JP7059633B2 - エポキシ樹脂、製造方法、エポキシ樹脂組成物及びその硬化物 - Google Patents
エポキシ樹脂、製造方法、エポキシ樹脂組成物及びその硬化物 Download PDFInfo
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- JP7059633B2 JP7059633B2 JP2017553281A JP2017553281A JP7059633B2 JP 7059633 B2 JP7059633 B2 JP 7059633B2 JP 2017553281 A JP2017553281 A JP 2017553281A JP 2017553281 A JP2017553281 A JP 2017553281A JP 7059633 B2 JP7059633 B2 JP 7059633B2
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Images
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
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Description
以下、本発明を詳細に説明する。
本発明のエポキシ樹脂は、芳香環上の置換基として炭素数4~8のアルキル基を有する、モノアルキルジヒドロキシベンゼンを原料とするエポキシ樹脂であって、前記モノアルキルジヒドロキシベンゼンのエポキシ化物のピークトップの分子量+(20~40)の範囲で検出される化合物(α)を、前記エポキシ樹脂のGPCチャートにおいて、ピーク面積%が0.1~0.8%の範囲で含有することを特徴とする。
<GPC測定条件>
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 G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G4000HXL」
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」
測定条件: 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ワークステーション EcoSEC―WorkStation」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)。
東ソー株式会社製「Agilent 1220 Infinity LC」、
カラム: 東ソー株式会社製「TSK-GEL ODS-120T」
検出器: VWD
データ処理:東ソー株式会社製「Agilent EZChrom Elite」
測定条件: カラム温度 40℃
展開溶媒 A液:水/アセトニトリル=50/50wt%
B液:アセトニトリル
展開条件 A液/B液=95/5(15min)
リニアグラジエント(20min)
A液/B液=0/100(20min)
流速 1.0ml/min
測定波長 254nm
で表されるエポキシ樹脂であることが好ましく、前述のように、成型収縮率の観点から、構造式(1)中のR1がブチル基又はオクチル基であることがより好ましく、t-ブチル基であることが最も好ましい。
前記のように、本発明のエポキシ樹脂は、前述の化合物(α)あるいは(β1)、(β2)を特定量含む。このようなエポキシ樹脂(A)を得る方法としては、炭素数4~8のアルキル基を芳香環上の置換基として1個有するモノアルキルジヒドロキシベンゼンのエポキシ化物と、前述の化合物(α)あるいは(β1)、(β2)をあらかじめ用意し、これらを特定比率になるように混合することで得ることができる。更には、原料のモノアルキルジヒドロキシベンゼンと、ジアルキルジヒドロキシベンゼン等とを予め混合してから、これをエポキシ化する方法であってもよい。後者の製造方法を用いると、工業的な生産性に優れると共に、得られるエポキシ樹脂の均一性にもより一層優れたものとすることが容易となる。
本発明のエポキシ樹脂は、硬化剤を併用できるものである。前記エポキシ樹脂に硬化剤を配合することで、硬化性のエポキシ樹脂組成物を作製することができる。以下、本発明のエポキシ樹脂をエポキシ樹脂(A)と記載することがある。
本発明のエポキシ樹脂組成物は、半導体封止材料、半導体装置、プリプレグ、プリント回路基板、ビルドアップ基板、ビルドアップフィルム、繊維強化複合材料、繊維強化樹脂成型品、導電ペースト等に適用することができる。
本発明のエポキシ樹脂組成物から半導体封止材料を得る方法としては、前記エポキシ樹脂組成物、前記硬化促進剤、及び無機充填剤等の配合剤とを必要に応じて押出機、ニ-ダ、ロ-ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ,アルミナ,窒化ケイ素などの高充填化、または溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率はエポキシ樹脂組成物100質量部当たり、無機充填剤を30質量%~95質量%の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐半田クラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明のエポキシ樹脂組成物から半導体装置を得る方法としては、前記半導体封止材料を注型、或いはトランスファー成型機、射出成型機などを用いて成型し、さらに50~200℃で2~10時間の間、加熱する方法が挙げられる。
本発明のエポキシ樹脂組成物からプリプレグを得る方法としては、有機溶剤を配合してワニス化した硬化性樹脂組成物を、補強基材(紙、ガラス布、ガラス不織布、アラミド紙、アラミド布、ガラスマット、ガラスロービング布など)に含浸したのち、用いた溶剤種に応じた加熱温度、好ましくは50~170℃で加熱することによって、得る方法が挙げられる。この時用いる樹脂組成物と補強基材の質量割合としては、特に限定されないが、通常、プリプレグ中の樹脂分が20質量%~60質量%となるように調製することが好ましい。
本発明のエポキシ樹脂組成物からプリント回路基板を得る方法としては、前記プリプレグを、常法により積層し、適宜銅箔を重ねて、1~10MPaの加圧下に170~300℃で10分~3時間、加熱圧着させる方法が挙げられる。
本発明のエポキシ樹脂組成物からビルドアップ基板を得る方法としては、工程1~3を経由する方法が挙げられる。工程1では、まず、ゴム、フィラーなどを適宜配合した前記硬化性樹脂組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる。工程2では、必要に応じて、エポキシ樹脂組成物が塗布された回路基板に所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって、前記基板に凹凸を形成させ、銅などの金属をめっき処理する。工程3では、工程1~2の操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップしてビルドアップ基板を成型する。なお、前記工程において、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行うとよい。また、本発明のビルドアップ基板は、銅箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170~300℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
本発明のエポキシ樹脂組成物からビルドアップフィルムを得る方法としては、例えば、支持フィルム上に硬化性樹脂組成物を塗布したのち、乾燥させて、支持フィルムの上に樹脂組成物層を形成する方法が挙げられる。本発明のエポキシ樹脂組成物をビルドアップフィルムに用いる場合、該フィルムは、真空ラミネート法におけるラミネートの温度条件(通常70℃~140℃)で軟化し、回路基板のラミネートと同時に、回路基板に存在するビアホール或いはスルーホール内の樹脂充填が可能な流動性(樹脂流れ)を示すことが肝要であり、このような特性を発現するよう前記各成分を配合することが好ましい。
本発明のエポキシ樹脂組成物から繊維強化複合材料(樹脂が強化繊維に含浸したシート状の中間材料)を得る方法としては、エポキシ樹脂組成物を構成する各成分を均一に混合してワニスを調整し、次いでこれを強化繊維からなる強化基材に含浸した後、重合反応させることにより製造する方法が挙げられる。
本発明のエポキシ樹脂組成物から繊維強化成型品(樹脂が強化繊維に含浸したシート状部材が硬化した成型品)を得る方法としては、型に繊維骨材を敷き、前記ワニスを多重積層してゆくハンドレイアップ法やスプレーアップ法、オス型・メス型のいずれかを使用し、強化繊維からなる基材にワニスを含浸させながら積み重ねて成型、圧力を成型物に作用させることのできるフレキシブルな型をかぶせ、気密シールしたものを真空(減圧)成型する真空バッグ法、あらかじめ強化繊維を含有するワニスをシート状にしたものを金型で圧縮成型するSMCプレス法、繊維を敷き詰めた合わせ型に前記ワニスを注入するRTM法などにより、強化繊維に前記ワニスを含浸させたプリプレグを製造し、これを大型のオートクレーブで焼き固める方法などが挙げられる。なお、前記で得られた繊維強化樹脂成型品は、強化繊維とエポキシ樹脂組成物の硬化物とを有する成型品であり、具体的には、繊維強化成型品中の強化繊維の量は、40質量%~70質量%の範囲であることが好ましく、強度の点から50質量%~70質量%の範囲であることが特に好ましい。
本発明のエポキシ樹脂組成物から導電ペーストを得る方法としては、例えば、微細導電性粒子を該硬化性樹脂組成物中に分散させる方法が挙げられる。前記導電ペーストは、用いる微細導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
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 G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G4000HXL」
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」
測定条件: 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ワークステーション EcoSEC-WorkStation」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)。
装置:日本電子株式会社製 AL-400
測定モード:逆ゲート付きデカップリング
溶媒:重水素化ジメチルスルホキシド
パルス角度:45°パルス
試料濃度 :30wt%
積算回数 :4000回
FD-MSスペクトルは、日本電子株式会社製の二重収束型質量分析装置「AX505H(FD505H)」を用いて測定した。
東ソー株式会社製「Agilent 1220 Infinity LC」、
カラム: 東ソー株式会社製「TSK-GEL ODS-120T」
検出器: VWD
データ処理:東ソー株式会社製「Agilent EZChrom Elite」
測定条件: カラム温度 40℃
展開溶媒 A液:水/アセトニトリル=50/50wt%
B液:アセトニトリル
展開条件 A液/B液=95/5(15min)
リニアグラジエント(20min)
A液/B液=0/100(20min)
流速 1.0ml/min
測定波長 254nm
温度計、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながら4-t-ブチルカテコール164.7g、3,5-ジ-t-ブチルカテコール1.3g、エピクロルヒドリン555g(6.0モル)、n-ブタノール165gを仕込み溶解させた。50℃に昇温した後に、20%水酸化ナトリウム水溶液440g(2.2モル)を3時間要して添加し、その後更に50℃で1時間反応させた。反応終了後、150℃減圧下で未反応エピクロルヒドリンを留去した。次に、得られた粗エポキシ樹脂にメチルイソブチルケトン300gとn-ブタノール50gとを加え溶解した。更にこの溶液に10質量%水酸化ナトリウム水溶液15部を添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水100gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去してエポキシ樹脂(A-1)240gを得た。得られたエポキシ樹脂のエポキシ当量は209g/eqであった。得られたエポキシ樹脂のGPCチャートを図1、FD-MSのスペクトルを図2に、13C-NMRスペクトルを図3に、HPLCチャートを図4に示す。エポキシ樹脂中の化合物(α)の面積比率はGPC測定において0.70%であり、HPLC測定に基づく、(β1+β2)/(γ)は0.24であった。
4-t-ブチルカテコールを165.5g、3,5-ジ-t-ブチルカテコールを0.5g、エピクロルヒドリンを370g(4.0モル)、n-ブタノールを110gに変更した以外は合成例1と同様にしてエポキシ樹脂(A-2)を得た。得られたエポキシ樹脂のエポキシ当量は371g/eqであった。得られたエポキシ樹脂のGPCチャートを図5に、HPLCチャートを図6に示す。エポキシ樹脂中の化合物(α)の面積比率は0.21%であり、HPLC測定に基づく、(β1+β2)/(γ)は0.92であった。
温度計、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながら4-t-ブチルカテコール165.0g、3,5-ジ-t-ブチルカテコール1.0g、エピクロルヒドリン555g(6.0モル)、n-ブタノール165gを仕込み溶解させた。70℃に昇温した後に、50%テトラメチルアンモニウムクロライド水溶液を5g添加して6時間反応させた。その後、20%水酸化ナトリウム水溶液440g(2.2モル)を3時間要して添加し、その後更に50℃で1時間反応させた。反応終了後、150℃減圧下で未反応エピクロルヒドリンを留去した。次に、得られた粗エポキシ樹脂にメチルイソブチルケトン300gとn-ブタノール50gとを加え溶解した。更にこの溶液に10質量%水酸化ナトリウム水溶液15部を添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水100gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去してエポキシ樹脂(A-3)を得た。得られたエポキシ樹脂のエポキシ当量は179g/eqであった。得られたエポキシ樹脂のGPCチャートを図7に、HPLCチャートを図8示す。エポキシ樹脂中の化合物(α)の面積比率は0.55%であり、HPLC測定に基づく、(β1+β2)/(γ)は0.14であった。
t-ブチルカテコールの市販品である、DIC-TBCを166.0g(DIC株式会社製)、エピクロルヒドリンを740g(8.0モル)、n-ブタノールを222gに変更した以外は合成例1と同様にしてエポキシ樹脂(A-4)を得た。得られたエポキシ樹脂のエポキシ当量は198g/eq、25℃での粘度は1,030mPa・sであった。得られたエポキシ樹脂のHPLCチャートを図9に示す。エポキシ樹脂中のHPLCによる(β1+β2)/(γ)面積比率は0.19であった。
温度計、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながらDIC-TBCを166.0g、エピクロルヒドリン555g(6.0モル)を仕込み溶解させた。110℃に昇温した後に、50%テトラメチルアンモニウムクロライド水溶液を5g添加して3時間反応させた。その後、20%水酸化ナトリウム水溶液440g(2.2モル)を3時間要して添加し、その後更に50℃で1時間反応させた。反応終了後、150℃減圧下で未反応エピクロルヒドリンを留去した。次に、得られた粗エポキシ樹脂にメチルイソブチルケトン300gとn-ブタノール50gとを加え溶解した。更にこの溶液に10質量%水酸化ナトリウム水溶液15部を添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水100gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去してエポキシ樹脂(A’-1)を得た。得られたエポキシ樹脂のエポキシ当量は240g/eq、25℃での粘度は2,690mPa・sであった。得られたエポキシ樹脂のHPLCチャートを図10に示す。エポキシ樹脂中のHPLCによる(β1+β2)/(γ)の面積比率は0.44であった。
温度計、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながらDIC-TBCを166.0g、エピクロルヒドリン1110g(12.0モル)を仕込み溶解させた。40℃に昇温した後に、ベンジルトリメチルアンモニウムクロライドを7.4g添加して48時間反応させた。その後、20%水酸化ナトリウム水溶液440g(2.2モル)を3時間要して添加し、その後更に50℃で1時間反応させた。反応終了後、150℃減圧下で未反応エピクロルヒドリンを留去した。次に、得られた粗エポキシ樹脂にメチルイソブチルケトン300gとn-ブタノール50gとを加え溶解した。更にこの溶液に10質量%水酸化ナトリウム水溶液15部を添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水100gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去してエポキシ樹脂(A’-2)を得た。得られたエポキシ樹脂のエポキシ当量は205g/eq、25℃での粘度は3,560mPa・sであった。得られたエポキシ樹脂のHPLCチャートを図11に示す。エポキシ樹脂中のHPLCによる(β1+β2)/(γ)の面積比率は0.09であった。
・エポキシ樹脂A-1:合成例1で得られたエポキシ樹脂
・エポキシ樹脂A-2:合成例2で得られたエポキシ樹脂
・エポキシ樹脂A-3:合成例3で得られたエポキシ樹脂
・エポキシ樹脂A-4:合成例4で得られたエポキシ樹脂
・エポキシ樹脂A’-1:比較合成例1で得られたエポキシ樹脂
・エポキシ樹脂A’-2:比較合成例2で得られたエポキシ樹脂
・N-655-EXP-S:クレゾールノボラック型エポキシ樹脂(DIC株式会社製「N-655-EXP-S」、エポキシ当量:201g/eq)
・N-770:フェノールノボラック型エポキシ樹脂(DIC株式会社製「N-770」、エポキシ当量:190g/eq)
・HP-5000:メトキシナフタレン変性ノボラック型エポキシ樹脂(DIC株式会社製「HP-5000」、エポキシ当量:250g/eq.)
・NC-3000:ビフェニルアラルキル型エポキシ樹脂(日本化薬株式会社製「NC-3000」、エポキシ当量:278g/eq)
・NC-2000L:フェノールアラルキル型エポキシ樹脂(日本化薬株式会社製「NC-2000L」、エポキシ当量:238g/eq)
・YX-4000:ビフェニル型エポキシ樹脂(三菱化学株式会社製「YX-4000」、エポキシ当量:188g/eq)
・硬化剤TD-2131:フェノールノボラック樹脂 (DIC株式会社製「TD-2131」、水酸基当量:104g/eq)
・硬化剤Me-THPA:メチルテトラヒドロフタル酸無水物
・硬化促進剤1,2-DMZ:1,2-ジメチルイミダゾール
・TPP:トリフェニルホスフィン
・溶融シリカ:球状シリカ「FB-560」電気化学株式会社製
・シランカップリング剤:γ-グリシドキシトリエトキシキシシラン「KBM-403」信越化学工業株式会社製
・カルナウバワックス:「PEARL WAX No.1-P」電気化学株式会社製
前記で作製した成型物を厚さ0.8mmの硬化物を幅5mm、長さ54mmのサイズに切り出し、これを試験片1とした。この試験片1を粘弾性測定装置(DMA:レオメトリック社製固体粘弾性測定装置「RSAII」、レクタンギュラーテンション法:周波数1Hz、昇温速度3℃/分)を用いて、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、260℃での貯蔵弾性率を熱時弾性率として測定した。
トランスファー成型機(コータキ精機製、KTS-15-1.5C)を用いて、金型温度150℃、成型圧力9.8MPa、硬化時間600秒の条件下で、樹脂組成物を注入成型して、縦110mm、横12.7mm、厚さ1.6mmの試験片を作製した。その後試験片を175℃で5時間ポストキュアし、金型キャビティの内径寸法と、室温(25℃)での試験片の外径寸法とを測定し、下記式により収縮率を算出した。
収縮率(%)={(金型の内径寸法)-(25℃での硬化物の縦方向の寸法)}/(175℃での金型キャビティの内径寸法)×100(%)
これらの結果を表1に示す。
先で得た硬化性組成物を、幅90mm、長さ110mm、高さ2mmの型枠内に流し込み、75℃で2時間硬化後、更に120℃で3時間硬化させた。得られた硬化物をダイヤモンドカッターで幅5mm、長さ50mmに切り出し、これを試験片とした。次に、粘弾性測定装置(エスアイアイ・ナノテクノロジー社製「DMS6100」)を用いて試験片の両持ち曲げによる動的粘弾性を測定し、tanδが最大となる値の温度をガラス転移温度(Tg)として評価した。なお、動的粘弾性測定の測定条件は、温度条件 室温~260℃、昇温速度3℃/分、周波数1Hz、歪振幅10μmとした。
先で得たエポキシ樹脂組成物を幅90mm、長さ110mm、高さ4mmの型枠内に流し込み、90℃で2時間硬化後、更に110℃で3時間硬化させた。JIS K6911に準拠して、硬化物の曲げ強度及び曲げ弾性率を測定した。
金属シャーレにエポキシ樹脂を1g秤量し、125℃又は150℃の乾燥機内で1時間加熱し、加熱前後の質量変化より揮発分を評価した。
Claims (19)
- 炭素数4~8のアルキル基を芳香環上の置換基として1個有するモノアルキルジヒドロキシベンゼンと、炭素数4~8のアルキル基を芳香環上の置換基として2個有するジアルキルジヒドロキシベンゼンとを予め混合してから、これをエポキシ化する方法であるエポキシ樹脂の製造方法であり、
前記モノアルキルジヒドロキシベンゼンと、前記ジアルキルジヒドロキシベンゼンとの質量比(モノアルキルジヒドロキシベンゼン/ジアルキルジヒドロキシベンゼン)が99.1/0.9~99.9/0.1の範囲であり、
前記モノアルキルジヒドロキシベンゼンのエポキシ化物のピークトップの分子量+(20~40)の範囲で検出され、下記構造式で表される化合物(α)を、前記エポキシ樹脂のGPCチャートにおいて、ピーク面積%が0.1~0.8%の範囲で含有するエポキシ樹脂の製造方法。
- 前記モノアルキルジヒドロキシベンゼンが、炭素数4~8のアルキル基を芳香環上の置換基として1個有するモノアルキルカテコールである請求項1記載のエポキシ樹脂の製造方法。
- 前記モノアルキルジヒドロキシベンゼンがモノアルキルカテコールであり、前記ジアルキルジヒドロキシベンゼンがジアルキルカテコールである請求項1記載のエポキシ樹脂の製造方法。
- 芳香環上の置換基がブチル基又はオクチル基である請求項1~4の何れか1項記載のエポキシ樹脂の製造方法。
- 芳香環上の置換基がt-ブチル基である請求項1~5の何れか1項記載のエポキシ樹脂の製造方法。
- 前記エポキシ樹脂のエポキシ当量が170g/eq~400g/eqである請求項1~6の何れか1項記載のエポキシ樹脂の製造方法。
- 前記エポキシ樹脂のエポキシ当量が170g/eq~250g/eqである請求項1~6の何れか1項記載のエポキシ樹脂の製造方法。
- 前記エポキシ樹脂の25℃における粘度が300~2500mPa・sである請求項1~8の何れか1項記載のエポキシ樹脂の製造方法。
- 請求項1~9の何れか1項記載の製造方法により得られたエポキシ樹脂と、硬化剤とを含有するエポキシ樹脂組成物の製造方法。
- 更に、前記エポキシ樹脂以外の、その他のエポキシ樹脂を含有する請求項10記載のエポキシ樹脂組成物の製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物の硬化物の製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物と無機充填材とを含有する半導体封止材料の製造方法。
- 請求項13に記載の製造方法により得られた半導体封止材料の硬化物を含む半導体装置の製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物と補強基材とを有する含浸基材の半硬化物であるプリプレグの製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物の板状賦形物と銅箔とからなる回路基板の製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物の硬化物と基材フィルムとからなるビルドアップフィルムの製造方法。
- 請求項10又は11記載の製造方法により得られたエポキシ樹脂組成物と強化繊維とを含有する繊維強化複合材料の製造方法。
- 請求項18記載の製造方法により得られた繊維強化複合材料の硬化物である繊維強化成形品の製造方法。
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