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Synthesis method of bismaleimide containing adamantane side group triarylamine

A bismaleimide and synthesis method technology, applied in organic chemistry and other fields, can solve problems such as steric regularity and polymer solubility constraints, and achieve high free volume, improved solubility, and excellent benefits

Pending Publication Date: 2021-08-10
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The triarylamine structure is a structure with at least three benzene rings. Due to the existence of multiple benzene ring structures, the polymer will have certain heat resistance, but its spatial regularity has certain restrictions on improving the solubility of the polymer.

Method used

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  • Synthesis method of bismaleimide containing adamantane side group triarylamine
  • Synthesis method of bismaleimide containing adamantane side group triarylamine
  • Synthesis method of bismaleimide containing adamantane side group triarylamine

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Effect test

preparation example Construction

[0024] The synthetic preparation method of the triarylamine bismaleimide containing adamantane side group mainly comprises following route:

[0025] Synthesis of triarylamine diamine containing adamantane side group:

[0026]

[0027] p-adamantylaniline and p-halogenated nitrobenzene, in which the halogen atom can be chlorine, bromine, fluorine, preferably fluorine atom, dissolved in dimethyl sulfoxide according to the molar ratio of 1:2~2.1, at 110°C-150 Reaction at ℃ for 12-16h, using cesium fluoride as a catalyst, the dosage is 50%-90% of the p-halogenated nitrobenzene substance, after the reaction, pour the mother liquor into water to precipitate, then suction filter, wash and dry Obtain dinitro compounds, and then use acetonitrile to carry out recrystallization;

[0028] The palladium-carbon catalytic reduction system is selected for the dinitro compound, and the triarylamine diamine compound is obtained under the action of hydrazine hydrate, and finally recrystallize...

Embodiment 1

[0036] Take 0.1 mol of p-adamantylaniline and 0.21 mol of p-fluoronitrobenzene, dissolve them in a three-neck flask with a thermometer and a magnetic rotor containing 100 ml of dimethyl sulfoxide, and add 0.16 mol of fluorine after the dissolution is complete Cesium chloride was heated to 120°C for 15 hours. After the reaction was complete, the solution was poured into water, stirred rapidly, settled for 12 hours, filtered and washed several times with suction, and dried to obtain a yellow solid crude product. The crude dinitro compound was recrystallized from acetonitrile.

[0037] Take 0.1 mol of the recrystallized dinitro compound, add it to a three-necked flask with a thermometer and a magnetic rotor containing 100 ml of ethanol, add 10% palladium carbon based on the mass of the dinitro compound, stir evenly, and slowly Hydrazine hydrate was added to raise the temperature to reflux temperature, and the reaction was carried out for 12 hours. After the reaction is complete...

Embodiment 2

[0040] Take 0.5 mol of p-adamantylaniline and 1.1 mol of p-chloronitrobenzene and dissolve them in a three-neck flask containing 500 ml of dimethyl sulfoxide with a thermometer and a magnetic rotor. After the dissolution is complete, add 0.8 mol of fluorinated cesium, heated to 150 ° C for 15 hours. After the reaction was complete, the solution was poured into water, stirred rapidly, settled for 12 hours, filtered and washed several times with suction, and dried to obtain a yellow solid crude product. The crude dinitro compound was recrystallized from acetonitrile.

[0041]Take 0.4 mol of the recrystallized dinitro compound and add it to a three-neck flask with a thermometer and a magnetic rotor containing 350 ml of ethanol. Based on the mass of the dinitro compound, add 5% palladium carbon, stir evenly, and slowly add Hydrazine hydrate was warmed up to reflux temperature and reacted for 12h. After the reaction is complete, remove the palladium carbon by suction filtration w...

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Abstract

The invention discloses a synthesis method of bismaleimide containing adamantane side group triarylamine, and relates to a synthesis method of a resin polymer. The synthesis method comprises the following steps: synthesizing adamantane side group triarylamine diamine from adamantane-containing aniline, and then conducting reacting with maleic anhydride to synthesize bismaleimide. Adamantane and a triarylamine group are introduced into bismaleimide at the same time. The bismaleimide has the characteristics of excellent thermal stability, mechanical property, corrosion resistance, low flammability and the like, and is widely applied to advanced composite materials and high-frequency substrate materials in the fields of aerospace, information electronics and the like. The synthesized bismaleimide has good solubility in a common solvent, the heat-resistant stability and the mechanical property are obviously improved, and wide application of the bismaleimide is facilitated.

Description

technical field [0001] The invention relates to a method for synthesizing a resin polymer, in particular to a method for synthesizing a bismaleimide containing an adamantane side group triarylamine. Background technique [0002] Thermosetting resins are used in all aspects of life because of their outstanding mechanical properties, high specific strength and strong modulus, and good corrosion resistance. With the development of aerospace and information technology, the requirements for materials are becoming more and more stringent, so it is necessary to develop thermosetting resins with higher performance to meet the needs of use. [0003] As a high-performance resin derived from polyimide with reactive groups, bismaleimide has excellent thermal properties, mechanical properties, corrosion resistance, etc., and is widely used in aerospace advanced composite components , High-frequency circuit boards in the electronics industry and other fields. However, the traditional di...

Claims

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Application Information

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IPC IPC(8): C07D207/452
CPCC07D207/452
Inventor 张鑫王佩瑶马亚辉张德浩张泽昊牛永安
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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