WO2005068542A1 - Polymer solutions - Google Patents

Polymer solutions Download PDF

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Publication number
WO2005068542A1
WO2005068542A1 PCT/GB2005/000058 GB2005000058W WO2005068542A1 WO 2005068542 A1 WO2005068542 A1 WO 2005068542A1 GB 2005000058 W GB2005000058 W GB 2005000058W WO 2005068542 A1 WO2005068542 A1 WO 2005068542A1
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Prior art keywords
electrocatalyst
water
polymer
solvent
solution
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PCT/GB2005/000058
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French (fr)
Inventor
Howard Matthew Colquhoun
Zhixue Zhu
Martin Philip Hogarth
Original Assignee
Johnson Matthey Public Limited Company
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Publication of WO2005068542A1 publication Critical patent/WO2005068542A1/en

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/88—Processes of manufacture
    • H01M4/8878—Treatment steps after deposition of the catalytic active composition or after shaping of the electrode being free-standing body
    • H01M4/8892—Impregnation or coating of the catalyst layer, e.g. by an ionomer
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/8605—Porous electrodes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/8663—Selection of inactive substances as ingredients for catalytic active masses, e.g. binders, fillers
    • H01M4/8673—Electrically conductive fillers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/88—Processes of manufacture
    • H01M4/8825—Methods for deposition of the catalytic active composition
    • H01M4/8828—Coating with slurry or ink
    • 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
    • H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
    • 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
    • C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
    • C08J2381/06—Polysulfones; Polyethersulfones
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/90—Selection of catalytic material
    • H01M4/92—Metals of platinum group
    • 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

Definitions

  • POLYMER SOLUTIONS The present invention relates to novel polymer solutions and electrocatalyst inks comprising ion-conducting polymers.
  • Sulphonated polyarylethersulphone and polyaryletherketone polymers are useful membrane materials and have been used in ultra-filtration processes such as reverse osmosis and nanofiltration.
  • US 5,693,740 discloses sulphonated polyarylethersulphone copolymers of the formula (I):
  • PEM polymer electrolyte fuel cells.
  • the most commonly used polymers in polymer electrolyte membranes are perfiuorinated sulphonic acid polymers such as Nafion® and Flemion®. However, the perfiuorinated polymers are expensive. Solutions of ion-conducting polymers are used to incorporate ion-conducting polymer into electrocatalyst layers in fuel cell membrane electrode assemblies. Ion- conducting polymer is added to electrocatalyst layers to improve the three-phase interface between the gaseous reactants (e.g. air or hydrogen), the electrocatalyst surface and polymer electrolyte membrane.
  • gaseous reactants e.g. air or hydrogen
  • a wide variety of solvents are employed in ion- conducting polymer solutions, but, if possible, it is desirable to use aqueous solutions of ion-conducting polymers. This eliminates the safety risks posed by flammable and potentially hazardous organic solvents.
  • polymers To be useful in a fuel cell, polymers must not be directly soluble in water at fuel cell temperatures. If the polymers were soluble, they would dissolve during fuel cell operation and the cell would fail.
  • the present inventors have succeeded in providing aqueous solutions of sulphonated polyarylethersulphone or polyaryletherketone polymers wherein the polymers are not soluble in water at temperatures of up to 100°C.
  • the present invention provides a polymer solution comprising a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water.
  • the solvent is at least 95% water, preferably the solvent is at least 99% water.
  • the solvent percentages are weight percentages based on the total weight of the solvent.
  • the solutions are safe to handle and can be used to manufacture electrocatalyst layers comprising sulphonated polyarylethersulphone or polyaryletherketone polymers.
  • the solutions are made by dissolving the sulphonated polyarylethersulphone or polyaryletherketone polymer in a first solvent.
  • the first solvent comprises a non- aqueous component that has a lower boiling point than water.
  • the non-aqueous component is a polar solvent such as acetone, tetrahydrofuran (THF), methyl ethyl ketone (MEK) or 1,2 dimethoxy ethane.
  • the first solvent may contain only the non- aqueous component, but it may also be a mixture of the non-aqueous component and water.
  • a preferred first solvent is a 30:70 (v/v) mixture of water and acetone.
  • the solution of polymer in the first solvent does not contain water
  • water is added.
  • the non-aqueous component is removed from the polymer solution, e.g. by heating or by distillation. It is surprising that as the non-aqueous component is removed, the polymer does not precipitate from solution. Instead, when the non-aqueous component is removed, an aqueous polymer solution that is stable for up to several months is provided.
  • the solid content of the polymer solution is suitably more than lwt% and less than 10wt%. Solutions with higher solid contents are likely to be viscous and may even solidify. Solutions with lower solid contents are unlikely to be useful for incorporating polymer into electrocatalyst layers.
  • the polymer solution according to the invention comprises a polymer of formula (I) :
  • the polymer of formula (I) is a copolymer containing monomer units of formula m and n.
  • the ratio of m:n is suitably in the range from 10:1 to 1:10, preferably from 3:1 to 1:5, most preferably about 1:1 to 1:4.
  • the m:n ratio affects the equivalent weight of the polymer and therefore affects the water uptake of the polymer.
  • the polymer of formula (I) may be prepared by a polycondensation route as described in US 5,693,740.
  • the invention yet further provides an electrocatalyst ink comprising at least one electrocatalyst and a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water.
  • the solvent is at least 95% water, preferably the solvent is at least 99% water.
  • the solvent percentages are weight percentages based on the total weight of the solvent.
  • the electrocatalyst ink may be prepared by mixing one or more electrocatalysts with the aqueous polymer solution according to the invention. Alternatively, the electrocatalyst ink may be prepared by mixing the electrocatalyst with the polymer dissolved in the first solvent, and then removing the non-aqueous component to provide an ink wherein the solvent is at least 90% water.
  • Electrocatalyst metals for use in the present invention may be selected from (i) the platinum group metals (i.e. platinum, palladium, rhodium, ruthenium, iridium and osmium), (ii) gold or silver, (iii) a base metal or base metal oxide, or an alloy or mixture comprising one or more of these metals.
  • the preferred electrocatalyst metal for use in the present invention comprises platinum.
  • the electrocatalyst metal may be unsupported, or supported on a conductive substrate, and preferably is supported on, for example a high surface area particulate carbon.
  • the solids content of the electrocatalyst ink is between 5 and 50 weight %, preferably between 10 and 40 weight %, based on the weight of the ink.
  • the weight ratio of the electrocatalyst (the one or more electrocatalyst metals plus any catalyst support) to the polymer is between 1:1 and 10:1.
  • the present invention further provides two processes for preparing electrocatalyst layers on substrates, wherein sulphonated polyarylethersulphone or polyaryletherketone polymers are incorporated into the electrocatalyst layers.
  • a first process comprises a step wherein an electrocatalyst ink according to the invention is applied onto the substrate by any method known to the skilled person, e.g. printing or spraying.
  • the second process comprises a step wherein an electrocatalyst ink is applied onto the substrate to form an electrocatalyst layer, and comprises a subsequent step wherein a polymer solution according to the invention is applied to the electrocatalyst layer, e.g. by spraying or printing.
  • the substrate is suitably a gas diffusion substrate, a polymer electrolyte membrane or a transfer substrate such as a decal blank. Electrocatalyst layers may be applied to gas diffusion substrates or membranes by transferring the layer from a transfer substrate.
  • the weight ratio of the electrocatalyst (the one or more electrocatalyst metals plus any catalyst support) to the sulphonated polyarylethersulphone or polyaryletherketone polymer in the electrocatalyst layer is suitably between 1:1 and 10:1.
  • the present invention yet further provides a process for preparing a membrane electrode assembly (MEA) comprising a step of preparing an electrocatalyst layer by the process of the invention.
  • MEA membrane electrode assembly
  • the polymer electrolyte membrane in the MEA may comprise the same sulphonated polyarylethersulphone or polyaryletherketone polymer as is found in the electrocatalyst layer, or a different membrane material may be used.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Sustainable Energy (AREA)
  • Sustainable Development (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inert Electrodes (AREA)
  • Fuel Cell (AREA)

Abstract

A polymer solution comprising a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, is disclosed. The solvent is at least 90% water. The polymer solution may be used to prepare electrocatalyst inks and electrocatalyst layers for use in fuel cells.

Description

POLYMER SOLUTIONS The present invention relates to novel polymer solutions and electrocatalyst inks comprising ion-conducting polymers.
Sulphonated polyarylethersulphone and polyaryletherketone polymers are useful membrane materials and have been used in ultra-filtration processes such as reverse osmosis and nanofiltration. US 5,693,740 discloses sulphonated polyarylethersulphone copolymers of the formula (I):
Figure imgf000002_0001
Solutions of this polymer in N-methylpyrrolidone (NMP) and in a mixture of methoxyethanol (57%), methanol (38%), sulphuric acid (0.25%) and water (4.75%) are disclosed.
Increasingly, sulphonated polyarylethersulphone and polyaryletherketone polymers are being considered for use as membranes in polymer electrolyte membrane
(PEM) fuel cells. The most commonly used polymers in polymer electrolyte membranes are perfiuorinated sulphonic acid polymers such as Nafion® and Flemion®. However, the perfiuorinated polymers are expensive. Solutions of ion-conducting polymers are used to incorporate ion-conducting polymer into electrocatalyst layers in fuel cell membrane electrode assemblies. Ion- conducting polymer is added to electrocatalyst layers to improve the three-phase interface between the gaseous reactants (e.g. air or hydrogen), the electrocatalyst surface and polymer electrolyte membrane. A wide variety of solvents are employed in ion- conducting polymer solutions, but, if possible, it is desirable to use aqueous solutions of ion-conducting polymers. This eliminates the safety risks posed by flammable and potentially hazardous organic solvents.
To be useful in a fuel cell, polymers must not be directly soluble in water at fuel cell temperatures. If the polymers were soluble, they would dissolve during fuel cell operation and the cell would fail. The present inventors have succeeded in providing aqueous solutions of sulphonated polyarylethersulphone or polyaryletherketone polymers wherein the polymers are not soluble in water at temperatures of up to 100°C. Accordingly the present invention provides a polymer solution comprising a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water. Suitably the solvent is at least 95% water, preferably the solvent is at least 99% water. (NB: The solvent percentages are weight percentages based on the total weight of the solvent). The solutions are safe to handle and can be used to manufacture electrocatalyst layers comprising sulphonated polyarylethersulphone or polyaryletherketone polymers.
The solutions are made by dissolving the sulphonated polyarylethersulphone or polyaryletherketone polymer in a first solvent. The first solvent comprises a non- aqueous component that has a lower boiling point than water. Suitably, the non-aqueous component is a polar solvent such as acetone, tetrahydrofuran (THF), methyl ethyl ketone (MEK) or 1,2 dimethoxy ethane. The first solvent may contain only the non- aqueous component, but it may also be a mixture of the non-aqueous component and water. A preferred first solvent is a 30:70 (v/v) mixture of water and acetone.
If the solution of polymer in the first solvent does not contain water, water is added. Then the non-aqueous component is removed from the polymer solution, e.g. by heating or by distillation. It is surprising that as the non-aqueous component is removed, the polymer does not precipitate from solution. Instead, when the non-aqueous component is removed, an aqueous polymer solution that is stable for up to several months is provided.
The solid content of the polymer solution is suitably more than lwt% and less than 10wt%. Solutions with higher solid contents are likely to be viscous and may even solidify. Solutions with lower solid contents are unlikely to be useful for incorporating polymer into electrocatalyst layers.
In a preferred embodiment, the polymer solution according to the invention comprises a polymer of formula (I) :
Figure imgf000004_0001
The polymer of formula (I) is a copolymer containing monomer units of formula m and n. The ratio of m:n is suitably in the range from 10:1 to 1:10, preferably from 3:1 to 1:5, most preferably about 1:1 to 1:4. The m:n ratio affects the equivalent weight of the polymer and therefore affects the water uptake of the polymer. The polymer of formula (I) may be prepared by a polycondensation route as described in US 5,693,740.
The invention yet further provides an electrocatalyst ink comprising at least one electrocatalyst and a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water.
Suitably the solvent is at least 95% water, preferably the solvent is at least 99% water. (NB: The solvent percentages are weight percentages based on the total weight of the solvent). The electrocatalyst ink may be prepared by mixing one or more electrocatalysts with the aqueous polymer solution according to the invention. Alternatively, the electrocatalyst ink may be prepared by mixing the electrocatalyst with the polymer dissolved in the first solvent, and then removing the non-aqueous component to provide an ink wherein the solvent is at least 90% water.
The term "electrocatalyst" will be well understood by a person skilled in the art to mean a catalyst that when incorporated into a gas diffusion electrode facilitates an electrochemical reaction. Electrocatalyst metals for use in the present invention may be selected from (i) the platinum group metals (i.e. platinum, palladium, rhodium, ruthenium, iridium and osmium), (ii) gold or silver, (iii) a base metal or base metal oxide, or an alloy or mixture comprising one or more of these metals. The preferred electrocatalyst metal for use in the present invention comprises platinum. The electrocatalyst metal may be unsupported, or supported on a conductive substrate, and preferably is supported on, for example a high surface area particulate carbon.
Suitably the solids content of the electrocatalyst ink is between 5 and 50 weight %, preferably between 10 and 40 weight %, based on the weight of the ink. Suitably the weight ratio of the electrocatalyst (the one or more electrocatalyst metals plus any catalyst support) to the polymer is between 1:1 and 10:1.
The present invention further provides two processes for preparing electrocatalyst layers on substrates, wherein sulphonated polyarylethersulphone or polyaryletherketone polymers are incorporated into the electrocatalyst layers. A first process comprises a step wherein an electrocatalyst ink according to the invention is applied onto the substrate by any method known to the skilled person, e.g. printing or spraying. The second process comprises a step wherein an electrocatalyst ink is applied onto the substrate to form an electrocatalyst layer, and comprises a subsequent step wherein a polymer solution according to the invention is applied to the electrocatalyst layer, e.g. by spraying or printing. The substrate is suitably a gas diffusion substrate, a polymer electrolyte membrane or a transfer substrate such as a decal blank. Electrocatalyst layers may be applied to gas diffusion substrates or membranes by transferring the layer from a transfer substrate.
The weight ratio of the electrocatalyst (the one or more electrocatalyst metals plus any catalyst support) to the sulphonated polyarylethersulphone or polyaryletherketone polymer in the electrocatalyst layer is suitably between 1:1 and 10:1.
The present invention yet further provides a process for preparing a membrane electrode assembly (MEA) comprising a step of preparing an electrocatalyst layer by the process of the invention. The polymer electrolyte membrane in the MEA may comprise the same sulphonated polyarylethersulphone or polyaryletherketone polymer as is found in the electrocatalyst layer, or a different membrane material may be used.
The invention will now be described by reference to examples which are not intended to be limiting of the invention:
EXAMPLE 1: Polvmer Solution
Figure imgf000006_0001
The ionomer shown above (0.25 g, m = n, equivalent weight 620 g mol"1, IN. = 1.69 dL g"1) was dissolved in a mixture of water (3 rnL) and acetone (7 mL) to form a homogeneous non-viscous solution. Careful evaporation of acetone under vacuum at room temperature gave an aqueous ionomer solution, stable for at least one month at room temperature. EXAMPLE 2: Polymer Solution
0.25g of an ionomer with the general formula shown in example 1, but wherein m = 2n (equivalent weight 504 g mol"1) was dissolved in a mixture of water (3 mL) and acetone (7 mL). Acetone was evaporated off under weak vacuum to provide a sample having a weight of 3.25g. At this point, proton NMR showed that there was about 2wt% of acetone remaining in the solution. The sample was then evaporated under high vacuum at room temperature for an extended period of time. The amount of acetone in the solution was reduced to 0.075wt%. The resulting aqueous solution was clear and stable.

Claims

1. A polymer solution comprising a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water.
2. A polymer solution according to claim 1, wherein the solvent is at least 95% water.
3. A polymer solution according to claim 1 or claim 2, wherein the solid content of the polymer solution is more than lwt% and less than 10wt%.
4. A polymer solution according to any preceding claim, comprising a polymer of formula (I):
Figure imgf000008_0001
5. A process for preparing a polymer solution according to any preceding claim, comprising steps of: a) dissolving the sulphonated polyarylethersulphone or polyaryletherketone polymer in a first solvent, wherein the first solvent comprises a non-aqueous component that has a lower boiling point than water, to provide a first solution; b) if the first solution does not contain water, adding water to the first solution; and c) removing the non-aqueous component from the first solution.
6. A process according to claim 4, wherein the non-aqueous component is acetone, tetrahydrofuran, methyl ethyl ketone, dimethyl ether or 1,2 dimethoxy ethane.
7. A process according to claim 5 or claim 6, wherein the first solvent further comprises water.
8. A process according to any one of claims 5 to 7, wherein the non-aqueous component is removed from the first solution by heating or distillation.
9. An electrocatalyst ink comprising at least one electrocatalyst and a sulphonated polyarylethersulphone or polyaryletherketone polymer that is not directly soluble in water at temperatures of up to 100°C, characterised in that the solvent is at least 90% water.
10. An electrocatalyst ink according to claim 9, wherein the solvent is at least 95% water.
11. An electrocatalyst ink according to claim 9 or claim 10, wherein the solids content of the electrocatalyst ink is between 5 and 50 weight %, based on the weight of the ink.
12. An electrocatalyst ink according to any one of claims 9 to 11, wherein the weight ratio of the electrocatalyst to the polymer is between 1 : 1 and 10:1.
13. A process for preparing an electrocatalyst layer on a substrate, comprising a step wherein an electrocatalyst ink according to any one of claims 9 to 12 is applied onto the substrate.
14. A process for preparing an electrocatalyst layer on a substrate, comprising a step wherein an electrocatalyst ink is applied onto the substrate to form an electrocatalyst layer, and comprising a subsequent step wherein a polymer solution according to any one of claims 1 to 4 is applied to the electrocatalyst layer.
PCT/GB2005/000058 2004-01-13 2005-01-12 Polymer solutions WO2005068542A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007003568A1 (en) * 2005-06-30 2007-01-11 Basf Aktiengesellschaft Aqueous formulations containing polyaromatic compounds with acid groups
US20100316929A1 (en) * 2006-12-28 2010-12-16 Basf Se Aqueous formulations comprising polyaromatic compounds bearing acid groups and/or salts of acid groups, process for producing them, further formulations produced using the aqueous formulations and use of the further formulations in fuel cells

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013765A (en) * 1988-04-30 1991-05-07 Akzo N.V. Method for sulfonating aromatic polyether sulfones
WO1998055534A2 (en) * 1997-06-06 1998-12-10 Aventis Research & Technologies Gmbh & Co Kg. Method for producing solutions of polymers functionalized by acid groups by microwave radiation
EP0932213A1 (en) * 1996-06-28 1999-07-28 Sumitomo Chemical Company, Limited Polymer electrolyte for fuel cell
WO2003082956A1 (en) * 2002-04-01 2003-10-09 Virginia Tech Intellectual Properties, Inc. Sulfonated polymer composition for forming fuel cell electrodes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013765A (en) * 1988-04-30 1991-05-07 Akzo N.V. Method for sulfonating aromatic polyether sulfones
EP0932213A1 (en) * 1996-06-28 1999-07-28 Sumitomo Chemical Company, Limited Polymer electrolyte for fuel cell
WO1998055534A2 (en) * 1997-06-06 1998-12-10 Aventis Research & Technologies Gmbh & Co Kg. Method for producing solutions of polymers functionalized by acid groups by microwave radiation
WO2003082956A1 (en) * 2002-04-01 2003-10-09 Virginia Tech Intellectual Properties, Inc. Sulfonated polymer composition for forming fuel cell electrodes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007003568A1 (en) * 2005-06-30 2007-01-11 Basf Aktiengesellschaft Aqueous formulations containing polyaromatic compounds with acid groups
US7776957B2 (en) 2005-06-30 2010-08-17 Basf Aktiengesellschaft Aqueous formulations containing polyaromatic compounds with acid groups
US20100316929A1 (en) * 2006-12-28 2010-12-16 Basf Se Aqueous formulations comprising polyaromatic compounds bearing acid groups and/or salts of acid groups, process for producing them, further formulations produced using the aqueous formulations and use of the further formulations in fuel cells

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