Rockwell International Corporation

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

Edward F Witucki

Milton B Frankel

Joseph E Flanagan

Leslie F Warren, Jr

Patricia H Cunningham

Dean O Woolery, Ii

William P Moran

Paul R Newman

Lyle V Monney

Louis Maus

Frederick D Raniere

John A Walker

Wallace W Thompson

A method for stabilizing shelf life conductivity of conductive coatings such as polypyrrole or nickel sulfide on a substrate such as fiberglass, by incorporating in such conductive coating a polyphenol or a polysiloxane. The polyphenol is derived from a phenolic material in the form of a phenol-formaldehyde monomer or an oligomer of phenol-formaldehyde, and the polysiloxane is derived from a siloxane. Upon heating, the phenolic material cures to a polyphenol and the siloxane is converted to a polysiloxane, forming the stabilizing material on the conductive polypyrrole or nickel sulfide coated substrate. The phenolic material is preferably incorporated directly into the solution formulation for preparing the conductive nickel sulfide or polypyrrole on the substrate, and the polyphenol stabilizer is formed together with the conductive coating on the substrate by heating. In the case of the silane or siloxane material, the conductive polypyrrole or nickel sulfide preferably is formed first on the substrate, and the conductive coated substrate is contacted with a solution of the siloxane followed by heating to convert the siloxane to a polysiloxane protective overcoating.

Stabilizing shelf life conductivity of conductive substrate coatings

A method for stabilizing shelf life conductivity of conductive coatings such as polypyrrole or nickel sulfide on a substrate such as fiberglass, by incorporating in such conductive coating a polyphenol or a polysiloxane. The polyphenol is derived from a phenolic material in the form of a phenol-formaldehyde monomer or an oligomer of phenolformaldehyde, and the polysiloxane is derived from a siloxane. Upon heating, the phenolic material cures to a polyphenol and the siloxane is converted to a polysiloxane, forming the stabilizing material on the conductive polypyrrole or nickel sulfide coated substrate. The phenolic material is preferably incorporated directly into the solution formulation for preparing the conductive nickel sulfide or polypyrrole on the substrate, and the polyphenol stabilizer is formed together with the conductive coating on the substrate by heating. In the case of the silane or siloxane material, the conductive polypyrrole or nickel sulfide preferably is formed first on the substrate, and the conductive coated substrate is contacted with a solution of the siloxane followed by heating to convert the siloxane to a polysiloxane protective overcoating.

Stabilizing shelf life conductivity of conductive coatings

A process for producing 1,5-diazido-3-nitrazapentane (DANPE) which comprises the steps of nitrating diethanolamine with nitric acid in a halogenated solvent such as methylene chloride to form 1,5-dinitrato-3-nitrazapentane (DINA) as intermediate, solvent transferring such intermediate from the halogenated solvent to dimethylsulfoxide, adding sodium azide to the resulting solution to form DANPE as product, and solvent transferring such product from the dimethylsulfoxide to another halogenated solvent, e.g. methylene chloride. Thus, both DINA intermediate and DANPE product are prepared in solution, and both can also be purified in solution, eliminating the necessity for isolating the neat, hazardous compounds. The DANPE product can be further solvent transferred from the halogenated solvent to ethyl acetate to form an ethyl acetate solution of DANPE, which can be used to furnish the DANPE as an energetic plasticizer, e.g. in the production of gun propellants.

Process for preparing 1,5-diazido-3-nitrazapentane

1,9-Difluoro-1,1,3,5,5,7,9,9-octanitro-3,7-diazanonane, C.sub.7 H.sub.8 F.sub.2 N.sub.10 O.sub.16, is disclosed as a new energetic oxidizer for solid propellants. A method for producing the new oxidizer is also disclosed.

1,9-difluoro-1,1,3,5,7,9,9-octanitro-3,7-diazanonane and method of

Production of electrically conductive polypyrrole of enhanced stability by treating a liquid pyrrole with a solution of a strong oxidant, capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing the pyrrole by such strong oxidant in the presence of a relatively large organic dopant anion, and precipitating a conductive polypyrrole. The strong oxidant, e.g., Fe.sup.3+ ion, and dopant anion, which can be an alkyl or aryl sulfonate, e.g., methylbenzenesulfonate, or a perfluorinated carboxylate, e.g., trifluoroacetate, anion, can be derived from a single compound, e.g., ##STR1## the anion serving as dopant for the polypyrrole.

Chemical synthesis of conducting polypyrrole

Production of electrically conductive composite or structural materials comprising a dielectric substrate, e.g. fiberglass fabric, and a layer of a pyrrole polymer on the substrate, by treating the substrate with a solution of a strong oxidant containing a substantially non-nucleophilic anion, e.g. ferric chloride, drying the substrate and exposing the so treated substrate with the vapors of a pyrrole and oxidizing the pyrrole by the strong oxidant and depositing a polypyrrole layer or film on the substrate.

Process for applying an electrically conducting polymer to a substrate

Production of electrically conductive polypyrrole powder, by treating a liquid pyrrole with a solution of a strong oxidant, capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing the pyrrole by such strong oxidant in the presence of a substantially non-nucleophilic anion and precipitating a conductive polypyrrole powder. The strong oxidant, e.g., Fe.sup.3+ ion, and non-nucleophilic anion, e.g., sulfate or chloride ion, can be derived from a single compound, e.g., FeCl.sub.3 or Fe.sub.2 (SO.sub.4).sub.3. The anion serves as dopant for the polypyrrole. The reaction can be carried out in aqueous solution or in an organic solvent medium, such as acetonitrile.

Process for producing polypyrrole powder and the material so produced

A method of stabilizing electrically conductive polymers to hostile environments is disclosed. The method comprises encapsulating the conductive polymer, e.g., polypyrrole or polyaniline, as a powder, a free-standing film or preferably in the form of a composite of a substrate, such as fiberglass fabric, impregnated with the conductive polymer, with a suitable resin, preferably an epoxy resin, as an encapsulating agent. The preferred method involves pre-pregging the fabric of the conductive composite with an epoxy resin and curing the resulting system.

Method of stabilizing conductive polymers

Production of electrically conductive composites comprising a dielectric porous substance, e.g., fiberglass fabric, and a pyrrole polymer in the pores of such substance, by treating the porous substance with a liquid pyrrole, and then treating the resulting porous substance with a solution of a strong oxidant in the presence of a non-nucleophilic anion, such as ferric chloride. The pyrrole monomer is oxidized to a pyrrole polymer, which precipitates in the interstices of the porous material. Alternatively, the dielectric porous material can first be treated with a solution of strong oxidant and non-nucleophilic anion followed by treatment with liquid pyrrole, to precipitate an electrically conductive polypyrrole in the pores of the material. The resulting composite of porous material, e.g., fiberglass fabric, containing polypyrrole is electrically conductive while the other properties of such impregnated conductive porous material are substantially unaffected. Several treatments of the porous substance with the pyrrole and oxidant solutions can be carried out to increase the electrical conductivity of the composite.

Process for producing electrically conductive composites and composites

This invention involves the synthesis of a novel family of azido nitramino ethers and their utilization as energetic plasticizers for advanced solid propellant compositions. They include the novel compounds bis (2-azidoethoxymethyl) nitramine and 1,12-diazido-3,10-dioxa-5,8-dinitrazadodecane.

Azido nitramino ether containing solid propellants

Azido nitramino ethers

This invention involves the synthesis of a novel family of azido esters and their utilization as energetic plasticizers for advanced solid propellant compositions. This family includes as an illustrative member, the novel compound 6-azidohexyl-6-azidohexanoate.

Azido esters

This invention involves the synthesis of a novel family of azido fluorodinitro amines and their utilization as energetic plasticizers for advanced solid propellant compositions.

Azido fluorodinitro amines

This invention involves the synthesis of a novel family of azido nitrocarbamates and their utilization as energetic liquid plasticizers for advanced solid propellant compositions. The novel family of plasticizers is represented specifically by the novel compound, 1,3-diazido-2-propyl-N-nitro-N-trinitropropyl carbamate.

Growing community of inventors

Van Nuys, CA, United States of America

Edward F Witucki