JPWO2015146504A1 - エポキシ樹脂、エポキシ樹脂の製造方法、硬化性樹脂組成物、その硬化物、繊維強化複合材料、及び成形品 - Google Patents
エポキシ樹脂、エポキシ樹脂の製造方法、硬化性樹脂組成物、その硬化物、繊維強化複合材料、及び成形品 Download PDFInfo
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Abstract
Description
本発明のエポキシ樹脂は、フェノールとヒドロキシベンズアルデヒドとの重縮合物のポリグリシジルエーテルであって、下記構造式(1)
東ソー株式会社製「Agilent 1220 Infinity LC」、
カラム: 東ソー株式会社製「TSK−GEL ODS−120T」
検出器: VWD
データ処理:東ソー株式会社製「Agilent EZChrom Elite」
測定条件: カラム温度 40℃
展開溶媒 A液:水/アセトニトリル=50/50wt%
B液:アセトニトリル
展開条件 A液/B液=95/5(15min)
リニアグラジエント(20min)
A液/B液=0/100(20min)
流速 1.0ml/min
測定波長 254nm
測定装置 :東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0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(50μl)
東ソー株式会社製「Agilent 1220 Infinity LC」、
カラム: 東ソー株式会社製「TSK−GEL ODS−120T」
検出器: VWD
データ処理:東ソー株式会社製「Agilent EZChrom Elite」
測定条件: カラム温度 40℃
展開溶媒 A液:水/アセトニトリル=50/50wt%
B液:アセトニトリル
展開条件 A液/B液=95/5(15min)
リニアグラジエント(20min)
A液/B液=0/100(20min)
流速 1.0ml/min
測定波長 254nm
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0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(50μl)
窒素導入管、冷却管、温度計、ディーンスターク装置および撹拌機をセットしたフラスコに、フェノール1128g(12.0mol)、サリチルアルデヒド122g(1.0mol)、パラトルエンスルホン酸12.5gを入れ、撹拌しながら45分間かけて120℃まで昇温した。反応により生じた縮合水をディーンスターク装置にて留去しながら120℃で3時間反応させた。反応終了後、49%水酸化ナトリウム水溶液5.1gを加えて中和し、脱水回路に切り替えて、3時間かけて180℃まで昇温した。傾注に水蒸気を吹き込みながら余剰のフェノールを一部除去し、軟化点108℃、水酸基当量98g/eqのフェノール樹脂中間体(1)280gを得た。
窒素導入管、冷却管、温度計、ディーンスターク装置および撹拌機をセットしたフラスコに、フェノール940g(10.0mol)、サリチルアルデヒド122g(1.0mol)、パラトルエンスルホン酸10.7g、トルエン1062gを入れ、撹拌しながら45分間かけて120℃まで昇温した。反応により生じた縮合水をディーンスターク装置にて留去しながら120℃で3時間反応させた。反応終了後、49%水酸化ナトリウム水溶液5.1gを加えて中和し、脱水回路に切り替えて、3時間かけて180℃まで昇温した。傾注に水蒸気を吹き込みながら余剰のフェノールを一部除去し、軟化点117℃、水酸基当量98g/eqのフェノール樹脂中間体(2)277gを得た。
フェノール樹脂中間体(1)98g(1.0mol)を、「TPM−113」に変更した以外は実施例1と同様にしてエポキシ樹脂(1’)を得た。エポキシ樹脂(1’)のGPCチャート図を図5に、HPLCチャート図を図6に示す。エポキシ樹脂(1’)のエポキシ当量は169g/eq、150℃での溶融粘度は1.0dPa・sであった。また、GPCチャート図から算出されるエポキシ樹脂(1’)中の3核体(X)の含有量は65.8%、HPLCチャート図から算出される3核体(X)中の[o,p,p]結合体(x1)の含有量は20.2%、[o,o,p]結合体(x2)の含有量は52.1%[o,o,o]結合体(x3)の含有量は27.7%であった。その結果を表1に示す。
下記要領で硬化性樹脂組成物を配合し、それらの硬化物について各種評価を行った。配合量及び各種評価試験の結果を表2〜4に示す。なお、表中の各成分の詳細は以下の通りである。
エポキシ樹脂(1) :実施例1で製造されたエポキシ樹脂
エポキシ樹脂(2) :実施例2で製造されたエポキシ樹脂
エポキシ樹脂(1’):比較製造例1で製造されたエポキシ樹脂
酸無水物硬化剤 :メチルテトラヒドロフタル酸無水物(DIC株式会社製「EP
ICLON B−570H」酸無水物基当量166g/eq)
1,2−DMZ :1,2−ジメチルイミダゾール
ジシアンジアミド :三菱化学株式会社製「JERキュアDICY−7」
DCMU :N,N−ジメチル−N’−(3,4−ジクロロフェニル)尿素
(保土ヶ谷化学工業株式会社製「DCMU」)
4,4’−ジアミノジフェニルスルホン
:和歌山精化工業株式会社製「SEIKACURE−S」
下記表2〜4に示す割合で各成分を配合し、溶融混練により均一混合して実施例3〜比較例3の硬化性樹脂組成物を得た。
実施例3〜4、比較例1で得られた硬化性樹脂組成物を幅90mm、長さ110mm、高さ2mmの型枠内に流し込み、150℃で1時間プレス成形し硬化物を得た。これをダイヤモンドカッターにて幅5mm、長さ50mmに切り出し、エスアイアイ・ナノテクノロジー社製「DMS6100」を用いて以下の条件による両持ち曲げによる動的粘弾性を測定した。貯蔵弾性率(E’)のオンセット温度をガラス転移温度(Tg)として評価した。その結果を表2に示す。
[測定条件]
測定温度範囲:室温〜260℃
昇温速度:3℃/分
周波数:1Hz(正弦波)
歪振幅:10μm
実施例5〜8、比較例2〜3で得られた硬化性樹脂組成物を幅90mm、長さ110mm、高さ2mmの型枠内に流し込み、150℃で1時間プレス成形し硬化物を得た。これをダイヤモンドカッターにて幅5mm、長さ50mmに切り出し、エスアイアイ・ナノテクノロジー社製「DMS6100」を用いて以下の条件による両持ち曲げによる動的粘弾性を測定した。tanδが最大値となる温度をガラス転移温度(Tg)として評価した。その結果を表3、4に示す。
[測定条件]
測定温度範囲:室温〜260℃
昇温速度:3℃/分
周波数:1Hz(正弦波)
歪振幅:10μm
実施例3〜6、比較例1〜2で得られた硬化性樹脂組成物を幅90mm、長さ110mm、高さ2mmの型枠内に流し込み、150℃で1時間プレス成形し硬化物を得た。JIS K6911に準拠して、硬化物の曲げ強度及び曲げ弾性率を測定した。その結果を表2、3に示す。
実施例7〜8、比較例3で得られた硬化性樹脂組成物を幅90mm、長さ110mm、高さ2mmの型枠内に流し込み、150℃で1時間プレス成形したのち、さらに3時間加熱して硬化物(試験片2)を得た。得られた試験片2の曲げ強度及び曲げ弾性率を、JIS K6911に準拠して測定した。その結果を表4に示す。
実施例3〜8、比較例2〜3で得られた硬化性樹脂組成物から得られた前記硬化物を温度121℃、湿度100%の環境下に6時間静置した後、先と同様の方法でガラス転移温度、曲げ強度及び曲げ弾性率を測定した。さらに、湿熱試験前の値に対する湿熱試験後の値を計算し、物性保持率として評価した。その結果を表3〜4に示す。
Claims (15)
- 樹脂中の前記3核体(X)の含有量が、GPC測定における面積比率で70%以上である請求項1記載のエポキシ樹脂。
- エポキシ当量が160〜170g/当量である請求項1記載のエポキシ樹脂。
- 前記ヒドロキシベンズアルデヒドが、オルソヒドロキシベンズアルデヒドである請求項1記載のエポキシ樹脂。
- フェノールとオルソヒドロキシベンズアルデヒドとを、両者のモル比[(フェノール):(ヒドロキシベンズアルデヒド)]が1:0.05〜1:0.25となる割合で反応させて得られるフェノール樹脂中間体得、次いで、得られたフェノール樹脂中間体とエピクロルヒドリンとを反応させて得られる請求項5のエポキシ樹脂。
- フェノールとオルソヒドロキシベンズアルデヒドとを、両者のモル比[(フェノール):(ヒドロキシベンズアルデヒド)]が1:0.05〜1:0.25となる割合で反応させてフェノール樹脂中間体得、次いで、得られたフェノール樹脂中間体とエピクロルヒドリンとを反応させることを特徴とするエポキシ樹脂の製造方法。
- 150℃での溶融粘度が1mPa・s〜100mPa・sの範囲である請求項1記載のエポキシ樹脂。
- 請求項1記載のエポキシ樹脂と、硬化剤とを含有する硬化性樹脂組成物。
- 前記硬化剤が、酸無水物、ジシアンジアミド化合物又は芳香族アミン化合物のいずれかである請求項10記載の硬化性樹脂組成物。
- 請求項10記載の硬化性樹脂組成物を硬化させてなる硬化物。
- 請求項1記載のエポキシ樹脂と、硬化剤と、強化繊維とを含有する繊維強化複合材料。
- 前記硬化剤が、酸無水物、ジシアンジアミド化合物又は芳香族アミン化合物のいずれかである請求項13記載の繊維強化複合材料。
- 請求項13記載の繊維強化複合材料を硬化させてなる成形品。
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US9975987B2 (en) | 2018-05-22 |
KR20160137993A (ko) | 2016-12-02 |
US20170121451A1 (en) | 2017-05-04 |
CN106133021A (zh) | 2016-11-16 |
JP2018003033A (ja) | 2018-01-11 |
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JP6309973B2 (ja) | 2018-04-11 |
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