JP4735410B2 - 硬化剤の製造法,及びこれを用いた熱硬化性樹脂組成物 - Google Patents
硬化剤の製造法,及びこれを用いた熱硬化性樹脂組成物 Download PDFInfo
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- JP4735410B2 JP4735410B2 JP2006135035A JP2006135035A JP4735410B2 JP 4735410 B2 JP4735410 B2 JP 4735410B2 JP 2006135035 A JP2006135035 A JP 2006135035A JP 2006135035 A JP2006135035 A JP 2006135035A JP 4735410 B2 JP4735410 B2 JP 4735410B2
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Description
1.酸性置換基と不飽和マレイミド基を有する硬化剤の製造法であって、(a)1分子中に少なくとも2個のベンゼン環に結合した1級アミノ基を有する化合物と、(b)無水マレイン酸と、を(c)有機溶剤中で反応させ、マレイミド樹脂を製造する工程、前記マレイミド樹脂と(d)下記一般式(I)に示す酸性置換基を有するアミン化合物を反応させる工程、を含む硬化剤の製造法。
本発明は、酸性置換基と不飽和マレイミド基を有する硬化剤の製造法であって、(a)1分子中に少なくとも2個のベンゼン環に結合した1級アミノ基を有する化合物と、(b)無水マレイン酸と、を(c)有機溶剤中で反応させ、マレイミド樹脂を製造する工程、前記マレイミド樹脂と(d)下記一般式(I)に示す酸性置換基を有するアミン化合物を反応させる工程、を含む硬化剤の製造法である。
製造例1:酸性置換基と不飽和マレイミド基を有する硬化剤(1−1)の製造
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積1リットルの反応容器に、ジアミノジフェニルメタン:99.00gと無水マレイン酸:98.00g、及びシクロヘキサノン:417.67g、トルエン:41.77gを入れ、90℃に昇温して均一に溶解した。次いで還流温度まで昇温し、発生する縮合水を除去しながら5時間反応させた。次いでp−アミノフェノール:27.25gを添加し、120℃で5時間反応させて酸性置換基(フェノール性水酸基)と不飽和マレイミド基を有する硬化剤の溶液(1−1)を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積1リットルの反応容器に、ジアミノジフェニルメタン:99.00gと無水マレイン酸:98.00g、及びN,N−ジメチルホルムアミド:417.67g、トルエン:41.77gを入れ、90℃に昇温して均一に溶解した。次いで還流温度まで昇温し、発生する縮合水を除去しながら5時間反応させた。次いでp−アミノ安息香酸:34.25gを添加し、120℃で5時間反応させて酸性置換基(カルボキシル基)と不飽和マレイミド基を有する硬化剤の溶液(1−2)を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積1リットルの反応容器に、ジアミノジフェニルメタン:99.00gと無水マレイン酸:98.00g、及びシクロヘキサノン:197.00g、無水酢酸:112.20gを入れ、90℃に昇温して均一に溶解した。次いで、還流温度まで昇温し5時間反応させた後、減圧下で溶媒を除去した。次いで常圧に戻した後、プロピレングリコールモノメチルエーテル:112.20gとp−アミノフェノール:27.25gを添加し、120℃で5時間反応させて酸性置換基(フェノール性水酸基)と不飽和マレイミド基を有する硬化剤の溶液(1−3)を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、2,2−ビス(4−(4−アミノフェノキシ)フェニル)プロパン:205.00gと無水マレイン酸:98.00g、及びシクロヘキサノン:600.00g、トルエン:60.00gを入れ、90℃に昇温して均一に溶解した。次いで還流温度まで昇温し、発生する縮合水を除去しながら5時間反応させた。次いでm−アミノフェノール:27.25gを添加し、120℃で5時間反応させて酸性置換基(フェノール性水酸基)と不飽和マレイミド基を有する硬化剤の溶液(1−4)を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積1リットルの反応容器に、ジアミノジフェニルメタン:99.00gと無水マレイン酸:98.00g、及びシクロヘキサノン:417.67g、トルエン:41.77gを入れ、90℃に昇温して均一に溶解した。次いでp−トルエンスルホン酸:14.00gを添加してから還流温度まで昇温し、発生する縮合水を除去しながら5時間反応させた。次いでp−アミノフェノール:27.25gを添加し、120℃で15時間反応させたが、p−アミノフェノールの付加反応が進行せず、酸性置換基(フェノール性水酸基)と不飽和マレイミド基を有する硬化剤が得られなかった。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積1リットルの反応容器に、ジアミノジフェニルメタン:99.00gと無水マレイン酸:98.00g、及びN、N−ジメチルホルムアミド:417.67g、酢酸:60.00g、酢酸ナトリウム:82.00gを入れ、60℃に昇温して均一に溶解した。次いで還流温度まで昇温し5時間反応させた。次いでp−アミノフェノール:27.25gを添加し、120℃で15時間反応させたが、p−アミノフェノールの付加反応が進行せず、酸性置換基(フェノール性水酸基)と不飽和マレイミド基を有する硬化剤が得られなかった。
製造例1〜4で得られた成分(A)である酸性置換基と不飽和マレイミド基を有する硬化剤、成分(B)であるエポキシ樹脂、成分(C)であるアミン化合物、またエポキシ硬化剤としてフェノールノボラック樹脂、無機充填剤(難燃剤)として水酸化アルミニウム、溶剤にメチルエチルケトンを使用して表1と表2に示した配合割合(重量部)で混合して樹脂分70mass%の均一なワニスを得た。次に、上記ワニスをペットフィルム上に塗布し、160℃で5分加熱乾燥してキャスティング法によりBステージ化した後、粉砕し粉体とした。次に、このBステージ化した粉体を内容積200×100×1mmの金型内に充填し、油圧プレス装置で180℃−1時間−1.5MPaの条件で加熱加圧し、板状の成形品を得た。これを適宣切断し、特性試験に供した。また、18μmの電解銅箔を上下に配置し、同様に加熱加圧し銅張りの成形品を作製し、銅箔接着性(ピール強度)の評価試験に用いた。
(1)銅箔接着性(銅箔ピール強度)の評価
銅張りの成形品を銅エッチング液に浸漬することにより、1cm幅の銅箔を形成して試験片を作製し、レオメータを用いてピール強度を測定した。
(2)ガラス転移温度(Tg)の測定
5mm角の試験片を作製し、TMA試験装置(デュポン社製、TMA2940)を用い、試験片の熱膨張特性を観察することにより評価した。
(3)難燃性の評価
長さ127mm、幅12.7mmに切り出した試験片を作製し、UL94の試験法(V法)に準じて評価した。
(4)比誘電率及び誘電正接の測定
25mm角の試験片を作製し、Hewllet・Packerd社製比誘電率測定装置(製品名:HP4291B)を用いて、周波数1GHzでの比誘電率及び誘電正接を測定した。
Claims (2)
- (A)請求項1記載の硬化剤の製造法により製造された硬化剤、(B)1分子中に少なくとも2個のエポキシ基を有するエポキシ樹脂、(C)1分子中に少なくとも2個のアミノ基を有する化合物、を含有する熱硬化性樹脂組成物。
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JP5614048B2 (ja) * | 2010-02-02 | 2014-10-29 | 日立化成株式会社 | 熱硬化性絶縁樹脂組成物、並びにこれを用いたプリプレグ、積層板及び多層プリント配線板 |
KR102142753B1 (ko) * | 2009-03-27 | 2020-09-14 | 히타치가세이가부시끼가이샤 | 열경화성 수지 조성물, 및 이를 이용한 프리프레그, 지지체 부착 절연 필름, 적층판 및 인쇄 배선판 |
WO2011111471A1 (ja) * | 2010-03-11 | 2011-09-15 | ナミックス株式会社 | フィルム用組成物、ならびに、それによる接着フィルムおよびカバーレイフィルム |
JP2011105945A (ja) * | 2011-01-04 | 2011-06-02 | Hitachi Chem Co Ltd | 硬化剤の製造法,及びこれを用いた熱硬化性樹脂組成物 |
JP6379697B2 (ja) * | 2014-06-05 | 2018-08-29 | Dic株式会社 | 硬化性樹脂組成物、硬化物および硬化剤 |
JP6822610B2 (ja) | 2019-02-14 | 2021-01-27 | Dic株式会社 | 硬化性樹脂組成物、硬化物、酸変性マレイミド樹脂および硬化剤 |
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