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Dibenzoxazine monomer containing ortho-position maleimide groups and preparation method thereof

A technology of maleimide group and maleimide function, which is applied in the field of bisbenzoxazine monomer and its preparation, can solve the problem of low yield, long reaction time, and no reports involving ortho horses Solve problems such as the synthesis and use of imide bis-benzoxazine, and achieve the effects of excellent overall performance of the resin, reduced synthesis reaction time, and simple preparation process

Active Publication Date: 2017-02-01
CHANGZHOU HONGFA ZONGHENG ADVANCED MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These p-maleimide functionalized benzoxazine monomers generally have the defects of long reaction time and low yield
But so far, there is no report involving the synthesis and use of ortho-maleimide dibenzoxazine

Method used

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  • Dibenzoxazine monomer containing ortho-position maleimide groups and preparation method thereof
  • Dibenzoxazine monomer containing ortho-position maleimide groups and preparation method thereof
  • Dibenzoxazine monomer containing ortho-position maleimide groups and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 30.6g of 2-aminophenol and 30g of maleic anhydride were added to the ice bath system of 80mL dimethylformamide (DMF), then 15g of phosphorus pentoxide and 8g of concentrated sulfuric acid dissolved in 50mL of DMF were added thereto, and the reaction After 30 minutes, the reaction device was placed in an oil bath at 70° C. for 6 hours. After the reaction, the reaction solution was poured into 200ml of deionized water to obtain a large amount of precipitation. After suction filtration, it was washed three times with a large amount of water and ethanol, and dried in a vacuum oven at 50° C. to obtain 43.5 g of the product ortho-maleimide functionalized phenol with a yield of 82%.

[0030] Weigh 30g of ortho-maleimide phenol obtained in the previous step, 15.7g of 4,4'-diaminodiphenylmethane, 9.5g of paraformaldehyde, and 80ml of toluene, respectively, and add them to In the reaction bottle of the tube, heat at a rate of 10°C / h to 120°C for 6h. After the reaction was finis...

Embodiment 2

[0032] The ortho-maleimide functionalized phenol was prepared referring to the operation steps of Example 1.

[0033] Add 30g of o-maleimide phenol, 16.8g of 4,4'-diaminobenzophenone, 9.5g of paraformaldehyde, and 80ml of xylene into a reaction flask equipped with a stirrer, a thermometer, and a condenser , heated to 130°C at a rate of 10°C / h for 6h. After the reaction was finished, deionized water was added to the reaction solution for precipitation, and a large amount of precipitate was obtained. The precipitate was washed 3 times with 5% sodium hydroxide solution, then washed with water, filtered, and dried under vacuum for 12 hours to obtain Product 46.4g, yield 92%.

Embodiment 3

[0035] The ortho-maleimide functionalized phenol was prepared referring to the operation steps of Example 1.

[0036] Add 30g of o-maleimide phenol, 17.2g of 4,4'-diaminodisulfide, 9.5g of paraformaldehyde, and 80ml of xylene into a reaction flask equipped with a stirrer, a thermometer and a condenser, respectively. Heating to 120°C at a rate of 10°C / h for 6h. After the reaction was finished, deionized water was added to the reaction solution for precipitation, and a large amount of precipitate was obtained. The precipitate was washed 3 times with 5% sodium hydroxide solution, then washed with water, filtered, and dried under vacuum for 12 hours to obtain Product 41.1g, yield 81%.

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Abstract

The invention discloses a dibenzoxazine monomer containing ortho-position maleimide groups and a preparation method thereof. The molecular formula is show in the following picture, wherein R1 is any one of following structures. The introduced ortho-position maleimide groups weaken the rigidity of molecules, effectively shorten the time for synthesis of benzoxazine and improve the machinability of benzoxazine resin. In addition, except for oxazine ring curing cross-linking of dibenzoxazine, the maleimide groups at the two ends of a molecule further can carry out secondary bi-crosslinking, and therefore the thermal stability of the resin is greatly improved. The preparation technology is simple, the comprehensive performance of the resin is excellent, and the dibenzoxazine monomer is suitable for matrix resin of high-performance compound materials.

Description

technical field [0001] The invention relates to a thermosetting resin and a preparation method thereof, in particular to a bisbenzoxazine monomer containing an ortho-maleimide group and a preparation method thereof. Background technique [0002] Benzoxazine resin, its chemical structural formula is usually: [0003] [0004] Benzoxazine resin is a new type of thermosetting resin, which can be obtained through dehydration and cyclocondensation of phenol, amine, and aldehyde compounds. Under the action of heat and / or catalyst, the oxazine ring undergoes ring-opening and cross-linking to form a dense spatially cross-linked network structure. Compared with traditional phenolic resins, benzoxazine resins have good heat resistance, chemical corrosion resistance, excellent flame retardancy and excellent mechanical properties. Among them, the most outstanding feature of benzo is its flexible structure controllability. The target product can be prepared by introducing phenol sou...

Claims

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Application Information

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IPC IPC(8): C07D413/14
CPCC07D413/14
Inventor 张侃谈昆伦商枝坤王瑾赟季小强刘时海
Owner CHANGZHOU HONGFA ZONGHENG ADVANCED MATERIAL TECH
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