content_image/926077.jpg content_image/926093.jpg content_image/926076.jpg
# 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 

## (65) Prior Publication Data 

US 2009/0043068 Al Feb. 12, 2009 

(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. 

## (56) References Cited 

<img src='content_image/926077.jpg'>

## Related U.S. Application Data 

## U.S. PATENT DOCUMENTS 

<img src='content_image/926093.jpg'>

# (IO) Patent No.: US 7,718,753 B2 

# May 18, 2010 (45) Date of Patent: 

<img src='content_image/926076.jpg'>

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. 

## (57) ABSTRACT 

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 

## OTHER PUBLICATIONS 

## 10 Claims, 1 Drawing Sheet 

