JP2021084936A - 硬化性組成物、硬化物及び接着剤 - Google Patents
硬化性組成物、硬化物及び接着剤 Download PDFInfo
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- JP2021084936A JP2021084936A JP2019213203A JP2019213203A JP2021084936A JP 2021084936 A JP2021084936 A JP 2021084936A JP 2019213203 A JP2019213203 A JP 2019213203A JP 2019213203 A JP2019213203 A JP 2019213203A JP 2021084936 A JP2021084936 A JP 2021084936A
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- polyol
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- epoxy resin
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Abstract
Description
本発明は、ポリオキシエチレンユニットとポリオキシプロピレンユニットとポリオキシテトラメチレンユニットとを含むポリオール(a1)と、ポリイソシアネート(a2)と、を必須の原料とするイソシアネートプレポリマー(A)と、エポキシ樹脂(B)と、硬化剤又は硬化促進剤(C)と、を含有することを特徴とする。
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)
の何れかで表される構造部位であり、nは繰り返し数を表す。]
で表されるものが挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。
の何れかで表される化合物などが挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。中でも、硬化物における柔軟性と靱性に優れることから、前記一般式(3−1)又は(3−2)で表される化合物が好ましい。
窒素雰囲気下、三井ケミカル&SKCポリウレタン(MCNS)社製ポリオキシエチレン(PE)−ポリオキシプロピレン(PP)コポリマーであるポリエーテルポリオール(アクトコールEP−450 Mn:3800 官能基数:3) 194質量部、三菱ケミカル社製ポリテトラメチレングリコール(PTMG−3000 Mn:3000 官能基数:2) 582質量部、住化コベストロウレタン社製イソホロンジイソシアネート(IPDI)126質量部を混合し、触媒としてネオスタン U-820 0.1部を投入し、80℃で5時間反応せしめ、次いでブロック化剤としてパラターシャリーブチルフェノール(PTBP)98質量部を投入し90℃で5時間反応せしめブロックイソシアネート樹脂(1)を得た。
合成例1と同様の処方で、表1の配合組成より、ブロックイソシアネートプレポリマー(2)−(6)を得た。
EP−450:MCNS社製PE−PPポリオール(Mn:3800 官能基数:3)
EP−551:MCNS社製PE−PPポリオール(Mn:3800 官能基数:3)
T−3000:MCNS社製PPポリオール(Mn:3000 官能基数:3)
EP−3033: MCNS社製PPポリオール(Mn:6600 官能基数:4)
PTMG−3000:三菱ケミカル社製ポリテトラメチレングリコール(Mn:3000 官能基数:2)
PTMG−4000:三菱ケミカル社製ポリテトラメチレングリコール(Mn:4000 官能基数:2)
IPDI:住化コベストロウレタン社製イソホロンジイソシアネート
HMDI:東ソー社製ヘキサメチレンジイソシアネート
TDI:MCNS社製トリレンジイソシアネート T−80
DMP:大塚化学社製3,5−ジメチルピラゾール
BPF:DIC株式会社製 ビスフェノールF
合成例1で合成したブロックイソシアネート樹脂(1) 20質量部、DIC株式会社製ビスフェノールA型エポキシ樹脂EPICLON 850−S 70質量部、DIC株式会社製ゴム変性エポキシ樹脂EPICLON TSR−601 10質量部、硬化剤としてジシアンジアミド(DICY) 5質量部、硬化促進剤として3,4−ジクロロフェニル−N,N−ジメチル尿素(DCMU)1質量部、フィラーとして炭酸カルシウム(CaCO3)を20質量部混合し、硬化性組成物(1)を得た。この硬化性組成物(1)について、170℃で30分かけて硬化した硬化物について、接着性評価と耐湿熱試験を行った。
<引張剪断試験>
JIS K6859 (接着剤のクリープ破壊試験)方法で25℃の条件で島津製作所製 AUTOGRAPH AG−XPlus 100kNを用いて引張せん断強度を測定した。併せて破壊状態についても凝集破壊(CF)の面積比率(%)で評価を行った。
<T字剥離試験>
JIS K6854−3 (接着剤の剥離接着強さ試験)方法で25℃の条件で島津製作所株式会社製 AUTOGRAPH AG−IS 1kNを用いて剥離強度を測定した。
上記 JIS K6859<引張剪断試験>方法で作成した試験片を温度:70℃、湿度:90%の環境下で2週間保管後、5時間以内にJIS K6859 (接着剤のクリープ破壊試験)方法で25℃の条件で島津製作所製AUTOGRAPH AG−XPlus 100kNを用いて引張せん断強度を測定した。併せて破壊状態についても凝集破壊(CF)の面積比率で評価を行った。
実施例1のブロックイソシアネート樹脂(1)に替えて表2に示したブロックイソシアネートを用いた以外は実施例1と同様にして配合した硬化性組成物について同様の評価を実施した。またその評価結果を表2にまとめた。
合成例1と同様の処方で表3の配合組成より、比較用のブロックイソシアネートプレポリマー(7)−(10)を得た。
実施例1のブロックイソシアネートプレポリマー(1)に替えて表4に示したブロックイソシアネートプレポリマーを用いた以外は実施例1と同様にして配合した硬化性組成物について同様の評価を実施した。またその評価結果を表4にまとめた。
Claims (13)
- ポリオキシエチレンユニットとポリオキシプロピレンユニットとポリオキシテトラメチレンユニットとを含むポリオール(a1)と、
ポリイソシアネート(a2)と、を必須の原料とするイソシアネートプレポリマー(A)と、
エポキシ樹脂(B)と、
硬化剤又は硬化促進剤(C)と、を含有することを特徴とする硬化性組成物。 - 前記イソシアネートプレポリマー(A)が、前記ポリオール(a1)中の水酸基の合計量に対して、過剰のイソシアネート基となるようにポリイソシアネート(a2)を用いてなるポリウレタンをブロック化剤(a3)でブロックしてなるブロックイソシアネートプレポリマーである請求項1記載の硬化性組成物。
- 前記ブロック化剤(a3)が1価のフェノール化合物である請求項2記載の硬化性組成物。
- 前記ポリオール(a1)が、ポリオキシエチレンユニットとポリオキシプロピレンユニットを含むポリオール(a1−1)と、ポリオキシテトラメチレンポリオール(a1−2)と、の混合物である請求項1〜3の何れか1項記載の硬化性組成物。
- 前記ポリオール(a1−1)が、ポリオキシエチレン−ポリオキシプロピレン共重合体である請求項4記載の硬化性組成物。
- 前記ポリオール(a1−1)と前記ポリオキシテトラメチレンポリオール(a1−2)との使用割合が、(a1−1)/(a1−2)で表される質量比として10/90〜60/40の範囲である請求項4又は5記載の硬化性組成物。
- 前記ポリオール(a1)中のポリオキシエチレンユニットとポリオキシプロピレンユニットとの質量比が30/70〜1/99の範囲である請求項1〜6の何れか1項記載の硬化性組成物。
- 前記ポリオール(a1)の数平均分子量が1000〜7000の範囲である請求項1〜7の何れか1項記載の硬化性組成物。
- 前記ポリイソシアネート(a2)がジイソシアネートである請求項1〜8の何れか1項記載の硬化性組成物。
- 前記エポキシ樹脂(A)のエポキシ当量が150〜250g/eqの範囲である請求項1〜9の何れか1項記載の硬化性組成物。
- 前記イソシアネートプレポリマー(A)と前記エポキシ樹脂(B)との使用割合が、(A)/(B)で表される質量比として10/90〜30/70の範囲である請求項1〜10の何れか1項記載の硬化性組成物。
- 請求項1〜11の何れか1項記載の硬化性組成物の硬化物。
- 請求項1〜11の何れか1項記載の硬化性組成物からなる接着剤。
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JP2003506506A (ja) * | 1999-07-28 | 2003-02-18 | バイエル アクチェンゲゼルシャフト | 無溶剤室温硬化性反応系および接着剤、封止剤、注型用化合物、成形品または塗料の製造におけるその使用 |
WO2012017724A1 (ja) * | 2010-08-06 | 2012-02-09 | Dic株式会社 | ウレタン樹脂組成物、コーティング剤、皮革様シートの表皮層形成用ウレタン樹脂組成物、並びに積層体及び皮革様シート |
JP2014001381A (ja) * | 2012-05-24 | 2014-01-09 | Toho Chem Ind Co Ltd | 一液型止水剤 |
WO2020255844A1 (ja) * | 2019-06-18 | 2020-12-24 | Dic株式会社 | 硬化性組成物、硬化物及び接着剤 |
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