JP2022007637A - 多価ヒドロキシ樹脂、その製造方法、及びそれを含むエポキシ樹脂組成物、並びにエポキシ樹脂硬化物 - Google Patents
多価ヒドロキシ樹脂、その製造方法、及びそれを含むエポキシ樹脂組成物、並びにエポキシ樹脂硬化物 Download PDFInfo
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- epoxy resin
- resin
- resin composition
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- polyvalent hydroxy
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 58
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- 239000011347 resin Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 239000012774 insulation material Substances 0.000 abstract 1
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- 235000010290 biphenyl Nutrition 0.000 description 3
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- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
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Abstract
Description
本発明の樹脂組成物には、これら硬化剤の1種又は2種以上を混合して用いることができる。そして、本発明のエポキシ樹脂組成物の場合、一般式(1)で表される多価ヒドロキシ樹脂の配合量は、硬化剤全体中、5~100wt%、好ましくは60~100wt%の範囲であることがよい。硬化物の信頼性と熱伝導性の観点から、別種の硬化剤としては、好ましくは2価のフェノール類が好ましく、さらに好ましくは、4,4’-ビフェノール、2,2’-ビフェノール、ハイドロキノン、レゾルシン、ナフタレンジオール、4,4’-ジヒドロキシジフェニルエーテルである。
100mLの共栓付フラスコに約6mg/eqの試料を精秤し、無水酢酸/ピリジン=3/1(容量比)で混合した試薬を3mL加え、冷却管を付け、ホットプレートで5分間加熱還流させ、5分間の放冷の後、1mLの水を加える。その液を、0.5mol/LのKOH/MeOH溶液で電位差滴定することで算出した。
電位差滴定装置を用い、溶媒としてメチルエチルケトンを使用し、臭素化テトラエチルアンモニウム酢酸溶液を加え、電位差滴定装置にて0.1mol/L過塩素酸-酢酸溶液を用いて測定した。
示差走査熱量分析装置(エスアイアイ・ナノテクノロジー株式会社製 EXSTAR6000 DSC/6200)により、昇温速度5℃/分の条件で、DSCピーク温度を求めた。すなわち、このDSCピーク温度を樹脂の融点とした。
BROOKFIELD社製、CAP2000H型回転粘度計を用いて、150℃にて測定した。
JIS-K-2207に従い環球法にて測定した。
本体(東ソー株式会社製、HLC-8220GPC)にカラム(東ソー株式会社製、TSKgelG4000HXL、TSKgelG3000HXL、TSKgelG2000HXL)を直列に備えたものを使用し、カラム温度は40℃にした。また、溶離液にはテトラヒドロフラン(THF)を使用し、1mL/分の流速とし、検出器は示差屈折率検出器を使用した。測定試料はサンプル0.1gを10mLのTHFに溶解し、マイクロフィルターで濾過したものを50μL使用した。データ処理は、東ソー株式会社製GPC-8020モデルIIバージョン6.00を使用した。また、標準ポリスチレンによる検量線により数平均分子量(Mn)を求めた。
熱機械測定装置(エスアイアイ・ナノテクノロジー株式会社製 EXSTAR6000TMA/6100)により、昇温速度10℃/分の条件でTgを求めた。
熱重量/示差熱分析装置(エスアイアイ・ナノテクノロジー製 EXSTAR6000TG/DTA6200、)を用いて、窒素雰囲気下、昇温速度10℃/分の条件において、10%重量減少温度(Td10)を測定した。また、700℃における重量減少を測定し、残炭率として算出した。
熱伝導率は、NETZSCH製LFA447型熱伝導率計を用いて非定常熱線法により測定した。
フーリエ変換型赤外分光光度計(Perkinelmer Inc.製、 Frontier Gold FT-IR Spectrometer)を使用して、全反射測定法(ATR法)により波数400~4000cm-1の吸光度を測定した。
質量分析計JMS-T100GCV(日本電子社製)を用いて測定した。試料をアセトンに溶解し、測定に供した。
ディーンスターク管を取り付けたフラスコに、ハイドロキノン300.0g、パラホルムアルデヒド28.9g、ジエチレングリコールジメチルエーテル263.1gを仕込み、窒素気流下、攪拌しながら100℃程度まで昇温して溶解させた。次にp-トルエンスルホン酸0.33gを加えて160℃まで昇温し、脱水させながら6時間反応させて、多価ヒドロキシ樹脂を生成させた。ジエチレングリコールジメチルエーテルを留去し、メチルイソブチルケトンを加えた後、中和、水洗、濾過を行い、次にメチルイソブチルケトンを減圧留去し、一般式(2)に係る多価ヒドロキシ樹脂aを295.1g得た。この多価ヒドロキシ樹脂aのOH当量は59g/eq.であった。数平均分子量は430であり、n(数平均)が0~5の混合物であった。
参考例1で得られた多価ヒドロキシ樹脂aを50.0g(約0.85モル)、p-ヒドロキシ安息香酸58.5g(約0.42モル)、クロロベンゼン200.0g、p-トルエンスルホン酸1.9gを仕込み、窒素気流下、攪拌しながら120℃まで昇温し、系中の水分を還流脱水しながら5時間反応させた。室温まで冷却後に濾過、水洗を繰り返し、減圧乾燥することで黄褐色粉末状のエステル基含有多価ヒドロキシ樹脂Aを44.9g得た。数平均分子量は484であり、n(数平均)が0~5の混合物であった。なお、n=0体の含有量(GPC面積%)は11面積%であった。GPCチャートを図1に、IRチャートを図2に、FD-MSスペクトルを図3に示す。DSCによる融点は177℃、193℃、247℃の3か所のピーク温度が確認された。OH当量は、仕込み比率、GPC、FD-MSから各成分を分析した結果から算出し、119g/eq.であった。
p-ヒドロキシ安息香酸の代わりに6-ヒドロキシ‐2-ナフトエ酸79.7g(約0.42モル)を用いた他は実施例1と同様にして反応を行い、茶褐色粉状のエステル基含有多価ヒドロキシ樹脂87.9gを得た(多価ヒドロキシ樹脂B)。この樹脂のOH当量は、計算値で156g/eq.であった。
ディーンスターク管を取り付けたフラスコに、ハイドロキノン50.0g、p-ヒドロキシ安息香酸39.9g、ホウ酸0.75g、硫酸3.1g、キシレン400gを仕込み、窒素気流下、攪拌しながら130℃まで昇温し、系中の水分を還流脱水しながら5時間反応させた。室温まで冷却後に濾過、中和後、水洗を繰り返し行い、更にメタノールで洗浄後、減圧乾燥することで白色結晶を54.1g得た。OH当量は、計算値で115g/eq.であり、DSCによる融点は240℃であった。
ヒドロキノン50.0g、4,4’-ジヒドロキシビフェニル100.0gをエピクロルヒドリン1000g、ジエチレングリコールジメチルエーテル150gに溶解し、60℃にて48%水酸化ナトリウムを16.5g加え1時間攪拌した。その後、減圧下(約130Torr)、48%水酸化ナトリウム水溶液148.8gを3時間かけて滴下した。この間、生成する水はエピクロルヒドリンとの共沸により系外に除き、留出したエピクロルヒドリンは系内に戻した。滴下終了後、さらに1時間反応を継続して脱水後、エピクロルヒドリンを留去し、メチルイソブチルケトン600gを加えた後、水洗により塩を除いた。その後、85℃にて48%水酸化ナトリウムを13.5g添加して1時間攪拌し、温水200mLで水洗した。その後、分液により水を除去後、メチルイソブチルケトンを減圧留去し、白色結晶状の変性エポキシ樹脂(エポキシ樹脂A)224gを得た。エポキシ当量は138であり、加水分解性塩素は320ppm、キャピラリー法による融点は10
4℃から141℃であり、150℃での粘度は3.4mPa・sであった。
エポキシ樹脂成分として、参考例3のエポキシ樹脂(エポキシ樹脂A)、4,4’-ジヒドロキシジフェニルエーテルのエポキシ化物(エポキシ樹脂B:日鉄ケミカル&マテリアル(株)製、YSLV-80DE163g/eq.)、ビフェニル系エポキシ樹脂(エポキシ樹脂C:ジャパンエポキシレジン製、YX-4000H、エポキシ当量188g/eq.)、又はフェノールノボラック型のエポキシ樹脂(エポキシ樹脂D:日鉄ケミカル&マテリアル(株)製、YDPN-638、エポキシ当量177g/eq.)を使用し、硬化剤として、実施例1の多価ヒドロキシ樹脂A(硬化剤A)、実施例2の多価ヒドロキシ樹脂B(硬化剤B)、参考例1の多価ヒドロキシ樹脂a(硬化剤C)、ハイドロキノン(硬化剤D)、フェノールノボラック樹脂(硬化剤E:水酸基当量105、軟化点67℃)、又は参考例2のハイドロキノンとp-ヒドロキシ安息香酸の反応物(硬化剤F)を使用した。また、硬化促進剤としてトリフェニルホスフィンを使用し、表1に示す配合でエポキシ樹脂組成物を得た。表中の数値は配合における重量部を示す。このエポキシ樹脂組成物を用いて175℃にて成形し、175℃にて5時間ポストキュアを行い、硬化物試験片を得た後、各種物性測定に供した。
Claims (6)
- 数平均分子量が3000以下である請求項1に記載の多価ヒドロキシ樹脂。
- エポキシ樹脂及び硬化剤を含むエポキシ樹脂組成物において、硬化剤の一部または全部として、請求項1または2に記載の多価ヒドロキシ樹脂を用いることを特徴とするエポキシ樹脂組成物。
- エポキシ樹脂が2官能の結晶性エポキシ樹脂であることを特徴とする請求項4に記載のエポキシ樹脂組成物。
- 請求項4または5に記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物。
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