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Carboxyl-containing difluoro monomer, preparation method of difluoro monomer and application of difluoro monomer to preparation of carboxyl-containing polyarylether

A technology of difluoromonomer and polyarylene ether, which is applied in the field of difluoromonomer and its preparation, can solve problems such as reducing mechanical properties, and achieve the effects of improving conductivity, hydrophilic performance and antifouling performance.

Inactive Publication Date: 2015-11-11
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, most ionized polyarylethers introduce polar groups into the polymer, such as the introduction of sulfonic acid groups, which improve the proton conductivity and hydrophilicity but also reduce the mechanical properties of the material itself.

Method used

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  • Carboxyl-containing difluoro monomer, preparation method of difluoro monomer and application of difluoro monomer to preparation of carboxyl-containing polyarylether
  • Carboxyl-containing difluoro monomer, preparation method of difluoro monomer and application of difluoro monomer to preparation of carboxyl-containing polyarylether
  • Carboxyl-containing difluoro monomer, preparation method of difluoro monomer and application of difluoro monomer to preparation of carboxyl-containing polyarylether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Synthetic 3-[4-(2,6-difluorobenzoyl) phenyl] propionic acid monomer

[0033] In the first step, under an argon atmosphere, add 100g (0.63mol) of 2,6-difluorobenzoic acid and 400mL of thionyl chloride to a 1000mL three-necked flask equipped with mechanical stirring, and drop 2mL of N,N-dimethyl Formamide, stirred after adding, heated to reflux of thionyl chloride, and reacted for 8 hours. After the reaction was completed, the thionyl chloride was removed by atmospheric distillation, and the colorless transparent liquid A was obtained by distillation under reduced pressure, that is, 2,6-difluorobenzene formyl chloride. 77.8g after weighing;

[0034] In the second step, under an argon atmosphere, add 31.72g (0.24mol) of anhydrous aluminum trichloride to a 1000mL three-necked flask equipped with a mechanical stirrer and a drying tube, dilute with 150mL of dichloromethane, and slowly drop it in an ice-water bath. 21g (0.11mol) of 2,6-difluorobenzoyl chloride ...

Embodiment 2

[0036] Example 2: Synthesis of biphenyl-type polyethersulfone with a carboxyl content of 20%

[0037] Put 1.1610g (0.004mol) of 3-[4-(2,6-difluorobenzoyl)phenyl]propionic acid and 4.5946 4,4'-dichlorodiphenyl sulfone into a 100mL three-necked flask equipped with mechanical stirring g (0.016mol), 3.7242g (0.02mol) of 4,4'-diphenol, 3.3170g (0.024mol) of potassium carbonate, the molar ratio of feeding is 1:4:5:6, the solvent sulfolane is 30mL, and toluene is 12mL. Azeotropic dehydrating agent. The reaction was carried out under the protection of argon, and the toluene was evaporated after adding water at 150°C for 3 hours, and the temperature was raised to 190°C for 15 hours, and the material was discharged in deionized water to obtain a white solid, which was washed with distilled water and ethanol and dried to obtain 8.2426g of a white solid.

[0038] The white solid of the final product is a biphenyl type polyethersulfone with a carboxyl content of 20%, and its H NMR spectru...

Embodiment 3

[0040] Example 3: Synthesis of biphenyl-type polyethersulfone with a carboxyl content of 25%

[0041] Put 1.4513g (0.005mol) of 3-[4-(2,6-difluorobenzoyl)phenyl]propionic acid, 4.3074 g (0.015mol), 3.7242g (0.02mol) of 4,4'-diphenol, 3.3861g (0.027mol) of potassium carbonate, the molar ratio of feeding is 1:3:4:5.4, the solvent sulfolane is 30mL, and toluene is 12mL. Azeotropic dehydrating agent. The reaction was carried out under the protection of argon, with water at 150°C for 3 hours, then the toluene was distilled off, the temperature was raised to 190°C for 15 hours, and the material was discharged in deionized water to obtain a white solid, which was washed with distilled water and ethanol and dried to obtain 8.1364 g of a white solid.

[0042] The white solid of the final product is a biphenyl type polyethersulfone with a carboxyl content of 25%. Its H NMR spectrum is shown in figure 1 , see the infrared spectrum figure 2 , see the TGA diagram image 3 , see the DS...

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Abstract

The invention provides a carboxyl-containing difluoro monomer, a preparation method of the difluoro monomer and application of the difluoro monomer to preparation of carboxyl-containing polyarylether, and belongs to the technical field of difluoro monomers and preparation of the difluoro monomers. The preparation method comprises the following steps: under argon atmosphere, using 2,6-difluorobenzoic acid as a raw material, thionyl chloride as a solvent and a reactant, and N,N-dimethylformamide as a catalyst to prepare 2,6-difluorobenzoyl chloride; under argon atmosphere and anhydrous condition, using anhydrous aluminium trichloride, 2,6-difluorobenzoyl chloride and 3-phenylpropionic acid as raw materials to prepare the white crystal difluoro monomer, namely, 3-[4-(2,6-difluorobenzoyl) phenyl] propionic acid. Compared with the common polyarylether polymer, the carboxyl-containing polyarylether prepared and synthesized in the invention introduces ionizable polar groups, can be applied to membrane separation technology, and can be used for promoting the hydrophilic performance and anti-fouling performance of a water separation membrane and improving the conductivity of a proton exchange membrane due to the electronegative carboxyl.

Description

technical field [0001] The invention belongs to the technical field of difluoromonomers and their preparation, in particular to a carboxyl-containing difluoromonomer, a preparation method and the application of the difluoromonomer in the preparation of carboxyl-containing polyarylethers. Background technique [0002] Polyarylether materials are composed of two types of materials, namely polyarylether ketone materials and polyarylether sulfone materials. [0003] As a class of semi-crystalline thermoplastic special engineering materials, polyaryletherketone has the characteristics of high heat resistance, radiation resistance, chemical resistance, fatigue resistance, impact resistance, creep resistance, wear resistance, flame retardancy, and excellent electrical properties; Polyarylethersulfone is a kind of amorphous high-temperature-resistant special engineering plastics. The representative ones are polysulfone, polyethersulfone and biphenyl polyethersulfone. The simultaneou...

Claims

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Application Information

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IPC IPC(8): C07C59/88C07C51/373C08G65/40
CPCC07C51/373C07C51/60C08G65/4018C07C59/88C07C63/70
Inventor 姜振华李苏庞金辉李丹琦谢韫吉
Owner JILIN UNIV
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