Patents Examined by Dolph H. Torrence
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Patent number: 4565570Abstract: 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: GrantFiled: March 11, 1985Date of Patent: January 21, 1986Assignee: Stauffer Chemical CompanyInventors: Jeff K. Curtis, William J. Michaely
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Patent number: 4560515Abstract: 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: GrantFiled: November 14, 1983Date of Patent: December 24, 1985Assignee: Shell Oil CompanyInventors: Donald W. Stoutamire, Charles H. Tieman
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Patent number: 4551526Abstract: 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: GrantFiled: September 26, 1984Date of Patent: November 5, 1985Assignee: American Hospital Supply CorporationInventors: Khuong H. X. Mai, Ghanshyam Patil
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Patent number: 4551537Abstract: 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: GrantFiled: September 26, 1984Date of Patent: November 5, 1985Assignee: American Hospital Supply CorporationInventors: Khuong H. X. Mai, Ghanshyam Patil
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Patent number: 4548756Abstract: 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: GrantFiled: December 7, 1984Date of Patent: October 22, 1985Assignee: Ciba Geigy CorporationInventor: Henry Martin
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Patent number: 4547322Abstract: 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: GrantFiled: March 19, 1984Date of Patent: October 15, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shinsuke Fukuoka, Masazumi Chono, Tomonari Watanabe, Masashi Kohno
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Patent number: 4547522Abstract: 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: GrantFiled: June 14, 1983Date of Patent: October 15, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4545921Abstract: 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: GrantFiled: December 29, 1983Date of Patent: October 8, 1985Assignee: Thomson-CSFInventors: Jean-Claude Dubois, Gilles Ravaux, Pierre Le Barny
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Patent number: 4544510Abstract: 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: GrantFiled: October 25, 1983Date of Patent: October 1, 1985Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Johannes van Berkel, Wilhelmus N. Ruyters
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Patent number: 4544508Abstract: 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: GrantFiled: January 9, 1985Date of Patent: October 1, 1985Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann
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Patent number: 4544763Abstract: 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: GrantFiled: October 19, 1984Date of Patent: October 1, 1985Assignee: Basf Wyandotte CorporationInventor: Thirumurti Narayan
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Patent number: 4543215Abstract: 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: GrantFiled: November 2, 1983Date of Patent: September 24, 1985Assignee: BASF AktiengesellschaftInventors: Fritz Brunnmueller, Michael Kroener
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Patent number: 4541963Abstract: 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: GrantFiled: November 14, 1984Date of Patent: September 17, 1985Assignee: May & Baker LimitedInventors: Leslie R. Hatton, Edgar W. Parnell, David A. Roberts
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Patent number: 4541961Abstract: 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: GrantFiled: August 29, 1983Date of Patent: September 17, 1985Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4541962Abstract: 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: GrantFiled: May 7, 1984Date of Patent: September 17, 1985Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4540791Abstract: 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: GrantFiled: July 8, 1983Date of Patent: September 10, 1985Assignee: Ciba-Geigy CorporationInventors: Luigi Cassar, Abul Iqbal, Alain C. Rochat
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Patent number: 4540522Abstract: 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: GrantFiled: October 7, 1983Date of Patent: September 10, 1985Assignee: Monsanto CompanyInventors: John P. Chupp, Terry M. Balthazor
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Patent number: 4539159Abstract: 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: GrantFiled: April 23, 1984Date of Patent: September 3, 1985Assignee: The Dow Chemical CompanyInventor: Mark R. Johnson
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Patent number: 4539156Abstract: 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: GrantFiled: December 14, 1984Date of Patent: September 3, 1985Assignee: Mobay Chemical CorporationInventors: John E. Dewhurst, Jeffrey F. Dormish, Richard S. Pantone
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Patent number: 4539158Abstract: 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: GrantFiled: December 14, 1984Date of Patent: September 3, 1985Assignee: Mobay Chemical CorporationInventors: John E. Dewhurst, Jeffrey F. Dormish, Richard S. Pantone