Functional trifluorovinyl monomers and their copolymerization with fluoroolefins

Abstract

Functional trifluorovinyl monomers and their copolymerization with fluoroolefins Functional trifluorovinyl monomers, process for the copolymerization of trifluorovinyl monomers with fluoroolefins and use of these trifluorovinyl monomers in forming fluoroelastomers. Copolymers resulting from this copolymerization process and process for crosslinking these copolymers.

1 - 19 . (canceled)  
     
     
         20 . A compound corresponding to the formula I  
       CF 2 ═CF═(CH 2 ) m —W  (I)  
       chosen from the compounds in which 
 (i) m has the value 1, 2 or 3 and 
 W is selected from the group consisting of  
                     
  group, a  
                     
  group and a  
                     
  group,  
 in which  
 R 1 , R 2 , R 3  and R 4  independently are selected from the group consisting of a hydrogen atom, a C 1 -C 20  alkyl group and an optionally substituted aryl group,  
 R 5  and R 6  independently are selected from the group consisting of a hydrogen atom, a C 1 -C 20  alkyl group or an optionally substituted aryl group, with the proviso that, when R 5  represents a hydrogen atom, R 6  is other than a phenyl group when m has the value 1;  
 
 (ii) m has the value 3 and 
 W represents a  
                     
  group  
 in which  
 R 7  and R 8  independently are selected from the group consisting of a hydrogen atom, a C 1 -C 20  alkyl group and an optionally substituted aryl group;  
 
 (iii) m has the value 1 and W represents a CH(OH)CH 2 OH group;  
 (iv) W represents a Y-Z group chosen from 
 (1) a Y-Z group in which 
 Y represents an oxygen atom and  
 Z is selected from the group consisting of a CH 2 CH 2 OH group and a CH 2 COOH group and  
 
 m has the value 1, 2 or 3  
 (2) a Y-Z group in which 
 Y represents an oxygen atom and  
 Z represents a COCH 3  group, and  
 
 m has the value 1 or 3  
 (3) a Y-Z group in which 
 Y represents a sulphur atom and  
 Z is selected from the group consisting of a hydrogen atom, a CH 2 CH 2 OH group, a CH 2 COOH group and a COCH 3  group, and  
 
 m has the value 3.  
 
 
     
     
         21 . The compound according to  claim 20 , wherein the compound of formula I corresponds to the compound of the formula II  
       CF 2 ═CF—C 3 H 6 —Y-Z  (II)  in which Y-Z represents a Y-Z group as defined in  claim 20 .    
     
     
         22 . The compound according to  claim 20 , wherein the compound of formula I corresponds to the compound of the formula  
       CF 2 ═CF—CH 2 —CH(OH)—CH 2 OH.  
     
     
         23 . A copolymerization process which comprises reacting a compound corresponding to the formula I′ 
       CF 2 ═CF—(CH 2 ) m —W′  (I′)  in which    m has the value 1, 2 or 3,    W′ is selected from the group consisting of    (i) W′ is selected from the group consisting of a CH(OH)CH 2 OH group, a CH═CH 2  group,    a                           group, a                           group,    a                           group, and a                           group    in which    R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  independently are selected from the group consisting of a hydrogen atom, a C 1 -C 20  alkyl group and an optionally substituted aryl group or    (ii) W′ represents a Y-Z group chosen from    a Y-Z group in which    Y represents an oxygen atom and    Z is selected from the group consisting of a CH 2 CH 2 OH group, a CH 2 COOH group and a COCH 3  group, and    (iii) W′ represents a Y-Z group chosen from    a Y-Z group in which    Y represents a sulphur atom and    Z is selected from the group consisting of a hydrogen atom, a CH 2 CH 2 OH group, a CH 2 COOH group and a COCH 3  group,    with a compound corresponding to the formula III    CF 2 ═CX 2   (III)    in which    X independently is selected from the group consisting of a hydrogen atom and a fluorine atom,    so as to obtain a fluorocopolymer.    
     
     
         24 . The copolymerization process according to  claim 23 , in which Y represents an oxygen atom, Z represents a COCH 3  group and the copolymer obtained corresponds to the formula V  
       
         
           
           
               
               
           
         
       
       wherein n, p and r independently representing natural integers.  
     
     
         25 . The copolymerization process according to  claim 23 , in which Y represents a sulphur atom, Z represents a COCH 3  group and the copolymer obtained corresponds to the formula VI  
       
         
           
           
               
               
           
         
         wherein n, p and r independently representing natural integers.  
       
     
     
         26 . A copolymerization process which comprises reacting a compound corresponding to the formula I′ 
       CF 2 ═CF—(CH 2 ) m —W′  (I′)  in which    m has the value 1, 2 or 3,    W′ is selected from the group consisting of a CH(OH)CH 2 OH group, a CH═CH 2  group, 
 a  
                     
  group, a  
                     
  group,  
 a  
                     
  group, a  
                     
  group and a Y-Z group,  
 in which  
   R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  independently are selected from the group consisting of a hydrogen atom, a C 1 -C 20  alkyl group and an optionally substituted aryl group, 
 Y is selected from the group consisting of an oxygen atom and a sulphur atom and  
 Z is selected from the group consisting of a hydrogen atom, a CH 2 CH 2 OH group, a CH 2 COOH group and a COCH 3  group, with a compound corresponding to the formula III  
 CF 2 ═CX 2   (III)  
 in which  
 X independently is selected from the group consisting of a hydrogen atom and a fluorine atom,  
 and with an olefinic compound of formula CH 2 ═CH—R′ in which R′ is selected from the group consisting of a hydrogen atom and a C 1 -C 4  alkyl group, so as to obtain a copolymer corresponding to the formula IX  
                     
 in which  
 l, n, p and r independently represent natural integers.  
   
     
     
         27 . The process according to  claim 26 , wherein Z is selected from the group consisting of a CH 2 CH 2 OH group, a CH 2 COOH group and a COCH 3  group.  
     
     
         28 . The process according to  claim 26 , wherein the olefinic compound is propylene.  
     
     
         29 . The process according to  claim 27 , wherein the olefinic compound is propylene.  
     
     
         30 . A method for forming fluoroelastomers which comprises using the process according to  claim 26.