JP5684275B2 - エネルギー線硬化性樹脂組成物とそれを用いた接着剤及び硬化体 - Google Patents
エネルギー線硬化性樹脂組成物とそれを用いた接着剤及び硬化体 Download PDFInfo
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- JP5684275B2 JP5684275B2 JP2012534867A JP2012534867A JP5684275B2 JP 5684275 B2 JP5684275 B2 JP 5684275B2 JP 2012534867 A JP2012534867 A JP 2012534867A JP 2012534867 A JP2012534867 A JP 2012534867A JP 5684275 B2 JP5684275 B2 JP 5684275B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
しかし、このようなエネルギー線硬化性樹脂組成物はカチオン重合開始剤のアニオン部位にヒ素(As)やアンチモン(Sb)といった毒性の強い元素が用いられているため、取り扱いや環境に対する影響への懸念といった問題があった。更に該アニオン部位の分解によりフッ化物イオンを放出し、金属に対する腐食性(以下、「腐食性」と称する)を示すため、使用が限定されるといった問題があった。
(1)(A)カチオン重合性化合物、(B)式(1)で表される光カチオン重合開始剤、(C)フェノール系酸化防止剤とキノン系酸化防止剤からなる群のうちの1種又は2種以上を含有することを特徴とするエネルギー線硬化性樹脂組成物。
(3)(A)成分100質量部、(B)成分0.1〜10質量部、(C)成分0.01〜20質量部を含有することを特徴とする(1)又は(2)のいずれか1項に記載のエネルギー線硬化性樹脂組成物。
(4)(D)式(2)で表される塩を含有することを特徴とする(1)〜(3)のいずれか1項に記載のエネルギー線硬化性樹脂組成物。
(6)光増感剤を含有することを特徴とする(1)〜(5)のいずれか1項に記載のエネルギー線硬化性樹脂組成物。
(7)前記(1)〜(6)のいずれか1項に記載のエネルギー線硬化性樹脂組成物が硬化してなる硬化体。
(8)前記(1)〜(6)のいずれか1項に記載のエネルギー線硬化性樹脂組成物からなる接着剤。
本願明細書において、エネルギー線硬化性樹脂組成物とは、エネルギー線を照射することによって硬化させることができる樹脂組成物を意味する。ここで、エネルギー線とは、紫外線、可視光線等に代表されるエネルギー線を意味する。
本願明細書において、貯蔵安定性とは、長期間にわたる保存後も、増粘やゲル化が生じることがないことをいう。
本実施形態に係るエネルギー線硬化性樹脂組成物は、(A)カチオン重合性化合物を必須成分とする。
光カチオン重合開始剤は、エネルギー線を照射することによりカチオン種が発生する以下に記載の化合物である。
本実施形態に係るエネルギー線硬化性樹脂組成物は、酸化防止剤として、フェノール系酸化防止剤とキノン系酸化防止剤からなる群のうちの1種又は2種を含有することが必須である。
本実施形態に係るエネルギー線硬化性樹脂組成物は、貯蔵安定性の点で、(D)式(2)で表されるホスフィンオキサイド誘導体を使用しても良い。(D)式(2)で示される塩は、1種のみ又は2種以上を選択して任意の割合で使用することができる。
本実施形態に係るエネルギー線硬化性樹脂組成物は、フィラー(無機充填剤)を更に含有していてもよい。
(光増感剤)
本実施形態に係るエネルギー線硬化性樹脂組成物は、各種光増感剤を併用してもよい。光増感剤とは、エネルギー線を吸収して、光カチオン重合開始剤からカチオンを効率よく発生させる化合物をいう。
本実施形態の目的を損なわない範囲で、アクリルゴム、ウレタンゴム等の各種エラストマー、メタクリル酸メチル−ブタジエン−スチレン系グラフト共重合体やアクリロニトリル−ブタジエン−スチレン系グラフト共重合体等のグラフト共重合体、溶剤、増量材、補強材、可塑剤、増粘剤、染料、顔料、難燃剤及び界面活性剤等の添加剤が含有されても良い。
本実施形態に係るエネルギー線硬化性樹脂組成物の製造方法については、上記の材料を十分に混合できれば特に制限はない。材料の混合方法としては、特に限定されないが、プロペラの回転に伴う撹拌力を利用する撹拌法、自転公転による遊星式撹拌機等の通常の分散機を利用する方法等が挙げられる。これらの混合方法は、低コストで、安定した混合を行えるので好ましい。
本実施形態において、エネルギー線硬化性樹脂組成物の硬化、接着に用いられる光源としては、特に限定されないが、ハロゲンランプ、メタルハライドランプ、ハイパワーメタルハライドランプ(インジウム等を含有する)、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、キセノンランプ、キセノンエキシマランプ、キセノンフラッシュランプ、ライトエミッティングダイオード(以下、LEDという)等が挙げられる。これらの光源は、それぞれの光重合開始剤の反応波長に対応したエネルギー線の照射を効率よく行える点で、好ましい。
(A)成分のカチオン重合性化合物として下記を用いた。
(A−1)3,4−エポキシシクロヘキセニルメチル−3’,4’−エポキシシクロヘキセンカルボキシレート(ダイセル化学社製「セロキサイド2021P」)
(A−2)ビスフェノールF型エポキシ樹脂(ジャパンエポキシレジン社製「YL−938U」)
(A−3)ノボラックフェノール型エポキシ樹脂(ジャパンエポキシレジン社製 「EP−152」)
(A−4)ポリプレングリコール型エポキシ樹脂(阪本薬品工業社製「SR−PTMG」)
(A−5)ジ(1−エチル−3−オキセタニル)メチルエーテル(東亜合成社「OXT221」)
(B−1)ビス-(4-t-ブチル-フェニル)-ヨードニウム-トリス(トリフルオロメタンスルホニル)メチド(チバジャパン社製「CGI*BBI C1」)
(B−2)トリフェニルスルホニウム-トリス(トリフルオロメタンスルホニル)メチド (チバジャパン社製「CGI*TPS C1」)
(B−3)トリス-{4-アセチル-スルファニル}-フェニル}-スルホニウム-トリス(トリフルオロメタンスルホニル)メチド(チバジャパン社製「GSID26−1」)
比較のために、下記の光カチオン開始剤(B−4およびB−5)を用いた。
(B−4)ヨードニウム{4−(2−メチルプロピル)フェニル}(ヘキサフルオロフォスフェイト)(プロピレンカーボネート溶媒中に75質量%含有)(チバジャパン社製「Irgacure−250」)
(B−5)芳香族スルホニウムPF6塩(アデカ社製「アデカオプトマーSP−150」)
(C−1)ペンタエリスリチル・テトラキス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート](チバジャパン社製「Irganox−1010」)
(C−2)オクタデシル−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート(チバジャパン社製「Irganox−1076」)
(C−3)2,5−ジ−tert−ブチル−ハイドロキノン(川口化学工業社製「DBHQ」)
(C−4)4,4‘−チオビス(6−テトラ−ブチル1−3−メチルフェノール)(住友化学社製SUMILIZER WX−R)
(D−1)ポリリン酸ナトリウム(関東化学社製)
比較のために、リンオキサイド化合物である亜リン酸ジエチル(D−2)を用いた。
(D−2)亜リン酸ジエチル(和光純薬工業社製)
表1に示す種類の原材料を、表1に示す組成割合で混合し、実施例1〜9の樹脂組成物を調製した。光硬化性、引張剪断接着強さおよび保存貯蔵安定性について、後述する評価を行い、結果を表1に示した。
表2に示す種類の原材料を、表2に示す組成割合で混合し、比較例1〜3の樹脂組成物を調製した。評価の結果を表2に示した。
表3に示す種類の原材料を、表3に示す組成割合で混合し、実施例10〜13の樹脂組成物を調製した。評価の結果を表3に示した。
レオメーター(アートンパール社製「MCR−301」)ではUV照射下の剛性率を測定することができる。測定は、調製した樹脂組成物を直径8mmの円形のプレートで両面から挟み、該樹脂組成物にUV(365nmの照度:150mW/cm2)を照射しながら25℃(±0.5℃)、周波数10Hzで行った。UV照射開始後200秒までに、貯蔵剛性率G’が1.00E+4(1.00×104)以上に増加したものを良好と判断して、記号「○」を付した。一方、UV照射開始後200秒までに、貯蔵剛性率G’が1.00E+4に満たなかったものを不良と判断して、記号「×」を付した。
引張せん断接着強さ:JIS K 6850に従い測定した。具体的には被着材とした耐熱ガラス(商品名「耐熱パイレックス(登録商標)ガラス」、25mm×25mm×2.0mm)を用いて、接着部位を直径8mmの円形として、作製した該樹脂組成物にて、2枚の耐熱ガラスを張り合わせ、UV照射器を使用し、積算光量52000mJ/cm2(365nmの照度:400mW/cm2、ウシオ電機社製「SP−7(水銀キセノンランプ搭載UV硬化装置)」)の条件にて硬化させ、引張り強さ試験片を作製した。作製した試験片は、23℃、湿度50%の環境で、万能試験機を使用して、引張せん断接着強さを測定した。
組成物の初期粘度(V0)を測定した後、容器に入れて蓋をした状態(密閉系)で、40℃の高温環境下における養生促進試験を行い、4週間後の組成物の粘度(V4)を測定した。そして、式:V4/V0に従って粘度変化率を求めた。粘度変化率が4以下のものを保存貯蔵安定性良好と判断した。
組成物の粘度はE型粘度計を用い、温度25℃、回転数10rpmの条件下で測定した。
Claims (7)
- 請求項1記載の式(1)におけるBが、CF3で表されることを特徴とするエネルギー線硬化性樹脂組成物。
- (A)成分100質量部、(B)成分0.1〜10質量部、(C)成分0.01〜20質量部を含有することを特徴とする請求項1又は2記載のエネルギー線硬化性樹脂組成物。
- (E)フィラーを含有することを特徴とする請求項1〜3のいずれか1項に記載のエネルギー線硬化性樹脂組成物。
- 光増感剤を含有することを特徴とする請求項1〜4のいずれか1項に記載のエネルギー線硬化性樹脂組成物。
- 請求項1〜5のいずれか1項に記載のエネルギー線硬化性樹脂組成物が硬化してなる硬化体。
- 請求項1〜5のいずれか1項に記載のエネルギー線硬化性樹脂組成物からなる接着剤。
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