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
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
  • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
  • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
  • C08J3/095—Oxygen containing compounds
• • 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
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
  • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
  • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
  • C08J3/096—Nitrogen containing compounds
• • 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
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/20—Diluents or solvents
• • 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
  • C09D9/00—Chemical paint or ink removers
  • C09D9/005—Chemical paint or ink removers containing organic solvents
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
  • C11D7/5013—Organic solvents containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
  • C11D7/5022—Organic solvents containing oxygen
• • 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
  • H01M4/00—Electrodes
  • H01M4/02—Electrodes composed of, or comprising, active material
  • H01M4/04—Processes of manufacture in general
  • H01M4/0402—Methods of deposition of the material
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M4/00—Electrodes
  • H01M4/02—Electrodes composed of, or comprising, active material
  • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
  • H01M4/621—Binders
  • H01M4/622—Binders being polymers
  • H01M4/623—Binders being polymers fluorinated polymers
• • 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
  • C08L2201/00—Properties
  • C08L2201/56—Non-aqueous solutions or dispersions
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M4/00—Electrodes
  • H01M4/02—Electrodes composed of, or comprising, active material
  • H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
• • 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

• the invention relates to solutions of solutions of polyvinylidene fluoride (PVDF) or copolymers of 1,1-difluoroethylene in a solvent which comprises N-formylmorpholine (NFM), N-acetylmorpholine (N-formylmorpholine). NAM) or mixtures thereof and additionally contains a co-solvent selected from alkylene carbonate, mono-, di- or polyalkylene glycol dialkyl ethers or mixtures thereof.
• PVDF polyvinylidene fluoride
• PVDF Due to its thermal and chemical resistance, PVDF is used, for example, for coating pipes or for producing membranes and gaskets.
• PVDF is used as a binder. It can also be used as a separator membrane in batteries and accumulators, for coating electrical measuring probes or photovoltaic units.
• PVDF is usually either melt processed or dissolved in a solvent and applied as a solution to the desired surface or formed into the desired shape, e.g. by spinning, film casting, knife coating, calendering, casting or injection molding. During or after the coating process or the production of the moldings, the solvent is removed.
• the solvent used must therefore meet special requirements: It must solve PVDF as well as possible. At the same time, in the subsequent removal of the solvent as homogeneous as possible coatings or moldings with a uniform surface and good mechanical properties.
• US 31 10692 discloses the use of NFM or NAM as a solvent for polyvinyl fluoride.
• Polyvinyl fluoride is the polymer of vinyl fluoride (C2H3F). PVDF, however, is not or only partially soluble in pure NFM.
• Solvent mixtures of NFM and a different aprotic solvent are mentioned in WO 201 1/147822 as a solvent for pesticides.
• the solvent preferably contains at least 20% by weight, more preferably at least 30% by weight, very preferably at least 50% by weight, of NFM, NAM or mixtures thereof.
• the solvent contains NFM, preferably it contains NFM in the amounts indicated above.
• the co-solvent is alkylene carbonate, mono-, di- or polyalkylene glycol dialkyl ethers or mixtures thereof.
• the mono-, di- or Polyalkylenglycoldiethern are in particular at normal conditions (20 ° C, 1 bar) liquid compounds.
• the mono-, di- or polyalkylene glycol diethers are preferably those of the formula I.
• R 1 and R 2 independently of one another represent a C 1 - to C 4 -alkyl group
• R 3 and R 4 independently represent an ethylene, propylene or butylene group and n is an integer between 0 and 4.
• R 1 and R 2 are identical.
• R 1 and R 2 are a methyl group.
• R 3 and R 4 are identical. Particularly preferably, R 3 and R 4 are a propylene group.
• N is preferably 1 or 2, more preferably n is 1, that is to say particularly preferred are the dialkylene glycol dialkyl ethers of the formula I.
• a particularly preferred dialkylene glycol dialkyl ether is dipropylene glycol dimethyl ether (R 1 and R 2 are both methyl, R 3 and R 4 are both propylene and n is 1).
• Dipropylene glycol dimethyl ethers may exist in various isomeric forms or as a mixture of isomers.
• proglyme dipropylene glycol dimethyl ether
• proglyme is often a mixture of three regioisomers which differ in the position of the propylene groups:
• dipropylene glycol dimethyl ether is often a mixture of stereoisomers (enantiomers and diastereomers).
• the co-solvent is preferably 1,2-propylene carbonate or dialkylene glycol dialkyl ethers of the formula I.
• the co-solvent is particularly preferably 1,2-propylene carbonate or dipropylene glycol dimethyl ether.
• the co-solvent is dipropylene glycol dimethyl ether.
• the solvent mixture contains at least 5% by weight, more preferably at least 10% by weight, of the co-solvent in addition to the above amounts or preferred amounts of NFM or NAM.
• the solvent may additionally contain further solvents.
• solvents As other solvents called its hydrophobic solvent such.
• the other solvents may also be hydrophilic, protic compounds, for example water or alcohols, such as methanol, ethanol, propanol or butanol, or hydrophilic, apoptotic compounds, for example ketones, such as acetone, cyclohexanone, butan-2-one, (methyl Ethyl ketone (MEK), methyl isobutyl ketone (MIBK) or isophorone, ethers such as tetrahydrofuran, dioxane, diethyl ether, tert-butyl methyl ether, esters such as the methyl, ethyl, propyl or butyl ester of formic acid, vinegar -, succinic, glutaric,
• NFM 5 to 95 wt.% NFM, NAM or mixtures thereof, in particular NFM, and
• solvent mixtures which consist of
• Very particularly preferred solvent mixtures are suitable which from 45 to 80 wt.% NFM, NAM or mixtures thereof, in particular NFM, and
• the solvent mixture contains no further solvents;
• the solvent mixture consists exclusively of NFM, NAM or mixtures thereof and the co-solvent.
• the solvent mixture consists exclusively of NFM and dipropylene glycol dimethyl ether (proglyme).
• the solutions contain PVDF or copolymers of 1, 1 difluoroethylene, preferably copolymers, which consist of at least 70 wt.% Of 1, 1 -difluoroethylene.
• PVDF consists exclusively of 1, 1-difluoroethylene.
• PVDF and the above copolymers may, for. B. have a number average molecular weight Mn of 10,000 to 3,000,000, in particular from 50,000 to 2,000,000 g / mol.
• Mn number average molecular weight
• the molecule large-weight can be determined by gel permeation chromatography (GPC) (eluent: dimethylacetamide, standard: polystyrene).
• the solutions preferably contain PVDF or copolymers which consist of at least 90% by weight, more preferably at least 95% by weight, of 1,1-difluoroethylene.
• the solutions contain PVDF.
• Such monomers may be hydrophilic monomers or non-hydrophilic monomers.
• the monomers may be fluorine-free or fluorine-containing. Fluorine-containing monomers are, for example, mono-, tri- or tetrafluoroethylene.
• Hydrophilic monomers are in particular those having an acid group, which may optionally also be in the form of a salt, having a hydroxyl group, a nitrile group, an amino group which may optionally also be in the form of a salt, an amide group, a lactam group or an epoxy group.
• Monomers having an acid group are e.g., those having a carboxylic acid, sulfonic acid or phosphonic acid group, wherein the above acid groups may also be present as a salt.
• Salts with an inorganic cation such as alkali cations or an ammonium cation or organic cations, e.g. B. by organic groups substituted ammonium cations.
• Monomers having a hydroxyl group are e.g. Hydroxy-alkyl (meth) acrylates, in particular hydroxy-C 2 -C 8 -alkyl (meth) acrylates such as hydroxyethyl (meth) acrylate, hydroxybutyl (meth) acrylate or hydroxy-2-ethylhexyl (meth) acrylate.
• Monomers having a nitrile group are e.g. Acrylonitrile or methacrylonitrile.
• Monomers having an amino group are z. As substituted by an amino group alkyl (meth) - acrylates.
• Monomers having an amide group are e.g. As acrylamide or methacrylamide.
• Monomers having a lactam group are e.g. For example, N-vinylpyrrolidone, N-vinylimidazole or N-vinyl caprolactam.
• Monomers having an epoxy group are e.g. B. (meth) glycidyl acrylate.
• Non-hydrophilic monomers are, for example, monomers having an acrylic or methacrylic group, e.g. B. C1 to C8 alkyl (meth) acrylates, such as methyl (meth) acrylate, ethyl (meth) acrylate,
• the solutions contain 1 to 60 wt.%, Particularly preferably 1 to 50 wt.%, Most preferably 1 to 40 wt.% PVDF or copolymers of 1, 1 difluoroethylene, based on the total weight of the solutions.
• the solutions contain at least 5 wt.%, In particular at least 10 wt.% Very particularly preferably at least 20 wt.% PVDF or copolymers of 1, 1 difluoroethylene based on the total weight of the solutions.
• PVDF or Copoiymeren can be solved in a simple manner, optionally supported by temperature increase in the solvent.
• PVDF or the copolymers may initially also be present as a solution in another solvent, for example in N-methylpyrrolidone, and then converted by a solvent exchange into the above solution according to the invention.
• the temperature of the solvent or of the solvent mixture for example, can be determined. be increased to 30 to 175 ° C, in particular to 40 to 165 ° C, particularly preferably to 50 to 160 ° C.
• PVDF or the copolymers may also be prepared directly in the above solvent, for example by radical polymerization of the 1,1-difluoroethylene and optionally further monomers.
• the solutions according to the invention may contain, in addition to the solvent and the PVDF or the copolymers, further constituents.
• further constituents include, in addition to the solvent and the PVDF or the copolymers, further constituents.
• initiators when PVDF or the copolymers were prepared in the solvent, and stabilizers, such as antioxidants, UV inhibitors, emulsifiers, flow control agents or other additives, which are helpful or necessary for the intended use of the solution.
• the proportion by weight of the further components may, for. B. 0 to 40 wt.%, In particular 0 to 20 wt.% Or 0 to 10 wt.% Or 0 to 5 wt.% Be.
• the solutions can be used for the production of coatings or moldings.
• Shaped bodies are in addition to piping, hoses, plates, cables, fittings, flanges see, fittings, seals z.
• coatings powders, fibers, films, films and membranes.
• they are also suitable for the production of coatings on electrodes, in particular electrodes, which are used in lithium accumulators.
• the solutions can be introduced into a hollow body of the desired shape or coated onto the desired surface.
• the solvent can easily, e.g. by increasing the temperature, be removed. In this case, the desired shaped body or the desired coating is formed.
• the solvent according to the invention dissolves PVDF and the copolymers of 1,1-difluoroethylene very well. Stable solutions can be obtained. In particular, the solutions of 15 to 100 ° C are stable and the PVDF or copolymer remains dissolved in this temperature range. When using the solutions according to the invention very homogeneous coatings and moldings are obtained with good mechanical properties.
• PVDF Polyvinylidene fluoride
• the solvent mixture was heated to 100 to 120 ° C for this purpose.
• PVDF was added stepwise in amounts of 7.5 grams to the solvent mixture and stirred at 100 to 120 ° C after each step until everything was dissolved.
• PVDF Polyvinylidene fluoride
• the solvent mixture was heated to 100 to 120 ° C for this purpose.
• PVDF was added stepwise in amounts of 7.5 grams to the solvent mixture and stirred at 100 to 120 ° C after each step until everything was dissolved.
• the solvent used was only NFM. As described above, initially 7.5 grams of PVDF were added. This amount of PVDF could not or hardly be dissolved in pure NFM even when heated to 100 to 120 ° C. Also, heating to the boiling point of the solvent did not result in a solution of the added PVDF.

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• 2015
  • 2015-06-12 JP JP2016575213A patent/JP2017520661A/ja not_active Withdrawn
  • 2015-06-12 CN CN201580034082.4A patent/CN106661233A/zh not_active Withdrawn
  • 2015-06-12 US US15/319,909 patent/US20170130045A1/en not_active Abandoned
  • 2015-06-12 WO PCT/EP2015/063137 patent/WO2015197380A1/de active Application Filing
  • 2015-06-12 EP EP15728012.4A patent/EP3161079A1/de not_active Withdrawn

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