Patents Examined by Dolph H. Torrence
  • Patent number: 4372893
    Abstract: Selective reduction of compounds containing reducible nitro-, nitroso-, nitrilo-, oximes or double bonds is effected by the use of a metal macrocyclic compound in prereduced form, such as a metal phthalocyanine or a metal porphyrin.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: February 8, 1983
    Inventor: Heiner Eckert
  • Patent number: 4372776
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.3 each is hydrogen or R.sup.1 and R.sup.3 together form a second carbon-to-nitrogen bond, R.sup.2 is hydrogen or cyano, R.sup.4 is alkyl and Ar is one of certain aromatic moieties.The compounds can be used as abscission agents for the loosening of fruit and/or leaves on plants.
    Type: Grant
    Filed: October 16, 1981
    Date of Patent: February 8, 1983
    Assignee: Shell Oil Company
    Inventors: Janet A. Day, Robert J. G. Searle
  • Patent number: 4371473
    Abstract: 2-(2-fluoro-4-biphenylyl)propionic acid is prepared from 2-amino-4-methyl-biphenyl via a series of novel intermediates. In particular 2-amino-4-methylbiphenyl is converted to 2-fluoro-4-methylbiphenyl, the methyl group is brominated to form 2-fluoro-4-monobromomethylbiphenyl which is transformed into 2-(2-fluoro-4-biphenylyl)acetonitrile. This acetonitrile is then converted to flurbiprofen via the corresponding propionitrile or it may be converted into flurbiprofen via the intermediate ethyl-2-(2-fluoro-4-biphenylyl)-2-cyanopropionate.
    Type: Grant
    Filed: September 22, 1980
    Date of Patent: February 1, 1983
    Assignee: Ethyl Corporation
    Inventors: Edward J. Zaiko, Paul F. Ranken
  • Patent number: 4370278
    Abstract: 2-(Fluoronitrobenzene)alkyl cyanides are prepared by reacting a fluoronitrobenzene with an alpha-substituted alkyl cyanide in a substantially anhydrous aprotic solvent and in the presence of a base so that the alkyl cyanide reactant undergoes a nucleophilic substitution reaction on an unsubstituted carbon atom of the fluoronitrobenzene during which the alpha-substituent of the alkyl cyanide reactant functions as a leaving group. Use of 2-fluoronitrobenzene and an alpha-substituted propionitrile (e.g., 2-chloropropionitrile) produces a novel compound, 2-(3-fluoro-4-nitrobenzene)propionitrile. Reduction of the nitro substituent produces another novel compound, 2-(4-amino-3-fluorobenzene)proprionitrile. This can readily be converted to 2-(3-fluoro-4-biphenylyl)propionitrile by means of a Gomberg-Bachmann reaction with an aromatic hydrocarbon or substituted aromatic hydrocarbon which in turn can be converted on hydrolysis into the corresponding 2-(2-fluoro-4-biphenylyl)propionic acid.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: January 25, 1983
    Assignee: Ethyl Corporation
    Inventors: Barbara C. Stahly, G. P. Stahly
  • Patent number: 4370277
    Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is H, halogen, alkyl or alkoxy; R.sup.2 is H, halogen, alkyl or CF.sub.3 ; R.sup.3 is H, Cl, Br, alkyl or CN; R.sup.4 is H, halogen, alkyl, phenyl or halophenyl; and R.sup.5 is H, alkyl, alkinyl or CN; are starting materials for the manufacture of valuable insecticides of the pyrethroid type.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: January 25, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Welter, Hilmar Mildenberger
  • Patent number: 4370345
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 denotes H, halogen, alkyl or CF.sub.3, R.sup.2 denotes H, halogen, alkyl or CF.sub.3, R.sup.3 denotes H, halogen, CN or alkyl, R.sup.4 denotes H, halogen, alkyl, phenyl or halogenophenyl, R.sup.5 denotes H, alkyl, alkynyl or CN and R.sup.6 denotes substituted dimethylcyclopropyl or 2-phenylisobutyl radicals, are effective insecticides and acaricides of the pyrethroid type.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: January 25, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Welter, Hilmar Mildenberger, Werner Knauf, Anna Waltersdorfer, Werner Bonin
  • Patent number: 4369146
    Abstract: A method for chlorinating the carboxylic group of .alpha.-aminoacids (e.g. hydroxyphenyl-glycine) is described wherein the aminoacid is suspended in an optionally solvate-forming solvent, treated with an excess of gaseous HCl and then with a chlorinating agent having the general formula [SO.sub.a Cl.sub.2.R.sub.1 R.sub.2 NCHO] (e.g. SO Cl.sub.2.(CH.sub.3).sub.2 NCHO).A typical compound thus obtained is the dioxane hemisolvate of D(-)2-(p-hydroxyphenyl)glycyl chloride hydrochloride.
    Type: Grant
    Filed: May 7, 1981
    Date of Patent: January 18, 1983
    Assignee: Chimica Bulciago S.r.l.
    Inventors: Rodolfo Maggi, Gian P. Maggi, Giuliano Marcon
  • Patent number: 4366170
    Abstract: Antimicrobial compounds of the formulas: ##STR1## where R.sup.1 and R.sup.2 are hydrogen; halo; C.sub.1-4 alkyl; C.sub.1-4 alkoxy; hydroxy; nitro; cyano; or trifluoromethyl;m is 0 or 1; andn is 1 or 2.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: December 28, 1982
    Assignee: Merck & Co., Inc.
    Inventors: John E. Engelhart, Marshall R. Angeles, Michael J. D'Errico
  • Patent number: 4364875
    Abstract: The method of preparing a compound of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl of 1 to 8 carbon atoms, trifluoromethyl or acetyl;n is 1 when R.sub.1 has all the defined meanings, or 2 or 3 when R.sub.1 is halogen or alkyl;R.sub.2 is hydrogen; alkyl of 1 to 16 carbon atoms; alkenyl of 2 to 16 carbon atoms; alkinyl of 2 to 16 carbon atoms; monosubstituted alkyl of 2 to 6 carbon atoms, where the substituent is hydroxyl, alkoxy of 1 to 4 carbon atoms, phenoxy, halo-phenoxy, (alkyl of 1 to 4 carbon atoms) phenoxy, (alkoxy of 1 to 4 carbon atoms)phenoxy, nitro-phenoxy, cyano-phenoxy, amino or (alkyl of 1 to 4 carbon atoms)thio; benzyl; halo-benzyl; --NR.sub.3 R.sub.4 ; --CHR.sub.3 --COOR.sub.4 ; or --CHR.sub.3 --CONR.sub.4 R.sub.5, whereR.sub.3, R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 8 carbon atoms; andX.sub.1 and X.sub.2 are each hydrogen or halogen,which comprises reacting a compound of the formula ##STR2## wherein n, R.sub.1, X.sub.1 and X.sub.
    Type: Grant
    Filed: July 7, 1981
    Date of Patent: December 21, 1982
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Richard Sehring, Wolfgang Buck
  • Patent number: 4363767
    Abstract: The invention relates to liquid-crystalline nematic mixtures which are used in electro-optical components, as well as to methods for their preparation.The object of the invention is liquid-crystalline mixtures for electro-optical arrangements possessing high positive electrical anisotropy at a high clarification point, as well as methods for their preparation.According to the invention, liquid-crystalline nematic mixtures are used, wherein at least one component is a 1,4-disubstituted benzene derivative and the other compound is an ester of 4-[2,2-dicyano-ethenyl]-phenol of the general formula ##STR1## wherein R.sup.1 denotes added groups of various characters such as alkyl or alkoxy for example, X is aromatic, cycloaliphatic or a heterocyclic ring system such as phenyl or cyclohexyl for example; and Y is a connector such as carbonyloxy, azomethine, azoxy.These are prepared by reaction with reactive acid derivatives, particularly acid chlorides, or by a Knoevenagel-condensation by reacting respective 4-subst.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: December 14, 1982
    Assignee: VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik
    Inventors: Dietrich Demus, Wolfgang Weissflog, Horst Zaschke, Rudolf Wolff, Horst Kresse
  • Patent number: 4362670
    Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of a palladium catalyst.
    Type: Grant
    Filed: September 3, 1981
    Date of Patent: December 7, 1982
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4361518
    Abstract: A process for production of tertiary benzyl isocyanates by reaction at low temperatures of the corresponding halides with an excess of isocyanic acid.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: November 30, 1982
    Assignee: American Cyanamid Company
    Inventors: Balwant Singh, William A. Henderson, Jr.
  • Patent number: 4360689
    Abstract: New .alpha.-halobenzyl esters, intermediates for .alpha.-cyanobenzyl pyrethroid esters, are prepared by treating a benzaldehyde derivative with a pyrethroid acid halide. The resulting .alpha.-halobenzyl ester is treated with a water-soluble compound capable of generating cyanide ions (CN.sup.-) to give the corresponding .alpha.-cyanobenzyl esters.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: November 23, 1982
    Assignee: Shell Oil Company
    Inventor: Charles H. Tieman
  • Patent number: 4360476
    Abstract: A method of concentrating a solution of methylene diphenyl diisocyanate in diphenyl oxide, which includes cooling the solution until part of the solution crystallizes, thereby forming a solid phase having a lower concentration of the methylene diphenyl diisocyanate, and a liquid phase having a higher concentration of the methylene diphenyl diisocyanate than in the original solution, and then separating the solid and liquid phases. The method is particularly applicable to the concentration of solutions of 4,4'-methylene diphenyl diisocyanate in diphenyl oxide.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: November 23, 1982
    Assignee: The Dow Chemical Company
    Inventor: John G. Green
  • Patent number: 4360478
    Abstract: New .alpha.-halobenzyl esters, intermediates for .alpha.-cyanobenzyl pyrethroid esters, are prepared by treating a benzaldehyde derivative with a pyrethroid acid halide. The resulting .alpha.-halobenzyl ester is treated with a water-soluble compound capable of generating cyanide ions (CN.sup.-) to give the corresponding .alpha.-cyanobenzyl esters.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: November 23, 1982
    Assignee: Shell Oil Company
    Inventor: Charles H. Tieman
  • Patent number: 4360466
    Abstract: This disclosure describes novel N'-[2,6-dichloro-4-(substituted-benzylideneamino)phenyl]-N,N-dimethylforma midines which possess activity as hypotensive agents and as diuretics.
    Type: Grant
    Filed: November 25, 1981
    Date of Patent: November 23, 1982
    Assignee: American Cyanamid Company
    Inventors: Walter E. Meyer, Andrew S. Tomcufcik, Joseph W. Marsico, Jr.
  • Patent number: 4359428
    Abstract: Fluorinated anthranilic acid and anthranilonitrile, and a novel process for their preparation by reacting 2,6-difluorobenzonitrile with ammonia and, if the acid is required, hydrolyzing the resulting 6-fluoroanthranilonitrile with a basic compound.The two novel end products are valuable intermediates for the preparation of compounds which are useful for controlling various animal pests and plant pests.
    Type: Grant
    Filed: November 5, 1981
    Date of Patent: November 16, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Jacobs, Heinz-Guenter Oeser
  • Patent number: 4359426
    Abstract: The instant invention is directed to a process for the production of an aromatic isocyanate containing aromatically bound sulfochloride groups, comprising:(I) reacting(a) an isocyanate or carbamic acid chloride which contains at least one aromatically bound isocyanate group and/or at least one aromatically bound carbamic acid chloride group, successively or simultaneously at 0.degree. to 170.degree. C. with(b) a sulfonating agent and(c) an organic compound containing at least one aromatically bound trihalo methyl group and(II) removing hydrogen chloride from the reaction mixture at 20.degree. to 170.degree. C.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: November 16, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Dieterich, Heinz U. Blank, Erich Wolters, Norbert Langenfeld
  • Patent number: 4357347
    Abstract: Phenylcarbamoylbenzimidates of the formula ##STR1## wherein X.sub.1 is selected from the group consisting of methyl, trifluoromethyl, chlorine, fluorine and bromine; X.sub.2 is selected from the group consisting of hydrogen, methyl, trifluoromethyl, chlorine, fluorine and bromine; R is alkyl of from 1 to 5 carbon atoms; X.sub.3 and X.sub.4 can be the same or different and are selected from the group consisting of hydrogen, chlorine and bromine; X.sub.5 is selected from the group consisting of hydrogen, chlorine, bromine and trifluoromethyl; and X.sub.6 is selected from the group consisting of cyano and nitro; with the proviso that when X.sub.1 and X.sub.2 are chlorine or when X.sub.1 is fluorine and X.sub.2 is hydrogen then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are respectively not 1-methylethyl, chlorine, hydrogen, chlorine and nitro; with the further proviso that when X.sub.1 is fluorine and X.sub.2 is hydrogen then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: November 2, 1982
    Assignee: The Upjohn Company
    Inventor: Stephen J. Nelson
  • Patent number: 4357255
    Abstract: Waste polyurethane materials are made re-usable by converting them to liquid mixtures. Such liquid mixtures are made by reacting up to 70 parts by weight of polyurethane with a low-melting polyisocyanate at 100.degree. to 250.degree. C. in the presence of a catalyst. Suitable catalysts include the acid and neutral salts, phenolates, enolates and alcoholates of a metal of the 3rd, 4th or 5th Main Group or 1st, 2nd, 4th, 7th or 8th subgroup of the Periodic System of elements. The thus-produced mixtures contain isocyanates and are suitable as an isocyanate component in the production of polyurethane plastic materials.
    Type: Grant
    Filed: August 26, 1981
    Date of Patent: November 2, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ingo Stemmler, Hanns-Peter Muller, Kuno Wagner