Polycarboxylic Acid Patents (Class 560/146)
  • Patent number: 5078907
    Abstract: A bleach precursor compound, its peroxygen derivative, and detergent compositions containing these materials are disclosed herein. The bleach precursors structurally comprise a pair of different diesters, one ester containing an electrically-charged functional group. Perhydrolysis of the precursor in the presence of hydrogen peroxide and a basic aqueous media generates a peroxycarboxylic acid.
    Type: Grant
    Filed: November 1, 1989
    Date of Patent: January 7, 1992
    Assignee: Lever Brothers Company, division of Conopco, Inc.
    Inventors: Stephen A. Madison, Pamela C. Lam
  • Patent number: 4959391
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: September 25, 1990
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
  • Patent number: 4918213
    Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
  • Patent number: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4847376
    Abstract: The present invention provides a lipase substrate of the general formula: ##STR1## wherein A is an alkylene or alkenylene radical containing up to 16 carbon atoms, R and R.sub.1, which can be the same or different, each signify an alkyl, alkenyl or acyl radical containing up to 20 carbon atoms or an optionally alkyl-substituted aryl or aralkyl radical containing up to 8 carbon atoms in the alkyl moiety and wherein one of R and R.sub.1 can also be a hydrogen atom, X is the residue of an aromatic hydroxy or thiol compound, and each Y and Z, independently from each other, is --S-- or --O--, Z also --CH.sub.2 --.The present invention also provides a process and a reagent for the optical determination of lipase.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: July 11, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ulrich Neumann, Martina Junius, Hans-Georg Batz
  • Patent number: 4772745
    Abstract: Photosensitive anthracene compounds containing two anthracene rings joined by a flexible linkage, and containing a functional group as an annular substituent on one of the anthracene rings, react with polymers to form materials useful in information proceedings.
    Type: Grant
    Filed: August 18, 1986
    Date of Patent: September 20, 1988
    Assignee: The United States of America as represented by the Secretary of Commerce
    Inventors: Qui Tran-Cong, Charles C. Han
  • Patent number: 4760087
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: July 26, 1988
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
  • Patent number: 4739079
    Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 19, 1988
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4684737
    Abstract: A process for producing a substituted phthalic acid which comprises heating a substituted tetrahydrophthalic acid compound having a substituent in at least one of the 3-, 4-, 5- and 6-positions in the presence of sulfur to dehydrogenate it, and heat-treating the product in the presence of water optionally together with an organic solvent. As required, the heat-treated product is dehydrocyclized to form a substituted phthalic acid anhydride.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: August 4, 1987
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Hiroshi Horino, Michiro Ohnaka, Atsushi Hayashi, Yoshiko Ikeno
  • Patent number: 4632785
    Abstract: Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids of half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids.Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20.degree. C.) which makes the present method particularly suitable to systems for molding polyisocyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: December 30, 1986
    Assignee: The Dow Chemical Company
    Inventor: Edward A. Barsa
  • Patent number: 4612386
    Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: September 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga
  • 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: 4547582
    Abstract: A method of producing alkyl 3-hydroxy-4-(4-hydroxyphenoxy)pentanoate which comprises the steps of: (a) reacting 4-benzyloxyphenol with an alkali hydroxide and 2-chloropropionic acid in the presence of a suitable solvent and at a temperature sufficient to cause formation of 2-(4-benzyloxyphenoxy)propionic acid; (b) reacting said 2-(4-benzyloxyphenoxy)propionic acid with a compound selected from phosgene, oxalyl chloride, thionyl chloride, or phosphorus trichloride, in the presence of a suitable catalyst and solvent and at a temperature sufficient to cause formation of 2-(4-benzyloxyphenoxy)propionyl chloride; (c) reacting said 2-(4-benzyloxyphenoxy)propionyl chloride with 2,2-dimethyl-1,3-dioxan-4,6-dione and pyridine, all in the presence of a suitable solvent and at a temperature sufficient to cause formation of 5-[2-(4-benzyloxyphenoxy)propionyl]-2,2-dimethyl-1,3-dioxan-4,6-dione; (d) reacting said 5-[2-(4-benzyloxyphenoxy)propionyl]-2,2-dimethyl-1,3-dioxan-4,6-dione with an alkyl alcohol for a period of tim
    Type: Grant
    Filed: October 5, 1984
    Date of Patent: October 15, 1985
    Assignee: Stauffer Chemical Company
    Inventor: Peter K. Wehrenberg
  • Patent number: 4521614
    Abstract: Esters, e.g., alkyl adipates, are facilely prepared by carbonylation among an alcohol, carbon monoxide and a monoolefin, e.g., an alkyl pentenoate, in the presence of a catalytically effective amount of cobalt and a tertiary nitrogen base, and optionally hydrogen, said reaction being carried out in an aromatic hydrocarbon reaction medium bearing from 1 to 3 nuclear substituents, and said substituents comprising cyano or a radical of the formula R--Y-- having up to 20 carbon atoms, wherein Y is a direct valence bond, an oxygen atom, a sulfur atom, a carbonyl group or a carbonyloxy group (--CO--O--), with R being bonded to the oxygen of the group --CO--O--, and R is alkyl, aralkyl or or aryl, or a cyano substituted such R--Y-- radical, or a radical R--Y-- which includes one of the divalent bridges --O--, --CO-- or --CO--O-- along its skeletal carbon chain, with the proviso that at least one of said substituents is either cyano or a radical R--Y-- wherein Y is other than a direct valence bond.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: June 4, 1985
    Assignee: Rhone-Poulenc Chimie De Base
    Inventor: Jean Jenck
  • Patent number: 4504418
    Abstract: Biodegradable non-ionic surface-active agents containing carbonate groups or residues of carboxylic esters can be prepared by reacting hydrophilic polyoxyalkylene glycols derived from the same or different alkylene oxide glycols with monofunctional alcohols. The compositions of the invention contain both hydrophilic and hydrophobic groups in the molecule making them suitable for use as surface-active agents. The residues of the monofunctional alcohols provide hydrophobic groups in the molecule of the surface-active agent.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: March 12, 1985
    Assignee: BASF Wyandotte Corporation
    Inventor: William K. Langdon
  • Patent number: 4500463
    Abstract: Polyprenyl carboxylic acid derivatives having the general formula (I): ##STR1## in which n is an integer of from 2 to 4, R.sub.1 represents the hydrogen atom or a protecting group for the carboxylic acid group, and R.sub.2 represents a hydroxymethyl, formyl or carboxyl group, are disclosed. A process for the preparation of the polyprenyl carboxylic acid derivative involving microbiological oxidation using a strain belonging to the genus Nocardia is disclosed. The compounds have anti-ulcer activity and hypotensive activity. The compounds also are useful as intermediates for preparing polyprenyl carboxylic acids of the formula ##STR2## and esters thereof, wherein l is an integer of from 4 to 11. The polyprenyl carboxylic acids and esters thereof have hypotensive activity and anti-ulcer activity.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: February 19, 1985
    Assignees: Eisai Co., Ltd., Agency of Industrial Science & Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Yuichi Inai, Yoshiyuki Kohara, Yoshiyuki Kawakami, Tomio Tsurugi
  • Patent number: 4451664
    Abstract: An improved process for preparing diaryl esters of a monohydroxy aromatic compound with dicarboxylic acids is disclosed, in which the esterification reaction is optimized by continuously removing water and/or other by-products of the reaction from the reactor, while supplying to the reactor a make-up amount of the monohydroxy aromatic compound containing no more than about 100 ppm of water. The make-up stream may be obtained by stripping the by-product stream of water and other by-products of the reaction.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: May 29, 1984
    Assignee: Occidental Chemical Corporation
    Inventor: Gautam R. Ranade
  • Patent number: 4381307
    Abstract: Novel derivatives of known bio-affecting carboxylic acids R-COOH are disclosed, said derivatives having the structural formula ##STR1## wherein Y and Y' are each H or C.sub.1 -C.sub.4 alkyl; n is 0 or 1; R.sub.1 and R.sub.2 are each selected from a variety of unsubstituted or substituted hydrocarbon radicals, or are combined so that --NR.sub.1 R.sub.2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R.sub.3 is H or one of a variety of other substituents. Salts and N-oxides of compounds of formula (I) and the corresponding diacyloxy derivatives of known bio-affecting carboxylic acids HOOC-R'-COOH are disclosed also.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: April 26, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Kenneth B. Sloan
  • 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: 4361703
    Abstract: N-acetyl-para-aminophenyl N'acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl-N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
    Type: Grant
    Filed: March 23, 1981
    Date of Patent: November 30, 1982
    Assignee: Sterling Drug Inc.
    Inventors: George Margetts, Roderic S. Andrews, Jean Legros
  • Patent number: 4315830
    Abstract: A method for altering the characteristics of liquid telechelic polymers by means of reducing the reactive group content and adjusting the viscosity of a given liquid telechelic polymer. This is accomplished by means of a two stage process which comprises reacting some of the polymer's available reactive groups with a difunctional reactant and adding a diluent to produce a final composition of desired viscosity and reactive group content.
    Type: Grant
    Filed: January 19, 1972
    Date of Patent: February 16, 1982
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: David M. French, J. T. L. Rosborough, Clyde J. Swedenberg
  • 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: 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: 4311850
    Abstract: Muconic acid monoesters of alkanediols of 2-6 carbons and of phenol are prepared by copper (II) oxidative cleavage of phenols, catechols or orthobenzoquinones. The products are useful as comonomers in polyamides and other polymers. The alkanediol or phenol is introduced into the copper (II) reactant or catalyst.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: January 19, 1982
    Assignee: Allied Corporation
    Inventors: Timothy R. Demmin, Milorad M. Rogic
  • 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: 4293555
    Abstract: Disclosed are 6- and 6,6-disubstituted-2-substituted-oxapen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from hydrogen, alkyl, alkoxyl, aralkyl, aryl, heterocyclyl and heterocyclylalkyl; R is selected from hydrogen, --OR, --SR, --NR.sub.2, alkyl, aryl, aralkyl, heterocyclyl, or heterocyclylalkyl. Such compounds and their pharmaceutically acceptable salt, and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: October 10, 1979
    Date of Patent: October 6, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Frank P. DiNinno
  • Patent number: 4282151
    Abstract: New reactive asymmetrical dicarboxylic acid ester compounds of the formula ##STR1## wherein R.sub.1 is an alkyl radical containing up to 3 carbon atoms or is a digoxin or digitoxin residue, R.sub.2 and R.sub.3, which may be the same or different, are alkoxy radicals containing up to 3 carbon atoms or together represent an oxygen atom, X is a cyanomethoxy, succinimide-N-oxy, N-methyl-pyridiniumoxy, 2,4-dinitrophenoxy, 2,4,5-trichlorophenoxy, pentachlorophenoxy, phenylthio, p-nitrophenoxy, n-nitrophenylthio, piperidyl-N-oxy, phthalimido-N-oxy or benztriazol-N-oxy radical and n is 2, 3, 4 or 5, are useful for the preparation of reagents for the investigation of cardiac glycosides (Digitalis glycosides).
    Type: Grant
    Filed: March 6, 1978
    Date of Patent: August 4, 1981
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans-Georg Batz, Hans-Ralf Linke, Klaus Stellner, Gunter Wiemann
  • Patent number: 4282373
    Abstract: Compounds of the formula (II): ##STR1## wherein X is halogen, hydroxyl or functionalized hydroxyl; Y is halogen, hydroxyl or alkoxy; R.sup.1 is a carboxylic acid group and ester thereof and amide derivative thereof or cyano; and R.sup.2 is hydrogen, a hydrocarbon, a heterocycle, a carboxylic acid group, a carboxylic acid ester, a carboxylic acid amide derivative, acyl, cyano, isocyano or an optionally substituted imine of the formula --CH.dbd.NZ or --N.dbd.CH.sub.2 wherein Z is hydrogen, alkyl, aryl, sulphonyl, --SR.sup.a, sulphoxide --SR.sup.a, or sulphonate --SR.sup.a wherein R.sup.a is alkyl of 1 to 6 carbon atoms or aryl, are useful as intermediates for the ultimate production of penicillins or cephalosporins.
    Type: Grant
    Filed: May 7, 1979
    Date of Patent: August 4, 1981
    Assignee: Beecham Group Limited
    Inventors: Angela W. Guest, Andrew W. Taylor, Robert Ramage
  • Patent number: 4271311
    Abstract: Esterification of phenolic compounds which comprises reacting a phenolic compound and a carboxylic acid using a catalyst consisting essentially of an alkali metal compound and a boron compound wherein said alkali metal compound is at least one member selected from the group consisting of alkali metal salts of boric acid, alkali metal polyborates, alkali metal hydroxides, and alkali metal borohydrides and said boron compound is at least one member selected from the group consisting of boric acid, boric anhydride, alkali metal polyborates, alkali metal salts of boric acid and alkali metal borohydrides.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company (Indiana)
    Inventors: William W. Knickmeyer, James Spanswick, James R. Stephens
  • Patent number: 4243572
    Abstract: A plasticizer for polyvinyl butyral wherein the plasticizer is an alkyl alkylaryl adipate and particularly a benzyl alkyl adipate. The plasticized polyvinyl butyral is specially useful in the manufacture of transparent sheets and particularly as an interlayer for laminated safety glass.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: January 6, 1981
    Assignee: Saint-Gobain Industries
    Inventor: Daniel Dages
  • Patent number: 4234740
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as the starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal or a salt thereof; a compound selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid; and a halogen compound.
    Type: Grant
    Filed: November 28, 1978
    Date of Patent: November 18, 1980
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga, Takumi Kadota
  • Patent number: 4234733
    Abstract: A process for producing an aliphatic carboxylic acid and an aliphatic carboxylic acid esters ofa phenol which comprises reacting a phenol of the general formula ##STR1## wherein n is an integer of 1 to 6, m is an integer of 0 to 5, the sum of n and m is 6, and R represents hydrogen, alkyl, aryl, alkenyl, carbinol, acyl, acyloxy, formyl, carboxy, halogen, sulfo, nitro, nitroso, amino, amido, or cyano, and two or more R groups may be the same or different, and the substituents R may be bonded to each other to form a penta- or hexa-carboxylic or heterocyclic ring, and an aliphatic carboxylic acid ester or an aliphatic ether with carbon monoxide, and separating and recovering the aliphatic carboxylic acid from the reaction mixture.
    Type: Grant
    Filed: October 24, 1978
    Date of Patent: November 18, 1980
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4227015
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4208341
    Abstract: Muconic acid monoesters of alkanediols of 2-6 carbons and of phenol are prepared by copper (II) oxidative cleavage of phenols, catechols or orthobenzoquinones. The products are useful as comonomers in polyamides and other polymers. The alkanediol or phenol is introduced into the copper (II) reactant or catalyst.
    Type: Grant
    Filed: January 8, 1979
    Date of Patent: June 17, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Timothy R. Demmin, Milorad M. Rogic
  • Patent number: 4145559
    Abstract: Esters of 4-substituted 2-methyleneglutaric acids are prepared by reacting an ester of acrylic acid with an ester of an .alpha.-substituted acrylic acid, such as an ester of methacrylic acid, in the presence of a tertiary organic phosphine, an organic phosphorus triamide, an organic phosphonous diamide, or an organic phosphinous amide.
    Type: Grant
    Filed: November 6, 1974
    Date of Patent: March 20, 1979
    Assignee: Rohm and Haas Company
    Inventors: Joseph W. Nemec, Richard B. Wuchter
  • Patent number: 4138580
    Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as a starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal in combination with one or more compounds selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid.
    Type: Grant
    Filed: September 29, 1977
    Date of Patent: February 6, 1979
    Assignee: Ube Industries, Ltd.
    Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga
  • Patent number: 4129586
    Abstract: Compounds which contain azo or peroxide linkages as well as the radical of an ultraviolet light stabilizing group are described. These compounds function as polymerization initiators which cause an ultraviolet light stabilization group to be chemically bound to the polymer.
    Type: Grant
    Filed: June 6, 1977
    Date of Patent: December 12, 1978
    Assignee: Pennwalt Corporation
    Inventors: Chester S. Sheppard, Ronald E. MacLeay
  • Patent number: 4086338
    Abstract: New carboxyalkylacylamino acids which are derivatives of proline, pipecolic acid and azetidine-2-carboxylic acid and have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: February 11, 1977
    Date of Patent: April 25, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David W. Cushman, Miguel Angel Ondetti
  • Patent number: 4062788
    Abstract: Lubricating compositions are provided which comprise a major amount of oil of lubricating viscosity and an effective amount of dichlorophenyl esters of hydrocarbyl dicarboxylic acids. The lubricating compositions have improved load-bearing properties. Also provided are novel dichlorophenyl esters of malonic and lower alkyl substituted malonic acid.
    Type: Grant
    Filed: August 16, 1976
    Date of Patent: December 13, 1977
    Assignee: Shell Oil Company
    Inventor: Hendrik Schadenberg
  • Patent number: 4056543
    Abstract: Methylenemalonates are prepared by reacting a substituted norbornene with an electrophilic material in the presence of a lithium amide complex and pyrolyzing. The resulting acrylates are useful as fast setting, polymerizable adhesives.
    Type: Grant
    Filed: September 7, 1976
    Date of Patent: November 1, 1977
    Assignee: Eastman Kodak Company
    Inventor: Ignazio Salvatore Ponticello
  • Patent number: 4053430
    Abstract: This invention relates to novel water-soluble esters of oxalic acid, and to compositions that are useful for generating chemiluminescent emission by reacting said esters of oxalic acid with hydrogen peroxide in the presence of water and a fluorescent compound, and to a process for generating chemiluminescent emission by using said compositions.
    Type: Grant
    Filed: July 16, 1976
    Date of Patent: October 11, 1977
    Assignee: American Cyanamid Company
    Inventor: Arthur Gaudens Mohan