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(12) United States Patent (10) Patent No.: US 7,713,449 B2 Adachi Et Al

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(12) United States Patent (10) Patent No.: US 7,713,449 B2 Adachi Et Al USOO7713449B2 (12) United States Patent (10) Patent No.: US 7,713,449 B2 Adachi et al. (45) Date of Patent: May 11, 2010 (54) POLYMERELECTROLYTIC MATERIAL 6,447,943 B1* 9/2002 Peled et al. ................... 429/33 POLYMERELECTROLYTIC PART, 6,773,844 B2 8/2004 Nakano et al. MEMBRANEELECTRODE ASSEMBLY, AND 6,794,480 B2 9, 2004 Goto et al. POLYMERELECTROLYTE FUEL CELL 6,828,353 B1* 12/2004 Charnocket al. ............. 521/27 2002fOO45085 A1* 4/2002 Formato et al. ............... 429/33 (75) Inventors: Shinya Adachi, Ritto (JP); Daisuke 2002fOO91225 A1 7/2002 McGrath et al. IZuhara, Otsu (JP); Masataka 2008.0075999 A1 3/2008 Izuchara et al. Nakamura, Otsu (JP); Nobuaki Ito, Otsu (JP) (73) Assignee: Toray Industries, Inc., Chuo-ku, Tokyo FOREIGN PATENT DOCUMENTS (JP) JP 53-26777 3, 1978 (*) Notice: Subject to any disclaimer, the term of this JP 56-34329 8, 1981 patent is extended or adjusted under 35 JP 64-22932 1, 1989 U.S.C. 154(b) by 1215 days. JP 5-271460 10, 1993 JP 8-180891 T 1996 (21) Appl. No.: 10/548,110 JP 10-340732 12/1998 (22) PCT Filed: Mar. 5, 2004 JP 2-208322 3, 2000 JP 2001-504636 4/2001 (86). PCT No.: PCT/UP2004/OO2894 JP 2001-192531 T 2001 JP 2001-294705 10, 2001 S371 (c)(1), JP 2001-294.706 10, 2001 (2), (4) Date: Sep. 6, 2005 JP 2002-110200 4/2002 JP 2002-226575 8, 2002 (87) PCT Pub. No.: WO2004/0798.44 JP 2002-524.631 8, 2002 PCT Pub. Date: Sep. 16, 2004 JP 2002-260687 9, 2002 JP 2002-293889 10, 2002 (65) Prior Publication Data JP 2002-324.559 11, 2002 US 2006/O180796 A1 Aug. 17, 2006 JP 2003-12835 1, 2003 (30) Foreign Application Priority Data - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 2003-059569 Mar. 6, 2003 (JP) (Continued) Apr. 22, 2003 (JP) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 2003-116685 Apr. 24, 2003 (JP) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 2003-12O115 OTHER PUBLICATIONS (51) Int. Cl. Walker et al., “Proton-Conducting Polymers with Reduced Methanol HOB I/2 (2006.01) Formation.” J. Apl. Polymer Sci., 1999, V(74), pp. 67-73.* HOLM 8/02 (2006.01) C08G 79/04 (2006.01) (Continued) C08G 75/02 (2006.01) Primary Examiner Stanley Silverman C08G 75/20 (2006.01) Assistant Examiner—Kallambella Vijayakumar C08, 9/28 (2006.01) (74) Attorney, Agent, or Firm Morrison & Foerster LLP (52) U.S. Cl. .................... 252/511; 252/500; 252/182.1; 429/30; 429/33; 429/40: 429/46; 429/188: (57) ABSTRACT 429/314; 204/296; 205/637; 528/337; 528/373; 528/171 (58) Field of Classification Search ................... 429/30, A polymer electrolytic material has excellent proton conduc 429/33, 41, 188, 311, 314, 317, 303, 42, tivity and excellent fuel shutting property, and accordingly 429/500, 511; 252/182.1; 204/296; 205/637 provide a polymer electrolytic fuel cell with a high efficiency. See application file for complete search history. This polymer electrolytic material has an unfreezable water ratio Rw 1 defined by the following expression (S1) in a range (56) References Cited of 20 to 100% by weight in hydrated state: U.S. PATENT DOCUMENTS 5,013,765 A 5, 1991 Sluma et al. in which Winfrepresents the unfreezable water content per 1 5,403,675 A 4/1995 Ogata et al. g of the polymer electrolytic material in dry state and Wfc 5,741,408 A * 4, 1998 Helmer-Metzmann et al. .......................... 204/252 represents the low freezing point water content per 1 g of the 6,103,414 A 8/2000 Cabasso et al. polymer electrolytic material in dry state. 6,365,294 B1 * 4/2002 Pintauro et al. ............... 429/33 6,444,343 B1* 9/2002 Prakash et al. ................ 429/33 39 Claims, No Drawings US 7,713,449 B2 Page 2 FOREIGN PATENT DOCUMENTS Smith, C.D. et al. (1991). “Unique Characteristics Derived From Poly(Arylene Ether Phosphine Oxide)s.” High Performance Poly JP 2003-217342 T 2003 JP 2003-217343 T 2003 mers vol. 3(4):211-229. JP 2003-217365 T 2003 Yanagimachi, Satomi et al. (2002). "Synthesis of Phosphonated JP 2005-0 19055 1, 2005 poly(4-phenoxybenzoyl-1,4-phenylene).” Polymer Preprints, Japan JP 2005-174897 6, 2005 vol. 51(4):750. WO WO-98.22989 5, 1998 Wang, Fet al.(2000). “Synthesis of Sulfonated Poly (Arylene Ether WO WOOOf 15691 * 3f2OOO Sulfone)S Via Direct Polymerization.” Polymer Preprints vol. WO WO-01/19896 3, 2001 41(1):237-238. WO WO-2004-036679 4/2004 Lee, W. et al. (1996). “Proton Transport Through Polyethylene OTHER PUBLICATIONS Tetrafluoroethylene-Copolymer-Based Membrane Containing Sulfonic Acid Group Prepared by RIGP” J. Electochem Soc. , 143 Bailly, Christian et al.(1987). “The Sodium Salts of Sulphonated (9): 2795-2799. Poly(Aryl-Ether-Ether-Ketone) (PEEK): Preparation and Character Greenley, R. (1999). "Q and e Values for Free Radical Copolymer ization.” Polymer vol. 28:1009-1016. Nolte, R. et al. (1993). “Partially Sulfonated Poly(Arylene Ether izations of Vinyl Monomers and Telogens.” Chapter II in Polymer Sulfone)- A Versatile Proton Conducting Membrane Material for Handbook. John Wiley & Sons, Inc. pp. 309-319. Modern Energy Conversion Technologies,” Journal of Membrane Takenaka, H. et al. (1985). "Studies on Solid Polymer Electrolyte Science vol. 83:211-220. Water Electrolysis II, Preparation Methods for Membrane Tang, Hao et al.(1999). "Polyphosphazene Membranes. III. Solid Electrocatalyst Composite.” Denki Kagaku 53(4): 261. State Characterization and Properties of Sulfonated Polybis(3- Ticianelli, E. A. et al. “Method to Advance Technology of Proton methylphenoxy) phosphazene),” Journal of Applied Polymer Science Exchange Membrane Fuel Cells.” Mass Transfer 135(9): 2209-2214. vol. 71:387-399. Hatakana, T. (2002). “Direct Methanol Fuel Cell.” R& D Review of Wang, Feng et al. (2002). “Direct Polymerization of Sulfonated Toyota CRDL, 37(1):59-64 (English language translation of Poly(Arylene Ether Sulfone) Random(statistical) Copolymers: Can abstract). didates for New Proton Exchange Membranes,” Journal of Mem International Search Report mailed on Jun. 29, 2004, directed to brane Science vol. 197:231-242. International Patent Application No. PCT/JP2004/002894; 8 pages. Young, S.K. et al.(2002). "Nafion R/ORMOSILl Nanocomposites via polymer-in situ sol-gel reactions. 1. Probe of ORMOSIL Phase International Preliminary Report on Patentability and Written Opin Nanostructures By 'Si Solid-state NMR Spectroscopy.” Polymers ion mailed Feb. 13, 2006, directed to International Patent Application vol. 432311-2320. No. PCT/JP2004/002894; 14 pages. Wang, Huanting etal. (2002). “Nafion-bifunctional Silica Composite International Search Report mailed on Dec. 6, 2005, directed to Proton Conductive Membranes,” Journal of Material Chemistry vol. International Patent Application No. PCT/JP2005/015703: 4 pages. 12: 834-837. International Preliminary Report on Patentability and Written Opin Ishikiryama, Kazuhiko et al.(1995). "Pore Size Distribution (PSD) ion mailed Mar. 20, 2007, directed to International Patent Application Measurements of Silica Gels by Means of Differential Scanning No. PCT/JP2005/015703; 7 pages. Calorimetry.” Journal of Colloid and Interface Science vol. 171:91 102. * cited by examiner US 7,713,449 B2 1. 2 POLYMERELECTROLYTIC MATERIAL, lytic membrane is called as fuel cross-over (FCO) or chemical POLYMERELECTROLYTIC PART, short to cause a problem of decrease of fuel cell output and MEMBRANEELECTRODE ASSEMBLY, AND energy capacity. POLYMERELECTROLYTE FUEL CELL Further, in a direct fuel cell, properties different from those of conventional PEFC using hydrogen gas as fuel are TECHNICAL FIELD required. That is, with respect to the direct fuel cell, in the anode, fuel Such as an aqueous methanol solution is reacted in The invention relates to a polymer electrolytic material, a the catalytic layer of the anode to generate proton, electron, polymer electrolytic part, a membrane electrode assembly, and carbon dioxide and the electron is transmitted to the and a polymer electrolytic fuel cell. 10 electrode substrate, the proton is transmitted to the polymer electrolyte, and the carbon dioxide passes the electrode sub BACKGROUND ART strate and is release to the outside of the system. Therefore, in addition to the required characteristics of the anode of a Fuel cells are electric power generation apparatuses with conventional PEFC, permeability of fuel such as an aqueous little emission of Substances, a high energy efficiency, and a 15 methanol solution and discharge property of carbon dioxide low load on the environments. Therefore, they have again are also required. Further in the cathode of the direct fuel cell, been in the limelight along with the increased concerns for in addition to the reactions similar to those in a conventional global environmental preservation in recent years. As electric PEFC, reaction of fuel such as methanol passed through the power generation apparatuses for relatively small scale electrolytic membrane and an oxidizing gas Such as oxygen decentralized power generation facilities and transportable or air is caused in the catalytic layer of the cathode to produce bodies such as automobiles and ships, the fuel cells are water. Therefore, the water to be produced is more than that expected to be future power generation apparatuses. Further, produced in a conventional PEFC and it is required to further it is expected that the fuel cells are to be disposed in compact efficiently discharge water. type mobile apparatuses such as cellular phones and personal Conventionally, perfluoro type proton conductive polymer computers in place of the secondary batteries such as nickel 25 membranes represented by Nafion (trade name, manufac tured by Du Pont de Nemours & Co.) have been used as hydrogen batteries and lithium ion batteries. polymer electrolytic membranes. However, these perfluoro With respect to polymer electrolyte fuel cells (hereinafter, type proton conductive polymer membranes have high per sometimes referred to also as PEFC), direct type fuel cells in meation quantities of fuel Such as methanol in the direct type which fuel such as methanol is directly supplied (hereinafter, 30 fuel cells and thus there are problems that the cell output and sometimes referred to also as DFC) are also spotlighted in the energy capacity are insufficient.
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