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)
  • Patent number: 11274075
    Abstract: 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: Grant
    Filed: September 6, 2017
    Date of Patent: March 15, 2022
    Assignee: CONOPCO, INC.
    Inventors: Van Au, Bijan Harichian
  • Patent number: 8993792
    Abstract: 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: Grant
    Filed: February 4, 2013
    Date of Patent: March 31, 2015
    Assignee: Evonik Industries AG
    Inventors: Christian Hartung, Dominik Schuch, Wolfgang Berkels, Peter Muss, Ursula Westerholt, Sascha Herrwerth, Joerg Peggau, Oliver Springer, Hans Henning Wenk, Ralf Klein
  • Publication number: 20130204021
    Abstract: 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: Application
    Filed: February 4, 2013
    Publication date: August 8, 2013
    Applicant: Evonik Industries AG
    Inventors: Christian Hartung, Dominik Schuch, Wolfgang Berkels, Peter Muss, Ursula Westerholt, Sascha Herrwerth, Joerg Peggau, Oliver Springer, Hans Henning Wenk, Ralf Klein
  • Publication number: 20130102803
    Abstract: 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: Application
    Filed: April 11, 2012
    Publication date: April 25, 2013
    Inventors: Timothy Roland Kapsner, Danial Thomas Nowlaw, III
  • Publication number: 20120264955
    Abstract: 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: Application
    Filed: April 13, 2012
    Publication date: October 18, 2012
    Applicant: SARTEC CORPORATION
    Inventors: Clayton V. McNeff, Daniel Thomas Nowlan, Larry C. McNeff, Peter G. Greuel, Bingwen Yan
  • Patent number: 8105993
    Abstract: 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: Grant
    Filed: May 1, 2007
    Date of Patent: January 31, 2012
    Assignee: Huntsman Petrochemical LLC
    Inventors: Prakasa R. Anantaneni, George A. Smith, Martin J. Renner
  • Patent number: 8008239
    Abstract: 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: Grant
    Filed: August 11, 2004
    Date of Patent: August 30, 2011
    Assignee: Huntsman Petrochemical LLC
    Inventors: Prakasa R. Anantaneni, John Gray, Marty J. Renner, George A. Smith, David C. Lewis, Donald H. Champion, Christopher J. Whewell
  • Publication number: 20110112317
    Abstract: A detergent composition comprising an esterified substituted benzene sulfonate, a hydrogen peroxide source, a soil suspending polymer, and an organic catalyst.
    Type: Application
    Filed: January 14, 2011
    Publication date: May 12, 2011
    Inventors: Jeffrey John Scheibel, Scott Leroy Cron, Xinbei Song, Kevin Patrick Christmas, Gregory Scot Miracle
  • Patent number: 7579311
    Abstract: 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: Grant
    Filed: May 2, 2007
    Date of Patent: August 25, 2009
    Assignee: Conopco, Inc.
    Inventors: Badreddine Ahtchi-Ali, Michael Gerard Clarke, Florencio Ratuiste, Congling Quan
  • Patent number: 6963004
    Abstract: The invention relates to a process for catalyzing a DEFI reaction using Group 4 metal based catalyst (according to IUPAC).
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: November 8, 2005
    Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc.
    Inventors: Badreddine Ahtchi-Ali, Natasha Pfeiffer Campbell, John Robert Winters
  • Patent number: 6562874
    Abstract: 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: Grant
    Filed: December 7, 1999
    Date of Patent: May 13, 2003
    Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.
    Inventors: Leonora Ilardi, Lee Ann Gallagher, Michael Massaro
  • Patent number: 6303802
    Abstract: 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: Grant
    Filed: June 9, 1999
    Date of Patent: October 16, 2001
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kiyoshi Musha, Kazuhiko Hayashi
  • Patent number: 6184399
    Abstract: 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: Grant
    Filed: September 16, 1999
    Date of Patent: February 6, 2001
    Assignee: Akzo Nobel NV
    Inventors: Claus-Peter Zok, Franz Jansen, Albert van de Berg
  • Patent number: 6069262
    Abstract: 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: Grant
    Filed: October 6, 1997
    Date of Patent: May 30, 2000
    Assignee: Finetex, Inc.
    Inventors: Ismail I. Walele, Samad A. Syed
  • Patent number: 5994289
    Abstract: 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: Grant
    Filed: September 25, 1997
    Date of Patent: November 30, 1999
    Assignee: Clariant GmbH
    Inventor: Bernd Nestler
  • Patent number: 5877140
    Abstract: 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: Grant
    Filed: March 20, 1997
    Date of Patent: March 2, 1999
    Inventors: Frederick Edward Hardy, Barry Thomas Ingram, Christian Leo Marie Vermote
  • Patent number: 5840941
    Abstract: 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: Grant
    Filed: May 8, 1996
    Date of Patent: November 24, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Viliam Tittel, Dirk Buhring
  • Patent number: 5777140
    Abstract: 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: Grant
    Filed: March 27, 1996
    Date of Patent: July 7, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Dirk Buhring
  • Patent number: 5763632
    Abstract: 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: Grant
    Filed: February 7, 1996
    Date of Patent: June 9, 1998
    Assignee: Henkel Corporation
    Inventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
  • Patent number: 5741917
    Abstract: 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: Grant
    Filed: March 27, 1996
    Date of Patent: April 21, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Dirk Buhring
  • Patent number: 5739365
    Abstract: 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: Grant
    Filed: July 28, 1995
    Date of Patent: April 14, 1998
    Assignee: PPG Industries, Inc.
    Inventors: Robert G. Briody, Amy E. Doty, Cheruthur Govindan, Louis J. Nehmsmann, Alan E. Wang
  • Patent number: 5646320
    Abstract: 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: Grant
    Filed: June 16, 1994
    Date of Patent: July 8, 1997
    Assignee: Henkel Corporation
    Inventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
  • Patent number: 5523432
    Abstract: 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: Grant
    Filed: April 7, 1994
    Date of Patent: June 4, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Rainer Rueben, Manfred Biermann, Timothy J. Cassady
  • Patent number: 5519154
    Abstract: 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: Grant
    Filed: January 10, 1994
    Date of Patent: May 21, 1996
    Assignee: Huntsman Corporation
    Inventor: Carter G. Naylor
  • Patent number: 5473089
    Abstract: 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: Grant
    Filed: April 14, 1994
    Date of Patent: December 5, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernhard Gutsche, Timothy J. Cassady, Lutz Jeromin, Gerhard Wollmann, Norman Milstein, Hans-Christian Raths
  • Patent number: 5434276
    Abstract: 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: Grant
    Filed: December 27, 1993
    Date of Patent: July 18, 1995
    Assignee: Finetex, Inc.
    Inventors: Ismail I. Walele, Samad A. Syed
  • Patent number: 5393466
    Abstract: The present invention provides novel fatty acid esters of alkoxylated isethionic acid and compositions comprising these compounds.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: February 28, 1995
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Leonora Ilardi, Mark Rerek, Michael Massaro, Christine Wenzel
  • Patent number: 5384421
    Abstract: 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: Grant
    Filed: August 21, 1992
    Date of Patent: January 24, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: James F. Day, Wolf-Dieter Mueller, Rainer H. R. Muth
  • Patent number: 5368776
    Abstract: 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: Grant
    Filed: October 20, 1993
    Date of Patent: November 29, 1994
    Assignee: Rhein Chemie Rheinau GmbH
    Inventors: Volker Schafer, Robert Kohler, Alfred Pauli, Achim Fessenbecker
  • Patent number: 5359127
    Abstract: 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: Grant
    Filed: October 6, 1992
    Date of Patent: October 25, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerd Reinhardt
  • Patent number: 5300665
    Abstract: 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: Grant
    Filed: September 16, 1992
    Date of Patent: April 5, 1994
    Assignee: Rhone-Poulenc Surfactants and Specialties, L.P.
    Inventors: David J. Tracy, Mitchell B. Ferguson, Gordon Wall
  • Patent number: 5292915
    Abstract: 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: Grant
    Filed: February 4, 1992
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Boettcher, Manfred Schwartz