JP5801653B2 - 低温硬化性エポキシ組成物 - Google Patents
低温硬化性エポキシ組成物 Download PDFInfo
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- 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
- C08G59/40—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 characterised by the curing agents used
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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
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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
- C08G59/40—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 characterised by the curing agents used
- C08G59/50—Amines
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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
- C08G59/40—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 characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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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
- C08G59/40—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 characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
- C08G59/40—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 characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- C08G59/623—Aminophenols
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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Description
(a)フェノール樹脂、及び
(b)エポキシ樹脂と、1つの第一級アミン又は第二級アミン及び少なくとも2つの第三級アミンを有する次の一般式のメチル化ポリアルキレンポリアミンとの反応生成物である変性アミン化合物:
本発明の実施態様として、以下の態様を挙げることができる:
《態様1》
1つの第一級アミン又は第二級アミン及び少なくとも2つの第三級アミンを有するメチル化ポリアルキレンポリアミンのエポキシアダクトであって、フェノール樹脂でブロックされているメチル化ポリアルキレンポリアミンのエポキシアダクトを、少なくとも1種含有する組成物。
《態様2》
(a)次の一般式を有するフェノール樹脂:
(b)エポキシ樹脂と、1つの第一級アミン又は第二級アミン及び少なくとも2つの第三級アミンを有する、次の一般式のメチル化ポリアルキレンポリアミンとの反応生成物である、変性アミン化合物:
《態様3》
熱硬化エポキシ樹脂における硬化剤又は促進剤としての、態様2に記載の組成物。
《態様4》
前記エポキシ樹脂が、多官能エポキシ樹脂、多価フェノールのグリシジルエーテル、二価フェノールのグリシジルエーテル、並びにレゾルシノール、ヒドロキノン、ビス−(4−ヒドロキシ−3,5−ジフルオロフェニル)−メタン、1,1−ビス−(4−ヒドロキシフェニル)−エタン、2,2−ビス−(4−ヒドロキシ−3−メチルフェニル)−プロパン、2,2−ビス−(4−ヒドロキシ−3,5−ジクロロフェニル)プロパン、2,2−ビス−(4−ヒドロキシフェニル)−プロパン及びビス−(4−ヒドロキシフェニル)−メタンのグリシジルエーテルからなる群より選択される、少なくとも1つの物質を含む、態様3に記載の組成物。
《態様5》
前記二価フェノールが、次の構造を有する、態様4に記載の組成物:
《態様6》
前記多官能エポキシ樹脂が、ノボラック樹脂のグリシジルエーテルを含む、態様4に記載の組成物。
《態様7》
前記多官能エポキシ樹脂が、ビスフェノールAのジグリシジルエーテル(DGEBA)、鎖伸長している又は高分子量であるDGEBA、ビスフェノールFのジグリシジルエーテル、エポキシノボラック樹脂又はこれらの組合せからなる群より選択される、少なくとも1種の物質を含む、態様4に記載の組成物。
《態様8》
前記多官能エポキシ樹脂が、スチレンオキシド、シクロへキセンオキシド、エチレンオキシド、プロピレンオキシド及びブチレンオキシド、並びにフェノールクレゾール、tert−ブチルフェノール、他のアルキルフェノール、ブタノール、2−エチルヘキサノール、C 4 〜C 14 アルコール等のグリシジルエーテル、又はこれらの組合せをさらに含む、態様4に記載の組成物。
(a)次の一般式のフェノール樹脂:
(b)エポキシ樹脂と、1つの第一級又は第二級アミン及び少なくとも2つの第三級アミンを有する次の一般式のメチル化ポリアルキレンポリアミンとの反応生成物である、変性アミン化合物:
N’−(3−ジメチルアミノプロピル)−N,N−ジメチル−プロパン−1,3−ジアミン(Polycat(商標)15触媒):Air Products and Chemicals,Inc製
ポリ(N−メチル)アゼチジン:Air Products and Chemicals,Inc製
Epon828及びEpon834:Hexion製
Cab−O−Sil M−5:Cabot製
CTBN/Epon8282アダクト(HyPox RA1340):CVC製
フェノール樹脂(AlNovol PN320):Cytec Specialty Chemicals製
378グラムのN’−(3−ジメチルアミノプロピル)−N,N−ジメチル−プロパン−1,3−ジアミンを、機械的攪拌機、熱電対、電気加熱マントル及び窒素パージを備えた3リットルの4つ口ガラス容器に充填する。この容器を、窒素下で80℃まで加熱する。温度が安定したら、189.7グラムのEpon828を、2〜3時間にわたって、測定して入れる。添加完了後に、その混合体を80℃で2時間保持する。20分にわたって、温度をゆっくりと150〜160℃へと上げ、そして735グラムのフェノール樹脂を60〜90分にわたって加える。その混合体を、さらに1時間攪拌しながら160℃で維持する。
9グラムのポリ(N−メチル)アゼチジンを、機械的攪拌機、熱電対、電気加熱マントル及び窒素パージを備えた3リットルの4つ口ガラス容器に充填する。この容器を、窒素下で80℃まで加熱する。温度が安定したら、10.1グラムのEpon828を、2〜3時間にわたって測定して入れる。添加完了後に、その混合体を、80℃で2時間保持する。20分にわたって、温度をゆっくりと150〜160℃へと上げ、そして17グラムのフェノール樹脂を60〜90分にわたって加える。その混合体を、さらに1時間攪拌しながら160℃で維持する。この生成物を、上記の温度で反応器から注ぎ出し、そして室温まで冷却させた後、粉砕プロセスを開始する。
9グラムのポリ(N−メチル)アゼチジンを、機械的攪拌機、熱電対、電気加熱マントル及び窒素パージを備えた3リットルの4つ口ガラス容器に充填する。この容器を窒素下で80℃まで加熱する。温度が安定したら、10.1グラムのEpon834を、2〜3時間にわたって、測定して入れる。添加完了後に、その混合体を、80℃で2時間保持する。20分にわたって、温度をゆっくりと150〜160℃へと上げ、そして9グラムのフェノール樹脂を60〜90分にわたって加える。その混合体を、さらに1時間攪拌しながら160℃で維持する。この生成物を、上記の温度で反応器から注ぎ出し、そして粉砕プロセスの開始前に室温まで冷却させる。
Claims (13)
- 請求項1に記載の反応生成物と、少なくとも1種の第2のエポキシ樹脂とを含む、組成物。
- 前記第2のエポキシ樹脂が、レゾルシノール、ヒドロキノン、ビス−(4−ヒドロキシ−3,5−ジフルオロフェニル)−メタン、1,1−ビス−(4−ヒドロキシフェニル)−エタン、2,2−ビス−(4−ヒドロキシ−3−メチルフェニル)−プロパン、2,2−ビス−(4−ヒドロキシ−3,5−ジクロロフェニル)プロパン、2,2−ビス−(4−ヒドロキシフェニル)−プロパン及びビス−(4−ヒドロキシフェニル)−メタンのグリシジルエーテルからなる群より選択される、少なくとも1つの物質を含む、請求項2に記載の組成物。
- 前記第2のエポキシ樹脂が、多官能エポキシ樹脂を含む、請求項2に記載の組成物。
- 前記第2のエポキシ樹脂が、多価フェノールのグリシジルエーテルを含む、請求項2に記載の組成物。
- 前記多官能エポキシ樹脂が、ノボラック樹脂のグリシジルエーテルを含む、請求項4に記載の組成物。
- 前記多官能エポキシ樹脂が、ビスフェノールAのジグリシジルエーテル(DGEBA)、鎖伸長している又は高分子量であるDGEBA、ビスフェノールFのジグリシジルエーテル、エポキシノボラック樹脂又はこれらの組合せからなる群より選択される、少なくとも1種の物質を含む、請求項4に記載の組成物。
- 前記多官能エポキシ樹脂が、フェノール、クレゾール、tert−ブチルフェノール、他のアルキルフェノール、ブタノール、2−エチルヘキサノール、C4〜C14アルコールのグリシジルエーテル、並びにスチレンオキシド、シクロへキセンオキシド、エチレンオキシド、プロピレンオキシド及びブチレンオキシド、又はこれらの組合せからなる群より選択される、少なくとも1種の物質を含む、請求項4に記載の組成物。
- 前記ポリアルキレンポリアミンが、ポリ(N−メチル)アゼチジンである、請求項2に記載の組成物。
- 前記第2のエポキシ樹脂が、ビスフェノールAのポリグリシジルエーテルを含む、請求項3に記載の組成物。
- フェノール樹脂と変性アミン化合物との反応生成物を含む組成物であって、前記変性アミン化合物が、1つの第一級アミン及び少なくとも2つの第三級アミンを有するポリ(N−メチル)アゼチジンとエポキシ樹脂との反応生成物である、組成物。
- さらに、ジシアンジアミド又は酸無水物を含む、請求項1〜12のいずれか一項に記載の組成物。
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US37899510P | 2010-09-01 | 2010-09-01 | |
US61/378,995 | 2010-09-01 | ||
US13/075,403 US9279032B2 (en) | 2010-09-01 | 2011-03-30 | Low temperature curable epoxy compositions |
US13/075,403 | 2011-03-30 |
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JP2012052113A JP2012052113A (ja) | 2012-03-15 |
JP5801653B2 true JP5801653B2 (ja) | 2015-10-28 |
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US (1) | US9279032B2 (ja) |
EP (1) | EP2426159B1 (ja) |
JP (1) | JP5801653B2 (ja) |
KR (1) | KR101239296B1 (ja) |
CN (1) | CN102558508B (ja) |
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WO2013069787A1 (ja) * | 2011-11-09 | 2013-05-16 | 東ソー株式会社 | エポキシ硬化剤 |
US9080007B2 (en) | 2013-02-28 | 2015-07-14 | Air Products And Chemicals, Inc. | Anhydride accelerators for epoxy resin systems |
EP2981565B1 (en) | 2013-04-05 | 2017-10-04 | Evonik Degussa GmbH | One component epoxy curing agents comprising hydroxyalkylamino cycloalkanes |
US9546243B2 (en) | 2013-07-17 | 2017-01-17 | Air Products And Chemicals, Inc. | Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions |
US11084959B2 (en) | 2016-06-22 | 2021-08-10 | 3M Innovative Properties Company | Curable compositions including a chromonic network, articles, and methods |
CN107522847B (zh) * | 2016-06-22 | 2020-05-15 | 3M创新有限公司 | 热活化的可固化组合物中的发色网络、制品和方法 |
RU2740475C2 (ru) | 2016-12-06 | 2021-01-14 | Эвоник Корпорейшн | Органофильные глины и буровые растворы, содержащие их |
US10450406B2 (en) * | 2017-08-30 | 2019-10-22 | Saudi Arabian Oil Company | Fluorinated polyimide-based epoxy materials |
EP3660069B1 (de) * | 2018-11-29 | 2024-01-03 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
CN113402731B (zh) * | 2021-07-09 | 2022-06-21 | 山西生物质新材料产业研究院有限公司 | 一种基于酶解木质素的固化促进剂、制备方法及其应用 |
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US8143331B2 (en) | 2007-02-07 | 2012-03-27 | Air Products And Chemicals, Inc. | Alkylated polyalkyleneamines and uses thereof |
US8735512B2 (en) | 2008-04-09 | 2014-05-27 | Air Products And Chemicals, Inc. | Curing agent for low temperature cure applications |
JP5517326B2 (ja) * | 2008-06-27 | 2014-06-11 | 株式会社Adeka | 一液型シアネート−エポキシ複合樹脂組成物 |
US7910667B1 (en) | 2009-09-11 | 2011-03-22 | Air Products And Chemicals, Inc. | Low temperature curable epoxy compositions containing phenolic-blocked urea curatives |
-
2011
- 2011-03-30 US US13/075,403 patent/US9279032B2/en not_active Expired - Fee Related
- 2011-08-26 EP EP11006993.7A patent/EP2426159B1/en not_active Not-in-force
- 2011-08-31 JP JP2011188895A patent/JP5801653B2/ja not_active Expired - Fee Related
- 2011-08-31 CN CN201110294288.4A patent/CN102558508B/zh not_active Expired - Fee Related
- 2011-08-31 KR KR1020110087735A patent/KR101239296B1/ko active IP Right Grant
Also Published As
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EP2426159B1 (en) | 2015-03-25 |
JP2012052113A (ja) | 2012-03-15 |
CN102558508B (zh) | 2015-07-29 |
KR20120022674A (ko) | 2012-03-12 |
US9279032B2 (en) | 2016-03-08 |
KR101239296B1 (ko) | 2013-03-06 |
EP2426159A1 (en) | 2012-03-07 |
CN102558508A (zh) | 2012-07-11 |
US20120077943A1 (en) | 2012-03-29 |
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