Fluorinated, acrylamide-functional monomers

Abstract

Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula y hydrogen or methyl; R2 and R3 independently can be an alkyl, cycloalkyl, or aryl group, or R2 and R3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms; R4 and R5 are independently hydrogen or lower alkyl; a is 0 or 1; b is 1 or 2; X is a single bond, CH2, CH2OCH2, and CH2CH2OCH2; and RF is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2. Novel polymers and copolymers can be prepared from the monomers of the invention.

We claim: 
     
       1. A compound having the formula ##STR8## wherein R 1  and R 6  are independently hydrogen or methyl; R 2  and R 3  independently are alkyl, cycloalkyl, or aryl group, or R 2  and R 3  taken together with the carbon to which they are joined form a carbocyclic ring containing 4 to 12 ring atoms;   R 4  and R 5  are independently hydrogen or lower alkyl;   a is 0 or 1;   b is 1 or 2;   X is a single bond, CH 2 , CH 2  OCH 2 , or CH 2  CH 2  OCH 2  ; and   R F  is an alkyl, cycloalkyl, or aryl group when b is 1 and alkylene when b is 2, wherein at least 50 percent of the hydrogen atoms have been replaced by fluorine.   
     
     
       2. The compound according to claim 1 wherein R 1  is hydrogen. 
     
     
       3. The compound according to claim 1 wherein R 2  and R 3  are independently lower alkyl of C 1  to C 4 . 
     
     
       4. The compound according to claim 1 wherein R 6  is hydrogen. 
     
     
       5. The compound according to claim 1 wherein a is 1 and R 4  and R 5  are hydrogen. .Iadd.6. A compound having the formula ##STR9##.Iaddend. wherein R 1  and R 6  are independently hydrogen or methyl;   R 2  and R 3  independently are alkyl, cycloalkyl, or aryl group, or R 2  and R 3  taken together with the carbon to which they are joined form a carbocyclic ring containing 4 to 12 ring atoms;   R 4  and R 5  are independently hydrogen or lower alkyl;   a is 0 or 1;   b is 1 or 2;   X is a single bond, CH 2 , CH 2  OCH 2 , or CH 2  CH 2  OCH 2  ; and R F  is ##STR10##   
     
     
        .Iadd.7.  The compound according to claim 6 wherein R 1  is H, R 2  is CH 3 , R 3  is CH 3 ,   a is 0,   R 6  is H,   X is CH 2 , and   b is 1. .Iaddend.