Preparing Directly From Hetero Ring Containing Compound Patents (Class 564/487)
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Publication number: 20080261814Abstract: The present invention generally relates to a process for preparing the alkoxylated alkylamines and/or alkyl ether amines. The process consists of three stages, and utilizes an alkali catalyst. The alkoxylated alkyl amines and alkoxylated alkyl ether amines prepared by the process possess the peaked distribution and contain less hazardous by-product.Type: ApplicationFiled: September 23, 2005Publication date: October 23, 2008Applicants: MONSANTO TECHNOLOGY LLC, AKZO NOBEL N.V.Inventors: Shawn Zhu, Giao Nguyen, Kha Nguyen, Alberto Slikta, David Eaton, David Becher, Henry Agbaje, Michael Seitz
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Patent number: 7432399Abstract: 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: GrantFiled: November 2, 2004Date of Patent: October 7, 2008Assignee: The United States of America as represented by the Secretary of the NavyInventors: Jozef Verborgt, Arthur Anthony Webb
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Patent number: 7307184Abstract: The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the ?-position to prepare oxazolidinone derivatives of ?-hydroxyethylamine compounds having an inverted steric configuration at the ?-position carbon, which comprises introducing a step of treating in contact with water with heating under acidic to neutral conditions into the process. Also, the present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the ?-position to prepare ?-hydroxyethylamine compounds having an inverted steric configuration at the ?-position carbon, which comprises subjecting the oxazolidinone derivatives prepared as described above to a step of treating in contact with water under basic conditions.Type: GrantFiled: May 23, 2002Date of Patent: December 11, 2007Assignee: Kaneka CorporationInventors: Hiroshi Murao, Koki Yamashita, Toshihiro Takeda, Yasuyoshi Ueda
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Patent number: 7220883Abstract: Process for the preparation of primary amines of formula (I): where R3 represents an alkyl, cycloalkyl or aralkyl group, by reaction of a triazolium salt of formula (II): where R1 and R2 represent hydrogen or an alkyl, aralkyl or aryl group, R4 represents an alkyl or aralkyl group or a residue of an organic polymer functionalized by an alkylating group, and A? represents a halogen, alkylsulphonate, arylsulphonate, alkyl sulphate, hydrogensulphate, hemisulphate, perchlorate or hydroxide, with a hydride, in order to obtain an amine of formula (I), which is isolated, if desired, and intermediates.Type: GrantFiled: July 28, 2003Date of Patent: May 22, 2007Assignee: Clariant (France)Inventors: Muriel Serradeil Albalat, Jean-Claude Vallejos, Christian Roussel, Didier Wilhelm
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Patent number: 7189879Abstract: A new process for the production of 1-hydroxymethyl-1,3,5-triazapentane, trihydrochloride is described.Type: GrantFiled: May 24, 2005Date of Patent: March 13, 2007Assignee: Schering AGInventors: Johannes Platzek, Jan Huebner, Orlin Petrov
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Patent number: 7026515Abstract: A readily available and inexpensive natural ?-amino acid is converted into a compound represented by formula (1), which is then reacted with an organometallic reagent represented by formula (2) to give an optically active 5-hydroxyoxazolidine represented by formula (3), which is then treated with an acid to provide an optically active aminoketone represented by formula (4). The product is then converted into an optically active aminoalcohol represented by formula (5) or (6) by, for example reduction.Type: GrantFiled: November 9, 2001Date of Patent: April 11, 2006Assignee: Mitsui Chemicals, Inc.Inventors: Hidetoshi Tsunoda, Kunio Okumura, Kengo Otsuka
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Patent number: 6924315Abstract: The present invention provides compounds useful as surfactants having formula (1), including isomers thereof: wherein a and b are integers independently selected from about 3 to about 6; x is an integer from about 1 to about 12; (m+n) is from about 1 to about 4; the R1 groups are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms; and when (m+n) is equal to or greater than 2, each R1 may be independently R2 or R3, wherein R2 and R3 are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms. The invention also provides a method for reducing surface tension in a waterborne composition or an industrial process by the incorporation of a surfactant having formula (1) and an aqueous composition comprising a surfactant having formula (1).Type: GrantFiled: March 13, 2003Date of Patent: August 2, 2005Assignee: Air Products and Chemicals, Inc.Inventors: Christine Peck Kretz, Michael Edward Ford, Kevin Rodney Lassila
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Patent number: 6906224Abstract: A process for producing ?-aminohalomethyl ketones or N-protected ?-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, ?-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.Type: GrantFiled: October 30, 2003Date of Patent: June 14, 2005Assignee: Ajinomoto Co., Inc.Inventors: Tomoyuki Onishi, Naoko Hirose, Takayuki Suzuki, Takashi Nakano, Masakazu Nakazawa, Kunisuke Izawa
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Publication number: 20040210089Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.Type: ApplicationFiled: October 30, 2003Publication date: October 21, 2004Applicant: Ajinomoto Co., Inc.Inventors: Tomoyuki Onishi, Naoko Hirose, Takayuki Suzuki, Takashi Nakano, Masakazu Nakazawa, Kunisuke Izawa
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Patent number: 6800764Abstract: A process is provided for preparing chirally pure S-enantiomers of &agr;-amino acids comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of the formula (R)2CH(CH2)nCH2X; b) adding the organometallic reagent to carbon dioxide to afford a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride, acid anhydride, or thionyl chloride in the presence of a tertiary amine base; d) reacting the product of step c) with an alkali metal salt of S-4-benzyl-2-oxazolidinone; e) treating the product of step d) with a strong non-nucleophilic base to form an enolate anion; f) trapping the enolate anion with 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an &agr;-azido acid; h) reducing the &agr;-azido acid to the &agr;-amino acid; and i) recrystallizing the &agr;-amino acid to the chirally pure &agr;-amino acid.Type: GrantFiled: November 26, 2002Date of Patent: October 5, 2004Assignee: WyethInventors: Anthony Frank Kreft, Madelene Miyoko Antane, Derek Cecil Cole, Dennis Martin Kubrak, Lynn Resnick, Joseph Raymond Stock, Zheng Wang
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Patent number: 6790996Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.Type: GrantFiled: October 17, 2002Date of Patent: September 14, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch
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Patent number: 6646150Abstract: The present invention provides a process for industrially producing (aminomethyl)trifluoromethylcarbinol derivatives, in particularly, optically active compounds thereof, which are useful as starting compounds for drugs such as protease inhibitors, etc.Type: GrantFiled: June 13, 2002Date of Patent: November 11, 2003Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Fuminori Sato, Tomoki Omodani, Ryotaro Shiratake, Yasunao Inoue, Takashi Deguchi
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Patent number: 6613944Abstract: The present invention includes a number of novel intermediates such as the (S)-secondary alcohol of formula (VIIIA) X2—CH2—C*H(OH)—CH2—NH—CO—RN (VIIIA) and processes for production of pharmacologically useful oxazolidinones.Type: GrantFiled: January 28, 2003Date of Patent: September 2, 2003Assignee: Pharmacia & Upjohn CompanyInventor: Bruce Allen Pearlman
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Patent number: 6528687Abstract: A process for the preparation of an enantiomerically enriched chiral amine of formula (10), or the opposite enantiomer thereof, from an inline of formula (11) wherein (i) R1 is aryl, R2 is alkyl and R3 is aryl or aryl-CH2—, or (iii) R2 is linked with R1 and/or R3 to form one or more rings and R3 or R1 (if not in a ring) is H or a non-interfering organic group, the number of C atoms in each of R1, R2 and R3 being up to 30, comprises asymmetric hydrogenation of the imine in the presence of a base and, as catalyst, a ruthenium complex of a chiral diphosphine and a chiral diamine.Type: GrantFiled: July 23, 2001Date of Patent: March 4, 2003Assignee: Chirotech Technology LimitedInventors: Christopher James Cobley, Julian Paul Henschke, James Andrew Ramsden
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Patent number: 6521564Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.Type: GrantFiled: November 30, 2000Date of Patent: February 18, 2003Assignee: Roche Vitamins, Inc.Inventors: Oliver Gerald Degischer, Felix Roessler
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Patent number: 6350714Abstract: The present invention relates to a process for preparing a catalyst by activating a catalytic composition which comprises a) at least one metal of group IB or IIB or a compound thereof, b) where appropriate a carrier which comprises treating the composition with an alkyne of the general formula I R1—C≡C—R2 (I) in which R1 is alkyl, cycloalkyl, aryl, hydroxyalkyl, haloalkyl, alkoxy or alkoxyalkyl, R2 is a hydrogen atom, alkyl, cycloalkyl or aryl, and a carbonyl compound of the general formula II in which R3 and R4 are, independently of one another, a hydrogen atom, alkyl, haloalkyl, cycloalkyl or aryl, to catalysts obtainable by this process, and to alkynylations and aminoalkylations employing these catalysts.Type: GrantFiled: May 31, 2000Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Arnd Böttcher, Jochem Henkelmann, Thomas Preiss, Melanie Brunner
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Patent number: 6312538Abstract: A new compound, 1,1-diamino-2,2-dinitroethylene suitable for use as an explosive, as well as an intermediate for preparing the compound consisting of a heterocyclic 5- or 6-ring of the general formula wherein n=at least 1. The compound is prepared by nitrating a heterocyclic 5- or 6-ring containing the structural element wherein Y is an alkoxy group, with a nitrating acid at a low temperature, preferably 0-30° C., and selecting the acidity of the nitrating acid for obtaining a substantial yield of a product containing the structural element and hydrolyzing said product in an aqueous medium for separating 1,1-diamino-2,2--dinitroethylene which is recovered as a precipitate.Type: GrantFiled: January 18, 2000Date of Patent: November 6, 2001Assignee: Totalforsvarets ForskningsinstitutInventors: Nikolai Latypov, Abraham Langlet, Ulf Wellmar
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Patent number: 6307067Abstract: Nucleophilic oxygen species, such as primary alcohols, carboxylates, and water, are added to vinyl epoxides in a highly regioselective and enantioselective manner, providing a convenient route to enantiomerically enriched 1,2-diols and oxygen-containing heterocycles. The reaction employs a chiral Pd(0) complex and a borane or borate as co-catalysts Also described are similar additions of nitrogen nucleophiles, and the addition of carbonates to vinyl epoxides using a chiral Pd(0) catalyst.Type: GrantFiled: September 7, 1999Date of Patent: October 23, 2001Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Ernest John McEachern, Francisco Dean Toste, Barry Martin Trost
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Patent number: 6075168Abstract: This invention concerns a process for the production of diethanolamine (DEA) by contacting monoethanolamine (MEA) and ethylene oxide (EO) in a reactive distillation column. The process may achieve high selectivity to DEA.Type: GrantFiled: August 21, 1998Date of Patent: June 13, 2000Assignee: Huntsman Petrochemical CorporationInventors: Ralph M. DiGuilio, Michael W. McKinney
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Process for the preparation of protected 3-amino-1,2-dihydroxypropane acetal and derivatives thereof
Patent number: 6040464Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.Type: GrantFiled: May 27, 1999Date of Patent: March 21, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang -
Patent number: 6028225Abstract: Hydroxy-substituted hydroxylamine antioxidants can be prepared by reacting hydroxylamine or a mono-substituted hydroxylamine, in free base form, with an epoxide. The antioxidant reaction product can be used without isolation from the reaction solution, and combined with a color developing agent to provide a photographic color developing composition in either concentrated or working strength formulations. The method for preparing the antioxidant is rapid and efficient because of the use of the free base form of the hydroxylamine reactant, higher temperatures (at or above 50.degree. C.) and certain molar ratios of reactants.Type: GrantFiled: September 15, 1998Date of Patent: February 22, 2000Assignee: Eastman Kodak CompanyInventor: Lynda W. McGarry
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Patent number: 5922916Abstract: The present invention relates to a process for preparing 5-methylene cyclic carbamates either by cyclization of an alkynyl amine with carbon dioxide in the presence of a copper catalyst or by forming an isocyanate from a substituted acetoacetamide followed by hydrolysis. The 5-methylene cyclic carbamates by either method are converted to 5-(chloromethylene) cyclic carbamates, using trichloroisocyanuric acid, followed by hydrolysis to a chloroketoamine.The chloroketoamine from the process of this invention additionally can be reacted with an organic acid chloride to form an amide compound which is useful as a fungicide.Type: GrantFiled: April 13, 1998Date of Patent: July 13, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens, Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
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Patent number: 5906998Abstract: In the decomposition of a polymer containing a urethane linkage and/or urea linkage in the presence of a decomposing agent, the amount of evolved carbon dioxide is measured and the decomposition reaction is conducted until a total amount of evolved carbon dioxide reaches a specified value to obtain a liquid decomposition product. According to the present invention, a decomposition product having constant quality can be obtained in a simple manner.Type: GrantFiled: August 20, 1996Date of Patent: May 25, 1999Assignees: Sumitomo Bayer Urethane Co., Inc., Toyota Jidosha Kabushiki KaishaInventors: Yuji Hoshino, Takaaki Masuda, Hiroshi Ikuta, Hisao Mitobe
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Patent number: 5831129Abstract: N-Hydroxyalkyl-substituted aminoalkynes of the formula I ##STR1## are prepared by reacting an alkyne with a 1-oxa-3-azaheterocyclo-alkane in a reaction with heterogeneous catalysis by a catalyst which comprises a compound of a metal of the first or second sub-group.Type: GrantFiled: October 7, 1997Date of Patent: November 3, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Preiss, Jochem Henkelmann, Joachim Wulff-Doring, Susanne Stutz, Thomas Ruhl
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Patent number: 5824821Abstract: The invention provides a process for the production of a 2,3-dihydroxypropylamino compound, said process comprising the reaction steps of:(i) obtaining an allylamino compound;(ii) epoxidizing said allylamino compound to yield an epoxypropylamino compound; and(iii) hydrolysing said epoxypropylamino compound to yield a 2,3-dihydroxypropylamino compound.This process may be used to produce simple 2,3-dihydroxypropylamino compounds such as APD or complex ones such as BAPD (an intermediate in the production of iohexol).Type: GrantFiled: February 7, 1997Date of Patent: October 20, 1998Assignee: Nycomed Imaging ASInventors: David Redick Lane, Janis Vasilevskis
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Patent number: 5801202Abstract: Disclosed is an amine derivative represented by the following formula (1) or an acid addition salt thereof: ##STR1## wherein R.sup.1 represents a group ##STR2## a cyclopentyl group, cyclohexyl group, or a cycloheptyl group, R.sup.2 is a hydrogen atom or C1-C3 alkyl group which may be substituted by one or more hydroxyl groups, m is an integer falling in the range from 3 to 5 inclusive, and n is an integer falling in the range from 9 to 11 inclusive. Also, intermediates useful in the manufacture of the amine derivative (1), compositions for external application to the skin containing the amine derivative, and keratinization improvers containing the amine derivative as an active component are described. The compound (1) has excellent keratinization improving action, pigmentation preventing action, etc.Type: GrantFiled: May 30, 1997Date of Patent: September 1, 1998Assignee: Kao CoprorationInventors: Taketoshi Fujimori, Hiroshi Kusuoku, Akira Yamamuro, Yukihiro Yada, Kazuhiko Higuchi, Genji Imokawa, Naoki Kondo, Yoshinori Masukawa, Hajime Tokuda, Hisashi Tsujimura
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Patent number: 5777165Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.Type: GrantFiled: June 7, 1995Date of Patent: July 7, 1998Assignee: The Procter & Gamble CompanyInventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
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Patent number: 5770773Abstract: A process for the preparation of 5-amino-1,3-dioxanes of formula (I), comprising the catalytic hydrogenation of the new oximes of formula (II) is described.Type: GrantFiled: March 28, 1997Date of Patent: June 23, 1998Assignee: Zambon Group S.p.A.Inventors: Antonio Nardi, Marco Villa
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Patent number: 5723673Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.Type: GrantFiled: June 7, 1995Date of Patent: March 3, 1998Assignee: The Procter & Gamble CompanyInventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
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Patent number: 5693865Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: December 11, 1996Date of Patent: December 2, 1997Assignee: Monsanto CompanyInventor: Peter Gerrard Ruminski
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Patent number: 5679862Abstract: A process for the amination of aliphatic alkane derivatives such as alcohols (mono and polyhydric) which uses catalytic distillation to take advantage of the condensing distillate within the distillation reaction zone in the distillation column reactor. The operation of the distillation column reactor results in both a liquid and vapor phase within the distillation reaction zone. The catalyst is prepared in the form of a distillation structure. The reaction is carried out in a distillation column reactor at a low hydrogen partial pressure, e.g. in the range of 0.1 psia to less than 10 psia.Type: GrantFiled: March 25, 1996Date of Patent: October 21, 1997Assignee: Chemical Research & Licensing CompanyInventors: Speros Peter Nemphos, Dennis Hearn
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Patent number: 5663372Abstract: Described herein is a process for the preparation of 5-amino-1,3-dioxanes of formula (I), wherein R and R.sub.1 have the meanings reported in the description, comprising the catalytic hydrogenation of the new oximes of formula (II).Type: GrantFiled: October 10, 1996Date of Patent: September 2, 1997Assignee: Zambon Group S.p.A.Inventors: Antonio Nardi, Marco Villa
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Patent number: 5625098Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in aqueous/hydroxy solvents such as water and/or methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.Type: GrantFiled: June 5, 1995Date of Patent: April 29, 1997Assignee: The Procter & Gamble CompanyInventors: Junan Kao, Jeffrey J. Scheibel, Robert E. Shumate, Cynthia M. Stark, Roland G. Severson, Jr., Kevin L. Garber, Scott A. VanDiest
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Patent number: 5610227Abstract: The present invention provides anionic polymerization initiators, comprising lithium amino magnesiate complexes, resulting in diene polymer and copolymer elastomers. The invention initiators have stable living ends at high polymerization temperatures and produce polymers containing a high level of tertiary amine functionality. Such polymers exhibit an increased efficiency in coupling termination reactions, and elastomers and products prepared from such polymers exhibit reduced hysteresis properties. Methods are also provided for preparing the initiators, the polymers and the elastomers.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: Bridgestone/Firestone, Inc.Inventors: Thomas A. Antkowiak, James E. Hall
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Patent number: 5600001Abstract: Azines of formula (I): ##STR1## in which R and R' either are identical and represent an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 3 to 5 carbon atoms, or together form a radical of formula (II):--CHR.sub.1 --(CR.sub.2 R.sub.3).sub.n --CHR.sub.4 -- (II)in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, identical or different, represent a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n represents 0 or 1, in their different stereoisomer forms, their preparation process and their use.Type: GrantFiled: February 22, 1996Date of Patent: February 4, 1997Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5541321Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5541320Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbot LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5488166Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.Type: GrantFiled: January 23, 1995Date of Patent: January 30, 1996Assignee: Virginia Tech Intellectual Properties, Inc.Inventor: Tomas Hudlicky
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Patent number: 5468841Abstract: 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: GrantFiled: April 13, 1994Date of Patent: November 21, 1995Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
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Patent number: 5436339Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: July 14, 1992Date of Patent: July 25, 1995Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5426228Abstract: Described herein is a novel method of preparing selectively diastereomers of sphingosine bases and their analogues of general formula (1a) or (1b) ##STR1## where R is an aliphatic or aromatic substituent containing a straight, branched or cyclic chain, which may include one or several heteroatoms as chain members and one or several functional groups as substituents. The method comprises the steps of:a) converting a starting material into an intermediate product in the form of .alpha.,.beta.-unsaturated ketone having the general formula (4a) or (4b) ##STR2## where R is as defined above and PG are any protecting groups compatible with the method,b) reducing said .alpha.,.beta.-unsaturated ketone to an aminoalcohol with DIBAL in toluene to obtain selectively an anti-diastereomer, andc) removing the protecting groups to obtain the free sphingosine base or its analogue according to formula (1a) or (1b).Type: GrantFiled: June 27, 1994Date of Patent: June 20, 1995Inventors: Ari Koskinen, Paivi Koskinen
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Patent number: 5410081Abstract: Compounds of the formula (I) ##STR1## are prepared by reacting 2-mercaptoethanol with compounds of the general formula (II) ##STR2## the substituents having the definition given in the description.Type: GrantFiled: June 24, 1994Date of Patent: April 25, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Kunde, Karl-Josef Herd
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Patent number: 5368760Abstract: Cystamine is produced by a method which comprises reacting a 2,2-dialkyl thiazolidine represented by the general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 independently are alkyl groups of 1 to 5 carbon atoms, with a peroxide in the presence of water. An alkylene oxide adduct of cystamine is produced by a method which comprises reacting the reaction mixture obtained as described above further with an alkylene oxide. These cystamine and alkylene oxide adduct of cystamine are useful as an additive for an aqueous lubricant.Type: GrantFiled: June 25, 1993Date of Patent: November 29, 1994Assignee: Nippon Shokubai Co., Ltd.Inventors: Jun Okamoto, Yujiro Goto, Masao Kitano, Seiichi Suzuki
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Methods for regenerating a sulfur scavenging compound from a product of a sulfur scavenging reaction
Patent number: 5347003Abstract: Methods are provided whereby an N-C-N compound is regenerated from a product of a sulfur scavenging reaction, in which said N-C-N compound removes a sulfur atom from a sulfur compound, to form the original N-C-N compound. The N-C-N compound is represented by the formula (I): ##STR1## The product includes a hetero compound having sulfur, carbon and nitrogen atoms in its backbone. In one embodiment, the product is mixed with (1) a nitrogen compound represented by the formula (II): ##STR2## and (2) an alkaline compound selected from alkali metal, alkaline earth metal and transition metal compounds, to form a solution, slurry or dispersion. The hetero compound is reacted with the nitrogen compound in the presence of the alkaline compound, such that a sulfur atom of the hetero compound is replaced by a nitrogen atom of the nitrogen compound. If necessary, the pH of the solution may be adjusted to about 8 to about 13 to facilitate the reaction. In alternative embodiments, the product also includes an amine complex.Type: GrantFiled: March 5, 1993Date of Patent: September 13, 1994Assignee: Quaker Chemical CorporationInventors: Edward A. Trauffer, Robert D. Evans -
Patent number: 5344990Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: October 5, 1993Date of Patent: September 6, 1994Assignee: Abbott LaboratoriesInventors: William R. Baker, Stephen L. Condon
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Patent number: 5334764Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.Type: GrantFiled: May 6, 1993Date of Patent: August 2, 1994Assignee: The Procter & Gamble CompanyInventors: Jeffrey J. Scheibel, Daniel S. Connor, Robert E. Shumate, James B. St. Laurent
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Patent number: 5326873Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.Type: GrantFiled: June 5, 1992Date of Patent: July 5, 1994Assignee: Eastman Kodak CompanyInventors: Stephen A. Godleski, Yann Hung
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Patent number: 5274054Abstract: Adducts which are obtainable by reacting cycloaliphatic or heterocycloaliphatic polyamines containing at least two primary groups with polyfunctional epoxides containing more than two epoxy groups per molecule in such amounts as to supply 10-100 equivalents of active hydrogen atoms bound to amino nitrogen per one epoxide equivalent, are suitable hardeners for epoxy adhesives, especially adhesives for metals and thermosetting plastics.Type: GrantFiled: April 1, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: Roland Moser, Hans Lehmann, Daniel Bar
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Patent number: 5262570Abstract: A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines of the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined,in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).Type: GrantFiled: January 11, 1993Date of Patent: November 16, 1993Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuuji Shimasaki, Hideaki Tsuneki, Youichi Hino, Tetsuro Hayashi, Michio Ueshima
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Patent number: 5235107Abstract: A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines f the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined, in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).Type: GrantFiled: April 10, 1991Date of Patent: August 10, 1993Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuuji Shimasaki, Hideaki Tsuneki, Youichi Hino, Tetsuro Hayashi, Michio Ueshima