WO2015063417A2 - Compositions stables de nanotubes de carbone - polymeres electrolytes - Google Patents

Compositions stables de nanotubes de carbone - polymeres electrolytes Download PDF

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Publication number
WO2015063417A2
WO2015063417A2 PCT/FR2014/052751 FR2014052751W WO2015063417A2 WO 2015063417 A2 WO2015063417 A2 WO 2015063417A2 FR 2014052751 W FR2014052751 W FR 2014052751W WO 2015063417 A2 WO2015063417 A2 WO 2015063417A2
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Prior art keywords
composition
carbon nanotubes
formula
nitroxide
radical
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Ceased
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PCT/FR2014/052751
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English (en)
French (fr)
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WO2015063417A3 (fr
Inventor
Christophe Navarro
Wiljan SMAAL
Muhammad MUMTAZ
Eric Cloutet
Cyril Brochon
Georges Hadziioannou
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Centre National de la Recherche Scientifique CNRS
Arkema France SA
Universite de Bordeaux
Institut Polytechnique de Bordeaux
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Centre National de la Recherche Scientifique CNRS
Arkema France SA
Universite de Bordeaux
Institut Polytechnique de Bordeaux
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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 KR1020167011367A priority Critical patent/KR101817453B1/ko
Priority to CN201480059287.3A priority patent/CN105916887A/zh
Priority to JP2016527164A priority patent/JP6243026B2/ja
Priority to US15/033,455 priority patent/US10199135B2/en
Priority to EP14825388.3A priority patent/EP3063183B9/fr
Priority to PL14825388T priority patent/PL3063183T3/pl
Publication of WO2015063417A2 publication Critical patent/WO2015063417A2/fr
Publication of WO2015063417A3 publication Critical patent/WO2015063417A3/fr
Anticipated expiration legal-status Critical
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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
    • C08F2/00—Processes of 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
    • C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/16—Halogens
    • C08F12/20—Fluorine
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/30—Sulfur
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/38—Esters containing sulfur
    • 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
    • C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C08K3/041—Carbon nanotubes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/24—Conductive material dispersed in non-conductive organic material the conductive material comprising carbon-silicon compounds, carbon or silicon
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/80—Constructional details
    • H10K30/81—Electrodes
    • H10K30/82—Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
    • H10K30/821—Transparent electrodes, e.g. indium tin oxide [ITO] electrodes comprising carbon nanotubes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • H10K50/828—Transparent cathodes, e.g. comprising thin metal layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/221—Carbon nanotubes
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/10—Transparent films; Clear coatings; Transparent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/81—Anodes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to stable compositions of carbon nanotubes and of electrolyte polymers, these electrolyte polymers being characterized by the presence of phosphonyl imide or sulfonyl imide or phosphoric acid functions.
  • the invention also relates to the manufacture of transparent electrodes comprising these compositions of carbon nanotubes and electrolyte polymers.
  • Carbon nanotubes are very promising materials in fields as diverse as high-performance materials as electronics. They exist in the form of single-walled and multi-walled nanotubes. Unfortunately they can hardly be used alone because they are in the form of aggregates, which in particular do not allow a light transmission when for example they are deposited on a support. However, given the size of the nanotube fibrils and their intrinsic conductivity, they are good candidates for making transparent electrodes. Electrolyte polymers have been widely used in applications as varied as lithium batteries as ionic conductors (Murata K., Izuchi S., Y. Yoshihisa Y., Electrochimica Acta 2000, 45, 1501), to produce organic transistors (A. Malti , M. Berggren, X.
  • the invention relates to a composition comprising carbon nanotubes and an electrolyte (co) -polymer, which
  • R aik or F, CF 3 , CF 3 FA - H, Li, N (R ') 4 R' - alkyl, aryl
  • the carbon nanotubes used in the invention may be mono, bi or multiwall.
  • the electrolyte (co) polymers used in the invention include entities of formula (I). They are homopolymers of an entity corresponding to formula (I), copolymers comprising at least one entity corresponding to formula (I) or block copolymers of which at least one of the blocks comprises one or more entities corresponding to the formula (I).
  • the electrolyte polymers are copolymers comprising at least one entity corresponding to formula (I)
  • the proportion of the entities corresponding to formula I represents more than 50% by weight of the copolymer, preferably more than 80% by weight, and of more preferably more than 90% by weight.
  • the remaining monomeric entities consist of any possible type of monomers capable of radical polymerization.
  • the electrolyte polymers are block copolymers, they may be diblock, triblock or multiblock copolymers, provided that unless one of the blocks comprises one or more entities corresponding to the formula (I), the other blocks comprising monomers which may be chosen from (meth) acrylates, typically acrylic or methacrylic acid, acrylamide, methacrylamide, styrene, N-vinylpyrrolidone, 4-vinylpyridine and more precisely methacrylate methyl, methacrylic acid and styrene.
  • monomers typically acrylic or methacrylic acid, acrylamide, methacrylamide, styrene, N-vinylpyrrolidone, 4-vinylpyridine and more precisely methacrylate methyl, methacrylic acid and styrene.
  • radical polymerization controlled by nitroxides or RAFT (radical addition transfer fragmentation) and more preferably the RAFT.
  • RAFT radical addition transfer fragmentation
  • the controlled radical polymerization is made from alkoxyamines derived from the stable free radical (1).
  • the radical R 1 has a molar mass greater than 15.034 g / mol.
  • the radical R 1 can be a halogen atom such as chlorine, bromine or iodine, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group such as an alkyl or phenyl radical, or an ester - COOR or an alkoxyl group -OR, or a phosphonate group -PO (OR) 2 > as soon as it has a molar mass greater than 15.0342.
  • the monovalent radical R 1 is in the ⁇ -position with respect to the nitrogen atom of the nitroxide radical.
  • the remaining valences of the carbon atom and the nitrogen atom in the formula (1) can be linked to various radicals such as a hydrogen atom, a hydrocarbon radical such as an alkyl, aryl or aryl radical. -alkyl, comprising from 1 to 10 carbon atoms. It is not excluded that the carbon atom and the nitrogen atom in the formula (1) are connected to each other via a divalent radical, so as to form a ring. Preferably, however, the remaining valencies of the carbon atom and the nitrogen atom of the formula (1) are attached to monovalent radicals.
  • the radical R 1 has a molar mass greater than 30 g / mol.
  • the radical R 1 may, for example, have a molar mass of between 40 and 450 g / mol.
  • the radical R 1 may be a radical comprising a phosphoryl group, said radical R 1 may be represented by the formula:
  • R and R which may be the same or different, may be selected from alkyl, cycloalkyl, alkoxyl, aryloxyl, aryl, aralkyloxy, perfluoroalkyl, aralkyl, and may include from 1 to 20 carbon atoms.
  • R 1 and / or R 1 may also be a halogen atom such as a chlorine or bromine or fluorine or iodine atom.
  • the radical R - may also comprise at at least one aromatic ring, as for the phenyl radical or the naphthyl radical, the latter being able to be substituted, for example by an alkyl radical comprising from 1 to 4 carbon atoms.
  • alkoxyamines derived from the following stable radicals are preferred:
  • the alkoxyamines used in controlled radical polymerization must allow good control of the sequence of monomers. Thus they do not all allow good control of certain monomers.
  • the alkoxyamines derived from TEMPO only make it possible to control a limited number of monomers, the same goes for the alkoxyamines derived from 2,2,5-tri-methyl-4-phenyl-3-azahexane-3-nitroxide. (TIPNO).
  • alkoxyamines derived from nitroxides corresponding to formula (1) particularly those derived from nitroxides corresponding to formula (2) and even more particularly those derived from N-tert-butyl-1-diethylphosphono-2, 2-dimethylpropyl nitroxide allow to expand to a large number of monomer controlled radical polymerization of these monomers.
  • alkoxyamines also influences the economic factor. The use of low temperatures will be preferred to minimize industrial difficulties.
  • Alkoxyamines derived from nitroxides corresponding to formula (1), particularly those derived from nitroxides corresponding to formula (2) and even more particularly those derived from N-tert-butyl-1-diethylphosphono-2, 2-dimethylpropyl nitroxide, will thus be preferred.
  • the controlled radical polymerization is carried out by RAFT, and more particularly by means of the RAFT agent corresponding to the following formula 2:
  • R represents an alkyl group having 1 to 22 carbon atoms, and preferably 10 to 18 carbon atoms.
  • the synthesis of block copolymers can be done by first preparing the macro - initiator polyelectrolyte block and then, secondly, the monomers of the second block can be polymerized, possibly accompanied by other steps of synthesis of other blocks taking into account. other monomers. It is also possible to prepare a macro-initiator block by any other chemistry (anionic, cationic, ring opening, polycondensation) including one or two terminations allowing subsequent priming of the monomers comprising the entities (I).
  • electrolytic polymers are usefully used to disperse single- or multi-walled carbon nanotubes in electrolyte-NTC polymer mass proportions varying from 1:10 to 10: 1 and preferably from 1:10 to 1: 1.
  • the aqueous dispersions of these compositions are stable. They can be shaped into thin film by techniques such as "spray coating” or “roll to roll” for large areas.
  • the films resulting from these preparations have good electrical conductivity, good optical transmission, good thermal stability as well as good mechanical properties. They can advantageously replace titanium and indium oxide (ITO) as a transparent electrode in the fields of optoelectronics and more particularly OLEDs (organic light emitting diodes) or even photovoltaic organic cells.
  • ITO indium oxide
  • electrolyte polymers can also be used alone, that is to say without NTC, in the manufacture of membranes useful for fuel cells, as ionic conductors or stabilizers of particles other than CNTs.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Dispersion Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Electromagnetism (AREA)
  • Graft Or Block Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Battery Electrode And Active Subsutance (AREA)
  • Polymerization Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Photovoltaic Devices (AREA)
  • Conductive Materials (AREA)
  • Non-Insulated Conductors (AREA)
  • Hybrid Cells (AREA)
PCT/FR2014/052751 2013-10-31 2014-10-29 Compositions stables de nanotubes de carbone - polymeres electrolytes Ceased WO2015063417A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020167011367A KR101817453B1 (ko) 2013-10-31 2014-10-29 탄소 나노튜브 및 중합체 전해질을 포함하는 안정한 조성물
CN201480059287.3A CN105916887A (zh) 2013-10-31 2014-10-29 包含碳纳米管和聚合物电解质的稳定组合物
JP2016527164A JP6243026B2 (ja) 2013-10-31 2014-10-29 カーボンナノチューブ−電解質ポリマーの安定な組成物
US15/033,455 US10199135B2 (en) 2013-10-31 2014-10-29 Stable compositions of carbon nanotubes-electrolytic polymers
EP14825388.3A EP3063183B9 (fr) 2013-10-31 2014-10-29 Compositions stables de nanotubes de carbone - polymeres electrolytes
PL14825388T PL3063183T3 (pl) 2013-10-31 2014-10-29 Trwałe kompozycje nanorurek węglowych i polimerów elektrolitowych

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FR13.60685 2013-10-31
FR1360685A FR3012461B1 (fr) 2013-10-31 2013-10-31 Compositions stables de nanotubes de carbone - polymeres electrolytes

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WO2015063417A2 true WO2015063417A2 (fr) 2015-05-07
WO2015063417A3 WO2015063417A3 (fr) 2015-06-25

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US (1) US10199135B2 (https=)
EP (1) EP3063183B9 (https=)
JP (1) JP6243026B2 (https=)
KR (1) KR101817453B1 (https=)
CN (1) CN105916887A (https=)
FR (1) FR3012461B1 (https=)
HU (1) HUE038006T2 (https=)
PL (1) PL3063183T3 (https=)
TW (1) TWI538950B (https=)
WO (1) WO2015063417A2 (https=)

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CN110415888B (zh) * 2019-06-14 2021-12-28 江西力能新能源科技有限公司 一种含有固态电解质的碳纳米管油系导电浆料及其制备方法

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TW201538598A (zh) 2015-10-16
US20160276057A1 (en) 2016-09-22
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EP3063183B1 (fr) 2017-10-11
HUE038006T2 (hu) 2018-09-28
KR20160064207A (ko) 2016-06-07
KR101817453B1 (ko) 2018-01-11
JP2016539217A (ja) 2016-12-15
WO2015063417A3 (fr) 2015-06-25
CN105916887A (zh) 2016-08-31
EP3063183A2 (fr) 2016-09-07
TWI538950B (zh) 2016-06-21
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