WO2023080349A1 - Composition de peinture dissipatrice de chaleur à base d'uréthane du type monocomposant et procédé de préparation associé - Google Patents

Composition de peinture dissipatrice de chaleur à base d'uréthane du type monocomposant et procédé de préparation associé Download PDF

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WO2023080349A1
WO2023080349A1 PCT/KR2022/003161 KR2022003161W WO2023080349A1 WO 2023080349 A1 WO2023080349 A1 WO 2023080349A1 KR 2022003161 W KR2022003161 W KR 2022003161W WO 2023080349 A1 WO2023080349 A1 WO 2023080349A1
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heat
diisocyanate
dissipating
weight
graphite
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PCT/KR2022/003161
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English (en)
Korean (ko)
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김태한
이상헌
육수경
유민숙
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퓨어만 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • 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
    • C09D7/40—Additives
    • 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
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic

Definitions

  • This application relates to a heat-dissipating paint composition in which a subject and a curing agent are contained in one composition mixture.
  • thermosetting paints consist of two components: a main agent and a hardener. Before coating, the two components are mixed in a fixed ratio, then dried and cured by heating.
  • Urethane-based paints are composed of a main component mainly composed of polyol and a curing agent mainly composed of diisocyanate. Polyol and isocyanate react even at room temperature from the moment they are mixed to form a urethane bond. In general, isocyanate is highly reactive, can react with itself to form dimers and trimers, and is sensitive to moisture. Therefore, generally, pigments and various additives are added to a polyol-based main component.
  • urethane paint After mixing the two components, the main agent and the hardener, as the urethane reaction progresses, the viscosity of the mixture (paint) gradually increases, and at some point the coating properties fall. Companies sometimes add a dilution solvent at the point when the viscosity of the paint increases excessively during the coating process. However, since the solid content of the paint is different, it is insufficient to secure a constant quality of the coating film properties. Therefore, urethane paint has a specific pot life or workable time, so the user must be able to finish the work within that time.
  • One embodiment of the present application 25 to 45% by weight of polyol; 7 to 20% by weight of thermally conductive particles; 5 to 10% by weight of additives; 6 to 15% by weight of block isocyanate; and 10 to 50% by weight of an acetate-based solvent.
  • the thermally conductive particles may include at least one or more graphite selected from the group consisting of expanded graphite, impression graphite, artificial graphite, and earthy graphite; and metal particles; can include
  • the composition may have a pot life of 120 hours or more at room temperature.
  • the room temperature may be 15 °C to 25 °C.
  • the composition is exfoliated to separate graphene nanoplates (GNPs) or graphene from graphite by milling. Specifically, the composition is exfoliated by milling for 1 to 6 hours to separate graphene nanoplates (GNPs) or graphene from expanded graphite.
  • the composition may include two or more of graphite particles, graphene nanoplate particles, and graphene particles after milling, or all of them. After the milling, the graphite particles, graphene nanoplate (GNP) particles, or graphene particles may have a diameter of 0.1 ⁇ m to 50 ⁇ m.
  • the milling bead may be zirconia having a diameter of 0.05 mm to 3.0 mm.
  • the composition may further include 0.5 to 1.5% by weight of a nonionic surfactant based on the total weight of the composition.
  • the nonionic surfactant is a phosphoric acid ester of polyethoxylated alkylphenol, an ethoxylated alkylphenol, a sulfuric acid ester, polyoxyethylene tristyrylphenyl ether, ethylene oxide/propylene oxide block copolymer , polyethylene glycol mono(tristyrylphenyl) ether, sorbitan monostearate, polyoxyethylene dodecyl monoether, polyoxyethylene-polyoxypropylene block copolymer, polyoxyethylene monolaurate, polyoxyethylene monohexadecyl Ether, polyoxyethylene monooleate, polyoxyethylene mono(cis-9-octadecenyl) ether, polyoxyethylene monostearate, polyoxyethylene monooctadecyl ether, polyoxyethylene dioleate, polyoxyethylene distea Late, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, poly
  • the acetate-based solvent is N-butyl acetate, ethyl acetate, amyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl acetate, diethylene glycol ethyl acetate, It may be at least one selected from the group consisting of ethylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, and propylene glycol methyl ether acetate (PGMEA).
  • PGMEA propylene glycol methyl ether acetate
  • the metal particles are at least one selected from the group consisting of aluminum, iron, copper, zinc, tin, nickel, antimony, magnesium, and chromium, and a flake type having a diameter of 5 to 40 ⁇ m.
  • the thermally conductive particles may include at least one carbon selected from the group consisting of carbon black, single-walled carbon nanotubes, multi-walled carbon nanotubes, graphene, and carbon fibers; and heat dissipating filler; At least one or more of them may be further included.
  • the thermally conductive particles include 5 to 15% by weight of graphite; and 1 to 6% by weight of metal particles; including, 1 to 5% by weight of carbon; and 1 to 5% by weight of a heat dissipating filler.
  • the heat dissipating filler is porous silica, alumina, magnesium oxide, aluminum nitride, boron nitride, silicon nitride, aluminum hydroxide, magnesium hydroxide, boron carbide, zirconia, silicon nitride, boron oxide and silicon oxide. It may be at least one or more selected from the group consisting of.
  • the polyol resin is acrylic polyol, caprolactone polyol, epoxy polyol, ester polyol, ether polyol, polycarbonate polyol, and various diol compounds including polyethylene glycol, polypropylene glycol, and polytetramethylene glycol. It may be at least one or more selected from among.
  • the block diisocyanate is hexamethylene diisocyanate (HDI, hexamethylene diisocyanate), isophorone diisocyanate (IPDI, isophorone diisocyanate), tetramethylene diisocyanate, pentamethylene diisocyanate ( Pentamethylene diisocyanate), toluene diisocyanate (TDI), butane diisocyanate, pentane diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, 4, 4'-dicyclohexylmethane-4,4'-diisocyanate (HMDI, dicyclohexylmethane-4,4'-diisocyanate), 4,4'-methylenebisphenyl isocyanate (MDI, 4,4'-methylenebis (phenyl isocyanate)], norbornene diisocyanate (norbornene di
  • At least one or more selected from the group consisting of dimethyl pyrazole (DMP, 3,5-dimethyl pyrazole), dimethyl malonate (DEM, dimethyl malonate), methyl ethyl ketone oxime (MEKO), and caprolactam ( ⁇ -CAP, caprolactam) is reacted with at least one blocking agent selected from the group consisting of isocyanate group.
  • DMP dimethyl pyrazole
  • DEM dimethyl malonate
  • MEKO methyl ethyl ketone oxime
  • caprolactam ⁇ CAP, caprolactam
  • the additive may include at least one selected from the group consisting of a matting agent, a colorant, an adhesion promoter, a dispersing agent, an antisettling agent, an antifoaming agent, and a leveling agent.
  • the adhesion promoter may be epoxy ester phosphate acid.
  • the anti-settling agent may be a urea-based compound.
  • One embodiment of the present application provides a method for producing a one-component urethane heat-dissipating paint comprising preparing a dispersion by milling the heat-dissipating paint composition.
  • the step of ultrasonicating graphite or exfoliating the graphite at high pressure may be further included.
  • One embodiment of the present application provides a heat-dissipating coating film formed by applying a heat-dissipating paint composition on a substrate and firing at 120 ° C. to 180 ° C. for 5 to 60 minutes.
  • One embodiment of the present application provides an article on which the heat dissipation coating film is formed.
  • the heat-dissipating paint composition of the present application forms a coating film with excellent adhesiveness with one coating, prevents peeling from the surface of the heat-dissipating part during use, and maintains high durability against thermal shock and salt spray from the outside.
  • the heat-dissipating paint composition of the present application has the advantage that it can be coated on various substrates without a working time restriction and has excellent heat-dissipating performance.
  • the heat-dissipating paint composition of the present application has no time constraints in the entire process of preparing the paint before coating, such as mixing and stirring the main agent and hardener, causing process defects such as measurement error, mixing, infiltration of foreign substances or moisture, and increase in viscosity at room temperature. It has the advantage of being able to eliminate several factors that
  • the heat-dissipating paint composition of the present application is advantageous in securing process stability and consistency of coating film quality.
  • FIG. 1(a) shows an aluminum plate
  • FIG. 1(b) shows an aluminum plate coated with a heat dissipating paint.
  • the one-component urethane heat-dissipating paint composition of the present application uses blocked isocyanate as a curing agent, which is not reactive below a certain temperature.
  • the isocyanate group of the block isocyanate is chemically bonded to a specific compound, and when a certain temperature level is reached, the chemical bond is thermally decomposed to expose the isocyanate, and the urethane reaction with the polyol proceeds.
  • the heat-dissipating paint composition of the present application has a working time of 120 hours or more, so there is no limitation in the process of preparing the paint before coating and actual working time.
  • One embodiment of the present application based on the total weight of the composition, 25 to 45% by weight of a polyol; 7 to 20% by weight of thermally conductive particles; 5 to 10% by weight of additives; 6 to 15% by weight of block isocyanate; and 10 to 40% by weight of an acetate-based solvent.
  • the thermally conductive particles may include at least one graphite selected from the group consisting of expanded graphite, impression graphite, artificial graphite, and earthy graphite. Preferably, it may be expanded graphite.
  • the expanded graphite may be exfoliated into graphene nanoplates (GNPs) or graphene through various processes such as milling, ultra-high pressure dispersion, and ultrasonic waves.
  • GNP refers to a state composed of hundreds of graphene layers by exfoliation between graphene layers constituting graphite. Expanded graphite is easily separated between layers when an external force is applied due to the widening of the space between the graphene layers of the graphite, and as a result, a certain portion of graphene and GNP are generated.
  • the expanded graphite is pre-exfoliated using an ultra-high pressure disperser or ultrasonic waves, and then mixed with polyol constituting the binder and other particles and additives, and treated in a mixing-milling process to prepare a heat-dissipating paint, and separate pre-treatment and exfoliation It was confirmed that peeling could occur only with the milling process after mixing with other components such as binders without any process.
  • the milling speed and the size of zirconia (ZrO 2 ) used as milling beads affect peeling, and the diameter of zirconia is preferably 0.2 to 3.0 mm. Further, the diameter of zirconia is more preferably 0.5 to 2.0 mm. In the case of milling beads having a size of 0.5 to 2.0 mm, the graphite exfoliation effect is excellent even after milling for 2 to 5 hours.
  • the graphite is wet for 1 hour to 6 hours, specifically for 2 hours to 6 hours, more specifically for 2 hours to 5 hours
  • Graphite is exfoliated by milling, and the diameter of the particles after milling may be 0.1 to 50 ⁇ m.
  • expanded graphite having a diameter of 3 to 100 ⁇ m was crushed and exfoliated to a size of 0.1 to 50 ⁇ m after milling for 2 to 5 hours.
  • composition is exfoliated so that graphene nanoplates (GNP) and graphene are separated from graphite by milling, so that graphite, graphene nanoplates (GNP), and graphene may all be included.
  • GNP graphene nanoplates
  • GNP graphene nanoplates
  • natural graphite such as impression graphite and earthy graphite
  • impression graphite and earthy graphite does not easily delaminate the layers of graphite even if sufficient milling time is maintained, so the heat dissipation efficiency does not change significantly depending on the milling time.
  • natural graphite has advantages in that it is easy to control the viscosity of paint and has excellent productivity.
  • the composition may be mixed by adding a block diisocyanate-based curing agent after the milling.
  • the expansion side edge may be graphite in which interlayer expansion is performed by heat treatment after acid treatment.
  • the heat-dissipating paint composition may have a viscosity of 300 cps or more to 2,000 cps or less at 25 °C. When the viscosity is within the above range, it may be more advantageous in terms of the sedimentation rate of the thermally conductive particles and the stability of the dispersion process. If it is less than 300 cps, it may be difficult to create a heat-dissipating coating film due to dripping of the composition, phase separation may occur during paint storage, and if it exceeds 2,000 cps, the coating process may not be easy, and the thickness of the coating film may be too thick. can
  • the composition may further include a tin (tin) urethane curing catalyst such as dibutyl tin dilaurate, and may further include various diol compounds as spacers.
  • a tin (tin) urethane curing catalyst such as dibutyl tin dilaurate
  • various diol compounds as spacers.
  • the thermally conductive particles may include metal particles.
  • the metal particles may be at least one selected from the group consisting of aluminum, iron, copper, zinc, tin, nickel, magnesium, chromium, and zirconium.
  • the metal particles, specifically aluminum powder can use flake-type particles with a diameter of 5 to 40 ⁇ m, and in addition to heat dissipation properties, they can produce a pearl effect on the coating film and help to strengthen the surface of the coating film. there is.
  • the thermally conductive particles may further include at least one carbon selected from the group consisting of carbon black, single-walled carbon nanotubes, multi-walled carbon nanotubes, graphene, and carbon fibers.
  • Carbon nanotubes are a modified form of graphene, and can be divided into single-wall carbon nanotubes (SWCNT), in which a single layer of graphene is rolled into a tube, and multi-wall carbon nanotubes composed of several layers. wall carbon nanotubes (MWCNTs).
  • SWCNT single-wall carbon nanotubes
  • MWCNTs wall carbon nanotubes
  • Carbon nanotubes have excellent mechanical properties and have a very high aspect ratio (length/diameter), so they have excellent tensile stress and excellent thermal conductivity, so their application range is diverse. In addition, it has the properties of a conductor or a semiconductor depending on its winding shape, its energy gap varies according to its diameter, and it has a quasi-one-dimensional structure, so it exhibits a unique quantum effect.
  • MWCNTs can also give a thermal bridge effect between graphite or GNPs produced during milling, and graphene particles.
  • Graphene is a material with an atom-sized honeycomb structure made of carbon atoms. It has a thickness of 0.2 nm and has very high physical and chemical stability. It conducts electricity 100 times better than copper and has electron mobility 100 times higher than silicon. fast. In addition, its strength is more than 200 times stronger than steel, its thermal conductivity is more than twice as high as that of diamond, which has the highest thermal conductivity, and it transmits most of the light, so it is transparent and has excellent elasticity.
  • carbon fiber When carbon fiber has a strength of 10 to 20 g/d and a specific gravity of 1.5 to 2.1, it has excellent heat resistance and impact resistance, is strong against chemicals, and has high resistance to pests. During the heating process, molecules such as oxygen, hydrogen, nitrogen, etc. escape and the weight is reduced, so it is lighter than metal (aluminum), but has excellent elasticity and strength compared to metal (iron), and has electrical conductivity and high thermal conductivity.
  • the carbon material dispersion formed of such a carbon material is mixed with the graphite material, the carbon material such as carbon nanotubes contained in the carbon material dispersion is connected by covalent bonds between the particles of the graphite material, thereby improving the thermal conductivity and providing excellent heat dissipation performance.
  • the particle size of the carbon material may be preferably 200 nm to 1 ⁇ m.
  • the amount of carbon may be 1% to 5% by weight in the heat dissipating paint composition.
  • the graphite and the carbon may have a weight ratio of 1:1 to 10:1 in the filler.
  • the thermally conductive particles may further include a heat dissipating filler.
  • the heat dissipating filler is porous silica (SiO 2 ), alumina (alumina), aluminum oxide (Al 2 O 3 ), magnesium oxide, zinc oxide, silicon carbide (SiC), aluminum nitride, boron nitride, silicon nitride, hydroxide It may be at least one selected from the group consisting of aluminum, magnesium hydroxide, boron carbide (B 4 C), and silicon nitride (Si 3 N 4 ).
  • the heat dissipating filler may serve to facilitate milling in the milling process.
  • the heat dissipating filler may have an average particle diameter of 1 to 10 ⁇ m. If it exceeds the above range, the adhesion to the substrate is reduced, and workability may be deteriorated.
  • the heat dissipating filler may be selected without limitation as long as it has excellent thermal conductivity and heat dissipation in its material.
  • the shape of the heat dissipating filler is not limited, and may be porous or non-porous in structure, and may be selected differently depending on the purpose. However, preferably, it is preferable to achieve excellent heat dissipation performance, easy formation of a heat dissipation coating film, uniform heat dissipation performance after forming the heat dissipation coating film, and surface quality of the heat dissipation coating film.
  • a filler whose surface is modified with a functional group such as a silane group, an amino group, an amine group, a hydroxyl group, a carboxyl group, or the like may be used.
  • the functional group may be directly bonded to the surface of the filler, or carbon number It may be indirectly bonded to the filler via a substituted or unsubstituted aliphatic hydrocarbon having 1 to 20 atoms or a substituted or unsubstituted aromatic hydrocarbon having 6 to 14 carbon atoms.
  • the binder determines the thermal and mechanical strength of the coating film, so it can be selected according to the purpose.
  • Urethane resin binders have the advantage of being able to design from thin films with high strength and heat resistance to flexible and elastic thin films.
  • the polyol is acrylic polyol, caprolactone polyol, epoxy polyol, ester polyol, ether polyol, polycarbonate polyol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene glycol, diethylene glycol, 1,3-butanediol, 1 ,4-butanediol, neopentylglycol, 3-methyl-1,5-pentanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 1 ,2-hexanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, 1,8-decanediol, octanedecanedio
  • any polymer having a hydroxyl group capable of forming a main chain of a polyurethane compound may be used. Due to the polyol component, excellent reworkability characteristics such as residue reduction can be expressed.
  • polyester polyol which is widely used in polyurethane production, exhibits a disadvantage in that adhesion to a metal interface is poor when used alone, and as a result, it is weak against thermal shock. Therefore, when considering interfacial adhesion, impact resistance, hardness, and curing characteristics, a three-component polyol may be used by mixing acrylic polyol and polyester polyol or adding caprolactone polyol to further improve adhesion and impact resistance.
  • the type and mixing ratio of resin can be variously selected in consideration of strength, hardness, and heat resistance (Tg) according to the requirements of the properties of the coating film.
  • the block diisocyanate is a compound in which diisocyanate and a blocking agent are combined, hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), tetramethylene diisocyanate ), Pentamethylene diisocyanate, Toluene diisocyanate (TDI), Butane diisocyanate, Pentane diisocyanate, Trimethylhexamethylene diisocyanate, Lysine diisocyanate (lysine diisocyanate), 4,4'-dicyclohexylmethane-4,4'-diisocyanate (HMDI, dicyclohexylmethane-4,4'-diisocyanate), 4,4'-methylenebisphenyl isocyanate (MDI, 4,4'-methylenebis (phenyl isocyanate) )], norbornene diisocyanate, hydrogenated xylene diisocyanate, hydrogenated di
  • Blocked diisocyanate is thermally decomposed at 110 to 180° C. to expose isocyanate groups and react with polyol to form urethane polymer chains.
  • diisocyanate HDI, isophorone diisocyanate, hydrogenated xylene diisocyanate, and hydrogenated diphenylmethane diisocyanate are preferred because they are industrially available, and the coating film obtained from the polyisocyanate composition tends to have better weather resistance and flexibility there is
  • the blocked isocyanate resin may be included in an amount of 6 to 15 wt% based on 100 wt% of the total curing agent composition. If less than 6% by weight is added, curing with the main material hardly occurs, and adhesion and hardness may deteriorate. If added in excess of 15% by weight, excessive isocyanate groups are generated to lower the curing density and physical properties of the coating film may be deteriorated.
  • blocked diisocyanate depends on the curing temperature and time, it can be selected according to the purpose and conditions of film formation. In general, deblocking is performed at a temperature of 120 to 140 ° C or higher, but when ⁇ -CAP is used as a blocking agent, a relatively high temperature of 160 ° C or higher is required.
  • the composition may use a curing catalyst that is dibutyl tin dilaurate.
  • Urethane resin causes a curing reaction between polyol and diisocyanate at a sufficiently fast rate even at a relatively low temperature, but in the present invention, since the deblocking of the block diisocyanate occurs first and then the curing reaction proceeds, When a reduction in is especially required, the use of a catalyst helps to reduce the overall reaction rate.
  • the solvent may be selected according to the selected binder resin, curing agent, etc., so the present invention is not particularly limited thereto, and any solvent capable of properly dissolving each component may be used as the solvent.
  • the solvent may specifically use an acetate solvent, more specifically N-butyl acetate, acetate, ethyl acetate, amyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl acetate, diethylene glycol At least one selected from the group consisting of ethyl acetate, ethylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, and propylene glycol methyl ether acetate (PGMEA) may be used.
  • PMEA propylene glycol methyl ether acetate
  • the smaller the added amount of the solvent the higher the viscosity but may decrease the stability in the dispersion process.
  • the solvent may be 10% to 50% by weight of the heat dissipating paint composition. If the solvent is less than 10% by weight of the heat dissipating paint composition, the resin does not dissolve well, adhesion is not excellent, dispersibility is not good, and the viscosity becomes high, and if it is more than 50% by weight, the substrate for heat dissipation Gaps may be formed when the heat dissipating paint composition is coated, and the heat dissipation effect may be reduced because it is not easy to control the thickness.
  • the viscosity can be adjusted by adding a similar amount of the solvent to the resin.
  • the weight ratio of the resin to the solvent may be 1:1.
  • the content of the solvent can be adjusted according to the condition of the spray coater. In the case of bar coating, it may contain less than spray coating, as the viscosity should be slightly higher.
  • the solvent may be volatilized during a curing process after coating the heat dissipating paint composition on a substrate. After coating the heat dissipating paint composition on a substrate for heat dissipation, the solvent included in the heat dissipating paint composition may be volatilized and thus the solvent component may not be present.
  • the composition may further include at least one or more selected from the group consisting of a matting agent, a colorant, an adhesion promoter, a dispersing agent, an antisettling agent, an antifoaming agent, and a leveling agent as an additive.
  • the matting agent serves to increase the emissivity of the colorant and the surface of the coating film to minimize the decrease in color loss due to light, air, moisture or extreme temperatures.
  • the matting agent may include at least one selected from the group consisting of titanium dioxide, aerogel silica, hydrogel silica, urea formaldehyde resin and benzoguamine formaldehyde resin, preferably silica.
  • the matting agent may be spherical particles having a diameter of 0.01 to 0.5 ⁇ m.
  • the matting agent may be included in 2 to 5% by weight based on the total weight of the composition.
  • the silica matting agent it also affects the viscosity of the paint composition, but when an excessive amount is added, the viscosity becomes too high, and spraying may not be smooth during spray coating.
  • the above-described heat-dissipating paint composition may further include a dispersant and a solvent for improving the dispersibility of the heat-dissipating filler and realizing a uniform heat-dissipating coating film.
  • the antifoaming agent prevents the generation and retention of air bubbles during mixing of each composition and prevents the generation of air bubbles or craters on the surface of a coating film.
  • the leveling agent may improve the uniformity of the coating film and reduce surface roughness.
  • the above-described heat-dissipating paint composition may be used as a pH adjuster, a viscosity adjuster, a thixotropy imparting agent, an antioxidant, a heat stabilizer, a light stabilizer, an ultraviolet absorber, a colorant, a flame retardant, an anti-mold, and the like.
  • a pH adjuster a viscosity adjuster
  • a thixotropy imparting agent an antioxidant
  • a heat stabilizer a light stabilizer
  • an ultraviolet absorber a colorant
  • a flame retardant an anti-mold, and the like.
  • One type or two or more types of additives may be added.
  • the various additives described above may be those known in the art and are not particularly limited in the present invention.
  • the antioxidant may be a known component employed in the art as an antioxidant of a heat-dissipating paint composition.
  • the antioxidant is tri-methyl phosphate, tri-phenyl phosphate, tris (2, 4-di-tert-butylphenyl) phosphate, triethylene glycol-bis-3- (3-tert-butyl-4-hydride) Roxy-5-methylphenyl)propionate, 1,6-hexane-diol-3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythrityl-tetrakis(3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 2-hydroxybenzophenone, 2-hydroxyphenylbenzothiazole, hindered amine, organic nickel compound, salicylate, cinnamate derivatives, resorcinol monobenzoate, oxanilide, and p-hydroxybenzoate may include at least one
  • the antioxidant may preferably be included in an amount of 0.1 to 3% by weight based on the total weight of the composition. If the antioxidant is provided in less than 0.1 parts by weight, discoloration and cracking of the coating film may occur over a long time, and if the antioxidant is provided in more than 3 parts by weight, brittleness and strength of the coating film may be weakened.
  • the adhesion promoter may be epoxy ester phosphate acid.
  • the adhesion enhancer improves the interfacial adhesion between the coating film and the adherend, and prevents peeling and cracking of the coating film even during thermal shock and long-term use.
  • the adhesion promoter may be included in an amount of 3 to 10% by weight based on the total weight of the composition.
  • the dispersant may be included in an amount of 0.1 to 1.5% by weight based on the total weight of the composition. If it is less than 0.1% by weight, the filler may not be well dispersed, and aggregation may increase. If the dispersant is provided in excess of 1.5% by weight, the adhesion strength of the adherend may be weakened, pin holes and orange peel may occur on the surface of the coating film, and there is a risk of deterioration in adhesive strength.
  • the dispersant may be included to increase the dispersibility of the heat dissipating paint composition, to make the density even, and to appropriately adjust the rheology control.
  • the dispersing agent it is preferable to use a nonionic surfactant.
  • a nonionic surfactant When the heat-dissipating paint composition of the present application is stored for 4 weeks or more, the effect of improving the storage stability of the nonionic surfactant is more excellent.
  • the anti-settling agent controls the flowability of the composition and serves to prevent or slow down the sedimentation and caking phenomena of the particles.
  • the anti-settling agent may use a urea-based compound or an amide-based compound, and may prevent sedimentation of thermally conductive particles having a high specific gravity.
  • the heat-dissipating paint composition includes an anti-settling agent dispersed in the binder resin, and in this case, the anti-settling agent may be included in an amount of 0.5 to 1% by weight based on the total weight of the composition.
  • the composition may be put into a stirrer and stirred for 10 minutes to 1 hour at a speed of, for example, 50 rpm to 300 rpm. If the stirring time is too short, it is difficult to achieve uniform mixing, and even if the stirring time is too long, it is difficult to expect a more uniform mixing effect.
  • the milling may be performed by at least one method selected from the group consisting of roll milling, ball milling, jet milling, screw mixing, attrition milling, bead milling, basket milling, revolution mixing, and super mill.
  • the step of sonicating the graphite may further include.
  • One embodiment of the present application provides a heat-dissipating coating film formed by applying a heat-dissipating paint composition on a substrate and firing at 120° C. to 180° C. for 10 minutes to 1 hour.
  • the coating may use various methods including at least one selected from the group consisting of spray coating, roll printing, dipping coating, comma coating, gravure coating, and slit die coating.
  • the thickness of the coating can be used for manufacturing various heat dissipation substrates and coating heat sinks, and may be formed to a thickness of 10 ⁇ m to 100 ⁇ m, more specifically, 20 ⁇ m to 70 ⁇ m, in consideration of optimal heat dissipation characteristics. If the thickness is more than the above, there is a possibility of cost increase and cracking, and if it is less than that, good heat dissipation performance cannot be exhibited.
  • the coating of the heat-dissipating paint composition When the coating of the heat-dissipating paint composition is formed on the substrate, it is thermally cured so that the solvent volatilizes (or evaporates) and the heat-dissipating paint composition is cured.
  • the substrate can be used without limitation for various metal materials such as aluminum and copper, as well as glass and plastic, and has excellent heat dissipation and adhesion, as well as excellent hardness, solvent resistance and water resistance.
  • the drying may be performed at a temperature higher than the temperature at which the solvent volatilizes (or evaporates), higher than the temperature required for deblocking of the blocking device, and lower than the melting temperature of the substrate. For example, it may be performed for 10 minutes to 1 hour at a temperature of 100 ° C to 180 ° C depending on the type of blocking group. If the thermal curing time is too short, it is difficult to complete the curing, and if the thermal curing time is too long, it may be difficult to expect a further thermal curing effect. Temperature and time are also set according to the characteristics of the blocking machine.
  • the heat-dissipating paint prepared by the heat-dissipating material manufacturing method can effectively emit heat, has a fast heat release rate and high heat emissivity, and is coated with a heat-dissipating paint composition having excellent adhesion to a three-dimensional substrate. Heat dissipation efficiency can be greatly improved by coating on a heat dissipation substrate, various heat sinks, copper foil films, aluminum sheets, etc.
  • the present application includes an article including a heat-dissipating coating film cured by treating at least a portion of an outer surface of the heat-dissipating coating composition according to the present application.
  • the article may be a heat dissipation part for lighting, and specifically may be a heat dissipation heat sink for lighting.
  • the heat dissipation heat sink for lighting may include a heat sink and a heat dissipation coating layer formed on at least a part or all of an outer surface of the heat sink.
  • the heat dissipation paint composition according to the present application is an electronic device component including mobile devices, TVs, wearable devices and flexible devices, LED lamps, ECU (electronic control unit), EV, in addition to the above-described heat dissipation unit, circuit board and lighting parts Automotive parts including batteries and inverters, RF equipment, digital equipment, telecommunications devices including server devices and setup boxes, network devices, solar panels, LEDs and AI/AIN PCBs (Printed Circuit Boards), etc. It can be applied to parts for lighting including devices, lighting cases and sockets.
  • a heat dissipation busbar for EV high voltage switching relay for example, a heat dissipation busbar for EV high voltage switching relay, a heat dissipation case for EV high voltage switching relay, a heat dissipation DC-DC converter for vehicles, It can be applied to automobile parts including at least one selected from the group consisting of automobile engine cooling devices, automobile LED headlamps, and PTC heaters.
  • the automotive part may be a heat-dissipating bus bar for an EV high-voltage relay including a heat-dissipating coating film cured by treating at least a portion of an outer surface of the heat-dissipating paint composition according to the present application.
  • the EV high voltage relay busbar may be a known EV high voltage relay busbar commonly used in the art, and the material, size, thickness, and shape of the busbar are the desired input of the EV high voltage relay to be implemented. As the voltage and / or output voltage can be changed according to the internal design in consideration, the present application is not particularly limited thereto.
  • the automotive part may be a heat dissipation case for an EV high voltage switching relay including a heat dissipation coating film cured by treating at least a portion of an outer surface of the heat dissipation paint composition according to the present application.
  • the case for the EV high voltage switching relay may be a case for a known EV high voltage relay commonly used in the art.
  • the EV high voltage switching relay case may include the above-described EV high voltage relay busbar, and the material, size, thickness and shape of the case may be determined by the shape and number of busbars located inside the EV high voltage relay to be implemented. As it is possible to change according to the internal design of the present application is not particularly limited thereto.
  • the automotive part may be a heat-dissipating DC-DC converter including a heat-dissipating coating film cured by treating at least a portion of an outer surface of the heat-dissipating paint composition according to the present application.
  • the DC-DC converter functions to convert DC power of a specific voltage into DC power of another voltage, and may be a known DC-DC converter commonly used in the art. Since the size and shape of the DC-DC converter can be changed according to the internal design of a device to be implemented, the present application is not particularly limited thereto.
  • the automotive part may be a heat dissipation engine cooling device including a heat dissipation coating film cured by treating at least a portion of an outer surface of the heat dissipation paint composition according to the present application.
  • a heat dissipation coating film may be formed on a part of a radiator included in the heat dissipation engine cooling device or, for example, a part or all of the radiator included in the heat dissipation engine cooling device.
  • the radiator may be a known radiator commonly used in the art, and since the material, size and shape of the radiator can be changed according to the internal design of the engine cooling device to be implemented, the present application is specifically limited thereto. I never do that.
  • the automotive part may be a heat-dissipating LED headlamp including a heat-dissipating coating film cured by treating at least a portion of an outer surface of the heat-dissipating paint composition according to the present application.
  • the LED headlamp may be a known LED headlamp commonly used in the art, and the material, size and shape of the LED headlamp depend on the design of the vehicle to be implemented and / or the internal design of the LED headlamp. As changes are possible, this application is not particularly limited thereto.
  • the automotive part may be a heat-dissipating PTC heater for an electric vehicle including a heat-dissipating coating film cured by treating at least a portion of an outer surface of the heat-dissipating paint composition according to the present application.
  • the PTC heater may include PTC fins, and as a heat dissipation coating film is formed on some or all of the PTC fins, heat dissipation efficiency may be improved and power consumption of the electric vehicle may be reduced.
  • the PTC pin is in the art
  • PTC pin It may be a known PTC pin that can be commonly used, and since the material, size, and shape of the PTC pin can be changed according to the internal design of the PTC heater to be implemented, the present application is not particularly limited thereto.
  • Example 1 It was the same as in Example 1 except that 'BI-7982 (blocked HDI trimer, Bexended Co.) 60 parts by weight' was used instead of 'TPA-B80X (blocked polyHDI, Asahi Kasehi Co.) 43 parts by weight' of Example 1.
  • the viscosity of the final paint was 520 cps.
  • Example 1 It is the same as Example 1 except for 50 parts by weight of acrylic polyol (OH value 90) instead of '40 parts by weight of acrylic polyol (OH value 90), 10 parts by weight of caprolactone polyol (OH value 280, MW 400)' of Example 1.
  • Example 2 It is the same as in Example 1 except for adding 2 parts by weight of dibutyl tin laurate.
  • Example 1 It is the same as Example 1 except that impression graphite was used instead of expanded graphite in Example 1.
  • Example 1 It is the same as Example 1 except that 'TPA-B80X (blocked polyHDI, Asahi Kasehi Co., Ltd.) 43 parts by weight' of Example 1 was not used. Instead, 20 parts by weight of the HDI trimer with respect to 100 parts by weight of the prepared paint was well stirred and mixed, and then spray coating was performed, followed by curing at 80 ° C for 30 minutes.
  • 'TPA-B80X blocked polyHDI, Asahi Kasehi Co., Ltd.
  • Example 1 Same as Example 1 except that milling was performed for 1.5 hours instead of 3 hours.
  • Example 1 The coating compositions of Examples 1 to 5 were coated by spraying, and after spraying, curing was performed by heating for 30 minutes in a chamber set at 150 ° C. However, in the case of Comparative Example 1 and Comparative Example 2, which are two-component, curing was performed at 80 ° C. for 30 minutes.
  • the temperature inside the chamber was adjusted to 40 °C.
  • FIG. 1(a) is an aluminum plate
  • FIG. 1(b) is an aluminum plate coated with a heat dissipating paint.
  • 2 shows a sample for evaluating heat dissipation performance.
  • a heat dissipation coating film 10 is formed on both sides of an aluminum plate 100 and a ceramic heater 30 is attached using a thermal grease 20 .
  • T1 represents the temperature of the heating element
  • T2 represents the temperature of the outside
  • T3 represents the temperature of the chamber.
  • the lead of the MITSUBUSHI hardness measurement pencil is left as it is, and the tree is cut into a length of about 5 to 6 mm, and the tip of the pencil is sharpened and the tip of the pencil is ground with sandpaper.
  • Pot life refers to the time during which paint coating is possible.
  • the viscosity of two-component paint increases as the curing reaction proceeds immediately after mixing the main agent and the hardener. After a certain time, the viscosity rises to such an extent that spraying is impossible even when diluted with a solvent.
  • the thermal decomposition temperature of the blocking agent is actually 120 ° C. or higher, the pot life can be said to be long enough not to interfere with the general production process.
  • Example 5 shows that the curing time can be shortened by using a urethane reaction catalyst.
  • excessive use of the catalyst may deteriorate the physical properties of the coating film.
  • Comparative Example 2 shows that the milling time should be at least 2 hours or more, preferably 3 hours or more. If the milling time is less than 2 hours, the grinding and peeling of the particles are not sufficiently performed, and as a result, the surface of the coating film is rough, deterioration in adhesion occurs, and heat dissipation properties are also deteriorated.
  • heat dissipation efficiency is 10% before milling, 30% after milling for 1 hour, 50% after milling for 2 hours, and 55% after milling for 3 hours. It can be confirmed that this is good and the heat dissipation efficiency is very good when milling for 3 hours or more. In the case of 3 hours or more and 6 hours or less, there was no difference in heat dissipation efficiency. However, in the case of impression graphite, heat dissipation efficiency was 20% before milling, but it was confirmed that heat dissipation efficiency was 25% after 1 hour of milling. Heat radiation efficiency was expressed as temperature reduction efficiency (based on °C) compared to existing commercially available paints.
  • Example 1 The thermal conductivity of Example 1 was measured according to the milling time at 25° C. and is shown in FIGS. 4 and 5 and Table 2 below.
  • the vertical thermal conductivity of the coating film formed by milling the composition of Example 1 for 3 hours was 1.4 W/m.K.
  • the horizontal thermal conductivity of the coating film formed by milling for 3 hours was 5.2 W/m.K, so it can be seen that the thermal conductivity was very excellent when milled for 3 hours.
  • FIG. 6 shows expanded graphite before milling
  • FIG. 7 shows a SEM picture of expanded graphite after milling for 3 hours
  • FIG. 8 shows a TEM picture of expanded graphite after milling for 3 hours.
  • the curing reaction begins at the point of mixing the main agent and the hardener.
  • the pot life measured in the invention previously filed by the inventor of the present application is around 6 hours.
  • the one-component type is not limited by pot life in the actual production process.
  • Two-component paints have a fundamental problem in that the physical properties of the coating film continuously change over time due to the change over time of the coating solution in which the actual subject and the hardener are mixed, in addition to the limitation of pot life.
  • the one-component type has a fundamental advantage in that it can guarantee uniformity of coating quality because the change over time during coating operation is relatively small and there is no risk due to work error or work mistake due to metering and mixing of the main agent and hardener.

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)
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Abstract

La présente demande concerne une composition de peinture dissipatrice de chaleur comprenant : 25 à 45 % en poids d'un polyol ; 7 à 20 % en poids de particules conductrices de la chaleur ; 5 à 10 % en poids d'un additif ; 10 à 40 % en poids d'un solvant ; et 6 à 15 % en poids d'un isocyanate bloc. La composition de peinture dissipatrice de chaleur de la présente invention est constituée d'un agent principal et d'un agent de durcissement dans un type monocomposant et ainsi facilite le travail de revêtement, est exempte de vie en pot du fait qu'il n'y a aucune restriction quant à la durée de vie en pot, améliore le rendement du travail et donne des revêtements de qualité constante.
PCT/KR2022/003161 2021-11-02 2022-03-07 Composition de peinture dissipatrice de chaleur à base d'uréthane du type monocomposant et procédé de préparation associé WO2023080349A1 (fr)

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JP6428032B2 (ja) * 2014-08-06 2018-11-28 Jnc株式会社 樹脂組成物、それを用いた放熱塗料および電子部品
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