WO2011069281A1 - 一种全氟离子交换树脂及其制备方法和应用 - Google Patents

一种全氟离子交换树脂及其制备方法和应用 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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WIPO (PCT)
Prior art keywords
ion exchange
exchange resin
reaction
monomer
sulfonyl
Prior art date
Application number
PCT/CN2009/001432
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English (en)
French (fr)
Chinese (zh)
Inventor
张永明
秦胜
高自宏
张恒
魏茂祥
李勇
王军
Original Assignee
山东东岳神舟新材料有限公司
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 山东东岳神舟新材料有限公司 filed Critical 山东东岳神舟新材料有限公司
Priority to EP09851961.4A priority Critical patent/EP2511311B1/de
Priority to JP2012542328A priority patent/JP5577411B2/ja
Priority to US13/514,954 priority patent/US9023554B2/en
Priority to PCT/CN2009/001432 priority patent/WO2011069281A1/zh
Priority to CA2783850A priority patent/CA2783850C/en
Publication of WO2011069281A1 publication Critical patent/WO2011069281A1/zh

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00Copolymers 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
    • C08F214/18Monomers containing fluorine
    • C08F214/184Monomers containing fluorine with fluorinated vinyl ethers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16Organic material
    • B01J39/18Macromolecular compounds
    • B01J39/20Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00Copolymers 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
    • C08F214/18Monomers containing fluorine
    • C08F214/26Tetrafluoroethene
    • C08F214/262Tetrafluoroethene with fluorinated vinyl ethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F216/00Copolymers 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
    • C08F216/12Copolymers 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
    • C08F216/14Monomers containing only one unsaturated aliphatic radical
    • C08F216/1466Monomers containing sulfur
    • C08F216/1475Monomers containing sulfur and oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20Manufacture of shaped structures of ion-exchange resins
    • C08J5/22Films, membranes or diaphragms
    • C08J5/2206Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218Synthetic macromolecular compounds
    • C08J5/2231Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00Fuel cells; Manufacture thereof
    • H01M8/10Fuel cells with solid electrolytes
    • H01M8/1016Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018Polymeric electrolyte materials
    • H01M8/102Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
    • H01M8/1023Polymeric 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
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00Fuel cells; Manufacture thereof
    • H01M8/10Fuel cells with solid electrolytes
    • H01M8/1016Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018Polymeric electrolyte materials
    • H01M8/1069Polymeric electrolyte materials characterised by the manufacturing processes
    • H01M8/1072Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. insitu polymerisation or insitu crosslinking
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00Characterised 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
    • C08J2327/02Characterised 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
    • C08J2327/12Characterised 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
    • C08J2327/18Homopolymers or copolymers of tetrafluoroethylene
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30Hydrogen technology
    • Y02E60/50Fuel cells
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing 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).

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  • 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)
PCT/CN2009/001432 2009-12-11 2009-12-11 一种全氟离子交换树脂及其制备方法和应用 WO2011069281A1 (zh)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP09851961.4A EP2511311B1 (de) 2009-12-11 2009-12-11 Perfluoriertes ionenaustauschharz, herstellungsverfahren und verwendung
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
PCT/CN2009/001432 WO2011069281A1 (zh) 2009-12-11 2009-12-11 一种全氟离子交换树脂及其制备方法和应用
CA2783850A CA2783850C (en) 2009-12-11 2009-12-11 Perfluorinated ion exchange resin, preparation method and use thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2009/001432 WO2011069281A1 (zh) 2009-12-11 2009-12-11 一种全氟离子交换树脂及其制备方法和应用

Publications (1)

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

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2009/001432 WO2011069281A1 (zh) 2009-12-11 2009-12-11 一种全氟离子交换树脂及其制备方法和应用

Country Status (5)

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

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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EP2511311B1 (de) 2009-12-11 2013-11-27 Shandong Huaxia Shenzhou New Material Co., Ltd. Perfluoriertes ionenaustauschharz, herstellungsverfahren und verwendung
CA2784539C (en) * 2009-12-15 2015-06-30 Shandong Huaxia Shenzhou New Material Co., Ltd High exchange capacity perfluorinated ion exchange resin, preparation method and use thereof
EP3018157B1 (de) * 2013-07-03 2017-11-15 Asahi Glass Company, Limited Verfahren zur herstellung eines fluorhaltigen polymers
US9932480B2 (en) * 2014-07-03 2018-04-03 Toyota Motor Engineering & Manufacturing North America, Inc. PEG-assisted deposition of crack-free titania nanocrystalline coatings over Al flakes
KR102212936B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
KR102212933B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
KR102212938B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
KR102212934B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
KR102212937B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
KR102212932B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
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KR102212935B1 (ko) * 2019-07-12 2021-02-05 (주)상아프론테크 과불소계 술폰화 이오노머 제조용 조성물, 이를 이용한 과불소계 술폰화 이오노머, 이를 포함하는 pemfc용 복합 전해질막 및 이를 포함하는 pemfc용 막-전극 접합체
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CN115490798A (zh) * 2022-09-28 2022-12-20 国家电投集团氢能科技发展有限公司 抗氧化离子交换树脂及其制备方法和全氟离子交换膜

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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
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EP2511311A1 (de) 2012-10-17
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