WO2011069281A1 - Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation - Google Patents

Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation Download PDF

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Publication number
WO2011069281A1
WO2011069281A1 PCT/CN2009/001432 CN2009001432W WO2011069281A1 WO 2011069281 A1 WO2011069281 A1 WO 2011069281A1 CN 2009001432 W CN2009001432 W CN 2009001432W WO 2011069281 A1 WO2011069281 A1 WO 2011069281A1
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WO
WIPO (PCT)
Prior art keywords
ion exchange
exchange resin
reaction
monomer
sulfonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2009/001432
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English (en)
Chinese (zh)
Inventor
张永明
秦胜
高自宏
张恒
魏茂祥
李勇
王军
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Dongyue Shenzhou New Material Co Ltd
Original Assignee
Shandong Dongyue Shenzhou New Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shandong Dongyue Shenzhou New Material Co Ltd filed Critical Shandong Dongyue Shenzhou New Material Co Ltd
Priority to JP2012542328A priority Critical patent/JP5577411B2/ja
Priority to US13/514,954 priority patent/US9023554B2/en
Priority to CA2783850A priority patent/CA2783850C/fr
Priority to EP09851961.4A priority patent/EP2511311B1/fr
Priority to PCT/CN2009/001432 priority patent/WO2011069281A1/fr
Publication of WO2011069281A1 publication Critical patent/WO2011069281A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/184—Monomers containing fluorine with fluorinated vinyl ethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16—Organic material
    • B01J39/18—Macromolecular compounds
    • B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1466—Monomers containing sulfur
    • C08F216/1475—Monomers containing sulfur and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
    • H01M8/1023—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
    • H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. in situ polymerisation or in situ crosslinking
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • 3282875 is the first publication published by DuPont on the synthesis of sulfonyl fluoride monomer and the preparation of sulfonic acid resin.
  • the emulsion polymerization reaction in aqueous system is adopted.
  • US 3,560,568 is a patent published by DuPont for the preparation of short-side sulfonyl fluoride monomer, sulfonic acid resin and its properties.
  • the conditions of the ternary copolymerization reaction include: the reaction temperature may be 15-100 ° C, preferably 20-80 ° C, the reaction pressure is 2-10 MPa, preferably 2-6 MPa, the reaction time It can be from 1 to 10 hours, preferably from 2 to 8 hours.
  • the invention is a ternary copolymerization of tetrafluoroethylene (TFE) with two short-side sulfonyl fluoroether ether monomers having different structures to obtain a high molecular weight functional perfluoro ion exchange resin, and the terpolymer has high Chemical stability, high ion exchange capacity and good high temperature mechanical stability.
  • the perfluorinated ion exchange resin provided by the present invention still follows the rule that the smaller the ion exchange capacity and the greater the mechanical strength, the ion exchange capacity can reach 0.56 - 2.63 mmol / g (dry resin). Among them, the mechanical strength of the resin having an ion exchange capacity of 1.28-1.95 mmol/g exceeds 30 MPa.
  • the fluorine core magnetic integral value shows that the molecular weight of the tetrafluoroethylene monomer in the polymer structure is 81%.
  • the mole percentage of the sulfonyl fluoride side olefin ether monomer (I) is 10%
  • the mole percentage of the sulfonyl fluoride side olefin ether monomer (II) is 9.0%
  • the total ion exchange capacity is 1.33 mmol/g ( Dry resin).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Sustainable Energy (AREA)
  • Electrochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerization Catalysts (AREA)

Abstract

L'invention porte sur une résine échangeuse d'ions perfluorée, dont la formule de structure est représentée par la formule M. L'invention porte également sur un procédé de préparation de la résine échangeuse d'ions perfluorée, comprenant la copolymérisation ternaire du monomère tétrafluoroéthylène et de deux sortes de monomères éther de vinyle contenant du fluor sulfoné en présence d'un initiateur. La résine échangeuse d'ions perfluorée de l'invention permet de satisfaire aux exigences de résistance mécanique et de capacité d'échange d'ions en même temps et a une bonne stabilité thermique.
PCT/CN2009/001432 2009-12-11 2009-12-11 Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation Ceased WO2011069281A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2012542328A JP5577411B2 (ja) 2009-12-11 2009-12-11 パーフルオロイオン交換樹脂、その調製法および使用
US13/514,954 US9023554B2 (en) 2009-12-11 2009-12-11 Perfluorinated ion exchange resin, preparation method and use thereof
CA2783850A CA2783850C (fr) 2009-12-11 2009-12-11 Resine echangeuse d'ions perfluoree, son procede de preparation et son utilisation
EP09851961.4A EP2511311B1 (fr) 2009-12-11 2009-12-11 Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation
PCT/CN2009/001432 WO2011069281A1 (fr) 2009-12-11 2009-12-11 Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2009/001432 WO2011069281A1 (fr) 2009-12-11 2009-12-11 Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation

Publications (1)

Publication Number Publication Date
WO2011069281A1 true WO2011069281A1 (fr) 2011-06-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2009/001432 Ceased WO2011069281A1 (fr) 2009-12-11 2009-12-11 Résine échangeuse d'ions perfluorée, son procédé de préparation et son utilisation

Country Status (5)

Country Link
US (1) US9023554B2 (fr)
EP (1) EP2511311B1 (fr)
JP (1) JP5577411B2 (fr)
CA (1) CA2783850C (fr)
WO (1) WO2011069281A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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CN111097553A (zh) * 2019-11-26 2020-05-05 南京源泉环保科技股份有限公司 一种处理氰化镀镉废水的固体材料及其制作方法与应用

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* Cited by examiner, † Cited by third party
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CA2783850C (fr) 2009-12-11 2016-07-12 Shandong Huaxia Shenzhou New Material Co., Ltd Resine echangeuse d'ions perfluoree, son procede de preparation et son utilisation
WO2011072418A1 (fr) * 2009-12-15 2011-06-23 山东东岳神舟新材料有限公司 Résine échangeuse d'ions perfluorée de forte capacité d'échange, sa méthode de synthèse et ses applications
JP6319311B2 (ja) * 2013-07-03 2018-05-09 旭硝子株式会社 含フッ素ポリマーの製造方法
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Citations (25)

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Publication number Priority date Publication date Assignee Title
US2393967A (en) 1942-12-24 1946-02-05 Du Pont Process for polymerizing tetrafluoroethylene
US3041317A (en) 1960-05-02 1962-06-26 Du Pont Fluorocarbon sulfonyl fluorides
GB1034197A (en) 1963-09-13 1966-06-29 Du Pont Sulphonic acid derivatives of fluorocarbon vinyl ethers, and polymers thereof
US3282875A (en) 1964-07-22 1966-11-01 Du Pont Fluorocarbon vinyl ether polymers
US3560568A (en) 1968-11-26 1971-02-02 Du Pont Preparation of sulfonic acid containing fluorocarbon vinyl ethers
EP0031724A2 (fr) 1979-12-27 1981-07-08 E.I. Du Pont De Nemours And Company Membranes renforcées, procédé et dispositif pour leur production et leur utilisation comme membranes échangeuses d'ions en cellules de chlore-alcali ou comme catalyseurs
US4789717A (en) 1986-04-29 1988-12-06 Ausimont S.P.A. Process for the polymerization in aqueous dispersion of fluorinated monomers
US4864006A (en) 1986-06-26 1989-09-05 Ausimont S.P.A. Process for the polymerization in aqueous dispersion of fluorinated monomers
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JP5577411B2 (ja) 2014-08-20
US9023554B2 (en) 2015-05-05
US20120237851A1 (en) 2012-09-20
CA2783850C (fr) 2016-07-12
JP2013513667A (ja) 2013-04-22

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