US2009269644A1PendingUtilityA1

Proton conducting materials

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Assignee: 3M INNOVATIVE PROPERTIES COPriority: Apr 24, 2008Filed: Apr 24, 2009Published: Oct 29, 2009
Est. expiryApr 24, 2028(~1.7 yrs left)· nominal 20-yr term from priority
Inventors:Steven J. HamrockMark S. SchabergNeeraj SharmaJohn E. Abulu
Y02E60/50C08J 5/20H01M 8/1051C08F 8/40C08J 5/2237C07F 9/3834H01M 8/1039C08F 8/32H01M 8/1023C08J 2327/12C08F 8/36C08J 5/225C07F 9/4021
63
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Claims

Abstract

Materials are provided that may be useful as ionomers or polymer ionomers, including compounds including bis sulfonyl imide groups which may be highly fluorinated and may be polymers.

Claims

exact text as granted — not AI-modified
1 . A compound according to the formula:
   (R 1 —O—) 2 —P(═O) m —Ar—SO 2 NH—SO 2 —R 2      wherein each R 1  is independently chosen from the group consisting of hydrogen, alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, polymers, metals, metal oxides, metal phosphates, metal phosphonates and inorganic particles,   wherein m is 0 or 1,   wherein Ar is an aromatic group which may include heterocycles and polycycles and may be substituted, and   wherein R 2  is chosen from the group consisting of alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers.   
     
     
         2 . The compound according to  claim 1  wherein Ar is phenylene. 
     
     
         3 . The compound according to  claim 1  wherein R 2  is chosen from the group consisting of alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers and Ar is phenylene-R 3 , wherein R 3  is chosen from the group consisting of hydrogen, alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers. 
     
     
         4 . The compound according to  claim 1  wherein R 2  is a fluoropolymer. 
     
     
         5 . The compound according to  claim 1  wherein R 2  is substituted with one or more acid groups selected from the group consisting of sulfonic acid groups and phosphonic acid groups. 
     
     
         6 . A compound according to the formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is chosen from the group consisting of metals, metal oxides, metal phosphates, metal phosphonates and inorganic particles, 
         wherein m is 0 or 1, 
         wherein Ar is an aromatic group which may include heterocycles and polycycles and may be substituted, and 
         wherein R 2  is chosen from the group consisting of alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers. 
       
     
     
         7 . The compound according to  claim 6  wherein Ar is phenylene. 
     
     
         8 . The compound according to  claim 6  wherein R 2  is Ar is phenylene-R 3 , wherein R 3  is chosen from the group consisting of hydrogen, alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers. 
     
     
         9 . The compound according to  claim 6  wherein any R 1  is a metal or metal oxide wherein the metal is selected from the group consisting of Zr, Ti, Th and Sn. 
     
     
         10 . The compound according to  claim 6  wherein every R 1  is a metal or metal oxide wherein the metal is selected from the group consisting of Zr, Ti, Th and Sn. 
     
     
         11 . The compound according to  claim 6  wherein any R 1  is a metal or metal oxide wherein the metal is selected from the group consisting of tetravalent metals. 
     
     
         12 . The compound according to  claim 6  wherein every R 1  is a metal or metal oxide wherein the metal is selected from the group consisting of tetravalent metals. 
     
     
         13 . The compound according to  claim 6  wherein R 2  is a fluoropolymer. 
     
     
         14 . The compound according to  claim 6  wherein R 2  is substituted with one or more acid groups selected from the group consisting of sulfonic acid groups and phosphonic acid groups. 
     
     
         15 . A compound according to the formula:
   R 1   n —Ar—SO 2 NH—SO 2 —R 2      wherein each R 1  is independently chosen from the group consisting of hydrogen, alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, polymers, metals, metal oxides, metal phosphates, metal phosphonates and inorganic particles,   wherein n is 1, 2 or 3,   wherein Ar is an aromatic group which may include heterocycles and polycycles and may be substituted, and   wherein R 2  is chosen from the group consisting of alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers.   
     
     
         16 . The compound according to  claim 15  wherein Ar is phenylene. 
     
     
         17 . The compound according to  claim 15  wherein R 2  is Ar is phenylene-R 3 , wherein R 3  is chosen from the group consisting of hydrogen, alkyl, alkylene or aryl groups which may contain heteroatoms and which may be substituted, and polymers. 
     
     
         18 . The compound according to  claim 15  wherein R 2  is a fluoropolymer. 
     
     
         19 . The compound according to  claim 15  wherein R 2  is substituted with one or more acid groups selected from the group consisting of sulfonic acid groups and phosphonic acid groups. 
     
     
         20 . The compound according to  claim 15  wherein R 1  is substituted with one or more acid groups selected from the group consisting of sulfonic acid groups and phosphonic acid groups. 
     
     
         21 . A polymer electrolyte comprising a highly fluorinated backbone and first pendant groups which comprise groups according to the formula:
   —SO 2 —NH—SO 2 —ArA n      wherein Ar is an aromatic group of 5-24 carbon atoms which may include heterocycles and polycycles and may be substituted,   where A is selected from the group consisting of —SO 3 H and —PO 3 H 2 ,   where n is between 1 and q, where q is one-half the number of carbons in Ar.   
     
     
         22 . A polymer electrolyte according to  claim 21  wherein A is —SO 3 H. 
     
     
         23 . A polymer electrolyte according to  claim 21  wherein n is 1. 
     
     
         24 . A polymer electrolyte according to  claim 21  wherein n is 2. 
     
     
         25 . A polymer electrolyte according to  claim 21  wherein Ar is Ph. 
     
     
         26 . A polymer electrolyte according to  claim 21  wherein Ar is fluorinated. 
     
     
         27 . A polymer electrolyte according to  claim 21  wherein Ar is perfluorinated. 
     
     
         28 . A polymer electrolyte according to  claim 21  where n=1, A is —SO 3 H and Ar is perfluorinated. 
     
     
         29 . A polymer electrolyte according to  claim 21  where n=1 and A is —SO 3 H, wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are bound to adjacent carbons of Ar. 
     
     
         30 . A polymer electrolyte according to  claim 21  where n=1 and A is —SO 3 H, and wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are bound to adjacent carbons of Ar in at least 95% of said first pendent groups. 
     
     
         31 . A polymer electrolyte according to  claim 21  where n=1 and A is —SO 3 H, and wherein Ar is Ph and wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are ortho to each other. 
     
     
         32 . A polymer electrolyte according to  claim 21  where n=1 and A is —SO 3 H, and wherein Ar is Ph and wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are ortho to each other in at least 95% of said first pendent groups. 
     
     
         33 . A polymer electrolyte according to  claim 21  where n=1, A is —SO 3 H and Ar is Ph and wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are meta to each other. 
     
     
         34 . A polymer electrolyte according to  claim 21  where n=1, A is —SO 3 H and Ar is Ph wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and sulfonic acid (—SO 3 H) are meta to each other in at least 95% of said first pendent groups. 
     
     
         35 . A polymer electrolyte according to  claim 21  comprising a perfluorinated backbone. 
     
     
         36 . A polymer electrolyte according to  claim 21  comprising second pendant groups which comprise groups according to the formula: —SO 3 H. 
     
     
         37 . A polymer electrolyte according to  claim 36  wherein the ratio of first to second pendant groups is p, where p is between 0.01 and 100. 
     
     
         38 . A polymer electrolyte according to  claim 36  wherein the ratio of first to second pendant groups is p, where p is between 0.1 and 10. 
     
     
         39 . A polymer electrolyte according to  claim 36  wherein the ratio of first to second pendant groups is p, where p is between 0.1 and 1. 
     
     
         40 . A polymer electrolyte according to  claim 36  wherein the ratio of first to second pendant groups is p, where p is between 1 and 10. 
     
     
         41 . A polymer electrolyte according to  claim 21  where n=1, A is —PO 3 H 2  and Ar is Ph wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and phosphonic acid (—PO 3 H 2 ) are para to each other. 
     
     
         42 . A polymer electrolyte according to  claim 21  where n=1, A is —PO 3 H 2  and Ar is Ph wherein the bis sulfonyl imide (—SO 2 —NH—SO 2 —) and phosphonic acid (—PO 3 H 2 ) are para to each other in at least 95% of said first pendent groups. 
     
     
         43 . A polymer electrolyte membrane comprising the polymer electrolyte according to  claim 21 . 
     
     
         44 . The polymer electrolyte membrane according to  claim 43  additionally comprising a porous support. 
     
     
         45 . A polymer electrolyte membrane comprising a polymer electrolyte which is the polymer electrolyte according to  claim 21  after crosslinking. 
     
     
         46 . A polymer electrolyte membrane comprising a polymer electrolyte which is the polymer electrolyte according to  claim 21  wherein A is —PO 3 H 2 , after crosslinking by attachment of phosphonate groups of said first pendent groups to inorganic particles. 
     
     
         47 . The polymer electrolyte membrane according to  claim 46  wherein said inorganic particles comprise Zr. 
     
     
         48 . A fuel cell membrane electrode assembly comprising an electrode comprising the polymer electrolyte according to  claim 21 . 
     
     
         49 . A method of making a compound according to  claim 29  comprising the step of reacting a sulfonamide-functional polymer with an aromatic disulfonyl anhydride. 
     
     
         50 . A method of making a compound according to  claim 31  comprising the step of reacting a sulfonamide-functional polymer with 1,2 benzenedisulfonyl anhydride.

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