Polymerizable sulfonate ionic liquids and liquid polymers therefrom

Abstract

Disclosed is a new ionic liquid monomer salt and methods of is synthesis and polymerization. The ionic liquid monomer salt is prepared by mixing equimolar amounts of an amine, such as tris[2-(2-methoxyethoxy)-ethyl]amine and an acid functionalized polymerizable monomer, such as 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS), which is stirred at ambient temperature until salt formation is complete. Also disclosed is a new ionic liquid polymer salts and method for making the same. The synthesis of AMPS-ammonium salt polymer is accomplished by adding 2,2′-azobisisobutyronitrile (AIBN) to the ionic liquid monomer salt and heating the homogeneous melt at 70° C. for 18 hr.

What is claimed as new and desired to be protected by Letters Patent of the United States is: 
     
       1. An ionic liquid monomer salt having the formula: 
       
         
           
           
               
               
           
         
         wherein R, R′, and/or R″ are each independently selected from H, or
 —(CH 2 ) n CH 3  where n=1 to 12, or 
 —(CH 2 CH 2 O) n CH 3  where n=1 to 4, or 
 —(CH) 3 (Si(CH 3 ) 2 O) n CH 3  where n=1 to 6, or 
 —(CF 2 ) n CF 3 , —CH 2 (CF 2 ) n CF 3  where n=1 to 8. 
 
       
     
     
       2. A method for making an ionic liquid monomer salt comprising:
 mixingforming a solvent-free mixture of an equimolar amount of a sulfonic acid functionalized monomer having the formula: 
 
       
         
           
           
               
               
           
         
         with the organic amine base having the general formula: 
       
       
         
           
           
               
               
           
         
         
           wherein R, R′, and/or R″ are each independently selected from H, or
 —(CH 2 ) n CH 3  where n=1 to 12, or 
 —(CH 2 CH 2 O) n CH 3  where n=1 to 4, or 
 —(CH) 3 (Si(CH 3 ) 2 O) n CH 3  where n=1 to 6, or 
 —(CF 2 ) n CF 3 , —CH 2 (CF 2 ) n CF 3  where n=1 to 8; and 
 
         
         stiffingstirring said solvent-free mixture under an inert atmosphere until said sulfonic acid functionalized monomer is dissolved, wherein the dissolution completes formation of the ionic liquid monomer salt. 
       
     
     
       3. A method for making an ionic liquid polymer salt comprising:
 forming a solvent-free mixture by providing the ionic liquid monomer salt of  claim 1 having the general formula: 
 
       
         
           
           
               
               
           
         
         wherein R, R′, and/or R″ are each independently selected from H, or
 —(CH 2 ) n CH 3  where n=1 to 12, or 
 —(CH 2 CH 2 O) n CH 3  where n=1 to 4, or 
 —(CH) 3 (Si(CH 3 ) 2 O) n CH 3  where n=1 to 6, or 
 —(CF 2 ) n CF 3 , —CH 2 (CF 2 ) n CF 3  where n=1 to 8; 
 
         adding a free radical polymerization catalyst to said ionic liquid monomer salt; and  
         stiffingstirring said solvent-free mixture under an inert atmosphere with application catalyst-specific polymerization conditions.