Patents by Inventor Klaus Hintzer

Klaus Hintzer 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).

  • 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
  • Publication number: 20230087560
    Abstract: A compound having structural formula (II): where R2 is H, CH3, CF3, CH2CF2CF2H, or CH2CF2CF2CF2H; where R2f is a perfluoroalkyl group having 1-4 carbon atoms, optionally comprising either or both of a catenated nitrogen heteroatom and a catenated oxygen heteroatom; where R2f? is CF3 or CF2CF3; and where R2f? is CF3 or CF2CF3; with the proviso that when R2f? is CF3, then R2f? is CF3, and when R2 is H or CH3, then R2f is not CF3.
    Type: Application
    Filed: January 11, 2021
    Publication date: March 23, 2023
    Inventors: William M. Lamanna, Klaus Hintzer, Markus Hirschberg, David J. Lundberg
  • Publication number: 20230090482
    Abstract: A composite includes a fluorinated polymer and nanoparticles of a metal salt. The metal salt has a solubility product of not more than 1×10?4. The fluorinated polymer includes a fluorinated polymer backbone chain and a plurality of groups represented by formula —SO2X, in which each X is independently —NZH, —NZSO2(CF2)1-6SO2X?, —NZ[SO2(CF2)dSO2NZ]1-10SO2(CF2)dSO2X? or —OZ, and Z is independently a hydrogen, an alkali-metal cation, or a quaternary ammonium cation, X? is independently —NZH or —OZ, and each d is independently 1 to 6. A polymer electrolyte membrane, an electrode, and a membrane electrode assembly including the composite are also provided.
    Type: Application
    Filed: April 9, 2021
    Publication date: March 23, 2023
    Inventors: Arne Thaler, Andreas Rosin, Mark W. Muggli, Klaus Hintzer, Patrick K. Heimerdinger, Thorsten Gerdes, Denis Duchesne, Gregg D. Dahlke
  • Publication number: 20230056130
    Abstract: The copolymer includes divalent units represented by formula —[CF2—CF2]—, at least one divalent unit represented by formula (I): and at least one divalent unit independently represented by formula (II): A is —N(RFa)2 or a is non-aromatic, 5- to 8-membered, perfluorinated ring comprising one or two nitrogen atoms in the ring and optionally comprising at least one oxygen atom in the ring, each RFa is independently linear or branched perfluoroalkyl having 1 to 8 carbon atoms and optionally interrupted by at least one catenated O or N atom, each Y is independently —H or —F, with the proviso that one Y may be —CF3, h is 0, 1, or 2, each i is independently 2 to 8, and j is 0, 1, or 2. A catalyst ink and polymer electrolyte membrane including the copolymer are also provided.
    Type: Application
    Filed: December 18, 2020
    Publication date: February 23, 2023
    Inventors: Lisa P. Chen, Gregg D. Dahlke, Denis Duchesne, Klaus Hintzer, Matthew J. Lindell, Sean M. Smith, Arne Thaler, Michael A. Yandrasits
  • 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
  • Publication number: 20230002297
    Abstract: The process produces a fluorinated olefin from a fluorinated copolymer having at least one of sulfonic acid groups, carboxylic acid groups, or salts thereof. The process includes heating the fluorinated copolymer at a first temperature not more than 450° C. to decompose at least one of the sulfonic acid groups, carboxylic acid groups, or salts thereof to form a partially pyrolyzed intermediate and subsequently heating the partially pyrolyzed intermediate at a second temperature of at least 550° C. to produce the fluorinated olefin.
    Type: Application
    Filed: December 17, 2020
    Publication date: January 5, 2023
    Inventors: Arne Thaler, Achim Schmidt-Rodenkirchen, Mark W. Muggli, Konstantin Mierdel, Klaus Hintzer, Thorsten Gerdes, Denis Duchesne, Gregg D. Dahlke
  • Publication number: 20220372193
    Abstract: Described herein is method of functionalizing fluorinated polymers, wherein a reaction compound is grafted onto a fluorinated polymer, wherein the fluorinated polymer comprises at least one Br, I, and Cl group and is free of —CH2CH2— linkages. In one embodiment, the functionalized fluorinated polymer comprises a perfluorinated polymer backbone with pendent groups therefrom is disclosed, wherein at least one pendent group is according to formula I: where Rf is a bond, or a divalent perfluorinated group, optionally comprising at least one in-chain ether linkage; Z is I, Br, or Cl; and X comprises a functional group selected from the group consisting of an alcohol; phosphorous acid and salts thereof; phosphoric acid and salts thereof; a silane; an amine; an amide; a hydrocarbon, optionally comprising an in-chain oxygen, nitrogen, or sulfur linkage; a carboxylic acid and salts thereof; an ester; a sulfonyl fluoride, a sulfonic acid and salts thereof; and combinations thereof.
    Type: Application
    Filed: November 6, 2020
    Publication date: November 24, 2022
    Inventors: Frans A. Audenaert, Klaus Hintzer, Alain G. Verschuere
  • 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
  • Publication number: 20220073664
    Abstract: The composition includes a curable fluoropolymer having nitrogen-containing cure sites and a curative including an organo onium cation and an anion represented by Formula (I) or Formula (II). The composition is free of metal cations or has not more than 20 parts per million metal cations and free of silicon dioxide or has less than 0.5 percent by weight silicon dioxide, based on the total weight of the composition. In some cases, the composition consists of the curable fluoropolymer and the curative. Shaped articles including the composition, a fluoroelastomer prepared by curing the composition, a method of making a fluoroelastomer article, and a process for making the composition are also described.
    Type: Application
    Filed: December 17, 2019
    Publication date: March 10, 2022
    Inventors: Tatsuo Fukushi, Tamon Aoki, Qilin Chan, Miguel A. Guerra, Klaus Hintzer, Florian D. Jochum, Michael H. Mitchell, Allen M. Sohlo, Yuta Suzuki
  • Publication number: 20220049079
    Abstract: Described herein is a method of making a curable perfluoroelastomer, wherein the curable perfluoroelastomer comprises particles of a semi crystalline fluoropolymer, wherein the semi crystalline fluoropolymer is a TFE copolymer comprising no more than 1 wt % of at least one additional fluorinated monomer. The method comprises: (a) obtaining an amorphous perfluoropolymer and the particles of the semi crystalline fluoropolymer; and (c) dry blending the amorphous perfluoropolymer and the particles to form a curable perfluoroelastomer.
    Type: Application
    Filed: December 19, 2019
    Publication date: February 17, 2022
    Inventors: Tatsuo Fukushi, Klaus Hintzer, Florian D. Jochum, Michael H. Mitchell, Tho Q. Nguyen, Peter J. Scott, Allen M. Sohlo, Yuta Suzuki, Karl D. Weilandt, Steffen Vowinkel
  • Patent number: 11248117
    Abstract: Described herein is a curable composition comprising an amorphous fluoropolymer having an iodine, bromine and/or nitrile cure site; a peroxide cure system comprising a peroxide and a Type II coagent; and a photoinitiator, wherein the curable composition is substantially free of a binder material. Also described herein, are methods of curing the curable composition using actinic radiation and articles thereof.
    Type: Grant
    Filed: July 17, 2018
    Date of Patent: February 15, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Xuan Jiang, Jeffrey N. Bartow, Robert J. DeVoe, Tatsuo Fukushi, Klaus Hintzer, Tho Q. Nguyen, Sheng Ye, Fee Zentis
  • Publication number: 20220033635
    Abstract: Described herein is a latex blend comprising (i) an amorphous perfluoropolymer and (ii) an aqueous dispersion of semi crystalline fluoropolymer particles, wherein the particles comprise a TFE homopolymer or a TFE copolymer comprising no more than 1 wt % of a second fluorinated monomer, wherein the semi crystalline fluoropolymer particles (a) have an MFI (372° C. with 2.16 kg) of less than 50 g/10 min or (b) are not melt processible and have an SSG of less than 2.190, wherein the semi crystalline fluoropolymer particles have an average diameter greater than 100 nm.
    Type: Application
    Filed: December 19, 2019
    Publication date: February 3, 2022
    Inventors: Klaus Hintzer, Tamon Aoki, Tatsuo Fukushi, Florian D. Jochum, Peter J. Scott, Yuta Suzuki, Karl D. Weilandt, Steffen Vowinkel
  • Patent number: 11230053
    Abstract: Provided are methods for making shaped fluoropolymer by additive processing using a polymerizable binder. Also are 3D printable compositions for making shaped fluoropolymer articles and articles comprising a shaped fluoropolymer.
    Type: Grant
    Filed: January 19, 2017
    Date of Patent: January 25, 2022
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Jeffrey N. Bartow, Carsten Franke, Robin E. Wright, Fee Zentis, Klaus Hintzer, Gabriele H. Gottschalk-Gaudig, Bernd Gangnus, Malte Korten, Gallus Schechner, Wolfgang Neumann
  • Patent number: 11193037
    Abstract: An aqueous dispersion comprising a tetrafluoroethylene core-shell polymer and at least one surfactant corresponding to the general formula R10-[CH2CH20]n[R20]m-R3 wherein R1 represents a linear or branched aliphatic hydrocarbon group having at least 8 carbon atoms, preferably 8 to 18 carbon atoms, R2 represents an alkylene having 3 carbon atoms, R3 represents hydrogen, a C1-C3 alkyl group, or a C1-C3 hydroxyalkyl group, n has a value of 0 to 40, m has a value of 0 to 40 and the sum of n+m is at least 2, wherein the dispersion is free of fluorinated emulsifiers or contains them in an amount of less than 50 ppm based on the weight of the dispersion and wherein the core-shell polymer contains an outer shell of tetrafluoroethylene homopolymer. Further provided are methods of making the dispersions, coating compositions comprising the dispersions and article coated by the coating composition.
    Type: Grant
    Filed: January 29, 2015
    Date of Patent: December 7, 2021
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Michael C. Dadalas, Klaus Hintzer, Arnd Kurz, Tilman C. Zipplies, Kai Helmut Lochhaas
  • Patent number: 11179886
    Abstract: Provided are method of producing a shaped fluoropolymer articles. The methods include subjecting a composition comprising a fluoropolymer to additive processing in an additive processing device. Also provided are articles obtained with the methods and 3D-printable compositions.
    Type: Grant
    Filed: January 19, 2017
    Date of Patent: November 23, 2021
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Xuan Jiang, Jeffrey N. Bartow, Carsten Franke, Fee Zentis, Klaus Hintzer, Gabriele H. Gottschalk-Gaudig, Sebastian F. Zehentmaier
  • Publication number: 20210340294
    Abstract: The present disclosure relates to a fluoropolymer powder for additive manufacturing of fluoropolymers having an average particle size (d50) in a range from 20 to 100 micrometers, preferably 30 to 70 micrometers, more preferably from 30 to 65 micrometers, most preferably from 30 to 60 micrometers and an average particle size (d90) in a range from 60 to 120 micrometers, and a bulk density of at least 800 g/l and no greater than 2000 g/l when measured according to DIN EN ISO 60:2000-1. Also provided are uses of the powder, processes of making the powders, articles produced by using the powder and processes for additive manufacturing using the powder.
    Type: Application
    Filed: October 16, 2019
    Publication date: November 4, 2021
    Inventors: Andreas M. Gledmacher, Fee Zentis, Michael Maerz, Klaus Hintzer, Harald Kaspar, Jens Eichler, Gabriele H. Gottschalk-Gaudig
  • 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