Plural Rings Patents (Class 562/488)
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Patent number: 5475132Abstract: R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated or hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.Type: GrantFiled: May 27, 1994Date of Patent: December 12, 1995Assignee: Rhone-Poulenc AgrochimieInventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
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Patent number: 5453538Abstract: A process for the manufacture of aromatic dicarboxylic acids is disclosed using a low bromine to metals ratio facilitated by the use of cerium along with the cobalt and manganese catalyst. Aromatic dicarboxylic acids such as terephthalic acid are useful in the manufacture of fiber, films, bottles and molded products.Type: GrantFiled: February 14, 1994Date of Patent: September 26, 1995Assignee: Amoco CorporationInventors: Jeffrey L. Broeker, Walter Partenheimer, Bruce I. Rosen
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Patent number: 5403952Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.Type: GrantFiled: October 8, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
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Patent number: 5354899Abstract: There is disclosed a mass production process of 1,4,5,8-naphthalene tetracarboxylic acid with high collection efficiency. In the presence of an alkaline metallic catalyst, 1,3-butadiene was added to the ethyl radicals of ethyl-p-xylene, and cyclized to 1,4,5,8-tetramethyl-1,2,3,4-tetrahydronaphthalene which was further dehydrogenated and oxidized to obtain 1,4,5,8-naphthalene tetracarboxylic acid, so that a constant supply of inexpensive 1,4,5,8-naphthalene tetracarboxylic acid can be achieved as an intermediate raw material for dye, pigment, resins, or the like.Type: GrantFiled: June 4, 1993Date of Patent: October 11, 1994Assignee: Sumikin Chemical Co.Inventors: Toshio Sato, Ikuo Ito, Kyoichi Takeda
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Patent number: 5334754Abstract: Provided is a process for preparing 2,5-diphenylterephthalic acid, which is useful in preparing certain polyesters, especially liquid-crystalline polyesters. In this process, p-xylene is di-alkylated with cyclohexene to provide 2,5-dicyclo-hexyl-p-xylene, which is in turn dehydrogenated to provide 2,5-diphenylxylene. 2,5-Diphenylxylene is then oxidized to provide 2,5-diphenylterephthalic acid by utilization of a cobaltous/manganous/bromide oxidation system.Type: GrantFiled: August 14, 1992Date of Patent: August 2, 1994Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Ernest W. Arnold, III, Eric J. Fugate, Dewey W. Fuller, Jr.
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Patent number: 5334752Abstract: Novel difunctionalized cyclobutabenzene monomers of the general formula: ##STR1## wherein Z can be hydrogens or a cyclobutane ting; and X and Y are carbox amino, alcohol, isocyanate, acid halide, or bis-acyl fluoride groups. In a particularly preferred embodiment, the cyclobutabenzene derivative is 1,2-dihydrocyclobutabenzene-3,6-carboxylic acid. The difunctionalized cyclobutabenzene monomer can form part of a polymer backbone chain, but has an additional functionality, the butane ring, which can be easily opened to produce strong, covalent bond crosslinking between polymer chains. The crosslinking can be induced simply by heating the polymer to a temperature in excess of 300.degree. C.Type: GrantFiled: July 1, 1992Date of Patent: August 2, 1994Assignee: The Board of Regents acting for and on behalf of University of MichiganInventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker
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Patent number: 5322954Abstract: Disclosed is a method of making a 4-substituted phthalic anhydride. A halomaleic (including halofumaric anhydride (or the acid or ester thereof) is made by the reaction of-maleic anhydride with chlorine or bromine. The halomaleic anhydride is reacted with a conjugated diene to form a first cycloadduct having the formula ##STR1## The first cycloadduct is heated to eliminate HX and produce a second cycloadduct having the formula ##STR2## The second cyclo adduct is dehydrogenated to produce a 4substituted phthalic anhydride which has the formula ##STR3## where R.sub.1, R.sub.2, and R.sub.4 are preferably H and R.sub.3 is preferably Cl or F.Type: GrantFiled: May 28, 1993Date of Patent: June 21, 1994Assignee: Occidental Chemical CorporationInventors: Karl W. Seper, Jeffrey S. Stults, Gary H. Olsen
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Patent number: 5274185Abstract: A high purity naphthalene dicarboxylic acid (NDCA) is easily and rapidly produced by reacting a dialkylester of NDCA within a temperature range of 70.degree.-350.degree. C.Type: GrantFiled: July 13, 1992Date of Patent: December 28, 1993Assignee: Kawasaki Steel CorporationInventors: Tadahiro Yoshino, Tadao Wakui
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Patent number: 5256817Abstract: A method for purifying a naphthalenedicarboxylic acid comprising contacting an impure naphthalenedicarboxylic acid with hydrogen in the presence of a hydrogenation catalyst and a solvent comprising a low molecular weight carboxylic acid, at a temperature of at least about 500.degree. F., and a pressure sufficient to maintain the solvent at least partially in the liquid phase and thereafter recovering purified naphthalenedicarboxylic acid.Type: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Amoco CorporationInventors: David L. Sikkenga, Stephen V. Hoover
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Patent number: 5254719Abstract: A process for preparing purified dimethyl-2,6-naphthalenedicarboxylate by the esterification of 2,6-naphthalenedicarboxylic acid is disclosed, and which process provides for the efficient removal of residual oxidation catalyst metals from the dimethyl-2,6-naphthalenedicarboxylate and efficient removal of particulate contaminants.Type: GrantFiled: May 31, 1991Date of Patent: October 19, 1993Assignee: Amoco CorporationInventors: Juergen K. Holzhauer, David A. Young
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Patent number: 5243067Abstract: A 3,4,3',4'-substituted biphenyl compound represented by the general formula (II): ##STR1## wherein, one of R.sup.1 and R.sup.2 is a -CH.sub.3 group and the one other is a --COOR.sup.5 group, --COOH group, or --COCl group, and one of R.sup.3 and R.sup.4 is a -CH.sub.3 group and the other one is a --COOR.sup.5 group, --COOH group, or --COCl group, is produced by the steps of oxidatively coupling an o-toluic acid alkyl ester in the presence of a catalyst containing a mixture of palladium salts with 1,10-phenanthroline or .alpha.,.alpha.'-bipyridine, a chelating product of a palladium salt with 1,10-phenanthroline, or a chelating products of a palladium salt with .alpha.,.alpha.Type: GrantFiled: February 20, 1991Date of Patent: September 7, 1993Assignee: Ube Industries, Ltd.Inventors: Akinori Shiotani, Michinori Suzuki, Fumio Matsuo
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Patent number: 5202469Abstract: Partially fluorinated dicarboxylic acid and the acid chloride thereof, a process for its preparation and its use.The compound of the formula (I) ##STR1## and the acid chloride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of the ions of cobalt, manganese and bromine in an acid organic medium. The compounds can be used for the preparation of linear polycarboxamides and polycarboxylic acid esters.Type: GrantFiled: June 20, 1991Date of Patent: April 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5185454Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.Type: GrantFiled: October 2, 1990Date of Patent: February 9, 1993Assignee: Bayer AktiengesellschaftInventors: Axel Bader, Dieter Arlt
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Patent number: 5183926Abstract: Aromatic dicarboxylic acids of the formula ##STR1## in which R.sup.1, R.sup.2, m, n, and X have the meaning mentioned in the description,can be prepared from the bisphenols, on which they are based, of the formula ##STR2## if the bisphenols are first reacted to give the bissulphonates, the sulphonate groups are removed catalytically with H.sub.2 and the hydrocarbons obtained in this way are doubly acylated in a known manner and the acyl groups are oxidized to the carboxyl groups.Many of the aromatic dicarboxylic acids which can be prepared in this way are new.Type: GrantFiled: September 13, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventors: Richard Weider, Thomas Scholl
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Patent number: 5183590Abstract: A composition and method for inhibiting corrosion of ferrous metals in contact with an aqueous solution comprising adding to the system from 0.1 to 500 ppm of an aminohydroxysuccinic acid compound selected from group consisting of compounds of the generalized formulas: ##STR1## wherein R is H or C.sub.1 to C.sub.6 alkyl, optionally substituted with --OH, --CO.sub.2 H, --SO.sub.3 H or phenyl, C.sub.4 C.sub.7 cycloalkyl, or phenyl which is optionally substituted with --OH, or --CO.sub.2 H, and R' is H, C.sub.1 to C.sub.6 alkyl, optionally substituted with --OH or CO.sub.2 H; and ##STR2## wherein R' is as above, and Z is selected from the group consisting of i) --(CH.sub.2).sub.n -- wherein n is an integer from 2 to 10, ii) --(CH.sub.2).sub.2 --X--(CH.sub.2).sub.2 -- wherein X is --O--, --S--, --NR"--; wherein R" is selected from the group consisting of H, C.sub.1 to C.sub.6 alkyl, hydroxyalkyl, carboxyallkyl, acyl, --C(O)OR"' wherein R"' is C.sub.1 C.sub.Type: GrantFiled: October 24, 1991Date of Patent: February 2, 1993Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Vladimir Jovancicevic, Judith A. Hartman, Robert P. Kreh
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Patent number: 5183933Abstract: Provided is a continuous process for producing 2,6-naphthalenedicarboxylic acid by the liquid phase oxidation of 2,6-dimethylnaphthalene comprising continuously adding to a reaction zone the oxidation reaction components comprising 2,6-dimethylnaphthalene, a source of molecular oxygen, a solvent comprising an aliphatic monocarboxylic acid, and a catalyst comprising cobalt, manganese and bromine components, wherein the atom ratio of manganese to cobalt is about 5:1 to about 0.3:1, the total of cobalt and manganese is at least about 0.40 weight percent based on the weight of solvent, and maintaining the contents of the reaction zone at a temperature of about 370.degree. F. to about 420.degree. F. and at a pressure sufficient to maintain at least a portion of the monocarboxylic acid in the liquid phase thereby oxidizing the 2,6-dimethylnaphthalene to 2,6-naphthalenedicarboxylic acid.Type: GrantFiled: October 15, 1991Date of Patent: February 2, 1993Assignee: Amoco CorporationInventors: Jon J. Harper, George E. Kuhlmann, Keith D. Larson, Rosemary F. McMahon, Paul A. Sanchez
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Patent number: 5177258Abstract: Biaryl derivatives are produced by coupling an aryl halide in an aqueous alkaline solution in the presence of a palladium catalyst, using formic hydrazide as the reducing agent.Type: GrantFiled: May 21, 1992Date of Patent: January 5, 1993Assignee: Bromine Compounds, Ltd.Inventors: Abram Becker, Ariel A. Ewenson, Bertha Croitoru
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Patent number: 5175352Abstract: A process for preparing 2,6-naphthalenedicarboxylic acid comprising oxidation reaction of 2,6-diisopropylnaphthalene or an oxidation product thereof with molecular oxygen in a solvent containing an aliphatic carboxylic acid in the presence of a catalyst comprising cobalt and manganese as heavy metals and a bromine compound is disclosed, in which said oxidation reaction is carried out in the presence of at least one nitrogen-containing compound selected from the group consisting of a pyridine compound, ammonia, a carboxylic acid ammonium salt, urea, a urea derivative, an amine, and a carboxylic acid amide. 2,6-Naphthalenedicarboxylic acid can be obtained at higher purity and in increased yield.Type: GrantFiled: January 6, 1992Date of Patent: December 29, 1992Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara
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Patent number: 5175354Abstract: The process of this invention for preparing 2,6-naphthalene-dicarboxylic acid comprises a reaction step (Step A) wherein 2,6-naphthalene-dicarboxylic acid potassium salts consisting of 2,6-naphthalene-dicarboxylic acid dipotassium salt and/or 2,6-naphthalene-dicarboxylic acid monopotassium salt are allowed to react with benzene-carboxylic acids in the presence of water to yield 2,6-naphthalene-dicarboxylic acid and benzene-carboxylic acid potassium salts and a separation step (Step B) wherein the crystallized 2,6-naphthalene-dicarboxylic acid is separated from the benzene-carboxylic acid potassium salts dissolved in the aqueous solution and provides 2,6-naphthalene-dicarboxylic acid, useful as raw material for polymers, at low cost on a commerical scale with recycle of potassium.Type: GrantFiled: April 1, 1991Date of Patent: December 29, 1992Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel CorporationInventors: Shuichi Mitamura, Yasuhisa Tsutsumi, Yoshimi Kata, Atsushi Kawada, Naoya Okabayashi
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Patent number: 5153334Abstract: Partially fluorinated tetracarboxylic acid and the dianhydride thereof, a process for their preparation and their useA compound of the formula ##STR1## and the dianhydride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of at least 2 heavy metal salts and also bromine in an acid organic medium. The compounds can be employed for the preparation of partially fluorinated polycondensates, such as polyimides, polycarboxamides, esters of polyamidecarboxylic acids, polyamides and imide-oligomers.Type: GrantFiled: June 20, 1991Date of Patent: October 6, 1992Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5144066Abstract: A method of producing naphthalenedicarboxylic acids by the oxidation of dialkyl-substituted naphthalene with a gas containing molecular oxygen under liquid phase conditions in an organic solvent and in the presence of a catalyst comprising copper and bromine, or a catalyst comprising copper, bromine and at least one kind of element/compound selected from the group of consisting of amine compounds and heavy metallic elements which are vanadium, manganese, iron, cobalt, nickel, palladium and cerium. And a method of producing diaryldicarboxylic acids by the oxidation of dialkyl-substituted diaryl compounds with a gas containing molecular oxygen in an organic solvent and in the presence of the same catalyst. These methods permit high yields of naphthalenedicarboxylic acids of high purity and of diaryldicarboxylic acids of high purity with the use of small amounts of catalyst.Type: GrantFiled: June 25, 1991Date of Patent: September 1, 1992Assignee: Nippon Shokubai Co., Ltd.Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi
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Patent number: 5141959Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is CH.dbd.CY--C(CH.sub.3).dbd.CHX wherein X and Y are different and each is of the formula ##STR2## wherein R' and R" independently are H or alkyl of C.sub.1-6 and R.sub.1 includes all possible geometric isomers are demonstrated effective in treating inflammation, both topically and internally. The mechanism appears to be the inhibition of phospholipase A.sub.2 enzymes.Type: GrantFiled: September 21, 1990Date of Patent: August 25, 1992Assignee: Bristol-Myers Squibb CompanyInventors: F. Ivy Carroll, Anita Lewin, Kenneth Tramposch, Stephen A. Steiner
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Patent number: 5142098Abstract: The invention relates to novel monoesters and diesters of 9,10-endoethano-9,10-dihydroanthracene-11,11-dicarboxylic acid.These novel monoesters and diesters correspond to the following structural chemical formula (II): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and can represent H, an alkali metal or alkaline earth metal atom, a linear or branched alkyl group having from 1 to 6 carbon atoms, an alicyclic group having form 3 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, defined in their cis or trans variety, or an alkynyl group having from 2 to 6 carbon atoms, the said groups optionally being substituted by one or more functional groups such as ether, epoxide, halogeno, cyano, ester, aldehyde, ketone, aryl etc., where R.sup.1 and R.sup.2 cannot be H or ethyl simultaneously. These addition products constitute valuable intermediates for the preparation of methylidenemalonates in high yields and with a high purity.Type: GrantFiled: March 23, 1990Date of Patent: August 25, 1992Assignee: Laboratoires UPSAInventors: Nicole Bru-Magniez, Christian De Cock, Jacques Poupaert, Jean-Luc De Keyser, Pierre Dumont
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Patent number: 5139702Abstract: A composition useful for treating aqueous systems comprising a naphthylamine polycarboxylic acid having the formula: ##STR1## wherein X is CO.sub.2 H or SO.sub.3 H, Y is H, C.sub.1 to C.sub.6 alkyl, CO.sub.2 H or SO.sub.3 H, R is H, C.sub.1 to C.sub.6 alkyl, CO.sub.2 R' or COR', R' is C.sub.1 to C.sub.6 alkyl, n is an integer from 1 to 20, and water soluble salts thereof.Type: GrantFiled: October 24, 1991Date of Patent: August 18, 1992Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Robert P. Kreh, Lai-Duien G. Fan
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Patent number: 5136081Abstract: The invention provides a process for the preparation of fungicidally active cyclopentene derivatives of the general formula ##STR1## cyclopentane derivatives of the general formula ##STR2## and cyclohexane derivatives of the general formula ##STR3## in which n, R, R.sup.1, R.sup.2, R.sup.5, X and Y are as herein defined. Compounds of formula II and III are also provided which are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: September 11, 1989Date of Patent: August 4, 1992Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
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Patent number: 5113010Abstract: The invention is concerned with a novel route for making 4,4'-bis(carboalkoxystilbene) derivatives. The process involved is a variation of the Wittig process and allows the compound to be obtained in a less costly and safer way.Type: GrantFiled: December 11, 1990Date of Patent: May 12, 1992Assignee: Lever Brothers Company, division of Conopco, Inc.Inventors: Matthew E. Langer, Ferial Khorshahi
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Patent number: 5110982Abstract: A process for producing 2,6-naphthalene dicarboxlic acid which comprises oxidizing a 2-alkyl-6-acyl naphthalene with molecular oxygen-containing gas in the presence of a catalyst containing cobalt, manganese and bromine in an acetic acid solvent, characterized in that the oxygen concentration in the exhaust gas is controlled so as to satisfy the following equation:15/(X+7.5)+0.1.ltoreq.Y.ltoreq.90/(X+8)+0.4 (1)wherein Y is oxygen concentration (volume %) in the exhaust gas and X (cm) is a distance between the inlet for an oxygen gas and the surface of the reaction solution in a static state, and the catalyst further contains an aromatic acid in which at least two carboxylic acid groups are in an orthposition or its precursor as a co-catalyst, and that part of all of the mother liquor from which the 2,6-naphthalene dicarboxylic acid crystal has been separated is cooled to remove the precipitated impurities, and thereafter is reused in the oxidation reaction, is disclosed.Type: GrantFiled: January 25, 1991Date of Patent: May 5, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Masato Inari
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Patent number: 5095144Abstract: A process for dimerizing an aromatic halogen compound is disclosed, which comprises the step of: subjecting an aromatic halogen compound having at least one halogen atom bonded to an aromatic nucleus carbon to a dehalogenation-dimerization reaction in the presence of a catalyst, water, a reducing agent, and a halogen acceptor, the catalyst comprising a carrier supported thereon palladium and iron.Type: GrantFiled: July 17, 1990Date of Patent: March 10, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Takahiko Takewaki, Yoshio Katsuro
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Patent number: 5081290Abstract: There is provided a process for the partial oxidation of a polymethylbenzene to the corresponding aromatic polycarboxylic acid, which process comprises contacting in a reaction zone said polymethylbenzene with molecular oxygen in the presence of an oxidation catalyst comprising at least one heavy-metal compound, said heavy-metal compound being acetate free, a source of bromine, and a non-metal acetate compound, the concentration of acetate in the reaction zone being employed to control the rate of oxidation and the selectivity of oxidation.There is also provided the catalyst that is employed in the process.Type: GrantFiled: June 21, 1990Date of Patent: January 14, 1992Assignee: Amoco CorporationInventors: Walter Partenheimer, Diane J. Graziano
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Patent number: 5081281Abstract: Biphenyl tetracarboxlic acid esters and derivatives thereof are prepared by the coupling reaction of 4-halogen substituted o-benzenedicarboxylic acid ester, carried out in an aprotic polar solvent in the presence of a pre-prepared triphenylphosphine-nickel chloride or trialkylphosphine-nickel chloride catalyst, zinc powder as the reducing agent, and an alkali metal halide promoting agent. The ester may be hydrolyzed in basic solution to afford the corresponding acid. The acid may be heated or boiled with acetic anhydride to afford the biphenyl dianhydride.Type: GrantFiled: October 6, 1989Date of Patent: January 14, 1992Assignee: Changchun Institute of Applied ChemistryInventors: Mengxian Ding, Zugiang Wang, Zhenghua Yang, Jing Zhang
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Patent number: 5055612Abstract: A process for the preparation of naphthalene mono or polycarboxylic acids, such as 2,6-naphthalene dicarboxylic acid, is disclosed which includes oxidizing a naphthalene compound such as 2,6-diisopropylnaphthalene in a specific solvent with molecular oxygen in the presence of a catalyst containing a heavy metal compound and a bromine compound. The solvent is an aliphatic monocarboxylic acid and may further contain benzene and/or water. By controlling the ratio of the amount of catalyst metal to the feed rate of the raw material naphthalene compound, the yield of desired product can be controlled.Type: GrantFiled: December 19, 1989Date of Patent: October 8, 1991Assignees: NKK Corporation, Chiyoda CorporationInventors: Yakudo Tachibana, Kazuhiko Tate, Masami Ono, Nobuhiro Takei, Jun Miki, Hiroaki Taniguchi, Yoshimi Shiroto, Misunori Shimura, Yoshio Fukui
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Patent number: 5047560Abstract: Highly pure 3,3',4,4'-biphenyltetracarboxylic acid (BPTA) and dianhydride thereof (BPDA) are produced by heating crude BPTA to give BPDA, treating the BPDA with hot water to give highly pure BPTA, and in the case of highly pure BPDA, heat treating the pure BPTA to give highly pure BPDA.Type: GrantFiled: March 9, 1990Date of Patent: September 10, 1991Assignees: Hitachi, Ltd., Japan Carlit Co., Ltd., Kanto KoatsuInventors: Fusaji Shoji, Nobuo Aoki, Jun Kurita, Tsuyoshi Aoyama, Toshiyuki Kiriyu, Yoshinori Matsuzaki
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Patent number: 4987238Abstract: A process for the preparation of high-purity perfluorinated compounds, specifically of an aromatic tetracarboxylic acid and its anhydride, 5,5'-[2,2,2-trifluoro-1-(trifluoromethyl)-ethylidene]bis-1,3-isobenzofuran dione, by a multi-step treatment of the crude compounds. The metal ion content of the compounds treated is reduced considerably. After polymerization with an aromatic diamine, the anhydride is used in microelectronics.Type: GrantFiled: August 2, 1989Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventor: Freimund Rohrscheid
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Patent number: 4965394Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: May 23, 1989Date of Patent: October 23, 1990Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4950786Abstract: A method for making 2,6-naphthalene dicarboxylic acid by the oxidation of 2,6-diisopropylnaphthalene or its oxidation derivatives in the presence of a catalyst comprising cobalt, manganese, cerium and bromine components is disclosed.Type: GrantFiled: May 4, 1989Date of Patent: August 21, 1990Assignee: Amoco CorporationInventors: Paul A. Sanchez, David A. Young, George E. Kuhlmann, Walter Partenheimer, Wayne P. Schammel
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Patent number: 4942257Abstract: A method of manufacturing an alkali metal salt of 2,3,6,7-naphthalenetetracarboxylic acid. Either a sodium salt or a mixture of sodium salt and potassium salt of at least one naphthalenecarboxylic acid selected form the group consisting of naphthoic acids and naphthalenepolycarboxylic acids is heated to an elevated temperature in an inert gas atmosphere in the presence of a Henkel reaction catalyst and halogenated sodium.Type: GrantFiled: August 31, 1989Date of Patent: July 17, 1990Assignee: NKK CorporationInventors: Yakudo Tachibana, Kazuhiko Tate, Toshifumi Suzuki, Kouji Chiba
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Patent number: 4933491Abstract: A method for purifying a naphthalene dicarboxylic acid produced by the liquid phase oxidation of a kialkylnaphthalene or partially oxidized derivative thereof in the presence of a catalyst comprising a bromine-containing component and at least one of a cobalt- or manganese-containing component.Type: GrantFiled: October 2, 1989Date of Patent: June 12, 1990Assignee: Amoco CorporationInventors: Rusins Albertins, Stephen J. Pietsch, Juergen K. Holzhauer, Hobe Schroeder
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Patent number: 4931584Abstract: The invention relates to novel monoesters and diesters of 9,10-endoethano-9,10-dihydroanthracene-11,11-dicarboxylic acid.These novel monoesters and diesters correspond to the following structural chemical formula (II): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and can represent H, an alkali metal or alkaline earth metal atom, a linear or branched alkyl group having from 1 to 6 carbon atoms, an alicyclic group having from 3 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, defined in their cis or trans variety, or an alkynyl group having from 2 to 6 carbon atoms, the said groups optionally being substituted by one or more functional groups such as ether, epoxide, halogeno, cyano, ester, aldehyde, ketone, aryl etc., where R.sup.1 and R.sup.2 cannot be H or ethyl simultaneously. These addition products constitute valuable intermediates for the preparation of methylidenemalonates in high yields and with a high purity.Type: GrantFiled: March 1, 1988Date of Patent: June 5, 1990Assignee: Laboratoires UPSAInventors: Nicole Bru-Magniez, Christian De Cock, Jacques Poupaert, Jean-Luc De Keyser, Pierre Dumont
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Patent number: 4925977Abstract: An improved method for the preparation of a naphthalene dicarboxylic acid by liquid-phase catalytic oxidation of a diisopropylnaphthalene in a lower fatty acid-based solvent is disclosed wherein a catalyst system comprising bromine and the heavy metals cerium, cobalt, and manganese is used. The cerium compound used as a cerium source for the catalyst can be recovered from crystals of the naphthalene dicarboxylic acid product by dissolving the crystals in an alkali solution and separating the cerium compound as insolubles from the solution.Type: GrantFiled: December 15, 1988Date of Patent: May 15, 1990Assignee: Sumikin Chemical Co., Ltd.Inventors: Teruaki Yamada, Yoshiji Doko, Kazuki Sugiura
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Patent number: 4912233Abstract: Disclosed are a para- or meta-terphenyl-3,4,3",4"-tetracarboxylic acid or a dianhydride and a process for preparing the same. The para- or meta-terphenyl-3,4,3",4"-tetracarboxylic acid or a dianhydride thereof according to the present invention is a novel compound which is useful as a raw material for a polyimide having higher heat resistance and so on.Type: GrantFiled: October 21, 1988Date of Patent: March 27, 1990Assignee: Hitachi Chemical Company, Ltd.Inventors: Tohru Kikuchi, Toshiyuki Fujita, Takayuki Saito
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Patent number: 4900843Abstract: A method of dehalogeno-dimerizing an aromatic halide compound substituted by at least one halogen atom substituted on the aromatic ring using a palladium catalyst on support in the presence of water, a reducing agent and a halogen acceptor is disclosed. The method is characterized by using the palladium catalyst on support immersed in a hydrohalogenic acid prior to the dehalogeno-dimerization reaction.Type: GrantFiled: May 31, 1988Date of Patent: February 13, 1990Assignee: Mitsubishi Chemical Industries LimitedInventors: Mitsumasa Kitai, Yoshio Katsuro, Shigenori Kawamura, Masumi Hino, Keiichi Sato
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4895975Abstract: A diacetylene compound of the formula: ##STR1## wherein X is a hydroxyl group, a halogen atom, an alkoxy group, a monovalent hydrocarbon group having from 1 to 20 carbon atoms or a --OM group wherein M is an alkali metal, and each of Y.sub.1 and Y.sub.2 which may be the same or different is a hydrogen atom, a monovalent organic group having from 1 to 20 carbon atoms or a halogen atom.Further described a process for producing a polymer containing diacetylene group in its main chain using a diacetylene compound of the above.Type: GrantFiled: March 9, 1988Date of Patent: January 23, 1990Assignee: Kozo Iizuka, Director-General of Agency of Industrial Science and TechnologyInventor: Eisuke Fujiwara
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Patent number: 4883898Abstract: A new class of chemiluminescent compounds is described which has the ability to emit light which corresponds to the fluorescence of the compounds' breakdown products. This chemiluminescence is stimulated by the energetic decomposition of the chemiluminescent compound. These chemiluminescent compounds have the following structure: ##STR1## wherein X is hydrogen or an electron-withdrawing group; and Y is hydrogen or an electron-withdrawing group and both X and Y are not hydrogen.Type: GrantFiled: December 10, 1987Date of Patent: November 28, 1989Assignee: University of ChicagoInventor: Nien-chu C. Yang
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Patent number: 4873366Abstract: Disclosed in the present invention is a process for producing 2,6-naphthalenedicarboxylic acid comprising oxidizing 2,6-diisopropylnaphthalene or its partially oxidized intermediate with molecular oxygen in a solvent containing at least 50% by weight of an aliphatic monocarboxylic acid, having not more than three carbon atoms, in the presence of a catalyst composed of (i) a heavy metal comprising cobalt and/or manganese and (ii) bromine, and a salt of an inorganic acid having an acid dissociation constant Ka smaller than 1.34.times.10.sup.-5 (at 25.degree. C.) and a vapor pressure lower than that of the aliphatic monocarboxylic acid used as the solvent. According to the process of this invention, 2,6-naphthalenedicarboxylic acid of high bulk density can be obtained in a high yield and with high purity.Type: GrantFiled: April 5, 1988Date of Patent: October 10, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Toshiharu Matsuda, Atsushi Sasakawa, Shoichiro Hayashi, Yutaka Konai
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Patent number: 4863640Abstract: Fluorinated aromatic hydrocarbons including fluorinated aromatic carboxylic acids fluorinated aromatic dianhydrides and fluorinated aromatic dialkyl esters that serve as precursor monomers for high temperature fluorinated polyimides. The fluorinated aromatic carboxylic acid monomer comprises: ##STR1## wherein X is hydrogen, carboxyl, sulfonic acid, hydroxy, alkyl, halogen or nitro and hydrates of said acids. The fluorinated aromatic dianhydride monomer comprises: ##STR2## wherein x is hydrogen, carboxyl, sulfonic acid, hydroxy, alkyl, halogen or nitro. The fluorinated aromatic dialkyl ester monomer comprises: ##STR3## wherein X is hydrogen, carboxyl, sulfonic acid, hydroxy, alkyl, halogen or nitro and Y is an alkyl group and hydrates of said esters.Type: GrantFiled: May 27, 1986Date of Patent: September 5, 1989Assignee: United Technologies CorporationInventor: Daniel A. Scola
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Patent number: 4847407Abstract: Disclosed are phenyl esters of stilbenedicarboxylic acid. The carboxylate portions of the compounds are bonded at the meta or para positions of the stilbene moiety.Type: GrantFiled: September 15, 1988Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventor: John C. Morris
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Patent number: 4820868Abstract: Disclosed is a process for the preparation of a naphthalene-2,6-dicarboxylic acid dialkali metal salt which comprises heating an alkali metal salt of naphthoic acid and/or a dialkali metal salt of naphthalene-dicarboxylic acid under pressure with carbon dioxide gas in the presence of a catalyst, wherein an aprotic polycyclic aromatic compound having 2 or 3 rings is used as a reaction medium. Naphthalene-2,6-dicarboxylic acid dialkali metal salt can be obtained in high yield and selectivity with a good reproducibility of the reaction.Type: GrantFiled: September 29, 1986Date of Patent: April 11, 1989Assignee: Nippon Steel CorporationInventors: Shuichi Mitamura, Koichi Fujishiro, Hiroharu Inoue
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Patent number: 4818771Abstract: Diphenic acid bis(dicyclohexylamide) represented by the following formula: ##STR1## A process for producing diphenic acid bis(dicyclohexylamide) represented by the above formula, which comprises dimerizing a diazonium salt of o-aminobenzoic acid in the presence of a reducing agent, followed by acidification to give 2,6'-dicarboxylbiphenyl; converting this dicarboxylic acid to 2,6'-dichloroformylbiphenyl by chlorination; and reacting this acid chloride with dicyclohexylamine.Sustained release antimicrobial compositions comprising a clathrate compound consisting of a microbial agent and diphenic acid bis(dicyclohexylamide) represented by the above formula.Type: GrantFiled: December 12, 1986Date of Patent: April 4, 1989Assignee: Kurita Water Industries, Ltd.Inventors: Fumio Toda, Ayako Sekikawa, Hideo Sugi, Kenji Tahara
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Patent number: 4814472Abstract: There are disclosed diethynylated diphenyl hexafluoropropane compounds, which are suitable for forming copolymers and carbon-carbon composites. These compounds are prepared in high yields by first providing a dihalogenated diphenyl hexafluoropropane compound, coupling the dihalogenated compound with ethynyltrimethylsilane in the presence of an organometallic catalyst to form a silylated ethynyl terminated diphenyl substituted compound and subsequently desilylating the compound to form the desired diethynylated diphenyl hexafluoropropane compound.Type: GrantFiled: February 14, 1985Date of Patent: March 21, 1989Assignee: Hughes Aircraft CompanyInventor: Kreisler S. Y. Lau