Nitramines (i.e., Compounds Containing Nitro Bonded Directly To Amino Nitrogen) Patents (Class 564/107)
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Patent number: 8853282Abstract: 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: GrantFiled: May 22, 2014Date of Patent: October 7, 2014Assignee: Sumitomo CorporationInventor: Ian Cottrell
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Publication number: 20130121909Abstract: 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: ApplicationFiled: December 18, 2012Publication date: May 16, 2013Inventors: Igor Leonidovich Petrov, Yuriy Alekseevich Skryabin, Olga Alexander Shenderova
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Patent number: 7981393Abstract: 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: GrantFiled: January 21, 2005Date of Patent: July 19, 2011Assignee: Försvarets MaterielverkInventors: Carin Vörde, Henrik Skifs
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Publication number: 20090270509Abstract: 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: ApplicationFiled: July 2, 2009Publication date: October 29, 2009Applicant: Noxilizer, Inc.Inventors: Ernst V. Arnold, Blaine G. Doletski, Robert E. Raulli
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Patent number: 6833478Abstract: 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: GrantFiled: July 13, 2001Date of Patent: December 21, 2004Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Mark A. Petrie, Paul E. Penwell, David C. Bomberger
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Patent number: 6790836Abstract: 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: GrantFiled: August 6, 2002Date of Patent: September 14, 2004Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Shouichi Hiraga, Masashi Kawasaki, Atsushi Akao, Asayuki Kamatani, Masayuki Hagiwara, Toshiaki Mase, Fumio Nakano
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Publication number: 20040063783Abstract: 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: ApplicationFiled: April 3, 2003Publication date: April 1, 2004Inventors: Claude Lardy, Jean-Yves Nioche, Lidia Caputo, Jacques Decerprit, Jean-Yves Ortholand, Didier Festal, Daniel Guerrier
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Publication number: 20040039229Abstract: 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: ApplicationFiled: August 22, 2003Publication date: February 26, 2004Inventors: Kirstin F. Warner, Louis F. Cannizzo, Robert M. Hajik
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Patent number: 6653506Abstract: 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: GrantFiled: September 16, 2002Date of Patent: November 25, 2003Assignee: TPL, Inc.Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael Miks
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Publication number: 20030191346Abstract: The invention relates to a method for producing DNDA that is advantageous in economical, chemical and process engineering terms.Type: ApplicationFiled: June 2, 2003Publication date: October 9, 2003Inventors: Rainer Schirra, Heinz-Gerd Emans, Leonard Lichtblau
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Patent number: 6603018Abstract: A method is provided for the synthesis of nitramines and the recovery of the nitramines from a clathrate.Type: GrantFiled: January 29, 2002Date of Patent: August 5, 2003Assignee: Alliant Techsystems Inc.Inventors: Thomas K. Highsmith, Jami M. Hanks, Stephen P. Velarde, Jeffrey Bottaro
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Patent number: 6255512Abstract: 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: GrantFiled: October 7, 1999Date of Patent: July 3, 2001Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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Patent number: 6147209Abstract: 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: GrantFiled: December 8, 1992Date of Patent: November 14, 2000Assignee: Cordant Technologies Inc.Inventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 6068823Abstract: 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: GrantFiled: January 15, 1999Date of Patent: May 30, 2000Assignee: The University of Houston SystemInventors: Ramiro Sanchez, Graciela Lubertino
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Patent number: 6063960Abstract: 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: GrantFiled: December 15, 1998Date of Patent: May 16, 2000Assignee: TPL, Inc.Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael W. Miks
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Patent number: 5789617Abstract: 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: GrantFiled: September 2, 1992Date of Patent: August 4, 1998Assignee: Aerojet-General CorporationInventors: Thomas G. Archibald, Gerald E. Manser
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Patent number: 5780769Abstract: 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: GrantFiled: August 26, 1996Date of Patent: July 14, 1998Assignee: The United States of America as represented by the Secretary of the NavyInventors: Thomas P. Russell, Indu B. Mishra
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Patent number: 5659080Abstract: 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: GrantFiled: May 28, 1996Date of Patent: August 19, 1997Assignees: Nissan Motor Co., Ltd., Hosoya Fireworks Co., Ltd.Inventors: Shigeru Suzuki, Shigefumi Miyazaki, Hideo Hatano, Kazuo Shiino, Toshio Onda
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Patent number: 5585373Abstract: 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: GrantFiled: November 18, 1994Date of Patent: December 17, 1996Assignee: Taiho Pharmaceutical Co., LtdInventors: Zhang Z. Ping, Zhen J. Sheng, Zhang Q. Rong, Zhang J. Liang, Singh Rajeshwar, Tomohiro Yamashita, Toshiyuki Toko, Hiroshi Matsumoto
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Patent number: 5415852Abstract: 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: GrantFiled: October 30, 1992Date of Patent: May 16, 1995Assignee: SRI InternationalInventors: Robert J. Schmitt, Jeffrey C. Bottaro, Paul E. Penwell, David C. Bomberger
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Patent number: 5382595Abstract: 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: GrantFiled: October 13, 1992Date of Patent: January 17, 1995Assignee: Eisai Co., Ltd.Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
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Patent number: 5360478Abstract: 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: GrantFiled: June 28, 1991Date of Patent: November 1, 1994Assignee: Phasex CorporationInventors: Val J. Krukonis, P. M. Gallagher, M. P. Coffey
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Patent number: 5254324Abstract: 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: GrantFiled: June 18, 1990Date of Patent: October 19, 1993Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David S. Ross
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Patent number: 5243075Abstract: 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: GrantFiled: July 13, 1992Date of Patent: September 7, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Donna M. Cason-Smith
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Patent number: 5186770Abstract: 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: GrantFiled: June 29, 1984Date of Patent: February 16, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventors: Theodore C. Adams, Jr., Horst G. Adolph
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Patent number: 5020731Abstract: 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: GrantFiled: July 6, 1990Date of Patent: June 4, 1991Assignee: Thiokol CorporationInventors: Carlos Somoza, Lee C. Estabrook
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Patent number: 4588748Abstract: 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: GrantFiled: September 25, 1984Date of Patent: May 13, 1986Assignee: SynthelaboInventor: Jean-Pierre Kaplan
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Patent number: 4513148Abstract: 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: GrantFiled: July 1, 1982Date of Patent: April 23, 1985Assignee: The United States of America as represented by the Secretary of the NavyInventor: George W. Nauflett
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Patent number: 4476322Abstract: 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: GrantFiled: July 1, 1982Date of Patent: October 9, 1984Assignee: The United States of America as represented by the Secretary of the NavyInventors: Marguerite S. Chang, Robert R. Orndoff
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Patent number: 4469888Abstract: 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: GrantFiled: June 25, 1982Date of Patent: September 4, 1984Assignee: The United States of America as represented by the Secretary of the NavyInventors: Robert C. Gill, George W. Nauflett
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Patent number: 4418212Abstract: 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: GrantFiled: July 1, 1982Date of Patent: November 29, 1983Assignee: The United States of America as represented by the Secretary of the NavyInventors: Marguerite S. Chang, Robert R. Orndoff
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Patent number: 4391992Abstract: A method for the N-denitration of secondary N,2,6-trinitroanilines with phase transfer catalysts.Type: GrantFiled: October 8, 1980Date of Patent: July 5, 1983Assignee: American Cyanamid CompanyInventors: William A. Daniels, Rainer K. Zawadzki
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Patent number: 4264614Abstract: 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: GrantFiled: November 16, 1979Date of Patent: April 28, 1981Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Barry J. Price, John Bradshaw