Patents Examined by Dolph H. Torrence
  • Patent number: 4565570
    Abstract: A compound having the structural formula ##STR1## wherein R is halogen, including fluorine, chlorine, bromine and iodine, preferably chlorine, methyl, ethyl, ethenyl, ethinyl, carboxaldehyde, methoxy, nitro, trifluoromethyl or cyano, --S(O).sub.n CH.sub.3, wherein n is 0, 1 or 2; --NH.sub.2, --NHCH.sub.3, --N(CH.sub.3).sub.2, or --SO.sub.2 NH.sub.2 ; provided that when R is hydrogen, W must be hydrogen and that when R is chlorine, W cannot be 4- or 6-chlorine; R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl or allyl; W is halogen, including fluorine, chlorine, bromine and iodine; trifluoromethyl, methyl, C.sub.1 -C.sub.3 thioalkyl, --NHC(O)CH.sub.3, or methoxy, provided that methoxy cannot be located in the 4-position on the ring; and X is in either the 2- or 3-position and can be halogen, including fluorine, chlorine, bromine, and iodine; thiomethyl, methyl or hydrogen.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: January 21, 1986
    Assignee: Stauffer Chemical Company
    Inventors: Jeff K. Curtis, William J. Michaely
  • Patent number: 4560515
    Abstract: Optically-active alpha-cyano esters are prepared by treating a non-symmetrical ketene with a racemic or an optically-active alpha-hydroxynitrile or with an aldehyde and cyanide ions in the presence of an optically-active amine catalyst.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: December 24, 1985
    Assignee: Shell Oil Company
    Inventors: Donald W. Stoutamire, Charles H. Tieman
  • Patent number: 4551526
    Abstract: Described is a process for preparing alpha-aminonitriles having the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 aralkyl, unsubstituted or substituted aryl or heteroaryl or alternatively, R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 12 member cycloalkyl group, or with a heteroatom form a 3 to 12 member heterocyclic group and R.sub.3 and R.sub.4 together with the nitrogen atom form a 3 to 12 member heterocyclic group and R.sub.3 and R.sub.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: November 5, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: Khuong H. X. Mai, Ghanshyam Patil
  • Patent number: 4551537
    Abstract: Disclosed is a process for preparing optically active alpha-aminonitriles of the formula ##STR1## by the reaction of alpha-trimethylsilyloxynitriles with optically active alpha-methylbenzylamine in the presence of a loweralkyl alcohol.In the above formula, R denotes C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 aralkyl or unsubstituted or substituted aryl or heteroaryl.In general, R-alpha-methylbenzylamine gave I and III as the major and the minor products, respectively. Whereas, S-alpha-methylbenzylamine gave II and IV as the major and the minor products, respectively.The compounds so prepared are intermediates in the preparation of optically active aminoacids.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: November 5, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: Khuong H. X. Mai, Ghanshyam Patil
  • Patent number: 4548756
    Abstract: Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.
    Type: Grant
    Filed: December 7, 1984
    Date of Patent: October 22, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 4547322
    Abstract: Manufacture of a diphenylmethane diisocyanate for an N-phenylcarbamate is economically accomplished in high yield with high selectivity by a method which comprises (A) a process of methylenation for the formation of a condensation product containing at lest 80 mol % of a dinuclear diphenylmethane dicarbamate by the steps of (1) causing a methylenating agent to react upon at least 2 moles of an N-phenylcarbamate, based on 1 mole of the methylene group of said methylenating agent, in a liquid phase in the presence of an aqueous inorganic acid solution, (2) separating the resultant reaction mixture into the aqueous inorganic acid solution and an organic phase reaction mixture containing substantially none of said inorganic acid, and (3) subsequently treating said organic phase reaction mixture in the presence of an N-phenylcarbamate and a carboxylic acid having a pKa of not more than 4 in an aqueous solution at a temperature of 25.degree. C.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: October 15, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono, Tomonari Watanabe, Masashi Kohno
  • Patent number: 4547522
    Abstract: Novel cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein A is selected from the group consisting of --O--, --CH.sub.2 -- and ##STR2## R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and optionally unsaturated cycloalkyl and cycloalkylalkyl of 3 to 8 carbon atoms optionally substituted with at least one alkyl group and the double bond in the 3-side chain has the Z geometry in all possible stereoisomeric forms and mixtures of stereoisomers having insecticidal, nematocidal and animal and vegetable acaricidal activities and their preparation.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: October 15, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4545921
    Abstract: The invention relates to a group of organic compounds of the substituted 2-hydroxyfluorene ester type, which has a smectic A mesomorphous phase. The invention also relates to the process for producing molecules of this group.The compound according to the invention is in accordance with the general chemical formula ##STR1## whereby n can be between 1 and 15 and X=Br or CN. The invention applies to the field of liquid crystals and to display means using such crystals.
    Type: Grant
    Filed: December 29, 1983
    Date of Patent: October 8, 1985
    Assignee: Thomson-CSF
    Inventors: Jean-Claude Dubois, Gilles Ravaux, Pierre Le Barny
  • Patent number: 4544510
    Abstract: A process for preparing a compound according to formula I containing substantially equimolar amounts of the 1R cis S- and the 1S cis R-isomers (the cis-2 enantiomer pair) and substantially free of the 1R cis R- and the 1S cis S-isomers (the cis-1 enantiomer pair), ##STR1## wherein R.sup.1 and R.sup.2 are each independently selected from chlorine, bromine and methyl, which process comprises contacting the cis-1 enantiomer pair, alone or in the presence of the cis-2 enantiomer pair, with an organic amine base containing from 5 to 7 carbon atoms and being a secondary amine containing two branched alkyl groups or being a tertiary amine, and then separating off a solid compound containing the cis-2 enantiomer pair and substantially free of the cis-1 enantiomer pair, characterized in that the reaction mixture is in the form a solid-liquid slurry.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: October 1, 1985
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Johannes van Berkel, Wilhelmus N. Ruyters
  • Patent number: 4544508
    Abstract: A process for the preparation of the enantiomeric pairs (1R-3R-.alpha.S+1S-3S-.alpha.R) and (1R-3S-.alpha.S+1S-3R-.alpha.R) from a mixture of all 8 stereoisomers of the compound .alpha.R/S-cyano-3-phenoxy-4-fluorobenzyl 3R/S-(2,2-dichlorovinyl)-2,2-dimethyl-1R/S-cyclopropanecarboxylate, comprising dissolving the mixture in a secondary or tertiary alkylamine having 2-6 C atoms per alkyl radical, subjecting the solution to crystallization whereby the enantiomeric pairs (1R-3R-.alpha.S+1S-3S-.alpha.R) and (1R-3S-.alpha.S+1S-3R-.alpha.R) crystallize out from the solution, and separating the crystallized material. The crystals are enriched in the most active components.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: October 1, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann
  • Patent number: 4544763
    Abstract: Urethane-modified polyisocyanates prepared from toluene diisocyanate are desirable for economic, processing, and product property reasons. Such products should be low in viscosity to allow spray application and low in free TDI content to avoid undue physiological hazard.By use of prescribed reaction condition and reactant ratios, a suitable product can be prepared from hydroxyl-terminated polyoxyalkylene compounds, toluene diisocyanate, and diphenylmethane diisocyanate.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: October 1, 1985
    Assignee: Basf Wyandotte Corporation
    Inventor: Thirumurti Narayan
  • Patent number: 4543215
    Abstract: Novel .alpha.-iminodiacetonitriles are prepared by a process in which an aldehyde-cyanohydrin or a haloacetonitrile is reacted with an aminonitrile, the reaction being carried out in the presence of a lower alkanol in the case of the preparation of symmetric .alpha.-iminodiacetonitriles, and in the presence of an auxiliary base in the case of the preparation employing a haloacetonitrile. The .alpha.-iminodiacetonitriles obtainable by the process of the invention are useful starting materials for the preparation of dyes, fungicides, bactericides, herbicides, textile assistants, anticorrosion agents, complex-forming agents, stabilizers in electroplating baths and inhibitors for antifreezes.
    Type: Grant
    Filed: November 2, 1983
    Date of Patent: September 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz Brunnmueller, Michael Kroener
  • Patent number: 4541963
    Abstract: New N-phenylpyrazole derivatives of the formula: ##STR1## (wherein R.sup.12 represents a chlorine atom, R.sup.13 represents a hydrogen, fluorine or chlorine atom, R.sup.14 represents a hydrogen or fluorine atom and R.sup.15 represents a hydrogen, fluorine or chlorine atom, with the proviso that when R.sup.14 represents a fluorine atom, R.sup.15 represents a fluorine or chlorine atom, or R.sup.12, R.sup.13 and R.sup.15 each represents a fluorine atom and R.sup.14 represents a hydrogen or fluorine atom) possess useful herbicidal properties.
    Type: Grant
    Filed: November 14, 1984
    Date of Patent: September 17, 1985
    Assignee: May & Baker Limited
    Inventors: Leslie R. Hatton, Edgar W. Parnell, David A. Roberts
  • Patent number: 4541961
    Abstract: Nitriles, such as 2-(2-fluoro-4-biphenyl)propionitrile, contaminated with ketones having similar boiling points are purified by treating the nitrile/ketone mixture with an alkali metal borohydride, e.g., sodium borohydride, to complex the ketone. After complexing of the ketone, the nitrile can be separated therefrom by distillation.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: September 17, 1985
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4541962
    Abstract: 4-(3-Cyano-4-nitrophenyl)phenols are prepared by reacting a 2-cyano-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 2-cyano-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: September 17, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4540791
    Abstract: A process for producing a compound of the formula ##STR1## wherein A is aryl or alkyl, R.sub.1 is an aromatic radical and R.sub.2 is hydrogen, alkyl, aryl, cyano, --COOalkyl or --COOaryl, which process comprises reacting 1 mol of an aromatic nitrile of the formula R.sub.1 --CN (II) with 1 mol of an acetic ester of the formula (X)(R.sub.2)CH--COOA (III) in which X is halogen, in the presence of zinc, in an inert organic solvent and at a temperature of less than 80.degree. C.; hydrolyzing in an alkaline medium the formed reaction product; and then isolating the compound of the formula I.The compounds of the formula I are valuable intermediates for producing heterocyclic compounds.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: September 10, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Luigi Cassar, Abul Iqbal, Alain C. Rochat
  • Patent number: 4540522
    Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 10, 1985
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Terry M. Balthazor
  • Patent number: 4539159
    Abstract: An improved process for preparing derivatives of mercaptophenols containing nitrile, carbonyl, sulphone or ester groups characterized by reacting the components in a polar solvent with an amine catalyst. The catalyst can be removed from the product by co-distillation with the solvent to leave a relatively pure product free of contaminant without the need for further purification steps. The preferred amine catalysts are tertiary amines.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: September 3, 1985
    Assignee: The Dow Chemical Company
    Inventor: Mark R. Johnson
  • Patent number: 4539156
    Abstract: The present invention is directed to a process for the preparation of a stable, liquid adduct comprising reacting a mixture of 1,3-butane diol and propylene glycol with diphenylmethane diisocyanate at a temperature of from about 25.degree. C. to about 120.degree. C. in an amount such that the resultant product has an isocyanate group content of from about 20 to about 30 percent by weight, and wherein the ratio of mole equivalents of 1,3-butane diol to mole equivalents of propylene glycol is from 0.05:0.95 to 0.95:0.05, with the further proviso that(i) if the 4,4'-isomer content of the diphenylmethane diisocyanate is equal to or greater than 90 percent by weight, then said ratio is from 0.45:0.55 to 0.70:0.30, and(ii) if the 4,4'-isomer content of the diphenylmethane diisocyanate is less than 90 percent by weight, but not less than 70 percent by weight, then said ratio is from 0.30:0.70 to 0.85:0.15.The invention is also directed to a product produced from such process.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: September 3, 1985
    Assignee: Mobay Chemical Corporation
    Inventors: John E. Dewhurst, Jeffrey F. Dormish, Richard S. Pantone
  • Patent number: 4539158
    Abstract: The present invention is directed to a process for the preparation of a stable, liquid adduct comprising reacting a mixture of 1,3-butane diol and neopentyl glycol with diphenylmethane diisocyanate at a temperature of from about 25.degree. C. to about 120.degree. C. in an amount such that said adduct has an isocyanate group content of from about 20 to about 30 percent by weight, and wherein the ratio of mole equivalents of 1,3-butane diol to mole equivalents of neopentyl glycol is from 0.05:0.95 to 0.95:0.05, with the further proviso that(i) if the 4,4'-isomer content of the diphenylmethane diisocyanate is equal to or greater than 98 percent by weight, then said ratio is from 0.30:0.70 to 0.65:0.35,(ii) if the 4,4'-isomer content of the diphenylmethane diisocyanate is less than 98 percent by weight but not less than 90 percent by weight, then said ratio is from 0.30:0.70 to 0.75:0.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: September 3, 1985
    Assignee: Mobay Chemical Corporation
    Inventors: John E. Dewhurst, Jeffrey F. Dormish, Richard S. Pantone