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Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin

A technology of epoxy curing resin and compound, applied in the direction of organic chemistry, can solve the problems of rapid curing and poor stability of single liquid, achieve effective curing and improve the stability of single liquid

Inactive Publication Date: 2009-10-21
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a curing agent for curing the epoxy resin, imidazole is used, but the epoxy resin-imidazole mixture solution has the problem of rapid start of curing and extremely poor one-component stability (one-component stability).

Method used

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  • Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin
  • Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin
  • Clathrate compound, curing catalyst, composition for forming cured resin, and cured resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Under heating and reflux, 20 ml of a methanol solution of 10 mmol (1.10 g) of 2-ethyl-4-methylimidazole was added to 20 ml of a methanol solution of 5 mmol (1.05 g) of 5-nitroisophthalic acid while stirring. Then, crystals were precipitated immediately after heating was stopped, and clathrate (0.5 g, 33%) was obtained by filtering and vacuum drying after standing overnight at room temperature. Analysis of the obtained clathrate by NMR revealed that it was a 1:1 clathrate crystal. The obtained clathrate (5-NO2IPA-2E4MZ) 1 HNMR spectra and X-ray diffraction patterns are shown in Figure 18 and Figure 19 . For comparison, the X-ray diffraction pattern of 5-nitroisophthalic acid (5-NO2-IPA) is shown in Figure 19 . The thermal analysis (TG / DTA) diagram of the clathrate crystal obtained is shown in figure 1 . In addition, the thermal analysis (DSC) diagram based on the temperature change of the obtained clathrate crystal is shown in figure 2 , the thermal analysis ...

Embodiment 2

[0102] Add 15mmol (3.33g) of 5-tert-butylisophthalic acid and 18mmol (1.98g, 1.2eq.) of 2-ethyl-4-methylimidazole into 60ml of methanol, stir in an eggplant-shaped flask, and carry out Heat to reflux for 30 minutes to dissolve the crystals. Then, the precipitated crystal was filtered and vacuum-dried at room temperature to obtain an inclusion compound (2.34 g, 47%). Analysis of the obtained clathrate by NMR revealed that it was a 1:1 clathrate crystal. The thermal analysis (TG / DTA) diagram of the clathrate crystal obtained is shown in Figure 4 . In addition, the thermal analysis (DSC) diagram based on the temperature change of the obtained clathrate crystal is shown in Figure 5 , the thermal analysis (DSC) diagram at a fixed temperature (80 °C) is shown in Figure 6 .

Embodiment 3

[0104] Except having made 2-ethyl-4-methylimidazole into 16.5 mmol (1.81g, 1.1eq.), it carried out similarly to Example 2 (2.08g, 42%). The obtained clathrate was analyzed by NMR, and the result was a 1:1 clathrate crystal, and the thermal analysis (TG / DTA) chart was also consistent with the clathrate obtained in Example 2.

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Abstract

The present invention provides a curing catalyst (inclusion compound) for which the curing reaction is suppressed at low temperatures, allowing an improvement in the one-pot stability, but which can effectively cure a resin upon heat treatment. The inclusion compound comprises at least an isophthalic acid compound represented by a formula (I) [wherein R1 represents a C1 to C6 alkyl group or the like] and an imidazole compound represented by a formula (II) [wherein R2 represents a hydrogen atom or a C1 to C10 alkyl group or the like, and R3 to R5 each independently represents a hydrogen atom or a nitro group or the like].

Description

technical field [0001] The present invention relates to a novel inclusion compound, a curing catalyst containing the inclusion compound, a cured resin-forming composition using the curing catalyst, a method for producing a cured resin using the curable resin-forming composition, and a method for producing a cured resin using the curable resin-forming composition. The cured resin obtained by the method. Background technique [0002] Epoxy resins are widely used in various fields due to their excellent mechanical properties and thermal properties. Imidazole is used as a curing agent for curing the epoxy resin, but the mixture liquid of epoxy resin-imidazole has the problem of rapid start of curing and extremely poor one-liquid stability (one-liquid stability). [0003] Therefore, as a curing agent, it has been proposed to use an imidazole acid addition salt obtained by adding hydroxybenzoic acid to imidazole (see Patent Document 1), and to use a tetrahydric phenol compound (f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/54C07C63/24C07C205/57C08G59/68
CPCC07C205/57C07C63/24C08G59/686C07D233/64C07D233/58C07D233/54
Inventor 金子优美天野仓夏树
Owner NIPPON SODA CO LTD
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