FR3089978B1 - Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs - Google Patents

Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs Download PDF

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Publication number
FR3089978B1
FR3089978B1 FR1873062A FR1873062A FR3089978B1 FR 3089978 B1 FR3089978 B1 FR 3089978B1 FR 1873062 A FR1873062 A FR 1873062A FR 1873062 A FR1873062 A FR 1873062A FR 3089978 B1 FR3089978 B1 FR 3089978B1
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Prior art keywords
copolymer
group
fluorinated polymers
photoactive groups
representing
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Active
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FR1873062A
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English (en)
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FR3089978A1 (fr
Inventor
Cyril Brochon
Thibaut Soulestin
Dos Santos Fabrice Domingues
Konstantinos Kallitsis
Eric Cloutet
Georges Hadziioannou
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.)
Centre National de la Recherche Scientifique CNRS
Arkema France SA
Universite de Bordeaux
Institut Polytechnique de Bordeaux
Original Assignee
Centre National de la Recherche Scientifique CNRS
Arkema France SA
Universite de Bordeaux
Institut Polytechnique de Bordeaux
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Priority to FR1873062A priority Critical patent/FR3089978B1/fr
Application filed by Centre National de la Recherche Scientifique CNRS, Arkema France SA, Universite de Bordeaux, Institut Polytechnique de Bordeaux filed Critical Centre National de la Recherche Scientifique CNRS
Priority to TW108146050A priority patent/TW202035478A/zh
Priority to PCT/FR2019/053074 priority patent/WO2020128265A1/fr
Priority to JP2021534710A priority patent/JP2022513497A/ja
Priority to US17/414,444 priority patent/US20220098343A1/en
Priority to KR1020217022419A priority patent/KR20210104822A/ko
Priority to CN201980091709.8A priority patent/CN113423740A/zh
Priority to EP19845701.2A priority patent/EP3898713A1/fr
Publication of FR3089978A1 publication Critical patent/FR3089978A1/fr
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Publication of FR3089978B1 publication Critical patent/FR3089978B1/fr
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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
    • 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
    • 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
    • C08F214/222—Vinylidene fluoride with fluorinated vinyl ethers
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/06—Oxidation
    • 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
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/16—Homopolymers or copolymers or 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • 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
    • C09D127/22—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 modified by chemical after-treatment
    • 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
    • H10N30/01—Manufacture or treatment
    • H10N30/07—Forming of piezoelectric or electrostrictive parts or bodies on an electrical element or another base
    • H10N30/074—Forming of piezoelectric or electrostrictive parts or bodies on an electrical element or another base by depositing piezoelectric or electrostrictive layers, e.g. aerosol or screen printing
    • H10N30/077—Forming of piezoelectric or electrostrictive parts or bodies on an electrical element or another base by depositing piezoelectric or electrostrictive layers, e.g. aerosol or screen printing by liquid phase deposition
    • 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
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
    • 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
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
    • 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
    • C08J2327/00—Characterised by the use of 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; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of 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; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of 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; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/16—Homopolymers or copolymers of vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L’invention concerne un copolymère comprenant des unités issues de monomères fluorés de formule (I) : (I) CX1X2=CX3X4 dans laquelle chacun des X1, X2, X3 et X4 est indépendamment choisi parmi H, F et des groupements alkyles comprenant de 1 à 3 atomes de carbone qui sont optionnellement partiellement ou complétement fluorés, les atomes H et/ou F des monomères fluorés étant partiellement remplacés par des groupements photoactifs de formule -Y-Ar-R, dans le copolymère ; Y représentant un atome d’oxygène, ou un groupement NH, ou un atome de soufre, Ar représentant un groupement aryle, de préférence un groupement phényle, et R étant un groupement monodenté ou bidenté comprenant de 1 à 30 atomes de carbone. La présente invention concerne également un procédé de préparation de ce copolymère, une composition comprenant ce copolymère, ainsi qu’un film obtenu à partir dudit copolymère. Figure pour l’abrégé : Fig. 1.
FR1873062A 2018-12-17 2018-12-17 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs Active FR3089978B1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
FR1873062A FR3089978B1 (fr) 2018-12-17 2018-12-17 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs
PCT/FR2019/053074 WO2020128265A1 (fr) 2018-12-17 2019-12-16 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs
JP2021534710A JP2022513497A (ja) 2018-12-17 2019-12-16 光活性基を含む架橋性電気活性フルオロポリマー
US17/414,444 US20220098343A1 (en) 2018-12-17 2019-12-16 Crosslinkable electroactive fluoropolymers comprising photoactive groups
TW108146050A TW202035478A (zh) 2018-12-17 2019-12-16 包含光活性基團的可交聯電活性氟聚合物
KR1020217022419A KR20210104822A (ko) 2018-12-17 2019-12-16 광활성 기를 포함하는 가교가능한 전기활성 플루오르화된 폴리머
CN201980091709.8A CN113423740A (zh) 2018-12-17 2019-12-16 包含光活性基团的能交联的电活性氟化聚合物
EP19845701.2A EP3898713A1 (fr) 2018-12-17 2019-12-16 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1873062A FR3089978B1 (fr) 2018-12-17 2018-12-17 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs

Publications (2)

Publication Number Publication Date
FR3089978A1 FR3089978A1 (fr) 2020-06-19
FR3089978B1 true FR3089978B1 (fr) 2021-09-10

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FR1873062A Active FR3089978B1 (fr) 2018-12-17 2018-12-17 Polymères fluorés électroactifs réticulables comprenant des groupements photoactifs

Country Status (8)

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US (1) US20220098343A1 (fr)
EP (1) EP3898713A1 (fr)
JP (1) JP2022513497A (fr)
KR (1) KR20210104822A (fr)
CN (1) CN113423740A (fr)
FR (1) FR3089978B1 (fr)
TW (1) TW202035478A (fr)
WO (1) WO2020128265A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4506166B2 (ja) * 2003-12-12 2010-07-21 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子用単量体、有機エレクトロルミネッセンス素子用重合体、有機エレクトロルミネッセンス素子、表示装置及び照明装置
US20070166838A1 (en) 2003-12-22 2007-07-19 Koninklijke Philips Electronics N.V. Method for patterning a ferroelectric polymer layer
FR2896250B1 (fr) 2006-01-13 2012-08-17 Arkema Agent d'extrusion a base de pvdf
EP2065409B1 (fr) * 2006-09-28 2015-04-01 Asahi Glass Company, Limited Nouveau polymère fluoré
GB0814955D0 (en) 2008-08-18 2008-09-24 3M Innovative Properties Co Azide-containing fluoropolymers and their preparation
JP6169097B2 (ja) 2011-12-16 2017-07-26 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． フッ化ビニリデン−トリフルオロエチレンポリマーに基づく架橋性組成物
EP2791191B1 (fr) * 2011-12-16 2016-03-16 Solvay Specialty Polymers Italy S.p.A. Polymères réticulables de fluorure de vinylidène et de trifluoroéthylène
WO2015128337A1 (fr) 2014-02-28 2015-09-03 Solvay Specialty Polymers Italy S.P.A. Polymères fluorés réticulables
EP2960280A1 (fr) 2014-06-26 2015-12-30 E.T.C. S.r.l. Compositions photo-réticulables, des couches minces diélectriques structurées ayant un valeur k élevé et des appareils contentants celles-ci.

Also Published As

Publication number Publication date
JP2022513497A (ja) 2022-02-08
US20220098343A1 (en) 2022-03-31
WO2020128265A1 (fr) 2020-06-25
FR3089978A1 (fr) 2020-06-19
EP3898713A1 (fr) 2021-10-27
CN113423740A (zh) 2021-09-21
TW202035478A (zh) 2020-10-01
KR20210104822A (ko) 2021-08-25

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