Having -s(=o)(=o)-o-x Attached Indirectly To The Single Bonded Oxygen Of The Carboxyl Group By A Single Carbon Or A Chain Consisting Of Carbons, Which Chain Or Carbon May Include A Ring, Wherein X Is Hydrogen Or A Cation (e.g., Isethionates, Etc.) Patents (Class 554/92)
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Patent number: 11274075Abstract: The invention comprises a process for preparing mixtures of DEFI and amide taurate (ATA) having excellent yields of ATA and substantial absence of browning of final ATA and DEFI mixtures. The process permits much greater flexibility in ratios of DEFI to ATA. The invention further relates to mixtures prepared by processes of the invention.Type: GrantFiled: September 6, 2017Date of Patent: March 15, 2022Assignee: CONOPCO, INC.Inventors: Van Au, Bijan Harichian
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Patent number: 8993792Abstract: The invention relates to polyglycol ether-free, polyglycerol partial ester-based sulphosuccinates, the preparation thereof, and the use of these in cosmetic formulations and also in cleaning compositions in the industrial and domestic sector and formulations comprising these sulphosuccinates.Type: GrantFiled: February 4, 2013Date of Patent: March 31, 2015Assignee: Evonik Industries AGInventors: Christian Hartung, Dominik Schuch, Wolfgang Berkels, Peter Muss, Ursula Westerholt, Sascha Herrwerth, Joerg Peggau, Oliver Springer, Hans Henning Wenk, Ralf Klein
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Publication number: 20130204021Abstract: The invention relates to polyglycol ether-free, polyglycerol partial ester-based sulphosuccinates, the preparation thereof, and the use of these in cosmetic formulations and also in cleaning compositions in the industrial and domestic sector and formulations comprising these sulphosuccinates.Type: ApplicationFiled: February 4, 2013Publication date: August 8, 2013Applicant: Evonik Industries AGInventors: Christian Hartung, Dominik Schuch, Wolfgang Berkels, Peter Muss, Ursula Westerholt, Sascha Herrwerth, Joerg Peggau, Oliver Springer, Hans Henning Wenk, Ralf Klein
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Publication number: 20130102803Abstract: A surfactant represented by the formula: wherein: R1 is CH3(CH2)m and may be interrupted with at least one heteroatom selected from the group consisting of amine, ether, ester, amide, sulfur, sulfur monoxide, sulfer dioxide, sulfamate, hydroxy, or mixtures thereof; and m=6-16 n=0 or 1 R2=H or CH3; and R3=H, SO3X, CO(CH)2COOH, or COCH(SO3X)CH2COOX1; wherein X and X1 are the same or different, and each is selected from NH4+, an alkali metal, or an H atom.Type: ApplicationFiled: April 11, 2012Publication date: April 25, 2013Inventors: Timothy Roland Kapsner, Danial Thomas Nowlaw, III
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Publication number: 20120264955Abstract: Embodiments of the invention include processing lipid feedstocks into various products. Embodiments of the invention include processing lipid feedstocks into various products. In an embodiment, the invention includes a method of processing a lipid feedstock comprising combining triglycerides from the lipid feedstock with water to form a first reaction mixture, contacting the first reaction mixture with a first metal oxide catalyst at a temperature of greater than 200 degrees Celsius to form a first product mixture including free fatty acids and glycerin, combining the free fatty acids with a diol to form a second reaction mixture, and contacting the second reaction mixture with a second metal oxide catalyst at a temperature of greater than 200 degrees Celsius to form a second product mixture. Other embodiments are also included herein.Type: ApplicationFiled: April 13, 2012Publication date: October 18, 2012Applicant: SARTEC CORPORATIONInventors: Clayton V. McNeff, Daniel Thomas Nowlan, Larry C. McNeff, Peter G. Greuel, Bingwen Yan
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Patent number: 8105993Abstract: Methods and compositions are provided for forming ester based compositions. The ester based compositions may be used in consumer products. In one aspect, a method is provided for producing acyl alkylisethionate esters by the esterification of a sulfonate composition having two or more sulfonate isomers with fatty acid(s). In another aspect, a method is provided for forming an ester based composition including a blend of acyl alkylisethionate and acylisethionate esters.Type: GrantFiled: May 1, 2007Date of Patent: January 31, 2012Assignee: Huntsman Petrochemical LLCInventors: Prakasa R. Anantaneni, George A. Smith, Martin J. Renner
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Patent number: 8008239Abstract: The present invention provides acylalkylisethionate esters useful in consumer products. The acylalkylisethionate esters are produced by reacting one or more carboxylic acids with one or more alkyl-substituted hydroxyalkyl sulfonates under esterification reaction conditions. The alkyl-substituted hydroxyalkyl sulfonates used as a raw material in producing the esters are prepared by reacting bisulfite with one or more alkylene oxides.Type: GrantFiled: August 11, 2004Date of Patent: August 30, 2011Assignee: Huntsman Petrochemical LLCInventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
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Publication number: 20110112317Abstract: A detergent composition comprising an esterified substituted benzene sulfonate, a hydrogen peroxide source, a soil suspending polymer, and an organic catalyst.Type: ApplicationFiled: January 14, 2011Publication date: May 12, 2011Inventors: Jeffrey John Scheibel, Scott Leroy Cron, Xinbei Song, Kevin Patrick Christmas, Gregory Scot Miracle
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Patent number: 7579311Abstract: The present invention relates to process for producing bars comprising 20 to 70% by wt. acyl isethionate and 15% to 35% free fatty acid and which is made by process where excess fatty acids made during production of acyl isethionate is removed by neutralization rather than by “stripping”. The bar retains remarkably desirable consumer properties.Type: GrantFiled: May 2, 2007Date of Patent: August 25, 2009Assignee: Conopco, Inc.Inventors: Badreddine Ahtchi-Ali, Michael Gerard Clarke, Florencio Ratuiste, Congling Quan
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Patent number: 6963004Abstract: The invention relates to a process for catalyzing a DEFI reaction using Group 4 metal based catalyst (according to IUPAC).Type: GrantFiled: December 23, 2003Date of Patent: November 8, 2005Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc.Inventors: Badreddine Ahtchi-Ali, Natasha Pfeiffer Campbell, John Robert Winters
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Patent number: 6562874Abstract: Composition may be prepared in a single DEFI reactor comprising mixtures of (1) DEFI (directly esterified fatty acyl isethionate) and (2) a compound produced by the reaction of (a) isethionate with a fatty acid replacement (e.g., a multicarboxylic fatty acid, a fatty acid); or (b) fatty acid with an isethionate replacement (e.g., C2-C24 alcohols, C2-C20 organic acids, amines). Such mixtures are milder than DEFI alone while retaining substantially same foaming benefit.Type: GrantFiled: December 7, 1999Date of Patent: May 13, 2003Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.Inventors: Leonora Ilardi, Lee Ann Gallagher, Michael Massaro
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Patent number: 6303802Abstract: A fatty acid and/or an alkyl ester of a fatty acid and isethionic acid are allowed to react at a temperature of not more than 130° C. The present invention provides a process for preparing a fatty ester of isethionic acid or a salt thereof exhibiting an ameliorated hue and smell and in which few by-products are produced.Type: GrantFiled: June 9, 1999Date of Patent: October 16, 2001Assignee: Asahi Denka Kogyo K.K.Inventors: Kiyoshi Musha, Kazuhiko Hayashi
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Patent number: 6184399Abstract: A process is provided for preparing a fatty acyl isethionate salt of the formula R1C(O)OR2SO3M which comprises reacting at least one fatty acid of the formula R1C(O)OH with at least one hydroxyalkanesulfonic acid salt of the formula HOR2SO3M in the presence of a catalyst, and distilling off water, wherein R1 is a linear or branched, saturated or unsaturated hydrocarbon having 5 to 31 carbon atoms, R2 is a linear, saturated or unsaturated hydrocarbon having 2 to 4 carbon atoms, and M is lithium, sodium, potassium, or ammonium and is characterised in that a foam control agent comprising a silicone oil is added. The foam control agent is added preferably once the reaction mixture is homogeneous. The process is suitably carried out with substantially equimolar amounts of fatty acid and hydroxyalkanesulfonic acid salt, preferably without distilling off any fatty acid.Type: GrantFiled: September 16, 1999Date of Patent: February 6, 2001Assignee: Akzo Nobel NVInventors: Claus-Peter Zok, Franz Jansen, Albert van de Berg
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Patent number: 6069262Abstract: Compositions of matter comprising fatty acid esters of hydroxyalkyl sulfonate salts, in particular sodium cocoyl isethionate (SCI) and process for preparing same. The esters are useful for personal care cleansing products, such as bar and liquid soaps, skin and hair care products.Type: GrantFiled: October 6, 1997Date of Patent: May 30, 2000Assignee: Finetex, Inc.Inventors: Ismail I. Walele, Samad A. Syed
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Patent number: 5994289Abstract: Surfactant mixtures containing acyloxyalkanesulfonates, which are prepared by mixing different acyloxyalkanesulfonates, the total quantity of acyloxyalkanesulfonates comprising a mixture of ammonium and alkali metal and/or alkaline-earth metal cations.Type: GrantFiled: September 25, 1997Date of Patent: November 30, 1999Assignee: Clariant GmbHInventor: Bernd Nestler
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Patent number: 5877140Abstract: The present invention relates to anionic compounds and their application in detergent compositions. The compounds have the dual benefits of surfactancy and suds suppression.Type: GrantFiled: March 20, 1997Date of Patent: March 2, 1999Inventors: Frederick Edward Hardy, Barry Thomas Ingram, Christian Leo Marie Vermote
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Patent number: 5840941Abstract: Process for the preparation of flowable, anhydrous acyloxyalkanesulfonates and their useIn the process of the invention, in the context of the esterification of fatty acids with hydroxyalkanesulfonates, the reaction product (molten mass) at 180.degree. to 250.degree. C. is sheared in such a manner during the cooling to 150.degree. to 50.degree. C. that the mean particle size of the product is <100 .mu.m. The acyloxyalkanesulfonate product thus obtained is still highly flowable, pumpable and the like, even at temperatures in the range from 60.degree. to 100.degree. C. and be stored in the fluid state without change at these temperature even over a long period.Type: GrantFiled: May 8, 1996Date of Patent: November 24, 1998Assignee: Hoechst AktiengesellschaftInventors: Viliam Tittel, Dirk Buhring
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Patent number: 5777140Abstract: Process for the preparation of acyloxyalkanesulfonates having improved properties The acyloxyalkanesulfonates are obtained in accordance with the invention by direct esterification in which at least one fatty acid is esterified with at least one ammonium hydroxyalkanesulfonate of the formula HO-A-SO.sub.3.sup.- + NR.sup.1 R.sup.2 R.sup.3 R.sup.4 in which A is a C.sub.2 -C.sub.4 -alkylene and R.sup.1.sub.1 R.sup.2.sub.1 R.sup.3 and R.sup.4 are hydrogen or a C.sub.1 -C.sub.4 -alkylene group in the presence of an esterification catalyst at a temperature of not more than 200.degree. C., with removal of the water present. This process gives a product of high acyloxyalkane-ammonium sulfonate content without the need for a consistency regulator to be added.Type: GrantFiled: March 27, 1996Date of Patent: July 7, 1998Assignee: Hoechst AktiengesellschaftInventor: Dirk Buhring
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Patent number: 5763632Abstract: Fatty acid esters of isethionate salts are made by reacting ethylene oxide and a bisulfite salt in an aqueous solution while maintaining the pH in the range of from about 5.5 to about 6.5 and while maintaining the temperature in the range of from 25.degree. C. to 85.degree. C. to form an isethionate salt. The isethionate salt is then esterified with a fatty acid to produce a product having little or no unwanted fatty acid esters of ethylene glycol.Type: GrantFiled: February 7, 1996Date of Patent: June 9, 1998Assignee: Henkel CorporationInventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
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Patent number: 5741917Abstract: Process for the preparation of acyloxyalkanesulfonates having improved propertiesThe acyloxyalkanesulfonates are prepared according to the invention by esterification of branched fatty acids with hydroxyalkanesulfonates. Because of the specific fatty acid, the use of a consistency regulator is not required. Highly concentrated acyloxyalkanesulfonates are obtained which, as a further advantageous property, have good water solubility.Type: GrantFiled: March 27, 1996Date of Patent: April 21, 1998Assignee: Hoechst AktiengesellschaftInventor: Dirk Buhring
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Patent number: 5739365Abstract: A method is disclosed for preparing ammonium hydroxyalkyl sulfonate by a process of reacting ammonium bisulfite and alkylene oxide wherein the pH is maintained at a relatively low value throughout most of the time of reaction of ammonium bisulfite and alkylene oxide in order to minimize the quantity of impurities, e.g. alkylene glycol and alkanolamine, in the ammonium hydroxyalkyl sulfonate. Ammonium alkanoyl alkyl sulfonates prepared by reacting such ammonium hydroxyalkyl sulfonates with fatty acids form aqueous solutions which are clear at ambient temperatures, and thus are useful as surfactants in clear liquid products.Type: GrantFiled: July 28, 1995Date of Patent: April 14, 1998Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, Amy E. Doty, Cheruthur Govindan, Louis J. Nehmsmann, Alan E. Wang
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Patent number: 5646320Abstract: Fatty acid esters of isethionate salts are made by reacting ethylene oxide and a bisulfite salt, that may be made in situ, in aqueous ammonia while maintaining (1) the pH in the range of about 5.5 to about 6.5 and (2) the temperature in the range of 25.degree. C. to 85.degree. C. to form an isethionate salt. The isethionate salt is then esterified with a fatty acid to produce a product having little or no unwanted fatty acid esters of ethylene glycol.Type: GrantFiled: June 16, 1994Date of Patent: July 8, 1997Assignee: Henkel CorporationInventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
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Patent number: 5523432Abstract: Quaternary ammonium salts of fatty acid hydroxyalkanesulfonic acids are made by reacting a hydroxyalkanesulfonic acid of the formula (I):HO--(C.sub.n H.sub.2n)--SO.sub.3 H (I):wherein n=2 to 4 with a fatty acid having from 6 to 18 carbon atoms at a temperature range of from about 60.degree. C. to about 120.degree. C. and at a reduced pressure followed b reaction with an amine in an organic solvent.Type: GrantFiled: April 7, 1994Date of Patent: June 4, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hans-Christian Raths, Rainer Rueben, Manfred Biermann, Timothy J. Cassady
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Patent number: 5519154Abstract: A process for producing ethoxylated ester surfactants in high yield has been discovered which employs no halogen-containing reactants or intermediates. Allyl alcohol is reacted with ethylene oxide to give an allyl alcohol ethoxylate; the ethoxylate in turn is reacted with a bisulfite salt (e.g. sodium metabisulfite) to give an ethylene glycol propanesulfonate or polyethylene glycol propanesulfonate in high yield. The propanesulfonate is then reacted with a fatty acid to give the ethoxylated ester surfactant.Type: GrantFiled: January 10, 1994Date of Patent: May 21, 1996Assignee: Huntsman CorporationInventor: Carter G. Naylor
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Patent number: 5473089Abstract: Ammonium fatty acid hydroxyalkanesulfonates are made by a process in which (a) ammonium hydroxyalkanesulfonate corresponding to general formula (I):HO--(C.sub.n H.sub.2n)--SO.sub.3 NH.sub.4 (I)wherein n=2 to 4, is subjected to the esterification reaction with a fatty acid corresponding to the formula (II)R--COOH (II)wherein RCO is an aliphatic, linear or branched acyl radical containing 6 to 18 carbon atoms, in the presence of an esterification catalyst, characterized in that (a) before the esterification reaction, the starting compounds corresponding to formulae (I) and (II) are dried at a temperature of 120.degree. C. to 160.degree. C. and under a pressure of 100 to 700 mbar; (b) the esterification reaction is carried out at a temperature above 160.degree. C. to 195.degree. C. and under a pressure of 250 mbar to atmospheric pressure; (c) water of solution and water of reaction formed are directly removed from the reaction mixture; (d) the catalyst is neutralized with a base on completion of the reaction.Type: GrantFiled: April 14, 1994Date of Patent: December 5, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernhard Gutsche, Timothy J. Cassady, Lutz Jeromin, Gerhard Wollmann, Norman Milstein, Hans-Christian Raths
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Patent number: 5434276Abstract: A process for the preparation of an N-acyl tauride comprising reacting an aliphatic or alicyclic carboxylic acid having from 6 to 22 carbon atoms with a taurine salt having the formula:HNR.sub.1 --CHR.sub.2 --CHR.sub.3 --SO.sub.3 Mwherein R.sub.1 is H or a C.sub.1 to C.sub.20 hydrocarbon radical; R.sub.2 and R.sub.3 are each independently H, or C.sub.1 -C.sub.6 hydrocarbon radical; M is a salt forming radical selected from the group consisting of alkali metals and alkaline earth metals; in a substantially inert atmosphere in the presence of an alkali metal borohydride, wherein the alkali metal is selected from the group of sodium, potassium, lithium and ammonium to produce a reaction product containing N-acyl tauride.Type: GrantFiled: December 27, 1993Date of Patent: July 18, 1995Assignee: Finetex, Inc.Inventors: Ismail I. Walele, Samad A. Syed
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Patent number: 5393466Abstract: The present invention provides novel fatty acid esters of alkoxylated isethionic acid and compositions comprising these compounds.Type: GrantFiled: April 12, 1993Date of Patent: February 28, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Leonora Ilardi, Mark Rerek, Michael Massaro, Christine Wenzel
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Patent number: 5384421Abstract: This invention discloses an improved method for making salts of acylisethionates using a direct esterification of a fatty acid with one or more salts of a selected hydroxyalkanesulfonic acid in the presence of a catalyst selected from the described group. This method may be used at temperatures below 200 degrees C.Type: GrantFiled: August 21, 1992Date of Patent: January 24, 1995Assignee: Hoechst Celanese CorporationInventors: James F. Day, Wolf-Dieter Mueller, Rainer H. R. Muth
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Patent number: 5368776Abstract: A method for improving the corrosion inhibition of lubricating oils especially those of vegetable origin which comprises adding an efficient amount of the reaction product of an epoxidized fatty acid ester, especially an epoxidized methyl ester of an unsaturated fatty acid and a sulphonic acid and a process for producing these reaction products.Type: GrantFiled: October 20, 1993Date of Patent: November 29, 1994Assignee: Rhein Chemie Rheinau GmbHInventors: Volker Schafer, Robert Kohler, Alfred Pauli, Achim Fessenbecker
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Patent number: 5359127Abstract: Process for the preparation of acyloxyalkanesulfonatesProcess for the preparation of acyloxyalkanesulfonates of the formula ##STR1## where R denotes C.sub.7 -C.sub.21 -alkyl or C.sub.7 -C.sub.21 -alkenyl, A denotes C.sub.2 -C.sub.4 -alkylene and M denotes an alkali metal atom or an alkaline earth metal atom, by esterification of carboxylic acids using salts of hydroxyalkanesulfonic acids, under mild reaction conditions, carboxylic acids of the general formula R--CO.sub.2 H being esterified using a salt of the formula HO--A--SO.sub.3 M in the presence of aqueous hydrochloric acid.Type: GrantFiled: October 6, 1992Date of Patent: October 25, 1994Assignee: Hoechst AktiengesellschaftInventor: Gerd Reinhardt
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Patent number: 5300665Abstract: Fatty acid esters of hydroxyalkylsulfonates and fatty acid amides of aminoalkylsulfonates are prepared by heating an excess of the fatty acids with the sulfonate until the water of condensation is removed. The excess fatty acid is removed by distillation and the isolated fatty acid ester or amide product is directly and rapidly cooled to minimize decomposition and color degradation.Type: GrantFiled: September 16, 1992Date of Patent: April 5, 1994Assignee: Rhone-Poulenc Surfactants and Specialties, L.P.Inventors: David J. Tracy, Mitchell B. Ferguson, Gordon Wall
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Patent number: 5292915Abstract: The invention relates to compounds containing carbonate groups and carbonyl groups and having the general formula ##STR1## in which R stands for a C.sub.1 -C.sub.4 -alkyl radical, an aryl radical, or a radical R.sup.1, whereR.sup.1 has the following formula ##STR2## in which R.sup.2 to R.sup.6 stand for H, alkyl, OH, O-alkyl, SH, S-alkyl, halogen, N(alkyl).sub.2, or N(alkyl)(aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 stand for a radical of the formula ##STR3## in which A, B and C stand for alkylene, cycloalkylene, oxaalkylene, polyoxaalkylene or arylene, k and l both stand for an integer from 1 to 80, and the end group Z stands for alkyl, aryl, alkoxycarbonyl, alkoxycarbonyloxy, or aryl.These compounds are suitable for use as emulsifiers for dispersions.Type: GrantFiled: February 4, 1992Date of Patent: March 8, 1994Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Manfred Schwartz