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WO2025220605A1 - Composition de revêtement antisalissure de type non chimique, procédé de formation de film de revêtement antisalissure l'utilisant, et article sur lequel est formé un film de revêtement antisalissure - Google Patents

Composition de revêtement antisalissure de type non chimique, procédé de formation de film de revêtement antisalissure l'utilisant, et article sur lequel est formé un film de revêtement antisalissure

Info

Publication number
WO2025220605A1
WO2025220605A1 PCT/JP2025/014468 JP2025014468W WO2025220605A1 WO 2025220605 A1 WO2025220605 A1 WO 2025220605A1 JP 2025014468 W JP2025014468 W JP 2025014468W WO 2025220605 A1 WO2025220605 A1 WO 2025220605A1
Authority
WO
WIPO (PCT)
Prior art keywords
mass
antifouling coating
resin
less
coating composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/014468
Other languages
English (en)
Japanese (ja)
Inventor
清樹 石丸
賢史 河野
恵美 坂野
浩吉 田口
洸太 中島
衛司 野村
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.)
BASSERU CHEMICAL Co Ltd
Original Assignee
BASSERU CHEMICAL Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASSERU CHEMICAL Co Ltd filed Critical BASSERU CHEMICAL Co Ltd
Priority to AU2025252539A priority Critical patent/AU2025252539A1/en
Priority to KR1020257029705A priority patent/KR20250168201A/ko
Publication of WO2025220605A1 publication Critical patent/WO2025220605A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular

Definitions

  • the present invention relates to a novel, chemical-free antifouling paint composition that can inhibit the adhesion of marine organisms and seaweed to marine materials, underwater structures, fishing nets, etc., a method for forming an antifouling coating using the same, and an article on which the antifouling coating is formed.
  • Marine organisms attach to the surfaces of marine materials, underwater structures, fishing nets, and other items used in the fields of fisheries, fishing, and maritime transportation.
  • Marine organisms such as barnacles, hydroids, hairy bryozoans, and sea bass attach to marine materials, underwater structures, and fishing nets, clogging the mesh and causing problems such as deterioration of water quality, fish disease, and net damage.
  • Various antifouling paints have been used to prevent marine organisms from attaching to marine materials, underwater structures, and fishing nets, which cause these problems.
  • antifouling paints containing organotin compounds as antifouling ingredients were used as ship bottom paints, etc., but their use has been restricted in recent years due to their toxicity, and there is a demand for the development of alternative antifouling paints.
  • Patent Document 1 discloses an aqueous antifouling paint composition containing an emulsion resin, a dispersion resin, and a marine organism repellent.
  • Patent Document 2 a resin is produced by binding a seawater-soluble additive such as rosin to the carboxyl group of a hydrolyzable resin. This resin is then mixed with a marine life repellent to produce an antifouling paint composition, which maintains its antifouling effect.
  • a seawater-soluble additive such as rosin
  • Patent Document 3 discloses an antifouling paint composition that uses a sulfur-containing organopolysiloxane block vinyl copolymer to soften the paint film and prevent it from peeling off due to tidal changes.
  • antifouling paints containing marine organism repellents have been used on marine materials, underwater structures, fishing nets, etc. to prevent the attachment of marine organisms and seaweed.
  • antifouling agents marine organism repellents
  • the present invention was made in light of these circumstances, and aims to provide a chemical-free antifouling paint composition that can exert antifouling effects over a long period of time and suppress the accumulation of chemicals in marine products, an antifouling coating formed using the same, and an article on which the coating is formed.
  • a chemical-free antifouling coating composition for forming a coating film that inhibits the attachment of aquatic organisms on a surface of an article that comes into contact with water comprising: a resin (A) having an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less and a weight-average molecular weight (Mw) of 50,000 or more and 350,000 or less, and being one or more resins selected from the group consisting of acrylic resins, acrylic silicone resins, polyester resins, alkyd resins, and alkyd rosin resins; and an implantation inhibitor (B) being one or more selected from the group consisting of silicone compounds and aliphatic hydrocarbon compounds, the chemical-free antifouling coating composition being free of an aquatic organism repellent that is one or more selected from the group consisting of cuprous oxide, bis(2-sulf
  • the chemical-free antifouling coating composition according to ⁇ 1> further comprising a coating adhesion promoter (C) which is one or more selected from the group consisting of rosin and a silane coupling agent.
  • C coating adhesion promoter
  • ⁇ 3> The chemical-free antifouling coating composition according to ⁇ 2>, containing the rosin having an acid value of 100 mgKOH/g or more and 220 mgKOH/g or less and a softening point of 78°C or more and 100°C or less in an amount of 0.5% by mass or more and 10% by mass or less relative to the non-volatile components.
  • the silicone compound comprises one or more silicone oils selected from the group consisting of polyether-modified silicone oil, alkyl-modified silicone oil, alcohol-modified silicone oil, fluorine-modified silicone oil, amino-modified silicone oil, mercapto-modified silicone oil, epoxy-modified silicone oil, carboxyl-modified silicone oil, higher fatty acid-modified silicone oil, and higher fatty acid-containing silicone oil, and the content of the silicone oil is 5% by mass to 50% by mass based on the non-volatile components;
  • the aliphatic hydrocarbon compound is one or more selected from the group consisting of polyolefin, wax, liquid paraffin, and
  • the silicone compound comprises one or more silicone powders selected from the group consisting of a silicone composite powder having an average particle size of 0.2 ⁇ m to 60 ⁇ m, a silicone rubber powder having an average particle size of 1 ⁇ m to 30 ⁇ m, and a silicone resin powder having an average particle size of 0.2 ⁇ m to 8.0 ⁇ m, and the content of the silicone powder is 0.5% by mass to 2.0% by mass of the non-volatile components.
  • a method for forming an antifouling coating film comprising the steps of applying the chemical-free antifouling coating composition according to any one of ⁇ 1> to ⁇ 7> to an article, and drying the applied coating film of the chemical-free antifouling coating composition.
  • the present invention provides a chemical-free antifouling paint composition that can inhibit the adhesion of aquatic organisms without containing chemicals, and that reduces the risk of water pollution due to the release of chemicals or the accumulation of chemicals in aquatic organisms. Also provided are a method for forming an antifouling coating using the chemical-free antifouling paint composition, and an article on which the coating is formed.
  • FIG. 1 is a photograph of an ABS compose coated with the chemical-free antifouling coating composition of the present invention after a sea immersion test. This is a photograph of an undyed ABS Compose (left, Comparative Example 3) after an underwater immersion test, and a photograph of an ABS Compose coated with a chemical-free paint (right, Comparative Example 4).
  • the present invention relates to a chemical-free antifouling coating composition (hereinafter, sometimes abbreviated as "the coating composition of the present invention") that contains: a resin (A) having an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less and a weight-average molecular weight (Mw) of 50,000 or more and 350,000 or less, the resin being one or more selected from the group consisting of acrylic resins, acrylic silicone resins, polyester resins, and alkyd resins; and an implantation inhibitor (B) being one or more selected from the group consisting of silicone compounds and aliphatic hydrocarbon compounds, and that does not contain an aquatic organism repellent that is one or more selected from the group consisting of cuprous oxide, bis(2-sulfidopyridin-1-olato)copper, and bis(N,N-dimethyldithiocarbamate)N,N'-ethylenebis(thiocarbamoylthiozin
  • the coating composition of the present invention is used to form a coating film that inhibits the attachment of aquatic organisms on the surface of an article that comes into contact with water.
  • Each component is described in detail below.
  • the resin (A) contained in the coating composition of the present invention has an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less and a weight average molecular weight (Mw) of 50,000 or more and 350,000 or less, and is one or more types of resin selected from the group consisting of acrylic resins, acrylic silicone resins, polyester resins, alkyd resins, and alkyd rosin resins.
  • Resin (A) preferably contains an acrylic resin.
  • the acrylic resin may be a single type or a combination of two or more types.
  • the acrylic resin is primarily (50 mol% or more) composed of structural units derived from alkyl (meth)acrylate monomers, but is not limited to homopolymers.
  • the acrylic resin may also be a copolymer of alkyl (meth)acrylate monomers and copolymerizable monomers.
  • the amount of structural units derived from alkyl (meth)acrylate monomers in the acrylic resin is, for example, 80 mol% or more, 85 mol% or more, 90 mol% or more, or 95 mol% or more.
  • acrylic resins include polyalkyl (meth)acrylate and alkyl (meth)acrylate-(meth)acrylic acid copolymer.
  • alkyl (meth)acrylate refers to at least one of alkyl acrylate and alkyl methacrylate
  • (meth)acrylic acid refers to at least one of acrylic acid and methacrylic acid.
  • the alkyl (meth)acrylate-(meth)acrylic acid copolymer may also be obtained by partially hydrolyzing the alkyl ester groups of polyalkyl(meth)acrylate.
  • the acid value of the resin used as resin (A) is 0 to 10 mgKOH/g, preferably 0 to 5 mgKOH/g, from the perspective of long-term storage stability.
  • acid value refers to the "amount (mg) of KOH required to neutralize the free acid in 1 g of the nonvolatile content of the product," and is expressed in units of mgKOH/g. Acid value can be evaluated using the titration method described in the same standard.
  • resin (A) can contain a first acrylic resin having an acid value of 0 mgKOH/g and a second acrylic resin having an acid value of 1 mgKOH/g or more and 10 mgKOH/g or less (preferably 1 mgKOH/g or more and 5 mgKOH/g or less).
  • resin (A) can contain the first acrylic resin and the second acrylic resin in a mass ratio of 100:0 to 90:10 or 100:0 to 95:5.
  • resin (A) can be one or more acrylic resins having an acid value of 3 to 10 mgKOH/g, or one or more acrylic resins having an acid value of 3 to 5 mgKOH/g.
  • the weight average molecular weight (Mw) of the resin used as resin (A) is 50,000 or more and 350,000 or less from the viewpoint of film formation, and is preferably 50,000 or more and 300,000 or less to maintain the effect over a longer period of time, and more preferably 100,000 or more and 250,000 or less.
  • the molecular weight can be measured using any known method, such as GPC (gel permeation chromatography) analysis.
  • resin (A) is one or more resins selected from the group consisting of acrylic resins, acrylic silicone resins, polyester resins, alkyd resins, and alkyd rosin resins, and each resin may have an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less, and a weight average molecular weight (Mw) of 50,000 or more and 300,000 or less.
  • resin (A) is one or more types of acrylic resins, each of which has an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less and a weight average molecular weight (Mw) of 50,000 or more and 350,000 or less, preferably 50,000 or more and 300,000 or less.
  • Mw weight average molecular weight
  • resin (A) is one or more acrylic resins selected from the group consisting of polyalkyl acrylate resins, polyalkyl methacrylate resins, alkyl acrylate-acrylic acid copolymer resins, and alkyl methacrylate-methacrylic acid copolymer resins, and each acrylic resin can have an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less and a weight average molecular weight (Mw) of 50,000 or more and 350,000 or less, preferably 50,000 or more and 300,000 or less.
  • Mw weight average molecular weight
  • the content of resin (A) can be, for example, 25% by mass or more and 80% by mass or less, 28% by mass or more and 75% by mass or less, 30% by mass or more and 70% by mass or less, 33% by mass or more and 60% by mass or less, or 35% by mass or more and 50% by mass or less of the non-volatile components of the coating composition of the present invention (this refers to all components contained in the chemical-free antifouling coating composition excluding volatile components such as solvents; also referred to as the solid content).
  • the coating composition of the present invention contains an implantation inhibitor (B) for inhibiting the implantation of aquatic organisms on the surface of the coating film.
  • the implantation inhibitor (B) is one or more compounds selected from the group consisting of silicone compounds and aliphatic hydrocarbon compounds.
  • the coating composition of the present invention may contain one or more implantation inhibitors (B). Each component will be described in detail below.
  • silicone compounds examples include silicone oil and silicone powder.
  • silicone oils include polyether-modified silicone oil, alkyl-modified silicone oil, alcohol-modified silicone oil, fluorine-modified silicone oil, amino-modified silicone oil, mercapto-modified silicone oil, epoxy-modified silicone oil, phenyl-modified silicone oil, carboxyl-modified silicone oil, higher fatty acid-modified silicone oil, and higher fatty acid-containing silicone oil, with polyether-modified silicone oil being preferred.
  • the silicone oil may be one of these, or a combination of two or more.
  • the content of silicone oil is preferably 5% by mass or more and 50% by mass or less, more preferably 10% by mass or more and 40% by mass or less, and even more preferably 25% by mass or more and 40% by mass or less, based on the non-volatile components of the coating composition of the present invention.
  • the total content of the silicone oils be within the above numerical range.
  • the hydrophilic-lipophilic balance (HLB) of the silicone oil is preferably 1 or more and 8 or less, and more preferably 2 or more and 6 or less.
  • silicone powders examples include silicone composite powders with an average particle size of 0.2 ⁇ m to 60 ⁇ m, silicone rubber powders with an average particle size of 1 ⁇ m to 30 ⁇ m, and silicone resin powders with an average particle size of 0.2 ⁇ m to 8.0 ⁇ m. These may be used alone or in combination of any two or more. Specific examples of silicone powders include KMP-600, KMP-601, KMP-602, KMP-605, X-52-7030, KMP-402, KMP-597, KMP-598, KMP-590, KMP-706, X-52-854, and X-52-1621 manufactured by Shin-Etsu Chemical Co., Ltd.
  • the content of silicone powder is preferably 0% by mass or more and 2.0% by mass or less, more preferably 0.5% by mass or more and 2.0% by mass or less, even more preferably 0.5% by mass or more and 1.5% by mass or less, and particularly preferably 0.5% by mass or more and 1.0% by mass or less, relative to the non-volatile components of the coating composition of the present invention.
  • the total content of the silicone powders be within the above numerical range.
  • Aliphatic hydrocarbon compounds include polyolefins, waxes, liquid paraffin, and petrolatum. Among these, those with a weight-average molecular weight of 150 or more and 3,000 or less are preferably used. Furthermore, those that are liquid at room temperature and normal pressure are preferred. These may be used alone or in combination of two or more.
  • polystyrene resin examples include polybutenes (polybutene, polyisobutene, etc.), ethylene- ⁇ -olefin copolymers, etc., with polybutenes being preferred. These may be used alone or in combination of two or more.
  • waxes examples include hydrocarbon waxes such as solid paraffin, and animal waxes such as lanolin. These may be used alone or in combination of two or more.
  • petrolatum examples include white petrolatum and yellow petrolatum. These may be used alone or in combination of two or more types.
  • aliphatic hydrocarbon compounds include NOF Polybutene (registered trademark, the same applies hereinafter) 0N, NOF Polybutene 015N, NOF Polybutene 3N, NOF Polybutene 10N, NOF Polybutene 30N, and NOF Polybutene 200N manufactured by NOF Corporation; Lucant (registered trademark, the same applies hereinafter) HC-40, Lucant HC-600, Lucant HC-600, Lucant HC-1100, and Lucant HC-2000 manufactured by Mitsui Chemicals, Inc.; and Nippon Seiro Co., Ltd.
  • waxes examples include ParaffinWax-115, ParaffinWax-120, ParaffinWax-125, ParaffinWax-130, ParaffinWax-135, ParaffinWax-140, ParaffinWax-145, ParaffinWax-150, ParaffinWax-155, HNP-3, HNP-5, HNP-6, HNP-10, HNP-11, HNP-12, and HNP-51 manufactured by Paraffin Wax.
  • the content of the aliphatic hydrocarbon compounds is preferably 15% by mass or more and 40% by mass or less, more preferably 15% by mass or more and 35% by mass or less, and even more preferably 18% by mass or more and 32% by mass or less, relative to the non-volatile components of the coating composition of the present invention.
  • the total content of the aliphatic hydrocarbon compounds be within the above numerical range.
  • the implantation inhibitor (B) can be a combination of silicone oil and polyolefin, or a combination of silicone oil, polyolefin, and silicone powder.
  • the implantation inhibitor (B) can be a polyether-modified silicone oil and a polybutene, or a polyether-modified silicone oil, a polybutene, and a silicone powder.
  • the coating composition of the present invention preferably contains a coating adhesion promoter (C) which is one or more selected from the group consisting of rosin and silane coupling agents.
  • a coating adhesion promoter which is one or more selected from the group consisting of rosin and silane coupling agents.
  • the coating composition of the present invention containing the coating adhesion promoter (C) can suppress adhesion of aquatic organisms without containing the aquatic organism repellent, and is less likely to peel off the coating film even when used in marine environments with tidal fluctuations, reducing the risk of water pollution due to the release of chemicals or their accumulation in aquatic organisms.
  • the paint composition of the present invention contains a coating adhesion promoter (C).
  • the coating adhesion promoter (C) can be selected depending on the material and shape of the substrate.
  • the coating adhesion promoter (C) may be used alone or in combination of any two or more types.
  • rosins examples include modified rosins (maleic rosin, fumaric rosin, specially modified rosin, etc.), modified rosin esters (maleic rosin ester, fumaric rosin ester, etc.), and unmodified rosin.
  • modified rosins maleic rosin, fumaric rosin, specially modified rosin, etc.
  • modified rosin esters maleic rosin ester, fumaric rosin ester, etc.
  • unmodified rosin Specific examples include Haritac F-75, Haritac FG-90, and Harimac T-80 manufactured by Harima Chemical Co., Ltd.
  • the acid value of the rosin is preferably 100 mg KOH/g or more and 200 mg KOH/g or less.
  • the softening point of the rosin is preferably 78°C or more and 100°C or less. More preferably, the acid value of the rosin is 140 mg KOH/g or more and 200 mg KOH/g or less, and the softening point is 75°C or more and 90°C or less. These may be used alone or in combination of any two or more types.
  • the rosin content is preferably 0.5% by mass or more and 10% by mass or less, and more preferably 0.9% by mass or more and 9% by mass or less, based on the non-volatile components of the coating composition of the present invention.
  • the rosin content may also be 1% by mass or more and 10% by mass or less, based on the non-volatile components of the coating composition.
  • the total content of the rosins is within the above numerical range.
  • the rosin contains rosins with an acid value of 100 mg KOH/g or more and 220 mg KOH/g or less and a softening point of 78°C or more and 100°C or less, within the above numerical range.
  • silane coupling agents include vinyl-modified silane coupling agents, epoxy-modified silane coupling agents, styryl-modified silane coupling agents, methacryl- and acrylic-modified silane coupling agents, amino-modified silane coupling agents, mercapto-modified silane coupling agents, butadiene polymer-modified silane coupling agents, acid anhydride-functional group-containing butadiene polymer-modified silane coupling agents, styrene-butadiene polymer-modified silane coupling agents, hydrolyzable silyl group silane coupling agents, multifunctional group silane coupling agents, methoxy-type silanes, ethoxy-type silanes, silazanes, siloxanes, etc.
  • More preferred examples include X-12-1267B, X-12-1287A, X-12-1281A, X-12-5263HP, KBM-3086, KBM-1003, KBE-1003, KBM-303, KBM-402, KBM-403, KBE-402, KBE-403, KBM-1403, KBM-502, KBM-503, KBE-502, KBE503, KBM-5103, KBM-602, KBM-603, KBM-903, KBE-903, KBE-9103P, KBM-573, and KBM-575, all manufactured by Shin-Etsu Chemical Co., Ltd.
  • Particularly preferred are aminosilane coupling agents, acid anhydride functional group-containing butadiene polymer-modified silane coupling agents, and hydrolyzable silyl group silane coupling agents.
  • the content of the silane coupling agent is preferably 0.2% by mass or more and 2.0% by mass or less, and more preferably 0.5% by mass or more and 1.5% by mass or less, based on the non-volatile components of the coating composition of the present invention.
  • the paint composition of the present invention does not contain one or more aquatic organism repellents selected from the group consisting of cuprous oxide (copper(I) oxide), copper bis(2-sulfidopyridin-1-olato), and N,N'-ethylenebis(thiocarbamoylthiozinc) bis(N,N-dimethyldithiocarbamate).
  • Cuprous oxide, copper bis(2-sulfidopyridin-1-olato), and N,N'-ethylenebis(thiocarbamoylthiozinc) bis(N,N-dimethyldithiocarbamate) are widely used as antifouling agents.
  • the paint composition of the present invention by including resin (A) and implantation inhibitor (B), can exhibit long-term antifouling effects even without these antifouling agents.
  • an antifouling agent is an agent that prevents the adhesion of organisms to the bottom of a ship or fishing net in seawater.
  • antifouling agents examples include triphenylborane-amine complex compounds, tetraalkylthiuram diyl sulfide compounds, copper powder, copper rhodanide, copper naphthenate, sodium pyrithione, soluble glass, zinc bis(2-sulfidopyridin-1-olato), bisdimethyldithiocarbamoyl, zinc ethylenebisdithiocarbamate, zinc methyldithiocarbamate, zinc ethylenedithiocarbamate, manganese ethylenebisdithiocarbamate, 2,4,5,6-tetrachloroisophthalonitrile, 2,3-dichloro-N-(2 N,N'-ethyl-6'-methylphenyl)maleimide, 4,5-dichloro-2-n-octyl-isoazolin-3(2H)-one, 2-methylthio-4-t-butylamino-6-cyclopropylamino-
  • the coating composition of the present invention may have a total content of the resin (A) and the implantation inhibitor (B) of 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the non-volatile components of the coating composition of the present invention.
  • the coating composition of the present invention comprises resins (A), (B), and (C), wherein resin (A) is one or more types of acrylic resin, and implantation inhibitor (B) is a silicone oil and polyolefin, or a silicone oil, a polyolefin, and a silicone powder, preferably a polyether-modified silicone oil and polybutenes, or a polyether-modified silicone oil, a polybutenes, and a silicone powder, and may be free of an aquatic organism repellent selected from the group consisting of cuprous oxide (copper(I) oxide), bis(2-sulfidopyridin-1-olato)copper, and bis(N,N-dimethyldithiocarbamate)N,N'-ethylenebis(thiocarbamoylthiozinc).
  • resin (A) is one or more types of acrylic resin
  • implantation inhibitor (B) is a silicone oil and polyolefin, or a silicone oil, a polyolefin, and
  • the coating composition of the present invention contains resins (A), (B), and (C), and the total content of resin (A), implantation inhibitor (B), and coating adhesion promoter (C) can be 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the non-volatile components of the coating composition of the present invention.
  • the coating composition of the present invention may contain a solvent.
  • solvents include aromatic hydrocarbon solvents such as xylene, toluene, ethylbenzene, and trimethylbenzene; aliphatic hydrocarbon solvents such as heptane; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and alcohol solvents such as ethanol, isopropyl alcohol, and n-butanol. These may be used alone or in combination of two or more. Of these, aromatic hydrocarbon solvents are preferred, and xylene is more preferred.
  • the coating composition of the present invention can be produced using any known apparatus and method.
  • the method for forming an antifouling coating of the present invention comprises the steps of applying the above-described chemical-free antifouling coating composition of the present invention to an article and drying the coating film of the applied chemical-free antifouling coating composition.
  • Application to articles such as fishery materials, underwater structures, and fishing nets can be carried out by immersion, brushing, roll coating, spraying, or the like.
  • the coating film can be dried under any conditions, such as natural drying, to form an antifouling coating.
  • Examples of goods include fishery materials, underwater structures, and fishing nets.
  • Examples of fishery materials include floats, buoys, ropes, compose, and fishing gear.
  • Examples of underwater structures include various facilities such as undersea cables, undersea tunnels, and power generation facilities, as well as piping for various facilities and bridges. Of these, fishery materials and fishing nets are preferred.
  • the antifouling coating method of the present invention allows for the production of articles having an antifouling coating formed thereon.
  • the antifouling coating formed contains a resin (A) having an acid value of 0 mgKOH/g or more and 10 mgKOH/g or less, a weight-average molecular weight (Mw) of 50,000 or more and 350,000 or less, and at least one resin selected from the group consisting of acrylic resins, acrylic silicone resins, polyester resins, and alkyd resins, and an implantation inhibitor (B) being at least one selected from the group consisting of silicone compounds and aliphatic hydrocarbon compounds, but does not contain an aquatic organism repellent selected from the group consisting of cuprous oxide, bis(2-sulfidopyridin-1-olato)copper, and bis(N,N-dimethyldithiocarbamate)N,N'-ethylenebis(thiocarbamoylthiozinc).
  • A having an acid value of 0 mgKOH/g or more and 10 mg
  • the antifouling coating formed may have a silicone oil content of 5 to 50% by mass, preferably 10 to 40% by mass, and more preferably 25 to 40% by mass, an aliphatic hydrocarbon compound content of 15 to 40% by mass, preferably 15 to 35% by mass, and more preferably 18 to 32% by mass, a silicone powder content of 0 to 2.0% by mass, preferably 0.5 to 2.0% by mass, more preferably 0.5 to 1.5% by mass, and even more preferably 0.5 to 1.0% by mass, a rosin content of 0 to 10% by mass, preferably 0.5 to 10% by mass, and more preferably 0.9 to 9% by mass, and a silane coupling agent content of 0 to 2.0% by mass, preferably 0.2 to 2.0% by mass, and more preferably 0.5 to 1.5% by mass.
  • the antifouling coating formed can have a total content of the resin (A), implantation inhibitor (B), and coating adhesion promoter (C) of 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more.
  • Resin (A) a solvent-based (xylene) acrylic resin (40% non-volatile component) was used as the base resin for the chemical-free antifouling coating composition. These resins are hereinafter referred to as Base Resin 1 to Base Resin 13 in each table.
  • Base Resin 1 to Base Resin 8 had an acid value of 0 mgKOH/g, and their weight-average molecular weights (Mw) are as shown in Table 1.
  • Base Resin 9 to Base Resin 13 had a weight-average molecular weight (Mw) of 200,000, and their acid values are as shown in Table 2.
  • Implantation inhibitor (B) The following was used as the implantation inhibitor (B).
  • Example 5 To 59.9 parts by mass of xylene, 20.5 parts by mass of polyolefin (NOF Polybutene 0N, implantation inhibitor (B)) and 38.0 parts by mass of silicone oil (KF-6020, implantation inhibitor (B)) were sequentially added with stirring, and the mixture was mixed and stirred for 10 minutes. Further, 103.8 parts by mass of base resin 5 (polyalkyl acrylate, weight average molecular weight 200,000, acid value 0 mgKOH/g) was added, and the mixture was mixed and stirred for 30 minutes.
  • base resin 5 polyalkyl acrylate, weight average molecular weight 200,000, acid value 0 mgKOH/g
  • Example 14 To 59.9 parts by mass of xylene, 20.5 parts by mass of polyolefin (NOF polybutene 0N, implantation inhibitor (B)) and 38.0 parts by mass of silicone oil (KF-6020, implantation inhibitor (B)) were sequentially added with stirring, and the mixture was mixed and stirred for 10 minutes. Further, 101.2 parts by mass of base resin 5 (polyalkyl acrylate, weight average molecular weight 200,000, acid value 0 mgKOH/g) and 2.6 parts by mass of base resin 10 (alkyl acrylate-acrylic acid copolymer, weight average molecular weight 200,000, acid value 3 mgKOH/g) were sequentially added, and the mixture was mixed and stirred for 30 minutes.
  • base resin 5 polyalkyl acrylate, weight average molecular weight 200,000, acid value 0 mgKOH/g
  • base resin 10 alkyl acrylate-acrylic acid copolymer, weight average molecular weight 200,000, acid value 3 mgKOH/
  • Tables 1 and 2 show the results of the sea immersion test 1 and the storage stability test. Furthermore, as Comparative Example 1, a commercially available copper-based antifouling paint was used instead of the chemical-free antifouling paint composition of the present invention, and the marine immersion test-1 and storage stability test were carried out. The results are also shown in Table 1.
  • Example 27 To 61.9 parts by mass of xylene, 20.7 parts by mass of polyolefin (NOF Polybutene 0N, implantation inhibitor (B)) and 38.4 parts by mass of silicone oil (KF-6020, implantation inhibitor (B)) were sequentially added with stirring, and mixed and stirred for 10 minutes. 98.6 parts by mass of Base Resin 5 (weight average molecular weight 200,000) and 5.2 parts by mass of Base Resin 10 (acid value 3 mgKOH/g) were then sequentially added and mixed and stirred for 10 minutes. 1.0 part by mass of rosin (Hamatack FG-90) was then added and mixed and stirred for 30 minutes. The ratio of rosin to non-volatile components is shown in Table 4.
  • the chemical-free antifouling coating compositions of Examples 18 to 26 were produced using the same production procedure as in Example 17 above, except for the formulations shown in Table 3.
  • the chemical-free antifouling coating compositions of Examples 28 to 36 were produced using the same production procedure as in Example 27 above, except for the formulations shown in Table 4.
  • the obtained chemical-free antifouling coating composition was subjected to the following marine immersion test-2 and the above storage stability test. The results are shown in Tables 3 and 4.
  • Comparative Example 2 a commercially available copper-based antifouling paint was used instead of the chemical-free antifouling paint composition of the present invention, and marine immersion test-2 and storage stability test were carried out. The results are also shown in Table 3.
  • Example 47 Under stirring, 61.9 parts by weight of xylene, polyolefin (NOF polybutene 0N, implantation inhibitor (B)) 20.7 parts by weight, silicone oil (KF-6020, implantation inhibitor (B)) 38.4 parts by weight were sequentially added, mixed and stirred for 10 minutes, further base resin 5 (weight average molecular weight 200,000) 98.6 parts by weight, base resin 10 (acid value 3 mg KOH / g) 5.2 parts by weight were sequentially added, mixed and stirred for 10 minutes, silane coupling agent (X-12-1287A) 0.2 parts by weight was added and mixed and stirred for 30 minutes.
  • the ratio of silane coupling agent to non-volatile components is as shown in Table 8.
  • the chemical-free antifouling coating compositions of Examples 38 to 46 were produced using the same production procedure as in Example 37 above, except for the formulations shown in Table 7.
  • the chemical-free antifouling coating compositions of Examples 48 to 56 were produced using the same production procedure as in Example 47 above, except for the formulations shown in Table 8.
  • the obtained chemical-free antifouling coating composition was subjected to the above-mentioned marine immersion test-2 and storage stability test. The results are shown in Tables 7 and 8.
  • Chemical-free antifouling coating compositions of Examples 58 to 66 were produced using the same production procedures as in Example 57 above, except that the formulations shown in Table 11 were used.
  • the obtained chemical-free antifouling coating composition was subjected to the above-mentioned marine immersion test-2 and storage stability test. The results are shown in Table 11.
  • Chemical-free antifouling coating compositions of Examples 68 to 76 were produced using the same production procedures as in Example 67 above, except that the formulations shown in Table 14 were used.
  • the obtained chemical-free antifouling coating composition was subjected to the above-mentioned marine immersion test-2 and storage stability test. The results are shown in Table 14.
  • Chemical-free antifouling coating compositions of Examples 78 to 86 were produced using the same production procedures as in Example 77 above, except that the formulations shown in Table 17 were used.
  • the obtained chemical-free antifouling coating composition was subjected to the above-mentioned marine immersion test-2 to evaluate adhesion of aquatic organisms and cleaning after 6 months of immersion. Furthermore, the obtained chemical-free antifouling coating composition was subjected to a storage stability test. The results are shown in Table 17.
  • ABS resin adhesion test The ABS resin adhesion test was carried out using a 1 mm thick, 6 cm x 8 cm board (Japan Test Panel (wood)) in accordance with JIS K5600-5-6: General test methods for paints, Part 5: Mechanical properties of coatings, Section 6: Adhesion (cross-cut method).
  • “1 mm width” and “2 mm width” indicate the width of the cross-cuts made on the surface of the coating
  • “100/100” indicates that no peeling was observed after removal of the adhesive tape in any of the 100 squares made by the cross-cuts
  • “50/50” indicates that no peeling was observed after removal of the adhesive tape in any of the 50 squares made by the cross-cuts.
  • Example 87 the chemical-free antifouling coating composition of Example 79 was applied to an ABS compose (diameter 47 mm, length 2 m), dried, and immersed in the sea for 6 months.
  • the ABS compose was immersed in the sea for 6 months without being coated with any paint.
  • a paint having a composition in which the antifouling agents (cuprous oxide and bis-2-pyridinethiol copper salt) were removed from the antifouling agent-containing paint (Bassel Chemical's Bowmow (registered trademark) CU#1500) was applied to an ABS compose, dried, and then immersed in the sea for 6 months.
  • the antifouling agents cuprous oxide and bis-2-pyridinethiol copper salt
  • Figure 1 shows a photograph of the ABS compose of Example 87 after an underwater immersion test.
  • Figure 2 shows a photograph of the ABS compose of Comparative Example 3 (left) and the ABS compose of Comparative Example 4 (right) after an underwater immersion test.
  • Figure 1 no adhesion of aquatic organisms was observed in Example 87.
  • Figure 2 adhesion of aquatic organisms was suppressed in Comparative Example 4 compared to Comparative Example 3, where no paint was applied, but adhesion of aquatic organisms was still observed.
  • Figures 1 and 2 demonstrate that applying the chemical-free antifouling coating composition of the present invention provides excellent antifouling effects.

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Abstract

La présente invention concerne une nouvelle composition de revêtement antisalissure de type non chimique qui est capable de supprimer l'adhérence d'organismes marins et d'algues à du matériel de pêche, une structure sous-marine, un filet de pêche et similaire.　Une composition de revêtement antisalissure de type non chimique selon la présente invention contient : une résine (A) qui a un indice d'acide de 0 mgKOH/g à 10 mgKOH/g, limites incluses, et une masse moléculaire moyenne en poids (Mw) de 50 000 à 350 000, limites incluses, et qui est composée d'une ou de plusieurs résines qui sont choisies parmi une résine acrylique, une résine de silicone acrylique, une résine de polyester, une résine alkyde et une résine de colophane alkyde ; et un inhibiteur de fixation (B) qui est un ou plusieurs composés choisis parmi un composé de silicone et un composé hydrocarboné aliphatique. Cette composition de revêtement antisalissure de type non chimique ne contient aucun répulsif d'organismes aquatiques qui consiste en une ou plusieurs substances choisies parmi l'oxyde cuivreux, le cuivre bis(2-sulfidopyridin-1-olato), et le bis(N,N-acide diméthyldithiocarbamique)N,N'-éthylène bis(zinc thiocarbamoylthio).
PCT/JP2025/014468 2024-04-19 2025-04-11 Composition de revêtement antisalissure de type non chimique, procédé de formation de film de revêtement antisalissure l'utilisant, et article sur lequel est formé un film de revêtement antisalissure Pending WO2025220605A1 (fr)

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AU2025252539A AU2025252539A1 (en) 2024-04-19 2025-04-11 Non-chemical type antifouling coating composition, method for forming antifouling coating film using same, and article on which antifouling coating film is formed
KR1020257029705A KR20250168201A (ko) 2024-04-19 2025-04-11 무약형 방오 도료 조성물, 그것을 사용한 방오성 피막의 형성 방법, 및 방오성 피막이 형성된 물품

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JP2001131413A (ja) * 1999-11-04 2001-05-15 Kurume Research Park:Kk 海洋生物付着防止ゴム組成物及びそれを使用した海洋生物付着防止方法
JP2010013591A (ja) * 2008-07-07 2010-01-21 Shin-Etsu Chemical Co Ltd 水中生物付着防止塗料組成物及びそれを用いた水中構造物
JP2010090246A (ja) * 2008-10-07 2010-04-22 Nippon Fine Chem Co Ltd 防汚塗料組成物およびそれを用いた防汚方法
WO2017022661A1 (fr) * 2015-07-31 2017-02-09 中国塗料株式会社 Composition de matériau de revêtement anti-salissures, film de revêtement anti-salissures, substrat anti-salissures, composé de colophane pour composition de matériau de revêtement anti-salissures et procédé de fabrication de composition de matériau de revêtement anti-salissures
WO2018182023A1 (fr) * 2017-03-31 2018-10-04 日東電工株式会社 Composition pour formation de film de revêtement, film de revêtement, et feuille adhésive
JP2020026533A (ja) * 2018-08-17 2020-02-20 ヨトゥン アーエス 防汚組成物
WO2022181298A1 (fr) * 2021-02-26 2022-09-01 バッセル化学株式会社 Composition de peinture antisalissure à base aqueuse, revêtement antisalissure formé par utilisation de cette dernière et filet de pêche, navire et structure sous-marine dont la surface porte un revêtement

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JP5480370B2 (ja) * 2010-04-20 2014-04-23 株式会社クレハ 水中防汚材、溶融成形物及び塗料
SG11202100680WA (en) * 2018-07-27 2021-02-25 Chugoku Marine Paints Antifouling paint composition, antifouling coating, substrate with antifouling coating, production method thereof, and repair method

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JPH07133447A (ja) * 1993-11-09 1995-05-23 Japan Steel & Tube Constr Co Ltd 生物付着防止用組成物
JP2001131413A (ja) * 1999-11-04 2001-05-15 Kurume Research Park:Kk 海洋生物付着防止ゴム組成物及びそれを使用した海洋生物付着防止方法
JP2010013591A (ja) * 2008-07-07 2010-01-21 Shin-Etsu Chemical Co Ltd 水中生物付着防止塗料組成物及びそれを用いた水中構造物
JP2010090246A (ja) * 2008-10-07 2010-04-22 Nippon Fine Chem Co Ltd 防汚塗料組成物およびそれを用いた防汚方法
WO2017022661A1 (fr) * 2015-07-31 2017-02-09 中国塗料株式会社 Composition de matériau de revêtement anti-salissures, film de revêtement anti-salissures, substrat anti-salissures, composé de colophane pour composition de matériau de revêtement anti-salissures et procédé de fabrication de composition de matériau de revêtement anti-salissures
WO2018182023A1 (fr) * 2017-03-31 2018-10-04 日東電工株式会社 Composition pour formation de film de revêtement, film de revêtement, et feuille adhésive
JP2020026533A (ja) * 2018-08-17 2020-02-20 ヨトゥン アーエス 防汚組成物
WO2022181298A1 (fr) * 2021-02-26 2022-09-01 バッセル化学株式会社 Composition de peinture antisalissure à base aqueuse, revêtement antisalissure formé par utilisation de cette dernière et filet de pêche, navire et structure sous-marine dont la surface porte un revêtement

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