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Side-chain phthalonitrile modified benzoxazine resin, preparation method and application

A technology of phthalonitrile and benzoxazine, which is applied in the field of side-chain phthalonitrile modified benzoxazine resin and its preparation, can solve the problems of high brittleness of cured products, high curing reaction temperature and thermal stability Insufficient and other problems, to achieve the effect of improving thermodynamic performance, simple preparation method and high yield

Inactive Publication Date: 2016-01-20
国科广化(南雄)新材料研究院有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But it also has obvious disadvantages, such as high curing reaction temperature, high brittleness of cured products and insufficient thermal stability for use under many harsh conditions.

Method used

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  • Side-chain phthalonitrile modified benzoxazine resin, preparation method and application
  • Side-chain phthalonitrile modified benzoxazine resin, preparation method and application
  • Side-chain phthalonitrile modified benzoxazine resin, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] (1) Add 279g (3mol) of aniline, 122g (1mol) of p-hydroxybenzaldehyde and 13g of aniline hydrochloride in a 500mL flask equipped with a magnetic stirrer, then logical N 2 And gradually raise the temperature to 120° C. for 12 hours. After the reaction is completed, cool down to room temperature, add 200 mL of absolute ethanol, heat up and reflux for 2 hours again, filter after cooling down, wash the filtered solid with a small amount of absolute ethanol and water, remove aniline and aniline hydrochloride, and finally recrystallize 3 times with absolute ethanol 142 g of purple-red needle crystals were obtained, with a yield of 49%.

[0055] (2) In a 500mL flask equipped with a magnetic stirrer, add 14.66g (50.5mmol) of the compound of formula 2, 13.96g (101mmol) of anhydrous potassium carbonate, 8.66g (50mmol) of 4-nitrophthalonitrile and 250mL After the addition of acetonitrile, the temperature was gradually raised to 80°C for 12 hours. After the reaction was completed,...

Embodiment 2

[0060] (1) Add 279g (3mol) of aniline, 122g (1mol) of p-hydroxybenzaldehyde and 13g of aniline hydrochloride in a 500mL flask equipped with a magnetic stirrer, then logical N 2 And gradually raise the temperature to 150° C. for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, 200 mL of absolute ethanol was added, and the temperature was raised to reflux for another 2 hours. After cooling down to room temperature, filter, and wash the filtered solid with a small amount of absolute ethanol and water to remove aniline and aniline hydrochloride, and finally recrystallize 3 times with absolute ethanol to obtain 116 g of purple-red needle-like crystals, with a yield of 40%.

[0061] (2) In a 500mL flask equipped with a magnetic stirrer, add 14.66g (50.5mmol) of the compound of formula 2, 13.96g (101mmol) of anhydrous potassium carbonate, 8.66g (50mmol) of 4-nitrophthalonitrile and 250mL of DMF , After the addition, react at room temperatur...

Embodiment 3

[0064] (1) Add 279g (3mol) of aniline, 122g (1mol) of p-hydroxybenzaldehyde and 13g of aniline hydrochloride in a 500mL flask equipped with a magnetic stirrer, then logical N 2 And gradually raise the temperature to 135° C. for 8 hours. After the reaction was completed and cooled down to room temperature, 200 mL of absolute ethanol was added, and the temperature was raised to reflux again for 2 hours. After cooling down to room temperature, filter and wash the filtered solid with a small amount of absolute ethanol and water to remove aniline and aniline hydrochloride, and finally recrystallize 3 times with absolute ethanol to obtain 122 g of purple-red needle-like crystals, with a yield of 42%.

[0065] (2) In a 500mL flask equipped with a magnetic stirrer, add 14.66g (50.5mmol) of the compound of formula 2, 13.96g (101mmol) of anhydrous potassium carbonate, 8.66g (50mmol) of 4-nitrophthalonitrile and 250mL of DMF , After the addition, react at 60°C for 24 hours. After the r...

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Abstract

The invention belongs to the field of benzoxazine resin in polymer synthetic materials and discloses side-chain phthalonitrile modified benzoxazine resin, a preparation method and an application. The resin has a general structural formula shown in a formula I, wherein n is an integer larger than or equal to 1. By means of the characteristic of strong molecular structure design of a benzoxazine monomer, a polymerizable phthalonitrile group is introduced into an aromatic diamine compound through a conventional chemical reaction, then the aromatic diamine compound carrying the phthalonitrile group, paraformaldehyde and bisphenol A have condensation polymerization, and the side-chain phthalonitrile modified benzoxazine resin is prepared. Phthalonitrile which is a polymerizable group is introduced into benzoxazine, so that phthalonitrile can participate in curing, the crosslinking density of polybenzoxazine resin can be further increased, and the thermal stability of polybenzoxazine can be further improved. The preparation method is simple and convenient, a synthesis period is short, the yield is high, and raw materials are easy to obtain.

Description

technical field [0001] The invention belongs to the field of benzoxazine resins in polymer synthetic materials, and in particular relates to a side-chain phthalonitrile-modified benzoxazine resin, a preparation method and an application thereof. Background technique [0002] Material science and technology is an important support for the development of the national economy and the basis for the advancement of high and new technologies such as national defense and information. So far, high-performance polymer-based composites widely used in aerospace applications are mainly based on thermosetting resin matrices. The commonly used thermosetting resins mainly include phenolic resins, benzoxazine resins and bisphthalonitrile resins. [0003] Benzoxazine is a kind of monomer containing N, O heterocyclic structure, which is generally obtained by condensation reaction of phenolic compounds, primary amine compounds and formaldehyde. In 1944, Holly and Cope accidentally discovered ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06
Inventor 吕满庚郑剑王莹梁利岩吴昆
Owner 国科广化(南雄)新材料研究院有限公司
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