N-vinylformamide derivatives, polymers formed therefrom and synthesis thereof

Abstract

A method of synthesizing a compound having the formula: comprising the step of: reacting a N-vinylformamide salt having the formula with a compound having the formula XRR 1 ; wherein X is Br, Cl or I, M is an alkali metal or an alkali earth metal, R 1 is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2 is H, provided R 1 is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3 is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4 is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5 wherein R 5 and R 5 are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.

1 .- 10 . (canceled)  
   
   
       11 . A method of synthesizing a copolymer comprising the step of reacting a compound having the formula:  
     
       
         
         
             
             
         
       
     
     with at least one vinyl compound having at least one vinyl group, wherein R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       12 . The method of  claim 11  wherein the vinyl compound is N-vinylformamide.  
   
   
       13 . The method of  claim 12  wherein the copolymer includes the following repeat units:  
     
       
         
         
             
             
         
       
     
     wherein m and n are integers.  
   
   
       14 . The method of  claim 13  further comprising the step of hydrolizing the copolymer to form a copolymer having the repeat units:  
     
       
         
         
             
             
         
       
     
   
   
       15 . The method of  claim 14  wherein the hydrolysis occurs in acidic or basic conditions.  
   
   
       16 . The method of  claim 11  wherein the vinyl compound has the formula CH 2 ═CH—R 6 , wherein R 6  is —OC(O)—CH 3 , —C(O)—O—R 7 , wherein R 7  is an alkyl group, or —C(O)OH.  
   
   
       17 . The method of  claim 16  wherein R 7  is a methyl group.  
   
   
       18 . A polymer having the formula:  
     
       
         
         
             
             
         
       
     
     wherein m is an integer, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       19 . A copolymer produced by reaction of a compound having the formula:  
     
       
         
         
             
             
         
       
     
     with N-vinylformamide, wherein the copolymer includes the following repeat units:  
     
       
         
         
             
             
         
       
     
     and wherein m and n are independently, integers, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       20 . The copolymer of  claim 18  wherein the copolymer is hydrolyzed to from a copolymer with the repeat units:  
     
       
         
         
             
             
         
       
     
   
   
       21 . A polymer having the formula:  
     
       
         
         
             
             
         
       
     
     wherein m is an integer, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       22 . A polymer having the formula:  
     
       
         
         
             
             
         
       
     
     wherein m is an integer, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group, the polymer having end groups that are either.  
   
   
       23 . A random copolymer including the following repeat units:  
     
       
         
         
             
             
         
       
     
     and wherein m, n, o and p are independently, integers, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       24 . A polymer including the following repeat units:  
     
       
         
         
             
             
         
       
     
     and wherein m and n are independently, integers, R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       25 . A compound having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 1  is a C0-C25 alkylene group, a C0-C25 fluroalkylene group or a C0-C25 perfluoro alkylene group, R 2  is H, provided R 1  is not absent, an alkyl group, a fluroalkyl group, a perfluoroalkyl group, an aryl group, a hydroxy group, a polyether group, a heterocyclic group of 5 or 6 atoms wherein at least one of the atoms is not a carbon and is N, O, or S, —OR 3 , wherein, R 3  is an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, —C(O)R 4 , —C(O)OR 4 , —OC(O)R 4 , wherein R 4  is an H, an alkyl group, a fluoroalkyl group, a perfluoroalkyl group, or an aryl group, a phthalimide group or NR 5 R 5  wherein R 5  and R 5  are independently H, —C(O)R 4 , an alkyl, a fluoroalkyl group, a perfluoroalkyl group or an aryl group.  
   
   
       26 . The compound of  claim 25  wherein X is Br.  
   
   
       27 . The compound of  claim 25  wherein R 1  is a C1-C10 alkylene group.  
   
   
       28 . The compound of  claim 25  wherein R 2  is a C1-C10 alkyl group.  
   
   
       29 . The compound of  claim 25  wherein R 1  is a C1-C10 perfluoroalkylene group.  
   
   
       30 . The compound of  claim 25  wherein R 2  is a C1-C10 perfluoroalkyl group.  
   
   
       31 . The compound of  claim 25  wherein R 2  is a phthalimide group.