Acyclic Patents (Class 568/589)
  • Patent number: 11230508
    Abstract: The present disclosure generally pertains to green oxidizer compositions and method of synthesizing and using the same. Such green oxidizers are stable, may be used in conventional bipropellant thrusters, including, but not limited to LDACS applications, and offer several benefits over conventional oxidizers with respect to toxicity and/or corrosion. The present disclosure also relates to methods of synthesizing poly-nitrated oxetane, a green oxidizer, in an Argon-rich environment.
    Type: Grant
    Filed: July 23, 2018
    Date of Patent: January 25, 2022
    Assignee: Board of Trustees of the University of Alabama, for and on behalf of the University of Alabama in Huntsville
    Inventors: James Edwin Smith, Jr., Chen Zhang, Yu Lei
  • Patent number: 8871983
    Abstract: The present invention provides compounds, or pharmaceutically acceptable salts or analogs thereof, which exhibit anti-tumor activity. The present invention also includes methods for inhibiting the growth of cancer cells by contacting an effective amount of a compound of the present invention with the cancer cells in vitro or in vivo.
    Type: Grant
    Filed: August 10, 2009
    Date of Patent: October 28, 2014
    Assignee: University of Florida Research Foundation, Inc.
    Inventors: Stanislav I. Svetlov, Anatoliy Vakulenko
  • Patent number: 8802896
    Abstract: Disclosed is a polyether compound which is useful as a curing agent or the like, a curing agent using the compound and a producing method of the compound. The polyether compound of the present invention is represented by the following general formula (1). (In the formula, R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or —C(?O)—C(R3)?CH2. R3 represents a hydrogen atom or a methyl group. R1, R2 and R3 may be the same as or different from each other.
    Type: Grant
    Filed: September 30, 2013
    Date of Patent: August 12, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Akihito Amao, Hirotaka Kitagawa
  • Patent number: 8664247
    Abstract: The present invention provides acyclic, geminal-dinitro organic compounds, methods of synthesizing the compounds, pharmaceutical compositions, therapeutic methods, and medical kits for treating various conditions using such compounds and pharmaceutical compositions. The compounds and compositions are useful in the treatment of cancer.
    Type: Grant
    Filed: August 24, 2012
    Date of Patent: March 4, 2014
    Assignees: RadioRx, Inc., Alliant Techsystems Inc.
    Inventors: Jan Scicinski, Bryan T. Oronsky, Robert Wardle, Louis Cannizzo, Nicholas A. Straessler
  • Patent number: 8641816
    Abstract: Provided are new functionalized surfactants and methods of their preparation and use. The surfactants are compounds of formula I: wherein R1, R2, and R3 are as defined herein.
    Type: Grant
    Filed: October 21, 2010
    Date of Patent: February 4, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Matthias S. Ober, Edward D. Daugs, Wanglin Yu, Cynthia L. Rand
  • Patent number: 8410316
    Abstract: The compound (I) or a salt thereof has an excellent controlling activity against pests. Then the compound (I) or a salt thereof is useful for an active ingredient of a pesticidal composition.
    Type: Grant
    Filed: August 31, 2011
    Date of Patent: April 2, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeyuki Itoh, Atsushi Iwata
  • Publication number: 20130053418
    Abstract: The present invention provides acyclic, geminal-dinitro organic compounds, methods of synthesizing the compounds, pharmaceutical compositions, therapeutic methods, and medical kits for treating various conditions using such compounds and pharmaceutical compositions. The compounds and compositions are useful in the treatment of cancer.
    Type: Application
    Filed: August 24, 2012
    Publication date: February 28, 2013
    Inventors: Jan Scicinski, Bryan T. Oronsky, Robert Wardle, Louis Cannizzo, Nicholas A. Straessler
  • Publication number: 20110105507
    Abstract: Provided are new functionalized surfactants and methods of their preparation and use. The surfactants are compounds of formula I: wherein R1, R2, and R3 are as defined herein.
    Type: Application
    Filed: October 21, 2010
    Publication date: May 5, 2011
    Inventors: Matthias S. Ober, Edward D. Daugs, Wanglin Yu, Cynthia L. Rand
  • Publication number: 20100130749
    Abstract: The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren Inter alia the invention relates to a process for the manufacture of a compound of the formula I. or a salt thereof, wherein R1 as well as Act are as defined in the specification, and processes of manufacturing this compound as well as intermediates in this process.
    Type: Application
    Filed: April 1, 2008
    Publication date: May 27, 2010
    Inventor: Gottfried Sedelmeier
  • Publication number: 20100094062
    Abstract: A cetane number increasing process and additive for diesel fuel, this additive being obtained by means of a less complex and more economic process which seeks to use by products in excess of supply on the market and to optimize the installed capacity of existing plants, the process producing a mixture of nitrated glycerol diethers is represented by the following general formula (I) where R can be: a hydrogen atom; or an R?—O group; and where R? can be an alkene or alkyne or an unsaturated hydrocarbon formed by a number of carbon atoms ranging from 4 to 10 carbons.
    Type: Application
    Filed: April 18, 2007
    Publication date: April 15, 2010
    Inventors: Carlos René Klotz Rabello, Yuri Kokitsu Ferreira, Raphael Bezerra de Menezes
  • Publication number: 20090176893
    Abstract: The present invention provides for a composition comprising a siloxane having the formula: M1DM2 wherein M1=(R1)(R2)(R3)SiO1/2; M2=(R4)(R5)(R6)SiO1/2 and D=(R7)(Z)SiO2/2 where R1, R2, R3, R4, R5, R6 and R7 are each independently selected from the group consisting of 1 to 4 carbon monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 4 to 9 carbons containing an aryl group; Z is a pendant hydrophilic ionic group selected from the group consisting of R8—RA, R9—RC, and R10—RZ; RA being an anionic substituent, RC a cationic substituent or RZ a zwitterionic substituent on the D group wherein the composition is resistant to hydrolysis under either basic or acidic conditions.
    Type: Application
    Filed: December 26, 2007
    Publication date: July 9, 2009
    Applicant: MOMENTIVE PERFORMANCE MATERIALS INC.
    Inventors: Mark D. Leatherman, George A. Policello, Wenqing N. Peng, Liping Zheng, Roland Wagner, Suresh K. Rajaraman, Zijun Xia
  • Publication number: 20090143623
    Abstract: Provided is a production process of a cyanoethyl ether by reacting an alcohol and acrylonitrile in a two-phase system of a non-ether solvent/an aqueous alkali solution.
    Type: Application
    Filed: November 24, 2008
    Publication date: June 4, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Taiji Katsumata, Takayuki Ito, Masayuki Harada
  • Patent number: 7432399
    Abstract: A polyol monomer comprising the formula: R1 and R3 are —H, aliphatic, aromatic, or ether; R2 is aliphatic, aromatic, ester, ether, or acrylic, and R1 contains a hydroxyl group, R3 contains a hydroxyl group, R2 contains —O—CH2—CH(OH)—, or any combination thereof. The polyol monomer may be made by reacting an epoxy and an amine. Either the epoxy contains more than one epoxide groups, the amine contains a hydroxyl group, or both. A thermoset made by reacting the polyol monomer with a polyisocyanate.
    Type: Grant
    Filed: November 2, 2004
    Date of Patent: October 7, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Jozef Verborgt, Arthur Anthony Webb
  • Patent number: 7288681
    Abstract: A synthesis of an energetic prepolymer used as a high-energy binder for an insensitive and high performance explosive is disclosed. More specifically, provided are a novel compound 2-nitratoethyl oxirane expressed by formula III, a novel compound poly(2-nitratoethyl oxirane) expressed by formula IV, obtained by polymerization of 2-nitratoethyl oxirane used as a monomer and a preparation method thereof.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: October 30, 2007
    Assignee: Agency for Defense A Korean Non-Profit Organization
    Inventors: Jin Seuk Kim, Jin Rai Cho, Keun Deuk Lee, Jae Kyoung Kim
  • Patent number: 7223803
    Abstract: An activated, substantially water soluble poly(ethylene glycol) is provided having of a linear or branched poly(ethylene glycol) backbone and at least one terminus linked to the backbone through a hydrolytically stable linkage, wherein the terminus is branched and has proximal reactive groups. The free reactive groups are capable of reacting with active moieties in a biologically active agent such as a protein or peptide thus forming conjugates between the activated poly(ethylene glycol) and the biologically active agent.
    Type: Grant
    Filed: December 21, 2005
    Date of Patent: May 29, 2007
    Assignee: Nektar Therapeutics AL, Corporation
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 7135600
    Abstract: The present invention relates to novel compounds of Formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: November 14, 2006
    Assignee: Glaxo Group Limited
    Inventors: Keith Biggadike, Diane Mary Coe, Stephen Barry Guntrip, Brian Edgar Looker, Panayiotis Alexandrou Procopiou
  • Patent number: 7030278
    Abstract: An activated, substantially water soluble poly(ethylene glycol) is provided having of a linear or branched poly(ethylene glycol) backbone and at least one terminus linked to the backbone through a hydrolytically stable linkage, wherein the terminus is branched and has proximal reactive groups. The free reactive groups are capable of reacting with active moieties in a biologically active agent such as a protein or peptide thus forming conjugates between the activated poly(ethylene glycol) and the biologically active agent.
    Type: Grant
    Filed: September 23, 2003
    Date of Patent: April 18, 2006
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 6984759
    Abstract: Process for the perfluoropolyether preparation having reactive end groups —CH2NH2, —CHO, —CH2OH, by reduction of the corresponding perfluoropolyethers having —CN, —COCl, —CHO end groups by using gaseous hydrogen in the presence of a catalyst constituted by Pd, Rh, or Ru, supported on solid metal fluorides, at a temperature from 20° C. to 150° C. and under a pressure between 1 and 50 atm.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: January 10, 2006
    Assignee: Solvay Solexis S.p.A.
    Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
  • Patent number: 6649780
    Abstract: Cationic lipids are provided which are useful in the preparation of liposomes and other lipid vesicle carriers. The lipids of the invention are particularly useful as carriers of nucleic acids and other negatively charged substances, for delivery to cells.
    Type: Grant
    Filed: December 17, 1999
    Date of Patent: November 18, 2003
    Assignees: Valentis, Inc., Max-Planck-Gesellschaft zur Foerderung der Wissaschaften B.V.
    Inventors: Hansjörg Eibl, Jinkang Wang, Yi Lin Zhang
  • Patent number: 6608230
    Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 19, 2003
    Assignee: WE-DEA Aktiengesellschaft für Mineraloel und Chemie
    Inventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
  • Patent number: 6458837
    Abstract: The invention discloses stable diesters of chelating agents of divalent metal ions, processes for their preparation and pharmaceutical compositions thereof. Most preferred compounds according to the present invention are stable lipophilic diesters comprising a covalent conjugate of a BAPTA and a pharmaceutically acceptable alcohol. The diesters are useful in a method for treating a condition or disease related to an excess of divalent metal ions, and in particular for the treatment of a condition or disease related to elevated levels of intracellular calcium ions, such as in brain or cardiac ischemia, stroke, epilepsy, Alzheimer's disease or cardiac arrhythmia and in open heart surgery.
    Type: Grant
    Filed: March 27, 2000
    Date of Patent: October 1, 2002
    Assignee: D-Pharm Ltd.
    Inventors: Alexander Kozak, Israel Shapiro
  • Patent number: 6380439
    Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
    Type: Grant
    Filed: January 25, 2000
    Date of Patent: April 30, 2002
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
  • Patent number: 6372927
    Abstract: The process for preparing an alkylene oxide adduct, including the steps of feeding an organic compound having active hydrogen and an alkylene oxide to a reaction column packed with a solid catalyst, and carrying out addition reaction of the organic compound having active hydrogen with an alkylene oxide in a gas-liquid fixed bed reaction, wherein the alkylene oxide is in a state of gas and the organic compound having active hydrogen is in a state of liquid.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: April 16, 2002
    Assignee: Kao Corporation
    Inventors: Nobuhiro Tatsumi, Yoshikazu Ogura, Takanobu Katayama, Osamu Tabata
  • Patent number: 6362254
    Abstract: An activated, substantially water soluble poly(ethylene glycol) is provided having of a linear or branched poly(ethylene glycol) backbone and at least one terminus linked to the backbone through a hydrolytically stable linkage, wherein the terminus is branched and has proximal reactive groups. The free reactive groups are capable of reacting with active moieties in a biologically active agent such as a protein or peptide thus forming conjugates between the activated poly(ethylene glycol) and the biologically active agent.
    Type: Grant
    Filed: March 11, 1999
    Date of Patent: March 26, 2002
    Assignee: Shearwater Corporation
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 6191315
    Abstract: Most generally, the invention provides a method for making a neutralized polyether polyol, comprising the steps of a) Polymerizing one or more alkylene oxides in the presence of an alkaline catalyst to form a polyalkylene oxide intermediate; and b) Neutralizing the intermediate, after the polymerization step a) is complete, with an organic acid of general formula where R1 is hydrogen, methyl, or ethyl; R2 is methyl or ethyl; and R3 is an alkyl, aryl, or aralkyl group containing one to twelve carbon atoms. The invention also comprises the novel compositions made by the above process.
    Type: Grant
    Filed: February 11, 1999
    Date of Patent: February 20, 2001
    Assignee: BASF Corporation
    Inventors: Chacko Thankachan, Brian J. Betke, Michael C. Welch
  • Patent number: 6133211
    Abstract: Block copolyethers having general formula (I):RX--(CH.sub.2 --CHR.sub.1 --O--).sub.x --(--CH.sub.2 CHR.sub.2 --O--).sub.y --(--CH.sub.2 --CHR.sub.3 --O--).sub.z --R.sub.4wherein:R is selected from H, alkyl, alkylaryl;X is selected from O, S and N;R.sub.1, R.sub.2 and R.sub.3 are selected from H, CH.sub.3, and C.sub.2 -C.sub.10 alkyl radicals;R.sub.4 is selected from H, alkyl, acyl;x,y,z represent the number of ether units and are integers which have such values that the molecular weight of the compound having general formula (I) is between 600 and 4000, and in addition (x+z)/y is between 1.5 and 5.0; with the proviso that:a) either R.sub.1 and R.sub.3 are selected from H and CH.sub.3, in which case R.sub.2 is selected from C.sub.2 to C.sub.10 alkyl radicals,b) or R.sub.1 and R.sub.3 are selected from C.sub.2 -C.sub.10 alkyl radicals, in which case R.sub.2 is selected from H and CH.sub.3.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: October 17, 2000
    Assignee: Agip Petroli S.p.A.
    Inventors: Sandra Cobianco, Alessandro Lezzi, Alberto Forlini, Emilio Gatti
  • Patent number: 6037496
    Abstract: 3-{N-[2-(N',N'-dimethylamino ethoxy)ethyl]-N-methylamino}propionamide is a new compound which is useful as a catalyst in the production of polyurethane foams.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard Van Court Carr, Ning Chen, Mark Leo Listemann, Richard Paul Underwood
  • Patent number: 6037455
    Abstract: The present invention is directed to novel propoxyphene derivatives which are synthesized for the covalent attachment to antigens (proteins or polypeptides) for the preparation of antibodies or receptors to propoxyphene and propoxyphene metabolites. The resulting novel antigens may be used for the production of antibodies or receptors using standard methods. Once generated, the antibodies or receptors and the novel derivatives which are covalently attached to proteins, polypeptides or labels may be used in the immunoassay process.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: March 14, 2000
    Assignee: Biosite Diagnostics Incorporated
    Inventor: Kenneth F. Buechler
  • Patent number: 5871675
    Abstract: The invention relates to a novel process for the production of tinted mouldings, in particular tinted contact lenses, in which a crosslinkable tinted polymer comprising units containing a crosslinkable group and units containing a reactive dye radical is crosslinked in solution, and to tinted mouldings, in particular tinted contact lenses, obtainable by this process.
    Type: Grant
    Filed: September 18, 1997
    Date of Patent: February 16, 1999
    Assignee: Novartis AG.
    Inventors: Achim Muller, Thomas Pohlmann, Bernhard Seiferling
  • Patent number: 5869715
    Abstract: For use in transporting biologically active species into and through membrane barriers, a cationic amine compound is utilized that has the general structure: ##STR1## wherein R.sub.4 and R.sub.5 are a pair of same or different lipoyl moieties selected from a group consisting of an alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, or alkynoyl groups and for R.sub.1 R.sub.2, and R.sub.3 at least two are hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl groups or at least one amine bonded halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group or a mixture of at least one halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group and at least one hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl group, and X.sup.- is an anion.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: February 9, 1999
    Assignee: The Reagents of the University of California
    Inventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam
  • Patent number: 5801260
    Abstract: Novel substrates of phospholipases, lysophospholipases and lipases are disclosed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 1, 1998
    Assignee: LaJolla Pharmaceuticals Co.
    Inventors: Lin Yu, Robert John Termansky
  • Patent number: 5708092
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: January 13, 1998
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: 5616745
    Abstract: New lipopolyamines of general formula (I), their salts, their preparation and their use. ##STR1## n=1 to 5 and m=2 to 6 R represents a radical ##STR2## (R.sub.1 and R.sub.2 : aliphatic radical containing 12 to 22 carbon atoms; R: hydrogen atom or alkyl radical optionally substituted with phenyl), or a radical ##STR3## (X=CH.sub.2, CO; R.sub.3 and R.sub.4 aliphatic radical containing 11 to 21 carbon atoms), their preparation and their use.The lipopolyamines of general formula (I) are especially useful as vectors for the transfection of eukaryotic cells.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 1, 1997
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Jean-Paul Behr, Jean-Philippe Loeffler
  • Patent number: 5491261
    Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: February 13, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
  • Patent number: 5468841
    Abstract: The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: November 21, 1995
    Assignee: Aerojet General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
  • Patent number: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • 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: 5326829
    Abstract: Disclosed herein is a method of preparing an activated polyether polyol by reacting an aminoalcohol with a polyether terminated with a leaving group.
    Type: Grant
    Filed: October 7, 1992
    Date of Patent: July 5, 1994
    Assignee: Miles Inc.
    Inventors: William E. Slack, Rick L. Adkins
  • 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: 5258544
    Abstract: Disclosed is a process for the preparation of 2-aryl-1-cyclohexene-1-carboxaldehydes from 1-arylcyclohexenes which are intermediates for trans-6-[(2-arylsubstituted cycloalkenyl and substituted cycloalkyl)alkenyl and alkyl]-3,4,5,6-tetrahydro-2H-pyran-2-ones.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: November 2, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
  • Patent number: 5117055
    Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: May 26, 1992
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 4855508
    Abstract: The invention comprises a novel preparation of energetically substituted diether compounds and novel diether compounds not previously reported. In one embodiment certain isomeric forms of dibromoalkanes are converted to corresponding isomers of bromoalkyl trifluoromethanesulfonate esters by reaction with silver trifluoromethanesulfonate (triflate) in a variety of solvents. The triflate substituent in the bromoalkyl triflate esters is then easily displaced by alcohols, including non-nucleophilic ones such as those that contain nitro. The intermediates are similarly reacted to make energetic diethers, selectively under mild conditions. The energetically substituted diether compounds are particularly useful as energetic curatives and plasticizers for rocket propellant binders as well as stable solid oxidizers and industrial explosives.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: August 8, 1989
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Robert D. Chapman, John L. Andreshak, Scott A. Shackelford
  • Patent number: 4745208
    Abstract: 2,2,2-trinitroethyl 2-nitroxyethyl ether (TNEN), C(NO.sub.2).sub.3 CH.sub.2 CH.sub.2 CH.sub.2 ONO.sub.2, which is prepared by the following reaction sequence:C(NO.sub.2).sub.3.sup.- K.sup.+ +ClCH.sub.2 OCH.sub.2 CH.sub.2 BR.fwdarw.C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 Br C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 Br+AgNO.sub.3 .fwdarw.C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 ONO.sub.2.2,2,2-trinitroethyl 2-nitroxyethyl ether is useful an an energetic plasticizer, for example in LOVA gun propellants.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: May 17, 1988
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Kyung E. Kim
  • Patent number: 4727199
    Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventor: Stephen W. King
  • Patent number: 4594430
    Abstract: Geminal dinitro compounds are prepared by reacting an organic nitro compound having a replaceable hydrogen on the carbon to which the nitro group is attached with a source of nitrite ions in the presence of an oxidizing agent and a catalytic amount of an alkali metal ferricyanide.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: June 10, 1986
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Vytautas Grakauskas, Lee C. Garver, Kurt Baum
  • Patent number: 4549015
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: October 22, 1985
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4433179
    Abstract: A process for the preparation of allyl ethers of the formulaR--O--CH.sub.2 --CH.dbd.CH.sub.2).sub.nin which R and n are as defined in claim 1, by reacting hydroxy compounds of the formulaR--OH).sub.nwith allyl chloride or allyl bromide by phase transfer catalysis, 0.8 to 5 mols of allyl chloride or allyl bromide, 1 to 6 mols of aqueous or solid sodium hydroxide and, as the phase transfer catalyst, 2 to 20 mol % of a quaternary ammonium salt, a quaternary ammonium base or a crown ether being employed per hydroxyl equivalent of the compound of the formula II, and the reaction being carried out in the temperature range from 20.degree. to 100.degree. C.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: February 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Charles E. Monnier
  • 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: 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