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Thermosetting polyphenylquinoxaline resin, its preparation method and application

A technology of polyphenylquinoxaline and polymerization reaction, which is applied in the field of high-performance thermosetting and high-temperature-resistant resins, can solve problems such as no systematic reports, and achieve the effect of excellent high-temperature resistance performance.

Inactive Publication Date: 2012-05-09
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This has laid a good foundation for the development of phenylethynyl-terminated PPQ, which has not been systematically reported at home and abroad.

Method used

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  • Thermosetting polyphenylquinoxaline resin, its preparation method and application
  • Thermosetting polyphenylquinoxaline resin, its preparation method and application
  • Thermosetting polyphenylquinoxaline resin, its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Example 1. Synthesis of phenylethynyl-terminated PPQ (in formula I, Y=-) with a designed molecular weight of 2500 g / mol

[0045] 1) Tetraketone compound 9 shown in formula II, the synthesis of 9-bis[(4-benziloxy)phenyl]fluorene

[0046] Add 53.60g (0.21mol) of 4-nitrobenzil, 35.04g (0.10mol) of 9,9-bis[(4-hydroxyphenoxy ) phenyl] fluorene and 240 mL of anhydrous dimethyl sulfoxide. Under nitrogen protection, the temperature was raised to 60° C., and 69.11 g (0.50 mol) of anhydrous potassium carbonate was added. Maintain a constant temperature for nitro nucleophilic substitution reaction 24h. After cooling to room temperature, the reaction solution was poured into 2000 mL of 1 mol / L hydrochloric acid solution. Add 600mL chloroform for extraction. The organic phase was repeatedly washed with water until neutral, and dried by adding anhydrous magnesium sulfate. Chloroform was distilled off under reduced pressure to obtain a crude product. The crude product was washed...

Embodiment 2

[0066] Example 2, the synthesis of phenylethynyl-terminated PPQ (in formula I, Y=-) with a designed molecular weight of 5000 g / mol

[0067] 1) Tetraketone compound 9 shown in formula II, the synthesis of 9-bis[(4-benziloxy)phenyl]fluorene

[0068] Add 53.60g (0.21mol) of 4-nitrobenzil, 35.04g (0.10mol) of 9,9-bis[(4-hydroxyphenoxy ) phenyl] fluorene and 240 mL of anhydrous dimethyl sulfoxide. Under the protection of nitrogen, the temperature was raised to 60° C., and 62.19 g (0.45 mol) of anhydrous potassium carbonate was added. Maintain a constant temperature for nitro nucleophilic substitution reaction 24h. After cooling to room temperature, the reaction solution was poured into 2000 mL of 1 mol / L hydrochloric acid solution. Add 600mL chloroform for extraction. The organic phase was repeatedly washed with water until neutral, and dried by adding anhydrous magnesium sulfate. Chloroform was distilled off under reduced pressure to obtain a crude product. The crude product...

Embodiment 3

[0084] Example 3, the synthesis of phenylethynyl-terminated PPQ (in formula I, Y=-O-) with a designed molecular weight of 2500 g / mol

[0085] Add 13.1898g (17.20mmol) in a 250mL there-necked flask equipped with mechanical stirring, thermometer, nitrogen inlet, step 1) of embodiment 1) to prepare tetraketone compound 9 shown in gained formula II, 9-bis[(4-benzoic acid Acyloxy)phenyl]fluorene, 4.8415g (15.60mmol) 4-phenylethynyl benzil and 50g NMP, stirred at room temperature for 20min to mix well, then added 5.7568g (25.00mmol) 3,3',4, 4'-Tetraaminodiphenyl ether and 45 g NMP. . Under the protection of nitrogen, the temperature was raised to 120° C., and the reaction was carried out at constant temperature for 4 hours. After cooling to room temperature, the reaction solution was poured into water, and a yellow precipitate precipitated out. A yellow solid was obtained by filtration. The yellow solid was pulverized and then repeatedly washed with water and filtered. The obtain...

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Abstract

The invention discloses a polyphenylquinoxaline polymer, its preparation method and application. The polymer has a structure general formula as shown in formula I. With an aromatic tetraone compound, an aromatic tetramine compound and an aromatic end-capping agent as raw materials, the polymer is prepared by a high temperature polycondensation method. By designing an appropriate molecular weight, the polymer material can obtain good fusion performance, and can obtain a good thermal property and a mechanical property through high temperature curing reaction of a reactive terminal group. The material of the invention can be used as high performance engineering plastics, a high temperature resistance adhesive, a fiber reinforced resin matrix composite material and its products, etc., and can be applied in the high technology fields of aerospace, petrochemical engineering, and automobiles, etc.

Description

technical field [0001] The invention belongs to the field of high-performance thermosetting high-temperature-resistant resins, and relates to a thermosetting polyphenylquinoxaline resin and a preparation method and application thereof. Background technique [0002] Polyphenylquinoxaline (PPQ) is a class of aromatic heterocyclic polymer materials prepared by polymerization of aromatic tetraketone monomers and tetraamine monomers. Its special molecular structure endows it with many excellent properties, such as excellent heat resistance and heat resistance stability, good mechanical properties, hydrolysis resistance, low moisture absorption rate, etc. These outstanding performance characteristics make it very potential as a High-performance engineering plastics, composite matrix resins, and high-temperature-resistant adhesives are used in high-tech fields such as aviation, aerospace, and space (Rabilloud G. High performance polymers 2. Polyquinoxalines and polyimides. Editions...

Claims

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Application Information

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IPC IPC(8): C08G73/06C07D241/42C08L79/04C08K7/06C08K7/14C08K7/10C09J179/04
Inventor 杨士勇李诚刘金刚
Owner INST OF CHEM CHINESE ACAD OF SCI
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