Aqueous Monomer Compositions and Methods of Making and Using the Same

Abstract

Aqueous compositions of carboxylic acids, carboxylate esters, and carboxylate salts are generally disclosed, including methods of using such compounds to make various polymers, including, but not limited to, polyesters, polyamides, and polycarbamates. In certain embodiments, the carboxylic acids, carboxylate esters, and carboxylate salts are derived from a renewable source, such as a natural oil.

1 . An aqueous composition, the composition comprising:
 water; and   a compound of formula (I)   
       
         
           
           
               
               
           
         
         wherein:
 X 1  is C 12-36  alkylene, C 12-24  alkenylene, C 12-36  heteroalkylene, or C 12-24  heteroalkenylene, each of which is optionally substituted one or more times by substituents selected independently from R 3 ; 
 R 1  and R 2  are independently —OH, —O—R 4 , or —O − Z + ; 
 R 3  is a halogen atom, —OH, —NH 2 , oxo, C 1-6  heteroalkyl, or C 2-6  heteroalkenyl; 
 R 4  is C 1-6  alkyl or C 2-24  heteroalkyl, each of which is optionally substituted one or more times by —OH; and 
 
         Z +  is a positively charged counterion; 
         provided that at least one of R 1  and R 2  is not —OH. 
       
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . The aqueous composition of  claim 1 , wherein X 1  is C 12-36  alkylene, which is optionally substituted one or more times with substituents selected independently from —OH and C 1-6  oxyalkyl. 
     
     
         5 . (canceled) 
     
     
         6 . The aqueous composition of  claim 1 , wherein X 1  is —(CH 2 ) 12 —, —(CH 2 ) 14 —, —(CH 2 ) 16 —, —(CH 2 ) 18 —, —(CH 2 ) 20 —, or —(CH 2 ) 22 —. 
     
     
         7 . The aqueous composition of  claim 6 , wherein X 1  is —(CH 2 ) 16 —. 
     
     
         8 . (canceled) 
     
     
         9 . The aqueous composition of  claim 8   claim 1 , wherein X 1  is C 12-36  oxyalkylene, which is optionally substituted one or more times with substituents selected independently from oxo, —OH, and C 1-6  oxyalkyl. 
     
     
         10 . The aqueous composition of  claim 9 , wherein X 1  is a moiety of formula (II) 
       
         
           
           
               
               
           
         
       
       wherein:
 X 2  and X 4  are independently C 12-20  alkylene; and 
 X 3  is C 2-10  alkylene; and 
 n is an integer from 1 to 10. 
 
     
     
         11 . The aqueous composition of  claim 10 , wherein X 2  and X 4  are independently —(CH 2 ) 12 —, —(CH 2 ) 14 —, —(CH 2 ) 16 —, —(CH 2 ) 18 —, —(CH 2 ) 20 —, or —(CH 2 ) 22 —. 
     
     
         12 . The aqueous composition of  claim 11 , wherein X 2  and X 4  are —(CH 2 ) 16 —. 
     
     
         13 . The aqueous composition of  claim 10 , wherein X 3  is —(CH 2 ) 2 —, —(CH 2 ) 4 —, —(CH 2 ) 6 —, —(CH 2 ) 8 —, or —(CH 2 ) 10 —. 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . The aqueous composition of  claim 10 , wherein n is 1, 2, 3, 4, or 5. 
     
     
         17 . (canceled) 
     
     
         18 . (canceled) 
     
     
         19 . The aqueous composition of  claim 1 , wherein R 1  is —OH. 
     
     
         20 . The aqueous composition of  claim 1 , wherein R 1  is —O − Z + . 
     
     
         21 . The aqueous composition of  claim 1 , wherein R 1  is —O—R 4 . 
     
     
         22 . The aqueous composition of  claim 1 , wherein R 2  is —OH. 
     
     
         23 . The aqueous composition of  claim 1 , wherein R 2  is —O − Z + . 
     
     
         24 . The aqueous composition of  claim 1 , wherein R 2  is —O—R 4 . 
     
     
         25 . (canceled) 
     
     
         26 . The aqueous composition of  claim 1 , wherein Z +  is an ammonium compound. 
     
     
         27 . (canceled) 
     
     
         28 . (canceled) 
     
     
         29 . The aqueous composition of  claim 26 , wherein Z+ is selected from the group consisting of: ammonium cation, triethylammonium cation, and N,N-dimethylethanolammonium cation. 
     
     
         30 . (canceled) 
     
     
         31 . The aqueous composition of  claim 1 , wherein R 4  is C 2-24  oxyalkyl, which is optionally substituted one or more times by —OH. 
     
     
         32 . The aqueous composition of  claim 31 , wherein R 4  is —CH 2 CH 2 —(O—CH 2 —CH 2 ) p —O—R 9 , wherein p is an integer from 0 to 10, and R 9  is a hydrogen atom, methyl, or ethyl. 
     
     
         33 - 48 . (canceled)