Alkyl-containing phthalonitrile resin based on autocatalytic curing and preparation method thereof

A technology of alkyl phthalonitrile resin and alkyl phthalonitrile, which is applied to the preparation of organic compounds, carboxylic acid nitrile preparation, chemical instruments and methods, etc., and can solve the problem of increasing the preparation of phthalonitrile resin Problems such as cost, limitation of wide range of applications, complex synthesis and purification

Active Publication Date: 2020-08-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the phthalonitrile resin structure obtained by catalysis of phenolic hydroxyl group, primary ammonia and secondary amine contains triazine ring, isoindoline and phthalocyanine at the same time, the resin structure is complex and difficult to control, and the conversion rate of nitrile group is reduced
In addition, the synthesis and purification of the above-mentioned self-catalyzed phthalonitrile monomers formed by introducing active groups such as phenolic hydroxyl groups, primary ammonia, and secondary amines are often complicated (Hu J, Liu Y, Jiao Y, et al. Self- promoted phthalimide-containing phthalonitrile resins with sluggish curing process and excellent thermal stability[J].RSC Advances,2015,5(21):16199-16206.), the synthesis of monomers usually includes multi-stage reactions, and its purification is filtered and washed in methanol Further recrystallization is often required on the basis of phthalonitrile resin, which increases the preparation cost of phthalonitrile resin and further limits its wide range of applications

Method used

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  • Alkyl-containing phthalonitrile resin based on autocatalytic curing and preparation method thereof
  • Alkyl-containing phthalonitrile resin based on autocatalytic curing and preparation method thereof
  • Alkyl-containing phthalonitrile resin based on autocatalytic curing and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0067] (1) Preparation of phthalonitrile monomer derived from bisphenol F

[0068] In this embodiment, bisphenol F (CAS No.: 620-92-8) and 4-nitrophthalonitrile are used as raw materials, and potassium carbonate is used as a catalyst. The bisphenol F (CAS No.: 620-92-8) , The mol ratio of 4-nitrophthalonitrile and salt of wormwood is 1.0:2.3:1.1, and the described bisphenol F consumption is 3.01g, and the structural formula of described bisphenol F is as follows:

[0069]

[0070] Dissolving bisphenol F and 4-nitrophthalonitrile in 20 mL of NMP solvent, then adding potassium carbonate to the resulting solution, and then incubating at 30°C for 12 hours to obtain a reaction solution containing a solid reaction product; The reaction solution was filtered to obtain a solid reaction product, which was then washed with deionized water and methanol (each washing solution was washed twice), and the solid reaction product was collected, and the solid reaction product was dried at 10...

Embodiment 2

[0088] (1) Preparation of phthalonitrile monomer derived from dihydric phenol

[0089] In this embodiment, dihydric phenol (CAS No.: 2081-08-05) and 4-nitrophthalonitrile are used as raw materials, and potassium carbonate is used as a catalyst. The dihydric phenol, 4-nitrophthalonitrile The mol ratio with salt of wormwood is 1.0:2.3:1.1, and described dihydric phenol consumption is 3.2g, and the structural formula of described dihydric phenol is as follows:

[0090]

[0091] Dihydric phenol and 4-nitrophthalonitrile were dissolved in 25 mL of NMP solvent, potassium carbonate was added to the resulting solution, and then reacted at 30° C. for 10 hours to obtain a reaction solution containing a solid reaction product; the obtained The reaction solution was filtered to obtain a solid reaction product, which was then washed with deionized water and methanol (each wash was washed twice), and the resulting solid reaction product was collected, and the solid reaction product was d...

Embodiment 3

[0099] (1) Preparation of phthalonitrile monomer derived from dihydric phenol

[0100] In this embodiment, dihydric phenol (CAS No.: 1576-13-2) and 4-nitrophthalonitrile are used as raw materials, and potassium carbonate is used as a catalyst. The dihydric phenol, 4-nitrophthalonitrile The mol ratio with salt of wormwood is 1.0:2.3:1.1, and described dihydric phenol consumption is 3.3g, and the structural formula of described dihydric phenol is as follows:

[0101]

[0102] Dihydric phenol and 4-nitrophthalonitrile were dissolved in 26 mL of DMSO solvent, potassium carbonate was added to the resulting solution, and then reacted at 25° C. for 15 hours to obtain a reaction solution containing a solid reaction product; the obtained The reaction solution was filtered to obtain a solid reaction product, which was then washed with deionized water and methanol (each wash was washed twice), and the resulting solid reaction product was collected, and the solid reaction product was d...

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Abstract

The invention discloses alkyl-containing phthalonitrile resin based on autocatalytic curing and a preparation method thereof. The alkyl-containing phthalonitrile resin is prepared by curing an alkyl-containing phthalonitrile monomer which has both self-catalysis and self-curing characteristics and is used as a raw material, wherein the monomer has a structural formula as described in the specification. According to the invention, the alkyl-containing phthalonitrile monomer is used as the raw material; since an alkyl group is introduced as a catalytic unit and can provide active hydrogen protons to initiate the crosslinking of a cyano group, the autocatalytic curing of the monomer can be realized, and the curing rate of the monomer is obviously improved; and the prepared alkyl-containing phthalonitrile resin shows excellent thermal stability and thermal oxygen stability.

Description

technical field [0001] The invention belongs to the technical field of phthalonitrile resins, and relates to a phthalonitrile resin prepared from an alkyl-containing phthalonitrile monomer having both self-catalysis and curing properties as a raw material and a preparation method thereof. Background technique [0002] Due to its high thermal stability, thermal oxygen stability, low flammability, chemical corrosion resistance and excellent high-temperature mechanical properties, phthalonitrile resin has been widely used as a matrix resin for high-performance composite materials in aerospace, etc. high-tech field. [0003] Phthalonitrile resins are formed by curing phthalonitrile monomers. However, in the existing phthalonitrile resin preparation process, if no curing agent is added, the curing of phthalonitrile monomer is an extremely slow process (generally at 300 ° C, the viscosity cannot be significantly increased for more than a week) , resulting in difficult processing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/54C07C253/30C07D213/30C08G73/06
CPCC07C255/54C07D213/30C08G73/0672C07C2601/14
Inventor 杨刚曾科谭伟李仁可刘洋柳郑州胡江淮
Owner SICHUAN UNIV
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