Carbamic Acid Patents (Class 560/157)
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Patent number: 4914227Abstract: A process for preparing a 2-carbamoyloxyalkyl-1,4-dihydropyridine derivative represented by the general formula: ##STR1## which comprises: (a) reacting a 3-amino-3-carbamoyloxyalkylacrylic acid derivative represented by the general formula: ##STR2## with a benzylidene compound represented by the general formula: ##STR3## (b) reacting the 3-amino-3-carbamoyloxyalkylacrylic acid derivative of the general formula II with an aldehyde compound represented by the general formula: ##STR4## and a .beta.-keto-ester compound represented by the general formula:R.sup.4 --CO--CH.sub.2 --COOR.sup.2 (V)(c) reacting a 3-carbamoyloxyalkylpropiolic acid derivative represented by the general formula: ##STR5## with the benzylidene compound of the general formula III and ammonia or its salt; or(d) reacting the 3-carbamoyloxyalkylpropiolic acid derivative of the general formula VI with the aldehyde compound of the general formula IV, the .beta.-keto-ester compound of the general formula V and ammonia or its salt.Type: GrantFiled: May 16, 1986Date of Patent: April 3, 1990Assignee: Banyu Pharmaceutical Company, Ltd.Inventors: Tetsuji Miyano, Kunio Suzuki, Ryosuke Ushijima, Susumu Nakagawa
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Patent number: 4877540Abstract: Methylolated and optionally etherified urethanes containing fluoroalkyl ligans with formaldehyde, with or witout subsequent etherification, and are in the form of their solutions or aqueous dispersions suitable for the treatment of textiles and leather.Type: GrantFiled: August 8, 1988Date of Patent: October 31, 1989Assignee: Cassella AktiengesellschaftInventors: Fritz Engelhardt, Karl Hintermeier, Manfred Muller, Norbert Munch, Hans Wagener
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Patent number: 4827020Abstract: 1-propargyl-2,4-dioxoimidazolidine is a very useful intermediate for synthesizing insecticidal and acaricidal compounds of pyrethroid type. Here are disclosed a method for producing 1-propargyl-2,4-dioxoimidazolidine, the starting material compounds thereof and a method for producing said starting material compounds. According to the present invention, said useful intermediate can be easily produced than before.Type: GrantFiled: March 4, 1988Date of Patent: May 2, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Hideo Kohsaka, Yoshihiko Oue
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Patent number: 4824670Abstract: The present invention relates to new carbazates of the general formula (I), ##STR1## wherein A is C.sub.3-10 alkyl, C.sub.3-10 alkenyl, C.sub.2-10 haloalkyl, trifluoromethyl, phenyl-C.sub.1-3 alkyl, phenyl-C.sub.2-3 -alkenyl, naphthyl-C.sub.1-3 alkyl; phenyl optionally substituted by one or more identical or different substituent(s) selected from C.sub.1-4 alkyl, halogen, C.sub.1-4 alkoxy and hydroxy; C.sub.3-7 cycloalkyl-C.sub.1-3 alkyl; optionally nitro-substituted furyl; diphenyl-hydroxy-methyl or indazolyl optionally substituted by one or more C.sub.1-4 alkoxy group(s) andR represents C.sub.1-4 alkyl,with the proviso that if R stands for ethyl, A is other than tertiary butyl, and acid addition salts thereof, a process for the preparation thereof and feed-additives comprising the same.The compounds of the general formula (I) may be used in animal husbandry due to their weight-gain increasing and fodder utilization improving effect.Type: GrantFiled: December 11, 1985Date of Patent: April 25, 1989Assignee: Egis GyogyszergyarInventors: Ildiko Ratz nee Simonek, Pal Benko, Edit Bernenyi nee Poldermann, Karoly Magyar
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Patent number: 4818426Abstract: A bleach precursor compound, its peroxygen acid derivative, and detergent compositions containing these materials are disclosed herein. The bleach precursor structurally comprises a quaternized ammonium or phosphonium group linked to a carbonate moiety having a leaving group. Upon perhydrolysis in the presence of hydrogen peroxide and a basic aqueous media, there is generated a peroxycarbonic acid bleach.Type: GrantFiled: March 30, 1988Date of Patent: April 4, 1989Assignee: Lever Brothers CompanyInventors: Robert W. R. Humphreys, Stephen A. Madison
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Patent number: 4816598Abstract: The invention relates to 4-amino-butanoic acid derivatives of general formula: ##STR1## in which: M represents an alkali metal atom,R represents a protected amino group,R.sub.1 represents a labile group,R.sub.2 represents hydrogen, a branched- or straight-chain alkyl radical having from 1 to 6 carbon atoms, a lower methyloxyalkyl, a lower methylthioalkyl, a lower (lower alkyl)-aminoalkyl, a lower di-(lower alkyl)-aminoalkyl or a lower hydroxyalkyl radical or R.sub.2 represents one of the radicals of general formulae:Cy--A--, Cy--O--A'--, R--A'-- or R.sub.Type: GrantFiled: June 16, 1987Date of Patent: March 28, 1989Assignee: SanofiInventors: Marcel Descamps, Walter Verstraeten
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Patent number: 4806674Abstract: A process for preparing urethanes by reacting a primary or secondary amine with carbon monoxide, an alcohol, a catalytic quantity of a compound or complex of palladium, platinum or rhodium and a stoichiometric quantity of a copper(II) salt of a monocarboxylic acid. When the amine is aromatic, the process is conducted in the presence of a selected Lewis base promoter and a compound or complex of palladium.Type: GrantFiled: January 27, 1986Date of Patent: February 21, 1989Assignee: E. I. Du Pont De Nemours and CompanyInventor: Francis J. Waller
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Patent number: 4793993Abstract: Keratinous material, such as human hair, in which disulfide linkages have been ruptured to form disulfide linkages can be set using diimidates, and disuccinimidyl compounds as disclosed herein.Type: GrantFiled: August 24, 1987Date of Patent: December 27, 1988Assignee: Chesebrough-Pond's Inc.Inventors: Patricia Siuta-Mangano, Herbert Edelstein
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Patent number: 4776875Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.Type: GrantFiled: March 26, 1986Date of Patent: October 11, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
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Patent number: 4751015Abstract: A bleach precursor compound, its peroxygen acid derivative, and detergent compositions containing these materials are disclosed herein. The bleach precursor structurally comprises a quaternized ammonium or phosphonium group linked to a carbonate moiety having a leaving group. Upon perhydrolysis in the presence of hydrogen peroxide and a basic aqueous media, there is generated a peroxycarbonic acid bleach.Type: GrantFiled: March 17, 1987Date of Patent: June 14, 1988Assignee: Lever Brothers CompanyInventors: Robert W. Humphreys, Stephen A. Madison
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Patent number: 4751273Abstract: Vinyl ether terminated urethane resins may be prepared by reacting the product obtained by the addition of acetylene to an organic polyol with an isocyanate-containing compound at temperatures ranging from about ambient to about 125.degree. C. The thus prepared resin may then be cured by irradiation from an electron beam, thermally or by exposure to an ultraviolet light to cure the resin and form a coating material.Type: GrantFiled: July 6, 1987Date of Patent: June 14, 1988Assignee: Allied-Signal, Inc.Inventors: Stephen C. Lapin, David W. House
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Patent number: 4749806Abstract: The present invention relates to a process for the synthesis of isocyanates and of isocyanate derivatives. Isocyanates are obtained by reacting an organic halide with a metal cyanate in an organic medium in the presence of a catalyst consisting of a complex of nickel with at least one organic ligand, in which complex the nickel is in the zero oxidation state.A carbamate or a urea, respectively, are obtained by a subsequent reaction with a hydroxy compound or a primary or secondary amine.Isocyanates and their derivatives are used especially either as refined synthesis agents for the production of pesticides and medications, or as monomers or comonomers for the preparation of many macromolecular compounds.Type: GrantFiled: August 25, 1987Date of Patent: June 7, 1988Assignee: Societe Nationale des Poudres et ExplosifsInventors: Igor Tkatchenko, Rabih Jaouhari, Michel Bonnet, Gordon Dawkins, Serge Lecolier
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Patent number: 4740610Abstract: The invention describes a process for the preparation of N,o-substituted mono- and/or polyurethanes of formulaR.sup.1 [--NHCOOR.sup.2 ].sub.n,in whichR.sup.1 is an aliphatic, cycloaliphatic, aromatic, araliphatic, or heterocyclic radical, which may be substituted,R.sup.2 is an aliphatic, cycloaliphatic, or araliphatic radical which may be substituted with alkoxy or polyoxyalkylene groups, andn is a whole number from 1 to 5,through the reaction of N-substituted allophanates and/or polyallophanates with alcohols R.sup.2 OH in the presence or absence of catalysts at temperatures of at least 160.degree. C., preferably from 165.degree. to 250.degree. C.Type: GrantFiled: August 21, 1986Date of Patent: April 26, 1988Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
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Patent number: 4740600Abstract: Surfactants which are blocked against surfactant action (identified herein as "photolabile blocked surfactants") by a photolabile protective or masking group but which, on exposure to actinic radiation, become unblocked are provided. Coating compositions in which surfactant is formed on irradiation are provided by blending the photolabile blocked surfactant with polymeric film-forming materials.Compositions containing the photolabile blocked surfactants are useful when employed as protective coatings on various substrates or as the adhesive in a pressure sensitive adhesive tape. Although initially well adhering to a substrate, such compositions may be readily removed from the substrate following exposure of the same to suitable radiation which unblocks the surfactant to permit it to regain its surfactant activity.Type: GrantFiled: January 6, 1986Date of Patent: April 26, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert L. Eian, John E. Trend
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Patent number: 4734521Abstract: .beta.,.gamma.-Unsaturated non-epoxide ethers react with carboxylic acids, carbamates or sulfonamides to form the corresponding .beta.,.gamma.-unsaturated esters, carbamates or sulfonamides. The reaction is catalyzed with sulfonated polystyrene beads and is promoted by copper (I) chloride.Type: GrantFiled: August 5, 1987Date of Patent: March 29, 1988Assignee: The Dow Chemical CompanyInventor: Kevin A. Frazier
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Patent number: 4725680Abstract: The invention relates to a process for preparing carbamic acid derivatives of formula: ##STR1## in which R.sup.1 or R.sup.2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R.sup.1 and R.sup.2 together form a ring, and Y denotes OR, SR, ##STR2## groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R.sup.3 and R.sup.4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R.sup.6 and R.sup.7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical.According to the process, a compound of formula ##STR3## is reacted with an .alpha.-halogenated derivative of formula ##STR4## at a temperature of -5.degree. to 150.degree. C.Type: GrantFiled: February 14, 1985Date of Patent: February 16, 1988Assignee: Societe Nationale des Poudres et ExplosifsInventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
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Patent number: 4713480Abstract: An amino-protected L-aspartic acid, such as t-butyloxycarbonyl-beta-benzyl-L-aspartic acid, is prepared by first forming the amino-protected compound in the presence of a tertiary amine base having a pK.sub.a value of about 9 to about 12, water, and a water-immiscible polar organic solvent so as to produce a non-aqueous solution containing a salt form of amino-blocked-beta-benzyl-L-aspartic acid. The thus produced non-aqueous solution is then isolated, or next acidified and treated further to ultimately recover therefrom the amino-protected L-aspartic acid in crystalline form.Type: GrantFiled: January 7, 1987Date of Patent: December 15, 1987Assignee: Ortho Pharmaceutical CorporationInventor: John M. Pascone
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Patent number: 4705885Abstract: Polymerizable carbamoyloxyalkyldicarboxylic acid esters, carrying hydroxyl groups, of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or allyl or hydroxyalkyl having in each case 1 to 30 carbon atoms in the alkyl radical, R.sup.2 represents alkyl or hydroxyalkyl having in each case 1 to 30 carbon atoms in the alkyl radical or the radical ##STR2## subject to the proviso that R.sup.1 is hydrogen and x is an integer from 2 to 20, R.sup.3 represents linear or branched alkylene having 2 to 5 carbon atoms, R.sup.4 represents hydrogen or methyl and R.sup.5 represents hydroxyalkyl or hydroxyaminoalkyl having in each case 2 to 20 carbon atoms in the alkyl radical or an alkyl radical of this type which also contains ester and/or ether groups, and a process for their preparation.The esters according to the invention can be used for the preparation of copolymers.Type: GrantFiled: February 6, 1986Date of Patent: November 10, 1987Assignee: Hoechst AGInventors: Christoph Just, Dieter Plath, Gerd Walz
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Patent number: 4695645Abstract: The invention describes a process for the preparation of N,o-substituted mono- and/or polyurethanes of formulaR.sup.1 [--NHCOOR.sup.2 ].sub.n,in whichR.sup.1 is an aliphatic, cycloaliphatic, aromatic, araliphatic, or heterocyclic radical, which may be substituted,R.sup.2 is an aliphatic, cycloaliphatic, or araliphatic radical which may be substituted with alkoxy or polyoxyalkylene groups, andis a whole number from 1 to 5,through the reaction of N-substituted allophanates and/or polyallophanates with alcohols R.sup.2 OH in the presence or absence of catalysts at temperatures of at least 160.degree. C., preferably from 165.degree. to 250.degree. C.Type: GrantFiled: July 20, 1984Date of Patent: September 22, 1987Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
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Patent number: 4694097Abstract: Carbamate esters are produced by reacting at ambient or elevated temperature an amine with carbon monoxide and an alcohol in the presence of a protonic acid, a dehydrating agent, for example a molecular sieve, and a catalyst comprising (a) at least one metal selected from the group palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the components (a) and (b) being in the form of elemental metals or compounds thereof. The presence of the dehydrating agent reduces the formation of by-product carbon dioxide.Type: GrantFiled: April 25, 1986Date of Patent: September 15, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith
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Patent number: 4687872Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.Type: GrantFiled: December 9, 1985Date of Patent: August 18, 1987Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm
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Patent number: 4684722Abstract: Antibacterial activity is exhibited by monocyclic .beta.-lactam antibiotics having in the 1-position an --O--SO.sub.3 H activating group and in the 3-position an acylamino group of the formula ##STR1## wherein R.sub.3 and R.sub.4 are each independently hydrogen or alkyl.Type: GrantFiled: January 6, 1986Date of Patent: August 4, 1987Assignee: E. R. Squibb & Sons, Inc.Inventor: Joseph E. Sundeen
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Patent number: 4668703Abstract: This invention is for .gamma.-allenyl-.gamma.-aminobutyric acid derivatives which are .gamma.-aminobutyric acid transaminase inhibitors.Type: GrantFiled: July 1, 1985Date of Patent: May 26, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Alexander Krantz, Arlindo L. Castelhano, Diana H. Pliura
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Patent number: 4663472Abstract: A process for the transesterification of urethanes comprises reacting a urethane with an alcohol at elevated temperature in the presence of a Lewis base containing catalyst.The process is particularly useful when the alcohol used is a polyol since the product of the transesterification is a polyurethane. Since urethanes can be generated from amines and organic carbonates using the methods of the prior art, the present invention provides processes for the manufacture of polyurethanes from amines which avoid the use of either phosgene or isocyanates both of which are extremely toxic.Type: GrantFiled: January 30, 1985Date of Patent: May 5, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4629804Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.Type: GrantFiled: March 4, 1985Date of Patent: December 16, 1986Assignee: Catalytica AssociatesInventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
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Patent number: 4622408Abstract: The novel reagent, vinyl phenylthiocarbonate, is prepared. It is useful for the introduction of the vinyloxycarbonyl protecting group which is a valuable protecting group for amines, amino acids, peptides, proteins and phenols.Type: GrantFiled: October 22, 1981Date of Patent: November 11, 1986Assignee: Merck & Co., Inc.Inventor: Angelina J. Duggan
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Patent number: 4621149Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.Type: GrantFiled: December 10, 1984Date of Patent: November 4, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shinsuke Fukuoka, Masazumi Chono
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Patent number: 4618710Abstract: An optically active alpha-amino acid derivative having the formula: ##STR1## wherein: X is OH, Cl, Br, I, or OCOR.sub.3 ;Y is a radical selected to stabilize the alpha carbon atom of the alpha-amino acid derivative sufficiently to prevent significant change in symmetry thereof during replacement of X with an alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, alkenaryl or alkynaryl radical, or such radical having one or more chemical constituents thereon; andR.sub.1 and R.sub.2 are different from one another and are each hydrogen or an alkyl, aryl, alkenyl, alkynyl, alkaryl, aralkyl, alkenaryl, or alkynaryl radical, or such radical having one or more non-protic chemical constituents thereon is conventionally synthesized from the corresponding alpha-amino acid. The ##STR2## portion of the above derivative is converted to a ketone functionality without racemization.Type: GrantFiled: September 13, 1982Date of Patent: October 21, 1986Assignee: The Regents of the University of Calif.Inventors: Henry Rapoport, Thomas F. Buckley, III
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Patent number: 4607082Abstract: Disclosed are novel catalyst systems and method for curing a peroxide-curable ethylenically unsaturated (e.g. acrylic or vinyl) composition wherein the catalyst system is a combination of the peroxide curing agent and a Cu.sup.+1 activator or a combination of a peroxide curing agent and an activator system comprising a furfuryl alcohol and an acid catalyst. Also disclosed is a new catalyst system for curing ring compounds (e.g. epoxides) which comprises a combination of ferrocene and a diazonium salt of a Lewis acid. Preferred curable compositions are adhesives and especially acrylic adhesives and epoxy adhesives. Also disclosed is a new adhesion promoter which improves the adhesion of acrylic adhesive.Type: GrantFiled: July 2, 1984Date of Patent: August 19, 1986Assignee: Three Bond Co., Ltd.Inventor: Vincent D. McGinniss
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Patent number: 4603216Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst comprising a bis phosphine ligand.Type: GrantFiled: September 16, 1983Date of Patent: July 29, 1986Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
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Patent number: 4600793Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a halide-free ruthenium catalyst is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a primary amine in the reaction solution.Type: GrantFiled: September 16, 1983Date of Patent: July 15, 1986Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm, Donald H. Valentine
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Patent number: 4595533Abstract: Esters of carbamic acids containing at least one hydrogen atom attached to the carbamic nitrogen atom are reacted with organic carbonates to produce esters of carbamic acids having a greater degree of organic substitution on the carbamic nitrogen atom than the reactant esters. Preferably, the reactant esters are alkylated using dialkyl carbonates.Type: GrantFiled: September 23, 1982Date of Patent: June 17, 1986Assignee: PPG Industries, Inc.Inventor: Ralph B. Thompson
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Patent number: 4594098Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, CF.sub.3, benzyl cyclohexyl, cyanoethyl, phenyl or OH and A denotes, inter alia, the groups --CO--, CHOH or CH--NH.sub.2 and --COR.sub.3 denotes a carboxyl, carboxylic ester or carboxamido group, are active herbicides.Type: GrantFiled: July 16, 1985Date of Patent: June 10, 1986Assignee: Hoechst AktiengesellschaftInventors: Klaus Bauer, Hermann Bieringer, Helmut Burstell, Jean Kocur
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Patent number: 4594441Abstract: A process for the preparation of urethanes. Urethanes having the general formula R.sub.1 (NHCOOR.sub.2).sub.n are reacted with an alcohol at a temperature of 120.degree. to 400.degree. C. in amounts such that, for every mol of the urethane, at least one mol of the alcohol is present. R.sub.1 is a radical obtained by removing the isocyanate groups from an n-functional organic isocyanate, which isocyanate has a boiling point greater than 100.degree. C. at atmospheric pressure. R.sub.2 is a radical obtained by removing the hydroxyl group from a monohydric alcohol which has a boiling point greater than 140.degree. C. at atmospheric pressure.Type: GrantFiled: May 14, 1984Date of Patent: June 10, 1986Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
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Patent number: 4593116Abstract: Urethanes are made by reacting an organic nitro compound with an organic compound containing at least one hydroxyl group in the presence of carbon monoxide, hydrogen and a catalyst system. The carbon monoxide and hydrogen are used in quantities such that the molar ratio of CO to H.sub.2 is from 0.3:1 to 3:1. The catalyst system is made up of at least one noble metal or compound of a noble metal from Group VIIIB of the Periodic System of Elements, at least one organic nitrogen base and a co-catalyst combination of iron or copper oxidic or hydroxidic compound and a chloride compound. The product urethanes are useful in the production of isocyanates and pesticides.Type: GrantFiled: June 13, 1984Date of Patent: June 3, 1986Assignee: Bayer AktiengesellschaftInventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
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Patent number: 4588825Abstract: This application relates to a stereospecific process for preparing specific enantiomers of 4-amino-4,5-dihydro-2-furancarboxylic acid and C.sub.1-6 lower alkyl esters thereof. These compounds are .gamma.-aminobutyric acid transaminase inhibitors useful in the treatment of epilepsy.Type: GrantFiled: March 13, 1985Date of Patent: May 13, 1986Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Joseph P. Burkhart, Gene W. Holbert
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Patent number: 4582923Abstract: Urethanes are made by reacting a primary amine with carbon monoxide and a compound containing at least one hydroxyl group in the presence of an oxidizing agent and a catalyst system. The catalyst system is made up of (i) a noble metal and/or a noble metal compound of a metal of the Eighth Secondary Group of the Periodic System of Elements and (ii) an oxidizing quinoid and/or a compound capable of being converted to an oxidizing quinoid compound under the reaction conditions. The catalyst system may optionally include (iii) metal compounds of elements of the Third to Fifth Main Groups and/or First to Eighth Secondary Groups of the Periodic System of Elements and/or (iv) a tertiary amine. This reaction is generally carried out at a temperature of from 100.degree. to 300.degree. C. and at a pressure of from 5 to 500 bars. The product urethanes are useful in the production of isocyanates and pesticides.Type: GrantFiled: May 17, 1985Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Gunter Stammann, Robert Becker, Johann Grolig, Helmut Waldmann
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Patent number: 4578506Abstract: The title compounds, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 PY where Y=oxygen or sulfur, are prepared by reacting a tetrakis(N-carbalkoxylaminomethyl)phosphonium salt having the formula (RO.sub.2 CNHCH.sub.2).sub.4 P.sup.+ X.sup.- with ammonia or a primary or secondary amine, followed by an oxidizing or sulfurizing agent. The products, after methylolation with formaldehyde, are useful as finishing agents for imparting flame retardant properties to cotton fabrics.Type: GrantFiled: March 8, 1982Date of Patent: March 25, 1986Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Arlen W. Frank
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Patent number: 4574159Abstract: After pyrolysis of N-.alpha.-methoxyethyl-O-methylurethane, it is possible to obtain very pure O-methyl-N-vinylurethane by cooling the pyrolysate and separating off the crystalline product. After separating off the O-methyl-N-vinylurethane, it is possible to react the mother liquor with methanol in the presence of bases and then to pass the reaction product to another pyrolysis.Type: GrantFiled: May 25, 1984Date of Patent: March 4, 1986Assignee: Bayer AktiengesellschaftInventor: Jurgen-Rolf Hassdenteufel
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Patent number: 4559383Abstract: High solids, solvent-based resin composition comprises novel chain-extendable, crosslinkable urethane modified polyhydroxy oligomers, crosslinking agent and, preferably, catalyst(s). The composition cures at elevated temperature to provide a coating on a substrate, such as steel, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate. The novel oligomers can be the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises three or more hydroxy, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with approximately one molar equivalent of a monofunctional blocking agent.Type: GrantFiled: December 27, 1983Date of Patent: December 17, 1985Assignee: Ford Motor CompanyInventors: Joseph W. Holubka, Ray A. Dickie
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Patent number: 4554188Abstract: High solids, solvent-based resin composition comprises novel chain-extendable, crosslinkable urethane modified polyhydroxy oligomers, crosslinking agent and, preferably, catalyst(s). The composition cures at elevated temperature to provide a coating on a substrate, such as steel, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate. The novel oligomers can be the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises three or more hydroxy, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with approximately one molar equivalent of a monofunctional blocking agent.Type: GrantFiled: January 5, 1983Date of Patent: November 19, 1985Assignee: Ford Motor CompanyInventors: Joseph W. Holubka, Ray A. Dickie
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Patent number: 4536314Abstract: Detergent compositions, detergent additive products and bleaching compositions containing aliphatic peroxyacid bleach precursors of formula ##STR1## are provided, where L is a leaving group of defined formula whose conjugate acid has a pKa of from 6 to 13 and ##STR2## is a non linear acyl group, the carboxylic acid derivative of which has a logP.sub.OCT in the range from 1.9 to 4.0 (where P.sub.OCT is the partition coefficient between octanol and water). New precursor compounds are provided in which ##STR3## is a C.sub.7 -C.sub.17 branched aliphatic acyl group containing a linear chain of at least 5 carbon atoms extending from and including the carbonyl carbon wherein the branching is on at least the 2- and/or 3- carbon atom.Type: GrantFiled: February 22, 1984Date of Patent: August 20, 1985Assignee: The Procter & Gamble CompanyInventors: Frederick E. Hardy, David J. Kitko, Cushman M. Cambre
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Patent number: 4532347Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.Type: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4532317Abstract: Aromatic polyamines containing aromatic primary amino groups as well as urethane and polyester groups are made by hydrolyzing an isocyanate in the presence of a basic material and water to form a carbamate and then converting the carbamate groups to amino groups. The isocyanate starting material contains aromatic isocyanate groups (as well as urethane and polyester groups) and has an NCO content of from 0.5 to 11.5 wt %. The basic compound is selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal silicates, alkali metal sulfides, alkali metal cyanides, tetraalkylammonium hydroxides and mixtures thereof. Water is used in a quantity such that at least one mole of water is present for each equivalent of NCO groups. The carbamate groups may be converted to amino groups by treating the carbamate-containing mixture with a proton donor or with heat or with a solvent. The product polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: June 21, 1983Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4532266Abstract: Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.Type: GrantFiled: March 19, 1982Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
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Patent number: 4522763Abstract: Novel N-alkoxycarbonyl- and N-alkoxythiocarbonyl-amidines and a process for the preparation of alkoxycarbonyl- and alkoxythiocarbonyl- amidines by reacting an amidine with an ester of chlorocarbonic acid or chlorothiocarbonic acid in the presence of an inorganic acid acceptor and a 2-phase aqueous/organic solvent mixture at from 0.degree. to 60.degree.0 C.The novel end products which can be prepared by this process are useful starting materials for crop protection agents, and can be used in particular for the preparation of novel, selective herbicides.Type: GrantFiled: July 14, 1982Date of Patent: June 11, 1985Assignee: BASF AktiengesellschaftInventor: Gerhard Hamprecht
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Patent number: 4520029Abstract: Some new compounds, farnesyl farnesyl carboxylate, N-farnesyl farnesyl carboxamide and N-farnesyl farnesyl carbamate are disclosed, which are novel mucosal stabilizing agents showing anti-inflammative and anti-ulcerative activities. These new compounds are prepared by the reaction of farnesyl carboxylic acid with farnesol or farnesylamine.Type: GrantFiled: June 27, 1983Date of Patent: May 28, 1985Assignee: Kotobuki Seiyaku Co., Ltd.Inventor: Tsuyoshi Tomiyama
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Patent number: 4507464Abstract: Polyisocyanates are produced by phosgenating a primary polyamine in the presence of at least one compound containing at least one primary and/or secondary alcoholic hydroxyl group in accordance with techniques known in the art. The reactants are used in quantities such that the equivalent ratio of primary amino groups to alcoholic hydroxyl group of from 1:0.005 to 1:0.99 is maintained during the phosgenation reaction. Where phosgenation is carried out in a two-stage process, the compound containing alcoholic hydroxyl groups must at least be present in the required quantity during the second stage. The primary polyamine may optionally be converted into a phosgenatable salt or a carbon dioxide adduct prior to being phosgenated to form the polyisocyanate. The polyisocyanates thus-produced may then be used in the production of polyurethanes or polyamines.Type: GrantFiled: February 10, 1984Date of Patent: March 26, 1985Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4504628Abstract: An addition polymerizable UV stabilizer is prepared by reacting an isocyanatoalkyl ester of an addition polymerizable carboxylic acid (such as 2-isocyanatoethyl methacrylate) with an UV stabilization functionality bearing an active hydrogen moiety which is reactive with the isocyanate (such as 2-hydroxy-4-(2-hydroxyethoxy)benzophenone).Type: GrantFiled: April 14, 1983Date of Patent: March 12, 1985Assignee: The Dow Chemical CompanyInventor: Mark R. Johnson
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Patent number: 4501915Abstract: An improved process for the preparation of N-alkyl-monosubstituted carbamates by reacting an aliphatic primary amine, urea and a monohydric aliphatic alcohol in the presence of a strongly basic tertiary amine catalyst and optionally an inert solvent.Type: GrantFiled: July 30, 1980Date of Patent: February 26, 1985Assignee: Atlantic Richfield CompanyInventor: John J. McCoy