WO2024203429A1 - 三液型塗料組成物用のキット、三液型塗料組成物及び型内被覆方法 - Google Patents

三液型塗料組成物用のキット、三液型塗料組成物及び型内被覆方法 Download PDF

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Publication number
WO2024203429A1
WO2024203429A1 PCT/JP2024/010162 JP2024010162W WO2024203429A1 WO 2024203429 A1 WO2024203429 A1 WO 2024203429A1 JP 2024010162 W JP2024010162 W JP 2024010162W WO 2024203429 A1 WO2024203429 A1 WO 2024203429A1
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Prior art keywords
range
acid
mass
hydroxyl
containing compound
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PCT/JP2024/010162
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English (en)
French (fr)
Japanese (ja)
Inventor
克斗 小村
晴河 中岡
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Kansai Paint Co Ltd
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Kansai Paint Co Ltd
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Priority to JP2024533873A priority Critical patent/JP7628221B1/ja
Priority to CN202480008451.1A priority patent/CN120569447A/zh
Priority to EP24779558.6A priority patent/EP4692260A1/en
Publication of WO2024203429A1 publication Critical patent/WO2024203429A1/ja
Anticipated expiration legal-status Critical
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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4202—Two or more polyesters of different physical or chemical nature
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • C08G18/4241—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
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    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
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    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • 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
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    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • C—CHEMISTRY; METALLURGY
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    • 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
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Definitions

  • the present invention relates to a kit for a three-component paint composition, a three-component paint composition, and an in-mold coating method using the kit or the three-component paint composition.
  • VOCs volatile organic compounds
  • Patent Document 1 discloses a two-component coating material composition comprising a coating base component A and a curing component B, wherein the coating base component A comprises: i. one or more polyols A1 selected from the group of polyols containing ester groups and having a hydroxyl value of 300 to 500 mg KOH/g and a hydroxyl group functionality of more than 2; ii.
  • R 1 -(OH) p (wherein R 1 is a p-valent branched, cyclic or linear, saturated or unsaturated aliphatic hydrocarbon radical having 5 to 18 carbon atoms, the radical R 1 optionally containing one or more tertiary amino groups, and p is 2 to 6), which do not contain ether groups and ester groups; and iii.
  • R 2 is a saturated or unsaturated aliphatic hydrocarbon radical having from 6 to 30 carbon atoms
  • R 3 is H, the radical PO(OH) 2 , or a radical of an optionally partially phosphorylated mono- or disaccharide or a radical of an optionally partially phosphorylated alditol
  • AO represents one or more alkylene oxide radicals selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide
  • r is 0 or 1 and s is 0 to 30, iv.
  • the present invention relates to a two-component coating material composition, characterized in that the composition comprises at least one additive A9 selected from the group consisting of wetting agents and/or dispersants, rheological aids and flow control agents, and the curing component B comprises i.
  • the two-component coating material composition comprises a solids content of at least 96% by weight according to ASTM D2369 (2015), based on the total weight of the two-component coating material composition, and the molar ratio of NCO groups in the curing component B to acidic hydrogen atoms of hydroxyl groups, primary amino groups and secondary amino groups in the paint base component A is 1:1.15 to 1:0.95, which allows damage-free release from normally metal mold surfaces without the use of external mold release agents, while ensuring very good adhesion to the substrate, and can be recoated with further coating films, such as base coats and clear coats, forming a surface of very good quality without costly and inconvenient cleaning and/or polishing steps.
  • Patent Document 1 has a low VOC content in the resulting two-component coating composition, but there is a problem in that the time required for cleaning the coating equipment is required when multiple colors are produced.
  • the present invention aims to provide a kit for a three-component paint composition that has a low VOC content, can shorten the process of cleaning the painting equipment when multiple colors are used, and can form a coating film that has excellent hardness and adhesion and suppresses color unevenness.
  • kits for a three-liquid type coating composition comprising a base agent (A) containing an isocyanate-reactive group-containing compound (a1), a curing agent (B) containing a polyisocyanate compound (b1), and a pigment paste (C) containing an isocyanate-reactive group-containing compound (c1) and a pigment (c2), wherein the viscosity (V A ) of the base agent (A) at a shear rate of 100 sec -1 and a temperature of 65°C is within the range of 20 to 1800 mPa ⁇ s, the viscosity (V B ) of the curing agent (B) at a shear rate of 100 sec -1 and a temperature of 65°C is within the range of 20 to 1800 mPa ⁇ s, and the viscosity (V C ) of the pigment paste (C) at a shear rate of 100 sec -1 and a temperature of 65
  • the present invention relates to the following items ⁇ 1> to ⁇ 7>.
  • a kit for a three-component coating composition comprising (A) (a1) a base agent containing an isocyanate-reactive group-containing compound, (B) (b1) a curing agent containing a polyisocyanate compound, and (C) (c1) a pigment paste containing an isocyanate-reactive group-containing compound and (c2) a pigment, wherein the base agent (A) has a viscosity (V A ) at a shear rate of 100 sec -1 and a temperature of 65°C in the range of 20 to 1800 mPa ⁇ s, the curing agent (B) has a viscosity (V B ) at a shear rate of 100 sec -1 and a temperature of 65°C in the range of 20 to 1800 mPa ⁇ s, and the pigment paste (C) has a viscosity (V C ) at a shear rate of 100 sec -1 and a temperature of 65°C in the range of 20 to 1800 mPa ⁇ s.
  • V A
  • ⁇ 2> The three-component coating composition according to ⁇ 1>, having a solid content of 95% by mass or more.
  • ⁇ 3> The kit according to ⁇ 1> or ⁇ 2>, wherein the solid content concentration of the pigment paste (C) is within the range of 85 to 98 mass%.
  • ⁇ 4> The kit according to any one of ⁇ 1> to ⁇ 3>, wherein the isocyanate-reactive group-containing compound (c1) includes an isocyanate-reactive group-containing compound having a number average molecular weight in the range of 250 to 2500.
  • An in-mold coating method comprising a step of injecting an in-mold coating paint composition between a molded substrate and an inner wall of a mold, curing the in-mold coating paint composition, and then removing the coated molded article from the mold, wherein the in-mold coating paint composition is a three-component paint composition formed from the kit described in any one of ⁇ 1> to ⁇ 6>, or the three-component paint composition described in ⁇ 7>.
  • the present invention provides a kit for a three-component paint composition that has a low VOC content, can shorten the process of cleaning the painting equipment when multiple colors are used, and can form a coating film that has excellent hardness and adhesion and suppresses color unevenness.
  • kit for a three-component coating composition is a kit comprising a base agent (A) containing an isocyanate-reactive group-containing compound (a1), a curing agent (B) containing a polyisocyanate compound (b1), and a pigment paste (C) containing an isocyanate-reactive group-containing compound (c1) and a pigment (c2), wherein the viscosity (V A ) of the base agent (A) at a shear rate of 100 sec -1 and a temperature of 65°C is within the range of 20 to 1800 mPa ⁇ s, the viscosity (V B ) of the curing agent (B) at a shear rate of 100 sec -1 and a temperature of 65°C is within the range of 20 to 1800 mPa ⁇ s, and the viscosity (V C ) of the pigment paste
  • kit according to the present invention can form a three-component paint composition that has a low VOC content, can shorten the process of cleaning the painting equipment when multiple colors are used, and can form a coating film that has excellent hardness and adhesion and suppresses color unevenness.
  • pigment paste (C) tank and piping are washed when changing colors, or a pigment paste (C) tank is prepared for each color and only the piping is washed. Since the volume of pigment paste (C) tanks, which are used in small amounts, is often small, when the pigment paste (C) tank and piping are washed, the labor required to wash the small-volume pigment paste (C) tank is small, and when multiple pigment paste (C) tanks are prepared, the pigment paste (C) tanks are small, so the burden on the painting site is small.
  • the present inventors conducted extensive research and found that, when the viscosity (V A ) of the main agent (A) is within the range of 20 to 1800 mPa ⁇ s at a shear rate of 100 sec -1 and a temperature of 65° C., the viscosity (V B ) of the curing agent (B) is within the range of 20 to 1800 mPa ⁇ s at a shear rate of 100 sec -1 and a temperature of 65° C., and the viscosity (V C ) of the pigment paste (C) is within the range of 20 to 1800 mPa ⁇ s at a shear rate of 100 sec -1 and a temperature of 65° C., it is possible to form a coating film that is excellent in hardness and adhesion and has reduced color unevenness, even in the case of a three-component coating composition with a low VOC content.
  • the three-liquid paint composition with low VOC content suppresses color unevenness and has excellent hardness and adhesion. It is presumed that this is because the three liquids of the base agent (A), hardener (B), and pigment paste (C) mix easily, allowing the entire coating to harden uniformly.
  • the solids concentration of the three-component paint composition formed from the kit of the present invention or the three-component paint composition of the present disclosure is preferably 95% by mass or more, more preferably 96% by mass or more, and even more preferably 97% by mass or more, from the viewpoints of reducing the VOC content in the resulting paint composition and preventing hardness and color unevenness of the coating film formed.
  • the upper limit of the solids concentration is 100% by mass.
  • solid content refers to non-volatile components such as resins, hardeners, and pigments that remain after drying at 80°C for 30 minutes.
  • the solid content can be determined, for example, by weighing a sample into a heat-resistant container such as an aluminum foil cup, spreading the sample on the bottom of the container, drying at 80°C for 30 minutes, and weighing the mass of the components remaining after drying.
  • solid content concentration means the mass ratio of the above solid content in the composition. Therefore, the solid content concentration of the composition can be calculated, for example, by weighing out 1.0 g of the composition into a heat-resistant container such as an aluminum foil cup, spreading the composition on the bottom of the container, drying at 80°C for 30 minutes, weighing the mass of the components in the composition remaining after drying, and determining the ratio of the mass of the components remaining after drying to the total mass of the composition before drying.
  • the viscosity (V A ) of the base agent (A) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. and the viscosity (V B ) of the curing agent (B) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. are determined from the viewpoints of hardness and adhesion of the coating film to be formed, etc. It is more preferable that 0.4 ⁇ (V B )/(V A ) ⁇ 2.0 is satisfied, It is more preferable that 0.4 ⁇ (V B )/(V A ) ⁇ 1.5 is satisfied.
  • the viscosity (V A ) of the base agent (A) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. and the viscosity (V C ) of the pigment paste (C) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. are determined from the viewpoint of color unevenness of the formed coating film, etc. It is more preferable that 0.3 ⁇ (V C )/(V A ) ⁇ 2.5 is satisfied, It is more preferable that 0.4 ⁇ (V C )/(V A ) ⁇ 2.0 is satisfied.
  • the main component (A) contains an isocyanate-reactive group-containing compound (a1).
  • the isocyanate-reactive group-containing compound (a1) is a compound having at least one isocyanate-reactive group in one molecule.
  • the isocyanate-reactive group is not particularly limited as long as it is a group that is reactive with an isocyanate group.
  • examples of the isocyanate-reactive group include a hydroxyl group, an amino group, and a thiol group. From the viewpoint of the hardness, adhesion, and color unevenness of the coating film to be formed, it is preferable that the isocyanate-reactive group contains at least one selected from a hydroxyl group and an amino group, and it is more preferable that the isocyanate-reactive group contains a hydroxyl group.
  • examples of the isocyanate-reactive group-containing compound (a1) include a hydroxyl group-containing compound (a11), an amino group-containing compound (a12), a thiol group-containing compound (a13), etc., and from the viewpoint of the hardness, adhesion, and color unevenness of the coating film to be formed, it is preferable to include at least one compound selected from the hydroxyl group-containing compound (a11) and the amino group-containing compound (a12), and it is more preferable to include the hydroxyl group-containing compound (a11).
  • the above-mentioned isocyanate-reactive group-containing compound (a1) preferably contains an isocyanate-reactive group-containing compound having a number average molecular weight in the range of 250 to 2500, more preferably in the range of 300 to 1800, and even more preferably in the range of 300 to 1500, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl-containing compound (a11) is a compound having at least one hydroxyl group in one molecule.
  • the hydroxyl-containing compound (a11) includes, for example, hydroxyl-containing polyester resin, hydroxyl-containing polycaprolactone resin, hydroxyl-containing polyether resin, hydroxyl-containing polycarbonate resin, hydroxyl-containing acrylic resin, hydroxyl-containing polyurethane resin, hydroxyl-containing epoxy resin, hydroxyl-containing alkyd resin, etc., and among them, from the viewpoints of reducing the VOC content in the obtained coating composition, and the hardness, adhesion and color unevenness of the coating film formed, it is preferable to include at least one resin selected from hydroxyl-containing polyester resin, hydroxyl-containing polycaprolactone resin and hydroxyl-containing polyether resin, and more preferably to include at least one resin selected from hydroxyl-containing polyester resin and hydroxyl-containing polycaprolactone resin.
  • Each of these can be
  • the above hydroxyl-containing polyester resin can usually be produced by an esterification reaction or transesterification reaction between an acid component and an alcohol component.
  • the acid component compounds that are commonly used as polycarboxylic acids in the production of the hydroxyl group-containing polyester resin can be used.
  • examples of such polycarboxylic acids include aliphatic polybasic acids, alicyclic polybasic acids, and aromatic polybasic acids.
  • the above-mentioned aliphatic polybasic acids are generally aliphatic compounds having two or more carboxyl groups in one molecule, acid anhydrides of the aliphatic compounds, and esters of the aliphatic compounds.
  • the aliphatic polybasic acids include aliphatic polycarboxylic acids such as succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, octadecanedioic acid, citric acid, and butanetetracarboxylic acid; anhydrides of the aliphatic polybasic acids; and lower alkyl esters of the aliphatic polybasic carboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
  • the above-mentioned aliphatic polybasic acids can be used alone or in combination of two or
  • the alicyclic polybasic acid is generally a compound having one or more alicyclic structures and two or more carboxyl groups in one molecule, an acid anhydride of the compound, and an esterification product of the compound.
  • the alicyclic structure can be mainly a 4- to 6-membered ring structure.
  • alicyclic polybasic acid examples include alicyclic polybasic carboxylic acids such as 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, 3-methyl-1,2-cyclohexanedicarboxylic acid, 4-methyl-1,2-cyclohexanedicarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, and 1,3,5-cyclohexanetricarboxylic acid; anhydrides of the alicyclic polybasic carboxylic acids; and lower alkyl esters of the alicyclic polybasic carboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
  • the above alicyclic polybasic acids can be used alone or in combination of two or more kinds.
  • the aromatic polybasic acids are generally aromatic compounds having two or more carboxyl groups in one molecule, acid anhydrides of the aromatic compounds, and esters of the aromatic compounds.
  • aromatic polybasic acids include aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, 4,4'-biphenyldicarboxylic acid, trimellitic acid, and pyromellitic acid; anhydrides of the aromatic polycarboxylic acids; and lower alkyl esters of the aromatic polycarboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
  • the aromatic polybasic acids can be used alone or in combination of two or more kinds.
  • acid components other than the above-mentioned aliphatic polybasic acids, alicyclic polybasic acids, and aromatic polybasic acids can also be used.
  • Such acid components are not particularly limited, and examples thereof include fatty acids such as coconut oil fatty acid, cottonseed oil fatty acid, hempseed oil fatty acid, rice bran oil fatty acid, fish oil fatty acid, tall oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, tung oil fatty acid, rapeseed oil fatty acid, castor oil fatty acid, dehydrated castor oil fatty acid, and safflower oil fatty acid; monocarboxylic acids such as isononanoic acid, neodecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, benzoic acid, p-tert-butylbenzoic acid, cyclohex
  • a polyhydric alcohol having two or more hydroxyl groups in one molecule can be suitably used.
  • the polyhydric alcohol include ethylene glycol, propylene glycol, diethylene glycol, trimethylene glycol, tetraethylene glycol, triethylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, 3-methyl-1,2-butanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,2-pentanediol, 1 ,5-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,3-dimethyltrimethylene glycol, tetramethylene glycol, 3-methyl-4,3-pentanediol,
  • Alcohol components other than the above polyhydric alcohols can also be used.
  • examples of such alcohol components include, but are not limited to, monoalcohols such as methanol, ethanol, propyl alcohol, butyl alcohol, isobutyl alcohol, pentyl alcohol, 2-ethylhexyl alcohol, stearyl alcohol, benzyl alcohol, phenethyl alcohol, and 2-phenoxyethanol; and alcohol compounds obtained by reacting monoepoxy compounds such as propylene oxide, butylene oxide, and "Cardura E10P" (product name, manufactured by Hexion, glycidyl ester of synthetic highly branched saturated fatty acid) with an acid.
  • monoalcohols such as methanol, ethanol, propyl alcohol, butyl alcohol, isobutyl alcohol, pentyl alcohol, 2-ethylhexyl alcohol, stearyl alcohol, benzyl alcohol, phenethyl alcohol, and 2-phenoxyethanol
  • monoepoxy compounds
  • the method for producing the hydroxyl-containing polyester resin is not particularly limited, and can be carried out according to a conventional method.
  • the acid component and the alcohol component are heated in a nitrogen gas flow at about 150 to 250°C for about 5 to 10 hours, and an esterification reaction or transesterification reaction between the acid component and the alcohol component is carried out to produce the hydroxyl-containing polyester polyol resin.
  • the acid component and the alcohol component are subjected to an esterification reaction or an ester exchange reaction, these components may be added to a reaction vessel at once, or one or both may be added in several portions.
  • the hydroxyl-containing polyester resin may be first synthesized, and then the resulting hydroxyl-containing polyester resin may be reacted with an acid anhydride to half-esterify it into a carboxyl- and hydroxyl-containing polyester resin.
  • the carboxyl-containing polyester resin may be first synthesized, and then the alcohol component may be added to produce the hydroxyl-containing polyester resin.
  • a catalyst known per se such as dibutyltin oxide, antimony trioxide, zinc acetate, manganese acetate, cobalt acetate, calcium acetate, lead acetate, tetrabutyl titanate, or tetraisopropyl titanate, can be used as a catalyst to promote the reaction.
  • the hydroxyl-containing polyester resin may be modified with a fatty acid, a monoepoxy compound, a polyisocyanate compound, or the like during or after the production of the resin.
  • fatty acids include coconut oil fatty acids, cottonseed oil fatty acids, hempseed oil fatty acids, rice bran oil fatty acids, fish oil fatty acids, tall oil fatty acids, soybean oil fatty acids, linseed oil fatty acids, tung oil fatty acids, rapeseed oil fatty acids, castor oil fatty acids, dehydrated castor oil fatty acids, safflower oil fatty acids, and the like.
  • An example of the monoepoxy compound that can be suitably used is "Cardura E10P" (trade name, manufactured by Hexion, glycidyl ester of synthetic highly branched saturated fatty acid).
  • the polyisocyanate compounds include, for example, aliphatic diisocyanate compounds such as lysine diisocyanate, hexamethylene diisocyanate, and trimethylhexane diisocyanate; alicyclic diisocyanate compounds such as hydrogenated xylylene diisocyanate, isophorone diisocyanate, methylcyclohexane-2,4-diisocyanate, methylcyclohexane-2,6-diisocyanate, 4,4'-methylenebis(cyclohexylisocyanate), 1,3-(isocyanatomethyl)cyclohexane, and 1,4-(isocyanatomethyl)cyclohexane; tolylene
  • the polyisocyanate include aromatic diisocyanate compounds such as diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, and diphenylmethane diisocyanate
  • the hydroxyl value of the hydroxyl-containing polyester resin is preferably within the range of 50 to 800 mgKOH/g, more preferably within the range of 100 to 700 mgKOH/g, and even more preferably within the range of 300 to 600 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl-containing polyester resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 350 to 1500, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film to be formed.
  • the glass transition temperature (Tg) of the hydroxyl-containing polyester resin is preferably within the range of -80 to 10°C, more preferably within the range of -70 to 5°C, and even more preferably within the range of -60 to 0°C, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc.
  • the number average molecular weight and the weight average molecular weight are values obtained by converting the retention time (retention volume) measured using a gel permeation chromatograph (GPC) into the molecular weight of polystyrene using the retention time (retention volume) of a standard polystyrene with a known molecular weight measured under the same conditions.
  • GPC gel permeation chromatograph
  • the gel permeation chromatograph uses "HLC-8120GPC” (trade name, manufactured by Tosoh Corporation), and uses a total of four columns, “TSKgel G4000HXL”, “TSKgel G3000HXL”, “TSKgel G2500HXL” and “TSKgel G2000HXL” (trade names, all manufactured by Tosoh Corporation), and uses a differential refractometer as a detector.
  • the mobile phase is tetrahydrofuran, the measurement temperature is 40° C., and the flow rate is 1 mL/min.
  • the glass transition temperature can be measured, for example, using a differential scanning calorimeter "DSC-50Q" (Shimadzu Corporation, product name), by placing the sample in a measuring cup, vacuum suctioning to completely remove the solvent, and then measuring the change in heat quantity in the range of -100°C to 150°C at a heating rate of 3°C/min, and taking the first change in the baseline on the low temperature side as the static glass transition temperature.
  • DSC-50Q differential scanning calorimeter
  • the content of the hydroxyl-containing polyester resin is preferably within the range of 50 to 100 mass%, more preferably within the range of 60 to 95 mass%, and even more preferably within the range of 70 to 90 mass%, based on the total solid content of the hydroxyl-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing polycaprolactone resin can be obtained, for example, by ring-opening polymerization of ⁇ -caprolactone using a dihydric to tetrahydric polyhydric alcohol as an initiator.
  • the dihydric or higher polyhydric alcohol include polyhydric alcohol compounds obtained by reacting ethylene glycol, glycerin, trimethylolethane, trimethylolpropane, diglycerin, ditrimethylolpropane, 1,2,6-hexanetriol, pentaerythritol, tris(2-hydroxyethyl)isocyanuric acid, and dimethylolalkanoic acid with a monoepoxy compound (for example, "Cardura E10P; glycidyl ester of synthetic highly branched saturated fatty acid” manufactured by HEXION Specialty Chemicals).
  • a monoepoxy compound for example, "Cardura E10P; glycidyl ester of synthetic highly branched saturated
  • the hydroxyl group-containing polycaprolactone resin may be a commercially available product, such as "PLACCEL 205", “PLACCEL 205H”, “PLACCEL L205AL”, “PLACCEL 205U”, “PLACCEL 208", “PLACCEL 210", “PLACCEL 210N”, “PLACCEL 210CP”, “PLACCEL 212”, “PLACCEL L212AL”, “PLACCEL 220", “PLACCEL 220N”, “PLACCEL 220CPB”, “PLACCEL 220CPT", “PLACCEL 220L ...
  • the hydroxyl value of the hydroxyl-containing polycaprolactone resin is preferably within the range of 50 to 900 mgKOH/g, more preferably within the range of 100 to 750 mgKOH/g, and even more preferably within the range of 130 to 600 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl group-containing polycaprolactone resin is preferably within the range of 250 to 2500, more preferably within the range of 280 to 1500, and even more preferably within the range of 300 to 1000, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film to be formed.
  • the content of the hydroxyl-containing polycaprolactone resin is preferably within the range of 5 to 100 mass %, more preferably within the range of 10 to 75 mass %, and even more preferably within the range of 10 to 50 mass %, based on the total solid content of the hydroxyl-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, and the like of the coating film to be formed.
  • hydroxyl group-containing polyether resin examples include alkylene oxide adducts of hydroxyl group-containing monomers described below, ring-opening (co)polymers of alkylene oxides or cyclic ethers (such as tetrahydrofuran), etc. Specific examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, (block or random) copolymers of ethylene glycol-propylene glycol, polyhexamethylene glycol, polyoctamethylene glycol, etc.
  • the hydroxyl group-containing polyether resins may be used alone or in combination of two or more.
  • the hydroxyl value of the hydroxyl-containing polyether resin is preferably within the range of 50 to 600 mgKOH/g, more preferably within the range of 70 to 500 mgKOH/g, and even more preferably within the range of 90 to 400 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl group-containing polyether resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1500, and even more preferably within the range of 350 to 1000, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polyether resin is preferably within the range of 20 to 100 mass%, more preferably within the range of 40 to 100 mass%, and even more preferably within the range of 50 to 100 mass%, based on the total solid content of the hydroxyl-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing polycarbonate resin is a compound obtained by a conventional polycondensation reaction between a known polyol component and a carbonylating agent.
  • the polyol component include a diol component and a polyhydric alcohol component such as a trihydric or higher alcohol.
  • the diol components include linear diols such as 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, and 1,10-decanediol; 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 2-ethyl-1,6-hexanediol, 2,2-diethyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-methyl-1,8-octanediol, 2,2
  • suitable diols include branched diols such as 1,3-cyclohexanediol, 1,
  • the trihydric or higher alcohols include glycerin, trimethylolethane, trimethylolpropane, a dimer of trimethylolpropane, and pentaerythritol; polylactone polyols obtained by adding lactone compounds such as ⁇ -caprolactone to these trihydric or higher alcohols; and the like. These trihydric or higher alcohols can be used alone or in combination of two or more kinds.
  • the carbonylating agent may be any known agent. Specific examples include alkylene carbonate, dialkyl carbonate, diallyl carbonate, phosgene, etc., and one or more of these may be used in combination. Among these, preferred examples include ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, diphenyl carbonate, etc.
  • the hydroxyl value of the hydroxyl-containing polycarbonate resin is preferably within the range of 50 to 800 mgKOH/g, more preferably within the range of 70 to 700 mgKOH/g, and even more preferably within the range of 90 to 600 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film to be formed.
  • the number average molecular weight of the hydroxyl group-containing polycarbonate resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 400 to 1500, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polycarbonate resin is preferably within the range of 5 to 80 mass%, more preferably within the range of 10 to 50 mass%, and even more preferably within the range of 10 to 40 mass%, based on the total solid content of the hydroxyl-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl-containing acrylic resin can be produced, for example, by copolymerizing a hydroxyl-containing polymerizable unsaturated monomer and another polymerizable unsaturated monomer that is copolymerizable with the hydroxyl-containing polymerizable unsaturated monomer by a method known per se, such as a solution polymerization method in an organic solvent or an emulsion polymerization method in water.
  • the hydroxyl-containing polymerizable unsaturated monomer is a compound having one or more hydroxyl groups and one or more polymerizable unsaturated bonds in one molecule.
  • the hydroxyl-containing polymerizable unsaturated monomer include monoesters of (meth)acrylic acid and dihydric alcohols having 2 to 8 carbon atoms, such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate; ⁇ -caprolactone-modified monoesters of (meth)acrylic acid and dihydric alcohols having 2 to 8 carbon atoms; N-hydroxymethyl (meth)acrylamide; allyl alcohol; and (meth)acrylates having a polyoxyethylene chain with a hydroxyl group at the molecular end.
  • monomers that fall under the category of (xvii) polymerizable unsaturated monomers having an ultraviolet absorbing functional group described below should be defined as other polymerizable unsaturated monomers that are copolymerizable with the above-mentioned hydroxyl group-containing polymerizable unsaturated monomers, and are excluded from hydroxyl group-containing polymerizable unsaturated monomers. These can be used alone or in combination of two or more kinds.
  • polymerizable unsaturated monomers that can be copolymerized with the above-mentioned hydroxyl group-containing polymerizable unsaturated monomers include, for example, the following monomers (i) to (xx). These polymerizable unsaturated monomers can be used alone or in combination of two or more kinds.
  • Alkyl or cycloalkyl (meth)acrylates for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, tridecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate
  • Nitrogen-containing polymerizable unsaturated monomers (meth)acrylonitrile, (meth)acrylamide, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, methylene bis(meth)acrylamide, ethylene bis(meth)acrylamide, and adducts of glycidyl (meth)acrylate and amine compounds.
  • (xii) Polymerizable unsaturated monomers having two or more polymerizable unsaturated groups in one molecule: allyl (meth)acrylate, ethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, etc.
  • Epoxy group-containing polymerizable unsaturated monomers glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3,4-epoxycyclohexylethyl (meth)acrylate, 3,4-epoxycyclohexylpropyl (meth)acrylate, allyl glycidyl ether, and the like.
  • (xiv) (meth)acrylates having a polyoxyethylene chain with an alkoxy group at the molecular terminal glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3,4-epoxycyclohexylethyl (meth)acrylate, 3,4-epoxycyclohexylpropyl (meth)acrylate, allyl gly
  • (xv) Polymerizable unsaturated monomers having a sulfonic acid group: 2-acrylamido-2-methylpropanesulfonic acid, 2-sulfoethyl (meth)acrylate, allylsulfonic acid, 4-styrenesulfonic acid, and the like; sodium salts and ammonium salts of these sulfonic acids.
  • (xvii) Polymerizable unsaturated monomers having an ultraviolet absorbing functional group: 2-hydroxy-4-(3-methacryloyloxy-2-hydroxypropoxy)benzophenone, 2-hydroxy-4-(3-acryloyloxy-2-hydroxypropoxy)benzophenone, 2,2'-dihydroxy-4-(3-methacryloyloxy-2-hydroxypropoxy)benzophenone, 2,2'-dihydroxy-4-(3-acryloyloxy-2-hydroxypropoxy)benzophenone, 2-(2'-hydroxy-5'-methacryloyloxyethylphenyl)-2H-benzotriazole, and the like.
  • Light-stable polymerizable unsaturated monomers 4-(meth)acryloyloxy-1,2,2,6,6-pentamethylpiperidine, 4-(meth)acryloyloxy-2,2,6,6-tetramethylpiperidine, 4-cyano-4-(meth)acryloylamino-2,2,6,6-tetramethylpiperidine, 1-(meth)acryloyl-4-(meth)acryloylamino-2,2,6,6-tetramethylpiperidine, 1-(meth)acryloyl-4-cyano-4-(meth)acryloylamino-2,2,6,6-tetramethylpiperidine, 4-crotonoyloxy-2,2,6,6-tetramethylpiperidine, 4-crotonoylamino-2,2,6,6-tetramethylpiperidine, 1-crotonoyl-4-crotonoyloxy-2,2,6,6-tetramethylpiperidine, and the like.
  • (xix) Polymerizable unsaturated monomers having a carbonyl group: acrolein, diacetone acrylamide, diacetone methacrylamide, acetoacetoxyethyl methacrylate, formyl styrene, vinyl alkyl ketones having 4 to 7 carbon atoms (for example, vinyl methyl ketone, vinyl ethyl ketone, vinyl butyl ketone), and the like.
  • (xx) Polymerizable unsaturated monomers having an acid anhydride group: maleic anhydride, itaconic anhydride, citraconic anhydride, etc.
  • a polymerizable unsaturated group refers to an unsaturated group that can undergo radical polymerization.
  • examples of such polymerizable unsaturated groups include vinyl groups, (meth)acryloyl groups, (meth)acrylamide groups, vinyl ether groups, allyl groups, propenyl groups, isopropenyl groups, and maleimide groups.
  • (meth)acrylate means acrylate and/or methacrylate.
  • (meth)acrylic acid means acrylic acid and/or methacrylic acid.
  • (meth)acryloyl means acryloyl and/or methacryloyl.
  • (meth)acrylamide means acrylamide and/or methacrylamide.
  • the hydroxyl value of the hydroxyl-containing acrylic resin is preferably within the range of 5 to 240 mgKOH/g, more preferably within the range of 20 to 220 mgKOH/g, and even more preferably within the range of 25 to 200 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film to be formed.
  • the number average molecular weight of the hydroxyl-containing acrylic resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 500 to 1500, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the glass transition temperature (Tg) of the hydroxyl-containing acrylic resin is preferably within the range of -60 to 80°C, more preferably within the range of -50 to 70°C, and even more preferably within the range of -40 to 60°C, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • W1, W2, ... Wn are the mass fractions of each monomer
  • T1, T2 ... Tn are the glass transition temperatures Tg (K) of the homopolymers of each monomer.
  • the glass transition temperature of the homopolymer of each monomer is the value according to POLYMER HANDBOOK Fourth Edition, edited by J. Brandrup, E. h. Immergut, and E. A. Grulke (1999).
  • the glass transition temperature of a monomer not described in the document is the value according to POLYMER HANDBOOK Fourth Edition, edited by J. Brandrup, E. h. Immergut, and E. A. Grulke (1999).
  • the static glass transition temperature is determined as the temperature when the polymer is synthesized so that the static glass transition temperature is about 10,000.
  • the content of the hydroxyl-containing acrylic resin is preferably within the range of 5 to 100 mass%, more preferably within the range of 10 to 75 mass%, and even more preferably within the range of 15 to 50 mass%, based on the total solid content of the hydroxyl-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • examples of the hydroxyl group-containing compound (a11) include hydroxyl group-containing monomers such as ethylene glycol, propylene glycol, diethylene glycol, trimethylene glycol, tetraethylene glycol, triethylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, and 3-methyl-1,2-butanediol.
  • hydroxyl group-containing monomers such as ethylene glycol, propylene glycol, diethylene glycol, trimethylene glycol, tetraethylene glycol, triethylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, and 3-methyl-1,2-but
  • the content of the hydroxyl group-containing monomer is preferably within the range of 5 to 100 mass %, more preferably within the range of 5 to 50 mass %, and even more preferably within the range of 5 to 30 mass %, based on the total solid content of the hydroxyl group-containing compound (a11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl group-containing compound (a11) is preferably within the range of 50 to 100 mass%, more preferably within the range of 60 to 100 mass%, and even more preferably within the range of 70 to 100 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (a1), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • amino group-containing compound (a12) is a compound having at least one primary amino group and/or secondary amino group in the molecule.
  • the amino group-containing compound (a12) may, for example, be an aliphatic polyamine such as ethylenediamine, pentamethylenediamine, hexamethylenediamine, trimethylhexamethylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, N,N'-bis-(3-aminopropyl)ethylenediamine, or tetraethylenepentamine; 1,2-cyclohexanediamine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, 4-methyl-1,3-cyclohexanediamine, 2-methyl-1,3-cyclohexanediamine, isophoronediamine, 4,4'-methylenebis(cyclohexylamine), 3,3'-dimethyl-4,4'-methylenebis(cyclohexylamine), or N,N'- Alicyclic polyamines such as (isophoronediamino)bispropionitrile, N,N'-di-sec
  • polyaspartic acid ester compounds examples include tetraethyl, N,N'-[methylenebis(cyclohexane-4,1-diyl)]bisaspartate tetraethyl, N,N'-[methylenebis(2-methylcyclohexane-4,1-diyl)]bisaspartate tetraethyl, ⁇ - ⁇ 2-[(1,4-diethoxy-1,4-dioxobutan-2-yl)amino]propyl ⁇ - ⁇ - ⁇ 2-[(1,4-diethoxy-1,4-dioxobutan-2-yl)amino]propoxy ⁇ poly[oxy(methylethylene)]; and aminosilane compounds such as N- ⁇ (aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl)- ⁇ -aminopropylmethyldimethoxysilane, and
  • the amino group-containing compound (a12) preferably contains at least one compound selected from aliphatic polyamines, alicyclic polyamines, polyether polyamine compounds, and polyaspartic acid ester compounds, more preferably contains at least one compound selected from alicyclic polyamines and polyaspartic acid esters, and even more preferably contains a polyaspartic acid ester compound, from the viewpoints of reducing the VOC content in the resulting coating composition, and of the hardness, adhesion, and color unevenness of the coating film formed.
  • polyaspartic acid ester compound examples include Desmophen NH1220, Desmophen NH1420, Desmophen NH1422, Desmophen NH1423, Desmophen NH1520, Desmophen NH1521, and Desmophen NH1522.
  • the content of the amino group-containing compound (a12) is preferably within the range of 10 to 100 mass%, more preferably within the range of 40 to 95 mass%, and even more preferably within the range of 50 to 90 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (a1), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the thiol group-containing compound (a13) is a compound having at least one thiol group in one molecule.
  • Examples of the thiol group-containing compound (a13) include pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, tetraethylene glycol bis(3-mercaptopropionate), tetramethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), trimethylolpropane dipropanethiol, pentaerythritol hexakis(3-mercaptopropionate), trimethylolpropane dipropanethiol, Examples include erythritol tripropanethiol, pentaerythritol tetrapropanethiol, 1,4-bis(mercaptomethyl)benzene
  • the content of the thiol group-containing compound (a13) is preferably within the range of 10 to 100 mass%, more preferably within the range of 30 to 95 mass%, and even more preferably within the range of 50 to 90 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (a1), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the isocyanate-reactive group-containing compound (a1) in the main component (A) is preferably within the range of 30 to 99.5% by mass, more preferably within the range of 50 to 99% by mass, and even more preferably within the range of 70 to 98% by mass, based on the total amount of the main component (A), from the viewpoints of reducing the VOC content in the resulting coating composition, and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the main component (A) may further contain an ultraviolet absorbing agent and/or a light stabilizer, and may also contain other additives, such as an internal mold release agent, a solvent (organic solvent, water), a pigment, a catalyst, a dehydrating agent, an antioxidant, a surface conditioner, an antifoaming agent, an emulsifier, a surfactant, an antifouling agent, a wetting agent, a thickener, a dye, an anti-scratch agent, a gloss adjuster, etc., that are commonly used in the field of coating.
  • an ultraviolet absorbing agent and/or a light stabilizer may also contain other additives, such as an internal mold release agent, a solvent (organic solvent, water), a pigment, a catalyst, a dehydrating agent, an antioxidant, a surface conditioner, an antifoaming agent, an emulsifier, a surfactant, an antifouling agent, a wetting agent, a thickener, a dye, an anti-
  • UV absorbing agent a conventionally known agent can be used, for example, a benzotriazole-based absorbent, a triazine-based absorbent, a salicylic acid derivative-based absorbent, a benzophenone-based absorbent, etc.
  • the ultraviolet absorbing agent may have a polymerizable unsaturated group.
  • benzotriazole-based absorbents include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-t-butylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole.
  • Examples include benzotriazole, 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole, 2-(2'-hydroxy-4'-octoxyphenyl)benzotriazole, 2- ⁇ 2'-hydroxy-3'-(3",4",5",6"-tetrahydrophthalimidomethyl)-5'-methylphenyl ⁇ benzotriazole, and 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole.
  • triazine-based absorbents include 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-isooctyloxyphenyl)-1,3,5-triazine, 2-[4((2-hydroxy-3-dodecyloxypropyl)-oxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-((2-hydroxy-3-tridecyloxypropyl)-oxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, and 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.
  • salicylic acid derivative-based absorbents include phenyl salicylate, p-octylphenyl salicylate, and 4-tert-butylphenyl salicylate.
  • benzophenone-based absorbents include 4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone trihydrate, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, and naphthalene.
  • Examples include thorium 2,2'-dihydroxy-4,4'-dimethoxy-5-sulfobenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 5-chloro-2-hydroxybenzophenone, resorcinol monobenzoate, 2,4-dibenzoylresorcinol, 4,6-dibenzoylresorcinol, hydroxydodecylbenzophenone, and 2,2'-dihydroxy-4(3-methacryloxy-2-hydroxypropoxy)benzophenone.
  • ultraviolet absorbents include "TINUVIN 1130", “TINUVIN 900”, “TINUVIN 928”, “TINUVIN 384-2”, “TINUVIN 479”, “TINUVIN 477”, “TINUVIN 405", "TINUVIN 400” (product names manufactured by BASF, TINUVIN is a registered trademark), and "RUVA 93” (product name manufactured by Otsuka Chemical Co., Ltd.).
  • the content of the ultraviolet absorber is preferably within the range of 0.5 to 10 mass %, more preferably within the range of 0.8 to 5.0 mass %, and even more preferably within the range of 1.0 to 4.0 mass %, based on the total amount of the main component (A), from the viewpoint of the weather resistance and adhesion of the coating film to be formed.
  • the light stabilizer is used as a radical chain inhibitor that captures active radical species generated during the deterioration process of the coating film, and examples thereof include light stabilizers of hindered amine compounds.
  • hindered amine compounds include bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidinyl)sebacate, bis(N-methyl-2,2,6,6-tetramethyl-4-piperidinyl)sebacate, 4-benzoyloxy-2,2',6,6'-tetramethylpiperidine, bis(1,2,2,6,6-pentamethyl-4-piperidyl) ⁇ [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl ⁇ butylmalonate
  • Examples of the light stabilizer include, but are not limited to, monomeric types such as poly([6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidyl)imino]hexamethylene[(2,2,6,6-t
  • light stabilizers include, for example, "TINUVIN 123", “TINUVIN 152", “TINUVIN 249", “TINUVIN 292” (BASF product names, TINUVIN is a registered trademark), "HOSTAVIN 3058” (Clariant product names, Hostavin is a registered trademark), and "ADEKA STAB LA-82" (ADEKA Corporation product names, ADEKA STAB is a registered trademark).
  • the content of the light stabilizer is preferably within the range of 0.5 to 10 mass %, more preferably within the range of 0.8 to 9.0 mass %, and even more preferably within the range of 1.0 to 8.0 mass %, based on the total amount of the main component (A), from the viewpoint of the weather resistance and adhesion of the coating film to be formed.
  • the main component (A) contains an internal mold release agent from the viewpoint of the releasability between the formed coating film and the mold.
  • the above internal mold release agents include, for example, saturated fatty acids such as stearic acid and palmitic acid; saturated fatty acid salts such as zinc stearate, aluminum stearate, magnesium stearate, calcium stearate, sodium stearate, potassium stearate, barium stearate, zinc palmitate, aluminum palmitate, magnesium palmitate, calcium palmitate, and sodium palmitate; lauric acid amide, myristic acid amide, palmitic acid amide, stearic acid amide, N,N-dimethyllauric acid amide, N,N-dimethylmyristic acid amide, N,N-dimethylpalmitic acid amide, N,N-dimethylstearic acid amide, N,N-diethyllauric acid amide, N,N-diethyl ...
  • saturated fatty acids such as stearic acid and palmitic acid
  • saturated fatty acid salts such as zinc stearate, aluminum stearate, magnesium stearate
  • Saturated fatty acid amides such as ristinoamide, N,N-diethylpalmitamide, and N,N-diethylstearamide; unsaturated fatty acids such as palmitoleic acid and oleic acid; unsaturated fatty acid salts such as zinc palmitoleate, aluminum palmitoleate, magnesium palmitoleate, calcium palmitoleate, sodium palmitoleate, potassium palmitoleate, barium palmitoleate, zinc oleate, aluminum oleate, magnesium oleate, calcium oleate, sodium oleate, potassium oleate, and barium oleate; palmitoleic acid amide, oleic acid amide, erucic acid amide, behenic acid amide, N-oleyl palmitic acid amide, and N-stearyl erucic acid amide unsaturated fatty acid amides such as N,N-dimethyloleic acid amide, and N,N-
  • fatty acid esters include fatty acid esters such as behenic acid monoglyceride, behenic acid diglyceride, behenic acid triglyceride, behenyl behenate, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, stearyl stearate, palmityl palmitate, methyl stearate, butyl stearate, methyl laurate, methyl palmitate, isopropyl palmitate, biphenyl biphenate, sorbitan monostearate, and 2-ethylhexyl stearate; soybean oil lecithin, silicone oil, and fatty acid alcohol dibasic acid esters, which can be used alone or in combination of two or more.
  • soybean oil lecithin silicone oil
  • fatty acid alcohol dibasic acid esters which can be used alone or
  • the content of the internal release agent is preferably within the range of 0.4 to 5.0 mass%, more preferably within the range of 0.5 to 4.0 mass%, and even more preferably within the range of 0.5 to 3.0 mass%, based on the total amount of the main component (A), from the viewpoints of the adhesion of the coating film to be formed and the releasability of the coating film to be formed from the mold.
  • solvents examples include organic solvents, water, etc.
  • organic solvent examples include ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; ester-based solvents such as ethyl acetate, butyl acetate, methyl benzoate, ethyl ethoxypropionate, ethyl propionate, and methyl propionate; ether-based solvents such as tetrahydrofuran, dioxane, and dimethoxyethane; glycol ether-based solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and 3-methoxybutyl acetate; aromatic solvents such as toluene, xylene, and "Swasol 1000" (trade name, high-boiling
  • the content of the solvent is preferably within the range of 0.1 to 5 mass%, more preferably within the range of 0.3 to 4 mass%, and even more preferably within the range of 0.5 to 3 mass%, based on the total amount of the main component (A).
  • any of the conventionally known catalysts can be used.
  • the catalyst include tin octylate, dibutyltin diacetate, dibutyltin di(2-ethylhexanoate), dibutyltin dilaurate, dioctyltin diacetate, dioctyltin di(2-ethylhexanoate), dioctyltin dineodecanoate, dioctyltin diversatate, dibutyltin oxide, dibutyltin sulfide, dioctyltin oxide, dibutyltin fatty acid salts, lead 2-ethylhexanoate, zinc octylate, zinc naphthenate, zinc fatty acids, bismuth octanoate, bismuth 2-ethylhexanoate, bismuth oleate, bismuth ne
  • DABCO 1,8-diazabicyclo[5.4.0.]-7-undecene
  • DBU 1,5-diazabicyclo[4.3.0.]-5-nonene
  • DBN N-methyl-N'-(2-dimethylaminoethyl)piperazine, N-ethylmorpholine, 1,2-dimethylimidazole, dimethylethanolamine, dimethylaminoethoxyethanol, N-methyl-N'-(2-hydroxyethyl)piperazine, 2-hydroxyethyl-1,4-diazabicyclo[2.2.2.
  • ]octane 1,1'- ⁇ [3-(dimethylamino)propyl]imino ⁇ bis(2-propanol), bis(2-dimethylaminoethyl)ether, bis(2-morpholinoethyl)ether, and other tertiary amine compounds, neutralized salts of the tertiary amine compounds; and quaternary ammonium salts, such as carboxylates of tetraalkylammonium, tetraarylammonium, and alkylarylammonium, and halides of tetraalkylammonium, tetraarylammonium, and alkylarylammonium, and these can be used alone or in combination of two or more kinds.
  • the amount of the catalyst is preferably within the range of 0.005 to 5.0 mass %, and more preferably within the range of 0.01 to 3.0 mass %, based on the total amount of the main component (A).
  • the coating composition of the present invention may contain organic acids such as acetic acid, propionic acid, butyric acid, isopentanoic acid, hexanoic acid, 2-ethylbutyric acid, naphthenic acid, octylic acid, nonanoic acid, decanoic acid, 2-ethylhexanoic acid, isooctanoic acid, isononanoic acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, neodecanoic acid, versatic acid, isobutyric anhydride, itaconic anhydride, acetic anhydride, citraconic anhydride, propionic anhydride, maleic anhydride, butyric anhydride, citric anhydride, trimellitic anhydride, pyromellitic anhydride, and phthalic anhydride; inorganic acids such as hydrochlor
  • the dehydrating agent conventionally known inorganic dehydrating agents and organic dehydrating agents can be used.
  • the inorganic dehydrating agent include calcium compounds such as calcium hydride, calcium oxide (quicklime), calcium chloride, calcium sulfate (gypsum), etc.; barium compounds such as barium oxide, etc.; magnesium compounds such as magnesium sulfate, etc.; sodium compounds such as sodium sulfate, sodium carbonate, etc.; copper compounds such as copper sulfate, etc.; inorganic silicon compounds such as silica gel, etc.; aluminum compounds such as aluminum oxide (hydraulic alumina, lithium aluminum hydride, non-crystalline silica alumina, crystalline aluminosilicates (molecular sieves), etc., and these can be used alone or in combination of two or more kinds.
  • organic dehydrating agent examples include alkyl orthoformates; alkyl orthoacetates; alkyl orthoborates; vinylsilanes; alkoxysilane compounds; monoisocyanate compounds; aliphatic acid anhydrides such as acetic anhydride, and aromatic acid anhydrides such as benzoic anhydride. These can be used alone or in combination of two or more kinds.
  • the amount of the dehydrating agent blended is preferably within the range of 0.1 to 5.0 mass %, and more preferably within the range of 0.3 to 3.0 mass %, based on the total amount of the main component (A).
  • the viscosity (V A ) of the main agent (A) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. is within the range of 20 to 1800 mPa ⁇ s.
  • the viscosity (V A ) of the main agent (A) at a shear rate of 100 sec -1 and a temperature of 65° C. is preferably within the range of 50 to 1500 mPa ⁇ s, more preferably within the range of 100 to 1000 mPa ⁇ s, and even more preferably within the range of 150 to 800 mPa ⁇ s, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film formed.
  • the solids concentration of the main agent (A) is preferably within the range of 95 to 100 mass %, more preferably within the range of 96 to 99.5 mass %, and even more preferably within the range of 97 to 99 mass %, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film to be formed.
  • the content of the main component (A) in the kit according to the present invention and in the three-component paint composition according to the present disclosure is, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, color unevenness, and the like of the coating film to be formed, preferably in the range of 10 to 70 mass %, more preferably in the range of 15 to 60 mass %, and even more preferably in the range of 25 to 50 mass %, based on the total amount of the three-component paint composition.
  • the curing agent (B) contains a polyisocyanate compound (b1).
  • the polyisocyanate compound (b1) is a compound having at least two isocyanate groups in one molecule, and includes, for example, aliphatic polyisocyanates, alicyclic polyisocyanates, araliphatic polyisocyanates, aromatic polyisocyanates, and derivatives of the polyisocyanates.
  • the polyisocyanate compound (b1) preferably contains the aliphatic polyisocyanate from the viewpoints of reducing the VOC content in the resulting coating composition and improving the hardness, adhesion, and color unevenness of the coating film formed.
  • aliphatic polyisocyanates examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, 2,4,4- or 2,2,4-trimethylhexamethylene diisocyanate, dimer acid diisocyanate, methyl 2,6-diisocyanatohexanoate (common name: lysine diisocyanate), aliphatic diisocyanates such as 2,6-diisocyanatohexanoate 2-isocyanatoethyl, 1,6-diisocyanato-3-isocyanatomethylhexane, 1,4,8-triisocyanatooctane, 1,6,11-triisocyanatoundecane, 1,8
  • the alicyclic polyisocyanates include, for example, alicyclic diisocyanates such as 1,3-cyclopentene diisocyanate, 1,4-cyclohexane diisocyanate, 1,3-cyclohexane diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (common name: isophorone diisocyanate), methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 1,3- or 1,4-bis(isocyanatomethyl)cyclohexane (common name: hydrogenated xylylene diisocyanate) or mixtures thereof, and norbornane diisocyanate; 1,3,5-triisocyanatocyclohexane, 1,3,5-trimethylisocyanatocyclohexane, 2-(3-isocyanatopropyl)-2,5-di
  • aromatic aliphatic polyisocyanate examples include aromatic aliphatic diisocyanates such as 1,3- or 1,4-xylylene diisocyanate or mixtures thereof, ⁇ , ⁇ '-diisocyanato-1,4-diethylbenzene, 1,3- or 1,4-bis(1-isocyanato-1-methylethyl)benzene (common name: tetramethylxylylene diisocyanate) or mixtures thereof; and aromatic aliphatic triisocyanates such as 1,3,5-triisocyanatomethylbenzene.
  • aromatic aliphatic diisocyanates such as 1,3- or 1,4-xylylene diisocyanate or mixtures thereof, ⁇ , ⁇ '-diisocyanato-1,4-diethylbenzene, 1,3- or 1,4-bis(1-isocyanato-1-methylethyl)benzene (common name: tetramethylxylylene diiso
  • aromatic polyisocyanate examples include aromatic diisocyanates such as m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4'-diphenyl diisocyanate, 1,5-naphthalene diisocyanate, 2,4'- or 4,4'-diphenylmethane diisocyanate or mixtures thereof, 2,4- or 2,6-tolylene diisocyanate or mixtures thereof, 4,4'-toluidine diisocyanate, and 4,4'-diphenylether diisocyanate; aromatic triisocyanates such as triphenylmethane-4,4',4''-triisocyanate, 1,3,5-triisocyanatobenzene, and 2,4,6-triisocyanatotoluene; and aromatic tetraisocyanates such as 4,4'-diphenylmethane-2,2',5,5'-tetraisocyanate.
  • aromatic diisocyanates such as
  • the derivatives of the polyisocyanate include, for example, dimers, trimers, biurets, allophanates, uretdione, uretonimine, isocyanurates, iminooxadiazinedione, polymethylene polyphenyl polyisocyanates (crude MDI, polymeric MDI), crude TDI, etc., of the polyisocyanate compounds described above.
  • the coating film to be formed it is preferable to include at least one selected from allophanates, uretdione, and isocyanurates, more preferably to include at least one selected from uretdione and isocyanurates, and even more preferably to include isocyanurates.
  • polyisocyanates and their derivatives may be used alone or in combination of two or more.
  • polyisocyanates it is preferable to use aliphatic diisocyanates, aliphatic triisocyanates, alicyclic diisocyanates, araliphatic diisocyanates, and their derivatives alone or in combination of two or more.
  • the polyisocyanate compound (b1) may be a prepolymer obtained by reacting the polyisocyanate or a derivative thereof with a compound capable of reacting with the polyisocyanate under conditions of excess isocyanate groups.
  • the compound capable of reacting with the polyisocyanate include compounds having active hydrogen groups such as hydroxyl groups and amino groups. Specifically, polyhydric alcohols, low molecular weight polyester resins, amines, water, etc. may be used.
  • the polyhydric alcohol the polyhydric alcohols exemplified in the hydroxyl group-containing polyester resin can be used.
  • the polyisocyanate compound (b1) is preferably used in such a ratio that the ratio of the isocyanate groups in the polyisocyanate compound (b1) to the isocyanate reactive groups in the isocyanate reactive group-containing compound (a1) and the isocyanate reactive group-containing compound (c1) described below is in the range of 0.7 to 2.0, and more preferably in the range of 0.9 to 1.5.
  • the content of the polyisocyanate compound (b1) in the curing agent (B) is preferably within the range of 30 to 100 mass%, more preferably within the range of 40 to 99.5 mass%, and even more preferably within the range of 50 to 99 mass%, based on the total amount of the curing agent (B), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the curing agent (B) can further contain a curing agent other than the polyisocyanate compound (b1).
  • the curing agent (B) can appropriately contain other additive components that are usually used in the field of painting, such as ultraviolet absorbers, light stabilizers, internal mold release agents, solvents (organic solvents, water), pigments, catalysts, dehydrating agents, antioxidants, surface conditioners, defoamers, emulsifiers, surfactants, antifouling agents, wetting agents, thickeners, dyes, scratch resistance improvers, gloss adjusters, etc., as necessary.
  • ⁇ Curing Agent Other Than Polyisocyanate Compound (b1)> As the curing agent other than the polyisocyanate compound (b1), for example, a carbodiimide group-containing compound can be mentioned.
  • the carbodiimide group-containing compound is a compound having at least one carbodiimide group in one molecule, and for example, a compound obtained by subjecting isocyanate groups of an isocyanate group-containing compound to a carbon dioxide-removal reaction can be used.
  • a compound having a carbodiimide group and two or more isocyanate groups is not included in the carbodiimide group-containing compound, but is included in the polyisocyanate compound (b1).
  • carbodiimide group-containing compound commercially available products can be used.
  • commercially available product names include “Carbodilite V-02B”, “Elastostab H01”, “Carbodilite V-03”, “Carbodilite V-09”, “Carbodilite V-09GB”, “Carbodilite V-09M”, and “Carbodilite V-04PF” (all of which are product names manufactured by Nisshinbo Chemical Co., Ltd.), “Stabaxol I”, “Stabaxol I LF”, “Stabaxol P", “Stabaxol P100", and “Stabaxol P200” (all of which are product names manufactured by LANXESS Co., Ltd.), etc.
  • the carbodiimide group-containing compound preferably contains a solvent-free carbodiimide group-containing compound from the viewpoints of reducing the VOC content in the resulting coating composition and preventing adhesion and color unevenness of the coating film formed.
  • the number average molecular weight of the carbodiimide group-containing compound is preferably within the range of 500 to 5,000, more preferably within the range of 600 to 3,000, and even more preferably within the range of 700 to 1,500, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the carbodiimide group-containing compound is preferably within the range of 0.5 to 5.0 mass%, more preferably within the range of 0.8 to 4.0 mass%, and even more preferably within the range of 1.0 to 3.0 mass%, based on the total amount of the curing agent (B), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • solvent for example, the solvents exemplified for the main component (A) can be used.
  • the content of the solvent is preferably within the range of 0.1 to 5 mass%, more preferably within the range of 0.2 to 4 mass%, and even more preferably within the range of 0.3 to 3 mass%, based on the total amount of the curing agent (B).
  • ⁇ Dehydrating Agent> As the dehydrating agent, for example, the dehydrating agents exemplified in the main component (A) can be used.
  • the amount of the dehydrating agent is preferably within the range of 0.1 to 5 mass %, and more preferably within the range of 0.3 to 3 mass %, based on the total amount of the curing agent (B).
  • the viscosity (V B ) of the curing agent (B) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. is within the range of 20 to 1800 mPa ⁇ s.
  • the viscosity (V B ) of the curing agent (B) at a shear rate of 100 sec -1 and a temperature of 65° C. is preferably within the range of 50 to 1500 mPa ⁇ s, more preferably within the range of 100 to 1000 mPa ⁇ s, and even more preferably within the range of 150 to 600 mPa ⁇ s, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film formed.
  • the solids concentration of the curing agent (B) is preferably within the range of 95 to 100% by mass, more preferably within the range of 96 to 100% by mass, and even more preferably within the range of 97 to 100% by mass, from the viewpoints of reducing the VOC content in the resulting coating composition, and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the curing agent (B) in the kit according to the present invention and in the three-component paint composition according to the present disclosure is preferably within the range of 20 to 80 mass %, more preferably within the range of 30 to 75 mass %, and even more preferably within the range of 40 to 70 mass %, based on the total amount of the three-component paint composition, from the viewpoints of reducing the VOC content in the resulting paint composition, and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the pigment paste (C) contains an isocyanate-reactive group-containing compound (c1) and a pigment (C2).
  • the isocyanate-reactive group-containing compound (c1) is a compound having at least one isocyanate-reactive group in one molecule.
  • the above-mentioned isocyanate-reactive group-containing compound (c1) preferably contains an isocyanate-reactive group-containing compound having a number average molecular weight in the range of 250 to 2500, more preferably in the range of 300 to 1800, and even more preferably in the range of 300 to 1500, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the isocyanate-reactive group is not particularly limited as long as it is a group that is reactive with an isocyanate group.
  • examples of the isocyanate-reactive group include a hydroxyl group, an amino group, and a thiol group. From the viewpoint of the hardness, adhesion, and color unevenness of the coating film to be formed, it is preferable that the isocyanate-reactive group contains at least one selected from a hydroxyl group and an amino group, and it is more preferable that the isocyanate-reactive group contains a hydroxyl group.
  • examples of the isocyanate-reactive group-containing compound (c1) include a hydroxyl group-containing compound (c11), an amino group-containing compound (c12), a thiol group-containing compound (c13), etc., and from the viewpoint of the hardness, adhesion, and color unevenness of the coating film to be formed, it is preferable to include at least one compound selected from the hydroxyl group-containing compound (c11) and the amino group-containing compound (c12), and it is more preferable to include a hydroxyl group-containing compound (c11).
  • the hydroxyl group-containing compound (c11) is a compound having at least one hydroxyl group in one molecule.
  • the hydroxyl group-containing compound (c11) includes, for example, hydroxyl group-containing polyester resin, hydroxyl group-containing polycaprolactone resin, hydroxyl group-containing polyether resin, hydroxyl group-containing polycarbonate resin, hydroxyl group-containing acrylic resin, hydroxyl group-containing polyurethane resin, hydroxyl group-containing epoxy resin, hydroxyl group-containing alkyd resin, etc., and among them, from the viewpoints of reducing the VOC content in the obtained coating composition, and the hardness, adhesion and color unevenness of the coating film formed, it is preferable to include at least one resin selected from hydroxyl group-containing polyester resin, hydroxyl group-containing polycaprolactone resin and hydroxyl group-containing polyether resin, and more preferably to include at least one resin selected from hydroxyl group-containing polyester resin and hydroxyl
  • the hydroxyl group-containing polyester resin for example, the hydroxyl group-containing polyester resin exemplified in the main component (A) can be used.
  • the hydroxyl value of the hydroxyl-containing polyester resin is preferably within the range of 50 to 800 mgKOH/g, more preferably within the range of 100 to 700 mgKOH/g, and even more preferably within the range of 300 to 600 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl group-containing polyester resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 350 to 1500, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the glass transition temperature (Tg) of the hydroxyl-containing polyester resin is preferably within the range of -80 to 10°C, more preferably within the range of -70 to 5°C, and even more preferably within the range of -60 to 0°C, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polyester resin is preferably within the range of 50 to 100 mass%, more preferably within the range of 60 to 95 mass%, and even more preferably within the range of 75 to 90 mass%, based on the total solid content of the hydroxyl-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing polycaprolactone resin for example, the hydroxyl group-containing polycaprolactone resins exemplified in the main component (A) can be used.
  • the hydroxyl value of the hydroxyl-containing polycaprolactone resin is preferably within the range of 50 to 900 mgKOH/g, more preferably within the range of 100 to 750 mgKOH/g, and even more preferably within the range of 130 to 600 mgKOH/g, from the viewpoints of the hardness and adhesion of the coating film to be formed.
  • the number average molecular weight of the hydroxyl group-containing polycaprolactone resin is preferably within the range of 250 to 2500, more preferably within the range of 280 to 1500, and even more preferably within the range of 300 to 1000, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polycaprolactone resin is preferably within the range of 5 to 100 mass%, more preferably within the range of 10 to 75 mass%, and even more preferably within the range of 10 to 50 mass%, based on the total solid content of the hydroxyl-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing polyether resin for example, the polyether resins exemplified in the main component (A) can be used.
  • the hydroxyl value of the hydroxyl-containing polyether resin is preferably within the range of 50 to 600 mgKOH/g, more preferably within the range of 70 to 500 mgKOH/g, and even more preferably within the range of 90 to 400 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl group-containing polyether resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1500, and even more preferably within the range of 350 to 1000, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polyether resin is preferably within the range of 20 to 100 mass%, more preferably within the range of 40 to 100 mass%, and even more preferably within the range of 50 to 100 mass%, based on the total solid content of the hydroxyl-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing polycarbonate resin for example, the polycarbonate resins exemplified in the main component (A) can be used.
  • the hydroxyl value of the hydroxyl-containing polycarbonate resin is preferably within the range of 50 to 800 mgKOH/g, more preferably within the range of 70 to 700 mgKOH/g, and even more preferably within the range of 90 to 600 mgKOH/g, from the viewpoints of the hardness and adhesion of the coating film to be formed.
  • the number average molecular weight of the hydroxyl group-containing polycarbonate resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 400 to 1500, from the viewpoints of reducing the VOC content in the resulting paint composition and preventing adhesion and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing polycarbonate resin is preferably within the range of 5 to 80 mass%, more preferably within the range of 10 to 50 mass%, and even more preferably within the range of 10 to 40 mass%, based on the total solid content of the hydroxyl-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing acrylic resin for example, the acrylic resins exemplified in the main component (A) can be used.
  • the hydroxyl value of the hydroxyl-containing acrylic resin is preferably within the range of 5 to 240 mgKOH/g, more preferably within the range of 20 to 220 mgKOH/g, and even more preferably within the range of 25 to 200 mgKOH/g, from the viewpoint of the hardness and adhesion of the coating film formed.
  • the number average molecular weight of the hydroxyl-containing acrylic resin is preferably within the range of 250 to 2500, more preferably within the range of 300 to 1800, and even more preferably within the range of 500 to 1500, from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the glass transition temperature (Tg) of the hydroxyl-containing acrylic resin is preferably within the range of -60 to 80°C, more preferably within the range of -50 to 70°C, and even more preferably within the range of -40 to 60°C, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the content of the hydroxyl-containing acrylic resin is preferably within the range of 5 to 100 mass%, more preferably within the range of 10 to 75 mass%, and even more preferably within the range of 15 to 50 mass%, based on the total solid content of the hydroxyl-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the hydroxyl group-containing compound (c11) for example, the hydroxyl group-containing monomers exemplified in the main component (A) can be used.
  • the content of the hydroxyl group-containing monomer is preferably in the range of 5 to 100 mass %, more preferably in the range of 5 to 50 mass %, and even more preferably in the range of 5 to 30 mass %, based on the total solid content of the hydroxyl group-containing compound (c11), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film to be formed.
  • the content of the hydroxyl group-containing compound (c11) is preferably within the range of 50 to 100 mass%, more preferably within the range of 60 to 100 mass%, and even more preferably within the range of 70 to 100 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (c1), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • amino group-containing compound (c12) As the amino group-containing compound (c12), for example, the amino group-containing compound (c12) exemplified in the main component (A) can be used.
  • the isocyanate-reactive group-containing compound (c1) contains the amino group-containing compound (c12)
  • the content of the amino group-containing compound (c12) is preferably within the range of 10 to 100 mass%, more preferably within the range of 40 to 95 mass%, and even more preferably within the range of 50 to 90 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (c1), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film to be formed.
  • the thiol group-containing compound (c13) for example, the thiol group-containing compound (c13) exemplified in the main component (A) can be used.
  • the content of the thiol group-containing compound (c13) is preferably within the range of 10 to 100 mass%, more preferably within the range of 30 to 95 mass%, and even more preferably within the range of 50 to 90 mass%, based on the total solid content of the isocyanate-reactive group-containing compound (c1), from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, and color unevenness of the coating film to be formed.
  • the content of the isocyanate-reactive group-containing compound (c1) in the pigment paste (C) is preferably within the range of 10 to 99 mass %, more preferably within the range of 15 to 90 mass %, and even more preferably within the range of 20 to 80 mass %, based on the total amount of the pigment paste (C), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness, adhesion, and color unevenness of the coating film formed.
  • Examples of the pigment (c2) include luster pigments, color pigments, extender pigments, etc.
  • the pigments may be used alone or in combination of two or more kinds.
  • Examples of the above-mentioned luster pigments include aluminum (including vapor-deposited aluminum), copper, zinc, brass, nickel, glass flakes, aluminum oxide, mica, aluminum oxide coated with titanium oxide and/or iron oxide, and mica coated with titanium oxide and/or iron oxide.
  • the color pigment examples include titanium oxide, zinc oxide, carbon black, molybdenum red, Prussian blue, cobalt blue, azo pigments, phthalocyanine pigments, quinacridone pigments, isoindoline pigments, threne pigments, perylene pigments, dioxazine pigments, diketopyrrolopyrrole pigments, and heat-shielding pigments.
  • the extender pigment examples include clay, kaolin, barium sulfate, barium carbonate, calcium carbonate, talc, silica, and alumina white.
  • the content of the pigment (c2) in the pigment paste (C) is preferably within the range of 1.0 to 70 mass%, more preferably within the range of 1.0 to 65 mass%, even more preferably within the range of 2.0 to 64 mass%, and even more preferably within the range of 3.0 to 62 mass%, based on the total amount of the pigment paste (C), from the viewpoints of reducing the VOC content in the resulting paint composition and of the hardness and color unevenness of the coating film formed.
  • the pigment paste (C) may further contain an ultraviolet absorbing agent and/or a light stabilizer, and may also contain other additives, such as an internal mold release agent, a solvent (organic solvent, water), a pigment, a catalyst, a dehydrating agent, an antioxidant, a surface conditioner, an antifoaming agent, an emulsifier, a surfactant, an antifouling agent, a wetting agent, a thickener, a dye, an agent for improving scratch resistance, and a gloss adjuster, which are commonly used in the field of coatings, as required.
  • an ultraviolet absorbing agent and/or a light stabilizer may also contain other additives, such as an internal mold release agent, a solvent (organic solvent, water), a pigment, a catalyst, a dehydrating agent, an antioxidant, a surface conditioner, an antifoaming agent, an emulsifier, a surfactant, an antifouling agent, a wetting agent, a thickener, a dye, an agent for
  • the ultraviolet absorbing agent for example, the ultraviolet absorbing agents exemplified in the main component (A) can be used.
  • the content of the ultraviolet absorber is, from the viewpoints of the weather resistance and adhesion of the coating film to be formed, preferably in the range of 0.5 to 10 mass %, more preferably in the range of 0.8 to 5.0 mass %, and even more preferably in the range of 1.0 to 4.0 mass %, based on the total amount of the pigment paste (C) coating composition.
  • the light stabilizer for example, the light stabilizers exemplified in the main component (A) can be used.
  • the content of the light stabilizer is preferably within the range of 0.5 to 10 mass %, more preferably within the range of 0.8 to 9.0 mass %, and even more preferably within the range of 1.0 to 8.0 mass %, based on the total amount of the pigment paste (C), from the viewpoints of the weather resistance and adhesion of the coating film to be formed.
  • the pigment paste (C) may contain an internal mold release agent from the viewpoint of releasability between the coating film to be formed and the mold.
  • the internal mold release agent for example, the internal mold release agents exemplified in the main component (A) can be used.
  • the content of the internal release agent is preferably in the range of 0.4 to 8.0 mass %, more preferably in the range of 0.5 to 7.0 mass %, and even more preferably in the range of 0.5 to 6.0 mass %, based on the total amount of the pigment paste (C), from the viewpoints of the adhesion of the coating film to be formed and the releasability between the coating film to be formed and the mold.
  • the solvent for example, the solvents exemplified for the main component (A) can be used.
  • the content of the solvent is preferably within the range of 2 to 15 mass %, more preferably within the range of 2 to 13 mass %, and even more preferably within the range of 2 to 10 mass %, based on the total amount of the pigment paste (C).
  • the catalysts exemplified for the main component (A) can be used.
  • the blending amount of the catalyst is preferably within the range of 0.01 to 5.0 mass %, and more preferably within the range of 0.1 to 3.0 mass %, based on the total amount of the pigment paste (C).
  • the dehydrating agent for example, the dehydrating agents exemplified in the main component (A) can be used.
  • the blending amount of the dehydrating agent is preferably within the range of 0.1 to 5.0 mass % and more preferably within the range of 0.3 to 3.0 mass % based on the total amount of the pigment paste (C).
  • the viscosity (V C ) of the pigment paste (C) at a shear rate of 100 sec ⁇ 1 and a temperature of 65° C. is within the range of 20 to 1800 mPa ⁇ s.
  • the viscosity (V C ) of the pigment paste (C) at a shear rate of 100 sec -1 and a temperature of 65° C. is preferably within the range of 50 to 1500 mPa ⁇ s, more preferably within the range of 100 to 1000 mPa ⁇ s, and even more preferably within the range of 150 to 800 mPa ⁇ s, from the viewpoints of reducing the VOC content in the resulting coating composition and of the hardness, adhesion, color unevenness, etc. of the coating film to be formed.
  • the solids concentration of the pigment paste (C) is preferably within the range of 84 to 99% by mass, more preferably within the range of 85 to 98% by mass, even more preferably within the range of 87 to 98% by mass, and even more preferably within the range of 90 to 98% by mass, from the viewpoints of reducing the VOC content in the resulting paint composition and of the adhesion and color unevenness of the coating film formed.
  • the content of the pigment paste (C) in the kit according to the present invention and in the three-component paint composition according to the present disclosure is preferably within the range of 3 to 50 mass %, more preferably within the range of 4 to 40 mass %, and even more preferably within the range of 5 to 30 mass %, based on the total amount of the three-component paint composition, from the viewpoints of reducing the VOC content in the resulting paint composition, and of the hardness, adhesion, and color unevenness of the coating film formed.
  • the kit according to the present invention and the three-component coating composition according to the present disclosure can be applied onto a substrate to form a wet coating film (uncured coating film), and then the wet coating film can be cured to form the desired coating film.
  • the substrate is preferably a resin material from the viewpoint of adhesion of the coating film to be formed.
  • the resin material include acrylic resins such as polymethyl methacrylate, polyester resins such as polyethylene terephthalate, polyethylene naphthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate, epoxy resins such as commercially available products such as Epicoat (product name: manufactured by Yuka Shell Epoxy Co., Ltd.), polycarbonate resins, polyimide resins, novolac resins, phenolic resins, acrylonitrile-butadiene-styrene (ABS) resins, acrylonitrile-ethylene-styrene (AES) resins, and acrylic resins such as acrylic terephthalate.
  • acrylic resins such as polymethyl methacrylate
  • polyester resins such as polyethylene terephthalate,
  • the resin examples include lylonitrile-styrene-acrylate (ASA) resin, vinyl chloride resin, vinylidene chloride resin, polyurethane resin, cellulose ester resin (e.g., triacetyl cellulose, diacetyl cellulose, propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, nitrocellulose), polyamide resin, polystyrene resin (e.g., syndiotactic polystyrene), polyolefin resin (e.g., polypropylene, polyethylene, polymethylpentene), polysulfone resin, polyethersulfone resin, polyarylate resin, polyetherimide resin, polyetherketone resin, various fiber reinforced plastic materials (hereinafter sometimes abbreviated as FRP materials or simply FRP), and polymer alloys thereof.
  • ASA lylonitrile-styrene-acrylate
  • vinyl chloride resin vinylidene chloride resin
  • the substrate may also be, for example, a resin material coated with a primer paint, an intermediate coat paint, a top coat paint, or the like, so that a primer layer, an intermediate coat layer, or a top coat layer, or the like, has already been formed.
  • the substrate may be treated (physical treated) by at least one physical method selected from plasma treatment, corona discharge treatment, active energy ray treatment, flame treatment, blast treatment, polishing treatment, etc.
  • the three-component coating composition formed from the kit according to the present invention and the three-component coating composition according to the present disclosure are applied directly onto a substrate.
  • the uses of the three-component paint composition formed from the kit according to the present invention and the substrate to which the three-component paint composition according to the present disclosure is applied are not particularly limited, and examples thereof include outer panel parts of automobile bodies such as passenger cars, trucks, motorcycles, buses, etc.; automobile interior and exterior parts such as bumpers, center pillars, mirrors, door handles, instrument panels, door trims, center consoles, etc.; furniture and building material-related parts such as chairs, vanity mirrors, window frames, gates, etc.; and outer panel parts of household electrical appliances such as mobile phones and audio equipment.
  • the method for applying the three-component coating composition formed from the kit according to the present invention and the three-component coating composition according to the present disclosure to a substrate is not particularly limited.
  • the composition can be applied by air spray, airless spray, rotary atomizing coater, dip coating, applicator, brush, roller, in-mold coating, etc. Electrostatic application may be performed during application.
  • the coating thickness when cured, is preferably within the range of 5 to 2000 ⁇ m, more preferably within the range of 10 to 1500 ⁇ m, and even more preferably within the range of 15 to 1000 ⁇ m.
  • the three-component paint composition formed from the kit of the present invention and the three-component paint composition disclosed herein can be cured by heating the three-component paint composition.
  • Heating can be performed by any method known in the art. Specifically, for example, hot air, hot gas, infrared heater, IR radiator, oven, heat roller, hot press, microwave, etc. In the present invention, from the viewpoint of ease of operation, etc., it is preferable to perform heating by hot air, infrared heater, hot press, etc.
  • the heating temperature is preferably within the range of 30 to 200°C, more preferably within the range of 50 to 180°C, and even more preferably within the range of 70 to 160°C, from the viewpoints of productivity, workability, and thermal stability of the substrate.
  • the heating time is preferably within the range of 20 seconds to 60 minutes, and more preferably within the range of 40 seconds to 10 minutes.
  • the three-component paint composition of the present invention can also be used effectively in coating by the in-mold coating method.
  • This in-mold coating method has the advantage of being able to use paint compositions that usually have a low VOC content, and also reduces the air conditioning energy required during coating, thereby reducing the environmental impact.
  • the in-mold coating method according to the present invention comprises the steps of injecting the coating composition of the present invention (hereinafter, when the coating composition of the present invention is used in the in-mold coating method, it will be referred to as the in-mold coating coating composition) between a molded substrate and the inner wall of a mold, curing the in-mold coating coating composition, and then removing the coated molded article from the mold.
  • the in-mold coating method can be any conventional method that involves molding and coating inside a mold, without any particular restrictions. Specifically, for example, the methods described in JP-A-2000-141407 and JP-A-2008-525212 can be used.
  • the resin molding mold used when molding the resin material and the in-mold coating mold used when coating the in-mold with the in-mold coating paint composition may be the same or different.
  • a resin material heated and melted in an injection cylinder is injected between the resin molding dies having the shape of the desired molded product, cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molded product made of the resin material.
  • the main agent (A), the curing agent (B) and the pigment paste (C) are mixed to prepare an in-mold coating paint composition, a gap sufficient for injecting the in-mold coating paint composition is provided between the surface of the molded product made of the resin material and the in-mold coating die, the in-mold coating paint composition is injected between the surface of the molded product made of the resin material and the inner wall of the in-mold coating die, the in-mold coating die is closed, and an uncured in-mold coating film is formed on the molded product made of the resin material.
  • the uncured in-mold coating film formed on the molded product made of the resin material is heated and molded into the desired shape, and an in-mold coated molded product having a cured in-mold coating film formed on the molded product made of the resin material can be obtained.
  • the resin molding die and the in-mold coating die are different, for example, a resin material that is heated and melted in an injection cylinder is injected between the resin molding dies having the shape of the desired molded product, cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molded product made of the resin material and removed.
  • the main agent (A), the curing agent (B) and the pigment paste (C) are mixed to prepare an in-mold coating paint composition
  • the in-mold coating die is brought close to the surface of the resin molding, a gap sufficient for injecting the in-mold coating paint composition is provided between the surface of the molded product made of the resin material and the in-mold coating die, the in-mold coating paint composition is injected between the surface of the molded product made of the resin material and the inner wall of the in-mold coating die, the in-mold coating die is closed, and an uncured in-mold coating film is formed on the molded product made of the resin material.
  • an external mold release agent may be applied to the mold.
  • the external mold release agent for example, a fluorine-based, silicone-based, surfactant-based, wax-based, or other external mold release agent can be used.
  • the heating temperature when melting the resin in the injection cylinder is determined arbitrarily depending on the type of resin material, etc., but is preferably set to 80 to 300°C.
  • the temperature of the mold when injecting the resin material is determined arbitrarily depending on the molding time, type of resin material, etc., but is preferably set to 30 to 120°C.
  • the base agent (A), the curing agent (B), and the pigment paste (C) it is preferable to heat the base agent (A), the curing agent (B), and the pigment paste (C) separately before mixing them, from the viewpoints of the hardness, adhesion, and color unevenness of the coating film to be formed.
  • the temperature is preferably within the range of 30 to 100°C, more preferably within the range of 40 to 90°C, and even more preferably within the range of 50 to 80°C, from the viewpoints of the hardness, adhesion and color unevenness of the coating film to be formed.
  • the flash point of the base agent (A) is preferably 70° C. or higher, and more preferably 100° C. or higher
  • the flash point of the curing agent (B) is preferably 70° C. or higher, and more preferably 100° C. or higher
  • the flash point of the pigment paste (C) is preferably 70° C. or higher, and more preferably 100° C. or higher.
  • the molding time of the resin material may be until the resin material is completely solidified, but it is sufficient that the resin material is solidified to a strength that does not impair the molded shape when the in-mold coating paint composition is injected, and usually, about 20 seconds to 60 minutes is preferable.
  • the amount of the in-mold coating composition injected is an amount sufficient to obtain a desired film thickness, and is preferably an amount sufficient to obtain a cured film thickness of 15 to 2000 ⁇ m.
  • the heating temperature when the uncured in-mold coating film is heated is preferably within the range of 20 to 160°C, more preferably within the range of 40 to 150°C, and even more preferably within the range of 60 to 140°C.
  • the heating time for heating the uncured in-mold coating film is preferably within the range of 20 seconds to 10 minutes, more preferably within the range of 30 seconds to 5 minutes, and even more preferably within the range of 40 seconds to 4 minutes.
  • the pressure is preferably within the range of 2 to 14 MPa from the viewpoints of the hardness and adhesion of the coating film to be formed.
  • Production Examples 2 to 11 Main components (A-1) to (A-11) were obtained in the same manner as in Production Example 1, except that the blending compositions in Production Example 1 were as shown in Table 1 below. ⁇ Measurement of Viscosity (V A ) of Main Component (A) at Shear Rate of 100 sec ⁇ 1 and Temperature of 65° C.> The viscosity (V A ) of the main components (A-1) to (A-11) obtained in Production Examples 1 to 11 was measured at a shear rate of 100 sec -1 and a temperature of 65° C. according to the following method. The results are also shown in Table 1.
  • V A viscosity at a shear rate of 100 sec -1 and a temperature of 65°C was measured using a cone and plate viscometer "MCR-302e” (trade name, manufactured by Anton Paar, diameter 25 mm, cone and plate inclined at 2°).
  • Viscosity (V B ) of Curing Agent (B) at Shear Rate of 100 sec ⁇ 1 and Temperature of 65° C. The viscosity (V B ) of the curing agents (B-1) to (B-8) obtained in Production Examples 12 to 19 at a shear rate of 100 sec -1 and a temperature of 65° C. was measured according to the following method. The results are also shown in Table 2.
  • the temperature was increased from 20°C to 80°C at a rate of 5°C/min, and the viscosity ( VB ) at a shear rate of 100 sec -1 and a temperature of 65°C was measured using a cone and plate viscometer "MCR-302e” (trade name, manufactured by Anton Paar, diameter 25 mm, cone and plate inclined at 2°).
  • the resulting mixed solution was then placed in a wide-mouthed glass bottle, glass beads with a diameter of about 1.3 mm were added as a dispersion medium, the bottle was sealed, and the bottle was dispersed for 3 hours using a paint shaker to obtain a pigment paste (C-1) with a solids concentration of 92.0%.
  • Production Examples 21 to 81 Pigment pastes (C-2) to (C-62) were obtained in the same manner as in Production Example 20, except that the blending compositions in Production Example 20 were as shown in Table 3 below.
  • the temperature was increased from 20°C to 80°C at a rate of 5°C/min, and the viscosity ( VB ) at a shear rate of 100 sec -1 and a temperature of 65°C was measured using a cone and plate viscometer "MCR-302e” (trade name, manufactured by Anton Paar, diameter 25 mm, cone and plate inclined at 2°).
  • Example 1 Preparation of in-mold coated molding (M1)
  • "Dialac TW20” product name, Techno UMG, acrylonitrile-styrene-acrylate resin (ASA resin)
  • ASA resin acrylonitrile-styrene-acrylate resin
  • a kit consisting of the base agent (A-1) obtained in Production Example 1, the curing agent (B-1) obtained in Production Example 12, and the pigment paste (C-1) obtained in Production Example 20 was prepared, and each kit was heated to 65 ° C.
  • the base agent (A-1), the curing agent (B-1), and the pigment paste (C-1) were mixed in a container equipped with a stirrer so that the mass ratio of (A-1) / (B-1) / (C-1) was 30.3 / 62.1 / 7.6, and mixed uniformly to obtain an in-mold coating paint composition No. 1 with a solid content concentration of 98.9%.
  • the resin molding die was opened, and the above-mentioned in-mold coating composition No.
  • the base agent (A-1), the curing agent (B-1), and the pigment paste (C-1) were mixed in a container equipped with a stirrer so that the mass ratio of the base agent (A-1), the curing agent (B-1), and the pigment paste (C-1) was 30.3/62.1/7.6 in the ratio of (A-1)/(B-1)/(C-1), and mixed uniformly to obtain in-mold coating paint composition No. 1 with a solid content concentration of 98.9%.
  • the resin molding die was opened, and the above-mentioned in-mold coating composition No. 1 was injected between the obtained flat "Makroblend UT235M” molded product and the coating film-coated die.
  • the inside of the coating film-coated die was heated to 80°C and, while maintaining the temperature, pressurized at a molding pressure of 5 MPa and maintained for 1 minute, after which the pressure was reduced and the coating film-coated die was opened, producing an in-mold coated molded product (M2-1) in which the flat "Makroblend UT235M" molded product was coated with a coating film with a cured film thickness of 200 ⁇ m.
  • Example 2 to 59 Comparative Examples 1 to 26 In-mold coated moldings (M1-2) to (M1-85) and (M2-2) to (M2-85) were produced in the same manner as in Example 1, except that the blending compositions in Example 1 were as shown in Table 4 below.
  • the Martens hardness (N/ mmm2 ) of the cured coating film of each of the in-mold coated moldings obtained in Examples 1 to 59 and Comparative Examples 1 to 26 was measured using a "Fisherscope (registered trademark) HM2000S" (product name, manufactured by Fisher Instruments Inc.) and evaluated based on the following criteria.
  • the measurement conditions were as follows: indenter: square pyramidal Vickers indenter (material: diamond, facing angle: 136°), maximum test load: 20 mN, pressing speed: 20 mN/25 seconds, temperature: 21 ⁇ 2°C, humidity: 50 ⁇ 5% relative humidity. ⁇ and ⁇ are acceptable.
  • ⁇ : Martens hardness is 110 N/mm2 or more , ⁇ : Martens hardness is 100 N/mm 2 or more and less than 110 N/mm 2 ; ⁇ : Martens hardness is 75 N/ mm2 or more and less than 100 N/ mm2 . ⁇ : Martens hardness is less than 75 N/ mm2 .
  • ⁇ 100 square grid coating films remain, and there are no small chips or lifting of the coating film at the edges of the cutter cuts.
  • ⁇ 100 square grid coating films remain, and small edge chips or lifting of the coating film occurs at the edge of the cutter cut.
  • ⁇ 90 to 99 grid-like coating films remain.
  • x The number of remaining cross-hatched coating films is 89 or less.

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PCT/JP2024/010162 2023-03-31 2024-03-15 三液型塗料組成物用のキット、三液型塗料組成物及び型内被覆方法 Ceased WO2024203429A1 (ja)

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CN202480008451.1A CN120569447A (zh) 2023-03-31 2024-03-15 三液型涂料组合物用套组、三液型涂料组合物、及模内涂敷方法
EP24779558.6A EP4692260A1 (en) 2023-03-31 2024-03-15 Kit for three-component coating composition, three-component coating composition, and in-mold coating method

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JPH0214273A (ja) * 1988-07-01 1990-01-18 Dainichiseika Color & Chem Mfg Co Ltd 塗料組成物
JPH0841208A (ja) * 1993-09-06 1996-02-13 Nippon Oil & Fats Co Ltd 硬化性組成物、熱潜在性酸触媒、塗装仕上げ方法及び塗装物品、並びに成形方法及び成形品
JP2017534477A (ja) * 2014-08-22 2017-11-24 コベストロ・エルエルシー 複数の型穴を有する型を使用したインモールドコーティングのための方法、およびそれによりコーティングされた基板
JP2020183455A (ja) * 2019-04-26 2020-11-12 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物
JP6949291B1 (ja) * 2020-04-10 2021-10-13 関西ペイント株式会社 塗料組成物及び型内被覆方法
JP2022071676A (ja) * 2020-10-28 2022-05-16 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物
JP2022071678A (ja) * 2020-10-28 2022-05-16 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物

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JP2000141407A (ja) 1998-08-31 2000-05-23 Dainippon Toryo Co Ltd 型内被覆方法
DE102004062510A1 (de) 2004-12-24 2006-07-06 Bayer Materialscience Ag Verfahren zum Formen und Beschichten eines Substrats

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JPH01240577A (ja) * 1988-03-22 1989-09-26 Tanabe Kagaku Kogyo Kk ポリウレタン成形物用モールドコート塗料
JPH0214273A (ja) * 1988-07-01 1990-01-18 Dainichiseika Color & Chem Mfg Co Ltd 塗料組成物
JPH0841208A (ja) * 1993-09-06 1996-02-13 Nippon Oil & Fats Co Ltd 硬化性組成物、熱潜在性酸触媒、塗装仕上げ方法及び塗装物品、並びに成形方法及び成形品
JP2017534477A (ja) * 2014-08-22 2017-11-24 コベストロ・エルエルシー 複数の型穴を有する型を使用したインモールドコーティングのための方法、およびそれによりコーティングされた基板
JP2020183455A (ja) * 2019-04-26 2020-11-12 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物
JP6949291B1 (ja) * 2020-04-10 2021-10-13 関西ペイント株式会社 塗料組成物及び型内被覆方法
JP2022071676A (ja) * 2020-10-28 2022-05-16 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物
JP2022071678A (ja) * 2020-10-28 2022-05-16 日本ペイント・オートモーティブコーティングス株式会社 ２液型コーティング組成物

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JPWO2024203429A1 (https=) 2024-10-03

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