Unsaturation In Alcohol Moiety Patents (Class 560/201)
  • Patent number: 4693849
    Abstract: 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: Grant
    Filed: September 13, 1985
    Date of Patent: September 15, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4670582
    Abstract: Process for the preparation of carboxylate esters of alpha-ethylenically unsaturated alcohols by reacting an ethylenically unsaturated compound with carbon monoxide and an enolizable ketone in the presence of a catalytic system formed by combining a palladium catalyst, a triarylphosphine and a protonic acid having a pK.sub.a below 1.5, except hydrohalogenic acids and carboxylic acids.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: June 2, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4633008
    Abstract: A phenol derivative represented by the formula ##STR1## wherein R.sup.1 is a secondary or tertiary hydrocarbon residue of having 3 to 8 carbon atoms, R.sup.2 is a hydrocarbon residue having 1 to 12 carbon atoms, X is ##STR2## wherein R.sup.3, R.sup.4 and R.sup.5 each is an alkylene group having 1 to 4 carbon atoms, Z is an n-valent group and n is an integer of 1 to 8.This compound is effective to prevent the oxidation of organic materials.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: December 30, 1986
    Assignee: Mitsubishi Yuka Fine Chemicals Co., Ltd.
    Inventors: Akiyoshi Oonishi, Kenji Tanaka, Makoto Tadeka, Kazuhiko Konno, Masaki Saito
  • Patent number: 4612386
    Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: September 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga
  • Patent number: 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: 4590244
    Abstract: A composition containing acid halide functional materials, which are useful in the preparation of nylon block polymers, selected from the group consisting of: ##STR1## wherein, X is a halogen;a is an integer equal to 1, 2 or 3;b is an integer equal to 2 or more;R is a di- or a poly-valent group selected from hydrocarbon groups and hydrocarbon groups containing ether linkages;Z is a segment of: (1) a polyether; (2) a polyester containing polyether polyester hydrocarbon segments, (3) a hydrocarbon; (4) a polysiloxane; or (5) combinations thereof.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: May 20, 1986
    Assignee: Monsanto Company
    Inventors: James D. Gabbert, Albert Y. Garner, Ross M. Hedrick
  • Patent number: 4582927
    Abstract: Diesters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or alkyl of from 1 to about 20 carbon atoms, and X and Y are alkyl, alkenyl or dienyl of from about 12 to about 18 carbon atoms, useful as low calorie synthetic oils suitable for consumption by mammals.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: April 15, 1986
    Assignee: Frito-Lay, Inc.
    Inventor: John Fulcher
  • Patent number: 4518796
    Abstract: A method for preparing a carboxylic ester by reacting an aldehyde with an alcohol in the presence of oxygen with a catalyst, characterized in that the catalyst is a solid catalyst comprising palladium and bismuth, which may form an intermetallic compound, and which catalyst may comprise an alkali metal compound or an alkaline earth metal compound. The aforesaid catalyst avoids decomposition reactions simultaneously with the desired reaction, and therefore, the desired compound can be obtained in a high yield.
    Type: Grant
    Filed: May 13, 1980
    Date of Patent: May 21, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Yoshio Suzuki, Setsuo Yamamatsu, Tatsuo Yamaguchi
  • Patent number: 4515974
    Abstract: Fumaric acid monoesters can be prepared by introducing a hydroxyl compound at a rate corresponding to the progress of the reaction into a solution or a melt of maleic anhydride, which may optionally be substituted, if appropriate in the presence of a cis-trans catalyst. New fumaric acid monoesters can be formed by the process.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 7, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Zecher, Rudolf Merten
  • 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: 4473371
    Abstract: Perfluoroalkyl esters of the formula ##STR1## wherein R.sub.1 denotes C.sub.2 -C.sub.20, preferably C.sub.4 -C.sub.14 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl, R.sub.2 denotes C.sub.3 -C.sub.4 -alkylene, R.sub.3 denotes C.sub.2 -C.sub.5 -.omega.-epoxyalkyl or C.sub.1 -C.sub.18, preferably C.sub.1 -C.sub.5 -alkyl, which can be substituted by 1 or 2 halogen atoms, preferably chlorine atoms, by hydroxyl groups, by a group of the formula ##STR2## by 1 to 3 groups of the formula --OCO--CX.dbd.CY--COO--(CH.sub.2).sub.m --R.sub.1 or by, in each case, one lower alkoxy, epoxy, lower acyloxy, lower alkoxycarbonyl, lower acylamino, lower hydroxylalkylthio, lower trialkylamino, lower trialkylammonium, phenyl, phenoxy or furanyl group or R.sub.3, in the case where b=0, also denotes C.sub.3 -C.sub.18 -alkenyl, which can be subsituted by hydroxyl groups or a phenyl group; C.sub.3 -C.sub.8 -alkynyl, which can be substituted by hydroxyl groups; cyclohexyl; phenyl, which can be substituted by 1-3 C.sub.1 -C.sub.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erich Schinzel, Emmerich Paszthory
  • Patent number: 4423071
    Abstract: Mono-, di-, tri- and tetra-esters derived from an acid of the general formula:R--OHin which R represents an acyl radical of the general formula: ##STR1## in which n represents 0 or 1, m represents 0, 1, 2, 3 or 4, R.sub.1 and R.sub.2 each represent a straight- or branched-chain alkyl radical having from 1 to 5 carbon atoms, R.sub.3 represents hydrogen or a straight- or branched-chain alkyl radical having from 1 to 5 carbon atoms, the sum of the carbon atoms in R.sub.1 and R.sub.2 being from 4 to 10 when R.sub.3 represents hydrogen and the sum of the carbon atoms in R.sub.1, R.sub.2 and R.sub.3 being from 6 to 15 when R.sub.3 is different from hydrogen, or R.sub.1 and R.sub.2 when they are taken together represent a tetramethylene, pentamethylene or hexamethylene radical and R.sub.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: December 27, 1983
    Assignee: Sanofi
    Inventors: Michel Chignac, Claude Grain, Fernand Jammot, Charles Pigerol, Pierre Eymard, Bernard Ferrandes
  • Patent number: 4408029
    Abstract: The present invention provides a relatively low molecular weight polymer comprising units derived from an unsaturated dicarboxylic acid and units derived from octadienol. The polymer exhibits a fluid viscosity of at least about 200 cp when measured in the neat state at room temperature using a Brookfield viscosimeter. The unsaturated dicarboxylic acids from which the polymer units are derived include fumaric acid, maleic acid, and mixtures thereof. The octadienol from which the polymer units are derived commonly comprises a mixture of 2,7-octadien-1-ol and 1,7-octadien-3-ol. Preferably, the polymer exhibits a fluid viscosity of about 700-900 cp. The process for preparing the polymer comprises reacting octadienol with an unsaturated dicarboxylic acid selected from fumaric acid, maleic acid, lower alkyl diesters of said acid, and mixtures thereof in the presence of an esterification catalyst. Preferably, the esterification catalyst comprises dibutyltin oxide and is present in an amount of about 0.
    Type: Grant
    Filed: October 21, 1982
    Date of Patent: October 4, 1983
    Assignee: Eastman Kodak Company
    Inventors: Jerome L. Stavinoha, Anthony W. McCollum
  • Patent number: 4400531
    Abstract: 4-Vinyl-2-methylenebutanedioic acid and its esters, as well as amide and nitrile analogs of these compounds, are disclosed. These compounds are capable of undergoing a rapid free radical cyclopolymerization reaction. The compounds, themselves, may be used as film-formers (for example, in paints or plastics) or may be used as groups pendant from a backbone, especially a low molecular weight backbone, to form other, more complex film-forming polymer precursor materials.
    Type: Grant
    Filed: August 7, 1981
    Date of Patent: August 23, 1983
    Assignee: The Procter & Gamble Company
    Inventor: Rodney D. Bush
  • Patent number: 4399301
    Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: August 16, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4365054
    Abstract: A glycol and terephthalic and other aromatic acids are esterified using alkali metal titanates as catalysts and the catalysts are used in polymerization of the ester.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: December 21, 1982
    Assignee: The Firestone Tire & Rubber Company
    Inventor: Bernard D. Stabley, Jr.
  • Patent number: 4361710
    Abstract: A process for the preparation of butane-1,4-diol by catalytic hydrogenation of a mixture obtained by treating maleic anhydride with an aliphatic alcohol at elevated temperatures, wherein a monohydric or dihydric aliphatic alcohol of boiling point above 180.degree. C. is used and the mixture of maleic acid and the alcohol is obtained by washing a gaseous reaction mixture, which contains maleic anhydride and is obtained in the catalytic oxidation of hydrocarbons by air, with the alcohol.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: November 30, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Rolf Schnabel, Rolf Platz
  • Patent number: 4283414
    Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.
    Type: Grant
    Filed: June 8, 1979
    Date of Patent: August 11, 1981
    Assignee: ICI Australia Limited
    Inventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
  • Patent number: 4262137
    Abstract: Isopropenyl esters and half isopropenyl ester-half carboxylic acid products are prepared by reacting at a temperature of about 150.degree.-160.degree. C. at maximum pressures of from about 400 to 1000 psi for about 10 to 20 hours in the presence of a suitable catalyst and in N-methyl-2-pyrrolidone, a saturated or unsaturated aliphatic or aromatic dicarboxylic acid with methylacetylene or with a gas containing a mixture of methylacetylene, allene and some inert short chain hydrocarbons.
    Type: Grant
    Filed: September 21, 1977
    Date of Patent: April 14, 1981
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Leonard S. Silbert, Samuel Serota
  • Patent number: 4254282
    Abstract: Lactones of the formula ##STR1## wherein R is hydrogen or a CX.sub.3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: March 3, 1981
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Daiei Tunemoto
  • Patent number: 4252727
    Abstract: A resin for coatings, particularly useful as a medium for printing inks and paints, comprising a modified polymer produced by adding at least one .alpha.,.beta.-unsaturated dicarboxylic acid or anhydride thereof to at least one liquid conjugated diolefinic polymer having a number average molecular weight of 150 to 3,000, a viscosity of 2 to 5,000 cps at 30.degree. C. and at least 50% of cis-1,4 structure and subjecting the resulting adduct to diesterification with at least one alcohol having 1 to 27 carbon atoms and whereby the acid value owing to the carboxyl group or the carboxylic anhydride group of the resulting modified polymer being made not more than 10.
    Type: Grant
    Filed: February 5, 1976
    Date of Patent: February 24, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Seimei Yasui, Minoru Hino, Kunio Izumi, Otsugu Hayashi
  • Patent number: 4249019
    Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: February 3, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
  • Patent number: 4192953
    Abstract: Polyprenyl derivatives having the formula ##STR1## in which R.sup.1 and R.sup.2 may be the same or different and each represents hydrogen atom, hydroxyl group, an alkoxy group having 1-8 carbon atoms, an aliphatic acyloxy group having 2-18 carbon atoms, an aromatic acyloxy group or an araliphatic acyloxy group having 2-3 carbon atoms in the aliphatic acyl moiety, R.sup.3 represents hydrogen atom, an alkyl group having 1-8 carbon atoms, an aliphatic acyl group having 2-18 carbon atoms, an aromatic acyl group or an araliphatic acyl group having 2-3 carbon atoms in the aliphatic acyl moiety, n is an integer of 1-4 and, when n is an interger of 2-4, R.sup.2 's may be the same or different; provided that, when n is 1 or 2, at least one of R.sup.2 and R.sup.2 's is hydroxyl group, an alkoxy group, an aliphatic acyloxy group, an aromatic acyloxy group or an araliphatic acyloxy group. These derivatives are useful as medicines for treating peptic ulcer.
    Type: Grant
    Filed: January 4, 1979
    Date of Patent: March 11, 1980
    Assignee: Sankyo Company Limited
    Inventors: Hiroshi Mishima, Akira Ogiso, Shinsaku Kobayashi
  • Patent number: 4160864
    Abstract: An adhesive composition comprising monomeric methyl allyl methylenemalonate is useful for bonding together a wide range of materials.
    Type: Grant
    Filed: September 7, 1976
    Date of Patent: July 10, 1979
    Assignee: Eastman Kodak Company
    Inventors: Ignazio S. Ponticello, John M. McIntire
  • Patent number: 4151360
    Abstract: Asymmetric synthesis of optically active 3,7,11-trimethyl-dodecan-1-ol, an intermediate for producing optically active vitamin E, from isovaleraldehyde or prenal including intermediates in this synthesis.
    Type: Grant
    Filed: May 16, 1977
    Date of Patent: April 24, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Gabriel Saucy
  • Patent number: 4112235
    Abstract: Carboxylic acids may be esterified by reaction with esters in the presence of a catalytic amount of a tin halide catalyst, the reaction being effected at temperatures ranging from about 0.degree. to about 150.degree. C.
    Type: Grant
    Filed: October 28, 1976
    Date of Patent: September 5, 1978
    Assignee: UOP Inc.
    Inventor: Louis Schmerling
  • Patent number: 4086278
    Abstract: 1-Alkenyl thioethers of glycols are described. The alkenyl thioethers possess central nervous system activity and are useful as tranquilizers.
    Type: Grant
    Filed: March 15, 1976
    Date of Patent: April 25, 1978
    Assignee: Ortho Pharmaceutical Corporation
    Inventor: Allen Frederick Hirsch
  • Patent number: 4069385
    Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.
    Type: Grant
    Filed: June 3, 1976
    Date of Patent: January 17, 1978
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Araki, Tsuneyuki Nagase
  • Patent number: 4068082
    Abstract: Esters are prepared by reaction of acyl halides and alcohols or hydroxyalkyl esters and acid halides in the presence of a tertiary amine and polar aprotonic solvents. Bis(2-methacrylatoethyl) phthalate is prepared by the reaction of phthaloyl chloride with 2-hydroxyethyl methacrylate in pyridine and acetone. Bis-phenol-A-bis(2-methacrylatoethyl)ether is prepared from 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane and methacryl chloride in acetone.
    Type: Grant
    Filed: September 19, 1973
    Date of Patent: January 10, 1978
    Assignee: Lee Pharmaceuticals
    Inventors: Donald G. Stoffey, Jan Alexander Orlowski
  • Patent number: 4056543
    Abstract: Methylenemalonates are prepared by reacting a substituted norbornene with an electrophilic material in the presence of a lithium amide complex and pyrolyzing. The resulting acrylates are useful as fast setting, polymerizable adhesives.
    Type: Grant
    Filed: September 7, 1976
    Date of Patent: November 1, 1977
    Assignee: Eastman Kodak Company
    Inventor: Ignazio Salvatore Ponticello
  • Patent number: 4049698
    Abstract: A process comprisingA. reacting an ester of malonic acid having the formula ##STR1## with formaldehyde and a diene having the formula ##STR2## in the presence of an amine catalyst at about reflux temperature to form a compound having the formula ##STR3## wherein R.sup.1 and R .sup.2 are the same or different and each represents alkyl of 1 to about 10 carbon atoms, cyclohexyl or alkenyl of 2 to about 4 carbon atoms and each R.sup.3 is the same or different and represents hydrogen, methyl or ethyl.
    Type: Grant
    Filed: August 5, 1976
    Date of Patent: September 20, 1977
    Assignee: Eastman Kodak Company
    Inventors: Gary Fred Hawkins, Robert Lee Gass