Unsaturated Patents (Class 562/595)
  • Patent number: 5149695
    Abstract: 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: Grant
    Filed: March 13, 1989
    Date of Patent: September 22, 1992
    Inventors: Peter P. Speiser, Rajendra K. Joshi
  • Patent number: 5142098
    Abstract: 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: Grant
    Filed: March 23, 1990
    Date of Patent: August 25, 1992
    Assignee: Laboratoires UPSA
    Inventors: Nicole Bru-Magniez, Christian De Cock, Jacques Poupaert, Jean-Luc De Keyser, Pierre Dumont
  • Patent number: 5106541
    Abstract: 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: Grant
    Filed: January 9, 1990
    Date of Patent: April 21, 1992
    Assignee: Henkel Research Corporation
    Inventors: William E. Fristad, Alan G. Olivero, Steven Young, Christopher S. Sykes, Brock M. Siegel
  • Patent number: 5099034
    Abstract: 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: Grant
    Filed: June 27, 1990
    Date of Patent: March 24, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tadashi Yoshida, Hiroshi Itazaki, Hitoshi Arita, Yoshimi Kawamura, Koichi Matsumoto
  • Patent number: 5081292
    Abstract: .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: Grant
    Filed: April 30, 1990
    Date of Patent: January 14, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Denis, Jean Jenck, Robert Perron
  • Patent number: 5077433
    Abstract: 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: Grant
    Filed: April 30, 1990
    Date of Patent: December 31, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean Jenck, Philippe Denis, Philippe Kalck, Helene Deweerdt
  • Patent number: 5064563
    Abstract: 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: Grant
    Filed: April 27, 1990
    Date of Patent: November 12, 1991
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Shigeru Yamaguchi, Tokihiro Yokoi, Shorbu Shioji, Yoshio Irie, Teruaki Fujiwara
  • Patent number: 5041622
    Abstract: 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: Grant
    Filed: November 28, 1990
    Date of Patent: August 20, 1991
    Assignee: The Lubrizol Corporation
    Inventor: William M. LeSuer
  • Patent number: 5028446
    Abstract: 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: Grant
    Filed: November 6, 1990
    Date of Patent: July 2, 1991
    Assignee: Kraft General Foods, Inc.
    Inventors: Fouad Z. Saleeb, Philip R. Morreale, Randal P. McKay, Susan M. Vidal
  • Patent number: 5001260
    Abstract: 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: Grant
    Filed: January 13, 1986
    Date of Patent: March 19, 1991
    Assignee: Union Camp Corporation
    Inventor: Kathryn S. Hayes
  • Patent number: 4950785
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: August 21, 1990
    Assignee: Presidenza del Consilglio dei Ministri Ufficio del Ministro per il coordinamento delle iniziative per la ricerca scientifica e tecnologica
    Inventors: Roberto Santi, Giuseppe Cometti
  • Patent number: 4950783
    Abstract: 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: Grant
    Filed: October 24, 1986
    Date of Patent: August 21, 1990
    Assignee: Schering Corporation
    Inventors: Elijah H. Gold, Wei K. Chang
  • Patent number: 4929396
    Abstract: 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: Grant
    Filed: October 17, 1984
    Date of Patent: May 29, 1990
    Assignee: Celgene Corporation
    Inventors: Sol J. Barer, Peter C. Maxwell, Jih-Han Hsieh
  • Patent number: 4925973
    Abstract: 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: Grant
    Filed: June 13, 1989
    Date of Patent: May 15, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Helene Deweerdt, Jean Jenck, Philippe Kalck
  • Patent number: 4897473
    Abstract: 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: Grant
    Filed: May 1, 1981
    Date of Patent: January 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Bernard D. Dombek
  • Patent number: 4895982
    Abstract: 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: Grant
    Filed: June 20, 1986
    Date of Patent: January 23, 1990
    Assignee: Union Camp Corporation
    Inventors: Mark S. Pavlin, Kathryn S. Hayes
  • Patent number: 4889873
    Abstract: 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: Grant
    Filed: November 17, 1987
    Date of Patent: December 26, 1989
    Assignee: Schering Corporation
    Inventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
  • Patent number: 4888393
    Abstract: 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: Grant
    Filed: May 19, 1988
    Date of Patent: December 19, 1989
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Frank C. Cesare, William P. Whelan, Jr., Henno A. Petersen, Thomas S. Coolbaugh, Robert G. Davis
  • Patent number: 4874700
    Abstract: 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: Grant
    Filed: September 20, 1985
    Date of Patent: October 17, 1989
    Assignee: Huels Aktiengesellschaft
    Inventor: Reinhold Seipenbusch
  • Patent number: 4857657
    Abstract: 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: Grant
    Filed: November 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Denis, Jean-Marc Frances
  • Patent number: 4851439
    Abstract: 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: Grant
    Filed: December 30, 1985
    Date of Patent: July 25, 1989
    Inventors: Peter P. Speiser, Rajendra K. Joshi
  • Patent number: 4849500
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: July 18, 1989
    Assignee: GTE Laboratories Incorporated
    Inventor: Michael F. Rubner
  • Patent number: 4808747
    Abstract: 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: Grant
    Filed: March 14, 1985
    Date of Patent: February 28, 1989
    Assignee: Huls AG
    Inventor: Walter K. Homann
  • Patent number: 4801407
    Abstract: 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: Grant
    Filed: May 25, 1982
    Date of Patent: January 31, 1989
    Assignee: Interox Chemicals Limited
    Inventors: Geoffrey J. Hignett, Iain S. MacKirdy
  • Patent number: 4795824
    Abstract: 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 alco
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: January 3, 1989
    Assignee: Davy McKee (London) Limited
    Inventors: John W. Kippax, Colin Rathmell
  • Patent number: 4736044
    Abstract: 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: Grant
    Filed: November 14, 1983
    Date of Patent: April 5, 1988
    Assignee: Amoco Corporation
    Inventor: Joseph B. Hanson
  • Patent number: 4732708
    Abstract: 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: Grant
    Filed: February 20, 1986
    Date of Patent: March 22, 1988
    Assignee: Kemira Oy
    Inventors: Rainer Ekman, Christer Eckerman, Tapio Mattila, Elias Suokas
  • Patent number: 4731467
    Abstract: 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: Grant
    Filed: January 12, 1987
    Date of Patent: March 15, 1988
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Antonius J. M. Breed
  • Patent number: 4709091
    Abstract: 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: Grant
    Filed: March 27, 1985
    Date of Patent: November 24, 1987
    Assignee: Kao Corporation
    Inventors: Yasuhisha Fukumoto, Moboru Moriyama
  • Patent number: 4699997
    Abstract: 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: Grant
    Filed: September 28, 1982
    Date of Patent: October 13, 1987
    Assignee: Allied Corporation
    Inventors: Anthony F. Preziosi, Gordhanbhai N. Patel, Robert G. Denkewalter, Ray H. Baughman
  • Patent number: 4692548
    Abstract: 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: Grant
    Filed: May 14, 1986
    Date of Patent: September 8, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4689344
    Abstract: 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: Grant
    Filed: June 22, 1984
    Date of Patent: August 25, 1987
    Assignee: Epis S.A.
    Inventor: Jacob Bar-Tana
  • Patent number: 4638079
    Abstract: 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: Grant
    Filed: January 17, 1985
    Date of Patent: January 20, 1987
    Assignee: Mallinckrodt, Inc.
    Inventors: Ervin B. Inskip, Joseph M. Patane
  • Patent number: 4629807
    Abstract: 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: Grant
    Filed: February 6, 1986
    Date of Patent: December 16, 1986
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4623747
    Abstract: 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: Grant
    Filed: May 13, 1985
    Date of Patent: November 18, 1986
    Assignee: Union Camp Corporation
    Inventors: Kathryn S. Hayes, Jerome R. Olechowski
  • Patent number: 4622425
    Abstract: 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: Grant
    Filed: December 15, 1982
    Date of Patent: November 11, 1986
    Assignee: Rhone-Poulenc Industries
    Inventor: Pierre Gagne
  • Patent number: 4613694
    Abstract: 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: Grant
    Filed: September 30, 1980
    Date of Patent: September 23, 1986
    Assignee: Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.p.A.
    Inventors: Pier P. Rossi, Salvatore Marchetti
  • Patent number: 4611087
    Abstract: 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: Grant
    Filed: November 2, 1983
    Date of Patent: September 9, 1986
    Assignee: KAO Corporation
    Inventors: Osamu Yamashita, Noboru Moriyama, Shoji Ootani, Katsuyo Wasamoto
  • Patent number: 4578205
    Abstract: 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: Grant
    Filed: February 1, 1985
    Date of Patent: March 25, 1986
    Assignee: Texaco, Inc.
    Inventors: Ernest L. Yeakey, George P. Speranza, Carol A. Triebel, David R. McCoy
  • Patent number: 4568757
    Abstract: 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: Grant
    Filed: January 30, 1984
    Date of Patent: February 4, 1986
    Assignee: Research Triangle Institute
    Inventors: Frank I. Carroll, Anita H. Lewin
  • Patent number: 4562283
    Abstract: 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: Grant
    Filed: December 14, 1984
    Date of Patent: December 31, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Schnabel, Hans M. Weitz
  • Patent number: 4547323
    Abstract: 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: Grant
    Filed: March 21, 1984
    Date of Patent: October 15, 1985
    Assignee: SCM Corporation
    Inventor: Gary M. Carlson
  • Patent number: 4529721
    Abstract: 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: Grant
    Filed: September 21, 1983
    Date of Patent: July 16, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
  • Patent number: 4519954
    Abstract: 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: Grant
    Filed: December 29, 1982
    Date of Patent: May 28, 1985
    Assignee: The Standard Oil Company
    Inventors: James D. Burrington, Fred A. Pesa, Elizabeth A. Maher, Robert K. Grasselli
  • 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: 4450281
    Abstract: 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: Grant
    Filed: December 29, 1982
    Date of Patent: May 22, 1984
    Assignee: Chevron Research Company
    Inventor: Robert H. Wollenberg
  • Patent number: 4420621
    Abstract: 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: Grant
    Filed: December 17, 1980
    Date of Patent: December 13, 1983
    Assignee: Lever Brothers Company
    Inventors: Eddie N. Gutierrez, Vincent Lamberti
  • Patent number: 4414393
    Abstract: 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: Grant
    Filed: November 5, 1981
    Date of Patent: November 8, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Dexter, Roland A. E. Winter
  • Patent number: 4396774
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: August 2, 1983
    Assignee: Standard Oil Company (Indiana)
    Inventor: John G. Schaffhausen
  • Patent number: 4388471
    Abstract: 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: Grant
    Filed: April 30, 1982
    Date of Patent: June 14, 1983
    Assignee: Chevron Research Company
    Inventor: Robert H. Wollenberg