公开(公告)号：US11795126B2

公开(公告)日：2023-10-24

申请号：US17904611

申请日：2021-02-19

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Markus E. Hirschberg ,  Klaus Hintzer ,  Thomas G. Kolbeck ,  Matthias Wieland ,  Peter Bauer ,  Achim Schmidt-Rodenkirchen ,  Thorsten Gerdes

IPC: C07C17/367 ,  B01J8/08 ,  B01J8/10 ,  C08J11/14 ,  C10B53/07

CPC classification number: C07C17/367 ,  B01J8/085 ,  B01J8/10 ,  C08J11/14 ,  C10B53/07 ,  B01J2208/00442 ,  B01J2208/00867 ,  B01J2208/00884 ,  C08J2327/12 ,  C07C17/367 ,  C07C21/18 ,  C07C17/367 ,  C07C21/185

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.

公开(公告)号：US11492431B2

公开(公告)日：2022-11-08

申请号：US16645882

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

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.

公开(公告)号：US11028198B2

公开(公告)日：2021-06-08

申请号：US16325831

申请日：2017-08-01

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

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

IPC: C08F214/26 ,  C08F214/28 ,  H01B3/44 ,  C08L27/18 ,  C08L27/20 ,  C08F214/18

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.

公开(公告)号：US20240002228A1

公开(公告)日：2024-01-04

申请号：US18254671

申请日：2021-12-14

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

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

IPC: C01B7/19

CPC classification number: C01B7/196 ,  C01B32/40

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：US20230357172A1

公开(公告)日：2023-11-09

申请号：US17911567

申请日：2021-02-25

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

Inventor： Sean M. Smith ,  Klaus Hintzer ,  Markus E. Hirschberg ,  William M. Lamanna

IPC: C07D207/16 ,  C07C211/24 ,  C07C43/192 ,  C07D241/06 ,  C07D223/04 ,  C07C49/167 ,  C07C49/395 ,  C07C49/403 ,  C07D265/30 ,  C07D221/00 ,  C07C43/17 ,  C07D207/22

CPC classification number: C07D265/30 ,  C07C43/17 ,  C07C43/192 ,  C07C49/167 ,  C07C49/395 ,  C07C49/403 ,  C07C211/24 ,  C07D207/16 ,  C07D207/22 ,  C07D221/00 ,  C07D223/04 ,  C07D241/06

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.

公开(公告)号：US20200303755A1

公开(公告)日：2020-09-24

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: H01M8/1039 ,  C08F214/26 ,  H01M4/86 ,  H01M8/1004 ,  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：US20190202951A1

公开(公告)日：2019-07-04

申请号：US16325831

申请日：2017-08-01

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

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

IPC: C08F214/26 ,  C08F214/28 ,  C08L27/18 ,  C08L27/20 ,  H01B3/44

CPC classification number: C08F214/262 ,  C08F214/26 ,  C08F214/28 ,  C08L27/18 ,  C08L27/20 ,  C08L2203/16 ,  C08L2203/18 ,  H01B3/445

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.

公开(公告)号：US20220227696A1

公开(公告)日：2022-07-21

申请号：US17614608

申请日：2020-06-02

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

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

IPC: C07C69/65 ,  C08F214/18 ,  C07C67/347 ,  C07C57/52 ,  C07C51/09 ,  C07F7/18 ,  C07C57/76 ,  C07C51/60

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. A process for making the compound is also disclosed. A fluoropolymer made from the compound and a method of making the fluoropolymer are also disclosed.

公开(公告)号：US11155661B2

公开(公告)日：2021-10-26

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 ,  H01M8/1039 ,  C09D127/24 ,  C09D127/18 ,  H01M4/86 ,  H01M8/1004 ,  H01M8/1018

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.

公开(公告)号：US10737998B2

公开(公告)日：2020-08-11

申请号：US16065454

申请日：2016-12-12

Applicant: 3M INNOVATIVE PROPERTIES COMPANY

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

IPC: C07C51/58 ,  C07C69/96 ,  C07C59/135 ,  C07C68/00 ,  C07C45/42 ,  C07C67/14 ,  C07C51/04 ,  C07C51/00 ,  C07C67/00 ,  B01J23/28

Abstract: Methods of converting a fluorinated compound into a fluorinated acyl fluoride or derivative thereof, the method including reacting the fluorinated compound with a catalytic amount of at least one transition metal compound and an oxygen-containing compound to form the fluorinated acyl fluoride or derivative thereof. Compounds formed using such methods are also included, including for example and derivatives thereof, or combinations thereof.