公开(公告)号：US20180370888A1

公开(公告)日：2018-12-27

申请号：US16065502

申请日：2016-12-20

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Klaus Hintzer ,  Zai-Ming Qiu ,  Gerd-Volker Röschenthaler ,  Romana Pajkert ,  Sergey N. Tverdomed

IPC: C07C41/30 ,  C07C43/12 ,  C07C249/02 ,  C07C251/08 ,  C07C253/18 ,  C07C255/03

Abstract: Methods of converting a fluorinated vinyl ether to a saturated partially fluorinated ether, the method comprising: reacting the fluorinated vinyl ether with an amine, ammonia, or combination thereof to form the saturated partially fluorinated ether.

公开(公告)号：US09828320B2

公开(公告)日：2017-11-28

申请号：US15529104

申请日：2015-11-20

Applicant: 3M Innovative Properties Company

Inventor： Klaus Hintzer ,  Markus E. Hirschberg ,  Kai Helmut Lochhaas ,  Werner Schwertfeger ,  Oleg Shyshkov ,  Arne Thaler

IPC: C07C41/14 ,  C07C45/44 ,  C07C45/51 ,  C07C253/10 ,  C07C407/00 ,  C07C303/30

CPC classification number: C07C41/14 ,  C07C41/01 ,  C07C45/44 ,  C07C45/518 ,  C07C51/58 ,  C07C253/00 ,  C07C253/10 ,  C07C303/24 ,  C07C303/30 ,  C07C407/00 ,  C25B1/28 ,  C25B1/30 ,  C07C43/17 ,  C07C43/123 ,  C07C43/126 ,  C07C305/26 ,  C07C255/10 ,  C07C53/48

Abstract: Described herein are three methods for making halogenated fluorinated ether-containing compounds using a fluorinated olefin or hexafluoropropylene oxide.

公开(公告)号：US11905178B2

公开(公告)日：2024-02-20

申请号：US18254671

申请日：2021-12-14

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Klaus Hintzer ,  Thomas W. Schoettle ,  Arne Thaler ,  Achim Schmidt-Rodenkirchen ,  Thorsten Gerdes ,  Konstantin Mierdel

IPC: C01B7/19 ,  C01B32/50 ,  C01B32/40

CPC classification number: C01B7/196 ,  C01B32/40 ,  C01B32/50

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.

公开(公告)号：US11377510B2

公开(公告)日：2022-07-05

申请号：US16646638

申请日：2018-09-14

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Lisa P. Chen ,  Gregg D. Dahlke ,  Denis Duchesne ,  Steven J. Hamrock ,  Klaus Hintzer ,  Markus E. Hirschberg ,  Arne Thaler ,  Tilman C. Zipplies

IPC: C08F214/26 ,  C08F2/10 ,  C08F8/12 ,  C08F214/18 ,  C08J5/22 ,  C08F8/44 ,  C09D11/52 ,  H01M8/10 ,  H01M4/86 ,  C08F216/14 ,  H01M8/1004 ,  H01M8/1039 ,  H01M8/1023

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.

公开(公告)号：US20210276946A1

公开(公告)日：2021-09-09

申请号：US16613900

申请日：2018-05-17

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Klaus Hintzer ,  Markus E. Hirschberg ,  Romana Pajkert ,  Gerd-Volker Röschenthaler ,  Sergey N. Tverdomed

IPC: C07C303/26 ,  C07C309/06 ,  C07C41/14 ,  C07C43/12

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.

公开(公告)号：US20210070686A1

公开(公告)日：2021-03-11

申请号：US16955618

申请日：2018-12-19

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Klaus Hintzer ,  William M. Lamanna ,  Sean M. Smith ,  Gerd-Volker Röschenthaler ,  Romana Pajkert ,  Sergey N. Tverdomed

IPC: C07C51/31 ,  C07F13/00 ,  C07C41/02

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.

公开(公告)号：US10723683B2

公开(公告)日：2020-07-28

申请号：US16065502

申请日：2016-12-20

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Klaus Hintzer ,  Zai-Ming Qiu ,  Gerd-Volker Röschenthaler ,  Romana Pajkert ,  Sergey N. Tverdomed

IPC: C07C41/30 ,  C07C249/02 ,  C07C253/18 ,  C07C41/18 ,  C07C43/12 ,  C07C251/08 ,  C07C255/13

Abstract: Methods of converting a fluorinated vinyl ether to a saturated partially fluorinated ether, the method comprising: reacting the fluorinated vinyl ether with an amine, ammonia, or combination thereof to form the saturated partially fluorinated ether.

公开(公告)号：US20190185599A1

公开(公告)日：2019-06-20

申请号：US16325795

申请日：2017-08-01

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Klaus Hintzer ,  Markus E. Hirschberg ,  Herbert Koenigsmann ,  Tilman C. Zipplies ,  Harald Kaspar

IPC: C08F214/26 ,  C08F2/26 ,  C09D127/18

CPC classification number: C08F214/262 ,  C08F2/24 ,  C08F2/26 ,  C08F214/26 ,  C08F2500/12 ,  C08F2500/24 ,  C08F2800/20 ,  C08K5/09 ,  C09D127/18

Abstract: Disclosed is a tetrafluoroethylene copolymer, methods of making the polymer, and articles comprising the polymer and methods of making the articles.

公开(公告)号：US20180273663A1

公开(公告)日：2018-09-27

申请号：US15762267

申请日：2016-09-22

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Gregg D. Dahlke ,  Denis Duchesne ,  Klaus Hintzer ,  Markus E. Hirschberg ,  Kai H. Lochhaas ,  Arne Thaler ,  Tilman C. Zipplies

IPC: C08F214/26 ,  C08F8/22 ,  H01M8/1004 ,  H01M8/1039 ,  H01M4/86

CPC classification number: C08F214/262 ,  C08F8/22 ,  C09D127/18 ,  C09D127/24 ,  H01M4/8668 ,  H01M8/1004 ,  H01M8/1039 ,  H01M2008/1095 ,  H01M2300/0082 ,  Y02P70/56

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—SO2—X, 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.

公开(公告)号：US20250002510A1

公开(公告)日：2025-01-02

申请号：US18707247

申请日：2022-10-26

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Mark W. Muggli ,  Romana M. Pajkert ,  Gerd-Voker Röschenthaler ,  Sergey N. Tverdomed

IPC: C07F9/40 ,  B01J39/05 ,  B01J39/20 ,  B01J47/12 ,  C08F216/20 ,  C25B13/08 ,  H01M8/10 ,  H01M8/1027 ,  H01M8/1034 ,  H01M8/1039

Abstract: Described herein is method of making a multifunctional compound by starting with a H—(OR)n—P(═O)(ORh1)2 and performed a series of reactions to form a functionalized phosphorous compound such as CF2═CF—CFY2—(OR)n—P(═O)(OQ)2(VIIA) CF2X3CF═CF—(OR)n—P(═O)(OQ)2(VIIB), or CF2X3CHFC(═O)—(OR)n—P(═O)(OH)2(VIB) Where: R is a C1-C4 alkenyl group; X3 is F or —(OR)n—P(═O)(OQ)2; n is 0 or 1; Y2 is —F, —Cl, —Br, —H, or a fluoroalkyl group comprising 1 to 3 carbon atoms, wherein the fluoroalkyl group optionally comprises at least one of an ether linkage, Cl, Br, or I; and Q is an alkyl group having 1 to 6 carbon atoms and optionally comprising at least one catenated ether linkage, —Si(CH3)3, —Si(CH2CH3)3, —H, a metallic cation, or a quaternary ammonium cation can be disposed on a metal surface. Such compounds may be used in generating ionomeric polymers and/or applied onto metal substrates.