Method of making and polymerizing perfluoroalkylene acetylene co

Details Method of making and polymerizing perfluoroalkylene acetylene co Method of making and polymerizing perfluoroalkylene acetylene co

1980-12-24

1982-08-31

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

556475, C07F 708

Patent

active

043473768

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 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.

REFERENCES:
patent: 2735859 (1956-02-01), Wagner
patent: 2735860 (1956-02-01), Pines et al.
patent: 2737520 (1956-03-01), Wagner
patent: 2849472 (1958-08-01), Pines et al.
patent: 3223686 (1965-12-01), Naita et al.

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