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Phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer, phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile)condensate, and preparation method of oligomer

A technology of phthalonitrile and poly(arylene ether nitrile), which is applied to cured products and their preparation, and the field of phthalonitrile-terminated poly(arylene ether nitrile) oligomers containing fluorene structure, which can solve the problem of unmentioned oligomers. , cured product and its preparation method, etc., to achieve the effect of good solubility

Active Publication Date: 2018-04-13
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polyimide resins, bismaleimide resins and epoxy resins containing fluorene structures all exhibit excellent thermo-oxidative properties and mechanical properties. Body (CN 103288680 A), but this patent does not mention oligomers containing fluorene structure, cured products and their preparation methods

Method used

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  • Phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer, phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile)condensate, and preparation method of oligomer
  • Phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer, phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile)condensate, and preparation method of oligomer
  • Phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer, phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile)condensate, and preparation method of oligomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] 1) Add 8g (0.0465mol) of dichlorobenzonitrile, 32.59g (0.093mol) of bisphenol fluorene, 25.71g (0.186mol) of anhydrous potassium carbonate, 80mL of NMP and 20mL of toluene into the three-port port with water separation and condensation reflux device In the flask, under the protection of nitrogen, heat to 130-145°C to divide water for 4 hours, slowly distill out toluene after the completion of water separation, control the reaction temperature by distilling the speed and amount of toluene, continue to react at 150-200°C for 4 hours, cool to 80 Below ℃;

[0074] 2) Add 16.9 g (0.098 mol) of 4-nitrophthalonitrile to the reaction liquid in step 1), and react at a temperature of 80° C. for 12 hours;

[0075] 3) Filter the reaction solution described in step 2), remove the catalyst, recover the solvent under reduced pressure at 40-80°C in the filtrate, pour the residue into 5wt% hydrochloric acid solution for sedimentation, filter, and stir and wash with deionized water for 2...

Embodiment 2

[0085] 1) Add 8g (0.0465mol) of dichlorobenzonitrile, 21.73g (0.062mol) of bisphenol fluorene, 17.14g (0.128mol) of anhydrous potassium carbonate, 80mL of NMP and 20mL of toluene into the three-port port with water separation and condensation reflux device In the flask, under the protection of nitrogen, heat to 130-145°C to separate the water for 3 hours, slowly distill out the toluene after the completion of the water separation, control the reaction temperature by distilling the speed and amount of toluene to continue the reaction at 150-200°C for 5 hours, cool to 80 Below ℃;

[0086] 2) Add 5.90 g (0.065 mol) of 4-nitrophthalonitrile to the reaction solution in step 1), and react at a temperature of 80° C. for 12 hours.

[0087] 3) Filter the reaction solution described in step 2), remove the catalyst, recover the solvent under reduced pressure at 40-80° C. from the filtrate, pour the residue into 8 wt% hydrochloric acid solution for sedimentation, filter, and stir and wash...

Embodiment 3

[0092] 1) Add 8g (0.0465mol) of dichlorobenzonitrile, 20.37g (0.058mol) of bisphenol fluorene, 16.06g (0.116mol) of anhydrous potassium carbonate, 80mL of NMP and 20mL of toluene into the three-port port with water separation and condensation reflux device In the flask, under the protection of nitrogen, heat to 130-145°C to divide water for 2.5 hours, slowly distill out toluene after water separation, control the reaction temperature by distilling the speed and amount of toluene at 150-200°C for 6 hours, cool to 80 Below ℃;

[0093] 2) Add 4.43 g (0.061 mol) of 4-nitrophthalonitrile to the reaction solution described in step 1), and react at a temperature of 85° C. for 12 hours.

[0094] 3) Filter the reaction solution described in step 2), remove the catalyst, recover the solvent under reduced pressure at 40-80° C. from the filtrate, pour the residue into 8 wt% hydrochloric acid solution for sedimentation, filter, and stir and wash with deionized water 2-3 times until The fi...

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Abstract

The invention discloses a phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer, a phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) condensate, and a preparation method of the oligomer. The phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer has chain segments with different lengths and a large-volume side group structure, so the oligomer has a low melting point and a good dissolvability, can be dissolved in DMF, NMP and other strong polar solvents, and also can be dissolved in THF, dichloromethane and a toluene and acetonitrile mixed solvent. The phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) condensate has excellent heat stability and mechanical performances, the 5% decomposition temperature in a nitrogen atmosphere is 499-528 DEG C, the residue mass rate at 1000 DEG C is 69-73.2%, and the bending strength is higher than 500 MPa. Thepreparation method of the phthalonitrile-terminated fluorine structure-containing poly(arylene ether nitrile) oligomer is simple and controllable, and can be applied to industrial production.

Description

technical field [0001] The invention relates to the technical field of high-performance resin matrix, in particular to a phthalonitrile-terminated polyarylether nitrile oligomer containing a fluorene structure, a cured product and a preparation method thereof. Background technique [0002] In recent years, phthalonitrile resin has attracted much attention as an important class of high-performance thermosetting resin matrix. The triazine ring and phthalocyanine ring skeleton structure formed in the curing process of the monomer endows phthalonitrile polymer with Excellent thermal oxygen stability and mechanical properties, but its high melting point and melt viscosity lead to poor processing performance, which limits its further application. In order to broaden the processing window and improve processing performance, the researchers prepared cyano-terminated oligomers containing bisphenol A (US 2016 0168326 A1) and polyaryletherketone (WO 2015183518 A1), but the introduction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/16C07C253/30C08G73/06
CPCC07C255/16C08G73/06C08G73/0638
Inventor 王广兴周恒郭颖刘翔丁江楠赵彤
Owner INST OF CHEM CHINESE ACAD OF SCI
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