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WO2023140053A1 - Agent de traitement de surface, matériau traité ayant un revêtement, et procédé de fabrication associé - Google Patents

Agent de traitement de surface, matériau traité ayant un revêtement, et procédé de fabrication associé Download PDF

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Publication number
WO2023140053A1
WO2023140053A1 PCT/JP2022/047769 JP2022047769W WO2023140053A1 WO 2023140053 A1 WO2023140053 A1 WO 2023140053A1 JP 2022047769 W JP2022047769 W JP 2022047769W WO 2023140053 A1 WO2023140053 A1 WO 2023140053A1
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WIPO (PCT)
Prior art keywords
group
resins
surface treatment
treatment agent
resin
Prior art date
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Ceased
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PCT/JP2022/047769
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English (en)
Japanese (ja)
Inventor
禎秀 檀上
直将 石神
裕貴 鹿沼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nihon Parkerizing Co Ltd
Original Assignee
Nihon Parkerizing Co Ltd
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Filing date
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Application filed by Nihon Parkerizing Co Ltd filed Critical Nihon Parkerizing Co Ltd
Priority to CN202280089222.8A priority Critical patent/CN118556115A/zh
Priority to KR1020247023795A priority patent/KR20240121856A/ko
Publication of WO2023140053A1 publication Critical patent/WO2023140053A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
    • C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00

Definitions

  • the present invention relates to a surface treatment agent that forms a film on a material to be treated. Moreover, it is related with the to-be-processed material which has a film
  • Patent Literature 1 discloses a water-based metal surface treatment agent containing a specific organosilicon compound (P) and at least one organic polymer (Q) selected from urethane resins, epoxy resins, acrylic resins, phenol resins, polyester resins and polyolefin resins. It is disclosed that a metal material treated with this surface treatment agent has not only excellent corrosion resistance and adhesion, but also acid resistance and alkali resistance.
  • P specific organosilicon compound
  • Q organic polymer
  • Patent Document 2 discloses a polysiloxane compound (A) having a urea group and an X group [the X group is one or more groups selected from -COOR, -SO 3 R and -NR 2 , and R is a hydrogen atom, or an alkyl group optionally having an alkoxy group or a hydroxyl group], and the ratio of the number of urea groups to X groups in one molecule (urea group/X group) is within the range of 0.01 to 0.45. It is disclosed that a film having excellent acid resistance, solvent resistance and post-coating corrosion resistance can be formed using a composition containing a polysiloxane compound (A).
  • the present invention [1] ⁇ X ⁇ [X ⁇ -COOR ⁇ -SO 3 R ⁇ -NR 2 ⁇ 1 ⁇ 2 ⁇ R ⁇ ] ⁇ 1 ⁇ X ⁇ ( ⁇ /X ⁇ ) ⁇ 0.01 ⁇ 0.45 ⁇ (A) ⁇ Zr ⁇ Ti ⁇ Hf ⁇ Bi ⁇ (B) ⁇ / ⁇ (C) ⁇ [2]
  • the metal compound (B) is a metal compound containing Zr.
  • a method for producing a material to be treated having a film comprising a step of contacting the surface of the material to be treated or the surface thereof with the surface treatment agent according to any one of [1] to [3], and drying the surface of the material to be treated or the surface treatment agent brought into contact with the surface of the material to be treated.
  • a material to be treated having a film produced by the method described in [4]. and so on.
  • the present invention it is possible to provide a new surface treatment agent containing a polysiloxane compound that has both solvent resistance and alkali resistance.
  • the new surface treatment agent forms a film with excellent rust resistance and corrosion resistance after painting, it is possible to prolong the life of the object to be treated and to use resources efficiently.
  • the surface treatment agent according to the present invention will be described below.
  • the surface treatment agent according to this embodiment contains a polysiloxane compound (A), a metal compound (B) and/or a water-soluble or water-dispersible resin (C).
  • the surface treatment agent may contain components other than these.
  • the polysiloxane compound (A) has a urea group (urea bond) and an X group [the X group is one or more groups selected from -COOR, -SO 3 R and -NR 2 , and R is a hydrogen atom, or an alkoxy group or an alkyl group optionally having a hydroxyl group], and the ratio of the number of urea groups to the number of X groups in one molecule (urea group/X group) is within the range of 0.01 to 0.45.
  • the polysiloxane compound has one or more Si groups to which hydroxyl groups or alkoxy groups are bonded.
  • the polysiloxane compound may further have an epoxy group, or may have a structure (--CH(OH)CH 2 OH) in which the epoxy group is ring-opened by hydrolysis.
  • the X group is, for example, a carboxyl group, an alkoxycarbonyl group, a sulfone group, an alkylsulfone group, an amino group, an N-alkylamino group, an N,N-dialkylamino group, an N-(alkoxyalkyl)amino group, an N-(hydroxyalkyl)amino group, an N,N-di(alkoxyalkyl)amino group, an N,N-di(hydroxyalkyl)amino group, etc.
  • the polysiloxane compound may have one or two or more thereof.
  • Combinations of two or more groups include, for example, a combination of a carboxyl group and an amino group, a combination of an alkoxycarbonyl group and an amino group, a combination of a sulfone group and an amino group, a combination of an alkylsulfone group and an amino group, a combination of a carboxyl group and an N-alkylamino group, a combination of an alkoxycarbonyl group and an N-alkylamino group, a combination of a sulfone group and an N-alkylamino group, a combination of an alkylsulfone group and an N-alkylamino group, a combination of a carboxyl group and an N,N-dialkylamino group, and an alkoxycarbonyl group.
  • each alkyl moiety and each alkylene moiety in an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylsulfone group, an N-alkylamino group, an N,N-dialkylamino group, an N-(alkoxyalkyl)amino group, an N-(hydroxyalkyl)amino group, an N,N-di(alkoxyalkyl)amino group, and an N,N-di(hydroxyalkyl)amino group may be linear or branched.
  • alkyl groups and alkyl moieties include alkyl groups having 1 to 20 carbon atoms, and alkyl groups having 1 to 12 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups are preferred.
  • alkylene moiety examples include an alkylene chain having 1 to 20 carbon atoms, and an alkylene chain having 1 to 12 carbon atoms such as a methylene chain, ethylene chain, propylene chain, butylene chain, pentylene chain, hexylene chain, peptylene chain, octylene chain, nonylene chain, decylene chain, undecylene chain, and dodecylene chain is preferable.
  • the two alkyl moieties, alkoxyalkyl moieties and hydroxyalkyl moieties may be the same or different.
  • the weight average molecular weight of the polysiloxane compound is not particularly limited, and is, for example, within the range of 1,000 to 1,000,000, preferably within the range of 5,000 to 500,000, and more preferably within the range of 10,000 to 100,000.
  • the weight average molecular weight is, for example, a value determined by gel permeation chromatography (GPC) and obtained as a polystyrene-equivalent molecular weight.
  • Polysiloxane compound (A) for example, an isocyanate compound (a1), an aminosilane compound (a2), and an aqueous medium are sequentially blended at a predetermined ratio and reacted at a predetermined temperature (preferably 40 to 80 ° C.). Can be produced by.
  • the amine compound (a3) may be further blended in addition to the isocyanate compound (a1) and the aminosilane compound (a2).
  • the amino group of the polysiloxane compound obtained by the production may be reacted with an alkyl halide or alkylene oxide to produce a polysiloxane compound having an N-alkylamino group or an N,N-dialkylamino group.
  • alkyl portion of the alkyl halide are the same as above.
  • Halogen in halogenated alkyl includes, for example, a fluorine atom, a chlorine atom, a bromine atom and the like.
  • alkylene oxides include ethylene oxide, propylene oxide, and butylene oxide, but are not limited to these.
  • polycondensation catalysts such as dibutyltin diacetate, dibutyltin dilaurate, and lead naphthenate
  • known hydrolysis catalysts such as acidic catalysts
  • amine catalysts that are polycondensation catalysts and hydrolysis catalysts may be used.
  • the isocyanate compound (a1) means a compound having one or more isocyanate groups.
  • the isocyanate compound (a1) may have two or more isocyanate groups.
  • the isocyanate compound (a1) may further have a Si group to which a hydroxyl group or an alkoxy group is bonded.
  • Examples of the isocyanate compound (a1) include 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 1,4-diisocyanatobutane, 1,6-diisocyanatohexane, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-cyclohexylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 2,4′-dicyclohexylmethane diisocyanate, and isophorone diisocyanate. It is not limited. In addition, these isocyanate compounds may use 1 type, and may use 2 or more types together.
  • the aminosilane compound (a2) means a compound having one or more amino groups and a Si group to which a hydroxyl group or an alkoxy group is bonded.
  • Examples of the aminosilane compound (a2) include, but are not limited to, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-[2-(2-aminoethylaminoethylamino)propyl]trimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and the like.
  • One of these aminosilane compounds may be used, or two or more of them may be used in combination.
  • the amine compound (a3) is a compound having one or more amino groups, is not particularly limited as long as it does not correspond to the aminosilane compound (a2), and may further have a COOR group and/or an SO 3 R group. ⁇ (a3) ⁇ ; ⁇ ; ⁇ 4- ⁇ ; ⁇ 2- ⁇ -1- ⁇ 4- ⁇ -1- ⁇ SO 3 R ⁇ (R ⁇ ) ⁇ ; ⁇ ; ⁇ ( ⁇ );1- ⁇ N- ⁇ N- ⁇ -1,3- ⁇ N- ⁇ -1,3- ⁇ N- ⁇ ;4- ⁇ 4- ⁇ -N,N- ⁇ 1,1- ⁇ 2-( ⁇ ) ⁇ N,N- ⁇ -1,3- ⁇ N,N- ⁇ -1,3- ⁇ N,N- ⁇ -1,3- ⁇ N,N- ⁇ ;4-[(2- ⁇ ) ⁇ ]- ⁇ N-( ⁇ ) ⁇ ;p-(p- ⁇ ) ⁇ 3- ⁇ -4-(2- ⁇ ) ⁇ N-(2- ⁇ )-1,3- ⁇ N-(2- ⁇ )-1,3- ⁇ N-( ⁇ ) ⁇ ;4-[ ⁇ ( ⁇ ) ⁇
  • a urea group is obtained by reacting the isocyanate group in the isocyanate compound (a1) with the amino group in the aminosilane compound (a2) or the amine compound (a3).
  • the ratio of the number of urea groups to the number of X groups in one molecule is not particularly limited as long as it is in the range of 0.01 to 0.45, preferably in the range of 0.05 to 0.4, more preferably in the range of 0.1 to 0.35.
  • a polysiloxane compound containing a urea group and an X group with a ratio (urea group/X group) within the range of 0.01 to 0.45 can be produced by appropriately adjusting the amount of the isocyanate compound (a1), the aminosilane compound (a2), the amine compound (a3), and the like.
  • the isocyanate compound (a1) and aminosilane compound (a2), or the isocyanate compound (a1), aminosilane compound (a2) and amine compound (a3) may be further blended with a silicon-containing compound (a4).
  • the silicon-containing compound (a4) does not correspond to the isocyanate compound (a1) and aminosilane compound (a2), but means a compound containing Si, preferably a compound in which a hydroxyl group, an alkoxy group, or a halo group is bonded to Si.
  • silicon-containing compound (a4) examples include vinyltrichlorosilane, vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, vinyltris(2-methoxyethoxy)silane, vinyltriethoxysilane, vinyltrimethoxysilane, 3-(methacryloyloxy)propyltrimethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxysilane.
  • the aqueous medium is not particularly limited as long as it is water or a mixture of water and a water-miscible organic solvent.
  • the mass % of water in the mixture may be 50 mass % or more, and is more preferably 80 mass % or more, 90 mass % or more, 95 mass % or more, and 99 mass % or more in this order.
  • the water-miscible organic solvent is not particularly limited as long as it is miscible with water.
  • examples include ketone solvents such as acetone and methyl ethyl ketone; amide solvents such as N,N'-dimethylformamide and dimethylacetamide; alcohol solvents such as methanol, ethanol and isopropanol; ether solvents such as ethylene glycol monobutyl ether and ethylene glycol monohexyl ether;
  • ketone solvents such as acetone and methyl ethyl ketone
  • amide solvents such as N,N'-dimethylformamide and dimethylacetamide
  • alcohol solvents such as methanol, ethanol and isopropanol
  • ether solvents such as ethylene glycol monobutyl ether and ethylene glycol monohexyl ether
  • One of these water-miscible organic solvents may be mixed with water, or two or more thereof may be mixed with water.
  • the content of the polysiloxane compound (A) in the surface treatment agent is not particularly limited, but the solid content conversion mass concentration (meaning the total solid content conversion mass concentration when two or more compounds are blended) is usually 50 mg/L or more, preferably 5,000 mg/L or more, and usually 100,000 mg/L or less, preferably 50,000 mg/L or less.
  • a coating film having better corrosion resistance can be formed by forming a coating film after forming a coating film using a surface treatment agent having a concentration of the polysiloxane compound (A) within the above range.
  • Metal compound (B) is a compound containing a metal element selected from the group consisting of Zr, Ti, Hf and Bi.
  • the metal compound (B) dissolves in the surface treatment agent, and the metal element exists as ions.
  • the ions may be metal ions, complex ions, or oxide ions.
  • the metal compound (B) include hexafluorozirconic acid, zirconium nitrate, zirconyl nitrate, zirconium carbonate, zirconium acetate, zirconium hydroxide, zirconium oxide, hexafluorotitanic acid, titanium nitrate, titanyl nitrate, titanium hydroxide, titanium oxide, hexafluorohafnium acid, hafnium nitrate, hafnium oxide, hexafluorobismuthic acid, bismuth nitrate, bismuth carbonate, bismuth hydroxide, bismuth oxide, and the like. It may be its salt.
  • These metal compounds (B) may be contained in the surface treatment agent alone or in combination of two or more.
  • the content of the metal compound (B) in the surface treatment agent is not particularly limited, but the metal-equivalent mass concentration (meaning the total metal-equivalent mass concentration when two or more compounds are blended) is usually 10 mg/L or more, preferably 1,000 mg/L or more, and usually 20,000 mg/L or less, preferably 10,000 mg/L or less.
  • a coating film having better corrosion resistance can be formed by forming a coating film after forming a coating film using a surface treatment agent having a concentration of the metal compound (B) within the above range.
  • Resin (C) is a water-soluble or water-dispersible resin and is selected from the group consisting of polyvinyl resins, acrylic resins, polyvinylidene chloride resins, epoxy resins, urethane resins, polyester resins, polyamide resins, polyimide resins, phenol resins, silicone resins, and fluorine resins.
  • a modified product obtained by modifying the side chain of a homopolymer of these resins with another compound, or a copolymer obtained by combining two or more of these resins or modified products may be used.
  • the weight average molecular weight of the resin (C) is not particularly limited as long as it is 2,000 or more, preferably 4,000 or more, more preferably 10,000 or more.
  • the upper limit is preferably 1,000,000 or less.
  • These resins (C) may contain only one type in the surface treatment agent, or may contain two or more types.
  • the content of the resin (C) in the surface treatment agent is not particularly limited, it is usually 10 mg/L or more, preferably 1,000 mg/L or more, and usually 20,000 mg/L or less, preferably 10,000 mg/L or less, as a solid content conversion mass concentration (meaning a total solid content conversion mass concentration when two or more resins are blended).
  • the surface treatment agent of the present embodiment usually contains water and/or an organic solvent, and may consist only of the above components (A) to (C) and water and/or an organic solvent, or may contain other components.
  • Other ingredients include preservatives, surfactants, thickeners, pigments, dyes, cross-linking agents, antibacterial agents, antifungal agents, and the like.
  • organic solvents examples include ketone solvents such as acetone and methyl ethyl ketone; amide solvents such as N,N'-dimethylformamide and dimethylacetamide; alcohol solvents such as methanol, ethanol and isopropanol; ether solvents such as ethylene glycol monobutyl ether and ethylene glycol monohexyl ether; One of these organic solvents may be mixed with water, or two or more thereof may be mixed with water.
  • ketone solvents such as acetone and methyl ethyl ketone
  • amide solvents such as N,N'-dimethylformamide and dimethylacetamide
  • alcohol solvents such as methanol, ethanol and isopropanol
  • ether solvents such as ethylene glycol monobutyl ether and ethylene glycol monohexyl ether
  • One of these organic solvents may be mixed with water, or two or more thereof may be mixed with water.
  • the surfactant is not particularly limited as long as it can improve the wettability of the composition containing the polysiloxane compound, and cationic, anionic, amphoteric, nonionic surfactants can be used.
  • cationic surfactants such as alkylamine salts and alkyltrimethylammonium halides
  • anionic surfactants such as alkylsulfonate esters, polyoxyethylene alkylphenyl ether sulfates, sodium dodecyldiphenyl ether disulfonate and sodium dodecyl sulfate
  • amphoteric surfactants such as alkylaminopropionates and alkyldimethylbetaines
  • nonionic surfactants and the like.
  • These may be used individually by 1 type, and may be used in combination of 2 or more type.
  • Known thickeners, pigments, dyes, cross-linking agents, antibacterial agents, and antifungal agents can also be used.
  • the surface treatment agent according to this embodiment can be produced by mixing the above components (A) to (C) with water and/or an organic solvent. When it contains other components, it can be produced by mixing the other components together.
  • the surface treatment agent of the present embodiment has durability, corrosion resistance, and paint adhesion by contacting the surface of the material to be treated or the surface thereof by a method such as a coating method or an immersion method, and then drying to form a film having an excellent appearance.
  • the contact time, drying temperature, and drying time are not particularly limited, and the drying can be carried out under the conditions commonly used.
  • Materials to be treated are typically metal materials, but are not limited to these, and include plastics, rubbers, ceramics, glass, fibers, magnetic materials, and the like.
  • films can be formed on materials used in electronic parts and micro-equipment parts that constitute industrial products such as automobiles, home appliances, OA equipment, medical equipment, medical equipment, cooking utensils, ships, building materials, and the like.
  • the material to be treated Before contacting the surface treatment agent to the material to be treated, the material to be treated may be degreased or pickled, washed with water after each treatment, or dried after washing with water.
  • the chemical conversion treatment may be performed after performing the degreasing treatment and the pickling treatment, or the chemical conversion treatment may be performed without performing the degreasing treatment and the pickling treatment.
  • the type of chemical conversion treatment is not particularly limited, and one or more of a chromate chemical conversion treatment, a zinc phosphate chemical conversion treatment process, a bismuth substitution plating process, a phosphate iron chemical conversion treatment process, a zirconium chemical conversion treatment process, a titanium chemical conversion treatment process, a hafnium chemical conversion treatment process, and the like can be performed.
  • a coating may be further applied on the film surface formed by the surface treatment agent of this embodiment.
  • the coating method is not particularly limited, and known methods such as rolling coating, spray coating, hot spray coating, airless spray coating, electrostatic coating (e.g., electrostatic powder coating), roller coating, curtain flow coating, brush coating, bar coating, fluidization dipping method, electrodeposition coating, and the like can be applied.
  • the coating on the surface of the coated substrate may be dried.
  • the surface of the material to be treated having the film formed from the polysiloxane compound of the present embodiment or the composition containing it may or may not be washed with water.
  • the surface of the substrate after washing with water or not washing with water may or may not be dried.
  • paints examples include known paints such as oil paints, cellulose derivative paints, phenol resin paints, alkyd resin paints, aminoalkyd resin paints, urea resin paints, unsaturated resin paints, vinyl resin paints, acrylic resin paints, epoxy resin paints, polyurethane resin paints, silicone resin paints, fluororesin paints, anticorrosive paints, antifouling paints, powder paints, water-based paints, solvent paints, and electrodeposition paints.
  • one coating or two or more coatings may be performed using the same or different paints. Drying is a process of drying and hardening the applied paint.
  • drying methods include natural drying, reduced pressure drying, convection heat drying (e.g., natural convection heat drying, forced convection heat drying), radiation drying (e.g., near-infrared drying, far-infrared drying), ultraviolet curing drying, electron beam curing drying, vapocure, baking drying, and the like.
  • convection heat drying e.g., natural convection heat drying, forced convection heat drying
  • radiation drying e.g., near-infrared drying, far-infrared drying
  • ultraviolet curing drying e.g., near-infrared drying, far-infrared drying
  • electron beam curing drying e.g., vapocure, baking drying, and the like.
  • powder coating such as spray coating, electrostatic powder coating, and fluidized bed coating.
  • powder coatings include those containing a polyester resin and, as a curing agent, a blocked isocyanate curing agent, a ⁇ -hydroxyalkylamide curing agent (see, for example, JP-A-2011-88083) or triglycidyl isocyanurate.
  • Baking is performed in a predetermined temperature range for a certain period of time. An example is 150-250° C. for 20 minutes.
  • Known methods can be applied as coating methods such as spray coating, electrostatic coating, and bar coating using solvent coating.
  • solvent paints include those containing resins such as melamine resins, acrylic resins, urethane resins and polyester resins, and organic solvents such as thinners. Baking is performed in a predetermined temperature range for a certain period of time. An example is 130° C. for 20 minutes.
  • a known method can be used as a coating method for electrodeposition coating using an electrodeposition paint.
  • electrodeposition paints include those containing resins such as epoxy resins and acrylic resins. Baking is performed in a predetermined temperature range for a certain period of time. An example is 130-250° C. for 20 minutes.
  • the coating film obtained by painting may be a single layer or multiple layers.
  • the paints for forming various coating films, the coating method using the paints, the drying method of the coated substrate, and the like may be the same or different.
  • the unit of the compounding amount of each raw material described in the table is parts by mass.
  • Isocyanate compound (a1) (a1-1): 3-isocyanatopropyltriethoxysilane (a1-2): 1,4-diisocyanatobutane/aminosilane compound (a2) (a2-1): 3-aminopropyltriethoxysilane (a2-2): N-2-(aminoethyl)-3-aminopropyltrimethoxysilane/amino compound (a3) (a3-1): ethylenediamine (a3-2): 4-aminobenzenesulfonic acid/silicon-containing compound (a4) (a4-1): 3-glycidoxypropyltriethoxysilane (a4-2): tetraethoxysilane
  • ⁇ Metal compound (B) (B-1) Zirconium acetate (zirconium compound, ZrO2 equivalent content 30%, manufactured by Nippon Light Metal Co., Ltd.) (B-2) Zirconium nitrate (zirconium compound, ZrO2 equivalent content 20%, manufactured by Nippon Light Metal Co., Ltd.) (B-3) Zircon hydrofluoric acid 40% (zirconium compound, manufactured by Morita Chemical Industry Co., Ltd.) (B-4) TC-400 (titanium compound, Ti content 8.2%, manufactured by Matsumoto Fine Chemical Co., Ltd.) (B-5) 40% titanium hydrofluoric acid (titanium compound, manufactured by Morita Chemical Industry Co., Ltd.) ⁇ Resin (C) (C-1) F-2125D (urethane resin, solid content: 30%, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (C-2) A-655 (acrylic resin, solid content: 45%, manufactured by Kusumoto Kas
  • compositions of Examples 1 to 79 and Comparative Examples 1 to 6 were appropriately diluted on the surface of the treated material that had been washed and dried, each of which was applied by a bar coating method and dried at a maximum plate temperature (PMT) of 150°C to prepare treated materials having various films (Examples 1 to 79 and Comparative Examples 1 to 6).
  • PMT maximum plate temperature
  • two kinds of films having a film weight after drying of 50 mg/m 2 and 1000 mg/m 2 were prepared.
  • Treated materials with a coating weight of 50 mg/m 2 were used for temporary rust prevention evaluation , corrosion resistance evaluation after solvent coating, corrosion resistance evaluation after powder coating, and corrosion resistance evaluation after electrodeposition coating.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Dispersion Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Other Surface Treatments For Metallic Materials (AREA)

Abstract

La présente invention vise à fournir un nouvel agent de traitement de surface contenant un composé polysiloxane. La présente invention concerne par conséquent un agent de traitement de surface comprenant : un composé polysiloxane (A) qui a un groupe urée et un groupe X [groupe X est un ou plusieurs groupes sélectionné parmi -COOR, SO3R, et -NR2, et R représente un atome d'hydrogène ou un groupe alkyle ayant éventuellement un groupe alcoxy ou un groupe hydroxyle], et dans lequel le rapport (groupe urée/groupe X) du nombre de groupes urée sur le nombre de groupes X est de 0,01 à 0,45 ; un composé métallique (B) contenant un métal sélectionné dans Le groupe constitué par Zr, Ti, Hf et Bi ; et/ou une résine soluble dans l'eau ou dispersible dans l'eau (C) sélectionnée dans le groupe constitué par les résines polyvinyle, les résines acryliques, les résines chlorure de polyvinylidène, les résines époxy, les résines uréthane, les résines polyester, les résines polyamide, les résines polyimide, les résines phénol, les résines silicone et les résines fluorées.
PCT/JP2022/047769 2022-01-21 2022-12-23 Agent de traitement de surface, matériau traité ayant un revêtement, et procédé de fabrication associé Ceased WO2023140053A1 (fr)

Priority Applications (2)

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CN202280089222.8A CN118556115A (zh) 2022-01-21 2022-12-23 表面处理剂以及具有皮膜的被处理材料及其制造方法
KR1020247023795A KR20240121856A (ko) 2022-01-21 2022-12-23 표면 처리제 그리고 피막을 갖는 피처리재 및 그 제조 방법

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JP2022007542A JP2023106679A (ja) 2022-01-21 2022-01-21 表面処理剤並びに皮膜を有する被処理材及びその製造方法
JP2022-007542 2022-01-21

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JP2025060180A (ja) * 2023-09-29 2025-04-10 日本パーカライジング株式会社 金属表面処理剤、金属材料の製造方法および金属材料
JP7773521B2 (ja) * 2023-12-20 2025-11-19 日本ペイント・サーフケミカルズ株式会社 表面処理金属部材の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH073206A (ja) * 1993-06-18 1995-01-06 Nippon Shokubai Co Ltd ガスバリヤ用表面処理用組成物
JP2006036996A (ja) * 2004-07-29 2006-02-09 Sakai Kagaku Kogyo Kk ウレタン・シリコーン相溶化剤、ウレタンエマルションおよびシリコーン内包量の相対量を測定する方法
JP2013253184A (ja) * 2012-06-08 2013-12-19 Kansai Paint Co Ltd カチオン電着塗料組成物
WO2021118114A2 (fr) * 2019-12-12 2021-06-17 주식회사 포스코 Composition de revêtement de tôle d'acier électro-galvanisée ayant une résistance à la chaleur et une capacité d'adhésion à une bande excellentes, tôle d'acier traitée en surface l'utilisant et procédé de fabrication de celle-ci

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4683581B2 (ja) 2005-02-02 2011-05-18 日本パーカライジング株式会社 水系金属材料表面処理剤、表面処理方法及び表面処理金属材料
CN111936558B (zh) 2018-04-12 2022-03-18 日本帕卡濑精株式会社 聚硅氧烷化合物和组合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH073206A (ja) * 1993-06-18 1995-01-06 Nippon Shokubai Co Ltd ガスバリヤ用表面処理用組成物
JP2006036996A (ja) * 2004-07-29 2006-02-09 Sakai Kagaku Kogyo Kk ウレタン・シリコーン相溶化剤、ウレタンエマルションおよびシリコーン内包量の相対量を測定する方法
JP2013253184A (ja) * 2012-06-08 2013-12-19 Kansai Paint Co Ltd カチオン電着塗料組成物
WO2021118114A2 (fr) * 2019-12-12 2021-06-17 주식회사 포스코 Composition de revêtement de tôle d'acier électro-galvanisée ayant une résistance à la chaleur et une capacité d'adhésion à une bande excellentes, tôle d'acier traitée en surface l'utilisant et procédé de fabrication de celle-ci

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JP2023106679A (ja) 2023-08-02
CN118556115A (zh) 2024-08-27
KR20240121856A (ko) 2024-08-09

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