Classifications

• • 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
  • 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
  • C08F220/04—Acids; Metal salts or ammonium salts thereof
  • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• • 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
• • 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
  • C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
  • C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • C08L33/04—Homopolymers or copolymers of esters
  • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
  • C08L33/062—Copolymers with monomers not covered by C08L33/06
  • C08L33/064—Copolymers with monomers not covered by C08L33/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
• • 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
  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon 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
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/03—Powdery paints
  • C09D5/031—Powdery paints characterised by particle size or shape
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
  • H01G11/52—Separators
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M10/00—Secondary cells; Manufacture thereof
  • H01M10/05—Accumulators with non-aqueous electrolyte
  • H01M10/052—Li-accumulators
  • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
  • H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
  • H01M50/409—Separators, membranes or diaphragms characterised by the material
  • H01M50/411—Organic material
  • H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
  • H01M50/426—Fluorocarbon polymers
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M8/00—Fuel cells; Manufacture thereof
  • H01M8/02—Details
  • H01M8/0202—Collectors; Separators, e.g. bipolar separators; Interconnectors
  • H01M8/0204—Non-porous and characterised by the material
  • H01M8/0221—Organic resins; Organic polymers
• • 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
  • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
  • Y02E60/10—Energy storage using batteries

Definitions

• composition in powder form based on at least one fluoropolymer and at least one coating of
• said PI polymer comprises monomeric units carrying at least one of the following functions selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid esters, epoxy, amide, hydroxyl groups , carbonyl, mercapto, sulfide, oxazoline, phenolics, ester, ether, siloxane, sulfonic, sulfuric, phosphoric, or phosphonic; preferably monomeric units carrying at least one of the following functions selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid esters, hydroxyl, carbonyl and mercapto.
• said composition has a crystallization temperature of said composition is Te ⁇ -3.7496x + 122 with x being the mass content of comonomer Ml based on the total weight of said polymer PI. More particularly, said composition has a crystallization temperature of said composition is Te ⁇ -3.7496x + 120 with x being the mass content of comonomer Ml based on the total weight of said polymer PI. Preferably, said composition has a crystallization temperature of said composition is Te ⁇ -3.7496x + 118 with x being the mass content of comonomer Ml based on the total weight of said polymer PI.
• Said PI polymer can also be designated by the abbreviation PVDF.
• the PI polymer is a copolymer of vinylidene fluoride (VDF) and hexafluoropropylene (HFP)) (P(VDF-HFP)), having a weight percentage of hexafluoropropylene monomer units of 20 to 30%, advantageously 20 to 25% by weight relative to the weight of said PI polymer.
• the PI polymer is a copolymer of vinylidene fluoride and tetrafluoroethylene (TFE).
• the PI polymer is a VDF-TFE-HFP terpolymer.
• the PI polymer is a VDF-TrFE-TFE terpolymer (TrFE being trifluoroethylene).
• the mass content of VDF is at least 10%, the comonomers being present in variable proportions.
• the function is introduced by a chemical reaction which may be grafting, or a copolymerization of the vinylidene fluoride (VDF) monomer with a monomer bearing at least one of said functional groups and a vinyl function capable of copolymerizing with the VDF monomer, according to techniques well known to those skilled in the art, or by adsorption of a polymer carrying the functionality in the PI polymer.
• said monomeric units come from a polymer comprising these and having a molar mass of less than 100,000 g/mol, preferably less than 50,000 g/mol, in particular less than 20,000 g/mol. The latter can be grafted onto or adsorbed by said PI polymer.
• the functional group carries a carboxylic acid function which is a (meth)acrylic acid type group chosen from acrylic acid, methacrylic acid, hydroxyethyl(meth)acrylate, hydroxypropyl(meth) acrylate and hydroxyethylhexyl(meth)acrylate.
• said PI polymer may comprise monomeric units originating from a monomer selected from the group consisting of acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate and hydroxyethylhexyl methacrylate.
• the units carrying the carboxylic acid function further comprise a heteroatom chosen from oxygen, sulfur, nitrogen and phosphorus.
• the functionality is introduced via the transfer agent used during the synthesis process.
• the transfer agent is a polymer with a molar mass less than or equal to 20,000 g/mol and carrying functional groups chosen from the groups: carboxylic acid, carboxylic acid anhydride, carboxylic acid esters, epoxy groups (such as glycidyl), amide, hydroxyl, carbonyl, mercapto, sulfide, oxazoline, phenolics, ester, ether, siloxane, sulfonic, sulfuric, phosphoric, phosphonic; preferably carboxylic acid, carboxylic acid anhydride, carboxylic acid esters.
• An example of such a transfer agent are acrylic acid oligomers.
• the transfer agent can be grafted onto or adsorbed by the PI polymer.
• the content of functional groups in said PI polymer is at least 0.01 molar%, preferably at least 0.1 molar%, and at most 15 molar%, preferably at most 10 molar%.
• the PI polymer preferably has a high molecular weight.
• high molecular weight as used here, is meant a PI polymer having a melt viscosity greater than 100 Pa.s, preferably greater than 500 Pa.s, more preferably greater than 1000 Pa.s, according to ASTM D-3835 method measured at 232°C and 100 sec-1.
• the PI polymer carrying functional groups can crosslink either by self-condensation of its functional groups, or by reaction with a catalyst and/or a crosslinking agent, such as melamine resins, epoxy resins and similar, as well as known low molecular weight crosslinking agents such as di- or higher polyisocyanates, polyaziridines, polycarbodiimides, polyoxazolines, dialdehydes such as glyoxal, acetoacetates, malonates, acetals, thiols and di- and trifunctional acrylates, cycloaliphatic epoxy molecules, organosilanes such as epoxysilanes and amino silanes, carbamates, diamines and triamines, inorganic chelating agents such as certain zinc and zirconium salts, titaniums, glycouriles and other aminoplasts.
• a catalyst and/or a crosslinking agent such as melamine resins, epoxy resins and similar, as well as known low molecular weight crosslink
• the PI polymer comprises a crosslinking agent chosen from the group consisting of isocyanates, diamines, adipic acid, dihydrazides and their combinations.
• the homopolymer PVDF and VDF copolymers are composed of bio-based VDF.
• biosourced means “from biomass”. This improves the ecological footprint of the separator.
• the biosourced VDF can be characterized by a renewable carbon content, that is to say carbon of natural origin and coming from a biomaterial or biomass, of at least 1 atomic % as determined by the carbon content. 14C according to standard NF EN 16640.
• renewable carbon indicates that the carbon is of natural origin and comes from a biomaterial (or biomass), as indicated below.
• the bio-carbon content of the VDF can be greater than 5%, preferably greater than 10%, preferably greater than 25%, preferably greater than or equal to 33%, preferably greater than 50% , preferably greater than or equal to 66%, preferably greater than 75%, preferably greater than 90%, preferably greater than 95%, preferably greater than 98%, preferably greater than 99%, advantageously equal to 100% .
• they are prepared by an emulsion polymerization process in the absence of fluorinated surfactant.
• Polymerization of vinylidene fluoride preferably results in a latex generally having a solids content of 10 to 60% by weight, preferably 10 to 50%, and having a weight average particle size of less than 1 micrometer, preferably less than 1000 nm, preferably less than 800 nm, and more preferably less than 600 nm.
• the weight average size of the particles is generally at least 20 nm, preferably at least 50 nm, and advantageously the average size is in the range of 100 to 400 nm.
• the polymer particles can form agglomerates whose weight average size is 1 to 30 micrometers, and preferably 2 to 20 micrometers. Agglomerates may break into discrete particles during formulation and application to a substrate.
• Said heterocycle may be saturated or unsaturated or aromatic.
• Said heterocycle can be monocyclic or bicyclic.
• Said heterocycle may be a pyrrole, pyrrolidine, pyridine, piperidine, pyrimidine, pyrazine, 1,4-dihydropyridine, indole, oxindole, isatin, quinoline, isoquinoline, quinazoline, imidazoline, pyrazolidine, 2-pyrrolidone, deltalactam, succinimide, 2- ring. imidazolidinone, 4-imidazolidinone.
• Said heterocycle may be substituted by one or more C1-C5 alkyl groups.
• the Ci-Cis alkyl is optionally substituted by said heterocycle.
• the latter can be linked to the alkyl chain by the nitrogen atom or any other atoms forming the heterocycle.
• the heterocycle is 2-pyrrolidone, delta-lactam, succinimide, 2-imidazolidinone, 4-imidazolidinone.
• R is selected from the group consisting of -NHC(CH3)2CH2C(O)CH3
• the heterocycle is as defined above, in particular the heterocycle is 2-pyrrolidone, deltalactam, succinimide, 2-imidazolidinone, 4-imidazolidinone.
• alkyl (meth)acrylate includes alkyl acrylates and alkyl methacrylates.
• the substituent R' is selected from the group consisting of H, methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, n-dodecyl, amyl, isoamyl, hexyl, 2-ethylhexyl, lauryl, n-octyl, hydroxyethyl, hydroxybutyl, hydroxypropyl, ethyl substituted with a ureido group, hydroxy ethyl, hydroxy propyl, hydroxy butyl.
• the alkyl (meth)acrylate can be methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, t -butyl, n-dodecyl acrylate, amyl acrylate, isoamyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, diacetone acrylamide, lauryl, n-octyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, acrylic acid, methacrylic acid, acrylic acid methyl methacrylate, ureido methacrylate and mixtures thereof.
• step b) the polymer PI and said at least one monomer M2 are brought into contact for a sufficiently long period to allow said monomer M2 to impregnate the particles of the polymer PI before carrying out the polymerization of that -this.
• This contact duration is at least 5 minutes, preferably 10 minutes, in particular at least 15 minutes, more particularly at least 20 minutes.
• the monomer M2 is added before the initiator. This makes it possible to arrive at the preferred compositions of the present invention.
• Said process also comprises a step c) during which said at least one monomer M2 is polymerized.
• Step c) is preferably carried out in the presence of water.
• Step c) of polymerization of said at least monomer M2 is carried out in the presence of an initiator.
• Said initiator may be a persulfate type initiator such as sodium persulfate, potassium persulfate, barium persulfate, or ammonium persulfate; alkali metal bisulfites; peroxides such as benzoyl peroxide, or dicumyl peroxide; hydroperoxides such as methyl hydroperoxide or tert-butyl hydroperoxide; acyloins such as benzoin; peracetates such as methyl peracetate, tert-butyl peracetate; perbenzoates such as tert-butyl perbenzoate; peroxalates such as dimethyl peroxalate or di(tert-butyl) peroxalate; azo-type compounds such as azo-bisisobutyronitrile or dimethyl azo-bis-isobutyrate.
• the initiator is preferably added in a content of 0.005 to 1% by weight based on the weight of said at least one monomer
• step c) is implemented in the presence of a chain transfer agent.
• the chain transfer agent may be an oxygenated compound such as an alcohol, carbonate, ketone, ester, ether; a halocarbon or hydrohalocarbon compound such as chlorocarbons, hydrochlorocarbons, chlorofluorocarbons, hydrochlorofluorocarbons; ethane or propane.
• Step c) can be carried out at a temperature of 20°C to 160°C.
• Step c) can be carried out at a pressure of 280 to 20,000 kPa.
• Said composition obtained in step c) is preferably obtained in the form of a latex, that is to say in the form of a dispersion in an aqueous medium.
• said composition is an aqueous dispersion obtained by emulsion polymerization of 5 to 100, preferably 5-95 parts by weight of a mixture of monomers having at least one monomer M2 chosen from the group consisting of alkyl acrylates including alkyl groups have 1-18 carbon atoms and alkyl methacrylates whose alkyl groups have 1-18 carbon atoms and optionally an ethylenically unsaturated compound copolymerizable with alkyl acrylates and alkyl methacrylates, in an aqueous medium in the presence of 100 parts by weight of particles of a PI polymer as defined above.
• the particles of the PI polymer serve as seeds for the polymerization of the M2 monomers.
• PI polymer particles can be added in any state to the polymerization system, as long as they are dispersed in an aqueous medium in particle form.
• As the PI polymer is generally produced as an aqueous dispersion, it is convenient for the as-produced aqueous dispersion to be used as seed particles.
• the measurement is carried out by laser diffraction on a powder with a focal length of 100mm.
• the polymer chains PI and P2 are entangled to form an interpenetrating polymer network (IPN) as defined by IUPAC; which is different from a mixture of preformed polymers.
• IPN interpenetrating polymer network
• the polymer chains PI and P2 are entangled to form a sequential interpenetrating polymer network as defined by IUPAC.
• the mass ratio P1/P2 preferably varies from 95/5 to 5/95, in particular from 95/5 to 40/60, preferably from 90/10 to 50/50.
• the PI polymer is a copolymer of vinylidene fluoride and at least one comonomer compatible therewith as described above.
• the PI polymer may be a copolymer of vinylidene fluoride (VDF) and hexafluoropropylene (HFP) (P(VDF-HFP)), having a weight percentage of hexafluoropropylene monomer units of 2 to 30 %, advantageously from 2 to 25%, preferably from 2 to 20% by weight relative to the weight of the PI polymer; or a copolymer of vinylidene fluoride and tetrafluoroethylene (TFE); or a copolymer of vinylidene fluoride and chlorotrifluoroethylene (CTFE); or a VDF-TFE-HFP terpolymer as described above.
• VDF vinylidene fluoride
• HFP hexafluoropropylene
• CTFE chlorotrifluoroethylene
• the separator coating according to the invention presents an excellent compromise of properties for the intended application: good dry adhesion and good resistance to electrolyte solvent(s) characterized by good retained integrity.
• the comparative examples with a crystallization temperature higher than the value defined by the equation -3.7496x + 130 show at least one very unfavorable property.

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• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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• 2022
  • 2022-09-09 FR FR2209040A patent/FR3139572A1/fr active Pending
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