Polytetramethylene Glycols Patents (Class 568/617)
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Patent number: 5951829Abstract: A method of separating heteropoly compounds from mixtures of polyethers, polyesters and/or polyether esters, a protic component and heteropoly compounds, wherein the protic component is removed from the mixture and subsequently separating off the heteropoly compound as a separate phase. The polymer phase which remains is preferably brought into further contact with a solid adsorbent that is capable of adsorbing heteropoly compounds.Type: GrantFiled: March 27, 1997Date of Patent: September 14, 1999Assignee: BASF AktiengesellschaftInventors: Hans-Jurgen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Muller
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Patent number: 5939590Abstract: Tetrahydrofuran/but-2-yne-1,4-diol copolymers containing C--C triple bonds and having an average molecular weight M.sub.n of from 500 to 3500 Dalton and a content of from 0.5 to 3 mol of triple bonds/mol of copolymer and blends of these copolymers with polytetrahydrofuran having an average molecular weight M.sub.n of from 500 to 3500 Dalton, processes for their preparation and their use.Type: GrantFiled: August 26, 1997Date of Patent: August 17, 1999Assignee: Basf AktiengesellschaftInventors: Christoph Sigwart, Rolf Fischer, Rainer Becker, Klaus-Dieter Plitzko, Gerd Heilen, Christof Palm, Peter Groll
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Patent number: 5907054Abstract: The present invention provides a process for the production of an ester of polyoxyalkylene glycol on an industrially favorable basis which comprises the ring opening polymerization of a cyclic ether in the presence of a carboxylic anhydride and a solid acid polymerization catalyst to obtain a polymer esterified at some or all of the ends thereof, wherein the water content in the reaction system is maintained at not more than 30 ppm by weight during the polymerization reaction.Type: GrantFiled: June 2, 1997Date of Patent: May 25, 1999Assignee: Mitsubishi Chemical CorporationInventors: Tohru Setoyama, Yoshio Kabata, Mitsuharu Kobayashi
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Patent number: 5892130Abstract: Disclosed is an oxyalkylene-modified polyoxybutylene alcohol having an improved viscosity index. Notably enhancement of the viscosity index is obtained when the polyoxybutylene alcohol contains an internal oxypropylene or oxyethylene block; and wherein the total amount of converted butylene oxide in the molecule is from 99 to 75 parts per 100 parts by weight of the total converted alkylene oxide.Type: GrantFiled: May 1, 1997Date of Patent: April 6, 1999Assignee: The Dow Chemical CompanyInventor: Ronald van Voorst
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Patent number: 5886138Abstract: A process for the continuous and discontinuous production of tetrahydrofuran polymers by homopolymerizing tetrahydrofuran or copolymerizing tetrahydrofuran with 1,2-alkylene oxides in the presence of compounds with reactive hydrogen or carboxylic acid anhydrides on an acid-treated, calcined and granulated aluminium silicate catalyst which may consist of amorphous aluminium silicate, a zeolite or kaolin. By keeping the concentration of carboxylic acid anhydride or alkylene oxide constant below 1 wt. % in the polymerization recipe throughout the polymerization it is possible to largely prevent the formation of cyclic ethers and to obtain a polymer with a very narrow molecular weight distribution. In granular form, the catalysts exhibit a hitherto unknown activity and form polymers with a very narrow molecular weight distribution and low color and acid numbers.Type: GrantFiled: July 30, 1997Date of Patent: March 23, 1999Inventor: Herbert Muller
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Patent number: 5852218Abstract: A method for converting the diester of a polyether polyol (e.g., the diacetate ester of polytetramethylene ether, PTMEA) to a corresponding dihydroxy polyether polyol (e.g., polytetramethylene ether glycol, PTMEG) involving reactive distillation wherein a diester of polyether polyol is fed to the top portion of the column along with an effective amount of at least one alkali metal oxide or alkaline earth metal oxide, hydroxide or alkoxide catalyst (e.g., sodium methoxide) and with a C.sub.1 to C.sub.4 alkanol (e.g., methanol) while simultaneously adding to the bottom of the reactive distillation column hot alkanol vapor to sweep any alkanol ester formed by alkanolysis of the diester of polyether polyol upwardly. Such a process is useful for achieving high levels of conversion PTMEA to PTMEG on a commercial scale with the overhead from the column being amenable to azeotropic separation of the methyl acetate and recycle of the methanol.Type: GrantFiled: December 14, 1995Date of Patent: December 22, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai
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Patent number: 5773648Abstract: A process for the preparation of polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.10 monocarboxylic acids by the polymerization of tetrahydrofuran over a heterogeneous catalyst in the presence of one of the telogens water, 1,4-butanediol or polytetrahydrofuran having a molecular weight of from 200 to 700 dalton or a C.sub.1 -C.sub.10 monocarboxylic acid or mixtures of these telogens, wherein a supported catalyst is used as catalyst, which contains a catalytically active amount of an oxygen-containing tungsten or molybdenum compound or mixtures of these compounds on an oxidic support material and which was calcined at temperatures ranging from 500.degree. to 1000.degree. C. following the application of the precursor compounds of said oxygen-containing molybdenum and/or tungsten compounds to the support material precursor.Type: GrantFiled: March 7, 1997Date of Patent: June 30, 1998Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Christoph Sigwart, Michael Hesse, Rolf Fischer, Karsten Eller, Gerd Heilen, Klaus-Dieter Plitzko
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Patent number: 5741946Abstract: Cyclic ethers are polymerized or copolymerized in homogeneous liquid phase using very low concentrations of heteropolyacid catalyst to produce essentially linear polyoxyalkylene polymers. The product of the polymerization contains less than 2 weight percent cyclic oligomer by-product and has a molecular weight distribution (M.sub.w /M.sub.n) between 1 and 2. Alcohols, acyl-containing compounds and alkalies can be used as end-caping groups to terminate polymerization or modify the properties of the polymer produced. The process produces novel polyoxyalkylene copolymers and block copolymers that are useful as lubricants. The copolymers have a high viscosity index and are compatible with mineral oil and synthetic hydrocarbon lubricants. Preferred comonomers are tetrahydrofuran, C.sub.2 -C.sub.20 monoepoxides and oxetan.Type: GrantFiled: October 16, 1996Date of Patent: April 21, 1998Assignee: Mobil Oil CorporationInventor: Liwen Wei
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Patent number: 5731476Abstract: Polyethers of polyhydric compounds are prepared by the liquid phase reaction of polyhydric compound and the reaction being carried out with separate liquid phases comprised of a polar polyhydric compound phase and an organic polyether containing phase.Type: GrantFiled: December 1, 1995Date of Patent: March 24, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Edward T. Shawl, Haven S. Kesling, Jr., Vijai P. Gupta
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Patent number: 5714638Abstract: Polyoxyalkylene glycol monoethers of monohydric alcohols are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a monohydric alcohol and of an anhydrous heteropoly acid catalyst.Type: GrantFiled: February 1, 1995Date of Patent: February 3, 1998Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5703194Abstract: 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: June 7, 1995Date of Patent: December 30, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Thomas G. Archibald
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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: 5668250Abstract: 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: June 7, 1995Date of Patent: September 16, 1997Assignee: Aerojet-General CorporationInventor: Aslam A. Malik
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Patent number: 5659068Abstract: Polyoxyalkylene glycol monoesters of carboxylic acids are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a carboxylic acid and of an anhydrous heteropolyacid catalyst.Type: GrantFiled: May 31, 1994Date of Patent: August 19, 1997Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5648557Abstract: Cyclic ethers are polymerized or copolymerized in homogeneous liquid phase using very low concentrations of heteropolyacid catalyst to produce essentially linear polyoxyalkylene polymers. The product of the polymerization contains less than 2 weight percent cyclic oligomer by-product and has a molecular weight distribution (M.sub.w /M.sub.n) between 1 and 2. Alcohols, acyl-containing compounds and alkalies can be used as end-caping groups to terminate polymerization or modify the properties of the polymer produced. The process produces novel polyoxyalkylene copolymers and block copolymers that are useful as lubricants. The copolymers have a high viscosity index and are compatible with mineral oil and synthetic hydrocarbon lubricants. Preferred comonomers are tetrahydrofuran, C.sub.2 -C.sub.20 monoepoxides and oxetan.Type: GrantFiled: October 27, 1994Date of Patent: July 15, 1997Assignee: Mobil Oil CorporationInventor: Liwen Wei
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Patent number: 5641857Abstract: Polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.20 -monocarboxylic acids or polytetrahydrofuran monoethers of monohydric C.sub.1 -C.sub.20 -alcohols, having an average molecular weight of from 250 to 10,000 Dalton and liquid at room temperature, are prepared by the cationic polymerization of tetrahydrofuran in the presence of a telogen by a process in which tetrahydrofuran is polymerized in the presence of water, 1,4-butanediol and/or polytetrahydrofuran having an average molecular weight of from 200 to 700 Dalton and/or of a C.sub.1 -C.sub.20 -monocarboxylic acid and/or of a monohydric C.sub.1 -C.sub.20 -alcohol with the aid of a catalytic amount of a zeolite catalyst which has an SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 4:1 to 100:1 and in which the population ratio P of the acid centers on the external surface of the zeolite to the total number of acid centers of the zeolite is 0.03/l or more.Type: GrantFiled: November 7, 1995Date of Patent: June 24, 1997Assignee: BASF AktiengesellschaftInventors: Roman Dostalek, Rolf Fischer, Ulrich Mueller, Rainer Becker
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Patent number: 5641853Abstract: A process for polymerizing oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound and an accelerator which is a selected vinyl ester or a selected phosphorous compound.Type: GrantFiled: February 28, 1996Date of Patent: June 24, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5637673Abstract: Improved double metal cyanide (DMC) catalysts are disclosed. The catalysts comprise a DMC compound, an organic complexing agent, and from about 5 to about 80 wt. % of a polyether polyol that has tertiary hydroxyl groups. Compared with other DMC catalysts, those of the invention have excellent activity for epoxide polymerization, and they can be used to make polyols having very low unsaturation even at high epoxide polymerization temperatures.Type: GrantFiled: May 16, 1996Date of Patent: June 10, 1997Assignee: ARCO Chemical Technology, L.P.Inventor: Bi Le-Khac
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Patent number: 5608117Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-l-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.Type: GrantFiled: August 28, 1995Date of Patent: March 4, 1997Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5585458Abstract: A method for preparing polyether glycol is disclosed. An ester end-capped polyalkylene ether and an alcohol are subjected to alcoholysis at a temperature of 35.degree.-150.degree. C. and a pressure of 1-10 atm in the presence of a mixed metal oxide as a catalyst. The mixed metal oxide includes an alkaline earth metal oxide and at least one component selected from alumina, silica, and zinc oxide.Type: GrantFiled: June 27, 1995Date of Patent: December 17, 1996Assignee: Industrial Technology Research InstituteInventors: Wen-Fa Lin, Yu-Wen Chen, Jih-Chen Huang, Hsueh-Ying Chen
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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: 5488180Abstract: This invention relates to complex hydrophobe compounds and to alkoxylation products, i.e., condensation reaction products of alkylene oxides and complex hydrophobe compounds having at least one active hydrogen. This invention also relates to alkoxylation products that have beneficial, narrow molecular weight ranges.Type: GrantFiled: May 29, 1992Date of Patent: January 30, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard D. Jenkins, David R. Bassett, Danny E. Smith, John N. Argyropoulos, James E. Loftus, Gregory D. Shay
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Patent number: 5478920Abstract: When selected silicon compounds are added to cationic polymerizations of cyclic ethers such as oxiranes and tetrahydrofurans, the rate of polymerization is often increased, and novel polyethers are produced. The polyether products are useful as monomers and macromonomers, particularly after hydrolysis of silicon containing end groups.Type: GrantFiled: July 16, 1993Date of Patent: December 26, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville E. Drysdale
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Patent number: 5476971Abstract: Glycerine di-t-butyl ether is prepared by the liquid phase reaction of glycerine and the reaction being carried out with separate liquid phases comprised of isobutylene and glycerine.Type: GrantFiled: January 13, 1995Date of Patent: December 19, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Vijai P. Gupta
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Patent number: 5466759Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-1-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.Type: GrantFiled: October 24, 1994Date of Patent: November 14, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5463020Abstract: Polytetrahydrofuran or C.sub.2 -C.sub.10 -alkylene oxide/tetrahydrofuran copolymers having a molecular weight of from 250 to 20,000 Dalton are prepared by the cationic polymerization of tetrahydrofuran or tetrahydrofuran and C.sub.2 -C.sub.10 -alkylene oxides in the prsence of a promoter by a process in which the catalyst used is a mixture of one or more C.sub.2 -C.sub.6 -di- or tricarboxylic acids with boric acid.Type: GrantFiled: June 30, 1994Date of Patent: October 31, 1995Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
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Patent number: 5434315Abstract: Polyether glycols, especially poly(tetramethylene ether) glycols, having a narrow molecular weight distribution (e.g., Mw/Mn=1.2 to 1.80), are made by a process which consists of separating the low molecular weight fraction in an ultrafiltration module. In these units, molten PTMEG is fed at temperatures in the range of 30.degree. to 150.degree. C. and pressures ranging between 25 and 1500 psi. The PTMEG retentate from the ultrafiltration unit is also characterized by water content <25 ppm and low to negligible concentration of oligomeric cyclic ethers.Type: GrantFiled: February 22, 1994Date of Patent: July 18, 1995Assignee: E. I. du Pont de Nemours and CompanyInventors: Suriyanarayanan Dorai, William W. Goudie, Sarah E. Ochsenhirt, Dhiren V. Patel, James R. Cavall
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Patent number: 5416240Abstract: Polyoxyalkylene glycols are prepared by a process in which tetrahydrofuran is polymerized with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals in the absence of water and in the presence of a monohydric alcohol or of a monocarboxylic acid with the aid of an anhydrous heteropoly acid catalyst, and the polyoxyalkylene glycol is liberated from the resulting polyoxyalkylene glycol monoethers or polyoxyalkylene glycol monoesters by cleavage of the monoether or monoester bond.Type: GrantFiled: March 2, 1993Date of Patent: May 16, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Franz Merger, Herbert Mueller
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Patent number: 5414143Abstract: Polyoxyalkylene glycol monoethers of monohydric alcohols are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerised in the absence of water and in the presence of a monohydric alcohol and of an anhydrous heteropoly acid catalyst.Type: GrantFiled: March 2, 1993Date of Patent: May 9, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5410093Abstract: An improved method for recovering purified poly(tetramethylene ether) glycol or similar polyether polyol from an aqueous solution of polymer containing an alkaline metal catalyst residue involving the addition of a stoichiometric excess of magnesium sulfate or sulfite followed by evaporation of water and separation of molten polymer from precipitated solid phase (i.e., from magnesium hydroxide, alkaline metal sulfate/sulfite, and excess magnesium sulfate/sulfite). Such a process results in essentially complete removal of any basic transesterification catalyst and water without significant lost of poly(tetramethylene ether) glycol or the like.Type: GrantFiled: February 17, 1994Date of Patent: April 25, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Suriyanarayanan Dorai
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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: 5302255Abstract: Polyether glycols, especially poly(tetramethylene ether) glycol (PTMEG) having a narrow molecular weight distribution of about 1.25 to 1.80, or dispersity of 1.05 to 1.90, are made by a process involving distilling the low molecular weight fraction in unit operations including at least one short-path distillation evaporator. Two short-path distillation evaporators, in series, are desirable if significant narrowing of the PTMEG is required. In these units, PTMEG is subjected to temperatures in the range of 270.degree.-400.degree. C. with the hold-up time varying between 10-200 seconds. The required vacuum to force the separation of the low molecular weight PTMEG varies between 0.001 mm and 1.0 mbar. PTMEG residue from the distillation unit is also characterized by its low water content and low concentration of oligomeric cyclic ethers.Type: GrantFiled: September 15, 1992Date of Patent: April 12, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Frank L. Rawling, Jr., James A. Schultz
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Patent number: 5298670Abstract: Polytetramethylene ether glycols (PTMEG) are fractionated with liquid propane in an extractor under high pressure. Fractions are separated by altering the extraction pressure, which alters the solvent power of the propane. The polydispersities of all extracted PTMEG fractions are generally below 1.3. The addition of a cosolvent, preferably tetrahydrofuran, can effectively lower the initial extraction pressure and increase the efficiency of the extraction.Type: GrantFiled: April 2, 1993Date of Patent: March 29, 1994Assignee: Industrial Technology Research InstituteInventors: Wen-Fa Lin, Jun-Yi Chen
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Patent number: 5284980Abstract: Treatment of poly(tetramethylene ether) glycols with acid catalysts at elevated temperatures leads to a chain coupling with rapid increase in molecular weight. Various alcohols including diols and triols can be incorporated into poly(tetramethylene ether) glycol backbone with modified properties and performance.Type: GrantFiled: October 26, 1992Date of Patent: February 8, 1994Assignee: E. I. du Pont de Nemours and CompanyInventors: Gerfried Pruckmayr, Robert B. Osborne
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Patent number: 5282929Abstract: Polyether glycols, especially poly(tetramethylene ether) glycol (PTMEG) having a narrow molecular weight distribution of about 1.90 to 2.07, or dispersity of 1.50 to 1.90, are made by a process wherein the low molecular weight fraction in unit operations using at least one short-path distillation evaporator. In these units, PTMEG is subjected to temperatures in the range of 150.degree.-190.degree.C. with the hold-up time varying between 10-200 seconds. The required vacuum to force the separation of the low molecular weight PTMEG varies between 0.001 mm and 1.0 mbar. PTMEG residue from the distillation unit is also characterized by its low water content and low concentration of oligomeric cyclic ethers.Type: GrantFiled: September 15, 1992Date of Patent: February 1, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Frank L. Rawling, Jr., James A. Schultz
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Patent number: 5254745Abstract: Polyoxyalkylene polyols initiated with melamine and coinitiated with toluene diamine and oxyalkylated with one or more alkylene oxides have relatively low viscosity and are suitable for preparing polyurethane foams.Type: GrantFiled: November 12, 1991Date of Patent: October 19, 1993Assignee: BASF CorporationInventor: Joachim Jahme
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Patent number: 5210283Abstract: Tetrahydrofuran is polymerized in the presence of a carboxylic acid anhydride and a solid acid catalyst that has been calcined at a temperature greater than about 600.degree. C. Calcined bleaching earth catalysts give THF polymer products having a narrow molecular weight distribution; calcining amorphous silica-aluminas improves their activity toward THF polymerization.Type: GrantFiled: May 18, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Andrew P. Kahn, Robert G. Gastinger, Gangfeng Cai
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Patent number: 5208379Abstract: Waste or scrap polyurethane may be conveniently and economically converted to useful active-hydrogen containing polyethers and polyamines by contacting the polyurethane with water, strong base, and an activating agent such as a quaternary ammonium compound containing at least 15 carbon atoms or an organic sulfonate containing at least 7 carbon atoms. The activating agent helps to accelerate the rate of base catalyzed hydrolysis.Type: GrantFiled: May 14, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Macarevich
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Patent number: 5208385Abstract: A process for producing tetrahydrofuran polymers having a narrow molecular weight distribution is disclosed. Tetrahydrofuran is polymerized in the presence of a carboxylic acid anhydride and amorphous silica-alumina. The process overcomes the need for costly post-treatment techniques such as distillation and selective solvent extraction.Type: GrantFiled: February 19, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Andrew P. Kahn, Robert G. Gastinger, Rangasamy Pitchai
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Patent number: 5180856Abstract: New polyethers based on tetrahydrofuran, with good lubricant properties. The invention concerns polyethers produced by copolymerizing tetrahydrofuran and glycidyl ether in the presence of alkanols. The new polyethers are useful as lubricants.Type: GrantFiled: August 12, 1991Date of Patent: January 19, 1993Assignee: Huels AktiengesellschaftInventors: Michael Stehr, Heinz-Werner Voges
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Patent number: 5180857Abstract: A process for reducing the molecular weight of polytetramethylene ether glycol without significant conversion of polytetramethylene ether glycol to tetrahydrofuran monomer is disclosed. The process involves a two-step procedure. The first step comprises reacting polytetramethylene ether glycol with a perfluoroalkyl carboxylic acid to form a perfluoroalkyl ester of polytetramethylene ether glycol. That ester is, in the second step, converted back to polytetramethylene ether glycol of reduced molecular weight by hydrolysis or alcoholysis.Type: GrantFiled: March 10, 1992Date of Patent: January 19, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai
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Patent number: 5162475Abstract: Describes alpha-beta ethylenically unsaturated poly(alkyleneoxy) compounds that display surfactant activity and that polymerize when used in the emulsion polymerization of ethylenically unsaturated monomers, including vinyl monomers. Certain of the polymer products are useful in imparting improved hand or feel to textile fabrics.Type: GrantFiled: June 27, 1991Date of Patent: November 10, 1992Assignee: PPG Industries, Inc.Inventors: Robert H. Tang, Paritosh M. Chakrabarti, Edward J. Rish, William A. Williams
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Patent number: 5155283Abstract: A process for forming polytetramethylene ether glycol having a number average molecular weight of 600 to 2,200 by contacting tetrahydrofuran with 5 to 50 wt %, based on tetrahydrofuran, trifluoromethane sulfonic acid monohydrate and water at 20.degree. to 75.degree. C. is disclosed.Type: GrantFiled: July 19, 1991Date of Patent: October 13, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Gary A. Hida
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Patent number: 5149862Abstract: A process for polymerizing tetrahydrofuran to produce polytetramethylene ether glycol or ester-capped polytetramethylene ether glycol is disclosed. The reaction mass is carried out at 10.degree. to 80.degree. C. and preferably 20.degree. to 60.degree. C. In a preferred aspect of the invention, a mixture of acetic anhydride and acetic acid is present in the reaction mixture.Type: GrantFiled: February 26, 1991Date of Patent: September 22, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Melvin C. Baker, James A. Schultz
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Patent number: 5130470Abstract: A process for polymerizing tetrahydrofuran using a fluorinated resin containing sulfonic acid groups a trifluoromethane sulfonic acid as catalyst and a mixture of maleic acid and maleic anhydride as weight control agent. The product has the formula ##STR1## which can be hydrogenated to produce polytetramethylene ether glycol. The preferred molecular weight range of the polytetramethylene ether glycol is 600 to 4,000.Type: GrantFiled: March 27, 1991Date of Patent: July 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Willard L. Quon, Kirk M. Schall, Gary A. Hida
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Patent number: 5130413Abstract: A process for producing an unsaturated group-terminated high-molecular weight polyalkylene oxide by adding an alkali metal and/or an alkali metal compound capable of producing an alkali metal hydroxide on reaction with water to a hydroxyl-terminated polyalkylene oxide having a repeating unit represented by formula --R.sup.1 --O-- (wherein R.sup.1 represents a divalent alkylene group having from 2 to 8 carbon atoms) to substitute the hydrogen atom of the hydroxyl end group with an alkali metal (alkoxidation) the resulting polyalkylene oxide is reacted with a polyhalogen compound to increase the molecular weight of the polyalkylene oxide and then additional alkali metal and/or alkali metal compound is added before reacting the resulting high-molecular weight polyalkylene oxide with an unsaturated halogen compound to introduce an unsaturated group to the molecular chain terminals.Type: GrantFiled: August 30, 1990Date of Patent: July 14, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yukimitsu Asai, deceased, by Keiji Asai, legal representative, by Yoshie Asai, legal representative, Hiroyuki Kawata, Tooru Nakagawa
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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: RE35360Abstract: A process for reducing the molecular weight of polytetramethylene ether glycol without significant conversion of polytetramethylene ether glycol to tetrahydrofuran monomer is disclosed. The process involves a two-step procedure. The first step comprises reacting polytetramethylene ether glycol with a perfluoroalkyl carboxylic acid to form a perfluoroalkyl ester of polytetramethylene ether glycol. That ester is, in the second step, converted back to polytetramethylene ether glycol of reduced molecular weight by hydrolysis or alcoholysis.Type: GrantFiled: June 22, 1994Date of Patent: October 22, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai