Plural Oxygens Bonded Directly To The Same Carbon (e.g., Acetals, Ketals, Orthoesters, Orthocarbonates, Etc.) Patents (Class 568/590)
  • Patent number: 8704004
    Abstract: Disclosed is an energetic reactive plasticizer for a plastic bonded explosive (PBX), and specifically an energetic reactive plasticizer for PBX which has high performance and insensitiveness without a plasticizer leak by being bonded with a polymer binder for a plastic bonded explosive.
    Type: Grant
    Filed: February 7, 2013
    Date of Patent: April 22, 2014
    Assignee: Agency for Defense Development
    Inventors: Young Hwan Kwon, Jin Seuk Kim, Bum Jae Lee, In Joo Bae
  • Publication number: 20140031593
    Abstract: Disclosed is an energetic reactive plasticizer for a plastic bonded explosive (PBX), and specifically an energetic reactive plasticizer for PBX which has high performance and insensitiveness without a plasticizer leak by being bonded with a polymer binder for a plastic bonded explosive.
    Type: Application
    Filed: February 7, 2013
    Publication date: January 30, 2014
    Applicant: AGENCY FOR DEFENSE DEVELOPMENT
    Inventor: Agency for Defense Development
  • Patent number: 8350092
    Abstract: The invention relates to a process for preparing ?-aminoacetals substantially in racemic form, comprising a step of oxidizing optically enriched ?-aminoacetals to the corresponding oximes, in the presence of a catalyst, and a step of reducing the oximes thus obtained.
    Type: Grant
    Filed: May 21, 2008
    Date of Patent: January 8, 2013
    Assignee: Clariant Specialty Fine Chemicals (France)
    Inventors: Muriel Albalat, Geraldine Primazot, Didier Wilhelm, Jean-Claude Vallejos
  • Publication number: 20090216049
    Abstract: Bis(dinitroalkyl)acetals and formals having the formula (1) particularly bis(2,2-dinitropropyl)acetal and bis(2,2-dinitropropyl)formal are produced by oxidative nitration of compounds having the formula (2): preferably via a sodium or other alkali metal, or alkaline earth metal, salt of compounds of Formula (2). Certain of the compounds of formula (1) are novel. All of the intermediates of formula (2) are novel and form another aspect of this invention, as does a process for their production by reacting an aldehyde with a nitroalkanol. The process can readily produce a mixture of the dinitro compounds known as BDNPA and BDNPF (also known as A/F) using the non-explosive intermediates, BNPA and BNPF, both of which are novel.
    Type: Application
    Filed: April 20, 2006
    Publication date: August 27, 2009
    Applicant: Dimension Technology Chemical Systems, Inc.
    Inventors: Renato R. Rindone, Michael Kenneth Free, Robert Allan Morrison, JR.
  • Patent number: 7321052
    Abstract: A process for the preparation of a fuel oil (diesel fuel or heating oil) composition which is a mixture of an alkanol tranesterified fatty acid ester triglyceride and an acetal of glycerol is described. The process preferably provides a prestep of the formation of at least some of the alkanol transesterified triglyceride containing the glycerol for use in the formation of the acetal of glycerol. The composition can also be formed from a reaction of 1,1-dimethoxy- or 1,1-diethoxyethane and glycerol to form the acetal in the alkanol transesterified triglyceride.
    Type: Grant
    Filed: February 28, 2006
    Date of Patent: January 22, 2008
    Assignee: Board of Trustees of Michigan State University
    Inventors: Dennis J. Miller, Lars Peereboom, Aspi K. Kolah, Navinchandra S. Asthana, Carl T. Lira
  • Patent number: 7208637
    Abstract: Disclosed are novel compounds that can be used as an energetic binder used for improving the performance and the properties of a high explosive, and a preparation method thereof.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: April 24, 2007
    Assignee: Agency for Defence a Korean Non-Profit Org.
    Inventors: Jin Seuk Kim, Jin Rai Cho, Keun Deuk Lee, Jae Kyoung Kim
  • Patent number: 6770782
    Abstract: The present invention provides a new process for the isolation of hydroxy citric acid in the form of a potassium salt from Garcinia fruit. The present invention also provides compositions containing the potassium hydroxy citrate for use as appetite suppressants.
    Type: Grant
    Filed: May 22, 1998
    Date of Patent: August 3, 2004
    Assignee: Sabinsa Corporation
    Inventors: Muhammed Majeed, Vladimir Badmaev, Ramaswamy Rajendran
  • Patent number: 6160172
    Abstract: The present invention is directed to a new soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of general formula I:where X is IA group metal: Li or Na or K or Rb or Cs or Frwhere Y is IIA group metal: Be or Mg or Ca or Sr or Ba or Rawhere the concentration of X in the salt varies from 1.5-51.0%,the concentration of Y in the salts varies from 2.0-50.9%,the concentration of HCA in the salt varies from 31.0-93.0% depending on the nature of X and Y.This invention more particularly relates to new soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of general formula II.
    Type: Grant
    Filed: April 14, 1998
    Date of Patent: December 12, 2000
    Assignee: Vittal Mallya Scientific Research Foundation
    Inventors: Karanam Balasubramanyam, Bhaskaran Chandrasekhar, Candadai Seshadri Ramadoss, Pillarisetti Venkata Subba Rao
  • Patent number: 5783732
    Abstract: 2:2 mixed orthocarbonates of the formula ##STR1## wherein R.noteq.R' and wherein R and R' are --C(NO.sub.2).sub.3, --CF(NOb.2).sub.2, --CF.sub.2 (NO.sub.2), --C(NO.sub.2).sub.2 CH.sub.3, --CH(NO.sub.2)CH.sub.3, --CH(NO.sub.2)CH.sub.3, --CH.sub.2 (NO.sub.2), --CF.sub.3, or --CF.sub.2 CF.sub.3, and methods of preparation.Additionally, orthoformates of the formula ##STR2## wherein R is --C(NO.sub.2).sub.2 CH.sub.3, --CF.sub.2 (NO.sub.2), --CH(NO.sub.2)CH.sub.3, and --CH.sub.2 (NO.sub.2), and methods of preparation.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: July 21, 1998
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: William H. Gilligan
  • Patent number: 5648556
    Abstract: A nonsolvent process of synthesizing bis(2,2-dinitropropyl)acetal (BDNPA) is disclosed. In the process, 2,2-dinitropropanol (DNPOH) is reacted at low temperature with an acetaldehyde source in the presence of an acid catalyst, such as a Lewis acid catalyst or protic acid catalyst. To inhibit by product formation, the reaction temperature is maintained from about -30.degree. C. to 30.degree. C. Upon completion of the reaction, the reaction solution is quenched with water and washed with an aqueous hydroxide solution. The hydroxide concentration should be sufficient to neutralize any acid formed during the quenching step and to solubilize unreacted 2,2-dinitropropanol as well as other aqueous soluble byproducts in the reaction solution. The BDNPA product is extracted with methyl tert-butyl ether (MTBE) or equivalent solvent. The organic solvent is evaporated to yield usable BDNPA product. The resulting yield is at least 50% based on the starting quantity of 2,2-dinitropropanol.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: July 15, 1997
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle
  • Patent number: 5449835
    Abstract: A nonsolvent process of synthesizing bis(2,2-dinitropropyl)formal (BDNPF) is disclosed. In the process, 2,2-dinitropropanol (DNPOH) is reacted at low temperature with a formaldehyde source in the presence of a protic acid catalyst, such as H.sub.2 SO.sub.4, HCl, H.sub.3 PO.sub.4, or HBr. To inhibit byproduct formation, the reaction temperature is maintained from about -30.degree. C. to 30.degree. C. Upon completion of the reaction, the reaction solution is quenched with water and washed with an aqueous hydroxide ion solution. The hydroxide ion concentration should be sufficient to neutralize the protic acid catalyst during the quenching step and to solubilize unreacted 2,2-dinitropropanol as well as other aqueous soluble byproducts in the reaction solution. The BDNPF product is extracted with a low boiling temperature polar organic solvent, such as methyl tert-butyl ether (MTBE) or equivalent solvent. The organic solvent is evaporated to yield usable BDNPF product.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: September 12, 1995
    Assignee: Thiokol Corporation
    Inventors: R. Scott Hamilton, Robert B. Wardle
  • Patent number: 5426247
    Abstract: A process for the preparation of vitamin A which preferably comprises bringing cyclogeranyl sulphone into contact with a C.sub.10 aldehyde acetal, halogenating the derivative obtained and then removing the halogen group and the sulphone, removing the acetal group and isomerizing the retinal obtained to the desired configuration. Also disclosed are compounds useful as intermediates in the synthesis of vitamin A and processes for preparation of these intermediate compounds.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: June 20, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Pierre Chabardes
  • Patent number: 5290912
    Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: March 1, 1994
    Assignee: Asahi Glass Company Ltd.
    Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
  • Patent number: 5233078
    Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: August 3, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Klaus Halbritter
  • Patent number: 5216051
    Abstract: The invention relates to novel tri-acetal polyol compounds and to a crystalline polyolefin composition having dispersed therein a nucleating agent composed of one or more of said polyol acetals.
    Type: Grant
    Filed: October 28, 1991
    Date of Patent: June 1, 1993
    Assignee: Allied-Signal Inc.
    Inventors: Tammy L. Smith, Julie R. Schollmeyer, Yash P. Khanna, Kristina A. Miller, Divarakaran Masilamani
  • Patent number: 5196599
    Abstract: A method of preparing difluoroformals of the formula(RCH.sub.2 O).sub.2 CF.sub.2,wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.su), --C(NO.sub.2).sub.2 CH.sub.3, or a fluoroalkyl group such as --CF.sub.3 or --CF.sub.2 CF.sub.3, by reacting the corresponding dichloroformals with hydrogen fluoride in pyridine. These difluoroformals are useful as energetic explosive and propellant ingredients.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: March 23, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William H. Gilligan, Michael E. Sitzmann
  • Patent number: 5155281
    Abstract: A method of preparing dichloroformals of the formula(RCH.sub.2 O).sub.2 CCl.sub.2by reaction of one mole of a thionocarbonate of the formula(RCH.sub.2 O).sub.2 C.dbd.Swith two moles of benzenesulfenyl chloride, chlorobenzenesulfenyl chloride, r methanesulfenyl chloride wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.sub.2), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, or --CF.sub.2 CF.sub.3. These energetic dichloroformals are useful as explosive and propellant ingredients and as intermediates in the synthesis of other energetic explosive and propellant ingredients.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: October 13, 1992
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan
  • Patent number: 5145972
    Abstract: The present invention relates to a process for preparing halo acetals of ethylenic aldehydes by reaction of a halogen cation with enamine followed by a hydrolysis and reaction with an alcohol, a glycol or an orthoformate. These halo acetals are used as intermediate for the synthesis of vitamins A and E.It also relates to a new compound of formula (IV), ##STR1## to a process for preparing it from halo acetals of ethylenic aldehydes by reaction with triethyl phosphate, and to its use for the preparation of retinal by reaction with .beta.-ionylideneacetaldehyde.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: September 8, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5103053
    Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with a dialkylacetal.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: April 7, 1992
    Assignee: Ethyl Corporation
    Inventors: Joe D. Sauer, Kim R. Smith, James E. Borland
  • 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: 4804786
    Abstract: 4-Monoacetals of (E)-2-methylbut-2-ene-1,4-dial of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each an aliphatic hydrocarbon radical of 1 to 12 carbon atoms, cycloalkyl of 5 to 7 carbon atoms or benzyl, or R.sup.1 and R.sup.2 together form an ethylene or propylene radical which may furthermore be substituted by lower alkyl, are prepared by a process in which a compound of the general formula II ##STR2## where either R.sup.3 and R.sup.4 are both one of the groups ##STR3## where R.sup.1 and R.sup.2 have the above meanings, or R.sup.3 is one of the groups ##STR4## and R.sup.4 is formyl ##STR5## is reacted, at from 20.degree. to 200.degree. C., in the presence of an acidic compound, with the compound of the formula IIIR.sup.5 --OH (III)where R.sup.5 is hydrogen, alkyl of 1 to 12 carbon atoms or hydroxyalkyl of 2 to 5 carbon atoms, and, where R.sup.3 and R.sup.4 are each ##STR6## R.sup.5 is alkyl, and where R.sup.3 and R.sup.4 are each ##STR7## R.sup.5 is hydrogen, and where R.sup.
    Type: Grant
    Filed: January 16, 1987
    Date of Patent: February 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Bernhard Schulz
  • Patent number: 4756777
    Abstract: Bis(2-fluoro-2,2-dinitroethoxy)(1-fluoro-1,1-dinitro-2-propoxy)methane wh is useful as an energetic coplasticizer with bis(2-fluoro-2,2-dinitroethyl)formal in plastic-bonded explosives.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: July 12, 1988
    Assignee: The United States of America as represent by the Secretary of the Navy
    Inventors: William M. Koppes, Horst G. Adolph
  • Patent number: 4705899
    Abstract: 1:3 "mixed" orthocarbonates of the formula[CF(NO.sub.2).sub.2 CH.sub.2 O].sub.3 C--ORwherein R is--CH.sub.2 C(NO.sub.2).sub.3,--CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3,--CH.sub.2 CH.sub.2 NO.sub.2,--CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OH,--CH.sub.2 C(NO.sub.2).sub.2 CH.sub.2 OC[OCH.sub.2 CF(NO.sub.2).sub.2 ].s3,--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 OH,--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 OC[OCH.sub.2 CF(NO.sub.2).sub.2 ].sub.3,--CH.sub.2 CF.sub.3,--CH.sub.2 CH.sub.3, and ##STR1## and a method of preparation.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: November 10, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan
  • Patent number: 4703116
    Abstract: Polysaccharide aldehydes having the formula Sacch--O--CH.sub.2 --CH.dbd.CH--CHO, ##STR1## such as starch, cellulose, and gum aldehydes, are useful for imparting wet, dry, or temporary wet strength to paper. They are prepared by a non-oxidative method which involves reacting the polysaccharide base, in the presence of alkali, with a derivatizing acetal reagent having the general structure ##STR2## and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R.sup.11 and R.sup.12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R.sup.11 or R.sup.12 is one of the groups when n is 2, or R.sup.11 and R.sup.12 are not present when n is 3; R.sup.13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R.sup.14 and R.sup.15 are individually a hydrogen or a methyl group; R.sup.16, R.sup.17, and R.sup.
    Type: Grant
    Filed: February 14, 1986
    Date of Patent: October 27, 1987
    Assignee: National Starch and Chemical Corporation
    Inventors: Daniel B. Solarek, Patrick G. Jobe, Martin M. Tessler, Robert L. Billmers, Diane J. Lamb, John J. Tsai
  • Patent number: 4499309
    Abstract: Energetic orthoformates of the formula ##STR1## wherein R and R' vary independently and R is --CH.sub.2 C(NO.sub.2).sub.2 H.sub.3,--CH.sub.2 C(NO.sub.2).sub.3,--CH.sub.2 CF(NO.sub.2).sub.2,--CH.sub.2 CF.sub.2 (NO.sub.2), or--CH.sub.2 CF.sub.3,R' is--CH.sub.2 CF(NO.sub.2).sub.2,--CH.sub.2 F.sub.2 (NO.sub.2), or--CH.sub.2 CF.sub.3,and Y is --F, --N.sub.3, --C.tbd.N, ##STR2## and methods of preparation.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: February 12, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan
  • Patent number: 4453021
    Abstract: 2,2-dinitropropyl 2-fluoro-2,2-dinitroethyl formal which is prepared by the ollowing processes: ##STR1##
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: June 5, 1984
    Assignee: The United States of Americaas represented by the Secretary of the Navy
    Inventor: Horst G. Adolph
  • Patent number: 4449000
    Abstract: A 1:1:2 mixed orthocarbonate of the formula ##STR1## wherein R and R" are each one of the following groups--CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3,--CH.sub.2 C(NO.sub.2).sub.3,--CH.sub.2 CF(NO.sub.2).sub.2,--CH.sub.2 CF.sub.2 (NO.sub.2), and--CH.sub.2 CF.sub.3, andR' is one of the followingCH.sub.2 CF(NO.sub.2).sub.2,CH.sub.2 CF.sub.2 (NO.sub.2), andCH.sub.2 CF.sub.3,provided that R.noteq.R', R.noteq.R", and R'.noteq.R". These 1:1:2 orthoconates are produced by the following reaction sequence: ##STR2## wherein R, R', and R" are as defined above. By choosing R and R" to be the same and either --CH.sub.2 (NO.sub.2).sub.2 CH.sub.3 or --CH.sub.2 C(NO.sub.2).sub.3 in the above reaction, 1:3 mixed orthocarbonates of the formula ##STR3## wherein R.noteq.R', R".noteq.R', R=R", and R and R" are each CH.sub.2 C(NO.sub.2).sub.2 CH.sub.3,CH.sub.2 C(NO.sub.2).sub.3,CH.sub.2 CF.sub.2 (NO.sub.2), orCH.sub.2 CF.sub.3,and R' is CH.sub.2 CF(NO.sub.2).sub.2, CH.sub.2 CF.sub.2 (NO.sub.2) or CH.sub.2 CF.sub.3 may be prepared.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: May 15, 1984
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan
  • Patent number: 4426540
    Abstract: Vinyl ethers are prepared by reacting divinyl ether with a primary alcohol in the presence of a catalytic amount of red mercuric oxide and trifluoroacetic acid. The vinyl ethers so produced are particularly useful as monomers which can be polymerized into energetic macromolecular binder materials with excellent mechanical, physical and energetic properties.
    Type: Grant
    Filed: June 10, 1976
    Date of Patent: January 17, 1984
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Scott A. Shackelford, Raymond R. McGuire, Robert E. Cochoy
  • Patent number: 4424146
    Abstract: The present invention relates to the novel compound acetaldehyde ethyl 6-dihydrolinalyl acetal, useful as a fragrance material. The invention also provides a method of preparing this compound from 6-dihydrolinalool, and fragrance compositions which include the compound.
    Type: Grant
    Filed: October 7, 1981
    Date of Patent: January 3, 1984
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Michael R. Britten-Kelley, Odd Hansen
  • Patent number: 4424398
    Abstract: A process for synthesizing energetic ethers, esters and acetals is disclosed that comprises reacting certain alcohols with certain alkenes or alkynes in the presence of mercuric or mercurous sulfate. The products obtained are particularly useful as plasticizers, monomers or prepolymers for propellant binder systems.
    Type: Grant
    Filed: September 25, 1974
    Date of Patent: January 3, 1984
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Raymond R. McGuire, Robert E. Cochoy, Scott A. Shackelford
  • Patent number: 4374241
    Abstract: Nitropolyformals of the formula H--OCH.sub.2 C(NO.sub.2).sub.2 ZC(NO.sub.sub.2 CH.sub.2 OCH.sub.2 --OCH.sub.2 C(NO.sub.2).sub.2 ZC(NO.sub.2).sub.2 CH.sub.2 OH wherein Z is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 OCH.sub.2 --, or --CH.sub.2 NHCH.sub.2 -- and wherein the average molecular weight of the nitropolyformal molecules is from about 1,000 to about 50,000. The nitropolyformals are prepared by reacting a diol of the formula HOCH.sub.2 C(NO.sub.2).sub.2 ZC(NO.sub.2).sub.2 CH.sub.2 OH, wherein Z is defined as above, with formaldehyde in the presence of concentrated sulfuric acid. These polymers are useful as energetic binders in explosives and propellants.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: February 15, 1983
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Horst G. Adolph
  • Patent number: H184
    Abstract: 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane, CF.sub.3 CHb.2 OCH[OCH.sub.2 CF(NO.sub.2).sub.2 ].sub.2, is an energetic plasticizer useful in plastic-bonded explosives. Of particular importance is its miscibility with fluoropolymers.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: January 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Horst G. Adolph
  • Patent number: H350
    Abstract: An energetic plasticizer which is a mixture of bis(2,2,2-trinitroethyl)fol, bis(2,2-dinitropropyl)formal, and a new compound 2,2-dinitropropyl 2,2,2-trinitroethyl formal.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: October 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst D. Adolph, Kyung E. Kim
  • Patent number: H351
    Abstract: 4,4,10,10-tetranitro-6,8-dioxatridecane-1,13-diol polyformal, HO(CH.sub.2ub.3 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 (CH.sub.2).sub.3 O[CH.sub.2 O(CH.sub.2).sub.3 C(NO.sub.2).sub.2 CH.sub.2 OCH.sub.2 OCH.sub.2 C(NO.sub.2).sub.2 (CH.sub.2).sub.3 O].sub.n H, which has high energy, high thermal stability, and which is useful as a prepolymer for plastic-bonded explosive compositions.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: October 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Kyung E. Kim, Horst G. Adolph
  • Patent number: H352
    Abstract: Bis(2-fluoro-2,2-dinitroethoxy) 2,2,3,3,4,4,4-heptafluorobutoxymethane, (F), CF.sub.3 CF.sub.2 CF.sub.2 CH.sub.2 OCH[OCH.sub.2 CF(NO.sub.2).sub.2 ].sub.2, is an energetic plasticizer with a melting point of -18.degree. C. and thermal stability up to 150.degree. C. HFBF is miscible with polyfluoro- and polynitropolymers and useful as a plasticizer in plastic-bonded explosives.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: October 6, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: William M. Koppes, Horst G. Adolph