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：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：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.

公开(公告)号：US11292763B2

公开(公告)日：2022-04-05

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 ,  C07C41/14 ,  C07C309/06 ,  C07C303/24 ,  C07C305/26

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：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.