Abstract: Nitroorganic compounds of the formula ##STR1## wherein x and y may be the same or different and are selected from --NO --NO.sub.2. Methods of preparing these compounds are also disclosed.
Type:
Grant
Filed:
March 31, 1983
Date of Patent:
June 5, 1984
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Dorothy A. Cichra, Horst G. Adolph, Mortimer J. Kamlet
Abstract: A 1:1:2 mixed orthocarbonate of the formula ##STR1## wherein R and R" are each one of the following groups--CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3,--CH.sub.2 C(NO.sub.2).sub.3,--CH.sub.2 CF(NO.sub.2).sub.2,--CH.sub.2 CF.sub.2 (NO.sub.2), and--CH.sub.2 CF.sub.3, andR' is one of the followingCH.sub.2 CF(NO.sub.2).sub.2,CH.sub.2 CF.sub.2 (NO.sub.2), andCH.sub.2 CF.sub.3,provided that R.noteq.R', R.noteq.R", and R'.noteq.R". These 1:1:2 orthoconates are produced by the following reaction sequence: ##STR2## wherein R, R', and R" are as defined above. By choosing R and R" to be the same and either --CH.sub.2 (NO.sub.2).sub.2 CH.sub.3 or --CH.sub.2 C(NO.sub.2).sub.3 in the above reaction, 1:3 mixed orthocarbonates of the formula ##STR3## wherein R.noteq.R', R".noteq.R', R=R", and R and R" are each CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3,CH.sub.2 C(NO.sub.2).sub.3,CH.sub.2 CF.sub.2 (NO.sub.2), orCH.sub.2 CF.sub.3,and R' is CH.sub.2 CF(NO.sub.2).sub.2, CH.sub.2 CF.sub.2 (NO.sub.2) or CH.sub.2 CF.sub.3 may be prepared.
Type:
Grant
Filed:
February 18, 1983
Date of Patent:
May 15, 1984
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Michael E. Sitzmann, William H. Gilligan
Abstract: 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.
Type:
Grant
Filed:
March 25, 1982
Date of Patent:
February 21, 1984
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: This invention involves the synthesis of a novel family of azido fluorodinitro amines and their utilization as energetic plasticizers for advanced solid propellant compositions.
Type:
Grant
Filed:
April 12, 1983
Date of Patent:
February 21, 1984
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: A liquid monopropellant comprising a mixture of a 1-nitroxy-3-nitrazaalkane oxidizer such as 1-nitroxy-3-nitrazapentane (NNPE) or 1-nitroxy-3-nitrazabutane and mixtures thereof; an energetic azido fuel such as azido alcohols represented by 1-azidoethanol, 1,3-diazidopropanol; azidonitramines represented by 1-azido-3-nitrazapentane, and 1,5-diazido-3-nitrazapentane and mixtures thereof; and a diluent such as methanol and ethylene glycol and mixtures thereof.
Abstract: Vinyl ethers are prepared by reacting divinyl ether with a primary alcohol in the presence of a catalytic amount of red mercuric oxide and trifluoroacetic acid. The vinyl ethers so produced are particularly useful as monomers which can be polymerized into energetic macromolecular binder materials with excellent mechanical, physical and energetic properties.
Type:
Grant
Filed:
June 10, 1976
Date of Patent:
January 17, 1984
Assignee:
The United States of America as represented by the Secretary of the Air Force
Inventors:
Scott A. Shackelford, Raymond R. McGuire, Robert E. Cochoy
Abstract: A process for synthesizing energetic ethers, esters and acetals is disclosed that comprises reacting certain alcohols with certain alkenes or alkynes in the presence of mercuric or mercurous sulfate. The products obtained are particularly useful as plasticizers, monomers or prepolymers for propellant binder systems.
Type:
Grant
Filed:
September 25, 1974
Date of Patent:
January 3, 1984
Assignee:
The United States of America as represented by the Secretary of the Air Force
Inventors:
Raymond R. McGuire, Robert E. Cochoy, Scott A. Shackelford
Abstract: A high explosive composition comprising2 to 57% ammonium nitrate2 to 50% ethylenediamine dinitrate1 to 10% potassium nitrate1 to 80% nitroguanidineThese explosive compositions possess physical and explosive properties corable to those of explosive compositions based on TNT (2,4,6-trinitrotoluene); but they are relatively insensitive and less costly to manufacture and can be loaded into projectiles with existing melt/cast loading facilities.
Type:
Grant
Filed:
July 19, 1982
Date of Patent:
December 20, 1983
Assignee:
The United States of America as represented by the Secretary of the Army
Abstract: This invention involves the synthesis of a novel family of azido fluorodinitro amines and their utilization as energetic plasticizers for advanced solid propellant compositions.
Type:
Grant
Filed:
February 19, 1982
Date of Patent:
December 6, 1983
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: 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.
Type:
Grant
Filed:
April 21, 1982
Date of Patent:
December 6, 1983
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: Unsymmetrical carbonates of the formula ##STR1## are prepared by the following reaction sequence ##STR2## where R and R' can each be --CH.sub.2 C(NO.sub.2).sub.3, CH.sub.2 CF(NO..2).sub.2, --CH.sub.2 CF.sub.2 (NO.sub.2), --CH.sub.2 CCl(NO.sub.2).sub.2, --CH.sub.2 CF.sub.3, --CH.sub.2 CCl.sub.3, --CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3, or --CH.sub.2 CF.sub.2 CF.sub.2 H, provided that R.noteq.R' and wherein R" is a lower alkyl group of from 1 to 6 carbon atoms.Also included are symmetrical 1,3-bis(halo- and nitroalkyl carbonyldioxy)-2,2-dinitropropanes of the formula ##STR3## which are synthesis by the following reaction sequence ##STR4## wherein R and R" are as defined above. The carbonates of this invention are useful as energetic additives to propellants and explosive.
Type:
Grant
Filed:
March 3, 1982
Date of Patent:
October 25, 1983
Assignee:
The United States of America as represented by the Secretary of the Navy
Abstract: An improved bonding agent for a solid rocket propellant, having the general formula[X.sub.2 N(CH.sub.2 CH.sub.2 NX).sub.n CH.sub.2 CH.sub.2 NX.sub.2 ] (HO.sub.3 SC.sub.6 H.sub.4 CH.sub.3).sub.zwherein n is an integer having a value of 1 to 11, X is --H or --CH.sub.2 CH.sub.2 CN; wherein the amount of --CH.sub.2 CH.sub.2 CN, expressed as y, is in the approximate range of 0.15 (n+4) to 0.45 (n+4), the amount of HO.sub.3 SC.sub.6 H.sub.4 CH.sub.3, expressed as z, is in the approximate range of 0.01 (n+4) to 0.25 (n+4), and the ratio y:z is in the range of 1.5:1 to 3:1.
Type:
Grant
Filed:
June 28, 1982
Date of Patent:
October 18, 1983
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: A method of producing a priming composition comprising reacting components to produce a primary explosive and a by-product which remains in the composition.
Type:
Grant
Filed:
September 3, 1976
Date of Patent:
September 20, 1983
Assignee:
Imperial Metal Industries (Kynoch) Limited
Abstract: 2-hydroxymethyl-1,3-propanediol trinitrate, processes for its preparation, and compounds related thereto are disclosed. The final product is useful as a platicizer of relatively low volatility in double based propellant compositions and as a liquid explosive.
Abstract: Water-soluble protein is coated onto particles of nitramines by making a rry of nitramine powder in a water solution of the protein and removing the water by evaporation or by filtration after previously precipitating the protein by addition of ethanol. The protein coating acts as a bonding agent to enhance the bond strength between propellant binders and the nitramine particles, resulting in substantial enhancement of desirable propellant properties.
Type:
Grant
Filed:
October 9, 1981
Date of Patent:
June 21, 1983
Assignee:
The United States of America as represented by the Secretary of the Army
Abstract: A multi-component propellant charge is disclosed wherein one component is energetic high-strength composite resin, which is plasticized by an energetic plasticizer and supports the other components during the high-acceleration stage of the propellant's performance.
Type:
Grant
Filed:
September 22, 1980
Date of Patent:
June 14, 1983
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Craig Johnson, Paul Dendor, Harry L. Hodgkins
Abstract: A crosslinked binder for crosslinked single and double base propellant is provided. The binder is prepared from nitrocellulose, certain polyester diols which contain both aliphatic and aromatic ester functionality and a polyfunctional isocyanate having an NCO functionality of at least three. The propellant prepared from the binder exhibits improved mechanical property aging characteristics under conditions of high humidity.
Type:
Grant
Filed:
September 11, 1980
Date of Patent:
June 7, 1983
Assignee:
Hercules Incorporated
Inventors:
Robert J. Baczuk, Anderson E. Robinson, Jr.
Abstract: A gas generant propellant composition having low flame temperatures comprng (a) an elastomeric binder consisting of a mixture of polyethylene capped polypropylene glycol and a dihydroxy tetrazole selected from the group having the formulas: ##STR1## (b) a curative agent such as the biuret trimer of hexamethylene diisocyanate; (c) a plasticizer agent such as 1-methyl-5 (methoxyethyl) tetrazole; (d) a coolant agent such as oxamide; and (e) a deflagrating agent selected from the group consisting of: dihydrazinium 3,6-bis(5-tetrazolyl)-1,2-dihydrotetrazine, dinitrosopentamethylenetetramine, the reaction product of glyoxal and hydrazine and the ammonium salt of 5-nitramino tetrazole.
Type:
Grant
Filed:
October 14, 1980
Date of Patent:
November 9, 1982
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Russell Reed, Jr., Benjamin Y. S. Lee, Ronald A. Henry
Abstract: It has been discovered that when co-nitrating a mixture of trimethylolethane and diethylene glycol, a storage stable spent acid can be obtained if during the co-nitration an excess of from about 60 to about 100% by weight of nitric acid over that stoichiometrically required is employed.
Abstract: Fluorodinitro compounds are proposed as new compositions of matter which are useful as energetic ingredients for propellant and explosive formulations.
Abstract: 2-Hydroxymethyl-1,3-propanediol trinitrate, processes for its preparation, and compounds related thereto are disclosed. The final product is useful as a plasticizer of relatively low volatility in double based propellant compositions and as a liquid explosive.
Abstract: An improved explosive composition is disclosed and comprises a major portion of an explosive having a detonation velocity between about 1,500 and 10,000 meters per second and a minor amount of a getter additive comprising a non-explosive compound or mixture of non-explosive compounds capable of chemically reacting with free radicals or ions under shock initiation conditions of 2,000 calories/cm.sup.2 or less of energy fluence.
Abstract: Unsymmetrical carbonates of the formula ##STR1## are prepared by the following reaction sequence ##STR2## where R and R' can each be --CH.sub.2 C(NO.sub.2).sub.3, CH.sub.2 CF(NO..2).sub.2, --CH.sub.2 CF.sub.2 (NO.sub.2), --CH.sub.2 CCl(NO.sub.2).sub.2, --CH.sub.2 CF.sub.3, --CH.sub.2 CCl.sub.3, --CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3, or --CH.sub.2 CF.sub.2 CF.sub.2 H, provided that R.noteq.R' and wherein R" is a lower alkyl group of from 1 to 6 carbon atoms.Also included are symmetrical 1,3-bis(halo- and nitroalkyl carbonyldioxy)-2,2-dinitropropanes of the formula ##STR3## which are synthesis by the following reaction sequence ##STR4## wherein R and R" are as defined above. The carbonates of this invention are useful as energetic additives to propellants and explosive.
Type:
Grant
Filed:
January 13, 1981
Date of Patent:
June 1, 1982
Assignee:
The United States of America as represented by the Secretary of the Navy
Abstract: An improved explosive composition is disclosed and comprises a major portion of an explosive having a detonation velocity between about 1500 and 10,000 meters per second and a minor amount of a donor additive comprising a non-explosive compound or mixture of non-explosive compounds which when subjected to an energy fluence of 1000 calories/cm.sup.2 or less is capable of releasing free radicals each having a molecular weight between 1 and 120. Exemplary donor additives are dibasic acids, polyamines and metal hydrides.
Abstract: Incorporation of various flame coolants, particularly ferrous oxalate, cupric oxalate and submicron size Fe.sub.3 O.sub.4 in N,N'-dihydroxyethane diamide containing gas generants results in cooler flame temperature and reduced HCN content. Use of downstream coolants further reduces evolved gas temperature and also further reduces HCN content. Devices incorporating these propellants are useful inflators for many devices such as helicopter flotation bags, cargo pallet soft-landing bags, aircraft escape slides, inflatable life rafts and similar items. They are particularly suitable when these items must be man-rated.
Type:
Grant
Filed:
May 4, 1979
Date of Patent:
November 3, 1981
Assignee:
Thiokol Corporation
Inventors:
Richard A. Biddle, Calvin W. Vriesen, Ernest S. Sutton
Abstract: An energetic liquid monopropellant comprising a mixture of bis (2,2-dinitropropyl) acetal; bis (2,2-dinitropropyl) formal; and bis (2,2,2-fluorodinitroethyl) formal.
Type:
Grant
Filed:
January 10, 1980
Date of Patent:
October 27, 1981
Assignee:
The United States of America as represented by the Secretary of the Air Force
Inventors:
Milton B. Frankel, Harry A. Arbit, Glen D. Artz, John C. Gray
Abstract: A liquid monopropellant, suitable as a gun propellant, is obtained from a quid composition comprising from about 70 to about 95 weight percent of a liquid nitrated organic compound and from about 5 to 30 weight percent of a diester represented by the formula ROOC(CH.sub.2).sub.n COOR wherein R represents an alkyl of 3 to 5 carbon atoms and n is either 5 or 7.
Type:
Grant
Filed:
June 17, 1980
Date of Patent:
September 29, 1981
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Joseph E. Mastroianni, William F. Newton
Abstract: Dimethyl 2,2,2-trinitroethylmalonate, diethyl 2,2,2-trinitroethylmalonate, imethyl 2-fluoro-2,2-dinitroethylmalonate, diethyl 2-fluoro-2,2-dinitroethylmalonate, dimethyl 2,2-dinitropropylmalonate, diethyl 2,2-dinitropropylmalonate, and methods of preparing these compounds. These compounds are useful as energetic additives to propellants and explosives.
Type:
Grant
Filed:
August 20, 1980
Date of Patent:
September 22, 1981
Assignee:
The United States of America as represented by the Secretary of the Navy
Abstract: A solid propellant gas generator based upon dialkali tetranitroethane salts which produces high electron densities for magnetohydrodynamic (MHD) applications.
Abstract: The impact resistance of particulate RDX and HMX explosives is increased h a minimum loss of explosive output by admixture of about 1 to 9% of a particulate second explosive of the group 1,3,6,8-tetranitrocarbazole, 2,4,6,2', 4',6'-hexanitrooxanilide and ammonium picrate. Pressable explosive compositions of even greater impact resistance are obtained by coating the particulate dual explosive with 1 to 5% of a binder, such as petrolatum.
Type:
Grant
Filed:
June 20, 1979
Date of Patent:
February 17, 1981
Assignee:
The United States of America as represented by the Secretary of the Army
Abstract: The addition of monobasic cupric .beta.-resorcylate to a double base propant plasticized by only nitrate esters having primary nitroxy groups in order to obtain a plateau burning characteristic.
Type:
Grant
Filed:
November 29, 1973
Date of Patent:
December 16, 1980
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Albert T. Camp, Elmer R. Csanady, Paul R. Mosher
Abstract: At least one combustion modifier is incorporated in liquid propellants by ssolving the modifier in at least one solvent such as alkoxypolyethylene glycol ether or a bis(alkoxypolyethylene glycol) formal to form a solution and mixing the resulting solution with the energetic component of the liquid propellant. Similar solutions of combustion modifier are also suitable for use as casting liquids in cast double-base propellants.
Type:
Grant
Filed:
March 14, 1975
Date of Patent:
July 29, 1980
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Albert T. Camp, Kurt F. Mueller, George W. Nauflett
Abstract: Insensitive, high performance explosives obtained by combining certain enetic, high density inorganic compounds with insensitive, underoxidized organic nitro compounds.
Type:
Grant
Filed:
May 4, 1978
Date of Patent:
June 10, 1980
Assignee:
The United States of America as represented by the Secretary of the Navy
Abstract: A method for synthesizing glycidyl 2,2-dinitro-2-2 fluoroethoxide which comprises adding sodium hydroxide to a reaction mixture of epibromohydrin and 2,2-dinitro-2-fluoroethanol in the presence of carbon tetrachloride as a solvent for the reaction mixture.
Type:
Grant
Filed:
March 14, 1974
Date of Patent:
September 18, 1979
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: An oxidizer that is soluble in a polar solvent selected from ethanol, diel ether, and acetone is used in a propellant composition mixing procedure to effect an improved dispersion of the oxidizer. The soluble oxidizer is selected from the reaction products formed by reacting together an equivalent amount of a first reactant selected from triethanol amine or diethanol amine with an equivalent amount of a second reactant perchloric acid when the soluble perchlorate salt is desired for use. The soluble oxidizer is selected from the reaction products formed by reacting together an equivalent amount of a first reactant selected from triethanol amine or diethanol amine with an equivalent amount of a second reactant nitric acid when the soluble nitrate salt is desired for use. The dissolved oxidizer is added to the binder portion of the propellant during mixing. After being widely dispersed, the soluble oxidizer and binder portion are mixed under low vacuum and mild heat (e.g., 110.degree. F. to 120.degree. F.
Type:
Grant
Filed:
April 14, 1978
Date of Patent:
May 15, 1979
Assignee:
The United States of America as represented by the Secretary of the Army
Abstract: Energetic silicon compounds of the general formulae ##STR1## The gem dinitro compounds are prepared from alkyl bromide silanes by sod nitrite displacement and oxidative nitration. The compounds are then fluorinated. To prepare the polysiloxanes, phenyl blocking groups are used during synthesis of the fluoro dinitro moiety and are then replaced with bromine and the monomer is hydrolyzed.
Type:
Grant
Filed:
August 19, 1977
Date of Patent:
February 13, 1979
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Kurt Baum, Duane A. Lerdal, Jerald S. Horn
Abstract: A method of producing trinitromethane comprising reacting isopropyl alcohol with nitric acid, wherein the reaction is maintained within a temperature range of from about 25.degree. to about 85.degree. C to produce said trinitromethane and recovering the trinitromethane so produced. It is a particular advantage of the present method that no catalyst is required.
Type:
Grant
Filed:
December 5, 1977
Date of Patent:
October 24, 1978
Assignee:
Rockwell International Corporation
Inventors:
Milton B. Frankel, Frank C. Gunderloy, Jr., Dean O. Woolery, II
Abstract: Nitroaliphatic difluoroformals of the formula RCH.sub.2 OCF.sub.2 OCH.sub.2 R' wherein R = FC(NO.sub.2).sub.2 -- and R' = F.sub.2 C(NO.sub.2)-- or CF.sub.3 --; or R = R' = CF.sub.3 OCH.sub.2 C(NO.sub.2).sub.2 --. The compounds are prepared in accordance with the following reaction: ##STR1## carried out at temperatures of from about 95.degree. C to about 150.degree. C. The compounds are especially useful as energetic plasticizers in explosive compositions.
Type:
Grant
Filed:
December 16, 1975
Date of Patent:
October 17, 1978
Assignee:
The United States of America as represented by the United States Department of Energy
Abstract: Increasing the stability of composite energetic compositions containing ctalline high-energy nitrates or nitrites by the inclusion of saligenin into the composition.
Type:
Grant
Filed:
March 25, 1977
Date of Patent:
June 27, 1978
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Joel M. Schnur, Richard S. Miller, James P. Sheridan, A. D. Britt
Abstract: A composition of matter comprising at least one nitrato-alkanol and a stabilizingly effective amount of one or more derivatives of carbamic acid. The composition is useful as a component of explosive compositions.
Abstract: Dinitrocyanoalkyl epoxides having the general formula: ##STR1## wherein R is a lower alkylene radical containing from 1 through 5 carbon atoms and n is 0 or 1.
Abstract: Nitramine propellants absent a pressure exponent shift in the burning rate curves are prepared by matching the burning rate of a selected nitramine or combination of nitramines within 10% of burning rate of a plasticized active binder so as to smooth out the break point appearance in the burning rate curve.
Type:
Grant
Filed:
May 16, 1977
Date of Patent:
May 30, 1978
Inventors:
Alan M. Acting Administrator of the National Aeronautics and Space Administration, with respect to an invention of Lovelace, Norman S. Cohen, Leon D. Strand
Abstract: A method for producing 1,3-bis (2,2,2-fluorodinitroethoxy) -2,2-bis (difluoramino) propane by effecting a reaction between difluoramine and 1,3-bis(2,2,2-fluorodinitroethoxy)-2-propanone in a strong acid medium to produce a new high energy plasticizer for advanced energetic propellants.
Type:
Grant
Filed:
October 29, 1976
Date of Patent:
February 21, 1978
Assignee:
The United States of America as represented by the Secretary of the Air Force
Abstract: A composition of matter comprising at least one nitrato-alkanol and a stabilizingly effective amount of one or more derivatives of carbamic acid. The composition is useful as a component of explosive compositions.
Abstract: Blasting oil contained in the effluent from the production of explosives containing nitroglycerine is recovered by extracting with nitroaromatics which make part of the final explosive, the resulting extract being used completely in the explosive production. Residues of nitroaromatics may be removed from the purified effluent by means of an extraction liquid being sparely water-soluble, such as toluene or xylene or a mixture thereof.