Ortho Fused Patents (Class 560/28)
-
Patent number: 4339592Abstract: A urethane is produced by reacting an organic nitro compound with carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst and a co-catalyst. This reaction is conducted in the liquid phase at elevated temperature and pressure. The catalyst employed is an element and/or compound of an element from the group of noble metals of the 8th Secondary Group of the Periodic Table. The co-catalyst used is formed from (1) a component taken from the group consisting of iron oxychloride, a mixture of iron compounds containing iron oxychloride and oxide-chloride combinations and (2) metallic iron or an iron alloy in finely divided or high surface form. The oxides which may be used in the oxide-chloride combinations of co-catalyst component (1) are the oxides and/or oxide hydrates of tetravalent tin, trivalent chromium, hexavalent molybdenum, hexavalent tungsten, pentavalent vanadium, divalent iron and trivalent iron.Type: GrantFiled: February 26, 1981Date of Patent: July 13, 1982Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Christian Rasp, Gunter Stammann, Johann Grolig
-
Patent number: 4338455Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: February 11, 1981Date of Patent: July 6, 1982Assignee: Merck & Co., Inc.Inventor: Jacob A. Zupan
-
Patent number: 4337349Abstract: Dimethacrylates are provided having the following chemical structure: ##STR1## where n represents a number of 2 to 8;R.sub.1 and R.sub.2 are the same or different and are hydrogen or groups of the formula: ##STR2## where R.sub.3 is an aliphatic, aromatic or cycloaliphatic group having 1 to 14 carbon atoms. These compounds are useful in dental material which cures to form polymers having high mechanical strength, low water sorption, resistance to staining, good color stability when exposed to short-wave radiation (e.g., sunlight) and good chemical resistance to the oral environment. Also provided are a method for polymerizing these compounds in situ on teeth and a tooth comprising polymers of these compounds.Type: GrantFiled: June 2, 1980Date of Patent: June 29, 1982Assignee: Scientific Pharmaceuticals, Inc.Inventors: Jan A. Orlowski, David V. Butler, Patrick D. Kidd
-
Patent number: 4335246Abstract: Substituted arylamine dye intermediates and their preparation are disclosed.Type: GrantFiled: September 24, 1979Date of Patent: June 15, 1982Assignee: Aziende Colori Nazionali Affini ACNA S.p.A.Inventors: Francesco De Feo, Giovanni Burei, Roberto Cipolli
-
Patent number: 4332724Abstract: There is provided a process for the preparation of an amido or an ureido derivative of certain 4,5,6,7-tetrahydro-7-oxobenzo[b]thiophenes or certain 1,2,3,4-tetrahydro-4-oxonaphthalenes which can be employed as an animal growth regulant. The process comprises: oxidizing in the presence of a cobalt catalyst a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a substituent selected from the group consisting of alkanoyl C.sub.1 -C.sub.7, halogen-substituted alkanoyl C.sub.1 -C.sub.7, carboalkoxy C.sub.1 -C.sub.4, ##STR2## and ##STR3## R.sub.3 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ; R.sub.4 is selected from the group consisting of hydr ogen, alkyl C.sub.1 -C.sub.8, alkanoyl C.sub.2 -C.sub.4, halogen-substituted alkanoyl (C.sub.2 -C.sub.Type: GrantFiled: November 16, 1977Date of Patent: June 1, 1982Assignee: American Cyanamid Co.Inventors: Terence J. Bentley, William H. Gastrock, Goro Asato
-
Patent number: 4315861Abstract: A process is disclosed for preparing a carbamic acid phenyl ester of the formula (I) ##STR1## wherein R is alkyl having 1 to 8 carbon atoms, aryl, cycloalkyl having 5 or 6 carbon atoms, or aralkyl having 7 to 16 carbon atoms, wherein the aryl, cycloalkyl or aralkyl is unsubstituted or substituted by at least one alkyl group having 1 to 8 carbon atoms;R.sub.1 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cyanomethyl, 1,3-dioxolan-2-yl, or carboalkoxyamino wherein the alkoxy group contains 1 to 4 carbon atoms;R.sub.2 is hydrogen, halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms; orR.sub.1 and R.sub.2 form together a carbocyclic ring or a heterocyclic ring fused to the phenyl ring wherein the carbocyclic ring of the heterocyclic ring is unsubstituted or substituted by at least one alkyl having 1 to 8 carbon atoms, which comprises acylating a phenol of the formula (II) ##STR2## with a compound of the formula (IV) ##STR3## in the presence of a base.Type: GrantFiled: March 23, 1981Date of Patent: February 16, 1982Assignee: Chinoin Gyogyszer RTInventors: Gyorgy Lugosi, Antal Simay, Janos Bodnar, Istvan Turcsan, Istvan Jelinek, Eva Somfai, Laszlo Simandi
-
Patent number: 4306075Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
-
Patent number: 4304922Abstract: Production of urethanes by the oxycarbonylation reaction of N,N'-disubstituted ureas and organic compounds containing at least one hydroxyl group with carbon monoxide in the presence of molecular oxygen and/or organic nitro compounds and a catalyst system comprising (a) a noble metal and/or noble metal compound of the eighth subgroup of the periodic system of elements and (b) a compound of an element and/or elements of the third to fifth main group and/or first to eighth subgroup of the periodic system of elements characterized in that said compounds are capable of undergoing Redox reactions under the reaction conditions.Type: GrantFiled: February 27, 1980Date of Patent: December 8, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gunter Stammann
-
Patent number: 4297501Abstract: A process for producing urethanes by reacting primary amines, carbon monoxide and organic hydroxyl compounds in the presence of molecular oxygen and/or organic nitro compounds as oxidizing agents and a catalyst system comprising a noble metal and/or a compound of a noble metal of the 8th subgroup of the Periodic System of Elements and a compound capable of undergoing Redox reactions under reaction conditions of the 3rd to 5th main group and/or 1st to 8th subgroup of the Periodic System of Elements.Type: GrantFiled: February 27, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
-
Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
-
Patent number: 4284572Abstract: Copolymerizable blocked isocyanate diols are prepared by reacting a blocking agent with an isocyanate group of an organic diisocyanate under controlled conditions, thereby forming a blocked isocyanate group, and reacting the second isocyanate group in a subsequent step with the amine portion of a selected amine diol under anhydrous conditions. The resultant products are used to prepare self-crosslinkable, linear polyurethanes of high molecular weight.Type: GrantFiled: December 15, 1978Date of Patent: August 18, 1981Assignee: National Starch and Chemical CorporationInventors: Henry Stanley, Dilip K. Ray-Chaudhuri
-
Patent number: 4282368Abstract: p-Substituted, aromatic carbamic acid esters are prepared by reacting an aromatic carbamic acid ester with an olefin in the presence of an inorganic acid or sulfonic acid.The aromatic carbamic acid esters obtainable by the process of the invention are active ingredients for pesticides and drugs, as well as valuable starting materials for the preparation of such ingredients and of dyes.Type: GrantFiled: June 2, 1980Date of Patent: August 4, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
-
Patent number: 4278805Abstract: A process for the preparation of an aryl-mono and/or polyurethane comprising the steps ofA. reacting a primary aromatic mono, di-, and/or polyamine with an O-alkyl carbamate in the presence of alcohol and catalysts, andB. separating the ammonia and other by-products from the aliphatic and/or cycloaliphatic di- and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.Type: GrantFiled: March 31, 1980Date of Patent: July 14, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
-
Patent number: 4275219Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: INTERx Research CorporationInventor: Jacob A. Zupan
-
Patent number: 4271188Abstract: Compounds having hypolipidaemic activity which are substituted aralkylanilines, their preparation and pharmaceutical compositions containing them.Type: GrantFiled: December 17, 1979Date of Patent: June 2, 1981Assignee: Beecham Group LimitedInventor: Richard M. Hindley
-
Patent number: 4268683Abstract: Carbamates are prepared from organic cabonates and aromatic amines in the presence of zinc or tin salts of monovalent organic compounds having a pKa value of at least 2.8 such as zinc naphthenate and which are soluble at the reaction conditions.Type: GrantFiled: February 21, 1980Date of Patent: May 19, 1981Assignee: The Dow Chemical CompanyInventor: Arthur E. Gurgiolo
-
Patent number: 4268684Abstract: Carbamates are prepared from organic carbonates and aromatic amines in the presence of zinc, tin or cobalt salts of monovalent organic compounds having a pKa value of less than 2.8 and compounds having more than one carboxyl group per molecule and oxides, sulfides and carbonates at a temperature of at least 200.degree. C.Type: GrantFiled: February 25, 1980Date of Patent: May 19, 1981Assignee: The Dow Chemical CompanyInventor: Arthur E. Gurgiolo
-
Patent number: 4267353Abstract: This invention relates to an improved process for the preparation of urethanes by the reaction of aromatic nitro compounds with alcohols and carbon monoxides in the presence of catalyst systems containing sulphur and/or selenium and/or compounds of these elements.Type: GrantFiled: August 22, 1979Date of Patent: May 12, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Armin Zenner
-
Patent number: 4262130Abstract: The present invention relates to an improved process for the production of urethanes (carbamic acid esters) by the reaction of organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of palladium and/or palladium compounds and a cocatalyst which consists of a mixture of one or more iron oxides and/or iron hydroxides and activating chloride-containing additives.Type: GrantFiled: January 17, 1980Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
-
Patent number: 4257804Abstract: Carbamic acid ester of the formula ##STR1## in which R and R.sub.1 are the same or different and are hydrogen, an aliphatic hydrocarbon residue which may also be substituted, a cycloaliphatic hydrocarbon residue which may also be substituted, an aromatic hydrocarbon residue which may also be substituted or a heterocyclic residue or wherein R and R.sub.1 together with the adjoining nitrogen atom form a heterocyclic residue.The compounds of the invention are herbicidal agents of particularly strong activity.Type: GrantFiled: April 10, 1979Date of Patent: March 24, 1981Assignee: Schering AktiengesellschaftInventors: Friedrich Arndt, Ludwig Nusslein
-
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
-
Patent number: 4254268Abstract: There is provided an oxidation process using potassium permanganate as oxidizing agent, for the preparation of certain animal growth promoters, namely, N-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)amides, 4,5,6,7-tetrahydro-7-oxobenzo[b]-thien-4-ylureas, N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)amides and 1,2,3,4-tetrahydro-4-oxo-1-naphthylureas, said process affording such compounds in markedly improved yields, and being readily suitable for scale-up.Type: GrantFiled: June 22, 1978Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: Henry L. Strong
-
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.
-
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
-
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
-
Patent number: 4235996Abstract: This disclosure describes 9,10-dihydroanthracene-9,10-dicarboxaldehyde-bis-hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers in mammals.Type: GrantFiled: September 19, 1978Date of Patent: November 25, 1980Assignee: American Cyanamid CompanyInventors: Ralph G. Child, Stanley A. Lang, Jr., Ving J. Lee, Yang-I Lin
-
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
-
Patent number: 4230635Abstract: Disclosed are novel substituted 4'-polyhaloisopropylsulfonanilides which are anti-hypertensive agents useful in the treatment of mammalian hypertension. Additionally, the compounds exhibit herbicidal and fungicidal activity. The compounds are prepared by contacting a 4-polyhaloisopropylaniline with the appropriate substituted-sulfonyl chloride.Type: GrantFiled: August 15, 1978Date of Patent: October 28, 1980Assignee: Schering CorporationInventor: Bernard R. Neustadt
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
Patent number: 4124545Abstract: Novel compounds which upon heating are converted into the corresponding phenol which is a catalyst for the trimerization of compounds having isocyanato groups to form isocyanurates have the formula: ##STR1## in which N REPRESENTS AN INTEGER OF FROM 1 TO 4A represents an aromatic hydrocarbon group obtained by removing the NCO group from a monomeric aromatic monoisocyanate containing 6 - 14 carbon atoms,R.sub.1 and R.sub.2 may be the same or different and represent a C.sub.1 to C.sub.6 alkyl group or a polymethylene chain containing 4 to 8 carbon atoms which together with the nitrogen atom form a heterocyclic ring,R.sub.3 may be hydrogen, chlorine, bromine or a C.sub.1 - C.sub.18 -alkyl group.Type: GrantFiled: June 22, 1977Date of Patent: November 7, 1978Assignee: Bayer AktiengesellschaftInventors: Jurgen Hocker, Hans-Joachim Diehr, Rudolf Merten
-
Patent number: 4113958Abstract: 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: October 22, 1976Date of Patent: September 12, 1978Assignee: The B. F. Goodrich CompanyInventor: Harold A. Tucker
-
Patent number: 4105792Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: May 25, 1976Date of Patent: August 8, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
-
Patent number: 4104043Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: December 12, 1972Date of Patent: August 1, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
-
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
-
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
-
Patent number: 4093447Abstract: New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted,R.sup.1, r.sup.2 and R.sup.3, which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen,R.sup.4 is alkyl, alkenyl, alkynyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R.sup.4' is hydrogen or is defined as R.sup.4 is defined above, andY and Y' are oxygen or sulfur.Are outstanding effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.Type: GrantFiled: November 17, 1975Date of Patent: June 6, 1978Assignee: Bayer AktiengesellschaftInventors: Carl Metzger, Gerhard Jager, Klaus Lurssen
-
Patent number: 4090862Abstract: Phenoxycarboxylic acid aryloxy(thio)carbonylaminomethyl ester compound of the formula ##STR1## wherein R.sup.1 is phenyl, substituted phenyl, benzyl, substituted benzyl, naphthyl or substituted naphthyl,R.sup.2 is hydrogen or alkyl of from 1 to 4 carbon atoms,R.sup.3 is phenyl or substituted phenyl,X is oxygen or sulfur, andn is 0, 1 or 2 exhibit outstanding plant growth regulant properties.Type: GrantFiled: December 22, 1976Date of Patent: May 23, 1978Assignee: Bayer AktiengesellschaftInventors: Rudolf Thomas, Klaus Lurssen
-
Patent number: 4080365Abstract: Aromatic urethanes can be produced in exceedingly improved yield when an aromatic nitro compound, an organic compound containing hydroxyl groups, and carbon monoxide are reacted in the presence of a catalyst composed of metallic (elemental) selenium or a selenium compound and a base serving as promoter, to which reaction system an aromatic amino compound and/or an aromatic urea compound which will be secondarily produced by the reaction has been previously added in order to suppress side reactions. For instance, when nitrobenzene, methanol and carbon monoxide are interacted in the presence of metallic selenium and triethylenediamine, the conversion of nitrobenzene is 68% and the percentage of formed methyl N-phenylcarbamate to the interacted nitrobenzene is 80%, whereas when the reaction is effected under the same reaction conditions indicated above with addition to the reaction system of aniline in an amount of about 15 wt.Type: GrantFiled: May 19, 1976Date of Patent: March 21, 1978Assignee: Mitsui Toatsu ChemicalsInventors: Yutaka Hirai, Katsuharu Miyata, Seiji Hasegawa
-
Patent number: 4076952Abstract: There are provided certain substituted-1,2,3,4-tetrahydro-4-imino-1-naphthylureas, methods of preparation thereof, and methods of use of said naphthylureas for enhancing feed efficiency and for promoting the growth rate of veterinary homothermic animals.Type: GrantFiled: March 25, 1977Date of Patent: February 28, 1978Assignee: American Cyanamid CompanyInventors: Goro Asato, Terence James Bentley
-
Patent number: RE30578Abstract: New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted,R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen,R.sup.4 is alkyl, alkenyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R.sup.4' is hydrogen or is defined as R.sup.4 is defined above, andY and Y' are oxygen or sulfur,are outstandingly effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.Type: GrantFiled: November 22, 1977Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Carl Metzger, Gerhard Jager, Klaus Lurssen