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Preparation method of tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenyl-methane

A technology of diaminodiphenylmethane and tetraglycidyl, which is applied in the field of preparation of tetraglycidylamine compounds, and can solve problems such as difficult separation, high cost of catalyst application, and high reaction temperature

Active Publication Date: 2010-03-10
SHANGHAI PLASTICS RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, US Pat.5,149,841 uses phase transfer catalyst tetramethylammonium chloride or tetrabutylammonium chloride to catalyze the reaction, the reaction temperature in the addition reaction stage is 98-100°C, and the reaction time is 6.5hr. US Pat.5,280.069 uses lanthanum nitrate, Benzyltrimethylammonium chloride is used as a catalyst, and the reaction temperature in the addition reaction stage is 80-90 ° C, and the reaction is 9 hours. The reaction temperature of the prior art is relatively high, and it brings certain difficulties to the separation during the product preparation process. The catalyst The application cost is obviously high

Method used

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  • Preparation method of tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenyl-methane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 254g (1mol) 3,3'-diethyl-4,4'-diaminodiphenylmethane, 740g (8mol) epichlorohydrin, trichloro Cobalt acetate 2g, 78g ethylene glycol and 45g water, after stirring and dissolving, be warming up to 60 ℃ and react for 7 hours, then add 320g acetone and 412g 30% by weight aqueous potassium carbonate solution and react at 55 ℃ for 5 hours, then add 900ml toluene to extract four Glycidyl-3,3'-diethyl-4,4'-diaminodiphenylmethane, steam out toluene, the product is reddish liquid resin, its performance is: epoxy value is 0.72 equivalent / 100 grams, The viscosity is 0.48Pa.s at 25°C.

[0019] 10g tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenylmethane product, 5g4,4'-diaminodiphenylsulfone and 0.3g fumed silicon dioxide were mixed together and placed in Cured at 160°C for 2 hours, cured at 210°C for 2 hours, the heat distortion temperature was 182.1°C, the impact modulus of the cast sample was 3.2Gpa, and the Rockwell hardness E 85.

Embodiment 2

[0021] Except epichlorohydrin 462.5g (5mol), potassium nitrate 1.3g, 1.2-propanediol 70g, water 40g, addition reaction at 50°C for 6 hours, add 373g of 30wt% sodium hydroxide aqueous solution, cyclization reaction at 50°C for 4 hours, Except adding 800ml of toluene for extraction, other charging amount reaction control parameters are the same as embodiment 1, the result epoxy value is 0.70 equivalent / 100 grams, viscosity 25℃ 0.40Pa.s, after 4,4'-diaminodiphenyl sulfone is cured, the performance index is also the same as that of Example 1.

Embodiment 3

[0023] Except epichlorohydrin 925g (10mol), glycerin 85g, cobalt monochloroacetate 2.5g, water 50g, add reaction at 70 ℃ for 4 hours, add 30wt% sodium hydroxide aqueous solution 247g and 30wt% potassium carbonate aqueous solution 165g, Carry out cyclization reaction at 60 DEG C for 3 hours, add 1000mol toluene to extract, other charging amount, reaction control parameter are the same as embodiment 1, the result epoxy value is 0.74 equivalent / 100 grams, viscosity 25℃ It is 0.51Pa.s, and the performance index is also the same as that of Example 1 after curing by 4,4'-diaminodiphenyl sulfone.

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Abstract

The invention relates to a preparation method of tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenyl-methane, which comprises the following steps: mixing 1 mol of 1,3,3'-diethyl-4,4'-diaminodiphenyl-methane, 5-10 mol of epoxy chloropropane, 0.5-1.0 percent by weight of Alpha-halogenated carboxylate catalyst (based on the weight of the 3,3'-diethyl-4,4'-diaminodiphenyl-methane), 70-85g of polyol and 40-50g of water in a reaction container, dissolving, and then raising the temperature to 50-70 DEG C, maintaining the temperature for 4-7h, continuously adding 320g of acetone and 373-412g of 30 percentby weight of sodium hydroxide water solution or 30 percent by weight of potassium carbonate or mixture of the 30 percent by weight of sodium hydroxide water solution and the 30 percent by weight of potassium carbonate for reacting for 3-5h at a temperature of 50-60 DEG C; adding 800-1,000ml of methylbenzene for extracting a target product, and evaporating the methylbenzene, wherein the product isa bit red liquid resin, the epoxy value of the resin is 0.70-0.74equivalent / 100g, the viscosity 25 DEG C is 0.40-0.51Pa.s, the heat deflection temperature of the resin after being cured by 4,4'-diaminodiphenylsulfone is 182.1 DEG C, the Rockwell hardness E is 85, and the impaction modulus is 3.2 Gpa.

Description

1. Technical field [0001] The present invention relates to a preparation method of tetraglycidylamine compound, more specifically to a preparation method of tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenylmethane. 2. Background technology [0002] Epoxy resins are used in many applications such as adhesives, coatings, casting materials, insulating potting materials and reinforced composite materials. Glycidyl ethers or esters derived from epichlorohydrin and bisphenols or dicarboxylic acids are generally suitable for the above purposes. However, the aerospace field requires applications at high temperatures and moderate performance. In the current situation, the molecular structure of epoxy resins is required to have both glycidyl and aromatic amino groups, and epoxy resins that combine glycidyl and aromatic amino groups. , is what we generally call glycidylamine compounds. Among these glycidylamine compounds, tetraglycidyl-4,4'-diaminodiphenylmethane is a typical represent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/36C07D301/27B01J31/04B01J27/25C08G59/32
Inventor 李伟烘胡志强黄慧琳
Owner SHANGHAI PLASTICS RES INST CO LTD
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