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High-purity epoxy compound and method for producing same

A technology of epoxy compound and manufacturing method, which is applied in the direction of organic chemical methods, chemical instruments and methods, chemical/physical processes, etc., can solve the problems of unpurified distillation, high viscosity, low purity, etc., and achieve less impurity content and lower Effect of high viscosity and chemical purity

Inactive Publication Date: 2012-12-12
TORAY FINE CHEMICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this production method, there are following problems: Since epichlorohydrin reacts with acetic acid simultaneously with 3,4'-diaminodiphenyl ether, a large amount of side reaction products are produced, and The resulting N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether becomes high viscosity
As a result, the obtained epoxy resin is far from the physical properties expected by reacting N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether with a curing agent.
[0008] In addition, since the low-purity N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether obtained by the conventional production method and the impurities contained therein have high boiling points, Therefore, if methods such as distillation and purification are used to separate and remove impurities and improve chemical purity, high-temperature distillation is required, and there are problems such as no purification or low yield during distillation.
Therefore, industrially usable epoxy compounds containing high-purity N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether have not yet been produced.

Method used

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  • High-purity epoxy compound and method for producing same
  • High-purity epoxy compound and method for producing same
  • High-purity epoxy compound and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] In a four-necked flask equipped with a thermometer, a cooling tube, and a stirrer, add 1500 g (16.2 moles) of epichlorohydrin and 675 g (2.5 times by weight / 3,4'-diaminodiphenyl ether) of 2-propanol. 270 g (1.35 mol) of 3,4'- diamino diphenyl ether was added. This mixed solution was stirred at a temperature of 80° C. for 21 hours to perform an addition reaction. From the addition reaction liquid, 1178 g of 2-propanol and a part of remaining epichlorohydrin were distilled off under reduced pressure. To the obtained concentrate, 540 g of toluene (2.0 times by weight / 3,4'-diaminodiphenyl ether) and 13.8 g (0.041 mol) of tetrabutylammonium bisulfate as a catalyst for the cyclization reaction were added, and then 675 g (8.1 mol) of 48% sodium hydroxide was added dropwise over 30 minutes at a temperature of °C, and then aged while stirring at a temperature of 30 °C for 4 hours to perform a cyclization reaction. After completion of the cyclization reaction, the generated sal...

Embodiment 2

[0092] In Example 1, the same procedure as in Example 1 was carried out except that 2-propanol was changed to 675 g of ethanol (2.5 times by weight / 3,4'-diaminodiphenyl ether). 575 g of a brown viscous liquid containing N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether as a main component (100% of theoretical yield) was obtained. The chemical purity of this epoxy compound was measured by the method described above using HPLC, and it was 87% (HPLC area %). The epoxy equivalent was 123 g / eq, and the viscosity measured at 40° C. using an E-type viscometer was 35 Pa·s.

Embodiment 3

[0094] In Example 1, the amount of 2-propanol as an addition reaction solvent was changed from 675 g to 1080 g (4.0 weight times / 3,4'-diaminodiphenyl ether), and the reaction time of the addition reaction was changed from It implemented similarly to Example 1 except having changed 21 hours into 25 hours, and having changed the quantity of the 2-propanol distilled off from the addition reaction liquid, and the residual epichlorohydrin into 1620 g. 565 g of a brown viscous liquid containing N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether as a main component (99% of theoretical yield) was obtained. The chemical purity of the epoxy compound was measured by the method described above using HPLC, and it was 91% (HPLC area %). The epoxy equivalent was 119 g / eq, and the viscosity measured at 40° C. using an E-type viscometer was 29 Pa·s.

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Abstract

The present invention provides an epoxy compound comprising highly pure N, N, N', N'-tetraglycidyl-3,4'-diaminodiphenyl ether and a method for producing the same. The highly pure N, N, N', N'-tetraglycidyl-3,4'-diaminodiphenyl ether is produced by means of an addition reaction step wherein, in a protic polar solvent, 3,4'-diaminodiphenyl ether is reacted with epicholorohydrin for at least 12 hours at 65-100 DEG C, forming N, N, N', N'-tetrakis(3-chloro-2-hydroxypropyl)-3,4'-diaminodiphenyl ether, and a cyclization reaction step wherein the aforementioned N, N, N', N'-tetrakis(3-chloro-2-hydroxypropyl)-3,4'-diaminodiphenyl ether is reacted with an alkali compound, causing dehydrochlorination.

Description

technical field [0001] The present invention relates to an industrially useful epoxy compound containing high-purity N,N,N',N'-tetraglycidyl-3,4'-diaminodiphenyl ether and a method for producing the same. Background technique [0002] Epoxy compounds are compounds widely used in the fields of organic chemistry and polymer chemistry, and are useful compounds in various fields of industrial use such as fine chemicals, pharmaceutical and agricultural chemical raw materials, and resin raw materials, as well as electronic information materials and optical materials. . [0003] In addition, polyfunctional epoxy compounds are cured with various curing agents, so that they are generally made into cured products with excellent mechanical properties, water resistance, chemical resistance, heat resistance and electrical properties. It is used in a wide range of fields such as composite materials. Among them, glycidylamine-type epoxy compounds are widely used in composite materials an...

Claims

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Application Information

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IPC IPC(8): C07D303/36C07D301/27B01J31/02C07B61/00
CPCB01J2231/40C07D303/36B01J31/0239C07D301/27B01J31/0268B01J31/02C07B61/00
Inventor 石川学哉加藤秀利中谷仁郎新井厚仁坂田宏明大皷宽
Owner TORAY FINE CHEMICALS CO LTD
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