Organosilicon compounds, their hydrolysis condensates, coating compositions, and coated articles

Abstract

To provide an organosilicon compound which gives a coating composition having hydrophilic and antifogging properties with excellent water resistance.SOLUTION: The present invention provides an organosilicon compound represented by a formula (1) (where the R1 moieties each independently represent a hydrogen atom, a C1-10 alkyl group, or a C6-10 aryl group, the R2 moieties each independently represent a C1-10 alkyl group or a C6-10 aryl group, X represents a C2-20 divalent saturated hydrocarbon group, which may be interposed by a sulfur atom, and n is an integer of 1-3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to organosilicon compounds, hydrolysis condensates thereof, coating compositions containing organosilicon compounds, and coated articles. [Background technology]

[0002] In recent years, there has been a growing demand for improvements in the clouding of substrates made from inorganic materials such as glass and organic materials such as plastics. Generally, improvements in substrate clouding are achieved by coating the surface of the substrate with a hydrophilic film. For example, a coating composition mainly composed of an organosilicon compound having a sulfobetaine structure in which the nitrogen atom in the nitrogen-containing heterocyclic structure has a positive charge is known as a coating agent that can impart hydrophilicity to a substrate (see Patent Documents 1 and 2).

[0003] However, the coated film to which the above coating composition is applied does not have sufficient water resistance, and when it comes into contact with water, the surface properties such as hydrophilicity and antifogging described above may deteriorate, and further improvement is desired. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2019-48966 [Patent Document 2] Japanese Patent Publication No. 2022-82176 [Overview of the project] [Problems that the invention aims to solve]

[0005] The present invention has been made in view of the above circumstances, and aims to provide an organosilicon compound that gives a coating composition with excellent hydrophilicity, anti-fogging properties, and water resistance. [Means for solving the problem]

[0006] As a result of diligent research to solve the above problems, the present inventors have discovered that a specific organosilicon compound having a glycerol derivative structure provides a coating composition that is excellent in water resistance and can impart durable hydrophilicity and anti-fogging properties to substrates formed from inorganic materials such as glass and organic materials such as plastics, thus completing the present invention.

[0007] In other words, the present invention is 1. An organosilicon compound represented by the following formula (1), [ka] (In the formula, R 1 Each of these independently represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, or an aryl group with 6 to 10 carbon atoms, and R 2 Each of the following independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms; X represents a divalent saturated hydrocarbon group having 2 to 20 carbon atoms, which may contain a sulfur atom; and n is an integer from 1 to 3. 2. One organosilicon compound represented by the following formula (2) or formula (3), [ka] (In the formula, R 1 , R 2 (And n have the same meaning as above, m is an integer from 1 to 10, and k is an integer from 2 to 10.) 3. A composition comprising a hydrolysis condensate of one or two organosilicon compounds, 4. A coating composition comprising one or two organosilicon compounds, a hydrolysis condensate of the organosilicon compound, or both. 5. A coated article having a substrate and a coating made of one of the coating compositions formed directly or via one or more other layers on at least one surface of the substrate. To provide. [Effects of the Invention]

[0008] The organosilicon compound of the present invention is excellent in water resistance and gives a coating composition capable of imparting sustainable hydrophilicity and antifogging properties to substrates such as glass.

Embodiments for Carrying out the Invention

[0009] Hereinafter, the present invention will be specifically described. The organosilicon compound of the present invention is represented by the following formula (1).

[0010]

Chemical formula

[0011] In formula (1), R 1 each independently represents an alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms, preferably 6 to 8 carbon atoms. R 1 The alkyl group may be linear, branched or cyclic. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, cyclohexyl groups and the like. R 1 Specific examples of the aryl group of R include phenyl group, tolyl group and the like. Among these, R 1 is preferably an alkyl group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group.

[0012] R 2 each independently represents an alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms, preferably 6 to 8 carbon atoms. Specific examples of these alkyl groups and aryl groups are the same as those exemplified for R 1 However, among them, a methyl group is preferred.

[0013] X represents a divalent saturated hydrocarbon group having 2 to 20 carbon atoms, which may contain a sulfur atom, and is preferably a group represented by the following formula.

[0014] [ka] (In the formula, m is an integer between 1 and 10, and k is an integer between 2 and 10.)

[0015] In other words, the organosilicon compound of the present invention is preferably a compound represented by the following formula (2) or formula (3).

[0016] [ka] (In the formula, R 1 , R 2 ,n,m, andk represent the same meanings as above.

[0017] In particular, with respect to m and k as described above, from the viewpoint of the hydroxyl group content per unit mass and anti-fogging properties of the organosilicon compound of the present invention, m is preferably an integer from 1 to 8, more preferably 3, and k is preferably an integer from 2 to 6, more preferably 5.

[0018] Specific examples of the organosilicon compounds of the present invention are given below, but are not limited to these.

[0019] [ka] (In the formula, Me represents a methyl group. The same applies below.)

[0020] The organosilicon compound represented by formula (1) above can be produced, for example, by a thiol-ene reaction between a mercapto group-containing silane compound represented by formula (I) below and a glycerol derivative represented by formula (II) below, or by a hydrosilylation reaction between a hydrosilane represented by formula (III) below and a glycerol derivative represented by formula (II) below.

[0021] [ka] (In the formula, R 1 , R 2 k, m, and n have the same meanings as above.

[0022] Specific examples of mercapto group-containing silane compounds represented by the above formula (I) are shown below, but are not limited to these. Among these, 3-mercaptopropyltrimethoxysilane represented by the following structural formula (4) is preferred.

[0023] [ka]

[0024] The glycerol derivative represented by the above formula (II) is preferably 7-octen-1,2,3-triol.

[0025] Specific examples of hydrosilanes represented by formula (III) above are shown below, but are not limited to these. Among these, trimethoxysilane represented by structural formula (5) below is preferred.

[0026] [ka]

[0027] The thiol-ene reaction between the mercapto group-containing silane compound represented by formula (I) and the glycerol derivative represented by formula (II) can be carried out according to known thiol-ene reactions.

[0028] In the thiol-ene reaction, catalysts such as organic peroxides and azo compounds may be used as needed. Specific examples of organic peroxides include benzoyl peroxide, cumene hydroperoxide, ditert-butyl peroxide, tert-butyl hydroperoxide, and dicumyl peroxide. Specific examples of azo compounds include 2,2'-azobispropane, 2,2'-dichloro-2,2'-azobispropane, 1,1'-azo(methylethyl)diacetate, 2,2'-azobisisobutane, 2,2'-azobisisobutylamide, 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis-2-methylpropionate methyl, 2,2'-dichloro-2,2'-azobisbutane, 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobisisobutyronitrile, 3,5-dihydroxymethylphenylazo-2-methylmalonodinitrile, 2,2'-azobis-2-methylvaleronitrile, 4,4'-azobis-4-cyanovalerate dimethyl, and 2,2'-azobis-2,4-dimethylvaleronitrile.

[0029] The amount of catalyst used is preferably 0.00001 to 10 parts by mass per 100 parts by mass of the total amount of the mercapto group-containing silane compound represented by formula (I) and the glycerol derivative represented by formula (II).

[0030] In thiol-ene reactions, solvents may be used as needed. Suitable solvents include alcohols such as methanol, ethanol, isopropanol, and t-butanol; ketones such as acetone and methyl isobutyl ketone; ethers such as dibutyl ether; esters such as ethyl acetate; aromatic hydrocarbons such as toluene; and aliphatic hydrocarbons such as hexane and decane. The reaction temperature for the thiol-ene reaction is preferably 0 to 150°C, more preferably 50 to 150°C, and if a solvent is used, it should be set according to the boiling point of the solvent. The reaction time is preferably 1 to 150 hours, more preferably 5 to 100 hours.

[0031] The preferred ratio of the mercapto group-containing silane compound represented by formula (I) and the glycerol derivative represented by formula (II) in the thiol-ene reaction is 0.75 to 1.25 moles, and more preferably 0.9 to 1.1 moles, of the glycerol derivative (II) per mole of the mercapto group-containing silane compound (I).

[0032] Furthermore, the hydrosilylation reaction between the hydrosilane represented by formula (III) and the glycerol derivative represented by formula (II) can be carried out according to known hydrosilylation reactions.

[0033] Examples of hydrosilylation reaction catalysts include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, and complexes of chloroplatinic acid with olefins, vinylsiloxanes, acetylene alcohol, etc. The amount added can be appropriately selected according to the desired curing rate, but is usually preferably 0.1 to 500 ppm, more preferably 1 to 200 ppm, in terms of the mass of platinum group metals relative to the total mass of the hydrosilane represented by formula (III) and the glycerol derivative represented by formula (II) used in the reaction.

[0034] There are no particular restrictions on the conditions for the hydrosilylation reaction, but a reaction temperature of 20 to 120°C and a reaction time of 1 to 8 hours are preferred, and a reaction temperature of 20 to 100°C and a reaction time of 1 to 6 hours are more preferred.

[0035] In the hydrosilylation reaction, the ratio of the hydrosilane represented by formula (III) to the glycerol derivative represented by formula (II) is preferably 0.75 to 1.25 moles, and more preferably 0.9 to 1.1 moles, of the glycerol derivative (II) per mole of hydrosilane (III).

[0036] The coating composition of the present invention contains one or more organosilicon compounds represented by the above formula (1) and their hydrolysis condensates. In particular, the organosilicon compound of the present invention represented by formula (1) above can be subjected to hydrolysis condensation to further improve the durability of the resulting film. When performing hydrolysis condensation, other organosilicon compounds may be added and co-hydrolysis condensation may be performed, as long as the objectives of the present invention are not impaired.

[0037] Other specific examples of organosilicon compounds include methyltrimethoxysilane, methyltrippropoxysilane, methyltriacetoxysilane, methyltributoxysilane, methyltripentoxysilane, methyltriamiloxysilane, methyltriphenoxysilane, methyltribenzyloxysilane, methyltriphenethyloxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, α-glycidoxyethyltrimethoxysilane, α-glycidoxyethyltriethoxysilane, and β-glycid Xyethyltrimethoxysilane, β-glycidoxyethyltriethoxysilane, α-glycidoxypropyltrimethoxysilane, α-glycidoxypropyltriethoxysilane, β-glycidoxypropyltrimethoxysilane, β-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltripropoxysilane, γ-glycidoxypropyltributoxysilane, γ-glycidoxypropyltriphenoxysilane, α-Glycidoxybutyltrimethoxysilane, α-Glycidoxybutyltriethoxysilane, β-Glycidoxybutyltriethoxysilane, γ-Glycidoxybutyltrimethoxysilane, γ-Glycidoxybutyltriethoxysilane, δ-Glycidoxybutyltrimethoxysilane, δ-Glycidoxybutyltriethoxysilane, (3,4-Epoxycyclohexyl)methyltrimethoxysilane, (3,4-Epoxycyclohexyl)methyltriethoxysilane, β-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane Lan, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltripropoxysilane, β-(3,4-epoxycyclohexyl)ethyltributoxysilane, β-(3,4-epoxycyclohexyl)ethyltriphenoxysilane, γ-(3,4-epoxycyclohexyl)propyltrimethoxysilane, γ-(3,4-epoxycyclohexyl)propyltriethoxysilane, δ-(3,4-epoxycyclohexyl)butyltrimethoxysilane, δ-(3,4-Epoxycyclohexyl)butyltriethoxysilane, glycidoxymethylmethyldimethoxysilane, glycidoxymethylmethyldiethoxysilane, α-glycidoxyethylmethyldimethoxysilane, α-glycidoxyethylmethyldiethoxysilane, β-glycidoxyethylmethyldimethoxysilane, β-glycidoxyethylethyldimethoxysilane, α-glycidoxypropylmethyldimethoxysilane, α-glycidoxypropylmethyldiethoxysilane, β-glycidoxypropylmethyldimethoxysilane, β-glycidoxypropylethyldimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-Glycidoxypropylmethyldiethoxysilane, γ-Glycidoxypropylmethyldipropoxysilane, γ-Glycidoxypropylmethyldibutoxysilane, γ-Glycidoxypropylmethyldiphenoxysilane, γ-Glycidoxypropylethyldimethoxysilane, γ-Glycidoxypropylethyldiethoxysilane, γ-Glycidoxypropylvinyldimethoxysilane, γ-Glycidoxypropylvinyldiethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, γ-chloropropyltrimethoxysilane, γ-chloropropyltriethoxysilane, γ-chloropropyltriacetoxysilane, 3,3,3-Trifluoropropyltrimethoxysilane, γ-Mercaptopropyltrimethoxysilane, γ-Mercaptopropyltriethoxysilane, β-Cyanoethyltriethoxysilane, Chloromethyltrimethoxysilane, Chloromethyltriethoxysilane, N-(β-Aminoethyl)γ-Aminopropyltrimethoxysilane, N-(β-Aminoethyl)γ-Aminopropylmethyldimethoxysilane, γ-Aminopropylmethyldimethoxysilane, N-(β-Aminoethyl)γ-Aminopropyltriethoxysilane, N-(β-Aminoethyl)γ-Aminopropylmethyldiethoxysilane, Dimethyldimethoxysilane, Phenylmethyldimethoxysilane, Dimethyldiethoxysilane, Phenylmethyldiethoxysilane, γ-Chloropropylmethyldimethoxysilane, γ-Chloropropyl Examples include diethyldiethoxysilane, dimethyldiacetoxysilane, γ-mercaptopropylmethyldimethoxysilane, γ-mercaptomethyldiethoxysilane, γ-ureidopropyltriethoxysilane, γ-ureidopropyltrimethoxysilane, γ-ureidopropyltripropoxysilane, (R)-N-1-phenylethyl-N'-triethoxysilylpropylurea, (R)-N-1-phenylethyl-N'-trimethoxysilylpropylurea, 3-isocyanatetopropyltriethoxysilane, trifluoropropyltrimethoxysilane, bromopropyltriethoxysilane, diethyldiethoxysilane, diethyldimethoxysilane, trimethylethoxysilane, trimethylmethoxysilane, etc., which can be used alone or in combination of two or more.

[0038] For hydrolysis condensation, catalysts such as acids (hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, oxalic acid, maleic acid, etc.), alkalis (ammonia, methylamine, ethylamine, etc.), or metal salts (hydrochloric acid, sulfuric acid, nitric acid, etc.) may be used. Solvents used in hydrolysis condensation reactions include alcoholic solvents such as methanol, ethanol, isopropanol, n-butanol, t-butanol, pentanol, ethylene glycol, propylene glycol, and 1,4-butanediol; etheric solvents such as diethyl ether, tetrahydrofuran, and dioxane; ketoneic solvents such as acetone and methyl ethyl ketone; aprotonic solvents such as dimethyl sulfoxide and N,N-dimethylformamide; water; and mixtures thereof. These solvents can be used individually or in combination of two or more. Among these, alcohol-based solvents and water are preferred.

[0039] The reaction temperature for hydrolysis condensation is preferably between 0°C and the boiling point of the solvent, more preferably between 0 and 120°C, and even more preferably between 5 and 80°C. The reaction time is preferably 10 minutes to 80 hours, more preferably 30 minutes to 50 hours, and even more preferably 30 minutes to 2 hours.

[0040] The coating composition of the present invention may further contain water, other organosilicon compounds as described above, alcohols such as methanol and ethanol, and other additives, to the extent that it does not impair the purpose of the present invention. Other additives include acids such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, oxalic acid, and maleic acid; alkalis such as ammonia, methylamine, and ethylamine; inorganic oxides; leveling agents; and surfactants.

[0041] In particular, since a highly durable hydrophilic film can be obtained, the coating composition of the present invention preferably contains an inorganic oxide. Preferred inorganic oxides include silica fine particles, alumina fine particles, titania fine particles, and magnesium fluoride fine particles, and these are more preferably used as colloidal solutions.

[0042] The leveling agent and surfactant mentioned above are included to improve the uniformity of the coating film, and can be appropriately selected from known products, but it is preferable to use commercially available products that are easily available.

[0043] The organosilicon compound represented by formula (1) contained in the coating composition of the present invention is silica sol (for example, aqueous silica sol: Na manufactured by Nissan Chemical Corporation). + The silanol group on a stable alkaline sol (ST-30L) or organosilica sol (such as IPA-ST manufactured by Nissan Chemical Corporation, preferably ST-30L) may be reacted with it.

[0044] In this case, specific examples and preferred examples of solvents used in the reaction include those similar to those exemplified in the hydrolysis condensation reaction described above. The reaction temperature is preferably between 0°C and the boiling point of the solvent, more preferably between 0 and 120°C, and even more preferably between 5 and 80°C. The reaction time is preferably 10 minutes to 80 hours, more preferably 30 minutes to 50 hours, and even more preferably 30 minutes to 2 hours.

[0045] In the present invention, the solution obtained by the method described above may be used as is as a coating composition, or, if necessary, the solution may be concentrated, diluted by adding a solvent, or the solvent in the solution may be replaced with another solvent before use. The content of the organosilicon compound represented by formula (1) and its hydrolysis condensate contained in the coating composition of the present invention is not particularly limited, but from the viewpoint of hydrophilicity, it is preferably 0.0001 to 50% by mass of the total composition, and more preferably 0.001 to 30% by mass.

[0046] The coating composition of the present invention can impart hydrophilicity to various substrates by being applied directly to at least one surface of them or via one or more other layers. Specific examples of materials that make up the base material include glass; synthetic resins {polymethyl methacrylate resin, polyethylene terephthalate resin, polybutylene terephthalate resin, polyethylene naphthalate resin, ABS resin, polycarbonate resin, polystyrene resin, epoxy resin, unsaturated polyester resin, melamine resin, diallyl phthalate resin, polyimide resin, urethane resin, nylon resin, polyethylene resin, polypropylene resin, polyvinyl chloride resin, fluororesins (polytetrafluoroethylene resin, polychlorotrifluoroethylene resin, polyvinylidene fluoride resin, perfluoroalkoxy fluororesins, tetrafluoroethylene-hexafluoropropylene copolymer resin, ethylene-tetrafluoroethylene copolymer resin, ethylene-chloro- Examples include: polyfluoroethylene copolymer resins, polybutadiene, polyisopropylene, SBR, nitrile rubber, EPM, EPDM, epichlorohydrin rubber, neoprene rubber, porsulfide, butyl rubber, etc.; metals (iron, aluminum, stainless steel, titanium, copper, brass, alloys thereof, etc.); cellulose, cellulose derivatives, cellulose analogs (chitin, chitosan, porphyran, etc.), natural fibers such as cotton, silk, and wool; regenerated fibers such as rayon; semi-synthetic fibers such as acetate; synthetic fibers such as vinylon, polyester, nylon, polyethylene, polypropylene, polyurethane, and polyaramid fibers; and composite fibers of these fibers (polyester / cotton, etc.). Their forms include substrates, sheets, films, and fibers. Furthermore, substrates whose surfaces have been treated with chemical conversion treatment, corona discharge treatment, plasma treatment, or acid or alkaline solutions, as well as decorative plywood coated with different types of paints on the substrate body and surface, can also be used. Other layers include those obtained by polyester resin coating, polyurethane resin coating, amino alkyd resin coating, lacquer coating, spray coating, and water-based wax coating.

[0047] The coating composition of the present invention can be applied to a substrate, and if necessary, heated and dried to form a coating film, thereby obtaining a hydrophilic coating film. Known coating methods can be used, such as bar coating, dip coating, spin coating, spray coating, float coating, brush coating, gravure coating, roll transfer, blade coating, air knife coating, slit coating, screen coating, inkjet, flexographic printing, etc. [Examples]

[0048] The present invention will be specifically described below with reference to examples and comparative examples, but the present invention is not limited to the following examples. Note that proton nuclear magnetic resonance ( 1 The 1H-NMR spectrum was measured in deuterium methanol (CD3OD) using a BURKER AVANCE III 400.

[0049] [1] Production of organosilicon compounds [Example 1-1] [ka]

[0050] In a nitrogen-purged 100 mL reaction vessel, 3.92 g of 3-mercaptopropyltrimethoxysilane, 3.48 g of 7-octen-1,2,3-triol (manufactured by Kuraray Co., Ltd., hereafter the same), 64.2 g of methanol, and 0.18 g of azobisisobutyronitrile (AIBN) were added, and the mixture was reacted at 60°C for 1 hour. After the reaction, 60 g of a 10% by mass methanol solution of organosilicon compound A-1 was obtained by filtration. 1 H-NMR (CD3OD): δ3.69~3.59ppm (s, 9H, -Si(OCH3)3), 3.83~3.28ppm (m, 4H, OCH-, OCH2-), 2. 62~2.45ppm(m, 4H, -SCH2-), 1.79~1.21ppm(m, 10H, -CH2-), 0.83~0.72ppm(m, 2H, -SiCH2-)

[0051] [Examples 1-2] [ka]

[0052] In a nitrogen-purged 100 mL reaction vessel, 5.32 g of 8-mercaptooctyltrimethoxysilane, 3.48 g of 7-octen-1,2,3-triol, 76.8 g of methanol, and 0.18 g of AIBN were added and reacted at 60°C for 1 hour. After the reaction, 70 g of a 10% by mass methanol solution of organosilicon compound B-1 was obtained by filtration. 1 H-NMR (CD3OD): δ3.70~3.59ppm (s, 9H, -Si(OCH3)3), 3.80~3.25ppm (m, 4H, OCH-, OCH2-), 2. 68~2.47ppm(m, 4H, -SCH2-), 1.81~1.20ppm(m, 20H, -CH2-), 0.82~0.71ppm(m, 2H, -SiCH2-)

[0053] [Examples 1-3] [ka]

[0054] In a 100 mL reaction vessel purged with nitrogen, 32.0 g of 7-octen-1,2,3-triol and 0.03 g of platinum catalyst CAT-PL-50T (manufactured by Shin-Etsu Chemical Co., Ltd.) were added. After raising the temperature to 80°C, 36.7 g of trimethoxysilane was added dropwise, and the reaction was carried out at 80°C for 2 hours. After the reaction, the excess trimethoxysilane was removed by distillation, and the mixture was filtered to obtain 50 g of organosilicon compound C-1. 1 H-NMR (CD3OD): δ3.68~3.61ppm(s, 9H, -Si(OCH3)3), 3.83~3.26ppm(m, 4H, OCH-, OCH2-), 1.75~1.30ppm(m, 8H, -CH2-), 0.82~0.73ppm(m, 2H, -SiCH2-)

[0055] [Comparative Example 1-1] [ka]

[0056] In a nitrogen-purged 100 mL reaction vessel, 4.9 g of 3-mercaptopropyltrimethoxysilane, 3.3 g of 3-allyloxy-1,2-propanediol (manufactured by Tokyo Chemical Industry Co., Ltd.), 74.0 g of methanol, and 0.24 g of AIBN were added, and the mixture was reacted at 60°C for 1 hour. After the reaction, 68 g of a 10% by mass methanol solution of organosilicon compound D-1 was obtained by filtration.

[0057] [Comparative Example 1-2] [ka]

[0058] In a 100 mL reaction vessel purged with nitrogen, 6.22 g of trimethoxy-3-(N,N-dimethylamino)propylsilane, 2.76 g of 1,3-propanesultone (manufactured by Tokyo Chemical Industry Co., Ltd.), and 35.9 g of methanol were added and the mixture was reacted at 25°C for 24 hours. After the reaction, 40 g of a 20% by mass methanol solution of organosilicon compound E-1 was obtained by filtration.

[0059] [Comparative Examples 1-3] [ka]

[0060] 5.07 g of trimethoxy-4-(N,N-dimethylamino)phenylsilane, 1.92 g of 1,3-propanesultone (manufactured by Tokyo Chemical Industry Co., Ltd.), and 5.31 g of methanol were added to a reactor and reacted at 25°C for 24 hours. After the reaction, 12 g of a 59% by mass methanol solution of organosilicon compound F-1 was obtained by filtration.

[0061] [2] Preparation of coating composition [Example 2-1] In a 200 mL nitrogen-purged mixing container, 50 g of a 10% methanol solution of organosilicon compound A-1 obtained in Example 1-1, 49.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition A-2.

[0062] [Example 2-2] In a 200 mL nitrogen-purged mixing container, 50 g of a 10% methanol solution of organosilicon compound B-1 obtained in Example 1-2, 49.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition B-2.

[0063] [Examples 2-3] In a 200 mL nitrogen-purged mixing container, 5 g of organosilicon compound C-1 obtained in Examples 1-3, 94.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition C-2.

[0064] [Comparative Example 2-1] In a 200 mL nitrogen-purged mixing container, 50 g of a 10% methanol solution of organosilicon compound D-1 obtained in Comparative Example 1-1, 49.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition D-2.

[0065] [Comparative Example 2-2] In a nitrogen-purged 200 mL mixing container, 25 g of a 20% by mass methanol solution of organosilicon compound E-1 obtained in Comparative Examples 1-2, 25 g of methanol, 49.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition E-2.

[0066] [Comparative Example 2-3] In a 200 mL nitrogen-purged mixing container, 8.5 g of a 59% by mass methanol solution of organosilicon compound F-1 obtained in Comparative Examples 1-3, 41.5 g of methanol, 49.95 g of deionized water, and 0.05 g of acetic acid were added and stirred at 25°C for 1 hour to obtain a colorless, transparent liquid coating composition F-2.

[0067] [3] Fabrication and evaluation of covered articles [Examples 3-1 to 3-3, Comparative Examples 3-1 to 3-3] In Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-3, 0.1 g of each coating composition A-2 to F-2 was dropped onto the surface of a glass plate measuring 5.0 cm in length, 15 cm in width, and 1.5 mm in thickness. After uniformly coating the entire surface using a nonwoven fabric, the plate was dried at 105°C for 10 minutes to produce a glass plate with a film made from each coating composition. The following tests were performed on each of the obtained coatings. The results are shown in Table 1.

[0068] (1) Anti-fogging properties The anti-fogging properties were evaluated by blowing exhaled air onto each of the above coatings, marking "×" if the surface of the coating fogged up and "○" if it did not fog up. Furthermore, the coatings were placed above a 40°C warm water bath, 3 cm above the water surface, for 60 seconds, and marked "◎" if the surface of the coating did not fog up. (2) Water stains In the anti-fogging evaluation described above, the coating film was placed in a 40°C hot water bath for 60 seconds for anti-fogging evaluation. After air-drying at 25°C for 10 minutes, the surface was illuminated with a 1,000 lm lamp, and visual inspection was performed to check for any water streaks on the coating film surface. The presence of water streaks was evaluated as "+", and the absence of water streaks was evaluated as "-". (3) Water resistance Each of the above coatings was immersed in water at 25°C for 24 hours and 240 hours, the surface water was absorbed with a paper wiper, and then it was air-dried at 25°C for 10 minutes to evaluate its anti-fogging properties. (4) Moisture resistance Each of the above coatings was left standing for 240 hours in a constant temperature and humidity chamber (KCL-2000W, Tokyo Rikakikai Co., Ltd.) set to 80°C and 95%RH. After that, they were air-dried at 25°C for 10 minutes, and the anti-fogging properties were evaluated. (5) Heat resistance Each of the above coatings was left standing for 240 hours in a constant temperature chamber (SPHH-201, ESPEC Corporation) set to 120°C. After that, it was left standing at 25°C for 10 minutes, and the anti-fogging properties were evaluated.

[0069] [Table 1]

[0070] As shown in Table 1, the glass plates treated with the coating compositions of Examples 3-1 to 3-3 exhibit excellent and long-lasting anti-fogging properties. On the other hand, Comparative Example 3-1 showed insufficient initial anti-fogging properties, and Comparative Example 3-2 showed water stains, as well as the loss of anti-fogging properties after the water resistance test and humidity resistance test, indicating poor durability. Furthermore, Comparative Example 3-3 showed insufficient anti-fogging properties after the 240-hour water resistance test and humidity resistance test.

Claims

1. An organosilicon compound represented by the following formula (1). 【Chemistry 1】 (In the formula, R 1 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms, R 2 Each of these independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, X represents a divalent saturated hydrocarbon group having 2 to 20 carbon atoms, which may contain a sulfur atom, and n is an integer from 1 to 3.

2. The organosilicon compound according to claim 1, represented by the following formula (2) or formula (3). 【Chemistry 2】 (In the formula, R 1 , R 2 (And n have the same meaning as above, m is an integer from 1 to 10, and k is an integer from 2 to 10.)

3. A coating composition comprising the organosilicon compound according to claim 1 or 2, a hydrolysis condensate of the organosilicon compound, or both.

4. A coated article having a base material and a coating made of the coating composition according to claim 3, formed directly on at least one surface of the base material or via one or more other layers.

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