Fluorochem, Inc.

Fluorchem Inc.

Ronald O Hunadi

Kurt Baum

Clifford D Bedford

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 reacting perfluoroalkylene diiodide having the formula I(CF.sub.2).sub.n I, wherein n is a whole number from 5 to about 20, inclusive with bis(trimethylsilyl)acetylene, and converting the reaction product to the diacetylene with KF. The diacetylene has the general formula HC.tbd.C(CF.sub.2).sub.n C.tbd.CH, wherein n is as set forth above, and it can be polymerized to produce a clear, hard, cross-linked resin suitable for use as a coating 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 formed by substituting perfluoroalkyl primary iodides for the diiodides in the above-described reaction. The resulting compounds (fluorinated monofunctional acetylenes) can be trimerized to yield liquids suitable as lubricating oils, hydraulic fluids, etc.

Method of making and polymerizing perfluoroalkylene acetylene compounds

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 formed by substituting perfluoroalkyl primary iodides for the diiodides in the above-disclosed sequence of reactions. The resulting compounds (fluorinated monofunctional acetylenes) can be trimerized to yield liquids suitable as lubricating oils, hydraulic fluids, etc.

Growing community of inventors

Los Angeles, CA, United States of America

Ronald O Hunadi