JP2006111809A - エポキシ樹脂,エポキシ樹脂組成物とその硬化物 - Google Patents
エポキシ樹脂,エポキシ樹脂組成物とその硬化物 Download PDFInfo
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- JP2006111809A JP2006111809A JP2004302771A JP2004302771A JP2006111809A JP 2006111809 A JP2006111809 A JP 2006111809A JP 2004302771 A JP2004302771 A JP 2004302771A JP 2004302771 A JP2004302771 A JP 2004302771A JP 2006111809 A JP2006111809 A JP 2006111809A
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- epoxy resin
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- resin composition
- carbon atoms
- formula
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 121
- 239000000203 mixture Substances 0.000 title claims abstract description 34
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 239000012948 isocyanate Substances 0.000 claims abstract description 16
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- 125000004036 acetal group Chemical group 0.000 claims abstract description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 6
- IEZWOVIWXFLQTP-UHFFFAOYSA-N hydroperoxyethene Chemical class OOC=C IEZWOVIWXFLQTP-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 methylene bisphenyl group Chemical group 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- KTIBRDNFZLYLNA-UHFFFAOYSA-N 2-(2-hydroxyethenoxy)ethenol Chemical compound OC=COC=CO KTIBRDNFZLYLNA-UHFFFAOYSA-N 0.000 claims description 9
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- 238000000034 method Methods 0.000 claims description 9
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
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- 239000000047 product Substances 0.000 description 15
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- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 4
- MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
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- 239000002966 varnish Substances 0.000 description 3
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
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- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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Abstract
Description
前記構造式(2)で表されるエポキシ樹脂(E−1)の合成
温度計、撹拌機、冷却間を取り付けたフラスコに,トリレンジイソシアネート(三井武田ケミカル社製:商品名コスモネートT−80)87.1g(0.50モル)とヒドロキシブチルビニルエーテル(ISP社製:商品名Rapi−Cure HBVE)116.2g(1.00モル)を仕込み50℃で1時間反応させた後、さらに80℃で1時間30分撹拌した。IR分析でイソシアネート基の吸収が消失し,ウレタン基の吸収が現れたことを確認した後に,室温でメチルアシッドフォスフェート(大八社製:商品名AP−1)0.6gとグリシドール(2,3−エポキシ−1−プロパノール)74.1g(1.00モル)を添加して,70℃で5時間反応を続けた。GPCでグリシドールが完全に消失したことを確認して得られた樹脂を取り出した。この樹脂のエポキシ当量は308g/eqであり,NMR(13C)(図1)とマススペクトル(図2)によって、構造式(2)の構造を有することを確認した。GPCによって測定された理論構造体(構造式(2)の構造)の含有率は59%であった。
前記構造式(3)で表されるエポキシ樹脂(E−2)の合成
トリレンジイソシアネートをジフェニルメタンジイソシアネート(三井武田ケミカル社製:商品名コスモネートPH)125.1g(0.50モル)に変更した以外は,実施例1と同様にして,目的のエポキシ樹脂を得た。エポキシ当量は340g/eq.であり,実施例1同様にNMRとマススペクトルによって,構造式(3)の構造を有することを確認した。GPCによって測定された理論構造体(構造式(3)の構造)の含有率は63%であった。
前記構造式(4)で表されるエポキシ樹脂(E−3)の合成
トリレンジイソシアネートを1,6−ヘキサメチレンジイソシアネート(東京化成工業社製)84.1g(0.50モル)に変更し,ヒドロキシブチルビニルエーテルをヒドロキシプロピルビニルエーテル102.1g(1.00モル)に変更した以外は,実施例1と同様にして,目的のエポキシ樹脂を得た。エポキシ当量は304g/eq.であり,実施例1同様にNMRとマススペクトルによって,構造式(4)の構造を有することを確認した。GPCによって測定された理論構造体(構造式(4)の構造)の含有率は52%であった。
下記構造式(7)で表される従来技術のウレタン変性エポキシ樹脂(E−4)の合成
公開特許公報昭60−260619号公報に従って合成した。ヘキサンジオール124.1g(1.05モル)とトリレンジイソシアネート348.3g(2.00モル)とジブチルスズジラウレート(東京化成工業社製)0.1gを仕込み80℃で5時間攪拌したのち、グリシドール140.8g(1.90モル)を加え80℃で8時間反応を続けた。GPCでグリシドールが完全に消失したことが確認して得られた樹脂を取り出した。この樹脂のエポキシ当量は324g/eqであった。
KIc=(3×P×L×a1/2)/(2×W×H2)
その結果を表1にまとめた。
Claims (11)
- ウレタン基(a)とアセタール基(b)とグリシジル基(c)とを含有するエポキシ樹脂と硬化剤を含有することを特徴とするエポキシ樹脂組成物。
- 前記エポキシ樹脂が、ジイソシアネート類とヒドロキシビニルエーテル類とグリシドール類の反応物である請求項1記載のエポキシ樹脂組成物。
- 前記エポキシ樹脂のエポキシ当量が218〜1000g/eq.の範囲である請求項1〜4のいずれか1つに記載のエポキシ樹脂組成物。
- イソシアネート類とヒドロキシビニルエーテル類とグリシドール類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。
- イソシアネート類とヒドロキシビニルエーテル類を反応させてウレタン変性ビニルエーテル類である中間体を製造する第1工程と、前記第1工程で得られた中間体とグリシドール類とを反応させてエポキシ樹脂を製造する第2工程からなる請求項6記載のエポキシ樹脂の製造方法。
- 一般式(1)
- 前記エポキシ樹脂がイソシアネート類とヒドロキシビニルエーテル類とグリシドール類とを反応させて得られるものである請求項8記載のエポキシ樹脂。
- 前記ジビニルエーテル類が、ポリオキシアルキレン骨格、シクロアルカン骨格及びアルキレン骨格からなる群から選ばれる1種以上の骨格を含有するものである請求項9記載のエポキシ樹脂。
- 請求項1〜5のいずれか1つに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。
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JP2011018814A (ja) * | 2009-07-10 | 2011-01-27 | Nippon Chemicon Corp | コンデンサ |
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JP2004156024A (ja) * | 2002-10-15 | 2004-06-03 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物、エポキシ樹脂の製造方法、新規エポキシ樹脂、及び新規フェノール樹脂 |
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JPS58145723A (ja) * | 1982-02-24 | 1983-08-30 | Mitsubishi Rayon Co Ltd | 熱硬化性樹脂組成物 |
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JPH08311152A (ja) * | 1995-05-24 | 1996-11-26 | Asahi Denka Kogyo Kk | ウレタン変成エポキシ樹脂組成物 |
JP2004156024A (ja) * | 2002-10-15 | 2004-06-03 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物、エポキシ樹脂の製造方法、新規エポキシ樹脂、及び新規フェノール樹脂 |
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JP2011018814A (ja) * | 2009-07-10 | 2011-01-27 | Nippon Chemicon Corp | コンデンサ |
JP2015081329A (ja) * | 2013-10-24 | 2015-04-27 | Dic株式会社 | ウレタン変性エポキシ樹脂、硬化性組成物、その硬化物、繊維強化複合材料、及び繊維強化樹脂成型品 |
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