JP6952684B2 - 硬化樹脂用組成物及びその硬化物 - Google Patents
硬化樹脂用組成物及びその硬化物 Download PDFInfo
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Description
(A1);下記式(1−1)のビスフェノールF―アニリン型(F−a型)ベンゾオキサジン化合物(四国化成株式会社製)
(B1);化合物(5−1)
上記式(6)に示す化合物(a)を、『土田詔一ら、「ブタジエンとシクロペンタジエンとのDiels−Alder反応−三量体の決定−」、石油学会誌、1972年、第15巻、3号、p189−192』に記載の方法に準拠して合成した。反応容器に15.9Lのクロロホルムと1.6kgの化合物(a)を投入し、0℃で撹拌しながら4.5kgのメタクロロ過安息香酸を滴下した。得られた混合物を室温まで昇温し、上記式(6)の反応を12時間行った。ろ過により副生したメタクロロ安息香酸を除去し、ろ液を1N水酸化ナトリウム水溶液で3回洗浄し、更に飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥し、ろ過により硫酸マグネシウムを除去し、ろ液を濃縮して粗体を得た。粗体に2kgのトルエンを加え室温で溶解した。これに6kgのヘプタンを滴下して晶析し、5℃で1時間熟成した。晶析物をろ取してヘキサンにより洗浄し、35℃で24時間減圧乾燥して、1.4kgの下記化合物(5−1)を白色固体として得た。
上記式(7)に示す化合物(b)を、化合物(a)と同様に上記文献に記載の方法に準拠して合成した。反応容器に59.2kgのクロロホルムと4.0kgの化合物(b)を投入し、−10℃で撹拌しながら10.6kgのメタクロロ過安息香酸を滴下した。得られた混合物を室温まで昇温し、上記式(7)の反応を12時間行った。ろ過により副生したメタクロロ安息香酸を除去し、ろ液を42.0kgの5%亜硫酸ナトリウム水溶液で洗浄した。有機層を41.6kgの1N水酸化ナトリウム水溶液で4回洗浄し、更に48.0kgの飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥し、ろ過により硫酸マグネシウムを除去し、ろ液を濃縮して5.1kgの粗体を得た。粗体に3.5kgのトルエンを加え室温で溶解した。これに13.7kgのヘプタンを滴下して晶析し、5℃で1時間熟成した。晶析物をろ取してヘプタンにより洗浄し、35℃で12時間減圧乾燥して、2.8kgの下記化合物(5−2)を白色固体として得た。
上記式(8)に示す化合物(c)を、化合物(a)と同様に上記文献に記載の方法に準拠して合成した。反応容器に600gのクロロホルムと40.0gの化合物(c)を投入し、−10℃で撹拌しながら100gのメタクロロ過安息香酸を滴下した。得られた混合物を室温まで昇温し、上記式(8)の反応を12時間行った。ろ過により副生したメタクロロ安息香酸を除去し、ろ液を400gの5%亜硫酸ナトリウム水溶液で洗浄した。有機層を400gの1N水酸化ナトリウム水溶液で4回洗浄し、更に400gの飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥し、ろ過により硫酸マグネシウムを除去し、ろ液を濃縮して46.2gの粗体を得た。粗体に30gのトルエンを加え室温で溶解した。これに130gのヘプタンを滴下して晶析し、5℃で1時間熟成した。晶析物をろ取してヘプタンにより洗浄し、35℃で12時間減圧乾燥して、30.2gの下記化合物(5−3)を白色固体として得た。
反応容器に10kgのジシクロペンタジエン、68kgの重曹、100Lのアセトン、及び130Lのイオン交換水を仕込み、10℃以下に冷却した。反応液の温度を30℃以下に維持するよう冷却を制御して、84kgのオキソンを徐々に添加し、撹拌しながら10時間反応を行った。100Lの酢酸エチルを用いた抽出を2回行い、得られた有機層を分取して合わせた。続いて、当該有機層を100Lの混合水溶液(20重量%の食塩と20重量%のチオ硫酸ナトリウムとを含有)にて洗浄し、更に100Lのイオン交換水で2回洗浄した。洗浄後の有機層を硫酸マグネシウムにて乾燥し、ろ過により硫酸マグネシウムを除去し、ろ液から有機溶媒を留去して、11kgの下記化合物(5−4)を白色固体として得た。
(B’);下記式(9)のセロキサイド(登録商標)2021P(ダイセル化学工業株式会社製)
(C1);下記式(10)のビス(4−ヒドロキシフェニル)スルフィド(TDP;東京化成株式会社製)
硬化樹脂用組成物を厚み3mmの型に注入し、加熱して硬化させた。得られた硬化物について以下の性能を測定した。硬化物調製条件については後述する。
ガラス転移温度Tgは、X−DSC−7000(日立ハイテクサイエンス社製)を使用し、N2流量20mL/分、昇温速度20℃/分の条件での示差走査熱量測定DSCにより求めた。
JIS K 7171に準拠し、硬化物の70mm×25mm×3mmの短冊状試験片を作製し、以下の条件で3点曲げ試験を行い、曲げ強度、曲げ弾性率、及び曲げひずみを測定した。
試験装置;5582万能材料試験機(インストロン社製)
試験速度;1.5mm/分
支点間距離;48mm
試験片の前処理;なし
試験温度;23℃
試験温度を120℃とした以外は曲げ試験1と同様にして測定した。
硬化物の試験片を90℃熱水中に72時間浸漬する前処理を行った後、曲げ試験1と同様にして測定した。
上記成分(A1)、(B1)、及び(C1)を表1に示す質量比でプラネタリーミキサーに投入し、50℃、真空下で1時間混練して、組成物1を調製した。なお、本実施例において「真空下」とは、真空ポンプにより減圧し、減圧度を−0.8MPa(ゲージ圧)以下とした雰囲気であることを意味する。
各成分の種類及び質量比、並びに硬化条件を表1及び2に示した通りとした以外は実施例1と同様に、実施例2〜7、10、参考例8、9、及び比較例1〜5の組成物及び硬化物をそれぞれ調製し、性能を評価した。結果を表1及び2に示す。また、実施例6のDSC測定結果、及びDSC測定により求めたTgを図1に示す。
Claims (5)
- (A)少なくとも2つのベンゾオキサジン環を有する多官能ベンゾオキサジン化合物と、(B)少なくとも1つのノルボルナン構造及び少なくとも2つのエポキシ基を有する多官能エポキシ化合物とを含有し、
前記多官能ベンゾオキサジン化合物(A)は第1のベンゾオキサジン化合物又は第2のベンゾオキサジン化合物であり、
前記第1のベンゾオキサジン化合物は下記式(1):
前記第2のベンゾオキサジン化合物は下記式(2):
前記多官能エポキシ化合物(B)が下記式に示す化合物:
硬化樹脂用組成物。 - 前記多官能エポキシ化合物(B)が固体エポキシ化合物である、
請求項1又は2に記載の硬化樹脂用組成物。 - 更に(C)イミダゾール類、芳香族アミン類、及び多官能フェノール類より選択される少なくとも1種の硬化剤を含有し、
100質量部の前記多官能ベンゾオキサジン化合物(A)に対する前記硬化剤(C)の含有割合が0質量部超40質量部以下である、
請求項1〜3のいずれかに記載の硬化樹脂用組成物。 - 請求項1〜4のいずれかに記載の硬化樹脂用組成物を硬化させた硬化物。
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JP2016091115 | 2016-04-28 | ||
JP2016091115 | 2016-04-28 | ||
JP2016188911 | 2016-09-27 | ||
JP2016188911 | 2016-09-27 | ||
PCT/JP2017/017066 WO2017188448A1 (ja) | 2016-04-28 | 2017-04-28 | 硬化樹脂用組成物及びその硬化物 |
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EP (1) | EP3450499B1 (ja) |
JP (1) | JP6952684B2 (ja) |
KR (1) | KR102324393B1 (ja) |
CN (1) | CN109071918B (ja) |
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JP6946088B2 (ja) * | 2017-07-14 | 2021-10-06 | Eneos株式会社 | 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置 |
PT3702390T (pt) | 2017-10-27 | 2024-02-05 | Eneos Corp | Composição para resina curada, produto curado da referida composição, método de produção para a referida composição e o referido produto curado, e dispositivo semicondutor |
TWI794314B (zh) * | 2017-10-27 | 2023-03-01 | 日商Jxtg能源股份有限公司 | 硬化樹脂用組合物、該組合物之硬化物、該組合物及該硬化物之製造方法、與半導體裝置 |
TWI802608B (zh) * | 2017-10-27 | 2023-05-21 | 日商Jxtg能源股份有限公司 | 硬化樹脂用組合物、該組合物之硬化物、該組合物及該硬化物之製造方法、與半導體裝置 |
WO2019186269A1 (en) * | 2018-03-30 | 2019-10-03 | Toray Industries, Inc. | Benzoxazine resin composition, prepreg, and fiber-reinforced composite material |
US10487077B1 (en) | 2018-06-14 | 2019-11-26 | Sabic Global Technologies B.V. | Bis(benzoxazinyl)phthalimidine and associated curable composition and composite |
KR20210036912A (ko) * | 2018-08-03 | 2021-04-05 | 에네오스 가부시키가이샤 | 경화 수지용 조성물, 상기 조성물의 경화물, 상기 조성물 및 상기 경화물의 제조방법, 및 반도체 장치 |
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EP3450499A1 (en) | 2019-03-06 |
KR102324393B1 (ko) | 2021-11-10 |
TWI762483B (zh) | 2022-05-01 |
WO2017188448A1 (ja) | 2017-11-02 |
CN109071918B (zh) | 2022-04-15 |
TW201803859A (zh) | 2018-02-01 |
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