(IO)  Patent No.:  US 7,718,753 B2  May 18, 2010  (45)  Date of Patent:  c12)  United States Patent  Capehart et al.  (54)  ORGANIC SUPERACIDS, POLYMERS,  DERIVED FROM ORGANIC SUPERACIDS,  AND METHODS OF MAKING AND USING  THESAME  (75)  Inventors:  Tenneille Weston Capehart,  Rochester,  MI (US);  Gail Capehart,  legal  representative, Rochester, MI (US);  Gerhard Maier,  Munich (DE);  Claude  Spino,  Sherbrooks (CA);  Thomas J.  Chapaton,  Sterling Heights, MI (US);  Markus Gross,  Kaufbeuren (DE);  Armand Soldera,  Sherbrooke (CA)  (73)  Assignee:  GM Global Technology Operations,  Inc.,  Detroit, MI (US)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 9 days.  (21)  Appl. No.:  12/136,979  (22)  Filed:  Jun.11,2008  (60)  Provisional application No. 60/943,744, filed on Jun.  13, 2007.  (51)  Int. Cl.  C0SG 75100  (2006.01)  (52)  U.S. Cl.  .......................................  528/171;  528/220  (58)  Field of Classification Search  ................. 528/171,  528/220, 373  See application file for complete search history.  OTHER PUBLICATIONS  (57)  ABSTRACT  10 Claims, 1 Drawing Sheet  (56)  References Cited  U.S. PATENT DOCUMENTS  (65)  Prior Publication Data  Related U.S. Application Data  2004/0186262 Al  2006/0068256 Al  *  2006/0249444 Al  9/2004 Maier et al.  3/2006 Arimura .. ... ... ... .. ... ... ... 429/33  11/2006 Maier et al.  4,320,224 A  4,474,932 A  RE34,085 E  3/ 1982 Rose et al.  10/ 1984 Bier et al.  9/ 1992 Rose et al.  US 2009/0043068 Al  Feb. 12, 2009  Burk et al., Superacidity of Neutral Bronsted Acids on Gas Phase,  Journal of Computational Chemistry, 1996, pp. 30-41, vol. 17, No. 1.  Koppel et al., Gas-Phase Acidities of Some Neutral Bronsted  Superacids: A DFT and ab Initio Study, Journal American Chemical  Society, 2000, pp. 5114-5124, vol. 122.  Gartin et al., Cooperative Intramilecular Hydrogen Bonding Effect  and Basicity-An Ab Initio and DFT Study ... , European Journal  Organic Chemistry, 2005, pp. 3206-3213.  Eikerling et al., Molecular Orbital Calculation of Proton Dissociation  and Hyrdation of Various Acidic Moieties  , J. New. Mat.  Electrochem. Systems, 2002, pp. 15-23, vol. 5.  Klamt et al., First Principles Calculations of Aqueous Pkalpha Values  for Organic and Inorganice Acids Using .  . , Journal Physical  Chemistry, A 2003, pp. 9380-9386, vol. 107.  Kallies, Berd, A Connected System of Programs for Performing a  Variety of Semiempirical and Ab Initio Molecular Orbital Calcula› tions, Gaussian 03, Revision 2.4, Jul. 20, 2005, 1-4.  Engman et al., New Alkoxylated Dibenzo[l,4]dichalcogenines as  Donors for Low-Dimenisonal Materials .  . , J. Chem. Society,  Perkins Trans. 1, 1988, pp. 2095-2101.  Hoffmann et al., Poly( ether ketone )s by Fluoride Catalyst Systems,  Macromolecules, 1994, pp. 3575-3579, vol. 27.  Cao et al., Synthesis and Properties of Poly(ether ether ketone)› Poly(ether sulfone) Block Copolymers, Polymer, Aug. 1994, pp.  3549-3556, vol. 35, Issue 16.  * cited by examiner  Primary Examiner-Randy  Gulakowski  Assistant Examiner-Shane  Fang  (74)  Attorney, Agent, or  Firm-Reising Ethington P.C.  One embodiment of the invention contemplates a proton  exchange membrane for use in a variety of fuel cells. The  proton exchange membrane may comprise a solid phase  organic based copolymer material in which a first structural  unit is derived from a polymerizable organic super acid. The  organic super acid may comprise an acid group such as a  sulfonic acid group or a carboxylic acid group.  US007718753B2 