JP2019172884A - 硬化性組成物及びその硬化物 - Google Patents
硬化性組成物及びその硬化物 Download PDFInfo
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- JP2019172884A JP2019172884A JP2018064716A JP2018064716A JP2019172884A JP 2019172884 A JP2019172884 A JP 2019172884A JP 2018064716 A JP2018064716 A JP 2018064716A JP 2018064716 A JP2018064716 A JP 2018064716A JP 2019172884 A JP2019172884 A JP 2019172884A
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- Prior art keywords
- group
- aromatic
- compound
- unsaturated bond
- polymerizable unsaturated
- Prior art date
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- Granted
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- -1 aromatic ester compound Chemical class 0.000 claims abstract description 200
- 229920000642 polymer Polymers 0.000 claims abstract description 33
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- 239000004065 semiconductor Substances 0.000 claims abstract description 8
- 239000003566 sealing material Substances 0.000 claims abstract description 6
- 150000001491 aromatic compounds Chemical class 0.000 claims description 136
- 125000003118 aryl group Chemical group 0.000 claims description 125
- 125000001424 substituent group Chemical group 0.000 claims description 85
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- 239000007795 chemical reaction product Substances 0.000 claims description 5
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- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
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- 239000005060 rubber Substances 0.000 description 1
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Abstract
Description
で表される重合性不飽和結合含有芳香族エステル化合物(A−1)や、2以上のフェノール性水酸基を有する第1の芳香族化合物と、フェノール性水酸基を有する第2の芳香族化合物と、2以上のカルボキシ基を有する第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物との反応生成物であり、前記第1の芳香族化合物、前記第2の芳香族化合物、並びに前記第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物の少なくとも1つが重合性不飽和結合含有置換基を有するものである重合性不飽和結合含有芳香族エステル化合物(A−2)等が挙げられる。
前記ポリカルボン酸化合物またはその誘導体は、置換または非置換の芳香族環基を有し、好ましくは炭素原子数が3〜30の範囲である。この際、「ポリカルボン酸化合物の誘導体」として、カルボン酸の酸ハロゲン化物等が挙げられる。
フェノール化合物は、置換または非置換の芳香族環基を有し、好ましくは炭素原子数3〜30の範囲である。この際、第2の芳香族環基および第2の芳香族環基の置換基は上述したものと同様である。
第1の芳香族化合物は、2以上のフェノール性水酸基を有する。2以上のフェノール性水酸基を有することにより、後述する第3の芳香族化合物等と反応することで重合性不飽和結合含有芳香族エステル化合物(A−2)中において、ポリエステル構造を形成しうる。
測定装置:東ソー株式会社製「HLC−8320 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 G4000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
検出器:RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC−WorkStation」
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−8320 GPC」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)。
第2の芳香族化合物は、フェノール性水酸基を有する。第2の芳香族化合物はフェノール性水酸基を1つ有することから、上述の第1の芳香族化合物および後述の第3の芳香族化合物等のポリエステル化の反応を停止させる機能を有する。
第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物は、2以上のカルボキシ基を有するカルボン酸、またはその誘導体、具体的には酸ハロゲン化物、エステル化物である(本明細書において、第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物を併せて「第3の芳香族化合物等」と称することがある)。第3の芳香族化合物等は、2以上のカルボキシ基等を有することにより、上述の第1の芳香族化合物と反応することで重合性不飽和結合含有芳香族エステル化合物(A−2)において、ポリエステル構造を形成しうる。なお、上述の第2の芳香族化合物と反応することで、ポリエステル化反応は停止する。
上述の第1の芳香族化合物、第2の芳香族化合物、並びに第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物(第3の芳香族化合物等)の少なくとも1つは重合性不飽和結合含有置換基を有する。すなわち、第1の芳香族化合物、第2の芳香族化合物、第3の芳香族化合物等すべてが重合性不飽和結合含有置換基を有していてもよいし、第1の芳香族化合物および第2の芳香族化合物が重合性不飽和結合含有置換基を有していてもよいし、第2の芳香族化合物のみが重合性不飽和結合含有置換基を有していてもよい。また、2種以上の第1の芳香族化合物、第2の芳香族化合物、第3の芳香族化合物等を用いる場合には、その一部のみが重合性不飽和結合含有置換基を有していてもよい。重合性不飽和結合含有置換基の炭素原子数は2〜30の範囲であることが好ましい。
重合性不飽和結合含有芳香族エステル化合物(A−2)の製造方法は特に制限されず、適宜公知の方法により製造することができる。
第1の芳香族化合物、第2の芳香族化合物、および第3の芳香族化合物等としては、上述したものが用いられる。
本発明の硬化性組成物は、前記重合性不飽和結合含有芳香族エステル化合物(A)が重合性不飽和結合を含有することから、前記芳香族エステル化合物(A)及び前記ジエン系ポリマー(B)のみでも硬化性を有する。他方で、前記芳香族エステル化合物(A)はエポキシ樹脂の硬化剤としても機能し、より高耐熱の硬化物を与え得ることから、本発明の硬化性組成物は更にエポキシ樹脂を含有することが好ましい。
本発明の硬化性組成物が前記エポキシ樹脂を含有する場合、前記芳香族エステル化合物(A)の他、エポキシ樹脂と硬化し得る他の硬化剤を併用してもよい。
他の樹脂の具体例としては、特に制限されないが、マレイミド樹脂、ビスマレイミド樹脂、ポリイミド樹脂、シアネートエステル樹脂、ベンゾオキサジン樹脂、トリアジン含有クレゾールノボラック樹脂、シアン酸エステル樹脂、スチレン−無水マレイン酸樹脂、ジアリルビスフェノールやトリアリルイソシアヌレート等のアリル基含有樹脂、ポリリン酸エステル、リン酸エステル−カーボネート共重合体、ポリフェニレンエーテル樹脂等が挙げられる。これらの他の樹脂は単独で用いても、2種以上を組み合わせて用いてもよい。
一実施形態において、組成物は溶媒を含んでいてもよい。前記溶媒は、組成物の粘度を調整する機能等を有する。
一実施形態において、組成物は添加剤を含んでいてもよい。当該添加剤としては、硬化促進剤、難燃剤、充填剤等が挙げられる。
硬化促進剤としては、特に制限されないが、リン系硬化促進剤、アミン系硬化促進剤、イミダゾール系硬化促進剤、グアニジン系硬化促進剤、尿素系硬化促進剤、過酸化物、アゾ化合物等が挙げられる。
難燃剤としては、特に制限されないが、無機リン系難燃剤、有機リン系難燃剤、ハロゲン系難燃剤等が挙げられる。
充填剤としては、有機充填剤、無機充填剤が挙げられる。充填剤は、伸びを向上させる機能、機械的強度を向上させる機能等を有する。
本発明の一実施形態によれば、上述の重合性不飽和結合含有芳香族エステル化合物(A)とポリアリーレンエーテル樹脂(B)とを含有する硬化性組成物を硬化してなる硬化物が提供される。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、オルソアリルフェノール268gとトルエン1200gを仕込み、系内を減圧窒素置換しながら内容物を溶解させた。次いで、イソフタル酸クロライド203gを仕込み、系内を減圧窒素置換しながら内容物を溶解させた。テトラブチルアンモニウムブロマイド0.6gを加えて溶解させ、窒素ガスパージを施しながら、系内を60℃以下に制御して、20%水酸化ナトリウム水溶液412gを3時間かけて滴下した。滴下終了後、同温度条件下で1時間撹拌を続けた。反応混合物を静置して分液させ、水層を取り除いた。得られた有機相に水を加えて約15分間撹拌し、静置して分液させ、水層を取り除いた。水層のpHが7になるまでこの水洗操作を繰り返した。水洗後の有機相を加熱減圧条件下で乾燥させ、下記構造式で示される重合性不飽和結合含有芳香族エステル化合物(A−1−1)370gを得た。重合性不飽和結合含有芳香族エステル化合物(A−1−1)のエステル基当量は199g/当量、アリル基当量は199g/当量、E型粘度(25℃)は6000mPa.sであった。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、ジシクロペンタジエンとフェノールとの重付加反応樹脂(水酸基当量165g/当量、軟化点85℃)165g、オルソアリルフェノール134g、及びトルエン1200gを仕込み、系内を減圧窒素置換しながら内容物を溶解させた。次いで、イソフタル酸クロライド203gを仕込み、系内を減圧窒素置換しながら溶解させた。テトラブチルアンモニウムブロマイド0.6gを加えて溶解させ、窒素ガスパージを施しながら、系内を60℃以下に制御して、20%水酸化ナトリウム水溶液412gを3時間かけて滴下した。滴下終了後、同温度条件下で1時間撹拌を続けた。反応混合物を静置して分液させ、水層を取り除いた。得られた有機相に水を加えて約15分間撹拌し、静置して分液させ、水層を取り除いた。水層のpHが7になるまでこの水洗操作を繰り返した。水洗後の有機相を加熱減圧条件下乾燥させ、重合性不飽和結合含有芳香族エステル化合物(A−2−1)385gを得た。重合性不飽和結合含有芳香族エステル化合物(A−2−1)の理論構造を下記に示す。重合性不飽和結合含有芳香族エステル化合物(A−2−1)のエステル基当量は214g/当量、アリル基当量は428g/当量、軟化点は82℃であった。
製造例2のジシクロペンタジエンとフェノールとの重付加反応樹脂165gをジアリルビスフェノールA160gに変更した以外は、製造例2と同様にして重合性不飽和結合含有芳香族エステル化合物(A−2−2)402gを得た。重合性不飽和結合含有芳香族エステル化合物(A−2−2)の理論構造を下記に示す。重合性不飽和結合含有芳香族エステル化合物(A−2−2)のエステル基当量は212g/当量、アリル基当量は212g/当量、軟化点は51℃であった。
下記表1〜3に示す割合で各成分を配合し、硬化性組成物を得た。得られた硬化性組成物について、下記要領で硬化物の耐熱性評価と誘電正接値の測定を行った。結果を表1〜3に示す。
・ジエン系ポリマー(B−1):日本曹達株式会社製「B−3000」、1,2−ポリブタジエンホモポリマー、数平均分子量(Mn)3,200、理論繰り返し構造は以下の通り。
硬化性組成物を11cm×9cm×2.4mmの型枠に流し込み、プレス機を用いて150℃で60分間、次いで175℃で90分間、更に200℃で90分間成形した。型枠から成形物を取り出し、230℃で4時間更に硬化させて硬化物を得た。
先で得た厚さ2.4mmの硬化物から幅5mm、長さ54mmの試験片を切り出した。レオメトリック社製「固体粘弾性測定装置RSAII」を用い、レクタンギュラーテンション法によるDMA(動的粘弾性)測定により、試験片の弾性率変化が最大となる(tanδ変化率が最も大きい)温度をガラス転移温度として測定した。測定条件は周波数1Hz、昇温速度が3℃/分とした。
先で得た硬化物を105℃で2時間加熱真空乾燥させた後、温度23℃、湿度50%の室内に24時間保管したものを試験片とした。アジレント・テクノロジー株式会社製「ネットワークアナライザE8362C」を用い、空洞共振法により試験片の1GHzでの誘電正接を測定した。
Claims (8)
- 重合性不飽和結合含有芳香族エステル化合物(A)と、ジエン系ポリマー(B)とを含有する硬化性組成物。
- 前記重合性不飽和結合含有芳香族エステル化合物(A)が、
2以上のフェノール性水酸基を有する第1の芳香族化合物と、
フェノール性水酸基を有する第2の芳香族化合物と、
2以上のカルボキシ基を有する第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物と、
の反応生成物であり、
前記第1の芳香族化合物、前記第2の芳香族化合物、並びに前記第3の芳香族化合物および/またはその酸ハロゲン化物、エステル化物の少なくとも1つが重合性不飽和結合含有置換基を有する、請求項1記載の硬化性組成物。 - 更に、エポキシ樹脂を含有する請求項1〜3の何れか一つに記載の硬化性組成物。
- 請求項1〜4の何れか一つに記載の硬化性組成物の硬化物。
- 請求項1〜4の何れか一つに記載の硬化性組成物を用いてなるプリント配線基板。
- 請求項1〜4の何れか一つに記載の硬化性組成物を用いてなる半導体封止材料。
- 請求項1〜4の何れか一つに記載の硬化性組成物を用いてなるビルドアップフィルム。
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