Patents by Inventor Horst G. Adolph

Horst G. Adolph 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: 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: 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: 6783613
    Abstract: The present invention is a modified HFPB polymer for use in propellants and explosives that is chemically degradable and also is compatible with commonly used energetic plasticizers. The HFPB polymer of the present invention contains ester linkages formed in the backbone of the polymer from a dicarboxylic acid containing either oxymeythylene or oxyethylene moeities. The ester and ether linkages change the polarity of the polybutadiene to make it compatible with polar energetic plasticizers. The ester linkages along with either oxymethylene or oxyethylene moeities make the polymer degradable to basic solutions while still maintaining the structural integrity necessary for a polybutadiene type binder.
    Type: Grant
    Filed: April 4, 2002
    Date of Patent: August 31, 2004
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Robert C. Gill, Horst G. Adolph
  • 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: 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: 6325876
    Abstract: A compound has the structure of 3,3-bis(difluoroamino)-1,5-dinitratopentane and is useful in energetic materials.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: December 4, 2001
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Nirupam J. Trivedi
  • Patent number: 5949016
    Abstract: A melt cast explosive containing bis(2,2-dinitropropyl)fumarate or 2,2-diropropyl-4,4-dinitropentanoate and a metal fuel such as aluminum, magnesium, boron, hafnium, zirconium or alloys or mixtures thereof. An inert thermoplastic elastomer diluent may be added to improve the strength of the explosive.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: September 7, 1999
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Edward E. Baroody, Carl Gotzmer, Horst G. Adolph
  • Patent number: 5410079
    Abstract: 5-ureido-1,3-diamino-2,4-6-trinitrobenzene, ##STR1## which is prepared by reacting 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene with urea.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: April 25, 1995
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael Chaykovsky, Horst G. Adolph
  • Patent number: 5266675
    Abstract: Energetic dihydroxy-terminated copolyformals which are formed from formalyde and dinitraminediol and fluorodiol comonomers wherein the dinitraminediol isHOCH.sub.2 N(NO.sub.2)CH.sub.2 N(NO.sub.2)CH.sub.2 N(NO.sub.2)CH.sub.2 OH,HOCH.sub.2 N(NO.sub.2)CH.sub.2 N(NO.sub.2)CH.sub.2 N(NO.sub.2)CH.sub.2 N(NO.sub.2)CH.sub.2 OH,or mixtures thereof, and wherein the fluorodiol isHOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH,HOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH,HOCH.sub.2 CF(CF.sub.3)OCF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH,HOCH.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 OH,HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.2 CH.sub.2 CH.sub.2 OH,HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.4 CH.sub.2 CH.sub.2 OH,HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 CH.sub.2 OH,HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.8 CH.sub.2 CH.sub.2 OH,HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.10 CH.sub.2 CH.sub.2 OH,or mixtures thereof andwherein the terminal functional groups are fluorodiol monomer hydroxy groups.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: November 30, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Donna M. Cason-Smith
  • Patent number: 5256220
    Abstract: A novel formulation of liquid propellants comprising a mixture of high eny ingredients consisting of bis(2-fluoro-2,2-dinitroethyl)amine, bis(2-fluoro-2,2-dinitroethyl)formal and bis(2,2,2-trinitroethyl)formal together with conventional liquid fuels and propellants to create a synergistic formulation having new and unexpected physical and chemical properties.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: October 26, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Edward E. Baroody, Horst G. Adolph, Mortimer J. Kamlet, Robert C. Gill, Herman S. Haiss
  • Patent number: 5250730
    Abstract: A process by which 1,7-dihydroxy-2,4,6-trinitro-2,4,6-triazaheptane or 1,9-dihydroxy-2,4,6,8-tetranitro-2,4,6,8-tetraazanonane is produced by hydrolyzing 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 with concentrated aqeuous hydrochloric acid comprising from 28 to 32 weight percent of hydrogen chloride with the remainder being water.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: October 5, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Donna M. Cason-Smith, Horst G. Adolph
  • 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: 4997499
    Abstract: A new compound 2,2-dinitrobutyl 2,2-dinitropropyl formal (DNBPF),CH.sub.3 C(NO.sub.2).sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.sub.2 CH.sub.3,and a energetic plasticizer which is a 1:1 eutectic mixture of DNBPF and bis(2,2-dinitropropyl) formal.
    Type: Grant
    Filed: May 22, 1984
    Date of Patent: March 5, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Horst G. Adolph
  • Patent number: 4988397
    Abstract: An energetic uncured binder composite mixture comprising(1) a hydroxy-terminated polyfluoroformal prepolymer of the general formulaHOCH.sub.2 (CF.sub.2).sub.n CH.sub.2 [OCH.sub.2 OCH.sub.2 (CF.sub.2).sub.n H.sub.2 ].sub.m OHwherein n is 3 or 4 and m is selected to provide a number average molecular weight of from about 1,000 to about 10,000 for the prepolymer; and(2) an energetic plasticizer which isbis(2,2-dinitropropyl)formal,bis(2,2-trinitroethyl)formal,bis(2-fluoro-2,2-dinitroethyl)formal,bis(2,2-difluoro-2-nitroethyl)formal,2,2-dinitropropyl 2-fluoro-2,2-dinitroethyl formal, or mixtures thereof;wherein the weight ratio of energetic plasticizer to prepolymer is from about 2:1 to about 5:1. This binder composite mixture is useful for preparing energetic plastic bonded explosives having high chemical and thermal stabilities.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: January 29, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Judah Goldwasser, G. William Lawrence
  • Patent number: H604
    Abstract: A process for preparing 1,4,4,5,5,6,6-heptafluoro-2-trifluoro-3-oxaheptan,7-diol polyformal by the following steps in order:(1) reacting 2,4,4,5,5,6,6-heptafluoro-2-trifluoromethyl-3-oxaheptane-1,7-diol with formaldehyde in 80-90% (w/w) sulfuric acid in the presence of methylene chloride to produce 2,4,4,5,5,6,6-heptafluoro-2-trifluoromethyl-3-oxaheptane-1,7-diol polyformal;(2) treating the reaction mixture with aqueous H.sub.2 O.sub.2 to destroy free formaldehyde;(3) removing methylene chloride from the reaction mixture;(4) extracting the product 2,4,4,5,5,6,6-heptafluoro-2-trifluoromethyl-3-oxaheptane-1,7-diol polyformal from the reaction mixture with ether;(5) agitating the ether extract with an aqueous solution of (a) H.sub.2 O.sub.2, (b) KOH or NaOH, and (c) NaCl or KCl to convert hemiformal end groups into hydroxy end groups; and(6) isolating the product 2,4,4,5,5,6,6-heptafluoro-2-trifluoromethyl-3-oxaheptane-1,7-diol polyformal.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: March 7, 1989
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Robert E. Farncomb, Horst G. Adolph
  • Patent number: H644
    Abstract: A process for preparing 2,2,2-trinitroethyl 2-nitroxyethyl ether by the fowing reaction sequence: ##STR1## 2,2,2-Trinitroethyl 2-nitroxyethyl ether is useful as an energetic plasticizer in propellants and explosives.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: June 6, 1989
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, Horst G. Adolph
  • Patent number: H730
    Abstract: Energetic dihydroxy-terminated copolyformals which are formed from formalyde and fluorodiol and nitrodiol comonomers where the fluorodiol is HOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH, HOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH, HOCH.sub.2 CF(CF.sub.3)OCF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH, HOCH.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.2 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.4 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.8 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.10 CH.sub.2 CH.sub.2 OH, or mixtures thereof, and the nitro diol is HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 OH, HOCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: February 6, 1990
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Lori A. Nock, Horst G. Adolph
  • Patent number: H784
    Abstract: Dihydroxy-terminated copolyformals formed fromA. formaldehyde andB. a diol comonomer mixture of(1) 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) and(2) a fluorodiol which is HOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 HOCH.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH, HOCH.sub.2 CF(CF.sub.3)OCF.sub.2 CF.sub.2 CF.sub.2 CH.sub.2 OH, HOCH.sub.2 CF.sub.2 OCF.sub.2 CF.sub.2 OCF.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.2 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.4 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.8 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 (CF.sub.2).sub.10 CH.sub.2 CH.sub.2 OH, or mixtures thereof. A fraction of the fluorodiol may be replaced with an equal number of moles of a suitable nitrodiol.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: June 5, 1990
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Lori A. Nock
  • Patent number: H786
    Abstract: Dihydroxy-terminated copolyformals formed fromA. formaldehyde andB. a diol comonomer mixture of(1) 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) and(2) a nitrodiol which is HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 , HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 OH, HOCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH, HOCH.sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 N(NO.sub.2)CH.sub.2 CH.sub.2 OH, or mixtures thereof.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: June 5, 1990
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Lori A. Nock
  • Patent number: H973
    Abstract: 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR1## which is prepared by reacting 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene with cyanotrimethylsilane to form 5-cyano-1,3-diamino-2,4,6-trinitrobenzene which is then hydrolyzed with a strong acid to form the DATBA.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: October 1, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael Chaykovsky, Horst G. Adolph