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Poly(aromatic (thio)ether sulfone material containing phosphonate group and preparation method and application of poly(aromatic (sulfide)ether sulfone material

A phosphonate group and aromatic technology, which is applied in the field of new polymer materials, synthesis of phosphonylated polyarylether polymers and their preparation, can solve the problems of easy deformation, increased water treatment costs, and weak resistance And other issues

Active Publication Date: 2014-11-19
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cellulose acetate membranes are easily attacked by microorganisms, easily deformed under high temperature or high pressure conditions, and are only suitable for a narrow pH range; aromatic polyamide composite membranes show considerable resistance to continuous exposure to oxidants such as free chlorine. Weak resistance, thus increasing the process of water treatment process and also increasing the cost of water purification treatment

Method used

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  • Poly(aromatic (thio)ether sulfone material containing phosphonate group and preparation method and application of poly(aromatic (sulfide)ether sulfone material
  • Poly(aromatic (thio)ether sulfone material containing phosphonate group and preparation method and application of poly(aromatic (sulfide)ether sulfone material
  • Poly(aromatic (thio)ether sulfone material containing phosphonate group and preparation method and application of poly(aromatic (sulfide)ether sulfone material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 3,3 ， -Bis(diethoxyphosphono)-4,4 ， - Preparation of difluorodiphenyl sulfone:

[0039] (1) 3,3 ， -Dibromo-4,4 ， - Preparation of difluorodiphenyl sulfone:

[0040]

[0041] To a 250 mL three-necked bottle, add 4,4， -25.4 g (0.1 mol) of difluorodiphenyl sulfone, 150 mL concentrated sulfuric acid, mechanically stirred to dissolve, added 39.2 g (0.22 mol) of N-bromosuccinimide in batches, reacted at room temperature overnight, and poured the reaction solution into In ice water, a solid was precipitated, filtered, washed with water, and recrystallized from toluene to obtain 30 g of white crystals, with a yield of 73%. 1 H-NMR (DMSO- d 6 ): δ = 8.46-8.44 (m, 2 H), 8.15-8.11 (m, 2 H), 7.65 (t, J = 8.8 Hz, 2 H) ppm.

[0042] (2) 3,3 ， -Bis(diethoxyphosphono)-4,4 ， - Preparation of difluorodiphenyl sulfone:

[0043]

[0044] Will 3,3 ， -Dibromo-4,4 ， -Difluorodiphenyl sulfone and triethyl phosphite are fed according to the ratio of 1:8.0, N 2 Protected, th...

Embodiment 2

[0046] 3,3 ， -Bis(diethoxyphosphono)-4,4 ， - Preparation of dichlorodiphenyl sulfone:

[0047] (1) 3,3 ， -Dibromo-4,4 ， - Preparation of dichlorodiphenyl sulfone:

[0048]

[0049] To a 250 mL three-necked bottle, add 4,4 ， -28.7 g (0.1 mol) of dichlorodiphenyl sulfone, 150 mL concentrated sulfuric acid, mechanically stirred to dissolve, added 39.2 g (0.22 mol) of N-bromosuccinimide in batches, reacted overnight at room temperature, poured the reaction solution into In ice water, a solid was precipitated, filtered, washed with water, and recrystallized from toluene to obtain 36 g of white crystals, with a yield of 81%. 1 H-NMR (DMSO- d 6 ): δ = 8.45-8.43 (m, 2 H), 8.06-8.04 (m, 2 H), 7.88 (t, J = 8.4 Hz, 2 H) ppm.

[0050] (2) 3,3 ， -Bis(diethoxyphosphono)-4,4 ， - Preparation of dichlorodiphenyl sulfone:

[0051]

[0052] Will 3,3 ， -Dibromo-4,4 ， -Dichlorodiphenyl sulfone and triethyl phosphite are charged according to the ratio of 1:8.0, N 2 Protected, ...

Embodiment 3

[0054] Preparation of phosphonate polymer (I-1):

[0055]

[0056] (Ⅰ-1)

[0057] Under nitrogen atmosphere, the 3,3 ， -Bis(diethoxyphosphono)-4,4 ， -difluorodiphenylsulfone (7.37 g, 14.0 mmol), 4,4 · -Dichlorodiphenylsulfone (1.72 g, 6.0 mmol), biphenol (3.72 g, 20.0 mmol), anhydrous potassium carbonate (3.18 g, 23.0 mmol), N,N-dimethylacetamide (DMAc, 56 mL), toluene (28 mL) were mixed and heated to 160°C, water was separated for 4 hours, the toluene was distilled off, the temperature was raised to 180°C, and the reaction was carried out for 36 hours. Slowly pour the reaction solution into 400 mL of deionized water to obtain a white strip polymer, change the water, keep the temperature at 80°C, boil in water three times, each time for 6 hours, dry, and then vacuum dry at 100°C for 24 hours to obtain white fibers The obtained polymer was 11.22 g, the yield was 95%, and the intrinsic viscosity was 0.54 dL / g.

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Abstract

The invention discloses a poly(aromatic (thio)ether sulfone material containing a phosphonate group. The preparation method comprises the following steps of mixing a monomer containing the phosphonate group and a bis(thio)phenol monomer (or two different bis(thio)phenol monomers) with a dihalide monomer at a certain ratio; in the presence of medium alkali, strong alkali and toluene, under the condition of heating to a certain temperature and in a high-boiling-point non-protonic solvent, firstly carrying out reflux and water diversion for a certain time and then evaporating toluene out, raising the reaction temperature and continuing the reaction for a certain time; after the reaction is completed, pouring the reaction liquid into deionized water, washing the obtained solids with deionized water for three times and carrying out vacuum drying to obtain a novel polymer containing the phosphonate group. The novel polymer containing the phosphonate group is hydrolyzed and neutralized to obtain a polymer containing a phosphonic acid or phosphate group and good nanofiltration / reverse osmosis desalination and proton conductive performances are achieved.

Description

[0001] The application was supported by the key project of Tianjin Science and Technology Commission (contract number: 12ZCDZSF07000) and the national "863" project (project number: 2012AA03A601). technical field [0002] The invention belongs to the technical field of polymer materials, and relates to the fields of nanofiltration, reverse osmosis membrane water treatment and fuel cell application materials preparation, in particular to the synthesis of phosphonylated polyarylether polymers and their preparation methods, and related A novel polymer material containing phosphonate, phosphonic acid, and phosphonate groups, and an efficient preparation method thereof. Background technique [0003] As an energy technology, fuel cells have the advantages of energy security, supply security and environmental friendliness. The proton exchange membrane is the core component of the fuel cell. The proton exchange membrane in the high-efficiency fuel cell has the following characterist...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/23C08G75/04H01M8/10B01D71/68C02F1/44H01M8/1027H01M8/1032H01M8/1034
CPCY02A20/131Y02E60/50
Inventor 张中标宋凡波李飞王智强汤红英宋爱茹
Owner TIANJIN NORMAL UNIVERSITY
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