JP6511772B2 - 熱硬化性組成物 - Google Patents
熱硬化性組成物 Download PDFInfo
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- JP6511772B2 JP6511772B2 JP2014220537A JP2014220537A JP6511772B2 JP 6511772 B2 JP6511772 B2 JP 6511772B2 JP 2014220537 A JP2014220537 A JP 2014220537A JP 2014220537 A JP2014220537 A JP 2014220537A JP 6511772 B2 JP6511772 B2 JP 6511772B2
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- parts
- curing
- methyl
- thermosetting composition
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 36
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000002723 alicyclic group Chemical group 0.000 claims description 15
- 150000008065 acid anhydrides Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 13
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- 238000001723 curing Methods 0.000 description 37
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- -1 hydrogen compound Chemical class 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
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- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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攪拌機、温度計を備えた反応容器に、水素化ナトリウム(純度は60%以上)28.6部、テトラヒドロフラン180部、シアヌル酸クロリド29.3部を仕込み、室温で攪拌した。3−シクロヘキセン−1−メタノール53.5部とテトラヒドロフラン120部を混合し、1時間かけてゆっくり滴下して加えた。加熱還流下で2時間反応させ1H−NMRで反応が完結しているのを確認した。4℃以下まで冷却し、水を加えて水素化ナトリウムを失活させた後、1N塩酸で中和した。トルエンで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジンを53.3部得た。収率89%。
攪拌機、温度計を備えた反応容器に、2,4,6−トリ(3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジン11.1部、炭酸水素ナトリウム33.6部、アセトン73部、水70部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)40部を4分割して1時間ごとに加えた。室温で一晩反応後、1H−NMRで反応が完結しているのを確認した。水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(3,4−エポキシシクロヘキサン−1−イルメトキシ)−1,3,5−トリアジンを9.4部得た。収率75%。
攪拌機、温度計を備えた反応容器に、水素化ナトリウム(純度は60%以上)27.0部、テトラヒドロフラン180部、シアヌル酸クロリド27.7部を仕込み、室温で攪拌した。5−ノルボルネン−1−メタノール56.0部とテトラヒドロフラン120部を混合し、1時間かけてゆっくり滴下して加えた。加熱還流下で2時間反応させ1H−NMRで反応が完結しているのを確認した。4℃以下まで冷却し、水を加えて水素化ナトリウムを失活させた後、1N塩酸で中和した。トルエンで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(5−ノルボルネン−1−イルメトキシ)−1,3,5−トリアジンを52.3部得た。収率85%。
攪拌機、温度計を備えた反応容器に、2,4,6−トリ(5−ノルボルネン−1−イルメトキシ)−1,3,5−トリアジン9.2部、炭酸水素ナトリウム25.4部、アセトン56部、水50部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)35部を4分割して1時間ごとに加えた。室温で一晩反応後、1H−NMRで反応が完結しているのを確認した。水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(5,6−エポキシノルボルナン−1−イルメトキシ)−1,3,5−トリアジンを8.2部得た。収率80%。
攪拌機、温度計を備えた反応容器に、水素化ナトリウム(純度は60%以上)2.5部、テトラヒドロフラン60部、シアヌル酸クロリド2.6部を仕込み、室温で攪拌した。(4−メチル−3−シクロヘキセン−1−イル)メタノール5.9部とテトラヒドロフラン40部を混合し、1時間かけてゆっくり滴下して加えた。加熱還流下で2時間反応させ1H−NMRで反応が完結しているのを確認した。4℃以下まで冷却し、水を加えて水素化ナトリウムを失活させた後、1N塩酸で中和した。トルエンで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(4−メチル−3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジンを4.1部得た。収率70%。
攪拌機、温度計を備えた反応容器に、2,4,6−トリ(4−メチル−3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジン3.7部、炭酸水素ナトリウム10.2部、アセトン22部、水20部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)14部を1時間かけて加えた。室温で一晩反応後、1H−NMRで反応が完結しているのを確認した。水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(4−メチル−3,4−エポキシシクロヘキサン−1−イルメトキシ)−1,3,5−トリアジンを3.3部得た。収率78%。
攪拌機、温度計を備えた反応容器に、水素化ナトリウム(純度は60%以上)2.5部、テトラヒドロフラン60部、シアヌル酸クロリド2.6部を仕込み、室温で攪拌した。2,4−ジメチル−3−シクロヘキセン−1−メタノール5.9部とテトラヒドロフラン40部を混合し、1時間かけてゆっくり滴下して加えた。加熱還流下で2時間反応させ1H−NMRで反応が完結しているのを確認した。4℃以下まで冷却し、水を加えて水素化ナトリウムを失活させた後、1N塩酸で中和した。トルエンで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(2,4−ジメチル−3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジンを5.3部得た。収率83%。
攪拌機、温度計を備えた反応容器に、2,4,6−トリ(2,4−ジメチル−3−シクロヘキセン−1−イルメトキシ)−1,3,5−トリアジン5.0部、炭酸水素ナトリウム12.4部、アセトン28部、水25部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)17部を1時間かけて加えた。室温で一晩反応後、1H−NMRで反応が完結しているのを確認した。水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥、溶媒を除去することで粗物を得た。粗物を少量の酢酸エチルに溶解させ、ヘキサンを加えて再沈殿させることで目的物である2,4,6−トリ(2,4−ジメチル−3,4−エポキシシクロヘキサン−1−イルメトキシ)−1,3,5−トリアジンを4.5部得た。収率80%。
CEL−2021P(3’,4’−エポキシシクロへキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート)・・・ダイセル化学製
jER−828(ビスフェノールA型エポキシ樹脂)・・・三菱化学製
MHHPA(メチルヘキサヒドロ無水フタル酸)・・・新日本理化製,リカシッドMH700
THPA(テトラヒドロ無水フタル酸)・・・新日本理化製,リカシッドTH
BDMA(N,N−ベンジルジメチルアミン)・・・和光純薬製
配合例1に示す樹脂組成物について、JIS−6901に準じて150℃におけるゲル化時間を測定した。さらに、150℃で2時間硬化させて作製した硬化物のガラス転移温度(Tg)と外観の色相を評価した。
セイコーインスツルメンツ社製DSC(示差走査熱量計、DSC6200R)により測定(昇温速度10℃毎分)し、2段階評価した。
○:Tgが180℃以上
×:Tgが180℃未満
○:熱硬化前から変化無し(無色透明)
△:熱硬化前に比べてやや黄色く着色
×:明らかな着色
Claims (3)
- 下記一般式(1)で表されるトリアジン環骨格を有する脂環式エポキシ化合物と、酸無水物系硬化剤とを含む熱硬化性組成物。
一般式(1)
(一般式(1)中、Xは、下記式1〜式4のいずれかの脂環式エポキシを表す。)
式1
式2
式3
式4
- さらに、一般式(1)以外のエポキシ化合物を含む、請求項1に記載の熱硬化性組成物。
- 請求項1または2記載の熱硬化性組成物を硬化して得られる硬化物。
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