JP2006335797A - エポキシ樹脂組成物、その硬化物、新規エポキシ樹脂及びその製造方法 - Google Patents
エポキシ樹脂組成物、その硬化物、新規エポキシ樹脂及びその製造方法 Download PDFInfo
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- JP2006335797A JP2006335797A JP2005159229A JP2005159229A JP2006335797A JP 2006335797 A JP2006335797 A JP 2006335797A JP 2005159229 A JP2005159229 A JP 2005159229A JP 2005159229 A JP2005159229 A JP 2005159229A JP 2006335797 A JP2006335797 A JP 2006335797A
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- epoxy resin
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 50
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
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Abstract
Description
で表される構造単位を有する芳香族環変性フェノールアラルキル型エポキシ樹脂が、耐湿性、耐熱性、耐衝撃性等の技術課題を解決するものとして開示されている(例えば、特許文献1参照)。これは一般的なフェノールアラルキル型エポキシ樹脂と異なり、フェノール類と芳香族系架橋剤とを反応させる際に、芳香族環含有化合物類を反応系に加えて得られる変性フェノールアラルキル樹脂をグリシジル化して得られるエポキシ樹脂の1種であり、一般的なフェノールアラルキル型エポキシ樹脂と比較して、芳香族性が上がり、エポキシ樹脂硬化物の難燃性の改良効果が認められるが、それでも要求レベルを十分満足できるレベルには至っていないばかりか、エポキシ当量が高いために架橋密度が低く、成形性(成形時の硬度)に劣るものであった。
で表されるメトキシ基変性フェノールノボラック樹脂が、耐湿性と耐衝撃性の技術課題を解決するものとして開示されている(例えば、特許文献2参照。)。該樹脂の水酸基当量は一般的なフェノールノボラック樹脂と比較して高まるために、得られる硬化物の耐湿性と耐衝撃性の改良効果は認められるものの、難燃性と成形性を満足できるレベルにまで改良するものではなく、更なる改良が求められている。また、上記のメトキシ基変性フェノールノボラック樹脂は、フェノール類とホルムアルデヒドとの反応で得られるノボラック前駆体(ジメチロール化物)の段階で、フェノール水酸基をジメチル硫酸やハロゲン化アルキル等を用いてアルコキシ基化して得られるものであり、アニソール等のアルコキシ基含有芳香族系化合物を出発原料として用いたものではない。これは、フェノール性水酸基をアルコキシ化して得られるアルコキシ基が、フェノール性水酸基の保護技術として広く用いられている様に、一般的には、強酸性環境下では容易に分解することが知られていることによる。つまり、芳香族性ヒドロキシ化合物類の多核体化反応に、アルコキシ基含有芳香族系化合物を出発原料として使用すれば、反応中に容易に分解することが懸念され、それを該反応系で共重合させようといった発想は、通常、当業者は持ちえず、メトキシ基変性フェノールノボラック樹脂の出発原料としてアルコキシ基含有芳香族系化合物が、一切、具体的に記載されていない技術的背景である。
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有するエポキシ樹脂と硬化剤とを含有することを特徴とするエポキシ樹脂組成物、及びその硬化物を提供するものである。
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有し、エポキシ当量が160〜275g/eq.の範囲であり、且つICI粘度計で測定した150℃における溶融粘度が0.3〜5.0dPa・sの範囲にあることを特徴とする新規エポキシ樹脂を提供するものである。
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有するものである。
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有し、エポキシ当量が160〜275g/eq.の範囲であり、且つICI粘度計で測定した150℃における溶融粘度が0.3〜5.0dPa・sの範囲であるエポキシ樹脂である。
本発明の製造方法は、2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)と芳香族系架橋剤(a3)とを反応させて得られる多価ヒドロキシ化合物(a)とエピハロヒドリン類とを反応させてエポキシ樹脂を得ることを特徴とする。
で表わされる構造単位と、下記一般式(6)
で表される構造単位を有する多価ヒドロキシ化合物等が挙げられるがこれらに限定されるものではない。これらは単独で用いてもよく、2種以上併用してもよい。
で表されるような構造を有するフェノールアラルキル樹脂、ナフトールアラルキル樹脂、ビフェニル変性フェノール樹脂、ビフェニル変性ナフトール樹脂等の高芳香族性、高水酸基当量性の多価ヒドロキシ化合物や窒素原子を含有するアミノトリアジン変性フェノール樹脂等の化合物、及び1分子中に下記一般式(5)
で表わされる構造単位と、下記一般式(6)
で表される構造単位を有する多価ヒドロキシ化合物等が難燃性や成形性に特に優れる硬化物が得られる点から好ましい。
1)150℃における溶融粘度:ASTM D4287に準拠
2)軟化点測定法:JIS K7234
3)GPC:
・装置:東ソー株式会社製 HLC−8220 GPC、カラム:東ソー株式会社製 TSK−GEL G2000HXL+G2000HXL+G3000HXL+G4000HXL
・溶媒:テトラヒドロフラン
・流速:1ml/min
・検出器:RI
4)NMR:日本電子株式会社製 NMR GSX270
5)MS :日本電子株式会社製 二重収束型質量分析装置 AX505H(FD505H)
温度計、冷却管、分留管、窒素ガス導入管、撹拌器を取り付けたフラスコに、レゾルシノール183.9g(1.67モル)と2−メトキシナフタレン131.3g(0.83モル)とパラキシレンジメトキサイド166.2g(1.00モル)を仕込み、パラトルエンスルホン酸7.2g(0.074モル)を加えて、150℃まで昇温した後に、副生するメタノールを分留管で捕集しながら2時間反応させた。反応終了後、更にメチルイソブチルケトン1500gを加え、分液ロートに移し水洗した。次いで洗浄水が中性を示すまで水洗後、有機層から未反応のレゾルシノールと2−メトキシナフタレン、及びメチルイソブチルケトンを加熱減圧下に除去し、多価ヒドロキシ化合物(a−1)を得た。これの軟化点は106℃(B&R法)、溶融粘度(測定法:ICI粘度計法、測定温度:150℃)は28dPa・s、水酸基当量は130g/eq.であった。
実施例1において、レゾルシノールを294.0g(2.67モル)、2−メトキシナフタレンを210.4g(1.33モル)に変更した以外は、実施例1と同様にして多価ヒドロキシ化合物(a−2)を得た。これの軟化点は90℃(B&R法)、溶融粘度(測定法:ICI粘度計法、測定温度:150℃)は5.0dPa・s、水酸基当量は120g/eq.であった。
特開平8−301980号公報の実施例1及び実施例7に準拠し、下記構造式
特開平8−301980号公報の実施例4及び実施例10に準拠し、下記構造式
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、三井化学株式会社製ミレックスXLC−4L 200g(水酸基1当量)、エピクロルヒドリン463g(5.0モル)、n−ブタノール139g、テトラエチルベンジルアンモニウムクロライド2gを仕込み溶解させた。65℃に昇温した後、共沸する圧力まで減圧して、49%水酸化ナトリウム水溶液90g(1.1モル)を5時間かけて滴下した。その後、同条件で0.5時間撹拌を続けた。この間、共沸によって留出してきた留出分をディーンスタークトラップで分離し、水層を除去し、油層を反応系内に戻しながら、反応を行った。その後、未反応のエピクロルヒドリンを減圧蒸留によって留去させた。それで得られた粗エポキシ樹脂にメチルイソブチルケトン590gとn−ブタノール177gとを加え溶解した。更にこの溶液に10%水酸化ナトリウム水溶液10gを添加して80℃で2時間反応させた後に洗浄液のPHが中性となるまで水150gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去し、下記構造式
エポキシ樹脂として上記A−1とA−2、比較用エポキシ樹脂としてA’−1とA’−3及び日本化薬製NC−3000(ビフェニルアラルキル型エポキシ樹脂、エポキシ当量:274g/eq)を用い、硬化剤として、上記で得られた多価ヒドロキシ化合物a−1、明和化成製MEH−7851SS(ビフェニルノボラック樹脂、水酸基当量:200g/eq)及び三井化学製XLC−LL(ザイロック樹脂、水酸基当量:176g/eq)を、硬化促進剤としてトリフェニルホスフィン(TPP)、難燃剤として縮合燐酸エステル(大八化学工業株式会社製PX−200)、水酸化マグネシウム(エア・ウォーター株式会社製エコーマグZ−10)、無機充填材として球状シリカ(株式会社マイクロン製S−COL)、シランカップリング剤としてγ−グリシドキシトリエトキシキシシラン(信越化学工業株式会社製KBM−403)、カルナバワックス(株式会社セラリカ野田製PEARL WAX No.1−P)、カーボンブラックを用いて表1〜2に示した組成で配合し、2本ロールを用いて85℃の温度で5分間溶融混練して本発明のエポキシ樹脂組成物を得た。硬化物の物性は、上記組成物を用いて、評価用サンプルを下記の方法で作成し、難燃性、成形性を下記の方法で測定した。
幅12.7mm、長さ127mm、厚み1.6mmの評価用サンプルを、トランスファー成形機を用い175℃の温度で90秒成形した後、175℃の温度で5時間後硬化して作成した。作成した試験片を用いUL−94試験法に準拠し、厚さ1.6mmの試験片5本を用いて、燃焼試験を行った。
2本ロールを用い作成した組成物を、トランスファー成形機を用い175℃の温度で90秒間、φ90mm、厚さ2.0mmの金型に充填し、90秒成形し、金型をあけた後、硬化物の表面硬度をショア硬度D計にて硬度を計測した。
*1:1回の接炎における最大燃焼時間(秒)
*2:試験片5本の合計燃焼時間(秒)
Claims (28)
- 1分子中に下記一般式(1)
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有するエポキシ樹脂(A)と硬化剤(B)とを含有することを特徴とするエポキシ樹脂組成物。 - エポキシ樹脂(A)が2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)と芳香族系架橋剤(a3)とを反応させて得られる多価ヒドロキシ化合物(a)と、エピハロヒドリン類とを反応させて得られるエポキシ樹脂である請求項1記載のエポキシ樹脂組成物。
- エポキシ樹脂(A)のエポキシ当量が160〜275g/eq.の範囲である請求項3記載のエポキシ樹脂組成物。
- エポキシ樹脂のICI粘度計で測定した150℃における溶融粘度が0.3〜5.0dPa・sの範囲である請求項3記載のエポキシ樹脂組成物。
- 前記一般式(1)中のX1が置換基を有していてもよいベンゼン環又はナフタレン環である請求項1記載のエポキシ樹脂組成物。
- 前記一般式(2)におけるR3がメチル基であり、mが1又は2であり、X2が置換基を有していてもよいベンゼン環又はナフタレン環である請求項1記載のエポキシ樹脂組成物。
- 硬化剤(B)が、水酸基を有さない芳香環を含む連結基によって水酸基を有する芳香環が連結された構造を含有する多価芳香族化合物である請求項1〜7の何れか1項記載のエポキシ樹脂組成物。
- 硬化剤(B)が、1分子中に下記一般式(5)
で表わされる構造単位と、下記一般式(6)
で表される構造単位を有する多価ヒドロキシ化合物である請求項1〜7の何れか1項記載のエポキシ樹脂組成物。 - 更に非ハロゲン系難燃剤(C)を含有する請求項8又は9記載のエポキシ樹脂組成物。
- 非ハロゲン系難燃剤(C)がリン系難燃剤、窒素系難燃剤、シリコーン系難燃剤、無機系難燃剤、有機金属塩系難燃剤からなる群から選ばれる1種以上の難燃剤である請求項10記載のエポキシ樹脂組成物。
- 半導体封止材用である請求項10又は11記載のエポキシ樹脂組成物。
- プリント回路基板用である請求項10又は11記載のエポキシ樹脂組成物。
- レジストインキ用である請求項10又は11記載のエポキシ樹脂組成物。
- 導電ペースト用である請求項10又は11記載のエポキシ樹脂組成物。
- 層間絶縁材料用である請求項10又は11記載のエポキシ樹脂組成物。
- 請求項1〜16の何れかに記載のエポキシ樹脂組成物を硬化させて得られることを特徴とする硬化物。
- 半導体装置である請求項17記載の硬化物。
- 1分子中に下記一般式(1)
で表わされる構造単位と、下記一般式(2)
で表される構造単位を有し、エポキシ当量が160〜275g/eq.の範囲であり、且つICI粘度計で測定した150℃における溶融粘度が0.3〜5.0dPa・sの範囲にあることを特徴とする新規エポキシ樹脂。 - 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)と芳香族系架橋剤(a3)とを反応させて得られる多価ヒドロキシ化合物(a)と、エピハロヒドリン類とを反応させてエポキシ樹脂を得ることを特徴とするエポキシ樹脂の製造方法。
- 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)が下記一般式(7)で表される化合物であり、アルコキシ基含有芳香族系化合物(a2)が下記一般式(8)で表される化合物であり、且つ、芳香族系架橋剤(a3)が架橋反応した後に下記一般式(9)で表される構造になる化合物である請求項20記載の製造方法。
- 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)とのモル比(a1)/(a2)が30/70〜98/2であり、且つ、2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)との合計モル数と芳香族系架橋剤(a3)のモル数との比{(a1)+(a2)}/(a3)が51/49〜97/3である請求項20記載の製造方法。
- 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)と芳香族系架橋剤(a3)とを反応させる際に酸触媒を使用する請求項20記載の製造方法。
- 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)が置換基を有していてもよいフェノール類及び/又はナフトール類である請求項20記載の製造方法。
- アルコキシ基含有芳香族系化合物(a2)が置換基を有していてもよいメトキシベンゼン類、ジメトキシベンゼン類、メトキシナフタレン類、及びジメトキシナフタレン類からなる群から選ばれる1種以上の化合物である請求項20記載の製造方法。
- 2〜4個のヒドロキシ基を有する芳香族系化合物(a1)とアルコキシ基含有芳香族系化合物(a2)と芳香族系架橋剤(a3)を実質的に同時に仕込んで反応を行い、その後にエピハロヒドリン類と反応させる請求項20〜26の何れか1項記載の製造方法。
- アルコキシ基含有芳香族系化合物(a2)1モルに対して2〜30モルの芳香族系架橋剤(a3)を反応させた後に、2〜4個のヒドロキシ基を有する芳香族系化合物(a1)を反応させ、その後にエピハロヒドリン類と反応させる請求項20〜26の何れか1項記載の製造方法。
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