JP6766323B2 - ポリウレタン変性エポキシ樹脂及び接着剤 - Google Patents
ポリウレタン変性エポキシ樹脂及び接着剤 Download PDFInfo
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- JP6766323B2 JP6766323B2 JP2015114865A JP2015114865A JP6766323B2 JP 6766323 B2 JP6766323 B2 JP 6766323B2 JP 2015114865 A JP2015114865 A JP 2015114865A JP 2015114865 A JP2015114865 A JP 2015114865A JP 6766323 B2 JP6766323 B2 JP 6766323B2
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- epoxy resin
- polyurethane
- modified epoxy
- equivalent
- compound
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Description
本発明のポリウレタン変性エポキシ樹脂は、水酸基含有エポキシ樹脂(A)とイソシアネート基含有ウレタン樹脂(B)とを反応させて得られ、エポキシ当量が240〜400g/当量の範囲であることを特徴とする。
の何れかで表される構造部位である。]
で表されるものが挙げられる。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
温度計、攪拌器、及び還流冷却器を備えたフラスコを窒素で置換し、ポリカプロラクトンジオール[株式会社ダイセル製「プラクセル230」重量平均分子量(Mw)3,000]871質量部、イソホロンジイソシアネート129質量部を混合し、触媒としてジオクチル錫触媒(日東化成株式会社製「ネオスタンU−820」)0.1質量部を添加し、70℃で3時間反応させて、イソシアネート基含有ウレタン樹脂(B−1)を得た。イソシアネート基含有ウレタン樹脂(B−1)のイソシアネート基含有量は2.4質量%であった。
反応原料を表1に示すとおりに変更した以外は、製造例1と同様にしてイソシアネート基含有ウレタン樹脂(B−2)〜(B−4)を得た。
「PTMG3000」・・・三菱化学株式会社製 ポリテトラメチレングリコール 重量平均分子量(Mw)3,000
「P−3010」・・・クラレ株式会社製 ポリ(3−メチル−1,5−ペンタンジオールアジペート) 重量平均分子量(Mw)3,000
「D−2000」・・・三井化学株式会社製 ポリプロピレングリコール 重量平均分子量(Mw)2,000
温度計、攪拌器、及び還流冷却器を備えたフラスコに、窒素雰囲気下、ビスフェノールF型エポキシ樹脂(DIC株式会社製「EPICLON 830」エポキシ当量167g/当量)481質量部、ビスフェノールF69質量部、及び触媒としてテトラメチルアンモニウムクロライド0.07質量部を仕込み、140℃まで加熱して撹拌しながら反応させ、エポキシ当量250g/当量、水酸基価85mgKOH/gの水酸基含有エポキシ樹脂(A−1)を得た。
温度計、攪拌器、及び還流冷却器を備えたフラスコを窒素で置換し、イソシアネート基含有ウレタン樹脂(B−1)350質量部、ビスフェノールF型エポキシ樹脂(DIC株式会社製「EPICLON 830」エポキシ当量167g/当量、水酸基価20mgKOH/g)650質量部を混合、70℃まで昇温して、イソシアネート基含有量がほぼ0になるまで反応させて、ポリウレタン変性エポキシ樹脂(1)を得た。ポリウレタン変性エポキシ樹脂(1)のエポキシ当量は255g/当量であった。
反応原料を表2に示すとおりに変更した以外は、実施例1と同様にしてポリウレタン変性エポキシ樹脂(2)〜(5)を得た。なお、「EPICLON 850」はエポキシ当量188g/当量、水酸基価20mgKOH/gのDIC株式会社製ビスフェノールA型エポキシ樹脂である。
温度計、攪拌器、及び還流冷却器を備えたフラスコに、窒素雰囲気下、ビスフェノールF型エポキシ樹脂(DIC株式会社製「EPICLON 830」エポキシ当量167g/当量)850質量部、イソシアネート含有ウレタン樹脂(B−4)150質量部を添加した。70℃まで加熱し、イソシアネート基含有量がほぼ0になるまで反応させて、ポリウレタン変性エポキシ樹脂(1‘)を得た。得られたポリウレタン変性エポキシ樹脂(1’)のエポキシ当量は200g/当量であった。
硬化性組成物(I)の調整及び評価
実施例1〜5及び比較製造例1で得たポリウレタン変性エポキシ樹脂を用いて下記要領で硬化性組成物(I)を調整し、その硬化物について各種評価試験を行った。結果を表3に示す。
変性エポキシ樹脂、ポリエーテルアミン(ハンツマン社製「JEFFAMINE D-230」活性水素当量57g/当量)を表3に示す割合で配合し、硬化性組成物(I)を得た。
先で得た硬化性組成物(I)を膜厚が2mmの金型に注入し、80℃、100℃、120℃で各3時間かけて硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(I)を用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、80℃、100℃、120℃で各3時間かけて硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
硬化性組成物(II)、(III)の調整及び評価
実施例1〜5で得たポリウレタン変性エポキシ樹脂を用いて下記要領で硬化性組成物(II)、(III)を調整し、その硬化物について各種評価試験を行った。結果を表4、5に示す。
ポリウレタン変性エポキシ樹脂、ジシアンジアミド、3,4−ジクロロフェニル−N,N−ジメチル尿素を表4に示す割合で配合し、硬化性組成物(II)を得た。
先で得た硬化性組成物(II)を膜厚が2mmになるように金型に注入し、180℃で1時間加熱し硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(II)用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、180℃で1時間加熱し硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
ポリウレタン変性エポキシ樹脂、アミド樹脂(DIC株式社製「ラッカマイド TD−960」活性水素当量78g/当量)を表5に示す割合で配合し、硬化性組成物(III)を得た。
先で得た硬化性組成物(III)を膜厚が2mmになるように金型に注入し、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。硬化物から1号ダンベル型のサンプルを切り出し、島津製作所株式会社製「AUTOGRAPH AG−IS 1kN」を用いて引張試験を行い、伸び率(%)で評価した。
先で得た硬化性組成物(III)用い2枚の鋼板を熱硬化接着した。接着層の膜厚は0.2mmとし、80℃、100℃、120℃で順に、それぞれ3時間ずつ加熱し硬化させた。得られた接着試験鋼板について、JIS K6859(接着剤のクリープ破壊試験)に基づき、島津製作所株式会社製「AUTOGRAPH AG-IS 10kN」を用いて引張せん断試験を行い、破断強度(MPa)で評価した。
Claims (8)
- 水酸基含有エポキシ樹脂(A)と
イソホロンジイソシアネートを原料とするイソシアネート基含有ウレタン樹脂(B)とを反応させて得られ、
エポキシ当量が240〜400g/当量の範囲である(ただし、オキサゾリドン環および/又はイソシアヌレート環を含むものを除く)ポリウレタン変性エポキシ樹脂であって、
前記水酸基含有エポキシ樹脂(A)が、下記構造式(1)で表される分子構造を有するものである(ただしnが0のみからなるものを除く)ことを特徴とするポリウレタン変性エポキシ樹脂。
- 前記水酸基含有エポキシ樹脂(A)と前記イソホロンジイソシアネートを原料とするイソシアネート基含有ウレタン樹脂(B)との反応質量比[(A)/(B)]が80/20〜55/45の範囲である請求項1記載のポリウレタン変性エポキシ樹脂。
- 前記水酸基含有エポキシ樹脂(A)の水酸基価が10〜100mgKOH/gの範囲である請求項1記載のポリウレタン変性エポキシ樹脂。
- 前記水酸基含有エポキシ樹脂(A)のエポキシ当量が155〜300g/当量の範囲である請求項1記載のポリウレタン変性エポキシ樹脂。
- 請求項1〜4の何れか一つに記載のポリウレタン変性エポキシ樹脂と、硬化剤又は硬化促進剤とを含有する硬化性組成物。
- 前記硬化剤又は硬化促進剤がポリエーテルアミン化合物又はアミド化合物である請求項5記載の硬化性組成物。
- 請求項5又は6記載の硬化性組成物を硬化させて得られる硬化物。
- 請求項1〜4の何れか一つに記載のポリウレタン変性エポキシ樹脂と、硬化剤又は硬化促進剤とを含有する接着剤。
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