Curing agent for anionically curable compounds, curable composition, cured product, novel imidazole-based compound and use of same

An imidazole-based compound, curing technology, applied in the direction of organic chemistry, bulk chemical production, etc., can solve the problems of imidazole-based curing agent, exhaust, etc., to achieve excellent uniform mixing, high storage stability, and easy operation Effect

Inactive Publication Date: 2015-02-04
THE NIPPON SYNTHETIC CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the mechanism that makes this curing agent latent can only generate primary amines, which cannot be applied to imidazole-based curing agents that do not have primary amines
In addition, this curing agent also has the problem of generating outgassing during curing

Method used

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  • Curing agent for anionically curable compounds, curable composition, cured product, novel imidazole-based compound and use of same
  • Curing agent for anionically curable compounds, curable composition, cured product, novel imidazole-based compound and use of same
  • Curing agent for anionically curable compounds, curable composition, cured product, novel imidazole-based compound and use of same

Examples

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Embodiment

[0079] Hereinafter, although an Example is given and this invention is demonstrated more concretely, this invention is not limited to the following Example unless the summary is exceeded.

Synthetic example 1

[0080] [Synthesis Example 1: Synthesis of Dimethyl 2-(2-butylimidazol-1-yl)succinate]

[0081] 9.5 g (0.06 mol) of diazabicycloundecene (DBU), 18 mL of acetonitrile, and 17.1 g (0.14 mol) of 2-butylimidazole were put into a 100 mL four-necked flask, and stirred at 25°C. 18.0 g (0.12 mol) of dimethyl fumarate was dripped there, and it was made to react at 25 degreeC for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, followed by extraction with 70 mL of dichloromethane and 50 mL of water. The fractionated organic layer was concentrated, and the obtained concentrate was purified by silica gel column chromatography (ethyl acetate / hexane=1 / 1) to obtain liquid 2-(2-butylimidazol-1-yl)succinic acid Dimethyl ester. The obtained dimethyl 2-(2-butylimidazol-1-yl)succinate was 13.1 g, and the yield was 39%.

[0082] 2-(2-butylimidazol-1-yl) dimethyl succinate begins the detachment reaction of the protecting group at a temperature of 17...

Synthetic example 2

[0083] [Synthesis Example 2: Synthesis of Dimethyl 2-(2-Undecylimidazol-1-yl)succinate]

[0084] 7.9 g (0.05 mol) of DBU, 15 mL of acetonitrile, and 25.5 g (0.11 mol) of 2-undecylimidazole were charged into a 100 mL four-necked flask, and stirred at 25°C. 15.0 g (0.10 mol) of dimethyl fumarate was dripped there, and it was made to react at 25 degreeC for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, followed by extraction with 70 mL of dichloromethane and 50 mL of water. The fractionated organic layer was concentrated, and the obtained concentrate was purified by silica gel column chromatography (ethyl acetate / hexane=3 / 2) to obtain liquid 2-(2-undecylimidazol-1-yl) Dimethyl succinate. The obtained dimethyl 2-(2-undecylimidazol-1-yl)succinate was 12.1 g, and the yield was 32%.

[0085] 2-(2-undecylimidazol-1-yl) dimethyl succinate begins the detachment reaction of the protecting group at a temperature of 194°C, 2-(2-undecyli...

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Abstract

The present invention provides: a curing agent for anionically curable compounds, which is composed of an imidazole-based compound wherein the 1-position of the imidazole skeleton is protected with a protecting group (A) that can be eliminated at a temperature of 50°C or more; a curable composition which contains the curing agent and an anionically curable compound; a cured product which is obtained by curing the composition; the above-mentioned novel imidazole-based compound; and use of the imidazole-based compound. The present invention provides a novel imidazole-based curing agent which is easily handled and has excellent storage stability and good curability even in cases where the curing agent is used as a one-pack type curing agent. This imidazole-based compound is exemplified by an imidazole-based compound represented by general formula (1). In formula (1), A represents a protecting group that can be eliminated at a temperature of 50°C or more; and each of R1-R3 independently represents a hydrogen atom, an alkyl group having 1-15 carbon atoms or a phenyl group.

Description

technical field [0001] The present invention relates to a curing agent for anion-curable compounds for curing anion-curable compounds such as epoxy compounds and episulfide compounds, a curable composition comprising the curing agent and anion-curable compounds, and the composition obtained by curing the composition A cured product and a novel imidazole-based compound useful as a curing agent for the anion-curable compound. In addition, the present invention also relates to the use of the aforementioned novel imidazole-based compound as a curing agent for anion-curable compounds. Background technique [0002] As a curing agent for curing anion-curable compounds such as epoxy compounds and episulfide compounds, curing agents for anion-curable compounds containing imidazole-based compounds (hereinafter also referred to as imidazole-based curing agents) are being used. However, when a liquid imidazole-based curing agent is used as a one-component curing agent, there is a probl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/40
CPCC07D231/12C08G59/5073C08L63/00Y02P20/55C08G59/40C08G75/08
Inventor 工藤健二有光晃二
Owner THE NIPPON SYNTHETIC CHEM IND CO LTD
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