Patents by Inventor Stefan Wershofen
Stefan Wershofen 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: 20240018097Abstract: The present invention relates to a process for preparing a polyisocyanate, namely an isocyanate group-terminated polyol polyanthranilic acid ester. The process comprises the step of reacting an anthranilic acid derivative selected from anthranilic acid halide (in particular anthranilic acid chloride), isatoic anhydride or a mixture thereof with a first polyol of a number-average molar mass of at least 200 g/mol and a functionality in the range of 2 to 8, and obtaining, as a result, a polyamine (namely a polyol polyanthranilic acid ester with amine terminal groups) and reacting the polyamine with phosgene and obtaining, as a result, a polyisocyanate (namely an isocyanate group-terminated polyol polyanthranilic acid ester). The invention further relates to the polyisocyanates obtained in this way, their use in polyaddition reactions, and polyaddition products obtainable by these reactions.Type: ApplicationFiled: December 9, 2021Publication date: January 18, 2024Inventors: Christos Karafilidis, Marina Reithmeier, Stefan Wershofen, Michael Schedler, Michael Baecker
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Publication number: 20230027482Abstract: The invention relates to a method for producing di- and polyisocyanates of the diphenylmethane series, in which (i) the liquid product flow created in the phosgenation, (ii) the reaction mixture present in an optionally provided reactor for carbamic acid chloride cleaving, (ii) the liquid product flow leaving such an optionally provided reactor for carbamic acid chloride cleaving, (iv) the reaction mixture present in the dephosgenation, or (v) the liquid product flow created in the dephosgenation, is treated with a gaseous hydrogen chloride flow in one stage in a bubble column or in a plate column within a contact time of 1 min to less than 30 min. The product flow treated din this way or in the reaction mixture treated in this way is fed directly (i.e. in particular without further treatment with an inert gas) to the next step of the reaction or workup.Type: ApplicationFiled: December 15, 2020Publication date: January 26, 2023Inventors: Stefan Wershofen, Enke Liu, Anke Hielscher, Richard Adamson, Ricardo Serra, Volker Michele, Juergen Spriewald
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Patent number: 11542223Abstract: The present invention relates to a process for preparing di- and polyamines of the diphenyl methane series. More specifically, the process comprises reacting aniline and formaldehyde by (1a) mixing aniline with hydrochloric acid to form aniline hydrochloride, and (1b) mixing the aniline hydrochloride with a first portion of aqueous formaldehyde; or (1c) mixing aniline with a first portion of aqueous formaldehyde to form an aminal, and (1d) mixing the aminal with hydrochloric acid; to obtain a first reaction product; (2) converting the first reaction product to a second reaction product comprising di- and polyamines of the diphenyl methane series in a cascade of 4 to 25 reaction zones arranged in series, wherein a second portion of aqueous formaldehyde is added to the second of the reaction zones, in which second reaction zone the temperature is equal to or up to 20° C.Type: GrantFiled: July 21, 2022Date of Patent: January 3, 2023Assignees: Covestro LLC, Covestro Deutschland AGInventors: Richard Adamson, Dolan OConnor, Stefan Wershofen
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Patent number: 11406964Abstract: The present invention relates to a catalyst for preparing carbamates, in particular aromatic carbamates, comprising a binary oxide having the formula L1-xMxO2, wherein L is a metal selected from the lanthanoid series and M is a metal selected from the group consisting of Sc, Y, Ti, Zr, Hf, metals from the lanthanoid series and metals from the actinoid series, and wherein x ranges from 0.01 to 0.05. The present invention also relates to a method for producing said catalysts and a method of utilizing said catalysts in the production of carbamates, in particular aromatic carbamates.Type: GrantFiled: March 26, 2019Date of Patent: August 9, 2022Assignee: Covestro Intellectual Property GmbH & Co. KGInventors: Stefan Wershofen, Anton Vidal-Ferran, José Luis Núñez Rico, Javier Perez-Ramirez, Begona Puertolas Lacambra, Amol P. Amrute
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Patent number: 10947187Abstract: The invention relates to a method for producing methylene-diphenylene-diisocyanate and optionally a mixture of methylene-diphenylene-diisocyanate and polymethylene-polyphenylene-polyisocyanate, wherein, in a step ?), a fraction (142) containing a methylene-diphenylene-diisocyanate and secondary components is provided, optionally via a step ?.1), the separating of methylene-diphenylene-diisocyanate and secondary components from a fraction (100) containing methylene-diphenylene-diisocyanate and polymethylene-polyphenylene-polyisocyanate, and wherein, in a step ?), the fraction (142) containing methylene-diphenylene-diisocyanate and secondary components is subjected to a purification comprising an isomer separation by distillation and/or crystallization in two or more sub-steps (a, b, . . . ), obtaining two or more methylene-diphenylene-diisocyanate-reinfractions (140-1, 140-2, . . .Type: GrantFiled: January 2, 2019Date of Patent: March 16, 2021Assignee: Covestro Intellectual Property GmbH & Co. KGInventors: Thomas Knauf, Peter Plathen, Dirk Manzel, Stefan Wershofen
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Publication number: 20210053031Abstract: The present invention relates to a catalyst for preparing carbamates, in particular aromatic carbamates, comprising a binary oxide having the formula L1-xMxO2, wherein L is a metal selected from the lanthanoid series and M is a metal selected from the group consisting of Sc, Y, Ti, Zr, Hf, metals from the lanthanoid series and metals from the actinoid series, and wherein x ranges from 0.01 to 0.05. The present invention also relates to a method for producing said catalysts and a method of utilizing said catalysts in the production of carbamates, in particular aromatic carbamates.Type: ApplicationFiled: March 26, 2019Publication date: February 25, 2021Inventors: Stefan Wershofen, Anton Vidal-Ferran, José Luis Núñez Rico, Javier Perez-Ramirez, Begona Puertolas Lacambra, Amol P. Amrute
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Patent number: 10858310Abstract: The invention relates to a method for producing an isocyanate, wherein a carbamate or thiolcarbomate is converted, in the presence of a catalyst, with separation of an alcohol or thioalcohol, at a temperature of at least 150° C., to the corresponding isocyanate, wherein a compound of the general formula (X)(Y)(Z—H) is used as a catalyst, in particular characterized in that the compound has both a proton donor function and a proton acceptor function. In the catalysts according to the invention, a separable proton is bound to a heteroatom, which is more electronegative than carbon. Said heteroatom is either identical to Z or a component thereof. In the catalysts according to the invention, there is additionally a proton acceptor function which is either identical to X or a component thereof. According to the invention, the proton donator and proton acceptor function are connected to each other by the bridge Y.Type: GrantFiled: August 31, 2018Date of Patent: December 8, 2020Assignee: Coverstro Deutschland AGInventors: Daniela Cozzula, Andreas Ernst, Matthias Leven, Walter Leitner, Thomas Ernst Mueller, Christoph Guertler, Stefan Wershofen, Gernot Jaeger, Franz Beggel, Jens Langanke
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Publication number: 20200361856Abstract: The invention relates to a method for producing an isocyanate, wherein a carbamate or thiolcarbomate is converted, in the presence of a catalyst, with separation of an alcohol or thioalcohol, at a temperature of at least 150° C., to the corresponding isocyanate, wherein a compound of the general formula (X)(Y)(Z—H) is used as a catalyst, in particular characterized in that the compound has both a proton donor function and a proton acceptor function. In the catalysts according to the invention, a separable proton is bound to a heteroatom, which is more electronegative than carbon. Said heteroatom is either identical to Z or a component thereof. In the catalysts according to the invention, there is additionally a proton acceptor function which is either identical to X or a component thereof. According to the invention, the proton donator and proton acceptor function are connected to each other by the bridge Y.Type: ApplicationFiled: August 31, 2018Publication date: November 19, 2020Inventors: Daniela Cozzula, Andreas Ernst, Matthias Leven, Walter Leitner, Thomas Ernst Mueller, Christoph Guertler, Stefan Wershofen, Gernot Jaeger, Franz Beggel, Jens Langanke
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Publication number: 20200331848Abstract: The invention relates to a method for producing methylene-diphenylene-diisocyanate and optionally a mixture of methylene-diphenylene-diisocyanate and polymethylene-polyphenylene-polyisocyanate, wherein, in a step ?), a fraction (142) containing a methylene-diphenylene-diisocyanate and secondary components is provided, optionally via a step ?.1), the separating of methylene-diphenylene-diisocyanate and secondary components from a fraction (100) containing methylene-diphenylene-diisocyanate and polymethylene-polyphenylene-polyisocyanate, and wherein, in a step ?), the fraction (142) containing methylene-diphenylene-diisocyanate and secondary components is subjected to a purification comprising an isomer separation by distillation and/or crystallization in two or more sub-steps (a, b, . . . ), obtaining two or more methylene-diphenylene-diisocyanate-reinfractions (140-1, 140-2, . . .Type: ApplicationFiled: January 2, 2019Publication date: October 22, 2020Inventors: Thomas Knauf, Peter Plathen, Dirk Manzel, Stefan Wershofen
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Patent number: 10807084Abstract: The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO2]—CH2—CHR—X—COOZn[Y], wherein [SiO2] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, —CH3, and —CH2CH3, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines.Type: GrantFiled: May 14, 2018Date of Patent: October 20, 2020Assignee: Covestro Deutschland AGInventors: Stefan Wershofen, Markus Dugal, Gernot Jaeger, Anton Vidal Ferran, Jose Luis Nuñez Rico
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Patent number: 10759736Abstract: The invention relates to a process for the preparation of di- and polyamines of the diphenylmethane series (MDA), in which firstly crude MDA is prepared and is then subjected to a distillation process, wherein the distillation process comprises the following: in a distillation column, separating off a stream containing aniline and water as head product so as to obtain the first product stream as sump product, in said distillation column or in an apparatus arranged downstream of said distillation column, performing a stripping with steam so as to obtain a gaseous stream containing aniline, water and MMDA, partially condensing this gaseous stream containing aniline, water and MMDA so as to obtain a liquid stream containing MMDA and water (and optionally aniline) and a gaseous stream containing aniline and water (and optionally MMDA), drying the liquid stream containing MMDA and water (and optionally aniline) obtained by the partial condensation so as to obtain the second product stream.Type: GrantFiled: October 10, 2019Date of Patent: September 1, 2020Assignee: Covestro Deutschland AGInventors: Stefan Wershofen, Richard Adamson, Georg Pirkl
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Patent number: 10689322Abstract: The present invention relates to a process for preparing di- and polyamines of the diphenylmethane series (MDA), a system for producing MDA and a process for operating a system for preparing MDA. The invention enables optimization of production standstills during operation of the MDA process with respect to time expenditure and optionally also with respect to energy and material consumption by means of a so-called recirculation mode for individual system components. During interruption of the process or interruption of the operation of individual system components, formaldehyde is not introduced into the reaction and the system components that are not affected by a revision, repair, or cleaning measure are operated in so-called recirculation mode.Type: GrantFiled: June 22, 2015Date of Patent: June 23, 2020Assignee: Covestro Deutschland AGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes
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Patent number: 10689323Abstract: The invention relates to a method for the preparation of di- and polyamines of the diphenylmethane series, care being taken during the shutdown of the production process that an excess of aniline and respect to formalin is ensured.Type: GrantFiled: September 24, 2018Date of Patent: June 23, 2020Assignee: Covestro Intellectual Property GmbH & Co. KGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes
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Publication number: 20200147594Abstract: The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO2]—CH2—CHR—X—COOZn[Y], wherein [SiO2] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, —CH3, and —CH2CH3, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines.Type: ApplicationFiled: May 14, 2018Publication date: May 14, 2020Inventors: Stefan Wershofen, Markus Dugal, Gernot Jaeger, Anton Vidal Ferran, Jose Luis Nuñez Rico
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Patent number: 10640453Abstract: The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities with alteration of the isomer composition in the resulting diamines of the diphenylmethane series (altering the 2,4?-MDA content). Adapting the molar ratios of the total used aniline to the total used formaldehyde and of the total used acid catalyst to the total used aniline, and adapting the reaction temperature, allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity, and allows the formation of undesired by-products to be avoided as far as possible; the intended modification to binuclear content is likewise achieved.Type: GrantFiled: December 18, 2017Date of Patent: May 5, 2020Assignee: Covestro Deutschland AGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes
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Patent number: 10640455Abstract: The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities with alteration of the content of diamines of the diphenylmethane series (altering the binuclear content). Adapting the molar ratio of the total used aniline to the total used formaldehyde and adapting the reaction temperature allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity, and allows the formation of undesired by-products to be avoided as far as possible; the intended modification to binuclear content is likewise achieved.Type: GrantFiled: December 18, 2017Date of Patent: May 5, 2020Assignee: Covestro Deutschland AGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes
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Patent number: 10633476Abstract: A method for producing a composition comprising polycarbodiimide, comprising the step of the reaction of a reaction mixture which contains an aromatic polyisocyanate and a carbodiimidising catalyst, wherein, before the reaction, the aromatic polyisocyanate is treated at a temperature of ?80° C. to ?150° C. and a pressure of ?1 mbar to ?500 mbar by passing through an inert gas and/or during the reaction, the reaction mixture is treated at a temperature of ?80° C. to ?150° C. and a pressure of ?1 mbar to ?500 mbar by passing through an inert gas and wherein the content of hydrolysable chlorine in the reaction mixture is ?10 ppm.Type: GrantFiled: February 25, 2016Date of Patent: April 28, 2020Assignee: Covestro Deutschland AGInventors: Hans-Detlef Arntz, Stefan Wershofen, Ernst Felske
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Patent number: 10633327Abstract: The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities. Adapting the respective molar ratios of the total used aniline to the total used formaldehyde and of the total used acid catalyst to the total used aniline allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity and ensures that no undesired fundamental changes occur in the product composition.Type: GrantFiled: December 18, 2017Date of Patent: April 28, 2020Assignee: Covestro Duetschland AGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes
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Publication number: 20200123096Abstract: The invention relates to a process for the preparation of di- and polyamines of the diphenylmethane series (MDA), in which firstly crude MDA is prepared and is then subjected to a distillation process, wherein the distillation process comprises the following: in a distillation column, separating off a stream containing aniline and water as head product so as to obtain the first product stream as sump product, in said distillation column or in an apparatus arranged downstream of said distillation column, performing a stripping with steam so as to obtain a gaseous stream containing aniline, water and MMDA, partially condensing this gaseous stream containing aniline, water and MMDA so as to obtain a liquid stream containing MMDA and water (and optionally aniline) and a gaseous stream containing aniline and water (and optionally MMDA), drying the liquid stream containing MMDA and water (and optionally aniline) obtained by the partial condensation so as to obtain the second product stream.Type: ApplicationFiled: October 10, 2019Publication date: April 23, 2020Inventors: Stefan WERSHOFEN, Richard ADAMSON, Georg PIRKL
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Patent number: 10626078Abstract: The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities. By adapting the temperatures in the acid-catalysed rearrangement step, the rearrangement reaction can be fully completed despite the change in dwell time inevitably associated with changed production capacity, with no undesired changes occurring in the product composition.Type: GrantFiled: December 18, 2017Date of Patent: April 21, 2020Assignee: Covestro Deutschland AGInventors: Thomas Knauf, Stefan Wershofen, Klaus-Gerd Gruner, Volker Hartjes