Nitrated Acyclic, Alicyclic Or Heterocyclic Amine Patents (Class 149/92)
  • Patent number: 7279572
    Abstract: A subject-matter of the present invention is a novel process for the synthesis of hexanitrohexaazaisowurtzitane (HNIW), a compound of use as energetic filler in powders, propellants and explosives. This process comprises a first stage of reaction of an ?,?-dicarbonyl derivative with a primary amine which makes it possible to form a hexasubstituted hexaazaisowurtzitane derivative. The HNIW is subsequently obtained directly, in a single reaction stage, by nitration of the hexasubstituted hexaazaisowurtzitane derivative. This process, in only 2 stages starting from a primary amine, is particularly simple and inexpensive.
    Type: Grant
    Filed: April 28, 2004
    Date of Patent: October 9, 2007
    Assignee: SNPE Materiaux Energetiques
    Inventors: Guy Cagnon, Geneviève Eck, Grégoire Herve, Guy Jacob
  • Patent number: 7129348
    Abstract: Hexabenzylhexaazaisowurtzitane is converted to tetracetyl, dibenzyl azaisowurtzitane. The benzyl groups are removed by catalytic transfer hydrogenolysis leaving a pair of available nitrogens. The available nitrogens are acetylated, and the resulting intermediate is converted to CL-20 with a strong nitrating agent.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: October 31, 2006
    Assignee: Alliant Techsystems Inc.
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 7052562
    Abstract: High explosives suitable for filling very small volume loading holes in micro-electric initiators for micro-electro-mechanical mechanisms, used as safe and arm devices, are prepared from slurries of crystalline energetic materials and applied using various methods. These methods include swipe loading, pressure loading and syringe loading. A volatile mobile phase may be added to the slurry so as to partially dissolve the energetic material so that, upon evaporation of the mobile phase, the energetic material precipitates and adheres to the loading hole.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: May 30, 2006
    Assignee: The United State of America as represented by the Secretary of the Army
    Inventors: Daniel Stec, III, Gartung Cheng, Brian E. Fuchs, Gerard Gillen, Neha Mehta
  • Patent number: 7033449
    Abstract: An explosive composition having a main explosive and an additive, such as 2,4-dinitrophenylhydrazine. The explosive composition is resistant to slow cook-off. The main explosive includes Composition B or a Composition B replacement. The 2,4-dinitrophenylhydrazine is present in the explosive composition at less than or equal to approximately 5% by weight. An insensitive munition resistant to slow cook-off is also disclosed, as is a method of forming the explosive composition having a main explosive and 2,4-dinitrophenylhydrazine and a method of mitigating slow cook-off violence.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: April 25, 2006
    Assignee: Alliant Techsystems Inc.
    Inventors: Ruth A. Schaefer, Robert L. Hatch, Daniel W. Doll
  • Patent number: 6997996
    Abstract: A high energy propellant, comprising an oxetane thermoplastic elastomer energetic binder admixed with a high energy explosive filler. The oxetane thermoplastic elastomer energetic binder preferably comprises from about five percent to about thirty percent by weight and the high energy explosive filler comprises from about seventy percent to about ninety-five percent by weight of the composition. A preferred propellant further includes an explosive plasticizer, preferably in an amount of about four percent to about seven percent of the plasticizer by weight of the propellant. The preferred filler is selected from the group consisting of CL-20, TNAZ, RDX and mixtures thereof. The preferred plasticizer is selected from the group consisting of TNAZ, BTTN, TMETN, TEGDN, BDNPA/F, methyl NENA, ethyl NENA and mixtures thereof.
    Type: Grant
    Filed: September 12, 2000
    Date of Patent: February 14, 2006
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Thelma G. Manning, Joseph L. Prezelski, Sam Moy, Bernard Strauss, James A. Hartwell, Arpad Juhasz
  • Patent number: 6992185
    Abstract: A method is provided in which 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,903,11]-dodecane (CL-20 or HNIW) is crystallized to its ?-polymorph by an inverse precipitation technique. A dry CL-20 solvent solution containing an amount of CL-20 dissolved in a CL-20 solvent is prepared. The dry solvent solution is added to a crystallizer containing a CL-20 non-solvent to cause precipitation of epsilon polymorph CL-20 crystals by the inverse precipitation technique. The precipitated epsilon polymorph CL-20 crystals are separated from the non-solvent and the solvent.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: January 31, 2006
    Assignee: Alliant Techsystems Inc.
    Inventor: R. Scott Hamilton
  • Patent number: 6984275
    Abstract: The present invention comprises an additive to a propelling charge that greatly reduces barrel erosion when used in a gun system compared to the current additives noted above. The invention provides both a high nitrogen to carbon monoxide ratio in the combustion products of the propelling charge in conjunction with a reduced flame temperature which both work to reduce gun-barrel erosion.
    Type: Grant
    Filed: February 12, 2003
    Date of Patent: January 10, 2006
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Christine Marie Walsh, Christine Dianne Knott, Charles Stanley Leveritt
  • Patent number: 6979022
    Abstract: A flexible inflator for an inflation assembly and related gas generating propellant compositions are provided. The flexible inflator includes at least one elongated strand of a propellant co-extruded with a moisture barrier. The propellant compositions are adapted for co-extrusion with a plastic sheath which forms the moisture barrier surrounding the propellant and include a binder fuel component effective to render the composition flexible and to impart sufficient adhesive properties such that the propellant composition and the plastic sheath adhere together, and an oxidizer.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: December 27, 2005
    Assignee: Autoliv ASP, Inc.
    Inventors: Bradley W. Smith, Ivan V. Mendenhall
  • Patent number: 6955732
    Abstract: The invention disclosed herein relates to an explosive capable of enhanced combustion efficiently capable of sustaining a high pressure over a period of time in a confined environment, such as an air tight room or a cave, where oxygen may be in limited supply. An embodiment of the present invention is a metal composite that combines a binder, a reactive metal and an oxidizer. In another embodiment, a plasticizer and a catalyst are added. In another embodiment of the present invention, a solid fuel-air explosive (SFAE) having an annular construction is used. In a typical annular construction, a cylindrical shell of SFAE surrounds the cylindrically shaped high explosive. The SFAE includes at least one of reactive metal and metal composite. In addition, the metal composite is formed from at least one reactive metal, at least one binder and an oxidizer.
    Type: Grant
    Filed: February 11, 2004
    Date of Patent: October 18, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: May L. Chan, Gary W. Meyers
  • Patent number: 6932878
    Abstract: A plastic mouldable explosive composition comprises a gelled binder and a particulate explosive filler contained in the binder, wherein the binder comprises a blend of polyethylene wax polymer together with a tackifying resin comprising a polyisobutene polymer. Desirably, the amount of the polyethylene wax polymer in the composition is in the range 2 to 35 percent by weight, the polyethylene polymer having a molecular weight in the inclusive range 3,000 to 15,000. Desirably, the polyisobutene polymer comprises a liquid polyisobutene having a molecular weight of from 500 to 7,000.
    Type: Grant
    Filed: July 5, 1991
    Date of Patent: August 23, 2005
    Assignee: BAE Systems plc
    Inventors: Deirdre Hallam, Ronald E. Hollands
  • Patent number: 6893516
    Abstract: An insensitive pressable explosive with a high level of energy comprises octogen grains or hexogen which are coated with a polysiloxane solution.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: May 17, 2005
    Assignee: Diehl Munitionssysteme GmbH & Co. KG
    Inventor: Karl Rudolf
  • Patent number: 6887324
    Abstract: A composition C4 substitute is provided, the substitute including 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,903,11]-dodecane (CL-20), optionally one or more nitramines other than CL-20, and silicone fluid. Also provided is an additive composition including CL-20 and bis(dinitropropyl)acetal and bis(dinitropropyl)formal (BDNPA/F). The additive composition is preferably combined with composition C-4.
    Type: Grant
    Filed: February 5, 2002
    Date of Patent: May 3, 2005
    Assignee: Alliant Techsystems Inc.
    Inventor: Kenneth E. Lee
  • Patent number: 6884307
    Abstract: Insensitive explosive molding powders are provided that include an explosive component, a binder and a plasticizer. The insensitive molding powders include explosive crystals that are bound by a binder system. Moreover, the insensitive high explosive molding powder of the present invention has a bi-/tri-/tetramodal grain composition comprising coarse grain (280-360 ?m with an upper limit of 500-700 ?m) and fine grain (e.g., 35-45 ?m) explosive crystals that a bonded by a binder system comprising a plasticizer and a binder. The molding powder of the present invention is coated in waterless solvent process having a solvent content of less than 0.01 wt. % and is immediately ready for pellet pressing.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: April 26, 2005
    Assignee: Diehl Munitionssysteme GmbH & Co. KG
    Inventors: Heinz Hofmann, Karl Rudolf
  • Patent number: 6881283
    Abstract: An explosive composition is provided that includes 85 to about 96 weight percent nitramine, based on the total composition weight, and about 4 to 15 weight percent plasticized binder. At least 80 weight percent of the total composition weight, and more preferably 85 to 96 weight percent of the total composition weight, comprises 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,903,11]-dodecane (CL-20) particles having an average particle size not greater than 30 microns as the nitramine. Methods for preparing an explosive from the explosive composition are also provide.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: April 19, 2005
    Assignee: Alliant Techsystems Inc.
    Inventors: Kenneth E. Lee, Paul C. Braithwaite, Steve Nicolich, Mark Mezger
  • Patent number: 6877435
    Abstract: This invention relates to a gas generator having two or more compartments, each with a separate initiator, with one compartment discharging before another, i.e., the compartments discharge sequentially. Each compartment has the same propellants, but the propellants have different geometries in each compartment, which results in different rates of gas evolution from each compartment. The new gas generator is designed to reach maximum inflation at the same time as the current, single stage gas generators. However, the new generator has a more rapid initial inflation, followed by a more gradual inflation rate in the subsequent stages, improving safety to occupants. The propellant used in new generator comprises (1) ammonium nitrate as the oxidizer, which is less toxic and corrosive than the currently-used azide, (2) a fuel such as CL-20, and (3) a binder such as polycaprolactone. No hot metal particles (e.g., CuO) are generated in the new system.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: April 12, 2005
    Assignee: Textron Systems Corporation
    Inventor: Sami Daoud
  • Publication number: 20040216822
    Abstract: An insensitive, yet fully energetic high explosive molding powder using sonochemically aminated 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) as an energetic binder, i.e., adhesive, is provided. The sonochemically aminated TATB is used at a relatively low weight % level (less than 15% by weight) in comparison to conventional crystalline TATB.
    Type: Application
    Filed: November 17, 2003
    Publication date: November 4, 2004
    Inventors: Heinz Hofmann, Karl Rudolf
  • Patent number: 6764562
    Abstract: The invention relates to a pyrotechnical composition which is intended both for a hybrid gas-generating material and for a purely pyrotechnical gas-generating material for use in gas-actuated car safety devices, and which comprises a first obligatory constituent in the form of 5-95 wt % of guanyl urea dinitramide and a second obligatory constituent in the form of 5-50 wt % of an oxidizing agent (calculated on the total amount of solids), together with—if it is necessary to increase the rate of burning—a combustion moderator in the form of 0-90 wt % of guanidine dinitramide or up to 10 wt % of finely divided metallic boron, as well as up to 10 wt % of a binder. The pyrotechnical composition according to the invention is characterized e.g. by a low pollutant emission, low smoke formation, and the fact that its rate of burning can be adjusted to suit any type of car safety device by varying the ratio between the constituents within the limits specified in the invention.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: July 20, 2004
    Assignee: Bofors Bepab AB
    Inventors: Svante Persson, Conny Sjöqvist
  • Publication number: 20040129356
    Abstract: A melt-cast explosive which shares comparable explosive properties to those of COMP B explosives and is melt-pourable and castable under conditions comparable to those of COMP B explosives, but experiences less impact, shock, and thermal sensitivity and avoids the issues of toxicity associated with COMP B. A fundamental and well-accepted component of COMP B, i.e., trinitrotoluene (TNT), is replaced with one or more mononitro-substituted or dinitro-substituted melt-cast binders, such as dinitroanisole, which can be melt-cast without presenting the toxicity drawbacks experienced with the use of TNT. The melt-cast binder can also be combined with a processing aid selected from the group consisting of alkylnitroanilines and arylnitroanilines. Preferably, the composition also includes coarse oxidizer particles and energetic filler in fine particulate form.
    Type: Application
    Filed: August 22, 2003
    Publication date: July 8, 2004
    Inventors: Daniel W. Doll, Jami M. Hanks, Thomas K. Highsmith, Gary K. Lund
  • Patent number: 6755990
    Abstract: “The invention is directed to a monopropellant composition for propulsion and/or gas generation, comprising a solution of hydrazinium nitroformate (HNF) and/or ammonium dinitramide (ADM) in water and/or an alkanol.
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: June 29, 2004
    Inventors: Ronald Peter van den Berg, Petrus Johannes Maria Elands, Johannes Maria Mul
  • Patent number: 6736913
    Abstract: A method for processing explosives containing a high loading of CL-20 may advantageously include a binder system having naphthenic oil and/or paraffinic oil. Solid energetic ingredients are added into the binder system and mixed to form a free-flowing suspension in which the solid energetic ingredients are homogeneously mixed and coated with the binder system. The binder system is then cured and cast to form a cross-linked explosive.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: May 18, 2004
    Assignee: Alliant Techsystems Inc.
    Inventor: Robert L. Hatch
  • Patent number: 6673174
    Abstract: Plastic bonded explosive (PBX) compositions utilizing CL-20 as the oxidizer, and particularly when the CL-20 is blended with particular combinations of binders and/or plasticizers, have been found to yield synergistic chemical combinations which demonstrate higher energy density and increased penetration power and impetus in military weapons and similar applications.
    Type: Grant
    Filed: August 14, 2001
    Date of Patent: January 6, 2004
    Assignee: Textron Systems Corporation
    Inventor: Sami Daoud
  • Patent number: 6641683
    Abstract: A melt-castable explosive composition not based on TNT consisting essentially of about 10 to 20 weight percent of a matrix material having a melting temperature of about 80° to 100° C., about 1 to 5 weight percent of a plasticizer, up to about 20 weight percent of a metal powder, up to about 20 weight percent of an oxidizer and about 70 to 89 weight percent of a high explosive. The matrix material is carnauba wax modified with ozokerite wax in a weight ratio of about 1:1 to 20:1.
    Type: Grant
    Filed: September 11, 2002
    Date of Patent: November 4, 2003
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Robert L. McKenney, Jr., John F. Leahy, Spencer T. Parkin, Thomas R. Krawietz
  • Patent number: 6635131
    Abstract: An apparatus comprises a vehicle occupant protection device and a gas generating material, which, when ignited, produces gas to actuate the vehicle occupant protection device. The gas generating material comprises a cubane compound having the general formula: wherein R is selected from the group consisting of H and NO2.
    Type: Grant
    Filed: March 26, 2001
    Date of Patent: October 21, 2003
    Assignees: TRW Inc., TRW Vehicle Safety Systems Inc.
    Inventors: Harold R. Blomquist, Douglas P. Campbell, Peter Staudhammer
  • Publication number: 20030192631
    Abstract: By virtue of at least 5% of octogen in relation to the hexogen explosive, insensitive behaviour is achieved in relation to high thermal loadings (Fast Cook Off).
    Type: Application
    Filed: September 24, 2002
    Publication date: October 16, 2003
    Applicant: Diehl Munitionssysteme GmbH & Co. KG
    Inventors: Heinz Hofmann, Karl Rudolf
  • Patent number: 6630040
    Abstract: Solutions and process are described useful to produce coated HE powder granules in an aqueous slurry agglomeration process. A reaction mixture is made utilizing a lacquer stock solution comprising a binder material dissolved in a substantially aqueous-immiscible organic lacquer solvent, and an aqueous HE powder slurry solution comprising a non-aqueous soluble HE powder and an at least partially aqueous-miscible organic co-solvent. The co-solvent acts as an entrainer and improves the immiscible of the lacquer solvent in the water phase of the aqueous HE powder slurry solution, resulting in formation of HE powder agglomerates that remain stable as the solvents are removed from the reaction mixture during the agglomeration process. Further, the process is adjustable to substantially eliminate organic solvent contamination of the waste water stream.
    Type: Grant
    Filed: January 31, 2002
    Date of Patent: October 7, 2003
    Assignee: Schlumberger Technology Corporation
    Inventor: Philip Kneisl
  • Patent number: 6627014
    Abstract: An apparatus (10) for inflating an inflatable vehicle occupant protection device comprises a container (12) for storing a supply of gas. A gas (26) is stored in the container (12) at an elevated pressure. The gas comprises an oxygen rich oxidizer gas. A gas generating material (84) is stored in the container (12) and is exposed to the oxidizer gas at the elevated pressure. The gas generating material (84) comprises a cellulose based binder blended with an anti-oxidant material. An igniter (52) is provided for igniting the gas generating material (84).
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: September 30, 2003
    Assignee: TRW Inc.
    Inventor: Harold R. Blomquist
  • Patent number: 6605233
    Abstract: A low-solids gas generating composition and a method of producing a gas. The gas is produced by combusting a mixture of a fuel selected from the group consisting of guanidine nitrate, nitroguanidine, cellulose, cellulose acetate, hexamine, 5 amino-tetrazole, 5 nitro-uracil, guanidine salt of 5 nitro-uracil, and mixtures thereof, an oxidizer selected from the group consisting of ceric ammonium nitrate, strontium nitrate, basic copper nitrate, a mixture of ammonium perchlorate and at least one alkali metal salt, and mixtures thereof, and a cupric oxalate hemi-hydrate coolant. The oxidizer-fuel mixture is within about 4 percent of stoichiometric balance, and the low-solids gas generating composition produces no more than about 0.082 cubic centimeters of solids per gram of gas generating composition on combustion.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: August 12, 2003
    Assignee: Talley Defense Systems, Inc.
    Inventors: Gregory D. Knowlton, Christopher P. Ludwig
  • Patent number: 6589375
    Abstract: A low-solids gas generating composition and a method of generating a gas with low solids by preparing and combusting the low-solids gas generating composition. The compositions of the invention include a mixture of a basic copper nitrate oxidizer and a fuel selected for the group consisting of 5-nitro-uracil, guanidine 5-nitro-uracil salt, ammonium 5-nitro-uracil salt, aminoguanidine 5-nitro-uracil salt, hydrazine 5-nitro-uracil salt, triamino 5-nitro-uracil salt, guanidine 5-nitro-barbituric acid salt, ammonium 5-nitro-barbituric acid salt, hydrazine 5-nitro-barbituric acid salt, aminoguanidine 5-nitro-barbituric acid salt, triaminoguanidine 5-nitro-barbituric acid salt, and mixtures thereof, wherein the oxidizer-fuel mixture is within about 4 percent of stoichiometric balance, and produces no more than about 0.06 cubic centimeters of solids per gram of gas generating composition on combustion.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: July 8, 2003
    Assignee: Talley Defense Systems, Inc.
    Inventors: Gregory D. Knowlton, Christopher P. Ludwig, Thomas M. Deppert, Dan McFadden, James Dupont, Christian Salafia
  • Patent number: 6562159
    Abstract: An insensitive melt cast explosive composition obtained by dissolving an energetic copolyurethane thermoplastic elastomer (“ETPE”) in melted trinitrotoluene (“TNT”) is disclosed. The resulting ETPE-TNT solution is easy to mix with other ingredients such as nitramines, plasticizers, aluminum and can be processed with the existing melt cast facilities. The energetic solution can be poured into shells and upon cooling to produce a recyclable plastic bonded explosive. Instead of melted TNT, the same process works equally well with melted Octol or melted Composition B to dissolve the ETPE.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: May 13, 2003
    Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National Defence
    Inventors: Guy Ampleman, Patrick Brousseau, Sonia Thiboutot, Charles Dubois, Emmanuela Diaz
  • Patent number: 6552051
    Abstract: Novel compounds are provided having the structural formula R[—N(NO2)—L—R1]n wherein R, L, R1 and n are defined herein. The compounds are useful in a variety of contexts, but are primarily to be used as high energy oxidizing agents in explosive compositions, propellant formulations, gas-generating compositions and the like. The compounds are also useful as pharmaceutical agents. Compositions containing the compounds are also provided, including energetic compositions, as are methods for using the novel compounds and compositions.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: April 22, 2003
    Assignee: SRI International
    Inventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
  • Patent number: 6550808
    Abstract: Gas generant compositions are provided which compositions react to produce nitrogen gas and which compositions include guanylurea nitrate and at least one transition metal-containing water-compatible oxidizer. Also, related methods of gas generation are provided.
    Type: Grant
    Filed: November 17, 2000
    Date of Patent: April 22, 2003
    Assignee: Autoliv ASP. Inc.
    Inventor: Ivan V. Mendenhall
  • Publication number: 20030041936
    Abstract: Method of synthesis of dinitro-diaza-alkanes and intermediate products thereto from alkylamines and esters, whereby a dialkyl ester of a dicarboxylic acid is reacted with an alkylamine in an aqueous medium to form the corresponding dialkyldiamide of the dicarboxylic acid;
    Type: Application
    Filed: November 1, 2001
    Publication date: March 6, 2003
    Inventor: Thomas Knott
  • Patent number: 6513834
    Abstract: An apparatus comprises a vehicle occupant protection device (14) and a gas generating material (18). The gas generating material (18), when ignited, produces a combustion gas that actuates the vehicle occupant protection device (14). At least about 45% by weight of the gas generating material (18) is a mono-propellant selected from the group consisting of 3-nitramino-4-nitrofurazan and hydroxylammonium 3-nitroamino-4-nitrofurazan. 0 to about 48% by weight of the gas generating material (18) is an oxidizer. 0 to about 15% by weight of the gas generating material (18) is a binder.
    Type: Grant
    Filed: August 29, 2000
    Date of Patent: February 4, 2003
    Assignee: TRW Inc.
    Inventor: Harold R. Blomquist
  • Patent number: 6512113
    Abstract: A process for preparing 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]-dodecane involves reacting at least one hexa-substituted piperazine derivative with at least one nitrate source and optionally at least one strong acid and heating the mixture to a temperature sufficient to induce an exothermic initial stage of the between the hexa-substituted piperazine derivative and the nitrate source. The mixture is maintained at a temperature in a range of at least ambient to not more than about 80° C. during the exothermic initial stage and at least a portion of a subsequent non-exothermic intermediate stage of the reaction by cooling the mixture during at least a portion of the exothermic initial stage of the reaction so that the reaction proceeds in a controlled manner. The mixture is then cooled to a temperature sufficiently low to prevent commencement of an exothermic NOx autocatalytic stage.
    Type: Grant
    Filed: June 8, 2000
    Date of Patent: January 28, 2003
    Assignee: Alliant Techsystems Inc.
    Inventors: Andrew J. Sanderson, Robert M. Hajik, Thomas K. Highsmith, Harold E. Johnston
  • Patent number: 6509473
    Abstract: New energetic salts of 1,2,4-triazole; 3,4,5-triamino-1,2,4-triazole and of 4-amino 1,2,4-triazole were synthesized, characterized and their thermal and safety properties evaluated as possible new propellant ingredients. Energetic anions, including the nitrate anion, NO3, the perchlorate anion, ClO4, & the dinitramide anion, N(NO2)2, were paired with the protonated heterocycles through facile, high yield synthetic routes to give crystalline, energetic salts. Using such a heterocycle system, either 1,2,4-triazole; 3,4,5-triamino-1,2,4-triazole or 4-amino 1,2,4-triazole, a new family of salts were synthesized through the direct reaction of the heterocycle with the corresponding acid form of the desired anion. These reactions were carried out in commonly available polar solvents, and at ambient temperatures, to give high purity, high yield products.
    Type: Grant
    Filed: October 16, 2000
    Date of Patent: January 21, 2003
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventor: Greg W. Drake
  • Patent number: 6472525
    Abstract: Disclosed is an acyl group-containing hexaazaisowurtzitane derivative represented by the following formula (I): W At Q(6−t), wherein t represents an integer of from 4 to 6, A independently represents an acyl group having 1 to 10 carbon atoms, each Q independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and W represents a hexavalent hexaazaisowurtzitane residue represented by the following formula (II): Also disclosed is a method for producing the above-mentioned acyl group-containing hexaazaisowurtzitane derivative. The acyl group-containing hexaazaisowurtzitane derivative of the present invention is useful as a precursor of a polynitrohexaazaisowurtzitane derivative which can be used not only as a material for explosives but also as an additive for propellants and explosives.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: October 29, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Tamotsu Kodama, Masahiro Tojo, Masanori Ikeda
  • Patent number: 6428724
    Abstract: A process for forming granules (e.g., alpha-HMX containing granules) from at least one particulate material comprises the steps of: (a) selecting particulates (e.g., alpha-HMX particulates) having a particle size distribution; and (b) fluidizing the particulates, whereby particulates agglomerate to form granules. Optionally, the particulates can be coated with one or more second materials, such as energetic materials or fuels. If one or more of the second materials comprise polymerizable monomers, the process can optionally further comprise the step of polymerizing those monomers in situ, either before or after the granule is formed.
    Type: Grant
    Filed: January 3, 2000
    Date of Patent: August 6, 2002
    Assignee: Schlumberger Technology Corporation
    Inventors: William J. Lukasavage, Karri A. Brock, Lawrence A. Behrmann, Wallace E. Voreck
  • Patent number: 6395899
    Abstract: Calculated performance improvements are expected from a particularly new class of compounds, geminal-bis(difluoramino)-substituted heterocyclic nitramines, when formulated into explosives and propellants. This invention involves novel and nonintuitive methods for the preparation of certain derivatives of 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine which are suitable precursors leading to 5,5-bis(difluoramino)hexahydro-1,3-dinitropyrimidine (RNFX). The invention also involves novel and nonintuitive methods for the preparation of RNFX, a specific member of a general class of compounds with the substructure 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine. RNFX is produced by the use of key intermediates, including tetrahydropyrimidin-5(4H)-ones, which allow formation of the target structural subcomponent, 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine, and a more specific substructure of 2,2-bis(difluoramino)-N,N′-dinitro-1,3-propanediamine.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: May 28, 2002
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Robert Dale Chapman, Ba Van Nguyen
  • Patent number: 6391130
    Abstract: In this process 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazatetracyclo-[5.5.0.05,903,11]-dodecane (“TADH”) is subjected to nitrolysis in the presence of a mixed acid to form HNIW. The mixed acid comprises at least one nitronium ion source (preferably nitric acid) and at least one strong acid (preferably sulfuric acid) capable of generating a nitronium ion from the source. The ratio of nitronium ion source to strong acid and the amount of TADH used are selected so that, in the event that the nitrolysis reaction is carried out at 85° C., 99% nitramine conversion will occur within ten minutes.
    Type: Grant
    Filed: February 15, 2000
    Date of Patent: May 21, 2002
    Assignee: Alliant Techsystems Inc.
    Inventors: Andrew J. Sanderson, Kirstin Warner, Robert B. Wardle
  • Patent number: 6368432
    Abstract: A gas generating composition for generating gas by a combustion reaction to inflate, for example, an airbag. The gas generating composition includes an oxidant and crystalline carbon powder that reacts with the oxidant. The oxidant is preferably ammonium nitrate. The crystalline carbon powder is preferably activated carbon powder. The gas generating composition preferably includes a high energy substance, binder and plasticizer.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: April 9, 2002
    Assignee: NOF Corporation
    Inventors: Kazuya Serizawa, Katsuhiko Takahashi, Kenji Nakamichi
  • Patent number: 6361630
    Abstract: An apparatus (10) comprises an inflatable vehicle occupant protection device (16) and a gas generating composition which when ignited produces gas to inflate the inflatable vehicle occupant protection device (16). The gas generating composition comprises a non-azide nitrogen containing organic fuel, an inorganic salt oxidizer, and a metal organic coolant selected from the group consisting of alkali metal formates, alkaline earth metal formates, alkali metal oxalates, and alkaline earth metal oxalates. The amount of metal organic coolant in the gas generating composition is a cooling amount.
    Type: Grant
    Filed: August 17, 1999
    Date of Patent: March 26, 2002
    Assignee: TRW Inc.
    Inventors: Abdel K. Helmy, Tracy N. Michon
  • Patent number: 6312538
    Abstract: A new compound, 1,1-diamino-2,2-dinitroethylene suitable for use as an explosive, as well as an intermediate for preparing the compound consisting of a heterocyclic 5- or 6-ring of the general formula wherein n=at least 1. The compound is prepared by nitrating a heterocyclic 5- or 6-ring containing the structural element wherein Y is an alkoxy group, with a nitrating acid at a low temperature, preferably 0-30° C., and selecting the acidity of the nitrating acid for obtaining a substantial yield of a product containing the structural element and hydrolyzing said product in an aqueous medium for separating 1,1-diamino-2,2--dinitroethylene which is recovered as a precipitate.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: November 6, 2001
    Assignee: Totalforsvarets Forskningsinstitut
    Inventors: Nikolai Latypov, Abraham Langlet, Ulf Wellmar
  • Patent number: 6309484
    Abstract: A propellent charge powder for barrel-type weapons having a plasticizer on the basis of nitramine and nitrocellulose, nitramine and energetic and non-energetic plastic binders, or nitrocellulose or an explosive, and wherein the plasticizer is a mixture of at least two chemically different dinitro diaza compounds. The plasticizer facilitates the production and use of the propellent charge powder possessing a low temperature coefficient.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: October 30, 2001
    Assignee: Diehl Stiftung & Co.
    Inventors: Walter Langlotz, Dietmar Müller
  • Patent number: 6277296
    Abstract: Fire suppressant compositions which are substantially free of ammonium nitrate and which comprise potassium nitrate in an amount sufficient to generate at least about 10 wt. % potassium carbonate when combusted. Most preferably, a guanidine salt, such as guanidine nitrate, is used in combination with the potassium nitrate. The compositions employed in the present invention have low pressure exponents, high burning rates and low flame temperatures.
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: August 21, 2001
    Assignee: Atlantic Research Corporation
    Inventors: Robert S. Scheffee, Jamie B. Neidert, Robert E. Black, III, Robert D. Lynch, James D. Martin
  • Patent number: 6277221
    Abstract: Solid pyrotechnic gas generant compositions and monopropellants are provided for use in inflators of automotive air bag restraint systems which, when combusted, produce acceptable burning rates, generate a high concentration of substantially innocuous gases, and a low concentration of substantially water insoluble non-toxic solid combustion products which limits the potential for asthmatic and pulmonary conditions. The propellant compositions provided are based on metal salts of lanthanide and rare earth elements, particularly lanthanide or rare earth nitrate salts and lanthanide or rare earth complexes with nitrogen-containing cations and nitrate anions. Scandium and cerium are preferred lanthanide and rare earth elements for these compositions.
    Type: Grant
    Filed: April 13, 1999
    Date of Patent: August 21, 2001
    Assignee: Atlantic Research Corporation
    Inventor: Norman H. Lundstrom
  • Patent number: 6265573
    Abstract: A process for separating a nitramine or nitramine intermediate from water and volatile organic compounds comprises the steps of: (a) feeding a liquid stream comprising a liquid nitramine or nitramine intermediate, water, and at least one volatile organic compound, into the upper half of a stripper column; (b) feeding a gas stream having a temperature of at least about 120° C. into the lower half of the stripper column, whereby the gas stream and the liquid stream come into countercurrent contact in the stripper column; (c) withdrawing a nitramine or nitramine intermediate stream from the bottom of the stripper column; and (d) withdrawing a waste stream comprising gas and one or more of water vapor, water, formaldehyde, and acetic acid, from the top of the column.
    Type: Grant
    Filed: January 3, 2000
    Date of Patent: July 24, 2001
    Assignee: Schlumberger Technology Corporation
    Inventor: William J. Lukasavage
  • Patent number: 6255512
    Abstract: Novel compounds are provided having the structural formula R[—N(NO2)—L—R1]n wherein R, L, R1 and n are defined herein. The compounds are useful in a variety of contexts, but are primarily to be used as high energy oxidizing agents in explosive compositions, propellant formulations, gas-generating compositions and the like. The compounds are also useful as pharmaceutical agents. Compositions containing the compounds are also provided, including energetic compositions, as are methods for using the novel compounds and compositions.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: July 3, 2001
    Assignee: SRI International
    Inventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
  • Patent number: 6241833
    Abstract: A low sensitivity gun propellant is disclosed having improved impetus and ballistic potential comprising RDX particles combined with at least one matrix component and plasticizer components including nitroglycerin and amounts of methyl nitrato ethyl nitramine and ethyl nitrate ethyl nitramine.
    Type: Grant
    Filed: July 16, 1998
    Date of Patent: June 5, 2001
    Assignee: Alliant Techsystems, Inc.
    Inventor: Lisa G. Brown
  • Patent number: 6238501
    Abstract: The invention is a composition containing high loadings of TNAZ that are made by crash precipitation with water as the precipitation agent. The compositions are in the form of powders, which can be formed and shaped by presseing, extrusion, etc. The TNAZ can be from about 94 to about 99% by weight of the composition.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: May 29, 2001
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Daniel Stec, III, Rao C. Surapaneni, Brian E. Travers
  • Patent number: 6217799
    Abstract: A water slurry method of making high performance explosive compositions and ordnances using the explosive compositions as an explosive ingredient for high performance, low sensitivity explosive applications is disclosed. The method involves combining an aqueous dispersion including CL-20 with a lacquer including at least one non-energetic binder and at least one plasticizer, then agitating the slurry to form CL-20 granules. The CL-20 may be present in the explosive formulation in a concentration of from about 85 wt % to about 96 wt %. The formulation is preferably sufficiently pressable and/or extrudable to permit it to be formed into grains suitable for ordnance and similar applications, including use as grenades, land mines, missile warheads, and demolition explosives.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: April 17, 2001
    Assignee: Cordant Technologies Inc.
    Inventors: Kenneth E. Lee, Robert L. Hatch, Paul Braithwaite