United States of America As Represented by the Secretary of the Air Force

Scm Corporation

Pcr, Inc.

Keith B Baucom

Burrell N Hamon

Ralph J De Pasquale

The invention relates to a novel fluorinated pre-polymer and novel process steps in producing the same. The pre-polymers are quinoxaline materials derived by reaction of diketone linkage containing perfluoro-compounds with an aromatic diamine. The diketone is produced by a bis-ketone. The polychloroketone is produced by reacting a keto-ylid with a chlorinating agent, e.g., chlorine. The keto-ylid is produced by oxidatively dechlorinating a polychloroketone which may be a monoketone or reacting a phosphorane with an acid halide of a polyoxy-perfluoroalkylene oxide wherein the perfluoro-oxyalkylene group contains two or three carbon atoms, and there are present from two or twenty perfluoro-oxyalkylene units in the oligomer. The quinoxalines, the polychloroketones and the diketones hereof are novel products. Cross-linking may be effected with a free radical generator.

Perfluoro-keto-ylids as precursors of polychloroketones, 1,2-diketones

The invention relates to a novel fluorinated pre-polymer and novel process steps in producing the same. The pre-polymers are quinoxaline materials derived by reaction of diketone linkage containing perfluoro-compounds with an aromatic diamine. The diketone is produced by oxidatively dechlorinating a polychloroketone which may be a monoketone or a bis-ketone. The polychloroketone is produced by reacting a keto-ylid with a chlorinating agent, e.g., chlorine. The keto-ylid is produced by reacting a phosphorane with an acid halide of a polyoxy-perfluoroalkylene oxide wherein the perfluoro-oxyalkylene group contains two or three carbon atoms, and there are present from two to twenty perfluoro-oxyalkylene units in the oligomer. The quinoxalines, the polychloroketones and the diketones hereof are novel products. Cross-linking may be effected with a free radical generator.

An improved method for synthesizing poly (carbonyl fluoride) oligomers by using bis(trifluoromethyl)trioxide as a reaction initiator in the photo-oxidation of F-3 methylbutene-1.

Method for the preparation of poly (carbonyl fluoride) oligomers

Method for the preparation of poly (carbonoyl fluoride) oligomers

F-3-Methylbutene-1 has been oxidized using oxygen and ultraviolet radiation to form poly(carbonyl fluoride) oligomers. The formation of fluoroformate terminated material is insignificant. This is in sharp contrast to the products derived from the prior art oxidation of F-propene (HFP) in which up to 60% fluoroformate terminated material was produced. F-Ethylene (TFE) can be added to the F-3-methylbutene-1 reaction gas stream without adversely affecting the product composition. The fluoride oligomers, after addition of one unit of hexafluoropropylene oxide, can be converted to s-triazines which have excellent properties as hydrualic fluids.

Method for synthesizing poly(carbonyl fluoride) oligomers

F-phenylalkylene oxide acetylenes having the formula C.sub.6 F.sub.5 C.tbd.C(CF.sub.2 OCF.sub.2).sub.n C.tbd.CC.sub.6 F.sub.5, where n ranges from 3 to 8, inclusive. The diacetylenes are useful as monomers for preparing fluorinated polyether elastomers.

F-Phenylalkylene oxide diacetylenes

Thermally and oxidatively stable perfluorinated tertiary amines of the formula: ##EQU1## ARE DISCLOSED, AS WELL AS THE PROCESS FOR MAKING THESE AND OTHER COMPOUNDS. The carbonyl group of imides or amides is reduced with SF.sub.4 using HF as the reaction solvent at a reaction temperature of 25.degree.-300.degree.C. Cyclic imides can be used as starting compounds, and tertiary amines containing unsaturated moieties can be produced. The perfluorinated tertiary amines have various uses in view of their high degree of thermal and oxidative stability, including uses as hydraulic fluids or transformer dielectric fluids.

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Gainesville, FL, United States of America

Keith B Baucom