Carbamic Acid Patents (Class 560/24)
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4258200Abstract: Carboxylic acid amides are produced by the catalytic reaction of an ester and an amine is shown. Organo cobalt salts are used as the catalyst. The process is particularly useful for producing dimethylacetamide by the reaction of methyl acetate and dimethylamine.Type: GrantFiled: March 11, 1980Date of Patent: March 24, 1981Assignee: Air Products and Chemicals, Inc.Inventor: Randall J. Daughenbaugh
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Patent number: 4251667Abstract: A process for the preparation of aromatic urethanes by reacting an aromatic amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: February 17, 1981Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4242520Abstract: A process for the production of carbamates is provided which comprises contacting an organic primary or secondary amine with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of a catalyst for the reaction and in the presence of at least one member selected from the group consisting of disulfides of the formulaR.sup.1 --S--S--R.sup.2wherein R.sup.1 and R.sup.2 comprise members selected from the group consisting of alkyl, aryl, cycloalkyl, alkaryl, aralkyl, heterocyclic, alkenyl, alkynyl, alkanoyl, aranoyl, halogenated derivatives of the foregoing groups, and derivatives of the foregoing groups in which one or more carbon atoms is replaced by an oxygen atom.Type: GrantFiled: January 29, 1979Date of Patent: December 30, 1980Assignee: Halcon Research & Development CorporationInventor: David Moy
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Patent number: 4236017Abstract: Semicarbazones and carbalkoxy hydrazones substituted in 2 position are synthesized by alkylation of the corresponding semicarbazones and carbalkoxy hydrazones, using alkyl halides or alkyl sulphates as alkylating agents.Type: GrantFiled: July 27, 1979Date of Patent: November 25, 1980Assignee: Montedison S.p.A.,Inventors: Pier M. Boschi, Franco Gozzo
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Patent number: 4236016Abstract: The instant invention relates to an improved process for the preparation of urethanes by the reaction of aromatic nitro compounds with alcohols and carbon monoxide in the presence of catalyst systems which contain selenium.Type: GrantFiled: February 21, 1979Date of Patent: November 25, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Armin Zenner
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Patent number: 4230876Abstract: The instant invention relates to an improved process for the preparation of urethanes by the reaction of aromatic nitro compounds with alcohols and carbon monoxide in the presence of catalyst systems which contain selenium.Type: GrantFiled: February 21, 1979Date of Patent: October 28, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Armin Zenner
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4230877Abstract: A method for increasing the 4,4' disubstituted isomer of the diphenylmethane dicarbamates produced by the acid catalyzed condensation of an N-aryl carbamic acid ester, such as ethylphenylcarbamate, with a carbonyl compound, such as formaldehyde, which comprises carrying out the condensation in a single phase system with a dilute solution of the N-aryl carbamic acid ester in an inert solvent having a dielectric constant of at least 20 at 20.degree. C. The solvent must have good solubility for the carbamates, which carbamates are employed in the solvent at concentrations of from about 0.1 to 50 weight percent to provide a product enriched with the 4,4'-diphenylmethane dicarbamate isomer.Type: GrantFiled: March 22, 1979Date of Patent: October 28, 1980Assignee: Atlantic Richfield CompanyInventors: Edward T. Shawl, Gerald A. Bullano
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Patent number: 4227008Abstract: Aromatic urethanes can be produced by interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system composed of a platinum group metal and/or a compound thereof serving as catalyst and a Lewis acid and/or a compound thereof as promoter under high temperature and high pressure conditions. For instance, the interaction of 2-amino-4-nitrotoluene, ethanol and carbon monoxide in the presence of palladium chloride and a ferrous chloride-pyridine complex under high temperature and high pressure conditions can yield 2,4-diethylcarbamatetoluene.Type: GrantFiled: July 25, 1978Date of Patent: October 7, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Katsuharu Miyata, Makoto Aiga, Seiji Hasegawa
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Patent number: 4224224Abstract: A method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and substituted aryl derivatives thereof is disclosed. The compounds are prepared by treating a 1-(carbocyclic aryl)-2-(2',3'-bis-carboalkoxyguanidino) ethane of the formula ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, R' is phenyl optionally substituted with the radial methylenedioxy or at least one hydroxy, halo, trifluoromethyl, C.sub.1 to C.sub.6 linear or branched alkoxy, or 1-naphthyl or 2-naphthyl and X is halo, mesyloxy or tosyloxy with a protic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide. 1-(Optionally substituted carbocyclic aryl)-2-(carboalkoxyguanidino) ethanes are also disclosed herein, such prepared by treating the above bis-carboalkoxyguanadino ethane with an aprotic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide.Type: GrantFiled: June 21, 1979Date of Patent: September 23, 1980Assignee: Syntex (U.S.A.) Inc.Inventors: Charles A. Dvorak, Colin C. Beard
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Patent number: 4222958Abstract: Diphenylamine of the formula ##STR1## wherein R.sub.1 and R.sub.4 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, amino, lower alkyl amino, acylamino, lower carbamylalkyl amino, lower hydroxyalkyl amino, lower carbalkoxy amino and ureido;R.sub.2 and R.sub.3 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, acylamino and ureido;R.sub.5 represents a member selected from the group consisting of hydrogen, halogen, lower alkyl and lower alkoxy;R.sub.6 represents a member selected from the group consisting of lower hydroxyalkyl, lower amino alkyl, lower acylamino alkyl, lower mesylamino alkyl, lower carbamylalkyl, lower sulfoalkyl, lower piperidinoalkyl, lower morpholinoalkyl, lower mono alkyl lower amino alkyl and lower dialkyl lower amino alkyl; andR.sub.Type: GrantFiled: May 17, 1977Date of Patent: September 16, 1980Assignee: L'OrealInventors: Gregoire Kalopissis, Andree Bugaut, Francoise Estradier
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Patent number: 4220747Abstract: Liquid phase processable crystalline diacetylene polymers are obtained by the solid state reaction of monomers having the formulaR.sub.1 --C.tbd.C--C.tbd.C--R.sub.2where R.sub.1 and R.sub.2 are independently selected from the group consisting of(a) CH.sub.3 (CH.sub.2).sub.m --(b) HO(CH.sub.2).sub.n -- and(c) R.sub.3 NHOCO(CH.sub.2).sub.p --where "m" is an integer of from 0 to 15, "n" is an integer of from 1 to 15, "p" is an integer of from 1 to 15, and R.sub.3 is a member selected from the group consisting of(i) C.sub.6 H.sub.5 (CH.sub.2).sub.r --(ii) CH.sub.3 (CH.sub.2).sub.r -- and(iii) C.sub.10 H.sub.7 (CH.sub.2).sub.r --where "r" is an integer of from 0 to 11; with the proviso that where R.sub.1 and R.sub.2 are the same and are either (b) or (c), neither "n" nor "p" equals 1; and with the further proviso that where R.sub.1 and R.sub.2 are different and are either (b) or (c), the sum of "n" plus "p" is greater than 2.Type: GrantFiled: June 28, 1976Date of Patent: September 2, 1980Assignee: Allied Chemical CorporationInventors: Anthony F. Preziosi, Kwok C. Yee, Ray H. Baughman
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Patent number: 4219661Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.Type: GrantFiled: April 23, 1979Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
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Patent number: 4210750Abstract: Alcohols are reacted with certain isocyanate compounds to produce the N-substituted carbamoyloxy derivatives which are cleaved to obtain the carbamate.Type: GrantFiled: November 17, 1976Date of Patent: July 1, 1980Assignee: Merck & Co., Inc.Inventors: Stephen Marburg, Janos Kollonitsch
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Patent number: 4196302Abstract: Novel quaternary phosphonium salts, bearing one or more carbamate groups attached through nitrogen, are prepared by condensing a hydroxymethyl phosphonium salt having the formula [R.sub.4-n P(CH.sub.2 OH).sub.n ].sup.+ X.sup.- with an alkyl carbamate having the formula NH.sub.2 CO.sub.2 R'. The products, which have the general formula [R.sub.4-n P(CH.sub.2 NHCO.sub.2 R').sub.n ].sup.+ X.sup.-, are useful as finishing agents for imparting flame retardant or durable press properties to cotton fabrics.Type: GrantFiled: March 6, 1979Date of Patent: April 1, 1980Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Arlen W. Frank
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Patent number: 4190582Abstract: Ethylenically unsaturated blocked aromatic diisocyanates are prepared which readily polymerize to form homopolymers and interpolymers with copolymerizable vinylidene monomers. Polymers can be prepared via emulsion polymerization, and exhibit excellent stability to hydrolysis when stored in latex form. The polymers cure at temperatures as low as 80.degree. C., and under acidic, neutral, or basic pH conditions. Homopolymers and interpolymers of the defined diisocyanates are useful as adhesives, and interpolymers of the ethylenically unsaturated blocked aromatic diisocyanates with acrylate monomers are particularly useful as binders for nonwoven fibers.Type: GrantFiled: June 19, 1978Date of Patent: February 26, 1980Assignee: The B. F. Goodrich CompanyInventor: Harold A. Tucker
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Patent number: 4189601Abstract: Ethylenically unsaturated blocked aromatic diisocyanates are prepared which readily polymerize to form homopolymers and interpolymers with copolymerizable vinylidene monomers. Polymers can be prepared via emulsion polymerization, and exhibit excellent stability to hydrolysis when stored in latex form. The polymers cure at temperatures as low as 80.degree. C., and under acidic, neutral, or basic pH conditions. Homopolymers and interpolymers of the defined diisocyanates are useful as adhesives, and interpolymers of the ethylenically unsaturated blocked aromatic diisocyanates with acrylate monomers are particularly useful as binders for nonwoven fibers.Type: GrantFiled: June 19, 1978Date of Patent: February 19, 1980Assignee: The B. F. Goodrich CompanyInventor: Harold A. Tucker
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Patent number: 4186269Abstract: An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration.Type: GrantFiled: December 31, 1975Date of Patent: January 29, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyate, Makoto Aiga
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Patent number: 4178455Abstract: In a process for preparing an aromatic urethane which comprises reacting an aromatic nitro compound, an organic compound containing at least one hydroxyl group, and carbon monoxide at elevated temperature and pressure in the presence of a catalytic system composed of a catalyst consisting of a platinum metal, a platinum metal compound, and/or a platinum metal compound-containing compound and a promoter consisting of a Lewis acid and/or a Lewis acid-containing compound, an organic primary amino compound, a urea compound, a biuret compound, an allophanate compound, or a mixture thereof is added to the reaction system whereby the reaction rate is increased and the yield of the desired product is enhanced. For example, 2,4-diethylcarbamatetoluene can be prepared in quantitatively high yield by reacting 2,4-dinitrotoluene, ethanol, carbon monoxide, and a small amount of aminonitrotoluene at elevated temperature and pressure in the presence of palladium chloride and ferrous chloride-pyridine complex.Type: GrantFiled: July 17, 1978Date of Patent: December 11, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyata, Makoto Aiga, Seiji Hasegawa
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Patent number: 4173563Abstract: The amidation and esterification of carboxylic acids with amines and hydroxyl group-containing compounds, respectively, are effected without incurring the drawbacks of reaction equilibrium by the reaction of the reactants, one of which has been activated in the reactive group by contact with a phosphonium salt obtained by reacting a phosphorous ester or phosphorous monoester salt with an organic base such as pyridine and an oxidizing agent such as halogens and mono or divalent mercury halide or acetate. The amidation can be applied to the preparation of peptides by the reaction of amino acids and/or peptides in which one of the reactive groups have been protected.Type: GrantFiled: June 12, 1978Date of Patent: November 6, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Noboru Yamazaki, Fukuji Higashi
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Patent number: 4172204Abstract: A method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and substituted aryl derivatives thereof is disclosed. The compounds are prepared by treating a 1-(carbocyclic aryl)-2-(2',3'-bis-carboalkoxyguanidino) ethane of the formula ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, R' is phenyl optionally substituted with the radical methylenedioxy or at least one hydroxy, halo, trifluoromethyl, C.sub.1 to C.sub.6 linear or branched alkoxy, or 1-naphthyl or 2-naphthyl and X is halo, mesyloxy or tosyloxy with a protic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide. 1-(Optionally substituted carbocyclic aryl)-2-(carboalkoxyguanidino) ethanes are also disclosed herein, such prepared by treating the above bis-carboalkoxyguanadino ethane with an aprotic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide.Type: GrantFiled: October 7, 1977Date of Patent: October 23, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Charles A. Dvorak, Colin C. Beard
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Patent number: 4171448Abstract: Novel quaternary phosphonium salts, bearing one or more carbamate groups attached through nitrogen, are prepared by condensing a hydroxymethyl phosphonium salt having the formula [R.sub.4-n P(CH.sub.2 OH).sub.n ].sup.+ X.sup.- with an alkyl carbamate having the formula NH.sub.2 CO.sub.2 R'. The products, which have the general formula [R.sub.4-n P(CH.sub.2 NHCO.sub.2 R').sub.n ].sup.+ X.sup.-, are useful as finishing agents for imparting flame retardant or durable press properties to cotton fabrics.Type: GrantFiled: November 29, 1978Date of Patent: October 16, 1979Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Arlen W. Frank
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Patent number: 4170708Abstract: Aromatic urethanes are produced by interacting an aromatic nitro compound, an organic compound containing hydroxyl groups and carbon monoxide in the presence of a catalyst composed of elemental selenium or a selenium compound and of a promoter composed of a bicyclic amidine together with a phenolic compound or a carboxylic acid. The interaction proceeds smoothly with the aid of a small amount of the promoter, attended with secondary production of amino compounds only in small amounts. For instance, 2,4-diethyldicarbamatetoluene is obtained at a yield of 87% by interacting 2,4-dinitrotoluene, ethanol and carbon monoxide in the presence of a catalytic system composed of metallic selenium, 1,8-diazabicyclo(5,4,0)-undecene-7 and acetic acid.Type: GrantFiled: March 8, 1976Date of Patent: October 9, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyata, Seiji Hasegawa
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Patent number: 4167489Abstract: Liquid crystalline compounds of the formula: ##STR1## wherein X is an electron-repelling radical and Z is an electron-attracting radical, and rings A, B and C are each unsubstituted or additionally substituted with 1 to 4 identical or different monovalent organic radicals.Type: GrantFiled: March 2, 1978Date of Patent: September 11, 1979Assignee: BBC Brown Boveri & Company, LimitedInventor: Maged A. Osman
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Patent number: 4164414Abstract: N-methylcarbanilic-[3-(ethoxycarbonylamino)-phenyl]-ester. The compound is a specific cotton herbicide. It is highly active against common weeds without causing harm to the cotton plants at any state of their development.Type: GrantFiled: February 22, 1977Date of Patent: August 14, 1979Assignee: Schering AktiengesellschaftInventors: Friedrich Arndt, Gerhard Boroschewski
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Patent number: 4164583Abstract: The present invention provides benz[f]isoindolines, useful in the treatment of aggression, a process for their preparation and compositions containing these compounds.Type: GrantFiled: June 22, 1978Date of Patent: August 14, 1979Assignee: Sandoz Ltd.Inventors: Roland Achini, Wolfgang Oppolzer, Emil Pfenninger
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Patent number: 4163019Abstract: A process for the production of 4,4'-methylene diphenyl diisocyanate (4,4'-MDI) to the substantial exclusion of other position isomers and of higher oligomers comprises a coupling reaction in which formaldehyde is condensed with an N-phenyl alkylcarbamate under mild conditions to produce the dialkyl carbamate of 4,4'-methylene diphenyl diisocyanate, and a catalytic exchange reaction in which the latter is reacted with phenyl isocyanate to produce with extremely high selectivity 4,4'-methylene diphenyl diisocyanate as product and N-phenyl alkylcarbamate which is recycled to the coupling reaction. In the overall process, formaldehyde and phenyl isocyanate are selectively converted to 4,4'-MDI. By substituting a higher aldehyde or a ketone for formaldehyde, the process may also be employed to produce other 4,4'-alkylidene diphenyl diisocyanates.Type: GrantFiled: July 10, 1978Date of Patent: July 31, 1979Assignee: Shell Oil CompanyInventor: Frank D. Mango
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Patent number: 4160077Abstract: A process for the cross-linking or chain extension of hycrocarbon polymers which contain ethylenically unsaturated groups which comprises forming an intimate mixture of the polymer with a carbamate of the formula: ##STR1## WHEREIN R.sub.1 is an optionally substituted hydrocarbyl radical, m is an integer, and A is H or an optionally substituted hydrocarbyl radical of valency m, and subjecting the mixture to heat.Novel compounds of preferred use include those in which m=1 and at least one of R and A is alkyl or 7 or more carbon atoms, or in which m=2 and A is phenylene or alkylene or alkenylene of 2 to 4 carbon atoms.Type: GrantFiled: January 6, 1978Date of Patent: July 3, 1979Assignee: Imperial Chemical Industries LimitedInventors: John L. Brooks, Richard Budziarek, David J. Harper
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Patent number: 4152350Abstract: This invention relates to an improved process for the preparation of polyisocyanate mixtures containing biuret groups by the reaction of organic diisocyanates with compounds which react with isocyanate groups to form biuret groups, to the polyisocyanate mixtures obtained by this process and to the use thereof for the preparation of polyurethane resins by the isocyanate polyaddition process.Type: GrantFiled: November 14, 1977Date of Patent: May 1, 1979Assignee: Bayer AktiengesellschaftInventors: Edgar Mohring, Kuno Wagner, Hanns P. Muller
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Patent number: 4150146Abstract: The invention relates to the preparation of unsymmetrically 1,3-disubstituted nitroso ureas from the corresponding N-substituted alkyl-N-nitrosocarbamoyl azide which is reacted with an amine, a diamine, an aminoalcohol, an aminoacid or an aminoacid derivative. The N-nitrosocarbamoyl azide is obtained by reacting the corresponding alkylcarbamoyl azide with nitrogen tetroxide in the cold. The alkylcarbamoyl azide is obtained by reacting the corresponding isocyanate with an alkali metal azide.The invention further relates to novel nitroso ureas obtained thereby, to novel N-substituted alkyl-N-nitrosocarbamoyl azides, and to novel therapeutic compositions containing, as the active ingredient, the novel nitroso ureas.Type: GrantFiled: May 25, 1977Date of Patent: April 17, 1979Inventor: Gerhard Eisenbrand
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Patent number: 4150142Abstract: The invention pertains to certain oxadiazolinones of the formula: ##STR1## in which R represents an alkyl radical containing 1 to 4 carbon atoms and R.sub.1 represents an alkyl radical containing 2 to 4 carbon atoms, an alkoxy radical of which the alkyl part contains 1 to 4 carbon atoms, an alkylthio radical of which the alkyl part contains 1 to 4 carbon atoms, or trifluoromethyl, and to their preparation and the compositions in which they are present, which compounds and compositions have utility as nematocides, acaricides and insecticides.Type: GrantFiled: January 23, 1976Date of Patent: April 17, 1979Assignee: Philagro S.A.Inventor: Roger Boesch
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Patent number: 4147716Abstract: A method of preparing an N-substituted carbamate comprising reacting by heating in sulfolane at a temperature ranging from about 65.degree. C. to about 100.degree. C. (1) an alkali metal cyanate, (2) at least one sulfolane-soluble organic halide of the formula RX wherein X is halogen and R represents a radical selected from the group consisting of alkyl, alkenyl, aralkyl and aralkenyl, and (3) at least one sulfolane-soluble non-aromatic monohydric or polyhydric alcohol, and isolating the N-substituted carbamate thereby produced from the resulting reaction mass.Type: GrantFiled: June 5, 1978Date of Patent: April 3, 1979Assignee: BASF Wyandotte CorporationInventor: Rack H. Chung
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Patent number: 4139563Abstract: Novel acetylenic derivatives of amines of the following general structure: ##STR1## WHEREIN Z is .beta.-methylthioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, or ##STR2## WHEREIN N IS 2 OR 3 AND R.sub.1 is hydrogen or lower alkyl of from 1 to 4 carbon atoms with the proviso that when R.sub.1 is other than hydrogen, n is 2; and each of R.sub.a and R.sub.b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; with the provisos that when Z is .beta.-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R.sub.b is hydrogen, and when Z is ##STR4## EACH OF R.sub.a and R.sub.Type: GrantFiled: July 1, 1977Date of Patent: February 13, 1979Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung
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Patent number: 4138422Abstract: Biologically active compositions are prepared by reacting an active hydrogen containing precursor with an isocyanate compound in the presence of solid particulate matter.Type: GrantFiled: July 24, 1974Date of Patent: February 6, 1979Assignee: Union Carbide CorporationInventors: John K. Chan, Erich Tobler, Herbert E. Johnson
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Patent number: 4134880Abstract: An aromatic urethane of high quality and excellent heat stability can be produced in high yield by reacting an aromatic nitro compound, a hydroxyl group-containing organic compound and carbon monoxide in the presence of a catalytic system composed of (1) palladium, ruthenium, rhodium or a compound thereof, (2) a Lewis acid, and (3) ammonia. The use of such catalytic system can suppress undesirable side reactions to a satisfactory extent and ensures the reaction to proceed without causing any corrosion of a stainless steel reactor. If necessary, water may be added to the reaction system to increase the reaction velocity, by which the unit cost of the catalyst can be reduced.Type: GrantFiled: January 19, 1978Date of Patent: January 16, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Katsuharu Miyata, Yutaka Hirai, Hiroshi Yoshida
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Patent number: 4130645Abstract: The present invention relates to novel methods for the protection of agricultural crops against plant pathogenic fungi comprising applying to the foliage of said crops a fungicidally effective amount of a compound selected from certain substituted phenylnitramines and certain novel salts of 2,3,5,6-tetrachlorophenylnitramine.The present invention further relates to certain novel substituted phenylnitramine and certain novel salts of 2,3,5,6-tetrachlorophenylnitramine and methods of preparation thereof.Type: GrantFiled: February 21, 1978Date of Patent: December 19, 1978Assignee: American Cyanamid CompanyInventors: Barrington Cross, David H. Dawe
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Patent number: 4129700Abstract: A novel class of compounds having the formula ##STR1## where Z is a substituted carbonate or carbamate, D is an alkynyl or an alkyl, and the R's may be alkyl.Type: GrantFiled: July 17, 1975Date of Patent: December 12, 1978Assignee: Pennwalt CorporationInventors: Orville L. Mageli, William A. Swarts
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Patent number: 4120853Abstract: The amidation and esterification of carboxylic acids with amines and hydroxyl group-containing compounds, respectively, are effected without incurring the drawbacks of reaction equilibrium by the reaction of the reactants, one of which has been activated in the reactive group by contact with a phosphonium salt obtained by reacting a phosphorous ester or phosphorous monoester salt with an organic base such as pyridine and an oxidizing agent such as halogens and mono or divalent mercury halide or acetate. The amidation can be applied to the preparation of peptides by the reaction of amino acids and/or peptides in which one of the reactive groups have been protected.Type: GrantFiled: July 13, 1977Date of Patent: October 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Noboru Yamazaki, Fukuji Higashi
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Patent number: 4111920Abstract: The present invention relates to new polyether urethanes corresponding to the general formula ##STR1## and to a process for their production. The polyether urethanes are stable for prolonged periods at temperatures of up to approximately 300.degree. C in aliphatic polyamide melts, and polyamides containing urethanes of this kind, more especially filaments and fibers of such polyamides or woven fabrics, knitted fabrics, nonwovens or pile fabrics produced from these filaments or fibers, show excellent antistatic properties.Type: GrantFiled: April 27, 1976Date of Patent: September 5, 1978Assignee: Bayer AktiengesellschaftInventors: Hans Egon Kunzel, Francis Bentz
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Patent number: 4105853Abstract: Trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are prepared by contacting a conjugated azomethine with a strong base in an inert organic solvent at sub-zero temperature and thereafter acylating the resulting product. The trans-N-acyl-N-alkyl-1-amino-1,3-butadienes are useful as intermediates in the formation of substituted decahydro-quinolines, Pumiliotoxin C, and can also be used as the diene in Diels-Alder reactions or can be copolymerized with vinyl compounds.Type: GrantFiled: September 21, 1977Date of Patent: August 8, 1978Assignee: CHON CorporationInventor: Wolfgang Oppolzer
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Patent number: 4102797Abstract: Novel compounds of the general formula: ##STR1## wherein R and R.sub.2 are hydrocarbyl groups, R.sub.1 is a hydrocarbylene group and R.sub.3 is hydrogen or a hydrocarbyl group, which groups R, R.sub.1, R.sub.2 and R.sub.3 may be substituted by or contain one or more heteroatoms or heterogroups, have utility as antioxidants for organic materials such as lubricating oils.Type: GrantFiled: May 3, 1976Date of Patent: July 25, 1978Assignee: Shell Oil CompanyInventor: Hendrik Schadenberg
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Patent number: 4100351Abstract: In the preparation of aromatic urethans, a dialkyl carbonate is reacted with an N-acyl derivative of an amine: thus, for example, by reacting acetanilide with a lower dialkyl carbonate, such as DMC or DEC, in the presence of titanium tetraphenate (Lewis' acid), phenylmethyl urethan is obtained with a yield over 90%. No toxic reactants are used and the reaction has outstandingly high yields and conversion ratings. The urethane in question are useful as weed-killers and pesticides in agriculture.Type: GrantFiled: March 24, 1977Date of Patent: July 11, 1978Assignee: Anic, S.p.A.Inventors: Ugo Romano, Renato Tesei
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Patent number: 4097673Abstract: Certain novel carbamates and thiolcarbamates are broad spectrum herbicides, which can be applied to the locus of undesired vegetation either preemergence or postemergence. Typical representatives of this class of compounds are methyl N-(N-cyclohexylcarbamoyl-N',N'-dimethylamidino)-N-methylcarbamate and methyl N-?1-(3-cyclohexyl-1-methylureido)-1-dimethylaminomethylene!carbamate.Type: GrantFiled: October 13, 1976Date of Patent: June 27, 1978Assignee: E. I. Du Pont de Nemours and CompanyInventor: Julius Jakob Fuchs
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Patent number: 4092480Abstract: Cephalosporin compounds having a substituted phenylglycyl substituent at the 7-position and any of a variety of groups at the 3-position are prepared by acylation of a 7-aminocephalosporanic acid. The compounds have anti-bacterial activity.Type: GrantFiled: April 28, 1977Date of Patent: May 30, 1978Assignee: SmithKline CorporationInventor: John Gerald Gleason
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Patent number: 4091227Abstract: Cephalosporins with a .alpha.-amino-(ureidophenyl)acetamido substituent at position 7 are prepared by acylation of a 7-aminocephalosporin with a derivative of .alpha.-amino-p(or m)-ureidophenylacetic acid. These compounds are antibacterial agents.Type: GrantFiled: October 10, 1976Date of Patent: May 23, 1978Assignee: SmithKline CorporationInventors: John Russel Eugene Hoover, Jerry Arnold Weisbach
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Patent number: 4091006Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: October 1, 1975Date of Patent: May 23, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4089649Abstract: Hydrophilic additives are provided which may be introduced into fibrous articles to provide improved water absorbency and charge dissipation properties which resist abrasion and laundering. The fibrous articles are treated by contacting the articles with at least one hydrophilic additive, polyfunctional reactant and nitrogen catalyst under conditions sufficient to incorporate hydrophilic additive, polyfunctional reactant and nitrogen catalyst in the articles, followed by heating the fibrous articles to obtain the desired fiber characteristics.Type: GrantFiled: March 4, 1976Date of Patent: May 16, 1978Assignee: Allied Chemical CorporationInventors: Frank Mares, Theodore Largman
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Patent number: 4085144Abstract: N,N'-Bridged-bis[(O and/or N-substituted)-2-alkyl-2-hydroxyethylamines] of the formula ##STR1## are prepared by condensing an epoxide of the formula ##STR2## and a diamine of the formula R'NH--X--NHR'. The products and dicarbanilates, acid-addition salts, N,N'-dioxides and N,N'-diammonium quaternary salts derived therefrom have antibacterial activity in vitro and are useful as antibacterial agents.Type: GrantFiled: November 8, 1976Date of Patent: April 18, 1978Assignee: Sterling Drug Inc.Inventors: Guy D. Diana, Royal A. Cutler
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Patent number: T994004Abstract: Diphenylmethane dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are produced by the condensation of N-aryl carbamic acid esters, such as ethylphenylcarbamate, with formaldehyde, para-formaldehyde or trioxane in the presence of strongly acidic sulfonated aromatic ion exchange resins or perfluoroalkane sulfonic acid resins, at temperatures of from ambient to about 150.degree. C. and optionally in the presence of an inert solvent.Type: GrantFiled: August 23, 1979Date of Patent: May 6, 1980Inventor: Edward T. Shawl