Polytetramethylene Glycols Patents (Class 568/617)
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Patent number: 5118869Abstract: A catalyst and process for preparing it and its use in polymerizing tetrahydrofuran to produce polytetramethylene ether glycol ether are disclosed. The catalyst is a blend of a fluorinated resin containing sulfonic acid groups and a fluorinated resin containing carboxylic acid groups. The catalyst is partially dried to contain from 1,000 to 2,000 ppm water, so that when it is used to polymerize tetrahydrofuran, the product polytetramethylene ether glycol will have a number average molecular weight of from 250 to 4,000.Type: GrantFiled: February 13, 1991Date of Patent: June 2, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Gerfried Pruckmayr, Marianne Marsi, Willard L. Quon
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Patent number: 5099074Abstract: A process for the preparation of polyether glycols by polymerization of tetrahydrofuran or copolymerization of tetrahydrofuran with oxiranes in the presence of from 20 to 500% w/w of a hydrocarbon, based on the weight of tetrahydrofuran used.Type: GrantFiled: October 26, 1990Date of Patent: March 24, 1992Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Gerhard Jeschek, Rolf Fischer, Hans-Juergen Weyer
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Patent number: 5097077Abstract: A process is described for the purification of crude polyalkylene ether glycols contaminated by heteropolyacids or salts thereof, by treatment with solvents, which comprises mixing the crude polyalkylene ether glycols with a liquid hydrocarbon and water, allowing the phases to separate, and isolating the purified polyalkylene ether glycols from the upper phase.Type: GrantFiled: October 5, 1990Date of Patent: March 17, 1992Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Gerhard Jeschek, Rolf Fischer, Hans-Juergen Weyer
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Patent number: 5053553Abstract: A process for preparing a narrow molecular weight distribution poly(tetramethylene ether) glycol (PTMEG) from a PTMEG starting material via liquid-liquid extraction which employs methanol, water and non-polar solvent wherein the amount of non-polar solvent is, by weight, less than the PTMEG starting material.Type: GrantFiled: June 25, 1990Date of Patent: October 1, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Suriyanarayanan Dorai
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Patent number: 5001277Abstract: Tetrahydrofuran has been polymerized and copolymerized to form polymers of 1000 to 10,000 molecular weight using fuming sulfuric acid with a cocatalyst selected from salts of Group VA metal halides and superacid salts. The cocatalyst salts may be, for example, NaPF.sub.6, NaSbF.sub.6, and LiO.sub.3 SCF.sub.3.Type: GrantFiled: April 30, 1990Date of Patent: March 19, 1991Assignee: Arco Chemical Technology, Inc.Inventor: Jonathan L. Schuchardt
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Patent number: 4988797Abstract: Cyclic ethers having 4 and 5 member rings are polymerized with a alcohol initiator and an acid catalyst. The acid catalyst is used at a molar ratio relative to hydroxyl groups of the alcohol initiator of between about 0.05:1 and about 0.5:1.Type: GrantFiled: March 14, 1989Date of Patent: January 29, 1991Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 4970295Abstract: A process for the preparation of polyethers is disclosed in which an oxetane monomer, or a mixture of an oxetane monomer and an oxolane monomer, and a carboxylic acid anhydride are contacted with a bleaching earth catalyst. The process yields ester-terminated polyethers which may be saponified to obtain hydroxy-terminated polyether polyols.Type: GrantFiled: February 27, 1989Date of Patent: November 13, 1990Assignee: ARCO Chemical Technology, Inc.Inventor: Jonathan L. Schuchardt
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Patent number: 4967015Abstract: Polytetrahydrofuran vinyl ethers of the general formulaH.sub.2 C.dbd.HC--[)O--CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --].sub.n O--R Iwhere R is hydrogen or the CH.dbd.CH radical and n is from 2 to 150, are prepared by a process in which polytetrahydrofuran of the general formulaH--[O--CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --].sub.n OH IIis reacted with acetylene.Type: GrantFiled: October 16, 1989Date of Patent: October 30, 1990Assignee: BASF AktiengesellschaftInventors: Michael Karcher, Heinz Eckhardt, Jochem Henkelmann
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Patent number: 4962237Abstract: A catalytic process for polymerizing epoxides using active hydrogen initiators forming polyols having low unsaturation levels and high primary hydroxyl levels. The catalysts useful in this process are prepared from catalyst precursors exemplified by hydrotalcite. This process is more reactive with less acidic active hydrogen initiators. The polyols can be used in urethanes without removal of the catalyst.Type: GrantFiled: January 2, 1990Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventor: David E. Laycock
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Patent number: 4954658Abstract: A process for reducing fluoride levels in PTMEG by heating aqueous PTMEG having an undesired level of fluoride (80'600 ppm) to a temperature in the range between about 200.degree. and 300.degree. C. for a period of time sufficient to reduce the fluoride content of said PTMEG. Preferably, heating is carried out with agitation to a temperature between about 225.degree. and about 275.degree. C. for about 1 minute to about 8 hours in the presence of an aqueous base, most preferably 240.degree. to 250.degree. C. in presence of aqueous lime.Type: GrantFiled: September 14, 1989Date of Patent: September 4, 1990Assignee: E. I. du Pont de Nemours and CompanyInventors: Suriyanarayanan Dorai, Richard E. Ernst
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Patent number: 4952673Abstract: A process for the purification of the polyetherdiols obtained by copolymerization of tetrahydrofuran and 1-alkene oxides by catalytic hydrogenation at temperatures up to 250.degree. C.Type: GrantFiled: August 1, 1988Date of Patent: August 28, 1990Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4933503Abstract: The molecular weight distribution of polytetrahydrofuran and of copolymers of tetrahydrofuran and alkylene oxides are narrowed by a process in which low molecular weight fractions are distilled off from the polymers under pressures of less than 0.3 mbar and at from 200.degree. to 260.degree. C., the distillation residue is mixed with a solvent mixture consisting of (a) an alkanol, (b) a hydrocarbon and (c) water, the content of the individual components a, b and c in the mixture being from 4 to 60% by weight, the phases formed are then separated from one another and the polymer having a narrower molecular weight distribution is isolated from the phase.Type: GrantFiled: August 15, 1988Date of Patent: June 12, 1990Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4879420Abstract: Process for preparing 2-alkyl-1,4-butanediols and mixtures with 1,4-butanediol which comprises bringing together, at an initial alkaline pH, and at a temperature and pressure suitable for reaction, a mixture of 4-hydroxybutyraldehyde and/or its cyclic acetal, 2-hydroxytetrahydrofuran, hydrogen, an unsubstituted aliphatic aldehyde, especially formaldehyde, and a hydrogenation catalyst. Also processes for preparing mixtures of tetrahydrofuran and 3-alkyltetrahydrofuran from the diol mixtures, and copolymers from the tetrahydrofuran mixtures.Type: GrantFiled: May 6, 1988Date of Patent: November 7, 1989Assignee: E.I. du Pont de Nemours and CompanyInventor: Richard E. Ernst
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Patent number: 4877906Abstract: A method for removing double metal cyanide complex catalyst from polyether polyols is disclosed which uses alkali metal compounds and phosphorous compounds to precipitate the residual catalyst, which may then be removed by filtration. In one embodiment, a propylene oxide polyol is treated with sodium metal dispsersion, capped with ethylene oxide, treated with magnesium silicate, and then filtered to remove at least a portion of the catalyst. Substantially complete catalyst removal is then achieved by treating the polyol with hypophosphorous or phosphorous acid to precipitate the remaining solubilized double metal cyanide complex catalyst residue, neutralizing the excess acid with magnesium silicate, and filtering.Type: GrantFiled: November 25, 1988Date of Patent: October 31, 1989Assignee: Arco Chemical Technology, Inc.Inventor: Stephen D. Harper
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Patent number: 4859801Abstract: Process for preparing 2-alkyl-1,4-butanediols and mixtures with 1,4-butanediol which comprises bringing together, at an initial alkaline pH, and at a temperature and pressure suitable for reaction, 2,3-dihydrofuran, hydrogen, an unsubstituted aliphatic aldehyde, especially formaldehyde, and a hydrogenation catalyst. Also processes for preparing mixtures of tetrahydrofuran and 3-alkyltetrahydrofuran from the diol mixtures, and copolymers from the tetrahydrofuran mixtures.Type: GrantFiled: May 26, 1988Date of Patent: August 22, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard E. Ernst
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Patent number: 4806694Abstract: Fluorine-containing polyols obtained by the free radical addition of a fluoro-olefin having the general formula: ##STR1## wherein Y represents F and Z represents Cl or F(CF.sub.2)n--wherein n is an integer from 0 to 10 or Y and Z together form a --(CF.sub.2)m-- chain wherein m represents an integer from 2 to 4 to a polyol wherein each hydroxyl group is directly attached to a group of the formula:--(CH.sub.2).sub.p O-- (2)wherein p is an integer of at least 4.Type: GrantFiled: September 10, 1987Date of Patent: February 21, 1989Assignee: Imperial Chemical Industries PLCInventors: Richard L. Powell, Brian Young
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Patent number: 4803299Abstract: Polytetramethylene ether glycol diesters having a low color number are prepared by catalytic polymerization of tetrahydrofuran in the presence of a carboxylic anhydride, a bleaching earth and from 2 to 0.2% by weight, based on the tetrahydrofuran, of an alkylene oxide.Type: GrantFiled: April 6, 1987Date of Patent: February 7, 1989Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4792627Abstract: A process for producing a polyether polyol with a content of 0.5 to 99.5% by weight of oxytetramethylene groups derived from tetrahydrofuran by copolymerizing tetrahydrofuran or a mixture of tetrahydrofuran and other cyclic ether copolymerizable therewith with a polyhydric alcohol having two or more hydroxyl groups per one molecule with the use of a heteropoly-acid and/or its salt as a catalyst, which comprises allowing 0.1 to 15 molecules of water per one heteropoly-anion to exist in the catalyst phase.The above-described polyether polyol is an industrially useful polymer which is a starting material for polyurethane to be used for spandex or a synthetic leather, etc.Type: GrantFiled: December 22, 1986Date of Patent: December 20, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
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Patent number: 4762951Abstract: The molecular weight distribution of polytetrahydrofuran and of copolymers of tetrahydrofuran and alkylene oxides is narrowed by a process in which the polymers are mixed with a solvent mixture consisting of (a) an alkanol, (b) a hydrocarbon and (c) water, the content of the individual components a, b and c in the mixture being from 8 to 60% by weight, after which the three phases formed are separated from one another and the polymer having the narrower molecular weight distribution is isolated from the two lower phases.Type: GrantFiled: March 4, 1987Date of Patent: August 9, 1988Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4751331Abstract: Polyether polyols are decolorized by heating to a temperature in excess of 95.degree. C. in the presence of water and air. The resulting polyols have minimal residual color, and can be used to prepare polyurethanes having low color.Type: GrantFiled: May 1, 1987Date of Patent: June 14, 1988Assignee: The Dow Chemical CompanyInventor: Elizabeth A. Efford
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Patent number: 4728722Abstract: A process for the batchwise preparation of polyoxybutylene polyoxyalkylene glycols by copolymerizing tetrahydrofuran with a 1,2-alkylene oxide in the presence of compounds containing reactive hydrogen, the polymerization being carried out over a bleaching earth catalyst or zeolite catalyst, and the 1,2-alkylene oxide being fed to the reaction mixture in such manner that the concentration of the 1,2-alkylene oxide in the reaction mixture is kept at below 2% by weight during the polymerization.Type: GrantFiled: February 12, 1987Date of Patent: March 1, 1988Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4677231Abstract: A process for purifying a polyalkylene ether, which comprises mixing a polyalkylene ether or a mixture of a polyalkylene ether and an organic solvent containing a heteropoly acid and/or its salt with at least one solvent for purification selected from hydrocarbons having 3 to 15 carbon atoms or halogenated hydrocarbons having 1 to 15 carbon atoms and separating by precipitation the phase composed mainly of the heteropoly acid and/or its salt, and a process wherein the polyalkylene ether or a mixture of a polyalkylene ether and an organic solvent containing a heteropoly acid and/or its salt is brought into contact with a solid adsorbent capable of adsorbing the heteropoly acid and/or its salt in the presence of at least one solvent for purification as described above, either further after the separation according to the process described above, or in the state unseparated.Type: GrantFiled: November 8, 1985Date of Patent: June 30, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Setsuo Yamamatsu, Shoichiro Tonomura
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Patent number: 4658065Abstract: A process for producing a polyether polyol with a content of 0.5 to 99.5% by weight of oxytetramethylene groups derived from tetrahydrofuran by copolymerizing tetrahydrofuran or a mixture of tetrahydrofuran and another cyclic ether copolymerizable therewith with a polyhydric alcohol having two or more hydroxyl groups per one molecule with the use of a heteropoly-acid and/or its salt as a catalyst, which comprises allowing 0.1 to 15 molecules of water per one heteropoly-anion to exist in the catalyst phase.The above-described polyether polyol is an industrially useful polymer which is a starting material for polyurethane to be used for spandex or a synthetic leather, etc.Type: GrantFiled: March 27, 1985Date of Patent: April 14, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
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Patent number: 4638097Abstract: The content of cyclic oligomeric ethers in polytetramethylene ether glycols or polyoxybutylene polyoxyalkylene glycols is reduced by a process in which a polytetramethylene ether glycol or polyoxybutylene polyoxyalkylene glycol which contains the said ethers and has a mean molecular weight of from 200 to 450 is mixed with a mixture of water and a hydrocarbon, and, after phase separation, the purified polytetramethylene ether glycol or polyoxybutylene polyoxyalkylene glycol is isolated from the aqueous phase.Type: GrantFiled: March 21, 1986Date of Patent: January 20, 1987Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4624299Abstract: A method of indirect liquid phase heat transfer which comprises continuously circulating between a heat generating and a heating source or water-soluble or water-dispersible polymer having a viscosity of less than about 100 centistokes at 100.degree. F., of the formula:R(OAR').sub.xwhereinR is a C.sub.5 to C.sub.36 linear branched or alicyclic aliphatic hydrocarbyl group;O is oxygen;A is a polyoxyalkylene residue having oxyalkylene units derived from ethylene oxide or ethylene oxide and at least one other lower alkylene oxide having 3 or 4 carbon atoms;R' is hydrogen, a C.sub.1 to C.sub.8 alkyl group or nonbornyl; andx is an integer having a value of 1 to 6, wherein for values of x greater than 1 each AR' may be the same or different.Type: GrantFiled: June 28, 1985Date of Patent: November 25, 1986Assignee: Union Carbide CorporationInventors: Ronald H. Harding, George E. Totten
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Patent number: 4617984Abstract: A method of indirect liquid phase heat transfer utilizing as a heat transfer fluid a composition comprising polytetra(methylene oxide) or poly(trimethylene oxide) homopolymers having molecular weights of from about 300 to about 1,000.Type: GrantFiled: June 28, 1985Date of Patent: October 21, 1986Assignee: Union Carbide CorporationInventors: Ronald H. Harding, George E. Totten
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Patent number: 4599460Abstract: Polyalkylene ether glycol copolymers having a number-average molecular weight of from 200 to 10,000 and having hydroxyl groups at both ends of the molecule are disclosed.Type: GrantFiled: August 13, 1985Date of Patent: July 8, 1986Assignee: Daicel Chemical Industries, Ltd.Inventors: Yuzo Toga, Ichiro Okamoto, Tatsuya Kanno
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Patent number: 4595537Abstract: A novel randomly polymerized polyglycerol, polytrimethylene- or -tetramethylene-oxide condensate of an 8-36 carbon aliphatic alcohol or fatty acid useful as a non-ionic surface active agent.Type: GrantFiled: June 28, 1985Date of Patent: June 17, 1986Assignee: Pola Chemical Industries, Inc.Inventors: Michio Ochiai, Hiromichi Sagitani
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Patent number: 4590054Abstract: The color level of poly(tetramethylene ether) glycol made by polymerizing tetrahydrofuran using fluosulfonic acid as the catalyst is significantly lower if the fluosulfonic acid contains no more than about 1200 ppm of iron sulfites.Type: GrantFiled: September 16, 1985Date of Patent: May 20, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: William W. Kasper, Willard L. Quon, Timothy D. Van Domelen
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Patent number: 4585592Abstract: In polyoxybutylene polyoxyalkylene glycols obtained by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen and under the catalytic action of a bleaching earth, the content of oligomeric cyclic ethers is reduced by distillation under reduced pressure at above 200.degree. C. after first treating the copolymer with oxygen or an oxygen-containing gas (air) at a temperature of from 20.degree. to 110.degree. C.Type: GrantFiled: February 28, 1985Date of Patent: April 29, 1986Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4584414Abstract: In the process of converting a poly(tetramethylene ether) diester to poly(tetramethylene ether) glycol by catalytic alcoholysis, using an alkali metal hydroxide or alkoxide as the catalyst, contamination of the polymer product can be reduced by reacting the catalyst with an acid after the alcoholysis reaction is complete, and then removing the reaction product from the reaction mass.Type: GrantFiled: December 21, 1984Date of Patent: April 22, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerfried Pruckmayr
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Patent number: 4569990Abstract: The color level of poly(tetramethylene ether) glycol made by polymerizing tetrahydrofuran using fluosulfonic acid as the catalyst is significantly lower if the fluosulfonic acid contains no more than about 1200 ppm of iron sulfites.Type: GrantFiled: August 27, 1984Date of Patent: February 11, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: William W. Kasper, Willard L. Quon, Timothy D. Van Domelen
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Patent number: 4568775Abstract: A process for producing a polyoxytetramethylene glycol or a copolymerized polyetherglycol by polymerizing tetrahydrofuran or a mixture of tetrahydrofuran with other cyclic ethers copolymerizable therewith, which comprises using a heteropoly-acid as a catalyst and permitting 0.1 to 15 mol of water per mol of the heteropolyacid to be present in the catalyst phase.The above-described polymer and copolymer are industrially useful polymers which can be used as the primary starting materials for polyurethanes to be used for a spandex and a synthetic leather, solvents, pressured fluids, etc.Type: GrantFiled: May 16, 1984Date of Patent: February 4, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Shoichiro Tonomura
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Patent number: 4564671Abstract: Polyoxybutylene polyoxyalkylene glycols are prepared by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen, by a continuous process in which the polymerization is carried out in a reactor over a fixed-bed clay catalyst and with recycling of the reaction mixture, and less than 30% by weight, based on the reaction mixture to be recycled, of a mixture of tetrahydrofuran, 1,2-alkylene oxide and a compound containing reactive hydrogen is added to the reaction mixture, which is recycled to the reactor after flowing through the latter.Type: GrantFiled: December 14, 1984Date of Patent: January 14, 1986Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4544774Abstract: The color level of poly(tetramethylene ether) glycol made by catalytically polymerizing tetrahydrofuran using fluosulfonic acid as the catalyst is significantly lower if the fluosulfonic acid contains aluminum.Type: GrantFiled: December 5, 1984Date of Patent: October 1, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Rudolph Pick
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Patent number: 4510333Abstract: In the preparation of poly(tetramethylene ether) glycol by the polymerization of tetrahydrofuran (THF) using a cationic initiator, molecular weight distribution (MWD) can be held within narrow limits by bringing the THF and the initiator together in a mol ratio such that the degree of polymerization will be at about a minimum and at a temperature which will promote about a maximum number of tertiary oxonium ions, then quickly cooling the reaction mass to -25.degree. C. to +25.degree. C., and then adding enough THF to complete the polymerization. When the desired molecular weight and MWD have been reached, the polymerization is quenched and the polymer isolated.Type: GrantFiled: June 5, 1984Date of Patent: April 9, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerfried Pruckmayr
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Patent number: 4510067Abstract: The instant invention relates to compositions containing (a) a high-foaming nonionic surfactant and (b) a foam reducing amount of a polyoxyalkylene compound of the formula:Y[(A).sub.m --(B).sub.n H].sub.2wherein Y is the residue formed by the removal of two atoms of active hydrogen from an initiator having a total of not more than 20 carbon atoms, preferably butanediol; A is a hydrophobic, heteric mixture of an oxytetramethylene radical, derived from tetramethylene oxide and a vicinal alkylene oxide radical derived from propylene oxide, B is primarily C.sub.2 H.sub.4 O; n is an integer such that the total weight of said B is about 5 to about 40 percent by weight of the total oxyalkylene residue weight of the compound and the total molecular weight of the hydrophobe, 2m is about 1000 to 3000.Type: GrantFiled: June 27, 1983Date of Patent: April 9, 1985Assignee: BASF Wyandotte CorporationInventor: Ahmet C. Ozmeral
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Patent number: 4500705Abstract: The oligomeric cyclic ether content of a tetrahydrofuran-, an alkylene oxide-, or a tetrahydrofuran/alkylene oxide polymerizate can be reduced by bringing the polymerizate into contact with an aliphatic- or cycloaliphatic hydrocarbon of 6-8 carbon atoms, and separating the polymerizate and the hydrocarbon phases.Type: GrantFiled: January 9, 1984Date of Patent: February 19, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry B. Copelin
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Patent number: 4481123Abstract: The new polyethers obtainable by polymerization of an 1,2-epoxyalkane with 8 to 26 carbon atoms, and a tetrahydrofuran in the presence of a hydroxyl compound of the formulaH-OR.sup.1in which R.sup.1 denotes hydrogen, an alkyl radical having 1 to 24 carbon atoms or a hydroxyalkyl radical having 2 to 40 carbon atoms are disclosed together with their use as lubricants.Type: GrantFiled: April 22, 1982Date of Patent: November 6, 1984Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Hentschel, Rolf Dhein, Siegfried Kussi, Hans Winter, Herbert Vojacek
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Patent number: 4480124Abstract: The subject invention relates to a process for purifying polytetramethylene ether glycol or the corresponding diester prepared by cationic polymerization of tetrahydrofuran comprising treating said glycol or diester with hydrogen in the presence of a hydrogen catalyst. The resulting products have a low color number.Type: GrantFiled: March 11, 1982Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4460796Abstract: Polytetramethylene etherglycols are purified by treating the alkaline catalysts with orthophosphoric acid in an equivalence ratio of from 1.5 to 2.5:3 and then separating off the inorganic salts formed.Type: GrantFiled: February 10, 1982Date of Patent: July 17, 1984Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4374970Abstract: Copolyether glycols are modified so that they contain 1-25%, by weight of .beta.,.beta.'-dihydroxyalkyl sulfide moieties.These modified copolyether glycols have enhanced resistance to degradation by heat and oxygen.The invention also relates to a method of making the modified copolyether glycols, to their use as stabilizers against the degradation of the polyether chains, and to polyurethanes made with them.Type: GrantFiled: July 7, 1981Date of Patent: February 22, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ivan M. Robinson
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Patent number: 4373084Abstract: Polypropylene ether glycol is modified so that it contains 1-25%, by weight of .beta.,.beta.'-dihydroxyalkyl sulfide moieties.These modified polypropylene ether glycols have enhanced resistance to degradation by heat and oxygen.The invention also relates to a method of making the modified PPG's, to their use as stabilizers against the degradation of the polyether chain, and to polyurethanes made with them.Type: GrantFiled: July 7, 1981Date of Patent: February 8, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ivan M. Robinson
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Patent number: 4371713Abstract: In the process for preparing polyether glycol comprising (A) polymerizing tetrahydrofuran or a mixture of tetrahydrofuran and other copolymerizable cyclic ether(s) in the presence of a ring-opening polymerization catalyst comprising fuming sulfuric acid and/or fluorosulfuric acid as principal component, (B) adding water or an aqueous alkali solution to the polymerization product, and heating said reaction product under the strongly acidic condition to hydrolyze the same and (C) washing the hydrolysis product comprising polytetramethylene glycol and polyether glycol having oxytetramethylene groups as principal constituent, the polymerization of the tetrahydrofuran or the mixture of tetrahydrofuran and other copolymerizable cyclic ether(s) in the (A) step is carried out by (1) contacting the same with a ring-opening polymerization catalyst at a temperature within the range of -30.degree. C. to 10.degree. C.Type: GrantFiled: October 29, 1981Date of Patent: February 1, 1983Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Shuichi Matsumoto, Kenji Yasuda, Masayuki Endoh, Kunihiro Harada
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Patent number: 4371687Abstract: Polytetramethylene ether glycol is modified so that it contains 1-25%, by weight of .beta.,.beta.'-dihydroxyalkyl sulfide moieties.These modified polytetramethylene ether glycols have enhanced resistance to degradation by heat and oxygen.The invention also relates to a method of making the modified PTMEG's, to their use as stabilizers against the degradation of the polyether chain, and to polyurethanes made with them.Type: GrantFiled: July 7, 1981Date of Patent: February 1, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ivan M. Robinson
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Patent number: 4329445Abstract: A modified montmorillonite clay is prepared by heating it, impregnating it with an organic liquid, acid-activating it with a strong acid, and then washing it with water until it is substantially free of acid anions. The modified clay is useful as a catalyst, particularly for the preparation of tetrahydrofuran/alkylene oxide copolymers.Type: GrantFiled: May 30, 1980Date of Patent: May 11, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thomas W. Del Pesco
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Patent number: 4299993Abstract: A method for increasing the primary hydroxyl end groups in polyethers includes the steps of charging a reaction vessel with tetrahydrofuran and propylene oxide, adding BF.sub.3 or a BF.sub.3 -containing catalyst and then polymerizing the first pair of monomers to form a copolymer. After the first copolymerization is at least 60 percent complete, the method further includes the steps of adding ethylene oxide to the copolymer and unreacted monomers in the reaction vessel, and polymerizing the contents therein to form a terpolymer predominantly terminated by primary hydroxyl groups. The reaction is thereafter terminated and the terpolymer is separated from the remaining contents of the reaction vessel, washed and dried. The resulting terpolymer has from about 20 to about 80 weight percent of tetrahydrofuran, from about 10 to about 60 weight percent of propylene oxide, from about five to about 40 weight percent of ethylene oxide and at least 60 mole percent of terminal primary hydroxyl groups.Type: GrantFiled: March 3, 1980Date of Patent: November 10, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: Tristram W. Bethea, Shingo Futamura
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Patent number: 4259405Abstract: There are disclosed lubricated synthetic yarn and processes therefore wherein heteric copolymers of tetrahydrofuran and at least one C.sub.3 to C.sub.4 alkylene oxide initiated with a polyhydric alcohol are utilized as lubricants. The copolymers have a molecular weight of about 500 to about 10,000 and are initiated with polyhydric alcohols having a total of not more than 20 carbon atoms which are free of elements other than carbon, hydrogen and oxygen. Said initiators have 2 to about 6 reactive hydrogen atoms. The heteric copolymers of the invention capped with at least one lower alkylene oxide residue are also useful as fiber lubricants.Type: GrantFiled: January 15, 1980Date of Patent: March 31, 1981Assignee: BASF Wyandotte CorporationInventors: David D. Newkirk, Basil Thir
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Patent number: 4259531Abstract: Polytetramethylene ether glycols with molecular weights of from 300 to 4500 are produced by polymerizing tetrahydrofuran with an adduct of antimony pentachloride with carboxylic acids or carboxylic acid esters as the catalyst in the presence of a carboxylic acid anhydride, e.g., acetic anhydride, as the promoter. Esterified, e.g., acetylated, polytetramethylene ether glycols produced are subsequently converted to polytetramethylene ether glycols by saponification or transesterification. The process causes substantially less environmental pollution than do prior art methods, yet it is both economical and flexible.Type: GrantFiled: December 15, 1978Date of Patent: March 31, 1981Assignee: BASF AktiengesellschaftInventors: Otto H. Huchler, Walter Mesch, Siegfried Winderl, Herbert Mueller, Herwig Hoffmann
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Patent number: 4251654Abstract: Tetrahydrofuran/alkylene oxide polymerizates containing no more than 3%, by weight, of oligomeric cyclic ethers are prepared by extracting the ethers from a raw polymerizate with water.Type: GrantFiled: August 14, 1979Date of Patent: February 17, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ivan M. Robinson, Engelbert Pechhold