Fluorocompound having highly fluorinated norbornane structure, fluoropolymer, and their production processes

Abstract

The present invention provides novel polymers obtained by polymerizing a compound of formula (1) which has a highly fluorinated norbornane structure. The invention also provides compounds represented by formulas (3) and (3A-1) below, as well as the following compounds:

1 . A polymer obtained by polymerizing a compound of formula (1): 
       
         
           
           
               
               
           
         
         wherein: 
         Z A , Z B , Z C , Z D , and Z E  each independently represent —CH(—OC(O)CT=CH 2 )—, —CF (—CHOC(O)CT=CH 2 )— or —CR A R B —, provided that at least one of Z A  to Z E  is —CH(—OC(O)CT=CH 2 )— or —CF(—CH 2 OC(O)CT=CH 2 )—, and at least one of Z A  to Z E  is —CR A R B —, wherein T is a hydrogen atom, a fluorine atom, a C 1-3  alkyl group or a C 1-3  fluoroalkyl group, and each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group comprising an etheric oxygen atom; 
         W A  and W B  each independently represent a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group comprising an etheric oxygen atom; and 
         n is 0, 1 or 2. 
       
     
     
         2 . The polymer of  claim 1 , wherein a molecular weight of the polymer is from 1×10 3  to 1×10 7 . 
     
     
         3 . The polymer of  claim 1 , wherein the polymer is a copolymer obtained by copolymerizing the compound of formula (1) with at least one other monomer. 
     
     
         4 . The polymer of  claim 3 , wherein the polymer comprises from 0.1 to 99.9 mol % of repeating units of the compound of formula (1) and from 0.1 to 99.9 mol % of repeating units of the at least one other monomer, based on an entirety of repeating units. 
     
     
         5 . The polymer of  claim 3 , wherein the polymer comprises at least 50 to 99.9 mol % of repeating units of the compound of formula (1) and less than 0.1 to 50 mol % of repeating units of the at least one other monomer, based on an entirely of repeating units. 
     
     
         6 . The polymer of  claim 3 , wherein the at least one other monomer is at least one selected from the group consisting of a (meth)acrylate, an unsaturated carboxylic amide, a styrene, a vinylsilane, an olefin, a fluoroolefin, a chloroolefin, a vinyl ester, a vinyl ether, (meth)acrylic acid, and acrylonitrile. 
     
     
         7 . The polymer of  claim 1 , wherein the polymer is a homopolymer made of only repeating units of the compound of formula (1) and having a weight average molecular weight of from 1,000 to 50,000. 
     
     
         8 . A compound of formula (3): 
       
         
           
           
               
               
           
         
         wherein: 
         X A , X B , X C , X D  and X E  each independently represent —C(O)—, —CF(C(O)G)- or —CR A R B —, provided that at least one of X A  to X E  is —C(O)— or —CF(—C(O)G)-, and at least one of X A  to X E  is —CR A R B —, wherein G is a halogen atom or a C 1-10  alkoxy group, and each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group comprising an etheric oxygen atom; 
         W A  and W B  each independently represent a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group comprising an etheric oxygen atom; and 
         n is 0, 1 or 2. 
       
     
     
         9 . The compound of  claim 8 , wherein each of X C , X D  and X E  represent —CR A R B — or each of XB, XD and XE represent —CR A R B —. 
     
     
         10 . The compound of  claim 8 , wherein X A  is —C(O)— and each of X B , X C , X D  and X E  is —CR A R B —. 
     
     
         11 . The compound of  claim 8 , wherein X A  is —CF(—C(O)G)- and each of X B , X C , X D  and X E  is —CR A R B —. 
     
     
         12 . The compound of  claim 8 , wherein G is a fluorine atom or a methoxy group. 
     
     
         13 . The compound of  claim 8 , wherein R A  and R B  are both fluorine atoms or C 1-16  perfluoroalkyl groups, or one of them is a fluorine atom and the other is a C 1-16  perfluoroalkyl group. 
     
     
         14 . The compound of  claim 8 , wherein when Z E  is —CR A R B — then Z E  is —CF 2 — or —C(CF 3 ) 2 —. 
     
     
         15 . The compound of  claim 8 , wherein W A  and W B  are both fluorine atoms, or one of them is a fluorine atom and the other is a trifluoromethyl group. 
     
     
         16 . A compound of formula (3A-1): 
       
         
           
           
               
               
           
         
         wherein: 
         X is —C(O)—, —CF(C(O)F)— or —CF(C(O)OCH 3 )—; 
         R 1 , R 2 , R 3  and R 4  each independently represent a fluorine atom or a C 1-16  perfluoroalkyl group; and 
         W 1  and W 2  each independently represent a fluorine atom or a trifluoromethyl group. 
       
     
     
         17 . The compound of  claim 16 , wherein R 3  and R 4  each represent a fluorine atom, or one of them is a fluorine atom and the other is a fluorine atom or a C 1-16  perfluoroalkyl group. 
     
     
         18 . The compound of  claim 16 , wherein W 1  and W 2  each represent a fluorine atom, or one of them is a fluorine atom and the other is a trifluoromethyl group. 
     
     
         19 . A compound selected from the group consisting of