Sri International

USA As Represented by Secretary of the Navy

Fluorochem, Inc.

Fluorchem Inc.

Clifford D Bedford

Kurt Baum

Ralph New Harris, Iii

Gary A Koolpe

Robert A Howd

Richard A Kenley

Ronald O Hunadi

Duane E Hilmas

Paritosh R Dave

Arnold T Nielsen

Farhad Forohar

Dane A Goff

Clifford L Coon

Michael Chaykovsky

Robert O Pick

Donald A Levins

Energetic nitramine containing cyclotriphosphazene which include 1,1,3,3,-tris-spiro(N,N'-dinitroethylenediamino)cyclotriphosphazene, 1,1-spiro(ethylenediamino)-3,3,5,5-bis-spiro(N,N'-dinitroethylenediamino)c yclotriphosphazene, 1,1,3,3-bis-spiro(N,N'-dinitroethylenediamino)-5,5-dichlorocyclotriphospha zene, 1,1,3,3-bis-spiro(N,N'-dinitroethylenediamino)-5,5-difluorocyclotriphospha zene, 1,1-spiro(N,N'-dinitroethylenediamino)-3,3,5,5-bis-spiro(ethylenediamino)c yclotriphosphazene, 1,1-spiro(ethylenediamino)-3,3-spiro(N,N'-dinitroethylenediamino)-5,5-dich lorocyclotriphosphazene, 1,1-spiro(ethylenediamino)-3,3-spiro(N,N'-dinitroethylenediamino)-5,5-difl uorocyclotriphosphazene, 1,1-spiro(N,N'-dinitroethylenediamino)-3,3,5,5-tetrachlorocyclotriphosphaz ene, and 1,1-spiro(N,N'-dinitroethylenediamino)-3,3,5,5-tetrafluorocyclotriphosphaz ene, which can be used in explosive compositions.

Spiro(N,N'-dinitroethylenediamino)cyclotriphosphazenes

A therapeutically effective class of low toxicity aldoxime-substituted functionalized imidazolium compounds and compositions is disclosed which is effective in the treatment of living species poisoned by organophosphorus chemicals which inactivate the enzyme acetylcholinesterase. In vivo administration of therapeutically effective amounts of these aldoxime-substituted imidazolium derivatives has been found to save mammals having inhibited acetylcholinesterase due to injection with lethal dosages of Soman.

Aldoxime-substituted imidazolium derivatives useful in the treatment of

A therapeutically effective class of low toxicity aldoxime-substituted trazolium derivatives is disclosed which is effective in the treatment of living species poisoned by organophosphorus chemicals which inactivate the enzyme acetylcholinesterase. In vivo administration of therapeutically effective amounts of these low toxicity aldoxime-substituted triazolium derivatives has been found to save mice having inhibited acetylcholinesterase due to injection with lethal dosages of Soman.

Aldoxime-substituted triazolium compounds useful in the treatment of

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.

1,3,5,5-Tetranitrohexahydropyrimidine, termed DNNC for convenience, useful as an oxident in explosive and rocket propellant compositions. Said compound has the structure ##STR1##

1,3,5,5-Tetranitrohexahydropyrimidine (DNNC)

Substituted gem-dinitroalkanes are prepared by reacting a nitro olefin, tetranitromethane and an alcohol or organolithium derivative. The substituted gem-dinitroalkanes are useful as explosives, plasticizers and binders.

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Silver Spring, MD, United States of America

Clifford D Bedford