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Preparation method of N, N'-dicyanoethyl-diaminodiphenyl methane

A technology of diaminodiphenylmethane and diaminodiphenyl, which is applied in the field of organic synthesis, can solve the problems of combustion and explosion, slow reactivity, and high reaction temperature, and achieve improved reactivity, high safety factor, and catalytic efficiency high effect

Pending Publication Date: 2021-11-16
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Aromatic amine curing agents usually have the characteristics of long service life and better heat resistance, chemical resistance, aging resistance, electrical properties and mechanical properties of the cured product, but there are also some defects: First, most aromatic amine curing agents Most of them are solid, and can only be cured with epoxy resin in the state of high temperature melting, and the alkalinity of aromatic amine is weaker than that of aliphatic amine, and the steric barrier of aromatic ring, the reactivity with epoxy resin is much slower , so it must be cured by heating, which will shorten the trial period of the compound and may have an adverse effect on the process performance of the product; second, aromatic amines are more toxic, and will release amine vapor under high temperature curing conditions, which is harmful to It is harmful to human health, so it is essential to take chemical modification to reduce its toxicity; thirdly, the epoxy resin product cured by aromatic amine is not tough enough, so if necessary, a flexible chain is connected to the amino terminal to improve the toughness and strength of the product
This method simplifies the preparation process to a certain extent, but the reaction temperature is too high, considering the risk of acrylonitrile being flammable and explosive under high heat, it is not suitable for industrial production

Method used

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  • Preparation method of N, N'-dicyanoethyl-diaminodiphenyl methane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Add 2.0mol acrylonitrile, 0.15mol hydroquinone, 0.04mol Zn(AcO) to a 2L reactor 2 and 0.04mol HAc at 30°C under a nitrogen atmosphere for 60 min until the catalyst was completely dissolved.

[0032] (2) Within half an hour, the reaction temperature was raised to 80° C., and at this moment, a THF solution containing 1.0 mol of diaminodiphenylmethane was continuously added dropwise to the reaction mixture (the mass ratio of diaminodiphenylmethane to THF was 1:1), the dropping time does not exceed 1 hour. After the dropping is completed, react at a temperature of 80-85°C for 12 hours until the reaction of diaminodiphenylmethane is complete. Take 3 drops of the reaction solution and dilute it to 1ml with ethanol Chromatographic analysis showed that 20 ppm of acrylonitrile remained and the conversion rate of diaminodiphenylmethane was 98.9%.

[0033](3) Transfer the material to a 1L flask, heat the oil bath to 110°C, remove low-boiling acrylonitrile and tetrahydrofuran ...

Embodiment 2

[0036] (1) Add 2.0mol acrylonitrile, 0.15mol hydroquinone, 0.04mol Cu(AcO) into a 2L reactor 2 and 0.04mol HAc at 30°C under a nitrogen atmosphere for 60 min until the catalyst was completely dissolved.

[0037] (2) Within half an hour, the reaction temperature was raised to 80° C., and at this moment, a THF solution of 1.0 mol diaminodiphenylmethane was continuously added dropwise to the reaction mixture (the mass ratio of diaminodiphenylmethane to THF was 1 : 1), the dropping time is no more than 1 hour, after the dropping is finished, react at a temperature of 80-85° C. for 12 hours until the reaction of diaminodiphenylmethane is complete, take 3 drops of the reaction solution and dilute it to 1 ml with ethanol Chromatographic analysis showed that 45 ppm of acrylonitrile remained, and the conversion rate of diaminodiphenylmethane was 97.2%.

[0038] (3) Transfer the material to a 1L flask, heat the oil bath to 110°C, remove low-boiling acrylonitrile and tetrahydrofuran aft...

Embodiment 3

[0041] (1) Add 2.0mol acrylonitrile, 0.15mol hydroquinone, 0.04mol Al(AcO) into a 2L reactor 3 and 0.04mol HAc at 30°C under a nitrogen atmosphere for 60 min until the catalyst was completely dissolved.

[0042] (2) Within half an hour, the reaction temperature was raised to 80° C., and at this moment, a THF solution of 1.0 mol diaminodiphenylmethane was continuously added dropwise to the reaction mixture (the mass ratio of diaminodiphenylmethane to THF was 1 : 1), the dropping time is no more than 1 hour, after the dropping is finished, react at a temperature of 80-85° C. for 12 hours until the reaction of diaminodiphenylmethane is complete, take 3 drops of the reaction solution and dilute it to 1 ml with ethanol Chromatographic analysis showed that acrylonitrile remained at 32 ppm and the conversion rate of diaminodiphenylmethane was 98.0%.

[0043] (3) Transfer the material to a 1L flask, heat the oil bath to 110°C, remove low-boiling acrylonitrile and tetrahydrofuran afte...

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Abstract

The invention discloses a preparation method of N, N'-dicyanoethyl-diaminodiphenyl methane, which comprises the steps of: adding acrylonitrile and a composite acid catalyst into a reaction kettle for reaction to generate an intermediate, and performing Michael addition reaction on the intermediate and diaminodiphenyl methane to obtain a cyanoethyl amine compound with stable character. The production method of N, N'-dicyanoethyl-diaminodiphenyl methane provided by the invention has the advantages of stable operation control, high yield, high product quality and the like, and fills the blank of the production technology of N, N'-dicyanoethyl-diaminodiphenyl methane in China. The obtained N, N'-dicyanoethyl-diaminodiphenyl methane has good reactivity with epoxy resin, isocyanate and the like, and compared with existing diaminodiphenyl methane, the N, N'-dicyanoethyl-diaminodiphenyl methane is lower in toxicity, shorter in trial period and higher in toughness.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of N,N'-dicyanoethyl-diaminodiphenylmethane. Background technique [0002] Epoxy resin is a kind of linear thermoplastic resin. Due to its excellent physical properties, electrical insulation properties and adhesion, it has been widely used in many fields such as coatings, composite materials and adhesives. However, due to environmental Oxygen resin itself cannot be cured, nor does it have any performance. Only when it is compounded with a curing agent to form a cured product with a three-dimensional three-dimensional network structure, can it have excellent practical value. Therefore, the curing agent is used in the use of epoxy resin. is an essential component. [0003] There are many kinds of epoxy resin curing agents, common ones are aliphatic amines, alicyclic amines, aromatic amines, polyamides, tertiary amines, modified amines, etc., and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/24B01J31/04
CPCC07C253/30B01J31/04B01J35/19C07C255/24
Inventor 于波张聪颖李鑫周萌张文清姜博顾志广智丁未尚永华
Owner WANHUA CHEM GRP CO LTD
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