Patents by Inventor Hans-Jurgen Kohle
Hans-Jurgen Kohle has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20230382829Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide, in the presence of a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase containing a solvent having a solubility in water at 20° C. of less than 500 mg/kg. The method then involves separating the liquid reaction mixture into an aqueous phase containing 1,2-propanediol and an organic phase; recycling at least a part of the separated organic phase to the reaction; and extracting the separated aqueous phase with an extractant solution containing the same phase transfer catalyst and solvent as used in the reaction to provide an extracted aqueous phase and an extract phase. The method further involves recycling at least a part of the extract phase to the reaction and recovering 1,2-propanediol from the extracted aqueous phase.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Georg Friedrich Thiele, Bernd Jaeger, Hans-Jürgen Köhle, Sebastian Imm, Marina Lazar
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Patent number: 11680228Abstract: Amides of an aliphatic polyamine with two or three molecules of 12-hydroxyoctadecanoic acid, wherein the polyamine comprises at least one primary amino group for each molecule of 12-hydroxyoctadecanoic acid and additionally at least one secondary and/or tertiary amino group, can be used in a lipase stable thickener composition comprising from 50 to 95% by weight of one or more of the amides, from 5 to 50% by weight of one or more diluents and from 0 to 10% by weight water, and such thickener compositions can be prepared by a step of heating a starting mixture comprising hydrogenated castor oil and one or more aliphatic polyamines and adding one or more diluents before or after the heating step.Type: GrantFiled: February 16, 2017Date of Patent: June 20, 2023Assignee: Evonik Operations GmbHInventors: Hans-Jürgen Köhle, Michael Klostermann, Gonglu Tian
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Patent number: 10696935Abstract: Liquid detergent compositions can be stably structured using amides of an aliphatic polyamine with two, three or four molecules of fully saturated hydroxyl alkyl acids, even in the presence of hydrolysing detergent ingredients such as lipase enzyme.Type: GrantFiled: January 31, 2019Date of Patent: June 30, 2020Assignee: The Procter & GambleInventors: Liesbet Maria Cornelia Detroch, Susana Fernandez-Prieto, Vincenzoi Guida, Michael Klostermann, Hans-Jurgen Kohle, Bruno Jean-Pierre Matthys, Johan Smets, Gonglu Tian
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Publication number: 20190161712Abstract: Liquid detergent compositions can be stably structured using amides of an aliphatic polyamine with two, three or four molecules of fully saturated hydroxyl alkyl acids, even in the presence of hydrolysing detergent ingredients such as lipase enzyme.Type: ApplicationFiled: January 31, 2019Publication date: May 30, 2019Inventors: Liesbet Maria Cornelia Detroch, Susana Fernandez-Prieto, Vincenzoi Guida, Michael Klostermann, Hans-Jurgen Kohle, Bruno Jean-Pierre Matthys, Johan Smets, Gonglu Tian
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Patent number: 10301574Abstract: A fabric enhancer composition comprising at least 0.1% by weight of fabric softening active of formula (A): {[R2]2N+[CH2—CH(CH3)—O—C(?O)—R1][CH(CH3)—CH2—O—C(?O)—R1]}X? wherein each R2 is independently either hydrogen, a short chain C1-C6 alkyl, C1-C3 hydroxyalkyl group, a poly(C2-3 alkoxy), or benzyl, wherein each R1 is independently a hydrocarbyl group or substituted hydrocarbyl group comprising 11 to 21 carbon atoms, and wherein X? is any fabric enhancer compatible anion. The composition comprises no more than 50% by weight of diester quaternary ammonium compound.Type: GrantFiled: October 6, 2015Date of Patent: May 28, 2019Assignee: The Procter & Gamble CompanyInventors: Marc Johan Declercq, Hans-Jurgen Kohle, Pieter Jan Maria Saveyn
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Patent number: 10221379Abstract: Liquid detergent compositions can be stably structured using amides of an aliphatic polyamine with two, three or four molecules of fully saturated hydroxyl alkyl acids, even in the presence of hydrolyzing detergent ingredients such as lipase enzyme.Type: GrantFiled: February 23, 2017Date of Patent: March 5, 2019Assignee: The Procter & Gamble CompanyInventors: Liesbet Maria Cornelia Detroch, Susana Fernandez-Prieto, Vincenzo Guida, Michael Klostermann, Hans-Jürgen Köhle, Bruno Jean-Pierre Matthys, Johan Smets, Gonglu Tian
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Patent number: 10214471Abstract: The process for preparing 1,2-propanediol from propene and hydrogen peroxide comprises the steps of a) reacting propene with hydrogen peroxide in the presence of a catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate, wherein the reaction is carried out in a liquid mixture comprising an aqueous phase having a pH of at most 6 and an organic phase, b) separating the biphasic mixture from step a) into an aqueous phase and an organic phase comprising propene oxide, c) recycling the propene oxide present in the separated organic phase into the reaction of step a) and d) separating 1,2-propanediol from the aqueous phase separated in step b).Type: GrantFiled: November 1, 2016Date of Patent: February 26, 2019Assignee: Evonik Degussa GmbHInventors: Holger Wiederhold, David Bolz, Bernd Jaeger, Hans-Jürgen Köhle, Sebastian Imm, Georg Friedrich Thiele
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Publication number: 20190055497Abstract: Amides of an aliphatic polyamine with two or three molecules of 12-hydroxyoctadecanoic acid, wherein the polyamine comprises at least one primary amino group for each molecule of 12-hydroxyoctadecanoic acid and additionally at least one secondary and/or tertiary amino group, can be used in a lipase stable thickener composition comprising from 50 to 95% by weight of one or more of the amides, from 5 to 50% by weight of one or more diluents and from 0 to 10% by weight water, and such thickener compositions can be prepared by a step of heating a starting mixture comprising hydrogenated castor oil and one or more aliphatic polyamines and adding one or more diluents before or after the heating step.Type: ApplicationFiled: February 16, 2017Publication date: February 21, 2019Inventors: Hans-Jurgen Kohle, Michael KLOSTERMANN, Gonglu TIAN
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Patent number: 10113137Abstract: A fabric softener active composition, comprising as component A at least 50% by weight of a bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.5 to 1.99, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of the fatty acid moieties, calculated for the free fatty acid, of from 0.5 to 50, and as component B a (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulphate fatty acid ester having the same fatty acid moieties as component A, and wherein the molar ratio of component B to component A is from 0.05 to 0.20.Type: GrantFiled: October 1, 2015Date of Patent: October 30, 2018Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Marc Johan Declercq, Pieter Jan Maria Saveyn
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Patent number: 10011806Abstract: In a method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester by quaternizing a tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate the quaternizing is carried out in the presence of a solid acid scavenger. The method can provide a fabric softener active composition, comprising from 65 to 98% by weight of at least one tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester, the corresponding non-quaternized tris-(2-hydroxyethyl)-amine fatty acid esters in amounts providing a total amine number of the composition of from 2 to less than 7 mg KOH/g, and from 1 to 1500 ppm methanol.Type: GrantFiled: November 3, 2014Date of Patent: July 3, 2018Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Axel Euler, Kurt Seidel, Peter Schwab
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Publication number: 20170298294Abstract: A fabric softener active composition, comprising as component A at least 50% by weight of a bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.5 to 1.99, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of the fatty acid moieties, calculated for the free fatty acid, of from 0.5 to 50, and as component B a (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulphate fatty acid ester having the same fatty acid moieties as component A, and wherein the molar ratio of component B to component A is from 0.05 to 0.20.Type: ApplicationFiled: October 1, 2015Publication date: October 19, 2017Applicant: Evonik Degussa GmbHInventors: Hans-Jürgen KÖHLE, Marc Johan DECLERCQ, Pieter Jan Maria SAVEYN
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Publication number: 20170247646Abstract: Liquid detergent compositions can be stably structured using amides of an aliphatic polyamine with two, three or four molecules of fully saturated hydroxyl alkyl acids, even in the presence of hydrolysing detergent ingredients such as lipase enzyme.Type: ApplicationFiled: February 23, 2017Publication date: August 31, 2017Inventors: Liesbet Maria Cornelia DETROCH, Susana FERNANDEZ-PRIETO, Vincenzo GUIDA, Michael KLOSTERMANN, Hans-Jürgen KÖHLE, Bruno Jean-Pierre MATTHYS, Johan SMETS, Gonglu TIAN
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Patent number: 9441187Abstract: Reacting at least one tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate at a molar ratio of dimethylsulfate to amine nitrogen of from 0.79 to 0.94 until the reaction mixture has a total amine number of from 7 to 20 mg KOH/g provides novel fabric softener active compositions with a low content of methanol, comprising from 65 to 98% by weight of tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid esters and from 1 to 1500 ppm methanol.Type: GrantFiled: April 24, 2013Date of Patent: September 13, 2016Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Ulrike Kottke, Dirk Kuppert, Dietmar Träumer, Kurt Seidel, Axel Euler
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Publication number: 20160102273Abstract: A fabric enhancer composition comprising at least 0.1% by weight of fabric softening active of formula (A): {[R2]2N+[CH2—CH(CH3)—O—C(?O)—R1][CH(CH3)—CH2—O—C(?O)—R1]}X? wherein each R2 is independently either hydrogen, a short chain C1-C6 alkyl, C1-C3 hydroxyalkyl group, a poly(C2-3 alkoxy), or benzyl, wherein each R1 is independantly a hydrocarbyl group or substituted hydrocarbyl group comprising 11 to 21 carbon atoms, and wherein X? is any fabric enhancer compatible anion. The composition comprises no more than 50% by weight of diester quaternary ammonium compound.Type: ApplicationFiled: October 6, 2015Publication date: April 14, 2016Inventors: Marc Johan DECLERCQ, Hans-Jurgen KOHLE, Pieter Jan Maria SAVEYN
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Publication number: 20150126431Abstract: In a method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester by quaternizing a tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate the quaternizing is carried out in the presence of a solid acid scavenger. The method can provide a fabric softener active composition, comprising from 65 to 98% by weight of at least one tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester, the corresponding non-quaternized tris-(2-hydroxyethyl)-amine fatty acid esters in amounts providing a total amine number of the composition of from 2 to less than 7 mg KOH/g, and from 1 to 1500 ppm methanol.Type: ApplicationFiled: November 3, 2014Publication date: May 7, 2015Applicant: Evonik Industries AGInventors: Hans-Jürgen Köhle, Axel Euler, Kurt Seidel, Peter Schwab
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Publication number: 20150080286Abstract: Reacting at least one tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate at a molar ratio of dimethylsulfate to amine nitrogen of from 0.79 to 0.94 until the reaction mixture has a total amine number of from 7 to 20 mg KOH/g provides novel fabric softener active compositions with a low content of methanol, comprising from 65 to 98% by weight of tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid esters and from 1 to 1500 ppm methanol.Type: ApplicationFiled: April 24, 2013Publication date: March 19, 2015Applicant: Evonik Industries AGInventors: Hans-Jürgen Köhle, Ulrike Kottke, Dirk Kuppert, Dietmar Träumer, Kurt Seidel, Axel Euler
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Patent number: 8883712Abstract: A fabric softening composition which comprises as component A a tertiary or quaternary ammonium salt of formulae (I) or (II): R1R2R3N+CH2CHR4OC(?O)R5X???(I) R1R2R3N+(CH2)3NHR(?O)R5X???(II) in which R1 is hydrogen, methyl or ethyl, R2 and R3, independently of one another, are C1-4 alkyl or C2-4 hydroxyalkyl, R4 is hydrogen or methyl, R5 is a linear C15-21 alkyl or alkenyl radical and X? is a monovalent anion, and as component B a nonionic softener with only one long-chain hydrocarbon radical bonded to a polar radical having at least one free hydroxy group, where fatty alcohol alkoxylate or fatty acid alkoxylate are excluded as component B, exhibits a good softening effect and forms storage-stable dispersions if the molar ratio of component A to component B is in the range from 2:1 to 1:3, the difference between the average chain length of the long-chain hydrocarbon radicals of components A and B is at most 2 carbon atoms and the hydrocarbon radicals of components A and B have on average in each case at mostType: GrantFiled: April 19, 2011Date of Patent: November 11, 2014Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Ulrike Kottke, Hans Henning Wenk, Harald Jakob
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Patent number: 8569224Abstract: A fabric softener active composition, comprising at least 50% by weight of a bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.5 to 1.99, wherein the average chain length of the fatty acid moieties is from 16 to 18 carbon atoms and the iodine value of the fatty acid moieties, calculated for the free fatty acid, is from 0.5 to 50, and from 0.5 to 5% by weight fatty acid provides high softening performance and good storage stability in aqueous dispersion and can be handled and processed in a liquid state without addition of a flammable solvent.Type: GrantFiled: March 26, 2011Date of Patent: October 29, 2013Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Ulrike Kottke, Harald Jakob, Jens Hildebrand
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Patent number: 8563499Abstract: A fabric softener active composition, comprising from 65 to 95% by weight of a bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.80 to 1.96, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of from 0 to 50, from 2 to 8% by weight of a fatty acid triglyceride having an average chain length of the fatty acid moieties of from 10 to 14 carbon atoms and an iodine value of from 0 to 15, and from 3 to 12% by weight of an alcohol selected from ethanol, 1-propanol and 2-propanol has low melt viscosity, high stability towards dealkylation in the molten state and low flammability.Type: GrantFiled: March 26, 2011Date of Patent: October 22, 2013Assignee: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Matthias Schöppner, Axel Euler, Harald Jakob, Saji John Meledathu, Todd L. Kurth, Delbert G. Young, Ingo Hamann, Georg Schick
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Publication number: 20130053299Abstract: A fabric softening composition which comprises as component A a tertiary or quaternary ammonium salt of formulae (I) or (II): R1R2R3N+CH2CHR4OC(?O)R5X???(I) R1R2R3N+(CH2)3NHR(?O)R5X???(II) in which R1 is hydrogen, methyl or ethyl, R2 and R3, independently of one another, are C1-4 alkyl or C2-4 hydroxyalkyl, R4 is hydrogen or methyl, R5 is a linear C15-21 alkyl or alkenyl radical and X? is a monovalent anion, and as component B a nonionic softener with only one long-chain hydrocarbon radical bonded to a polar radical having at least one free hydroxy group, where fatty alcohol alkoxylate or fatty acid alkoxylate are excluded as component B, exhibits a good softening effect and forms storage-stable dispersions if the molar ratio of component A to component B is in the range from 2:1 to 1:3, the difference between the average chain length of the long-chain hydrocarbon radicals of components A and B is at most 2 carbon atoms and the hydrocarbon radicals of components A and B have on average in each case at mType: ApplicationFiled: April 19, 2011Publication date: February 28, 2013Applicant: Evonik Degussa GmbHInventors: Hans-Jürgen Köhle, Ulrike Kottke, Hans Henning, Harald Jakob