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Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane

A compound and quaternization technology, which is applied in the field of anion exchange membrane, side chain quaternization polyketide and its preparation, can solve the problems of limited application range, achieve good mechanical properties and improve electrical conductivity

Active Publication Date: 2014-05-21
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the method, the side-chain quaternized biphenyl monomer is obtained by mixing 2,2′-dihydroxybiphenyl, potassium carbonate, a quaternizing agent and acetonitrile, and undergoing an etherification reaction. The synthesis and polymerization conditions of the method are simple; The anion exchange membrane prepared by polyketone containing quaternized directional groups has strong alkali resistance, but when the content of quaternary ammonium groups in the polymer is high (such as ion exchange capacity, i.e. IEC>2.0mmol / g), the obtained anion exchange membrane Anion exchange membranes swell greater than 30% at 80°C or higher, limiting their use

Method used

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  • Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane
  • Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane
  • Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Add 1.0mol 2,2′-dihydroxybinaphthalene, 2.2mol potassium carbonate, 2.0mol 4-bromobutyltrimethylammonium bromide and 3.5L dimethyl sulfoxide into a 6.0L reaction flask with nitrogen gas in turn, at 80°C Under mechanical stirring, react for 24h, then add 2.5molNH 4 PF 6 , continue to stir and react at 80°C for 1 h, cool to room temperature, pour into a large amount of water, filter, wash and dry to obtain a solid, the obtained solid is recrystallized by acetonitrile / ethanol with a weight ratio of 95 / 5, filtered, and vacuum dried, Get the anion as PF 6 - The side chain side chain quaternized binaphthyl monomer Q 4 BN (PF 6 - ).

[0087]

[0088] Utilize nuclear magnetic resonance to Q obtained in embodiment 1 4 BN (PF 6 - ) to detect and get the result: 1 HNMR(400MHz,DMSO)δ8.08(d,J=9.0Hz,2H),7.96(d,J=7.9Hz,2H),7.62(d,J=9.1Hz,2H),7.41–7.22(m, 4H),6.99(d,J=8.5Hz,2H),4.17–3.93(m,4H),3.04–2.85(m,4H),2.72(s,18H),1.47–1.28(m,4H),1.26 –1.05(m,4H).

Embodiment 2

[0090] The Q obtained in 0.01mol embodiment 1 is sequentially 4 BN(PF 6 - ), 1.00mol 4,4′-diphenyl ether dicarboxylic acid, 0.99mol 2,2′-dimethoxybinaphthalene and 4L Eaton’s reagent were added to a nitrogen-gassed reaction flask, stirred and reacted at 60°C for 24 hours, and the reaction solution was heated Pour into a large amount of deionized water to obtain a polymer precipitate, filter and wash repeatedly with deionized water until the filtrate is neutral, and then successively in 1.0mol / L NaNO 3 Soak in the solution at 60°C for 48 hours, and replace NaNO every 12 hours 3 solution; at 1.0mol / L Na 2 CO 3 Soak in the solution at 60°C for 48 hours, and replace Na every 12 hours 2 CO 3 solution; soak in deionized water at 60°C for 48 hours, and replace the deionized water every 12 hours, and then dry to obtain CO 3 2- The side chain quaternized polyketide compound shown in the formula I containing the binaphthyl structure that exists in the form. with CO 3 2- The s...

Embodiment 3

[0094] The side chain quaternized binaphthyl monomer Q that 0.01mol embodiment 1 obtains successively 4 BN(PF 6 - ), 1.00mol 4,4′-diphenyl ether dicarboxylic acid, 0.99mol 2,2′-dimethoxybinaphthalene and 4L Eaton’s reagent were added to a nitrogen-gassed reaction flask, stirred and reacted at 100°C for 4h, and the reaction solution was heated Pour a large amount of deionized water to obtain polymer precipitation, filter and wash repeatedly with deionized water until the filtrate is neutral, soak the obtained polymer with 0.1mol / L dilute NaOH solution at room temperature for 24 hours, and then repeatedly wash with deionized water until it is washed Liquid is neutral. Subsequent ion exchange treatment was the same as in Example 2.

[0095] in CF 3 SO 3 - Strong carbonyl absorption peaks and almost no carboxyl absorption peaks were observed in the infrared spectrum of the side chain quaternized polyketones, indicating the occurrence of polyacylation; H NMR spectra confirmed...

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Abstract

The invention provides polyketide with a quaternized side chain and a preparation method thereof as well as an anion-exchange membrane. The polyketide with the quaternized side chain is as shown in a formula I described in the specification. Compared with the prior art, the polyketide with the quaternized side chain has the advantages that firstly a main chain of the polyketide contains a rigid and hydrophobe naphtyl naphthalene structure, so that when the anion-exchange membrane prepared from the polyketide has relatively high ion exchange capacity, the relatively low swelling ratio still can be maintained; secondly, the anion-exchange membrane prepared from the polyketide with the quaternized side chain as shown in the formula I contains more quaternary ammonium groups, so that the electric conductivity of the anion-exchange membrane is improved; thirdly, the polyketide with the quaternized side chain as shown in the formula I contains more naphthalene nucleuses and ether bonds, therefore, the molecular weight of the polyketide is relatively high, and the prepared anion-exchange membrane has relatively good mechanical property.

Description

technical field [0001] The invention belongs to the technical field of polymers and ion exchange membranes, and in particular relates to side chain quaternized polyketide compounds, a preparation method thereof and an anion exchange membrane. Background technique [0002] Anion exchange membrane is a membrane material with positively charged ionic groups fixed on the membrane body, which can selectively pass through anions. It has excellent ion selectivity and mechanical properties. In recent years, it has been used in many fields such as electrolysis and fuel cells. It has been widely researched and applied, such as the concentration or desalination of salt solution by electrolysis, as a diaphragm for electrolyte electrolysis in the chlor-alkali industry, acid recovery from waste acid, as an anion selective electrode, as a battery diaphragm, etc. Anion exchange membranes are generally composed of three parts: polymer matrix, positively charged active groups, and movable ani...

Claims

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Application Information

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IPC IPC(8): C08G61/00C08L65/00C08J5/22
Inventor 张正辉徐铜文
Owner UNIV OF SCI & TECH OF CHINA
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