WO2018043807A1 - Liquide dispersé de pedot/pss, composition de revêtement antistatique photodurcissable préparée à partir du liquide dispersé et récipient de collecte de poussière comprenant la composition de revêtement - Google Patents

Liquide dispersé de pedot/pss, composition de revêtement antistatique photodurcissable préparée à partir du liquide dispersé et récipient de collecte de poussière comprenant la composition de revêtement Download PDF

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WO2018043807A1
WO2018043807A1 PCT/KR2016/012275 KR2016012275W WO2018043807A1 WO 2018043807 A1 WO2018043807 A1 WO 2018043807A1 KR 2016012275 W KR2016012275 W KR 2016012275W WO 2018043807 A1 WO2018043807 A1 WO 2018043807A1
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dispersion
pedot
pss
poly
ethylenedioxythiophene
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PCT/KR2016/012275
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English (en)
Korean (ko)
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김인선
임성택
염은희
이승조
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주식회사 포리스
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    • 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
    • C08J3/11—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids from solid polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • 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
    • C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C09D5/02—Emulsion paints including aerosols
    • 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
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/027—Dispersing agents
    • 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
    • C09D5/24—Electrically-conducting paints

Definitions

  • the present invention is a dust collector including a PEDOT / PSS dispersion, a photocurable antistatic coating composition prepared from the dispersion, and an antistatic coating film formed using the coating composition, wherein the poly (3,4-ethylene in the form of a solid powder Deoxythiophene) -polystyrenesulfonic acid (PEDOT / PSS), can be used to form an antistatic coating film having a high light transmittance and low surface resistance, chemically stable PEDOT / PSS dispersion, photocurable prepared with the dispersion It relates to a dust collecting container including an antistatic coating composition, and an antistatic coating film formed by using the coating composition.
  • antistatic agents for preventing static electricity.
  • carbon black may be used, surfactant may be used, metal salt compound may be used, and a conductive polymer may be used.
  • conductive polymers have advantages such as good conductivity and stability and are actively used as raw materials for various antistatic agents. When used alone, the conductive polymer is usually used together with a dopant due to low solubility in solvents, strong coagulation, lack of conductivity, and the like.
  • Representative examples include poly (3,4-ethylenedioxythiophene, hereinafter referred to as PEDOT).
  • PEDOT is used in the form of a water-soluble or water-dispersible mixture using polystyrene sulfonic acid (hereinafter referred to as PSS) as a dopant.
  • PSS polystyrene sulfonic acid
  • Commercialized PEDOT / PSS complexes include Hervios Clevios and Agfa Orgacon. Almost all PEDOT / PSS commercial products are supplied in a water-dispersible state, and antistatic agents using PEDOT / PSS are manufactured and sold using aquatic raw materials such as water-based polyurethanes. However, raw materials such as water-based polyurethanes are difficult to maintain high solids due to their inherent limitations, and have disadvantages such as low pencil hardness after coating, low UV stability, and susceptibility to moisture.
  • a mixed coating agent in which an organic solvent is mixed with a water-dispersed PEDOT / PSS raw material and an organic polymer showing high stability and hardness is used as a binder.
  • Such materials are commonly used as antistatic agents due to the limitation of conductivity.
  • the application field is not expanded.
  • a PEDOT / PSS mixture synthesized as a water dispersion is prepared using a solvent such as a solvent-exchange technique to prepare a conductive polymer solution having a water content of 30% or less, and then using a resin such as an ultraviolet curable acrylate.
  • UV curable antistatic agent " which must be accompanied by the solvent exchange process of PEDOT / PSS mixture prepared in the form of water dispersion, there is a high risk that the control of water content is not fully achieved and there is a disadvantage that it is not suitable for mass production .
  • a process of minimizing moisture content may be provided by adding and filtering a plurality of organic solvents that can be mixed with water to a PEDOT / PSS mixture synthesized as a water dispersion in several steps.
  • a dispersion aid mainly an acrylic copolymer
  • a PEDOT / PSS mixture provided as an aqueous dispersion to obtain a stable dispersion, and then an organic solvent of a kind that can be mixed with water.
  • the process of adding and filtering should be carried out in several stages.
  • This technique has a disadvantage that a specific type of acrylic copolymer must be used, and it is not easy to add a separate binder for adding functionality.
  • a PEDOT / PSS mixture having a solid content of 15 to 20% of water content can be provided by freeze drying the PEDOT / PSS mixture synthesized as a water dispersion.
  • a water free photocurable antistatic coating may be provided.
  • a method for producing a photocurable antistatic coating composition having a minimum moisture content by redispersing a solid PEDOT / PSS mixture prepared by a process provided in patent document EP 1309646B1 in an organic solvent is disclosed. Is being provided. In the redispersion of solid PEDOT / PSS mixture, the content of high boiling point solvent such as Dimethysulfoxide (DMSO), Ethyleneglycol (EG), Foramide (FA), etc. is used more than 90% by mass.
  • DMSO Dimethysulfoxide
  • EG Ethyleneglycol
  • FA Foramide
  • An object of the present invention is to use a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder, to form an antistatic coating film having a high light transmittance and low surface resistance
  • PEDOT / PSS polystyrenesulfonic acid
  • the present invention provides a dust collecting container including a chemically stable PEDOT / PSS dispersion, a photocurable antistatic coating composition prepared from the dispersion, and an antistatic coating film formed using the coating composition.
  • the present invention to solve the above problems, the first mixing step of preparing a mixed solvent by mixing an organic solvent and a dispersion aid; And a second mixing step of mixing poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder with the mixed solvent; and poly (3,4-ethylenedioxythiophene; Provided is a process for the preparation of a) -polystyrenesulfonic acid (PEDOT / PSS) dispersion.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • the mixed solvent and the mixture of poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) by the high shear mixer to disperse and mix may include; high shear mixer step of performing a second mixed solution to produce.
  • the bead mill step of performing additional dispersion of the second mixed solution to the bead mill may further include.
  • the dispersion aid is a first dispersion aid for aiding the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrene sulfonic acid (PEDOT / PSS) of the solid powder form; And a second dispersion aid for improving conductivity when the dispersion is coated.
  • PEDOT / PSS polystyrene sulfonic acid
  • the first dispersion aid comprises at least one of amines (Amine), acrylates (Acrylate), and polyols (Polyols)
  • the second dispersion aid is diethylene glycol (Diethylene glycol) ), Propylene glycol, tetramethylene glycol, sorbitol, N, N-dimethylformamide, ethylene glycol, N, N-dimethylacet N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide, formic acid, propylene carbonate, ethylene carbonate (ethylene carbonate), 2,6-difluoropyridine, 2,6-difluoropyridine, formamide, and N-methylformamide.
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid is 0.5 to 2.0% by weight
  • the organic solvent is 80 to 97% by weight
  • the dispersion aid 1 to 12 Weight percent.
  • the present invention comprises an organic solvent, a dispersion aid, and poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS), the organic solvent and the dispersion aid Poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT) prepared by mixing poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder / PSS) to provide a dispersion.
  • PEDOT poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • the organic solvent, the dispersing aid and the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) may be dispersed and mixed by a shearing force by a high shear mixer.
  • the dispersing aid and the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) is dispersed and mixed by shearing force by a high shear mixer, Further distribution may be performed.
  • an organic solvent, a dispersion aid, and poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) is mixed, and dispersion and mixing by shear force Or a dispersion preparation step of performing dispersion and mixing by shearing force and then further dispersing in a bead mill to prepare a dispersion;
  • a coating liquid preparation step of preparing a coating composition by performing dispersion and mixing by shearing force by a high shear mixer with respect to the coating mixture.
  • the first coating mixture preparation step the pre-coating mixture preparation step of preparing a pre-coating mixture by mixing an additional organic solvent, a curable binder, and an additive; And a dispersion mixing step of mixing the dispersion with the precoating mixture.
  • the coating composition poly (3,4-ethylenedioxythiophene)-polystyrene sulfonic acid (PEDOT / PSS) 0.1 to 2.0% by weight, dispersing aid 1.05 to 14% by weight, organic solvent 60 to 95% by weight, It may include 1 to 40% by weight of the curable binder, 0.01 to 3% by weight of the additive.
  • PEDOT / PSS poly(ethylenedioxythiophene)-polystyrene sulfonic acid
  • dispersing aid 1.05 to 14% by weight
  • organic solvent 60 to 95% by weight It may include 1 to 40% by weight of the curable binder, 0.01 to 3% by weight of the additive.
  • the dispersion aid is a first dispersion aid for aiding the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrene sulfonic acid (PEDOT / PSS) of the solid powder form; And a second dispersion aid for improving conductivity when the dispersion is coated, wherein the first dispersion aid is one or more of amines (Amines), acrylates (Acrylates), and polyols (Polyols).
  • the first dispersion aid is one or more of amines (Amines), acrylates (Acrylates), and polyols (Polyols).
  • the second dispersion aid is diethylene glycol (Diethylene glycol), propylene glycol (propylene glycol), tetramethylene glycol (tetramethylene glycol), sorbitol (sorbitol), N, N- dimethylformamide (N, N- dimethylformamide, ethylene glycol, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide , Formic acid, propylene carbonate, ethylene carbonate, 2,6-difluoropyridine, formamide, and N-methylformamide (N) -methylformamide) at least 1 It includes, the first dispersion aid is 0.5 to 2.0% by weight, the second dispersion aid may be 1 to 10% by weight.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrene sulfonic acid
  • the coating composition poly (3,4-ethylenedioxythiophene)-polystyrene sulfonic acid (PEDOT / PSS) 0.1 to 2.0% by weight, dispersing aid 1.05 to 14% by weight, the final organic solvent 60 to 95% by weight It may include 1 to 40% by weight of the curable binder, 0.01 to 3% by weight of the additive.
  • PEDOT / PSS poly(ethylenedioxythiophene)-polystyrene sulfonic acid
  • dispersing aid 1.05 to 14% by weight
  • the final organic solvent 60 to 95% by weight It may include 1 to 40% by weight of the curable binder, 0.01 to 3% by weight of the additive.
  • the dispersion aid is a first dispersion aid for aiding the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrene sulfonic acid (PEDOT / PSS) of the solid powder form; And a second dispersion aid for improving conductivity when the dispersion is coated, wherein the first dispersion aid is one or more of amines (Amines), acrylates (Acrylates), and polyols (Polyols).
  • the first dispersion aid is one or more of amines (Amines), acrylates (Acrylates), and polyols (Polyols).
  • the second dispersion aid is diethylene glycol (Diethylene glycol), propylene glycol (propylene glycol), tetramethylene glycol (tetramethylene glycol), sorbitol (sorbitol), N, N- dimethylformamide (N, N- dimethylformamide, ethylene glycol, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide , Formic acid, propylene carbonate, ethylene carbonate, 2,6-difluoropyridine, formamide, and N-methylformamide (N) -methylformamide) at least 1 It may include.
  • the first dispersion aid is 0.5 to 2.0% by weight
  • the second dispersion aid may be 1 to 10% by weight.
  • the present invention is a dust collector used in a vacuum cleaner, the dust collector includes a casing portion, and a coating layer provided on the inner wall of the casing portion, the coating layer, poly (3, 4 -Ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) 0.1 to 2.0% by weight, dispersing aid 1.05 to 14% by weight, organic solvent 60 to 95% by weight, curable binder 1 to 40% by weight, additives 0.01 to 3% by weight It includes, to provide a dust collector.
  • PEDOT / PSS poly (3, 4 -Ethylenedioxythiophene) -polystyrenesulfonic acid
  • the dispersion aid is a first dispersion aid for aiding the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrene sulfonic acid (PEDOT / PSS) of the solid powder form; And a second dispersion aid for improving conductivity when the dispersion is coated, wherein the first dispersion aid comprises one or more of Amine, Acrylate, and Polyol, and the second dispersion aid is diethylene glycol.
  • PEDOT / PSS polystyrene sulfonic acid
  • Dispersion according to an embodiment of the present invention can be utilized in various types of coating composition, it can exhibit an effect that can be utilized in a photocurable coating composition excellent in surface hardness, weather resistance, chemical resistance, water resistance and the like.
  • the coating composition according to an embodiment of the present invention may be coated on various kinds of substrates to achieve an effect of implementing an antistatic function.
  • the dust collecting container according to the embodiment of the present invention can exert an effect of forming a high antistatic function and high transparency.
  • the dust collecting container since no charge is accumulated in the dust, when the dust is removed from the dust collecting container, the dust of the dust collecting container is prevented from contaminating additional objects due to static electricity. Can be exercised.
  • an explosion hazard that may occur due to static electricity, an unpleasant feeling when contacting a user, etc. may be removed.
  • the coating composition according to an embodiment of the present invention When the coating composition according to an embodiment of the present invention is applied to a cyclone vacuum cleaner, the dust inside the dust collector is entangled with each other as the cleaner is operated, thereby rotating the inside of the dust collector. At this time, since the charge is not accumulated in the dust due to the antistatic effect of the coating composition, the electrostatic repulsive force is removed, so that the space between the dusts to be entangled becomes dense, and the antistatic dust collector in the same volume of dust collector is not. It can have the effect of storing more dust than dust collector.
  • Fig. 1 is a view schematically showing the steps of a method for preparing a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) dispersion according to an embodiment of the present invention.
  • PEDOT / PSS polystyrenesulfonic acid
  • FIG. 2 is a view schematically showing the steps of the manufacturing method of the coating composition according to an embodiment of the present invention.
  • FIG. 3 is a view schematically showing a three-dimensional view of the dust collecting container according to an embodiment of the present invention.
  • FIG. 4 is a schematic cross-sectional view of a dust collecting container according to an embodiment of the present invention.
  • an embodiment may not be construed as having any aspect or design described being better or advantageous than other aspects or designs. .
  • a “component surface” includes one or more component surfaces.
  • first and second may be used to describe various components, but the components are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another.
  • first component may be referred to as the second component, and similarly, the second component may also be referred to as the first component.
  • Fig. 1 is a view schematically showing the steps of a method for preparing a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) dispersion according to an embodiment of the present invention.
  • PEDOT / PSS polystyrenesulfonic acid
  • the organic solvent and the dispersion aid are mixed to prepare a mixed solvent.
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid has an ethylenedioxy group in the form of a ring in the structure of thiophene, and excellent stability to air or heat
  • the optical bandgap (760 nm to 780 nm or 1.6 eV to 1.7 eV) is lower than that of thiophene. Discoloration is possible and absorption band exists in the infrared region in the oxidation state to ensure transparency.
  • PEDOT / PSS is in the form of a solid powder, it is possible to use a pallet (trade name Orgacon Dry) provided by AGFA of Belgium.
  • the organic solvent is a ketone solvent, an alcohol solvent, an acetate solvent, an aromatic solvent, a glycol ether solvent, an acrylate monomolecular solvent, an amide solvent, an acrylate oligomer, a urethane acrylate polymer (Urethane acrylate polymer) or a mixed solvent of the organic solvent.
  • the organic solvent is methyl ethyl ketone (MEK), isopropyl alcohol, ethyl alcohol, n-butyl acetate, toluene ), Propylene glycol methyl ether (PGME), Propylene glycol methyl ether acetate (PGMEA), Hydroxyethyl methacrylate (HEMA), Hydroxyethy acrylate (HEA), and N, N-dimethylform amide (DMF) One or a mixed solvent of the organic solvent.
  • MEK methyl ethyl ketone
  • PGME Propylene glycol methyl ether
  • PMEA Propylene glycol methyl ether acetate
  • HEMA Hydroxyethyl methacrylate
  • HEMA Hydroxyethy acrylate
  • DMF N, N-dimethylform amide
  • the method for preparing a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) dispersion according to an embodiment of the present invention, after the second mixing step, the mixed solvent and poly
  • a high shear force may be generated using a high rotational force or the like, thereby forming a device including two or more rotors and stators.
  • Such a high shear mixer can be made into a second mixture by making the mixture more homogeneous by using a cavitation phenomenon.
  • the high shear mixer is dispersed and mixed for 1 hour or more at a rotational speed of about 6,000 rpm or more with respect to the mixed liquid. At this time, cooling is further performed to maintain the temperature of the mixed solution at 10 ° C.
  • the bead mill step of performing additional dispersion of the second mixed solution to the bead mill may further include.
  • the bead mill is in the form of a bead mill capable of nano dispersion.
  • the second mixed liquid may be more homogeneous and improved in dispersibility by the beads.
  • pulverization and dispersion are applied by applying an impact force to the target powder by using beads that are efficient in wet dispersion and wet grinding, for example, zirconia-containing beads, and thus, the second mixed liquid by the bead mill step.
  • Silver can be more homogeneous and improved dispersibility by the beads.
  • the beads preferably have a particle diameter of 50 ⁇ m to 200 ⁇ m, more preferably, beads having a particle size in the range of 80 ⁇ m to 120 ⁇ m.
  • the rotating speed of the rotating body of the bead mill is preferably used in the range of about 30 to 60Hz frequency.
  • the dispersion thus prepared should be stored in a cold storage device at or below 10 ° C. If stored for a long time at room temperature 20 °C or more, the dispersion of PEDOT / PSS shows a cohesive phenomenon, the conductivity may be sharply reduced.
  • the dispersion aid comprises a first dispersion aid for assisting in the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder; And a second dispersion aid for improving conductivity when the dispersion is coated.
  • PEDOT / PSS poly(ethylenedioxythiophene) -polystyrenesulfonic acid
  • the first dispersion aid comprises at least one of amines (Amine), acrylates (Acrylate), and polyols (Polyols)
  • the second dispersion aid is diethylene glycol (Diethylene glycol), Propylene glycol, tetramethylene glycol, sorbitol, N, N-dimethylformamide, ethylene glycol, N, N-dimethylacetamide ( N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide, formic acid, propylene carbonate, ethylene ethylene carbonate), 2,6-difluoropyridine, formamide, and N-methylformamide.
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid is 0.5 to 2.0% by weight.
  • the electrical conductivity is weakened, and when the PEDOT / PSS is 2.0 wt% or more, the manufacturing cost may be increased.
  • the organic solvent is 80 to 97% by weight.
  • the dispersibility may be weakened, and when the organic solvent is 97% or more, electrical conductivity may be weakened.
  • the dispersion aid is 1 to 12% by weight. More preferably, the first dispersion aid is 0.5 to 2.0% by weight, and the second dispersion aid is 1 to 10% by weight. More preferably, the first dispersion aid is 0.8 to 1.0% by weight, and the second dispersion aid is 1 to 5% by weight.
  • the content of the first dispersion aid and the second dispersion aid can improve the electrical conductivity when the dispersion is used as a coating composition while further dispersing the PEDOT / PSS solid powder.
  • PEDOT / PSS polystyrenesulfonic acid
  • Poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) dispersion is an organic solvent, a dispersion aid, and poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS).
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid has an ethylenedioxy group in the form of a ring in the structure of thiophene, and excellent stability to air or heat
  • the optical bandgap (760 nm to 780 nm or 1.6 eV to 1.7 eV) is lower than that of thiophene. Discoloration is possible and absorption band exists in the infrared region in the oxidation state to ensure transparency.
  • PEDOT / PSS is in the form of a solid powder, it is possible to use a pallet (trade name Orgacon Dry) provided by AGFA of Belgium.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • PDOT / PSS polystyrenesulfonic acid
  • the organic solvent is a ketone solvent, an alcohol solvent, an acetate solvent, an aromatic solvent, a glycol ether solvent, an acrylate monomolecular solvent, and an amide solvent, an acrylate oligomer, and a urethane acrylate. It includes any one of a polymer (Urethane acrylate polymer) or a mixed solvent of the organic solvent.
  • the organic solvent is methyl ethyl ketone (MEK), isopropyl alcohol, ethyl alcohol, n-butyl acetate, toluene ), Propylene glycol methyl ether (PGME), Propylene glycol methyl ether acetate (PGMEA), Hydroxyethyl methacrylate (HEMA), Hydroxyethy acrylate (HEA), and N, N-dimethylform amide (DMF) One or a mixed solvent of the organic solvent.
  • MEK methyl ethyl ketone
  • PGME Propylene glycol methyl ether
  • PMEA Propylene glycol methyl ether acetate
  • HEMA Hydroxyethyl methacrylate
  • HEMA Hydroxyethy acrylate
  • DMF N, N-dimethylform amide
  • the organic solvent, the dispersing aid and the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) may be dispersed and mixed by a shearing force by a high shear mixer.
  • the dispersing aid and the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid are dispersed and mixed by shearing force by a high shear mixer, the bead mill Additional distribution can be performed.
  • the dispersion aid comprises a first dispersion aid for aiding the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder; And a second dispersion aid for improving conductivity when the dispersion is coated.
  • PEDOT / PSS polystyrenesulfonic acid
  • the first dispersion aid comprises at least one of amines (Amine), acrylates (Acrylate), and polyols (Polyols)
  • the second dispersion aid is diethylene glycol (Diethylene glycol), Propylene glycol, tetramethylene glycol, sorbitol, N, N-dimethylformamide, ethylene glycol, N, N-dimethylacetamide ( N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide, formic acid, propylene carbonate, ethylene ethylene carbonate), 2,6-difluoropyridine, formamide, and N-methylformamide.
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid is 0.5 to 2.0 wt%
  • the organic solvent is 80 to 97 wt%
  • the dispersion aid is 1 to 12 wt% to be.
  • the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid is 0.5 to 2.0% by weight.
  • the electrical conductivity is weakened, and when the PEDOT / PSS is 2.0 wt% or more, the manufacturing cost may be increased.
  • the organic solvent is 80 to 97% by weight.
  • the dispersibility may be weakened, and when the organic solvent is 97% or more, electrical conductivity may be weakened.
  • the dispersion aid is 1 to 12% by weight. More preferably, the first dispersion aid is 0.5 to 2.0% by weight, and the second dispersion aid is 1 to 10% by weight. More preferably, the first dispersion aid is 0.8 to 1.0% by weight, and the second dispersion aid is 1 to 5% by weight.
  • the content of the first dispersion aid and the second dispersion aid can improve the electrical conductivity when the dispersion is used as a coating composition while further dispersing the PEDOT / PSS solid powder.
  • FIG. 2 is a view schematically showing the steps of the manufacturing method of the coating composition according to an embodiment of the present invention.
  • the method for preparing the coating composition shown in FIG. 2 includes mixing an organic solvent, a dispersing aid, and a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS), performing dispersion and mixing by shear force, or A dispersion preparation step (S1000) of preparing a dispersion by performing dispersion and mixing by shearing force and then further dispersing in a bead mill;
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • the organic solvent and the additional organic solvent may be a ketone solvent, an alcohol solvent, an acetate solvent, an aromatic solvent, a glycol ether solvent, an acrylate monomolecular solvent, an amide solvent, an acrylate oligomer, Urethane acrylate polymer (Urethane acrylate polymer) includes any one or a mixed solvent of the organic solvent.
  • the organic solvent and the additional organic solvent are methyl ethyl ketone (MEK), isopropyl alcohol, ethyl alcohol, n-butyl acetate, respectively. acetate, toluene, propylene glycol methyl ether (PGME), propylene glycol methyl ether acetate (PGMEA), hydroxyethyl methacrylate (HEMA), hydroxyethyl methacrylate (HEMA), and N, N-dimethylformamide (N, N- dimethylform amide (DMF)) or a mixed solvent of the organic solvent.
  • MEK methyl ethyl ketone
  • PGME propylene glycol methyl ether
  • PMEA propylene glycol methyl ether acetate
  • HEMA hydroxyethyl methacrylate
  • HEMA hydroxyethyl methacrylate
  • DMF N-dimethylformamide
  • the dispersion preparation step (S1000) may be in accordance with one embodiment of the method for producing a poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) dispersion described above.
  • the first coating mixture preparation step may include a precoating mixture preparation step (S2010) of preparing a precoating mixture by mixing an additional organic solvent, a curable binder, and an additive; And a dispersion mixing step (S2020) of mixing the dispersion with the precoating mixture.
  • S2010 precoating mixture preparation step
  • S2020 dispersion mixing step
  • the mass of the dispersion in the dispersion mixing step has a ratio of 10 to 35% with respect to the weight of the precoating mixture.
  • the additive may include at least one of a defoamer, a leveling agent, a humectant, and an initiator (photoinitiator or thermal initiator), and as such an additive, an alkoxy silane-based, polysiloxane-based, polyether siloxane copolymer , Non-silicone polymer, fluorinated silicone, organo modified polysiloxane, polycarboxylic acid, modified polyether, fatty acid derivative, surfactant, urethane copolymer, nonionic modified fatty acid derivative, polyacrylate, polyether siloxane copolymer, dimethyl Polysiloxanes, ultraviolet crosslinkable silicone polyethers, may be acrylates, ultraviolet crosslinkable silicone acrylates, ultraviolet crosslinkable silicone polyether acrylates, nonionic organic surfactants.
  • an initiator photoinitiator or thermal initiator
  • the coating composition prepared by the method for preparing the coating composition poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) 0.1 to 2.0% by weight, dispersion aid 1.05 to 14% by weight %, Organic solvent 60 to 95% by weight, curable binder 1 to 40% by weight, additives 0.01 to 3% by weight.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • dispersion aid 1.05 to 14% by weight %
  • Organic solvent 60 to 95% by weight Organic solvent 60 to 95% by weight
  • curable binder 1 to 40% by weight additives 0.01 to 3% by weight.
  • the organic solvent corresponds to the weight% of the organic solvent included in the initial dispersion and the organic solvent of the final coating composition including the additional organic solvent.
  • the coating composition may have high transparency and electrical conductivity.
  • the dispersion aid comprises a first dispersion aid for assisting in the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder; And a second dispersion aid for improving conductivity when the dispersion is coated.
  • PEDOT / PSS polystyrenesulfonic acid
  • the first dispersion aid comprises at least one of amines (Amine), acrylates (Acrylate), and polyols (Polyols)
  • the second dispersion aid is diethylene glycol (Diethylene glycol), Propylene glycol, tetramethylene glycol, sorbitol, N, N-dimethylformamide, ethylene glycol, N, N-dimethylacetamide ( N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide, formic acid, propylene carbonate, ethylene ethylene carbonate), 2,6-difluoropyridine, formamide, and N-methylformamide.
  • the first dispersion aid is 0.05 to 4.0% by weight
  • the second dispersion aid may be 1 to 10% by weight.
  • the coating composition according to an embodiment of the present invention is an organic solvent, a dispersion aid, and a dispersion containing poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS), an additional organic solvent, a curable binder, And a coating composition prepared by mixing the additives and performing dispersion and mixing by shearing force.
  • the coating composition is 0.1 to 2.0% by weight of poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS), 1.05 to 14% by weight of a dispersion aid, 60 to 95% by weight of the final organic solvent. , 1 to 40% by weight of the curable binder, 0.01 to 3% by weight of the additive.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid
  • a dispersion aid 60 to 95% by weight of the final organic solvent.
  • 1 to 40% by weight of the curable binder 0.01 to 3% by weight of the additive.
  • the dispersion aid comprises a first dispersion aid for assisting in the dispersion of the poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT / PSS) in the form of a solid powder; And a second dispersion aid for improving conductivity when the dispersion is coated.
  • PEDOT / PSS polystyrenesulfonic acid
  • the first dispersion aid comprises at least one of amines (Amine), acrylates (Acrylate), and polyols (Polyols)
  • the second dispersion aid is diethylene glycol (Diethylene glycol), Propylene glycol, tetramethylene glycol, sorbitol, N, N-dimethylformamide, ethylene glycol, N, N-dimethylacetamide ( N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, glycerol, ethylene cyanide, formic acid, propylene carbonate, ethylene ethylene carbonate), 2,6-difluoropyridine, formamide, and N-methylformamide.
  • the first dispersion aid is 0.05 to 4.0% by weight
  • the second dispersion aid may be 1 to 10% by weight.
  • PEDOT PSS dispersion: 13.51 wt%
  • Photoinitiator Irgacure 184 (brand name): 1.01 wt%
  • Photocrosslinked aliphatic acrylate polymer, Photocrosslinked acrylate oligomer, Photocurable acrylate monomer mixture 27.03 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), Ethanol, Dispersion Aid 1, and Dispersion Aid 2 was mixed into the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • PEDOT PSS dispersion: 10.37 wt%
  • Photoinitiator Irgacure 184 (trade name): 1.24 wt%
  • Photo-crosslinked aliphatic acrylate polymer, photo-crosslinked acrylate oligomer, photocurable acrylate monomer mixture 16.6 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), Ethanol, Dispersion Aid 1, and Dispersion Aid 2 was added to the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • PEDOT PSS dispersion: 10.71 wt%
  • Photoinitiator Irgacure 184 (trade name): 1.3 wt%
  • Photocrosslinked aliphatic acrylate polymer, Photocrosslinked acrylate oligomer, Photocurable acrylate monomer mixture 12.99% by weight
  • PEDOT: PSS dispersion mixture composed of PEDOT: PSS complex (solid), Toluene, acrylate monomer, Dispersion Aid 1, and Dispersion Aid 2 was added to the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • PEDOT PSS dispersion: 16.34 wt%
  • Photoinitiator Irgacure 184 (brand name): 0.98 wt%
  • Photocrosslinked aliphatic acrylate polymer Photocrosslinked acrylate oligomer, Photocurable acrylate monomer mixture: 26.14 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), Ethanol, Dispersion Aid 1, and Dispersion Aid 2 was added to the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • PEDOT PSS dispersion: 19.14 wt%
  • Photoinitiator Irgacure 184 (brand name): 0.98 wt%
  • Photocrosslinked aliphatic acrylate polymer Photocrosslinked acrylate oligomer, Photocurable acrylate monomer mixture: 21.59 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), Toluene, Acrylate monomer, Dispersion Aid 1, and Dispersion Aid 2 was mixed in the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • PEDOT PSS dispersion: 14.47 wt%
  • Photoinitiator Irgacure 184 (brand name): 0.93 wt%
  • Polyether siloxane copolymer 0.31 wt%
  • Photo-crosslinked aliphatic acrylate polymer 2.89 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), 2-Butanone, Acrylate monomer, Dispersion Aid 1, and Dispersion Aid 2 was added to the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • PEDOT PSS dispersion: 15.53 wt%
  • Photoinitiator Irgacure 184 (brand name): 0.93 wt%
  • Polyether siloxane copolymer 0.31 wt%
  • Photo-crosslinked aliphatic acrylate polymer 3.11 wt%
  • PEDOT: PSS dispersion mixture consisting of PEDOT: PSS complex (solid), 2-Butanone, Acrylate monomer, Dispersion Aid 1, and Dispersion Aid 2 was added to the mixture of (1). 30 minutes magnetic stirring
  • Spray coating coating composition to polycarbonate substrate (1.0mm thickness, 200mmX200mm size, no surface pretreatment)
  • Photocuring was carried out under a UV lamp of 400mJ at 4M / min.
  • Example 1 10e10.2 ohm / square 4992 hours 10e7.2 ohm / square
  • Example 2 10e10.2 ohm / square 4992 hours 10e7.2 ohm / square
  • Example 3 10e10.5 ohm / square 4992 hours 10e7.7 ohm / square
  • Example 4 10e7.0 ohm / square 4992 hours 10e7.2 ohm / square
  • Example 5 10e7.0 ohm / square 4728 hours 10e6.7 ohm / square
  • Example 6 10e5.5 ohm / square 4728 hours 10e6.6 ohm / square
  • Example 7 10e7.5 ohm / square 4728 hours 10e6.6 ohm / square
  • Example 8 10e3.9 ohm / square 4728 hours 10e4.2 ohm / square
  • Example 9 10e5.1 ohm / square 4728 hours 10e5.5 ohm / square
  • the surface resistance may increase slightly as in Example 4, Example 6, Example 8, and Example 9, but it can be seen that it maintains a sufficient value to implement the antistatic performance.
  • Example 8 The coating solution of Example 8 was carried out at room temperature indoor storage / 20 days and then coated on the same substrate in the same manner.
  • the surface resistance increased slightly depending on the time after the coating solution was prepared and the time after coating, but the characteristics such as transmittance and Haze were improved, and the surface resistance was sufficient to express the antistatic performance. It can be confirmed.
  • the following table is an antistatic performance comparison table according to the surface resistance value.
  • FIG. 3 is a view schematically showing a three-dimensional view of the dust collecting container according to an embodiment of the present invention.
  • 4 is a schematic cross-sectional view of a dust collecting container according to an embodiment of the present invention.
  • static electricity refers to a charge occurring in a frictional electric lamp and the like, and an electric phenomenon caused by the charge whose charge distribution does not change in time.
  • static electricity is generated due to charging between certain objects, the objects may stick to each other by electrostatic attraction.
  • the dust stuck to the dust collecting body 210 may not be removed well.
  • the dust collecting container 100 used in the vacuum cleaner according to an embodiment of the present invention, the casing 110, and the coating layer 120 provided on the inner wall of the casing,
  • the coating layer 120 poly (3,4-ethylenedioxythiophene)-polystyrene sulfonic acid (PEDOT / PSS) 0.1 to 2.0% by weight, dispersing aid 1.05 to 14% by weight, organic solvent 60 to 95% by weight, curable binder 1 To 40% by weight, and 0.01 to 3% by weight additive.
  • PEDOT / PSS poly (3,4-ethylenedioxythiophene)-polystyrene sulfonic acid
  • the coating layer 120 as described above is a coating layer containing a conductive polymer that provides excellent conductivity, and the conductive polymer includes PEDOT / PSS. Such a conductive polymer has an effect of lowering the surface resistance of the dust collector (100).
  • the casing part 110 of the dust collecting container 100 may be made of a synthetic resin, for example, a polycarbonate resin.
  • the polycarbonate resin has a high surface resistance of approximately 10 11 to 10 15 ohm / sqr. When the surface resistance is high, there is a high possibility of generating static electricity between the dust collecting container 100 and the dust.
  • the conductive polymer is provided on the surface of the dust collecting container 100, the surface resistance is lowered and the electrical conductivity is increased.
  • the charges charged in the dust collecting container 100 may be moved to the cleaner body or discharged in the air.
  • FIG. 5 is a view schematically showing a three-dimensional view of the dust collecting container according to an embodiment of the present invention.
  • 6 is a schematic cross-sectional view of a dust collecting container according to an embodiment of the present invention.
  • the description of the dust collector shown in FIGS. 3 and 4 may be equally applicable to the dust collector shown in FIGS. 5 and 6, and a description thereof will be omitted.
  • An embodiment is shown in which the casing portion 310 and the coating layer 320 are provided in the pain relief 300.
  • Dispersion according to an embodiment of the present invention can be utilized in various types of coating composition, it can exhibit an effect that can be utilized in a photocurable coating composition excellent in surface hardness, weather resistance, chemical resistance, water resistance and the like.
  • the coating composition according to an embodiment of the present invention may be coated on various kinds of substrates to achieve an effect of implementing an antistatic function.
  • the dust collecting container according to the embodiment of the present invention can exert an effect of forming a high antistatic function and high transparency.
  • the dust collecting container since no charge is accumulated in the dust, when the dust is removed from the dust collecting container, the dust of the dust collecting container is prevented from contaminating additional objects due to static electricity. Can be exercised.
  • an explosion hazard that may occur due to static electricity, an unpleasant feeling when contacting a user, etc. may be removed.
  • the coating composition according to an embodiment of the present invention When the coating composition according to an embodiment of the present invention is applied to a cyclone vacuum cleaner, the dust inside the dust collector is entangled with each other as the cleaner is operated, thereby rotating the inside of the dust collector. At this time, since the charge is not accumulated in the dust due to the antistatic effect of the coating composition, the electrostatic repulsive force is removed, so that the space between the dusts to be entangled becomes dense, and the antistatic dust collector in the same volume of dust collector is not. It can have the effect of storing more dust than dust collector.

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Abstract

La présente invention concerne un liquide dispersé de PEDOT/PSS, une composition de revêtement antistatique photodurcissable préparée à partir du liquide dispersé et un récipient de collecte de poussière comprenant la composition de revêtement et, plus particulièrement, un liquide dispersé de PEDOT/PSS qui est préparé à l'aide de poly(3,4-éthylènedioxythiophène)-poly(acide styrènesulfonique) (PEDOT/PSS) de type poudre solide et qui présente une transmittance élevée de la lumière, une faible résistance de surface et une stabilité chimique, une composition de revêtement antistatique photodurcissable préparée à partir du liquide dispersé et un récipient de collecte de poussière comprenant la composition de revêtement.
PCT/KR2016/012275 2016-09-02 2016-10-28 Liquide dispersé de pedot/pss, composition de revêtement antistatique photodurcissable préparée à partir du liquide dispersé et récipient de collecte de poussière comprenant la composition de revêtement WO2018043807A1 (fr)

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KR1020160112969A KR101958203B1 (ko) 2016-09-02 2016-09-02 Pedot/pss 분산액, 상기 분산액으로 제조된 광경화형 대전 방지 코팅조성물, 및 상기 코팅조성물을 포함하는 집진통

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US11180867B2 (en) 2019-03-20 2021-11-23 University Of Kentucky Research Foundation Continuous wet-spinning process for the fabrication of PEDOT:PSS fibers with high electrical conductivity, thermal conductivity and Young's modulus
WO2023114560A3 (fr) * 2021-07-06 2023-10-26 Northwestern University Compositions polymères pour transistors électrochimiques organiques à canaux verticaux et circuits logiques complémentaires

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KR20210088044A (ko) 2020-01-03 2021-07-14 삼성디스플레이 주식회사 유기 발광 표시 장치
KR102540680B1 (ko) * 2020-11-12 2023-06-08 주식회사 포리스 함유금속선택에 기반한 일함수 제어가 가능한 도전성 박막을 제조할 수 있는 코팅제

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WO2023114560A3 (fr) * 2021-07-06 2023-10-26 Northwestern University Compositions polymères pour transistors électrochimiques organiques à canaux verticaux et circuits logiques complémentaires

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