Carbamic Acid Patents (Class 560/24)
  • Patent number: 4610985
    Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
  • Patent number: 4606737
    Abstract: Fluorochemical allophanates containing one or more monovalent fluoroaliphatic radicals having at least three fully fluorinated terminal carbon atoms and one or more allophanate moieties, the radicals and moieties bonded together by hetero atom-containing or organic linking groups are provided. These fluorochemical allophanates are useful in the form of aqueous dispersions or emulsions or organic solutions in the treatment of fibrous substrates, such as textile fibers, to impart oil and water repellency.
    Type: Grant
    Filed: June 26, 1984
    Date of Patent: August 19, 1986
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Richard M. Stern
  • Patent number: 4603125
    Abstract: Compounds represented by the general formula (I): ##STR1## in which R.sub.1 represents ##STR2## A and B each represent H or a lower alkane optionally substituted with amino and/or hydroxyl functions, except that A and B are not both H; R.sub.3 represents H, OCH.sub.3, CH.sub.3, halogen, NH.sub.2, NO.sub.2, NHCH.sub.3, N.sub.3 (CH.sub.3).sub.2, N.sub.3, NHCOCH.sub.3, NHCOOCH.sub.3, N(CH.sub.3)COOCH.sub.3, CONH.sub.2 or CONHCH.sub.3 ; R.sub.4 represents H, alkyl, O-alkyl, CONH.sub.2, CONHCH.sub.3 or CONHCH.sub.2 CONHCH.sub.3, except that R.sub.3 and R.sub.4 taken together can represent --C.dbd.CH--CH.dbd.N--; R.sub.5 represents H, alkyl, O-alkyl, CONH.sub.2, CONHCH.sub.3 or CONH.sub.2 CH.sub.2 CONHCH.sub.3 ; R.sub.6 represents lower alkyl; R.sub.7 represents CH.sub.3 or C.sub.6 H.sub.5 (phenyl); R.sub.8 represents lower alkyl or C.sub.6 H.sub.5 (phenyl); R.sub.9 represents H, NHCOCH.sub.3, NH.sub.2 or N.dbd.CHN(CH.sub.3).sub.2 ; and R.sub.10 represents H or NH.sub.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: July 29, 1986
    Assignee: Development Finance Corporation of New Zealand
    Inventors: Graham J. Atwell, Bruce C. Baguley, William A. Denny, Gordon W. Rewcastle
  • Patent number: 4603216
    Abstract: 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: Grant
    Filed: September 16, 1983
    Date of Patent: July 29, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4600793
    Abstract: 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: Grant
    Filed: September 16, 1983
    Date of Patent: July 15, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine
  • Patent number: 4595533
    Abstract: 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: Grant
    Filed: September 23, 1982
    Date of Patent: June 17, 1986
    Assignee: PPG Industries, Inc.
    Inventor: Ralph B. Thompson
  • Patent number: 4594098
    Abstract: 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: Grant
    Filed: July 16, 1985
    Date of Patent: June 10, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Bauer, Hermann Bieringer, Helmut Burstell, Jean Kocur
  • Patent number: 4594441
    Abstract: 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: Grant
    Filed: May 14, 1984
    Date of Patent: June 10, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
  • Patent number: 4593116
    Abstract: 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: Grant
    Filed: June 13, 1984
    Date of Patent: June 3, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
  • Patent number: 4587056
    Abstract: A process for producing an aliphatic isocyanate from an aliphatic primary amine comprising a carbonylation step in which an aliphatic primary amine is allowed to react with carbon monoxide at a temperature of about 100.degree.-250.degree. C. in the presence of an aromatic hydroxyl compound having a pKa value of not more than about 11, molecular oxygen and a catalyst system comprising at least one member selected from palladium and rhodium metals and components thereof and at least one member selected from iodine and bromine and compounds thereof and a combined separation and recovery step comprising a pyrolysis-distillation reaction in which the mixture of carbonylated products is heated to a temperature of from about 100.degree. to 300.degree. C.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: May 6, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Tomonari Watanabe
  • Patent number: 4587261
    Abstract: The invention relates to new cycloalkane derivatives, a process for the preparation thereof and compositions--particularly feed additives and animal feeds--containing the same.The new compounds of the present invention correspond to the general formula I ##STR1## wherein n is 3, 4, 5 or 6;R denotes a phenyl group optionally carrying one or more substituent/s/ selected from the group consisting of halogen, lower alkoxy and lower alkyl;R.sup.1 and R.sup.2 each represent hydrogen or form together a valence bond;R.sup.3 represents lower alkoxy or a phenyl optionally substituted by one or more C.sub.1-12 alkoxy.The fodder additives and fodders according to the invention contain as active ingredient an amount of 1 ppm to 85% by weight of a compound of the general formula I in admixture with inert solid or liquid carriers or diluents and can be used to advantage in animal husbandry.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: May 6, 1986
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Pal Benko, Ildiko Ratz nee Simonek, Eva Rakoczy nee Pinter, Karoly Magyar, Jozsef Kelemen, Attila Mandi
  • Patent number: 4582855
    Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 15, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung T. Kam, William L. Matier
  • Patent number: 4582923
    Abstract: 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: Grant
    Filed: May 17, 1985
    Date of Patent: April 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Robert Becker, Johann Grolig, Helmut Waldmann
  • Patent number: 4570002
    Abstract: The invention relates to new carbazic acid derivatives, a process for the preparation thereof and compositions--particularly feed additives and animal feeds--containing the same.The new compounds according to the invention correspond to the formula (I)R.sup.1 .dbd.N--NH--COOR.sup.3 (I)whereinR.sup.1 stands for a C.sub.7-12 cycloalkylidene group, an indanylidene group or a group of the formula (IX) ##STR1## wherein A represents a phenyl group optionally carrying one or more identical or different substituents selected from the group consisting of halo nitro, hydroxy, C.sub.1-14 alkoxy, C.sub.1-4 alkyl, amino or C.sub.1-4 alkoxycarbonylhydrazino; phenyl-(C.sub.1-4 alkyl), C.sub.1-16 alkyl, C.sub.3-7 cycloalkyl or indolyl or a C.sub.3 -C.sub.6 cycloalkyl group substituted by a C.sub.3 -C.sub.6 cycloalkyl group;R.sup.2 denotes a hydrogen atom, a C.sub.1-16 alkyl or a C.sub.3-7 cycloalkyl group; andR.sup.3 represents a C.sub.1-4 alkyl group.
    Type: Grant
    Filed: January 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Pal Benko, Ildiko Ratz nee Simonek, Eva Rakoczy nee Pinter, Karoly Magyar, Jozsef Kelemen, Attila Mandi
  • Patent number: 4568763
    Abstract: N-acyl-acyloxy aromatic amines, e.g. 4-acetoxyacetanilide (AAA), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with hydroxylamine or a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement and accompanying acylation by contacting the ketoxime with a carboxylic acid anhydride and a Beckmann rearrangement catalyst to form the N-acyl-acyloxy aromatic amine.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: February 4, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4568761
    Abstract: A new and improved process for preparing tertiary aralkyl carbamates is disclosed. The process comprises reacting a mixture of a lower alkyl carbamate with a tertiary aralkyl halide at a temperature of about 50.degree. C. to about 100.degree. C. until formation of the tertiary aralkyl carbamate is substantially complete. In a preferred process, an alkenyl aromatic compound which is the olefin precursor of the aralkyl halide employed, is added to the reaction mixture to improve the yield of tertiary aralkyl carbamate products. The tertiary aralkyl carbamates prepared by the process of this invention are useful intermediates which may be thermally cracked in the presence of base catalysts to form tertiary aralkyl isoayanates.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: February 4, 1986
    Assignee: American Cyanamid Company
    Inventor: William A. Henderson, Jr.
  • Patent number: 4567287
    Abstract: Disclosed is an improved process for the preparation of carbamates by heating an organic carbonate and an aromatic urea or polyurea in the presence of aluminum as catalyst and a promoter comprising a combination of iodine and a mercury salt.High reaction temperatures are avoided by the process and conversions to carbamate products are high. Additionally, the process is economically attractive because even the common aluminum foil can be used as the catalyst.The products prepared by the process can be used in the production of insecticides, and, particularly, as intermediates in the preparation of organic mono- and polyisocyanates.
    Type: Grant
    Filed: August 8, 1984
    Date of Patent: January 28, 1986
    Assignee: The Upjohn Co.
    Inventors: Floro F. Frulla, Fred A. Stuber, Peter J. Whitman
  • Patent number: 4559383
    Abstract: 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: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventors: Joseph W. Holubka, Ray A. Dickie
  • Patent number: 4554188
    Abstract: 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: Grant
    Filed: January 5, 1983
    Date of Patent: November 19, 1985
    Assignee: Ford Motor Company
    Inventors: Joseph W. Holubka, Ray A. Dickie
  • Patent number: 4550188
    Abstract: Disclosed is an improved process for the preparation of carbamates by heating an organic carbonate and an aromatic amine in the presence of aluminum as catalyst and a promoter comprising a combination of iodine and a mercury salt.High reaction temperatures are avoided by the process and conversions to carbamate products are high. Additionally, the process is economically attractive because even the common aluminum foil can be used as the catalyst.The products prepared by the process can be used in the production of insecticides, and, particularly, as intermediates in the preparation of organic mono- and polyisocyanates.
    Type: Grant
    Filed: June 27, 1984
    Date of Patent: October 29, 1985
    Assignee: The Dow Chemical Company
    Inventors: Floro F. Frulla, Fred A. Stuber, Peter J. Whitman
  • Patent number: 4547524
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as herein defined useful as insecticides, is described.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: October 15, 1985
    Assignee: Hokko Chemical Industry Co., Ltd.
    Inventors: Kimiyoshi Kaneko, Hiromichi Ishikawa, Satoru Moriyama, Tsugio Uchiyama
  • Patent number: 4540497
    Abstract: Novel fluoroaliphatic radical-containing, substituted guanidines useful in the form of organic solutions or aqueous dispersions in the treatment of fibrous substrates, such as textile fibers, to impart oil and water repellency.
    Type: Grant
    Filed: November 9, 1982
    Date of Patent: September 10, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John C. Chang, Richard D. Howells
  • Patent number: 4535167
    Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co. Inc.
    Inventor: Roger M. Freidinger
  • Patent number: 4533745
    Abstract: Amino ketone enantiomers and their direct preparation are disclosed. The ketone may be reduced to yield carbinol enantiomer which has pharmaceutical activity.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: August 6, 1985
    Assignee: Merck & Co., inc.
    Inventor: David E. McClure
  • Patent number: 4532266
    Abstract: 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: Grant
    Filed: March 19, 1982
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
  • Patent number: 4532317
    Abstract: 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: Grant
    Filed: June 21, 1983
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4532347
    Abstract: 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: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4519834
    Abstract: The ethynyl-phenylureas of the formula I ##STR1## wherein X is hydrogen, halogen, lower alkyl, lower alkoxy, haloalkyl or nitro, Y is oxygen or sulfur, R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, phenyl or benzyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or benzyl, R.sub.1 and R.sub.2 together with the nitrogen atom to which they are bound are also a pyrrolidine, piperidine, morpholino or piperazine ring, R.sub.3 is hydrogen or lower alkyl, and R.sub.4 is hydrogen, alkyl, phenyl, pyridyl, alkenyl, cycloalkyl or cycloalkenyl, are novel substances. They are characterized by strong herbicidal activity.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: May 28, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Szczepanski
  • Patent number: 4515731
    Abstract: Catalytic asymmetric hydrogenation of the Z geometric isomer of a compound of the formula ##STR1## wherein at least one of R and R.sup.1 represents hydrogen and the other represents hydrogen, lower alkyl or aryl; R.sup.2 represents ##STR2## wherein R.sup.4 and R.sup.5 each independently represent hydrogen, lower alkyl or aryl, R.sup.6 represents hydrogen, lower alkyl, aryl or an alkali metal; and R.sup.3 represents ##STR3## wherein R.sup.7 and R.sup.8 each independently represent lower alkyl or aryl; provided that, when R.sup.3 is ##STR4## R.sup.2 is --CN, in the presence of a homogeneous, coordination complex catalyst comprising rhodium, iridium or ruthenium in combination with an optically active bis phosphine ligand provides an outstanding level of optical purity.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: May 7, 1985
    Assignee: Monsanto Company
    Inventors: Gerald L. Bachman, Billy D. Vineyard
  • Patent number: 4507464
    Abstract: 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: Grant
    Filed: February 10, 1984
    Date of Patent: March 26, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4504628
    Abstract: 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: Grant
    Filed: April 14, 1983
    Date of Patent: March 12, 1985
    Assignee: The Dow Chemical Company
    Inventor: Mark R. Johnson
  • Patent number: 4501756
    Abstract: Use of a compound of the formula: ##STR1## wherein X and Y are, same or different, each a lower alkyl group, a lower alkoxy group or a halogen atom and R is a methyl group or an ethyl group as a fungicidal agent against plantpathogenic fungi, particularly their drug-resistant strains.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: February 26, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiro Kato, Junya Takahashi, Katsuzo Kamoshita
  • Patent number: 4491670
    Abstract: Isocyanates, or derivatives thereof, are produced from nitrobenzene or 2,4-dinitrotoluene by reaction with carbon monoxide in the presence of an iron, ruthenium, rhodium, or platinum carbonyl as catalyst.
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: January 1, 1985
    Assignee: Indian Explosives Ltd.
    Inventors: Sumit Bhaduri, Krishna R. Sharma, Gopalkrishnan S. Kalpathi
  • Patent number: 4490551
    Abstract: A process for producing urethanes by reacting aromatic amino compounds with aliphatic, cycloaliphatic or araliphatic alcohols and carbon monoxide under conditions of elevated temperature and pressure characterized in that the reaction takes place in the presence of(a) selenium, selenium compounds, sulfur and/or sulfur compounds,(b) aromatic nitro compounds,(c) tertiary organic amines and/or alkali metal salts of weak acids,(d) oxidizing agents of a specified group and, optionally(e) ammonia and/or aliphatic, araliphatic, cycloaliphatic or heterocyclic amines containing at least one hydrogen atom bound to an amine nitrogen.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: December 25, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Armin Zenner
  • Patent number: 4490388
    Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with 4-(.beta.-amidinoethenyl)phenol represented by the formula (III) ##STR2## and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 25, 1984
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Takuo Aoyama, Yojiro Sakurai, Toyoo Nakayama, Shigeki Nunomura, Takashi Yaegashi, Toshiyuki Okutome
  • Patent number: 4489010
    Abstract: A compound having the structural formula ##STR1## wherein R is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl ammonium; R' is selected from the group consisting of C.sub.2 -C.sub.8 alkyl, C.sub.1 -C.sub.3 alkoxy, cyclopropyl, methacryl, C.sub.1 -C.sub.3 alkylmercapto, methylamino, ethylamino, C.sub.2 -C.sub.4 dialkylamino, C.sub.2 -C.sub.4 alkylalkoxyamino; and n equals the integer 0 or 1; and its use as a herbicide and as a herbicide intermediate.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: December 18, 1984
    Assignee: Stauffer Chemical Company
    Inventors: Eugene G. Teach, Jeffery T. Springer
  • Patent number: 4487952
    Abstract: Process for the preparation of esters of carbamic acids by carbonylation of aromatic nitrocompounds, with carbon monoxide, in the presence of alcohols and of catalyst consisting of metallic selenides.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: December 11, 1984
    Assignee: Anic S.p.A.
    Inventor: Villiam Giroldini
  • Patent number: 4486447
    Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: December 4, 1984
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4486429
    Abstract: Compounds of the formula I: ##STR1## in which R represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms and R.sub.1 and R.sub.2, which may be identical or different independently represent a hydrogen atom, an alkyl radical containing from 1 to 4 carbon atoms, a --CONH.sub.2 radical, a --CO.sub.2 alk.sub.1 radical in which alk.sub.1 represents an alkyl radical containing from 2 to 8 carbon atoms, or an--SO.sub.2 alk.sub.2 radical in which alk.sub.2 represents an alkyl radical containing from 1 to 8 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom form a heterocycle provided that R.sub.1 and R.sub.2 are not both hydrogen, as well as the alkali metal, alkaline earth metal, ammonium or amine salts of compounds of formula I in which R represents a hydrogen atom. These compounds are useful in treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias and gastric or gastroduodenal ailments accompanied by gastric hyperacidity.
    Type: Grant
    Filed: October 20, 1982
    Date of Patent: December 4, 1984
    Assignee: Roussel Uclaf
    Inventors: Mario Bianchi, Fernando Barzaghi
  • Patent number: 4480110
    Abstract: A process for the preparation of N,O-disubstituted urethanes. A substituted urea, an alcohol and a compound taken from the group consisting of N-unsubstituted urethanes, urea, polyurets and mixtures thereof at a temperature of 120.degree.-350.degree. C. The urethanes prepared by this process are particularly suitable for the preparation of isocyanates.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: October 30, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitk/a/ mper, Rudolf Fauss, Kurt Findeisen, Stefan Penninger, Hans-Joachim Scholl
  • Patent number: 4476316
    Abstract: N-Substituted carbamates are prepared by reacting a carbamate with an olefin in the presence of a cation exchanger containing sulfonic acid groups and of from 0.1 to 50 g of an alcohol per mole of starting material II.The N-substituted carbamates obtainable by the process of the invention are active ingredients and useful starting materials for the preparation of dyes, pesticides and drugs.
    Type: Grant
    Filed: January 19, 1983
    Date of Patent: October 9, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4474978
    Abstract: Process for the preparation of carbamates and/or derivatives thereof by reacting an organic compound containing at least one hydroxyl group with carbon monoxide and an organic nitrogeneous compound in the presence of a catalytic system based on palladium and a ligand according to the general formula: ##STR1## wherein L=N, P, As or Sb; R, R.sup.1, R.sup.2 and R.sup.3 are (un)substituted alkyl, aryl, alkaryl or aralkyl or R and R.sup.1 and/or R.sup.2 and R.sup.3 may form a ring together with the atom L to which they are attached; R.sup.4 and R.sup.5 are H or lower alkyl and n=2, 3 or 4, whereas carbon atoms between the groups L may be part of cyclic or non-cyclic unsaturated structures, and in the presence of an acid promoter.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: October 2, 1984
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Petrus W. N. M. Van Leeuwen
  • Patent number: 4472568
    Abstract: This invention relates to an improved process for the preparation of aromatic polyamines containing urethane and/or biuret and/or urea and/or isocyanurate groups and preferably also ether groups by the hydrolysis of poly-N-monoaryl-N',N'-dialkyl urea compounds (1-aryl-3,3-dialkyl ureas). The ureas are obtained by the reaction of secondary aliphatic, cycloaliphatic or saturated heterocyclic amines with divalent to tetravalent isocyanate compounds containing isocyanate end groups attached to aromatic residues. The ureas correspond to the general formula: ##STR1## wherein R.sup.1, R.sup.2 denote alkyl or cycloalkyl groups, or together form a ring andA denotes a divalent to tetravalent residue attached to the ureas by aromatic groups.Hydrolysis is carried out in the presence of water and up to two equivalents of a base containing hydroxide ions and/or up to two equivalents of a compound containing tertiary amino groups, optionally in the presence of solvents.
    Type: Grant
    Filed: October 28, 1982
    Date of Patent: September 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Grogler
  • Patent number: 4469882
    Abstract: A process for producing aromatic carbamates in high yield is described, which comprises reacting aromatic nitro compounds, organic compounds containing a hydroxy group, and carbon monoxide in the presence of a catalyst comprising: (1) a platinum group metal or its compound, (2) metallic vanadium or its compound, (3) metallic iron or its compound, (4) a halogen atom, and (5) a tertiary amine, wherein the amount of each component used and the composition are adjusted within specific ranges.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: September 4, 1984
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Tsutomu Takeuchi, Mineo Nishi, Toshio Irie, Hirotaka Ryuto
  • Patent number: 4459236
    Abstract: 1-Alkenyl isocyanates are prepared by reacting aldehydes with carbamates to give N-(1-alkenyl)-carbamates and splitting these compounds at elevated temperatures. The 1,2-unsaturated isocyanates obtained are valuable starting materials for the preparation of pest control agents, dyes, drugs, textile water repellents, detergents, plastics, bleaches and adhesives, since they possess an activated double bond or an activated .alpha.-carbon atom, in addition to a reactive isocyanate group.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: July 10, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Hans-Martin Hutmacher, Friedrich Towae
  • Patent number: 4443593
    Abstract: Waste or surplus polycarbonates are salvaged by reacting them with a hydroxy amine in an amount sufficient to cleave about 85% or more of the carbonate groups, thereby converting the polymer to a mixture of dihydroxy monomers--including novel dihydroxy carbamates--which may be converted to useful polymers by reaction with other difunctional monomers having at least one hydroxy-reactive functional group per molecule.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: April 17, 1984
    Assignee: The Dow Chemical Company
    Inventor: Guy R. Collins
  • Patent number: 4439616
    Abstract: Production of tertiary aralkyl isocyanates, such as tetramethyl xylylene diisocyanates, by thermal cracking of corresponding urethanes formed by addition of corresponding olefins and carbamic acid esters at moderate temperatures and in the presence of acid catalyst.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: March 27, 1984
    Assignee: American Cyanamid Company
    Inventors: Balwant Singh, Laurence W. Chang, Peter S. Forgione
  • Patent number: 4430505
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: February 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann
  • Patent number: 4430262
    Abstract: Isocyanates and derivatives thereof are prepared by oxidative conversion of compounds having at least one group ##STR1## wherein X represents OY or ##STR2## wherein Y is H, a metal ion or group NR.sup.3 R.sup.4 R.sup.5 R.sup.6 wherein each of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is H, alkyl or (substituted) (alk)aryl and Z is a (substituted) alkyl or aryl group. Phenyl isocyanate and derivatives thereof are preferably prepared electrochemically from the corresponding oxamides and oxanilides.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: February 7, 1984
    Assignee: Shell Oil Company
    Inventors: Rainer Engels, Jan H. H. Meurs
  • Patent number: H41
    Abstract: An unballasted arylhydrazide is disclosed the aryl moiety of which is substituted with a group of the formula ##STR1## where one of X and X' represents -NH-, the other represents a divalent chalcogen, and R represents an aliphatic or aromatic residue. The arylhydrazides, when applied to halftone imaging in conjunction with silver halide emulsions, photographic elements, and imaging processes, produce images of improved dot quality and low levels of pepper fog.
    Type: Grant
    Filed: August 2, 1985
    Date of Patent: April 1, 1986
    Assignee: Eastman Kodak Company
    Inventors: James C. Loblaw, Barbara B. Lussier