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Method for preparing bis[3-chlorin-4-di(2,3- epoxy propyl) aminophenyl] methane

A technology of dichlorodiaminodiphenylmethane and dichlorodiaminodiphenyl, which is applied in the field of preparation of tetraglycidylamine compounds, can solve the problems of long preparation route and complicated operation, and achieve less performance loss and low viscosity , Good effect of flame retardancy

Active Publication Date: 2010-11-03
SHANGHAI PLASTICS RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of disadvantages, the preparation route is long, the operation is complicated, and the phase transfer catalyst benzyltriethylammonium chloride is used during dehydrochlorination

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] After filling 1110g (12 moles) epichlorohydrin and 150g alcohol-water mixed solvent (wherein ethanol 27g, water 123g) in the four-neck flask that volume is three liters, stir and mix evenly, add 267g (1 mole) 3 in batches, 3'-dichlorodiaminodiphenylmethane reacted at 75°C for 14 hours, then added 30% by weight of sodium hydroxide aqueous solution 667g (5 moles of NaOH), reacted at 55°C for 4.5 hours, then extracted the organic phase with 1100ml toluene, removed salt, alkali and water. Reduced pressure at 80°C to 30mmHg and evaporated toluene to obtain 441g of light yellow transparent viscous resin with a yield of 90%, epoxy value of 0.62, and viscosity (50°C) of 3Pa.S.

Embodiment 2

[0015] In addition to epichlorohydrin addition of 740g (8 moles), epichlorohydrin and 3,3'-dichlorodiaminodiphenylmethane in 21g ethylene glycol and 129g water at 50 ° C for 20 hours, 30 weight The dripping amount of % sodium hydroxide aqueous solution is 800g (6 moles of NaOH), and in 50 ℃ of reaction except 6 hours, other formula and operating procedure are the same as embodiment 1, and the result product yield is 466g, yield 95%, epoxy value 0.64 , viscosity (50 ℃) 4Pa.S, other properties and cured product properties are the same as in Example 1.

Embodiment 3

[0017] In addition to adding 1480g (16 moles) of epichlorohydrin and 3,3'-dichlorodiaminodiphenylmethane in 38g of 1,2-propanediol and 112g of water at 100 ° C for 8 hours, dropwise added 30% by weight NaOH Aqueous solution 533g (4 moles of NaOH) was reacted at 50 DEG C for 6 hours, other formulas and operating steps were the same as in Example 1, and the result was bis[3-chloro-4-bis(2,3-epoxypropyl)aminophenyl] The yield of methane is 456g, the epoxy value is 0.67, and the yield is 93%. Other performances and cured product performances are the same as in Example 1.

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Abstract

The molar ratio of epichlorohydrin and 3,3'-dichloro-diaminodiphenyl-methane is 8 to 16:1, the reflux reaction is carried out in the mixed solvent of alcohol and water by the weight ratio of 1: 0.3 to 6 for 8 to 20 hours at 50 to 100 DEG C, 30 percent by weight of sodium hydroxide solution is added into the reaction product for reaction for 3 to 6 hours at 50 to 60 DEG C, the salt, the alkali andthe water are removed by toluene extraction, the toluene is distilled by reduced pressure, so as to get the light yellow sticky and thick resin, the yield is 90 to 95 percent, the epoxy value is 0.60to 0.70 and the viscosity (50 DEG C) is 2 to 4Pa.S. The epoxy resin is solidified for 2.5 hours at 180 to 190 DEG C by using methyl tetrahydrophthalic anhydride, the thermal deformation temperature of the solidified material is 165 DEG C, the Rockwell hardness is 90 and the oxygen index is 27.5.

Description

1. Technical field [0001] The present invention relates to a preparation method of tetraglycidylamine compound, more specifically to a preparation method of bis[3-chloro-4-bis(2,3-epoxypropyl)aminophenyl]methane. 2. Background technology [0002] As we all know, tetraglycidyl-4,4'diaminodiphenylmethane (TGDDM) is a compound with excellent heat resistance, which can be used as matrix resin for carbon fiber reinforced composite materials, various coatings, electrical insulation materials, layers pressure materials, structural materials and civil construction materials, etc. However, it has recently been found that the compound has a water absorption rate of 5%, and is very sensitive to moisture under high temperature and high humidity, and the glass transition temperature drops by about 100°C, resulting in a decrease in compressive strength and interlaminar shear strength. For this reason, the aerospace industry requires the emergence of a matrix resin for cutting-edge compos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/36
Inventor 李伟烘
Owner SHANGHAI PLASTICS RES INST CO LTD
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