Unsaturated Patents (Class 562/598)
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Patent number: 4962230Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.Type: GrantFiled: November 16, 1987Date of Patent: October 9, 1990Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4950788Abstract: Acrylic acid or other unsaturated carboxylic acid is made by hydrolysing the corresponding nitrile in the presence of excess sulphuric acid to form amide sulphate, adding amide in an amount such that the total amount of amide and nitrile fed to the process is greater than 1 mole per mole sulphuric acid, hydrolysing the amide sulphate and amide to the desired acid and separating the acid from the sulphate by-products.Type: GrantFiled: February 23, 1989Date of Patent: August 21, 1990Assignee: Allied Colloids LimitedInventors: David Farrar, Peter Flesher
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Patent number: 4945180Abstract: A novel process for the preparation of E-2-propyl-2-pentenoic acid and its physiologically compatible salts is described, in which di-n-propyl-ketone-cyanohydrin is used as the starting compound. The compound is either(a) dehydrated with thionyl chloride and the acid nitrile formed is subsequently saponified with a stoichiometric excess of potassium hydroxide, or(b) is initially converted into 2-hydroxy-2-propyl-pentanoic acid and the latter is subsequently dehydrated in the presence of a less than stoichiometric quantity of a tertiary amine at a temperature of at least 200.degree. C.The free acid is optionally converted into the salt form, preferably using the corresponding salts of carbon dioxide in an aqueous acetone solution.Type: GrantFiled: June 2, 1988Date of Patent: July 31, 1990Assignee: Desitin Arzneimittel GmbHInventor: Helmut Schafer
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Patent number: 4927967Abstract: A process for the production of organic carboxylic acids by the catalytic reaction of organic formate esters in contact with carbon monoxide and a homogeneous catalyst system of rhodium metal atom, a phosphorus containing ligand in which there is present at least one oxo oxygen atom attached to a phosphorus atom or a carbon atom to form a Z group and the ##STR1## group in said Z group is located at least one carbon atom removed and preferably from 2-4 carbon atoms removed from the phosphorus atom of the molecules represented by the formulas ##STR2## and a halogen source, under mild reaction conditions, wherein R' is H, aryl, alkaryl, aralkyl or alkyl, and wherein 1 or more of said R' groups can be substituted with a Z group but not more than 3 of said R' groups in the molecule are so substituted; a is an integer from 0-4; b is an integer from 0-3; and Z is P(O)R'R'; --C(O)OR" or C(O)R", wherein R" is R'.Type: GrantFiled: November 6, 1985Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Richard W. Wegman
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Patent number: 4925972Abstract: Alkyl pentenoates are prepared by(a) reacting butadiene or a butadiene-containing hydrocarbon mixture with carbon monoxide and an alkanol in the presence of a tertiary aromatic heterocyclic nitrogen base and a cobalt carbonyl catalyst at from 80.degree. to 160.degree. C. under from 100 to 1,000 bar to obtain a reaction mixture which contains alkyl pentenoate, C.sub.6 -diester, tertiary nitrogen base, alkanol, butadiene, hydrocarbon and by-product,(b) substantially removing from the reaction mixture obtained any excess hydrocarbon, nitrogen base, alkanol and alkyl pentenoate by distillation to obtain a residue which contains cobalt carbonyl catalyst,(c) bringing the residue which contains cobalt carbonyl catalyst into contact with a mixture of carbon monoxide and hydrogen at elevated temperature and elevated pressure, and(d) recycling the residue which contains cobalt carbonyl catalyst into alkyl pentenoate synthesis stage (a).Type: GrantFiled: July 12, 1989Date of Patent: May 15, 1990Assignee: BASF AktiengesellschaftInventors: Robert Maerkl, Wolfgang Harder
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Patent number: 4918225Abstract: The invention relates to a process for the preparation of pure cis- or trans-crotonic acid from a mixture of the two isomers by melt crystallization. To prepare trans-crotonic acid, an isomer mixture I containing at least 40% by weight of trans-crotonic acid is used as the starting material. On the other hand, if cis-crotonic acid is to be prepared, an isomer mixture II containing at least 80% by weight of cis-crotonic acid is used as the starting material. The particular isomer mixture is melted and then left to cool, trans-crotonic acid being allowed to crystrallize out of mixture I to a residual content of at least 35% by weight, and cis-crotonic acid being allowed to crystallize out of mixture II to a residual content of at least 75% by weight.Type: GrantFiled: October 2, 1985Date of Patent: April 17, 1990Assignee: Hoechst AktiengesellschaftInventors: Siegbert Rittner, Herbert Gortz, Knut Riedel
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Patent number: 4902334Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.Type: GrantFiled: October 31, 1984Date of Patent: February 20, 1990Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
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Patent number: 4898976Abstract: The ethanolamine salt of N-nitrosophenylhydroxylamine ("NPHA") is effective as a polymerization inhibitor for ethylenically unsaturated monomers. The ethanolamine salt can be prepared by reacting ethanolamine with the ammonium salt of NPHA. Advantageously, the ethanolamine salt is soluble in high concentrations in water and a variety of polar organic solvents.Type: GrantFiled: April 17, 1989Date of Patent: February 6, 1990Assignee: Mallinckrodt, Inc.Inventor: John W. Varwig
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Patent number: 4898853Abstract: This invention relates to acetylenic esters that are useful in the treatment of fungal diseases and hypercholesterolemic conditions.Type: GrantFiled: August 1, 1989Date of Patent: February 6, 1990Assignee: Merck & Co. Inc.Inventors: James V. Heck, Michael D. Lewis
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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: 4889949Abstract: The alkyl acrylates, e.g., methyl or ethyl acrylate, are improvedly dimerized, or codimerized with a conjugated diene, by contacting same with a catalytically effective amount of (a) at least one palladium source, (b) at least one organophosphorus(III) compound, and (c) at least one hydracid HY, the anion Y.sup.- of which does not coordinate with palladium ions.Type: GrantFiled: June 28, 1988Date of Patent: December 26, 1989Assignee: Rhone-Poulenc ChimieInventors: Pierre Grenouillet, Denis Neibecker, Igor Tkatchenko
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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: 4874889Abstract: 3-Pentenoates are prepared by isomerization of 2-pentenoates to 3-pentenoates by a process in which the 2-pentenoate is treaated with from 0.01 to 0.5 mole of cyclic tertiary amine having a pK.sub.a of >6 per mole of 2-pentenoate at from 50.degree. to 250.degree. C. and the 3-pentenoate is distilled off continuously.Type: GrantFiled: November 18, 1987Date of Patent: October 17, 1989Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Franz Merger, Hans-Juergen Gosch
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Patent number: 4871868Abstract: A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula ofA--X (I)wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula ofM--C.tbd.C--B (II)wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of--C.tbd.C--M (III)wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of ##STR1## wherein R.sup.1 and R.sup.2 independently represent a lower alkyl, and R.sup.3 represents a hydrogen or a lower alkyl.Type: GrantFiled: March 3, 1988Date of Patent: October 3, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Yuzuru Saito, Kokichi Yoshida
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Patent number: 4822913Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.Type: GrantFiled: October 28, 1983Date of Patent: April 18, 1989Assignee: Amoco CorporationInventor: Gary P. Hagen
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Patent number: 4797504Abstract: This invention relates to compositions and methods of inhibiting acrylate monomer polymerization at elevated temperatures comprising adding to the acrylate monomer an effective amount for the purpose of (a) a hydroxylamine having the formula ##STR1## wherein R and R' are the same or different and are hydrogen, alkyl, aryl, alkaryl or aralkyl groups, and (b) a para-phenylenediamine or derivative thereof having at least one N-H group. Preferably the phenylenediamine is a para-phenylenediamine having the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are hydrogen, alkyl, aryl, alkaryl, or aralkyl groups with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3 or R.sup.4 is hydrogen.Type: GrantFiled: October 7, 1986Date of Patent: January 10, 1989Assignee: Betz Laboratories, Inc.Inventor: Paul V. Roling
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Patent number: 4772740Abstract: The ethanolamine salt of N-nitrosophenylhydroxylamine ("NPHA") is effective as a polymerization inhibitor for ethylenically unsaturated monomers. The ethanolamine salt can be prepared by reacting ethanolamine with the ammonium salt of NPHA. Advantageously, the ethanolamine salt is soluble in high concentrations in water and a variety of polar organic solvents.Type: GrantFiled: March 5, 1985Date of Patent: September 20, 1988Assignee: Mallinckrodt, Inc.Inventor: John W. Varwig
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Patent number: 4734511Abstract: A method for producing .alpha.,.alpha.-dimethyl-.delta.-valerolactone which comprises carrying out the addition reaction of hydrogen bromide and 2,2-dimethyl-4-pentenoic acid in the presence or absence of a catalyst to synthesize 2,2-dimethyl-5-bromovaleric acid which is then subjected to ring-closure reaction by alkali treatment.Type: GrantFiled: October 16, 1986Date of Patent: March 29, 1988Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Takeshi Inagaki, Tuyoshi Irie, Katsumi Nakamura, Denzi Sato
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Patent number: 4727181Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.Type: GrantFiled: April 21, 1986Date of Patent: February 23, 1988Assignee: The Dow Chemical CompanyInventor: William J. Kruper, Jr.
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Patent number: 4693849Abstract: Unsaturated compounds of the formula: ##STR1## in which: Q denotes alkyloxycarbonyl, cyano or formyl, R.sub.1 denotes a saturated or unsaturated aliphatic radical, R.sub.2 denotes a hydrogen atom or an alkyl radical, R.sub.3 denotes a hydrogen atom or an aliphatic radical and R.sub.4 denotes a hydrogen atom or a saturated or unsaturated aliphatic radical which may be substituted, are useful as intermediates in the synthesis of vitamin E.Type: GrantFiled: September 13, 1985Date of Patent: September 15, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4692544Abstract: Certain substituted diaryl amines are used to inhibit the polymerization of ethylenically unsaturated monomers; for example, unsaturated carboxylic acids and derivatives thereof.Type: GrantFiled: August 23, 1985Date of Patent: September 8, 1987Assignee: Sandoz Ltd.Inventors: Richard N. Goerner, J. Michael Hipp, Ruth H. Hipp
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Patent number: 4681977Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: June 27, 1985Date of Patent: July 21, 1987Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4663480Abstract: Disclosed is a process for inhibiting polymerization of polymerizable ethylenically unsaturated monomers such as hydrocarbons, acids and esters, wherein manganese nitrite, i.e. Mn(NO.sub.2).sub.2, is employed as an inhibitor. A composition including a polymerizable ethylenically unsaturated monomer and Mn(NO.sub.2).sub.2 is also disclosed. In two preferred embodiments, acrylic acid and styrene, respectively, are the monomers.Type: GrantFiled: June 5, 1985Date of Patent: May 5, 1987Assignee: Mallinckrodt, Inc.Inventors: Ervin B. Inskip, Douglas C. Caskey, William E. Dummitt
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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: 4615838Abstract: Unsaturated compounds of the formula: ##STR1## in which: Q denotes alkyloxycarbonyl, cyano or formyl, R.sub.1 denotes a saturated or unsaturated aliphatic radical, R.sub.2 denotes a hydrogen atom or an alkyl radical, R.sub.3 denotes a hydrogen atom or an aliphatic radical and R.sub.4 denotes a hydrogen atom or a saturated or unsaturated aliphatic radical which may be substituted, are useful as intermediates in the synthesis of vitamin E.Type: GrantFiled: November 16, 1984Date of Patent: October 7, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4614827Abstract: A method for isolating a vinyl salt compound in solid form from an aqueous solution thereof by spray drying such an aqueous salt solution.Type: GrantFiled: July 10, 1984Date of Patent: September 30, 1986Assignee: Rohm GmbHInventors: Peter J. Arndt, Franz Wenzel, Manfred Muller, Fritz Schlosser
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Patent number: 4613680Abstract: Angelic acid or esters thereof which are useful as perfume materials are prepared by isomerizing tiglic acid or an ester thereof with an organic sulfinic acid as the catalyst, and novel esters of angelic acid represented by the formula ##STR1## wherein R represents 3-hexenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-2-pentenyl, 3-methyl-4-pentenyl, CH.sub.3 (CH.sub.2).sub.l - (in which l is an integer from 5 to 9), cyclopentyl, cyclohexyl, 2-methylpentyl, .alpha.-methylbenzyl, neryl or furfuryl are provided as part of said esters of angelic acid.Type: GrantFiled: February 24, 1984Date of Patent: September 23, 1986Assignee: Toray Industries, Inc.Inventors: Masanobu Naruto, Hisao Kondo, Go Hata
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Patent number: 4599443Abstract: A compound of the formula ##STR1## where R.sub.1 is hydrogen, lower alkyl, alkaline earth metal or alkali metal; or magnesium halide salts thereof, useful as intermediates for unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A.Type: GrantFiled: October 31, 1984Date of Patent: July 8, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
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Patent number: 4581365Abstract: The invention relates to new trichloroacryloyl oxime compounds of the general formula (I) ##STR1## wherein each of R.sup.1 and R.sup.2 represents a hydrogen atom, a lower alkyl group, a benzyl group, a benzylthio group, a lower alkylthio group, a cycloalkyl group, a halogen atom, a styryl group, a halogenophenylthio group, a naphthyl group, or a phenyl group which may optionally be substituted by at least one substituent selected from the class consisting of a halogen atom, a nitro group, a lower alkyl group, a lower alkoxy group, a phenoxy group, a benzyloxy group, a lower alkylthio group, a thiocyanato group, a di-lower alkylamino group, a halogenopyridyloxy group and a methylenedioxy group, or R.sup.1 and R.sup.2, together with the carbon atom to which they are bonded, may form an aliphatic ring, said ring being optionally substituted by at least one methyl group, and their use as fungicides.Type: GrantFiled: December 2, 1983Date of Patent: April 8, 1986Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Yasuo Yamada, Junichi Saito, Toshio Gotoh, Osamu Katsumata, Shinji Sakawa
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Patent number: 4560763Abstract: A base precursor for heat-developable photosensitive material is disclosed. The precursor is comprised of a compound represented by general formula (I) or (II):(R--C.tbd.C--CO.sub.2 H).sub.x.B (I)R--C.tbd.C--CO.sub.2 H).sub.2.B.sub.y (II)The substituents within the general formulae are defined within the specification. The use of this novel base precursor makes it possible to obtain a material which is very stable at normal temperatures and which smoothly decomposes under heating at 80.degree. C. or higher in order to release a basic constituent.Type: GrantFiled: March 30, 1984Date of Patent: December 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Hiroyuki Hirai
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Patent number: 4549974Abstract: The invention provides certain salts of sulfurized carboxylic acids and diamines and their use as friction reducing additives in lubricants or fuels. They are also antioxidants and useful in operations where an additive not corrosive to copper is required.Type: GrantFiled: September 23, 1983Date of Patent: October 29, 1985Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4542231Abstract: New and improved compositions are described of ethylenically unsaturated organic compounds capable of addition polymerization stabilized from unintentional or premature polymerization in the liquid phase by the addition of the combination cerium compounds which are soluble in the ethylenically unsaturated organic compounds and phenolic type inhibitors.Type: GrantFiled: July 5, 1983Date of Patent: September 17, 1985Assignee: Celanese CorporationInventors: Edward F. Dougherty, Mark O. Scates
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Patent number: 4536326Abstract: Acrylamide and related monomers are improved by incorporating therein an effective polymerization inhibitor in an amount greater than that which is inherently present in the monomer and a borane, i.e., sodium borohydride.Type: GrantFiled: January 4, 1984Date of Patent: August 20, 1985Assignee: American Cyanamid CompanyInventor: Joseph M. Schmitt
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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: 4528384Abstract: Novel polymers having high activity as cationic surface-active agents are prepared by the addition polymerization of ethylenically unsaturated aromatic sulfonium salts, e.g., ##STR1## When such polymers are heated and/or dried, they are irreversibly converted to inert, nonionic residues without the elimination of odorous by-products.The novel sulfonium salt polymers having relatively low molecular weight and low charge density are particularly useful as surfactants or emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers such as styrene, butadiene, alkyl acrylates and the like. The polymers having high molecular weight and high charge density are useful as thickeners and flocculants.Type: GrantFiled: June 30, 1980Date of Patent: July 9, 1985Assignee: The Dow Chemical CompanyInventors: Donald L. Schmidt, Thomas C. Klingler, Ritchie A. Wessling
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Patent number: 4504674Abstract: Alkyl acrylate esters are dimerized to dialkyl hexenedioates in the presence of a metal-treated ruthenium compound, an alcohol, optionally a phosphine, and optionally a carboxamide. The hexenedioate products are useful to prepare adipic acid.Type: GrantFiled: April 18, 1983Date of Patent: March 12, 1985Assignee: E. I. DuPont de Nemours & Co.Inventor: Ronald J. McKinney
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Patent number: 4502993Abstract: The invention relates to a process for the preparation of unsaturated aliphatic carboxylic acids by thermal cracking of the polymeric intermediate product ("polyester") which is formed in the catalytic reaction of aldehydes or ketones with ketene. The reaction mixture containing polyester is heated with water, and the polyester is then isolated and subjected to cracking. Or the polyester is first isolated and then heated with water and finally subjected to cracking. In both cases the temperature when the mixture is heated with water is the same as the boiling point, or is less than 40.degree. C. below the boiling point, of the aqueous mixture.Type: GrantFiled: May 19, 1982Date of Patent: March 5, 1985Assignee: Hoechst AktiengesellschaftInventors: Hermann Neu, G/u/ nter Roscher
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Patent number: 4503240Abstract: Process for the preparation of 8,12-epoxy-13,14,15,16-tetranorlabdane by way of converting farnesyl bromide to farnesyl cyanide, followed by the saponification of the farnesyl cyanide to homofarnesic acid which is then cyclized to norambreinolide in the presence of titanium tetrachloride, converting the norambreinolide with LiAlH.sub.4 to 8-hydroxy-13,14,15,16-tetranorlabdane-12-ol, and cyclization of the diol in the presence of POCl.sub.3 to 8,12-epoxy-13,14,15,16-tetranorlabdane. The resulting product exhibits an amber scent, used in perfumery.Type: GrantFiled: July 28, 1983Date of Patent: March 5, 1985Assignee: Consortium F/u/ r Elektrochemische Industrie GmbHInventors: Gerhard Staiger, Antonio Macri
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Patent number: 4492799Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.Type: GrantFiled: July 2, 1979Date of Patent: January 8, 1985Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4485256Abstract: Process for dimerizing alkyl acrylate esters to dialkyl hexenedioates in the presence of an alkali metal-treated or alkaline earth metal-treated ruthenium compound. The hexenedioate products are useful to prepare adipic acid.Type: GrantFiled: February 28, 1983Date of Patent: November 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 4480116Abstract: The present invention provides an improvement in methods for preparing and processing readily polymerizable acrylate monomers. The improvement comprises employing phenyl-para-benzoquinone, 2,5-di-phenyl-para-benzoquinone, and mixtures thereof as process inhibitors. The process inhibitors are present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2000 ppm, and most preferably about 500 ppm.Type: GrantFiled: March 2, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: Ambrose J. Clonce, Michael Palmer, Samuel L. Gott
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Patent number: 4477384Abstract: .alpha.-Substituted acrylic acids are prepared from carboxylic acids in high yield and high purity by novel process. The .alpha.-substituted acrylic acids are prepared by condensing a fatty acid with 2-amino-2-methylpropanol, neutralizing the resulting oxazoline reaction mixture, converting the oxazoline with paraformaldehyde to an intermediate which is heated with an azetrope such as cumene or xylene and the resulting methylene oxazoline hydrolyzed to obtain the desired product.Type: GrantFiled: February 20, 1981Date of Patent: October 16, 1984Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Samuel Serota, Warner M. Linfield
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Patent number: 4464304Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.Type: GrantFiled: June 30, 1982Date of Patent: August 7, 1984Assignee: Duke UniversityInventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
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Patent number: 4451665Abstract: Catalytic process for dimerizing a lower alkyl acrylate or methacrylate by contacting, at about 0.degree. to about 150.degree. C., the acrylate or methacrylate with the catalyst of the formula (RCN).sub.4 PdX.sub.2 wherein R is hydrocarbyl which contains no carbon-carbon unsaturation other than aromatic unsaturation and X is an anion which is incapable of displacing RCN from the cationic moiety of the palladium complex.Type: GrantFiled: December 30, 1982Date of Patent: May 29, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: William A. Nugent
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Patent number: 4434101Abstract: Methyl derivatives of arachidonic acid and intermediates thereto have been synthesized. These derivatives are inhibitors of SRS-A synthesis and are useful for treating and preventing allergic reactions.Type: GrantFiled: September 14, 1981Date of Patent: February 28, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Giuseppe Weber
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Patent number: 4423064Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.Type: GrantFiled: June 29, 1981Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4421865Abstract: A method of obtaining deuterated compounds from compounds having an abstractable proton comprises contacting the proton-containing compound with a porous ion exchange resin which contains at least some deuterons. The reverse process of substituting protons for deuterons in deuterated compounds is also described. Highly pure products can be obtained.Type: GrantFiled: June 8, 1981Date of Patent: December 20, 1983Assignee: Standard Oil Company (Sohio)Inventor: Jacob Shen
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Patent number: 4418181Abstract: The compositions described herein comprise polyimides having bis-maleimide terminal groups and having the formula: ##STR1## wherein Q is a trivalent aromatic radical, Ar is a divalent aromatic radical, Ar" is a tetravalent aromatic radical and n has a value of 0-20. Derivatives may be made of these compounds by homopolymerization, copolymerization with other copolymerizable materials and by reaction with Diels-Alder reactable materials.Type: GrantFiled: May 26, 1981Date of Patent: November 29, 1983Assignee: Plastics Engineering CompanyInventor: Walter J. Monacelli
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Patent number: 4409238Abstract: Novel insecticidal compositions are comprised of an active isovalerate having the structural formula: ##STR1## wherein Z.sup.1 is hydrogen, ##STR2## Z.sup.2 is either ##STR3## when Z.sup.1 is hydrogen, or hydrogen when Z.sup.1 is either ##STR4## A, when Z.sup.1 is ##STR5## is cyano or ethynyl or, when Z.sup.1 is other than ##STR6## is hydrogen, cyano or ethynyl; X and Y which may be the same or different are chlorine or bromine.Type: GrantFiled: December 26, 1979Date of Patent: October 11, 1983Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura
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Patent number: 4404398Abstract: Disclosed is a method of preparing alpha-beta and beta-gamma unsaturated monocarboxylic acids having electron withdrawing, electrophilic substituents at the site of unsaturation. The acids are prepared by reacting metal salts of the unsaturated acids with strong mineral acids under substantially anhydrous conditions.Type: GrantFiled: November 25, 1981Date of Patent: September 13, 1983Assignee: PPG Industries, Inc.Inventor: Norman R. DeLue