Polytetramethylene Glycols Patents (Class 568/617)
  • Patent number: 5118869
    Abstract: 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: Grant
    Filed: February 13, 1991
    Date of Patent: June 2, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Suriyanarayan Dorai, Gerfried Pruckmayr, Marianne Marsi, Willard L. Quon
  • Patent number: 5099074
    Abstract: 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: Grant
    Filed: October 26, 1990
    Date of Patent: March 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Mueller, Gerhard Jeschek, Rolf Fischer, Hans-Juergen Weyer
  • Patent number: 5097077
    Abstract: 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: Grant
    Filed: October 5, 1990
    Date of Patent: March 17, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Mueller, Gerhard Jeschek, Rolf Fischer, Hans-Juergen Weyer
  • Patent number: 5053553
    Abstract: 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: Grant
    Filed: June 25, 1990
    Date of Patent: October 1, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Suriyanarayanan Dorai
  • Patent number: 5001277
    Abstract: 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: Grant
    Filed: April 30, 1990
    Date of Patent: March 19, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Jonathan L. Schuchardt
  • Patent number: 4988797
    Abstract: 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: Grant
    Filed: March 14, 1989
    Date of Patent: January 29, 1991
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 4970295
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: November 13, 1990
    Assignee: ARCO Chemical Technology, Inc.
    Inventor: Jonathan L. Schuchardt
  • Patent number: 4967015
    Abstract: 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: Grant
    Filed: October 16, 1989
    Date of Patent: October 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Karcher, Heinz Eckhardt, Jochem Henkelmann
  • Patent number: 4962237
    Abstract: 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: Grant
    Filed: January 2, 1990
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventor: David E. Laycock
  • Patent number: 4954658
    Abstract: 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: Grant
    Filed: September 14, 1989
    Date of Patent: September 4, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Suriyanarayanan Dorai, Richard E. Ernst
  • Patent number: 4952673
    Abstract: 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: Grant
    Filed: August 1, 1988
    Date of Patent: August 28, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4933503
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: June 12, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4879420
    Abstract: 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: Grant
    Filed: May 6, 1988
    Date of Patent: November 7, 1989
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Richard E. Ernst
  • Patent number: 4877906
    Abstract: 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: Grant
    Filed: November 25, 1988
    Date of Patent: October 31, 1989
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Stephen D. Harper
  • Patent number: 4859801
    Abstract: 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: Grant
    Filed: May 26, 1988
    Date of Patent: August 22, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard E. Ernst
  • Patent number: 4806694
    Abstract: 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: Grant
    Filed: September 10, 1987
    Date of Patent: February 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard L. Powell, Brian Young
  • Patent number: 4803299
    Abstract: 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: Grant
    Filed: April 6, 1987
    Date of Patent: February 7, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4792627
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: December 20, 1988
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
  • Patent number: 4762951
    Abstract: 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: Grant
    Filed: March 4, 1987
    Date of Patent: August 9, 1988
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4751331
    Abstract: 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: Grant
    Filed: May 1, 1987
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventor: Elizabeth A. Efford
  • Patent number: 4728722
    Abstract: 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: Grant
    Filed: February 12, 1987
    Date of Patent: March 1, 1988
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4677231
    Abstract: 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: Grant
    Filed: November 8, 1985
    Date of Patent: June 30, 1987
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Setsuo Yamamatsu, Shoichiro Tonomura
  • Patent number: 4658065
    Abstract: 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: Grant
    Filed: March 27, 1985
    Date of Patent: April 14, 1987
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
  • Patent number: 4638097
    Abstract: 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: Grant
    Filed: March 21, 1986
    Date of Patent: January 20, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4624299
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: November 25, 1986
    Assignee: Union Carbide Corporation
    Inventors: Ronald H. Harding, George E. Totten
  • Patent number: 4617984
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: October 21, 1986
    Assignee: Union Carbide Corporation
    Inventors: Ronald H. Harding, George E. Totten
  • Patent number: 4599460
    Abstract: 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: Grant
    Filed: August 13, 1985
    Date of Patent: July 8, 1986
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yuzo Toga, Ichiro Okamoto, Tatsuya Kanno
  • Patent number: 4595537
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: June 17, 1986
    Assignee: Pola Chemical Industries, Inc.
    Inventors: Michio Ochiai, Hiromichi Sagitani
  • Patent number: 4590054
    Abstract: 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: Grant
    Filed: September 16, 1985
    Date of Patent: May 20, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William W. Kasper, Willard L. Quon, Timothy D. Van Domelen
  • Patent number: 4585592
    Abstract: 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: Grant
    Filed: February 28, 1985
    Date of Patent: April 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4584414
    Abstract: 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: Grant
    Filed: December 21, 1984
    Date of Patent: April 22, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gerfried Pruckmayr
  • Patent number: 4569990
    Abstract: 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: Grant
    Filed: August 27, 1984
    Date of Patent: February 11, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William W. Kasper, Willard L. Quon, Timothy D. Van Domelen
  • Patent number: 4568775
    Abstract: 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: Grant
    Filed: May 16, 1984
    Date of Patent: February 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Shoichiro Tonomura
  • Patent number: 4564671
    Abstract: 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: Grant
    Filed: December 14, 1984
    Date of Patent: January 14, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4544774
    Abstract: 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: Grant
    Filed: December 5, 1984
    Date of Patent: October 1, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Rudolph Pick
  • Patent number: 4510333
    Abstract: 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: Grant
    Filed: June 5, 1984
    Date of Patent: April 9, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gerfried Pruckmayr
  • Patent number: 4510067
    Abstract: 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: Grant
    Filed: June 27, 1983
    Date of Patent: April 9, 1985
    Assignee: BASF Wyandotte Corporation
    Inventor: Ahmet C. Ozmeral
  • Patent number: 4500705
    Abstract: 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: Grant
    Filed: January 9, 1984
    Date of Patent: February 19, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harry B. Copelin
  • Patent number: 4481123
    Abstract: 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: Grant
    Filed: April 22, 1982
    Date of Patent: November 6, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinz Hentschel, Rolf Dhein, Siegfried Kussi, Hans Winter, Herbert Vojacek
  • Patent number: 4480124
    Abstract: 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: Grant
    Filed: March 11, 1982
    Date of Patent: October 30, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4460796
    Abstract: 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: Grant
    Filed: February 10, 1982
    Date of Patent: July 17, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4374970
    Abstract: 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: Grant
    Filed: July 7, 1981
    Date of Patent: February 22, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ivan M. Robinson
  • Patent number: 4373084
    Abstract: 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: Grant
    Filed: July 7, 1981
    Date of Patent: February 8, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ivan M. Robinson
  • Patent number: 4371713
    Abstract: 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: Grant
    Filed: October 29, 1981
    Date of Patent: February 1, 1983
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Shuichi Matsumoto, Kenji Yasuda, Masayuki Endoh, Kunihiro Harada
  • Patent number: 4371687
    Abstract: 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: Grant
    Filed: July 7, 1981
    Date of Patent: February 1, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ivan M. Robinson
  • Patent number: 4329445
    Abstract: 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: Grant
    Filed: May 30, 1980
    Date of Patent: May 11, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thomas W. Del Pesco
  • Patent number: 4299993
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: November 10, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Tristram W. Bethea, Shingo Futamura
  • Patent number: 4259405
    Abstract: 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: Grant
    Filed: January 15, 1980
    Date of Patent: March 31, 1981
    Assignee: BASF Wyandotte Corporation
    Inventors: David D. Newkirk, Basil Thir
  • Patent number: 4259531
    Abstract: 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: Grant
    Filed: December 15, 1978
    Date of Patent: March 31, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Otto H. Huchler, Walter Mesch, Siegfried Winderl, Herbert Mueller, Herwig Hoffmann
  • Patent number: 4251654
    Abstract: 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: Grant
    Filed: August 14, 1979
    Date of Patent: February 17, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ivan M. Robinson, Engelbert Pechhold