JP4304592B2 - 硬化性樹脂組成物及びその硬化物 - Google Patents
硬化性樹脂組成物及びその硬化物 Download PDFInfo
- Publication number
- JP4304592B2 JP4304592B2 JP2003337326A JP2003337326A JP4304592B2 JP 4304592 B2 JP4304592 B2 JP 4304592B2 JP 2003337326 A JP2003337326 A JP 2003337326A JP 2003337326 A JP2003337326 A JP 2003337326A JP 4304592 B2 JP4304592 B2 JP 4304592B2
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- JP
- Japan
- Prior art keywords
- resin composition
- polyvalent
- curable resin
- compound
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000011342 resin composition Substances 0.000 title claims description 65
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- 229960000834 vinyl ether Drugs 0.000 claims description 39
- -1 vinyl ether compound Chemical class 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 34
- 239000011347 resin Substances 0.000 claims description 34
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000004780 naphthols Chemical class 0.000 claims description 6
- 239000008393 encapsulating agent Substances 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 2
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- 238000000034 method Methods 0.000 description 25
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- 125000001424 substituent group Chemical group 0.000 description 9
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
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- 239000003054 catalyst Substances 0.000 description 4
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- 238000013329 compounding Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
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- 229910003475 inorganic filler Inorganic materials 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 3
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 3
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- 239000011248 coating agent Substances 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
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Description
本発明で用いる多価ヒドロキシ化合物(A)は、ヒドロキシ基の55モル%以上が芳香族性のヒドロキシ基であることを必須とする。ヒドロキシ基の半数以上が脂肪族性、即ちアルコール性ヒドロキシ基の場合は、電気、電子用途等で求められる誘電特性(誘電率、誘電正接)を満たすものではなく、好ましくない。特に得られる硬化物の誘電特性に優れる点から、前記多価ヒドロキシ化合物(A)中のヒドロキシ基の60モル%以上が芳香族性のヒドロキシ基であることが好ましく、80〜100モル%が芳香族性のヒドロキシ基であることが最も好ましい。
表1に記載した配合に従って、各種多価ヒドロキシ化合物と各種多価ビニルエーテル化合物を加熱(80〜120℃)混合し、更に表1記載の触媒を添加し均一に混合し、硬化性樹脂組成物(実施例1〜6)を得た。その組成物を直径5cmの円形金型に注ぎ、オーブン内で80℃×2時間+100℃×2時間+150℃×2時間の硬化条件で硬化させて、直径5cm×厚み2.0mmの円形硬化物試験片を得た。その試験片を用いて、誘電特性の評価指標として誘電率及び誘電正接を測定し、表2にその結果を記す。
誘電特性評価器アジレントテクノロジー製4291Bを用いて、100MHz〜1GHzの周波数における誘電率と誘電正接を測定した。
非特許文献1記載の手法に従って、ビスフェノールA、トリメチロールプロパン、ジエチレングリコールジメチルエーテルを表1記載の配合比に従って均一に混合し硬化性樹脂組成物を得て、比較例1とした。実施例と同様にして反応を行ったが、得られた生成物は粘稠な液体であり、硬化物が得られなかった。
エポキシ樹脂として、EPICLON N−665−EXP(大日本インキ化学工業株式会社製 クレゾールノボラック型エポキシ樹脂、エポキシ当量 205g/eq)を用いて、表1記載の配合に従って硬化性樹脂組成物を得、比較例2とした。実施例と同様にして硬化物を得た後、誘電特性を評価し、表2にその結果を記す。
TD-2131:Phenolite TD-2131(大日本インキ化学工業株式会社製フェノールノボラック樹脂 軟化点80℃ GPCより算出した平均官能基数3.5)
TMP:トリメチロールプロパン
PE:ペンタエリスリトール
DEDVE:ジエチレングリコールジビニルエーテル
TEDVE:トリエチレングリコールジビニルエーテル
CHDVE:シクロヘキサンジメタノールジビニルエーテル
TCA:トリクロロ酢酸
TPP:トリフェニルホスフィン
EPICLON N-665-EXP:クレゾールノボラック型エポキシ樹脂(大日本インキ化学工業株式会社製)
Claims (8)
- 多価ヒドロキシ化合物(A)と多価ビニルエーテル化合物(B)を含有する硬化性樹脂組成物であり、多価ヒドロキシ化合物(A)中のヒドロキシ基の55モル%以上が芳香族性ヒドロキシ基であることを特徴とする、プリント基板用樹脂組成物、電子部品の封止材用樹脂組成物、レジストインキ及び導電ペーストからなる群から選択される少なくとも1つの用途に調製される硬化性樹脂組成物。
- 多価ヒドロキシ化合物(A)が1分子中に2個を超えるヒドロキシ基を有する多価芳香族性ヒドロキシ化合物である請求項1記載の硬化性樹脂組成物。
- 多価ビニルエーテル化合物(B)がジビニルエーテル化合物である請求項1記載の硬化性樹脂組成物。
- 多価ヒドロキシ化合物(A)中のヒドロキシ基と多価ビニルエーテル化合物(B)中のビニルエーテル基のモル比(ヒドロキシ基)/(ビニルエーテル基)が、4/10〜10/10である請求項1〜3の何れか1項記載の硬化性樹脂組成物。
- 多価ヒドロキシ化合物(A)のヒドロキシ当量が40〜250g/eqであり、且つ多価ビニルエーテル化合物(B)のビニルエーテル当量が40〜250g/eqである請求項4記載の硬化性樹脂組成物。
- 多価ヒドロキシ化合物(A)が、フェノール類或いはナフトール類とアルデヒド類との重縮合物、フェノール類或いはナフトール類とジエン類との重付加物、及びフェノール類或いはナフトール類アラルキル樹脂からなる群から選ばれる1種以上の化合物である請求項5記載の硬化性樹脂組成物。
- 多価ビニルエーテル化合物(B)がポリアルキレンジビニルエーテル類、脂肪族環状骨格を有するジビニルエーテル類、及びビスフェノール骨格を有するジビニルエーテル類からなる群から選ばれる1種以上の化合物である請求項5記載の硬化性樹脂組成物。
- 請求項1〜7の何れか1項記載の硬化性樹脂組成物を硬化させて得られることを特徴とする硬化物。
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