Polytetramethylene Glycols Patents (Class 568/617)
  • Patent number: 11505762
    Abstract: A composition comprising water, a glycol, and a polyalkylene glycol which has a biodegradability of at least 60% as determined using OECD 301F wherein the composition has a kinematic viscosity of at least 25 mm2/sec at 40° C. is useful as a rheology modifier, particularly in subsea applications. In some instances, the composition comprises 10 to 65 weight % water, 20 to 60 weight % of a glycol selected from ethylene glycol, diethylene glycol, triethylene glycol and tetra ethylene glycol, 10 to 40 weight % of a polyalkylene glycol, and 0 to 10% of additives based on total weight of the composition wherein the polyalkylene glycol has a—molecular weight of no more than 4000 g/mol and is characterized in that it is an oxyethylene/oxypropylene block copolymer having a weight percent of oxyethylene of at least 20% based on total weight of the copolymer.
    Type: Grant
    Filed: October 3, 2019
    Date of Patent: November 22, 2022
    Assignee: DOW GLOBAL TECHNOLOGIES LLC
    Inventor: Martin R. Greaves
  • Patent number: 9932316
    Abstract: Novel imidazolium salts of formula (I) are described in which R is a C1-C14 alkyl group, optionally substituted by one or more fluorine atoms, or a C2-C18 alkoxyalkyl group, R? is an alkyl group containing at least 8 carbon atoms, at least 6 of which are partially or entirely fluorinated, R? is hydrogen or C1-C3 alkyl, Z is an organic or inorganic anion, and Q is further defined. The compounds of formula (I) are liquid crystals over a wide temperature range, and are characterized by high conductivity, hydrophobicity and stability. These properties made them ideally suitable for use in devices based on electrochemical reactions, such as solar cells, fuel cells, electrochemical sensors, lithium batteries and capacitors, etc.
    Type: Grant
    Filed: June 10, 2010
    Date of Patent: April 3, 2018
    Assignee: DAUNIA SOLAR CELL S.R.L.
    Inventors: Giuseppe Resnati, Pierangelo Metrangolo, Antonio Abate, Francesco Matteucci
  • Patent number: 9434706
    Abstract: A 1,4-butanediol (1,4BG)-containing composition having high thermal stability, and having a concentration of 1,4-butanediol of 99.00% by weight or more and not more than 99.99% by weight and 2-pyrrolidone or N-methylpyrrolidone in a concentration, as converted into a nitrogen atom, of from 1.0 to 25 ppm by weight.
    Type: Grant
    Filed: January 8, 2014
    Date of Patent: September 6, 2016
    Assignee: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Yusuke Izawa, Masaru Utsunomiya, Norikazu Konishi, Kouta Tanaka, Takayuki Suzuki, Shinichirou Matsuzono
  • Patent number: 9051422
    Abstract: A water-soluble thermally polymerizable oxetane resin composition comprises (A) a water-soluble oxetane compound and (B) at least one heteropolyacid compound selected from heteropolyacids and heteropolyacid salts. The water-soluble oxetane compound may contain one or more oxetane functional groups in the molecule and one or more alcoholic OH groups in the molecule. The heteropolyacids include phosphotungstic acid, phosphomolybdic acid, silicotungstic acid, silicomolybdic acid or mixtures thereof. The heteropolyacid salts include phosphotungstic acid salts, phosphomolybdic acid salts, silicotungstic acid salts, silicomolybdic acid salts or mixtures thereof.
    Type: Grant
    Filed: September 13, 2007
    Date of Patent: June 9, 2015
    Assignee: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
    Inventors: Atsuhiko Katayama, Keiji Banno, Niranjan Kumar Shrestha, Toshihide Senzaki
  • Patent number: 9040753
    Abstract: A filtration method is disclosed for recovering purified polyether polyol comprising the steps of providing an aqueous solution of a polyether polyol containing an alkali metal catalyst residual formed from a transesterification process utilizing an alkali metal catalyst, contacting the aqueous solution with a stoichiometric excess of magnesium sulfate, magnesium sulfite or a combination thereof to form a second aqueous solution, wherein said stoichiometric excess is based on the amount of said alkali metal catalyst residual.
    Type: Grant
    Filed: July 19, 2012
    Date of Patent: May 26, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventor: Glen Jih-Chao Chen
  • Publication number: 20140378712
    Abstract: The present invention provides an improved process for converting a diester of polyether polyol, e.g., PTMEA, to the corresponding dihydroxy product, e.g., polytetramethylene ether glycol (PTMEG) continuously in a reaction zone, such as, for example, a reactive distillation system, for achieving virtually complete conversion of PTMEA to PTMEG, and recovery of PTMEG free of unreacted or unconverted PTMEA and alkanol ester by-product.
    Type: Application
    Filed: January 25, 2013
    Publication date: December 25, 2014
    Applicant: INVISTA North America S.a.r.l.
    Inventors: Suri N. Dorai, Clive Alexander Hamilton, Qun Sun
  • Publication number: 20140213828
    Abstract: A filtration method is disclosed for recovering purified polyether polyol comprising the steps of providing an aqueous solution of a polyether polyol containing an alkali metal catalyst residual formed from a transesterification process utilizing an alkali metal catalyst, contacting the aqueous solution with a stoichiometric excess of magnesium sulfate, magnesium sulfite or a combination thereof to form a second aqueous solution, wherein said stoichiometric excess is based on the amount of said alkali metal catalyst residual.
    Type: Application
    Filed: July 19, 2012
    Publication date: July 31, 2014
    Applicant: INVISTA North America S.a r.I.
    Inventor: Glen Jih-Chao Chen
  • Publication number: 20140058056
    Abstract: Provided herein is a non-naturally occurring microbial organism having a methanol metabolic pathway that can enhance the availability of reducing equivalents in the presence of methanol. Such reducing equivalents can be used to increase the product yield of organic compounds produced by the microbial organism, such as 1,4-butanediol (BDO). Also provided herein are methods for using such an organism to produce BDO.
    Type: Application
    Filed: August 26, 2013
    Publication date: February 27, 2014
    Applicant: Genomatica, Inc.
    Inventors: Anthony P. Burgard, Robin E. Osterhout, Stephen J. Van Dien, Cara Ann Tracewell, Priti Pharkya, Stefan Andrae
  • Patent number: 8481788
    Abstract: The present invention aims to provide a method for producing a polyalkylene oxide, which is capable of improving reduction in reactivity of a double metal cyanide complex catalyst in the case that a low molecular weight initiator is used, and producing the polyalkylene oxide with high productivity at low cost. The method for producing a polyalkylene oxide comprises carrying out a ring-opening addition reaction of an alkylene oxide with an initiator having at least one hydroxy group and having a molecular weight of not more than 300 per hydroxy group in the presence of a double metal cyanide complex catalyst in an organic solvent, wherein the organic solvent is used in an amount of 500 to 1,500 parts by weight relative to 100 parts by weight of the alkylene oxide used at the start of the reaction.
    Type: Grant
    Filed: January 21, 2009
    Date of Patent: July 9, 2013
    Assignee: Kaneka Corporation
    Inventors: Hidetoshi Odaka, Takuya Maeda, Kiyotaka Bito, Michihide Homma
  • Patent number: 8053607
    Abstract: A method for producing a polyether-polyol having a narrow molecular weight distribution, which comprises carrying out selective fractional extraction of the low-molecular weight component from a polyether-polyol (A) having an average molecular weight of from 500 to 4500 represented by formula (1): HO—[(CH2)4O]n—[(CR1R2)pO]q—H??(1) wherein R1 and R2, which may be the same or different, each represents a hydrogen atom or a linear or branched alkyl group having from 1 to 5 carbon atoms; n indicates a positive integer; p indicates an integer of from 1 to 8; and q indicates 0 or a positive integer, by the use of an aqueous solution (C) containing from 15 to 70 wt % sulfuric acid at a room temperature to 100° C., to thereby suitably determine the amount of the aqueous sulfuric acid solution to the overall organic layer and the sulfuric acid concentration in accordance with the molecular weight and molecular weight distribution of the intended polyether-polyol to be fractionally extracted.
    Type: Grant
    Filed: December 19, 2003
    Date of Patent: November 8, 2011
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Kazuaki Okabe, Hiroshi Nakaoka, Ikuhiko Kanehira
  • Patent number: 7795476
    Abstract: Compositions comprising polytetramethylene glycol and a volatile material (e.g. a perfume) are able to sustainedly release said volatile material and are easy to disperse in liquid and cream products.
    Type: Grant
    Filed: August 1, 2005
    Date of Patent: September 14, 2010
    Assignee: The Procter & Gamble Company
    Inventors: Italo Corzani, Calum MacBeath, Manuel Mariani
  • Patent number: 7544766
    Abstract: The present invention relates to a process for preparing polytetrahydrofuran, polytetrahydrofuran copolymer, diester or monoester by polymerizing tetrahydrofuran in the presence of at least one telogen and/or comonomer and of an acidic heterogeneous catalyst based on activated sheet silicates or mixed metal oxides in a fluidized bed.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: June 9, 2009
    Assignee: BASF SE
    Inventors: Stephan Schlitter, Martin Haubner, Peter Zehner, Michael Hesse, Alexander Weck, Rolf Pinkos, Thomas Graβler
  • Patent number: 7528287
    Abstract: This invention relates to a process comprising using ionic liquids for preparing poly(tetramethylene) glycol from tetrahydrofuran.
    Type: Grant
    Filed: September 22, 2006
    Date of Patent: May 5, 2009
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Jemma Vickery, Robert Miller
  • Patent number: 7402711
    Abstract: This invention relates to a process comprising using ionic liquids for preparing poly(tetramethylene)glycol from tetrahydrofuran.
    Type: Grant
    Filed: September 22, 2006
    Date of Patent: July 22, 2008
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Leo Ernest Manzer
  • Patent number: 7342142
    Abstract: A process comprising contacting PO3G having color with hydrogen in the presence of a hydrogenation catalyst, wherein the PO3G, after hydrogenation, has a APHA color of less than about 50.
    Type: Grant
    Filed: August 5, 2003
    Date of Patent: March 11, 2008
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Mayis Seapan, George Francis Diffendall, Francis Glenn Gallagher
  • Patent number: 7276573
    Abstract: The present invention provides a process for preparing mono- or diesters of polytetrahydrofuran or of tetrahydrofuran copolymers by polymerizing tetrahydrofuran in the presence of at least one telogen and/or of a comonomer over an acidic catalyst, wherein the polymerization reactor is started up using a mixture of polytetrahydrofuran, the mono- or diesters of polytetrahydrofuran and/or of the THF copolymers, tetrahydrofuran, any comonomer and at least one carboxylic acid and/or one carboxylic anhydride.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: October 2, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Pinkos, Achim Gerstlauer, Martin Haubner, Stephan Schlitter, Stefan Käshammer, Klaus-Peter Pfaff
  • Patent number: 7071364
    Abstract: A detergent composition having cold water solubility and exhibiting high calcium tolerance can be produced from biodegradable branched ether derivative compositions derived from a branched ether primary alcohol represented by the formula: wherein R1 represents hydrogen or a hydrocarbyl radical having from 1 to 3 carbon atoms, R2 represents a hydrocarbyl radical having from 1 to 7 carbon atoms, x is a number ranging from 0 to 16, preferably from 3 to 13, wherein the total number of carbon atoms in the alcohol ranges from 9 to 24.
    Type: Grant
    Filed: October 3, 2003
    Date of Patent: July 4, 2006
    Assignee: Shell Oil Company
    Inventors: Charles Lee Edwards, Kirk Herbert Raney, Paul Gregory Shpakoff
  • Patent number: 6989432
    Abstract: A copolymer with recurring constituent units derived by polymerizing tetrahydrofuran, ethylene oxide and at least one additional cyclic ether that can be substituted or unsubstituted that decreases the hydrophilicity imparted to the copolymer by the ethylene oxide.
    Type: Grant
    Filed: January 8, 2003
    Date of Patent: January 24, 2006
    Assignee: Invista North America S.a.r.l.
    Inventors: Gerfried Pruckmayr, Charles Francis Palmer, Jr., Gary Arthur Lodoen
  • Patent number: 6987201
    Abstract: The present invention provides acetic anhydride, a method of purifying crude acetic anhydride, and a method of producing polyoxytetramethylene glycol using acetic anhydride. A method of producing polyoxytetramethylene glycol by ring-opening-polymerizing tetrahydrofuran in the presence of acetic anhydride and an acid catalyst, wherein said ring-opening polymerization is conducted using acetic anhydride having a diketene concentration of 10 ppm or less to produce polyoxytetramethylene glycol.
    Type: Grant
    Filed: February 16, 2001
    Date of Patent: January 17, 2006
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Seiji Nishioka, Ryosuke Maeda, Toshifumi Fukui, Mitsuru Yamashita
  • Patent number: 6979752
    Abstract: A continuous process for converting by transesterification the diester of polytetramethylene ether (PTMEA) to the corresponding polytetramethylene ether glycol (PTMEG). The process is characterized by the fact that the feed, consisting of PTMEA along with an alkanol (preferably methanol) and with an alkali metal oxide, hydroxide or alkoxide catalyst (preferably sodium methaoxide) is made to react in two multistaged reactions in series. In the first reactant, including stages of retention in association with distillation trays of high efficiency, the bulk of conversion is achieved by stripping the alkanol ester formed in the transesterification with vapors of hot alkanol having a reduced content of alkanol ester. The transesterification is completed in the second reaction by stripping the effluent from the first reactor with vapors of hot alkanol almost free of alkanol ester.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: December 27, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Aldo Bertola, Salvatore Cassarino, Myriam Hobe
  • Patent number: 6972317
    Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: December 6, 2005
    Assignee: OMNOVA Solutions Inc.
    Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
  • Patent number: 6891013
    Abstract: The present invention provides, inter alia, novel fluorinated polyurethane elastomers (e.g., fluorinated thermoset polyurethane elastomers and fluorinated thermoplastic elastomers) prepared from polyether prepolymers formed from mono-substituted fluorinated oxetane monomers (FOX monomers) and tetrahydrofuran (THF). In addition, the present invention provides methods of making such fluorinated polyurethane elastomers.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: May 10, 2005
    Assignee: Aerojet-General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald
  • Patent number: 6858757
    Abstract: A process for preparing perfluoropolyoxyalkylenes having —OCF2H, —OCF2CF2H and —OCF(CF3)H end groups and a number average molecular weight from 120 to 3,000, by decarboxylation of the corresponding perfluoropolyoxyalkylenes having —OCF2COOH, —OCF2CF2COOH, —OCF(CF3)COOH end groups, in the presence of catalytic amounts of salts formed by perfluoropolyoxyalkylenes having end groups selected from —OCF2COOZ, —OCF2CF2COOZ and —OCF(CF3)COOZ, wherein Z is a monovalent cation of the group Ia or Ib or Z is —NR4+ wherein R is hydrogen or a C1-C4 alkyl, using ratios between Z and the —COOH equivalents of the perfluoropolyoxyalkylenes to be decarboxylated from 0.01 to 0.08, at a temperature between 120° C. and 180° C., in the presence of water, at pH <5 and at a pressure comprised between 2 and 80 atmospheres.
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: February 22, 2005
    Assignee: Solvay Solexsis S.p.A.
    Inventors: Giuseppe Marchionni, Gianfranco Spataro
  • Patent number: 6780928
    Abstract: A polyoxyalkylene monoalkyl ether which gives, in gel permeation chromatography, a chromatogram which satisfies a relation expressed by an equation: S1/S0≦0.
    Type: Grant
    Filed: August 22, 2003
    Date of Patent: August 24, 2004
    Assignee: NOF Corporation
    Inventors: Akinori Itoh, Susumu Honda, Tatsuya Matsui, Yoshihiro Hayashi
  • Patent number: 6699961
    Abstract: A process for the preparation of a DMC catalyst useful in the polymerization of alkylene oxides into polyether polyols, which process having the steps of (a combining an aqueous solution of a metal salt with an aqueous solution of a metal salt with an aqueous solution of a metal cyanide salt and reacting these solutions, wherein at least part of this reaction takes place in the presence of an organic complexing agent, thereby forming a dispersion of a solid DMC complex in an aqueous medium; (b) combining the dispersion obtained in step (a) with a liquid, which is essentially insoluble in water and which is capable of extracting the solid DMC complex formed in step (a) from the aqueous medium, and allowing a two-phase system to be formed consisting of a first aqueous layer and a layer containing the DMC complex and the liquid added; (c) removing the first aqueous layer; and (d) recovering the DMC catalyst from the layer containing the DMC catalyst.
    Type: Grant
    Filed: September 24, 2002
    Date of Patent: March 2, 2004
    Assignee: Shell Oil Company
    Inventors: Michiel Barend Eleveld, Riemer Alberts De Groot, Ronald Van Kempen, Johan Paul Smit
  • Patent number: 6680406
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: January 20, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6586564
    Abstract: The invention relates to double-metal cyanide (DMC) catalysts for preparing polyether polyols by the polyaddition of alkylene oxides on to starter compounds containing active hydrogen atoms, wherein the DMC catalysts are composed of: a) at least one DMC compound; b) at least one organic complexing ligand which is not a coronand; and c) at least one coronand. The DMC catalysts of the present invention have increased activity compared to known catalysts.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: July 1, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schäfer, Jörg Hofmann, Pieter Ooms
  • Patent number: 6570041
    Abstract: Disclosed is a high heat resistance and low viscosity polyoxytetramethylene glycol (PTMG) having the following characteristics (1) to (4): (1) a number average molecular weight of from 500 to 3000; (2) a molecular weight distribution of 1.8 or less in terms of the Mw/Mn ratio; (3) a content of high molecular weight PTMG molecules of from 2 to 5% by weight, wherein the high molecular weight PTMG molecules are PTMG molecules having molecular weights which are at least six times as large as the number average molecular weight of all PTMG molecules; and (4) a heteropolyacid content of from 10 to 900 ppb by weight.
    Type: Grant
    Filed: January 22, 2002
    Date of Patent: May 27, 2003
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Tamotsu Kodama, Takeshi Mori, Takaharu Akedo
  • Patent number: 6566563
    Abstract: A process for making OH-terminated compounds involving: (a) combining at least one CH2OH-terminated diol and a titanium-containing catalyst to form a reaction mixture; (b) heating the reaction mixture to a temperature of from 110 to 160° C. to form a heated reaction mixture; (c) continuously adding dimethyl carbonate to the heated reaction mixture; (d) continuously distilling all methanol released from the heated reaction mixture; (e) heating the reaction mixture to a temperature of from 190 to 240° C. to form an OH-terminated product; (f) removing unreleased methanol and dimethyl carbonate from the reaction mixture under a pressure of less than 100 mbar; and (g) deactivating the titanium-containing catalyst by adding from 0.8 to 2 equivalents, based on the catalyst, of a 1 to 20% by weight aqueous solution of phosphoric acid to the reaction mixture, at a temperature of from 80 to 120° C.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: May 20, 2003
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Alfred Westfechtel, Roland Gruetzmacher, Elke Grundt
  • Patent number: 6559278
    Abstract: The invention relates to a method for continuously or discontinuously producing tetrahydrofuran polymers by homopolymerization of tetrahydrofuran, alkyl-substituted tetrahydrofurans and/or alkylene oxides in the presence of carboxylic acid anhydrides or compounds containing reactive hydrogen using an optionally non-acidified or acid-activated calcined and granular natural amorphous aluminum silicate catalyst. The inventive method provides a means for substantially suppressing the formation of cyclic ethers and for obtaining a polymer with a narrow molecular weight distribution by keeping the concentration of carboxylic acid anhydrides or alkylene oxide constantly below 1 wt. % during polymerization. The catalysts have a long life span and lead to polymers that are characterized by highly uniform properties and a narrow molecular weight distribution even if a fairly impure monomer is used.
    Type: Grant
    Filed: March 30, 2001
    Date of Patent: May 6, 2003
    Inventor: Herbert Müller
  • Patent number: 6414109
    Abstract: Provided is a process for producing a tetrahydrofuran polymer using a heteropoly-acid catalyst wherein the content of Al in the heteropoly-acid is 4 ppm or less.
    Type: Grant
    Filed: February 11, 2000
    Date of Patent: July 2, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventor: Takaharu Akedo
  • Patent number: 6403842
    Abstract: Disclosed are a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and a carboxylic acid anhydride, wherein the carboxylic acid anhydride has a ketene dimer content of 50 ppm or lower, and a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and acetic anhydride, wherein the acetic anhydride is purified acetic anhydride obtained by treating acetic anhydride by contacting with at least one of a metal oxide and a mixed oxide, and optionally, distilling the acetic anhydride simultaneously with or after the contact treatment.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: June 11, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mitsuharu Kobayashi, Nobuyuki Murai
  • Patent number: 6395938
    Abstract: A method for controlling the molecular weight distribution of polyether glycol in producing polyether glycol having a specified number average molecular weight by polymerizing tetrahydrofuran as a starting monomer with the use of a heteropoly-acid as a catalyst, which method comprises conducting the polymerization in the presence of an amount of water which can form two phases of the organic phase and a catalyst phase, sampling the polymerization product during the polymerization to determine the molecular weight distribution and, when the molecular weight distribution thus found is narrower than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase wider, while, when the found molecular weight distribution is wider than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase narrower.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: May 28, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventor: Takaharu Akedo
  • Patent number: 6380351
    Abstract: The present invention provides, inter alia, novel fluorinated copolymers and coprepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains (FOX monomers) and tetrahydrofuran (THF). In addition, the present invention provides methods of making such copolymers and coprepolymers.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: April 30, 2002
    Assignee: Aerojet-General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald
  • Patent number: 6362312
    Abstract: In a process for preparing polytetrahydrofuran, polytetrahydrofuran copolymers or diesters or monoesters thereof comprises polymerizing tetrahydrofuran in the presence of at least one telogen and/or comonomer over an acid-activated calcium montmorillonite as catalyst, the calcium montmorillonite has a BET surface area of at least 300 m2/g, an acidity of at least 0.02 mmol/g at pKa<−3 and a pore volume of at least 0.40 cm3/g for pore sizes in the range from 30 to 200 Å.
    Type: Grant
    Filed: April 10, 2000
    Date of Patent: March 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Heinz Rütter, Michael Hesse, Rainer Becker
  • Patent number: 6359108
    Abstract: A process for polymerizing cyclic ethers over a heterogeneous catalyst comprises using a heterogeneous catalyst comprising one or more pillared interlayered clays (PILCs).
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: March 19, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Frank Stein, Christoph Sigwart, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Ulrich Müller
  • Patent number: 6355846
    Abstract: A process for producing a poly(tetramethylene ether) glycol (PTMEG) or copolymer having a narrowed molecular weight ratio of 1.9 to 2.07 and a dispersity of 1.2 to 1.65 from a starting PTMEG or copolymer with a broader molecular weight distribution having a dispersity of 1.9 to 2.3 and a molecular weight ratio of 2.3 to 2.6 is provided by feeding the PTMEG or copolymer and an effective amount of an inert solvent to a stripping apparatus and stripping at a temperature of 150 to 220 degrees C. and a pressure of 0.5 to 5 mm of mercury.
    Type: Grant
    Filed: October 17, 2000
    Date of Patent: March 12, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Suri Narayan Dorai, Richard Edward Ernst
  • Publication number: 20020019572
    Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.
    Type: Application
    Filed: April 19, 1999
    Publication date: February 14, 2002
    Inventor: PHILIP LEUNG
  • Publication number: 20020010080
    Abstract: Organo-Lewis acids of the formula BR′R″2 wherein B is boron, R′ is fluorinated biphenyl, and R″ is a fluorinated phenyl, fluorinated biphenyl, or fluorinated polycyclic fused ring group, and cationic metallocene complexes formed therewith. Such complexes are useful as polymerization catalysts.
    Type: Application
    Filed: July 5, 2001
    Publication date: January 24, 2002
    Inventors: Tobin J. Marks, You-Xian Chen
  • Patent number: 6313060
    Abstract: A resilient polyurethane foam produced by using a polyether polyol produced by reacting alkylene oxides with a polyhydroxy compound having at least 2 hydroxyl groups as an initiator in the presence of the catalyst for alkylene oxide ring-opening polymerization of the present invention, which is excellent in foam physical properties, vibration characteristics and molding properties.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: November 6, 2001
    Assignee: Asahi Glass Company, Limited
    Inventors: Kayoko Sugiyama, Hiroki Fukuda, Akio Horie, Hiroshi Wada
  • Publication number: 20010029309
    Abstract: The present invention provides acetic anhydride, a method of purifying crude acetic anhydride, and a method of producing polyoxytetramethylene glycol using acetic anhydride.
    Type: Application
    Filed: February 16, 2001
    Publication date: October 11, 2001
    Inventors: Seiji Nishioka, Ryosuke Maeda, Toshifumi Fukui, Mitsuru Yamashira
  • Patent number: 6291714
    Abstract: A continuous process for the production of polyadducts of alkylene oxide on a chain initiator with at least one active hydrogen comprises the step of: (a) providing n reaction units constituted by a tubular reactor (11), and a heat exchanger (14) downstream of the tubular reaction (11); (b) supplying the preheated chain initiator and the alkylene oxide to the reactor of the first reaction unit; (c) reacting the chain initiator with the alkylene oxide to obtain a first mixture; (d) cooling the first mixture by means of the heat exchanger (14); (e) supplying the reactor of the following reaction unit with the cooled mixture and with alkylene oxide; (f) repeating the procedure until the last reaction unit and then discharging the last mixture containing the desired product. The tubular reactors are vertical and the chain initiator and alkylene oxide are sprayed into the top of the reactor where a gas liquid reaction occurs.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: September 18, 2001
    Assignee: Linde Aktiengesellschaft
    Inventor: Pasquale Fanelli
  • Patent number: 6211401
    Abstract: Polytetrahydrofuran, tetrahydrofuran copolymers, diesters or monoesters of these polymers are prepared by polymerizing tetrahydrofuran in the presence of at least one telogen and/or comonomer on a heterogeneous carrier catalyst which contains on an oxidic carrier material as active mass a catalytically active amount of at least one oxygenous molybdenum and/or tungsten compound and, when the precursor compounds of the active mass have been applied to the carrier material precursor, has been calcined at temperatures of between 500° C. and 1000° C. The catalyst used contains a promotor which comprises at least one element or a compound of an element of the 2nd, 3rd including the lanthanides, 5th, 6th, 7th, 8th or 14th group of the periodic system of elements.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: April 3, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Christoph Sigwart, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Frank Stein, Ulrich Müller, Michael Hesse
  • Patent number: 6204357
    Abstract: The invention is directed to new double metal cyanide (DMC) catalysts, a process for the preparation of these catalysts, and to a process for the preparation of polyetherpolyols by the polyaddition of alkylene oxides to starter compounds which contain active hydrogen atoms, wherein the catalyst comprises the novel double metal cyanide (DMC) catalyst of the present invention. These new double metal cyanide (DMC) catalysts comprise a) one or more double metal cyanide compounds, b) one or more organic complex ligands, and c) one or more cyclodextrins, with the proviso that b) and c) are different compounds. The catalysts of this invention exhibit greatly increased activity during preparation of a polyetherpolyol.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: March 20, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta, Lambertus Groenendaal
  • Patent number: 6111147
    Abstract: Polytetrahydrofuran, copolymers of tetrahydrofuran and 2-butyne-1,4-diol, diesters of these polymers with C.sub.2 -C.sub.20 -monocarboxylic acids or monoesters of these polymers with C.sub.1 -C.sub.10 -monocarboxylic acids are prepared by polymerization of tetrahydrofuran in the presence of one of the telogens water, 1,4-butanediol, 2-butyne-1,4-diol, polytetrahydrofuran having a molecular weight of from 200 to 700 Dalton, a C.sub.1 -C.sub.10 -monocarboxylic acid or an anhydride of a C.sub.2 -C.sub.20 -monocarboxylic acid or a mixture of these telogens over a heterogeneous supported catalyst which comprises a catalytically active amount of an oxygen-containing molybdenum and/or tungsten compound on an oxidic support material and which has been calcined at from 5OO.degree. C. to 1OOO.degree. C.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Sigwart, Karsten Eller, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Frank Stein, Ulrich Mueller, Michael Hesse
  • Patent number: 6087460
    Abstract: The synthesis of the organo-Lewis acid perfluorobiphenylborane (PBB) and the activation of metallocenes for the formation of a variety of highly active homogeneous Ziegler-Natta metallocene olefin polymerization, copolymerization and ring-opening polymerization catalysts is described.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: July 11, 2000
    Assignee: Northwestern University
    Inventors: Tobin J. Marks, You-Xian Chen
  • Patent number: 6069226
    Abstract: Polytetramethylene ether glycol diester of the formula ##STR1## wherein R and R.sup.1 are identical or different and are alkyl radicals having 1-4 carbon atoms, and n is an integer from 2 to 200, are prepared by polymerizing tetrahydrofuran in the presence ofi) an acid-activated polymerization catalyst selected from synthetic amorphous aluminum silicates, zeolite and kaolin, which has been calcined at from 350.degree. to 700.degree. C. before use,ii) a carboxylic anhydride, andiii) from 1 to 10% by weight, based on the weight of the polymerization catalyst, of a metal from the 8th group of the Periodic Table of the Elements as a hydrogenation catalyst.
    Type: Grant
    Filed: October 21, 1997
    Date of Patent: May 30, 2000
    Assignee: BASF Aktiengesellschaft
    Inventor: Monika Muller
  • Patent number: 6040413
    Abstract: Thus, there is provided according to the present invention polyol compositions comprising(A) a polytetramethylene ether glycol, and(B) a trifunctional active hydrogen compound-initiated polyoxyalkylene polyether polyol having a degree of unsaturation of not greater than 0.04 milliequivalents per gram of said polyether polyol.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: March 21, 2000
    Assignee: BASF Corporation
    Inventors: Thomas L. Fishback, Duane A. Heyman, Curtis J. Reichel, Adam J. Jaglowski
  • Patent number: 6028229
    Abstract: A process for the production of end-capped nonionic surfactants corresponding to formula (I): ##STR1## in which R.sup.1 is an alkyl or alkenyl group containing 6 to 22 carbon atoms, n1 and n2 independently of one another represent 0 or a number from 1 to 10, m represents a number from 1 to 20 and R.sup.2 represents methyl or ethyl, by(a) etherifying a fatty alcohol polyglycol ether corresponding to formula (II): ##STR2## in which R.sup.1, n1, n2 and m are as defined above, with a dialkyl sulfate in the presence of a solid substantially water-free base and an alkali metal or alkaline earth metal hydride,(b) adding water to the crude ethers in such a quantity that phase separation occurs, and(c) removing the organic phase.
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: February 22, 2000
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Joaquim Bigorra Llosas, Nuria Bonastre, Rafael Pi Subirana, Antonio Trius Oliva
  • Patent number: 5962727
    Abstract: An improved method for manufacturing diesters of polytetramethylene ethers involving the polymerization of tetrahydrofuran (THF) optionally with one or more comonomers (e.g., 3-methyl THF, ethylene oxide, propylene oxide, or the like) utilizing a solid acid catalyst (e.g., Nafion.RTM.) and a carboxylic acid with carboxylic acid anhydride (e.g., acetic acid with acetic anhydride) as molecular weight control agents wherein setting the pressure of the reactor while simultaneously achieving removal of the heat of reaction by operating under solvent/monomer evaporative reaction conditions effectively controls the reaction temperature. Such a process is useful in producing high purity commercial grade PTMEA that advantageously avoids problems caused by the high heat of reaction when such a process is scaled up to commercial level.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: October 5, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Suriyanarayan Dorai, Donald Truszkowski