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Benzoxazine resin containing carbon-nitrogen and azo structures and preparation method thereof

A technology of benzoxazine and aminoazobenzene, which is applied in the field of benzoxazine resin and its preparation, can solve the problems of single function, limited application scope and application field, achieves low volume shrinkage rate, and expands the application market. and foreground, the effect of low softening temperature

Active Publication Date: 2018-12-14
SOUTHWEST PETROLEUM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] An object of the present invention is to provide a benzoxazine resin with fluorescence activity and ultraviolet light response ability, which contains Benzoxazine resin with carbon nitrogen C=N and azo N=N structures

Method used

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  • Benzoxazine resin containing carbon-nitrogen and azo structures and preparation method thereof
  • Benzoxazine resin containing carbon-nitrogen and azo structures and preparation method thereof
  • Benzoxazine resin containing carbon-nitrogen and azo structures and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of preparation method of the benzoxazine resin containing carbon nitrogen and azo structure, comprises the steps:

[0030] S1. Add 40 parts by weight of paraformaldehyde and 200 parts by weight of 4-aminoazobenzene (primary amine A) into the reactor, add 500 parts by weight of toluene, and mechanically stir at 300 rpm for 0.5 h at 30°C. Obtain the mixed solution; S2. Slowly add 125 parts by weight of p-hydroxybenzaldehyde to the mixed solution system, then raise the temperature to 120° C. and reflux for 6 hours under mechanical stirring at 400 rpm. After the reaction is completed, cool the system to room temperature, and After alkali washing and water washing for 3 times, the organic phase is separated, and the toluene is removed by rotary evaporation, and the product is dried to obtain an intermediate containing carbon nitrogen and azo structure; S3, 175 parts by weight of the intermediate prepared in step S2 and 180 parts by weight of Add N-phenyl-1,4-phenylene...

Embodiment 2

[0039] A kind of preparation method of the benzoxazine resin containing carbon nitrogen and azo structure, comprises the steps:

[0040] S1. Add 65 parts by weight of paraformaldehyde and 210 parts by weight of 4,4'-azodiphenylamine (primary amine A) into the reactor, add 1000 parts by weight of p-xylene, and set the temperature at 50°C at 500 rpm Stir mechanically for 1 hour to obtain a mixed solution; S2. Slowly add 250 parts by weight of o-hydroxybenzaldehyde to the mixed solution system, then raise the temperature of the system to 120° C., and reflux for 6 hours under mechanical stirring at 400 rpm. After the reaction is completed, the The system was cooled to room temperature, after washing with alkali and water for 4 times, the organic phase was separated, the toluene was removed by rotary evaporation, and the product was dried to obtain an intermediate containing an azo structure; S3, 300 parts by weight of an intermediate containing an azo structure and 150 parts by we...

Embodiment 3

[0043] A kind of preparation method of the benzoxazine resin containing carbon nitrogen and azo structure, comprises the steps:

[0044] S1. Add 30 parts by weight of paraformaldehyde and 90 parts by weight of aniline (primary amine A) into the reactor, add 400 parts by weight of p-xylene, and mechanically stir at 300 rpm at 60°C for 1 hour to obtain a mixed solution; S2. Add 120 parts by weight of p-hydroxybenzaldehyde to the mixed liquid system. After the p-hydroxybenzaldehyde is added, the system is refluxed for 4 hours under the condition of 140° C. and 400 rpm mechanical stirring. After the reaction was completed, the system was cooled to room temperature, washed twice with alkali and water, the organic phase was separated, the toluene was removed by rotary evaporation, and the product was dried to obtain an intermediate without an azo structure; S3, 240 parts by weight of The azo-containing intermediate and 195 parts by weight of 4-aminoazobenzene (primary amine B) were ...

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Abstract

The invention discloses benzoxazine resin containing carbon-nitrogen and azo structures. The resin is prepared through a ring opening polymerization reaction to a benzoxazine monomer containing the carbon-nitrogen and azo structures under heating condition. The preparation method includes: S1) adding paraformaldehyde, primary amine A and a dispersing medium into a reaction kettle and uniformly stirring the components; S2) adding hydroxybenzaldehyde, heating the mixture to 75-150 DEG C, performing a reflux reaction for 3-10 h, cooling the mixture to room temperature, and washing the products with alkali and water, separating an organic phase and removing the dispersing medium to obtain an intermediate; S3) adding the intermediate and a primary amine B to the dispersing medium, heating the mixture to 60-150 DEG C, performing a reflux reaction for 4-8 h, cooling and recrystallizing the product, and filtering and drying the product to obtain the benzoxazine monomer containing the carbon-nitrogen and azo structures; S4) performing the ring opening polymerization reaction to the monomer to obtain the benzoxazine resin. The resin has fluorescent activity and ultraviolet responding performance, and can be applied to the fields such as fluorescent probes, photochromic and optic-sensing devices, anti-fake products and biomedical technology.

Description

technical field [0001] The invention belongs to the technical field of organic polymer materials, and in particular relates to a benzoxazine resin containing carbon nitrogen and azo structures and a preparation method thereof. Background technique [0002] Photoactive materials can produce reversible discoloration effects under the irradiation of ultraviolet light and visible light, and their special optical properties have broad application prospects in optoelectronic fields such as optical information storage, anti-counterfeiting, and optical switches. According to the mechanism, organic photochromic materials are mainly divided into: (1) compounds such as spiropyran and spirooxazine with heterolytic bonds; (2) diarylethenes with homolytic bonds; (3) proton transfer tautomerism Structured salicylaldehyde aniline Schiff bases and (4) cis-trans isomers of azobenzene-type chemicals. Organic small molecule chemicals do not have processability and mechanical strength. After t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G14/073
CPCC08G14/06
Inventor 赵春霞刘佳男李云涛李姝靓李辉向东
Owner SOUTHWEST PETROLEUM UNIV
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