Unsaturated Patents (Class 562/595)
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Patent number: 5149695Abstract: Fumaric acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a metallic cation, andR.sub.2 is a saturated or unsaturated aliphatic C.sub.6 -C.sub.24 alkyl group, psoralen-9-yl, retinyl, .alpha.-tocopheryl (vitamin E), calciferyl, corticosteroid-21-yl or monosaccharid-.omega.-yl; a group of fumaric acid derivatives based on glycerol, alkane diol or polyol molecules; and fumaric acid derivatives of the formula ##STR2## wherein n is an integer from to 30 to 260,R.sub.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group,R.sub.4 is one of the R.sub.3 groups and n is the number of molecule repetitions, processes for their production and compositions containing same are described. These compounds are useful as drugs for the treatment of cryptogenically-caused diseases and have antisporiatic as well as antimicrobial action.Type: GrantFiled: March 13, 1989Date of Patent: September 22, 1992Inventors: Peter P. Speiser, Rajendra K. Joshi
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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: 5106541Abstract: Oligomers and addition products obtained from the reaction of a saturated or olefinically unsaturated carboxylic acid, alcohol, ether, or ester with a substituted or unsubstituted acetic anhydride in the presence of a Mn compound, and processes for their preparation.Type: GrantFiled: January 9, 1990Date of Patent: April 21, 1992Assignee: Henkel Research CorporationInventors: William E. Fristad, Alan G. Olivero, Steven Young, Christopher S. Sykes, Brock M. Siegel
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Patent number: 5099034Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are --COOR.sup.4, --COOR.sup.5, and --COOR.sup.6, respectively; R.sup.4, R.sup.5, and R.sup.6 each is hydrogen, lower alkyl, or alkali metal; W is hydroxyl; X, Y, and Z each is hydrogen or hydroxyl; a dotted line indicates the presence or absence of a single bond; or where W/R.sup.3, X/R.sup.1, and/or Z/R.sup.3 may be combined together, a lactone is formed, which compound is useful as a phospholipase A.sub.2 inhibitor. Process for the production of the compound (I) and a cell culture of a microorganism Circinotrichum falcatisporum RF-641 producing the same are also provided.Type: GrantFiled: June 27, 1990Date of Patent: March 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadashi Yoshida, Hiroshi Itazaki, Hitoshi Arita, Yoshimi Kawamura, Koichi Matsumoto
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Patent number: 5081292Abstract: .beta., .gamma.-Unsaturated carboxylic acids, e.g., 3-hexene-1,6-dioic acid, are selectively prepared by carbonylating (with carbon monoxide) an allyl alcohol, e.g., a butenediol, at an elevated temperature and under superatmospheric pressure, in the presence of a catalytically effective amount of a palladium-based catalyst and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: January 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean Jenck, Robert Perron
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Patent number: 5077433Abstract: The hexene-1,6-dioic acids, e.g., hex-3-ene-1,6-dioic acid, are prepared by reacting carbon monoxide and water with at least one diacyloxylated butene, in the presence of a catalytically effective amount of palladium and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: December 31, 1991Assignee: Rhone-Poulenc ChimieInventors: Jean Jenck, Philippe Denis, Philippe Kalck, Helene Deweerdt
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Patent number: 5064563Abstract: A specially defined amount of hydrogen peroxide is used as a polymerization catalyzer; a specially defined amount and a specially defined kind of a polyvalent metal ion is used; and a specially defined amount of an alkaline substance is used, in order to polymerize a monomer component consisting essentially of only maleic acid, or a monomer component composed of maleic acid and another water-soluble ethylenically unsaturated monomer, in a specially defined proportion in water, whereby a maleic acid polymer salt, preferably a copolymer salt, of improved biodegradability is produced. The maleic acid polymer salt obtained is superior in biodegradability, has a low residual monomer content, and is useful as a detergent builder and as a scale inhibitor, etc.Type: GrantFiled: April 27, 1990Date of Patent: November 12, 1991Assignee: Nippon Shokubai Co., Ltd.Inventors: Shigeru Yamaguchi, Tokihiro Yokoi, Shorbu Shioji, Yoshio Irie, Teruaki Fujiwara
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Patent number: 5041622Abstract: An improvement in known processes for preparing substituted carboxylic acids useful as acylating agents which comprise reacting (A) at least one aliphatic polymer of one or more lower olefins with (B) an acidic reactant selected from the group consisting of fumaric acid, itaconic acid, maleic acid, and the corresponding anhydrides, lower alkyl esters, acyl chlorides and acyl bromides, in the presence of chlorine can be improved by the steps of (i) reacting at a temperature of about 100.degree.-200.degree. C., a mixture of (A) and (B) in the presence of about 0.05 to 0.15 equivalent of chlorine per equivalent of (A) until all of the chlorine has reacted to provide a first intermediate product (ii) continuing the reaction in the absence of chlorine at a temperature of from about 180.degree.-250.degree. C. until a conversion of 0.4 to 1.1 equivalents of (B) per equivalent of (A) is attained to provide a second intermediate product, and (iii) reacting said second intermediate with about 0.2 to 1.Type: GrantFiled: November 28, 1990Date of Patent: August 20, 1991Assignee: The Lubrizol CorporationInventor: William M. LeSuer
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Patent number: 5028446Abstract: The present invention is concerned with a process for preparing rapidly solubilized calcium fumarate by first preparing a slurry of fumaric acid and water and a calcium containing base, combining under high shear conditions the calcium containing base with the fumaric acid slurry under temperatures not to exceed about 160.degree. F., quenching the reaction when at least one half of the fumaric acid is neutralized and wherein the mole ratio of the calcium to fumarate is at a mole ratio ranging from 1:2 to about 1:1, and drying the mixture.Type: GrantFiled: November 6, 1990Date of Patent: July 2, 1991Assignee: Kraft General Foods, Inc.Inventors: Fouad Z. Saleeb, Philip R. Morreale, Randal P. McKay, Susan M. Vidal
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Patent number: 5001260Abstract: A process for polymerizing unsaturated dicarboxylic acids comprises heating the acids in the presence of a catalytic proportion of an unactivated clay and water. The product dimer is distilled to separate unreacted monomer acids. The product dimers of 36, 40 and 44 content are useful as corrosion inhibitors, epoxy resin curing agents, lubricants and intermediates for synthetic polymeric resins and polymeric resin plasticizers.Type: GrantFiled: January 13, 1986Date of Patent: March 19, 1991Assignee: Union Camp CorporationInventor: Kathryn S. Hayes
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Patent number: 4950785Abstract: Process of synthetizing ethylene-tetracarboxylic esters by duplication of lonic compounds of the formula: ##STR1## wherein X=COOR, Y=COOR' and R and R' represent an organic group, characterized in that the duplication is an oxidative duplication conducted in the presence of a catalyst consisting of the salt of a transition metal.Type: GrantFiled: February 21, 1989Date of Patent: August 21, 1990Assignee: Presidenza del Consilglio dei Ministri Ufficio del Ministro per il coordinamento delle iniziative per la ricerca scientifica e tecnologicaInventors: Roberto Santi, Giuseppe Cometti
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Patent number: 4950783Abstract: Compositions containing (-)-5-{(R)-1-Hydroxy-2[(R)-1-methyl-3-phenylpropyl)amino]ethyl}salicylamid e exhibit potent vasodilating .beta.-adrenergic blocking properties and are useful for the treatment of hypertension.Type: GrantFiled: October 24, 1986Date of Patent: August 21, 1990Assignee: Schering CorporationInventors: Elijah H. Gold, Wei K. Chang
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Patent number: 4929396Abstract: This invention provides hexamethylenediamine muconate salt. This novel salt can be produced by bioconversion of toluene to muconic acid in the presence of hexamethylenediamine. Hydrogenation of this salt provides hexamethylenediamine adipate salt.Type: GrantFiled: October 17, 1984Date of Patent: May 29, 1990Assignee: Celgene CorporationInventors: Sol J. Barer, Peter C. Maxwell, Jih-Han Hsieh
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Patent number: 4925973Abstract: Diesters of hexene-1,6-dioic acid are efficiently and selectively prepared by reacting carbon monoxide and an alcohol with at least one diacyloxylated butene compound, in the presence of (a) a catalytically effective amount of a palladium-based catalyst and (b) a quaternary onium chloride or bromide of nitrogen or phosphorus.Type: GrantFiled: June 13, 1989Date of Patent: May 15, 1990Assignee: Rhone-Poulenc ChimieInventors: Helene Deweerdt, Jean Jenck, Philippe Kalck
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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: 4895982Abstract: Tricarboxylic acids are prepared by reacting unsaturated mono- and dicarboxylic acids of specific carbon atom content in the presence of a catalytic proportion of an unactivated clay and water. The product acids of 34, 35, 36, 38, or 40 carbon atoms are useful as corrosion inhibitors, epoxy resins curing agents, lubricants, polymeric resin plasticizers and intermediates for synthetic polymeric resins.Type: GrantFiled: June 20, 1986Date of Patent: January 23, 1990Assignee: Union Camp CorporationInventors: Mark S. Pavlin, Kathryn S. Hayes
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Patent number: 4889873Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.Type: GrantFiled: November 17, 1987Date of Patent: December 26, 1989Assignee: Schering CorporationInventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
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Patent number: 4888393Abstract: The invention relates to a novel low profile additive (LPA) for uncured polyester resins and the resultant molding compositions. The low profile additive is the reaction product of an ethylene/alphaolefin copolymer with a carboxylic acid or anhydride, to thereby form a non-thermoplastic carboxyl modified polyolefin. The novel LPA is a remarkably effective dimensional stabilizer and has displayed the ability to achieve net expansion in a cured polyester resin molding composition.Type: GrantFiled: May 19, 1988Date of Patent: December 19, 1989Assignee: Uniroyal Chemical Company, Inc.Inventors: Frank C. Cesare, William P. Whelan, Jr., Henno A. Petersen, Thomas S. Coolbaugh, Robert G. Davis
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Patent number: 4874700Abstract: L-malic acid is separated by means of electrodialysis from reaction mixtures derived from biotechnical conversion of fumarate into L-malate. Fumaric acid present in the acid concentrate from the dialysis is separated from L-malic acid without precipitation reactions using stepwise crystallization. Crystallized L-malic acid is produced in high purity and large yield. The alkali concentrate obtained during electrodialysis is recycled back into the biotechnical conversion. The process operates without appreciable losses of valuable materials and is very economical.Type: GrantFiled: September 20, 1985Date of Patent: October 17, 1989Assignee: Huels AktiengesellschaftInventor: Reinhold Seipenbusch
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Patent number: 4857657Abstract: Hexene-1,6-dioates, readily hydrogenated into adipates (which in turn are conveniently hydrolyzed into adipic acid), are prepared by reacting carbon monoxide, an alcohol and at least one dichlorobutene, in the presence of a catalytically effective amount of palladium or a palladium compound and no more than two equivalents (relative to the dichlorobutene) of a tertiary amine reaction promoter; in an alternate embodiment, the tertiary amine and the dichlorobutene are first converted into a quaternary ammonium chloride intermediate.Type: GrantFiled: November 16, 1987Date of Patent: August 15, 1989Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean-Marc Frances
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Patent number: 4851439Abstract: Fumaric acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a metallic cation, andR.sub.2 is a saturated or unsaturated aliphatic C.sub.6 -C.sub.24 alkyl group, psoralen-9-yl, retinyl, .alpha.-tocopheryl (vitamin E), calciferyl, corticosteroid-21-yl or monosaccharid-.omega.-yl; a group of fumaric acid derivatives based on glycerol, alkane diol or polyol molecules; and fumaric acid derivatives of the forumla ##STR2## wherein n is an interger from 30 to 260,R.sub.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group,R.sub.4 is one of the R.sub.3 groups and n is the number of molecule repetitions, processes for their production and compositions containing same are described. These compounds are useful as drugs for the treatment of cryptogenically-caused diseases and have antisporiatic as well as antimicrobial action.Type: GrantFiled: December 30, 1985Date of Patent: July 25, 1989Inventors: Peter P. Speiser, Rajendra K. Joshi
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Patent number: 4849500Abstract: Polyamide compositions which contain as part of their repeat structure a reactive diacetylene groups are disclosed. The cross-polymerized products of these polyamides are thermochromic polydiacetylene compounds. The compositions of the present invention do not exhibit a hysteresis effect during temperature cycling.Type: GrantFiled: March 7, 1986Date of Patent: July 18, 1989Assignee: GTE Laboratories IncorporatedInventor: Michael F. Rubner
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Patent number: 4808747Abstract: Alkylidene compounds and arylidene compounds are prepared by reacting the corresponding CH-acidic compounds with carbonyl compounds in the presence of a catalyst comprising a metal compound of a metal of Groups IIA, IIIA, IVA, IB, IIB, VIB, VIIB, or VIIIB of the periodic table of elements. The rate of reaction is increased by adding 1 to 40% water referred to the weight of catalyst used.Type: GrantFiled: March 14, 1985Date of Patent: February 28, 1989Assignee: Huls AGInventor: Walter K. Homann
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Patent number: 4801407Abstract: In the present invention, hydrated magnesium salts of the carboxylate group in certain aromatic or olefinically unsaturated peroxyacids such as monoperoxyphthalic acid or monoperoxymaleic acid are made by reacting the corresponding anhydride with aqueous hydrogen peroxide and a magnesium base, in the absence of a significant amount of free iron. By so doing, the process avoids the use of non-aqueous solvents such as ethyl acetate. Solid product can be obtained by using no more than enough hydrogen peroxide and water for solely a damp product to be obtained or by crystallization from an aqueous solution, preferably with recycle of the mother liquor. Preferably the reaction temperature is maintained at 5.degree. to 25.degree. C., employing 1.8 to 2.2 moles anhyhdride per mole of magnesium base, and 0.95 to 1.2 moles of hydrogen peroxide per mole of anhydride.The product can be used as a bleach and as a disinfectant.Type: GrantFiled: May 25, 1982Date of Patent: January 31, 1989Assignee: Interox Chemicals LimitedInventors: Geoffrey J. Hignett, Iain S. MacKirdy
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Patent number: 4795824Abstract: A process is described for the production of a dialkyl maleate by reaction of maleic anhydride with an alkyl alcohol in a monoesterification zone to form the corresponding monoalkyl maleate, followed by reaction of resulting monoalkyl maleate with further alkyl alcohol to form the corresponding dialkyl maleate, which includes the steps of supplying a first liquid feed comprising said monoalkyl maleate to a secondary esterification zone containing a charge of a solid esterification catalyst, supplying a second feed stream comprising said alkyl alcohol to said secondary esterification zone, maintaining said secondary esterification zone at an elevated temperature sufficient to form or to maintain therein a vaporous stream containing said alkyl alcohol, intimately contacting said first liquid feed in said secondary esterification zone in the presence of said catalyst with said vaporous feed stream, recovering from said secondary esterification zone a vaporous effluent stream containing, in addition to alkyl alcoType: GrantFiled: July 31, 1987Date of Patent: January 3, 1989Assignee: Davy McKee (London) LimitedInventors: John W. Kippax, Colin Rathmell
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Patent number: 4736044Abstract: A process for the production of a substituted alpha, beta dicarboxylic acid compound substantially free of tar and other resinous reaction byproducts comprising the reaction at conditions favoring the ENE reaction of an ethylenically unsaturated hydrocarbon and an ethylenically unsaturated alpha, beta dicarboxylic acid compound in the presence of a boron compound.Type: GrantFiled: November 14, 1983Date of Patent: April 5, 1988Assignee: Amoco CorporationInventor: Joseph B. Hanson
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Patent number: 4732708Abstract: The invention relates to a method for converting biopolyesters consisting of straight-chain hydroxyacid monomers containing 10 to 40 carbon atoms, such as suberin and cutin, into a plain mixture of organic acids and their salts containing only a few main components. The depolymerization is carried out according to the invention by oxidizing either with a strong oxidizer or by dehydrating oxidation with strong alkali at elevated temperature.Type: GrantFiled: February 20, 1986Date of Patent: March 22, 1988Assignee: Kemira OyInventors: Rainer Ekman, Christer Eckerman, Tapio Mattila, Elias Suokas
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Patent number: 4731467Abstract: Process for the preparation of diesters of 2-butenedioic acids by reacting an optionally substituted acetylenically unsaturated hydrocarbon having two carbon atoms less than said 2-butenedioic acid, carbon monoxide, a quinone in the presence of a of Group VIII noble metal or a compound thereof, and optionally, a redox agent.Type: GrantFiled: January 12, 1987Date of Patent: March 15, 1988Assignee: Shell Oil CompanyInventors: Eit Drent, Antonius J. M. Breed
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Patent number: 4709091Abstract: A polymer or copolymer of maleic acid is produced by neutralizing (I) maleic acid in an aqueous medium with (III) an alkali metal hydroxide or ammonia at a molar ratio of (I) to (III) in the range of 100:0 to 100:90, polymerizing (I) with a polymerization initiator, adding (III) a further amount of the alkali metal hydroxide or ammonia at a molar ratio of (I) to (III) in the range of 100:100 to 100:130 in total through the previous addition and this addition and continuing the polymerization to the complete effect.Type: GrantFiled: March 27, 1985Date of Patent: November 24, 1987Assignee: Kao CorporationInventors: Yasuhisha Fukumoto, Moboru Moriyama
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Patent number: 4699997Abstract: Water-soluble polyacetylenic alkali metal salts from monomers and polymers of carboxymethyl urethanes of di-, tetra-, and hexayne diols, or from the corresponding diacids; useful in thermal and irradiation exposure indicators and/or in detection and/or removal of nonalkali metal ions dissolved in aqueous media.Type: GrantFiled: September 28, 1982Date of Patent: October 13, 1987Assignee: Allied CorporationInventors: Anthony F. Preziosi, Gordhanbhai N. Patel, Robert G. Denkewalter, Ray H. Baughman
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Patent number: 4692548Abstract: The dimerization of acrylate esters and of ethene and the codimerization of acrylate esters with C.sub.2-4 -alkenes or 1,3-butadiene and of 1,3-butadiene with ethene in the presence of:(a) a Pd and/or Ru compound,(b) a compound containing one trivalent N or P atom, and(c) an Ag and/or Cu salt,yields at an increased reaction rate dimers of high linearity, when a quinone is also present.Type: GrantFiled: May 14, 1986Date of Patent: September 8, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4689344Abstract: A novel class of compounds has been found to be effective in blocking cholesterol and neutral lipid synthesis in-vivo without adversely affecting energy metabolism, useful for the treatment of obesity, hyperlipidemia and maturity-onset diabetes. The active compounds have the general formula ##STR1## or in-vivo hydrolyzable functional derivatives of the carboxylic groups thereof,whereinR.sub.1 and R.sub.2 each independently represents an unsubstituted or substituted hydrocarbyl or hetercyclyl radical;X and Y each independently represents hydrogen, optionally substituted lower alkyl, halogen, cyano, carboxy, lower alkoxycarbonyl or carbamoyl; andQ represents a diradical consisting of a linear chain of 8 to 14 carbon atoms, one or more of which may be replaced by heteroatoms, said chain being optionally substituted by inert substituents and one or more of said carbon or heteratom chain members optionally forming part of a ring structure.Type: GrantFiled: June 22, 1984Date of Patent: August 25, 1987Assignee: Epis S.A.Inventor: Jacob Bar-Tana
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Patent number: 4638079Abstract: Disclosed is a process for inhibiting polymerization of polymerizable ethylenically unsaturated monomers such as hydrocarbons, acids and esters, wherein a cobalt (III), nickel (II) or manganese (II) complex of N-nitrosophenylhydroxylamine is employed. A composition including a polymerizable ethylenically unsaturated monomer and the complex is also disclosed. In a preferred embodiment, polymerization of an acrylic acid or an acrylate ester is inhibited.Type: GrantFiled: January 17, 1985Date of Patent: January 20, 1987Assignee: Mallinckrodt, Inc.Inventors: Ervin B. Inskip, Joseph M. Patane
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Patent number: 4629807Abstract: A process for preparing aliphatic dicarboxylic acid esters from aliphatic, non-conjugated dienes via carbonylation in the presence of a homogeneous palladium-phosphine catalyst or a palladium-phosphine melt catalyst.Type: GrantFiled: February 6, 1986Date of Patent: December 16, 1986Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4623747Abstract: A process for producing long-chained diesters of C.sub.22 and C.sub.32 diacids. The process comprises the steps of reacting cyclohexanone with an alcohol of 1-6 carbon atoms and hydrogen peroxide in the presence of an acid catalyst and water at a temperature below the boiling point of the alcohol. Methoxycyclohexyl hydroperoxide is thus produced and reacted with a terpene diene in the presence of a transition metal salt in a nitrogen atmosphere to produce long-chained diesters of C.sub.22 and C.sub.32 diacids. These long-chained diesters are then separated from the reaction mixture.Type: GrantFiled: May 13, 1985Date of Patent: November 18, 1986Assignee: Union Camp CorporationInventors: Kathryn S. Hayes, Jerome R. Olechowski
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Patent number: 4622425Abstract: A process for the manufacture of low molecular weight polyacrylic acids or their salts is provided, particularly, their aqueous solutions. Acrylic acid in an aqueous solution containing a polymerization initiator is polymerized in the presence of acetic acid and/or propionic acid.The solutions obtained have a low viscosity and are very stable on storage.Type: GrantFiled: December 15, 1982Date of Patent: November 11, 1986Assignee: Rhone-Poulenc IndustriesInventor: Pierre Gagne
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Patent number: 4613694Abstract: Process for the concurrent preparation of olefinically unsaturated or satted .alpha.,.omega.-dialdehydes and .alpha.,.omega.-diacids, characterized by the fact that the monoozonide of a a mono- or polyunsaturated cycloolefine in solution in a polar solvent, is treated with water and subsequently with an alkaline aqueous solution at room pressure and at a temperature from -5.degree. C. to 70.degree. C., maintaining during the addition of the alkali, a pH not higher than 12, the dialdehyde and the diacid being subsequently isolated by known, conventional methods.Type: GrantFiled: September 30, 1980Date of Patent: September 23, 1986Assignee: Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.p.A.Inventors: Pier P. Rossi, Salvatore Marchetti
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Patent number: 4611087Abstract: Novel salts of alkenylsuccinic monoesters represented by the following formulas (I) or (II): ##STR1## in which R.sub.1 represents a hydrocarbon group, R.sub.2 represents a hydrogen atom or a methyl group, A represents an alkylene group having from 2 to 4 carbon atoms, B represents a carbonyl group or a methylene group, M is a monovalent or divalent cation.The monoesters can be emulsion-polymerized under optimum conditions while varying the hydrophilic and oleophilic balance depending on the type of monomer because they have hydrophobic hydrocarbon groups and oleophilic carboxylate groups and ether bonds of polyalkyleneoxy groups.The compounds according to the invention are an excellent reactive surface active agent, and also useful as an improver or modifier for polymer because they can impart hydrophilicity to hydrophobic resins when they are used in larger amounts as in the case of reactive surface active agents employed for ordinary.Type: GrantFiled: November 2, 1983Date of Patent: September 9, 1986Assignee: KAO CorporationInventors: Osamu Yamashita, Noboru Moriyama, Shoji Ootani, Katsuyo Wasamoto
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Patent number: 4578205Abstract: The use of methylene azelaic acid having the formula CH.sub.2 .dbd.C--[(CH.sub.2).sub.3 --COOH].sub.2 or an alkali metal salt thereof in glycol and water based automotive antifreeze formulations is described. Unlike natural dicarboxylic acids such as sebacic acid, methylene azelaic acid does not form a precipitate and drop out of solution, rendering the antifreeze unprotected against corrosion. The methylene azelaic acid component should be present in an amount of from 1.5 to 4.5 wt. % based on the glycol component.Type: GrantFiled: February 1, 1985Date of Patent: March 25, 1986Assignee: Texaco, Inc.Inventors: Ernest L. Yeakey, George P. Speranza, Carol A. Triebel, David R. McCoy
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Patent number: 4568757Abstract: A group of retinoids having "vitamin A type" activity which have the structure ##STR1## wherein R3 is a trimethylcyclohexenylethylene, tetramethyltetrahydronaphthalene or methoxytrimethylphenylethylene group;R1 and R2 which are different are selected from --OH, --OR4 and --NHR, provided one of R1 and R2 is OH; R4 is alkyl of 1 to 20 carbons; and R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, hydroxyalkyl of 1 to 4 carbons, alkylhydroxyalkyl of 1 to 4 carbons, phenyl, hydroxyphenyl and carboxyphenyl, and R5 is a lactone or lactam of the structure ##STR2## and X is oxygen or NR where R is as above, and the pharmaceutically acceptable salts thereof.Type: GrantFiled: January 30, 1984Date of Patent: February 4, 1986Assignee: Research Triangle InstituteInventors: Frank I. Carroll, Anita H. Lewin
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Patent number: 4562283Abstract: Maleic anhydride is separated off from gaseous reaction mixtures by a continuous process in which the gaseous reaction mixture containing the maleic anhydride is brought into contact with butanol, the gaseous substances obtained in this procedure are brought into contact with butyl maleate by a countercurrent method, and the liquid product is removed from the bottom.Type: GrantFiled: December 14, 1984Date of Patent: December 31, 1985Assignee: BASF AktiengesellschaftInventors: Rolf Schnabel, Hans M. Weitz
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Patent number: 4547323Abstract: The process comprises dimerizing methacrylic acid derivatives in the presence of an organic Co(II) glyoxime to produce 2,2-dimethyl-4-methyleneglutaric acid and/or derivatives thereof. Methacrylic acid derivatives include methacrylic acid or derivatives of methacrylic acid. The composition produced by the process comprises a glutaric dimer acid which can be further polymerized to form high molecular weight polymer useful as a binder in protective coatings.Type: GrantFiled: March 21, 1984Date of Patent: October 15, 1985Assignee: SCM CorporationInventor: Gary M. Carlson
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Patent number: 4529721Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.Type: GrantFiled: September 21, 1983Date of Patent: July 16, 1985Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
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Patent number: 4519954Abstract: A catalyst and a liquid phase process are provided for the dimerization of acrylic compounds. The process includes contacting an acrylic compound with the catalyst in the presence of hydrogen, wherein the catalyst comprises an inorganic oxide catalyst support, trivalent pendant atoms covalently bonded to the support and ruthenium complexed with said trivalent pendant atoms.Type: GrantFiled: December 29, 1982Date of Patent: May 28, 1985Assignee: The Standard Oil CompanyInventors: James D. Burrington, Fred A. Pesa, Elizabeth A. Maher, Robert K. Grasselli
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Patent number: 4500463Abstract: 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: GrantFiled: May 1, 1981Date of Patent: February 19, 1985Assignees: Eisai Co., Ltd., Agency of Industrial Science & TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Yuichi Inai, Yoshiyuki Kohara, Yoshiyuki Kawakami, Tomio Tsurugi
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Patent number: 4450281Abstract: Disclosed is a process for the preparation of substituted carboxylic acids and their derivatives in which the synthesis reaction is carried out at least partially thermally in the presence of a furan-type compound. The furan-type compound substantially increases yields and reduces the formation of undesirable resinous by-products.Type: GrantFiled: December 29, 1982Date of Patent: May 22, 1984Assignee: Chevron Research CompanyInventor: Robert H. Wollenberg
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Patent number: 4420621Abstract: Novel methods for preparing polycarboxylic compounds which are useful as metal sequestrants and food acidulants are disclosed. These compounds are aconitic acid and a mixture of aconitic acid, and the lactones of isocitric acid and alloisocitric acid. The compounds can be neutralized to the corresponding salts which, in turn, are metal sequestering agents. The novel methods include chlorination of propane-1,1,2,3-tetracarboxylic tetraesters.Type: GrantFiled: December 17, 1980Date of Patent: December 13, 1983Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4414393Abstract: Ultraviolet-absorbing stabilizers of the formula E-(G-R).sub.n, L-(G-E).sub.m, or [G-E.sub.1 -G-Q].sub.p where E is a radical derived from an oxanilide, benzalmalonate, .alpha.-cyanocinnamate or o-hydroxyphenylbenzotriazole, E.sub.1 is a radical derived from an oxanilide, G is --OCH.sub.2 CHOH--, R is alkyl, phenyl or --CH.sub.2 OT where T is alkyl or alkenyl, n is 1 or 2, m is 2 or 3, L is a direct bond, alkylene or other bis or tris radical, Q has the same meaning as L when m is 2, and p is 1 to 4, are particularly resistant to loss during weathering of outdoor thermoset or thermoplastic coating systems while exhibiting good stabilization efficacy and compatibility in said systems.Type: GrantFiled: November 5, 1981Date of Patent: November 8, 1983Assignee: Ciba-Geigy CorporationInventors: Martin Dexter, Roland A. E. Winter
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Patent number: 4396774Abstract: A process for the production of a substituted alpha, beta dicarboxylic acid compound substantially free of tar and other resinous reaction byproducts comprising the reaction of an ethylenically unsaturated long chain compound having at least 10 carbon atoms and an ethylenically unsaturated alpha, beta dicarboxylic acid compound at conditions favoring the ENE reaction in the presence of a catalytically effective amount of an alkyl aluminum halide.Type: GrantFiled: March 22, 1982Date of Patent: August 2, 1983Assignee: Standard Oil Company (Indiana)Inventor: John G. Schaffhausen
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Patent number: 4388471Abstract: Disclosed is a process for the preparation of substituted carboxylic acids and their derivatives in which the synthesis reaction is carried out at least partially thermally in the presence of a furan-type compound. The furan-type compound substantially increases yields and reduces the formation of undesirable resinous by-products.Type: GrantFiled: April 30, 1982Date of Patent: June 14, 1983Assignee: Chevron Research CompanyInventor: Robert H. Wollenberg