WO2023157917A1 - 水性塗料組成物及び複層塗膜形成方法 - Google Patents

水性塗料組成物及び複層塗膜形成方法 Download PDF

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Publication number
WO2023157917A1
WO2023157917A1 PCT/JP2023/005462 JP2023005462W WO2023157917A1 WO 2023157917 A1 WO2023157917 A1 WO 2023157917A1 JP 2023005462 W JP2023005462 W JP 2023005462W WO 2023157917 A1 WO2023157917 A1 WO 2023157917A1
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Prior art keywords
group
parts
coating film
polyisocyanate compound
acid
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PCT/JP2023/005462
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English (en)
French (fr)
Japanese (ja)
Inventor
裕二 鵜澤
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Kansai Paint Co Ltd
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Kansai Paint Co Ltd
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Publication date
Application filed by Kansai Paint Co Ltd filed Critical Kansai Paint Co Ltd
Priority to JP2024501430A priority Critical patent/JPWO2023157917A1/ja
Priority to CN202380020627.0A priority patent/CN118660945A/zh
Priority to CA3242355A priority patent/CA3242355A1/en
Priority to US18/730,994 priority patent/US20250154374A1/en
Priority to EP23756442.2A priority patent/EP4481010A4/en
Publication of WO2023157917A1 publication Critical patent/WO2023157917A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C09D201/08—Carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/02—Processes for applying liquids or other fluent materials performed by spraying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
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    • B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
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    • B05D7/56—Three layers or more
    • B05D7/57—Three layers or more the last layer being a clear coat
    • B05D7/572—Three layers or more the last layer being a clear coat all layers being cured or baked together
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    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • 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
    • 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
    • C09D5/022—Emulsions, e.g. oil in water
    • 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
    • C09D7/41—Organic pigments; Organic dyes
    • 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
    • C09D7/63—Additives non-macromolecular organic
    • 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
    • C09D7/65—Additives macromolecular
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B05D2201/02—Polymeric substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2202/00—Metallic substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2202/00—Metallic substrate
    • B05D2202/10—Metallic substrate based on Fe
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2401/00—Form of the coating product, e.g. solution, water dispersion, powders or the like
    • B05D2401/20—Aqueous dispersion or solution
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2502/00—Acrylic polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2503/00—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2150/00—Compositions for coatings

Definitions

  • a coating composition having high curability even when the heating temperature is relatively low is generally highly reactive, and it is not compatible with coating film performance such as hardness, chipping resistance and water resistance, and storage stability. There were enough cases.
  • Emulsion polymerization for preparing an emulsion of the core copolymer (I) can be carried out by a conventionally known method. For example, it can be carried out by emulsion polymerization of a polymerizable unsaturated monomer mixture using a polymerization initiator in the presence of an emulsifier.
  • An anionic emulsifier and a nonionic emulsifier can be preferably used as the emulsifier.
  • the gradient polymer layer can generally be obtained by a known polymerization method called power feed polymerization. Specifically, for example, when two types of monomer A (monomer mixture A) and monomer B (monomer mixture B) are polymerized, monomer B (monomer mixture B) is added to monomer A (monomer mixture A).
  • a gradient polymer layer can be obtained by introducing the monomer A (monomer mixture A) into a reaction vessel and performing a polymerization reaction while dropping into a vessel containing the.
  • the shell portion of the hydroxyl group- and carboxyl group-containing acrylic resin particles (A1'') preferably has a glass transition temperature of 0 to 120°C, more preferably 20 to 100°C, from the viewpoint of the water resistance of the resulting coating film. is more preferable, and 30 to 100°C is even more preferable.
  • hydroxyl group- and carboxyl group-containing polyester resin (A2) includes linseed oil fatty acid, coconut oil fatty acid, safflower oil fatty acid, soybean oil fatty acid, sesame oil fatty acid, perilla oil fatty acid, hemp oil fatty acid, tall oil fatty acid, and dehydrated castor oil.
  • Fatty acid-modified polyester resins modified with (semi)drying oil fatty acids such as fatty acids may also be used. Generally, it is suitable that the modified amount of these fatty acids is 30% by mass or less in terms of oil length.
  • the hydroxyl group- and carboxyl group-containing polyester resin (A2) may be partially reacted with a monobasic acid such as benzoic acid.
  • a method for modifying the hydroxyl group- and carboxyl group-containing polyester resin (A2) with an acrylic resin a known method can be used, for example, a polymerizable unsaturated group-containing polyester resin and a polymerizable unsaturated monomer Examples include a method of polymerizing a mixture, and a method of reacting a hydroxyl group- and carboxyl group-containing polyester resin and an acrylic resin with each other.
  • the content of the hydroxyl group- and carboxyl group-containing polyurethane resin (A3) is the resin solid content in the aqueous coating composition.
  • 2 to 70% by mass is preferable, 5 to 50% by mass is more preferable, and 10 to 40% by mass is even more preferable.
  • the aqueous dispersion (B) of a blocked polyisocyanate compound contains a blocked polyisocyanate compound (b1) and at least one anionic surfactant (b2) selected from sulfonates and sulfate ester salts. .
  • the blocked polyisocyanate compound (b1) is a compound obtained by blocking the isocyanate groups of the polyisocyanate compound (b11) with a blocking agent (b12).
  • the molecular weight of the spacer (b13) is in the range of 500 to 6,000 from the viewpoint of the low-temperature curability of the water-based coating composition of the present disclosure and the hardness, chipping resistance, and water resistance of the formed coating film. It is preferably in the range of 800 to 5,000, even more preferably in the range of 1,000 to 4,000.
  • the number of functional groups of the spacer (b13) is preferably 2 to 3, more preferably 2, from the viewpoint of storage stability of the aqueous coating composition of the present disclosure.
  • the nonionic hydrophilic group-containing compound has a number average molecular weight in the range of 200 to 2,000 from the viewpoint of the storage stability of the aqueous coating composition of the present disclosure and the water resistance of the formed coating film. is preferred.
  • the number average molecular weight is more preferably 300 or more, and even more preferably 400 or more.
  • the number average molecular weight is more preferably 1,500 or less, and even more preferably 1,200 or less, from the viewpoint of the water resistance of the coating film formed by the aqueous coating composition of the present disclosure.
  • the aqueous coating composition of the present disclosure has excellent storage stability, and even when cured at a relatively low temperature, the coating film exhibits excellent coating performance such as high hardness and water resistance, and good glass adhesion.
  • the aqueous dispersion of (B) the blocked polyisocyanate compound contains at least one anionic surfactant (b )
  • the stability of the emulsified state of the blocked polyisocyanate compound (b1) in water is improved, and the reaction with the hydroxyl group- and carboxyl group-containing resin (A) and the polycarbodiimide compound (C) is suppressed. and is presumed to have excellent storage stability.
  • the methylol group of the above methylolated melamine resin may be partially or completely etherified with a suitable alcohol.
  • suitable alcohols used for etherification include methyl alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, i-butyl alcohol, 2-ethyl-1-butanol, 2-ethyl-1 - hexanol and the like.
  • the bright pigment is preferably scale-like. Suitable bright pigments have a longitudinal dimension of 1 to 100 ⁇ m, particularly 5 to 40 ⁇ m, and a thickness of 0.001 to 5 ⁇ m, particularly 0.01 to 2 ⁇ m.
  • the amount of the bright pigment is 0.1 to 0.1 based on 100 parts by mass of the resin solid content in the water-based coating composition of the present disclosure. 100 parts by mass, preferably 1 to 50 parts by mass, more preferably 3 to 25 parts by mass.
  • the heating in step (4) can be performed by known means, for example, a drying furnace such as a hot air furnace, an electric furnace, an infrared induction heating furnace can be applied.
  • the heating temperature is 50 to 140°C, preferably 60 to 120°C, more preferably 70 to 90°C.
  • the heating time is not particularly limited, but is preferably 10 to 40 minutes, more preferably 20 to 40 minutes.
  • a viscosity change rate (%) of 100% or less is considered acceptable.
  • the storage stability results are also shown in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Paints Or Removers (AREA)
PCT/JP2023/005462 2022-02-18 2023-02-16 水性塗料組成物及び複層塗膜形成方法 Ceased WO2023157917A1 (ja)

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CA3242355A CA3242355A1 (en) 2022-02-18 2023-02-16 Aqueous coating composition and method of forming multilayer coating film
US18/730,994 US20250154374A1 (en) 2022-02-18 2023-02-16 Aqueous coating material composition and method for forming multilayer coating film
EP23756442.2A EP4481010A4 (en) 2022-02-18 2023-02-16 COMPOSITION OF AQUEOUS COATING MATERIAL AND METHOD FOR FORMING MULTILAYER COATING FILM

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EP4481010A4 (en) 2026-02-25
CA3242355A1 (en) 2023-08-24

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