Perfluoropolyvinyl modified aryl intermediates and monomers

Abstract

A compound of formula (I) wherein R f is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ; X is —F, or —OC 3 F 7 ; Y is —H, —Cl, or —Br; R is —OH, —(CH 2 ) n OH, —(OCH 2 CH 2 ) m OH, —(CH 2 ) n (OCH 2 CH 2 ) m OH, —O—C(O)—R 1 , —(CH 2 ) n O—C(O)—R 1 , —(OCH 2 CH 2 ) m OC(O)—R 1 , —C(O)NH w (CH 2 CH 2 OH) 2-w , —C≡N, —C≡CH, or —C(O)R 2 ; n is 1 to 10; m is 1 to 10; R 1 is C 1 to C 10 alkyl; R 2 is —H, C 1 to C 10 alkyl, —Cl, or —OCH 2 CH 2 OH; a is 1 to 5; b is 1 to 5; and w is 0, 1 or 2.

1 . (canceled) 
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . (canceled) 
     
     
         8 . (canceled) 
     
     
         9 . (canceled) 
     
     
         10 . (canceled) 
     
     
         11 . (canceled) 
     
     
         12 . (canceled) 
     
     
         13 . A method for producing compounds of Formula (XX) 
       
         
           
           
               
               
           
         
         wherein
 R f  is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ; 
 X is —F, or —OC 3 F 7 ; 
 Y is —H, —Cl, or Br; 
 R 6  is —OH, —(CH 2 ) n OH, —(OCH 2 CH 2 ) m OH, —O—C(O)—R 1 , —(CH 2 ) n O—C(O)—R 1 , —(OCH 2 CH 2 ) m OC(O)—R 1 ; —C(O)NH w (CH 2 CH 2 OH) 2-w , —C≡N, —C≡CH, —NO 2 , —C(O)R 2 , —C(O)—OR 4 ; or —CH═CH 2 ; 
 n is 1 to 10; 
 m is 1 to 10; 
 R 1  is C 1  to C 10  alkyl; 
 R 2  is —H, C 1  to C 10  alkyl, —Cl, or —OCH 2 CH 2 OH; 
 R 4  is —H, or C 1  to C 10  alkyl; 
 a is 1 to 5; 
 b is 1 to 5; 
 and w is 0, 1 or 2; 
 
         comprising contacting a compound of Formula (XXI) 
       
       
         
           
           
               
               
           
         
         
           wherein R 7  is —OH, —(CH 2 ) n OH, —(OCH 2 CH 2 ) m OH, —O—C(O)—R 1 , —(CH 2 ) n O—C(O)—R 1 , —(OCH 2 CH 2 ) m OC(O)—R 1 ; —C(O)NH w (CH 2 CH 2 OH) 2-w , —C≡N, —C≡CH, —NO 2 , —C(O)R 2 , —C(O)—OR 4 ; or —CH═CH 2 ; 
           n is 1 to 10; 
           m is 1 to 10; 
           R 1  is C 1  to C 10  alkyl; 
           R 2  is —H, C 1  to C 10  alkyl, —Cl, or —OCH 2 CH 2 OH; 
           R 4  is —H, or C 1  to C 10  alkyl; 
           a is 1 to 5; and 
           b is 1 to 5; 
         
         with one or more compounds of formula (XIV) 
       
       
         
           
           
               
               
           
         
         
           wherein R f  is —CF 3 , —C 2 F 5 , —CF 2 CFXCF 3 ; 
           X is —F, or —OC 3 F 7 ; and 
           Y is —H, —Cl, or —Br in the presence of a base and a solvent. 
         
       
     
     
         14 . A method of  claim 11 , wherein the solvent is tetrahydrofuran, carbon tetrachloride, or carbon tetrabromide. 
     
     
         15 . A method of  claim 12 , wherein the solvent is tetrahydrofuran. 
     
     
         16 . A method of  claim 11 , wherein the base is potassium carbonate, sodium carbonate, or potassium bicarbonate. 
     
     
         17 . A method of  claim 14 , wherein the base is potassium carbonate. 
     
     
         18 . A compound of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein
 R f  is —CF 3 , —C 2 F 5 , or —CF 2 CFXCF 3 ; 
 X is —F, or —OC 3 F 7 ; 
 Y is —H, —Cl, or —Br; 
 R is —C(O)—O—R 1  or —C(O)R 2 ; 
 R 1  is C 1  to C 10  alkyl; 
 R 2  is —H, C 1  to C 10  alkyl, —Cl, or —OCH 2 CH 2 OH; 
 a is 1 to 5; and, 
 b is 1 to 5.