Method of making and polymerizing perfluoroalkylene acetylene compounds

US4347376A · kind A · utility

Assignee

• Fluorochem, Inc. · US

Inventors

• Kurt Baum · Pasadena, US
• Clifford D. Bedford · Claremont, US
• Ronald O. Hunadi · Los Angeles, US

Key dates

• Filing date: Dec 24, 1980
• Grant date: Aug 31, 1982
• Expiry date: Dec 24, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F7/081
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A perfluoroalkylene .alpha.,.omega.-diacetylene compound having a fluorocarbon chain of from 5 to about 20 carbon atoms between two acetylene end groups, and a method of forming same by first carrying out the addition reaction of a perfluoroalkylene diiodide having the formula I(CF.sub.2).sub.n I, where n is a whole number from 5 to about 20, inclusive, and trimethylsilyacetylene in the presence of a free radical catalyst to form (CH.sub.3).sub.3 SiIC.dbd.CH(CH.sub.2).sub.n CH.dbd.CISi(CH.sub.3).sub.3 ; subjecting the (CH.sub.3).sub.3 SiIC.dbd.CH(CF.sub.2).sub.n CH.dbd.CISi(CH.sub.3).sub.3 to dehydrohalogenation with DBU under dry conditions to obtain (CH.sub.3).sub.3 SiC.tbd.C(CF.sub.2).sub.n C .tbd.CSi(CH.sub.3).sub.3 ; and removing the silyl group from the latter compound with excess DBU or KF to yield HC.tbd.C(CF.sub.2).sub.n C.tbd.CH as the perfluoroalkylene .alpha.,.omega.-diacetylene compound. The HC.tbd.C(CF.sub.2).sub.n C.tbd.CH compounds can be trimerized to produce clear, hard, cross-linked resins suitable for use as coatings on bearings and in the manufacture of aircraft windshields. Monofunctional counterparts of the HC.tbd.C(CF.sub.2).sub. n C.tbd.CH compounds can be …