Polyoxy Acid Moiety Patents (Class 560/186)
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Patent number: 5510512Abstract: Process for the preparation of 2-(dialkoxymethyl)carboxylic acid esters of the formula I ##STR1## by oxidizing .beta.-acetalization of acrylic acid esters with alcohols R.sup.1 OH, wherein R.sup.1 has the meaning mentioned, in the presence of oxygen as the oxidant and of a catalyst system based on one or more metals of the platinum group and/or compounds thereof and of a copper compound, comprises carrying out the reaction at a temperature of up to 80.degree. C. and in which the catalyst system contains 1 to 4 equivalents of anions, based on the sum of the metal atoms and metal cations, of which at most 3 equivalents are halide ions, the halogen having a molecular weight of at least 35.Type: GrantFiled: November 14, 1994Date of Patent: April 23, 1996Assignee: Hoechst AktiengesellschaftInventor: Heinz Strutz
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Patent number: 5502152Abstract: Disclosed is a polyoxyalkylene derivative which is useful for a carboxyl group-containing polyurethane resin, can easily introduce a carboxyl group into a polyurethane resin skeleton, and has a low melting point or is in a liquid state at normal temperature. The polyoxyalkylene derivative is represented by formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; R.sub.2 represents an alkylene group having from 1 to 6 carbon atoms or an arylene group having from 6 to 8 carbon atoms; A represents an alkylene group having from 4 to 7 carbon atoms; B represents an alkylene group having from 2 to 6 carbon atoms; l represents from 0 to 2; m represents from 0.1 to 35; n represents from 0.1 to 50; and 0.5<(m+n)<50.Type: GrantFiled: January 13, 1995Date of Patent: March 26, 1996Assignee: Hodogaya Chemical Co., Ltd.Inventors: Shigeru Shimada, Susumu Jinbo, Hideyuki Isii
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Patent number: 5466396Abstract: The present invention is directed to novel compounds having the formula: ##STR1## wherein R is a C.sub.8 -C.sub.24 substituted or unsubstituted alkyl or alkenyl group;m is 1 to 3;n is 1 to 5; andx is hydrogen or a C.sub.1 to C.sub.3 hydrocarbon.The compounds are mild and good foaming compounds which can be used in both personal washing bars and liquids.Type: GrantFiled: November 19, 1993Date of Patent: November 14, 1995Assignee: Lever Brothers CompanyInventors: Stephen A. Madison, Michael Massaro, Gail B. Rattinger, Christine Wenzel
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Patent number: 5457227Abstract: A novel, overall process for the preparation of a compound of the formula I: ##STR1## where R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group; andR.sup.3 is hydrogen, an alkyl group, or an aryl group, or salts thereof, useful as intermediates in the preparation of HMG-CoA reductase inhibitors; novel methods within the overall process; and novel intermediates produced by those methods.Type: GrantFiled: October 8, 1993Date of Patent: October 10, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, Yadagiri Pendri, Wen-Sen Li, David R. Kronenthal
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Patent number: 5412134Abstract: The protected cyclobutanone of the formula ##STR1## is treated with a dialkylaluminum chloride, an alkylaluminum dichloride, a trialkylaluminum compound, diphenylsilane in the presence of tris(triphenylphosphine) rhodium (I) chloride, or iridium tetrachloride to yield the corresponding diprotected cyclobutanol. This compound is useful as an intermediate in the preparation of antiviral agents.Type: GrantFiled: May 26, 1992Date of Patent: May 2, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Janak Singh, Gregory S. Bisacchi, Richard H. Mueller
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Patent number: 5387665Abstract: A resin for electrophotographic toner comprising a degradable polyester resin which is an amorphous poly (.alpha.-hydroxycarboxylic acid) prepared by direct dehydration-polycondensation of an .alpha.-hydroxycarboxylic acid and having, preferably, a number-average molecular weight ranging from 2000 to 7000. A further resin for electrophotographic toner comprising a degradable polyester resin which may be prepared by reacting an amorphous or semicrystalline poly (.alpha.-hydroxycarboxylic acid), having a number-average molecular weight ranging from 1000 to 7000 or 2000 to 7000 and prepared by direct dehydration-polycondensation of an .alpha.-hydroxycarboxylic acid, with a polyol having at least three hydroxyl groups or a polycarboxylic acid having at least three carboxyl groups in the molecule and, in case of the reaction product with the polyol can further be reacted with a diisocyanate to give an urethane-modified polyester. These polyesters can likewise be used as resins for toner.Type: GrantFiled: February 25, 1994Date of Patent: February 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Akira Misawa, Masanobu Ajioka
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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: 5315038Abstract: A new microorganism for breaking down moenomycins, a process for the breakdown, and the use of the breakdown products are disclosed. A new Bacillus species and the appropriate enzymes obtained therefrom can be used to break down phosphoglycolipid antibiotics. The breakdown products of moenomycins display antibiotic activity or can be used as building blocks for the synthetic preparation of transglycosylase inhibitors.Type: GrantFiled: April 20, 1993Date of Patent: May 24, 1994Assignee: Hoechst AktiengesellschaftInventors: Werner Aretz, Dirk Bottger, Gerhard Seibert, Alois Tumulka, Peter Welzel, Kurt Hobert
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Patent number: 5294731Abstract: A process for the preparation of .beta.-hydroxycarboxylates of the general formula I ##STR1## in which R.sup.1 and R.sup.2 individually denoteC.sub.1 -C.sub.20 alkyl optionally substituted by C.sub.1 -C.sub.8 alkoxy and/or halogen, C.sub.3 -C.sub.20 alkoxycarbonylalkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.5 -C.sub.30 acetalalkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.7 -C.sub.20 aralkenyl, hetaryl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl,or together denote a C.sub.2 -C.sub.8 alkylene chainand one or other of R.sup.1 and R.sup.2 denotes hydrogen, andR.sup.3 denotes hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl, andR.sup.4 denotes C.sub.1 -C.sub.20 alkyl, C.sub.Type: GrantFiled: March 23, 1993Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Wolfgang Siegel
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Patent number: 5282987Abstract: A carboxy ether of formula (II):[R--O(C.sub.3 H.sub.6 O).sub.x (C.sub.2 H.sub.4 O).sub.y (C.sub.3 H.sub.6 O).sub.z ].sub.2 CHCOOM (II)is disclosed. In formula (II) R is (i) a saturated or unsaturated, linear or branched group containing 6 to 20 carbon atoms, (ii) an alkylaromatic group or an alkylcycloaliphatic group, each containing a total of 4 to 16 carbon atoms in its alkyl group, (iii) a dialkylaromatic, dialkylcycloaliphatic, or trialkylcycloaliphatic group, each containing a total of 5 to 24 carbon atoms in its alkyl groups, or (iv) a trialkylaromatic group with a total of 7 to 28 carbon atoms in its alkyl groups; x is 0 to 15, y is 1 to 40, z is 0 to 15; and M is an alkali metal cation, an alkaline earth metal cation, an ammonium cation, an alkanolammonium cation, or a proton.Type: GrantFiled: August 5, 1991Date of Patent: February 1, 1994Assignee: Huels AktiengesellschaftInventors: Dieter Balzer, Heinz Riemer, Werner Friedrich
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Patent number: 5264611Abstract: A process for preparing a trans-.beta.-aroylacrylic ester which comprises reacting an aryl methyl ketone and an alkyl acetal of alkyl glyoxylate in the presence of an acid catalyst with heating.This process is excellent in operability, safety and ecomony and therefore is industrially advantageous process.Type: GrantFiled: January 6, 1992Date of Patent: November 23, 1993Assignee: Kanegafuchi Kagaku Kabushiki KaishaInventors: Yoshifumi Yanagida, Shingo Matsumoto, Satomi Takahashi
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Patent number: 5232633Abstract: Carbonated isethionate surfactants, compositions containing them and methods for their preparation are disclosed.Type: GrantFiled: June 19, 1992Date of Patent: August 3, 1993Assignee: Lever BrothersInventors: Leonora M. Ilardi, Stephen Madison, Deanne Oppermann
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Patent number: 5217582Abstract: A process is provided for separating high purity alkyl glycolate from a gaseous reaction mixture resulting from the catalyzed gas phase oxidation of alkyl glycolate. A hot solvent which is immiscible with water but selectively dissolves alkyl glycolate and alkyl glyoxylate is brought in contact with the gaseous reaction mixture, and water and alcohol vapors are removed from the hot solvent. The alkyl glyoxylate is removed from the solution by a first distillation and the alkyl glycolate and solvent are then separated in a second distillation.Type: GrantFiled: February 7, 1992Date of Patent: June 8, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: George E. Heinsohn, John F. Kook, John R. Kosak, Rudolf E. Svadlenak
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Patent number: 5214197Abstract: A novel 2,4-dihydroxyadipic acid derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R.sup.2 and R.sup.3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor.Type: GrantFiled: July 2, 1991Date of Patent: May 25, 1993Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Shigeo Hayashi, Noboru Ueyama, Kenji Inoue, Teruyoshi Koga, Satomi Takahashi
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Patent number: 5211721Abstract: Motor fuel compositions comprising gasoline are improved to control octane requirement increase (ORI) by including an ester of a carboxylic acid and a polyether polyol, preferably a polyether polyol including oxyethylene, oxypropylene and oxybutylene segments.Type: GrantFiled: July 15, 1991Date of Patent: May 18, 1993Assignee: Texaco Inc.Inventors: Rodney L. Sung, Daniel T. Daly
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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: 5136096Abstract: The bis-homotris compounds 4-amino-4-[1-(3-hydroxypropyl)]-1,7-heptanediol and 4-[1-(3-aminopropyl)]-4-[1-(3-hydroxypropyl)]-1, 7-heptanediol, and organic synthetic methods for their preparation are described. Unique multifunctional aminotriols, as well as their percursors, quaternary nitroalkanes are disclosed as building blocks for unimolecular micelles, as well as new series of cascade polymers. The quaternary nitro compounds which are disclosed allow the synthesis of a new aminotriol containing a quaternary carbon.Type: GrantFiled: March 26, 1991Date of Patent: August 4, 1992Assignee: University of South FloridaInventors: George R. Newkome, Charles N. Moorefield
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Patent number: 5099042Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.Type: GrantFiled: March 14, 1989Date of Patent: March 24, 1992Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5082967Abstract: Novel diheteroatom-substituted fatty acid analog substrates of myristoylating enzymes are provided which contain oxyen and/or sulfur in place of two methylene groups in carbon positions from 3 to 13 in the fatty acid chain of a C.sub.13 -C.sub.14 fatty acid analog or alkyl ester thereof in which said oxygen or sulfur atoms are separated by at least one methylene group.Type: GrantFiled: February 9, 1990Date of Patent: January 21, 1992Assignee: Washington UniversityInventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon, George W. Gokel
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Patent number: 5072005Abstract: Methyl 4-oxobutyrate and its methanol addition products, methyl 4,4-dimethoxybutyrate and gamma-methoxy-gamma-butyrolactone, which are useful as intermediates in the preparation of such industrially important compounds as gamma-butyrolactone, 1,4-butanediol and glutamic acid, are produced from the reaction of acrolein, carbon monoxide and methanol in the presence of a catalyst system which consists of (a) a Group VIII metal component selected from palladium metal or a palladium-containing composition which generates palladium metal under reaction conditions, (b) a hydrogen halide and (c) an arylarsine catalyst copromoter.Type: GrantFiled: July 9, 1987Date of Patent: December 10, 1991Assignee: National Distillers and Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5068422Abstract: A carboxy ether of formula (II):[R--O(C.sub.3 H.sub.6 O).sub.x (C.sub.2 H.sub.4 O).sub.y (C.sub.3 H.sub.6 O).sub.z ].sub.2 CHCOOM (II)is disclosed. In formula (II) R is (i) a saturated or unsaturated, linear or branched group containing 6 to 20 carbon atoms, (ii) an alkylaromatic group or an alkylcycloaliphatic group, each containing a total of 4 to 16 carbon atoms in its alkyl group, (iii) a dialkylaromatic dialkylcycloaliphatic, or trialkylcycloaliphatic group, each containing a total of 5 to 24 carbon atoms in it alkyl groups, or (iv) a trialkylaromatic group with a total of 7 to 28 carbon atoms in its alkyl groups; x is 0 to 15, y is 1 to 40, z is 0 to 15; and M is an alkali-earth metal cation, an alkaline earth metal cation, an ammonium cation, an alkylammonium cation, or a proton.Type: GrantFiled: December 13, 1989Date of Patent: November 26, 1991Assignee: Huels AktiengesellschaftInventors: Dieter Balzer, Heinz Reimer, Werner Friedrich
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Patent number: 5055613Abstract: The present invention relates to pentanedioic acid derivatives. The present invention further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions as hypolipidemic drugs.Type: GrantFiled: February 18, 1988Date of Patent: October 8, 1991Assignee: G. D. Searle & Co.Inventors: John S. Baran, Harman S. Lowrie
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Patent number: 5019298Abstract: Disclosed are optically active aromatic carboxylic acid derivatives represented by the formula (I): ##STR1## (wherein R.sub.2 represents an alkoxyalkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, which alkyl group may be substituted with a halogen atom; represents a number of 1 or 2; m represents a number of 0 or 1; and * indicates asymmetric carbon atom) and a process for producing such derivatives through the following reaction steps: ##STR2## The optically active aromatic carboxylic acid derivatives represented by the above-described formula (I) are useful as a liquid crystal material and can be also utilized as an intermeidate for the preparation of pharmaceuticals, agricultural chemicals and the like.Type: GrantFiled: April 25, 1988Date of Patent: May 28, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Takayuki Higashii
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Patent number: 5015760Abstract: Preparation of glyoxylic acid or derivatives thereof of the formula ##STR1## in which R denotes an alkyl radical with 1 to 10 C atoms and R.sub.1 denotes an alkyl radical with 1 to 4 C atoms, by ozonolysis of a dialkyl maleate, in which the alkyl radicals each have 1 to 10 C atoms, with the equivalent amount of ozone in an aliphatic alcohol of the formula R.sub.1 OH, and subsequent catalytic hydrogenation, in which the ozonolysis product is continuously introduced into a suspension of the hydrogenation catalyst in the alcohol of the formula R.sub.1 OH such that the peroxide content of the hydrogenation solution is not more than 0.1 mole/liter during the hydrogenation. Glyoxylic acid can be obtained from the resulting acetals of the formula I by hydrolysis.Type: GrantFiled: March 29, 1989Date of Patent: May 14, 1991Assignee: Chemie Linz AktiengesellschaftInventor: Alexander Sajtos
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Patent number: 4994602Abstract: A process for preparing an optically active 6-t-butoxy-3,5-dihydroxyhexanoic ester represented by formula: ##STR1## wherein t-Bu represents a t-butyl group; and R.sup.4 represents a lower alkyl group, which is useful as a precursor of a lactone moiety of campactin, mevinolin or analogues thereof is disclosed, comprising asymmetrically hydrogenating a 4-t-butoxyacetoacetic ester in the presence of a ruthenium-optically active phosphine complex to obtain an optically active 4-t-butyoxy-3-hydroxybutanoic ester, reacting the ester with a lithium enolate of an acetic ester to obtain an optically active 6-t-butyoxy-5-hydroxy-3-oxohexanoic ester, and asymmetrically hydrogenating the resulting ester in the presence of a ruthenium-optically active phosphine complex as a catalyst. The desired product can be obtained in good yield at high stereoselectivity.Type: GrantFiled: February 27, 1990Date of Patent: February 19, 1991Assignee: Takasago International CorporationInventors: Nobuo Seido, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 4983759Abstract: A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: ##STR1## wherein P.sup.1 and P.sup.2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of:reacting a butyronitrile derivative of the formula: ##STR2## wherein P.sup.1 and P.sup.2 are the same as defined above with an .alpha.-haloacetate of the formula:X--CH.sub.2 --COOR (III)wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: ##STR3## wherein P.sup.1, P.sup.2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).Type: GrantFiled: December 20, 1989Date of Patent: January 8, 1991Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Kenji Inoue, Satomi Takahashi, Keiichi Yonetsu, Noboru Ueyama
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Patent number: 4981989Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.Type: GrantFiled: November 8, 1989Date of Patent: January 1, 1991Assignee: American Cyanamid CompanyInventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
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Patent number: 4978741Abstract: A method of producing essentially haze-free isophthalic acid and polymethylolalkanoic acid-containing resins comprising reacting isophthalic acid, a polymethylolalkanoic acid, and a polyol in the presence of a catalytically effective amount of a catalyst selected from the group consisting of stannous oxalate, dibutyltin oxide, and tetrabutyl titanate at a temperature of between about 150.degree. C. and 230.degree. C. to produce haze-free resin.Type: GrantFiled: December 15, 1989Date of Patent: December 18, 1990Assignee: Questra Chemicals Corp.Inventor: Paul E. Eckler
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Patent number: 4948915Abstract: The reaction of a monohydroxyl or dihydroxyl alcohol with an alpha, beta-unsaturated ester in contact with a strongly basic anionic exchange resin in the hydroxyl or alkoxide form is unexpectedly and unpredictably enhanced by proper control of the water content in the reaction mixture and the temperature at which the reaction is carried out.Type: GrantFiled: July 22, 1986Date of Patent: August 14, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Brian T. Keen
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Patent number: 4923642Abstract: Quaternary ammonium compounds containing one or two long-chain ester or amide radicals of etherified hydroxycarboxylic acids and, for the remainder, short-chain radicals, which are liquid to pasty substances that may readily be dissolved or dispersed in water or alcohol/water mixtures. They may be used in dilute or concentrated, storable form for softening fabrics without the absorbency of the treated fabrics being adversely affected. The quaternary ammonium compounds are obtained by reaction of epoxyfatty acid esters with amines and subsequent quaternization.Type: GrantFiled: November 16, 1987Date of Patent: May 8, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Horst Rutzen, Horst Baumann, Bert Gruber
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4915875Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.Type: GrantFiled: November 4, 1986Date of Patent: April 10, 1990Assignee: The Dow Chemical CompanyInventors: Timothy R. Diephouse, Robert M. Strom
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Patent number: 4912187Abstract: An ester of a sterically hindered polyhydroxymonocarboxylic acid and a polyhydroxy-containing component, which ester is a solid at ambient temperature conditions, comprising the condensation product of said acid selected from the group consisting of dimethylolpropionic acid, trimethylolacetic acid, and mixtures thereof, and said polyhydroxy-containing component selected from the group consisting of pentaerythritol, trimethylolethane, and mixtures thereof, said product having a mol ratio of acid to polyhydroxy-containing component of at least about 1.75, a ring and ball softening point of at least about 50.degree. C., and an acid number of less than about 40.Type: GrantFiled: January 29, 1988Date of Patent: March 27, 1990Assignee: Questra Chemicals Corp.Inventor: Paul E. Eckler
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Patent number: 4889650Abstract: A synthetic traction fluid comprising, as a base oil, at least one ester or its derivative selected from monoesters, diesters, triesters and derivatives thereof represented by the formula: ##STR1## where Y is independently selected from ##STR2## --(CH.sub.2)n--OH A' is an ester linkage, n is an integer of 1 to 3, and R.sub.Type: GrantFiled: May 28, 1987Date of Patent: December 26, 1989Assignee: Toa Nenryo Kogyo, K.K.Inventors: Narihiko Yoshimura, Hirotaka Tomizawa, Yasuji Komatsu
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Patent number: 4870199Abstract: Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, andR.sub.2z is C.sub.1-4 alkyl, benzyl or allyl,comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formulaMg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formulaLi.sup..sym..crclbar. CH.sub.2 --COOR.sub.2yto obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl,R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, andR.sub.Type: GrantFiled: March 10, 1988Date of Patent: September 26, 1989Assignee: Sandoz Pharm. Corp.Inventors: Kau-Ming Chen, Goetz E. Hardtmann, Prasad K. Kapa, George T. Lee, Jerome Linder, Sompong Wattanasin
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Patent number: 4867849Abstract: There is disclosed an improved process for the manufacture of glyoxylic acid obtained by oxidation of glycolic acid. For processing purposes alkyl esters of these acids are employed. Increased efficiency is obtained by recovering glycolate rich streams from one or more distillation operations and after treatment to remove acetic acid by-product the streams are recycled to the oxidation reaction.Type: GrantFiled: July 25, 1988Date of Patent: September 19, 1989Inventors: Dario R. Cova, John M. Thorman
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Patent number: 4845268Abstract: A halogen-containing polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.2 --(CHClCF.sub.2 CF.sub.2 O).sub.b --(CCl.sub.2 CF.sub.2 CF.sub.2 O).sub.c --(CHFCF.sub.2 CF.sub.2 O).sub.d --(CFClCF.sub.2 CF.sub.2 O).sub.e --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.f --(I)wherein a, b, c, d, e and f are each an integer not less than 0 and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200and1.ltoreq.a+c+d+f,which may be prepared by ring-opening polymerizing 2,2,3,3-tetrafluorooxetane in the presence of an polymerization initiator to give a polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.a -- (II)wherein a is the same as defined above, and optionally fluorinating and/or chlorinating the polyether (II).Type: GrantFiled: December 9, 1986Date of Patent: July 4, 1989Assignee: Daikin Industries, Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
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Patent number: 4830769Abstract: The present invention relates to propoxylated guerbet alcohols and esters having an iodine number less than 7 and defined by the general formula: ##STR1## which alcohols and esters are useful, individually or in admixture, as lubricants in the working of metals.Type: GrantFiled: February 1, 1988Date of Patent: May 16, 1989Assignee: GAF CorporationInventors: Anthony J. O'Lenick, Jr., Raymond E. Bilbo
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Patent number: 4820385Abstract: An improved process for separating high purity alkyl glyoxylate from complex mixtures containing alkyl glyoxylate, alkyl glycolate, water, alcohol and miscellaneous impurities by an azeotropic distillation operation using an azeotroping agent selected from the group consisting of methylene dichloride, 1,1,1--trichloroethane, and benzene.Type: GrantFiled: February 18, 1988Date of Patent: April 11, 1989Assignee: Monsanto CompanyInventors: Dario R. Cova, John M. Thorman
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Patent number: 4814491Abstract: The invention relates to hemiacetals of glyoxylic esters and to a process for obtaining a glyoxylic ester having a C.sub.1 to C.sub.4 ester group from a mixture which essentially contains a glyoxylic ester of this type plus water and/or a C.sub.1 to C.sub.4 alcohol ROH. In this, the glyoxylic ester and the water and/or the alcohol are partly or completely in a chemically bonded form. A higher alcohol R'OH having a boiling point above 180.degree. C. is added, and distillation is carried out under a pressure not exceeding 800 mbar to remove first the water and/or the alcohol ROH and then the glyoxylic ester.Type: GrantFiled: May 11, 1988Date of Patent: March 21, 1989Assignee: Hoeschst AktiengesellschaftInventors: Robert K. Driscoll, Ernst I. Leupold, Joachim Schutz
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Patent number: 4812593Abstract: Bifunctional compounds of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl of 1 to 6 carbon atoms, R.sup.2 and R.sup.3 may furthermore be hydrogen, R.sup.2 is furthermore alkoxy and R.sup.4 is hydrogen, alkyl of 1 to 6 carbon atoms or alkoxy, and a double bond may be present between carbon atoms 2 and 3, are prepared by converting a tetraalkoxyalkane or a dialkoxyalkanoate of the formulae ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the above meanings, in the presence of a catalyst, such as a zeolite, in particular one of the pentasil type, and/or a phosphate and/or phosphoric acid on a carrier.Type: GrantFiled: August 6, 1987Date of Patent: March 14, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4766153Abstract: The invention relates to novel alkyl polyoxyalkylene carboxylate esters and to their use as surface active agents. The novel esters are especially useful as emollients in skin care compositions.Type: GrantFiled: April 1, 1987Date of Patent: August 23, 1988Assignee: Sandoz Ltd.Inventor: Robert V. Casciani
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Patent number: 4743401Abstract: A process for converting an allylic ether to its corresponding acetal is disclosed. In this process an allylic ether is contacted with an organic hydroxy compound and a catalytically effective amount of a cobalt compound to produce the corresponding acetal.Type: GrantFiled: October 3, 1986Date of Patent: May 10, 1988Assignee: National Distillers and Chemical CorporationInventors: Biau-Hung Chang, Ronnie M. Hanes
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Patent number: 4734522Abstract: Six-membered ring compounds of the formula I ##STR1## wherein A is a benzene or cyclohexane ring,X.sup.1 to X.sup.6 independently of one another in each case are H, --OR, --COOR, --SR, --SOR, --SO.sub.2 R or, if A is a cyclohexane ring, also --O--COR, andR is in each case an alkyl group which has up to 15 C atoms and in which one or two CH.sub.2 groups can be replaced by O atoms, at least three of the substituents X.sup.1 to X.sup.6 being other than H,can be used as constituents of discotic liquid-crystal phases for liquid-crystal display elements.Type: GrantFiled: January 7, 1986Date of Patent: March 29, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Wadi Poules, Rudolf Eidenschink, Bernhard Scheuble
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Patent number: 4719032Abstract: Cyclohexane derivatives of formula IR.sup.1 --Cy--CH.sub.2 --Q--(Cy).sub.m --O--(CO).sub.n --CH.sub.2 --R.sup.2 IwhereR.sup.1 denotes alkyl with 1 to 12 C atoms in which also one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,R.sup.2 denotes H, alkyl with 1 to 12 C atoms in which also one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --O--CO-- or --CO--O--,Cy denotes trans-1,4-cyclohexyleneQ denotes --CH.sub.2 -- or --O--,m denotes 1 or 2, andn denotes 0 or 1,are suitable as components of liquid-crystalline phases.Type: GrantFiled: March 21, 1986Date of Patent: January 12, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Andreas Wachtler, Joachim Krause, Reinhard Hittich, Bernhard Scheuble
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Patent number: 4692547Abstract: The invention relates to a process for the preparation of glyoxylic hemiacetal esters, in which first glycolic esters are oxydehydrogenated to give glyoxylic esters, and then the latter are reacted with an alcohol. The gaseous reaction mixture formed in the oxydehydrogenation is introduced, together with an excess of an alcohol which is suitable as an entraining agent, into a distillation column and then the water of reaction is distilled overhead together with other low-boilers and part of the excess alcohol, the glyoxylic hemiacetal ester and the remainder of the excess alcohol resulting as the bottom product.In a variant of the process, use is made of an additional inert entraining agent whose azeotrope with water boils below 90.degree. C. and below the alcohol which is used, and then the water of reaction is distilled overhead with the assistance of this entraining agent.Type: GrantFiled: December 18, 1985Date of Patent: September 8, 1987Assignee: Hoechst AktiengesellschaftInventors: Robert K. Driscoll, Ernst I. Leupold, Wolfgang Ebertz
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Patent number: 4681708Abstract: A process for converting an alkoxyalkadiene to an alkyl dialkoxyalkanoate is disclosed. The process involves contacting an alkoxyalkadiene with carbon monoxide and an alkanol in the presence of a catalytically effective amount of a cobalt catalyst.Type: GrantFiled: October 3, 1986Date of Patent: July 21, 1987Assignee: National Distillers and Chemical CorporationInventor: Biau-Hung Chang
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Patent number: 4658069Abstract: 9-methoxy-7-nonenal may be isomerized in the presence of methanol and ruthenium chloride to provide 1,1,9,9-tetramethoxynonane. The rates of reaction are increased by pre-formation of 1,1,9-trimethoxy-7-nonene and removal of the water generated prior to conducting the isomerization reaction.Type: GrantFiled: July 2, 1985Date of Patent: April 14, 1987Assignee: National Distillers and Chemical CorporationInventors: Ronnie M. Hanes, William D. Baugh
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Patent number: 4647688Abstract: Fatty ethers are provided which are lower alkyl ethers cyano-substituted lower alkyl ethers, ester ethers or amide ethers of fatty alcohols substituted with at least one of the following substituents: formyl, methylol, or acryloxymethyl. The substituted fatty ethers are useful as monomers in a wide variety of polymer systems.Type: GrantFiled: February 28, 1985Date of Patent: March 3, 1987Assignee: Henkel CorporationInventors: Michael J. Virnig, James P. Clark, Kenneth D. MacKay