Patents by Inventor Michael E. Sitzmann

Michael E. Sitzmann 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).

  • Patent number: 7375221
    Abstract: The present invention includes a method of making of azidoaminotriazole (5-azido-2H-[1,2,4]triazol-3-ylamine), nitrosoguanazine dimer (N3-[(1E)-3-(4,5-diamino-4H-1,2,4-triazol-3-yl)-1,2-dioxidotriaz-1-enyl]-4H-1,2,4-triazole-3,4,5-triamine), novel nitrosoguanazine salts, azidonitraminotriazole/salts and the making of azidonitraminotriazole and salts, and novel metal complexes of an azidonitramine (4,6-diazido-N-nitro-1,3,5-triazin-2-amine) and the making of these metal complexes of this azidonitramine. Azidoaminotriazole, nitrosoguanazine, and azidonitramine compounds, their intermediates, and their salts may generally relate to energetic compounds, while nitrosoguanazine compounds and their metal salts may also have commercial potential in biomedical and pharmaceutical applications.
    Type: Grant
    Filed: October 31, 2005
    Date of Patent: May 20, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: John William Fronabarger, Michael E. Sitzmann, Michael D. Williams
  • Patent number: 7271267
    Abstract: A nitrobenzodifuroxan compound having the chemical structure of: wherein two of the R1, R2, R3 and R4 comprise oxygen or are absent, and only one of R1 or R2 is present, and only one of R3 and R4 is present, and wherein x is hydrolyzed or hydrolyzable. The salt of the hydroxynitrobenzodifuroxan of this compound is useful in explosive compositions.
    Type: Grant
    Filed: October 31, 2005
    Date of Patent: September 18, 2007
    Assignee: The United States of America as represented by Secretary of the Navy
    Inventors: John William Fronabarger, Michael E. Sitzmann
  • Patent number: 7220328
    Abstract: Low-smoke gas generating compositions for producing a low order pressure pulse use a salt or complex of a triazolyl-tetrazinyl-triazine compound. The general chemical structure of the triazolyl-tetrazinyl-triazine is: wherein Z+, when present, is H+ or a cation; R1 is an electron donating group and wherein m=1, 2 or 3; t=0 or 1, and n=0, 1, 2 or 3; and when present, R is a complexing component and x=1, 2 or 3; wherein either Z or R may be absent.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: May 22, 2007
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 7145016
    Abstract: A nitrobenzodifuroxan compound having the chemical structure of: wherein two of the R1, R2, R3 and R4 comprise oxygen or are absent, and only one of R1 or R2 is present, and only one of R3 and R4 is present, and wherein x is hydrolyzed or hydrolyzable. The salt of the hydroxynitrobenzodifuroxan of this compound is useful in explosive compositions.
    Type: Grant
    Filed: August 28, 2003
    Date of Patent: December 5, 2006
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: John William Fronabarger, Michael E. Sitzmann
  • Patent number: 7015222
    Abstract: An agricultural composition comprising the chemical formula, or salt thereof, of: wherein Rx is —NH2, —OH, halogen, akylamino, SR1, carboxyalkyl, carboxy, or a sulfonamide moiety, wherein R1 is a H or a C1 to C6 alkyl moiety, and Ry and Rz, independently, are electron donating groups and an agriculturally acceptable carrier.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: March 21, 2006
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6919453
    Abstract: Colorant compositions, and intermediate chemical compositions of colorant compositions are made from 1,2,4-triazolo[4,3-a][1,3,5]triazine-3,5,7-substituted compounds.
    Type: Grant
    Filed: May 19, 2003
    Date of Patent: July 19, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6852182
    Abstract: A degradable prepolymer for explosive and propellant compositions having increased hydrolyzability comprising at one —O—CH2—O— linkage within the backbone of the prepolymer. The degradable prepolymer is useful as a binder for explosive and propellant compositions.
    Type: Grant
    Filed: May 9, 2001
    Date of Patent: February 8, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Michael E. Sitzmann
  • Patent number: 6846926
    Abstract: The present invention includes a salt compound having the chemical formula: having a tricyclic structure with the third ring having either six or seven atoms.
    Type: Grant
    Filed: May 19, 2003
    Date of Patent: January 25, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6833454
    Abstract: Chemical compounds having a bis(triazolo)triazine structure, including complexes and salts thereof, may be useful in either an intermediate or final product.
    Type: Grant
    Filed: January 15, 2003
    Date of Patent: December 21, 2004
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6673924
    Abstract: The present invention includes a precursor compound pertaining to a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine compound, particularly a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine-3,5,7-Triamine, and novel fused ring structures such as triazolyl-tetrazinyl-aminotriazine compounds, and complexes and salts thereof, and other such chemical structures.
    Type: Grant
    Filed: July 10, 2002
    Date of Patent: January 6, 2004
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6632305
    Abstract: The present invention includes a precursor compound pertaining to a 1,2,4-Triazolo[4,3-a][1,3,5]Triazine compound, particularly a 1,2,4-Triazolo[4,3-a][1,3,5]Triazine-3,5,7-Triamine, and novel fused ring structures such as triazolyl-tetrazinyl-aminotriazine compounds, and complexes and salts thereof, and other such chemical structures.
    Type: Grant
    Filed: June 14, 2002
    Date of Patent: October 14, 2003
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6602366
    Abstract: Pyrotechnic compositions use a salt or complex of a triazolyl-tetrazinyl-aminotriazine compound. The general chemical structure of the triazolyl-tetrazinyl-aminotriazine is: with values of the variables defined within the disclosure.
    Type: Grant
    Filed: June 14, 2002
    Date of Patent: August 5, 2003
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Publication number: 20030069247
    Abstract: The present invention includes a precursor compound pertaining to a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine compound, particularly a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine-3,5,7-Triamine, and novel fused ring structures such as triazolyl-tetrazinyl-aminotriazine compounds, and complexes and salts thereof, and other such chemical structures.
    Type: Application
    Filed: July 10, 2002
    Publication date: April 10, 2003
    Inventor: Michael E Sitzmann
  • Publication number: 20030013878
    Abstract: The present invention includes a precursor compound pertaining to a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine compound, particularly a 1,2,4-Triazolo[4,3-a][1,3,5] Triazine-3,5,7-Triamine, and novel fused ring structures such as triazolyl-tetrazinyl-aminotriazine compounds, and complexes and salts thereof, and other such chemical structures.
    Type: Application
    Filed: June 14, 2002
    Publication date: January 16, 2003
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Publication number: 20030013877
    Abstract: Pyrotechnic compositions use a salt or complex of a triazolyl-tetrazinyl-aminotriazine compound.
    Type: Application
    Filed: June 14, 2002
    Publication date: January 16, 2003
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6476280
    Abstract: The present invention is a method for synthesizing polynitropolyphenyls, and more particularly 2,2′,2″,4,4′,4″,6,6′,6″-nonanitroterphenyl (NONA), that employs only a dihalotrinitrobenzene as a starting material. The general method comprises reacting copper dust with dihalo-trinitrobenzene to form a dihalo-polynitropolyphenyl product. This product is then reduced through a high-yield conversion by heating it within a solvent with a reagent capable of providing a source of iodide and a proton source.
    Type: Grant
    Filed: January 11, 2002
    Date of Patent: November 5, 2002
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Michael E. Sitzmann
  • Patent number: 6423844
    Abstract: The present invention is a process for making a 1,2,4-triazolo[4,3-a][1,3,5]triazine-3,5,7-triamine, acid salt and a process for neutralizing the acid salt to make 1,2,4-triazolo[4,3-a][1,3,5]triazine-3,5,7-triamine. 1,2,4-triazolo[4,3-a][1,3,5]triazine-3,5,7-triamine can be used as a precursor for ingredients in propellants, explosives, pyrotechnics, gas generators, pharmaceuticals, and azo dyes. The general process involves ring closure of 2,4-diamino-6-hydrazino-s-triazine with an acid and a chemical of the general formula RCN where the R comprises a leaving group, then neutralizing said acid.
    Type: Grant
    Filed: June 6, 2001
    Date of Patent: July 23, 2002
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann
  • Patent number: 6395112
    Abstract: A degradable polymer has an ester component adjacent to a poly(oxyethylene) component in the polymer chain. The hydrophilic nature of the poly(oxyethylene) draws water close to the ester in the polymer chain, which increases the rate of hydrolysis of the ester. The degradable polymer is useful as a binder in for explosive and propellant compositions.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: May 28, 2002
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, Horst G. Adolph
  • Patent number: 5714714
    Abstract: A process for preparing ammonium dinitramide by:(1) nitrating either ethyl carbamate or methyl carbamate to form the corronding mononitrate compound, ethyl N-nitrocarbamate or methyl N-nitrocarbamate;(2) reacting the N-nitrocarbamate with ammonia under anhydrous conditions to produce the corresponding ammonium salt, ammonium ethyl N-nitrocarbamate or ammonium methyl N-nitrocarbamate;(3) nitrating the ammonium salt and then treating the reaction mixture with ammonia to produce ammonium dinitramide, ammonium nitrate, and regenerate the original ethyl carbamate or methyl carbamate compound.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: February 3, 1998
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, William M. Koppes, Michael E. Sitzmann, Lori A. Nock, Donna M. Cason-Smith
  • Patent number: 5441720
    Abstract: A pentafluorosulfanylnitramide salt that is ammonium pentafluorosulfanylnamide, sodium pentafluorosulfanylnitramide, potassium pentafluorosulfanylnitramide, lithium pentafluorosulfanylnitramide, or cesium pentafluorosulfanylnitramide. These salts are useful as energetic oxidizers in explosives and propellants.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: August 15, 1995
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Michael E. Sitzmann