And Cyclic Ether Patents (Class 568/620)
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Patent number: 5596059Abstract: Polyoxyalkylene polyether polyols suitable for preparation of flexible polyurethane foams are prepared by oxyalkylating an aqueous solution of one or more polyhydric, hydroxyl-functional solid initiators under conditions where both water as well as initiator are oxyalkylated. The polyols have calculated functionalities of between about 2.2 and 4.0 and hydroxyl numbers in the range of 10 to 180. The polyols may be used to prepare soft, high resiliency polyurethane flexible foams at low isocyanate indexes.Type: GrantFiled: July 26, 1995Date of Patent: January 21, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Stanley L. Hager, James E. Knight, Gregory F. Helma, Ben J. Argento
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Patent number: 5589431Abstract: Improved double metal cyanide catalysts are disclosed. The substantially amorphous catalysts of the invention are more active for polymerizing epoxides than conventional DMC catalysts, which have a substantial crystalline component. Polyol products made with the catalysts are unusually clear, have exceptionally low unsaturations, and contain no detectable amount of low molecular weight polyol impurities. A method of making the improved DMC catalysts, which involves intimately combining the reactants, is also disclosed.Type: GrantFiled: June 7, 1995Date of Patent: December 31, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Bi Le-Khac
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Patent number: 5563221Abstract: A process for making high-primary, low-unsaturation polyols is disclosed. A polyol made by double metal cyanide (DMC) catalysis is blended with a polyol made by basic catalysis, and the polyol blend is reacted with ethylene oxide to produce an ethylene oxide-capped potyol. The process overcomes problems of the conventional recatalysis approach to making EO-capped polyols from DMC-catalyzed polyols.Type: GrantFiled: June 21, 1995Date of Patent: October 8, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Jos e F. Pazos
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Patent number: 5536883Abstract: 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 greater than about 500. A method of preparing the catalysts is also disclosed. The catalysts are easy to prepare, have exceptional activity, and are readily removed, if desired, from polymer products. The catalysts are used for polymerizing epoxides.Type: GrantFiled: May 30, 1995Date of Patent: July 16, 1996Assignee: ARCO Chemical Technology, L.P.Inventor: Bi Le-Khac
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Patent number: 5505878Abstract: 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: May 18, 1994Date of Patent: April 9, 1996Assignee: Exxon Chemical Patents Inc.Inventors: Grahame N. Taylor, Richard Mgla
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Patent number: 5468841Abstract: The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.Type: GrantFiled: April 13, 1994Date of Patent: November 21, 1995Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
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Patent number: 5463019Abstract: 3-Azidomethyl-3-nitratomethyloxetane, a novel oxetane compound, is used as a monomer for the formation of homopolymers and copolymers with other known energetic oxetane monomers. The polyethers of the present invention can be subsequently cured to form elastomers suitable for use as energetic binders in propellant formulations or the like.Type: GrantFiled: January 23, 1995Date of Patent: October 31, 1995Assignee: Aerojet-General CorporationInventors: Gerald E. Manser, Aslam A. Malik, Thomas G. Archibald
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Patent number: 5444170Abstract: This invention pertains to an improved process for the hydrogenation of acetylenic compounds prepared by the condensation of ketones or aldehydes with acetylene wherein the acetylenic compounds are contacted with hydrogen in the presence of a hydrogenation catalyst under conditions for effecting hydrogenation. The improvement in the process resides in utilizing a novel cocatalyst system for hydrogenating the acetylenic compounds to paraffins. The cocatalyst converts the inhibiting impurity in the feed to a noninhibiting species and comprises palladium and platinum, typically in a ratio of from 1 to 40 weight parts palladium per weight part platinum.Type: GrantFiled: January 10, 1994Date of Patent: August 22, 1995Assignee: Air Products and Chemicals, Inc.Inventor: Gamini A. Vedage
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Patent number: 5416241Abstract: A method for purifying polyether polyols made with double metal cyanide (DMC) catalysts is disclosed. A poly(oxypropylene) polyol containing DMC catalyst residues is combined with an amount of an alkali metal compound sufficient to convert DMC residues to an insoluble species, but not sufficient to generate polyol alkoxide groups. The polyol is heated in the presence of water, and is then filtered and stripped. The method eliminates the need to use magnesium silicate in removing DMC catalysts from polyols.Type: GrantFiled: January 27, 1994Date of Patent: May 16, 1995Assignee: Arco Chemical Technology, L.P.Inventor: Jude T. Ruszkay
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Patent number: 5391679Abstract: Polyether siloxanes, which are linked to the polysiloxane backbone through Si--C bonds, are synthesized by reacting given polysiloxanes with a compound having at least one epoxide group in such amounts, that there are at least two epoxide groups per OH group, in the presence of Lewis acids at temperatures not exceeding 60.degree. C. or in the presence of complex catalysts, which accelerate the addition between epoxide groups and hydroxyl groups, at temperatures up to 140.degree. C., the reaction optionally being carried out in the presence of an inert solvent. The polyether siloxanes obtained have a defined functionality and are free of excess, unreacted polyol components.Type: GrantFiled: May 17, 1993Date of Patent: February 21, 1995Assignee: Th. Goldschmidt AGInventors: Georg Burkhart, Dietmar Schaefer, Andreas Weier, Dietmar Wewers
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Patent number: 5391722Abstract: The present invention relates to a process for making a polyol which comprises the steps of: (a) fabricating a propoxylated polyhydric initiator by reacting propylene oxide with a polyhydric initiator in the presence of an acid catalyst, said reaction being conducted in the absence of a KOH catalyst, to produce a propoxylated polyhydric initiator containing acid catalyst residue(s) and free of KOH catalyst residue, and (b) reacting said propoxylated polyhydric initiator containing acid catalyst residue(s) with an alkylene oxide in the presence of a double metal cyanide complex catalyst to produce a polyol.Type: GrantFiled: March 30, 1990Date of Patent: February 21, 1995Assignee: Olin CorporationInventors: Kiran B. Chandalia, John W. Reisch, Michael M. Martinez
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Patent number: 5380777Abstract: This invention is first, a difunctional poly(glycidyl nitrate) oligomer (PGN oligomer), second, nitrated PGN oligomer and third, the use of the nitrated PGN oligomer as a plasticizer, particularly as a plasticizer for binders used in and/or as energetic formulations. Examples of energetic formulations are propellants, pyrotechnics and explosives and other such compositions. More particularly, this invention is a difunctional poly(glycidyl nitrate) oligomer of the formula ##STR1## where n is 0 to 3, having a M.sub.n of from about 304 to about 994. Another embodiment is the nitrated difunctional poly(glycidyl nitrate) oligomer of the formula ##STR2## where n is 0 to 3, having a M.sub.n of from about 394 to about 1084.Type: GrantFiled: March 28, 1994Date of Patent: January 10, 1995Assignee: Thiokol CorporationInventors: Rodney Willer, Alfred G. Stern, Robert S. Day
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Patent number: 5374705Abstract: Polyether polyols are by reacting an alkylene oxide comprising propylene oxide with an initiator containing at least three active hydrogen atoms per molecule. The reaction is conducted in the presence of an alkoxylation catalyst which is barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, or mixtures thereof; and in the presence of from about 1 to about 10 weight percent, based on total weight of initiator, of a processing aid that is an organic monohydroxyl- or dihydroxyl-containing substance having a molecular weight of at least 30, or a mixture thereof. The processing aid enhances the ability to obtain polyether polyols having a reduced unsaturation content.Type: GrantFiled: December 27, 1993Date of Patent: December 20, 1994Assignee: The Dow Chemical CompanyInventors: David E. Laycock, Robert A. Sewell
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Patent number: 5364973Abstract: A productive process for making conventional and low-unsaturation polyether polyols is disclosed. The process involves continuous removal of allyl alcohol and lower allyl alcohol propoxylates from the polyol during manufacture. The process can be performed at high temperatures and/or low catalyst concentrations. Polyether polyols with exceptionally low monol contents can be prepared.Type: GrantFiled: May 6, 1993Date of Patent: November 15, 1994Assignee: Arco Chemical TechnologyInventor: Jose F. Pazos
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Patent number: 5357038Abstract: The present invention relates to a process for improving the polyurethane-forming reactivity of a propylene oxide-based ethylene oxide-free polyol produced using a double metal cyanide complex catalyst by incorporating therein a minor amount of a base prior to employing the polyol in a polyurethane-forming reaction. Also claimed is the base-containing polyol composition produced in accordance with the present invention.Type: GrantFiled: September 2, 1993Date of Patent: October 18, 1994Assignee: Olin CorporationInventors: John W. Reisch, Deborah M. Capone, Ronald S. Blackwell
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Patent number: 5342903Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.Type: GrantFiled: April 30, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
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Patent number: 5340916Abstract: The present invention relates to a process for the preparation of a hard foam containing urethane groups or urethane and isocyanurate groups by the polyisocyanate polyaddition process, by reactinga) a polyoxypropylene- or polyoxyethylene-polyoxypropylene-polyol containing secondary hydroxyl groups, having a functionality of from 3.5 to 4.3, a hydroxyl number of from 350 to 650 and a viscosity of from 500 to 2,500 mPa.multidot.s at 23.degree. C.Type: GrantFiled: October 26, 1992Date of Patent: August 23, 1994Assignee: BASF AktiengesellschaftInventors: Rolf Henn, Werner Hinz, Ludwig Schuster, Klaus Vorspohl
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Patent number: 5321167Abstract: An alkoxidation production low in alkylene oxide and 1,4-dioxane content is prepared by reacting an alkylphenol or fatty alcohol with an alkylene oxide in the presence of an alkali fatty alkoxide obtained by direct reaction of an alkali hydroxide with a fatty alcohol at elevated temperature.Type: GrantFiled: December 23, 1992Date of Patent: June 14, 1994Assignee: Huls AktiengesellschaftInventors: Egbert Schroer, Klaus Schulze, Ekkehard Wienhofer
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Patent number: 5313000Abstract: This invention relates to the production of hydroxy-terminated polymers in the 2,000-20,000 MW range suitable for use as prepolymers in curing reactions with isocyanates to produce elastomers. The process involves the continuous addition over periods of 25-50 hours of an oxirane (monoepoxide) or a mixture of an oxirane and an oxetane to a reaction mixture, consisting of stoichiometric excesses of oxonium ion-forming catalyst such as BF.sub.3 -etherate and a diol initiator dissolved in an inert solvent. Under these conditions, chain extension of the diol occurs and the formation of cyclic oligomers and other impurities is minimised. The mole ratio of the initiator to catalyst is maintained at above 10:1 to suppress the formation of cationic terminal species on the growing polymer chain.Type: GrantFiled: January 27, 1992Date of Patent: May 17, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern IrelandInventor: Malcolm J. Stewart
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Patent number: 5290912Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.Type: GrantFiled: January 10, 1992Date of Patent: March 1, 1994Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
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Patent number: 5266681Abstract: The present invention relates to a process for improving the polyurethane-forming reactivity of a propylene oxide-based ethylene oxide-free polyol produced using a double metal cyanide complex catalyst by incorporating therein a minor amount of a base prior to employing the polyol in a polyurethane-forming reaction. Also claimed is the base-containing polyol composition produced in accordance with the present invention.Type: GrantFiled: August 3, 1992Date of Patent: November 30, 1993Assignee: Olin CorporationInventors: John W. Reisch, Deborah M. Capone, Ronald S. Blackwell
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Patent number: 5256828Abstract: Disclosed is a process for producing narrow range glycols which comprises reacting a glycol with ethylene oxide in the presence of a heterogeneous catalyst consisting essentially of an alkali metal, alkaline earth metal or alkali metal halide impregnated into an inorganic solid oxide selected from the groups consisting of small pore faujasite zeolites, pentasil zeolites, small pore ferrierite zeolites, two-dimensional mordenite zeolites, .beta.-type zeolite, basic zeolites and Group IV oxides or mixtures thereof.Type: GrantFiled: February 25, 1993Date of Patent: October 26, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, John F. Knifton, Pei-Shing E. Dai
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Patent number: 5235114Abstract: A process for producing an ethylene oxide-capped polyol which is essentially free of catalyst residues, wherein the polyol is produced using a double metal cyanide catalyst, which comprises after polyol formation the steps of: (a) contacting a catalyst residue(s)-containing polyol with an effective amount of an oxidant (preferably selected from the group consisting of: oxygen-containing gas(es), peroxide(s), acids, and combinations thereof) to cause said catalyst residue(s) to form insoluble residues that are insoluble in the polyol; (b) separating the insoluble residues from the polyol to provide an essentially double metal cyanide catalyst residue-free polyol; (c) treating said double metal cyanide catalyst residue-free polyol with a base to provided a base-treated polyol; (d) contacting said base-treated polyol with ethylene oxide to produce an ethylene oxide-capped polyol containing base, wherein at least a portion of the secondary hydroxyl groups on said polyol are converted into primary hydroxyl groups,Type: GrantFiled: May 18, 1992Date of Patent: August 10, 1993Assignee: Olin CorporationInventors: John W. Reisch, Michael M. Martinez, Maurice Raes
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Patent number: 5227537Abstract: A method is described for the production of 6,12-dihydro-6-hydroxy-cannabidiol which is obtained by the reaction of olivetol and cis-p-menth-2-ene-1,8,-diol and the reaction thereof to yield trans-delta-9-tetrahydrocannabinol.Type: GrantFiled: January 8, 1992Date of Patent: July 13, 1993Assignee: Heinrich Mack Nachf.Inventors: Peter Stoss, Peter Merrath
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Patent number: 5210323Abstract: In the process described for the preparation of alkoxylates having a narrow distribution of homologs by reaction of compounds containing at least one hydroxyl group with alkylene oxide, complex compounds of antimony pentahalide with a special Lewis base are used as the catalysts. Alkoxylates having a narrow distribution of homologs and good color quality are obtained at a high conversion.Type: GrantFiled: May 28, 1992Date of Patent: May 11, 1993Assignee: Hoechst Aktiengese IlschaftInventors: Ignaz Wimmer, Rainer Kupfer
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5162589Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of sodium barium phosphate or potassium barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates.Type: GrantFiled: June 8, 1992Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Rudolf J. Wijngaarden, Kees Latjes
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Patent number: 5144093Abstract: A process for producing an ethylene oxide-capped polyol which is essentially free of catalyst residues, wherein the polyol is produced using a double metal cyanide catalyst, which comprises after polyol formation the steps of: (a) contacting a catalyst residue(s)- containing polyol with an effective amount of an oxidant (preferably selected from the group consisting of: oxygen-containing gas(es), peroxide(s), acids, and combinations thereof) to cause said catalyst residue(s) to form insoluble residues that are insoluble in the polyol; (b) separating the insoluble residues from the polyol to provide an essentially double metal cyanide catalyst residue-free polyol; (c) treating said double metal cyanide catalyst residue-free polyol with a base to provided a base-treated polyol; (d) contacting said base-treated polyol with ethylene oxide to produce an ethylene oxide-capped polyol containing base, wherein at least a portion of the secondary hydroxyl groups on said polyol are converted into primary hydroxyl groupsType: GrantFiled: April 29, 1991Date of Patent: September 1, 1992Assignee: Olin CorporationInventors: John W. Reisch, Michael M. Martinez, Maurice Raes
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Patent number: 5136106Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zirconium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: March 14, 1991Date of Patent: August 4, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5126493Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.Type: GrantFiled: April 5, 1991Date of Patent: June 30, 1992Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
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Patent number: 5122548Abstract: This invention relates to elastomeric polyisocyanate-based polymers, particularly polyurethane elastomeric polymers, prepared from polyol compositions comprising a polyoxyalkylene polyol having a hydroxyl equivalent weight of from about 800 to about 3000 and containing from 10 to 40 weight percent polymerized ethylene oxide wherein the ethylene oxide is distributed as a plurality of internal polyoxyethylene blocks having a molecular weight of from about 176 to about 600, and a polyoxyethylene cap use of such polyols. Polyols provides for polymers exhibiting desirable physical properties including good abrasion wear resistance.Type: GrantFiled: March 23, 1990Date of Patent: June 16, 1992Assignee: The Dow Chemical CompanyInventors: Rene Broos, Johan A. Thoen, Richard J. Elwell
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5114619Abstract: This invention is a process for the preparation of a polyol having an equivalent weight of 200 to 5000 by the reaction of a monoepoxy compound with an initiator containing an active hydrogen atom in the presence of a catalyst substance selected from the group consisting of barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, and mixtures thereof. The process comprises adding water during the reaction of the monoepoxy compound with the initiator. The quantity of water added is one percent or less by weight of the total weight of monoepoxy compound to be reacted with the initiator.Type: GrantFiled: July 14, 1989Date of Patent: May 19, 1992Assignee: The Dow Chemical CompanyInventor: A. J. Heuvelsland
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Patent number: 5110991Abstract: Disclosed is a novel method for alkoxylation alcohols by reacting the alcohols with epoxides over a heterogeneous catalyst comprising a fluoride of an element of Group I of the Periodic Table on an oxide of Group IIA or Group IIIA of the Periodic Table.Type: GrantFiled: April 1, 1991Date of Patent: May 5, 1992Assignee: Texaco Chemical CompanyInventors: Donald H. Champion, George P. Speranza
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5099042Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.Type: GrantFiled: March 14, 1989Date of Patent: March 24, 1992Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5059719Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.Type: GrantFiled: March 23, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5053554Abstract: Radiation curable compositions containing outstanding reactive diluents have been developed. The diluents are lower alkyl ether acrylates and methacrylates of particular alkoxylated and non-alkoxylated polyols.Examples are mono-methoxy trimethylolpropane diacrylate, mono-methoxy neopentyl glycol monoacrylate and mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide.Type: GrantFiled: January 30, 1990Date of Patent: October 1, 1991Assignee: Diamond Shamrock Chemical CompanyInventors: Francis A. Higbie, Robert A. LieBerman, Ira M. Rose
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Patent number: 5041688Abstract: The invention relates to a process for the preparation of polyglycerols (with more than 50% by weight of diglycerol) which are low in cyclic components, by reacting glycerol with chlorohydrins. In this reaction, glycerol is reacted with epichlorohydrin (instead of chlorohydrin) at temperatures from 20.degree. to 120.degree. C. and at certain mole ratios of glycerol to epichlorohydrin and in the presence of an acidic catalyst and the reaction mixture obtained, which has not been separated into its components, is reacted at a temperature from 50.degree. C. to 120.degree. C. according to the content of organically bound chlorine in the reaction mixture, with an alkaline-reacting, preferably aqueous solution. After the addition of water, the reaction mixture is desalinated via one or more cation and subsequent anion exchangers, dehydrated by distillation and the glycerol-polyglycerol mixture obtained is separated by fractional distillation into glycerol, diglycerol and higher polyglycerols.Type: GrantFiled: December 19, 1989Date of Patent: August 20, 1991Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5010047Abstract: A process for recovering double metal cyanide complex catalyst from a polymer such as polypropylene glycol in a form suitable for use as a polymerization catalyst is described. The process comprises the steps of (a) combining the polymer with a non-polar solvent to precipitate the catalyst and (b) filtering the resulting mixture in the presence of a filter aid to separate the polymer from the precipitated catalyst. In contrast to the prior art methods of catalyst removal, the process of the invention yields polymer uniformly low in color as well as recovered catalyst which may be reused in subsequent polymerizations.Type: GrantFiled: February 27, 1989Date of Patent: April 23, 1991Assignee: Arco Chemical Technology, Inc.Inventor: Jonathan L. Schuchardt
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Patent number: 5010187Abstract: Polyether polyols having an equivalent weight of from about 200 to about 5000 are prepared by the process of this invention. The process uses barium- or strontium-containing alkoxylation catalysts to provide products with reduced unsaturation in comparison to similar products produced with potassium hydroxide catalysis. The use of these catalysts also increases the capping efficiency with ethylene oxide to provide products with a higher primary hydroxyl content for the same weight percentage of ethylene oxide cap.Type: GrantFiled: November 18, 1988Date of Patent: April 23, 1991Assignee: Dow Chemical CompanyInventor: Albert J. Heuvelsland
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Patent number: 5010173Abstract: The present application relates to a novel method of stabilizing the molecular weight of alkoxylates and stable compositions. The polyoxyalkylene compounds have incorporated into them, from the time of reaction of the alkylene oxide, a free radical type inhibitor which significantly improves stability of both the polymer.Type: GrantFiled: June 4, 1990Date of Patent: April 23, 1991Assignee: LCE PartnershipInventors: Anthony J. O'Lenick, Jr., John C. Miller, J. Michael Clumpner
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Patent number: 4996310Abstract: There is described and claimed a polyol-polyether having a high content of ethylene oxide and low viscosity, greatly suitable for use in the preparation of rigid polyurethane foam.The polyol-polyether of this invention is of high quality and low cost, as well as having low viscosity, thus expediting handling in foaming machines.Type: GrantFiled: March 10, 1989Date of Patent: February 26, 1991Assignee: Polioles, S. A. de C.U.Inventor: Roberto M. Acosta
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Patent number: 4992594Abstract: A process is disclosed for the preparation of polyglycerols (containing more than 50% by weight of diglycerol) which have a low content of cyclic components, by reacting chlorohydrins. In this reaction .alpha.-monochlorohydrin and epichlorohydrin are reacted at temperatures of 20.degree. to 120.degree. C., preferably 50.degree. C. to 100.degree. C., in a molar ratio of epichlorohydrin to .alpha.-monochlorohydrin of 0.8:1 to 1:2.5 in the presence of acids or compounds having an acid reaction. A medium having an alkaline reaction, preferably an aqueous solution having an alkaline reaction, is added to the resulting unseparated reaction mixture, at a temperature of 50.degree. C. to 120.degree. C., preferably 80.degree. C. to 95.degree. C. The amount of this addition is based on the content of organically-bound chlorine in the reaction mixture. After the addition of water, the reaction mixture is desalinated via one or more cation exchangers and subsequently anion exchangers.Type: GrantFiled: January 3, 1990Date of Patent: February 12, 1991Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 4978805Abstract: Polyethers I ##STR1## R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.20 -alkyl, n and m are each from 1 to 30 and r is from 0 to 20, are used mainly as surfactants in detergent and cleaning agent formulations.Type: GrantFiled: June 9, 1989Date of Patent: December 18, 1990Assignee: BASF AktiengesellschaftInventors: Richard Baur, Stefan Birnbach, Alfred Oftring, Ekhard Winkler
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Patent number: 4971649Abstract: Tiles are laid using a tile adhesive which is based on a polymer dispersion and conventional additives and contains, as a thickener, a compound of the general formula I ##STR1## where R is a radical of dihydric to hexahydric alcohol of 2 to 10 carbon atoms, which radical is bonded via oxygen, R.sup.1 is alkyl, alkoxymethyl or alkenyloxymethyl or a mixture of these radicals, each having 16 to 30 carbon atoms in the alkyl, alkoxy or alkenyloxy radical, A is --CH.sub.2 CH.sub.2 --O-- (=EO) alone or as a mixture with ##STR2## --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --O--, where A is not less than 50, preferably not less than 70, mol % of --CH.sub.2 CH.sub.2 O--, x is from 12 to 500, y has a mean value (averaged over a large number of molecules) of from 0.3 to 5, preferably from 0.5 to 2, and n is an integer from 2 to 6.Type: GrantFiled: March 2, 1989Date of Patent: November 20, 1990Assignee: BASF AktiengesellschaftInventors: Oral Aydin, Peter Fickeisen, Rainer Hummerich, Hans-Helmut Goertz