JP6921134B2 - 室温イオン液体硬化剤 - Google Patents
室温イオン液体硬化剤 Download PDFInfo
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- JP6921134B2 JP6921134B2 JP2018567838A JP2018567838A JP6921134B2 JP 6921134 B2 JP6921134 B2 JP 6921134B2 JP 2018567838 A JP2018567838 A JP 2018567838A JP 2018567838 A JP2018567838 A JP 2018567838A JP 6921134 B2 JP6921134 B2 JP 6921134B2
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- Prior art keywords
- epoxy
- amine
- curing agent
- acid
- room temperature
- Prior art date
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- 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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Description
本発明は、アミンエポキシ硬化剤としての室温イオン液体、かかる液体塩化合物を含有する硬化性エポキシド系組成物、ならびにかかる化合物および組成物の製造方法に関する。
本開示は、速硬化性および/または低温硬化性のエポキシ系エポキシ硬化剤であって、建築用ブロックとしての室温イオン液体(RTIL)またはアミンエポキシ硬化剤のための促進剤を含むエポキシ硬化剤に関し、かかる液体塩化合物を含有する硬化性エポキシド系組成物に関し、さらにかかる化合物および組成物の製造方法に関する。
(a)式(I):
(b)6未満のpKa(酸解離定数の対数の負数)を有する有機酸と
の反応生成物である。
エポキシ硬化剤としての室温イオン液体およびかかる液体塩化合物を含有するエポキシ硬化性組成物、ならびにかかる化合物および組成物の製造方法が提供される。本開示によれば、室温イオン液体エポキシ硬化剤は、費用対効果が高く、特に周囲温度および低温でエポキシを速硬化し、かつ単独の速硬化剤として、または他のアミンエポキシ硬化剤との共硬化剤として適している。適切な用途としては、接着剤、エレクトロニクス、複合材、コーティング、プライマー、シーラント、硬化コンパウンド、建築用製品、床材製品、および複合製品が挙げられるが、これらに限定されない。さらに、このような接着剤、コーティング、プライマー、シーラント、または硬化コンパウンドは、金属、FRP複合材、プラスチックまたはセメント質基材に適用され得る。本開示によるエポキシハードナーは、室温および低温でのエポキシとの高い反応性、液体として使用する場合の使いやすさ、白化の低減または排除、低臭気および高いガラス転移温度(Tg)のような複数の重要な利点を備えている。室温イオン液体塩の別の重要な利点は、エポキシ樹脂のホモ重合をあまり誘導せず、かつ非常に優れた機械的特性に寄与し得ることである。
以下の合成例は、本発明の特定の態様または実施形態を例示するために示されており、添付の特許請求の範囲を限定するものではない。
1モルのアミンおよび60mlのn−ブタノールを、オーバーヘッド機械式撹拌器(overhead mechanical stirrer)、窒素注入口、滴下漏斗および熱電対を備えた四口丸底フラスコに装入した。反応物を撹拌し、高純度の窒素で0.5時間にわたりパージした。その後、200mLのn−ブタノールに溶けた1モルの酸を、ゆっくりと滴下し、滴下の間、温度が70℃よりも高くならないように維持した。反応を80℃でさらに2時間行い、次いで温度を110℃まで徐々に上げ、その一方で、真空をかけて、p−TSAからn−ブタノールおよび含まれる水を蒸留した。高真空下で1〜2時間保持した後、試料を収集し、含水量の試験に付した。含水量が規格を満たしたら、得られたアミン塩を室温に冷却し、粘稠な黄色の液体を得た。
149gのテトラエチレンペンタミン(TEPA)および40mlのn−ブタノールを、オーバーヘッド機械式撹拌器、窒素注入口、滴下漏斗および熱電対を備えた四口丸底フラスコに装入した。反応物を撹拌し、高純度の窒素で0.5時間にわたりパージした。その後、160mLのn−ブタノールに溶けた150gのp−トルエンスルホン酸(p−TSA)を、ゆっくりと滴下し、温度が70℃よりも高くならないように維持した。反応を80℃でさらに2時間行い、次いで温度を110℃まで徐々に上げ、その一方で、真空をかけて、p−TSAからn−ブタノールおよび含まれる水を蒸留した。高真空下で1〜2時間保持した後、試料を収集し、含水量の試験に付した。含水量が規格を満たしたら(すなわち1%未満)、得られたアミン塩を室温に冷却し、粘稠な蛍光黄色液体を得た。
実施例2は、348.6gのペンタエチレンヘキサミン(PEHA)を、溶媒としてのn−ブタノールの存在下で、285.2gのp−トルエンスルホン酸(p−TSA)H2Oと反応させることを除いて、実施例1の工程に従って行われ、粘稠な褐色の着色液体が得られた。
実施例3は、溶媒としてのn−ブタノールの存在下で、261.4gのN,N’−ビス(3−アミノプロピル)エチレンジアミン(Am4)を、285.2gのp−TSA.H2Oと反応させることを除いて、実施例1の工程に従って行われ、粘稠な淡色液体が得られた。
実施例4は、溶媒としてのn−ブタノールの存在下で、261.4gのAm4を、207.0gのサリチル酸(SA)と反応させることを除いて、実施例1の工程に従って行われ、中粘度(すなわち1,000〜10,000cps)の淡色液体が得られた。
実施例5は、溶媒としてのn−ブタノールの存在下で、261.4gのAm4を、225.1gのトリフルオロメタンスルホン酸(TFMSA)と反応させることを除いて、実施例1の工程に従って行われ、中粘度の淡色液体が得られた。
72部の実施例1および28部のベンジルアルコールで構成されたエポキシ硬化剤を準備する。ANCAMINE(登録商標)1637lvおよびANCAMINE(登録商標)1767を比較例(Air Products & Chemicals, Inc.から入手可能)で使用する。結果を第2表に示す。
72部の実施例3および28部のAMICURE PACMで構成される硬化剤を準備する。AMICURE PACMは、Air Products & Chemicals, Inc.の商標であり、PACMを表す。結果を第3表および図1に示す。
Claims (19)
- 前記少なくとも1種のポリアルキレンポリアミン化合物は、異種のポリアルキレンポリアミン化合物の混合物である、請求項1記載のエポキシ硬化剤。
- 前記少なくとも1種のポリアルキレンポリアミン化合物は、ポリアルキレンポリアミンの誘導体である、請求項1記載のエポキシ硬化剤。
- 前記ポリアルキレンポリアミンの誘導体が、アルキル化ポリアルキレンポリアミン、ベンジル化ポリアルキレンポリアミン、ヒドロキシアルキル化ポリアルキレンポリアミン、およびポリアルキレンポリアミン付加物からなる群から選択される1種以上の化合物である、請求項1記載のエポキシ硬化剤。
- 前記反応生成物を形成する反応混合物における成分(b)の成分(a)に対するモル比は、0より大〜1.8までである、請求項1記載のエポキシ硬化剤。
- 前記反応生成物を形成する反応混合物における成分(b)の成分(a)に対するモル比は、0.3〜1.3までである、請求項1記載のエポキシ硬化剤。
- 第2のアミンをさらに含み、前記第2のアミンは、第一級アミン、第二級アミン、第三級アミン、第四級アミン、またはそれらの誘導体である、請求項1記載のエポキシ硬化剤。
- 前記第2のアミンは、アミノエチルピペラジン、イソホロンジアミン、4,4’−メチレンビス(シクロヘキシルアミン)、エーテルアミン、およびそれらの組み合わせからなる群から選択される化合物である、請求項7記載のエポキシ硬化剤。
- 前記少なくとも1種のエポキシ樹脂は、ビスフェノールAジグリシジルエーテル、ビスフェノールFジグリシジルエーテル、およびエポキシノボラックからなる群から選択される化合物を含む、請求項9記載の硬化性エポキシ系組成物。
- (iii)第2のアミンをさらに含み、前記第2のアミンは、第一級アミン、第二級アミン、第三級アミン、第四級アミン、またはそれらの誘導体である、請求項9記載の硬化性エポキシ系組成物。
- 前記(iii)第2のアミンは、アミノエチルピペラジン、イソホロンジアミン、4,4’−メチレンビス(シクロヘキシルアミン)、エーテルアミン、およびそれらの組み合わせからなる群から選択される化合物である、請求項11記載の硬化性エポキシ系組成物。
- (iv)ベンジルアルコール、フルフリルアルコール、ポリエチレングリコール、およびそれらの組み合わせからなる群から選択される少なくとも1種の改質剤をさらに含む、請求項9記載の硬化性エポキシ系組成物。
- (v)アクリレートをさらに含む、請求項13記載の硬化性エポキシ系組成物。
- 前記(v)アクリレートは、ラウリルアクリレート、1,6−ヘキサンジオールジアクリレート、トリメチロールプロパントリアクリレート、ポリ(アルキレンオキシド)ジアクリレート、ポリウレタンジアクリレート、およびそれらの組み合わせからなる群から選択される、請求項14記載の硬化性エポキシ系組成物。
- 請求項9記載の硬化性エポキシ系組成物を混合することを含む硬化エポキシを形成する方法。
- 請求項9記載の硬化性エポキシ系組成物の接触生成物を含む硬化エポキシ樹脂。
- 請求項9記載の組成物から得られた物品。
- 前記物品は、接着剤、コーティング、プライマー、シーラント、硬化性コンパウンド、建築用製品、床材製品、または複合材製品である、請求項18記載の物品。
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EP3569630B1 (de) | 2018-05-17 | 2022-08-03 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
US11359048B2 (en) | 2018-05-17 | 2022-06-14 | Evonik Operations Gmbh | Fast-curing epoxy systems |
WO2020037502A1 (en) | 2018-08-21 | 2020-02-27 | Evonik Operations Gmbh | Fast curing epoxy system for producing rigid foam and use of the foam in composites or as insulation material |
CN109608893B (zh) * | 2018-12-04 | 2020-12-08 | 河南省交通规划设计研究院股份有限公司 | 桥面防水粘结层用废胎胶粉沥青材料及其制备方法 |
FR3091406B1 (fr) | 2018-12-31 | 2021-01-15 | Centre National De Recherche Scient Cnrs | Matériau pour l’isolation électrique et procédé de fabrication |
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US4229563A (en) * | 1979-08-03 | 1980-10-21 | Ameron, Inc. | Aromatic amidoamines |
US5618905A (en) * | 1995-04-11 | 1997-04-08 | Air Products And Chemicals, Inc. | Partially methylated polyamines as epoxy curing agents |
US6911109B2 (en) * | 2000-12-11 | 2005-06-28 | Henkel Corporation | Two-part, room temperature curable epoxy resin/ (meth)acrylate compositions and process for using same to bond substrates |
EP1436339B1 (en) * | 2001-08-28 | 2005-10-19 | Resolution Research Nederland B.V. | Low viscosity curing agents compositions in epoxy resin systems for low temperature cure applications |
US8518547B2 (en) * | 2007-02-07 | 2013-08-27 | Air Products And Chemicals, Inc. | Alkylated polyalkylene polyamines and uses thereof |
US8519091B2 (en) * | 2007-04-10 | 2013-08-27 | Air Products And Chemicals, Inc. | Polyalkyleneamine adducts as curing agents for thick layer water-based epoxy systems |
US9840588B2 (en) * | 2009-12-18 | 2017-12-12 | Hexion Inc. | Epoxy resin curing compositions and epoxy resin systems including same |
CN102432830B (zh) * | 2011-08-02 | 2013-04-10 | 华南理工大学 | 一种水性环氧树脂固化剂乳液及其制备方法 |
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WO2013081895A2 (en) * | 2011-12-01 | 2013-06-06 | Dow Global Tecnologies LLC | Liquid accelerator composition for hardeners |
WO2015144391A1 (en) * | 2014-03-28 | 2015-10-01 | Huntsman Advanced Materials (Switzerland) Gmbh | A process for manufacturing a fiber reinforced epoxy composite article, the composite articles obtained and the use thereof |
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US20220356298A1 (en) | 2022-11-10 |
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KR102586629B1 (ko) | 2023-10-11 |
US20190330412A1 (en) | 2019-10-31 |
KR20190022758A (ko) | 2019-03-06 |
EP3475330A1 (en) | 2019-05-01 |
CN109415488B (zh) | 2022-04-29 |
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WO2018000125A1 (en) | 2018-01-04 |
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