Nitramines (i.e., Compounds Containing Nitro Bonded Directly To Amino Nitrogen) Patents (Class 564/107)
  • Patent number: 8853282
    Abstract: A topical liquid formulation is provided which contains a combination of three active ingredients for treating fleas and ticks in domestic animals. Total concentration of the active hydrophobic and hydrophilic ingredients can exceed 60 weight percent. In contrast to commonly available flea treatments, the new insecticidal composition is safe and effective for both felines and canines and a single topical application can be effective for at least several weeks.
    Type: Grant
    Filed: May 22, 2014
    Date of Patent: October 7, 2014
    Assignee: Sumitomo Corporation
    Inventor: Ian Cottrell
  • Publication number: 20130121909
    Abstract: A method of purification and modification of carbon nanoproduct involves forcing a mixture of the dehydrated air or oxygen or ozone or any combination thereof through the carbon nanoproduct under pressure up to 0.8 MPa accompanied by mixing of the carbon nanoproduct and heating in the temperature range from +20 to +550° C. This abstract is not to be considered limiting, since other embodiments may deviate from the features described in this abstract.
    Type: Application
    Filed: December 18, 2012
    Publication date: May 16, 2013
    Inventors: Igor Leonidovich Petrov, Yuriy Alekseevich Skryabin, Olga Alexander Shenderova
  • Patent number: 7981393
    Abstract: A method of preparing salt of dinitramidic acid, comprising nitration of an initial compound with a nitrating acid mixture to form dinitramidic acid in a reaction mixture. A positive ion is added to the reaction mixture and forms with the dinitramide ion an ion pair complex which precipitates in the acidic reaction mixture, and the precipitate is separated from the mixture. The remaining spent acid can be reprocessed for recovery of acid for preparation of a new nitrating acid mixture. The preferred positive ion is the guanylurea ion which gives a precipitate of guanylurea dinitramide. The precipitate can be used as starting material for preparation of other dinitramide salts, such as KDN and ADN. The guanylurea ion can be formed in situ in the process by cyanoguanidine being reacted with the reaction mixture.
    Type: Grant
    Filed: January 21, 2005
    Date of Patent: July 19, 2011
    Assignee: Försvarets Materielverk
    Inventors: Carin Vörde, Henrik Skifs
  • Publication number: 20090270509
    Abstract: This invention relates to compositions comprising carbon-based diazeniumdiolates that release nitric oxide (NO). The carbon-based diazeniumdiolated molecules release NO spontaneously under physiological conditions without subsequent nitrosamine formation. The present invention also relates to methods of preparing the carbon-based diazeniumdiolated molecules, compositions comprising such molecules, methods of using such compositions, and devices employing such molecule compositions.
    Type: Application
    Filed: July 2, 2009
    Publication date: October 29, 2009
    Applicant: Noxilizer, Inc.
    Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
  • Patent number: 6833478
    Abstract: A method is provided for enhancing the solubility of an ionizable compound in a lipophilic medium by admixing the compound with an effective solubility-enhancing amount of an N,N-dinitramide salt. The ionizable compound, upon ionization, gives rise to a biologically active cationic species that ionically associates with the N,N-dinitramide anion N(NO2)2− following admixture with the N,N-dinitramide salt. The biologically active cationic species may be a pharmacologically active cation, in which case the method is useful for enhancing the penetration of the blood-brain barrier by the pharmacologically active cation. In other embodiments, the ionizable compounds are medical imaging or diagnostic agents, or agricultural agents such as pesticides. Salts of biologically active cations and N,N-dinitramide ion are also provided as novel compositions of matter.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: December 21, 2004
    Assignee: SRI International
    Inventors: Jeffrey C. Bottaro, Mark A. Petrie, Paul E. Penwell, David C. Bomberger
  • Patent number: 6790836
    Abstract: A process for preparing indolopyrrolocarbazole derivatives [I] by trating a compound [V] with a base in an inert solvent to prepare a compound [IV], reacting the compound [IV] with a compound [III]to prepare a compound [II], and deblocking the compound [II]; intermediates [II], [III] and [IV]; and a process for preparing compounds [III]: [wherein Y1 is hydrogen, C1-4 alkyl, phenyl, benzyloxymethyl, or aralkyl; R1, R2, R3, R4, R5, and R6 are each independently a hydroxyl-protecting group; R7 and R8 are each independently hydrogen or a hydroxyl-protecting group; and X is an acid molecule]. The above process is a safe and easy industrial process for preparing indolopyrrolocarbazole derivatives [1] useful as antitumor agents.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: September 14, 2004
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Shouichi Hiraga, Masashi Kawasaki, Atsushi Akao, Asayuki Kamatani, Masayuki Hagiwara, Toshiaki Mase, Fumio Nakano
  • Publication number: 20040063783
    Abstract: The present invention relates to a compound of formula (I) in which X, A, T, Y, G and R are as defined in Claim (1).
    Type: Application
    Filed: April 3, 2003
    Publication date: April 1, 2004
    Inventors: Claude Lardy, Jean-Yves Nioche, Lidia Caputo, Jacques Decerprit, Jean-Yves Ortholand, Didier Festal, Daniel Guerrier
  • Publication number: 20040039229
    Abstract: Nitramines are one of the more expensive and often the more plentiful ingredients found in energetic materials, such as solid rocket motor propellants, explosives, and pyrotechnics. By treating aluminized energetic material with an aqueous nitric acid solution containing not more than 55% by weight aqueous nitric acid at a weight ratio of aqueous nitric acid to energetic material of about 4:1 to about 6:1, most constituents of conventional aluminized energetic materials are digested into solution, with the exception of nitramines, which remain substantially insoluble in the aqueous nitric acid and can be recovered without requiring recrystallization of the nitramines. A mineral acid other than nitric acid, preferably hydrochloric acid, may be added to increase the rate of aluminum digestion. Treatment of the energetic material can be performed without volatile organic solvents, thus obviating ecological, cost, and safety concerns raised by the use of volatile organic solvents.
    Type: Application
    Filed: August 22, 2003
    Publication date: February 26, 2004
    Inventors: Kirstin F. Warner, Louis F. Cannizzo, Robert M. Hajik
  • Patent number: 6653506
    Abstract: Methods to recover nitramines from energetic materials yielding useable by-products and producing zero waste. The methods are used on materials containing HMX and RDX.
    Type: Grant
    Filed: September 16, 2002
    Date of Patent: November 25, 2003
    Assignee: TPL, Inc.
    Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael Miks
  • Publication number: 20030191346
    Abstract: The invention relates to a method for producing DNDA that is advantageous in economical, chemical and process engineering terms.
    Type: Application
    Filed: June 2, 2003
    Publication date: October 9, 2003
    Inventors: Rainer Schirra, Heinz-Gerd Emans, Leonard Lichtblau
  • Patent number: 6603018
    Abstract: A method is provided for the synthesis of nitramines and the recovery of the nitramines from a clathrate.
    Type: Grant
    Filed: January 29, 2002
    Date of Patent: August 5, 2003
    Assignee: Alliant Techsystems Inc.
    Inventors: Thomas K. Highsmith, Jami M. Hanks, Stephen P. Velarde, Jeffrey Bottaro
  • 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: 6147209
    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 8, 1992
    Date of Patent: November 14, 2000
    Assignee: Cordant Technologies Inc.
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 6068823
    Abstract: A direct fixation of NO.sub.2 and N.sub.2 O.sub.4 at room temperature and atmospheric pressure is described using bis(diorganoamino)magnesium compounds formed from reactions between donor-solvent free diorganomagnesium compounds and primary or secondary amines, yielding new compositions of matter having the general formulas [(R.sub.2 N).sub.i (R.sub.2 NN.sub.x O.sub.y)jMg].sub.m and [(R.sub.2 N).sub.i (R.sub.2 NN.sub.x O.sub.y).sub.j (N.sub.x O.sub.y).sub.k Mg].sub.m. Methods are also described to convert these new compositions of matter into useful organic compounds and nitrogen gas.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: May 30, 2000
    Assignee: The University of Houston System
    Inventors: Ramiro Sanchez, Graciela Lubertino
  • Patent number: 6063960
    Abstract: Methods to recover nitroamines from energetic pyrotechnic materials yielding useable by-products and producing zero waste. The methods are used on materials containing HMX and RDX.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: May 16, 2000
    Assignee: TPL, Inc.
    Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael W. Miks
  • Patent number: 5789617
    Abstract: This invention relates to novel neopentyl difluoroamino compounds which are useful as plasticizers and oxidizers in energetic formulations, such as propellants, explosives, and gasifiers. These neopentyl difluoroamino compounds can be prepared either: (1) by the direct fluorination of amine derivatives containing energetic pendant groups; or (2) by first preparing NF.sub.2 -derivatives and then substituting these derivatives with energetic pendant groups. In particular, mono- and bis-(difluoroaminomethyl) oxetanes are synthesized and further reacted to yield the corresponding dinitrate esters. It has been discovered that these NF.sub.2 -dinitrate esters are very useful as energetic plasticizers in high-energy formulations.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: August 4, 1998
    Assignee: Aerojet-General Corporation
    Inventors: Thomas G. Archibald, Gerald E. Manser
  • Patent number: 5780769
    Abstract: The thermal stability of an N,N-dinitramide salt of the formula M.sup.+ ?N(NO.sub.2).sub.2 !.sup.- where M.sup.+ is a nitrogen-containing cation, is improved by mixing with the N,N-dinitramide salt a compound of the formula ##STR1## where R, R' and R" are the same or different and are aryl or alkyl. A new composition of matter is formed by mixing the N,N-dinitramide salt and the prophosphatrane compound.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: July 14, 1998
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Thomas P. Russell, Indu B. Mishra
  • Patent number: 5659080
    Abstract: A synthetic method for ammonium dinitramide comprising a process for the formation of urea nitrate by reacting urea with diluted nitric acid; a process for the formation of nitrourea by reacting the urea nitrate with sulfuric acid; a process of reacting the nitrourea with a nitration reagent such as nitronium tetrafluoroborate, and then adding ammonia gas to the reaction mixture; and a process of filtering off the resultant by-product of crystals, concentrating its filtrate, adding ethyl acetate to this concentrated filtrate, filtering off the precipitate, concentrating again its filtrate under vacuum, and finally separating ADN as crystals by adding chloroform to the concentrated filtrate.Effects:ADN can be synthesized with the following features: urea as starting material is readily available and is cheaper in price, the process is uncomplicated and more simplified, the operation is safe, and the final product gives a high yield.
    Type: Grant
    Filed: May 28, 1996
    Date of Patent: August 19, 1997
    Assignees: Nissan Motor Co., Ltd., Hosoya Fireworks Co., Ltd.
    Inventors: Shigeru Suzuki, Shigefumi Miyazaki, Hideo Hatano, Kazuo Shiino, Toshio Onda
  • Patent number: 5585373
    Abstract: A derivative of 3-(7'-oxo-1'-aza-4'-oxabicyclo[3.2.0 ]hept-3'-yl)propionic acid represented by the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group optionally having one or more cycloalkyl groups, a lower acyl group, a benzoyl group optionally having one or more substituents or a benzyl group optionally having one or more substituents, R.sub.2 is a hydrogen atom or a carboxyl-protecting group, R.sub.3 is a hydroxyl group, an azido group, a benzenesulfonyloxy group optionally having one or more substituents, a lower alkylsulfonyloxy group optionally having one or more substituents, a tri-substituted silyloxy group or an amino group optionally having one or more substituents, provided that when R.sub.1 and R.sub.2 are hydrogen atoms, R.sub.3 is not an amino group, and a salt thereof.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: December 17, 1996
    Assignee: Taiho Pharmaceutical Co., Ltd
    Inventors: Zhang Z. Ping, Zhen J. Sheng, Zhang Q. Rong, Zhang J. Liang, Singh Rajeshwar, Tomohiro Yamashita, Toshiyuki Toko, Hiroshi Matsumoto
  • Patent number: 5415852
    Abstract: A method is disclosed for forming an ionically bonded dinitramide salt or acid useful as a stable oxidizer for solid fuel rocket propellant or explosive formulations is disclosed. The dinitramide salt is formed by the reaction of an N(alkoxycarbonyl)N-nitroamide and a nitronium-containing compound, at a temperature of from about +60.degree. C. to about -120.degree. C., followed by contacting the reaction mass with a base to form the dinitramide salt, or an alcohol to form the corresponding dinitramidic acid. The N(alkoxycarbonyl)N-nitroamide may be formed by first mixing the corresponding alkylcarbamate with an anhydride of one or more 1-20 carbon organic acids, then adding nitric acid to the reaction mixture. If the salt of the N(alkoxycarbonyl)N-nitroamide is to be formed, a base is then added until the pH reaches about 7-10. The nitronium-containing reactant may be a covalently bonded compound containing a NO.sub.2 -- group; a nitryl halide; or a nitronium salt having the formula (NO.sub.2.sup.+).sub.q X.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: May 16, 1995
    Assignee: SRI International
    Inventors: Robert J. Schmitt, Jeffrey C. Bottaro, Paul E. Penwell, David C. Bomberger
  • Patent number: 5382595
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: January 17, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5360478
    Abstract: Disclosed is a method for recrystallizing solid materials (e.g. RDX) from systems comprised of a solute, which is the eventual material recrystallized, a liquid which is a suitable solvent for the solute, and a gaseous component which is soluble within the solvent and whose presence therein causes the solvent to approach or attain a supersaturated state, thereby precipitating (recrystallizing) the solute material. By control of process parameters (pressure, temperature, time, and rate, rate of injection of gas, etc.) the operator can influence the properties of the material recrystallized.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: November 1, 1994
    Assignee: Phasex Corporation
    Inventors: Val J. Krukonis, P. M. Gallagher, M. P. Coffey
  • Patent number: 5254324
    Abstract: A N,N-dinitramide salt is disclosed having the formula MN(NO.sub.2).sub.2 where M is a cation selected from the class consisting of a metal ion and a nitrogen-containing ion. The dinitramide salt exhibits high temperature stability, high energy density, and an absence of smoke generating halogens, rendering it useful as an oxidizer in rocket fuels. The dinitramide salts are meltable and pumpable oxidizers which may be used in start-stop rocket engines instead of other less stable oxidizers.
    Type: Grant
    Filed: June 18, 1990
    Date of Patent: October 19, 1993
    Assignee: SRI International
    Inventors: Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David S. Ross
  • Patent number: 5243075
    Abstract: 1-acetoxy-2,4,6-trinitro-2,4,6-triazaheptane, 1,7-diacetoxy-2,4,6-trinitro-2,4,6-triazaheptane, or 1,9-diacetoxy-2,4,6,8-tetranitro-2,4,6,8-tetraazanonane is reacted with a mixture of concentrated hydrochloric acid and trifluoroacetic 2,4,6-triazaheptane, 1,7-dichloro-2,4,6-trinitro-2,4,6-triazaheptane, or 1,7-dichloro-2,4,6,8-tetranitro-2,4,6,8-tetraazanonane.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: September 7, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Donna M. Cason-Smith
  • Patent number: 5186770
    Abstract: Bis(2-nitro-2-azapropyl) ether which is prepared by reacting one mole 1-hydroxy-2-nitro-2-azapropane with one mole of 2-nitro-2-azapropyl trifluoroacetate or 2-nitro-2-azapropyl acetate.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: February 16, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Theodore C. Adams, Jr., Horst G. Adolph
  • Patent number: 5020731
    Abstract: Occluded acidity in particulate explosives is removed by slurrying the particles in an inert liquid and subjecting the slurry to wet-grinding. The inert liquid may include an alkaline salt at or near saturation. Separation of the ground explosive particles from the liquid phase results in a ground explosive material with much reduced acidity.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Thiokol Corporation
    Inventors: Carlos Somoza, Lee C. Estabrook
  • Patent number: 4588748
    Abstract: Benzylidene derivatives of the formula: ##STR1## wherein n is 3, R represents an amino or hydroxy radical, or a group --OM in which M is an alkali metal, X.sub.1 and X.sub.2 are both Cl, and X.sub.3 is hydrogen are new compounds possessing useful pharmacological properties; they are, more particularly, useful in the treatment of various diseases of the central nervous system.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: May 13, 1986
    Assignee: Synthelabo
    Inventor: Jean-Pierre Kaplan
  • Patent number: 4513148
    Abstract: The invention is an improved process for the production of methylnitramine y nitrating dimethylurea with a mixture of sulfuric acid and nitric acid with subsequent separation of 1,3-dimethyl-1,3-dinitrourea by the use of a suitable solvent with recovery of a dimethyl dinitrourea in organic solvent, with hydrolysis of the dimethyldinitrourea with hot water to yield methylnitramine.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: April 23, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George W. Nauflett
  • Patent number: 4476322
    Abstract: A process for preparing 2,4-dinitro-2,4-diazapentane by(1) nitrating dimethylurea to form dimethyldinitrourea;(2) hydrolyzing the dimethyldinitrourea to form methylnitramine;(3) reacting one mole of methylamine with one mole of formaldehyde in aqus solution to form 2-nitro-2-aza-1-propanol; and(4) reaction one mole of methylnitramine with each mole of 2-nitro-2-aza-1-propanol to form one mole of 2,4-dinitro-2,4-diazapentane.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: October 9, 1984
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Marguerite S. Chang, Robert R. Orndoff
  • Patent number: 4469888
    Abstract: The invention is a process for reacting methylnitramine with formaldehyde a halogenated solvent and reacting the methylnitramine with formaldehyde in the presence of a strong sulfuric acid catalyst at certain specific temperatures to yield a final product having a yield rate of 70% or greater dimethylmethylenedinitraamine.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: September 4, 1984
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Robert C. Gill, George W. Nauflett
  • Patent number: 4418212
    Abstract: A process for preparing 2,4-dinitro-2,4-diazapentane by(1) nitrating dimethylurea to form dimethyldinitrourea;(2) hydrolyzing the dimethyldinitrourea to form methylnitramine;(3) reacting one mole of methylamine with one mole of formaldehyde in aqus solution to form 2-nitro-2-aza-1-propanol; and(4) reaction one mole of methylnitramine with each mole of 2-nitro-2-aza-1-propanol to form one mole of 2,4-dinitro-2,4-diazapentane.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: November 29, 1983
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Marguerite S. Chang, Robert R. Orndoff
  • Patent number: 4391992
    Abstract: A method for the N-denitration of secondary N,2,6-trinitroanilines with phase transfer catalysts.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: July 5, 1983
    Assignee: American Cyanamid Company
    Inventors: William A. Daniels, Rainer K. Zawadzki
  • Patent number: 4264614
    Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, =CHNO.sub.2 or =NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: April 28, 1981
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Barry J. Price, John Bradshaw