Patents by Inventor Jeffrey C. Bottaro
Jeffrey C. Bottaro has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9598380Abstract: Described are methods for preparing salts of 5-nitrotetrazolate by reacting 5-aminotetrazole, an acid, and sodium nitrite in water in a batch reaction at an elevated temperature. As examples, the acid is nitric acid, sulfuric acid, perchloric acid, or hydrochloric acid, and the elevated temperature is at or above 65° C.Type: GrantFiled: June 5, 2015Date of Patent: March 21, 2017Assignees: SRI International, Pacific Scientific Energetic Materials Company, LLCInventors: Jeffrey C. Bottaro, Mark A. Petrie, Jon G. Bragg, John W. Fronabarger, Michael D. Williams
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Publication number: 20150361057Abstract: Described are methods for preparing salts of 5-nitrotetrazolate by reacting 5-aminotetrazole, an acid, and sodium nitrite in water in a batch reaction at an elevated temperature. As examples, the acid is nitric acid, sulfuric acid, perchloric acid, or hydrochloric acid, and the elevated temperature is at or above 65° C.Type: ApplicationFiled: June 5, 2015Publication date: December 17, 2015Inventors: Jeffrey C. Bottaro, Mark A. Petrie, Jon G. Bragg, John W. Fronabarger, Michael D. Williams
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Publication number: 20090139618Abstract: Novel compounds are provided in the form of a salt having the structure of formula (I) or formula (II) wherein: R1 is selected from the group consisting of H, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C5-C20 aryl, C6-C24 alkaryl, and C6-C24 aralkyl; R2 is H, C1-C24 alkyl or nitro; X is O or NR3 in which R3 is H, C1-C24 alkyl or nitro; Zm+ is a monovalent cation, a divalent cation, or a trivalent cation; M+ is an alkali metal cation; and m and n are 1, 2 or 3, with the proviso that the compound contains at least one nitro group. Exemplary such compounds are the ammonium salt of the N-hydroxyl-N?-nitrourea (NHNU) monoanion and the disodium salt of the NHNU dianion. Also provided, as novel compositions of matter, are N-hydroxyl-N?-nitrourea and N-hydroxyl-N-nitroguanidine in electronically neutral form. The compounds are useful in a variety of contexts, but are primarily useful as high energy oxidizing agents in explosive compositions, propellant formulations, gas-generating compositions, and the like.Type: ApplicationFiled: August 6, 2002Publication date: June 4, 2009Inventors: Mark A. Petrie, Jeffrey C. Bottaro, Paul E. Penwell, Allen L. Dodge
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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: 6617064Abstract: The present invention features methods for preparing stabilized &agr;-AlH3 and &agr;′-AlH3, compositions containing these alane polymorphs, e.g., energetic compositions such as rocket propellants, and methods for using the novel polymorphs as chemical reducing agents, polymerization catalysts, and as a hydrogen source in fuel cells and batteries. The method produces stabilized alane by treating &agr;-AlH3 with an acidic solution that optionally contains a stabilizing agent such as an electron donor, an electron acceptor, or a compound which coordinates the Al3+ ion.Type: GrantFiled: March 29, 2001Date of Patent: September 9, 2003Assignee: SRI InternationalInventors: Mark A. Petrie, Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David C. Bomberger
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Patent number: 6613926Abstract: Novel compounds are provided in the form of nucleoside pyrophosphate and triphosphate analogs. In these analogs, the pyrophosphate or triphosphate group is replaced with a moiety that is isosterically and electronically identical thereto, but is hydrolytically and enzymatically more stable. The compounds are useful as therapeutic agents, e.g., as antiviral agents, anticancer agents, metabolic moderators and the like. The invention also provides pharmaceutical compositions containing a compound of the invention as an active agent, and in addition provides methods of treating disease, including viral infections, cancer, bacterial infections, inflammatory and/or autoimmune diseases, and the like, by administering a compound of the invention to a patient in need of such treatment.Type: GrantFiled: November 1, 2000Date of Patent: September 2, 2003Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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Patent number: 6552051Abstract: 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: June 7, 2001Date of Patent: April 22, 2003Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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Publication number: 20030026850Abstract: 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: ApplicationFiled: July 13, 2001Publication date: February 6, 2003Inventors: Jeffrey C. Bottaro, Mark A. Petrie, Paul E. Penwell, David C. Bomberger
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Publication number: 20010044544Abstract: 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: ApplicationFiled: June 7, 2001Publication date: November 22, 2001Inventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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Publication number: 20010038821Abstract: The present invention features methods for preparing stabilized &agr;-AlH3 and &agr;′-AlH3, compositions containing these alane polymorphs, e.g., energetic compositions such as rocket propellants, and methods for using the novel polymorphs as chemical reducing agents, polymerization catalysts, and as a hydrogen source in fuel cells and batteries. The method produces stabilized alane by treating &agr;-AlH3 with an acidic solution that optionally contains a stabilizing agent such as an electron donor, an electron acceptor, or a compound which coordinates the Al3+ ion.Type: ApplicationFiled: March 29, 2001Publication date: November 8, 2001Inventors: Mark A. Petrie, Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David C. Bomberger
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Patent number: 6303774Abstract: Novel compounds are provided in the form of nucleoside pyrophosphate and triphosphate analogs. In these analogs, the pyrophosphate or triphosphate group is replaced with a moiety that is isosterically and electronically identical thereto, but is hydrolytically and enzymatically more stable. The compounds are useful as therapeutic agents, e.g., as antiviral agents, anticancer agents, metabolic moderators and the like. The invention also provides pharmaceutical compositions containing a compound of the invention as an active agent, and in addition provides methods of treating disease, including viral infections, cancer, bacterial infections, inflammatory and/or autoimmune diseases, and the like, by administering a compound of the invention to a patient in need of such treatment.Type: GrantFiled: August 20, 1999Date of Patent: October 16, 2001Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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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: 6228338Abstract: The present invention features methods for preparing stabilized &agr;-AlH3 and &agr;′-AlH3, compositions containing these alane polymorphs, e.g., energetic compositions such as rocket propellants, and methods for using the novel polymorphs as chemical reducing agents, polymerization catalysts, and as a hydrogen source in fuel cells and batteries. The method produces stabilized alane by treating &agr;-AlH3 with an acidic solution that optionally contains a stabilizing agent such as an electron donor, an electron acceptor, or a compound which coordinates the Al3+ ion.Type: GrantFiled: June 16, 1999Date of Patent: May 8, 2001Assignee: SRI InternationalInventors: Mark A. Petrie, Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David C. Bomberger
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Patent number: 6156136Abstract: Novel energetic compounds are provided comprising N,N'-azobis-nitroazoles or analogs thereof. The compounds are useful as igniter materials in a variety of energetic compositions, particularly gas-generating compositions for inflating automobile or aircraft occupant restraint devices. The compounds are also useful in solid rocket propellant compositions, and as primary explosives to be used as detonators, blasting caps, firearms, and the like. Methods for synthesizing the compounds and manufacturing energetic compositions therewith are provided as well.Type: GrantFiled: December 22, 1998Date of Patent: December 5, 2000Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell
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Patent number: 6096774Abstract: Novel compounds are provided having the structural formula R[--N(NO.sub.2)--L--R.sup.1 ].sub.n wherein R, L, R.sup.1 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, 1998Date of Patent: August 1, 2000Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Mark A. Petrie, Paul E. Penwell
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Patent number: 5889161Abstract: Novel energetic compounds are provided comprising N,N'-azobis-nitroazoles or analogs thereof. The compounds are useful as igniter materials in a variety of energetic compositions, particularly gas-generating compositions for inflating automobile or aircraft occupant restraint devices. The compounds are also useful in solid rocket propellant compositions, and as primary explosives to be used as detonators, blasting caps, firearms, and the like. Methods for synthesizing the compounds and manufacturing energetic compositions herewith are provided as well.Type: GrantFiled: May 13, 1998Date of Patent: March 30, 1999Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell
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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: 5316749Abstract: A method for forming an ionically bonded ammonium dinitramide salt having the formula NH.sub.4.sup.30 N(NO.sub.2).sub.2 - useful as a stable oxidizer for solid fuel rocket propellant or explosive formulations is disclosed. The ammonium dinitramide salt is formed by the reaction of ammonia and a nitronium-containing compound, such as a nitronium salt or a covalently bonded compound containing a NO.sub.2 - group, at a temperature of from about - 20.degree. C. to about 120.degree. C. The nitronium-containing compound may be either a covalently bonded compound containing a NO.sub.2 - group or a nitronium salt having the formula (NO.sub.2.sup.+).sub.n X.sup.-n, where X is the anion of the nitronium salt and n= 1-2.Type: GrantFiled: July 30, 1991Date of Patent: May 31, 1994Assignee: SRI InternationalInventors: Robert J. Schmitt, Jeffrey C. Bottaro, Paul E. Penwell, David C. Bomberger
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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: 5198204Abstract: A method is disclosed for forming a N,N-dinitramide salt having the formula MN(NO.sub.2).sub.2 where M is a cation selected form the class consisting of a metal ion and a nitrogen-containing ion, which comprises contacting a carbamate with a nitrating agent to form an acidic dinitramide intermediate reaction product, and neutralizing the acidic dinitramide with a compound selected from the class consisting of ammonia (NH.sub.3), hydrazine (N.sub.2 H.sub.4), a primary amine having the formula RNH.sub.2, a secondary amine having the formula RR'NH, and a salt having the formula AX; where R and R' are the same or different 1-6 carbon alkyls, A is a metal ion or a nitrogen-containing ion, and X is an anion selected from the class consisting of fluoride, chloride, hydroxyl, carbonate, alkoxide, and carboxyl anion, to form the corresponding dinitramide salt.Type: GrantFiled: June 18, 1990Date of Patent: March 30, 1993Assignee: SRI InternationalInventors: Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David S. Ross