Patents by Inventor Alfred G. Stern

Alfred G. Stern 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: 10131638
    Abstract: A synthesis for an azo intermediate, 5,5?-azobis(4-chloropyrimidine) is disclosed. 5,5?-azobis(4-chloropyrimidine) is a relatively stable azo compound in that decomposition does not occur until about 194° C. 5,5?-azobis(4-chloropyrimidine) is a product of oxidative dimerization of 5-amino-4-pyrimidine, which a water soluble compound. The azo intermediate is formed in an aqueous solution, but the azo intermediate is substantially insoluble in water; and as it forms it separates producing a reaction mixture that is a slurry. The azo intermediate is isolated by filtration. The azo intermediate is marginally soluble in acetone. The yield is at least 18%, and the oxidizing agent (bleach) is inexpensive, reaction conditions do not require extreme heat or cold, which taken together make the azo intermediate suitable for scaling up.
    Type: Grant
    Filed: March 12, 2018
    Date of Patent: November 20, 2018
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Patrick A. Caruana, Alfred G. Stern, Alex J. Zaita, Thao Vo
  • Patent number: 9296706
    Abstract: The present invention relates to methods for synthesizing energetic compounds and intermediates thereof. Specifically, the present invention relates to methods for synthesizing adamantanes and intermediates that are useful in such synthesis. Synthesized intermediates are useful in the synthesis of bicyclic and tricyclic substituted adamantanes. Examples of various intermediates are: acyclic 2-nitromalonaldehyde intermediates, 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-dienes and 2,6-dinitro-4,8,9,10-tetra-aza-4,8,9,10-tetra-substituted adamantanes. Intermediates synthesized according to the methods of the present invention are useful toward the synthesis of tetraaza-adamantanes, which can serve as precursors to potentially superior new high-energy-density compounds (HEDCs).
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: March 29, 2016
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Craig J. Diamond
  • Patent number: 8895736
    Abstract: The present invention relates to methods for synthesizing energetic compounds and intermediates thereof. Specifically, the present invention relates to methods for synthesizing adamantanes and intermediates that are useful in such synthesis. Synthesized intermediates are useful in the synthesis of bicyclic and tricyclic substituted adamantanes. Examples of various intermediates are: acyclic 2-nitromalonaldehyde intermediates, 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-dienes and 2,6-dinitro-4,8,9,10-tetra-aza-4,8,9,10-tetra-substituted adamantanes. Intermediates synthesized according to the methods of the present invention are useful toward the synthesis of tetraaza-adamantanes, which can serve as precursors to potentially superior new high-energy-density compounds (HEDCs).
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: November 25, 2014
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Craig J. Diamond
  • Patent number: 8853220
    Abstract: The present invention relates to methods for synthesizing energetic compounds and intermediates thereof. Specifically, the present invention relates to methods for synthesizing adamantanes and intermediates that are useful in such synthesis. Synthesized intermediates are useful in the synthesis of bicyclic and tricyclic substituted adamantanes. Examples of various intermediates are: acyclic 2-nitromalonaldehyde intermediates, 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-dienes and 2,6-dinitro-4,8,9,10-tetra-aza-4,8,9,10-tetra-substituted adamantanes. Intermediates synthesized according to the methods of the present invention are useful toward the synthesis of tetraaza-adamantanes, which can serve as precursors to potentially superior new high-energy-density compounds (HEDCs). The tricyclic intermediate compound has a structure of Formula III: where R is one of a benzyl, 4-methoxybenzyl, acetyl, nitro, formyl, allyl, and a carboethoxyl group.
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: October 7, 2014
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Craig J. Diamond
  • Patent number: 8273877
    Abstract: Substituted tetraazapentalenes have two benzenoid rings and eight substitutable positions. Substitutions are made of hydrogen or C—H groups in favor of amino groups, nitro groups or nitrogen atoms. The tetraazapentalenes are synthesized through an intermediate azo, which is made from a 1:1:1 molar ratio of a nitroaniline, sodium nitrite and an amine.
    Type: Grant
    Filed: November 18, 2011
    Date of Patent: September 25, 2012
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Patrick A. Caruana
  • Patent number: 7192649
    Abstract: A protective passivation layer is formed on the surface of an aluminum mass, such as bare aluminum particles, creating a protected aluminum mass. Formation of the protective layer onto the aluminum mass may occur from an in-situ process.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: March 20, 2007
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: R. Jason Jouet, Alfred G. Stern, David M. Rosenberg
  • Patent number: 7145003
    Abstract: A process for synthesizing 1,5-Dinosyl-3,3,7,7-tetrakis(difluoramino) octahydro-1,5-diazocine (DNTDFD) by reacting tetrahydro-1,5-bis(4-nitrobenzenesulfonyl)-1,5-diazocine-3,7-(2H, 6H) dione with HNF2/oleum initially approximately between ?5 and 0 degrees C., and allowing the temperature to rise to between 10 degrees C. and ambient temperature during said reaction to initiate difluoramination producing product DNTDFD. A 2:1 mixture of FREON® 11 refrigerant and pentane or cyclopentane, or pentane alone is used as a diluent and absorbent for the reagent difluoramine. The present invention reduces the time required to produce DNTDFD from about two weeks to one to three days and reduces the need to use relatively large quantities of FREON® 11, a compound which is damaging to the environment.
    Type: Grant
    Filed: November 24, 2003
    Date of Patent: December 5, 2006
    Assignee: The United States of America as represented by the Secrectary of the Navy
    Inventors: Horst G. Adolph, Alfred G. Stern
  • Patent number: 6706889
    Abstract: Dinitropyrazolopyrazole-amine salts are used as burn modifier ingredients in gun propellant compositions.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: March 16, 2004
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Jesse S. Moran, R. Jason Jouet, Michael E. Sitzman, Philip F. Pagoria, Gregory S. Lee
  • Patent number: 6395859
    Abstract: The present invention provides energetic thermoplastic elastomers which may be used as binders in propellant, explosive and pyrotechnic applications. The elastomers of the present invention are all hydrolyzable, allowing recycling of the elastomer's constituents and/or facilitating other constituents of the propellant, explosive or pyrotechnic. The elastomers of the present invention contain a first polymer, a second polymer having a repeating unit different from that of the first polymer, and a bridging group. Methods of preparing elastomers of the present invention include reaction of the first and second polymers with a dioic acid, or with an organic diisocyanate and a diol containing a formal linkage.
    Type: Grant
    Filed: March 22, 2000
    Date of Patent: May 28, 2002
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, 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: 5380777
    Abstract: This invention is first, a difunctional poly(glycidyl nitrate) oligomer (PGN oligomer), second, nitrated PGN oligomer and third, the use of the nitrated PGN oligomer as a plasticizer, particularly as a plasticizer for binders used in and/or as energetic formulations. Examples of energetic formulations are propellants, pyrotechnics and explosives and other such compositions. More particularly, this invention is a difunctional poly(glycidyl nitrate) oligomer of the formula ##STR1## where n is 0 to 3, having a M.sub.n of from about 304 to about 994. Another embodiment is the nitrated difunctional poly(glycidyl nitrate) oligomer of the formula ##STR2## where n is 0 to 3, having a M.sub.n of from about 394 to about 1084.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: January 10, 1995
    Assignee: Thiokol Corporation
    Inventors: Rodney Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5264596
    Abstract: Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: November 23, 1993
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5232526
    Abstract: This invention is for new compounds, namely, diethanolammoniummethylcubane nitrates, a composition of diethanolammonium methylcubyl nitrates - hydroxylammonium nitrate (HAN) solutions and their method of use as aqueous liquid gun propellant ingredients.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: August 3, 1993
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern
  • Patent number: 5162494
    Abstract: Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation of commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared direcly via nitration of (S) or (R) glycidol, respectively.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: November 10, 1992
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5120827
    Abstract: An improved process for producing poly(glycidyl nitrate) having a functionality substantially equivalent to the hydroxy functionality of the initiator employed in which a catalyst-initiator complex is reacted with glycidyl nitrate and wherein the ratio of mols catalyst/mols hydroxyls in the initiator is <1:1, the gylcidyl nitrate monomer is added to the catalyst-initiator complex reaction mixture at a rate in which the monomer is used up (reacted) essentially as fast as it is added, and the reaction temperature is maintained at a temperature within the range of from about 10.degree. to 25.degree. C.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: June 9, 1992
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Robert S. Day, Alfred G. Stern
  • Patent number: 5017356
    Abstract: Cyanogen is prepared from glyoxime by reaction with acetic anhydride to form N,N'-diacetoxyglyoxime which is then pyrolyzed to cyanogen.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: May 21, 1991
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Dennis Park, Alfred G. Stern