WO1999037725A1 - Composition de revetement - Google Patents

Composition de revetement Download PDF

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Publication number
WO1999037725A1
WO1999037725A1 PCT/JP1999/000148 JP9900148W WO9937725A1 WO 1999037725 A1 WO1999037725 A1 WO 1999037725A1 JP 9900148 W JP9900148 W JP 9900148W WO 9937725 A1 WO9937725 A1 WO 9937725A1
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WIPO (PCT)
Prior art keywords
group
resin
acid
coating
copolymer
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PCT/JP1999/000148
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English (en)
Japanese (ja)
Inventor
Haruhiko Mohri
Yasushi Yonei
Original Assignee
Daikin Industries, Ltd.
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Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO1999037725A1 publication Critical patent/WO1999037725A1/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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes

Definitions

  • the present invention relates to a paint composition that can prevent the attachment of stains such as rain streaks.
  • Japanese Patent Application Laid-Open No. 4-173881 discloses a technique for improving the properties. A reaction between a phenolic dextrin refine copolymer and a silane compound is being studied. Also, in the specification of US Pat. No. 3,342,845, Japanese Patent Application Laid-Open No.
  • silane compounds are sometimes used as a dehydrating agent during polymerization or pigment dispersion, but almost all silane compounds are used during production. Can react with water, and the paints produced from them have little effect on improving the antifouling adhesion. This is the current situation.
  • W094680, WO95Z02645 Japanese Patent Publication No. 7-148540, Japanese Patent Application Laid-Open No. 7-102211, Japanese Patent Application Laid-Open No. 7-136584, Japanese Patent Application Laid-Open No. 7-173842, Japanese Patent Application Laid-open No. Kaikai Hei 7-1094 35, Tokai Kaihei 7-61084, Tokai Hei 8-12922, Tokkai Hei 8-113755, Tokkai Hei 8-319448, Tokai Kaihei No.
  • the purpose of the present invention is to remarkably excel in air pollution and rain streaks, which do not accumulate and accumulate, antifouling adhesion, and especially initial hydrophilicity.
  • the purpose of the present invention is to provide a coating composition for forming a coated film. Disclosure of the invention
  • the present invention is a.
  • (B) Resin for paint It relates to a composition for coatings consisting of this.
  • the organic group having 1 to 10 carbon atoms is an ethyl group, a port pill group, a glycidinole group, a butyl group, or a 2-ethylhexyl group. It is preferred that at least one of the octyl groups be at least one.
  • a fluoropolymer having a hydroxyl group and / or a hydroxyl group is soluble in a solvent.
  • Unique combination of acrylic resin, acrylic resin, acrylic silicone resin, inorganic materials, and vinylidene fluoride that does not have a functional group Preference is given to a composite aqueous dispersion of a polymer and an acrylic copolymer, or an aqueous dispersion of a fluoroolefin-vinyl ether copolymer.
  • the gayne-containing compound (A) contains a methyl group as an essential component and acts as an antifouling agent.
  • easily removable substituents such as a methyl group are hardly collected on the coating film surface, and the ethyl group, Substituents that are difficult to remove, such as propyl groups, tend to collect on the surface of the coating film.
  • the alkoxy group bound to the gay component constituting the gay component-containing compound (A) is collected on the surface of the coating film.
  • it is decomposed and desorbed by the action of rainwater and other water, and can remove contaminants adhering to the surface of the coating film.
  • the time required to reach hydrophilicity is shorter than that of a conventional coating film, that is, the initial hydrophilicity is superior. Excellent antifouling adhesion It is intended to provide a coating.
  • the silicon-containing compound (A) in the present invention is:
  • R 1 R, R rio and R 4 are a methyl group, and the rest are each independently a C 1 -C 10.
  • scale 1 RR 3 number ratio against the total of your good beauty R 4 of main switch Le group have you to equation (1) is 0. 0 5 ⁇ 0. 9 5 , n is 2-1 0 (An integer of 0).
  • the silicon-containing compound (A) represented by the formula (1) is represented by the formula (2):
  • R 1 , R, R 3 and R 4 are a methylene group from the viewpoint of the initial hydrophilicity, and the remaining is And each independently represents an organic group having 1 to 10 carbon atoms. Further, the organic group having 1 to 10 carbon atoms may contain an oxygen atom or a nitrogen atom.
  • Examples of the organic group include an alkyl group, an alkoxyalkyl group, an acyl group, an aryl group, an aryl group, an oxym group, and an amino group. Alkylene groups and glycidyl groups are preferred.
  • the organic group having 1 carbon atom is, for example, a methyl group or a holmyl group, and the organic group having 2 carbon atoms is, for example, an ethyl group.
  • As an organic group having 3 carbon atoms such as an acetyl group, a methoxymethyl group, and the like, there are, for example, a propynole group, a methoxyethyl group, and a glycine group.
  • An organic group having 4 carbon atoms such as a zir group is, for example, a butyl group such as a butyl group, and a pentyl group as an organic group having 5 or more carbon atoms, for example. , Hexyl group, octyl group, 2-ethylhexyl group, phenyl group, benzyl group, benzyl group, etc. .
  • an ethyl group, a methylenol group, a propynolene group, a butyryl group, Glycidyl, 2—ethylhexyl and octyl groups are preferred, as well as ethyl, methyl and butyl groups. Is especially preferred.
  • the control of the number ratio of the methyl group to the sum of R 1 R 2 , R 3 and R 4 is performed, for example, by controlling the content of the gallium-containing compound represented by the above formula (1).
  • n is an integer of 2 to L 0, but it is preferably 4 to 30 from the viewpoint of surface hydrophilicity. It is particularly preferred that the value be 5 to 20 in terms of storage stability of the compound containing iodine.
  • the production of the compound (A) containing a gallium compound is carried out by mixing tetraalkoxysilane (which may be an oligomer) with a catalyst. It is obtained by heating in the presence.
  • the catalyst may be, for example, hydrochloric acid, sulfuric acid, acetic acid, paranorenens olenoic acid, ammonia, trimethinoleamine, trietinophenol.
  • reaction solvent examples include methanol, ethanol, and isoprono. No-nore, n-butano-no-no, t-butano-no-o-no-no-re, 2,2,2-trino-nore-no-e-no-no-re, 2, 2,3,3,3—Pentafole nozzles, alcohols such as ethanol, tetrahydrofuran, 1,4-dioxan , Ethers such as tetrahydropyran, acetone, acetic acid 2-ketones / esters such as methoxymethyl, N, N — Dimethylformamide, N, N — dimethylaminoacetamide, N—methylamineacetamide, N—methylamine pyrrolide, a mi de ethers etc.
  • the silicon-containing compound (A) has a number-average molecular weight measured by GPC (converted to polystyrene using tetrahydrofuran as a solvent). 500 or more: L 0000, particularly preferably 2,000 to 6000, is preferable from the viewpoints of hydrophilicity, storage stability of the compound containing a Ga, and appearance of the coating film.
  • the compounding amount of the silicon-containing compound (A) is 0.:! With respect to 100 parts by weight of the coating resin (B). It is up to 80 parts by weight, preferably 1 to 30 parts by weight. If the amount is less than 0.1 part by weight, there is a tendency that the anti-fouling property is reduced, and if the amount exceeds 80 parts by weight, the coating film is poor and the compatibility with the resin is reduced. May occur.
  • composition for paints of the present invention comprises (A) the above-mentioned specified compound containing a compound which acts as a pollution control agent and (B) a resin for paints. And (C) if necessary, a hardener and / or a hard catalyst.
  • the coating has a good antifouling, low antistatic and antistatic property. It gives properties such as reliability.
  • the resin for paint (B) is, for example, a fluorene resin which is soluble in a solvent and has a hydroxyl group and / or a carboxyl group.
  • the number average molecular weight (according to GPC) of the copolymer is from 1,000 to 100,000, and preferably from 1,500 to 300,000. If the molecular weight is less than 1,000, the curability and weather resistance tend to be insufficient, and if it exceeds 100,000, the workability and paintability tend to cause problems. There is.
  • the hydroxyl value of this copolymer is from 0 to 200 (mg K 0 H
  • the acid value is preferably from 0 to 100 (mg KOHZ g), more preferably from 0 to 50 (mg KOH / g). Said When the acid value decreases, curing tends to be poor, and the acid value tends to decrease.
  • a hydroxyl group and / or a carboxy resin are considered from the viewpoints of stain-proofing adhesion, stain-removing properties, and dust-proofing properties. It is also possible to use a solvent-soluble tetrafluoroethylene copolymer having a group.
  • Examples of the above-mentioned copolymer include Zefflu manufactured by Daikin Industries, Ltd., Lumifuron manufactured by Asahi Glass Co., Ltd., and Central Glass Co., Ltd. Marketed products such as Cefral Co., Ltd., Fluoronet by Ink Chemical Industry Co., Ltd. of Japan, ZAFLON by Toa Kasei Co., Ltd. are available. .
  • the acrylic polyol resin a known resin can be used.
  • the resin may have a hydroxyl group, a carboxyl group, an epoxy group, or an amino group.
  • the hydroxyl value of the acrylic polyol resin is 0 to 200 (mgKOH / g), and preferably 0 to 100 (mgKOH / g). If the hydroxyl value is too small, curing tends to be poor, and if it exceeds 200 (mg KOH g), there is a problem with the flexibility of the coating film. There is a tendency to be.
  • the acid value of the acrylic polyol resin is from 0 to 100 (mgKOH / g), and more preferably from 0 to 50 (mgKOH / g). If the acid value is too low, curing tends to be poor, and if the acid value exceeds 100 (mg KOH / g), there is a problem in the flexibility of the coating film. There is a tendency to be.
  • acrylic resins include, for example, Mitsubishi Rayon Co., Ltd.'s Dianal, and Dainippon Ink Chemical Industry Co., Ltd.'s Atari Co., Ltd. Dick, Hitaroid manufactured by Hitachi Chemical Co., Ltd. Commercial products such as Mitsui Toatsu Chemical Co., Ltd.'s register can be used.
  • the acrylic silicone monomer may be a hydroxyl group-containing monomer or other polymerizable unsaturated resin. What is necessary is just that it is polymerized together with the monomer.
  • the acrylic silicone resin may have a hydrolyzable silyl group, hydroxyl group, or epoxy group.
  • Acrylic silicone resins include, for example, Zemrack manufactured by Kaneka Kagaku Kagyo Co., Ltd. and Krymarmer manufactured by Sanyo Kasei Kogyo Co., Ltd. You can use commercial products.
  • the inorganic material examples include non-hydrolyzable group-containing metals (such as Si, Ti, and A1), alcohols, and non-hydrolyzable fluorine-containing organo-organic organos.
  • Nopoloxixan, metals (Si, Ti, A1, etc.), anorecoxide, etc. are exempt, and if they were commercial products, the Gunze industry Ecoleton Co., Ltd., Gloss Power manufactured by Nippon Synthetic Gum Co., Ltd., Poserin manufactured by Tobe Co., Ltd., Belcuri manufactured by Nippon Yushi SH, SR and DC series manufactured by Silicone Corporation, and KR manufactured by Shin-Etsu Chemical Co., Ltd.
  • fluorine resins having no functional group Japanese Patent Publication No. 43-103, No. 3-8282, No. Fluoride described in each gazette such as Kaihei 4 — 1 8 9 8 7 9 A vinylidene homopolymer or copolymer, etc.
  • a resin having no functional group it is not necessary to use a curing agent or a curing catalyst in the paint composition of the present invention. Absent .
  • Japanese Patent Application Laid-Open No. 3-77884 is disclosed as Japanese Patent Application Laid-Open No. 8-122021 , and as a commercially available product, for example, Zeffl manufactured by Daikin Industries, Ltd. In addition, Floren manufactured by Nihon Gosei Gum Kogyo Co., Ltd. is mentioned.
  • aqueous dispersion of the fluororefin-1-vinylinole-ester copolymer is described in, for example, Japanese Unexamined Patent Publication No.
  • Some of the commercially available products are, for example, Lumifront manufactured by Asahi Glass Co., Ltd., and Fumino manufactured by Dainippon Ink Chemicals Co., Ltd. You will be able to get more information.
  • the coating composition of the present invention may contain a curing agent and a hardening catalyst as long as the present invention does not impair the antifouling adhesion property. .
  • a dicocyanate compound for example, a dicocyanate compound, a block isocyanate compound, a melamine resin, a dibasic acid, a non-hydrolyzed
  • silane compounds containing functional groups, epoxy resins, or acid anhydrides are required, iso-cane from the viewpoints of weather resistance, acid resistance, and rain resistance
  • Block isocyanate and epoxy resin are preferred.
  • Examples of the above-mentioned isocyanate compound and the block isocyanate compound include, for example, 2, 4 — tri-range isocyanate. , Diphenylene methane 4, 4 '— Resilience, iso-reagent, iso-holo-zoni-so-zen, re-silient methyl ester Chromatic resiliency isolators, trimethyl resilience isolators, resilience isolators, trimmers Anet, n — pentane-1,4-diisocyanate, these trimers, these adducts ⁇ biuret Although these polymers have two or more isocyanate groups, they are also blocked and further isolated. It is not limited to these, but is limited to these.
  • the mixing ratio of the isolation to the resin for coating is preferably 0.5 to 5.0 in NC0Z0H (Mono ratio), and more preferably 0.8. ⁇ 1.2 is more preferred. Also, if the iso- nate is of the moisture-hardening type, then 1.:! ⁇ 1.5 is preferred.
  • the above-mentioned melamin resin may be, for example, besides the melamin resin, the melamin is a methylo-zole-i-i-d-a-r Laminate resin, methylated monomethylated Melamin is etherified with alcohols such as methanol, ethanol, butanol, etc. There are various types of resin such as buttery but not limited to melamin resin.
  • Epoxy Dagger compound is, for example,
  • CH 2 -CH-CH 2 one 0- CH 2 CH 2 - 0 - CH 2 _CH- CH 2
  • CH H2 It is not limited to these, but it is not limited to these.
  • the acid anhydrides include, for example, phthalic anhydride, tri-U-methritic anhydride, pyromellitic anhydride, and anhydrides 1, 2-cis-hexyl.
  • examples include, but are not limited to, dicarboxylic acid, anhydrous succinic acid, maleic anhydride, etc.
  • fumaric acid succinic acid, adipic acid, azelanic acid, seno ⁇ cinnamic acid, dodecanedioic acid, 1,2-cyclohexyl Dibasic acids such as oleic acid are also used as curing agents
  • the curing agent is used in an amount of 100 parts by weight or less, preferably 5 to 40 parts by weight, per 100 parts by weight of the coating resin ( ⁇ ).
  • Curing catalysts include, for example, organic tin compounds, organic acid phosphate esters, organic titanate compounds, acid phosphate esters and a Reaction with min, saturated or unsaturated polyvalent carboxylic acid or its anhydride, organic sulfonic acid, amide Compounds, aluminum chelates, titanium chelates, quinolone chelates, etc. It is badly.
  • organic tin compounds include dibutyl tin glaurate, dibutyl tin maleate, dioctinoles maleate, and the like. Eighth, dibutyls, jiacetate, etc. are given.
  • organic acid phosphoric acid ester examples include:
  • aminic compound examples include, for example, butinoreamin, octylamine, dibutinoreamin, mononoamine.
  • DBU dibenzyl Amin
  • DBU dibutinoreamin
  • salts such as carboxylic acid
  • chelate compounds include aluminum tris (ethyl acetate acetate) and aluminum tris (acetate). (China acetate), Ginore Consortium Textrax (Acetinolacetonate), Jisopro Box Services (Echilwa) Settlement) Titanium etc. are required.
  • One curing catalyst may be used, or two or more curing catalysts may be used in combination.
  • Preferred curing catalysts include an organic tin compound and an anoluminium chelate compound.
  • the combination of the coating resin and a curing agent and a Z or a hardening catalyst is not particularly limited. A better combination would be something like the following.
  • examples of the hardening agent include an isopropylate compound, a blockisomate compound and the like.
  • a curing catalyst can be used in combination.
  • a curing catalyst may be used.
  • the curing catalyst is used in an amount of 50 parts by weight or less, preferably 0.0001 to 10 parts by weight, based on 100 parts by weight of the resin for coating (B).
  • an organic solvent can be mixed into the coating composition.
  • organic solvent examples include hydrocarbons such as xylene, toluene, solvesso 100, solvesso 150, and hexane.
  • Solvents methyl acetate, ethyl acetate, ethyl acetate, ethyl acetate alcohol monomethyl ether, ethyl acetate alcohol, monoethyl acetate Tile ether, alcoholic acid ethyl alcohol, butyric acid monoethyl ether, diethyl ethyl alcohol monomethyl ether, acid Diethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethyl acetate acetate Solvents such as toluene, diethyl acetate glycol, etc., dimethyl ether ether, dimethyl alcohol, etc.
  • Ketone-based solvent N, N—dimethyl acetate amide, N—methyl acetoamide, acetate amide, N, N—dimethyl methyl amide
  • Amide-based solvents such as norem amide, N, N-methyl hol amide, and N-methyl hol arn amide
  • Snorrephonic acid such as Ester-based solvents, methanol, ethanol, isopropanol, butanol, ethylene glycol, diethylene grayed Li co Lumpur, Po Li et Chi les in g Li co over Honoré (polymerization degree 3 ⁇ 100), CFCH 2 0 H . F (CF 2) CH 2 0 H.
  • a liquid at room temperature is desired, and the trichloro-opening fluorene and the tetrachloride fluorene are preferred.
  • Tri-fluoro mouth Fluoro-Rotan, Jibromote, Fluoro-Rotan, HCFC-123, HCFC-141B.HCFC-22 5, Jikro-hexafluorocyclobutane, Tetracro mouth to xafluoro-butane, perfluoropentane, no, 0 — Fluoro-hexa, perforated heptane, perfluoro-octane, etc.
  • a fluorine atom In order to further dissolve the paint resin and the hardener, it is desirable to include a fluorine atom, a chlorine atom, and a carbon atom at the same time. It is preferable to use HCFC-123, HCFC-141b, HCFC-225, and Texa-fluoride.
  • the mixing ratio of the coating resin and the alcohol-based solvent is 1 to 50 parts by weight with respect to 100 parts by weight of the coating resin, and the curability and the appearance of the coating film are poor. It is even more preferred that the amount be 1 to 25 parts by weight from the point of view.
  • the coating composition of the present invention further includes, for example, a pigment, a pigment dispersant, a thickener, a repelling agent, a defoamer, a film-forming aid, an ultraviolet absorbing agent, and the like.
  • HALS HALS
  • anti-glazing agents fillers, colloidal silica, anti-fungal agents, silane coupling agents, anti-skinning agents, antioxidants, difficult Paints such as flame retardants, anti-sagging agents, antistatic agents, anti-oxidants, water-soluble resins (polyvinyl alcohol, polystyrene oxide, etc.) Excipients can also be incorporated.
  • the coating composition of the present invention can be used for coating objects such as metals, ceramics, plastics, cement, wood, and old coatings. If necessary, the undercoat layer and the middle coat layer can be provided as appropriate. There are no particular restrictions on the coating method, and the roll coating method, spraying method, brush coating method, roller method, flow coating method, and date method are not particularly limited. It is possible to adopt a tubing method.
  • the thickness of the coating film is usually from 1 to 100 m, preferably from l to 50; tm.
  • Uses of the articles coated with the coating composition of the present invention include, for example, waterproof sheets for construction, waterproof sheets for tunnels, and agricultural vinyls.
  • Roll sheet agricultural vinyl film, curing sheet, architectural protection sheet, vehicle protection sheet, mesh sheet, mesh sheet Inside the screen, Polycarbonate roof, Acrylic board wall, Polycarbonate wall, Gardanore, traffic light, Tunnel Walls, tunnel interior panels, road signs, billboards, high-speed road side walls, high-speed road noise barriers, road lights, bridges, bridge girders, piers, chimneys, wallpaper, tatami, mats, te -Blue Cross, Ventilation fans, marking finolems, geomembrane, billboards, postal posts, telephone poles, tents, cars, airplanes, ships, electric cars, etc. can give .
  • Zeffle LC — 9 7 4 (a product manufactured by Daikin Industries, Ltd.) 100 parts by weight (hereinafter referred to as “parts”) of vinylidene fluoride copolymer and acrylic resin for paints: 100 parts by weight of resin solids: 38%) and acetic acid Mix 150 parts of butyl, 3.8 parts of the compound containing the compound obtained in Synthesis Example 1 and mix well, and then stir well to obtain the paint composition of the present invention. I got it.
  • This coating composition was pre-painted (spray coating) with a fluorine coating (white) as the undercoating paint (film thickness 50 m).
  • the following tests were performed after painting on a metal plate (7 x 15 x 0.5 cm), drying at room temperature for 1 week, and applying a 40 / m-thick coated plate. . The results are shown in Table 1.
  • the painted board was exposed outdoors for 1 week, 2 weeks and 1 month on the 3rd floor rooftop of a building under Osaka Prefecture in the rainy season on a 3rd-floor roof at a slope of 30 ° on the south side.
  • the adhesion was evaluated.
  • the contamination resistance is measured by measuring the difference ( ⁇ L *) between the initial lightness of the coated plate and the lightness after exposure.
  • AL * is less than 0 or less than L
  • A is 1 to 1 or less.
  • a value of less than 2 was evaluated as B, a value of 3 to less than 5 as C, a value of 6 to less than 10 as D, and a value of 10 or more as E.
  • Example 3 The use of each of the components shown in Table 1 was carried out in the same manner as in Example 1 to prepare the coating composition of the present invention, and the evaluation was carried out in the same manner as in Example 1. The results are shown in Table 1.
  • LC-941 in Table 1 is Zeffl LC-941 manufactured by Daikin Industries, Ltd., which is a copolymer of vinylidene fluoride and a polymer. It is a paint varnish made of lily resin.
  • a coating composition of the present invention was prepared in the same manner as in Example 3 except that the compound containing the gay obtained in Synthesis Example 2 was used. It was evaluated in the same way as above. The results are shown in Table 1. Comparative Examples 1 to 3
  • a coating composition for comparison was prepared in the same manner as in Example 1 or Example 5 except that the components shown in Table 1 were used, and the same as Example 1 was carried out. It was evaluated as follows. The results are shown in Table 1.
  • Et 40, Et 48 and Me 56 are Eno Resilient 40 (manufactured by Konorecoat Co., Ltd.) Pentamer), ethyl silicate 48 (a tetramer of tetraethoxysilane) and a methyl silicate manufactured by Mitsubishi Kagaku Co., Ltd. — To 56 (the tetramer of tetramethyl silane).
  • Et 40, Et 48 and Me 56 are Eno Resilient 40 (manufactured by Konorecoat Co., Ltd.) Pentamer), ethyl silicate 48 (a tetramer of tetraethoxysilane) and a methyl silicate manufactured by Mitsubishi Kagaku Co., Ltd. — To 56 (the tetramer of t
  • a coating composition of the present invention was prepared in the same manner as in Example 5 except that the compound containing the gallium obtained in Synthesis Example 2 was used. And evaluated. The results are shown in Table 1. Comparative Examples 4 to 6
  • Example 1 Using each of the components shown in Table 1, a paint composition for comparison was prepared in the same manner as in Example 1 or Example 5, and the composition for Example 1 was used. It was evaluated in the same way. The results are shown in Table 1.
  • LC — 974 100 parts of Zeff Nore GK — A mixture of 66 parts of 500 and Zeffle GK — 34 parts of 501 (Either Daikin Industries, Ltd.)
  • the solvent was replaced with a solvent-soluble fluorofluorene copolymer (butyl acetate solution) manufactured by Co., Ltd. in the same manner as in Example 1 to obtain the paint of the present invention.
  • the composition for use was obtained.
  • This paint composition was evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • Example 7 The same procedure as in Example 7 was repeated except that the composition containing a gay element obtained in Synthesis Example 2 was used to prepare the coating composition of the present invention. It was evaluated in the same way as above. The results are shown in Table 1. Methyl group / Contact angle of water of compound ( ⁇ ) (degree)
  • (B) is a curing catalyst compound (A) (, IiISJl X H nosing power ⁇ ⁇ ("SO 1 3 5 5 7 1 week 2 weeks 1 month
  • the coating film containing the compound containing silicon according to the present invention is superior in the initial hydrophilicity and the stain resistance.
  • a coating composition which is capable of maintaining the appearance of a coating film stably for a long period of time, which is effective in preventing adhesion of rain streaks and the like. It can be provided at low cost.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de revêtement peu coûteuse permettant de former des films dont les propriétés de résistance aux taches et d'aspect de surface peuvent être conservées de manière stable pendant une durée prolongée. La composition comporte: (A) un composé de silicone représenté par la formule générale (1) (dans laquelle au moins un des éléments du groupe comprenant R?1, R2, R3 et R4¿ est méthyle, tandis que les autres sont chacun indépendamment un groupe organique en C¿1?-C10, et le rapport entre le nombre de groupes méthyle et le résultat de la somme de R?1, R2, R3 et R4¿ se situe entre 0,05 et 0,95; et n est un nombre entier compris entre 2 et 100); et (B) une résine de revêtement.
PCT/JP1999/000148 1998-01-26 1999-01-18 Composition de revetement WO1999037725A1 (fr)

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JP10/12467 1998-01-26
JP01246798A JP4192285B2 (ja) 1998-01-26 1998-01-26 塗料用組成物

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JP3559751B2 (ja) * 2000-06-30 2004-09-02 関西ペイント株式会社 塗料組成物
JP5403847B2 (ja) * 2005-01-05 2014-01-29 株式会社カネカ 耐汚染性付与組成物、塗料組成物および該塗料組成物から得られる塗膜
JP4637703B2 (ja) * 2005-09-29 2011-02-23 エスケー化研株式会社 装飾面の塗装仕上げ方法、及び装飾積層体
KR101270397B1 (ko) 2009-03-25 2013-06-07 다이킨 고교 가부시키가이샤 저오염성 상온 경화형 도료 조성물
EP2415844B1 (fr) 2009-03-31 2018-09-12 Daikin Industries, Ltd. Composition de revêtement à base d'une résine durcissable à température ambiante
JP5368951B2 (ja) * 2009-11-25 2013-12-18 パナソニック株式会社 撥水撥油性樹脂組成物及び塗装品
WO2014046119A1 (fr) * 2012-09-18 2014-03-27 ダイキン工業株式会社 Composition de revêtement, film de revêtement durci, feuille arrière pour module photovoltaïque, et module photovoltaïque

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JPH0812922A (ja) * 1993-07-14 1996-01-16 Asahi Glass Co Ltd 屋外物品表面を処理する方法
JPH08231856A (ja) * 1995-02-28 1996-09-10 Chuo Rika Kogyo Kk 硬化性組成物及びその製造方法
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