Processes Patents (Class 564/296)
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Publication number: 20080207940Abstract: The present invention relates to a method of removing SO2 contaminants from dimethyl sulfate (DMS) by treatment with an oxidizing agent, and to a process for the preparation of odour free fatty acid trialkanolamine esters quaternized with DMS which is substantially free of SO2 contaminants.Type: ApplicationFiled: March 8, 2006Publication date: August 28, 2008Applicant: AKZO Nobel N.V.Inventors: William Francis Joyce, Jeffrey Earl Telschow
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Publication number: 20080171863Abstract: The present invention relates to a method for preparation of organofluoro compounds containing radioactive isotope fluorine-18. More particularly, the present invention relates to a method for preparation of organofluoro compound by reacting fluorine salt containing radioactive isotope fluorine-18 with alkyl halide or alkyl sulfonate in the presence of alcohol of Chemistry (FIG. 1) as a solvent to obtain high yield of organofluoro compound. Synthesis reaction according to the present invention may be carried out under mild condition to give high yield of the organofluoro compounds and the reaction time is decreased, and thereby is suitable for the mass production of the organofluoro compounds.Type: ApplicationFiled: December 9, 2005Publication date: July 17, 2008Applicants: FUTURECHEM CO., LTD., THE ASAN FOUNDATIONInventors: Dae Hyuk Moon, Dae Yoon Chi, Dong Wook Kim, Seung Jun Oh, Jin-sook Ryu
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Patent number: 7342136Abstract: A process for preparing long chain internal fatty tertiary amines, quaternary amines and amine oxides via the selection of long chain internal olefins.Type: GrantFiled: November 10, 2005Date of Patent: March 11, 2008Assignee: Procter & Gamble CompanyInventors: Corey James Kenneally, Jeffrey John Scheibel
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Patent number: 7326814Abstract: The present invention relates to a process for the minimization of volatile organic sulphur byproducts in dimethyl sulfate quaternization of amines made with hypophosphorous acid, which leads to the formation of an odor stable product.Type: GrantFiled: December 23, 2003Date of Patent: February 5, 2008Assignee: Akzo Nobel N.V.Inventors: Elliot Band, Maurice Dery, William Joyce, Jeffrey Earl Telschow, Biing Ming Su, Michael Engel, John Nowak, Claude Peterson, Harold Providence, Phuong-Nga Trinh, Sandra Urquhart
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Patent number: 7268256Abstract: Provided is a method for purifying a quaternary alkyl ammonium salt enabling the obtainment of a particulate quaternary alkyl ammonium salt having a low water content at a high yield which is suitably used as an electrolyte in an electrolytic solution. The method for the purification of a quaternary alkyl ammonium salt comprises dispersing a quaternary alkyl ammonium salt to be purified into an organic solvent to allow it to form a suspension there. The alkyl groups constituting the quaternary alkyl ammonium salt have 1 to 5 carbon atoms each. The quaternary alkyl ammonium salt to be purified is dispersed into the organic solvent to make a suspension, and then the particles are washed with an alcohol solvent.Type: GrantFiled: April 17, 2003Date of Patent: September 11, 2007Assignee: Stella Chemifa Kabushiki KaishaInventors: Hirohisa Kikuyama, Masahide Waki, Shinji Hashiguchi, Tetsuo Nishida, Yasutaka Tashiro, Kenji Aoki
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Patent number: 7183434Abstract: The present invention relates to a continuous process for the quaternization of tertiary amines with an alkyl halide. The process is performed at a temperature between 50° C. and 140° C. by reacting a tertiary amine and an alkyl halide in a tubular reactor at a pressure sufficient to keep the alkyl halide dissolved in the reaction mixture. The molar ratio between the tertiary amine and the alkyl halide is from 1:1.3 to 1:2.9 and the pressure is suitably between 12 to 65 bar. The process could be performed either with or without a solvent present, preferably without a solvent. The process gives high product yields and low amounts of by-products.Type: GrantFiled: December 5, 2002Date of Patent: February 27, 2007Assignee: Akzo Nobel N.V.Inventors: Willem Hendrikus Baan, Jacobus Van Den Berg
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Patent number: 7105631Abstract: Process for the preparation of alkylated N- or amino, ammonium or spirobicyclic ammonium group-containing, crosslinked polymer gels, which is characterized in that a) in the crosslinkage step an aqueous solution of a polymer obtained by polymerization of the corresponding monomer is adjusted to a pH of 7.5–14 at a temperature of 0 to 90° C.Type: GrantFiled: September 2, 2003Date of Patent: September 12, 2006Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Michael Stanek, Marion Wagner, Gerhard Schoppel, Georg Haeubl, Ernst Wressnegger, Walter Raml
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Patent number: 7005548Abstract: The present invention relates to an economical and environmentally clean process for the preparation of high quality quaternary ammonium tribromides by oxidation of bromide (Br?) in an acidic medium by a biomimetic process involving transition metal ion mediated activation of hydrogen peroxide.Type: GrantFiled: December 31, 2002Date of Patent: February 28, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Mihir Kanti Choudhuri, Upasana Bora, Sanjay Kumar Dehury, Deepa Dey, Siddhartha Sankar Dhar, Wancydora Kharmawphlang, Boyapati Manoranjan Choudhary, Lakshmi Kantam Mannepalli
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Patent number: 6992222Abstract: The preparation of quaternary salt phenolate solutions is disclosed. The preparation entails mixing an aqueous hydroxide-containing solution with an organic phase that contains phenol and quaternary salt, distilling off the water and precipitating and filtering off the resulting salt.Type: GrantFiled: December 16, 2002Date of Patent: January 31, 2006Assignee: Bayer AktiengesellschaftInventors: Claus-Peter Reisinger, Sven Michael Hansen, Peter Fischer
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Patent number: 6967258Abstract: A quaternary ammonium hydroxycarboxylate is produced by quaternizing a tertiary amine with a hydroxycarboxylic ester represented by the following Formula 1: wherein R1 to R3 are as defined in the disclosure. By using only one tertiary amine having at least one substituent different from R1 of the ester moiety of the hydroxycarboxylic ester and by controlling the reaction conditions, a mixture of quaternary ammonium hydroxycarboxylates having different quaternary ammonium ions is produced. By reacting an inorganic acid with the quaternary ammonium hydroxycarboxylate or its mixture, a quaternary ammonium salt of inorganic acid or its mixture is produced.Type: GrantFiled: May 7, 2004Date of Patent: November 22, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yutaka Kanbara, Yasushi Higuchi, Tomoo Tsujimoto, Genki Nogami
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Patent number: 6900313Abstract: The invention relates to chiral ionic liquids of the general formula [A]n+[Y]n?, whereby n=1 or 2, the anion [Y]n? is the anion of an organic or inorganic proton acid and the cation [A]+ an optically active organic ammonium cation with up to 50 carbon atoms, at least one chirality center and at least one functional group that can produce a coordination by forming hydrogen bridges or by providing free electron pairs. At least one chirality center is provided with a distance of up to 5 atomic bonds from the functional group. The invention also relates to a method for producing said chiral ionic liquids and to the use thereof in methods for the asymmetric synthesis, the asymmetric catalysis and for separating racemates.Type: GrantFiled: January 29, 2001Date of Patent: May 31, 2005Inventors: Peter Wasserscheid, Wilhelm Keim, Carsten Bolm, Andreas Bösmann
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Patent number: 6794543Abstract: The invention provides a process for preparing arylpoly(oxalkyl)benzyl-dimethylammonium derivatives of the formula (1) which comprises reacting compounds of the formulae (2) and (3) where X=Br, Cl, R—SO3 with R=alkyl, alkylaryl R1=H, C1- to C16-alkyl or O—C1- to O—C16-alkyl in the ortho, meta or para position, R2=H, C1- to C4-alkyl or O—C1- to O—C4-alkyl, R3=H, C1- to C16-alkyl or O—C1- to O—C16-alkyl in the ortho, meta or para position, and n=1, 2, 3 or 4, at temperatures of from 60 to 160° C. in a solvent under the autogenous pressure.Type: GrantFiled: November 14, 2002Date of Patent: September 21, 2004Assignee: Clariant GmbHInventors: Klaus Raab, Gerhard Crass, Rudolf Aigner
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Patent number: 6790985Abstract: Phosphonium salts represented by the general formula (I) wherein R1 and R2 each represents a phenyl group which may be substituted by a lower alkyl group, R3 represents a phenylene group which may be substituted by a lower alkyl group, R7 and R8 each represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may be substituted and R9 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may be substituted; processes for producing the same and uses for the same; phosphines providing the same, and processes for producing said phosphines.Type: GrantFiled: April 1, 2002Date of Patent: September 14, 2004Assignee: Kuraray Co., Ltd.Inventors: Kazuyuki Yada, Kenji Shimoyamada, Masahiro Muranaka, Junichi Fuji, Shigeaki Suzuki
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Patent number: 6784317Abstract: A quaternary ammonium hydroxycarboxylate is produced by quaternizing a tertiary amine with a hydroxycarboxylic ester represented by the following Formula 1: wherein R1 to R3 are as defined in the disclosure. By using only one tertiary amine having at least one substituent different from R1 of the ester moiety of the hydroxycarboxylic ester and by controlling the reaction conditions, a mixture of quaternary ammonium hydroxycarboxylates having different quaternary ammonium ions is produced. By reacting an inorganic acid with the quaternary ammonium hydroxycarboxylate or its mixture, a quaternary ammonium salt of inorganic acid or its mixture is produced.Type: GrantFiled: April 19, 2002Date of Patent: August 31, 2004Assignee: Mitsubishi Gas Chemical Company, IncInventors: Yutaka Kanbara, Yasushi Higuchi, Tomoo Tsujimoto, Genki Nogami
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Patent number: 6740781Abstract: A process for the removal and recovery of quaternary salt (A) and base (D) from a reaction mixture is disclosed. The reaction mixture resulting from oxidative direct carbonylation contains in addition to (A) and (D), at least one hydroxyaromatic compound (B) and at least one reaction product (C) and optionally a solvent, and the process entails a) adding acid to the reaction mixture to cause conversion of (D) into a hydroxyaromatic compound (B2) b) separating the reaction mixture into b1.) that contains (C) and optionally (B) and/or (B2) and b2.) that contains (A) and optionally (B) and/or (B2), and c) reacting b1.) with a base (E) to re-form (D).Type: GrantFiled: December 16, 2002Date of Patent: May 25, 2004Assignee: Bayer AktiengesellschaftInventors: Peter Fischer, Sven Michael Hansen, Claus-Peter Reisinger
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Patent number: 6734325Abstract: A process for the separation and recycling of catalyst components from a chemical reaction mixture is disclosed. The process entails at least one extraction step.Type: GrantFiled: December 16, 2002Date of Patent: May 11, 2004Assignee: Bayer AktiengesellschaftInventors: Claus-Peter Reisinger, Sven Michael Hansen, Peter Fischer, Michael Traving
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Publication number: 20030153780Abstract: Perfluoroalkyl-substituted amines, acids, amino acids and thioether acid compounds containing a perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkene group as well as derivatives thereof, are described. They are useful as surfactants in a variety of applications where low surface tensions are required, including coating formulations for glass, wood, metal, cement, paper, textiles, as foam control agents in polyurethane foams and especially in aqueous fire-fighting formulations.Type: ApplicationFiled: July 24, 2002Publication date: August 14, 2003Inventors: Marlon Haniff, Ted Deisenroth, John Jennings, Karl Friedrich Mueller
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Patent number: 6586632Abstract: Quaternary ammonium dihydrogen phosphate or bisulfate salts are made by a process comprising the steps of: (1) forming a first mixture by contacting a quaternary ammonium halide with: (a) a water-insoluble organic solvent capable of forming a ternary azeotrope with water and hydrogen halide and (b) an amount of water and sulfuric acid or phosphoric acid sufficient to maintain the temperature of the first mixture in the range of from about 98° C. to about 105° C. when heated; (2) heating the first mixture to a temperature sufficient to separate a ternary azeotrope comprised of hydrogen halide, water and the water-insoluble organic solvent from the first mixture to form a second mixture comprised of water, sulfuric acid or phosphoric acid, the water-insoluble organic solvent and a quaternary ammonium dihydrogen phosphate or bisulfate salt.Type: GrantFiled: March 20, 2002Date of Patent: July 1, 2003Assignee: Cognis CorporationInventors: Phillip L. Mattison, Patrick M. McCurry, Jr.
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Patent number: 6583234Abstract: Disclosed is a process which comprises (a) reacting allyl bromide with diethyl amine in a molar ratio of at least about 1 mole of allyl bromide per about 1.15 moles of diethyl amine and in a molar ratio of no more than about 1 mole of allyl bromide per about 2 moles of diethyl amine, thereby generating allyl diethyl amine in a monomer reaction mixture; (b) subsequently filtering the monomer reaction mixture to remove impurities; (c) subsequently reacting the allyl diethyl amine with allyl bromide, thereby generating solid diallyl diethyl ammonium bromide; (d) subsequently isolating the solid diallyl diethyl ammonium bromide; (e) subsequently dissolving the diallyl diethyl ammonium bromide in a solvent and adding thereto a polymerization initiator to form a polymerization reaction mixture; (f) subsequently heating the polymerization reaction mixture in a vessel equipped with a reflux condenser to a temperature of from about 90 to about 100° C.Type: GrantFiled: July 26, 2001Date of Patent: June 24, 2003Assignee: Xerox CorporationInventors: Sheau V. Kao, Daniel A. Foucher, Mohammad J. Hossain, Christine E. Bedford, George Liebermann
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Patent number: 6576684Abstract: Disclosed are compositions from which radically initiated oligomers/polymers having a controlled molecular weight, low polydispersity and a vinyl or dienyl end group are prepared. Further subjects of the invention are a process for controlled radical polymerization, oligomers/polymers obtainable by said process and the use of specific addition fragmentation agents for the polymerization process. The addition fragmentation agents are new in part and these are also subject of the present invention. The addition fragmentation agents are of the formula (Ia), (Ib) or (Ic) where Y is a group which activates the double bond towards Michael addition.Type: GrantFiled: February 15, 2001Date of Patent: June 10, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Vincent Desobry, Peter Murer, Anne Schuwey
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Patent number: 6573405Abstract: An ionic liquid having a melting point of no more than 60° C., formed by the reaction of a quaternary ammonium compound of the formula: R1R2R3R4N+X− (I) or a mixture of two or more therof; with a halide of zinc, tin or iron, or a mixture of two or more thereof.Type: GrantFiled: September 24, 2001Date of Patent: June 3, 2003Assignee: Scionix LimitedInventors: Andrew P. Abbott, David L. Davies
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Patent number: 6541649Abstract: The present invention provides processes for the synthesis of novel cationic amphiphiles capable of facilitating transport of biologically active molecules into cells wherein the said amphiphiles contain N-hydroxyalkyl group and have at least one hydroxyalkyl group containing 1-3 carbon atoms directly linked to the positively charged nitrogen atom.Type: GrantFiled: December 4, 2001Date of Patent: April 1, 2003Assignee: Council of Scientific & Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Publication number: 20030036574Abstract: The invention provides ion exchange and electrochemical methods and devices employing anion exchange polymers produced by substantially simultaneous quaternization and polymerization reactions. Anion selective polymers are produced in accordance with the invention by combining, an ethylenic tertiary amine monomer, an alkylating agent having a boiling point temperature of at least about 100° C., and a cross-linking agent in the presence of a polymerizing agent for a time and at a temperature sufficient to form the polymer. The alkylating agent and the cross-linking agent may be the same compound, a cross-linking alkylating agent. The polymers may be produced in the presence of solvents and/or in the presence of diluting monomers which are incorporated into the polymers.Type: ApplicationFiled: June 24, 2002Publication date: February 20, 2003Inventors: Russell J. MacDonald, James A. Lech
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Patent number: 6521782Abstract: The present invention relates to a process for the manufacture of aqueous solutions of unsaturated quaternary ammonium salts. The salts can correspond to the following formula (I): in which R represents a methyl or benzyl radical, by reaction, in the presence of water, of N,N-dimethyl-amninoethyl acrylate (DAMEA) with a quaternizing agent of formula (II): R—Cl (II) in which R is as defined above. Generally, the reaction is carried out in a closed reactor, which includes all the DAMEA and has been pressurized by air or depleted air to 0.5 to 3 bar, by continuously introducing, at a temperature of 35 to 65° C., the quatenlizing agent (II) and the water, until a concentration of salt (I) in the water is obtained. The water starts to be introduced beginning when 0-20% of the amount by weight of the quaternizing agent (II) necessary for the reaction has been added and it being possible for the pressure at the end of the reaction to reach 9 bar.Type: GrantFiled: September 27, 2001Date of Patent: February 18, 2003Assignee: AtofinaInventors: Alain Riondel, Gilles Herbst, Marc Esch, Eric Delaunay, Peter Meyer
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Patent number: 6465419Abstract: Esters derived from alkanolamines, dicarboxylic acids and fatty alcohols and the cationic surfactants obtainable therefrom. Novel alkanolamine esters based on the esterification reaction of alkanolarnines, optionally alkoxylated, dicarboxylic acids and fatty alcohols, optionally alkoxylated, as well as the cationic surfactants and esterquats obtainable therefrom, are described. The cationic surfactants and esterquats thus obtained exhibit a high degree of efficacy in softening and conditioning natural and synthetic fibres such as textiles, paper and hair, and are therefore usable in treatments for softening and conditioning the said fibres. Novel aqueous fabric-softening compositions which contain the cationic surfactants and esterquats mentioned, optionally in combination with other active softening substances, are also described.Type: GrantFiled: June 7, 2001Date of Patent: October 15, 2002Assignee: Kao CorporationInventors: María José Bermejo Osés, Josep Ferrer Vilaret, Marisa Tomás Mumbrú
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Patent number: 6444846Abstract: There is provided a process for preparing tetraalkyl ammonium halide utilizing a catalytic amount of acetonitrile in a reaction under pressure and at an elevated temperature of an alkyl halide and a trialkyl halide and in which tetrafluoroborate can be subsequently prepared.Type: GrantFiled: April 19, 2001Date of Patent: September 3, 2002Assignee: Lithdyn InternationalInventors: W. Novis Smith, Joel McCloskey
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Patent number: 6414170Abstract: The present invention relates to a method for preparing a cationic surfactant in which physical chemical characteristics such as softness, antistatic properties, etc. as well as biodegradability are quite excellent due to having an ester group and a hydrophilic hydroxyl group in its molecules. A cationic surfactant of the present invention is prepared by reacting tertiary amine drivatives, fatty acid, and epihalohydrin, and prepared simply by reacting esterification and quaternary reactions in one step with a high yield. The above cationic surfactant is a high grade alkyl quaternary ammonium compound as represented in General Formula (1), wherein R1 is a C1-C4 alkyl group; R2 is a C7-C21 linear or branched alkyl or alkenyl group; A is OCOR3, NHCOR3 or OH; R3 is a C7-C21 linear or branched alkyl or alkenyl group; X is a halogen atom; and n is an integral number from 2 to 6.Type: GrantFiled: January 23, 2001Date of Patent: July 2, 2002Assignee: LG Chemical Ltd.Inventors: Dong-Il Kim, Jeong-Wook Ha, Tae-Seong Kim, Moon-Jeong Rang
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Patent number: 6414191Abstract: The present invention relates to a process for the continuous preparation of methoxyamine hydrochloride by cleavage of acetone oxime methyl ether by means of hydrogen chloride and water, wherein the cleavage is carried out in a reaction column having less than 20 theoretical plates and the amount taken off at the top is set to at least 30% of the amount of feed.Type: GrantFiled: September 11, 2001Date of Patent: July 2, 2002Assignee: BASF AktiengesellschaftInventors: Frank Heimann, Werner Peschel, Bernd Bartenbach, Horst Hartmann, Michael Keil, Josef Wahl
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Publication number: 20020062044Abstract: The present invention provides processes for the synthesis of novel cationic amphiphiles capable of facilitating transport of biologically active molecules into cells wherein the said amphiphiles contain N-hydroxyalkyl group and have at least one hydroxyalkyl group containing 1-3 carbon atoms directly linked to the positively charged nitrogen atomType: ApplicationFiled: December 4, 2001Publication date: May 23, 2002Applicant: Council of Scientific & Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Patent number: 6379294Abstract: A process for preparing an esterquat composition comprising (a) reacting a tertiary amine according to formula I: wherein R1 represents a C3-C6 hydrocarbon group, R2 represents a C3-C6 hydrocarbon group, a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a C3-C6 hydrocarbon group, R3 represents a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a —R4—OH group, R3 represents a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a —CH2[CH(OH)]nCH2OR5 group, R3 represents a —CH2[CH(OH)]nCH2OR5 group, R4 represents a C2-C4 hydrocarbon group, n is 1-4, and R5 represents H or a C1-C30 hydrocarbon group, with a C3-C6 hydrocarbyl halide or a di(C3-C6) hydrocarbyl sulfate, followed by (b) reaction with a C8-C30 acid halide, with the proviso that at least one hydroxy group is esterified.Type: GrantFiled: July 19, 2000Date of Patent: April 30, 2002Assignee: Akzo Nobel N.V.Inventors: Adrianus Buijs, Gerardus Van Gurp, Tjitte Nauta, Robert Smakman, Anne Marijke Wit-Van Grootheest
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Patent number: 6333433Abstract: The present invention provides processes for the synthesis of novel cationic amphiphiles capable of facilitating transport of biologically active molecules into cells wherein the said amphiphiles contain N-hydroxyalkyl group and have at least one hydroxyalkyl group containing 1-3 carbon atoms directly linked to the positively charged nitrogen atom.Type: GrantFiled: March 25, 1999Date of Patent: December 25, 2001Assignee: Council of Scientific Industrial ResearchInventors: Rajkumar Banerjee, Prasanta Kumar Das, Gollapudi Venkata Srilakshmi, Nalam Madhusudhana Rao, Arabinda Chaudhuri
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Publication number: 20010047112Abstract: This invention relates to stable aromatic amine compositions. These compositions comprise a) an organic compound containing at least one carboxylic acid group,, and b) an aromatic amine. This invention also relates to a process for stabilizing the color of aromatic amines, and to the use of these aromatic amines as initiators for the preparation of polyether polyols.Type: ApplicationFiled: September 17, 1999Publication date: November 29, 2001Inventor: RICK L. ADKINS
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Patent number: 6268534Abstract: A novel process for the synthesis of N,N-dioleyl-N,N-dimethylammonium chloride (DODAC) is described.Type: GrantFiled: February 19, 1999Date of Patent: July 31, 2001Assignee: Ribozyme Pharmaceuticals, Inc.Inventor: Jasenka Matulic-Adamic
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Patent number: 6235914Abstract: A process for making a tertiary amine ester of the following formula (I): the process comprising: (a) reacting a ketone or an aldehyde having the formula with a glycol to form a ketal or an acetal; (b) reacting the ketal or the acetal with acrylonitrile to form an ether nitrile; (c) reducing the ether nitrile to a tertiary amine ketal or a tertiary amine acetal; (d) hydrolyzing the tertiary amine ketal or the tertiary amine acetal to a tertiary amine diol; and (e) esterifying the tertiary amine diol to the tertiary amine ester of formula (I), wherein R1 and R2 are each independently a hydrogen atom or a linear, branched, or cyclic alkyl, alkylene, alkaryl, or aryl-containing group containing 1 to 18 carbon atoms; and each R3 are each independently of one another fatty acid radicals having 6-22 carbon atoms.Type: GrantFiled: August 18, 2000Date of Patent: May 22, 2001Assignee: Goldschmidt Chemical CompanyInventors: Philip Howard Steiger, Christopher Joseph Toney
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Patent number: 6194606Abstract: The present invention provides compounds having the formula: in which R is hydrogen or C1-C4alkyl, preferably hydrogen and Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, CF3, halogen (F, Cl, Br or I) or SO3M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C1-C4alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C1-C4alkyl and C1-C4hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.Type: GrantFiled: September 22, 1998Date of Patent: February 27, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
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Patent number: 6087303Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.l2 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.Type: GrantFiled: July 10, 1997Date of Patent: July 11, 2000Assignee: Lonza, Inc.Inventor: Leigh E. Walker
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Patent number: 6084131Abstract: A process for the preparation of protected dihydroxypropyl trialkylammonium salts, particularly in chiral form is described. In particular, a process for the preparation of (2,2-dimethyl-1,3-dioxolan-4-ylmethyl)trialkylammonium salts, particularly in chiral form is described. Furthermore, a process is described wherein the (2,2-dimethyl-1,3-dioxolan-4ylmethyl)trialkylammonium salts is a 2,2-dimethyl-1,3-dioxolan-4-ylmethyl trimethylammonium salt, preferably in chiral form. The protected dihydroxypropyl trialkylammonium salts lead to L-carnitine (9) when in chiral form (5).Type: GrantFiled: May 27, 1999Date of Patent: July 4, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6031137Abstract: This invention relates to stable aromatic amine compositions. These compositions comprise a) an organic compound containing at least one carboxylic acid group, and b) an aromatic amine. This invention also relates to a process for stabilizing the color of aromatic amines, and to the use of these aromatic amines as initiators for the preparation of polyether polyols.Type: GrantFiled: May 29, 1998Date of Patent: February 29, 2000Assignee: Bayer CorporationInventor: Rick L. Adkins
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Patent number: 5962709Abstract: Process for the aftertreatment of betaine and amphoteric surfactants comprising adjusting the pH to the range of from 11 to 14 by addition of an alkali metal hydroxide, followed by a thermal aftertreatment if the surfactant contains dichloroacetic acid residues.Type: GrantFiled: September 12, 1995Date of Patent: October 5, 1999Assignee: Henkel Kommanditgesellschaft auf Aktien (KGaA)Inventors: Gunter Uphues, Uwe Ploog, Rainer Jeschke, Renate Schick
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Patent number: 5929280Abstract: There is provided a simple method of producing in a good yield a tetraalkylammonium hydroxide aqueous solution in which the content of metal ions such as alkali metal ions is reduced to an extremely low level.High-purity trialkylamine and high-purity alkyl chloride are reacted with each other in ultrapure water to obtain an extremely high-purity tetraalkylammonium chloride aqueous solution substantially free from metal ions such as alkali metal ions, and then, the tetraalkylammonium chloride aqueous solution is subjected to electrolysis-dialysis in a solution state without drying it into a solid to produce a tetraalkylammonium hydroxide aqueous solution. Thereby, an extremely high-purity tetraalkylammonium hydroxide aqueous solution with little reduction in purity is obtained in a high yield.Type: GrantFiled: March 23, 1998Date of Patent: July 27, 1999Assignee: Tokuyama CorporationInventors: Tooru Nonaka, Yasunori Hirata, Masafumi Shibuya
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Patent number: 5919980Abstract: Improved surfactant recovery for recycle and reuse upon ultrafiltration of a surfactant-containing aqueous solution can be obtained using a betaine or amide oxide amphoteric surfactant in the aqueous cleaner/contaminant solution. The surfactant passes through the ultrafiltration membrane with the water in the permeate in very high amounts while the contaminants and other undesirable components are held back in the retentate.Type: GrantFiled: March 10, 1997Date of Patent: July 6, 1999Assignee: Rhodia Inc.Inventors: Manilal S. Dahanayake, Yun Brian Yang, Mark E. Ventura
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Patent number: 5880299Abstract: The invention relates to new esterquats which are obtained by reacting trialkanolamines with a mixture of fatty acids and dicarboxylic acids and quaternizing the resulting esters in known manner, optionally after alkoxylation. Cationic surfactants are obtained which show particularly high ecotoxicological compatibility, provide synthetic and natural fibers with a pleasant feel and, at the same time, reduce electrostatic charging between the filaments.Type: GrantFiled: October 24, 1996Date of Patent: March 9, 1999Assignee: Henkel CorporationInventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
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Patent number: 5869716Abstract: Esterquats based on natural fats and oils can be directly produced by subjecting fatty acid glyerine ester to ester interchange, in the presence of alkaline and/or alkaline earth boron hydrides and hypophosphoric acid or their alkaline and/or alkaline earth salts and possibly free fatty acid, with hydroxy-functionalised tertiary amines and quaternising the resultant products in the manner known per se.Type: GrantFiled: September 16, 1996Date of Patent: February 9, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rafael Pi Subirana, Joaquim Bigorra Llosas, Antonio Trius Oliva
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Patent number: 5851548Abstract: Lipid molecules bearing a cationic charge are described. These cationic lipids are useful in the delivery of biomolecules, such as oligonucleotides, nucleic acids, peptides, diagnostic imaging agents, proteins and drug molecules. In the form of liposomes, they can effectively be used for the intracellular delivery of biomolecules for therapeutic or diagnostic purposes.Type: GrantFiled: June 7, 1995Date of Patent: December 22, 1998Assignee: Gen-Probe IncorporatedInventors: Nanibhushan Dattagupta, Aditya Ranjan Das, C. Nagaraja Sridhar, Jasmin R. Patel
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Patent number: 5851982Abstract: To provide a liquid softener composition which is satisfactory in respects of softening effect, storage stability and water absorption properties, is excellent in biodegradability and is gentle with the environment. A liquid softener composition comprising 3 to 40% by weight of a quaternary ammonium salt (7-I) and water ##STR1## wherein R.sup.1 represents C.sub.20 -C.sub.44 alkyl or alkenyl group; R.sup.2, R.sup.3, and R.sup.4 are the same of different from each other and are C.sub.1 -C.sub.5 alkyl or hydroxyalkyl group; Y represents C.sub.2 -C.sub.4 alkylene group; m is a number of 0 to 20; n is an integer of 1 to 6; and X.sup.- represents an anion group.Type: GrantFiled: March 27, 1996Date of Patent: December 22, 1998Assignee: Kao CorporationInventors: Yuushi Sakata, Junichi Inokoshi, Osamu Tachizawa, Tohru Katoh, Uichiro Nishimoto, Yasuki Ohtawa, Akira Sakaguchi, Kohshiroh Sotoya, deceased, Noriko Yamaguchi
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Patent number: 5783534Abstract: A process for the production of a solid esterquat free from solvents comprising the steps ofA) forming a mixture comprising(i) at least one fatty acid triethanolamine ester corresponding to formula (I) ##STR1## in which R.sup.1 CO is a saturated and/or unsaturated acyl radical containing 6 to 22 carbon atoms, R.sup.2 and R.sup.3 independently of one another represent hydrogen or have the same meaning as R.sup.1 CO, and n, m and p together stand for O or for a number of from 1 to 10;(ii) at least one fatty alcohol polyglycol ether, and(iii) at least one fatty acid partial glyceride; andB) adding an alkylating agent to the above mixture to form said solid esterquat.Type: GrantFiled: July 15, 1996Date of Patent: July 21, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernd Wahle, Joaquim Bigorra Llosas, Rafael Pi, Antoni Soler Codina, Emili Brau Balague, Yvonne Reichert, Peter Waltenberger
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Patent number: 5763639Abstract: A process for preparing quaternized glycine nitriles of formula I ##STR1## comprising reaction of the corresponding precursor amine, aldehyde, hydrocyanic acid or alkali metal cyanide, and subsequent quaternization with an alkylating agent, wherein the reaction and quaternization are carried out successively in aqueous medium without isolation of an intermediate.Type: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
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Patent number: 5705663Abstract: The invention relates to quaternized triethanolamine difatty acid esters prepared from triethanolamine, fatty acid, fatty acid ester and a quaternizing agent and to a process for their preparation and to their use. The quaternized triethanolamine difatty acid esters thus prepared can be used to produce particularly storage-, temperature- and viscosity-stable rinse cycle laundry softeners having a high active content.Type: GrantFiled: December 7, 1995Date of Patent: January 6, 1998Assignee: Servo Delden B.V.Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
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Patent number: 5705695Abstract: The quaternary Zintl material (Et.sub.4 N).sub.4 ?Au(Ag.sub.1-x Au.sub.x).sub.2 Sn.sub.2 Te.sub.9 ! that contains 1-D semiconducting chains composed of four metallic elements is prepared by treating ethylenediamine extracts of a pentanary K--Au--Ag--Sn--Te alloy with Et.sub.4 NI.Type: GrantFiled: December 18, 1996Date of Patent: January 6, 1998Assignee: NEC Research Institute, Inc.Inventors: Robert C. Haushalter, Sandeep S. Dhingra
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Patent number: RE37555Abstract: The invention relates to a method of producing a mixture of a quaternary ammonium compound, fatty acid, fatty acid ester and tertiary amine salt in situ which is a highly functional mixture that is manufactured in a single step reaction whereby quaternization is completed without the aid of solvents, especially flammable solvents. The single step reaction process eliminates separate blending of individual components. The compositions obtained can be used as fabric softeners, in modified clays, as hair treating compounds and as disinfectants.Type: GrantFiled: June 11, 1999Date of Patent: February 19, 2002Assignee: Goldschmidt Chemical CompanyInventors: Jeannene A. Ackerman, Michael Miller, David E. Whittlinger