WO2013160621A1 - Copolymerisation radicalaire controlee a partir de trifluoroethylene - Google Patents

Copolymerisation radicalaire controlee a partir de trifluoroethylene Download PDF

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Publication number
WO2013160621A1
WO2013160621A1 PCT/FR2013/050920 FR2013050920W WO2013160621A1 WO 2013160621 A1 WO2013160621 A1 WO 2013160621A1 FR 2013050920 W FR2013050920 W FR 2013050920W WO 2013160621 A1 WO2013160621 A1 WO 2013160621A1
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WO
WIPO (PCT)
Prior art keywords
units
copolymer
trifluoroethylene
block
vinylidene fluoride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/FR2013/050920
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English (en)
French (fr)
Inventor
Bruno Ameduri
Ali Alaaeddine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Ecole Nationale Superieure de Chimie de Montpellier ENSCM
Ecole National Superieure dArts et Metiers ENSAM
Original Assignee
Arkema France SA
Ecole Nationale Superieure de Chimie de Montpellier ENSCM
Ecole National Superieure dArts et Metiers ENSAM
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Arkema France SA, Ecole Nationale Superieure de Chimie de Montpellier ENSCM, Ecole National Superieure dArts et Metiers ENSAM filed Critical Arkema France SA
Priority to US14/396,528 priority Critical patent/US9708419B2/en
Priority to EP13723870.5A priority patent/EP2841474A1/fr
Priority to CN201380033739.6A priority patent/CN104540861B/zh
Priority to KR1020147033297A priority patent/KR20150006865A/ko
Priority to JP2015507585A priority patent/JP6212542B2/ja
Publication of WO2013160621A1 publication Critical patent/WO2013160621A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/182—Monomers containing fluorine not covered by the groups C08F214/20 - C08F214/28
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/22—Vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C09D127/16—Homopolymers or copolymers of vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10N15/00—Thermoelectric devices without a junction of dissimilar materials; Thermomagnetic devices, e.g. using the Nernst-Ettingshausen effect
    • H10N15/10—Thermoelectric devices using thermal change of the dielectric constant, e.g. working above and below the Curie point
    • H10N15/15—Thermoelectric active materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10N30/00—Piezoelectric or electrostrictive devices
    • H10N30/80—Constructional details
    • H10N30/85—Piezoelectric or electrostrictive active materials
    • H10N30/857—Macromolecular compositions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2438/00—Living radical polymerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2438/00—Living radical polymerisation
    • C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]

Definitions

  • the additional monomer or monomers are chosen from fluorinated monomers, and preferably from 2,3,3,3-tetrafluoropropene, vinyl fluoride, 2-chloro-1,1-difluoroethylene, 2-bromo-1,1-difluoroethylene, hexafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, 1,1,1,3-tetrafluoropropene, 3, 3,3-trifluoro-2-bromoropropene, 1H-pentafluoropropene, 2H-pentafluoropropene, perfluoromethylvinylether, perfluoroethylvinylether, perfluoropropylvinylether, ⁇ -trifluoromethacrylic acid and its derivatives; or are chosen from hydrogenated monomers, and preferably from vinyl acetate, N-vinyl pyrrolidone,
  • the chain transfer agent is a mono-iodinated compound which is a 1-iodofluoroalkane, and which is preferably a compound of formula RF- (CH 2 CF 2 ) nl, in which n is a whole number ranging from 1 to 500, and R F represents a perfluorocarbon group, more particularly preferably selected from the groups CF 3 , C 2 F 5 , C 3 F 7 and C m F 2m + 1, m being an even integer ranging from 4 to 20.
  • the block copolymer comprises:
  • the invention also relates to a pyroelectric device comprising a film as described above.
  • Figure 6 shows a 19 F NMR spectrum in deuterated acetone of the same block copolymer.
  • This copolymerization is carried out as previously in a 100 mL HC-276 reactor by introducing respectively i-butyl peroxypivalate (0.904 g, 5.2 mmol), 2-mercaptopropionic acid methyl ester O-ethyl dithiocarbonate (Rhodixan; 0.81 g, 3.9 mmol) and 50 mL of 1,1,1,3,3-pentafluorobutane.
  • the reactor is then cooled to -60 ° C. (acetone / liquid nitrogen mixture), then TrFE (12.81 g, 0.156 mol) followed by VDF (15 g, 0.234 mmol) are then successively introduced therein.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Graft Or Block Polymers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
PCT/FR2013/050920 2012-04-26 2013-04-25 Copolymerisation radicalaire controlee a partir de trifluoroethylene Ceased WO2013160621A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US14/396,528 US9708419B2 (en) 2012-04-26 2013-04-25 Controlled free-radical copolymerization of trifluoroethylene
EP13723870.5A EP2841474A1 (fr) 2012-04-26 2013-04-25 Copolymerisation radicalaire controlee a partir de trifluoroethylene
CN201380033739.6A CN104540861B (zh) 2012-04-26 2013-04-25 三氟乙烯的受控自由基共聚合反应
KR1020147033297A KR20150006865A (ko) 2012-04-26 2013-04-25 트리플루오로에틸렌의 제어된 자유―라디칼 공중합
JP2015507585A JP6212542B2 (ja) 2012-04-26 2013-04-25 トリフルオロエチレンの制御フリーラジカル共重合

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1253838 2012-04-26
FR1253838A FR2989972B1 (fr) 2012-04-26 2012-04-26 Copolymerisation radicalaire controlee a partir de trifluoroethylene

Publications (1)

Publication Number Publication Date
WO2013160621A1 true WO2013160621A1 (fr) 2013-10-31

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PCT/FR2013/050920 Ceased WO2013160621A1 (fr) 2012-04-26 2013-04-25 Copolymerisation radicalaire controlee a partir de trifluoroethylene

Country Status (7)

Country Link
US (1) US9708419B2 (enExample)
EP (1) EP2841474A1 (enExample)
JP (1) JP6212542B2 (enExample)
KR (1) KR20150006865A (enExample)
CN (1) CN104540861B (enExample)
FR (1) FR2989972B1 (enExample)
WO (1) WO2013160621A1 (enExample)

Cited By (4)

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WO2015173194A1 (en) * 2014-05-12 2015-11-19 Solvay Specialty Polymers Italy S.P.A. Fluoroelastomers
FR3041348A1 (fr) * 2015-09-23 2017-03-24 Arkema France Terpolymeres du fluorure de vinylidene, du trifluoroethylene et du 1,3,3,3-tetrafluoropropene
WO2017068276A1 (fr) * 2015-10-19 2017-04-27 Arkema France Copolymeres fluores fonctionnalises
WO2023012208A1 (fr) 2021-08-04 2023-02-09 Piezomedic Dispositif et systeme d'echange d'energie et/ou de donnees, en particulier a des fins de localisation, avec au moins un implant et/ou au moins un organe dans un corps humain ou animal et/ou un appareil externe au corps, via des transducteurs piezoelectriques et/ou capacitifs.

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FR3004185B1 (fr) * 2013-04-03 2017-10-13 Arkema France Terpolymeres contenant du fluorure de vinylidene et du trifluoroethylene
US10377843B2 (en) * 2014-05-12 2019-08-13 Solvay Specialty Polymers Italy S.P.A. Method for the controlled polymerization of fluoromonomers
WO2016149238A1 (en) * 2015-03-16 2016-09-22 Arkema Inc. Modified fluoropolymers
JP6722754B2 (ja) * 2015-08-05 2020-07-15 ゼロックス コーポレイションＸｅｒｏｘ Ｃｏｒｐｏｒａｔｉｏｎ ＰＶＤＦ−ＴｒＦＥ共重合体の末端基の交換法
EP3594250B1 (en) 2017-03-09 2025-06-25 AGC Inc. Method for producing polymer
FR3065217B1 (fr) * 2017-04-14 2020-02-28 Arkema France Compositions reticulables a base de copolymeres fluores electroactifs
EP3639307B1 (en) 2017-06-16 2022-03-23 Carrier Corporation Electrocaloric heat transfer system comprising copolymers
MX2020003337A (es) * 2017-09-27 2020-10-28 Arkema Inc Copolimeros de olefinas halogenadas y co-monomeros halogenados.
FR3071500B1 (fr) * 2017-09-27 2020-05-15 Arkema France Synthese de latex de poly(fluorure de vinylidene) sans tensioactif par polymerisation en emulsion raft
EP3898717B1 (en) * 2018-12-20 2023-09-06 Solvay Specialty Polymers Italy S.p.A. Vinylidene fluoride polymer dispersion
CN109851705A (zh) * 2019-03-20 2019-06-07 济南大学 一种一锅法制备分子量可控的四氟乙烯共聚物的方法
CN118027319A (zh) * 2019-05-08 2024-05-14 大金工业株式会社 含氟聚合物
WO2021045209A1 (ja) * 2019-09-04 2021-03-11 ダイキン工業株式会社 含フッ素共重合体
EP4190828A4 (en) * 2020-07-30 2024-10-30 Daikin Industries, Ltd. METHOD FOR PRODUCING AN AQUEOUS DISPERSION OF FLUORINE-CONTAINING ELASTOMER, FLUORINE-CONTAINING ELASTOMER AND AQUEOUS DISPERSION
JP7137106B2 (ja) * 2020-09-03 2022-09-14 ダイキン工業株式会社 硬化性組成物
CN112226119A (zh) * 2020-09-19 2021-01-15 复旦大学 一种发光防水聚合物涂层的制备方法
KR102526902B1 (ko) 2021-07-02 2023-04-28 정세진 고내열 유연성 정온도계수 자율제어형 히팅케이블 제조방법
US20250059308A1 (en) * 2021-12-17 2025-02-20 Solvay Specialty Polymers Italy S.P.A. Method for the emulsion polymerization of fluoromonomer
WO2025053275A1 (ja) * 2023-09-06 2025-03-13 ダイキン工業株式会社 ポリマーおよび成形品

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Publication number Priority date Publication date Assignee Title
WO2015173194A1 (en) * 2014-05-12 2015-11-19 Solvay Specialty Polymers Italy S.P.A. Fluoroelastomers
FR3041348A1 (fr) * 2015-09-23 2017-03-24 Arkema France Terpolymeres du fluorure de vinylidene, du trifluoroethylene et du 1,3,3,3-tetrafluoropropene
WO2017051109A1 (fr) * 2015-09-23 2017-03-30 Arkema France Terpolymeres du fluorure de vinylidene, du trifluoroethylene et du 1,3,3,3-tetrafluoropropene
WO2017068276A1 (fr) * 2015-10-19 2017-04-27 Arkema France Copolymeres fluores fonctionnalises
WO2023012208A1 (fr) 2021-08-04 2023-02-09 Piezomedic Dispositif et systeme d'echange d'energie et/ou de donnees, en particulier a des fins de localisation, avec au moins un implant et/ou au moins un organe dans un corps humain ou animal et/ou un appareil externe au corps, via des transducteurs piezoelectriques et/ou capacitifs.
FR3125957A1 (fr) 2021-08-04 2023-02-10 Piezomedic Dispositif et système de localisation d’un implant ou d’un organe dans un corps humain ou animal, par émission-réception de signaux ultrasons via des transducteurs piézoélectriques et/ou capacitifs

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FR2989972A1 (fr) 2013-11-01
US9708419B2 (en) 2017-07-18
EP2841474A1 (fr) 2015-03-04
JP2015514854A (ja) 2015-05-21
US20150119523A1 (en) 2015-04-30
FR2989972B1 (fr) 2015-03-27
CN104540861A (zh) 2015-04-22
JP6212542B2 (ja) 2017-10-11
KR20150006865A (ko) 2015-01-19
CN104540861B (zh) 2016-08-24

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