Preparing Esters From Alkylene Oxides Patents (Class 560/93)
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Patent number: 10913820Abstract: A process for producing a cationic dyeable polyester includes the steps of: (a) subjecting a combination of a bis-hydroxy alkyl terephthalate monomer of Formula (1) defined herein and an organic diacid monomer mixture which includes an aromatic dicarboxylic acid monomer and a sulfo group-containing aromatic dicarboxylic acid dyeable monomer to an esterification reaction to form an esterification reaction product; and (b) subjecting the esterification reaction product to a polycondensation reaction.Type: GrantFiled: January 16, 2019Date of Patent: February 9, 2021Assignee: Far Eastern New Century CorporationInventors: Der-Ren Hwang, Cheng-Ting Wang, Yen-Hsien Li
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Patent number: 10336680Abstract: 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: GrantFiled: October 11, 2017Date of Patent: July 2, 2019Assignee: FAR EASTERN NEW CENTURY CORPORATIONInventors: Der-Ren Hwang, Cheng-Ting Wang, Hsiao-Chan Wang
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Patent number: 8759565Abstract: 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: GrantFiled: June 23, 2010Date of Patent: June 24, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Raja Hari Poladi, Gyorgyi Fenyvesi
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Patent number: 7863477Abstract: 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: GrantFiled: March 8, 2007Date of Patent: January 4, 2011Assignee: Eastman Chemical CompanyInventor: Bruce Roger DeBruin
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Patent number: 7659425Abstract: 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: GrantFiled: February 16, 2006Date of Patent: February 9, 2010Assignee: Bayer MaterialScience AGInventors: Jan Weikard, Christoph Gürtler
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Patent number: 7381354Abstract: 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: GrantFiled: May 21, 2007Date of Patent: June 3, 2008Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
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Patent number: 7258823Abstract: 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: GrantFiled: May 20, 2004Date of Patent: August 21, 2007Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
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Patent number: 7045564Abstract: 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: GrantFiled: August 29, 2003Date of Patent: May 16, 2006Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
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Patent number: 6765116Abstract: 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: GrantFiled: August 23, 2002Date of Patent: July 20, 2004Assignee: Shell Oil CompanyInventor: Charles Lee Edwards
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Patent number: 6740686Abstract: 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 oType: GrantFiled: November 27, 2000Date of Patent: May 25, 2004Assignee: Crompton CorporationInventors: Denis Ghesquiere, Remy Dumont
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Patent number: 6541656Abstract: 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: GrantFiled: February 8, 2001Date of Patent: April 1, 2003Assignee: Nippon Shokubai Company, Ltd.Inventors: Keiji Yurugi, Takafumi Kubo
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Patent number: 6100374Abstract: 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: GrantFiled: March 9, 1999Date of Patent: August 8, 2000Assignee: Mitsui Chemicals Inc.Inventors: Hiroshi Iwasaki, Satoshi Inoki, Hiromi Ueki
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Patent number: 5463020Abstract: Polytetrahydrofuran or C.sub.2 -C.sub.10 -alkylene oxide/tetrahydrofuran copolymers having a molecular weight of from 250 to 20,000 Dalton are prepared by the cationic polymerization of tetrahydrofuran or tetrahydrofuran and C.sub.2 -C.sub.10 -alkylene oxides in the prsence of a promoter by a process in which the catalyst used is a mixture of one or more C.sub.2 -C.sub.6 -di- or tricarboxylic acids with boric acid.Type: GrantFiled: June 30, 1994Date of Patent: October 31, 1995Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
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Patent number: 5332859Abstract: Described is a batchwise process for producing tetrabromophthalic diester flame retardants having consistent product characteristics.Type: GrantFiled: November 3, 1992Date of Patent: July 26, 1994Assignee: Great Lakes Chemical Europe, Ltd.Inventor: Brian Tarbit
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5189199Abstract: 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: GrantFiled: February 20, 1992Date of Patent: February 23, 1993Assignee: Eastman Kodak CompanyInventor: Stephen A. Godleski
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5015697Abstract: 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: GrantFiled: January 31, 1989Date of Patent: May 14, 1991Assignee: Amoco CorporationInventor: Wayne T. Riddick
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Patent number: 4970333Abstract: 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: GrantFiled: October 29, 1987Date of Patent: November 13, 1990Assignee: The Dow Chemical CompanyInventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
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Patent number: 4960952Abstract: 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: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4902816Abstract: 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: GrantFiled: March 28, 1988Date of Patent: February 20, 1990Assignee: ARCO Chemical Technology, Inc.Inventor: Kenneth G. McDaniel
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Patent number: 4780565Abstract: 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: GrantFiled: March 4, 1987Date of Patent: October 25, 1988Assignee: BP Chemicals LimitedInventor: John E. Hamlin
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Patent number: 4745211Abstract: 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: GrantFiled: September 15, 1987Date of Patent: May 17, 1988Assignee: Eastman Kodak CompanyInventors: Winston J. Jackson, Jr., Thomas H. Wicker, Jr.
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Patent number: 4701477Abstract: 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: GrantFiled: July 13, 1983Date of Patent: October 20, 1987Assignee: Chardonol, Division of Freeman CorporationInventors: Milton J. Altenberg, Johannes deJong
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Patent number: 4661582Abstract: 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: GrantFiled: May 5, 1986Date of Patent: April 28, 1987Assignee: General Electric CompanyInventor: Russell J. McCready
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Patent number: 4582926Abstract: 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: GrantFiled: April 9, 1984Date of Patent: April 15, 1986Assignee: BASF AktiengesellschaftInventors: Wolfgang Straehle, Matthias Marx
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Patent number: 4568774Abstract: 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: GrantFiled: October 1, 1984Date of Patent: February 4, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4560788Abstract: 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: GrantFiled: August 8, 1983Date of Patent: December 24, 1985Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akira Miyamoto, Senzo Shimizu, Masayoshi Okamura, Hiroka Tanisake, Yasumitsu Higuchi, Toshio Hidaka, Koji Yamamoto, Toshiyuki Abe
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Patent number: 4535178Abstract: 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: GrantFiled: September 29, 1982Date of Patent: August 13, 1985Assignee: BASF Wyandotte CorporationInventor: Curtis J. Reichel
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Patent number: 4485196Abstract: 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: GrantFiled: September 26, 1983Date of Patent: November 27, 1984Assignee: Texaco Inc.Inventors: George P. Speranza, Robert A. Grigsby, Jr., Michael E. Brennan
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Patent number: 4466922Abstract: 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: GrantFiled: September 13, 1982Date of Patent: August 21, 1984Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer
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Patent number: 4452997Abstract: 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: GrantFiled: December 23, 1982Date of Patent: June 5, 1984Assignee: BASF AktiengesellschaftInventors: Matthias Marx, Wolfgang Straehle
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Patent number: 4442238Abstract: 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: GrantFiled: November 22, 1982Date of Patent: April 10, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, George P. Speranza
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Patent number: 4442237Abstract: 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: GrantFiled: November 22, 1982Date of Patent: April 10, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Kenneth G. McDaniel
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Patent number: 4439549Abstract: 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: GrantFiled: November 22, 1982Date of Patent: March 27, 1984Assignee: Texaco Inc.Inventor: Michael E. Brennan
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Patent number: 4435592Abstract: 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: GrantFiled: September 29, 1982Date of Patent: March 6, 1984Assignee: BASF Wyandotte CorporationInventor: Curtis J. Reichel
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Patent number: 4405766Abstract: 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: GrantFiled: July 30, 1982Date of Patent: September 20, 1983Assignee: The Dow Chemical CompanyInventors: James L. Bertram, George A. Doorakian, Lawrence G. Duquette
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Patent number: 4395566Abstract: 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: GrantFiled: March 8, 1982Date of Patent: July 26, 1983Assignee: American Hoechst CorporationInventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
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Patent number: 4271312Abstract: 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: GrantFiled: April 7, 1971Date of Patent: June 2, 1981Assignee: Standard Oil Company (Indiana)Inventors: Wilford J. Zimmerschied, Delbert H. Meyer
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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: 4219665Abstract: 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: GrantFiled: June 30, 1978Date of Patent: August 26, 1980Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Ulrich Zeidler, Fanny Scheuermann
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Patent number: 4156700Abstract: 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: GrantFiled: July 21, 1976Date of Patent: May 29, 1979Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National DefenceInventors: Meude Tremblay, Guy Perrault, Gonzague Duchesne
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Patent number: 4144395Abstract: 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: GrantFiled: December 5, 1977Date of Patent: March 13, 1979Assignee: BASF Wyandotte CorporationInventors: John R. Murphy, Louis C. Pizzini
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Patent number: 4118426Abstract: 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: GrantFiled: May 10, 1977Date of Patent: October 3, 1978Assignee: Western Kentucky UniversityInventors: Norman L. Holy, Theodore E. Nalesnik
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Patent number: 4115415Abstract: 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: GrantFiled: October 22, 1976Date of Patent: September 19, 1978Assignee: Nisso Petrochemical Industries Co., Ltd.Inventors: Hiroshi Yoshihara, Takashi Tobita, Ryoichi Tomizawa, Kunio Ishikawa
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Patent number: 4069242Abstract: 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: GrantFiled: September 9, 1971Date of Patent: January 17, 1978Assignee: The Dow Chemical CompanyInventor: Arthur E. Gurgiolo