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).
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Patent number: 7145003Abstract: 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: GrantFiled: November 24, 2003Date of Patent: December 5, 2006Assignee: The United States of America as represented by the Secrectary of the NavyInventors: Horst G. Adolph, Alfred G. Stern
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Patent number: 6852182Abstract: 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: GrantFiled: May 9, 2001Date of Patent: February 8, 2005Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Michael E. Sitzmann
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Patent number: 6783613Abstract: 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: GrantFiled: April 4, 2002Date of Patent: August 31, 2004Assignee: The United States of America as represented by the Secretary of the NavyInventors: Robert C. Gill, Horst G. Adolph
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Patent number: 6395859Abstract: 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: GrantFiled: March 22, 2000Date of Patent: May 28, 2002Assignee: The United States of America as represented by the Secretary of the NavyInventors: Alfred G. Stern, Horst G. Adolph
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Patent number: 6395112Abstract: 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: GrantFiled: February 4, 2000Date of Patent: May 28, 2002Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael E. Sitzmann, Horst G. Adolph
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Patent number: 6325876Abstract: A compound has the structure of 3,3-bis(difluoroamino)-1,5-dinitratopentane and is useful in energetic materials.Type: GrantFiled: March 2, 2000Date of Patent: December 4, 2001Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Nirupam J. Trivedi
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Patent number: 5949016Abstract: 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: GrantFiled: July 29, 1991Date of Patent: September 7, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventors: Edward E. Baroody, Carl Gotzmer, Horst G. Adolph
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Patent number: 5410079Abstract: 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: GrantFiled: April 2, 1984Date of Patent: April 25, 1995Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael Chaykovsky, Horst G. Adolph
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Patent number: 5266675Abstract: 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: GrantFiled: July 13, 1992Date of Patent: November 30, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Donna M. Cason-Smith
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Patent number: 5256220Abstract: 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: GrantFiled: December 3, 1979Date of Patent: October 26, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventors: Edward E. Baroody, Horst G. Adolph, Mortimer J. Kamlet, Robert C. Gill, Herman S. Haiss
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Patent number: 5250730Abstract: 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: GrantFiled: July 13, 1992Date of Patent: October 5, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventors: Donna M. Cason-Smith, Horst G. Adolph
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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: 4997499Abstract: 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: GrantFiled: May 22, 1984Date of Patent: March 5, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventor: Horst G. Adolph
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Patent number: 4988397Abstract: 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: GrantFiled: April 30, 1986Date of Patent: January 29, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Judah Goldwasser, G. William Lawrence
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Patent number: H604Abstract: 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: GrantFiled: July 27, 1988Date of Patent: March 7, 1989Assignee: The United States of America as represented by the Secretary of the NavyInventors: Robert E. Farncomb, Horst G. Adolph
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Patent number: H644Abstract: 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: GrantFiled: July 27, 1988Date of Patent: June 6, 1989Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael E. Sitzmann, Horst G. Adolph
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Patent number: H730Abstract: 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: GrantFiled: August 2, 1989Date of Patent: February 6, 1990Assignee: The United States of America as represented by the Secretary of the NavyInventors: Lori A. Nock, Horst G. Adolph
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Patent number: H784Abstract: 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: GrantFiled: August 2, 1989Date of Patent: June 5, 1990Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Lori A. Nock
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Patent number: H786Abstract: 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: GrantFiled: August 2, 1989Date of Patent: June 5, 1990Assignee: The United States of America as represented by the Secretary of the NavyInventors: Horst G. Adolph, Lori A. Nock
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Patent number: H973Abstract: 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: GrantFiled: April 2, 1984Date of Patent: October 1, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael Chaykovsky, Horst G. Adolph