Benzoxazine resin containing quaternary ammonium group and its preparation method and application

A technology of quaternary ammonium group and benzoxazine, which is applied in the field of main chain type benzoxazine resin and its preparation, can solve the problems of reduced electrical conductivity and high price, and achieve excellent alcohol resistance, low cost, and excellent alkali stability sexual effect

Active Publication Date: 2021-06-29
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a commercial polyelectrolyte membrane, the problem of Nafion membrane (DoPont) is that its conductivity decreases under high temperature and low humidity conditions, and the price is expensive.
At present, the polyelectrolyte membrane based on the backbone type benzoxazine has not been reported yet.

Method used

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  • Benzoxazine resin containing quaternary ammonium group and its preparation method and application
  • Benzoxazine resin containing quaternary ammonium group and its preparation method and application
  • Benzoxazine resin containing quaternary ammonium group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1 Synthesis of quaternary ammonium group-containing main chain type benzoxazine based on bisphenol A and 4,4'-diaminodiphenylmethane

[0105] Dissolve 1.1g of bisphenol A, 2.0g of 4,4'-diaminodiphenylmethane, 1.6g of 4-(2-dimethylaminoethyl)phenol, 1.4g of formaldehyde and 0.2g of triethylamine in 30ml of dimethyl In sulfoxide, the temperature was raised to 90°C for 5h. Post-processing: remove the solvent under reduced pressure, wash with methanol, ethanol, and n-hexane in turn, and dry in vacuum at 70°C overnight to obtain the main chain type benzoxazine.

[0106] 1.1 g of main chain type benzoxazine and 0.3 g of methyl iodide were dissolved in 20 mL of dioxane, heated to 80° C. under magnetic stirring and reacted for 3 hours. After the reaction is finished, filter and vacuum-dry the filter cake to obtain a main-chain benzoxazine containing quaternary ammonium groups with a yield of 95%.

[0107] 1 H NMR (400MHz, d 6 -DMSO, ppm): δ=5.34 (d, J=17.6Hz, O-CH ...

Embodiment 2

[0109] Example 2 Synthesis of quaternary ammonium group-containing main chain type benzoxazine based on bisphenol S and 4,4'-diaminodiphenyl ether

[0110] Dissolve 1.5g of bisphenol S, 2.4g of 4,4'-diaminodiphenyl ether, 1.9g of 4-dimethylaminomethylphenol, 1.8g of formaldehyde and 0.3g of pyridine in 30mL of ethanol, heat up to 85°C for 12 hours . Post-processing: remove the solvent under reduced pressure, wash with methanol, ethanol, and n-hexane in turn, and dry in vacuum at 50°C overnight to obtain the main chain type benzoxazine.

[0111] Dissolve 1.5 g of main-chain benzoxazine and 0.6 g of bromoethane in 15 mL of dimethyl sulfoxide, raise the temperature to 90° C. under magnetic stirring, and react for 5 hours. After the reaction, filter and vacuum-dry the filter cake to obtain the main chain type benzoxazine containing quaternary ammonium groups, with a yield of 90%.

Embodiment 3

[0112] Example 3 Synthesis of quaternary ammonium group-containing main chain type benzoxazine based on bisphenol AF and 4,4'-diaminodiphenylsulfone

[0113] Dissolve 1.8g of bisphenol AF, 2.0g of 4,4'-diaminodiphenylsulfone, 1.9g of 4-dimethylaminomethylphenol, 1.8g of formaldehyde and 0.5g of triethylamine in 30mL of toluene, heat up to 90°C for reaction 20h. Post-processing: remove the solvent under reduced pressure, wash with methanol, ethanol, and n-hexane in turn, and dry in vacuum at 60° C. overnight to obtain the main chain type benzoxazine.

[0114] Dissolve 1.9 g of main-chain benzoxazine and 0.9 g of diethyl sulfate in 25 mL of N,N-dimethylformamide, raise the temperature to 90° C. under magnetic stirring, and react for 5 hours. After the reaction, filter and vacuum-dry the filter cake to obtain main-chain benzoxazine containing quaternary ammonium groups, with a yield of 84%.

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Abstract

The invention relates to a benzoxazine resin containing quaternary ammonium groups and its preparation method and application. The main chain containing quaternary ammonium groups is prepared by Mannich reaction and quaternization reaction of dihydric phenol, diamine, unit phenol and paraformaldehyde type benzoxazines. Then it was thermally cured to obtain a polybenzoxazine film containing quaternary ammonium groups. In the present invention, by designing and synthesizing the main chain type benzoxazine resin with quaternary ammonium groups, not only can the quaternary ammonium groups be introduced into the benzoxazine resin simply and efficiently, but also the cross-linked polybenzoxazine obtained by using it as a precursor film. The film not only has good film-forming properties, excellent alcohol resistance and thermal performance, but also has low cost, and is a strong candidate in the field of fuel cells.

Description

technical field [0001] The invention relates to a benzoxazine resin containing a quaternary ammonium group, in particular to a main chain type benzoxazine resin containing a quaternary ammonium group and a preparation method and application thereof. Background technique [0002] Fuel cells are clean energy sources with high power generation efficiency and low environmental pollution. Polyelectrolyte membranes are the core components of fuel cells. As a commercialized polyelectrolyte membrane, Nafion membrane (DoPont) has the problem that its conductivity decreases under high temperature and low humidity conditions, and the price is expensive. In addition, its poor alcohol resistance hinders its application in methanol fuel cells. Therefore, there is an urgent need to develop new polyelectrolyte membranes. [0003] Currently, polyelectrolyte membranes mainly include proton exchange membranes and anion exchange membranes (AEM). Compared with proton exchange membranes, AEM ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G14/12C08G14/073C08J5/22C08L61/34H01M8/1027H01M8/103
CPCC08G14/06C08G14/12C08J5/2256C08J2361/34H01M8/1027H01M8/103Y02E60/50
Inventor 鲁在君王峥张效全夏永全郗珍衣同刚
Owner SHANDONG UNIV
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