合物(A)のガラス転移温度(Tg)が0℃以上であることを特徴とする請求項1〜5のいずれかに記載の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1〜6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積層体。
- 前記、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7記載の積層体。
- 前記、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8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いずれか記載の樹脂組成物からなる樹脂層とを有する光学素子用積層体。
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