JP5464304B1 - エポキシ樹脂、エポキシ樹脂の製造方法、エポキシ樹脂組成物、その硬化物、及び放熱樹脂材料 - Google Patents
エポキシ樹脂、エポキシ樹脂の製造方法、エポキシ樹脂組成物、その硬化物、及び放熱樹脂材料 Download PDFInfo
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- JP5464304B1 JP5464304B1 JP2013532766A JP2013532766A JP5464304B1 JP 5464304 B1 JP5464304 B1 JP 5464304B1 JP 2013532766 A JP2013532766 A JP 2013532766A JP 2013532766 A JP2013532766 A JP 2013532766A JP 5464304 B1 JP5464304 B1 JP 5464304B1
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- epoxy resin
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- diglycidyl ether
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- HGJYOHAIVZXUML-UHFFFAOYSA-M potassium;3-(benzenesulfonyl)benzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 HGJYOHAIVZXUML-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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- H05K1/02—Details
- H05K1/0201—Thermal arrangements, e.g. for cooling, heating or preventing overheating
- H05K1/0203—Cooling of mounted components
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Abstract
Description
で表わされるフェニレンユニットまたは下記一般式(ii)
で表わされるナフチレンユニットを表わし、nは、0〜10の整数を表わす。]
で表わされることを特徴とするエポキシ樹脂は、配向性が高いことからその硬化物は熱伝導性が高く、更に基材密着性にも優れることを見出し、本発明を完成するに至った。
で表わされるフェニレンユニットまたは下記一般式(ii)
で表わされるナフチレンユニットを表わし、nは、0〜10の整数を表わす。]
で表わされることを特徴とするエポキシ樹脂に関する。
又は下記一般式(2)
で表わされるジオール化合物(a)と、炭素原子数1〜9の直鎖状アルキレンジオールのジグリシジルエーテル、前記直鎖状アルキレンジオールの炭素原子に炭素原子数1〜18のアルキル基が結合した構造を有する分岐状アルキレンジオールのジグリシジルエーテル、及び前記アルキレンジオール中の連続する2個のメチレン基の間にエーテル結合が存在するジオール化合物のジグリシジルエーテルからなる群から選ばれる一種類以上のジグリシジルエーテル化合物(q)とを反応させることを特徴とするエポキシ樹脂の製造方法に関する。
で表わされるフェニレンユニットまたは下記一般式(ii)
で表わされるナフチレンユニットを表わし、nは、0〜10の数を表わす。]
で表わされることを特徴とする。
又は下記一般式(2)
で表わされるジオール化合物(a)と、炭素原子数1〜9の直鎖状アルキレンジオールのジグリシジルエーテル、前記直鎖状アルキレンジオールの炭素原子に炭素原子数1〜18のアルキル基が結合した構造を有する分岐状アルキレンジオールのジグリシジルエーテル、及び前記アルキレンジオール中の連続する2個のメチレン基の間にエーテル結合が存在するジオール化合物のジグリシジルエーテルからなる群から選ばれる一種類以上のジグリシジルエーテル化合物(q)とを、常法に従って、反応させることによって容易に製造することができる。
測定装置 :東ソー株式会社製「HLC−8220 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−8020モデルIIバージョン4.10」
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−8020モデルIIバージョン4.10」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)製 AL−400
測定モード:SGNNE(NOE消去の1H完全デカップリング法)
溶媒 :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 :10000回
3)MSスペクトル:日本電子株式会社製 二重収束型質量分析装置 AX505H(FD505H)
温度計、冷却管、分留管及び撹拌器を取り付けたフラスコに、ビフェノール186質量部(1モル)及び1,6−ヘキサンジオールジグリシジルエーテル(阪本薬品製SR−16HL、エポキシ当量122g/eq)488質量部(2モル)を仕込み、150℃で、窒素を吹き込みながら撹拌し溶解した。その後、テトラメチルアンモニウムクロライド1.0gを水溶液として添加し、150℃で4時間攪拌することによって、エポキシ当量395g/eqのエポキシ樹脂(A−1)650質量部を得た。
実施例1において、ビフェノール186質量部(1モル)を2,6−ジヒドロキシナフタレン160質量部(1モル)に変更した以外は、実施例1と同様にして、エポキシ当量358g/eqのエポキシ樹脂(A−2)648質量部を得た。
実施例1において、ビフェノール186質量部(1モル)を4,4’−ジヒドロキシジフェニルエーテル202質量部(1モル)に変更した以外は、実施例1と同様にして、エポキシ当量365g/eqのエポキシ樹脂(A−3)690質量部を得た。
実施例1において、ビフェノール186質量部(1モル)を4,4’−ジヒドロキシベンゾフェノン214質量部(1モル)に変更した以外は、実施例1と同様にして、エポキシ当量560g/eqのエポキシ樹脂(A−4)702質量部を得た。
実施例1において、1,6−ヘキサンジオールジグリシジルエーテルをジエチレングリコールジグリシジルエーテル(ナガセケムテックス製EX−850、エポキシ当量123g/eq)492質量部(2モル)に変更した以外は、実施例1と同様にして、エポキシ当量394g/eqのエポキシ樹脂(A−5)652質量部を得た。
実施例1において、1,6−ヘキサンジオールジグリシジルエーテルを1,4−ブタンジオールジグリシジルエーテル(ナガセケムテックス製EX−214L、エポキシ当量109g/eq)436質量部(2モル)に変更した以外は、実施例1と同様にして、エポキシ当量367g/eqのエポキシ樹脂(A−6)622質量部を得た。
温度計、冷却管、分留管及び撹拌器を取り付けたフラスコに、99%メタノール200質量部、ビフェノール186質量部(1モル)及び6−ブロモ−ヘキサン−1−オール362質量部(2モル)を仕込み、75℃で、窒素を吹き込みながら撹拌し溶解した。次に、この溶液に、86%水酸化カリウム130質量部(2モル)を溶解させた99%エタノール溶液200質量部を30分間かけて添加し、更に撹拌しながら4時間加熱還流した。反応混合物を室温に冷却した後、30%硫酸を用いて反応液を中和し、濾過、水洗、乾燥を行い、白色結晶を得た。
比較合成例1において、ビフェノール186質量部(1モル)を4,4’−ジヒドロキシジフェニルエーテル202質量部(1モル)に変更した以外は、比較例1と同様にして、エポキシ当量の305g/eqのエポキシ樹脂(B−2)475質量部を得た。
温度計、冷却管、分留管及び撹拌器を取り付けたフラスコに、4,4’−ジヒドロキシジフェニルエーテル202質量部、エピクロルヒドリン462質量部及びジメチルスルホキシド231質量部を仕込み、内圧を約6kPaまで減圧した後、50℃で還流させながら、48%水酸化カリウム233質量部を60分間かけて滴下した。尚、反応中は水を系外に留去、除去しながら反応を行った。反応混合物に、48%水酸化カリウムを滴下した後、70℃に昇温し、同温度でさらに1時間還流させながら反応させた。反応終了後、反応混合物にメチルイソブチルケトン400質量部と水450質量部を加え、副生した塩化カリウム水溶液を棄却した。その後、水400質量部を用いてジメチルスルホキシドを洗浄除去した後、150℃まで昇温して、エピクロルヒドリンを減圧蒸留回収して、エポキシ当量188g/eqのエポキシ樹脂(B−3)304質量部を得た。
(エポキシ樹脂組成物の調整及び物性評価)
[熱伝導性試験用の硬化物作成条件]
下記、表1及び表2に記載の配合に従い、硬化剤としてDIC製のフェノールノボラック樹脂「TD−2131」を配合し、更に硬化触媒として、2−エチル−4−メチルイミダゾール(2E4MZ)を加え、無機充填材として球状アルミナ(平均粒径12.2μm)を400部加えた。
ミキサーで十分混合した後、100℃/5分間混練したものを冷却した上で、粉砕した。
硬化条件:150℃で1時間、更に175℃で6時間
成形後板厚:1.2mm、樹脂量20%
上記条件で作成した硬化物を試験片として用い、熱伝導性の評価を行った。結果を表1及び表2にまとめて示した。
下記、表1及び表2に記載の配合に従い、硬化剤としてDIC製のフェノールノボラック樹脂「TD−2131」を配合し、更に硬化触媒として2−エチル−4−メチルイミダゾール(2E4MZ)を加えた。
硬化条件:150℃で1時間、更に175℃で6時間
成形後板厚:0.2mm、樹脂量100%
上記条件で作成した硬化物を試験片として用い、耐熱分解性の評価を行った。結果を表1及び表2にまとめて示した。
下記、表1及び表2に記載の配合に従い、硬化剤としてDIC製のフェノールノボラック樹脂「TD−2131」を配合し、更に硬化触媒として2−エチル−4−メチルイミダゾール(2E4MZ)を加え、最終的に各組成物の不揮発分(N.V.)が58質量%となるようにメチルエチルケトンを配合して調整した。
プライ数:6
銅箔:18μm 日鉱金属株式会社製 TCR箔
プリプレグ化条件:160℃/2分
硬化条件:200℃、2.9MPa、2時間
成形後板厚:0.8mm、樹脂量40%
上記条件で作成した硬化物を試験片として用い、以下の各種の評価を行った。結果を表1及び表2にまとめて示した。
京都電子株式社製QTM−500熱導率計を用いて非定常熱線法により測定した。
150℃で15分間保持した後、昇温速度:5℃/分、雰囲気:窒素ガスフロー、サンプル量:6mgで5%質量が減少する温度を評価した。
試験片を各実施例及び比較例それぞれ3個を用意し、121℃プレッシャークッカー試験機に6時間放置した後、288℃半田浴に30秒浸漬した後における膨れの有無を目視にて確認した。膨れの無いものを○、膨れの有るものを×とした。
試験片を25mm×75mmの大きさに切り出し、JIS K 6911に従って、島津製作所株式会社製の「AUTOGRAPH AG−I」を用いて測定し、曲げのび率を求めた。
JIS−K6481に準拠した。
JIS−K6481に準拠した。
Claims (12)
- 下記一般式(I)
で表わされるフェニレンユニットまたは下記一般式(ii)
で表わされるナフチレンユニットを表わし、nは、0〜10の整数を表わす。]
で表わされることを特徴とするエポキシ樹脂。 - 下記一般式(1)
又は下記一般式(2)
で表わされるジオール化合物(a)と、炭素原子数1〜9の直鎖状アルキレンジオールのジグリシジルエーテル、前記直鎖状アルキレンジオールの炭素原子に炭素原子数1〜18のアルキル基が結合した構造を有する分岐状アルキレンジオールのジグリシジルエーテル、及び前記アルキレンジオール中の連続する2個のメチレン基の間にエーテル結合が存在するジオール化合物のジグリシジルエーテルからなる群から選ばれる一種類以上のジグリシジルエーテル化合物(q)とを反応させることを特徴とするエポキシ樹脂の製造方法。 - 請求項3又は4に記載の方法により製造されるエポキシ樹脂。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂と硬化剤を含有するエポキシ樹脂組成物。
- 請求項6記載のエポキシ樹脂組成物を硬化させて得られる硬化物。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂、硬化剤、及び無機質充填剤を含有し、前記無機質充填剤の割合が20〜95質量%の範囲にある放熱樹脂材料。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂、硬化剤、及び無機質充填剤を含有し、前記無機質充填剤の割合が20〜95質量%の範囲にある半導体封止材料。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂、硬化剤、及び有機溶媒を含有する組成物を補強基材に含浸した含浸基材を半硬化させて得られるプリプレグ。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂、硬化剤、及び有機溶媒を含有するワニスからなる板状賦形物と、板状賦形物の面に重ねた銅箔とを加熱加圧成型して得られる回路基板。
- 請求項1、2又は5の何れか一つに記載のエポキシ樹脂、硬化剤、及び有機溶媒を含有する組成物を基材フィルム上に塗布し、乾燥させて得られるビルドアップフィルム。
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