Thio Ether In Acid Moiety Patents (Class 560/152)
  • Patent number: 4774355
    Abstract: A process for preparing a pentaerythritol-tetrakis(3-alkylthio-propionate) represented by the general formula: ##STR1## wherein R represents an alkyl group having from 8 to 30 carbon atoms, is disclosed, comprising reacting an alkylmercaptan having from 8 to 30 carbon atoms with an acrylic ester or an acrylic amide to form a 3-alkylthio-propionic acid ester or a 3-alkylthio-propionic acid amide, hydrolyzing the ester or amide to form a 3-alkylthio-propionic acid, and then reacting this product with pentaerythritol. The desired product can easily be obtained at high purity and high yield by this process.
    Type: Grant
    Filed: October 24, 1986
    Date of Patent: September 27, 1988
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroyuki Omori, Teruhiko Ishii, Mitsumasa Kaitoh, Shoichiro Mori
  • Patent number: 4760061
    Abstract: Mono- or bis-complex esters or ethers of a phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined mono- or bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus; whereinA is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, whereinR.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, whereinR.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; whereinR.sup.12 is hydrogen or alkyl, and whereinR.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: July 26, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Philip N. Edwards, Brian S. Tait
  • Patent number: 4739105
    Abstract: Described are the esters of alkylthioalkanoic acids defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.3 alkyl; C.sub.3 hydroxyalkyl or C.sub.3 alkenyl; N represents 0, 1 or 2 amd M represents 0 or 1 and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: April 19, 1988
    Assignee: International Flavors & Frangrances Inc.
    Inventors: Thomas F. Courtney, Jr., Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Charles Wiener
  • Patent number: 4737300
    Abstract: The invention relates to material containing aldosemarcaptals of the formula I ##STR1## wherein n can be an integer from 2 to 6, and wherein R.sup.1 and R.sup.2 are identical or different, and in each case are C.sub.1 -C.sub.18 -alkyl, which is unsubstituted, substituted or interrupted by --O-- or --S--, or are --(CH.sub.2).sub.r --CO--N(C.sub.1 -C.sub.17 -alkyl).sub.2, r being 1 or 2, or are phenyl, benzyl or --(CH.sub.2).sub.r --CO--O--R.sup.3, in which r can be 1 or 2 and R.sup.3 is an alkali metal or C.sub.1 -C.sub.14 -alkyl; also wherein R.sup.1 and R.sup.2 are --CH.sub.2 --CH(OH)--R.sup.4, in which R.sup.4 is hydrogen, or C.sub.1 -C.sub.16 -alkyl, unsubstituted or substituted by --OH, or --CH.sub.2 --Y--(C.sub.1 -C.sub.15 -alkyl), in which Y is --O-- or --S--; or wherein R.sup.1 and R.sup.2 together form --(CH.sub.2).sub.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4701548
    Abstract: Described are thioalkanoic acid esters of phenylalkanols defined according to the structure: ##STR1## wherein M represents an integer selected from the group consisting of 1, 2 or 3; N is 0, 1 or 2; R.sub.1 represents methyl or hydrogen and R.sub.2 represents methyl or hydrogen.
    Type: Grant
    Filed: August 8, 1986
    Date of Patent: October 20, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Domenick Luccarelli, Jr., Kevin P. Miller, Charles Wiener
  • Patent number: 4689428
    Abstract: Described are methylthioalkanoic acid esters of cis-3-hexenol and citronellol defined according to the structure: ##STR1## wherein R.sub.2 represents cis-3-hexenyl or citronellyl and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: August 25, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock
  • Patent number: 4680310
    Abstract: Tetrahydronaphthalene derivatives of the formula ##STR1## wherein Y, m, n, R and R.sup.1 to R.sup.9 are as set forth herein, are described.These compounds have a pronounced calcium-antagonistic and anti-arrhythmic activity and can accordingly be used as medicaments, especially for the control or prevention of angina pectoris, ischaemia, arrhythmias and high blood pressure. The compounds of formula I can be prepared by the amination of a compound of the formula ##STR2## with a corresponding N-methyl-phenylalkylamine and optional subsequent O-acylation. Compounds of formula II and IV are also described and are within the scope of the invention.
    Type: Grant
    Filed: October 10, 1985
    Date of Patent: July 14, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Urs Hengartner, Henri Ramuz
  • Patent number: 4663476
    Abstract: Described are methylthioalkanoic acid esters of cis-3-hexenol and citronellol defined according to the structure: ##STR1## wherein R.sub.2 represents cis-3-hexenyl or cutronellyl and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: May 5, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock
  • Patent number: 4657956
    Abstract: Additives for rubber compositions, giving vulcanizates having improved retention of optimum physical properties, are compounds having the formula R--S--B--S--R where B is an organic bridging group and R is an electron-withdrawing group, for example CN, CCl.sub.3, a radical containing an activated methylene group linked to the sulphur atom or the enolic tautomer of a keto-activated methylene group. Also useful as stabilizing agents are oligomeric analogues of such compounds.
    Type: Grant
    Filed: September 13, 1985
    Date of Patent: April 14, 1987
    Assignee: Monsanto Europe, S. A.
    Inventors: Albert F. L. G. Devaux, Philippe G. Moniotte
  • Patent number: 4652670
    Abstract: Described are the cycloalkyl esters of mercaptoalkanoic acids defined according to the structure: ##STR1## wherein R.sub.1 represents hydrogen or methyl; R.sub.2 represents mono C.sub.1 -C.sub.4 alkyl substituted or unsubstituted C.sub.5 -C.sub.8 cycloalkyl; R.sub.3 represents hydrogen or methyl; and N represents 0, 1 or 2 and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: March 24, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Kevin P. Miller, Domenick Luccarelli, Jr., Charles Wiener
  • Patent number: 4649215
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which R.sup.1 represents a C.sub.1-3 -alkyl radical or a C.sub.1-3 -hydroxyalkyl radical of which the hydroxy group may be in esterified form,R.sup.2 represents an optionally unsaturated aliphatic radical having from 5 to 15 carbon atoms,R.sup.3 represents hydroxy, alkoxy or an optionally substituted amino group, and-X- represents a single bond, a methylene group or an optionally N-acylated primary aminomethylene groupwherein the O-atom of the hydroxy group is in the transconfiguration relative to the S-atom, are effective as leucotriene-antagonists since they eliminate the contractions of smooth muscles caused by leucotrienes and are therefore suitable for the treatment of allergic, especially asthmatic, conditions.
    Type: Grant
    Filed: June 25, 1985
    Date of Patent: March 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas von Sprecher, Ivan Ernest, Alan J. Main, Andreas Beck
  • Patent number: 4647691
    Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4634595
    Abstract: Described is a process for augmenting or enhancing the aroma or taste of a foodstuff comprising the step of adding to a foodstuff, a thioalkanoic acid ester of a phenylalkanol defined according to the structure: ##STR1## wherein M represents an integer selected from the group consisting of 1, 2 or 3; N is 0, 1 or 2; R.sub.1 represents methyl or hydrogen and R.sub.2 represents methyl or hydrogen.
    Type: Grant
    Filed: September 20, 1985
    Date of Patent: January 6, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Domenick Luccarelli, Jr., Kevin P. Miller, Charles Wiener
  • 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: 4631194
    Abstract: Described are the esters of alkylthioalkanoic acids defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.3 alkyl; C.sub.3 hydroxyalkyl or C.sub.3 alkenyl; N represents 0, 1 or 2 and M represents 0 or 1 and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: December 23, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Thomas F. Courtney, Jr., Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Charles Wiener
  • Patent number: 4624980
    Abstract: An N-t-alkyl-N-sec-alkyl secondary amine compound of the formula: ##STR1## wherein X, Y and Z are each independently selected from --H, --OH, or an alkyl group having from 1 to about 15 carbon atoms; and n is an integer of from 3 to about 6.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: November 25, 1986
    Assignee: Milliken Research Corporation
    Inventors: John W. Rekers, Edward W. Kluger
  • Patent number: 4604417
    Abstract: There are disclosed polymerizable thioester synergists which have utility in enhancing the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with the thioesters themselves, their use in oxidizable organics, their combination with polymerizable and/or conventional antioxidants, and with polymers which contain these thioesters as physical admixtures or segmeric units of the polymer.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: August 5, 1986
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4594254
    Abstract: Described are methylthioalkanoic acid esters of cis-3-hexenol and citronellol defined according to the structure: ##STR1## wherein R.sub.2 represents cis-3-hexenyl or citronellyl and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: June 10, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock
  • Patent number: 4590082
    Abstract: Described are the cycloalkyl esters of mercaptoalkanoic acids defined according to the structure: ##STR1## wherein R.sub.1 represents hydrogen or methyl; R.sub.2 represents mono C.sub.1 -C.sub.4 alkyl substituted or unsubstituted C.sub.5 -C.sub.8 cycloalkyl; R.sub.3 represents hydrogen or methyl; and N represents 0, 1 or 2 and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: May 20, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Manfred H. Vock, Kevin P. Miller, Domenick Luccarelli, Jr., Charles Wiener
  • Patent number: 4577025
    Abstract: A method for the preparation of an ester of .alpha.-thio-.alpha.-aromatic propionic acid derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, phenyl or benzothiazolyl, R.sup.2 is alkyl and Ar is an aromatic substituent.The method comprises reacting an ester of .alpha.-chloro-.alpha.-thiopropionic acid of the formula: ##STR2## with an aromatic compound of the formula ARH, in the presence of a Lewis acid. The method provides good reactivity and positional selectivity in the Friedel-Crafts reaction. Many esters of the formula (2) are useful as pharmaceuticals, agricultural chemicals, perfumes or their intermediates.
    Type: Grant
    Filed: August 26, 1983
    Date of Patent: March 18, 1986
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kazutaka Arai, Yoshio Ohara, Yashio Takakuwa, Toyoko Iizumi
  • Patent number: 4546198
    Abstract: Stereoisomerically-enriched esters are prepared by treating a non-symmetrical ketene with a racemic or chiral tertiary-base-substituted alkylcarbinol. Optional hydrolysis of the esters gives the corresponding optically-active carboxylic acids corresponding to the non-symmetrical ketene.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: October 8, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4540810
    Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: September 10, 1985
    Assignee: Texaco Development Corporation
    Inventor: John F. Knifton
  • Patent number: 4533747
    Abstract: The compounds represented by the formula (I) ##STR1## wherein m is 0, 1 or 2; p is 9, 10, 11, 12 or 13; R.sub.1 ' is hydrogen, ##STR2## and R.sub.2 ' is amino, --NHCH.sub.2 CO.sub.2 R.sub.3 ', ##STR3## --NHCH.sub.2 CONH.sub.2 or --OR.sub.3 ' wherein R.sub.3 ' is an alkyl radical containing one to six carbon atoms with the proviso that when m is 0, R.sub.1 ' is hydrogen are chemical intermediates in the synthesis of leukotriene antagonists of the formula (II) ##STR4## wherein m and p, are described above and R.sub.1 is hydrogen, amino or ##STR5## R.sub.2 is hydroxyl, amino, --NHCH.sub.2 CO.sub.2 H, ##STR6## --NHCH.sub.2 CONH.sub.2 ; and X is ##STR7## --CO.sub.2 H or --CH.sub.2 OH which are useful in the treatment of diseases in which leukotrienes are a factor, such as asthma.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: August 6, 1985
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Thomas W. Ku
  • Patent number: 4529810
    Abstract: Optically-active alpha-substituted carboxylic esters are prepared by treating a non-symmetrical ketene with an alcohol in the presence of an optically-active amine catalyst. Hydrolysis of the resulting esters, yields the optically-active acid corresponding to the non-symmetrical ketene.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: July 16, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4521613
    Abstract: Described is the genus of 4(hydrocarbylthio)acetoacetic esters defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.2 -C.sub.6 aliphatic hydrocarbyl and R.sub.2 represents hydrogen or C.sub.1 -C.sub.2 aliphatic hydrocarbyl and the uses of such 4(hydrocarbylthio)acetoacetic esters for augmenting or enhancing the aroma or taste of foodstuffs and chewing gums.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Thomas F. Courtney, Jr., Ranya Muralidhara
  • Patent number: 4511491
    Abstract: Phenolic compounds and methods of producing such phenolic compounds are disclosed, said compounds being of the formula: ##STR1## wherein n' is an integer from 1 to 3, and R.sub.1 is a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms.These compounds are suitable as stabilizers for synthetic resins with at least one sulfur compound of the following formulas: ##STR2## wherein R.sub.2 is an alkyl group having 4 to 20 carbon atoms, and ##STR3## wherein R.sub.3 is an alkyl group having 3 to 18 carbon atoms, and R.sub.4 and R.sub.5 each independently is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,in the ratio (I):(II) of 1:0.5-15 by weight.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: April 16, 1985
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamaki Ishii, Shinichi Yachigo, Yukoh Takahashi
  • Patent number: 4481148
    Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: November 6, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4460601
    Abstract: Dipeptides are claimed which consist of a mercaptoalkanoic acid and a derivative of said acid, namely an S-alkyl-, aralkyl-, aryl-, acyl- or aroyl derivative with methionine, a methionine ester or a methionine amide, as well as their salts with metallic cations and organic bases. These compounds have the property of protecting the liver against intoxications and have sedative and hypnotic properties.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: July 17, 1984
    Assignee: Maggioni Farmaceutici, S.p.A.
    Inventors: Giampaolo Picciola, Franco Ravenna, Mario Riva
  • Patent number: 4446264
    Abstract: Compounds prepared by reacting maleic anhydride, maleic acid or their esters with thiols; which exhibit a synergistic effect when combined with a phenolic antioxidant in the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oil, etc. are disclosed.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: May 1, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4443435
    Abstract: Novel, transient prodrug forms of biologically active agents containing mercapto groups have (i) the structural formula (I): ##STR1## wherein X is O, S, or NR.sup.5 ;R.sup.1 S is the residue of any biologically active agent R.sup.1 SH;R.sup.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 17, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4426403
    Abstract: This invention relates to a foodstuff which contains an amount of an ethyl-methylthio substituted alkyl ester having the following structure: ##STR1## wherein R and R' independently is either hydrogen or an alkyl group of from one to three carbon atoms and n is either zero or one.The ethyl-methylthio substituted alkyl ester will augment or enhance a fruity, vegetable or green pine needle flavor to the foodstuff.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: January 17, 1984
    Assignee: General Foods Corporation
    Inventors: Matthew J. Cyronak, Paul R. Zanno, Robert J. Soukup
  • Patent number: 4422870
    Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: December 27, 1983
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4362887
    Abstract: Compounds of the formula: ##STR1## wherein R, R' and R.sup.2 are alkyl radicals having 1 to 20 carbon atoms, phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms, aralkyl radicals having 7 to 12 carbon atoms, or cycloalkyl radicals having 5 to 12 carbon atoms; and wherein R.sup.3 is hydrogen or an alkyl radical having from 1 to 4 carbon atoms. These compounds have utility as synergistic stabilizers with phenolic type antioxidants for the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oils, etc.
    Type: Grant
    Filed: April 10, 1981
    Date of Patent: December 7, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Richard H. Kline
  • Patent number: 4349468
    Abstract: A new process for preparing a polyhydric alcohol 3-alkylthiopropionate polyolefin resin stabilizer is provided, comprising the steps of heating at 40.degree.-160.degree. C. an alpha-olefin having 6 to 28 carbon atoms with betamercaptopropionic acid or a lower alkyl betamercaptopropionate in the presence of an organic peroxide or azonitrile reaction initiator, esterifying the resulting 3-alkylthiopropionic acid or ester with pentaerythritol or tris(2-hydroxyethyl) cyanurate, and recovering the polyhydric alcohol 3-alkylthiopropionate polyolefin resin stabilizer from the mixture.Polyolefin resin compositions stabilized with the stabilizer prepared by the process of this invention, and stabilizer compositions comprising the stabilizer prepared by the process of this invention together with a phenol and/or an alkaline earth metal salt of a monocarboxylic acid are also provided.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: September 14, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Tohru Haruna
  • Patent number: 4342705
    Abstract: Vulcanizable rubber compositions are described which are inhibited from premature vulcanization by activated methylene di(thioethers) in which the adjacent activating groups are either carbonyl or cyano. Novel compounds are also described.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: August 3, 1982
    Assignee: Monsanto Company
    Inventors: Otto W. Maender, Eiichi Morita
  • Patent number: 4340707
    Abstract: What is disclosed are a liquid coating and binding agent, hardenable under the influence of ultraviolet radiation, comprising an oligomer of the formula[(CH.sub.2 .dbd.CHCOO).sub.m ROOCC.sub.2 H.sub.4 ].sub.2 Sor[(CH.sub.2 .dbd.CHCOO).sub.m ROOCC.sub.2 H.sub.4 S].sub.p R',and a method for its preparation by the reaction of hydrogen sulfide or of a polymercaptan of the formulaR'(SH)pwith a polyacrylic acid ester of the formula(CH.sub.2 .dbd.CHCOO).sub.m+1 R.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: July 20, 1982
    Assignee: Rohm GmbH
    Inventors: Peter Quis, Theodor Schroth
  • Patent number: 4313956
    Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: February 2, 1982
    Assignee: INTERx Research Corp.
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4311706
    Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: January 19, 1982
    Assignee: INTERx Research Corporation
    Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
  • Patent number: 4301296
    Abstract: Ester such as 3,6,9-trioxaundecane-1,11-bis(3-n-dodecylthiopropionate) when combined with conventional free amine antioxidants such as N,N'-diphenylparaphenylenediamine or with polymer bound antioxidants such as N-(4-anilinophenyl) methacrylamide produce improved antioxidant systems for SBR and NBR type polymers.
    Type: Grant
    Filed: September 29, 1980
    Date of Patent: November 17, 1981
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Joseph A. Kuczkowski
  • Patent number: 4293472
    Abstract: New ortho-alkylhydroxybenzyl substituted propanediol compounds of carboxylic acids, aldehydes, ketones, phosphites, phosphates, and phosphonates are disclosed. The propanediol compounds have in the molecule from one to four preferably from one to three ortho-alkylhydroxybenzylpropanediol units, each of which carries one to two ortho-alkylhydroxybenzyl groups, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a orthoalkylhydroxybenzylpropanediol compound and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.
    Type: Grant
    Filed: April 24, 1979
    Date of Patent: October 6, 1981
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4291057
    Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: September 22, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4276225
    Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: June 30, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hellmut Hoffmann
  • Patent number: 4267307
    Abstract: A sealant composition based on a mercaptan-terminated liquid polymer, fillers, plasticizer, and curing agent wherein the liquid mercaptan-terminated polymer employed is prepared from a mercapto acid or mercapto acid ester and a polyoxypropylene glycol, the polyoxypropylene glycol having been end-capped with ethylene oxide prior to esterification to give primary alcohol terminal groups. The cured sealant based on the ethylene oxide-end capped polymer exhibits a non-tacky surface, whereas a cured sealant based on a propylene oxide end-capped glycol exhibits a tacky surface.
    Type: Grant
    Filed: November 29, 1979
    Date of Patent: May 12, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Rector P. Louthan, Richard C. Doss
  • Patent number: 4260503
    Abstract: Epithio compounds or mercaptans of the formula I ##STR1## wherein X is an oxygen or sulfur atom, --CH.sub.2 --, --CH(R.sub.1)--, --COO--, --NH-- or --NR.sub.1 --, each of Y and Z is hydrogen or together they are a direct bond, Q is hydrogen if Y and Z together are a direct bond, or is --OH, --SH, --OR.sub.1, --SR.sub.1, --OOCR.sub.1, --S--CH.sub.2).sub.n OH, --S--CH.sub.2).sub.n COOR.sub.1, --NHR.sub.1 or --N(R.sub.1).sub.2, n is an integer from 1 to 10, each of R and R.sub.1 independently is a cyclic or acyclic hydrocarbon radical of aliphatic or aromatic character containing 4 to 30 carbon atoms which can be interrupted by oxygen or sulfur, with the proviso that the groups R and R.sub.1 contain a total number of 8 to 30 carbon atoms. These compounds have excellent suitability for use as additives for lubricants, especially as extreme pressure and antiwear additives.
    Type: Grant
    Filed: November 26, 1979
    Date of Patent: April 7, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Michaelis
  • Patent number: 4254020
    Abstract: Compounds of the formula: ##STR1## wherein R is selected from (1) alkyl radicals having 6 to 20 carbon atoms; (2) phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms; or (3) aralkyl radicals having 7 to 12 carbon atoms; and wherein R.sup.1 is selected from (1) alkylene radicals having 2 to 6 carbon atoms; (2) cycloalkylene radicals having 5 to 12 carbon atoms; (3) alkylcycloalkylene radicals of the formula --R.sub.3 --R.sub.2 (R.sub.4).sub.n, wherein R.sub.2 is a cycloalkylene radical having 5 to 12 carbon and R.sub.3 and R.sub.4 are alkylene radicals having 1 to 6 carbon atoms, and n equals 1 or 0; (4) or a group of the formula --R.sub.5 --YR.sub.6, wherein R.sub.5 and R.sub.6 are alkylene radicals having 2 to 6 carbon atoms and Y is oxygen, sulfur, or a 1,4-phenylene radical.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: March 3, 1981
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Richard H. Kline
  • Patent number: 4248723
    Abstract: Acetal and thioacetal derivatives of the formula I ##STR1## in which R.sub.1 and R.sub.2 are identical or different C.sub.1 -C.sub.12 alkyl or together are C.sub.4 -C.sub.7 alkylene, X and Y are identical or different and are each O or S and R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.9 aralkyl, carboxy-(C.sub.1 -C.sub.2)-alkyl, (C.sub.1 -C.sub.18 -alkoxy)-carbonyl-(C.sub.1 -C.sub.2)-alkyl, N-C.sub.1 -C.sub.18 -alkylated carbamoyl-(C.sub.1 -C.sub.2)-alkyl or an ammonium salt of an amine with carboxymethyl or 2-carboxyethyl, or two R.sub.3 radicals of an acetal/thioacetal group together are C.sub.2 -C.sub.4 alkylene.
    Type: Grant
    Filed: June 14, 1978
    Date of Patent: February 3, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Andreas Schmidt
  • Patent number: 4243585
    Abstract: 1,2,3,4-Tetrahydro-1,5-benzodiazocines having the following formula ##STR1## in which R.sup.1 is a hydrogen, alkyl radical having at most 6 carbon atoms, methoxyethyl, or benzyl radical,R.sup.2 is a halo, hydroxyl, acetoxy or benzoxy radical,R.sup.3 is a phenyl, 2-methylphenyl, 2-chlorophenyl, 2-bromophenyl, 2-fluorophenyl, 2-nitrophenyl, 2-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 3,4-dimethoxyphenyl, or 3,4,5-trimethoxyphenyl radical,R.sup.4 is a hydrogen, chloro, fluoro, bromo, trifluoromethyl, methyl, methoxy, or methylthio radical, andR.sup.5 is a hydrogen or methoxy radical, or R.sup.4 and R.sup.5 together are an ethylendioxy radical, or an acid addition salt of the said benzodiazocine, and processes of making the same are described.
    Type: Grant
    Filed: January 23, 1978
    Date of Patent: January 6, 1981
    Assignee: Kali-Chemie Aktiengesellschaft
    Inventors: Wolfgang Milkowski, Renke Budden, Siegfried Funke, Rolf Huschens, Hans-Gunther Liepmann, Werner Stuhmer, Horst Zeugner
  • Patent number: 4241217
    Abstract: Ester such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) when combined with conventional free amine antioxidants such as N,N'-diphenylparaphenylenediamine or with polymer bound antioxidants such as N-(4-anilinophenyl) methacrylamide produce improved antioxidant systems for SBR and NBR type polymers.
    Type: Grant
    Filed: May 26, 1978
    Date of Patent: December 23, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Joseph A. Kuczkowski
  • Patent number: 4239904
    Abstract: A process for the preparation of urethanes by reacting a tertiary amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: December 16, 1980
    Assignee: Atlantic Richfield Company
    Inventor: Haven S. Kesling, Jr.
  • Patent number: 4231956
    Abstract: The process of preparing thioethers by reacting aliphatic thioalcohols, e.g., mercaptans, including hydrogen sulfide with activated, alpha, beta unsaturated compounds ##STR1## capable of participating in the Michael Addition Rection* in which X is a suitable electron withdrawing group. The Addition, which is carried out in the presence of a catalytic base is greatly improved with respect to minimizing formation of side products by utilizing a specially selected catalyst comprising one or more cyclic tertiary nitrogen compounds having an excellent balance between reactivity and selectivity. The preparation of thioethers from acrylic acid derivatives especially esters (CH.sub.2 .dbd.CH--COOR', R'=C.sub.1 --C.sub.8) is preferred. The preparation of the dimethyl ester of 3,3'-thiodipropionic acid to result in dimethylthiodipropionate of relatively high purity is especially preferred.* See Vogel, PRACTICAL ORGANIC CHEMISTRY, p. 912-913, Third Enlarged Edition.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: November 4, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventors: Daniel S. Sullivan, III, Wilbur L. Bridges