Preparing Esters From Alkylene Oxides Patents (Class 560/93)
  • Patent number: 10336680
    Abstract: A process for preparing bis(2-hydroxyethyl) terephthalate, comprising a step of: subjecting ethylene oxide and terephthalic acid in a molar ratio of from 2:1 to 3:1 to a reaction at an elevated temperature in the presence of a solvent mixture containing water and a C6-C8 hydrocarbon in a weight ratio of from 1:1 to 3:1.
    Type: Grant
    Filed: October 11, 2017
    Date of Patent: July 2, 2019
    Assignee: FAR EASTERN NEW CENTURY CORPORATION
    Inventors: Der-Ren Hwang, Cheng-Ting Wang, Hsiao-Chan Wang
  • Patent number: 8759565
    Abstract: Disclosed are processes to prepare monocarboxylic acid esters (mono- and/or diesters) of polytrimethylene ether glycol that are substantially free of residues from the catalyst used to produce the polytrimethylene ether glycol esters, as well as methods for their preparation and end uses thereof. The esters, such as the bis-2-ethylhexanoate esters, have uses as functional fluids.
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: June 24, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Raja Hari Poladi, Gyorgyi Fenyvesi
  • Patent number: 7863477
    Abstract: A polyester production process employing an esterification system that uses a distillation column to recover alcohol produced from an esterification zone and then utilizes the recovered alcohol to form a paste, which is recirculated back to the esterification zone with little or no cooling.
    Type: Grant
    Filed: March 8, 2007
    Date of Patent: January 4, 2011
    Assignee: Eastman Chemical Company
    Inventor: Bruce Roger DeBruin
  • Patent number: 7659425
    Abstract: The present invention relates to a process for preparing hydroxyalkyl (meth)acrylates by reacting at least one compound A which contains at least one epoxide group with at least one compound B which contains at least one carboxylic acid group, wherein A and/or B also contains at least one (meth)acrylate group, in the presence of Lewis acid catalysts, each of which contains at least one directly bonded di(cyclo)alkylamino group.
    Type: Grant
    Filed: February 16, 2006
    Date of Patent: February 9, 2010
    Assignee: Bayer MaterialScience AG
    Inventors: Jan Weikard, Christoph Gürtler
  • Patent number: 7381354
    Abstract: Flame retardant formulations comprised of at least one bromine-containing polyol are produced by a process which comprises: A) heating a mixture formed from components comprised of (i) tetrabromophthalic anhydride, (ii) at least one aliphatic polyol, and (iii) at least one liquid straight chain aliphatic diester of a straight-chain alkane dicarboxylic acid to form an intermediate composition; and B) contacting all or a portion of the intermediate composition one or more times with (iv) at least one alkylene oxide that results in the formation of a liquid product formulation, and optionally, removing any excess alkylene oxide present; the amounts of (i), (ii), (iii), and (iv) used being proportioned to form a formulation having a bromine content of at least about 40 wt %, a viscosity at 25° C. of about 20,000 cps or less, and an acid number as determinable by aqueous sodium hydroxide titration and expressed in terms of potassium hydroxide, of less than about 1 milligram of KOH per gram of the formulation.
    Type: Grant
    Filed: May 21, 2007
    Date of Patent: June 3, 2008
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7258823
    Abstract: Flame retardant formulations comprised of at least one bromine-containing polyol are produced by a process which comprises: A) heating a mixture formed from components comprised of (i) tetrabromophthalic anhydride, (ii) at least one aliphatic polyol, and (iii) at least one liquid straight chain aliphatic diester of a straight-chain alkane dicarboxylic acid to form an intermediate composition; and B) contacting all or a portion of the intermediate composition one or more times with (iv) at least one alkylene oxide that results in the formation of a liquid product formulation, and optionally, removing any excess alkylene oxide present; the amounts of (i), (ii), (iii), and (iv) used being proportioned to form a formulation having a bromine content of at least about 40 wt %, a viscosity at 25° C. of about 20,000 cps or less, and an acid number as determinable by aqueous sodium hydroxide titration and expressed in terms of potassium hydroxide, of less than about 1 milligram of KOH per gram of the formulation.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: August 21, 2007
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7045564
    Abstract: A flame retardant formulation which is the combination of at least (1) at least one bromine-containing polyol flame retardant formed from the reaction of (a) tetrabromophthalic anhydride, (b) an aliphatic polyol, and (c) an epoxide, and (2) at least one aliphatic diester of an alkane dicarboxylic acid, with the proviso that the formulation has a viscosity at 25° C. of about 20,000 cps or less, and a bromine content of at least about 40 wt %. A flame retardant compound formed from A) tetrabromophthalic anhydride; B) diethylene glycol; C) at least one alpha-omega alkane diol, or at least one alpha-omega alkane diol and at least one aliphatic monool; and D) at least one alkylene oxide; with the proviso that the compound has a viscosity at 25° C. of about 60,000 cps or less, and a bromine content of at least about 43 wt %. Polymer compositions formed from (a) a polyurethane or a polyisocyanurate and (b) a formulation of the invention.
    Type: Grant
    Filed: August 29, 2003
    Date of Patent: May 16, 2006
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 6765116
    Abstract: A process to prepare an improved fluid rare earth phosphate catalyst composition useful in preparing alkylene oxide adducts of organic compounds having active hydrogen atoms is provided. The catalyst is prepared by dissolving a rare earth salt in a C9-C30 active hydrogen containing organic compound and then adding phosphoric acid to the organic compound rare earth mixture.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: July 20, 2004
    Assignee: Shell Oil Company
    Inventor: Charles Lee Edwards
  • Patent number: 6740686
    Abstract: The invention concerns a method for making a polyurethane foam by reacting at least a polyester polyol with at least a polyisocyanate in the presence of a foaming agent and a catalytic agent, such a polyester polyol having been previously obtained by reacting a reactive acid A comprising at least an aliphatic or aromatic polyacid with functionality not less than 2 with at least a polyol P2 with functionality equal to 2 and at least an aliphatic or aromatic polyacid with functionality not less than 2 with at least a polyol P2 with functionality equal to 2 and at least a polyol P3 with functionality not less than 3, being thereafter called AP2P3, wherein the catalytic agent at least partly consists of at least one amine polyester polyol AP2P3, wherein at least part of polyol P3 consists of at least a polyoxyalkylene polyalkanolamine having at least a tertiary amine function, the alkanol radicals of said polyalkanolamine being C1-C6, the alkylene oxide units being C2-C4 and the statistical mean of the number N o
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: May 25, 2004
    Assignee: Crompton Corporation
    Inventors: Denis Ghesquiere, Remy Dumont
  • Patent number: 6541656
    Abstract: Economical and efficient processes for producing an &agr;, &bgr;-unsaturated carboxylic acid heterocycle-inserted ester and an &agr;,&bgr;-unsaturated carboxylic acid polyheteroalkylene ester as well as a catalyst suited for use in economically and efficiently producing an &agr;,&bgr;-unsaturated carboxylic acid ester are provided. The invention provides (1) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid ester with a heterocyclic compound, (2) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid with a heterocyclic compound in the presence of a polymerization inhibitor and a metal oxide catalyst, and (3) a catalyst for the production of an &agr;,&bgr;-unsaturated carboxylic acid ester comprising a metal oxide.
    Type: Grant
    Filed: February 8, 2001
    Date of Patent: April 1, 2003
    Assignee: Nippon Shokubai Company, Ltd.
    Inventors: Keiji Yurugi, Takafumi Kubo
  • Patent number: 6100374
    Abstract: The process for preparing polyethylene naphthalate according to the invention is intended to obtain polyethylene naphthalate having a low impurity content from naphthalenedicarboxylic acid containing impurities.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: August 8, 2000
    Assignee: Mitsui Chemicals Inc.
    Inventors: Hiroshi Iwasaki, Satoshi Inoki, Hiromi Ueki
  • Patent number: 5463020
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
  • Patent number: 5332859
    Abstract: Described is a batchwise process for producing tetrabromophthalic diester flame retardants having consistent product characteristics.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: July 26, 1994
    Assignee: Great Lakes Chemical Europe, Ltd.
    Inventor: Brian Tarbit
  • Patent number: 5210325
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: May 11, 1993
    Assignee: Shell Oil Company
    Inventors: Richard A. Kemp, Paul R. Weider
  • Patent number: 5189199
    Abstract: A process is disclosed for the preparation of 1,4-dioxy-2-butenes by reacting 3,4-epoxy-1-butene with an oxygen nucleophile in the presence of a Pd(O) complex catalyst.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: February 23, 1993
    Assignee: Eastman Kodak Company
    Inventor: Stephen A. Godleski
  • Patent number: 5118870
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: June 2, 1992
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 5057628
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventors: Charles L. Edwards, Richard A. Kemp
  • Patent number: 5057627
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 5015697
    Abstract: A process is disclosed for preparing a composition comprising a polybutyl ketone and a hydroxyester of an epoxidized polybutene wherein the epoxide groups of said epoxidized polybutene are at least 70% trisubstituted. Acid compounds are reacted with epoxidized polybutenes to obtain compositions of increased reactivity as compared with polybutyl ketone compounds. These compositions are useful as chemical intermediates to modify such materials as polyesters and polyurethenes, for applications such as coatings, foams, and sealants.
    Type: Grant
    Filed: January 31, 1989
    Date of Patent: May 14, 1991
    Assignee: Amoco Corporation
    Inventor: Wayne T. Riddick
  • Patent number: 4970333
    Abstract: The production of esters via the reaction of an epoxide with a carboxylic acid hasbeen shown to give improved activity when a strong base macroporous anion exchange resin having an acrylic backbone is used in place of a styrene-divinylbenzene based anion exchange resin having an equivalent exchange capacity. Excellent results are obtained when acrylic acid and propylene oxide are reacted together in the presence of strong base macroporous anion exchange resins which have an acrylic backbone.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: November 13, 1990
    Assignee: The Dow Chemical Company
    Inventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
  • Patent number: 4960952
    Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4902816
    Abstract: Polyols containing polyether and polyester moieties, based on phthalic acid are described. A phthalic acid derivative is reacted with a polyether polyol to give the novel polyols which are useful not only in polyisocyanurate foams, but also polyurethane foams as well. The phthalic acid derivative may be phthalic acid, phthalic anhydride and an ester of phthalic acid, for example. The polyester polyol is made from an initiator selected from the group consisting of alkanolamines, alkyleneamines, arylamines, sucrose, glycerin, sorbitol, .alpha.-methylglucoside, .beta.-methylglucoside, and mixtures thereof. The polyester polyol may be made by alkoxylating the initiators.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: February 20, 1990
    Assignee: ARCO Chemical Technology, Inc.
    Inventor: Kenneth G. McDaniel
  • Patent number: 4780565
    Abstract: Alkylene glycol ether carboxylates are produced by reacting at elevated temperature an alkylene oxide and a carboxylate ester in the presence as catalyst of a [bis(trihydrocarbylphosphine)iminium].sub.2 MO.sub.4 compound wherein M is either molybdenum or tungsten.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: October 25, 1988
    Assignee: BP Chemicals Limited
    Inventor: John E. Hamlin
  • Patent number: 4745211
    Abstract: A process for preparation of a purified bis(2-hydroxyethyl) ester of 2,6-naphthalenedicarboxylic acid wherein 2,6-naphthalenedicarboxylic acid is reacted with a catalyst comprised of a tertiary amine and a titanium-containing compound in order to produce the ester.
    Type: Grant
    Filed: September 15, 1987
    Date of Patent: May 17, 1988
    Assignee: Eastman Kodak Company
    Inventors: Winston J. Jackson, Jr., Thomas H. Wicker, Jr.
  • Patent number: 4701477
    Abstract: A method for preparing aromatic polyols useful for the production of polyurethane and polyisocyanurate polymers involves digesting scrap polyalkylene terephthalate polymers with a digesting agent, typically a low molecular weight polyol. The digestion product is then treated with an alkylene oxide to produce a low viscosity polyol which displays excellent stability over long term storage.
    Type: Grant
    Filed: July 13, 1983
    Date of Patent: October 20, 1987
    Assignee: Chardonol, Division of Freeman Corporation
    Inventors: Milton J. Altenberg, Johannes deJong
  • Patent number: 4661582
    Abstract: Novel diimide diacids and modified polyetherimide esters are prepared therefrom by reacting diols, dicarboxylic acids and a combination of the novel diimide diacid and dimer acid. These compositions have many excellent properties which make them particularly useful for extrusion and molding applications.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: April 28, 1987
    Assignee: General Electric Company
    Inventor: Russell J. McCready
  • Patent number: 4582926
    Abstract: In order to prepare polyester or polyetherpolyester polyols, polyols, preferably di- to hexafunctional polyether polyols having hydroxyl numbers from 15 to 250 are esterified with at least one carboxylic acid anhydride, preferably phthalic acid anhydride, in the presence of N-methylimidazole, triethylenediamine, and/or triphenylphosphine as catalysts to form a carboxylic acid half-ester, and said half-ester is then oxyalkylated with at least one alkylene oxide, preferably ethylene oxide, in the presence of N-methylimidazole, triethylenediamine, triphenylphosphine, thiodialkylene glycol, employing a mixture of at least two of the compounds cited as catalysts.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: April 15, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Straehle, Matthias Marx
  • Patent number: 4568774
    Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: February 4, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4560788
    Abstract: A process for producing an oligoester which comprises:(a) the step of reacting isophthalic acid and propylene oxide in a reaction medium in the presence of a specific catalyst comprising a tetraalkyl ammonium compound to prepare an oligoester, and(b) the step of removing volatile components from the resulting oligoester by heating the oligoester at a temperature of 180.degree.-280.degree. C. is disclosed. The oligoester is used as an intermediate for preparing unsaturated polyesters.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: December 24, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Miyamoto, Senzo Shimizu, Masayoshi Okamura, Hiroka Tanisake, Yasumitsu Higuchi, Toshio Hidaka, Koji Yamamoto, Toshiyuki Abe
  • Patent number: 4535178
    Abstract: Polyether-ester polyols are prepared by reacting a polyether polyol, tetrahydrophthalic anhydride and an alkylene oxide in the presence of a catalyst selected from the group consisting of calcium naphthenate and cobalt naphthenate. These polyols may be used in preparing polyurethane products.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: August 13, 1985
    Assignee: BASF Wyandotte Corporation
    Inventor: Curtis J. Reichel
  • Patent number: 4485196
    Abstract: A mixture of aromatic polyester polyols useful in preparing rigid foams is described. The polyols are made by first reacting recycled polyethylene terephthalate (PET) scrap with an alkylene glycol to form a reaction product which is then reacted with an alkylene oxide, such as propylene oxide. The resultant mixture of aromatic polyester polyols is a homogeneous liquid which does not precipitate solids upon standing, as do some prior art PET-derived polyols.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: November 27, 1984
    Assignee: Texaco Inc.
    Inventors: George P. Speranza, Robert A. Grigsby, Jr., Michael E. Brennan
  • Patent number: 4466922
    Abstract: 3-Alkyl-3-acyloxy-4-hydroxybut-1-enes are prepared by a process in which a 3-alkyl-3,4-epoxybut-1-ene is treated with a carboxylic acid and a copper salt of a carboxylic acid.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: August 21, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Rolf Fischer
  • Patent number: 4452997
    Abstract: Polyester polyols and/or polyester-polyether polyols are prepared by reacting polyols preferably di- to hexafunctional polyether polyols with hydroxyl numbers of 30 to 200 with at least one carboxylic anhydride, preferably glutaric anhydride, resulting in a carboxylic acid half ester which is subsequently oxyalkylated with at least one alkylene oxide, preferably ethylene oxide in the presence of at least 1 thiodialkylene glycol, preferably thiodiethylene and/or thiodipropylene glycol.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: June 5, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Marx, Wolfgang Straehle
  • Patent number: 4442237
    Abstract: Mixtures of aromatic polyols containing tertiary amine and ester functionalities suitable for use in rigid foams prepared by reacting a phthalic acid residue with an alkylene glycol and an amino alcohol are described. These novel polyols may be blended with conventional polyols to yield rigid polyurethane foams with better flammability resistance as compared with foams made from conventional polyols alone.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 10, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Kenneth G. McDaniel
  • Patent number: 4442238
    Abstract: Mixtures of aromatic polyols containing amide and ester functionalities suitable for use in rigid foams prepared by reacting a phthalic acid residue with an amino alcohol and subsequent alkoxylation are described. These novel polyols may be blended with conventional polyols to yield rigid foams with better flammability resistance as compared with foams made from conventional polyols alone.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 10, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, George P. Speranza
  • Patent number: 4439549
    Abstract: Mixtures of aromatic polyols containing ester functionalities suitable for use in rigid polyurethane and polyisocyanurate foams are described. The mixtures are prepared by reacting a polyethylene terephthalate (PET) residue with an alkylene oxide in the presence of a basic catalyst. These novel polyol mixtures may be blended with conventional polyols to yield rigid foams with better flammability resistance as compared with foams made from conventional polyols alone.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: March 27, 1984
    Assignee: Texaco Inc.
    Inventor: Michael E. Brennan
  • Patent number: 4435592
    Abstract: Polyether-ester polyols are prepared by reacting a crude polyether polyol, tetrahydrophthalic anhydride and an alkylene oxide. These polyols may be used in preparing polyrethane products.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: March 6, 1984
    Assignee: BASF Wyandotte Corporation
    Inventor: Curtis J. Reichel
  • Patent number: 4405766
    Abstract: Tetrahydrocarbyl phosphonium bicarbonate salts are employed as catalysts to promote the reaction between (a) vicinal epoxides and (b) carboxylic acids or anhydrides. These catalysts are particularly useful in the preparation of vinyl ester resins.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: September 20, 1983
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4395566
    Abstract: An improved process for exterifying carboxyaromatics is disclosed wherein an anhydride of a carboxyaromatic, such as pyromellitic dianhydride, is reacted with a fluorinated alcohol and an epoxide to give a mixed ester capable of imparting oil and/or water repellency to textiles. The improvement comprises utilizing the epoxide as the reaction medium to reduce reaction times and waste water treatment requirements.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 26, 1983
    Assignee: American Hoechst Corporation
    Inventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
  • Patent number: 4271312
    Abstract: Chromium (III) catalysis of the reaction between ethylene oxides (ethylene oxide and 1,2-propylene oxide) and aromatic carboxylic acids at temperatures in the range from 50.degree. to 180.degree. C. are rapid but produce excessive amounts of diglycol ether ester (2-hydroxyethoxyethanol or 2-hydroxy-2-methylethoxy 2-methylethanol) which is present as the diglycol ether ester of the aromatic carboxylic acid and is a contaminent hard to remove from the desired 2-hydroxyethyl ester of the aromatic carboxylic acid. The use of an amine, in such ethylene oxide reaction with aromatic carboxylic acid suppresses the formation of diglycol ether and increases the conversion of aromatic carboxylic acid to the desired 2-hydroxyethyl ester thereof.
    Type: Grant
    Filed: April 7, 1971
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company (Indiana)
    Inventors: Wilford J. Zimmerschied, Delbert H. Meyer
  • 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: 4219665
    Abstract: Polycarboxylic acid-2-hydroxyalkyl esters of the formula ##STR1## wherein A is an aliphatic, cycloaliphatic, or aromatic radical which is optionally substituted or interrupted by heteroatoms, and/or optionally substituted by hydroxyl groups, R.sub.1 is hydrogen or an alkyl radical having 1 to 12 carbon atoms, and R.sub.2 is an alkyl radical having 10 to 22 carbon atoms, n.gtoreq.0 and m.gtoreq.2, with the proviso that m.gtoreq.n and the total of n+m.gtoreq.3, and their use as emulsifying agents and cosmetic emulsions containing them.
    Type: Grant
    Filed: June 30, 1978
    Date of Patent: August 26, 1980
    Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)
    Inventors: Ulrich Zeidler, Fanny Scheuermann
  • Patent number: 4156700
    Abstract: Useful hydroxyl-terminated polyolefin prepolymers, e.g. polybutadiene prepolymers, are provided which may be cross-linked with an epoxide to yield a polyether elastomeric material or with a mixture of an anhydride and an epoxide to form a polyester material. One such prepolymer is a carboxyl-terminated polyolefin, e.g. polybutadiene prepared by reacting a hydroxy-terminated polyolefin, e.g. polybutadiene with solid or liquid anhydrides. Polyether and polyester propellants containing up to about 88% of solid ammonium perchlorate in the powder form and aluminum powder may be prepared from the above two materials (binders). The physical and mechanical properties from these propellants depend on the ratios and on the order of addition of each ingredient, the curing temperature and the presence of surface-active agents. Polyester propellants may be made either by using the hydroxy-terminated polyolefin, e.g. polybutadiene prereacted with anhydrides or by mixing simultaneously all ingredients with the solids.
    Type: Grant
    Filed: July 21, 1976
    Date of Patent: May 29, 1979
    Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National Defence
    Inventors: Meude Tremblay, Guy Perrault, Gonzague Duchesne
  • Patent number: 4144395
    Abstract: Polyether-ester polyols are prepared in the presence of from 0.005 percent to 0.01 percent by weight (50-100 ppm) of a trialkylamine. The resulting polyols have improved color and are obtained in markedly reduced reaction times.
    Type: Grant
    Filed: December 5, 1977
    Date of Patent: March 13, 1979
    Assignee: BASF Wyandotte Corporation
    Inventors: John R. Murphy, Louis C. Pizzini
  • Patent number: 4118426
    Abstract: A process for the preparation of hydroxy ethers which comprises reacting an epoxide compound with an organic hydroxy compound in the presence of a PdCl.sub.2 /CuCl.sub.2 /O.sub.2 catalyst system, and recovering the hydroxy ether thus formed from the reaction mixture by a separation step such as distillation. An alternative catalyst system is K.sub.2 PdCl.sub.6 /CuCl.sub.2 /O.sub.2.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: October 3, 1978
    Assignee: Western Kentucky University
    Inventors: Norman L. Holy, Theodore E. Nalesnik
  • Patent number: 4115415
    Abstract: A process for the production of an alkylene glycol ether ester of an organic carboxylic acid which comprises the step of reacting an alkylene oxide with an ester of organic carboxylic acid in accordance with the following reaction equation: ##STR1## wherein R" is a substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms or a hydrogen atom;R'" is a substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms;R.sup.3 are each the same or different substituted or non-substituted hydrocarbon having 1 to 10 carbon atoms or a hydrogen atom;Q is simultaneously the same or different groups X, R, OR, SR, NR.sub.2 or PR.sub.2 (wherein X is a halogen atom selected from the group consisting of Cl, Br, and I, and R is the same or different substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms or a hydrogen atom, and a combination of all Q=R does not occur).
    Type: Grant
    Filed: October 22, 1976
    Date of Patent: September 19, 1978
    Assignee: Nisso Petrochemical Industries Co., Ltd.
    Inventors: Hiroshi Yoshihara, Takashi Tobita, Ryoichi Tomizawa, Kunio Ishikawa
  • Patent number: 4069242
    Abstract: A synergistic catalytic effect is realized in the esterification reaction between an organic carboxylic acid and a vicinal epoxide by using a catalyst system comprising: (a) a compound containing an amino and/or ammonium nitrogen atom, in combination with (b) a soluble compound containing an ionizable atom of iron or chromium.
    Type: Grant
    Filed: September 9, 1971
    Date of Patent: January 17, 1978
    Assignee: The Dow Chemical Company
    Inventor: Arthur E. Gurgiolo