WO2009093348A1 - Composition de revêtement antidépôt, revêtement antidépôt fabriqué avec cette composition, matière dont la surface est recouverte du revêtement, procédé de traitement antidépôt comprenant la formation du revêtement et kit de formation du revêtement antidépôt - Google Patents

Composition de revêtement antidépôt, revêtement antidépôt fabriqué avec cette composition, matière dont la surface est recouverte du revêtement, procédé de traitement antidépôt comprenant la formation du revêtement et kit de formation du revêtement antidépôt Download PDF

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Publication number
WO2009093348A1
WO2009093348A1 PCT/JP2008/061674 JP2008061674W WO2009093348A1 WO 2009093348 A1 WO2009093348 A1 WO 2009093348A1 JP 2008061674 W JP2008061674 W JP 2008061674W WO 2009093348 A1 WO2009093348 A1 WO 2009093348A1
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group
antifouling
aluminum
carbon atoms
aluminum compound
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PCT/JP2008/061674
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English (en)
Japanese (ja)
Inventor
Hiroshi Shimojitosho
Yasuo Imakura
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Nitto Kasei Co., Ltd.
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Publication of WO2009093348A1 publication Critical patent/WO2009093348A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • 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
    • C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
    • C09D5/1662—Synthetic film-forming substance
    • C09D5/1675—Polyorganosiloxane-containing compositions
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/057—Metal alcoholates

Definitions

  • the present invention relates to an antifouling coating composition for preventing the use of or existing in water under water-fouling-fouling organisms for a long period of time, and an antifouling coating film formed using the antifouling coating composition
  • the present invention relates to a coated product having the coating film on its surface, an antifouling treatment method for forming the coating film, and an antifouling coating film forming kit.
  • the above-described water fouling organisms adhere to an object used or present in water such as an underwater structure such as equipment.
  • the above-described water fouling organisms adhere to and grow on contact parts with water, causing a decrease in ship speed, a decrease in water flow, etc. It is known to cause significant resource losses. Therefore, in order to prevent the adhesion of chickenpox fouling organisms, studies have been made to solve the above problem by applying an antifouling paint.
  • an antifouling paint containing an antifouling compound such as a trialkyltin compound has been conventionally used as the antifouling paint.
  • Patent Documents 1 to 4 a silicone rubber-based antifouling paint that forms a coating film of silicone rubber alone or a mixture of silicone rubber and silicone oil has been proposed as a non-toxic antifouling paint.
  • An object of the present invention is to provide an antifouling coating composition that can form a coating film excellent in antifouling performance in water and has high environmental safety.
  • the present invention includes the following antifouling paint composition, an antifouling coating film formed using the composition, a coated product having the coating film on the surface, an antifouling treatment method for forming the coating film, and It relates to an antifouling coating film forming kit.
  • the aluminum compound (B) has the general formula [1]: Al (OR 1 ) 3 [1] (Wherein R 1 is an alkyl group having 1 to 10 carbon atoms, and R 1 may be the same or different.)
  • R 1 is an alkyl group having 1 to 10 carbon atoms, and R 1 may be the same or different.
  • HO-R 3 -Y [3] wherein R 3 is an alkylene group having 2 to 10 carbon atoms, Y is a group represented by the formula: —OR 4 , or a group represented by the formula: —NR 5 R 6 ; 4 is an alkyl group or aryl group having 1 to 10 carbon atoms, and R 5 and R 6 are the same or different and are a hydrogen atom
  • Aluminum compound (B) is represented by the general formula [4]
  • R 7 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group, or an aralkyl group
  • R 8 is a linear or branched alkyl group having 1 to 10 carbon atoms.
  • n is 1 or 2
  • two R 7 s may be the same or different from each other .
  • Aluminum compound (B) is represented by the general formula [5]
  • R 9 , R 10 , R 11 and R 12 are the same or different from each other and are hydrocarbon groups having 1 to 10 carbon atoms, n is an integer of 0 to 2, and n is 2) Sometimes the two R 9s may be the same or different from each other.
  • Item 3 The antifouling coating composition according to Item 1 or 2, which is an aluminum compound represented by the formula:
  • An antifouling treatment method for forming an antifouling coating film on the surface of an object to be coated using the antifouling coating composition according to any one of items 1 to 5.
  • an organopolysiloxane having a crosslinking reactive functional group (A) and an aluminum compound (B) as a condensation reaction catalyst are mixed to produce an organopolysiloxane rubber.
  • a container containing an organopolysiloxane (A) having a crosslinking reactive functional group and (2) a container containing an aluminum compound (B) as a catalyst for condensation reaction, and a silicone oil (C) Is a kit for forming an antifouling coating film, which is contained in the container (1) and / or the container (2).
  • the antifouling paint composition of the present invention comprises: (A) an organopolysiloxane having a crosslinking reactive functional group, (B) an aluminum compound as a condensation reaction catalyst, and (C) a silicone oil.
  • an organopolysiloxane rubber By containing the aluminum compound (B), an organopolysiloxane rubber can be suitably formed from the organopolysiloxane (A), and a coating film excellent in antifouling performance capable of suitably exhibiting the antifouling effect for a long period of time. Can be formed.
  • the composition of this invention contains an aluminum compound instead of a dialkyl tin compound as a curing catalyst, and is excellent in environmental safety.
  • composition of the present invention can be used as a one-pack type antifouling paint and is excellent in workability.
  • the organopolysiloxane (A) has at least one crosslinkable functional group on the silicon atom in the molecular chain, and further has an organic group other than the crosslinkable functional group.
  • crosslinking reactive functional group examples include an alkoxy group such as a hydroxyl group, a methoxy group, an ethoxy group, and a propoxy group; an aralkyloxy group such as a benzyloxy group.
  • Examples of the organic group generally include organic groups possessed by organopolysiloxane, specifically, alkyl groups such as methyl group, ethyl group, and propyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; vinyl Groups, alkenyl groups such as allyl groups; aralkyl groups such as benzyl groups; aryl groups such as phenyl groups and naphthyl groups; and alkyl halide groups such as 3,3,3-trifluoropropyl groups.
  • alkyl groups such as methyl group, ethyl group, and propyl group
  • cycloalkyl groups such as cyclopentyl group and cyclohexyl group
  • vinyl Groups alkenyl groups such as allyl groups
  • aralkyl groups such as benzyl groups
  • aryl groups such as phenyl groups and naphthyl groups
  • the organopolysiloxane (A) undergoes a condensation reaction in the presence of an aluminum compound (B) described later and in the presence of moisture (or moisture in the air) to form an organopolysiloxane rubber.
  • the crosslinkable functional group in the organopolysiloxane (A) undergoes a condensation reaction with the crosslinkable reactive functional group of another organopolysiloxane (A) or the hydrolyzable group in the crosslinker. Rubber is formed and becomes a coating.
  • the reaction temperature in such a condensation reaction is usually 80 ° C. or lower, preferably 50 ° C. or lower.
  • the organopolysiloxane (A) may previously form an organopolysiloxane rubber.
  • the organopolysiloxane (A) and the aluminum compound (B) are mixed in the presence of moisture to produce an organopolysiloxane rubber, and then the organopolysiloxane rubber and silicone are mixed.
  • examples thereof include an antifouling paint composition obtained by mixing with oil (C).
  • the organopolysiloxane (A) those used as a film forming component of conventional silicone rubber antifouling paints can be used. Specifically, the organopolysiloxane (A) is classified into a deacetone type, a dealcohol type, a deoxime type, a deacetic acid type, and the like depending on the reaction mode. In the present invention, the same type of organopolysiloxane (A) may be used, or two or more different types may be used in combination.
  • the organopolysiloxane (A) may be diluted with an arbitrary solvent depending on its physical properties.
  • the solvent for example, toluene, xylene and the like can be used.
  • the viscosity of the organopolysiloxane (A) and the diluted product thereof is preferably 500 to 100,000 mPa ⁇ s, more preferably 1,000 to 80,000 mPa ⁇ s.
  • the viscosity can be adjusted by diluting with the above solvent or mixing two or more kinds of organopolysiloxanes (A) at an arbitrary ratio.
  • organopolysiloxanes include KE-40RTV, KE-41, KE-42, KE-42RTV, KE-42S, KE-44, KE-44RTV, KE-45, KE-45TS, KE- 45TSRTV, KE-441, KE-445, KE-45TS, KE-47, KE-48, KE-66, KE-348, KE-3479, KE-347, KE-118, KE-347, KE-402, KE-420, KR-2706, KE-4348, KE-66RTV, KE-1251, KE-1253, KE-3490, KE-3491, KE-4525, KE-4866, FE123 (above, manufactured by Shin-Etsu Chemical Co., Ltd.) , SE5004, SE5007, SE5060, SE5070, SE5400, SE9140, SH237, SH 80 (above, manufactured by Toray Dow
  • the composition of the present invention contains an aluminum compound (B) as a condensation reaction catalyst for promoting the curing reaction (formation of organopolysiloxane rubber) of the organopolysiloxane (A).
  • an antifouling paint composition having high environmental safety can be obtained.
  • the antifouling coating film formed can effectively exhibit a desired antifouling performance.
  • the aluminum compound (B) it is particularly preferable to use at least one aluminum compound selected from the group consisting of the following (B-1) to (B-5).
  • composition of the present invention is represented by the general formula [1] as the aluminum compound (B): Al (OR 1 ) 3 [1] (Wherein R 1 is an alkyl group having 1 to 10 carbon atoms, and R 1 may be the same or different.)
  • reaction product of trialkoxyaluminum [1] and diol compound [2] is the aluminum compound (B-1), and the reaction product of trialkoxyaluminum [1] and alcohol compound [3]
  • the product is aluminum compound (B-2), and the reaction product of trialkoxyaluminum [1], diol compound [2] and alcohol compound [3] is aluminum compound (B-3).
  • the alkyl group having 1 to 10 carbon atoms represented by R 1 may be linear or branched.
  • hydrocarbon groups having 1 to 4 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and tert-butyl group. More preferably, they are a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • trialkoxyaluminum [1] examples include trimethoxyaluminum, triethoxyaluminum, tripropoxyaluminum, triisopropoxyaluminum, tributoxyaluminum, trisec-butoxyaluminum, tritert-butoxyaluminum, and tripentyloxyaluminum. , Trihexyloxyaluminum, triheptyloxyaluminum, trioctyloxyaluminum, trinonyloxyaluminum, tridecyloxyaluminum and the like. In particular, triisopropoxy aluminum is preferable.
  • the alkylene group having 2 to 10 carbon atoms represented by R 2 is a divalent group obtained by removing two hydrogen atoms on different carbon atoms of a linear, branched or cyclic alkane having 2 to 10 carbon atoms.
  • the group of is mentioned.
  • Examples of the straight chain, branched or cyclic alkane having 2 to 10 carbon atoms include ethane, propane, isopropane, butane, isobutane, pentane, isopentane, neopentane, cyclopentane, hexane, isohexane, cyclohexane, heptane, and octane.
  • Nonane, decane and the like Preferably, a divalent group obtained by removing two hydrogen atoms on the carbon atom at the 1-position and 3-position of a linear or branched alkane having 4 to 8 carbon atoms is exemplified.
  • the alkenylene group having 2 to 10 carbon atoms represented by R 2 is a divalent group obtained by removing two hydrogen atoms on different carbon atoms of a linear, branched or cyclic alkene having 2 to 10 carbon atoms. The group of is mentioned.
  • Examples of the straight-chain, branched or cyclic alkene having 2 to 10 carbon atoms include, for example, ethylene, propene, isopropene, cyclopropene, 1-butene, 2-butene, isobutene, 1-pentene, 2-pentene, isopentene, Examples include cyclopentene, hexene, isohexene, cyclohexene, heptene, octene, nonene, decene and the like.
  • the alkynylene group having 2 to 10 carbon atoms represented by R 2 is a divalent group obtained by removing two hydrogen atoms on different carbon atoms of a linear, branched or cyclic alkyne having 2 to 10 carbon atoms. The group of is mentioned.
  • Examples of the straight chain, branched or cyclic alkyne having 2 to 10 carbon atoms include acetylene, propyne, 1-butyne, 2-butyne, 1-pentyne, 2-pentyne, 1-isopentine, 1-hexyne, 2 -Hexyne, 1-isohexyne, 2-isohexyne, heptin, octyne, nonin, decyne and the like.
  • diol compound [2] examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butane.
  • the alkylene group having 2 to 10 carbon atoms represented by R 3 is a divalent group obtained by removing two hydrogen atoms on different carbon atoms of a linear, branched or cyclic alkane having 2 to 10 carbon atoms.
  • the group of is mentioned.
  • Examples of the straight chain, branched or cyclic alkane having 2 to 10 carbon atoms include ethane, propane, isopropane, butane, isobutane, pentane, isopentane, neopentane, cyclopentane, hexane, isohexane, cyclohexane, heptane, and octane. , Nonane, decane and the like.
  • An alkylene group having 2 to 6 carbon atoms is preferable, and an ethylene group is particularly preferable.
  • the alkyl group having 1 to 10 carbon atoms represented by R 4 may be linear or branched.
  • hydrocarbon groups having 1 to 4 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and tert-butyl group. More preferably, they are a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • aryl group represented by R 4 examples include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group, indenyl group, biphenylyl group, anthryl group, and phenanthryl group.
  • An aryl group having 6 to 10 carbon atoms is preferred. More preferred is a phenyl group.
  • the alkyl group having 1 to 10 carbon atoms represented by R 5 and R 6 may be linear, branched or cyclic.
  • 1 carbon atom such as methyl group, ethyl group, propyl group, butyl group, isobutyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.
  • it is a linear or branched alkyl group having 1 to 4 carbon atoms. More preferred is a methyl group.
  • Examples of the alcohol compound [3] include 2-methoxyethanol, 2-ethoxyethanol, ethylene glycol monoisopropyl ether, 2-butoxyethanol, ethylene glycol monobenzyl ether, 2-phenoxyethanol, 2-aminoethanol, 2-diethylaminoethanol.
  • 2-methoxyethanol, 2-butoxyethanol, and 2-dimethylaminoethanol are preferable.
  • the above aluminum compounds (B-1) to (B-3) are prepared by changing the number of equivalents of the diol compound [2] and / or the alcohol compound [3] to be reacted with the trialkoxyaluminum [1]. Can be manufactured.
  • the trialkoxyaluminum [1] and the diol compound [2] and / or the alcohol compound [3] are added and refluxed in an inert gas atmosphere, and then a by-product alcohol (R 1 OH) is distilled off under reduced pressure to obtain aluminum compounds (B-1) to (B-3).
  • the reaction temperature is generally about 80 to 120 ° C., and the reaction time is about 2 to 6 hours.
  • the chemical structure of the aluminum compound to be produced varies depending on the type and number of equivalents of the diol compound [2] and / or alcohol compound [3] to be added, and may exist as a mixture. It was decided that the aluminum compound obtained in the above will be defined by the production method.
  • the aluminum compound (B-1) can be produced by reacting 1 to 3 mol of the diol compound [2] with 1 mol of the trialkoxyaluminum [1].
  • the diol compound [2] 2-methyl-2,4-pentanediol
  • an aluminum compound (B-1) represented by the following (a) to (c) is mainly obtained. It is done.
  • the aluminum compound (B-2) can be produced by reacting 1 to 3 mol of the alcohol compound [3] with 1 mol of the trialkoxyaluminum [1].
  • an aluminum compound (B-2) represented by the following (d) to (g) can be obtained.
  • the aluminum compound (B-3) is produced by reacting 1-2 mol of the diol compound [2] and 1-2 mol of the alcohol compound [3] with 1 mol of the trialkoxyaluminum [1]. Can be manufactured.
  • 2-methyl-2,4-pentanediol is used as the diol compound [2]
  • the aluminum compound (B-3) represented by the following (h) to (i) can be obtained.
  • composition of the present invention is represented by the general formula [4] as the aluminum compound (B).
  • R 7 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group, or an aralkyl group
  • R 8 is a linear or branched alkyl group having 1 to 10 carbon atoms.
  • n is 1 or 2
  • two R 7 s may be the same or different from each other .
  • the aluminum compound (B-4) represented by these is contained.
  • Examples of the linear, branched or cyclic alkyl group having 1 to 10 carbon atoms represented by R 7 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Examples include pentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, cyclopentyl group, cyclohexyl group and the like.
  • a linear, branched or cyclic alkyl group having 2 to 8 carbon atoms is preferable.
  • propyl group isopropyl group, butyl group, isobutyl group, amyl group, isoamyl group, tert-amyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, cyclopentyl group, cyclohexyl group and the like.
  • Examples of the aryl group represented by R 7 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an indenyl group, a biphenyl group, an anthryl group, a phenanthryl group, and a benzyl group.
  • An aryl group having 6 to 10 carbon atoms is preferred. More preferably, it is represented by a phenyl group.
  • Examples of the aralkyl group represented by R 7 include a benzyl group and a phenethyl group. It is preferably represented by a benzyl group.
  • Examples of the linear or branched alkyl group having 1 to 10 carbon atoms represented by R 8 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and pentyl.
  • it is a hydrocarbon group having 1 to 4 carbon atoms. More preferably, they are a methyl group and an ethyl group.
  • Examples of the linear or branched alkoxy group having 1 to 10 carbon atoms represented by R 8 include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, penloxy group, hexyloxy group, heptyloxy Group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, phenoxy group and the like.
  • it is a linear or branched alkyl group having 2 to 8 carbon atoms. More preferred are a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
  • n 1, aluminum bis (acetylacetonate) methylate, aluminum bis (acetylacetonate) ethylate, aluminum bis (acetylacetonate) propylate, aluminum bis (acetylacetonate) isopropylate, aluminum bis (acetylacetonate) Butyrate, Aluminum bis (acetylacetonate) isobutyrate, Aluminum bis (acetylacetonate) sec-butylate, Aluminum bis (acetylacetonate) tert-butylate, Aluminum bis (acetylacetonate) amylate, Aluminum bis (acetylacetonate) isoamylate Aluminum bis (acetylacetonate) tert-amylate, aluminum bis (acetylacetonate) G) hexylate, aluminum bis (acetylacetonate) heptylate, aluminum bis (acetylacetonate) octylate, aluminum bis (acetylacetonate) 2-eth
  • the alkyl means an alkyl group having 1 to 10 carbon atoms, preferably a linear or branched alkyl group having 2 to 8 carbon atoms, more preferably a methyl group or an ethyl group.
  • composition of the present invention is represented by the general formula [5] as the aluminum compound (B).
  • R 9 , R 10 , R 11 and R 12 are the same or different from each other and are hydrocarbon groups having 1 to 10 carbon atoms, n is an integer of 0 to 2, and n is 2) Sometimes the two R 9s may be the same or different from each other.) It is preferable to contain the aluminum compound (B-5) represented by these.
  • Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by R 9 , R 10 , R 11 and R 12 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, Examples thereof include alkyl groups having 1 to 10 carbon atoms such as tert-butyl group, amyl group, isoamyl group, tert-amyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group and decyl group. .
  • it has 1 to 5 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, amyl group, isoamyl group, and tert-amyl group. And an alkyl group.
  • R 9 is isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, R 10 , R 11 and R 12 are the same or different from each other, methyl, ethyl, Mention is made of propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • the aluminum compound represented by the formula [5] include isopropoxybis (trimethylsiloxy) aluminum, butoxybis (trimethylsiloxy) aluminum, amyloxybis (trimethylsiloxy) aluminum, isoamyloxybis (trimethylsiloxy) aluminum, tert -Amyloxybis (trimethylsiloxy) aluminum, isopropoxybis (triisopropylsiloxy) aluminum, butoxybis (triisopropylsiloxy) aluminum, amyloxybis (triisopropylsiloxy) aluminum, isoamyloxybis (triisopropylsiloxy) aluminum, tert-amyloxybis (tri Isopropylsiloxy) aluminum, diisopropoxytrimethylsiloxyaluminum, Butoxytrimethylsiloxyaluminum, diamyloxytrimethylsiloxyaluminum, diisoamyloxytrimethylsiloxyaluminum, ditert-amyloxytrimethylsil
  • the aluminum compound (B-5) for example, trialkoxyaluminum and trialkylsilanol (and other alcohol if necessary) can be obtained so that a compound in which n in the general formula [5] is 0, 1, or 2 can be obtained.
  • the aluminum compound (B-5) can be produced by, for example, stirring and mixing the trialkoxyaluminum [6] and the silanol compound [7] and then distilling off the alcohol (R 9 OH) produced by substitution under reduced pressure. Thus, a method of obtaining the target aluminum compound (B-5) can be mentioned.
  • the reaction temperature is generally about 80 to 120 ° C., and the reaction time is about 2 to 4 hours.
  • the content of the aluminum compound (B) in the composition of the present invention is not limited, but is preferably 0.01 to 20 parts by weight, preferably 0.03 to 20 parts by weight with respect to 100 parts by weight of the organopolysiloxane (A). 10 parts by weight is more preferable.
  • the content of the aluminum compound (B) is less than 0.01 parts by weight, the catalytic ability may not be sufficiently exhibited.
  • the content of the aluminum compound (B) exceeds 20 parts by weight, the catalytic performance is not improved as much as it is accompanied, which may be disadvantageous economically.
  • the composition of the present invention may contain a compound used as a silicone curing catalyst, if necessary.
  • the compound include zinc naphthenate, cobalt naphthenate, cobalt octylate, zirconium naphthenate, tetrabutyl orthotitanate, tin (II) 2-ethylhexanoate, tin (II) neodecanoate, and 2-ethylhexanoic acid.
  • Examples thereof include bismuth (III), bismuth (III) neodecanoate, diethanolamine, and triethanolamine. These compounds can be used alone or in combination of two or more.
  • Silicone oil (C) is a component for raising the surface of the coating film formed by the composition of the present invention and imparting antifouling performance. Silicone oil (C) is excellent in compatibility with the organopolysiloxane rubber formed by the condensation reaction of the organopolysiloxane (A). Therefore, according to the composition of this invention, the coating film excellent in the coating-film performance which cannot produce peeling etc. can be formed suitably.
  • silicone oil (C) silicone oils conventionally used in silicone rubber antifouling paints can be used.
  • silicone oil is classified into straight silicone oil and modified silicone oil, both can be used in the composition of the present invention.
  • straight silicone oil examples include dimethyl silicone oil, phenylmethyl silicone oil, and diphenyl silicone oil.
  • Modified silicone oils are amino-modified, carboxyl-modified, epoxy-modified, polyether-modified, carbinol-modified, methylstyryl-modified, alkyl-modified, higher fatty acid ester-modified, hydrophilic special modification, higher alkoxy-modified, higher fatty acid depending on the type of modification. It may be classified into inclusion modification, fluorine modification and the like. Any of these modified silicone oils can be used, and amino-modified, epoxy-modified or polyether-modified silicone oils are particularly preferable.
  • Epoxy-modified silica Commercially available products such as SF8411 (product of Toray Dow Corning Silicone), ISI4730, XI42-301 (product of Toshiba Silicone), L-9300, T-29 (product of Nippon Unicar Company), KF-105 (above, Shin-Etsu Chemical) Industrial product), TSF4730 (above, product of Momentive Performance Materials) and the like, and commercially available products of polyether-modified silicone oil are ISI4460, ISI4445, ISI4446 (product of Toshiba Silicone), SH3746, SH8400, SH3749, SH3700 (product of Toray Dow Corning Silicone) KF6009, X22-4822 (product of Shin-Etsu Silicone), TSF4440, TSF4441, TSF4445, TSF4460 (above, Momentive Puff And products such as X-2-2160AS, KF-6001, KF-6002, KF-6003, X-22-170DX, X-22-176. (
  • the content of the silicone oil (C) in the composition of the present invention is not limited, but is preferably 10 to 200 parts by weight, and 50 to 150 parts by weight with respect to 100 parts by weight of the organopolysiloxane (A). More preferred.
  • the content of the silicone oil (C) is less than 10 parts by weight, the antifouling effect may not be exhibited for a long time.
  • content of this silicone oil (C) exceeds 200 weight part, there exists a possibility that the intensity
  • composition of this invention may contain a crosslinking agent as needed.
  • the cross-linking agent cross-links the organopolysiloxane (A) three-dimensionally to produce silicone rubber.
  • cross-linking agent for example, one molecule of a functional group that is hydrolyzed in the presence of moisture (may be moisture in the air) and reacts with the cross-linking reactive functional group in the organopolysiloxane (A).
  • a polyfunctional silane compound having two or more thereof can be used.
  • Examples of the functional group include acyloxy groups such as an acetoxy group, octanoyloxy group, and benzoyloxy group; alkoxy groups such as a methoxy group, ethoxy group, and propoxy group; ketoxime groups such as a methylethyl ketoxime group and a diethyl ketoxime group; Alkenyloxy groups such as isopropenyloxy group and 1-ethyl-2-methylvinyl group; alkylamino groups such as dimethylamino group, diethylamino group and butylamino group; alkylaminoxy groups such as dimethylaminoxy group and diethylaminoxy group Etc.
  • acyloxy groups such as an acetoxy group, octanoyloxy group, and benzoyloxy group
  • alkoxy groups such as a methoxy group, ethoxy group, and propoxy group
  • ketoxime groups such as a methylethyl keto
  • the polyfunctional silane compound may further have an organic group other than the functional group.
  • organic group include the same organic groups as those described above which the organopolysiloxane (A) has on a silicon atom.
  • Examples of the polyfunctional silane compound include methyltris (methylketoxime) silane, vinyltris (methylethylketoxime) silane, tetra (methylethylketoxime) silane, methyltri (N, N-diethylamino) silane, methyltriacetoxysilane, tetramethoxysilane, Tetraethoxysilane, tetrapropoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, methyltriethoxysilane, trimethoxyisopropoxysilane, methoxytriethoxysilane, dimethyldiethoxysilane, phenyltrimethoxysilane, partial hydrolysis of these Examples include polycondensates. These can be used alone or in admixture of two or more.
  • the content of the crosslinking agent in the composition of the present invention is not particularly limited and can be appropriately set according to the type and the like, but is usually 1 to 100 parts by weight with respect to 100 parts by weight of the organopolysiloxane (A). 100 parts by weight, preferably 3 to 80 parts by weight.
  • composition of the present invention may further contain an inorganic filler for the purpose of improving the physical properties of the coating film.
  • the inorganic filler examples include silica fine powder such as wet method silica and dry method silica, fumed titanium dioxide, diatomaceous earth, aluminum hydroxide, fine particulate alumina, magnesium oxide, zinc oxide, calcium carbonate, zinc carbonate and the like. Is mentioned. In addition, those having a hydrophobic surface treatment with dimethyldichlorosilane, hexamethyldisilazane, cyclic dimethylsiloxane or the like can be used. These inorganic fillers can be used singly or in combination of two or more.
  • the content of the inorganic filler in the composition of the present invention is usually 1 to 30 parts by weight, preferably 3 to 25 parts by weight with respect to 100 parts by weight of the organopolysiloxane (A).
  • Organic solvent The composition of the present invention is usually dissolved and dispersed in an organic solvent. Thereby, it can use suitably as a coating material.
  • organic solvent include xylene, toluene, mineral spirits, MIBK, butyl acetate and the like. Of these, xylene is particularly preferable. These organic solvents can be used alone or in admixture of two or more.
  • the antifouling coating composition of the present invention may contain a plasticizer as necessary.
  • the plasticizer include phosphate esters such as tricresyl phosphate, trioctyl phosphate, and triphenyl phosphate; phthalate esters such as dibutyl phthalate and dioctyl phthalate; adipic acid such as dibutyl adipate and dioctyl adipate Esters; sebacic acid esters such as dibutyl sebacate and dioctyl sebacate; epoxidized oils and fats such as epoxidized soybean oil and epoxidized linseed oil; alkyl vinyl ether polymers such as methyl vinyl ether polymer and ethyl vinyl polymer; polyethylene glycol , Polyalkylene glycols such as polypropylene glycol, etc., ethylenically unsaturated carboxylic acid ester polymer,
  • pigments such as coloring pigments, extender pigments, antirust pigments, sagging inhibitors, silane coupling agents, antifouling agents, and the like can be appropriately blended as necessary.
  • the antifouling paint composition of the present invention comprises the above-mentioned organopolysiloxane (A), aluminum compound (B), silicone oil (C), if necessary, a crosslinking agent, an inorganic filler, an organic It can be prepared by mixing and dispersing a solvent, a plasticizer and the like.
  • the addition amount of the organopolysiloxane (A) and the like may be appropriately adjusted so that the content of the organopolysiloxane (A) and the like is in the above-described range in the composition.
  • the organopolysiloxane (A) in the composition of the present invention has been converted to an organopolysiloxane rubber in advance
  • the organopolysiloxane (A) and the aluminum compound ( B) is mixed and usually at 25 to 80 ° C., preferably at 25 to 50 ° C., the crosslinking reactive functional group in the organopolysiloxane (A) and the crosslinking reactive functional group of another organopolysiloxane (A).
  • an organopolysiloxane rubber is produced by a condensation reaction with a hydrolyzable group in a crosslinking agent, and then the organopolysiloxane rubber and silicone oil (C) are mixed.
  • the antifouling treatment method of the present invention is characterized in that an antifouling coating film is formed on the surface of a coating film forming article using the antifouling coating composition.
  • the antifouling coating film is gradually dissolved from the surface and the coating film surface is constantly renewed, thereby preventing the adhesion of waterpox fouling organisms over a long period of time.
  • the antifouling effect can be exhibited continuously by overcoating the said composition.
  • the coating composition of the present invention absorbs moisture in the air and gradually cures, it is preferable to prepare it immediately before use and to paint as soon as possible after preparation.
  • coating formations include ships; fishing nets (aquaculture nets, stationary nets, etc.), fishing net accessories, etc .; jetty, tetrapots, port facilities, buoys, pipelines, bridges, powerhouse conduits, seabeds
  • Examples include underwater structures such as bases and offshore oil field drilling facilities.
  • the antifouling coating film of the present invention can be formed by applying the above antifouling coating composition to the surface (entirely or partly) of the coating film forming object.
  • the application of the antifouling coating composition can be carried out by a single application or by recoating a plurality of times by means known per se.
  • Examples of the coating method include brush coating, spraying, dipping, flow coating, and spin coating. These may be performed alone or in combination of two or more.
  • curing proceeds to form the antifouling coating film of the present invention.
  • Curing proceeds even at room temperature (25 ° C.), but curing can be promoted by heating to a temperature up to about 80 ° C., for example.
  • Antifouling coating film and coated article The antifouling coating film of the present invention can be formed using the composition of the present invention.
  • the thickness of the antifouling coating film of the present invention may be set as appropriate according to the type of coating film formation.
  • the cured film thickness is in the range of 50 to 300 ⁇ m, preferably 100 to 200 ⁇ m.
  • the coated product of the present invention has the antifouling coating film on the surface.
  • the coated product of the present invention may have the antifouling coating film on the entire surface or a part thereof.
  • the painted product of the present invention can continuously exhibit the antifouling effect, it can be suitably used as the above-mentioned ship (especially ship bottom), fishing equipment, underwater structure and the like.
  • the antifouling coating film when the antifouling coating film is formed on the ship bottom surface of the ship, the antifouling coating film gradually dissolves from the surface, and the coating film surface is constantly renewed, thereby preventing adhesion of waterpox fouling organisms. it can.
  • the antifouling coating film has a suitably controlled hydrolysis rate in seawater. Therefore, the ship can maintain antifouling performance for a long period of time. For example, even in a stationary state such as during berthing or during outfitting, there is little adhesion and accumulation of Minamata fouling organisms, and the antifouling effect can be exhibited for a long period of time.
  • the antifouling coating on the surface basically does not crack or peel off. Therefore, it is not necessary to perform another operation such as forming a coating film after the coating film is completely removed. Therefore, an antifouling coating film can be suitably formed by directly overcoating the antifouling coating film composition. Thereby, it is possible to easily and continuously maintain the antifouling performance at a low cost.
  • the antifouling coating film forming kit of the present invention is (1) a container containing the organopolysiloxane (A), and (2) a container containing the aluminum compound (B), and the silicone oil (C) comprises the container (1) and / or It is contained in this container (2).
  • the above kit can be used as a two-component antifouling paint, and is particularly excellent in storage stability.
  • the said kit can form the antifouling coating film excellent in antifouling performance similarly to the case where the said antifouling paint composition is used.
  • the shape, size, and the like of the container (1) and the container (2) are not particularly limited, and may be appropriately selected depending on the target film-forming object.
  • a tube-like container is preferable in terms of excellent workability.
  • the contents of the aluminum compound (B) and the silicone oil (C) in the kit are within the ranges explained in the items ⁇ Aluminum compound (B)> and ⁇ Silicone oil (C)>. It is preferable to set.
  • the container (1) and / or the container (2) may contain the cross-linking agent, inorganic filler, organic solvent, other additives, and the like as necessary.
  • the kit can form an antifouling coating film excellent in antifouling performance on the coating film-formed product, similarly to the antifouling coating composition.
  • the contents of the container (1) and the contents of the container (2) are mixed, and the resulting mixture is coated.
  • examples thereof include a method of coating the film-formed product, a method of coating the content of the container (1) on the film-formed product, and a method of coating the content of the container (2) thereon.
  • an organopolysiloxane rubber can be suitably formed from the organopolysiloxane (A), and a coating film excellent in antifouling performance can be formed.
  • the antifouling coating composition and the antifouling coating film forming kit of the present invention can form an antifouling coating film having excellent antifouling performance. Moreover, since the composition and kit of the present invention contain an aluminum compound instead of a dialkyltin compound as a curing catalyst, it is highly environmentally safe and has almost no problem of marine pollution even when dissolved in seawater.
  • reaction product had a molar ratio of triisopropoxyaluminum, hexylene glycol and 2-dimethylaminoethanol of 1: 1: 1.
  • Production Example 4 (Production of aluminum compound (B-4)) 24.63 g (0.10 mol) of tributoxyaluminum and 10.0 g (0.10 mol) of acetylacetone were weighed into a 100 ml eggplant-shaped flask equipped with a nitrogen introduction tube, and thoroughly mixed with a magnetic stirrer. Stirring was continued until the exotherm subsided and the internal temperature was close to room temperature, and then the produced butyl alcohol was distilled off under reduced pressure to obtain 26.1 g (yield) of a light yellow viscous liquid aluminum compound (B-4-1). 96%).
  • Production Example 5 (Production of aluminum compound (B-4)) 24.63 g (0.10 mol) of tributoxyaluminum and 20.0 g (0.20 mol) of acetylacetone were weighed into a 100 ml eggplant-shaped flask equipped with a nitrogen introduction tube, and thoroughly mixed with a magnetic stirrer. Stirring was continued until the exotherm subsided and the internal temperature was close to room temperature, and then the produced butyl alcohol was distilled off under reduced pressure to obtain 28.6 g (yield) of a light yellow viscous liquid aluminum compound (B-4-2). 96%).
  • Production Example 9 (Production of aluminum compound (B-5)) 20.4 g (0.10 mol) of triisopropoxyaluminum and 7.41 g (0.10 mol) of butyl alcohol were weighed into a 100 ml eggplant type flask equipped with a nitrogen introduction tube, and thoroughly mixed with a magnetic stirrer. After the generated isopropyl alcohol was distilled off under reduced pressure, 17.44 g (0.10 mol) of triisopropylsilanol was weighed and mixed well with a magnetic stirrer.
  • Test Example 1 (Curability test of organopolysiloxane composition) Tables 10 to 12 show the aluminum compounds (B) obtained in Production Examples 1 to 9 and various additives shown in Tables 10 to 12 with respect to 100 parts by weight of the organopolysiloxane (A) shown in Table 10.
  • Each organopolysiloxane composition was prepared by blending at the indicated ratio (parts by weight) and uniformly mixing in a stirring mixer in the absence of moisture (Reference Examples 1 to 15 and Comparative Reference Examples 1 to 4). The blending and mixing operations of each material were performed at 25 ° C. in the absence of moisture.
  • Each of the obtained organopolysiloxane compositions was coated on a glass plate so that the dry film thickness was 200 ⁇ m, and then left to stand in an atmosphere of 20 ° C. and 60% RH. The time until disappearance (curing time) was measured by finger touch.
  • Examples 1 to 15 and Comparative Examples 1 to 5 (Production of antifouling coating composition)
  • the organopolysiloxane compositions of Reference Examples 1 to 15 and Comparative Reference Examples 1 to 4 and the silicone oil (C) shown in Tables 13 to 15 were blended in the proportions (parts by weight) shown in Tables 13 to 15
  • an antifouling paint composition was produced by uniformly mixing and dispersing in a stirring mixer.
  • Test example 2 (antifouling test) A coated plate obtained by coating a sandblasted steel plate (100 ⁇ 300 ⁇ 2 mm) with an epoxy resin heavy-duty anticorrosive coating so that the dry coating film has a thickness of 200 ⁇ m was used. The coating composition obtained in Examples 1 to 15 and Comparative Examples 1 to 5 was brush-coated on the coated surface of this plate so that the dry coating film was about 150 ⁇ m, and dried in the air (in the presence of moisture). A test plate was prepared. This test plate was immersed in seawater in Owase Bay (Owase City, Mie Prefecture) 1.5 m below the sea level, and the degree of fouling by water fouling organisms was observed for 12 months.
  • Owase Bay Owase City, Mie Prefecture
  • the adhesion area (%) of the above fouling organisms is shown in Tables 13-15.
  • Example 16 Anti-fouling coating film forming kit It is obtained by uniformly mixing 100 parts by weight of Tosseal 371 (organopolysiloxane (A)), 15 parts by weight of tetraethoxysilane (crosslinking agent) and 15 parts by weight of xylene in a stirring mixer in the absence of moisture. The mixture was filled into tubes. This was designated as a container (1).
  • an antifouling coating film forming kit comprising the container (1) and the container (2) was produced.
  • the mixture of the container (1) was coated on a glass plate so that the dry film thickness was 200 ⁇ m, and then the mixture of the container (2) was coated thereon. Thereafter, the film was left in an atmosphere of 20 ° C. and 60% RH, and the time (curing time) until tackiness (stickiness) on the coating film surface disappeared was measured by finger touch. The curing time was 4.0 hours.
  • the mixture of the container (2) is applied from above.
  • the antifouling test was conducted in the same manner as in Test Example 2. After 3 months, 6 months and 12 months, the attached area of the fouling organisms was 0%.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

Cette invention concerne une composition de revêtement antidépôt capable de former un revêtement excellent en matière de lutte contre les dépôts, et qui garantit une haute protection de l'environnement. L'invention concerne une composition de revêtement antidépôt comprenant un organopolysiloxane avec groupe fonctionnel capable d'une réaction de réticulation (A), un composé à base d'aluminium comme catalyseur de réaction de condensation (B) et une huile de silicone (C).
PCT/JP2008/061674 2008-01-25 2008-06-26 Composition de revêtement antidépôt, revêtement antidépôt fabriqué avec cette composition, matière dont la surface est recouverte du revêtement, procédé de traitement antidépôt comprenant la formation du revêtement et kit de formation du revêtement antidépôt WO2009093348A1 (fr)

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JP2008015645A JP2009173815A (ja) 2008-01-25 2008-01-25 防汚塗料組成物、該組成物を用いて形成される防汚塗膜、該塗膜を表面に有する塗装物、該塗膜を形成する防汚処理方法、および防汚塗膜形成用キット
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CN104497869A (zh) * 2015-01-08 2015-04-08 佛山市思特四通化工有限公司 一种石英石防污剂及其制备方法和应用
WO2020209208A1 (fr) * 2019-04-09 2020-10-15 日東化成株式会社 Composition de revêtement antisalissure
WO2021106942A1 (fr) * 2019-11-29 2021-06-03 日東化成株式会社 Catalyseur de durcissement destiné à être utilisé pour le durcissement d'un polymère, composition durcissable à l'humidité, et procédé de production d'un produit durci
WO2021106943A1 (fr) * 2019-11-29 2021-06-03 日東化成株式会社 Catalyseur de durcissement destiné à être utilisé pour le durcissement d'un polymère, procédé de production dudit catalyseur de durcissement, composition durcissable à l'humidité, et procédé de production d'article durci

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JP6162967B2 (ja) * 2013-01-31 2017-07-12 株式会社フコク ゴム部材
KR102354241B1 (ko) * 2013-12-03 2022-01-21 아크조노벨코팅스인터내셔널비.브이. 기판 상에 에이징된 코팅층의 코팅 방법, 및 이 방법에 사용하기에 적합한 코팅 조성물
US10385221B2 (en) 2014-04-03 2019-08-20 Ppg Coatings Europe B.V. Erodible antifouling coating composition
JP7339765B2 (ja) * 2019-04-26 2023-09-06 住友ゴム工業株式会社 ゴルフボール
JP7339766B2 (ja) * 2019-04-26 2023-09-06 住友ゴム工業株式会社 ゴルフボール
JP7370561B2 (ja) * 2019-05-29 2023-10-30 日東化成株式会社 防汚塗料組成物

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CN104497869A (zh) * 2015-01-08 2015-04-08 佛山市思特四通化工有限公司 一种石英石防污剂及其制备方法和应用
WO2020209208A1 (fr) * 2019-04-09 2020-10-15 日東化成株式会社 Composition de revêtement antisalissure
WO2021106942A1 (fr) * 2019-11-29 2021-06-03 日東化成株式会社 Catalyseur de durcissement destiné à être utilisé pour le durcissement d'un polymère, composition durcissable à l'humidité, et procédé de production d'un produit durci
WO2021106943A1 (fr) * 2019-11-29 2021-06-03 日東化成株式会社 Catalyseur de durcissement destiné à être utilisé pour le durcissement d'un polymère, procédé de production dudit catalyseur de durcissement, composition durcissable à l'humidité, et procédé de production d'article durci
JPWO2021106942A1 (ja) * 2019-11-29 2021-12-02 日東化成株式会社 湿気硬化型組成物、硬化物の製造方法
JPWO2021106943A1 (ja) * 2019-11-29 2021-12-02 日東化成株式会社 湿気硬化型組成物、硬化物の製造方法
JP7048138B2 (ja) 2019-11-29 2022-04-05 日東化成株式会社 湿気硬化型組成物、硬化物の製造方法
JP7048139B2 (ja) 2019-11-29 2022-04-05 日東化成株式会社 湿気硬化型組成物、硬化物の製造方法

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