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 Reactive compounds containing perfluorovinyl groups

Details
Inventors: Clement, Katherine S.; Babb, David A.; Ezzell, Bobby R.; Richey, W. Frank;
Assignee: The Dow Chemical Company (Midland, MI)
Primary Examiner: Michl; Paul R.
Assistant Examiner: Szekely; Peter
Attorney, Agent or Firm:

A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I: (G)n-R-(X--CF.dbd.CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF.dbd.CF.sub.2) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups. A process for preparing a compound of Formula I comprises the steps of: (a) preparing a 2-halotetrafluoro compound of the Formula III: (Q--CF.sub.2 --CF.sub.2 -X).sub.m -R-(G").sub.n wherein R, X, m and n are as described for Formula I and Q is bromine, chlorine or iodine; and G" is a functional group, or a functional group suitable for conversion into G; (b) chemically modifying group G" to produce functional group G; and (c) dehalogenating the 2-halotetrafluoro compound to form the corresponding trifluorovinyl compound.

DETAILED DESCRIPTION OF THE INVENTION The invention includes compounds having at least one perfluorovinyl group and at least one functional group suitable for forming condensation polymers or a group suitable for conversion into such a functional group.
The functional group is preferably attached indirectly to the perfluorovinyl group via some linking structure thereto.
More preferably, the compounds have structures represented by Formula I: G.
sub.
n -R(-X--CF.
dbd.
CF.
sub.
2).
sub.
m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, preferably an integer of from 1 to about 4, more preferably from 1 to about 2; m is the number of (-X--CF.
dbd.
CF.
sub.
2) groups, preferably an integer of from 1 to about 3, more preferably from about 1 to about 2; G represents any reactive functional group or any group convertible into a reactive functional group, preferably any functional group suitable for reaction with di- or polyfunctional compounds to form polymers, which functional group (G) is, more preferably, insufficiently nucleophilic to react undesirably with perfluorovinyl groups at room temperature (e.
g.
25.
degree.
C.
), most preferably at temperatures used in subsequent reactions of the compound.
Alternatively, G is a group suitable for chemical conversion into a functional group suitable for reaction to form a polymer.
G is preferably selected from the group consisting of functional groups including hydroxyl groups (both alcoholic and phenolic), carboxylic acid groups, acyl halides such as chlorides, isocyanates, acyl azides, acetyl groups, primary or secondary amines, sulfide groups, sulfonic acid groups, sulfonamide groups, ketones, aldehydes, epoxy groups, primary or secondary amides, halo groups (e.
g.
chloro, bromo, iodo, and fluoro groups), nitro groups, cyano groups, anhydrides, imides, cyanate groups, vinyl, allyl, acetylene groups; and esters including thiocarboxylic and carboxylic esters, preferably lower alkyl esters such as methyl and ethyl esters, trihalomethyl groups including trichloromethyl groups, silicon-containing substituents such as alkyl silanes, siloxanes, chlorosilanes, phosphorus-containing groups such as phosphines, phosphate, phosphonate, boron-containing groups such as boranes, alkyl groups and alkoxy groups preferably containing from about 1 to about 12 carbon atoms when R is aromatic and the like



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