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WO2016009947A1 - Composition de peinture antisalissure - Google Patents

Composition de peinture antisalissure Download PDF

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Publication number
WO2016009947A1
WO2016009947A1 PCT/JP2015/069788 JP2015069788W WO2016009947A1 WO 2016009947 A1 WO2016009947 A1 WO 2016009947A1 JP 2015069788 W JP2015069788 W JP 2015069788W WO 2016009947 A1 WO2016009947 A1 WO 2016009947A1
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Prior art keywords
antifouling
group
paint composition
composition according
antifouling paint
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PCT/JP2015/069788
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English (en)
Japanese (ja)
Inventor
豊 藤木
聡一郎 谷野
田中　秀幸
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中国塗料株式会社
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Application filed by 中国塗料株式会社 filed Critical 中国塗料株式会社
Priority to JP2016534399A priority Critical patent/JP6309626B2/ja
Priority to SG11201700189UA priority patent/SG11201700189UA/en
Priority to CN201580038494.5A priority patent/CN106488962A/zh
Publication of WO2016009947A1 publication Critical patent/WO2016009947A1/fr

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    • 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
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • 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
    • 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
    • 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
    • C09D183/04—Polysiloxanes
    • 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

Definitions

  • the present invention can suppress spray dust scattering when spray-coated, and has excellent anti-fouling properties with excellent coating efficiency on the object to be coated.
  • the present invention relates to an antifouling paint composition capable of forming a dirty paint film.
  • An antifouling coating film formed from an organopolysiloxane antifouling coating composition is widely used to prevent aquatic organisms from adhering to ships, underwater structures, fishing nets, fishing gear, and the like.
  • the coating film formed from the organopolysiloxane antifouling paint composition prevents adhesion and fixation of macro organisms such as barnacles and mussels due to its characteristics such as low surface free energy and low elastic modulus.
  • high antifouling performance is also required for micro-organisms, such as prevention of adhesion of slime, which is a coating of bacterial secretions.
  • an antifouling agent such as cuprous oxide having physiological activity to the antifouling coating composition has been studied.
  • organopolysiloxane antifouling paints especially when applied by spraying, are likely to scatter as spray dust around them, so the sprayed paint does not adhere to the coated surface, and surfaces other than the coated surface When spraying the surface, the spray dust adhering to the surface causes the adhesion failure and repellency of the sprayed paint. For this reason, when applying an organopolysiloxane antifouling paint, it is necessary to carefully cure the surroundings of the coating area over a wide range in order to prevent dust adhesion, resulting in a problem that the workability is greatly reduced.
  • Patent Document 1 discloses an organopolysiloxane coating composition containing an antifouling agent, and describes that copper and inorganic copper compounds are preferable as the antifouling agent.
  • Patent Document 2 a polymer obtained by reacting an unsaturated isocyanate with dimethylpolysiloxane having at least one hydroxyl group in a molecule and copolymerizing a desired vinyl monomer with an inorganic and / or organic antifouling agent.
  • Patent Document 3 describes an adhesion-suppressing coating composition containing a binder system based on polysiloxane, a hydrophilic-modified polysiloxane, and a biocide.
  • Patent Document 4 discloses a nitrogen-containing antibacterial effect that is excellent in repelling large adhering organisms in water, including microorganisms that form slime, and that has a long duration, is safe for the human body, and has little environmental pollution. Antifouling materials containing compounds are described.
  • JP 2001-139816 A Japanese Patent Laid-Open No. 7-305001 Special table 2013-515122 gazette Japanese Patent Laid-Open No. 9-249507
  • the present invention is for solving the problems associated with the prior art, can form an antifouling film having high antifouling properties, has excellent coating efficiency, and spray dust during spray coating.
  • An object of the present invention is to provide an antifouling paint composition capable of suppressing the scattering of water.
  • Inorganic copper contained in the antifouling coating composition is preferably cuprous oxide and / or metallic copper.
  • the antifouling coating composition further contains copper pyrithione.
  • the antifouling coating composition preferably further contains (D) an antifouling agent other than inorganic copper (C) and copper pyrithione.
  • the (D) antifouling property-imparting agent is preferably a pyrithione salt other than copper pyrithione.
  • the antifouling coating composition preferably contains 0.5 to 60% by weight of (C) inorganic copper, more preferably 5 to 40% by weight.
  • the antifouling paint composition further contains (E) silicone oil.
  • the (E) silicone oil is preferably an organopolysiloxane represented by the following general formula [I].
  • each R 3 is independently an alkyl group, alkenyl group, aryl group, aralkyl group, alkoxy group or halogenated alkyl group having 1 to 10 carbon atoms; or a hydrocarbon having 1 to 10 carbon atoms at the end
  • a polyoxyalkylene group having 2 to 100 carbon atoms which may be capped with a silyl group having a group, a hydroxyl group or a condensation reactive group on a silicon atom, and u is an integer of 1 to 10,000.
  • the antifouling coating composition preferably further contains (F) a metal curing catalyst and / or (G) an organic solvent.
  • the antifouling coating film according to the present invention is obtained by curing the above antifouling coating composition.
  • the method for producing an antifouling coating film according to the present invention is characterized in that the antifouling coating composition is applied to obtain an antifouling coating film.
  • the antifouling substrate according to the present invention is characterized in that the substrate is coated with the above antifouling coating film. It is preferable that the base material is any one of a ship, an underwater structure, and a fishing gear.
  • the base material antifouling method according to the present invention is characterized in that the base material surface is coated with the above antifouling coating film.
  • a method for producing an antifouling substrate according to the present invention includes a step of applying the antifouling coating composition to a substrate, and a step of curing the antifouling coating composition applied to the substrate by the step. .
  • an organopolysiloxane antifouling paint composition capable of suppressing dust scattering during spray coating, providing an antifouling coating film having excellent coating efficiency and exhibiting high antifouling properties A thing is obtained.
  • the antifouling paint composition of the present invention has excellent coating efficiency during spray coating and can suppress dust scattering, so that the adhesion of paint, etc. on the surrounding coated surface due to spray dust scattering to the surroundings during coating It is possible to reduce adverse effects such as defects and repelling, shorten painting time, and reduce usage.
  • FIG. 1 is a schematic explanatory diagram of an apparatus for measuring the dust scattering rate during spray coating used in the examples.
  • the antifouling coating composition according to the present invention contains (A) an organopolysiloxane having two or more silanol groups in one molecule, (B) a crosslinking agent, and (C) inorganic copper.
  • A an organopolysiloxane having two or more silanol groups in one molecule
  • B a crosslinking agent
  • C inorganic copper.
  • each component will be described in order.
  • the organopolysiloxane (A) having two or more silanol groups in one molecule is preferably a compound represented by the following general formula [II].
  • each R 2 independently represents a hydrogen atom or an alkyl group, alkenyl group, aryl group, aralkyl group, alkoxy group or halogenated alkyl group having 1 to 10 carbon atoms.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group.
  • alkenyl group examples include vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, pentenyl group, heptenyl group, hexenyl group, and cyclohexenyl group.
  • aryl group examples include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
  • aralkyl group examples include benzyl group, 2-phenylethyl group, 2-naphthylethyl group, diphenylmethyl group and the like.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a methoxyethoxy group, and an ethoxyethoxy group.
  • halogenated alkyl group examples include groups formed by substituting some or all of the hydrogen atoms contained in the alkyl group with halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom.
  • R 2 is preferably a methyl group.
  • r is an integer of 1 to 3, preferably 1.
  • s is an integer of 10 to 10,000, preferably 100 to 1,000.
  • the organopolysiloxane (A) having two or more silanol groups in one molecule preferably has a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC) of 500 to 1,000,000. Preferably it is 5,000 to 100,000, more preferably 10,000 to 50,000.
  • the viscosity at 23 ° C. is preferably 20 to 100,000 mPa ⁇ s, more preferably 100 to 10,000 mPa ⁇ s, and further preferably 500 to 5,000 mPa ⁇ s. When the weight average molecular weight and the viscosity are in this range, it is preferable from the viewpoint of excellent manufacturing workability of the coating material, spray atomization property, coating film curability, and strength of the formed coating film.
  • the organopolysiloxane (A) having two or more silanol groups in one molecule is usually contained in the antifouling coating composition in an amount of 20 to 90% by weight, preferably 50 to 70% by weight.
  • the organopolysiloxane (A) is usually contained in an amount of 30 to 95% by weight, preferably 60 to 90% by weight, based on the weight of the solid content contained in the antifouling coating composition.
  • a coating film exhibiting good coating strength and rubber elasticity can be formed, and an antifouling coating film exhibiting antifouling properties for a long period of time is obtained. be able to.
  • the organopolysiloxane (A) having two or more silanol groups in one molecule commercially available ones can be used.
  • DMS-S35 product of GELEST
  • the crosslinking agent (B) is preferably an organosilane having two or more hydrolyzable groups in one molecule represented by the following general formula [III] and / or a partial hydrolysis condensate thereof.
  • R 4 independently represents a hydrocarbon group having 1 to 6 carbon atoms, for example, a linear or branched alkyl group such as a methyl group, an ethyl group or a propyl group, or a cyclohexyl group.
  • a cyclic alkyl group such as a vinyl group, an alkenyl group such as a vinyl group, or an aryl group such as a phenyl group, preferably a methyl group or an ethyl group.
  • Y is independently a hydrolyzable group, and examples thereof include an alkoxy group, a ketoxime group, an acyloxy group, an alkenyloxy group, an amino group, an amide group, and an aminooxy group.
  • alkoxy group and a ketoxime group include an alkoxy group, a ketoxime group, an acyloxy group, an alkenyloxy group, an amino group, an amide group, and an aminooxy group.
  • alkoxy group those having 1 to 10 carbon atoms are preferable, and one or more oxygen atoms may be interposed between carbon atoms.
  • methoxy group, ethoxy group, propoxy group, butoxy group, methoxy group An ethoxy group, an ethoxyethoxy group, etc. are mentioned.
  • ketoxime group examples include a dimethyl ketoxime group, a methyl ethyl ketoxime group, a diethyl ketoxime group, a methyl isopropyl ketoxime group, a cyclopentanoxime group, and a cyclohexanoxime group.
  • the acyloxy group is preferably an aliphatic group or an aromatic group represented by the formula: RCOO— (wherein R is an alkyl group having 1 to 10 carbon atoms or an aromatic group having 6 to 12 carbon atoms). Examples thereof include an acetoxy group, a propionoxy group, a butyroxy group, and a benzoyloxy group.
  • the alkenyloxy group is preferably one having 3 to 10 carbon atoms, and examples thereof include an isopropenyloxy group, an isobutenyloxy group, and a 1-ethyl-2-methylvinyloxy group.
  • amino group those having 1 to 10 carbon atoms are preferable.
  • amide group those having 2 to 10 carbon atoms are preferable, and examples thereof include an N-methylacetamide group, an N-ethylacetamide group, and an N-methylbenzamide group.
  • the aminooxy group preferably has 2 to 10 carbon atoms in total, and examples thereof include N, N-dimethylaminooxy group and N, N-diethylaminooxy group.
  • D is an integer from 0 to 2, preferably 0.
  • organosilanes can be used.
  • ethyl silicate 28 manufactured by Colcoat Co.
  • normal ethyl silicate manufactured by Tama Chemical Industries
  • silicate 40 manufactured by Tama Chemical Industries
  • alkyltrialkoxysilane include “KBM-13” (manufactured by Shin-Etsu Chemical).
  • the crosslinking agent (B) is generally contained in the antifouling coating composition in an amount of 0.1 to 50% by weight, usually 1 to 30% by weight, preferably 3 to 15% by weight. Is done. When the content of the crosslinking agent (B) is in this range, the curing rate of the antifouling coating composition can be appropriately maintained, and the coating film obtained by curing exhibits excellent coating strength and rubber properties. can do.
  • ⁇ (C) Inorganic copper> Inorganic copper (C) can suppress the spray dust scattering of the antifouling coating composition, can improve the coating efficiency to the coating object, and can improve the antifouling property of the antifouling coating film.
  • inorganic copper is normally used as an antifouling property imparting agent in an antifouling coating composition
  • the present inventors have found that inorganic copper has an effect of suppressing spray dust scattering, and the inorganic copper (C) By using it, it was possible to improve the antifouling property of the antifouling coating, to suppress the scattering of spray dust and to improve the coating efficiency to the object.
  • inorganic copper examples include cuprous oxide, metallic copper, copper oxide, copper thiocyanate, copper chloride, etc. Among them, cuprous oxide or metallic copper is preferable. Two or more of these may be used in combination.
  • cuprous oxides include “cuprous oxide NC-803”, “cuprous oxide NC-301” (manufactured by Nisshin Chemco), “RED COPP 97N Premium”, “LOLO TINT LM” (American Chemette Corporation),
  • metallic copper examples include “electrolytic copper powder # 6” (manufactured by JX Nippon Mining & Metals).
  • the content of inorganic copper (C) is usually 0.5 to 60% by weight, preferably 5 to 40% by weight, and more preferably 10 to 35% by weight in the antifouling coating composition.
  • the antifouling coating composition according to the present invention includes copper pyrithione, inorganic copper (C) and copper in addition to organopolysiloxane (A) having two or more silanol groups, a crosslinking agent (B), and inorganic copper (C).
  • the antifouling property-imparting agent other than inorganic copper (C) may be either organic or inorganic.
  • organic antifouling agents include pyrithione salt compounds, tetramethylthiuram disulfide, and carbamate compounds represented by the following general formula [IV] (eg, zinc dimethyldithiocarbamate, manganese-2 ethylenebisdithiocarbamate) 2,4,5,6-tetrachloroisophthalonitrile, 2- (p-chlorophenyl) -3-cyano-4-bromo-5-trifluoromethylpyrrole, (RS) -4- [1- (2,3- Dimethylphenyl) ethyl] -3H-imidazole, 4,5-dichloro-N-octyl-4-isothiazolin-3-one, pyridinetriphenylborane, p-isopropylpyridinemethyldiphenylborane, and the like. It is preferable that the pyrithione salt compound represented by this is included.
  • the pyrithione salt compound represented by this is included.
  • each R 3 independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group, an alkenyl group, an aryl group, an alkoxy group or a halogenated alkyl group, and M represents Zn. , Cu, Na, Mg, Ca, Ba, Fe, or Sr, and n is the valence of the metal M.
  • Any one type of antifouling agent other than inorganic copper (C) may be used alone, or a plurality of types may be used in combination.
  • the underwater antifouling property of the coating film can be further improved.
  • a pyrithione salt is preferable.
  • the antifouling property can be improved and the spray dust scattering suppression effect brought about by inorganic copper (C) can be further enhanced, and the coating can be applied to the object to be coated. Efficiency can be further improved.
  • the content of copper pyrithione is preferably 0.1 to 30% by weight, more preferably 0.5 to 15% by weight, and still more preferably 1 to 10% by weight in the antifouling coating composition.
  • the content of the antifouling agent (D) other than inorganic copper (C) and copper pyrithione is preferably 0.1 to 30% by weight in the antifouling coating composition.
  • Silicone oil other than organopolysiloxane (A) As the silicone oil (E) other than the organopolysiloxane (A), an organopolysiloxane represented by the following general formula [I] is preferably used.
  • each R 3 independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an aryl group, an aralkyl group, an alkoxy group, a halogenated alkyl group; or a terminal having 1 to 10 carbon atoms.
  • a polyoxyalkylene group having 2 to 100 carbon atoms which may be sealed with a silyl group having a hydrocarbon group, a hydroxyl group or a condensation reactive group on a silicon atom, and a methyl group and a phenyl group, or a methyl group And a polyoxyalkylene group.
  • u is an integer of 1 to 10,000.
  • silicone oil (E) in which R 3 is a methyl group and a phenyl group in the general formula [I] examples include, for example, “KF-54”, “KF-56”, “KF-50” (Shin-Etsu Chemical ( ), “SH510”, “SH550” (manufactured by Toray Dow Corning), “TSF431” (manufactured by Toshiba Silicone Co., Ltd.), and the like.
  • silicone oil (E) in which R 3 is a methyl group and a polyoxyalkylene group in the above general formula [I] “X-22-6548” (alkylene glycol-modified silicone oil, manufactured by Shin-Etsu Chemical Co., Ltd.) “FZ-2164” (alkylene glycol-modified silicone oil, manufactured by Toray Dow Corning Co., Ltd.), “X-22-4272” (terminal hydroxyl group-blocking / alkylene glycol-modified silicone oil, manufactured by Shin-Etsu Chemical Co., Ltd.), Examples include “BY16-839” (alicyclic epoxy-modified silicone oil, manufactured by Toray Dow Corning Co., Ltd.).
  • the content of the silicone oil (E) is usually 0.01 to 30% by weight, preferably 0.1 to 15% by weight in the antifouling coating composition. When the content of the silicone oil (E) is within this range, it is possible to improve sagging resistance by appropriately improving the thixotropy of the antifouling coating composition and to enable thick film coating. The antifouling performance of the antifouling coating film can be improved.
  • the metal curing catalyst (F) is a catalyst for accelerating each condensation reaction of the organopolysiloxane (A) and the crosslinking agent (B) having two or more silanol groups in one molecule or between them. Accelerating the curing reaction of the coating film so that a cured coating film can be obtained sooner after coating.
  • the metal curing catalyst (F) is preferably a tin-containing curing catalyst.
  • metal curing catalyst (F) for example, those described in JP-A-4-106156 (Patent No. 2522854) can be suitably used.
  • tin carboxylates such as tin naphthenate and tin oleate; dibutyltin diacetate, dibutyltin acetoacetonate, dibutyltin dilaurate, dibutyltin dioleate, dibutyltin oxide, dibutyltin dimethoxide, dibutyltin dipentoate, Dibutyltin dioctoate, dibutyltin dineodecanoate, dioctyltin dineodecanoate, bis (dibutyltin laurate) oxide, dibutylbis (triethoxysiloxy) tin, bis (dibutyltin acetate) oxide, dibutyltin bis (ethylmalate) and Tin compounds such
  • a commercially available metal curing catalyst (F) can be used.
  • “NEOSTAN U-100” manufactured by Nitto Kasei Co., Ltd.
  • Nitto Kasei Co., Ltd. can be used.
  • the content of the metal curing catalyst (F) is usually 10% by weight or less, preferably 1% by weight or less in the antifouling coating composition, and the lower limit when using the catalyst is preferably 0.00. 001% by weight, particularly preferably 0.01% by weight. When the content of the metal curing catalyst (F) is within this range, a coating composition having a good balance between the coating film curing rate and the pot life after the preparation of the coating is obtained.
  • (G) Organic solvent As the organic solvent (G), aromatic hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons, alcohols, ketones and esters can be used, and aromatic hydrocarbons and It is preferable to use an alcohol system in combination.
  • Alcohol may be a straight chain, branched chain or cyclic chain having an ether group contained in the chain, and examples thereof include methanol, ethanol, propanol, butanol, pentanol, and hexanol.
  • an alcohol having 5 or less carbon atoms is preferable, and n-butanol is more preferable.
  • alcohol is selected from these, a long time can be obtained as the pot life after mixing the paint.
  • the alcohol content is usually 1 to 20% by weight, preferably 3 to 10% by weight in the antifouling coating composition. When the alcohol content is within this range, a long time can be obtained as the pot life after mixing the paint.
  • aromatic hydrocarbon-based organic solvent examples include toluene, xylene, styrene, mesitylene, and the like.
  • Examples of the aliphatic hydrocarbon-based organic solvent include pentane, hexane, heptane, and octane.
  • Examples of the alicyclic hydrocarbon-based organic solvent include cyclohexane, methylcyclohexane, and ethylcyclohexane.
  • ketone organic solvent examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl carbonate and the like.
  • ester organic solvent examples include propylene glycol monomethyl ether acetate.
  • the antifouling paint composition contains an organic solvent (G)
  • the viscosity of the antifouling paint composition can be reduced and the coating workability can be improved.
  • a preferable amount of the organic solvent (G) is determined by the viscosity of the antifouling coating composition, but is usually 0 to 50% by weight in the antifouling coating composition. When there is too much content, malfunctions, such as a fall of sagging stop property, will generate
  • Silica (H) is an organopolysiloxane (A) or silicone oil (E) having two or more silanol groups in one molecule as described above. Before preparation of each component to be contained, it may be kneaded with an organopolysiloxane in advance.
  • Silica (H) is hydrophilic silica (surface untreated silica) such as wet method silica (hydrated silica), dry method silica (fumed silica, anhydrous silica), and hydrophobic wet silica and hydrophobic fumed silica. Hydrophobic silica that has been surface-treated, such as, can be used. These may be used alone or in combination of two or more.
  • the wet process silica is not particularly limited, but, for example, has an adsorbed water content of about 4 to 8%, a bulk density of 200 to 300 g / L, a primary particle diameter of 10 to 30 ⁇ m, and a specific surface area (BET surface area) of 10 m 2 / g or more. Can be used.
  • the dry silica is not particularly limited, and for example, a silica having a water content of 1.5% or less, a bulk density of 50 to 100 g / L, a primary particle diameter of 8 to 20 ⁇ m, and a specific surface area of 10 m 2 / g or more can be used.
  • Hydrophobic fumed silica is obtained by subjecting dry silica to a surface treatment with an organosilicon compound such as methyltrichlorosilane, dimethyldichlorosilane, hexamethyldisilazane, hexamethylcyclotrisiloxane, and octamethylcyclotetrasiloxane.
  • Hydrophobic fumed silica has little moisture adsorption over time, and the moisture content is usually 0.3% or less, and in many cases 0.1 to 0.2%.
  • Such hydrophobic fumed silica is not particularly limited, and for example, those having a primary particle diameter of 5 to 50 ⁇ m, a bulk density of 50 to 100 g / L, and a specific surface area of 10 m 2 / g or more can be used.
  • the moisture adsorbed on the surface of the silica is physically reduced and removed by heat treatment with the above-described organopolysiloxane.
  • the moisture content of the heat-treated hydrophobic fumed silica is usually 0.2% or less, preferably 0.1% or less, more preferably 0.05 to 0.1%.
  • Other physical property values such as bulk density are the same as those of the hydrophobic silica before heat treatment.
  • silica can be used. Examples thereof include “R974” and “RX200” manufactured by Nippon Aerosil.
  • silica (H) When silica (H) is used by kneading with the aforementioned organopolysiloxane, a heat-treated product formed by previously heat-treating the organopolysiloxane and silica, or the heat-treated product and the organopolysiloxane not heat-treated Preference is given to using a mixture of siloxanes. This is because the silica is preheated together with a part or all of the organopolysiloxane to improve the affinity of both components and to obtain effects such as suppressing silica aggregation.
  • This heat treatment is performed, for example, under normal pressure or reduced pressure at a temperature of 100 ° C. or higher and below the decomposition temperature of the blended components, preferably 100 to 300 ° C., more preferably 140 to 200 ° C., usually for about 3 to 30 hours. do it.
  • Silica is contained in the organopolysiloxane (A) in a proportion of usually 1 to 100% by weight, preferably 2 to 50% by weight, more preferably 5 to 30% by weight. If the content of silica is within the above range, the antifouling coating composition exhibits suitable thixotropy, so that a desired film thickness can be obtained by one coating, particularly spray coating, and high strength. A coating film with hardness is obtained.
  • the stability during preparation or storage of the resulting antifouling coating composition is increased, fluidity and thixotropy are improved, and sufficient for vertical coating surfaces and the like.
  • a coating film having a thickness can be formed with a small number of coatings, and effects such as excellent balance of physical properties such as hardness, tensile strength, and elongation of the resulting coating film can be obtained.
  • Fillers other than silica (H) As the filler (I) other than silica (H), conventionally known various organic and inorganic pigments and other fillers can be used.
  • organic pigments examples include carbon black, phthalocyanine blue, and bitumen.
  • Inorganic pigments are neutral and non-reactive such as titanium white (titanium oxide), bengara, barite powder, talc, chalk, iron oxide powder, etc .; lead white, red lead, zinc powder, lead oxide Examples thereof include those that are basic and reactive with acidic substances in the paint, such as powder (active pigments).
  • Other fillers include metal oxides such as diatomaceous earth and alumina; metal carbonates such as calcium carbonate, magnesium carbonate and zinc carbonate; other, asbestos, glass fiber, quartz powder, aluminum hydroxide, gold powder, silver powder, surface Examples thereof include treated calcium carbonate and glass balloon. Moreover, you may use what surface-treated these surfaces with the silane compound. Any one of these fillers may be used alone, or two or more thereof may be used in combination. These fillers can also contain various colorants such as dyes.
  • the strength of the coating film can be improved, and further, by concealing the undercoating film, deterioration of the undercoating film due to ultraviolet light can be prevented. it can.
  • the content of the filler (I) is preferably 0.1 to 30% by weight in the antifouling coating composition.
  • Anti-sagging and anti-settling agent include organic clay waxes (such as Al, Ca, Zn stearate salts, lecithin salts, alkyl sulfonates), organic waxes (polyethylene wax, polyethylene oxide wax, amide wax) , Polyamide wax, hydrogenated castor oil wax, etc.), mixtures of organic clay wax and organic wax, synthetic fine powder silica, and the like.
  • organic clay waxes such as Al, Ca, Zn stearate salts, lecithin salts, alkyl sulfonates
  • organic waxes polyethylene wax, polyethylene oxide wax, amide wax
  • Polyamide wax Polyamide wax, hydrogenated castor oil wax, etc.
  • mixtures of organic clay wax and organic wax synthetic fine powder silica, and the like.
  • the commercially available anti-sagging and anti-settling agent (J) can be used.
  • “Disparon 305” and “Disparon 4200-20” manufactured by Enomoto Kasei Co., Ltd., as well as “Disparon A630-20X” can be used.
  • the content of the anti-sagging and anti-settling agent (J) is usually 0.01 to 10% by weight, preferably 0.1 to 3% by weight in the antifouling coating composition.
  • the silane coupling agent (K) is a silane cup containing one or more groups such as an alkoxysilyl group, an amino group, an imino group, an epoxy group, a hydrosilyl group, a mercapto group, an isocyanate group, and a (meth) acryl group. Ring agents are preferred, and those having an amino group are particularly preferred.
  • silane coupling agent having an amino group examples include 3- (2-aminoethyl) aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3- (2- (2- Aminoethyl) aminoethyl) aminopropyltrimethoxysilane and the like.
  • Other silane coupling agents include, for example, 3-glycidoxypropylmethyldimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, N-phenylpropyltrimethoxysilane, N-phenylpropylene. Lutriethoxysilane and the like can also be mentioned.
  • silane coupling agent you may use the mixture of these several things.
  • silane coupling agent (K) in the antifouling coating composition, adhesion to the undercoat coating film or the substrate can be made stronger, or the strength of the coating film of the antifouling coating composition can be improved. it can.
  • the content of the silane coupling agent (K) is preferably 0.01 to 1% by weight in the antifouling coating composition.
  • Other coating film forming components As the other coating film-forming component (L), a coating film-forming component other than the main resin component, organopolysiloxane, can be used within a range not departing from the object of the present invention.
  • coating film forming components (L) include, for example, acrylic resins, acrylic silicone resins, unsaturated polyester resins, fluororesins, polybutene resins, silicone rubbers, urethane resins (rubbers), polyamide resins, and vinyl chloride copolymer resins. , Chlorinated rubber (resin), chlorinated olefin resin, styrene-butadiene copolymer resin, ethylene-vinyl acetate copolymer resin, vinyl chloride resin, alkyd resin, coumarone resin, trialkylsilyl acrylate (co) polymer (silyl resin) ), Poorly water-soluble or water-insoluble resins such as petroleum resins.
  • acrylic resins acrylic silicone resins, unsaturated polyester resins, fluororesins, polybutene resins, silicone rubbers, urethane resins (rubbers), polyamide resins, and vinyl chloride copolymer resins.
  • inorganic dehydrating agent (M) examples include anhydrous gypsum (CaSO 4 ), synthetic zeolite-based adsorbent (trade name: molecular sieve, etc.), silicates, and the like, and anhydrous gypsum and molecular sieve are preferably used. Such inorganic dehydrating agents can be used alone or in combination.
  • the inorganic dehydrating agent (M) also functions as a stabilizer, and the antifouling coating composition contains this component, thereby preventing deterioration due to moisture in the antifouling coating composition and further improving storage stability. Can do.
  • the content of the inorganic dehydrating agent (M) is preferably 0.1 to 10% by weight in the antifouling coating composition.
  • flame retardant examples of the flame retardant (N) include antimony oxide and paraffin oxide.
  • (O) thixotropic agent examples of the thixotropic property-imparting agent (O) include polyethylene glycol, polypropylene glycol, and derivatives thereof.
  • the antifouling coating composition of the present invention can be prepared by mixing the above components.
  • Component of antifouling paint composition The antifouling paint composition according to the present invention may be provided as a one-component paint comprising one component or may be provided as a multi-component paint comprising two or more components. In the case of a multi-component type comprising two or more components, the antifouling paint composition according to the present invention is prepared by mixing the components.
  • Multi-component antifouling paint composition / kit for preparing antifouling paint composition When the antifouling paint composition according to the present invention is provided as a multi-component paint comprising two or more components, each of these components (each solution) contains one or a plurality of components, respectively. After being packaged in a container, it is stored and stored in a container such as a can. The contents of these components are mixed and stirred at the time of painting to prepare an antifouling paint composition. That is, in one aspect, the present invention provides a kit comprising the above components for preparing the antifouling coating composition according to the present invention.
  • the component containing organopolysiloxane which is the main component of the binder resin of the antifouling coating composition, is referred to as “main agent” and reacts with the organopolysiloxane.
  • a component containing a compound used to construct a crosslinked structure is referred to as a “curing agent”.
  • an additional component referred to as an “additive” etc. .
  • the antifouling paint composition (kit for preparation thereof) may be produced in the form of a two-component type comprising such a main component (X) and a curing agent component (Y). It may be produced in the form of a three-component type consisting of component (X), curing agent component (Y) and additive component (Z).
  • the antifouling coating film is obtained by curing the antifouling coating composition.
  • the antifouling coating film obtained by curing the antifouling coating composition can further improve the resistance to macrobiological fouling, and can also suppress the adhesion of microfouling such as slime. A high effect can be obtained for applications that require high antifouling properties such as ships that are strongly required.
  • the antifouling substrate is obtained by coating the substrate with the antifouling coating film.
  • the production of the antifouling substrate is, for example, a method comprising a step of applying the antifouling coating composition to the substrate and a step of curing the antifouling coating composition applied to the substrate by the step, It can be performed by a method including a step of sticking an antifouling film obtained by curing the stain coating composition to a substrate.
  • Specific examples of the method for applying the antifouling coating composition to the substrate include a method in which the antifouling coating composition is sufficiently stirred and then applied to the substrate by spraying or other means.
  • Specific examples of the method of curing the applied antifouling coating composition include a method of allowing it to stand for 0.5 to 3 days in air at normal temperature or forcibly blowing and heating it under heating. By this method, an antifouling substrate obtained by coating the substrate with an antifouling coating film can be produced.
  • the antifouling coating composition is cured by using a known technique described in JP2013-129724A.
  • the method of sticking the film containing the antifouling coating film obtained by making it to a base material is mentioned.
  • an antifouling substrate obtained by coating the substrate with an antifouling coating film can be produced.
  • the film thickness of the antifouling coating film may be formed to a desired thickness depending on the application, etc., but the antifouling coating composition is usually 30 to 400 ⁇ m, preferably 50 to 300 ⁇ m / time, from once to a plurality of times. If the coating is cured after application, and the film thickness after curing is, for example, 100 to 1000 ⁇ m, an antifouling coating film excellent in coating film strength and antifouling performance is obtained.
  • the organopolysiloxane antifouling paint composition according to the present invention Has characteristics suitable for spray coating as described above. That is, when the antifouling paint composition according to the present invention is applied by spraying, it is possible to improve the antifouling property of the antifouling coating film, suppress spray dust scattering, and improve the application efficiency to the object.
  • the antifouling paint composition according to the present invention protects the surface of a substrate in contact with seawater or fresh water from adhesion of marine organisms in a wide range of industrial fields such as power generation, harbor / civil engineering construction, and shipbuilding (shipbuilding or repair). It can be used to maintain the original function of the substrate over a long period of time.
  • base materials include, for example, ships (shipboards, etc.), fishing materials (ropes, fishing nets, fishing gear, floats, buoys, etc.), underwater structures such as thermal and nuclear power plants, and seawater use Examples include equipment (seawater pumps, etc.), mega floats, gulf roads, submarine tunnels, harbor facilities, sludge diffusion prevention membranes for various civil engineering works such as canals and waterways.
  • the antifouling paint composition according to the present invention may be applied or impregnated directly on the substrate.
  • the antifouling paint composition according to the present invention is also applied to a base material whose material is fiber reinforced plastic (FRP), steel, wood, aluminum alloy, etc., such as a water supply / drain port of a nuclear power plant, a mega float, and a ship. Products can be prepared so that the adhesion to the surface of these substrates (materials) is good.
  • FRP fiber reinforced plastic
  • the base material to which the antifouling paint composition according to the present invention is applied may have a coating film already formed on the surface. That is, the antifouling coating composition according to the present invention may be applied to the surface of a base material such as a ship or an underwater structure to which a base material (undercoat) such as a rust preventive agent or primer has been applied in advance. Furthermore, the surface of a base material such as a ship that has already been coated with a conventional antifouling paint or that has been coated with the antifouling paint composition of the present invention, particularly an FRP ship or an underwater structure, The antifouling paint composition of the present invention may be overcoated for repair.
  • the kind of coating film which the antifouling paint composition according to the present invention directly contacts is not particularly limited, as in the case of applying a general organopolysiloxane antifouling paint, for example, epoxy resin, urethane resin And a coating film formed from a paint mainly composed of a silicone resin or the like.
  • the antifouling paint composition according to the present invention can be prepared such that the adhesion of the coating film to the surface is good.
  • Table 1 shows general names, chemical formulas, and the like of the components of the antifouling coating composition used in the present examples and comparative examples.
  • the weight average molecular weight Mw described in Table 1 was measured by GPC using a standard polystyrene calibration curve.
  • Antifouling paint compositions of Examples 1 to 10 and Comparative Examples 1 and 2 were prepared by preparing the main agent component (X) and the hardener component (Y) and mixing the main agent component (X) and the hardener component (Y). A product was prepared.
  • the numerical values relating to the main component (X) and the hardener component (Y) in Table 2 represent parts by weight.
  • the air was sucked from a suction port opened in a rectangular shape with a width of 900 mm and a height of 850 mm so that the wind speed was about 2 m / s.
  • a plate material having a painted surface F having a height of 850 mm and a width of 700 mm is installed so that one side of the painted surface F is in contact with one side of the intake port, and the painted surface F and the intake port are perpendicular to each other.
  • a weighed polyethylene sheet was attached.
  • a plate member having a lower surface B having a width of 450 mm and a width of 700 mm is installed so that two sides of the lower surface B are in contact with the one side of the intake port and the painted surface F, respectively, and a weighted polyethylene sheet is pasted on the entire lower surface B. I attached.
  • the antifouling paint composition is inserted into the spray gun G, and the gun tip (discharge point S) is installed at a distance of 700 mm from the painted surface F and at a height of 450 mm from the lower end of the painted surface F.
  • the antifouling paint compositions of Examples 1 to 10 and Comparative Examples 1 and 2 were discharged for 10 seconds from a spray gun at a discharge pressure of 5 kgf / cm 2 toward the center of the coating surface F in a direction perpendicular to the surface. .
  • the weight of the spray gun filled with the antifouling paint composition (the sum of the weight of the spray gun and the weight of the antifouling paint composition filled) before painting.
  • the weight of the antifouling paint composition discharged during each coating was calculated by subtracting the weight after coating from the weight of the above. The discharge weight was multiplied by the solid content ratio of each antifouling paint composition to obtain the discharged paint solid weight of the applied antifouling paint composition.
  • the polyethylene sheet affixed to the painted surface F and coated with each antifouling paint composition was dried for 24 hours, and then the weight (weight of the polyethylene sheet and the weight of the antifouling paint composition applied) And the weight of the polyethylene sheet before coating was subtracted from the weight to determine the weight of the coating material.
  • the polyethylene sheet affixed to the lower surface B and coated with each antifouling paint composition was dried for 24 hours, and then the weight (the weight of the polyethylene sheet and the weight of the antifouling paint composition applied) Total) was measured, and the weight of the polyethylene sheet before coating was subtracted from the weight to obtain the weight of the falling paint.
  • the dust scattering rate was calculated by the following formula, assuming that the weight of the sprayed paint dust is the weight of the sprayed paint solids minus the weight of the paint that has been applied to the painted surface and dropped to the lower surface.
  • test plate After the test plate is dried at room temperature for 7 days, it is immersed in seawater off Kure, Hiroshima Prefecture, and a water flow is generated at about 15 knots per hour using a rotating rotor. The water flow is applied to the antifouling coating surface of the test plate. The ratio of the area of the area where aquatic organisms adhered to the antifouling coating film surface of the test plate every three months was evaluated by visual observation. The dynamic antifouling property was evaluated at the evaluation points shown below.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
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Abstract

La présente invention concerne une composition de peinture antisalissure contenant (A) un organopolysiloxane présentant au moins deux groupes silanol dans une molécule, (B) un agent de réticulation et (C) du cuivre inorganique. Selon la présente invention, on obtient une composition de peinture antisalissure à base d'organopolysiloxane qui peut supprimer la dispersion de poussière au cours de la peinture par pulvérisation et qui donne un film de revêtement antisalissure doté d'une excellente efficacité de revêtement et présentant un degré élevé de capacité antisalissure. La composition de peinture antisalissure selon la présente invention peut présenter une excellente efficacité de revêtement pendant la peinture par pulvérisation et supprimer la dispersion de poussière, de sorte que la présente invention peut réduire des effets négatifs, tels qu'une faible adhérence de la peinture ou analogue et le refus à l'application sur une surface revêtue dans les environs, qui sont provoqués par la dispersion de poussière de pulvérisation dans les environs pendant la peinture, raccourcir le temps de peinture et réduire la consommation de peinture.
PCT/JP2015/069788 2014-07-14 2015-07-09 Composition de peinture antisalissure WO2016009947A1 (fr)

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JP2016534399A JP6309626B2 (ja) 2014-07-14 2015-07-09 防汚塗料組成物
SG11201700189UA SG11201700189UA (en) 2014-07-14 2015-07-09 Antifouling coating composition
CN201580038494.5A CN106488962A (zh) 2014-07-14 2015-07-09 防污涂料组合物

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JP2014-144373 2014-07-14
JP2014144373 2014-07-14

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WO2017099180A1 (fr) * 2015-12-11 2017-06-15 中国塗料株式会社 Composition de revêtement permettant de former un film de revêtement réduisant la résistance au frottement, film de revêtement, et substrat ayant un film de revêtement
CN111201338A (zh) * 2017-10-12 2020-05-26 日本帕卡濑精株式会社 表面处理剂、以及具有表面处理覆膜的金属材料及其制造方法
WO2020209208A1 (fr) * 2019-04-09 2020-10-15 日東化成株式会社 Composition de revêtement antisalissure
WO2020246434A1 (fr) * 2019-06-06 2020-12-10 日東化成株式会社 Composition de revêtement antisalissure
CN114605913A (zh) * 2022-03-21 2022-06-10 常熟理工学院 仿生高粘结力有机硅海洋防污涂料及其制备方法

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CN118048040A (zh) * 2024-02-18 2024-05-17 蓝海超杰特种材料(青岛)有限公司 一种防水防污聚硅氧烷聚合物及其制备和应用

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CN111201338A (zh) * 2017-10-12 2020-05-26 日本帕卡濑精株式会社 表面处理剂、以及具有表面处理覆膜的金属材料及其制造方法
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CN114605913A (zh) * 2022-03-21 2022-06-10 常熟理工学院 仿生高粘结力有机硅海洋防污涂料及其制备方法

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