JP5265461B2 - 結晶性変性エポキシ樹脂、エポキシ樹脂組成物及び結晶性硬化物 - Google Patents
結晶性変性エポキシ樹脂、エポキシ樹脂組成物及び結晶性硬化物 Download PDFInfo
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- JP5265461B2 JP5265461B2 JP2009149526A JP2009149526A JP5265461B2 JP 5265461 B2 JP5265461 B2 JP 5265461B2 JP 2009149526 A JP2009149526 A JP 2009149526A JP 2009149526 A JP2009149526 A JP 2009149526A JP 5265461 B2 JP5265461 B2 JP 5265461B2
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- epoxy resin
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Description
で表され、n=1体の含有率が50重量%以上であり、4,4'−ジヒドロキシジフェニルメタンの含有率が50重量%以下であるフェノール性化合物20〜100重量部を混合した混合物と、エピクロルヒドリンを反応させて得られ、エポキシ当量が160〜200の範囲であることを特徴とする常温で結晶性を有する変性エポキシ樹脂である。
1) 無機充填材の含有率が80〜96wt%であること。
2) 硬化剤がフェノール系硬化剤であること。
3) フェノール系硬化剤として、二官能性フェノール化合物を50wt%以上用いること。
4) 上記二官能性フェノール化合物が、ヒドロキノン、4,4’−ジヒドロキシビフェニル、4,4’−ジヒドロキシジフェニルエーテル、1,4−ビス(4−ヒドロキシフェノキシ)ベンゼン、4,4’−ジヒドロキシジフェニルメタン、4,4’−ジヒドロキシジフェニルスルフィド、1,5−ナフタレンジオール、2,7−ナフタレンジオール及び2,6−ナフタレンジオールからなる群より選ばれる少なくとも1種であること。
5) 無機充填材として、球状のアルミナを無機充填剤の50wt%以上用いること
なお、BPFはn=1体純度89wt%のビスフェノールF(本州化学製)である。このBPFは、一般式におけるnの平均値が1.06であり、n=1体における異性体構成比は、4,4’−体が33%、2,4’−体が45%、2,2’−体が21%である。
4,4’−ジヒドロキシビフェニル150g、BPF75gをエピクロルヒドリン1300g、ジエチレングリコールジメチルエーテル130gに溶解し、60℃にて減圧下(約130Torr)、48%水酸化ナトリウム水溶液193.0g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1200gを加えた後、水洗を行い塩を除いた。その後、85℃にて20%水酸化ナトリウムを30.0g添加して1時間攪拌し、温水1000mL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、白色結晶状のエポキシ樹脂304g(エポキシ樹脂A)を得た。エポキシ当量は163であり、加水分解性塩素は360ppm、キャピラリー法による融点は142℃から148℃であり、150℃での粘度は5.7mPa・sであった。また、示差走査熱量分析におけるピーク温度は137.6℃であった。チャートを図1に示す。
4,4’−ジヒドロキシビフェニル120g、BPF80g、エピクロルヒドリン1160g、ジエチレングリコールジメチルエーテル116g、48%水酸化ナトリウム水溶液170.7g、20%水酸化ナトリウムを27.0gを用いて実施例1と同様に反応させ、白色結晶状のエポキシ樹脂276g(エポキシ樹脂B)を得た。エポキシ当量は162であり、加水分解性塩素は310ppm、150℃での粘度は5.1mPa・sであった。また、示差走査熱量分析におけるピーク温度は128.3℃であった。
4,4’−ジヒドロキシビフェニル150g、フェノールノボラック(一般式(1)において、n=1体が56wt%、n=1体における異性体構成比は、4,4’−体36%、2,4’−体39%、2,2’−体25%、nの平均値1.65、水酸基当量104)50g、エピクロルヒドリン1160g、ジエチレングリコールジメチルエーテル116g、48%水酸化ナトリウム水溶液171.0g、20%水酸化ナトリウムを25.0gを用いて実施例1と同様に反応させ、白色結晶状のエポキシ樹脂288g(エポキシ樹脂C)を得た。エポキシ当量は164であり、加水分解性塩素は330ppm、150℃での粘度は7.4mPa・sであった。また、示差走査熱量分析におけるピーク温度は141.1℃であった。
4,4’−ジヒドロキシビフェニル80g、BPF120g、エピクロルヒドリン1140g、ジエチレングリコールジメチルエーテル114g、48%水酸化ナトリウム水溶液188.4g、20%水酸化ナトリウムを31.0gを用いて実施例1と同様に反応させ、白色結晶状のエポキシ樹脂281g(エポキシ樹脂D)を得た。エポキシ当量は162であり、加水分解性塩素は280ppm、150℃での粘度は4.1mPa・sであった。また、示差走査熱量分析におけるピーク温度は117.5℃であった。
4,4’−ジヒドロキシビフェニル75g、BPF150g、エピクロルヒドリン1280g、ジエチレングリコールジメチルエーテル128g、48%水酸化ナトリウム水溶液168.3g、20%水酸化ナトリウムを27.0gを用いて実施例1と同様に反応させ、柔らかい白色結晶状のエポキシ樹脂312g(エポキシ樹脂E)を得た。エポキシ当量は161であり、加水分解性塩素は390ppm、150℃での粘度は3.2mPa・sであった。また、示差走査熱量分析におけるピーク温度は106.4℃であった。
BPFに変えて、4,4’−ジヒドロキシジフェニルメタン(純度>99%)を用いて、実施例1と同様に反応させ、白色結晶状のエポキシ樹脂287gを得た。エポキシ当量は162であり、加水分解性塩素は583ppmであり、キャピラリー法による融点は152℃から168℃であった。結晶性の強い高融点化合物であるため150℃で溶融せず、エポキシ樹脂組成物の調製ができなかった。
エポキシ樹脂成分として、実施例1、実施例2、実施例3、比較例1、比較例2で得たエポキシ樹脂A〜E、ビフェニル系エポキシ樹脂(エポキシ樹脂F:ジャパンエポキシレジン製、YX−4000H;エポキシ当量195)、硬化剤として、4,4’−ジヒドロキシジフェニルエーテル(硬化剤A)、4,4’−ジヒドロキシジフェニルメタン(硬化剤B)、4,4’−ジヒドロキシビフェニル(硬化剤C)、フェノールアラルキル樹脂(硬化剤D:三井化学製、XL−225−LL;OH当量174、軟化点75℃)、硬化促進剤としてトリフェニルホスフィン、無機充填材として、球状アルミナ(平均粒径12.2μm)を用いて、表1に示す成分を配合し、ミキサーで十分混合した後、加熱ロールで約5分間混練したものを冷却し、粉砕してそれぞれ実施例4〜9、比較例4〜7のエポキシ樹脂組成物を得た。このエポキシ樹脂組成物を用いて、175℃、5分の条件で成形後、175℃で12時間ポストキュアを行い成形物を得て硬化物の物性を評価した。結果をまとめて表1に示す。なお、表1中の各配合物の数字は重量部を表す。
エポキシ樹脂成分として、4,4’−ジヒドロキシビフェニルにエピクロルヒドリンを反応させて得られたエポキシ樹脂(融点175℃)を用いた以外は実施例4と同様にしてエポキシ組成物を調製し、175℃、5分の同様な条件で成形を行ったが成形不良が発生し、硬化物を得ることができなかった。
(1)熱伝導率
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。
(2)融点、融解熱の測定(DSC法)
示差走査熱量分析装置(セイコーインスツル製DSC6200型)を用い、昇温速度10℃/分で測定した。
(3)線膨張係数、ガラス転移温度
線膨張係数及びガラス転移温度は、セイコーインスツル(株)製TMA120C型熱機械測定装置を用いて、昇温速度10℃/分にて測定した。
(3)吸水率
直径50mm、厚さ3mmの円盤を成形し、ポストキュア後、85℃、相対湿度85%の条件で100時間吸湿させた後の重量変化率とした。
Claims (12)
- 一般式(1)で表されるフェノール性化合物のn=1体の含有率が80重量%以上である請求項1に記載の結晶性変性エポキシ樹脂。
- (A)エポキシ樹脂、(B)硬化剤、及び(C)無機充填材を主成分とするエポキシ樹脂組成物において、エポキシ樹脂として請求項1または2に記載の結晶性変性エポキシ樹脂を50wt%以上用いることを特徴とするエポキシ樹脂組成物。
- 無機充填材の含有率が80〜96wt%である請求項3に記載のエポキシ樹脂組成物。
- 硬化剤がフェノール系硬化剤である請求項3または4に記載のエポキシ樹脂組成物。
- 硬化剤として、二官能性フェノール化合物を50wt%以上用いる請求項3〜5のいずれかに記載のエポキシ樹脂組成物。
- 二官能性フェノール化合物が、ヒドロキノン、4,4’−ジヒドロキシビフェニル、4,4’−ジヒドロキシジフェニルエーテル、1,4−ビス(4−ヒドロキシフェノキシ)ベンゼン、4,4’−ジヒドロキシジフェニルメタン、4,4’−ジヒドロキシジフェニルスルフィド、1,5−ナフタレンジオール、2,7−ナフタレンジオール及び2,6−ナフタレンジオールからなる群より選ばれる少なくとも1種である請求項6に記載のエポキシ樹脂組成物。
- 無機充填材として、球状のアルミナを50wt%以上用いる請求項3〜7のいずれかに記載のエポキシ樹脂組成物。
- 半導体封止用のエポキシ樹脂組成物であることを特徴とする請求項3〜8のいずれかに記載のエポキシ樹脂組成物。
- 請求項3〜9のいずれかに記載のエポキシ樹脂組成物を硬化して得られ、熱伝導率が4W/m・K以上であることを特徴とする結晶性硬化物。
- 硬化物の走査示差熱分析における融点のピークが150℃から300℃の範囲にある請求項10に記載の結晶性硬化物。
- 硬化物の走査示差熱分析における樹脂成分換算の吸熱量が5J/g以上である請求項11に記載の結晶性硬化物。
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