And Cyclic Ether Patents (Class 568/620)
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Patent number: 6531566Abstract: A polyoxyalkylene polyol or monool (I) of the general formula (1) below, in which not less than 40% of the terminally located hydroxyl-containing groups, namely —AO—H groups, are primary hydroxyl-containing groups of the general formula (2) below, or; a method of producing ring-opening polymerization products, by subjecting a heterocyclic compound to ring-opening addition polymerization with an active hydrogen-containing compound, using as a catalyst tris(pentafluorophenyl)borane, tris(pentafluorophenyl)aluminum, etc.Type: GrantFiled: March 7, 2001Date of Patent: March 11, 2003Assignee: Sanyo Chemical Industries, Ltd.Inventor: Munekazu Satake
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Patent number: 6512146Abstract: Improved water resistant acetal sizing agents including 1,1-octadecoxyoctadecane are provided along with methods for their synthesis including methods in which C8 to C30 alkyl bromides are reacted with a polyol under basic conditions and those in which a C8 to C30 primary alcohol is reacted with an organic base in the presence of a suitable oxidizing agent under basic conditions.Type: GrantFiled: December 20, 2000Date of Patent: January 28, 2003Assignee: Penford CorporationInventors: Edward P. Pauley, Katherine Sue Neighbor
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Patent number: 6504062Abstract: A process for the preparation of odor-lean polyether polyols from polyether polyol product stream obtained by reacting a starting compound having a plurality of active hydrogen atoms with one or more alkylene oxides, which process comprises the steps of: (a) contacting the polyether polyol product with an excess of acid having a pKa of less than 5 under hydrolysis conditions, (b) contacting the reaction mixture with excessive amount of water to form a two-phase system under hydrolysis conditions by adding an amount of water to form an organic phase and a water phase to reduce the amount of cyclic-ether compounds present in the polyether polyol product, and (c) recovering the odor-lean polyether polyol.Type: GrantFiled: September 6, 2000Date of Patent: January 7, 2003Assignee: Shell Oil CompanyInventors: Henricus Maria Johannes Brons, Hans De Vos
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Publication number: 20030004377Abstract: When the reaction solution formed during the addition of an alkylene oxide to an active hydrogen-containing compound has viscosity of not less than 10 mPa.Type: ApplicationFiled: May 13, 2002Publication date: January 2, 2003Inventors: Toru Inaoka, Yasuhiko Sato, Yoshiyuki Onda, Hiromichi Tanaka, Tsuyoshi Hirata
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Publication number: 20030004378Abstract: Polyetherpolyols are prepared by reacting diols or polyols with ethylene oxide, propylene oxide, butylene oxide or a mixture thereof in the presence of a multimetal cyanide complex catalyst by a process which is carried out in a vertical upright cylindrical reactor comprising a jet nozzle which is arranged in the upper reactor region and is directed downward and via which the starting materials and the reaction mixture are fed in, and comprising a take-off, preferably in the lower reactor region, via which the reaction mixture is fed back to the jet nozzle in an external circulation by means of a pump via an equilibration container, comprising a concentric guide tube which extends over the total length of the reactor, except for the reactor ends, and comprising a heat exchanger integrated in the annular space.Type: ApplicationFiled: July 5, 2002Publication date: January 2, 2003Inventors: Thomas Ostrowski, Kathrin Harre, Peter Zehner, Jorn Muller, Dieter Stutzer, Georg Heinrich Grosch, Jurgen Winkler, Stephan Bauer
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Publication number: 20020193640Abstract: Polyethylene glycol for use in fields with application to a living body wherein the sum of the contents of ethylene glycol and diethylene glycol in the polyethylene glycol is less than or equal to that expressed in the following formula [I]: 1 Sum ⁢ ⁢ of ⁢ ⁢ ethylene ⁢ ⁢ glycol ⁢ ⁢ and ⁢ ⁢ diethylene ⁢ ⁢ glycol ⁢ ⁢ contents ⁢ ⁢ ( ppm ) = 150 × 2900 × 0.Type: ApplicationFiled: March 27, 2002Publication date: December 19, 2002Applicant: NOF CORPORATIONInventors: Kenji Sakanoue, Kouzoh Sanchika, Tohru Yasukohchi
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Patent number: 6492565Abstract: The present invention relates to a process for the preparation of polyether polyols by the reaction of alkylene oxides and compounds containing active hydrogens, in the presence of specific Lewis acid metal compounds as catalysts, novel bis(perfluoroalkylsulfonic acid) compounds of Group 13 of the Periodic Table of the Elements, and to a process for the preparation thereof and the use thereof as catalysts for ring-opening polymerization of cyclic ethers.Type: GrantFiled: April 6, 2001Date of Patent: December 10, 2002Assignee: Bayer AktiengesellschaftInventors: Uwe Denninger, Jörg Hofmann, Pramod Gupta
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Publication number: 20020183560Abstract: Process for the preparation of odour-lean polyether polyols from a polyether polyol starting product which is obtained by reacting a starting compound having a plurality of active hydrogen atoms with one or more alkylene oxides, which process comprises the steps of: (a) contacting the neutralised or unneutralised polyether polyol product with an excess of an acid having a pKa of less than 5 under hydrolysis conditions, (b) contacting the reaction mixture with water under hydrolysis conditions, and (c) recovering the odour-lean polyether polyol.Type: ApplicationFiled: September 6, 2000Publication date: December 5, 2002Inventors: Henricus Maria Johannes Brons, Hans De Vos
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Patent number: 6486361Abstract: The invention relates to a process for the preparation of polyether polyols by means of double metal cyanide (DMC) catalysts, in which the induction phase is shortened markedly. By continuous dispensing of an alkylene oxide into the starter-catalyst mixture it is possible to achieve a substantial shortening of the induction phase by comparison with the batch-wise activation.Type: GrantFiled: March 20, 2002Date of Patent: November 26, 2002Assignee: Bayer AktiengesellschaftInventors: Stephan Ehlers, Jörg Hofmann, Manfred Dietrich, Pramod Gupta, Christian Steinlein, Horst Zwick
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Patent number: 6469218Abstract: The invention is directed to a process for preparing a polyether polyol by the polyaddition of an alkylene oxide on to a starter compound containing active hydrogen atoms under basic catalysis in the presence of phosphonium cations.Type: GrantFiled: May 1, 2002Date of Patent: October 22, 2002Assignee: Bayer AktiengesellschaftInventors: Ornulf Rexin, Rolf Mülhaupt
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Publication number: 20020147370Abstract: A continuous alkoxylation process for the production of polyether polyols is disclosed. The process comprises the use of a plurality of reaction modules each having an outer tube and an inner tube with annular chamber between them. A spiral reaction tube is spaced from the inner tube and winds around the inner tube within the annular chamber. The spiral reaction tube includes an inlet and an outlet, each of which extend through said outer tube. A heat exchange medium flows through the annular chamber and controls the reaction temperature in the spiral reaction tube. The process comprises continuously forming an initial reaction mixture of at least one [alkaline] alkylene oxide and an initiator having at least one reactive hydrogen which is reactive to the [alkaline] alkylene oxide.Type: ApplicationFiled: June 14, 2002Publication date: October 10, 2002Applicant: BASF CorporationInventors: Werner Hinz, Edward Michael Dexheimer
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Publication number: 20020147369Abstract: Polyetherols based on solid initiator substances and liquid, hydroxyl-containing coinitiators are prepared by a catalyzed addition reaction of alkylene oxides by a process in which the initiator combination contains ethoxy structures, the ratio of the average number of hydroxyl groups per mole of initiator combination to the number of ethoxy structures in the polyetherol being from 1:0.2 to 1:1.8 and the ratio of the amounts by weight of the ethoxy structures to the average molecular weight of the polyetherol being from 1:2 to 1:15.Type: ApplicationFiled: July 26, 2001Publication date: October 10, 2002Inventors: Stefan Dinsch, Jurgen Winkler, Gottfried Knorr, Michael Reichelt, Gerd Hoppner, Peter von Malotki
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Publication number: 20020128521Abstract: Disclosed is a process for making alkoxylates of organic compounds.Type: ApplicationFiled: January 19, 2001Publication date: September 12, 2002Inventors: Christian B. Priou, Patricia Beurdeley
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Patent number: 6441247Abstract: The present invention relates to a process for the preparation of polyether polyols by catalytic reaction of H-functional initiators with lower alkylene oxides, wherein the catalysts used are multimetal cyanide compounds and the H-functional initiators used are butane-1,4-diol, &agr;-hydroxy-&ohgr;-hydroxypoly(oxybutane-1,4-diyl), pentane-1,5-diol, decane-1,10-diol or mixtures of at least two of these compounds.Type: GrantFiled: July 26, 2001Date of Patent: August 27, 2002Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Kathrin Harre
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Patent number: 6429342Abstract: Ethoxylations of various initiator compounds are performed in the presence of metal cyanide catalysts. The catalysts surprisingly form a wide variety of polyether products that in most cases contain only small amounts of high molecular weight poly(ethylene oxide).Type: GrantFiled: July 7, 2000Date of Patent: August 6, 2002Assignee: Dow Global Technologies Inc.Inventors: Katherine S. Clement, Louis L. Walker, Richard M. Wehmeyer, Robert H. Whitmarsh, David C. Molzahn, William P. Dianis, David E. Laycock
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Patent number: 6420320Abstract: The invention is a high molecular weight polyether polyol prepared by the reaction of one or more compounds having one or more active hydrogen compounds with one or more alkylene oxides in the presence of a catalyst comprising calcium having counterions of carbonate and a C6-10 alkanoate in a solvent or dispersant which does not contain active hydrogen atoms. The polyether polyol prepared preferably has an equivalent weight of from about 10,000 to about 30,000, a polydispersity of 1.3 or less and a residual catalyst level of from more than 0 to about 2000 parts per million (ppm). In another embodiment the invention is a process for preparing such high molecular weight polyether polyols. The process comprises first, contacting one or more compounds having one or more active hydrogen atoms with one or more alkylene oxides in the presence of a catalyst. The catalyst comprises calcium having counterions of carbonate and a C6-10 alkanoate in a solvent, wherein the solvent does not contain active hydrogen atoms.Type: GrantFiled: September 7, 2000Date of Patent: July 16, 2002Assignee: The Dow Chemical CompanyInventors: Philip W. McGraw, Robert H. Whitmarsh
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Patent number: 6362126Abstract: Double-metal cyanide catalysts of the formula M1a[M2(CN)b(A)c]d. fM1gXn. h (H2O).Type: GrantFiled: September 9, 2000Date of Patent: March 26, 2002Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Ulrich Kammel
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Patent number: 6350920Abstract: Polyether polyols can be prepared by reacting polyols with epoxides in the presence of basic catalysts, by treating the polyether polyols containing the basic catalysts with OH-functional solid compounds of metals of groups III to VIII of the periodic system of the elements (Mendeleyev), the compounds being insoluble in the polyether polyols and having BET surface areas of from 10 to 1000 m2/g, isolating the solid inorganic compounds laden with the basic catalysts from the polyether polyol and using them in the reaction of polyols with epoxides, or bringing the isolated inorganic compounds laden with the basic catalysts into contact with the polyols that are to be used in the reaction with epoxides, separating those polyols from the inorganic compounds and delivering them to the reaction with epoxides.Type: GrantFiled: March 20, 2000Date of Patent: February 26, 2002Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Manfred Dietrich, Pramod Gupta, Pieter Ooms
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Patent number: 6326514Abstract: The invention provides a process for the preparation of ether carboxylic acids or alkali metal or ammonium salts thereof with low residual alcohol content, which comprises firstly converting a mono- or polyhydric alcohol into the corresponding alkoxide using a substoichiometric amount between 5 and 95 mol % of a basic compound, and then reacting the alkoxide with alkylene oxides, and, if necessary after distilling off the residual alcohol which remains, alkylating the highly alkaline reaction mixture, which comprises more than 5 mol % of alkoxylated alkoxides, directly with a chloroacetic acid derivative, and, if necessary, converting the alkylated product into the free ether carboxylic acid by acidification with mineral acid.Type: GrantFiled: June 19, 2000Date of Patent: December 4, 2001Assignee: Clariant GmbHInventors: Peter Klug, Rainer Kupfer, Ignaz Wimmer, Rüdiger Winter
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Patent number: 6323375Abstract: The present invention relates to highly active, substantially crystalline double metal cyanide (DMC) catalysts, a process for the preparation of these double metal cyanide catalysts, a process for producing polyether polyols by the polyaddition of alcohol ethers onto starter compounds containing active hydrogen atoms from these DMC catalysts, and to the polyether polyols produced by this process. The DMC catalysts of the invention comprise a) double metal cyanide compounds, b) organic complexing ligands, and c) functionalized polymers. These catalysts exhibit increased activity in the process for the production of polyether polyols.Type: GrantFiled: April 5, 2000Date of Patent: November 27, 2001Assignee: Bayer AktiengesellschaftInventors: Jörg Hofmann, Pramod Gupta, Robert-Joseph Kumpf, Pieter Ooms, Walter Schäfer, Michael Schneider
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Patent number: 6319999Abstract: For the semi-continuous production polyadducts of alkylene oxide by an addition reaction of alkylene oxide on a chain initiator having at least one active hydrogen, there is provided a reactor (1) constituted by a cylindrical body with two diameters, the upper part being of larger diameter than the lower part, heat-exchange means (2) and recycling ducts (13, 15) for the recycling of the reaction mixture from the bottom to the head of the reactor in order to obtain the final desired product, thereby enabling the production to be carried out with greater flexibility and reduced down times.Type: GrantFiled: September 27, 1999Date of Patent: November 20, 2001Assignee: Linde AktiengesellschaftInventor: Pasquale Fanelli
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Patent number: 6303833Abstract: A crystalline multimetal cyanide complex of the formula (I) M1a[M2(CN)bL1c]d*e(M1fXg)*hL2′iH2O (I) where M1 is at least one element from the group consisting of Zn(II), Fe(II), Co(III), Ni(II), Mn(II), Co(II), Sn(II).Type: GrantFiled: March 29, 2000Date of Patent: October 16, 2001Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Reinhard Lorenz, Dieter Junge, Eugen Gehrer, Ulrich Treuling
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Patent number: 6303533Abstract: A process for preparing double metal cyanide catalysts, comprising combining an aqueous solution of a metal salt of the formula M1m(X)n, with an aqueous solution of a cyanometallic acid of the formula HaM2(CN)b(A)c, where one or both aqueous solutions may comprises at least one water-miscible organic ligand selected from the group consisting of alcohols, aldehydes, ketones, ethers, polyethers, esters, ureas, amides, nitrites or sulfides, if desired, combining the aqueous suspension thus obtained with at least one water-miscible organic ligand selected from the above-mentioned group, which ligand may be identical to or different from any previously added ligand, and separating the resulting two-metal cyanide complex from the suspension.Type: GrantFiled: March 5, 1998Date of Patent: October 16, 2001Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Harald Larbig, Dieter Junge, Daniella Geelen, Peter de Vocht, Gerd Hoeppner
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Patent number: 6255434Abstract: The invention is a high molecular weight polyether polyol prepared by the reaction of one or more compounds having one or more active hydrogen compounds with one or more alkylene oxides in the presence of a catalyst comprising calcium having counterions of carbonate and a C6-10 alkanoate in a solvent or dispersant which does not contain active hydrogen atoms. The polyether polyol prepared preferably has an equivalent weight of from about 1000 to about 20,000, a polydispersity of about 1.3 or less and a residual catalyst level of from about 0 to about 2000 parts per million (ppm).Type: GrantFiled: April 27, 1999Date of Patent: July 3, 2001Assignee: The Dow Chemical CompanyInventors: Philip W. McGraw, Robert H. Whitmarsh, Paul E. Cranley, Raymond A. Plepys
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Patent number: 6207794Abstract: The present invention is a polyoxyalkylene polyol, its manufacture method, and derivatives, wherein: it is obtained using a phosphazenium compound as a catalyst; the hydroxyl value is 2˜200 mgKOH/g; total degree of unsaturation is 0.0001˜0.07 meq./g; the head-to-tail bond selectivity of the polyoxyalkylene polyol is 95 mole %; and when the maximum height of the peak of GPC elution curve is set to be 100%, W20 is defined as the peak width at the 20% peak height, and W80 is defined as the peak width at 80% peak height, the ratio of W20/W80 is 1.5 or greater, and less than 3.Type: GrantFiled: December 17, 1998Date of Patent: March 27, 2001Assignee: Mitsui Chemical, Inc.Inventors: Satoshi Yamasaki, Yasunori Hara, Satoshi Tamura, Fumio Yamazaki, Hitoshi Watanabe, Mikio Matsufuji, Shinsuke Matsumoto, Ariko Nishikawa, Tsukuru Izukawa, Masaaki Aoki, Tadahito Nobori, Usaji Takaki
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Patent number: 6191315Abstract: Most generally, the invention provides a method for making a neutralized polyether polyol, comprising the steps of a) Polymerizing one or more alkylene oxides in the presence of an alkaline catalyst to form a polyalkylene oxide intermediate; and b) Neutralizing the intermediate, after the polymerization step a) is complete, with an organic acid of general formula where R1 is hydrogen, methyl, or ethyl; R2 is methyl or ethyl; and R3 is an alkyl, aryl, or aralkyl group containing one to twelve carbon atoms. The invention also comprises the novel compositions made by the above process.Type: GrantFiled: February 11, 1999Date of Patent: February 20, 2001Assignee: BASF CorporationInventors: Chacko Thankachan, Brian J. Betke, Michael C. Welch
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Patent number: 6103850Abstract: There is provided an sealant made with an isocyanate or hydroxyl terminated prepolymer made by reacting a stoichiometric excess of an organic polyisocyanate with polyols made of at least a polyoxyalkylene polyether triol or a mixture thereof with a polyoxyalkylene polyether diol. The triol or diol has within its structure the nucleus of an initiator compound, an internal blocks of oxypropylene groups, and external blocks of oxyalkylene groups, wherein the internal blocks of oxypropylene are between said nucleus and said external blocks, said external blocks are made of oxyalkylene groups derived from a C.sub.4 or higher alkylene oxide. The amount of the internal blocks of oxypropylene groups is from 25 weight percent to 80 weight percent based on the weight of all oxyalkylene groups and initiator in the prepolymer The triol or diol has a compatibility index of 25.degree. C. or less, and may be part of a two component or a one component moisture cured sealant.Type: GrantFiled: November 21, 1996Date of Patent: August 15, 2000Assignee: BASF CorporationInventors: Curtis J. Reichel, Thomas L. Fishback, Gladys M. Aviles
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Patent number: 6077978Abstract: Acidification, neutralization, or removal of basic impurities from acid sensitive low molecular weight starter or acidification of a reactor heel prior to addition of acid sensitive low molecular weight starter allows direct oxyalkylation of continuously added acid sensitive low molecular weight starter to produce polyoxyalkylene acid sensitive low molecular weight starter-initiated or co-initiated polyols in the presence of a double metal cyanide catalyst. The preferred acid sensitive low molecular weight starter is glycerine.Type: GrantFiled: September 17, 1997Date of Patent: June 20, 2000Assignee: ARCO Chemical Technology L.P.Inventors: Kenneth G. McDaniel, Mark J. Perry, John E. Hayes
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Patent number: 6066683Abstract: Copolymer DMC-catalyzed polyoxypropylene polyols which exhibit processing latitude similar to base-catalyzed copolymer analogs and base-catalyzed homopolyoxypropylene analogs may be prepared by oxyalkylation with a mixture of propylene oxide and ethylene oxide such that a finite ethylene oxide content is maintained in the oxyalkylation reactor for the most substantial part of the oxyalkylation, the polyoxypropylene polyol having randomly distributed oxyethylene moieties which constitute 1.5 weight percent or more of the polyol product.Type: GrantFiled: April 3, 1998Date of Patent: May 23, 2000Assignee: Lyondell Chemical Worldwide, Inc.Inventors: Robert W. Beisner, Chiu Yan Chan, Thomas P. Farrell, Danny J. Frich, Mark R. Kinkelaar, Jack R. Reese, II, Donald F. Rohr, Wolfgang Schmidt, Andrew M. Thompson
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Patent number: 6022945Abstract: A catalyst for the polymerization of an alkylene oxide compound is disclosed. This catalyst is composed of a phosphazene compound or a phosphazenium salt which is derived from the phosphazene compound and an active hydrogen compound. A poly(alkylene oxide) can be efficiently produced by polymerizing the alkylene oxide compound in the presence of the catalyst and, when the catalyst is composed of the phosphazene compound, the active hydrogen compound. The poly(alkylene oxide) contains no metal component and compared with those produced using conventional amine-base catalysts, has also been improved significantly in odor.Type: GrantFiled: May 28, 1999Date of Patent: February 8, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Masahiro Kouno, Tadahito Nobori, Kazumi Mizutani, Usaji Takaki
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Patent number: 6008263Abstract: Copolymer DMC-catalyzed polyoxypropylene polyols which exhibit processing latitude similar to base-catalyzed copolymer analogs and homopolyoxypropylene analogs may be prepared by oxyalkylation with a mixture of propylene oxide and ethylene oxide such that a finite ethylene oxide content is maintained in the oxyalkylation reactor for the most substantial part of the oxyalkylation, the polyoxypropylene polyol having randomly distributed oxyethylene moieties which constitute 1.5 weight percent or more of the polyol product. Block copolymer polyols having external blocks containing lesser oxyethylene content than internal blocks and bicompositional compositions containing discrete multimodal and dissimilar and optionally multimodal polyols produced by a continuous addition of starter process are useful as polyols exhibiting greater processing latitude.Type: GrantFiled: April 3, 1998Date of Patent: December 28, 1999Assignee: Lyondell Chemical Worldwide, Inc.Inventors: Andrew M. Thompson, Wolfgang Schmidt, Donald F. Rohr, Jack R. Reese, II, Mark R. Kinkelaar, Danny J. Frich, Thomas P. Farrell, Chiu Yan Chan, Robert W. Beisner
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Patent number: 5998672Abstract: Double metal cyanide catalysts, prepared by drying a catalyst slurry by a non-agglomerative drying method such as spray drying or freeze drying, directly produces catalyst particles of fine particle size such that intensive grinding is not required. The catalysts thus produced are different from conventionally dried particles in that polyoxyalkylation may be conducted with less reactor fouling and a polyoxyalkylene product of lower unsaturation and narrower polydispersity may be obtained.Type: GrantFiled: November 11, 1998Date of Patent: December 7, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Ahmad Soltani-Ahmadi, Bi Le-Khac, Gerald A. Bullano
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Patent number: 5965778Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible by the use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.Type: GrantFiled: August 31, 1998Date of Patent: October 12, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
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Patent number: 5962748Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step comprising reacting propylene oxide with an initiator having at least two hydroxyl groups in the presence of a basic catalyst, a second step of contacting the polyether product of the first step having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: October 23, 1997Date of Patent: October 5, 1999Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5952457Abstract: A catalyst for the polymerization of an alkylene oxide compound is disclosed. This catalyst is composed of a phosphazene compound or a phosphazenium salt which is derived from the phosphazene compound and an active hydrogen compound. A poly(alkylene oxide) can be efficiently produced by polymerizing the alkylene oxide compound in the presence of the catalyst and, when the catalyst is composed of the phosphazene compound, the active hydrogen compound. The poly(alkylene oxide) contains no metal component and compared with those produced using conventional amine-base catalysts, has also been improved significantly in odor.Type: GrantFiled: September 4, 1996Date of Patent: September 14, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Masahiro Kouno, Tadahito Nobori, Kazumi Mizutani, Usaji Takaki
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Patent number: 5945568Abstract: A method for producing a glycol ether, which can maintain a high catalyst-activity and high productivity, can control reaction-selectivity and which comprises reacting an alkylene oxide with an alcohol in the presence of a catalyst, wherein the catalyst is an anion exchange resin which comprises, as the substrate, a polymer of a vinyl aromatic compound and which has a structure such that a quaternary ammonium group is bonded to the aromatic group via a linking group having a chain length of at least 3.Type: GrantFiled: May 28, 1997Date of Patent: August 31, 1999Assignee: Mitsubishi Chemical CorporationInventors: Koichi Nagata, Toshiyuki Furuya
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Patent number: 5877245Abstract: The reaction product ofA) a linking compound of formula IR.sup.1 (X).sub.3 (I)wherein each X group is a halogen or one X group is a halogen and two X groups with 2 carbon atoms from the R.sup.1 group and an oxygen atom form an epoxy group, and R.sup.1 is an alkanetriyl group containing from 3 to 10 carbon atoms;B) a compound of formula IIR.sup.2 (OA).sub.n --OH (II)wherein R.sup.2 is an aliphatic group containing from 4 to 36 carbon atoms, n is a number of from 1 to 200, and each OA group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group; andC) a compound of formula IIIH--(OA).sub.m --OH (III)wherein OA is as defined above, and m is a number of from 1 to 500;processes for its preparation; and methods for its use as a thickener in aqueous compositions.Type: GrantFiled: August 15, 1997Date of Patent: March 2, 1999Assignee: Henkel CorporationInventors: Michael S. Wiggins, David I. Devore
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Patent number: 5811594Abstract: Methyl-end-capped alkyl and/or alkenyl polyglycol ethers; a process for their production by methylation of products of the addition of ethylene oxide and propylene oxide to primary alcohols; to formulations containing these substances; and to the use of the substances for the production of surface-active formulations.Type: GrantFiled: March 7, 1997Date of Patent: September 22, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karl Schmid, Joaquim Bigorra Llosas
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Patent number: 5811595Abstract: The present invention concerns a process for preparing a highly pure adduct of one or more alkylene oxide(s) to a compound which is sufficiently reactive for an addition reaction, said process being carried out in a reaction system designed as a loop-type reactor and comprising the steps of (a) feeding a compound sufficiently reactive for the addition reaction to the reaction system and circulating said compound in the whole system; (b) deaerating the whole reaction system and injecting an inert gas; (c) adding said alkylene oxide(s) with mixing, said addition step taking place at a point of the reaction system which is upstream a heat exchanger which is assembled in the loop and serves as a means for heating; (d) quickly heating a partial amount of the reaction mixture containing freshly admixed alkylene oxide(s) to a temperature allowing a substantial degree of conversion of the reactants; (e) immediately cooling, after reaching said substantial degree of conversion of said reactants, said partial amount ofType: GrantFiled: July 10, 1995Date of Patent: September 22, 1998Inventor: Vincent Simon Ellis
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Patent number: 5789626Abstract: Highly active double metal cyanide (DMC) catalysts are disclosed. The catalysts comprise a DMC complex, and organic complexing agent, and from about 5 to about 80 wt. %, based on the amount of catalyst, of a polyether having a number average molecular weight less than about 500. The catalysts polymerize propylene oxide at a rate in excess of about 1 kg PO/g Co/min. at 100 ppm catalyst, based on the weight of finished polyether, at 105.degree. C. The catalysts, which are easy to prepare, give polyether polyols with exceptionally low unsaturation levels.Type: GrantFiled: January 8, 1997Date of Patent: August 4, 1998Assignee: Arco Chemical Technology, L.P.Inventor: Bi Le-Khac
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Patent number: 5780584Abstract: Highly active double metal cyanide (DMC) complex catalysts and methods for making them are disclosed. The catalysts contain less than about 0.2 moles of metal salt per mole of DMC compound in the catalyst, and unlike other highly active DMC catalysts, are substantially crystalline. Polyether polyols made from the catalysts have low unsaturation and are useful for making many types of polyurethane products.Type: GrantFiled: January 7, 1997Date of Patent: July 14, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Bi Le-Khac, Harry R. Hinney, Paul T. Bowman
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Patent number: 5728796Abstract: A process reaction between: (1) a compound that contains one or more epoxide moieties per molecule, and (2) a compound that contains one or more primary aliphatic hydroxyl groups per molecule; is catalyzed by: (3) a catalyst compound containing one or more trifluoromethanesulfonate moieties and one or more silyl moieties and run at a temperature of no more than 130.degree. C., such that the catalyst preferably catalyzes reaction at the primary aliphatic hydroxyl group, so that the resulting resin does not gel.Type: GrantFiled: May 31, 1996Date of Patent: March 17, 1998Assignee: The Dow Chemical CompanyInventors: Zeng K. Liao, James L. Bertram
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Patent number: 5714639Abstract: Improved double metal cyanide (DMC) catalysts useful for making epoxide polymers are disclosed. One catalyst is a paste of a double metal cyanide (DMC) compound, an organic complexing agent, and water. The paste comprises at least about 90 wt. % of particles having a particle size within the range of about 0.1 to about 10 microns as measured by light scattering in polyether polyol dispersions of the catalyst particles. Preferred catalysts have a bimodal particle size distribution. The paste catalyst is more active and simpler to prepare than powder DMC catalysts. Polyols made from the paste catalyst have low unsaturations, low viscosities, and narrow molecular weight distributions, and are useful in making a variety of polyurethane products.Type: GrantFiled: February 21, 1997Date of Patent: February 3, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Paul T. Bowman, Harry R. Hinney, Robert L. Meeker
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Patent number: 5698746Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step of contacting a polyether having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.Type: GrantFiled: November 4, 1996Date of Patent: December 16, 1997Assignee: Huntsman Petrochemical CorporationInventor: Timothy L. Lambert
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Patent number: 5689012Abstract: A continuous process for the preparation of polyoxyalkylene polyethers using DMC catalysts as the polyoxyalkylation catalyst employs continuous addition of alkylene oxide in conjunction with continuous addition of starter and catalyst to a continuous oxyalkylation reactor. Despite the continuous introduction of starter, the molecular weight distribution of the polyether product is quite narrow, as indicated by the exceptionally low polydispersity of the product. The presence of low molecular weight species during the majority of the polyoxyalkylation also substantially eliminates extremely high molecular weight fractions having molecular weights greater than 100,000 Da, again without appreciably broadening molecular weight distribution. By withdrawing intermediate molecular weight polyether product or diverting a portion of the end product to prepare a catalyst/starter mixture, rapid and sustained reaction rates can be achieved while employing low molecular weight starters.Type: GrantFiled: July 18, 1996Date of Patent: November 18, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Jose F. Pazos, T. Thomas Shih
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Patent number: 5686379Abstract: An alkoxylation catalyst comprising metal oxides, having a basicity point expressed in pKa value from 9 to 25 and an acidity point expressed in the amount of ammonia gas adsorbed from 50 to 500 .mu.mol/g, and a process for preparing an alkoxylate with the use of this catalyst. According to the present invention, an alkoxylate having a distribution of the number of moles of alkylene oxide added within a narrow range can be prepared and the reaction product is little contaminated with unreacted starting material and by-products. Further, the catalyst can easily be eliminated from the reaction product.Type: GrantFiled: August 21, 1995Date of Patent: November 11, 1997Assignee: Kao CorporationInventors: Tatsuhiro Imanaka, Toshihiro Tanaka, Jun Kono, Hiroshi Nagumo, Hiroyuki Tamaura
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Patent number: 5684096Abstract: Water-in-oil emulsions are broken by the use of adducts prepared by reacting high molecular weight polyalkylene glycol with ethylene oxide, or diglycidyl ether, or both ethylene oxide and diglycidyl ether. The adduct demulsifiers may be used alone or as a blend with other demulsifiers.Type: GrantFiled: February 14, 1996Date of Patent: November 4, 1997Assignee: Nalco/Exxon Energy Chemicals, L.P.Inventors: Grahame N. Taylor, Richard Mgla
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Patent number: 5668251Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: October 5, 1995Date of Patent: September 16, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Roland P. Carlson
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Patent number: 5650483Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3 -methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: October 5, 1995Date of Patent: July 22, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Gerald E. Manser, Thomas G. Archibald
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Patent number: 5648559Abstract: High resilience polyurethane foams exhibiting little or no shrinkage may be prepared from low unsaturation double metal cyanide catalyzed polyoxyalkylene polyols in amounts greater than 20 weight percent of the total polyol component, when low unsaturation poly(oxypropylene/oxyethylene) random polyols having less than 35 weight percent of an all polyoxypropylene block catalyzed by double metal cyanide catalysts and one or more external random polyoxypropylene/polyoxyethylene blocks each containing 2 weight percent or more oxyethylene moieties, and an unsaturation of less than 0.02 meq/g are employed.Type: GrantFiled: October 21, 1996Date of Patent: July 15, 1997Assignee: Arco Chemical Technology, L.P.Inventor: Stanley L. Hager