Benzoxazine resin containing quaternary ammonium group and preparation method and application of benzoxazine resin

A technology of quaternary ammonium group and benzoxazine, applied in the field of main chain type benzoxazine resin and its preparation, can solve problems such as high price and reduced conductivity

Active Publication Date: 2020-12-29
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 preparation method and application of benzoxazine resin
  • Benzoxazine resin containing quaternary ammonium group and preparation method and application of benzoxazine resin
  • Benzoxazine resin containing quaternary ammonium group and preparation method and application of benzoxazine resin

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 benzoxazine resin containing a quaternary ammonium group and a preparation method and application of the benzoxazine resin. A main chain type benzoxazine containing the quaternary ammonium group is prepared from dihydric phenol, diamine, monohydric phenol and paraformaldehyde through Mannich reaction and quaternization reaction. And then thermocuring is performed to obtainthe polybenzoxazine film containing the quaternary ammonium group. The main chain type benzoxazine resin containing the quaternary ammonium group is designed and synthesized, so that the quaternary ammonium group can be simply and efficiently introduced into the benzoxazine resin, and the cross-linked polybenzoxazine film is obtained by taking the benzoxazine resin as a precursor. The membrane not only has good membrane-forming property, excellent alcohol resistance and thermal property, but also is low in cost, and is a powerful 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 Applications(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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