Cardo structure-containing isatin aromatic hydrocarbon copolymer, preparation method and application thereof

A technology of isatin aromatics and copolymers, which is applied in the field of polymer materials and polymer ion exchange membrane preparation, can solve the problems of low battery performance, poor mechanical properties and chemical stability, etc., and achieve good mechanical properties and stable alkali resistance High performance, the effect of improving battery performance

Active Publication Date: 2020-03-06
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the key problems of poor mechanical properties and chemical stability and low battery performance in polymer ion membranes in current alkaline fuel cells, the present invention provides a Cardo-containing compound with good mechanical properties and high alkali resistance stability. Structural isatin aromatic copolymer, its electrolyte solution and its ion exchange membrane, preparation method and application

Method used

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  • Cardo structure-containing isatin aromatic hydrocarbon copolymer, preparation method and application thereof
  • Cardo structure-containing isatin aromatic hydrocarbon copolymer, preparation method and application thereof
  • Cardo structure-containing isatin aromatic hydrocarbon copolymer, preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0081] Synthesis of bromo N-methylhexylpiperidine salt: Dissolve 2mol of 1,6-dibromohexane in acetone to make a 20% solution, add 1mol of N-methylpiperidine, and react at 40°C for 24h. After centrifugation, the product was washed with acetone several times and dried to obtain bromo N-methylhexylpiperidine salt.

[0082] Add 9,9-dimethylfluorene, isatin and biphenyl into the reactor and stir at 0°C, add trifluoroacetic acid and the catalyst trifluoromethanesulfonic acid, so that the total monomer concentration is 30wt%. After reacting at 15°C for 50h, the product is a homogeneous viscous liquid. At the end of the reaction, pour the reaction solution into a large amount of deionized water, and put the precipitated polymer into 1M NaHCO 3 Excess acid is removed by stirring, washed with water, filtered, and dried in vacuum to obtain isatin-fluorene copolymer. Among them, the molar ratio of 9,9-dimethylfluorene to biphenyl is 6:4; the ratio of the total moles of 9,9-dimethylfluorene ...

Embodiment 2

[0094] The method for the synthesis of bromo N-methylhexylpyrrole salt is the same as in Example 1, wherein the volume concentration of 1,6-dibromohexane when dissolved in the solvent is 10%. The molar ratio of -methylpyrrole is 3:1, and the reaction is carried out at 10°C for 60h.

[0095] 1mmol of fluorene, 8mmol of bromohexane, 0.75ml of 50% NaOH aqueous solution and a small amount of tetrabutylammonium iodide were added to the reaction flask, and the refrigeration-circulation pumping was repeated three times and reacted at 80°C for 10h. Then it was purified with a silica gel column using n-hexane as the eluent to obtain 9,9-dihexylfluorene.

[0096] Add 9,9-dihexylfluorene, isatin and p-terphenyl into the reactor and stir at 0°C, add trifluoroacetic acid and the catalyst trifluoromethanesulfonic acid, so that the total monomer concentration is 10wt%. After reacting for 45 hours at 0°C, the product is a dark green uniform viscous liquid. At the end of the reaction, pour the vi...

Embodiment 3

[0103] The method for the synthesis of bromo N-methylhexylpiperidine salt is the same as in Example 1, wherein the volume concentration of 1,6-dibromohexane when dissolved in a solvent is 40%. The molar ratio of N-methylpiperidine was 10:1, and the reaction was conducted at 60°C for 48 hours.

[0104] Add 9,9-dimethylfluorene, isatin and p-terphenyl into the reactor and stir at 0°C, add trifluoroacetic acid and the catalyst trifluoromethanesulfonic acid, so that the total monomer concentration is 20wt%. After reacting at 5°C for 48h, the product is a dark green uniform viscous liquid. At the end of the reaction, pour the viscous reaction liquid into a large amount of deionized water, and put the precipitated polymer into 1M NaHCO 3 Excessive acid was removed by stirring in the mixture, washed with water, filtered, and dried in vacuum to obtain a copolymer of isatin dimethyl fluorene. Among them, the molar ratio of 9,9-dimethylfluorene to p-terphenyl is 8:2; the ratio of the tota...

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Abstract

Belonging to the field of preparation of polymer materials and polymer ion exchange membranes thereof, the invention relates to a Cardo structure-containing isatin aromatic hydrocarbon copolymer, a preparation method and application thereof. Specifically, by means of superacid catalyzed hydroxyalkylation polycondensation reaction, isatin, 9, 9-disubstituted fluorene and aromatic hydrocarbon are subjected to a multi-component copolymerization reaction to synthesize an isatin-aromatic hydrocarbon copolymer containing Cardo structure and ammonium cations, so that an electrolyte solution and a tough anion exchange membrane can be conveniently prepared, and the polymerization reaction is simple and practicable. A large-volume Cardo structure is introduced into the polymer, thus reducing the adsorption on a catalyst surface and improving the fuel cell performance; an isatin structure is introduced for crosslinking or functionalization so as to further improve the chemical stability and mechanical properties. The copolymer electrolyte solution and the ion exchange membrane have high ionic conductivity, excellent alkali resistance / oxidation resistance and mechanical properties, and have wide application in fuel cells, energy storage batteries, electrolysis and other electrochemical devices or membrane separation related fields.

Description

Technical field [0001] The invention belongs to the field of polymer materials and the preparation of polymer ion exchange membranes, and relates to an isatin aromatic copolymer containing Cardo structure, a preparation method and an application. Background technique [0002] As a clean hydrogen energy technology, polymer ion exchange membrane fuel cells have the advantages of room temperature start-up, high energy efficiency, and zero pollution. They are widely used in the fields of transportation, aerospace, ships, and military science and technology. At present, the proton exchange membrane fuel cell (PEMFC) requires precious metal platinum catalysts to operate, and expensive perfluoropolymer ion membranes such as the Nafion ion membrane of DuPont of the United States are used. Therefore, the high cost of PEMFC restricts its promotion and application. Alkaline anion exchange membrane fuel cell (AEMFC), operating under alkaline conditions, can use non-precious metal catalysts s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02H01M8/1004
CPCC08G61/02H01M8/1004C08G2261/124C08G2261/3142C08G2261/312Y02E60/50
Inventor 朱秀玲王亚洁张帅
Owner DALIAN UNIV OF TECH
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