Of Hydroxy Containing Compound Patents (Class 564/478)
  • Patent number: 11858875
    Abstract: A composition includes a perfluorinated propenylamine represented by the following general formula (1): Each occurrence of Rf1 and Rf2 is: (i) independently a linear or branched perfluoroalkyl group having 1-8 carbon atoms and optionally comprises one or more catenated heteroatoms; or (ii) bonded together to form a ring structure having 4-8 carbon atoms and that optionally comprises one or more catenated heteroatoms. At least 60 wt. % of the perfluorinated propenylamine is in the form of the E isomer, based on the total weight of the perfluorinated propenylamine in the composition.
    Type: Grant
    Filed: July 27, 2022
    Date of Patent: January 2, 2024
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: William M. Lamanna, Michael J. Bulinski, Sean M. Smith, Alexandre R. Monteil, Michael G. Costello, John G. Owens
  • Patent number: 9000218
    Abstract: The present application relates to a process for preparing secondary amines by aminating excess primary or secondary alcohols with primary amines in the liquid phase in the presence of copper-comprising catalysts.
    Type: Grant
    Filed: January 9, 2013
    Date of Patent: April 7, 2015
    Assignee: BASF SE
    Inventors: Christof Wilhelm Wigbers, Johann-Peter Melder, Bernd Stein
  • Publication number: 20140343323
    Abstract: Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceeding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.
    Type: Application
    Filed: May 29, 2014
    Publication date: November 20, 2014
    Applicant: RENNOVIA, INC.
    Inventors: Eric L. DIAS, James A. W. SHOEMAKER, Thomas R. BOUSSIE, Vincent J. MURPHY
  • Patent number: 8877977
    Abstract: Process for the preparation of polyalkylenepolyamines by homogeneously catalyzed alcohol amination, in which aliphatic amino alcohols are reacted with one another or aliphatic diamines or polyamines are reacted with aliphatic diols or polyols with the elimination of water in the presence of a homogeneous catalyst and in the presence of hydrogen gas. Polyalkylenepolyamines obtainable by such processes and polyalkylenepolyamines comprising hydroxy groups, secondary amines or tertiary amines. Uses of such polyalkylenepolyamines as adhesion promoters for printing inks, adhesion promoters in composite films, cohesion promoters for adhesives, crosslinkers/curing agents for resins, primers for paints, wet-adhesion promoters for emulsion paints, complexing agents and flocculating agents, penetration assistants in wood preservation, corrosion inhibitors, immobilizing agents for proteins and enzymes.
    Type: Grant
    Filed: November 19, 2012
    Date of Patent: November 4, 2014
    Assignee: BASF SE
    Inventors: Julia Strautmann, Thomas Schaub, Stephan Hueffer, Steffen Maas, Rocco Paciello
  • Patent number: 8865940
    Abstract: Disclosed are processes for preparing 1,6-hexanediol and synthetic intermediates useful in the production of 1,6-hexanediol from renewable biosources. In one embodiment, a process comprises contacting levoglucosenone with hydrogen in the presence of a first hydrogenation catalyst at a first temperature to form product mixture (I); and heating product mixture (I) in the presence of hydrogen and a second hydrogenation catalyst at a second temperature to form product mixture (II) which comprises 1,6-hexanediol. In one embodiment, the 1,6-hexanediol is converted to 1,6-diaminohexane.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta, Christina S Stauffer
  • Patent number: 8835690
    Abstract: The present invention relates to a process for the manufacture of APD and N-alkyl-APD wherein 1-CPD is reacted with aqueous ammonium or aqueous alkyl-amine under alkaline conditions and where the process is conducted in a continuous manner in a reactor comprising a tubular reactor wherein at least two reaction zones are established.
    Type: Grant
    Filed: February 9, 2012
    Date of Patent: September 16, 2014
    Assignee: Borregaard AS
    Inventor: Freddy Tjosas
  • Publication number: 20140228595
    Abstract: Processes include producing hexanediol (HDO), hexamethylenediamine (HMD), adiponitrile (ADN), adipamide (ADM) and derivatives thereof from fermentation broths containing diammonium adipate (DAA), monoammonium adipate (MAA) and/or adipic acid (AA).
    Type: Application
    Filed: September 12, 2011
    Publication date: August 14, 2014
    Applicant: BioAmber S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
  • Patent number: 8791302
    Abstract: A process for preparing an N,N-dialkylethanolamine of the formula I having high color stability where R1 and R2 are each independently a C1- to C8-alkyl group, by reacting ethylene oxide (EO) with a corresponding dialkylamine (R1R2NH) in the presence of water, wherein the reaction is effected continuously in a reactor, the reaction temperature is in the range from 90 to 180° C. and the residence time (RT) in the reactor is in the range from 1 to 7 min, the reactor output is treated thermally at a temperature in the range from 80 to 160° C. over a period in the range from 20 to 1000 min, and then the N,N-dialkylethanolamine is removed by distillation.
    Type: Grant
    Filed: December 16, 2011
    Date of Patent: July 29, 2014
    Assignee: BASF SE
    Inventors: Frank-Friedrich Pape, Johann-Peter Melder, Alfred Krause, Roland Bou Chedid, Martin Rudloff
  • Patent number: 8765634
    Abstract: A catalytically active composition comprising, prior to reduction with hydrogen: 10 to 75% by weight of an oxygen compound of zirconium, calculated as ZrO2; 1 to 30% by weight of an oxygen compound of copper, calculated as CuO; 10 to 50% by weight of an oxygen compound of nickel, calculated as NiO; 10 to 50% by weight of an oxygen compound of cobalt, calculated as CoO; and 0.1 to 10% by weight of one or more oxygen compounds of one or more metals selected from the group consisting of Pb, Bi, Sn, Sb and In, calculated as PbO, Bi2O3, SnO, Sb2O3 or In2O3, respectively.
    Type: Grant
    Filed: October 11, 2011
    Date of Patent: July 1, 2014
    Assignee: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
  • Publication number: 20140135471
    Abstract: Processes that, make nitrogen-containing compounds include converting succinic acid (SA) or monoammonium succinate (MAS) derived from a diammoniurn succinate (DAS)- or MAS-containing fermentation broth to produce such compounds Including diammobmane (DAB), succinic dinitrile (SDN), succinic amino nitrile (SAN), succinamide (DAM), and related polymers.
    Type: Application
    Filed: August 30, 2011
    Publication date: May 15, 2014
    Applicant: BIOAMBER S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
  • Patent number: 8697930
    Abstract: Convert a methylamine (e.g. monomethylamine, dimethylamine and trimethylamine) to a mixture of olefins (e.g. ethylene, propylene and butylene) by placing the methylamine, optionally in a mixture with at least one of ammonia and an inert diluent, in contact with a microporous acidic silicoaluminophosphate catalyst or a microporous aluminosilicate catalyst.
    Type: Grant
    Filed: May 31, 2011
    Date of Patent: April 15, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Robert G. Bowman, Eric E. Stangland, Rainer Bruening, Angelika Heilmann, Roland Wagner, Jason Lee Bronkema
  • Patent number: 8664445
    Abstract: A method for providing a secondary or tertiary amine with formula (R1R2NR3)2NR4 is provided, wherein each of R1 and R2 are chosen from the group consisting of a methyl group, an ethyl group, an iso-propyl group and an n-propyl group; R3 being an alkoxyalkyl group chosen from the group consisting of —CH2CH2OCH2CH2-, —CH2CH2OCH2CH2CH2- and —CH2CH2CH2OCH2CH2CH2-; R4 is chosen from the group consisting of a hydrogen, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group and a group with formula R1R2NR3. The method comprises the steps: (?)reacting R1R2NR3(OH) with ammonia, thereby providing a mixture comprising (R1R2NR3)2NR4; (?) separating (R1R2NR3)2NR4 from said mixture.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: March 4, 2014
    Assignees: Huntsman International LLC, Huntsman Corporation Hungary ZRT
    Inventors: Zsolt Gaspar, Heiko H. Humbert, Gabor Felber, Attila Gaspar, Robert A. Grigsby, Jr., Imre Kordas, Petra Emma Vanderstraeten
  • Patent number: 8618179
    Abstract: The present invention relates to a composition comprising a pesticide and an alkoxylate. Moreover, the invention relates to the alkoxylate, to a process for its preparation and to its use as adjuvant in pesticide-comprising spray mixtures. The invention furthermore relates to a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment. Furthermore, the invention relates to seed comprising the composition.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: December 31, 2013
    Assignee: BASF SE
    Inventors: Paul Klingelhoefer, Arend Jouke Kingma, Sophie Vogel, Kevin Huyghe, Gerd Haderlein, Gerhard Schnabel, Marc Nolte, Richard Roger Evans
  • Publication number: 20130338401
    Abstract: The present invention relates to a process for the manufacture of APD and N-alkyl-APD wherein 1-CPD is reacted with aqueous ammonium or aqueous alkyl-amine under alkaline conditions and where the process is conducted in a continuous manner in a reactor comprising a tubular reactor wherein at least two reaction zones are established.
    Type: Application
    Filed: February 9, 2012
    Publication date: December 19, 2013
    Applicant: BORREGAARD AS
    Inventor: Freddy Tjosas
  • Patent number: 8471065
    Abstract: In another exemplary embodiment, an amine functional curing agent has an Amine Hydrogen Functionality (AHF) of at least 7 and an Amine-Hydrogen Equivalent Weight (AHEW) of at least about 50.
    Type: Grant
    Filed: March 26, 2012
    Date of Patent: June 25, 2013
    Assignee: Huntsman Petrochemical LLC
    Inventors: Bruce L. Burton, Terry L. Renken
  • Patent number: 8383861
    Abstract: The present invention relates to processes for the manufacture of one or more ethanolamines and one or more ethyleneamines starting from the reaction of ethylene oxide with ammonia to produce one or more ethanolamines and the conversion of the ethanolamine(s) to ethyleneamine(s). The present invention also relates to separating alkylethyleneamines from ethyleneamines.
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: February 26, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: David Do, Christopher H. Domke, Jacinto Lopez-Toledo, David M. Petraitis, Thomas Z. Srnak
  • Patent number: 8293944
    Abstract: A reaction apparatus which is used for conducting a gas-liquid chemical reaction in a state that a liquid is in a continuous phase, wherein its reactor has therein a shear type stirring impeller for dispersing a raw reaction gas or a carrier gas and a film-formed catalyst, which apparatus is capable of producing a target reaction product; and a process for producing a tertiary amine in such reaction apparatus.
    Type: Grant
    Filed: January 19, 2012
    Date of Patent: October 23, 2012
    Assignee: Kao Corporation
    Inventors: Atsushi Hirota, Toru Nishimura
  • Patent number: 8288464
    Abstract: A compound having formula (I) wherein R1 is methyl or ethyl; R2 is hydrogen, methyl, CH2C(NH2)(R1)(CH2OH) or R2 groups combine to form a difunctional C2-C6 alkyl group; and X is a difunctional group selected from the group consisting of C2-C20 alkyl, C5-C20 cycloalkyl, C6-C10 aryl, C8-C20 aryl alkyl, C4-C20 heteroalkyl or C10-C20 aryl heteroalkyl.
    Type: Grant
    Filed: December 13, 2011
    Date of Patent: October 16, 2012
    Assignees: Dow Global Technologies LLC, ANGUS Chemical Company
    Inventors: Ian A. Tomlinson, Asghar A. Peera, Glenn Nelson Robinson
  • Publication number: 20120165463
    Abstract: A compound having formula (I) wherein R1 is methyl or ethyl; R2 is hydrogen, methyl, CH2C(NH2)(R1)(CH2OH) or R2 groups combine to form a difunctional C2-C6 alkyl group; and X is a difunctional group selected from the group consisting of C2-C20 alkyl, C5-C20 cycloalkyl, C6-C10 aryl, C8-C20 aryl alkyl, C4-C20 heteroalkyl or C10-C20 aryl heteroalkyl.
    Type: Application
    Filed: December 13, 2011
    Publication date: June 28, 2012
    Inventors: Ian A. Tomlinson, Asghar A. Peera, Glenn Nelson Robinson
  • Patent number: 8134030
    Abstract: A process for preparing a primary amine with a tertiary alpha-carbon atom by reacting a tertiary alcohol with ammonia in the presence of a heterogeneous catalyst, by performing the reaction in the presence of a non-microporous, non-zeolitic aluminosilicate as a catalyst, where the aluminosilicate has a molar Al/Si ratio in the range from 0.1 to 30.
    Type: Grant
    Filed: October 14, 2008
    Date of Patent: March 13, 2012
    Assignee: BASF SE
    Inventors: Marcus Sigl, Thomas Heidemann
  • Patent number: 8119843
    Abstract: A reaction apparatus which is used for conducting a gas-liquid chemical reaction in a state that a liquid is in a continuous phase, wherein its reactor has therein a shear type stirring impeller for dispersing a raw reaction gas or a carrier gas and a film-formed catalyst, which apparatus is capable of producing a target reaction product; and a process for producing a tertiary amine in such reaction apparatus.
    Type: Grant
    Filed: August 9, 2010
    Date of Patent: February 21, 2012
    Assignee: Kao Corporation
    Inventors: Atsushi Hirota, Toru Nishimura
  • Patent number: 8063252
    Abstract: Processes comprising: (i) providing a reactant selected from the group consisting of primary alcohols, secondary alcohols, aldehydes, ketones and mixtures thereof; and (ii) reacting the reactant with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary amines, secondary amines and mixtures thereof, in the presence of a catalyst comprising a zirconium dioxide- and nickel-containing catalytically active composition, to form an amine; wherein the catalytically active composition, prior to reduction with hydrogen, comprises oxygen compounds of zirconium, copper, nickel and cobalt, and one or more oxygen compounds of one or more metals selected from the group consisting of Pb, Bi, Sn, Sb and In.
    Type: Grant
    Filed: July 4, 2007
    Date of Patent: November 22, 2011
    Assignee: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
  • Patent number: 7999138
    Abstract: A process is disclosed for the production of olefins including ethylene, propylene, and butanes from methyl amine. The process comprises a reaction whereby methyl amine produces the olefin and ammonia by pyrolysis. The reaction is carried out in the gas phase at a temperature in the range of 400° C. to 700° C.
    Type: Grant
    Filed: January 21, 2010
    Date of Patent: August 16, 2011
    Inventor: John E. Stauffer
  • Patent number: 7951974
    Abstract: In the continuous process for preparing alkylamines by reacting C1-4-alkanols with ammonia in the gas phase in the presence of a shape-selective fixed-bed catalyst in a cooled reactor, the shape-selective fixed-bed catalyst is present in a single contiguous fixed bed in the reactor and tubes through which coolants are passed run within the fixed bed to regulate the temperature of the fixed bed.
    Type: Grant
    Filed: April 30, 2010
    Date of Patent: May 31, 2011
    Assignee: BASF Aktiengesellschaft
    Inventors: Marco Bosch, Roderich Röttger, Bernd Stein, Thomas Krug, Johann-Peter Melder, Theodor Weber
  • Publication number: 20110009627
    Abstract: The invention relates to a reactor for performing high-pressure reactions, comprising at least one tube (31) whose ends are each conducted through a tube plate (33) and which is bonded to the tube plate (33). The tube plates (33) and the at least one tube (31) are surrounded by an outer jacket, such that an outer space (39) is formed between the tube (31) and the outer jacket. The tube plates (33) each have at least one surface composed of a nickel-base alloy and the at least one tube (31) is in each case welded on to the surface composed of the nickel-base alloy. The surface composed of the nickel-base alloy points in each case in the direction of the particular reactor end. The outer jacket has a thickness which is sufficient to absorb tensile forces which occur between tube (31) and outer jacket owing to a temperature difference in the event of different expansion. The invention further relates to a process for starting up the reactor and for performing an exothermic reaction in the reactor.
    Type: Application
    Filed: January 21, 2009
    Publication date: January 13, 2011
    Applicant: BASF SE
    Inventors: Helmut Schmidtke, Wilhelm Ruppel, Helmut Berrsche, Johann-Peter Melder, Udo Rheude, Petr Kubanek, Gerhard Ruf, Wolfgang Gunkel, Wolfgang Mägerlein, Karl-Heinz Ross
  • Publication number: 20100298608
    Abstract: Disclosed is a process for producing a tertiary amine from a primary or secondary amine and alcohol as corresponding starting materials, which includes step (i) of dehydrogenating an alcohol to obtain an aldehyde, step (ii) of reacting the aldehyde with a primary or secondary amine to obtain a primary or secondary amine adduct, and step (iii) of hydrogenating the primary or secondary amine adduct to obtain a tertiary amine, wherein step (ii) is carried out independently of the other steps.
    Type: Application
    Filed: December 26, 2006
    Publication date: November 25, 2010
    Applicant: KAO CORPORATION
    Inventors: Shoji Hasegawa, Toru Nishimura, Atsushi Hirota
  • Publication number: 20100298600
    Abstract: Disclosed herein is a method for chemically attaching carboxyl, alcohol, amine or amide groups to the surface of nanodiamond (ND) in a liquid phase. Also disclosed herein are a functional ND compound obtained by the method and use thereof. The method includes treating synthetic ND with a size of 1 nm-1OO nm with sonication and a strong acid to provide ND-(COOH)n. The ND-(COOH)n compound is used as a starting material to provide ND compounds having alcohol, amine or amide groups attached to the surfaces thereof. The surface-functionalized ND compounds are characterized by using an X-ray diffractometer, FTIR, AFM, particle size analyzer and zeta sizer. The ND compounds show functionalities as well as high solubility to provide stable ND solutions in a liquid phase. Therefore, the ND compounds may be used as diamond coating agents. The powder of the ND compounds may be used as materials for producing composites of polymers, plastics, synthetic fibers, ceramics, etc.
    Type: Application
    Filed: October 9, 2008
    Publication date: November 25, 2010
    Applicant: NANODIAMOND INC.
    Inventor: Min Yung Lee
  • Publication number: 20100087684
    Abstract: The present invention relates to processes for the manufacture of one or more ethanolamines and one or more ethyleneamines starting from the reaction of ethylene oxide with ammonia to produce one or more ethanolamines and the conversion of the ethanolamine(s) to ethyleneamine(s). The present invention also relates to separating alkylethyleneamines from ethyleneamines.
    Type: Application
    Filed: October 6, 2009
    Publication date: April 8, 2010
    Inventors: David Do, Christopher H. Domke, Jacinto Lopez-Toledo, David M. Petraitis, Thomas Z. Srnak
  • Patent number: 7678755
    Abstract: A modified polyol compound having alkoxylation and having at least one anionic capping unit, uses of the modified polyol compound having alkoxylation and having at least one anionic capping unit and cleaning compositions comprising the same.
    Type: Grant
    Filed: April 15, 2009
    Date of Patent: March 16, 2010
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey John Scheibel, Julie Ann Menkhaus, Xinbei Song, Eva Schneiderman
  • Patent number: 7550631
    Abstract: Uses of a modified polyol compound having alkoxylation and having at least one anionic capping unit.
    Type: Grant
    Filed: September 24, 2007
    Date of Patent: June 23, 2009
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey John Scheibel, Julie Ann Menkhaus, Xinbei Song, Eva Schneiderman
  • Patent number: 7547805
    Abstract: The present invention relates to a process for the production of severely sterically hindered amino-ether alcohols using a catalyst based on the combination of one or more catalytically active metals supported in a dispersed form on one or more ordered mesoporous materials as support.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: June 16, 2009
    Assignee: Exxonmobil Research and Engineering Company
    Inventors: Andrzej Malek, Christine Nicole Elia, Adeana Richelle Bishop, Edmund John Mozeleski, Michael Siskin
  • Patent number: 7538080
    Abstract: A modified polyol compound having alkoxylation and having at least one anionic capping unit, uses of the modified polyol compound having alkoxylation and having at least one anionic capping unit and cleaning compositions comprising the same.
    Type: Grant
    Filed: September 24, 2007
    Date of Patent: May 26, 2009
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey John Scheibel, Julie Ann Menkhaus, Xinbei Song, Eva Schneiderman
  • Patent number: 7411095
    Abstract: A method for producing highly pure enamines, which comprises reacting an aldehyde or ketone with an amine and treating the resulting reaction mixture with an acidic aqueous solution at a temperature between 0° C. and 30° C.
    Type: Grant
    Filed: January 18, 2005
    Date of Patent: August 12, 2008
    Assignee: Sankyo Company, Limited
    Inventors: Rei Okazaki, Shunshi Kojima, Hideharu Yokokawa
  • Publication number: 20070179320
    Abstract: The invention provides a method for manufacturing a tertiary amine, including reacting a tertiary amine with an alcohol and a primary or secondary amine in a reactor loaded with a film type catalyst, controlling the superficial velocity of liquid in the reactor at 0.1 cm/s or more.
    Type: Application
    Filed: January 29, 2007
    Publication date: August 2, 2007
    Applicant: KAO CORPORATION
    Inventors: Atsushi Hirota, Toru Nishimura
  • Patent number: 6924315
    Abstract: 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: Grant
    Filed: March 13, 2003
    Date of Patent: August 2, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Christine Peck Kretz, Michael Edward Ford, Kevin Rodney Lassila
  • Patent number: 6855776
    Abstract: Improved amine-terminated polybutadienes (ATPBs) having one or two terminal groups of the formula —CHRNH2 wherein R is C1-C20 alkyl, are prepared by aminating a secondary hydroxyl-terminated polybutadiene having no ether groups. The ATPBs may be hydrogenated or partially hydrogenated, either prior to or after the animation, to saturate or partially saturate the polymers. Preferred ATPBs are of the formula H2NCHR-(polybutadiene)-CHRNH2 wherein R is C1-C20 alkyl. Polyureas, polyurethanes, crosslinked epoxies, polyamides, and other derivatives with improved properties can be prepared from the ATPBs. The resultant derivatives are useful in liquid binders for braking systems, electric potting compositions, coatings, adhesives, sealants, and water proofing membranes, for example.
    Type: Grant
    Filed: November 20, 2002
    Date of Patent: February 15, 2005
    Assignee: Sartomer Technology Company, Inc.
    Inventors: Herbert Shin-I Chao, John Schmidhauser, Alain Robert Drexler, Nan Tian
  • Patent number: 6469214
    Abstract: A process for the preparation of one or more ethanolamines (I), chosen from the group consisting of monoethanolamine, diethanolamine and triethanolamine, by conversion of one or more ethanolamines (II) different from the ethanolamine(s) (I), chosen from the group consisting of monoethanolamine, diethanolamine, triethanolamine. O,N,N-tris(2-hydroxyethyl) ethanol-N-(2-aminoethyl)-ethanolamine, N-(2-amine, hydroxy ethyl) piperazine, N-(2-hydroxyethyl)morpholine and N,N′-bis(2-hydroxyethyl)piperazine, where the ethanolamine(s) (II), optionally in the presence of ammonia, is/are treated with a strong base.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: October 22, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Johann-Peter Melder, Gerhard Schulz
  • Patent number: 6403834
    Abstract: The invention concerns a method for preparing tris(ether-amines) of formula (I): N[A—O—(B—O)n—R]3 wherein R, A, B and n are as defined in Claim 1, comprising the reaction, in liquid phase, of an alkylene-glycol monoether of formula (II): HO—A—O—(B—O)nR wherein R, A, B and n are as defined in Claim 1, with an ammonolysis agent selected among ammonia and an etheramine of formula (I′): H3-pN[A—O—(B—O)nR]p wherein: A, B, n and R are as defined in Claim 1 and p represent 1 or 2, at a temperature ranging between 100 and 250° C., by contacting reagents with a hydrogenation-dehydrogenation catalyst.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: June 11, 2002
    Assignee: Rhodia Chimie
    Inventors: Michel Alas, Albert Bouniot
  • Patent number: 5976202
    Abstract: Reaction products of polyolefins having predominantly a terminal double bond and a number average molecular weight of from 250 to 10,000, which possess an aliphatic hydrocarbon skeleton which is straight-chain or carries C.sub.1 -C.sub.4 -alkyl side chains, with from 1 to 10 mol, per equivalent of double bond, of one or more vinyl esters I ##STR1## are obtainable by reacting the stated polyolefins with the vinyl esters I in the presence of a free radical initiator at from 80 to 200.degree. C., it being possible for these reaction products subsequently to have been hydrolyzed to the corresponding alcohols or converted into the corresponding amines by reductive amination with amines II ##STR2## .
    Type: Grant
    Filed: July 20, 1995
    Date of Patent: November 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Peter Rath, Helmut Mach, Harald Schwahn, Hans-Joachim Muller, Wolfgang Reif, Thomas Ruhl
  • Patent number: 5808158
    Abstract: A process for producing primary amines which comprises reacting primary alcohols branched in position 2 with ammonia in the presence of a metal catalyst/co-catalyst.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: September 15, 1998
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Martin Conrads, Albert Thomas Hermann, Erich Scherf, Arwed Wagner
  • Patent number: 5696293
    Abstract: The present invention provides a catalyst composition for producing a polyether polyamine, comprising:(a) ruthenium and(b) at least one of metals selected from the group consisting of palladium, platinum, rhodium, osmium, iridium, rhenium, technetium, molybdenum and tungsten on a carrier.
    Type: Grant
    Filed: April 1, 1996
    Date of Patent: December 9, 1997
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Christopher Harold Phillips, Yoji Hirasawa, Keiichi Okajima, Julius John Batty, Brian Lewis Booth
  • Patent number: 5364971
    Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a ruthenium on alumina hydrogenation catalyst. The catalyst for the polyamine decolorization process preferably has at least 0.5 wt. % Ru. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenareal, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: November 15, 1994
    Assignee: Texaco Chemical Inc.
    Inventor: Wei-Yang Su
  • Patent number: 5362914
    Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a cobalt on alumina hydrogenation catalyst promoted with copper and chromium. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenated, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: November 8, 1994
    Assignee: Texaco Chemical Inc.
    Inventor: Wei-Yang Su
  • Patent number: 5331102
    Abstract: Color-containing alkanolamines or alkyleneamines, having color numbers of up to 100 PtCo or higher, can be treated with inorganic solid acidic catalysts. Inorganic support materials having bonded inorganic acid functionalities may be used as the inorganic solid acidic catalysts. In the presence of water, these inorganic solid acidic catalysts produce decolorized alkanolamines or alkyleneamines having color numbers of 20 PtCo or less. The process of decolorization can be carried out in batch or continuous mode processes thus providing low cost, high quality and high purity end products.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: July 19, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Charles A. Gibson
  • Patent number: 5256786
    Abstract: A process of reforming cyclic alkyleneamines to amine-extended cyclic alkyleneamines involving contacting a cyclic alkyleneamine or mixture of cyclic alkyleneamines in the liquid phase with a catalyst under reaction conditions. The catalyst is selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB and VB, and (d) specified tungsten oxides. For example, piperazine or a mixture of piperazine and aminoethylpiperazine is contacted with magnesium silicate to yield a mixture of amine-extended piperazines, including 1,2-bis(piperazinyl)-ethane and N,N'-bis(2-piperazinylethyl)piperazine.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: October 26, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5237113
    Abstract: Haloalcohols of the general formula IHal--X--OH (I)where X is straight-chain or branched, substituted or unsubstituted alkylene of 4 or more carbon atoms in the chain, which may be interrupted by one or more heteroatoms, and Hal is halogen, are prepared by reacting a diol of the general formula IIHO--X--OH (II)where X has the above meanings, with an aqueous hydrogen halide solution in a water-immiscible organic solvent which is inert under the reaction conditions, at from 50.degree. to 150.degree. C., using an excess of hydrogen halide, based on the diol of the general formula II, of from 10 to 200 mole percent and setting a volume ratio of inorganic phase: organic phase of from 1:2 to 1:50.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: August 17, 1993
    Assignee: BASF Altiengesellschaft
    Inventors: Rainer Becker, Wolfgang Mackenroth, Walter Seufert
  • Patent number: 5183923
    Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: February 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza
  • Patent number: 5103058
    Abstract: Process for producing aliphatic imines and/or amines from aliphatic monohydric alcohols, such as higher molecular weight oxo alcohols, including ether alcohols, comprising the steps of dehydrogenating the alcohol to an aldehyde in situ in the presence of a zinc oxide and/or zinc salt/metal hydroxide dehydrogenation catalyst and a soluble amount of a primary aliphatic amine which condenses immediately with the aldehyde under reflux conditions, with continuous water removal, to form the corresponding aliphatic imine (Schiff base). The corresponding aliphatic amine can be formed by reducing or reductively aminating the imine in known manner to form corresponding primary, secondary or tertiary amines as desired.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: April 7, 1992
    Assignee: Exxon Chemical Patents Inc
    Inventors: Roy L. Pruett, Michael J. Keenan, Edmund J. Mozeleski
  • Patent number: 5015773
    Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: May 14, 1991
    Assignee: BP Chemicals Limited
    Inventor: Ian D. Dobson
  • Patent number: 4994622
    Abstract: Mono- and di-lower alkylamines, e.g. methylamine or dimethylamine, are alkylated by reaction with C.sub.8-22 alcohol in the presence of hydrogen at a temperature of about 150.degree.-275.degree. C. in contact with a copper-zinc-alkaline earth metal base containing catalyst (e.g., CuO-ZnO-Ba(OH).sub.2) while removing water formed in the reaction.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: February 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer