Patents by Inventor Markus E. HIRSCHBERG

Markus E. HIRSCHBERG 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).

  • Patent number: 11905178
    Abstract: Methods of converting a variety of fluorinated materials into anhydrous hydrogen fluoride are described. The methods include thermally decomposing the fluorinated materials into a gaseous effluent comprising hydrogen fluoride and carbon dioxide. This gaseous effluent is then treated with carbon at a temperature of at least 830° C., converting the carbon dioxide to carbon monoxide (CO) and producing a gaseous product comprising the hydrogen fluoride, which can be condensed to generate anhydrous hydrogen fluoride. These methods can also be used to convert water contained in the gaseous effluent into hydrogen.
    Type: Grant
    Filed: December 14, 2021
    Date of Patent: February 20, 2024
    Assignee: 3M Innovative Properties Company
    Inventors: Markus E. Hirschberg, Klaus Hintzer, Thomas W. Schoettle, Arne Thaler, Achim Schmidt-Rodenkirchen, Thorsten Gerdes, Konstantin Mierdel
  • Publication number: 20240002228
    Abstract: Methods of converting a variety of fluorinated materials into anhydrous hydrogen fluoride are described. The methods include thermally decomposing the fluorinated materials into a gaseous effluent comprising hydrogen fluoride and carbon dioxide. This gaseous effluent is then treated with carbon at a temperature of at least 830° C., converting the carbon dioxide to carbon monoxide (CO) and producing a gaseous product comprising the hydrogen fluoride, which can be condensed to generate anhydrous hydrogen fluoride. These methods can also be used to convert water contained in the gaseous effluent into hydrogen.
    Type: Application
    Filed: December 14, 2021
    Publication date: January 4, 2024
    Inventors: Markus E. Hirschberg, Kalus Hintzer, Thomas W. Schoettle, Arne Thaler, Achim Schmidt-Rodenkirchen, Thorsten Gerdes, Konstantin Mierdel
  • Publication number: 20230357172
    Abstract: Described herein is a method to synthesize a perfluorinated allyl ether compound of formula (I) or a perfluorinated allyl amine compound of formula (II) Where Rf1 and Rf2 are (i) independently selected from a perfluorinated alkyl group comprising 1-7 carbon atoms, a perfluorinated aryl group comprising a 5- or 6-membered ring, or combinations thereof, and optionally comprising one or more catenated heteroatoms selected from N or O; or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one catenated O or N atom; and Rf3 is a perfluorinated alkyl group comprising 1-3 carbon atoms. The resulting perfluorinated allyl ether compounds disclosed herein may be used in polymer synthesis.
    Type: Application
    Filed: February 25, 2021
    Publication date: November 9, 2023
    Inventors: Sean M. Smith, Klaus Hintzer, Markus E. Hirschberg, William M. Lamanna
  • Patent number: 11795126
    Abstract: Mechanical stirred bed reactors that incorporate a screen are described. Methods of using such reactors to process perfluoropolymers to form perfluorinated olefin monomers are also described. The reactors and methods may be used to upcycle filled perfluorinated materials.
    Type: Grant
    Filed: February 19, 2021
    Date of Patent: October 24, 2023
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Markus E. Hirschberg, Klaus Hintzer, Thomas G. Kolbeck, Matthias Wieland, Peter Bauer, Achim Schmidt-Rodenkirchen, Thorsten Gerdes
  • Patent number: 11673861
    Abstract: A perfluorinated 1-alkoxypropene represented by general Formula (I), compositions that include such compounds, and methods and systems that include such compositions are provided, wherein Formula (I) is represented by: RfO—CF?CFCF3 wherein Rf is a linear, branched, or cyclic perfluoroalkyl group having 2 to 10 carbon atoms and optionally further including 1 to 3 nitrogen and/or 1 to 4 oxygen catenary heteroatoms.
    Type: Grant
    Filed: December 12, 2018
    Date of Patent: June 13, 2023
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Sean M. Smith, Michael G. Costello, Klaus Hintzer, Markus E. Hirschberg, William M. Lamanna
  • Publication number: 20230109030
    Abstract: Mechanical stirred bed reactors that incorporate a screen are described. Methods of using such reactors to process perfluoropolymers to form perfluorinated olefin monomers are also described. The reactors and methods may be used to upcycle filled perfluorinated materials.
    Type: Application
    Filed: February 19, 2021
    Publication date: April 6, 2023
    Inventors: Markus E. Hirschberg, Klaus Hintzer, Thomas G. Kolbeck, Matthias Wieland, Peter Bauer, Achim Schmidt-Rodenkirchen, Thorsten Gerdes
  • Patent number: 11551827
    Abstract: A dielectric fluid (i.e., dielectric composition) that includes a perfluorinated 1-alkoxypropene compound represented by the following general Formula (I): RfO—CF?CFCF3 wherein Rf is CF3— or CF3CF2—. Such dielectric fluids may be useful in various electrical devices.
    Type: Grant
    Filed: December 12, 2018
    Date of Patent: January 10, 2023
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Sean M. Smith, Michael G. Costello, Klaus Hintzer, Markus E. Hirschberg, William M. Lamanna, John G. Owens
  • Patent number: 11492431
    Abstract: The copolymer includes divalent units represented by formula —[CF2—CF2]—, divalent units represented by formula; and one or more divalent units independently represented by formula: The copolymer has an —SO2X equivalent weight in a range from 300 to 2000. A polymer electrolyte membrane that includes the copolymer and a membrane electrode assembly that includes such a polymer electrolyte membrane are also provided.
    Type: Grant
    Filed: September 14, 2018
    Date of Patent: November 8, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Lisa P. Chen, Gregg D. Dahlke, Denis Duchesne, Steven J. Hamrock, Klaus Hintzer, Markus E. Hirschberg, Arne Thaler, Tilman C. Zipplies
  • Publication number: 20220227696
    Abstract: The multifunctional compound is represented by formula X—C(R)RF—Y, in which X and Y are each independently —C(O)—O-M, —C(O)-HAL, —C(O)—NR12, —C?N, —C(O)NR1—SO2—Rf1-W, or a fluorinated alkenyl group that is optionally interrupted by one or more —O— groups. HAL is —F, —Cl, or —Br. Rf1 is a fluorinated alkylene group that is optionally interrupted by one or more —O— groups. W is —F, —SO2Z, —CF?CF2, —O—CF?CF2, or —O—CF2—CF?CF2. Z is —F, —Cl, —NR12, or —OM. Each R1 is a hydrogen atom or alkyl having up to four carbon atoms. M is an alkyl group, a trimethylsilyl group, a hydrogen atom, a metallic cation, or a quaternary ammonium cation. R is a bromine, chloride, fluorine or hydrogen atom; and RF is a fluorinated alkenyl group that is unsubstituted or substituted by at least one chlorine atom, aryl group, or a combination thereof or RF is a fluorinated alkyl group or arylalkylenyl group that is substituted by bromine or iodine and uninterrupted or interrupted by at least one —O— group.
    Type: Application
    Filed: June 2, 2020
    Publication date: July 21, 2022
    Inventors: Markus E. Hirschberg, Klaus Hintzer, Gerd-Volker Röschenthaler, Sergey N. Tverdomed, Romana Pajkert
  • Patent number: 11377510
    Abstract: The copolymer includes divalent units represented by formula —[CF2—CF2]—, divalent units represented by formula: (I), and one or more divalent units independently represented by formula: (II) When Z is hydrogen, the copolymer has an alpha transition temperature of up to 100 ?C. The copolymer has an —SO3Z equivalent weight in a range from 300 to 1400, and a variation of the copolymer in which —SO3Z is replaced with —SO2F has a melt flow index of up to 80 grams per ten minutes measured at a temperature of 265° C. and at a support weight of 5 kg. A catalyst ink or polymer electrolyte membrane including the copolymer are also provided.
    Type: Grant
    Filed: September 14, 2018
    Date of Patent: July 5, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Lisa P. Chen, Gregg D. Dahlke, Denis Duchesne, Steven J. Hamrock, Klaus Hintzer, Markus E. Hirschberg, Arne Thaler, Tilman C. Zipplies
  • Patent number: 11292763
    Abstract: A method includes combining first components including at least one of CF2?CF—CF2—OSO2Cl or CF2?CF—CF2—OSO2CF3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO2Cl)3 and hexafluoropropylene to provide CF2?CF—CF2—OSO2Cl. Another method includes combining second components including M(OSO2CF3)3 and hexafluoropropylene at a temperature above 0° C. to provide CF2?CF—CF2—OSO2CF3, wherein M is Al or B. The compound CF2?CF—CF2—OSO2Cl is also provided.
    Type: Grant
    Filed: May 17, 2018
    Date of Patent: April 5, 2022
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Klaus Hintzer, Markus E. Hirschberg, Romana Pajkert, Gerd-Volker Röschenthaler, Sergey N. Tverdomed
  • Patent number: 11155661
    Abstract: A method of making a copolymer is disclosed. The method includes copolymerizing components including tetrafluoroethylene and a compound represented by formula CF2?CF—O—(CF2)a—SO2X, wherein “a” is a number from 1 to 4, and X is —NZH, —NZ—SO2—(CF2)1-6—SO2X?, or —OZ, wherein Z is independently a hydrogen, an alkali metal cation, or a quaternary ammonium cation, and wherein X? is independently —NZH or —OZ. The components include at least 60 mole % of tetrafluoroethylene based on the total amount of components. A copolymer prepared by the method is also provided. A method of making a membrane using the copolymer is also provided. The present disclosure also provides a polymer electrolyte membrane that includes a copolymer made by the method and a membrane electrode assembly that includes such a polymer electrolyte membrane.
    Type: Grant
    Filed: September 22, 2016
    Date of Patent: October 26, 2021
    Assignee: 3M Innovative Properties Company
    Inventors: Gregg D. Dahlke, Denis Duchesne, Klaus Hintzer, Markus E. Hirschberg, Kai H. Lochhaas, Arne Thaler, Tilman C. Zipplies
  • Publication number: 20210276946
    Abstract: A method includes combining first components including at least one of CF2?CF—CF2—OSO2Cl or CF2?CF—CF2—OSO2CF3, a polyfluorinated compound having at least one ketone or carboxylic acid halide, and fluoride ion to provide a compound comprising at least one perfluorinated allyl ether group. A method includes combining second components including B(OSO2Cl)3 and hexafluoropropylene to provide CF2?CF—CF2—OSO2Cl. Another method includes combining second components including M(OSO2CF3)3 and hexafluoropropylene at a temperature above 0° C. to provide CF2?CF—CF2—OSO2CF3, wherein M is Al or B. The compound CF2?CF—CF2—OSO2Cl is also provided.
    Type: Application
    Filed: May 17, 2018
    Publication date: September 9, 2021
    Inventors: Klaus Hintzer, Markus E. Hirschberg, Romana Pajkert, Gerd-Volker Röschenthaler, Sergey N. Tverdomed
  • Publication number: 20210246886
    Abstract: A foamable composition includes a blowing agent, a foamable polymer or a precursor composition thereof, and a nucleating agent. The nucleating agent includes a compound having structural formula (I) R1SO2R2(SO2R3)n (I) where R1, R2, and R3 are each independently a fluoroalkyl group having from 1 to 10 carbon atoms that is linear, branched, or cyclic and optionally contain at least one catenated ether oxygen atom or a trivalent nitrogen atom, and n is 0 or 1.
    Type: Application
    Filed: April 23, 2019
    Publication date: August 12, 2021
    Inventors: William M. Lamanna, Sean M. Smith, Michael G. Costello, Michael J. Bulinski, John G. Owens, Markus E. Hirschberg, Klaus Hintzer, Bamidele O. Fayemi, Philip E. Tuma, Nicholas S. Johnson, Forrest A. Coughlin, Jay R. Nierengarten
  • Patent number: 11028198
    Abstract: A copolymer having tetrafluoroethylene units and second polymerized monomer units in a range from 0.2 to 1 percent by weight, based on the total weight of the copolymer. Rf is a linear or branched perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups, n is independently from 1 to 6, and z is 0, 1, or 2. The copolymer has a melt flow index in a range from 0.02 grams per 10 minutes to 19.4 grams per 10 minutes. The copolymer can be extruded to make articles, such as insulated cables. A method of making the copolymer is also disclosed.
    Type: Grant
    Filed: August 1, 2017
    Date of Patent: June 8, 2021
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Harald Kaspar, Klaus Hintzer, Markus E. Hirschberg, Herbert Koenigsmann, Karl D. Weilandt, Tilman C. Zipplies
  • Publication number: 20210070686
    Abstract: A method of making a polyfunctional polyfluorinated compound includes combining first components that include a polyfluorinated cyclic compound having 4 to 7 ring carbon atoms and at least one of osmium tetroxide, ruthenium tetroxide or a precursor thereof and forming a polyfluorinated dicarboxylic acid. Two of the ring carbon atoms of the polyfluorinated cyclic compound form a double bond or an epoxide. The precursor reacts with an oxidant to form ruthenium tetroxide. Methods also include converting the polyfluorinated dicarboxylic acid to a polyfluorinated dicarboxylic acid halide and converting the polyfluorinated dicarboxylic acid halide to other polyfunctional polyfluorinated compounds.
    Type: Application
    Filed: December 19, 2018
    Publication date: March 11, 2021
    Inventors: Markus E. Hirschberg, Klaus Hintzer, William M. Lamanna, Sean M. Smith, Gerd-Volker Röschenthaler, Romana Pajkert, Sergey N. Tverdomed
  • Publication number: 20200388412
    Abstract: A dielectric fluid (i.e., dielectric composition) that includes a perfluorinated 1-alkoxypropene compound represented by the following general Formula (I): RfO—CF?CFCF3 wherein Rf is CF3— or CF3CF2—. Such dielectric fluids may be useful in various electrical devices.
    Type: Application
    Filed: December 12, 2018
    Publication date: December 10, 2020
    Inventors: Sean M. Smith, Michael G. Costello, Klaus Hintzer, Markus E. Hirschberg, William M. Lamanna, John G. Owens
  • Publication number: 20200386488
    Abstract: A perfluorinated 1-alkoxypropene represented by general Formula (I), compositions that include such compounds, and methods and systems that include such compositions are provided, wherein Formula (I) is represented by: RfO—CF?CFCF3 wherein Rf is a linear, branched, or cyclic perfluoroalkyl group having 2 to 10 carbon atoms and optionally further including 1 to 3 nitrogen and/or 1 to 4 oxygen catenary heteroatoms.
    Type: Application
    Filed: December 12, 2018
    Publication date: December 10, 2020
    Inventors: Sean M. Smith, Michael G. Costello, Klaus Hintzer, Markus E. Hirschberg, William M. Lamanna
  • Publication number: 20200303755
    Abstract: The copolymer includes divalent units represented by formula —[CF2-CF2]—, divalent units represented by formula: (I), and one or more divalent units independently represented by formula: (II) When Z is hydrogen, the copolymer has an alpha transition temperature of up to 100 ?C. The copolymer has an —SO3Z equivalent weight in a range from 300 to 1400, and a variation of the copolymer in which —SO3Z is replaced with —SO2F has a melt flow index of up to 80 grams per ten minutes measured at a temperature of 265° C. and at a support weight of 5 kg. A catalyst ink or polymer electrolyte membrane including the copolymer are also provided.
    Type: Application
    Filed: September 14, 2018
    Publication date: September 24, 2020
    Inventors: Lisa P. Chen, Gregg D. Dahlke, Denis Duchesne, Steven J. Hamrock, Klaus Hintzer, Markus E. Hirschberg, Arne Thaler, Tilman C. Zipplies
  • Publication number: 20200277420
    Abstract: The copolymer includes divalent units represented by formula —[CF2—CF2]—, divalent units represented by formula: and one or more divalent units independently represented by formula: The copolymer has an —SO2X equivalent weight in a range from 300 to 2000. A polymer electrolyte membrane that includes the copolymer and a membrane electrode assembly that includes such a polymer electrolyte membrane are also provided.
    Type: Application
    Filed: September 14, 2018
    Publication date: September 3, 2020
    Inventors: Lisa P. Chen, Gregg D. Dahlke, Denis Duchesne, Steven J. Hamrock, Klaus Hintzer, Markus E. Hirschberg, Arne Thaler, Tilman C. Zipplies