From Polyhydroxy Containing Compound Patents (Class 568/619)
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Patent number: 5621148Abstract: (A) oligohydroxy-C.sub.3-8 -alkanes containing at least 3 hydroxy groups and (B) KOH, that contain at least 5% by weight of K.sup.+ and at least one alcoholic hydroxy group are eminently suitable as oxyalkylation catalysts, in particular for the oxyalkylation of ester group-containing substrates, before all of natural, vegetable or animal fats or oils or their modification products.Type: GrantFiled: February 1, 1995Date of Patent: April 15, 1997Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
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Patent number: 5616679Abstract: A polyalkylene glycol having the general formula:HO--[R--O--].sub.n Hin which n has a value of at least 2 and R is an alkylene radical containing at least 20 carbon atoms is provided. Preferred polyalkylene glycols have an alkylene radical which is a branched alkylene radical containing at least 10 carbon atoms in the main chain and a degree of polymerization such that n is from 4 to 7. The polyalkylene glycol is prepared by the acid-catalyzed polycondensation of a monomeric alkylene glycol at elevated temperature.Type: GrantFiled: November 14, 1995Date of Patent: April 1, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Matthias Fies, Roland Gr utzmacher, Alfred Westfechtel
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Patent number: 5608117Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-l-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.Type: GrantFiled: August 28, 1995Date of Patent: March 4, 1997Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Stephen N. Falling
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Patent number: 5539129Type: GrantFiled: July 22, 1994Date of Patent: July 23, 1996Assignee: L'OrealInventors: Alexandre Zysman, Henri Sebag, Alain Ribier, Guy Vanlerberghe, Claude Mahieu, Claude Berthelot
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Patent number: 5476971Abstract: Glycerine di-t-butyl ether is prepared by the liquid phase reaction of glycerine and the reaction being carried out with separate liquid phases comprised of isobutylene and glycerine.Type: GrantFiled: January 13, 1995Date of Patent: December 19, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Vijai P. Gupta
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Patent number: 5444170Abstract: This invention pertains to an improved process for the hydrogenation of acetylenic compounds prepared by the condensation of ketones or aldehydes with acetylene wherein the acetylenic compounds are contacted with hydrogen in the presence of a hydrogenation catalyst under conditions for effecting hydrogenation. The improvement in the process resides in utilizing a novel cocatalyst system for hydrogenating the acetylenic compounds to paraffins. The cocatalyst converts the inhibiting impurity in the feed to a noninhibiting species and comprises palladium and platinum, typically in a ratio of from 1 to 40 weight parts palladium per weight part platinum.Type: GrantFiled: January 10, 1994Date of Patent: August 22, 1995Assignee: Air Products and Chemicals, Inc.Inventor: Gamini A. Vedage
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Patent number: 5431822Abstract: A description is given of a process for the separation of at least one constituent from a mixture containing at least two polyglycerols having consecutive degrees of polymerization from 2 to 10, in which said mixture is passed into at least one column lined with an adsorbent particular phase through which flows a liquid eluent, said phase consisting of a cationic organic resin such as a styrene-divinyl benzene copolymer or an anionic resin, or a mineral phase chosen from among silicas, aluminas and zeolites in normal form or modified by grafting, said liquid eluent consisting of an aqueous phase to which is optionally added a strong acid. The process described can be performed continuously or batchwise and in simulated counter-current (SCC) or simulated cocurrent manner.Type: GrantFiled: February 15, 1994Date of Patent: July 11, 1995Assignee: Institut Francais du PetroleInventors: Gabriel Terneuil, Gerard Hotier, Daniel Lonchamp
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Patent number: 5401439Abstract: Oil demulsifiers are based on an alkoxylate having a polydispersity of at least 1.7, and the alkoxylates are prepared using a metal alcoholate as a catalyst.Type: GrantFiled: December 21, 1992Date of Patent: March 28, 1995Assignee: BASF AktiengesellschaftInventors: Guenther Elfers, Wilfried Sager, Hans-Henning Vogel, Knut Oppenlaender
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Patent number: 5393867Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of a palladium(O) catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, m/(n+m) is greater than 0.30 and up to 0.Type: GrantFiled: January 18, 1994Date of Patent: February 28, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Falling: Stephen N.
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Patent number: 5391722Abstract: The present invention relates to a process for making a polyol which comprises the steps of: (a) fabricating a propoxylated polyhydric initiator by reacting propylene oxide with a polyhydric initiator in the presence of an acid catalyst, said reaction being conducted in the absence of a KOH catalyst, to produce a propoxylated polyhydric initiator containing acid catalyst residue(s) and free of KOH catalyst residue, and (b) reacting said propoxylated polyhydric initiator containing acid catalyst residue(s) with an alkylene oxide in the presence of a double metal cyanide complex catalyst to produce a polyol.Type: GrantFiled: March 30, 1990Date of Patent: February 21, 1995Assignee: Olin CorporationInventors: Kiran B. Chandalia, John W. Reisch, Michael M. Martinez
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Patent number: 5386045Abstract: A process for producing alkoxylated mono-, di-, and tri-esters in which a starting material ester and an alkylene oxide are reacted in the presence of selected calcium based catalysts.Type: GrantFiled: August 5, 1992Date of Patent: January 31, 1995Assignee: Vista Chemical CompanyInventors: Upali Weerasooriya, Donald T. Robertson, John Lin, Bruce E. Leach, Cynthia L. Aeschbacher, Tonyette S. Sandoval
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Patent number: 5374705Abstract: Polyether polyols are by reacting an alkylene oxide comprising propylene oxide with an initiator containing at least three active hydrogen atoms per molecule. The reaction is conducted in the presence of an alkoxylation catalyst which is barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, or mixtures thereof; and in the presence of from about 1 to about 10 weight percent, based on total weight of initiator, of a processing aid that is an organic monohydroxyl- or dihydroxyl-containing substance having a molecular weight of at least 30, or a mixture thereof. The processing aid enhances the ability to obtain polyether polyols having a reduced unsaturation content.Type: GrantFiled: December 27, 1993Date of Patent: December 20, 1994Assignee: The Dow Chemical CompanyInventors: David E. Laycock, Robert A. Sewell
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Patent number: 5362494Type: GrantFiled: July 14, 1992Date of Patent: November 8, 1994Assignee: L'OrealInventors: Alexandre Zysman, Henri Sebag, Alain Ribier, Guy Vanlerberghe, Claude Mahieu, Claude Berthelot
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Patent number: 5349094Abstract: Oligoglycerol mixtures having a high diglycerol content are prepared by a process in which glycerol is condensed in the presence of zeolites corresponding to formula (I)M.sub.2/z O * Al.sub.2 O.sub.3 * x SIO.sub.2 * y H.sub.2 O (I)in which M is an alkali metal or alkaline earth metal having a valency of z, x is a number of 1.8 to 12 and y is a number of 0 to 8. The water of condensation which is formed during the reaction, is continuously removed from the reaction mixture and the reaction is terminated when the quantity of water theoretically necessary for the formation of diglycerol has been separated.Type: GrantFiled: June 12, 1992Date of Patent: September 20, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Eugene G. Harris, Udo Hees, Reinhard Bunte, Johannes W. Hachgenei, Peter Kuhm
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Patent number: 5342903Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.Type: GrantFiled: April 30, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
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Patent number: 5340916Abstract: The present invention relates to a process for the preparation of a hard foam containing urethane groups or urethane and isocyanurate groups by the polyisocyanate polyaddition process, by reactinga) a polyoxypropylene- or polyoxyethylene-polyoxypropylene-polyol containing secondary hydroxyl groups, having a functionality of from 3.5 to 4.3, a hydroxyl number of from 350 to 650 and a viscosity of from 500 to 2,500 mPa.multidot.s at 23.degree. C.Type: GrantFiled: October 26, 1992Date of Patent: August 23, 1994Assignee: BASF AktiengesellschaftInventors: Rolf Henn, Werner Hinz, Ludwig Schuster, Klaus Vorspohl
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Patent number: 5243086Abstract: A process for the preparation of a composition containing diglycerol, in which process at least a stoichiometric amount of isopropylideneglycerol is reacted with .alpha.-monochlorohydrin in the presence of at least one alkaline compound at sufficient temperatures to yield an intermediate product composition containing monoisopropylidenediglycerol and a salt. Most of the salt and water formed is removed from the intermediate product composition, and any unreacted isopropylideneglycerol is removed by distillation. The remaining intermediate product composition containing monoisopropylidenediglycerol is subsequently reacted with water in the presence of at least one acidic catalyst at sufficient temperatures to yield a product composition containing diglycerol and acetone and substantially no cyclic glycerols.Type: GrantFiled: September 25, 1992Date of Patent: September 7, 1993Assignee: Deutsche Solvay-WerkeInventors: Gerald Jakobson, Werner Siemanowski, Helmut Dillenburg
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Patent number: 5237113Abstract: Haloalcohols of the general formula IHal--X--OH (I)where X is straight-chain or branched, substituted or unsubstituted alkylene of 4 or more carbon atoms in the chain, which may be interrupted by one or more heteroatoms, and Hal is halogen, are prepared by reacting a diol of the general formula IIHO--X--OH (II)where X has the above meanings, with an aqueous hydrogen halide solution in a water-immiscible organic solvent which is inert under the reaction conditions, at from 50.degree. to 150.degree. C., using an excess of hydrogen halide, based on the diol of the general formula II, of from 10 to 200 mole percent and setting a volume ratio of inorganic phase: organic phase of from 1:2 to 1:50.Type: GrantFiled: November 9, 1992Date of Patent: August 17, 1993Assignee: BASF AltiengesellschaftInventors: Rainer Becker, Wolfgang Mackenroth, Walter Seufert
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Patent number: 5227537Abstract: A method is described for the production of 6,12-dihydro-6-hydroxy-cannabidiol which is obtained by the reaction of olivetol and cis-p-menth-2-ene-1,8,-diol and the reaction thereof to yield trans-delta-9-tetrahydrocannabinol.Type: GrantFiled: January 8, 1992Date of Patent: July 13, 1993Assignee: Heinrich Mack Nachf.Inventors: Peter Stoss, Peter Merrath
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Patent number: 5220046Abstract: A process for producing alkoxylated methyl esters to produce a narrow homolog distribution of the alkoxylate species in which a staring material methyl ester and an alkylene oxide are reacted in the presence of selected calcium based catalysts.Type: GrantFiled: August 22, 1991Date of Patent: June 15, 1993Assignee: Vista Chemical CompanyInventors: Bruce E. Leach, John Lin, Cynthia L. Aeschbacher, Donald T. Robertson, Tonyette S. Sandoval, Upali Weerasooriya
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5198598Abstract: Alkadienyl ethers are prepared by the telomerization of conjugated dienes with polyols by continuous addition of the alkadiene to a reaction mixtue comprised of the polyol, secondary alcohol solvent, a portion of the alkadiene to be added, and low palladium catalyst concentration.Type: GrantFiled: July 19, 1991Date of Patent: March 30, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karlheinz Hill, Steven D. Axt, Kenneth J. Weese
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Patent number: 5169989Abstract: An improved process for preparing a polyether polyol of reduced scorching properties comprising buffering of the alkaline polyether polyol before heating to remove water, and the use of said polyether polyol to prepare flexible foam slabstocks.Type: GrantFiled: March 1, 1991Date of Patent: December 8, 1992Assignee: Miles Inc.Inventors: Alfred L. Peterson, Mark S. Solomon, Kenneth E. Reed, Edward P. Squiller
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Patent number: 5164497Abstract: A decarboxylation process which comprises contacting a carboxylated compound with a metal oxide catalyst under conditions effective to decarboxylate the carboxylated compound.Type: GrantFiled: September 20, 1990Date of Patent: November 17, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson, Bernard C. Ream
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Patent number: 5130413Abstract: A process for producing an unsaturated group-terminated high-molecular weight polyalkylene oxide by adding an alkali metal and/or an alkali metal compound capable of producing an alkali metal hydroxide on reaction with water to a hydroxyl-terminated polyalkylene oxide having a repeating unit represented by formula --R.sup.1 --O-- (wherein R.sup.1 represents a divalent alkylene group having from 2 to 8 carbon atoms) to substitute the hydrogen atom of the hydroxyl end group with an alkali metal (alkoxidation) the resulting polyalkylene oxide is reacted with a polyhalogen compound to increase the molecular weight of the polyalkylene oxide and then additional alkali metal and/or alkali metal compound is added before reacting the resulting high-molecular weight polyalkylene oxide with an unsaturated halogen compound to introduce an unsaturated group to the molecular chain terminals.Type: GrantFiled: August 30, 1990Date of Patent: July 14, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yukimitsu Asai, deceased, by Keiji Asai, legal representative, by Yoshie Asai, legal representative, Hiroyuki Kawata, Tooru Nakagawa
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Patent number: 5126493Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.Type: GrantFiled: April 5, 1991Date of Patent: June 30, 1992Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
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Patent number: 5114619Abstract: This invention is a process for the preparation of a polyol having an equivalent weight of 200 to 5000 by the reaction of a monoepoxy compound with an initiator containing an active hydrogen atom in the presence of a catalyst substance selected from the group consisting of barium, strontium and their oxides, hydroxides, hydrated hydroxides or monohydroxide salts, and mixtures thereof. The process comprises adding water during the reaction of the monoepoxy compound with the initiator. The quantity of water added is one percent or less by weight of the total weight of monoepoxy compound to be reacted with the initiator.Type: GrantFiled: July 14, 1989Date of Patent: May 19, 1992Assignee: The Dow Chemical CompanyInventor: A. J. Heuvelsland
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Patent number: 5104575Abstract: This invention relates to heterogeneous (organic polymer-supported) calcium-containing catalysts and the use thereof in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen. In another aspect of this invention, processes are provided for preparing heterogeneous (organic polymer-supported) calcium-containing catalysts for alkoxylation using calcium oxide or calcium hydroxide as sources for the catalytically-active calcium. In a further aspect of this invention, alkoxylation products are provided that have beneficial, narrow molecular weight ranges and are essentially neutral in pH and free from catalyst residues.Type: GrantFiled: June 12, 1989Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Robert J. Knopf
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5053556Abstract: A one-step process for producing an alkenyl ether in only one step and under mild conditions by reacting an aldehyde of the formula ##STR1## with an alcohol of the formulaR.sup.3 --OHin the presence of an acidic catalyst in liquid phase, and recovering as the reaction product an alkenyl ether of the formula ##STR2## wherein R.sup.1 is a 2-8 C alkyl or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group,R.sup.2 is a 1-6 C alkyl,R.sup.3 is a linear or branched 6-12 C alkyl, a cyclohexyl, a hydroxyhexamethylenyl or ##STR3## wherein R' is H and n is 2 or 3, R.sup.4 is hydrogen or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group, andR.sup.5 is a 2-8 C alkyl or R--CH.dbd.CH-- wherein R is a 1-8 C alkyl.Type: GrantFiled: January 17, 1990Date of Patent: October 1, 1991Assignee: Chisso CorporationInventor: Noriyuki Ohnishi
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Patent number: 5003111Abstract: Novel polyether polyols are disclosed which contain an internal block of isobutylene oxide or a mixture of isobutylene oxide and a mono- or unsaturated alkylene oxide and an end-cap of a mono- or unsubstituted alkylene oxide to provide reactive primary or secondary hydroxyl end-groups. The polyether polyols are useful intermediates in the production of segmented elastomers. A process for the preparation of the novel polyols is also described in which an alkali metal catalyst and a crown ether cocatalyst are employed to afford polyols containing relatively low levels of unsaturation.Type: GrantFiled: February 14, 1989Date of Patent: March 26, 1991Assignee: Arco Chemical Technology, Inc.Inventor: Stephen D. Harper
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Patent number: 4994626Abstract: A process for preparing an etherified polyoxyalkylene derivative of the formula ##STR1## wherein R.sup.1 and R.sup.4 are identical or different and are each independently C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.6 -C.sub.20 aryl, C.sub.6 -C.sub.20 alkyl aryl, C.sub.6 -C.sub.20 cycloalkyl, and mixtures thereof, R.sup.2 and R.sup.3 are identical or different and independent of each other are H, CH.sub.3, CH.sub.3 CH.sub.2, and mixtures thereof, m, m' and n are identical or different and are each greater than or equal to zero, with the proviso that m+m'+n is from 3 to 300; by reacting a polyoxyalkylene compound of the formula.Type: GrantFiled: November 8, 1989Date of Patent: February 19, 1991Assignee: BASF CorporationInventors: Ronald E. Greenough, Jay G. Otten, Stefan Birnbach, Jochen Houben
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Patent number: 4978805Abstract: Polyethers I ##STR1## R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.20 -alkyl, n and m are each from 1 to 30 and r is from 0 to 20, are used mainly as surfactants in detergent and cleaning agent formulations.Type: GrantFiled: June 9, 1989Date of Patent: December 18, 1990Assignee: BASF AktiengesellschaftInventors: Richard Baur, Stefan Birnbach, Alfred Oftring, Ekhard Winkler
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Patent number: 4973763Abstract: A process for preparation of polyglycerol is provided, comprising the steps of (a) reacting glycerol or diglycerol with hydrogen chloride at between about 340.degree. K. and about 410.degree. K. to yield a mixture that comprises an .alpha.-monochlorohydrin of glycerol or an .alpha.-monochlorohydrin of diglycerol, (b) mixing the .alpha.-monochlorohydrins and an alkali metal glycerolate or an alkali metal diglycerolate at a temperature of between about 320.degree. K. and 410.degree. K. to yield a mixture of alkali metal chloride and glycerol and/or diglycerol and polyglyerol, (c) separating the alkali metal chloride from the glycerols and (d) separating the polyglycerol from glycerol and/or diglycerol.Type: GrantFiled: September 5, 1989Date of Patent: November 27, 1990Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Horst Linke, Werner Siemanowsky
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Patent number: 4962237Abstract: A catalytic process for polymerizing epoxides using active hydrogen initiators forming polyols having low unsaturation levels and high primary hydroxyl levels. The catalysts useful in this process are prepared from catalyst precursors exemplified by hydrotalcite. This process is more reactive with less acidic active hydrogen initiators. The polyols can be used in urethanes without removal of the catalyst.Type: GrantFiled: January 2, 1990Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventor: David E. Laycock
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Patent number: 4960953Abstract: A process for the preparation of polyglycerols which are low in cyclic components comprises reacting glycerol or diglycerol or a higher polyglycerol with epichlorohydrin at elevated temperatures; adding base corresponding to the organically bound chlorine content of the reaction mixture, at a temperature of 50.degree.-120.degree. C., to the unseparated reaction mixture obtained; desalting the resultant reaction mixture and recovering glycerol, diglycerol and higher polyglycerols by fractional distillation.Type: GrantFiled: March 24, 1989Date of Patent: October 2, 1990Assignee: Deutsche Solvay-Werke GmbHInventors: Gerald Jakobson, Werner Siemanowski
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Patent number: 4946984Abstract: This invention relates to the use of calcium sulfate as a catalyst in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen, that have beneficial, narrow molecular weight ranges.Type: GrantFiled: September 30, 1988Date of Patent: August 7, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Charles F. Hauser
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Patent number: 4927961Abstract: Polyoxylalkylene ether with an average molecular weight of 400 to 10,000 with at least one terminal hydroxyl group and at least one lateral --SO.sub.3 X group (X=hydrogen, alkali metal or ammonium ion) is disclosed. The polyoxyalkylene ether is obtainable byThe statistical or blockwise addition reaction of (a) .alpha.-alkylene oxides with 2 to 14 carbon atoms or mixtures hereof and (b) allyl and/or methallyl glycidyl ethers to monohydric to quadrihydric aliphatic alcohols with up to 8 carbon atoms, the ratio of component (a) to component (b) being selected so that at least one allyl ether group is linked to the average molecule,reacting the polymer by a known reaction with, based on the allyl ether groups, at least equimolar amounts of a compound of the formula HSO.sub.3 Y (Y=alkali or ammonium ion) andif necessary, exchanging the cation Y against a hydrogen ion also by a known procedure.Type: GrantFiled: September 29, 1989Date of Patent: May 22, 1990Assignee: Th. Goldschmidt AGInventors: Jurgen Fock, Dietmar Schedlitzki
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Patent number: 4922029Abstract: Etherified polyoxyalkylene derivatives of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl or C.sub.3 -C.sub.5 -alkenyl, R.sup.2 and R.sup.3 independently of one another are each hydrogen, methyl or ethyl, R.sup.4 is C.sub.1 -C.sub.4 -alkyl and m and n are identical or different and are each greater than or equal to 0, with the proviso that the sum of m and n is from 3 to 300, are prepared by reacting the corresponding hydroxyl-containing polyoxyalkylene derivative with a dialkyl sulfate in the presence of an alkali metal hydroxide by a process in which the reaction is carried out at from 20.degree. to 60.degree. C. in the presence of an aqueous solution of an alkali metal hydroxide, the concentration of alkali metal hydroxide during the entire duration of the reaction being not less than 35% by weight, based on the aqueous phase, and not less than 1 mole of dialkyl sulfate and not less than one mole of alkali metal hydroxide are used per mole equivalent of organic hydroxyl groups.Type: GrantFiled: August 5, 1988Date of Patent: May 1, 1990Assignee: BASF AktiengesellschaftInventors: Stefan Birnbach, Josef Mueller, Klaus Wulz, Jochen Houben
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Patent number: 4902658Abstract: This invention relates to heterogeneous (organic polymer-supported) calcium-containing catalysts and the use thereof in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen. In another aspect of this invention, processes are provided for preparing heterogeneous (organic polymer-supported) calcium-containing catalysts for alkoxylation using calcium oxide or calcium hydroxide as sources for the catalytically-active calcium. In a further aspect of this invention, alkoxylation products are provided that have beneficial, narrow molecular weight ranges and are essentially neutral in pH and free from catalyst residues.Type: GrantFiled: September 30, 1987Date of Patent: February 20, 1990Assignee: Union Carbide CorporationInventors: Stephen W. King, Robert J. Knopf
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Patent number: 4902834Abstract: A process is disclosed for the preparation of capped polyoxyalkylene block polyethers with exceptionally low hydroxyl numbers and correspondingly high capping efficiency. This improvement is accomplished through the use of cesium hydroxide catalysis during oxyethylation.Type: GrantFiled: August 30, 1988Date of Patent: February 20, 1990Assignee: BASF CorporationInventors: Jay G. Otten, Roger A. Ott
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Patent number: 4885402Abstract: Process for preparing polyglycerolated nonionic surfactants from (poly)hydroxylated organic compounds, by condensing glycerol monochlorohydrin with the said (poly)hydroxylated compound in the presence of a strong base, at a temperature below 150.degree. C. and in the presence of an aromatic solvent, removing the water formed by distillation as it forms.This process makes it possible to condense a relatively large quantity of glycerol monochlorohydrin in a single step, while limiting the formation of polyglycerols, and to obtain a good quality surfactant which is usable in cosmetic compositions.Type: GrantFiled: June 3, 1988Date of Patent: December 5, 1989Assignee: L'OrealInventor: Henri Sebag
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Patent number: 4814515Abstract: A method of manufacturing a modified polyhydroxy compound, which is characterized in that a polyhydroxy compound is heated for 30 minutes or more at a temperature ranging from 150.degree. to 250.degree. C. under stirring and in the presence of tin, tin compounds such as tin halogenide, tin hydroxide and tin oxide. The polyhydroxy compound modified by this method is effective in improving the foamability and mechanical strength of urethane foam, when it is used as a raw material in the manufacture of urethane foam.Type: GrantFiled: May 18, 1987Date of Patent: March 21, 1989Assignee: Human Industry CorporationInventors: Sadao Kumasaka, Satomi Tada, Hirokazu Wakabayashi
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Patent number: 4774363Abstract: This invention relates to compounds having the structure ##STR1## wherein M is an alkali metal and n is an integer having a value of from 0 to 12. The invention also relates to the method of preparing said metal derivatives of butenediol and to their catalytic use in vinylation reactions.Type: GrantFiled: October 16, 1987Date of Patent: September 27, 1988Assignee: GAF CorporationInventor: Lowell R. Anderson
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Patent number: 4754075Abstract: Narrow, balanced alkoxylation product mixture distributions having at least one alkoxylation product constituting more than 20 weight percent of the mixture can be provided by modified, calcium-containing catalysts. Catalysts for alkoxylation processes can be produced from lime and can, with modification, be used to make the narrow, balanced alkoxylation product mixture distribution.Type: GrantFiled: October 6, 1986Date of Patent: June 28, 1988Assignee: Union Carbide CorporationInventors: Robert J. Knopf, Louis F. Theiling, Jr.
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Patent number: 4727199Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: July 10, 1985Date of Patent: February 23, 1988Assignee: Union Carbide CorporationInventor: Stephen W. King
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Patent number: 4703069Abstract: This invention relates to polyether polyols having an average hydroxyl value in the range of 100 to 250 mgKOH/g, which are alkoxylated derivatives of a polyhydric alcohol being a mixture of compounds according to formula (I) or/and (II) ##STR1## wherein R.sup.1 is H, CH.sub.3 or OCH.sub.3,R.sup.2 is H, CH.sub.2 OH or CH.sub.2 C(CH.sub.2 OH).sub.3, andR.sup.3 and R.sup.4 areH, CH.sub.2 OH or CH.sub.2 OCH.sub.3.Type: GrantFiled: June 27, 1986Date of Patent: October 27, 1987Assignee: Imperial Chemical Industries plcInventors: James P. Brown, Ronald N. May, David Randall
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Patent number: 4677232Abstract: Process for the preparation of water-soluble or water-dispersible polyglycerolated nonionic surface-active agents.This process is characterized by the polyaddition of glycerol chlorohydrin and of a strong base, and preferably sodium or potassium hydroxide in an aqueous solution, to a (poly)hydroxylated compound.This process has the advantage of replacing glycidol, which is usually employed, by glycerol chlorohydrin, which is less costly, easier to store than glycidol, and also of avoiding the flash distillation of a flammable volatile solvent.Type: GrantFiled: December 13, 1985Date of Patent: June 30, 1987Assignee: L'OrealInventors: Henri Sebag, Guy Vanlerberghe
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Patent number: 4654377Abstract: The instant invention relates to an improved process for the preparation of low molecular weight polyalcohols by the catalytic hydrogenation of a mixture of different low molecular weight hydroxy aldehydes, hydroxy ketones and optionally also polyhydric alcohols such as is formed from the autocondensation of formaldehyde (such a mixture will hereinafter be referred to as "formose"). The invention also relates to the use of these polyalcohols for the production of polyurethane resins.Type: GrantFiled: April 28, 1986Date of Patent: March 31, 1987Assignee: Bayer AktiengesellschaftInventors: Edgar Mohring, Kuno Wagner, Hanns P. Muller
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Patent number: 4593135Abstract: A method for promoting the activity and/or extending the life of a cation-exchangeable layered clay catalyst in reactions susceptible to catalysis by protons which method comprises the addition to the catalyst of water as the sole additive. The quantity of water employed is suitably up to 40%, preferably up to 10% based on weight of reactants. The layered clay catalyst can be for example montmorillonite, bentonite or vermiculite. Suitable proton catalyzed reactions include formation of esters, (e.g. by reaction of olefin and carboxylic acid), ethers, aldehydes, thioethers and alkylation and cracking reactions.Type: GrantFiled: February 6, 1984Date of Patent: June 3, 1986Assignee: The British Petroleum Company P.L.C.Inventor: Reginald Gregory