公开(公告)号：US11198670B2

公开(公告)日：2021-12-14

申请号：US16338374

申请日：2017-09-29

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Masahiro Higashi ,  Satoru Yoneda ,  Akiyoshi Yamauchi ,  Sumi Ishihara ,  Yosuke Kishikawa ,  Hirokazu Aoyama

IPC: C07C235/06 ,  C07C69/67 ,  C07C305/10 ,  C07C309/13 ,  C07C69/34 ,  C07C235/12

Abstract: The invention provides a novel hydrocarbon-containing carboxylic acid, hydrocarbon-containing sulfonic acid, hydrocarbon-containing sulfuric acid ester, or a salt thereof, and a surfactant. Each of them is a compound represented by the following formula (1): CR1R2R4—CR3R5—X-A wherein R1 to R5 are each H or a monovalent substituent; at least one of R1 or R3 is a group represented by the formula: —Y—R6; at least one of R2 or R5 is a group represented by the formula: —X-A or a group represented by the formula: —Y—R6; and As at the respective appearances are the same as or different from each other, and are each —COOM, —SO3M, or —OSO3M.

公开(公告)号：US20210070688A1

公开(公告)日：2021-03-11

申请号：US17061453

申请日：2020-10-01

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Masahiro Higashi ,  Satoru Yoneda ,  Akiyoshi Yamauchi ,  Sumi Ishihara ,  Yosuke Kishikawa ,  Hirokazu Aoyama

IPC: C07C59/185 ,  B01F17/00 ,  C07C303/26

Abstract: A carboxylic acid or sulfonic acid salt containing a plurality of carbonyl groups, and a surfactant represented by the following formula: R1—C(═O)—R2—C(═O)—R3-A wherein R1, R2 and R3 are as defined herein, and A is —COOX or —SO3X, wherein X is H, a metal atom, NR44, imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R4s are each H or an organic group and are the same as or different from each other; and any two of R1, R2, and R3 optionally bind to each other to form a ring.

公开(公告)号：US09738589B2

公开(公告)日：2017-08-22

申请号：US15183163

申请日：2016-06-15

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Tatsuya Ohtsuka ,  Akihiro Gotou ,  Sumi Ishihara ,  Yoshihiro Yamamoto ,  Akinori Yamamoto ,  Yoshichika Kuroki ,  Yuzo Komatsu ,  Yousuke Kishikawa

IPC: C07C67/36 ,  B01J27/13 ,  B01J31/24 ,  B01J23/44 ,  B01J31/02

CPC classification number: C07C67/36 ,  B01J23/44 ,  B01J27/13 ,  B01J31/0237 ,  B01J31/24 ,  B01J31/2404 ,  B01J31/2409 ,  B01J2231/321 ,  B01J2231/49 ,  B01J2531/824 ,  C07C69/653

Abstract: The object of the present invention is to provide a process for producing α-fluoroacrylic acid ester at a high starting material conversion, high selectivity, and high yield. The present invention provides a process for producing the compound represented by the formula (1) wherein R represents alkyl optionally substituted with one or more fluorine atoms, the process comprising step A of reacting a compound represented by the formula (2) wherein X represents a bromine atom or a chlorine atom with an alcohol represented by the formula (3) wherein the symbol is as defined above, and carbon monoxide in the presence of a transition metal catalyst and a base to thereby obtain the compound represented by the formula (1).

公开(公告)号：US09732027B2

公开(公告)日：2017-08-15

申请号：US15107204

申请日：2014-12-26

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Akihiro Gotou ,  Manaho Miyazaki ,  Sumi Ishihara ,  Takashi Namikawa ,  Tatsuya Ohtsuka ,  Yosuke Kishikawa

IPC: C07C67/36

CPC classification number: C07C67/36 ,  C07C69/653 ,  C07C69/65

Abstract: An object of the present invention is to provide a process for producing α-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH  (3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).

公开(公告)号：US11999681B2

公开(公告)日：2024-06-04

申请号：US16498576

申请日：2018-03-30

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Satoru Yoneda ,  Masahiro Higashi ,  Akiyoshi Yamauchi ,  Sumi Ishihara ,  Yosuke Kishikawa ,  Marina Nakano ,  Shinnosuke Nitta ,  Hirokazu Aoyama

IPC: C07C305/10 ,  C07C303/24

CPC classification number: C07C305/10 ,  C07C303/24

Abstract: An alkyl sulfate ester containing a carbonyl group or a salt thereof. The compound is represented by the following formula:

R1—C(—O)—(CR22)n—(OR3)p—(CR42)q-L-OSO3X

wherein R1, R2, R3, R4, L, X, n, p and q are as defined herein. Also disclosed is a production method for making the alkyl sulfate ester.

公开(公告)号：US20220348699A1

公开(公告)日：2022-11-03

申请号：US17849364

申请日：2022-06-24

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Marina NAKANO ,  Masahiro Higashi ,  Sumi Ishihara ,  Yosuke Kishikawa

IPC: C08F14/26 ,  C08F2/38 ,  C08F2/26

Abstract: Provided is a method for producing a fluoropolymer, the method including a polymerizing step of polymerizing tetrafluoroethylene in an aqueous medium in the presence of an initiator, a chain transfer agent, and a surfactant to provide a fluoropolymer containing more than 80 mol % of a polymerized unit based on tetrafluoroethylene, the chain transfer agent including at least one selected from the group consisting of a dithioester compound, a dithiocarbamate compound, a trithiocarbonate compound, and a xanthate compound. Also provided is a fluoropolymer represented by the formula Af-CRP defined in the description.

公开(公告)号：US10479681B2

公开(公告)日：2019-11-19

申请号：US16261737

申请日：2019-01-30

Applicant: DAIKIN INDUSTRIES, LTD. ,  NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY

Inventor： Shoji Hara ,  Yosuke Kishikawa ,  Atsushi Shirai ,  Takashi Namikawa ,  Sumi Ishihara

IPC: C01B7/24 ,  C01D3/02 ,  C01D13/00 ,  C07C17/354 ,  C07C17/361 ,  C07C41/22 ,  C07C45/63 ,  C07C45/67 ,  C07C67/307 ,  C07C67/333 ,  C07C209/74 ,  C07C231/12 ,  C07C319/20 ,  C07D209/10 ,  C07D309/10 ,  C07D493/04

Abstract: An object of the present invention is to provide a novel substance that has a high reactivity as a fluorinating agent, is effectively used in various fluorination reactions, and is safely handled even in air. As the solution for achieving this object, the present invention provides a complex obtained by reacting bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals in a nonpolar solvent. This complex serves as a fluorinating agent that provides excellent fluorination performance and that is stable in air.

公开(公告)号：US09701614B2

公开(公告)日：2017-07-11

申请号：US15107204

申请日：2014-12-26

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Akihiro Gotou ,  Manaho Miyazaki ,  Sumi Ishihara ,  Takashi Namikawa ,  Tatsuya Ohtsuka ,  Yosuke Kishikawa

IPC: C07C67/36

Abstract: An object of the present invention is to provide a process for producing α-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH  (3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).

公开(公告)号：US12012470B2

公开(公告)日：2024-06-18

申请号：US17974402

申请日：2022-10-26

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Taketo Kato ,  Satoru Yoneda ,  Manabu Fujisawa ,  Kazuya Asano ,  Takahiro Kitahara ,  Masahiro Higashi ,  Akiyoshi Yamauchi ,  Sumi Ishihara ,  Yosuke Kishikawa ,  Shinnosuke Nitta ,  Marina Nakano ,  Hirotoshi Yoshida ,  Yoshinori Nanba ,  Kengo Ito ,  Chiaki Okui ,  Hirokazu Aoyama ,  Masamichi Sukegawa ,  Taku Yamanaka ,  Yuuji Tanaka ,  Kenji Ichikawa ,  Yohei Fujimoto ,  Hiroyuki Sato

IPC: C08F14/26 ,  C08K5/098 ,  C08K5/42

CPC classification number: C08F14/26 ,  C08K5/098 ,  C08K5/42 ,  C08K2201/014 ,  C08K2201/019

Abstract: A composition including a fluoropolymer and substantially free from a compound represented by the following formula (3): (H—(CF2)8—SO3)qM2, wherein M2 is H, a metal atom, NR54, imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent; R5s are each H or an organic group and are the same as or different from each other; and q is 1 or 2.

公开(公告)号：US11767379B2

公开(公告)日：2023-09-26

申请号：US16976945

申请日：2019-03-01

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Yoshinori Nanba ,  Kenji Ichikawa ,  Yohei Fujimoto ,  Hirotoshi Yoshida ,  Hiroyuki Sato ,  Taketo Kato ,  Kengo Ito ,  Sumi Ishihara ,  Masahiro Higashi ,  Satoru Yoneda ,  Hirokazu Aoyama ,  Masamichi Sukegawa ,  Yosuke Kishikawa ,  Takahiro Taira ,  Chiaki Okui ,  Taku Yamanaka

IPC: C08F14/26 ,  B29C55/00 ,  C08F2/22 ,  C08F2/44 ,  C08F261/06 ,  C08F114/26 ,  C08F214/26 ,  B29K27/18

CPC classification number: C08F14/26 ,  B29C55/005 ,  C08F2/22 ,  C08F2/44 ,  C08F114/26 ,  C08F214/26 ,  C08F261/06 ,  B29K2027/18

Abstract: A method for producing a fluoropolymer, which includes polymerizing a fluoromonomer in an aqueous medium in the presence of a polymer (1), the polymer (1) including a polymerized unit derived from a monomer CX2═CY(—CZ2—O—Rf-A), wherein X is the same or different and is —H or —F; Y is —H, —F, an alkyl group, or a fluorine-containing alkyl group; Z is the same or different and is —H, —F, an alkyl group, or a fluoroalkyl group; Rf is a C1-C40 fluorine-containing alkylene group or a C—C100 fluorine-containing alkylene group and having an ether bond; and A is —COOM, —SO3M, or —OSO3M, wherein M is —H, a metal atom, —NR74, imidazolium optionally having a substituent, pyridinium optionally having a substituent, or phosphonium optionally having a substituent, wherein R7 is H or an organic group, providing that at least one of X, Y, and Z contains a fluorine atom.