Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
  • Patent number: 4390721
    Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: June 28, 1983
    Assignee: Allen & Hanburys Limited
    Inventor: Stanley M. Roberts
  • Patent number: 4388322
    Abstract: Substituted 3-(1,2-dibromo-alkyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is halogen or optionally substituted phenyl or optionally substituted alkyl,R.sup.2 is hydrogen, halogen or optionally substituted alkyl, andY is the radical of an alcohol customary in pyrethroids, with the proviso that Y is a benzyloxy radical which is substituted by halogen and optionally substituted by at least one additional radical if R.sup.1 is halogen or methyl,which possess pesticidal properties. The acid moieties of such esters wherein R.sup.1 is optionally substituted phenyl are new compounds.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: June 14, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Wilhelm Stendel
  • Patent number: 4381313
    Abstract: Novel phenylalkanoic compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 independently from each other represent hydrogen or alkyl with 1 to 8 carbon atoms, salts of such compounds and salts thereof, therapeutic uses of the phenylalkanoic compounds, or of the pharmacologically safe salts thereof for treating inflammatory diseases, tussive states, pain symptoms and pyretic diseases and pharmaceutical composition containing the phenylalkanoic compounds or the pharmacologically safe salts together with a carrier and an optional adjuvant or additive.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: April 26, 1983
    Assignee: Hommel AG
    Inventors: Jean Heusser, Max Glasbrenner
  • Patent number: 4377593
    Abstract: The invention relates to .alpha.-isopropyl- and .alpha.-cyclopropylphenylacetates of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, allenyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl, R.sub.2 is unsubstituted or substituted alkenyl or alkynyl, R.sub.3 is isopropyl or cyclopropyl, and each of R.sub.4 and R.sub.5 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, or both together are the methylenedioxy radical.A process for the production of these compounds and their use in pest control are disclosed.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: March 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
  • Patent number: 4374263
    Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: February 15, 1983
    Assignee: The British Petroleum Company Limited
    Inventors: Ronald D. Hancock, Robert Mackison
  • 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: 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: 4365032
    Abstract: A monoester compound of a 2,2'-alkylidene bis(4,6-di-substituted phenol) useful as an antioxidant in synthetic polymers having good resistant to oxides of nitrogen fumes, represented by the formula (I), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a C.sub.1-4 alkyl group, a C.sub.5-6 cycloalkyl group or a methyl-substituted C.sub.5-6 cycloalkyl group; and one of R.sub.3 and R.sub.4 represents a hydrogen atom and the other represents a hydrogen atom or a C.sub.1-10 alkyl group or both of them represent a methyl group; R.sub.5 represents a C.sub.4-9 alkyl group, a C.sub.3-7 cycloalkyl group, a C.sub.2-4 alkenyl group, a phenyl group, a C.sub.1-4 alkyl-substituted phenyl group, a C.sub.1-4 alkoxy-substituted phenyl group, a mono- or di- C.sub.1-4 alkyl-substituted hydroxyphenyl group, a styryl group, a benzyl group or a pyridyl group, and a method of preparing such a monoester compound.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: December 21, 1982
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Akihiko Yosizato, Yoshinori Morifuji, Kunio Kondo, Masatsugu Yoshino
  • Patent number: 4362744
    Abstract: Disclosed are novel compounds of the formula ##STR1## in which R.sup.1 is hydrogen or methyl; R.sup.2 is phenyl or phenyl-methyl either of which is optionally ring substituted with lower alkyl or halogen; R is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substitutedphenyl)-2-methylpropylcarbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substitutedvinylcyclopropanecarbonyl group; and, with respect to the indanyl substituents, the 1,3-trans isomer is present in an isomeric excess over the corresponding 1,3-cis isomer. The compounds wherein R is other than hydrogen are insecticides, and the compounds wherein R is hydrogen are insecticide intermediates.
    Type: Grant
    Filed: March 19, 1981
    Date of Patent: December 7, 1982
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • 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: 4354036
    Abstract: A carboxylic acid ester, such as methyl propionate, is prepared by carbonylation of an olefin, such as ethylene in the presence of an alcohol by the use of a molybdenum-nickel or tungsten-nickel co-catalyst in the presence of a promoter comprising an organo-phosphorus compound or an organo-nitrogen compound wherein the phosphorus and nitrogen are trivalent and in the presence of a halide.
    Type: Grant
    Filed: May 28, 1981
    Date of Patent: October 12, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4352760
    Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: October 5, 1982
    Assignee: The Upjohn Company
    Inventor: Kirk M. Maxey
  • Patent number: 4347378
    Abstract: Esters and mixed ester-amides derived from glycolic acid by substitution at the hydroxyl and carboxyl functions were prepared by conventional procedures and tested for antimicrobial activity. All of the compounds tested showed some inhibition against four microorganisms under the test conditions, and some of them had potent activity. These new compounds have properties which make it possible for them to be used as biostatic agents in commercial products.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: August 31, 1982
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: August V. Bailey, Gordon J. Boudreaux, Gene Sumrell
  • Patent number: 4344961
    Abstract: Novel carboxylic acid esters of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are identical or different and each is hydrogen, halogen or alkyl or alkenyl of up to 5 carbon atoms,Y is 3-(2,2-dihalogenovinyl)-2,2-dimethyl-cyclopropyl or a radical of the formula ##STR2## where R.sup.4 is unbranched or branched alkyl, alkenyl or alkynyl of up to 4 carbon atoms or is an alicyclic radical of 3 to 7 carbon atoms,R.sup.5 is halogen, alkyl or alkoxy of up to 5 carbon atoms, trihalomethyl, cyano or nitro anda is from 0 to 3 andZ is a radical of the formula ##STR3## where X is oxygen, sulfur or --CH.sub.2 --,R.sup.6, R.sup.7 and R.sup.8 are halogen or alkyl, alkoxy or haloalkyl of up to 5 carbon atoms andb, c and d are from 0 to 3, their preparation and their use in insect and arachnid control.
    Type: Grant
    Filed: February 9, 1981
    Date of Patent: August 17, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd-Ulrich Schwarz, Karl Kiehs, Heinrich Adolphi
  • Patent number: 4343796
    Abstract: The invention relates to compounds of the formula: ##STR1## in which R.sub.1 and R.sub.2 are the same or different groups selected from hydrogen or acyl orR.sub.1 and R.sub.2 together may represent an acetal group, andX and Y are the same or different groups selected from hydroxy, an etherified hydroxy and an esterified hydroxy group,having valuable lipid lowering, anti-inflammatory and immuno-modulating properties.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 10, 1982
    Assignee: AKZO NV
    Inventor: Marinus B. Groen
  • Patent number: 4339594
    Abstract: Phenylacetic acid and the simple derivatives thereof are prepared by catalytic hydrogenation of mandelic acid and its appropriate derivatives in the presence of a noble metal catalyst in aqueous solution which is free from mineral acid, especially free from hydrochloric acid.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: July 13, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Spielmann, Georg Schaeffer
  • Patent number: 4336399
    Abstract: A process for producing a carboxylic acid and/or its ester, which comprises reacting an alcohol or ether with carbon monoxide in the presence of elemental nickel or a nickel compound, iodine or an iodine compound and an organic compound of a trivalent nitrogen-group element; wherein the iodine or iodine compound is selected from the following formulae (I) to (IV),RX.sub.n (I)wherein R represents a hydrogen atom or an alkyl or alkylene group, X represents an iodine or bromine atom, and n is an integer of 1 to 3, at least one of n.multidot.X's being an iodine atom,I.sub.2 or I.sub.3 - (II)RCOI (III)wherein R represents an alkyl group,MI.sub.2 (IV)wherein M represents an alkaline earth metal, and the amount of the iodine or iodine compound is such that the amount of the free iodine or iodine compound not chemically bonded to the nickel or nickel compound or the organic compound of a nitrogen-group element is at least 0.
    Type: Grant
    Filed: November 10, 1980
    Date of Patent: June 22, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
  • Patent number: 4335251
    Abstract: The present invention relates to the phenyl-propionic acid ester derivative of the following formula: ##STR1## The compound obtained by the present invention possesses a high degree of analgetic, antipyretic and anti-inflammatory activity and causes little side effects on the gastro-intestinal tracts, when administered orally and topically, and it may be useful as an oral and topical analgesic, antipyretic and anti-inflammatory agent.
    Type: Grant
    Filed: August 5, 1980
    Date of Patent: June 15, 1982
    Assignee: Hisamitsu Pharmaceutical Co. Inc.
    Inventors: Kanji Noda, Akira Nakagawa, Yuji Ishikura, Hiroyuki Ide
  • Patent number: 4335118
    Abstract: Phenylacetates of the formula ##STR1## wherein R.sub.1 is isopropyl or cyclopropyl, R.sub.2 is hydrogen, cyano, ethynyl, prop-1-ynyl or --CSNH.sub.2, and X.sub.1 is hydrogen, methyl, fluorine or chlorine, a process for their production and method of use thereof in pest control.
    Type: Grant
    Filed: October 9, 1980
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hanspeter Fischer, Rudolph C. Thummel, Rudolf Wehrli
  • Patent number: 4334042
    Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: June 8, 1982
    Assignee: Kuraray Co. Ltd.
    Inventors: Mitsuo Matsumoto, Masuhiko Tamura
  • Patent number: 4333950
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: June 8, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4334079
    Abstract: A process for preparing certain substituted benzyl esters of phenylacetic acids by esterification in a solvent in which the salt of the acid is insoluble, and in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: June 8, 1982
    Assignee: Eli Lilly and Company
    Inventors: James M. Greene, Charles A. Bunnell
  • Patent number: 4328356
    Abstract: Esters of arylacetic acids, more particularly lower alcohol esters of arylacetic acids, including those substituted on the methylene group, are prepared by rearrangement of the corresponding alpha-halo-alkylarylketones with Ag compounds in lower alcohols and in an acid medium. From the alkyl esters so prepared, their respective free acids can be obtained, if desired, by various means such as hydrolysis or the shift with mineral acids of the alkaline salts prepared by reaction with alkali, etc.
    Type: Grant
    Filed: February 15, 1980
    Date of Patent: May 4, 1982
    Assignee: Montedison S.p.A.
    Inventors: Claudio Giordano, Francesco Casagrande
  • Patent number: 4325877
    Abstract: 5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF.sub.3, CHF.sub.2 or CH.sub.2 F; R.sub.1 is H or akyl of 1-4 carbon atoms; and R.sub.2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R.sub.1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R.sub.2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R.sub.1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R.sub.2 -5-R.sub.1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br.sup.+ to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e.g., via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: April 20, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Brian W. Metcalf, Jerry L. Adams
  • Patent number: 4323513
    Abstract: This invention is concerned with improving ethylene glycol ester production from the reaction of carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and acyl compound by maintaining the combined concentration of methyl ester, ethylene glycol ester and water in the reaction medium at less than about 30 volume percent. In a preferred embodiment, a continuous process is operated in such a manner that the methyl ester, ethylene glycol ester and water products are removed from the reactor so as to maintain their total volume concentration in the reaction medium at less than about 30 percent.
    Type: Grant
    Filed: November 4, 1980
    Date of Patent: April 6, 1982
    Assignee: Union Carbide Corporation
    Inventor: Bernard D. Dombek
  • Patent number: 4316986
    Abstract: Carboxylic ester and acyl fluoride groups are interchanged in the presence of a metal fluoride catalyst or a metal fluoride/strong sulfonic acid catalyst combination to produce fluorinated mono- and diacyl fluorides.
    Type: Grant
    Filed: September 23, 1980
    Date of Patent: February 23, 1982
    Assignee: E. I. DuPont de Nemours & Company
    Inventors: David C. England, Robert L. Kraft, Carl G. Krespan
  • Patent number: 4316045
    Abstract: A process for the catalytic preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted in liquid medium with an organic peracid in the presence of a catalytic amount of an aryl iodide, to form the desired aryl carboxylate.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventor: Lawrence C. Costa
  • Patent number: 4316044
    Abstract: Isovaleric acid derivatives having the formula ##STR1## wherein typical representations of X is halophenyl, R.sub.1 is hydrogen or cyano, R.sub.2 is hydrogen or lower alkyl, and Y is halophenyl. These derivatives possess insecticidal and acaricidal properties. The process for their preparation is described.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: Nippon Soda Company Limited
    Inventors: Keiichi Ishimitsu, Isamu Kasahara, Tomio Yamada, Michihiko Matsuda, Hidemitsu Takahashi, Shuichi Soma
  • Patent number: 4316046
    Abstract: A process for the preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted with an aryliodoso carboxylate in liquid medium to form the desired aryl carboxylate. Promoters can be employed to increase the rate of reaction and improve selectivity to the aryl carboxylate.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventor: Lawrence C. Costa
  • Patent number: 4313956
    Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: February 2, 1982
    Assignee: INTERx Research Corp.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4311706
    Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: January 19, 1982
    Assignee: INTERx Research Corporation
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4310709
    Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka
  • Patent number: 4310540
    Abstract: Benzyl esters of the formula ##STR1## in which n is 1,2,3,4, or 5,R.sup.2 is hydrogen, C.sub.1-4 -alkyl, cyano or ethynyl,R.sup.3 is the radical of a carboxylic acid customary in pyrethroids or pyrethroid-like compounds, andat least one R.sup.1 is fluoroalkoxy or fluoroalkylmercapto, or two together are fluoromethylene- or fluoroethylene-dioxy, and the others, if present, are hydrogen or various radicals,which possess arthropodicidal properties. Various alcohols, amines, aldehydes, halides, and the like, corresponding to the alcohol moieties of the esters are also synthesized.
    Type: Grant
    Filed: April 16, 1979
    Date of Patent: January 12, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Behrenz, Ingeborg Hammann
  • Patent number: 4310688
    Abstract: The level of hydrolyzable chloride-containing impurities in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by reacting the impurities with a vicinal epoxide-containing compound and then fractionally distilling the mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) in a methylene chloride solution containing 0.084 weight percent of hydrolyzable chloride is contacted with a diglycidyl ether of bisphenol A at 23.degree. C. This reaction mixture is then fractionally distilled to separate the IEM from the methylene chloride first cut and the epoxy resin residue. The hydrolyzable chloride level of the distilled IEM product is only 0.03 weight percent.
    Type: Grant
    Filed: October 22, 1979
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4301044
    Abstract: Zwitterionic surfactant compounds are made readily biodegradable in the environment by the inclusion of a biochemically and/or hydrolytically labile chemical linkage located between the cationic and anionic charge centers of the compounds and anywhere from the second to the tenth atom distant from the cationic charge center. The biodegradable linkage is preferably an ester or amide. The alkoxylated zwitterionic surfactants herein exhibit outstanding particulate soil removal performance and are also effective in removing oily soils from fabrics, in addition to being readily biodegradable. Also described are detergent compositions containing the zwitterionic surfactants, and, optionally containing cosurfactants and detergent builders.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: November 17, 1981
    Assignee: The Procter & Gamble Company
    Inventors: George E. Wentler, Joseph McGrady, Eugene P. Gosselink, William A. Cilley
  • Patent number: 4301084
    Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Bernd Meissner
  • Patent number: 4301062
    Abstract: A novel diester compound of the formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a group of the formula (II): ##STR2## wherein n is an integer of 0 to 4; and m an integer of 1 to 5, is found to be capable of imparting excellent flame-retardancy to various inflammable polymeric materials such as polystyrene, polyester, polyamide, polyphenylene oxide, etc. without deleterious effects on other physical properties of such polymeric materials.
    Type: Grant
    Filed: October 11, 1979
    Date of Patent: November 17, 1981
    Assignee: Asahi Dow Limited
    Inventors: Izumi Yamashita, Kazuo Yoshida, Yuji Kusumi, Kunio Fukuda, Kichiya Tazaki
  • Patent number: 4299844
    Abstract: Anti-inflammatory naphthyl compounds, their preparation and pharmaceutical compositions containing the same. The anti-inflammatory activity has a wide spectrum coupled with low side effects such as gastrointestinal irritancy or oestrongenicity. The compounds possess a chiral center at C-2 and can exist as mixtures of optical isomers or as substantially pure optical isomers.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: November 10, 1981
    Assignee: Beecham Group Limited
    Inventor: Alexander C. Goudie
  • Patent number: 4296244
    Abstract: The present invention provides a novel organic compound, (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid, and a process for the preparation thereof comprising the steps of:a. converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b. cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,c. hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid, andd. hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: October 20, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4289896
    Abstract: Phosphonic acids are suitable catalysts for the transesterification of alkyl esters of carboxylic acids with aliphatic or cycloaliphatic diols containing more than 3 carbon atoms.
    Type: Grant
    Filed: September 17, 1979
    Date of Patent: September 15, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Lothar Buxbaum
  • Patent number: 4289892
    Abstract: Active hydrogen-containing fluorochemical is used as a foam stabilizer for polyurethane foams. For example, rigid or flexible polyurethane foams with high or low density and uniform cellular structure are prepared using fluoroaliphatic radical-substituted poly(oxyalkylene) polyols as foam stabilizers.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: September 15, 1981
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Fredrich A. Soch
  • Patent number: 4288385
    Abstract: The present invention relates to certain novel substituted 2,6-dinitroaniline compounds. It further relates to certain preemergence herbicidal methods employing said novel dinitroanilines for the selective control of certain grasses and broadleaved weeds in the presence of graminaceous crops, especially rice. This invention also relates to the postemergence control of crabgrass and certain broadleaved weeds in the presence of established turf grasses.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Co.
    Inventors: Albert W. Lutz, Robert E. Diehl
  • Patent number: 4285971
    Abstract: Halogenated phenol esters of the formula ##STR1## wherein X represents chlorine or fluorine and R represents hydrogen, alkyl of 1 to 22 carbon atoms, alkenyl of 2 to 22 carbon atoms, benzyl which is unsubstituted or substituted by chlorine or bromine atoms, or phenyl which is unsubstituted or substituted by alkyl or alkoxy, each of 1 to 4 carbon atoms, carboxyl, chlorine and/or bromine. The invention also relates to a method of protecting organic and inorganic material from attack by microorganisms, in particular of providing textiles with an antimicrobial and rotproof finish, of protecting wood from rot, and of preventing the formation of slime in the manufacture of paper.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: August 25, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Rene Muntwyler
  • Patent number: 4283414
    Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: August 11, 1981
    Assignee: ICI Australia Limited
    Inventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
  • Patent number: 4277617
    Abstract: Novel esters in the form of their stereoisomers and mixtures of stereoisomers of the formula ##STR1## wherein X is selected from the group consisting of fluorine, chlorine and bromine R.sub.1 is selected from the group consisting of ##STR2## Y.sub.1 and Y.sub.2 may both be methyl and when Y.sub.1 is hydrogen, Y.sub.2 is selected from the group consisting of ##STR3## and Y.sub.3 and Y.sub.4 are individually selected from the group consisting of fluorine, bromine and chlorine or the group consisting of hydrogen and methyl, Z is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, and when Y.sub.2 is ##STR4## R.sub.2 is selected from the group consisting of ##STR5## A is selected from the group consisting of ##STR6## and when Y.sub.2 is --CHBr--CCl.sub.2 Br, R.sub.2 is m-phenoxy-phenyl and when R.sub.1 is R.sub.1 ' and Y.sub.
    Type: Grant
    Filed: October 13, 1978
    Date of Patent: July 7, 1981
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute, Andre Teche
  • Patent number: 4277494
    Abstract: Acetates of the formula ##STR1## wherein X.sub.1 represents hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, X.sub.2 represents hydrogen or halogen, and Y represents hydrogen, halogen or methyl, processes for their manufacture and a method of controlling pests which comprises the use of these compounds.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: July 7, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Saleem Farooq, Peter Ackermann, Jozef Drabek, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
  • Patent number: 4276225
    Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: June 30, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hellmut Hoffmann
  • Patent number: 4275219
    Abstract: 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: Grant
    Filed: September 24, 1979
    Date of Patent: June 23, 1981
    Assignee: INTERx Research Corporation
    Inventor: Jacob A. Zupan
  • Patent number: 4274998
    Abstract: A novel diester compound of the formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a group of the formula (II): ##STR2## wherein X is bromine atom; Y at least one group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, hydroxyl group and primary, secondary or tertiary amino groups; p an integer of 0 to 4; q an integer of 1 to 4; r an integer 1 to 4 and (q+r) is equal to an integer of not more than 5, is found to be capable of imparting excellent flame-retardancy to various inflammable polymeric materials such as polystyrene, polyester, polyamide, polyphenylene oxide, etc. without deleterious effects on other physical properties of such polymeric materials.
    Type: Grant
    Filed: October 11, 1979
    Date of Patent: June 23, 1981
    Assignee: Asahi-Dow Limited
    Inventors: Izumi Yamashita, Kunio Fukuda, Kichiya Tazaki
  • Patent number: 4271186
    Abstract: The invention relates to certain new stilbene derivatives of the general formula ##STR1## in which R, R.sup.1 and R.sup.2 have the below mentioned meaning, to a process for their preparation and to their use as arthropodicides, especially as insecticides and acaricides.
    Type: Grant
    Filed: June 29, 1979
    Date of Patent: June 2, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Rainer Fuchs, Ingeborg Hammann, Wilhelm Stendel