JP5669289B2 - 新規エポキシ樹脂及びその製造方法、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及び該エポキシ樹脂を必須成分とする硬化物 - Google Patents
新規エポキシ樹脂及びその製造方法、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及び該エポキシ樹脂を必須成分とする硬化物 Download PDFInfo
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- JP5669289B2 JP5669289B2 JP2008135629A JP2008135629A JP5669289B2 JP 5669289 B2 JP5669289 B2 JP 5669289B2 JP 2008135629 A JP2008135629 A JP 2008135629A JP 2008135629 A JP2008135629 A JP 2008135629A JP 5669289 B2 JP5669289 B2 JP 5669289B2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/31—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/186—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with acids
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- Epoxy Resins (AREA)
Description
特許文献1には、プリント回路板において使用する感光画像形成性カチオン重合性組成物であって、多官能性エポキシ樹脂であるビスフェノールAノボラック型エポキシ樹脂及び、可塑剤としての役割を果す反応性希釈剤の混合物と、カチオン性光開始剤とからなる組成物を開示しているが、耐熱性は高いものの柔軟性は十分であるといえない問題があった。
本発明における新規エポキシ樹脂は一般式(1)で示されるものであり、式中のE1は一般式(4)、又は一般式(5)を示し、E3は一般式(2)一般式(3)、一般式(6)、又は一般式(7)のいずれかを示し、E2は一般式(8)〜一般式(11)のいずれかを示すが、E2の少なくとも1つが一般式(9)である。
本発明のエポキシ樹脂硬化物は本発明のエポキシ樹脂組成物を光照射及びまたは加熱することによって得られる。
冷却管を設置したセパラブルフラスコにTD−EL(4,7−メタノ−2,3−エポキシオクタヒドロ−1H−インデン−オール 丸善石油化学株式会社製)164.5部とリカシッドMH−700(メチルヘキサヒドロフタル酸無水物、新日本理化株式会社製)160.2部とトルエン17.0部を仕込み、窒素ガス雰囲気下撹拌しながら加熱昇温した。この時水酸基に対する酸無水物基は0.951であった。130℃で反応を行い酸無水物が無くなるまで反応を行った。この反応により1分子中にエポキシ基を1個持ち、且つカルボキシル基を1個持つ化合物が得られた。続いてセロキサイド2021 300.8部、ZX−1658 374.4部を加えて加熱して均一とした。触媒としてTPP−BB(n−ブチルトリフェニルホスホニウムブロマイド、北興化学工業株式会社製)を0.1部アセトンに溶解して系内に加えた。130℃で反応を行い、酸価が無くなったことを確認して反応終点とした。得られたエポキシ樹脂のエポキシ当量は210.4g/eqだった。図1にGPCによる分子量分布を、図2にFTIRの測定結果を示す。
TD−ELを227.9部、リカシッドMH−700を222.2部、セロキサイド2021を200.7部、ZX−1658を349.1部とし、トルエンは使用しなかった。それ以外は実施例1と同様な操作を行った。水酸基に対する酸無水物基は0.952であった。得られたエポキシ樹脂のエポキシ当量は272.1g/eqだった。
実施例1記載のセパラブルフラスコにTD−ELを267.1部、リカシッドMH−700を232.8部、セロキサイド2021を299.9部、ZX−1658を200.2部、トルエン26.3部を一括で仕込み、撹拌、昇温して均一にした。反応温度を90℃に保ち、酸無水物が無くなったことを確認するまで、保持した。この反応により1分子中にエポキシ基を1個持ち、且つカルボキシル基を1個持つ化合物が得られた。触媒としてTPP−BBを0.1部アセトンに溶解して系内に加えた。130℃で反応を行い、酸価が無くなったことを確認して反応終点とした。得られたエポキシ樹脂のエポキシ当量は313.9g/eqだった。
TD−ELを267.1部、リカシッドHNA−100(メチルナジック酸無水物、新日本理化株式会社製) 254.8部、セロキサイド2021を250.0部、ZX−1658 228.1部とし、トルエンは使用しなかった。それ以外は実施例1と同様な操作を行った。水酸基に対する酸無水物基は0.850であった。得られたエポキシ樹脂のエポキシ当量は342.1g/eqだった。
TD−ELを164.0部、リカシッドMH−700を159.9部、セロキサイド2021を309.9部、HBPA−DGE(水添BPA型エポキシ樹脂、丸善石油化学株式会社製)を366.1部、トルエンを36.0部とした以外は実施例3と同様な操作を行った。水酸基に対する酸無水物基は0.799であった。得られたエポキシ樹脂のエポキシ当量は271.6g/eqだった。
実施例1記載のセパラブルフラスコにペンタエリスリトール(三菱ガス化学株式会社製)43.3部、リカシッドMH−700を170.9部とトルエン37.8部を仕込み、窒素ガス雰囲気下撹拌しながら加熱昇温した。この時水酸基に対する酸無水物基は0.799であった。130℃で反応を行い酸無水物が無くなったことを確認してHBPA−DGEを785.8部加え、加熱して均一とした。触媒としてTPP−BBを0.1部アセトンに溶解して系内に加えた。150℃で反応を行い、酸価が無くなったことを確認して反応終点とした。得られたエポキシ樹脂のエポキシ当量は420.8g/eqだった。
ペンタエリスリトールを48.9部、リカシッドMH−700を138.3部、HBPA−DGEを403.1部、セロキサイド2021を403.1部とした以外は実施例1と同様な操作を行った。この時水酸基に対する酸無水物基は0.572であった。得られたエポキシ樹脂のエポキシ当量は273.5g/eqだった。
ペンタエリスリトールを38.5部、リカシッドHNA−100を207.6部、ZX−1658を261.2部、セロキサイド2021を492.8部とした以外は実施例1と同様な操作を行った。この時水酸基に対する酸無水物基は0.996であった。得られたエポキシ樹脂のエポキシ当量は252.6g/eqだった。
Claims (4)
- 1分子中に水酸基を1個持ち且つエポキシ基を1個持つ化合物と、酸無水物類を含むカルボン酸類と、エポキシ樹脂類とを反応することによって得られる下記一般式(1)で示される新規エポキシ樹脂組成物。
- 前記酸無水物類を含むカルボン酸類が1分子中にカルボキシル基を2個持つ化合物又は酸無水物である請求項1記載の新規エポキシ樹脂組成物。
- 請求項1又は2記載のエポキシ樹脂組成物を必須成分とし、硬化剤を含有してなる硬化性エポキシ樹脂組成物。
- 請求項3に記載の硬化性エポキシ樹脂組成物を熱硬化及び/又は光硬化させてなる硬化物。
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JP2008135629A JP5669289B2 (ja) | 2008-05-23 | 2008-05-23 | 新規エポキシ樹脂及びその製造方法、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及び該エポキシ樹脂を必須成分とする硬化物 |
KR1020107026048A KR101540831B1 (ko) | 2008-05-23 | 2009-05-19 | 신규 에폭시 수지 및 그의 제조방법, 그 에폭시 수지를 필수성분으로 하는 에폭시 수지 조성물 및 그 에폭시 수지를 필수성분으로 하는 경화물 |
PCT/JP2009/059484 WO2009142317A1 (ja) | 2008-05-23 | 2009-05-19 | 新規エポキシ樹脂及びその製造方法、該エポキシ樹脂を必須成分とするエポキシ樹脂組成物及び該エポキシ樹脂を必須成分とする硬化物 |
CN2009801181285A CN102037048B (zh) | 2008-05-23 | 2009-05-19 | 新型环氧树脂及其制造方法、以该环氧树脂为必需成分的环氧树脂组合物及以该环氧树脂为必需成分的固化物 |
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MA41308A (fr) * | 2014-12-22 | 2017-11-14 | Nippon Soda Co | Composition de résine époxy |
KR102454213B1 (ko) * | 2021-03-19 | 2022-10-14 | 한국화학연구원 | 산 무수물기반 에폭시 화합물, 이를 포함하는 에폭시 접착제 조성물 및 이로부터 제조된 경화물 |
KR102448685B1 (ko) * | 2021-03-26 | 2022-09-29 | 한국화학연구원 | 지방산 개질된 산 무수물기반 에폭시 화합물을 포함하는 에폭시 접착제 조성물 및 이로부터 제조된 경화물 |
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