Benzoxazine resin containing sulfonic group, and preparation method and application thereof

A technology containing sulfonic acid groups and benzoxazine, which is applied in the field of polymer materials, can solve the problems of poor acid and alkali resistance, high cost, and easy hydrolysis, and achieve good alcohol resistance, strong acid resistance, and high thermal stability. Effect

Active Publication Date: 2013-04-17
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The most commonly used proton exchange membrane at present is the proton exchange membrane named Nafion, which is produced by U.S. DuPont Company. It has the advantages of high proton conductivity and good chemical stability, but Nafion still has the following disadvantages: (1) high cost
[0013] However, the ester group bridging the sulfonic acid group and the benzene ring has the disadvantages of poor acid and alkali resistance and easy hydrolysis.

Method used

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  • Benzoxazine resin containing sulfonic group, and preparation method and application thereof
  • Benzoxazine resin containing sulfonic group, and preparation method and application thereof
  • Benzoxazine resin containing sulfonic group, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1 Synthesis of sulfonic acid-containing benzoxazine monomers based on aniline and sodium p-hydroxybenzenesulfonate

[0085] Dissolve 3.74mL of formaldehyde solution with a mass concentration of 37%, 2.34mL of aniline in 20mL of dioxane, and stir for 0.5h at room temperature, add 4.9g of sodium phenol p-sulfonate, heat up to 90°C, and react for 4h . Post-processing: the solvent was removed by rotary evaporation, and the crude product was vacuum-dried at 60°C to obtain a light yellow powder with a yield of 81%.

[0086] FTIR (KBr, cm -1 ):3331,3033(Ph-H),1600,1501(Ph),1233(stretch,C-O-C),932(oxazine ring).( figure 1 )

[0087] 1 H NMR (300MHz,H 2 O,ppm):4.28(s,2H,N-CH 2 -Ph),5.17(s,2H,N-CH 2 -O),6.74-7.68(m,8H,Ar-H).( figure 2 )

Embodiment 2

[0088] Example 2 Synthesis of sulfonic acid-containing benzoxazine monomers based on allylamine and sodium p-hydroxybenzenesulfonate

[0089] Add 1.0g of paraformaldehyde, 2.0mL of allylamine, 6.53g of sodium p-hydroxybenzenesulfonate, and 30mL of dioxane in sequence in a 100mL flask, stir and mix, gradually raise the temperature to reflux, and react at reflux temperature for 4h to obtain Orange yellow benzoxazine monomer solution, the reaction mixture was evaporated to remove the solvent, the obtained crude product was recrystallized with ethanol, and after drying, light yellow crystals were obtained with a yield of 81%.

[0090] FTIR (KBr, cm -1 ):3331,3033(Ph-H),1193cm -1 (asymmetric C-O-C stretching), 1035cm -1 (symmetric C-O-C stretching),920cm -1 (oxazine ring). ( image 3 )

[0091] 1 H NMR (300MHz,H 2 O, ppm): 3.28 (s, 2H, -CH 2 -CH=CH 2 ),3.55(s,2H,N-CH 2 -Ph),4.35(s,2H,N-CH 2 -O),4.99(m,1H,-CH 2 -CH=CH 2 ),5.13(m,1H,-CH=CH 2 ),5.96(m,1H,-CH=CH 2 ),7.26...

Embodiment 3

[0092] Example 3 Synthesis of sulfonic acid-containing benzoxazine monomers based on phenol and sodium p-aminobenzenesulfonate

[0093]Add 0.75g of paraformaldehyde, 4.87g of sodium p-aminobenzenesulfonate, 2.35g of phenol, and 20mL of dioxane in a 100mL flask in sequence, and react at 90°C for 6h to obtain a pale yellow solution. After washing and recrystallization, a white solid was obtained with a yield of 85%.

[0094] FTIR (KBr, cm -1 ):3331,3033(Ph-H),1600,1501(Ph),1233(stretch,C-O-C),945(trisubstituted benzene ring).

[0095] 1 H NMR (300MHz,H 2 O,ppm):4.59(s,2H,N-CH 2 -Ph),5.20(s,2H,N-CH 2 -O),6.83-7.26(m,8H,Ar-H).

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Abstract

The invention discloses a benzoxazine resins containing sulfonic groups. The method of the invention uses phenol or aminated compounds containing sulfonic groups and formaldehyde as raw materials, by Mannich reaction, to synthesize a series of novel benzoxazine monomers containing sulfonic groups. The benzoxazine monomers are heated to form a polybenzoxazine film containing sulfonic groups by ring-opening polymerization. The new synthesis process directly introduces sulfonic groups onto benzene rings, so the products have advantages of high heat stability, strong acid resistance, good dimension stability, good alcohol rejecting performance, low synthesis cost, and vast application prospect in the proton exchange membrane fuel cell field.

Description

technical field [0001] The invention relates to a sulfonic acid group-containing benzoxazine resin, in particular to a novel sulfonic acid group-containing benzoxazine resin and its preparation method and application. It belongs to the technical field of polymer materials. Background technique [0002] The fuel cell is a clean, efficient, green and environmentally friendly energy source, and the proton exchange membrane is its core component. The circuit supplies current to the outside world. Therefore, the performance of the proton exchange membrane plays a very important role in the performance of the fuel cell, and its quality directly affects the service life of the fuel cell. [0003] The most commonly used proton exchange membrane at present is the proton exchange membrane named Nafion, which is produced by U.S. Dupont Corporation. It has the advantages of high proton conductivity and good chemical stability, but Nafion still has the following disadvantages: (1) high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/16C08G73/00H01M8/10H01M8/1018H01M8/1069
CPCY02E60/50
Inventor 鲁在君姚丙建
Owner SHANDONG UNIV
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