JP2009132886A - 樹脂組成物並びにこれを用いたプリプレグ及び積層板 - Google Patents
樹脂組成物並びにこれを用いたプリプレグ及び積層板 Download PDFInfo
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- JP2009132886A JP2009132886A JP2008275153A JP2008275153A JP2009132886A JP 2009132886 A JP2009132886 A JP 2009132886A JP 2008275153 A JP2008275153 A JP 2008275153A JP 2008275153 A JP2008275153 A JP 2008275153A JP 2009132886 A JP2009132886 A JP 2009132886A
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Abstract
【解決手段】 特定構造のシアン酸エステル化合物および/またはそのオリゴマーからなるシアン酸エステル樹脂成分A、およびエポキシ樹脂およびマレイミド化合物からなる群から選ばれた少なくとも一種の成分Bとを含有する樹脂組成物、および成分Bとして少なくともエポキシ樹脂を含有する成分Bと成分Aとを含有する樹脂組成物を用いたプリプレグおよび積層板。
【選択図】 なし
Description
すなわち、本発明は、式(1)で示されるシアン酸エステル化合物および/またはそのオリゴマーからなるシアン酸エステル樹脂成分Aならびにエポキシ樹脂およびマレイミド化合物からなる群から選ばれた少なくとも一種の成分Bとを含有する樹脂組成物を提供する。
本発明はさらに上記式(1)で示されるシアン酸エステル化合物および/またはそのオリゴマーからなるシアン酸エステル樹脂成分A、およびエポキシ樹脂、またはエポキシ樹脂およびマレイミド化合物からなる成分Bとを含有する樹脂組成物を提供する。本発明はさらに無機充填材を含む上記樹脂組成物、エポキシ樹脂が非ハロゲン系エポキシ樹脂である上記樹脂組成物、上記樹脂組成物と基材とからなるプリプレグ、上記プリプレグを用いた積層板、および上記プリプレグから得られた金属箔張り積層板を提供する。
2.04 molの3,3−ビス(4−ヒドロキシフェニル)−1(3H)−イソベンゾフラノン(八代製薬製)及び4.49molのトリエチルアミンを塩化メチレン3250gに溶解させた(溶液1)。5.51molの塩化シアンを溶解した塩化メチレン溶液1462.45gに−10℃で溶液1を3時間かけて滴下した。30分撹拌した後、0.20molのトリエチルアミンを滴下し、さらに30分撹拌して反応を完結させた。得られた溶液を0.1N塩酸 3000mLにより洗浄した後、水1000mLによる洗浄を4回繰り返した。濃縮後、冷却し、黄白色結晶を得た。得られた結晶をn−ヘキサン2000mLにて洗浄した後、減圧乾燥することにより、白色結晶の3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノンを677g得た。このようにして得られたシアン酸エステル化合物は、赤外吸収スペクトル測定の結果、フェノール性OH基の吸収3200〜3600cm−1が消失し、シアン酸エステルのニトリルの吸収2264cm−1付近に吸収を有することが確認された。融点は130℃であった。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン 70重量部とビス(4−マレイミドフェニル)メタン(BMI−H、ケイ・アイ化成)30重量部とを160℃、10分間溶融混合したものを、注型用金型に流し込み、165℃で 15分間、真空脱泡した後、180℃で4時間、200℃で4時間、250℃で4時間加熱硬化させて、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表1に示す。
実施例1において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン 70重量部の代わりに、2,2―ビス(4−シアナートフェニル)プロパン(CX、三菱ガス化学製)70重量部を使用する以外は、実施例1と同様にして行い、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表1に示す。
実施例1において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン 70重量部の代わりに、フェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)70重量部を使用する以外は、実施例1と同様にして行い、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表1に示す。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノンを160℃、10分間溶融したものを、注型用金型に流し込み、165℃で 15分間、真空脱泡した後、180℃で4時間、200℃で4時間、250℃で4時間加熱硬化させて、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表1に示す。なお、シアン酸エステル樹脂の分子構造などによる反応阻害要因によって硬化が不十分であったためか、ガラス転移温度の測定が安定せず測定不能であった。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン50重量部とビス(4−マレイミドフェニル)メタン(BMI−H)50重量部とを160℃、10分間溶融混合したものを、注型用金型に流し込み、165℃で 15分間、真空脱泡した後、180℃で4時間、200℃で4時間、250℃で4時間加熱硬化させて、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表2に示す。
実施例2において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン 50重量部の代わりに、2,2―ビス(4−シアナートフェニル)プロパン(CX、三菱ガス化学製)50重量部を使用する以外は、実施例2と同様にして行い、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表2に示す。
実施例2において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン 50重量部の代わりに、フェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)50重量部を使用する以外は、実施例2と同様にして行い、厚み 3mm及び2mmの硬化物を得た。得られた硬化物の物性測定結果を表2に示す。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン45重量部とクレゾールノボラック型エポキシ樹脂(ESCN−220F, 住友化学工業製)55重量部ををメチルエチルケトンで溶解混合し、オクチル酸亜鉛 0.04重量部を混合してワニスを得た。このワニスをメチルエチルケトンで希釈し、厚さ 0.1mmのEガラスクロスに含浸塗工し、165℃で 6分間加熱乾燥して、樹脂含有量39重量%のプリプレグを得た。次に、このプリプレグを4枚重ね、厚さ18μmの電解銅箔を上下に配置し、圧力30kgf/cm2、温度220℃で120分間プレスを行い、厚さ 0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表3に示す。
実施例3において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン45重量部の代わりに、2,2−ビス(4−シアナートフェニル)プロパンのプレポリマー(BT2070、三菱ガス化学製)45重量部を使用する以外は、実施例3と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表3に示す。
実施例3において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン45重量部の代わりに、フェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)45重量部を使用する以外は、実施例3と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表3に示す。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン50重量部とビフェニルアラルキル型エポキシ樹脂(NC3000−H,日本化薬製)50重量部をメチルエチルケトンで溶解混合し、更に球状合成シリカ(SC−2050,アドマテックス製)100重量部、オクチル酸亜鉛 0.04重量部を混合してワニスを得た。このワニスをメチルエチルケトンで希釈し、厚さ 0.1mmのEガラスクロスに含浸塗工し、165℃で6分間加熱乾燥して、樹脂含有量45重量%のプリプレグを得た。次に、このプリプレグを4枚重ね、厚さ12μmの電解銅箔を上下に配置し、圧力30kgf/cm2、温度 220℃で120分間プレスを行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表4に示す。
実施例4において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン50重量部の代わりに、2,2−ビス(4−シアナートフェニル)プロパンのプレポリマー(BT2070,三菱ガス化学製)50重量部を使用する以外は、実施例4と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表4に示す。
実施例4において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン50重量部の代わりに、フェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)50重量部を使用する以外は、実施例4と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表4に示す。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン30重量部とビフェニルアラルキル型エポキシ樹脂(NC3000−H,日本化薬製)50重量部とビス(4−マレイミドフェニル)メタン(BMI−H、ケイ・アイ化成)20重量部をメチルエチルケトンで溶解混合し、更に球状合成シリカ(SC−2050,アドマテックス製)100重量部、オクチル酸亜鉛0.04重量部を混合してワニスを得た。このワニスをメチルエチルケトンで希釈し、厚さ 0.1mmのEガラスクロスに含浸塗工し、165℃で 14分間加熱乾燥してプリプレグを得た。次に、このプリプレグを4枚重ね、厚さ12μmの電解銅箔を上下に配置し、圧力30kgf/cm2、温度220℃で120分間プレスを行い、厚さ 0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表5に示す。
実施例5において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン30重量部の代わりに、2,2−ビス(4−シアナートフェニル)プロパンのプレポリマー(BT2070、三菱ガス化学製)30重量部を使用する以外は、実施例5と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表5に示す。
実施例5において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン30重量部の代わりに、フェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)30重量部を使用する以外は、実施例5と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表5に示す。
合成例1で得た3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン15重量部とフェノールノボラック型シアン酸エステル樹脂(PrimasetPT−30,ロンザ社製)15重量部とビフェニルアラルキル型エポキシ樹脂(NC3000−H,日本化薬製)50重量部とビス(4−マレイミドフェニル)メタン(BMI−H、ケイ・アイ化成)20重量部をメチルエチルケトンで溶解混合し、更に球状合成シリカ(SC−2050,アドマテックス製)100重量部、オクチル酸亜鉛0.06重量部を混合してワニスを得た。このワニスをメチルエチルケトンで希釈し、厚さ 0.1mmのEガラスクロスに含浸塗工し、165℃で 5分間加熱乾燥してプリプレグを得た。次に、このプリプレグを4枚重ね、厚さ12μmの電解銅箔を上下に配置し、圧力30kgf/cm2、温度220℃で120分間プレスを行い、厚さ 0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表6に示す。
実施例6において、3,3−ビス(4−シアナートフェニル)−1(3H)−イソベンゾフラノン15重量部の代わりに、2,2−ビス(4−シアナートフェニル)プロパンのプレポリマー(BT2070、三菱ガス化学製)15重量部を使用する以外は、実施例6と同様にして行い、厚さ0.4mmの銅張り積層板を得た。得られた銅張り積層板の物性測定結果を表6に示す。
1) ガラス転移温度 (単位 : ℃)
注型成形物 : サイズ 5mm×5mm×3mmの試験片を使用し、TMA装置(TA Instrument 2940型)にて、荷重5g、昇温10℃/分の条件下で測定。
積層板 : 両面銅張積層板の銅箔を全て除去したのち、JIS-C6481に準拠して、DMA法により測定。
2) 曲げ弾性率 (単位 : GPa)
サイズ 10mm×50mm×2mmの試験片を使用し、JIS−K6911に準じて、オートグラフ(島津製作所製、AG5000B)にて、常温で測定。
3) 吸湿耐熱性
50mm×50mmの銅張積層板サンプルの片面の半分以外の全銅箔をエッチング除去した試験片を、プレシッヤークッカー試験機(平山製作所製、PC−3型)で121℃、2気圧で3時間または5時間処理後、260℃のハンダ中に30秒浸漬した後の外観変化を目視で観察。(フクレ発生数/試験数)
4) 耐燃焼性
UL94垂直試験法に準拠して測定。
5) 銅箔ピール強度 (単位 : kgf/cm)
JIS−C6481に準拠して測定。
Claims (8)
- さらに無機充填材を含む請求項1に記載の樹脂組成物。
- 成分Bがエポキシ樹脂、またはエポキシ樹脂およびマレイミド化合物である請求項1に記載の樹脂組成物。
- エポキシ樹脂が非ハロゲン系エポキシ樹脂である、請求項3に記載の樹脂組成物。
- 請求項1に記載の樹脂組成物を硬化してなる硬化物。
- 請求項3に記載の樹脂組成物および基材とからなるプリプレグ。
- 請求項6に記載のプリプレグを硬化して得られる積層板。
- 請求項6に記載のプリプレグおよび金属箔を積層し、次いで硬化して得られる金属箔張り積層板。
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WO2011114687A1 (ja) * | 2010-03-15 | 2011-09-22 | 住友ベークライト株式会社 | 半導体封止用樹脂組成物およびこれを用いた半導体装置 |
JP2011202053A (ja) * | 2010-03-26 | 2011-10-13 | Sumitomo Bakelite Co Ltd | 樹脂ワニス、樹脂付きキャリア材料、プリプレグおよび積層板 |
WO2011142466A1 (ja) * | 2010-05-14 | 2011-11-17 | 日本化薬株式会社 | エポキシ樹脂、エポキシ樹脂組成物およびその硬化物 |
JP2014091782A (ja) * | 2012-11-02 | 2014-05-19 | Hitachi Chemical Co Ltd | プリプレグの保存方法、積層体、及び積層体梱包物 |
CN113710723A (zh) * | 2019-04-16 | 2021-11-26 | 汉高股份有限及两合公司 | 官能化α-当归内酯的用途 |
Also Published As
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KR20090043446A (ko) | 2009-05-06 |
TWI434871B (zh) | 2014-04-21 |
CN101423668A (zh) | 2009-05-06 |
EP2055728B1 (en) | 2010-08-04 |
DE602008002031D1 (de) | 2010-09-16 |
CN101423668B (zh) | 2012-05-23 |
KR101466181B1 (ko) | 2014-11-27 |
EP2055728A1 (en) | 2009-05-06 |
US20090110938A1 (en) | 2009-04-30 |
JP5239743B2 (ja) | 2013-07-17 |
HK1130277A1 (en) | 2009-12-24 |
TW200930739A (en) | 2009-07-16 |
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