Thio Ether In Acid Moiety Patents (Class 560/152)
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Patent number: 9388282Abstract: A process comprising contacting a reaction product composition comprising a poly(arylene sulfide) composition and a polar organic compound, wherein the polar organic compound comprises greater than or equal to about 1 wt. % thiophenol, with a C4-C30 ?,?-unsaturated ketone, a C4-C30 ?,?-unsaturated ester, a C4-C30 ?,?-unsaturated amide, or any combination thereof, wherein after the contacting, the polar organic compound comprises less than about 1 wt. % thiophenol. A process comprising contacting a composition comprising a polar organic compound and greater than or equal to about 1 wt. % thiophenol with a C4-C30 ?,?-unsaturated ketone, a C4-C30 ?,?-unsaturated ester, a C4-C30 ?,?-unsaturated amide, or any combination thereof, to form a composition comprising the polar organic compound and less than about 1 wt. % thiophenol.Type: GrantFiled: October 29, 2013Date of Patent: July 12, 2016Assignee: SOLVAY SPECIALTY POLYMERS USA, LLC.Inventors: Michael S. Matson, David A. Soules
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Publication number: 20140323651Abstract: The present invention relates to the use of a compound of formula (I): wherein: —R represents —OH or —NH2; —A1 represents a divalent alkylene radical, straight or branched, having from 2 to 20 carbon atoms; —A2 represents a divalent alkylene radical, straight or branched, having from 1 to 20 carbon atoms; —X1 and X2 represent, independently of each other, —NH— or ?O—; —A3 represents a divalent alkylene radical, straight or branched, having from 1 to 10 carbon atoms; —Z represents a hydrogen or a group of formula (A?): wherein A1, A3 and R are as defined above in formula (I), for the preparation of a polymer chosen among polyurethane, polyester and polyamide.Type: ApplicationFiled: November 15, 2012Publication date: October 30, 2014Inventors: Lise Maisonneuve, Thomas Lebarbe, Henri Cramail, Carine Alfos, Benoît Gadenne, Eric Cloutet
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Publication number: 20140171676Abstract: A method of preparing acrolein from glycerol or glycerine is disclosed. The method includes dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least (a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, or (b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, or (c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, or (d) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon.Type: ApplicationFiled: August 27, 2013Publication date: June 19, 2014Applicants: Centre National De La Recherche Scientifique, Adisseo France S.A.SInventors: Virginie BELLIERE-BACA, STEPHANE LORIDANT, JEAN-MARC MILLET, PASCALINE LAURIOL-GARBEY
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Publication number: 20140121143Abstract: A composition that includes one or more compounds represented by the formula (R1)a(X)(R2)b wherein R1 and R2 are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of an aliphatic polythiol, aromatic polythiol, cycloaliphatic polythiol, ester or acid containing thiol, or ester or acid containing polythiol, a is a value from 1 to 6, and b is a value from 0 to 6. The composition has a viscosity (Kv100) from 2 to 30 at 100° C., a viscosity index (VI) from 100 to 200, and a Noack volatility of no greater than 20 percent. The disclosure also relates to a process for producing the composition, a lubricating oil base stock and lubricating oil containing the composition, and a method thr improving one or more of solubility and dispersancy of polar additives in a lubricating oil by using as the lubricating oil a formulated oil containing the composition.Type: ApplicationFiled: October 25, 2012Publication date: May 1, 2014Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Abhimanyu Onkar Patil, Satish Bodige, Shuji Luo
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Publication number: 20130217909Abstract: A continuous process for obtaining acrolein by catalytic dehydration of glycerol or glycerin, in the presence of an acid catalyst, wherein said process comprises the concomitant regeneration of said catalyst and is carried out in a fluidized bed reactor, said reactor comprising two zones, a first zone, or lower zone, termed catalyst regeneration zone, in which a fluidization gas comprising oxygen is introduced, and a second zone, or upper zone, termed reaction zone, in which the glycerol or glycerin is introduced and converted into acrolein.Type: ApplicationFiled: October 26, 2011Publication date: August 22, 2013Applicants: ECOLE CENTRALE DE LILLE, ADISSEO FRANCE S.A.S.Inventors: Stephane Pariente, Virginie Belliere-Baca, Sebastien Paul, Nouria Fatah
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Publication number: 20130150611Abstract: The present invention relates to a process for producing a carboxylic acid ester, comprising a step of oxidizing an aldehyde by mixing an alcohol, carbon dioxide, the aldehyde and at least one compound selected from the group consisting of compounds represented by the formulae (2-1) and (2-2): wherein R2 represents an alkyl group optionally having a substituent or the like; R3 and R4 each independently represents an alkyl group optionally having a substituent or the like or R3 and R4 are linked together to form a divalent hydrocarbon group optionally having a substituent or the like; Y represents a group of —S— or a group of —N(R5)—, wherein R5 represents an alkyl group optionally having a substituent or the like, or R5 is linked to R4 to form a divalent hydrocarbon group optionally having a substituent; and R8 represents an alkyl group.Type: ApplicationFiled: August 25, 2011Publication date: June 13, 2013Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Koji Hagiya
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Publication number: 20120330049Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.Type: ApplicationFiled: December 21, 2010Publication date: December 27, 2012Applicants: ADISSEO FRANCE S.A.S., UNIVERSITE LILLE 1 - SCIENCES ET TECHNOLOGIES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
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Patent number: 8299293Abstract: A method for preparing ?-keto acids, especially ?-ketomethionine, and/or derivatives thereof, whereby an aldehyde is reacted with thiols to give a corresponding dithioacetal, the dithioacetal formed, is reacted with an electrophile in the presence of a strong base, and the resulting ?,?-(dithio)carboxylic acid is solvolyzed with acid-catalysis to release thiol and give the ?-keto acid or a derivative thereof. Umpolung of aliphatic or aromatic aldehydes is effected by reaction with thiols.Type: GrantFiled: July 9, 2008Date of Patent: October 30, 2012Assignee: Evonik Degussa GmbHInventors: Christoph Kobler, Martin Hateley, Philipp Roth, Barbara Jaeger, Christoph Weckbecker, Klaus Huthmacher
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Publication number: 20120264966Abstract: The present invention provides a lipid compound comprising at least one non-polar moiety and a polar moiety, wherein each or at least one non-polar moiety is of the formula X—Y—Z, wherein X is a hydrocarbyl chain, Y is selected from at least one of S, Se, SO2, SO, and O, and Z is an optional hydrocarbyl group, wherein the polar moiety is of the formula —[C(O)]mPHG, wherein PHG is a polar head group, and wherein m is the number of non-polar moieties.Type: ApplicationFiled: November 23, 2011Publication date: October 18, 2012Inventors: Andrew David MILLER, Michael R. JORGENSEN, Rolf Kristian BERGE, Jon SKORVE
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Publication number: 20110319580Abstract: The invention provides intermediates of the formula: as well as a method of their preparation by reacting a thiol having at least two hydroxyl groups with a mono-unsaturated organic compound in the presence of a base catalyst. A polymerizable urethane acrylate oligomer or urethane methacrylate oligomer is formed by reacting a polyisocyanate with the intermediate. The polymerizable urethane acrylate oligomer or urethane methacrylate is blended with a polymerization initiator to form a composition which is useful in such applications as adhesives.Type: ApplicationFiled: June 28, 2010Publication date: December 29, 2011Inventors: JAMES H. AERYKSSEN, Ahmet Nebioglu, Richard D. Zopf, Igor V. Khudyakov
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Patent number: 8071805Abstract: A process for producing a 2-hydroxy-4-(methylthio)butyrate compound represented by the formula (2): wherein A is a hydrogen atom or a group represented by R—CH2—, wherein R is a hydrogen atom or an alkyl group, which comprises the step of: reacting 4-(methylthio)-2-oxo-1-butanol with oxygen and a compound represented by the formula (1): A-OH??(1) wherein A is as defined above, in the presence of a copper compound.Type: GrantFiled: July 20, 2007Date of Patent: December 6, 2011Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Publication number: 20110288323Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerine, comprising dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, d) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, e) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, f) a titanium oxide and a mixed oxide or zirconium and at least onType: ApplicationFiled: December 16, 2009Publication date: November 24, 2011Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.SInventors: Virginie Belliere-Baca, Stephane Loridant, Jean-Marc Millet, Pascaline Lauriol-Garbey
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Publication number: 20110256071Abstract: One aspect of the present invention provides a compound represented by formula (I), wherein, R1 is hydrogen or an acetyl group and R2 is a C1-3 straight chain or branched alkyl group. Another aspect of the present invention provides flavor or fragrance compositions comprising at least one compound of formula (I).Type: ApplicationFiled: March 23, 2011Publication date: October 20, 2011Applicant: Takasago International CorporationInventors: Maureen Blandino, Henry Van Den Heuvel, Michael E. Lankin
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Patent number: 7902381Abstract: The invention relates to preparing derivatives of formula (1), wherein, in particular R1 and R2, identical or different, represent a hydrogen, flourine or chlorine atom, a hydroxy group, an alkyl radical and an alkoxy radical, R3 is an alkyl radical, a hydroxy group, or a methoxy radical, R4 is a hydrogen atom or a methyl radical and R5 and R6, identical or different, represent a hydrogen atom, an alkyl radical, an alkoxy radical, an alkylthio radical, and an alkylamino radical. The inventive method consists in reducing an amid of formula (9).Type: GrantFiled: April 8, 2005Date of Patent: March 8, 2011Assignee: Pierre Fabre MedicamentInventors: Bernard Vacher, Yves Brunel, Florence Castan-Cuisiat
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Publication number: 20100324314Abstract: PROBLEM To provide an environmentally-friendly method for producing industrially an ester compound. SOLUTION The present invention is a method for producing an ester compound which comprises subjecting a carboxylic acid and an alcohol to dehydration-condensation reaction using an involatile acid catalyst and then removing the residual acid catalyst by bringing a weak basic substance into contact with the residual acid catalyst.Type: ApplicationFiled: October 20, 2007Publication date: December 23, 2010Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.Inventors: Shigeaki Imazeki, Ryohiko Kinoshita
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Publication number: 20100266821Abstract: The present invention relates to a photoreactive compound for the preparation of a photoalignment material comprising thioether units, wherein the photoreactive compound is comprising at least one ene group and at least one photoalignment group, and further to a composition comprising at least one photoreactive compound and at least one polythiol, the use of this composition for the preparation of photoalignment materials, and their use for the alignment of liquid crystals or liquid crystal polymers, in electro-optical and optical elements, systems and devices.Type: ApplicationFiled: November 6, 2008Publication date: October 21, 2010Applicant: ROLIC AGInventors: Izabela Bury, Jean-Francois Eckert, Olivier Muller, Hubert Seiberle, Peggy Studer
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Patent number: 7615661Abstract: The present invention relates to thioester compounds and the incorporation and use of the new chemical entities as flavor and fragrance chemicals.Type: GrantFiled: March 12, 2008Date of Patent: November 10, 2009Assignee: International Flavors & Fragrances Inc.Inventors: Kathryn Bardsley, David O. Agyemang, Tao Pei
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Publication number: 20090232747Abstract: The present invention relates to thioester compounds and the incorporation and use of the new chemical entities as flavor and fragrance chemicals.Type: ApplicationFiled: March 12, 2008Publication date: September 17, 2009Inventors: Kathryn Bardsley, David O. Agyemang, Tao Pei
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Publication number: 20090192328Abstract: A process for producing a 2-hydroxy-4-(methylthio)butyrate compound represented by the formula (2): wherein A is a hydrogen atom or a group represented by R—CH2—, wherein R is a hydrogen atom or an alkyl group, which comprises the step of: reacting 4-(methylthio)-2-oxo-1-butanol with oxygen and a compound represented by the formula (1): A-OH??(1) wherein A is as defined above, in the presence of a copper compound.Type: ApplicationFiled: July 20, 2007Publication date: July 30, 2009Inventor: Koji Hagiya
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Publication number: 20090192325Abstract: Methods of enzymatically resolving acyloxyalkyl thiocarbonates useful in the synthesis of acyloxyalkyl carbamate prodrugs are disclosed.Type: ApplicationFiled: January 23, 2009Publication date: July 30, 2009Applicant: XenoPort, Inc.Inventors: Mark A. Gallop, Fenmei Yao, Maria J. Ludwikow, Ge Peng, Steven P. Raillard
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Publication number: 20080269506Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.Type: ApplicationFiled: May 29, 2008Publication date: October 30, 2008Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
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Patent number: 7271283Abstract: Disclosed herein are high refractive index monomers that are curable by ultraviolet light. These monomers may be a component of curable compositions useful in the preparation of optical articles. Also disclosed is a method of synthesizing the monomers.Type: GrantFiled: July 21, 2004Date of Patent: September 18, 2007Assignee: General Electric CompanyInventors: Bret Ja Chisholm, Paul Michael Smigelski, Jr., James Edward Pickett
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Patent number: 6916850Abstract: Certain known and novel pyruvate derivatives are particularly active in restoring or preserving metabolic integrity in oxidatively competent cells that have been subjected to oxygen deprivation. These pyruvate-derived compounds include, but are not limited to oximes, amides, pyruvate analogues, modified pyruvate analogues, esters of pyruvate (e.g., polyol-pyruvate esters, pyruvate thioesters, glycerol-pyruvate esters and dihydroxyacetone-pyruvate esters). Such pyruvate derivatives (including single tautomers, single stereoisomers and mixtures of tautomers and/or stereoisomers, and the pharmaceutically acceptable salts thereof) are useful in the manufacture of pharmaceutical compositions for treating a number of conditions characterized by oxidative stress.Type: GrantFiled: May 3, 2002Date of Patent: July 12, 2005Assignee: Galileo Pharmaceuticals, Inc.Inventors: Bing Wang, Guy Miller, Wei Zhang
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Patent number: 6734321Abstract: The invention relates to novel composite materials comprising (a) an inorganic or organic bulk material having covalently bound to its surface initiator moieties for radical polymerization; and (b) a hydrophilic surface coating obtainable by applying one or more different ethylenically unsaturated hydrophilic macromonomers of formula (1) as outlined in the claims to the bulk material surface provided with the initiator radicals and polymerizing said macromonomers. The composite materials of the invention have desirable characteristics regarding adherence to the substrate, durability, hydrophilicity, wettability, biocompatibility and permeability and are thus useful for the manufacture of biomedical articles such as ophthalmic devices.Type: GrantFiled: June 20, 2002Date of Patent: May 11, 2004Assignee: Novartis AGInventors: Peter Chabrecek, Jens Höpken, Dieter Lohmann
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Patent number: 6720445Abstract: Novel acetyloxymethyl esters are disclosed. Methods of treating an illness, including cancer, hemological disorders and inherited metabolic disorders, and treating or ameliorating other conditions using these compounds are also disclosed. The compounds are effective in the inhibition of histone deacetylase.Type: GrantFiled: December 21, 2000Date of Patent: April 13, 2004Assignee: Beacon Laboratories, Inc.Inventors: Hsuan-Yin Lan-Hargest, Norbert L. Wiech
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Publication number: 20040006224Abstract: A method of preparing a 2-alkyl amino acid involves the aziridination of an alkylacrylate and the opening of the aziridine ring by addition of a side chain. This method can result in the preparation of enantiomeric excess of a 2-alkyl amino acid. The invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine, a 2-alkyl cysteine, or a cysteine ester.Type: ApplicationFiled: May 15, 2003Publication date: January 8, 2004Applicant: Genzyme CorporationInventors: Mukund S. Chorghade, Mukund K. Gurjar, Bhanu M. Chanda
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Patent number: 6599940Abstract: One aspect of the present invention relates to 2-hydroxymethylglutamic acid and congeners thereof. A second aspect of the invention relates to a method of synthesizing 2-hydroxymethylglutamic acid and congeners thereof.Type: GrantFiled: September 13, 2001Date of Patent: July 29, 2003Assignee: Georgetown UniversityInventor: Alan P. Kozikowski
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Patent number: 6562995Abstract: Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. Methods of treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, using these compounds are also disclosed.Type: GrantFiled: December 21, 2000Date of Patent: May 13, 2003Assignee: Beacon Laboratories, Inc.Inventors: Hsuan-Yin Lan-Hargest, Norbert L. Wiech
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Patent number: 6479695Abstract: A process for the preparation of 2-hydroxy-4-methylthiobutyric acid ester which comprises (a) a first step of reacting 2-hydroxy-4-methylthiobutyronitrile with sulphuric acid to produce 2-hydroxy-4-methylthiobutyramide, and (b) a second step of reacting the 2-hydroxy-4-methylthiobutyramide with an alcohol to produce a 2-hydroxy-4-methylthiobutyric acid ester, the two steps being carried out in the same reaction medium.Type: GrantFiled: December 28, 2001Date of Patent: November 12, 2002Assignee: Aventis Animal Nutrition, S.A.Inventors: Michel Garrait, Claude Casse, Georges Gros
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Patent number: 6407281Abstract: A process for producing optically active cysteine derivatives with high optical purity and good quality which is economically advantageous and is high in productivity even on a commercial scale is provided.Type: GrantFiled: August 25, 2000Date of Patent: June 18, 2002Assignee: Kaneka CorporationInventors: Yasuyoshi Ueda, Hiroshi Murao, Takeshi Kondo, Noboru Ueyama, Hajime Manabe, Kenji Yoneda, Akira Nishiyama
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Patent number: 6395930Abstract: A method for enhancing the purity of a desired compound comprising: Step (a) treating a crude reaction product which contains at least one desired compound, unreacted starting materials and/or byproducts with at least one bifunctional quenching agent that is capable of selective covalent reaction with unwanted byproducts, or excess reagents; Step (b) allowing the quenching agent to covalently react with unreacted starting materials and/or byproducts to afford a derivatized compound of the quenching agent: and Step (c) isolating the desired compound is described as well as novel quenching agents and methods for their use in the rapid purification of synthetic intermediates and products in synthesis, combinatorial chemistry, and automated organic synthesis.Type: GrantFiled: May 25, 2000Date of Patent: May 28, 2002Assignee: Warner LambertInventor: Sham Nikam
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Patent number: 6365769Abstract: Novel mixtures of perfluoroalkyl halides and derivatives thereof are described. These mixtures contain some compounds with a straight perfluoroalkyl group and some with a branched perfluoroalkyl group. Methods of preparation and use are also described.Type: GrantFiled: February 15, 2000Date of Patent: April 2, 2002Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
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Patent number: 6288267Abstract: It has been discovered that compounds of the formula: and the pharmaceutically acceptable salts and esters thereof wherein X and Y are as defined below, inhibit the binding of VCAM-1 to VLA-4 and are useful in treating inflammation associated with chronic inflammatory diseases such as rheumatoid arthritis (RA), multiple sclerosis, (MS), asthma, and inflammatory bowel disease (I BD).Type: GrantFiled: February 17, 2000Date of Patent: September 11, 2001Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth Gregory Hull, Achytharao Sidduri, Jefferson Wright Tilley
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Patent number: 6248839Abstract: The invention relates to polymethacrylate acid-polyalkylene oxide block copolymers, to a process for their preparation and to their use as dispersants or suspension stabilizers for pigments and fillers, e.g. for metal oxides in ceramic materials, for pigments in inks used in ink jet printing and for fillers in thermosplastic and thermoset polymers.Type: GrantFiled: February 3, 1998Date of Patent: June 19, 2001Assignee: Th. Goldschmidt AGInventors: Eberhard Esselborn, Jürgen Fock, Arno Knebelkamp
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Patent number: 6187938Abstract: The invention relates to amino acid derivatives of general formula (I), wherein R1 is H or CH3, X is H or NR2R3, wherein R2 is H, CH3, COH or COCH3 and R3 is H, CH3 or COO—Z wherein Z is R2R3 NH+CHR1(CH2)nCOO(CH2)mCH2Y; Y is H, CH3 or NHR4, wherein R4 a COO—NH3+CH2(CH2)mOOC(CH2)nCH3, the meaning of group (CH2)m being selected from alkyls, secondary alkyls, monocycloalkyls, bicycloalkyls and tricycloalkyls having from 4 to 15 carbon atoms and n having a value of from 3 to 14.Type: GrantFiled: December 21, 1999Date of Patent: February 13, 2001Assignee: Bochemie, s.r.o.Inventors: Alexandr Hrabálek, Pavel Dole{haeck over (z)}al, Old{haeck over (r)}ich Farsa, Ale{haeck over (s)} Krebs, Ale{haeck over (s)} Kroutil, Martin Roman, Zde{haeck over (n)}ka {haeck over (S)}klubalová
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Patent number: 6051733Abstract: Polymeric compositions for the preparation of optical grade materials, and the optical materials prepared thereby, are provided. The compositions include a class of reactive and non-reactive additives, referred to as additive, in combination with a polymer and optionally a diluent. The additives are preferably the reaction product of a thiol containing compound and an unsaturated compound. The additives optimally have a refractive index between about 1.40 and 1.70, and preferably between 1.50 and 1.70; a relatively high Abbe number (between 25 and 60) and minimal color.Type: GrantFiled: July 25, 1997Date of Patent: April 18, 2000Assignee: UCB, S.A.Inventor: Peter Weissman
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Patent number: 6011170Abstract: This invention relates to a method comprising reacting an amino acid derivative of the following general formula (I); ##STR1## (wherein R.sup.1 represents an amino-protective group; R.sup.0 represents hydrogen or, taken together with R.sup.1, represents an amino-protecting group; R.sup.2 represents a carboxy-protecting group; X represents a leaving group) with a thiol compound of the following general formula (II) :R.sup.3 SH (II)(wherein R.sup.3 represents an alkyl group of 1 to 7 carbon atoms, an aryl group of 6 to 10 carbon atoms, or an aralkyl group of 7 to 10 carbon atoms) to give a cysteine derivative of the following general formula (III): ##STR2## (wherein R.sup.0, R.sup.1, R.sup.2, and R.sup.3 are as defined above), wherein the reaction is conducted in the presence of a base and water in an organic reaction solvent.Type: GrantFiled: April 22, 1999Date of Patent: January 4, 2000Assignee: Kaneka CorporationInventors: Takeshi Kondo, Akira Nishiyama, Noboru Ueyama, Hiroshi Murao, Hajime Manabe, Yasuyoshi Ueda
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Patent number: 6008409Abstract: A method for obtaining 2-hydroxy-4-methylthiobutyric acid (methionine-hydroxy analog, MHA) in primarily free form which is stable in storage by distilling a product solution containing MHA and by producing MHA product mixtures with improved storage stability from such a distillate. The distillate can be produced directly starting from MHA raw products from any MHA production process, which can optionally also contain solvent or water. The starting material may also be a commercial MHA product.Type: GrantFiled: December 29, 1997Date of Patent: December 28, 1999Assignee: Degussa AktiengesellschaftInventors: Hans-Albrechl Hasseberg, Hans-Joachim Hasselbach, Klaus Huthmacher, Volker Hafner, Harald Heinzel, Axel Ronneburg
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Patent number: 5948936Abstract: A method for the production of a sulfide group-containing thiol compound which comprises causing alkylene sulfide to react with a thiol compound in the presence of at least one basic catalyst selected from the group consisting of basic ion-exchange resins, quaternary ammonium compounds and alkyl pyridinium compounds, thereby inducing the ring-opening addition of the alkylene sulfide to the thiol compound. Further, a method for the production of a sulfide group-containing mercaptocarboxylic ester which comprises causing an alkylene sulfide to react with a mercaptocarboxylic ester.Type: GrantFiled: July 14, 1997Date of Patent: September 7, 1999Assignees: Nippon Shokubai Co. Ltd., Elf Atochem S.A.Inventors: Hirokazu Itoh, Kazuaki Abe, Takashi Tomita
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Patent number: 5945451Abstract: The present invention relates to new fluorobutenyl (thio)ethers of the formula (I) ##STR1## in which R.sup.1 represents hydrogen or halogen,R.sup.2 and R.sup.3 independently of one another represent hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl, aralkyl or hetaryl,R.sup.4 represents hydrogen, or represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, aralkyl, hetaryl and additionally represent a metal ion equivalent or an ammonium ion if Z represents oxygen,X represents oxygen or sulphur,Y represents oxygen or sulphur,Z represents oxygen, sulphur or the radical NR.sup.5 in whichR.sup.5 represents hydrogen, in each case optionally substituted alkyl, aryl, aralkyl, hetaryl or the radical ##STR2## in which R.sup.6 and R.sup.7 independently of one another represent hydrogen, in each case optionally substituted alkyl, aryl, aralkyl, or together represent optionally substituted alkanediyl andR.sup.Type: GrantFiled: June 16, 1997Date of Patent: August 31, 1999Assignees: Bayer Aktiengesellschaft, Monsanto CompanyInventors: Udo Kraatz, Jurgen Hartwig, Wolfram Andersch, Christoph Erdelen, Andreas Turberg, Norbert Mencke, Peter Gerrard Ruminski
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Patent number: 5925764Abstract: The present invention provides a process to prepare a pyridine-2,3-dicarboxylate derivative via the reaction of a dailkyl alkoxy(or alkylthio)oxalacetate with an appropriately substituted acrolein compound in the presence of an ammonia source and a solvent.The present invention also provides useful intermediate compounds of formula IV.Type: GrantFiled: June 15, 1998Date of Patent: July 20, 1999Inventor: Wen-Xue Wu
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Patent number: 5919971Abstract: This process for the synthesis of 3-mercaptopropionic acid esters by addition reaction of H.sub.2 S to the corresponding acrylic acid ester is carried out in the presence of a solid-support functionalized with basic guanidine functional groups, on condition that these groups are free of hydrogen that is directly attached to a nitrogen atom.Type: GrantFiled: November 21, 1997Date of Patent: July 6, 1999Assignee: Elf Acquitaine Exploration Production FranceInventor: Emmanuel Arretz
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Patent number: 5919985Abstract: An object is to provide a method for the production of a sulfide group-containing thiol compound which comprises using a solvent capable of effecting the ring-opening addition reaction of an alkylene sulfide to a thiol compound without inducing the alkylene sulfide to polymerize. A method for the production of a sulfide group-containing thiol compound, which comprises effecting the ring-opening addition reaction of an alkylene sulfide represented by the general formula (1): ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be identical or different, stand for a hydrogen atom, an alkyl group of 1 to 10 carbon atoms, or an aromatic group of 6 to 15 carbon atoms) to a thiol compound in a solvent of an amide compound or urea substituent-containing compound.Type: GrantFiled: December 9, 1997Date of Patent: July 6, 1999Assignees: Nippon Shokubai Co., Ltd., Elf Atochem SAInventors: Hirokazu Itoh, Kazuaki Abe, Takashi Tomita
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Patent number: 5807814Abstract: Oil soluble compounds having the formula: ##STR1## wherein R and R.sup.1 are independently cyano, alkoxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, alkylcarbonyl, arylcarbonyl, alkenylcarbonyl, alkylsulfonyl, arylsulfonyl, alkenylsulfonyl, substituted aminocarbonyl, alkylphosphoryl, arylphosphoryl, alkenylphosphoryl, aryl, or heterocyclics, or together form a carbocycle or heterocycle, and R.sup.2 and R.sup.3 are independently alkyl, alkenyl, hydroxyalkyl, sulfurized alkyl, alkoxycarbonylalkyl, arylalkyl, or borated hydroxyalkyl, with the proviso that R, R.sup.1, R.sup.2 and R.sup.3 together contain sufficient carbon atoms to render the compound oil soluble in an oil of lubricating viscosity. The compound are useful as wear protectants or extreme pressure agents to enhance wear protection or extreme pressure properties in lubricating oils and greases.Type: GrantFiled: July 5, 1996Date of Patent: September 15, 1998Assignee: Chevron Chemical CompanyInventor: Andrew W. Ho
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Patent number: 5739140Abstract: Novel compounds of Formula I and methods of making and using the compounds which are useful as fungicides, particularly in the agricultural field: ##STR1## wherein C.sub.1 and C.sub.2 are carbon atoms which are part of an aromatic ring; W is alkoxyimino, alkoxymethylene or alkylthiomethylene; R.sub.1 is independently selected from the group consisting of halogen, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, wherein the alkyl or alkoxy are optionally substituted by halogen, and p is 0, 1, or 2; Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, NR.sub.2 wherein R.sub.2 is hydrogen or a lower aliphatic group, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 S(O)--, --OCH.sub.2 --, --SCH.sub.2 --, --S(O)CH.sub.2 --, --CH.sub.2 ON.dbd.C(R.sub.3)-- or --CH.dbd.NB wherein B is --O--CO--, --N.dbd.CR.sub.3, or --CR.sub.3 R.sub.4 -- wherein R.sub.3 and R.sub.4 are independently hydrogen or C.sub.1 -C.sub.Type: GrantFiled: October 23, 1996Date of Patent: April 14, 1998Assignee: Monsanto CompanyInventors: William P. Clinton, Jim I. McLoughlin, Anita E. Otal, John J. Parlow, Dennis P. Phillion, Ajit S. Shah
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Patent number: 5696282Abstract: A process comprises contacting, in the presence of a catalyst, hydrogen sulfide or a mercaptan such as, for example, n-dodecyl mercaptan with an .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl acrylate wherein the catalyst comprises a pyridine derivative such as, for example, 4-(dimethylamino)pyridine or an ion exchange resin such as, for example, "AMBERLYST A-21" to produce a 3-hydrocarbylthio derivative of the .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl 3-(dodecylthio)propionate.Type: GrantFiled: March 26, 1996Date of Patent: December 9, 1997Assignee: Phillips Petroleum CompanyInventors: James E. Shaw, Harry Porter
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Patent number: 5672730Abstract: The present invention relates to a compound of the formula ##STR1## wherein n is an integer from 1 to 4, R is selected from the group consisting of hydrogen and methyl; wherein when n is 1, R.sup.1 is selected from the group consisting of alkyl radicals having 1 to 18 carbon atoms, aryl radicals having 6 to 12 carbon atoms, aralkyl radicals having 7 to 12 carbon atoms, cycloalkyl radicals having 5 to 12 carbon atoms and radicals of the formula: ##STR2## wherein x is an integer of from 1 to 7; wherein when n is 2, R.sup.1 is selected from the group consisting of alkylene radicals having 2 to 18 carbon atoms, cycloalkylene radicals having 5 to 12 carbon atoms, arylene radicals having 6 to 12 carbon atoms, ##STR3## polyalkyl glycol ether radicals having the following structure ##STR4## wherein x is an integer from 1 to 7.Type: GrantFiled: September 22, 1995Date of Patent: September 30, 1997Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood Storer Cottman
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Patent number: 5587499Abstract: These compounds are denoted by the following formula (I): ##STR1## in which: Z denotes H or a linear or branched alkyl radical,X denotes O or S,each of A and B independently denotes an alkylene radical, it being possible for this radical to be substituted,R denotes H or an alkali metal, or else a linear or branched alkyl radical,x has the value of 0 or 1, andy has the value of 0, 1 or 2,the radical A not existing if x and y are both equal to 0, X being incapable of denoting O when R=alkyl and when R=H with x=y=0, and B being incapable of denoting optionally substituted methylene when X=S, x=y=0 and R=alkyl.According to the invention, different simple and efficient processes are proposed for preparing these new compounds, which can be applied to the preparation of new polymers and copolymers.Type: GrantFiled: May 11, 1995Date of Patent: December 24, 1996Assignee: ELF Atochem S.A.Inventors: Mich ele Curci, Jean-Luc Mieloszynski, Daniel Paquer
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Patent number: 5574184Abstract: A lubricant additive having antiwear and antioxidant properties is the reaction product of a sulfur-containing carboxylic acid and an etheramine, preferably 3,3'-thiodipropionic acid and N-isoeicosyloxypropyl-1,3-diaminopropane which is post reacted with an aliphatic alcohol, preferably oleyl alcohol, an aliphatic amine, preferably a tert-C.sub.12 to C.sub.14 amine and/or a trialkyl phosphite, preferably a tributylphosphite. The post-reaction product contains at least one ester, amide and/or phosphonate functional group.Type: GrantFiled: March 10, 1995Date of Patent: November 12, 1996Assignee: Mobil Oil CorporationInventors: Shi-Ming Wu, Andrew G. Horodysky
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Patent number: 5525629Abstract: Hydroxamic acid derivatives of formula (I): ##STR1## wherein R.sup.1 represents hydrogen or an (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkyl, phenyl, substituted phenyl, phenyl(C.sub.1 -C.sub.6)alkyl, heterocyclyl, (C.sub.1 -C.sub.6)alkylcarbonyl, phenacyl or substituted phenacyl group;R.sup.2 represents hydrogen or a (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, phenyl(C.sub.1 -C.sub.6)alkyl, cycloalkyl(C.sub.1 -C.sub.6)alkyl or cycloalkenyl(C.sub.1 -C.sub.6)alkyl group,R.sup.3 represents a group --CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl or --CH.sub.2 CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl;R.sup.4 represents hydrogen or a (C.sub.1 -C.sub.6)alkyl or phenyl(C.sub.1 -C.sub.6)alkyl group;R.sup.5 represents hydrogen or a methyl group;n is 0, 1 or 2;and A represents a (C.sub.1 -C.sub.6)hydrocarbon chain optionally substituted with one or more (C.sub.1 -C.sub.Type: GrantFiled: November 4, 1993Date of Patent: June 11, 1996Assignee: British Bio-Technology LimitedInventors: Michael J. Crimmin, William A. Galloway, Andrew J. Gearing