JP6292937B2 - Film-forming coating agent and cured product thereof - Google Patents

Description

  The present invention relates to a film-forming coating agent used for a high-refractive index layer of an antireflection film and a cured product thereof, and in particular, mobile devices such as mobile phones, PDAs, and electronic papers using display methods such as liquid crystal and organic electroluminescence. The present invention relates to a film-forming coating agent suitably used for a high refractive index layer of an antireflection film in the display material and a cured product thereof.

Display materials for mobile devices such as mobile phones, PDAs, and electronic papers that use display methods such as liquid crystal and organic EL (electroluminescence) have a large effect on images due to reflection of light and objects, so anti-reflection performance is achieved. It is necessary to grant. As one method of preventing reflection, attaching an antireflection film to the surface of a display screen has been performed. This antireflection film has a hard coat layer having a high hardness and a high refractive index such as an acrylic resin on one side of a transparent substrate, and a low refractive index layer having a low refractive index such as a silicone resin or a fluorine resin. They are sequentially stacked. On the other hand, the antireflection film needs to be provided with antistatic performance in order to prevent dust adhesion due to static electricity. In order to impart antistatic performance, it was necessary to use a conductive material such as conductive inorganic fine particles for the hard coat layer.
As the hard coat layer, for example, Patent Document 1 discloses that polyfunctional acrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, or a mixture thereof as a main component, acrylamide as a curing retarder, metal An antistatic hard coat resin composition containing oxide fine particles as an essential component is disclosed. Since metal oxide fine particles are generally supplied as a dispersion of a low-boiling solvent (such as methanol), if the resin composition contains a low-boiling solvent, cracks and holes may occur during coating formation. There is sex. In Patent Document 1, acrylamide is used as a curing retarder in order to prevent cracks and pores, but this may cause a decrease in transparency due to yellowing of the antireflection film. Further, the hard coat layer is required to have a higher refractive index and antistatic performance.

JP 2011-208104 A

The present invention has been made in view of such circumstances, and is capable of forming a cured product having no cracks or holes, excellent transparency, a higher refractive index than conventional products, and excellent conductivity. An object of the present invention is to provide a coating agent for use (hereinafter sometimes abbreviated as a coating agent) and a cured product obtained by curing the coating agent.

The present invention has been made in order to solve such problems, and includes tin oxide, zirconia, a solvent having a boiling point of 100 ° C. or higher and 300 ° C. or lower, a dispersant, and one or more (meth) acryloyl in a molecule. The gist is a film-forming coating agent containing a compound having a group.
The coating agent for film formation of the present invention has a tin oxide content of 40 parts by mass or more and less than 100 parts by mass, and a zirconia content of more than 0 parts by mass and more than 60 parts by mass with respect to 100 parts by mass of the total amount of tin oxide and zirconia. The total content of tin oxide and zirconia is preferably 60 parts by mass or more and 90 parts by mass or less with respect to 100 parts by mass of the film-forming coating agent.
Moreover, this invention makes the hardened | cured material obtained by hardening | curing the said coating agent for film formation make a 2nd summary.

  According to the present invention, a resin composition for film formation, which is free from cracks or holes, has excellent transparency, can obtain a cured product having a higher refractive index than conventional products, and excellent conductivity, and the composition. The hardened | cured material obtained by hardening | curing can be provided.

  Hereinafter, preferred embodiments of the present invention will be described.

  The coating agent according to the present invention contains tin oxide, zirconia, a solvent having a boiling point of 100 ° C. or higher and 300 ° C. or lower, a dispersant, and a compound having one or more (meth) acryloyl groups in the molecule.

  The tin oxide in the present invention is a tin oxide compound, or a solvate or coordination compound thereof. Although not particularly limited, specifically, tin oxide, stannous oxide, stannic oxide, metastannic acid, antimony-doped tin oxide, indium-doped tin oxide, tin oxide-doped indium, aluminum-doped tin oxide, Examples include tungsten-doped tin oxide, titanium oxide-cerium oxide-tin oxide complex, titanium oxide-tin oxide complex, and solvates and coordination compounds thereof.

  The average particle diameter of the tin oxide is not particularly limited, but is preferably 1 nm or more and 1000 nm or less, and more preferably 3 nm or more and 300 nm or less. When the average particle diameter of tin oxide is within the above range, a cured product having excellent transparency can be obtained.

  The method for producing the tin oxide is not particularly limited. For example, a method of hydrolyzing or thermally hydrolyzing metal tin or a tin compound, a method of alkaline hydrolysis of an acidic solution containing tin ions, a solution containing tin ions as an ion exchange membrane, Any method such as a method of ion exchange with an ion exchange resin can be used.

  The zirconia of the present invention is a crystalline zirconium oxide particle, but may contain a crystal stabilizing material for crystal stabilization. Examples of the crystal stabilizing material include alkaline earth metal oxides such as MgO and CaO, and rare earth metal oxides such as lanthanide and Y2O3.

  As long as the crystal structure of the zirconia of the present invention is stable or metastable, it may be monoclinic, cubic, or tetragonal, or a mixed state thereof.

  The surface of the zirconia of the present invention may be coated with an organic compound capable of coordinating and / or bonding. Examples of the functional group capable of coordinating and / or bonding to the surface of zirconia particles include a carboxyl group, a hydroxy group, and an alkoxyl. Group, amine group, thiol group, amide group and the like.

  The content of tin oxide and zirconia of the present invention is such that the content of tin oxide is 40 parts by mass or more and less than 100 parts by mass, and the content of zirconia is more than 0 parts by mass with respect to 100 parts by mass of the total amount of tin oxide and zirconia. The amount is preferably 60 parts by mass or less. The content of tin oxide is more preferably 95 parts by mass or more and 45 parts by mass or less, and still more preferably 85 parts by mass or more and 50 parts by mass or less. The content of zirconia is more preferably 5 parts by mass or more and 55 parts by mass or less, and further preferably 15 parts by mass or more and 45 parts by mass or less. When the content of tin oxide and zirconia is included in the above range, the cured product has excellent transparency, refractive index, and antistatic performance.

  The coating agent of this invention contains the solvent whose boiling point is 100 to 300 degreeC.

The solvent of the present invention is not particularly limited as long as the boiling point is 100 ° C. or more and 300 ° C. or less. Specifically, cresol, xylene, ortho-dichlorobenzene, styrene, chlorobenzene, toluene, normal-butyl acetate, 2-ethoxyethyl acetate, normal-pentyl acetate, isopentyl acetate, isobutyl acetate, normal-propyl acetate, ethylene glycol mono-normal-butyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, 1.4 dioxane, propylene glycol monomethyl ether acetate, Propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, ethyl lactate, diethylene glycol dimethyl Ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, Ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether Polyethylene glycol monomethyl ether, methylcyclohexanol, methylcyclohexanone, cyclohexanol, cyclohexanone, 1.1.2.2-tetrachloroethane, tetrachloroethylene, isopentyl alcohol, 1-butanol, isobutyl alcohol, methyl-normal-butyl ketone, methyl isobutyl Ketones, and the like.
Of these, propylene glycol monomethyl ether, methyl isobutyl ketone, and propylene glycol monomethyl ether acetate are preferred because of the dispersion stability of the coating composition and the coating performance of the cured product.

  The coating agent of the present invention contains a dispersant.

  As the dispersant of the present invention, those commonly used in the technical field can be used. Although not particularly limited, specifically, 2-methacryloyloxyethyl succinic acid, 2-methacryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl acid phosphate, 2-acryloyloxyethyl succinic acid, 2-acryloyloxyethyl hexa Hydrophthalic acid, 2-acryloyloxyethylphthalic acid, 2-acryloyloxy-1-methylethylphthalic acid, 2-acryloyloxyethyl acid phosphate, ω-carboxy-polycaprolactone monoacrylate, acrylic acid dimer, propoxylated allyl Examples include methacrylates and acid-modified acrylate oligomers. Moreover, the dispersing agent described in JP 2012-007144 A, which is the prior art of the applicant of the present application, can also be suitably used. Among these, a dispersant or an acid-modified acrylate oligomer described in JP 2012-007144 A is preferable in terms of haze suppression of the cured product and dispersibility of the coating composition.

  The content of the dispersant in the present invention is not particularly limited, but is preferably 0.1 parts by mass or more and 50 parts by mass or less, and more preferably 1 part by mass or more and 30 parts by mass or less with respect to 100 parts by mass of the coating agent. If it is in the said range, it is excellent in the dispersion stability of coating composition, and it is possible to provide a high refractive index to hardened | cured material.

  The coating agent of the present invention contains a compound containing one or more (meth) acryloyl groups in the molecule.

  The compound containing one or more (meth) acryloyl groups in the molecule is not particularly limited, but is specifically as follows. That is, as a compound containing one (meth) acryloyl group in the molecule, 2-ethylhexyl (meth) acrylate, styrene, methyl methacrylate, acryloylmorpholine, tetrahydrofurfuryl (meth) acrylate, phenoxyethyl (meth) acrylate , Phenoxypropyl (meth) acrylate, benzyl (meth) acrylate, polyethoxyphenyl (meth) acrylate, polyethoxyphenyl (meth) acrylate, phenylbenzyl (meth) acrylate, orthophenylphenol (meth) acrylate, orthophenylphenoxyethoxy ( (Meth) acrylate, polyethoxyorthophenylphenoxyethoxy (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acryl Over DOO, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyl oxyethyl (meth) acrylate, phthalic acid mono hydroxyethyl (meth) acrylate.

  Examples of the compound containing a compound containing two (meth) acryloyl groups in the molecule include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di ( (Meth) acrylate, polytetramethylene di (meth) acrylate, 1,4-butanediol-di (meth) acrylate, 1,6-hexanediol-di (meth) acrylate, 1,9-nonanediol-di (meth) Acrylate, EO (ethylene oxide, the same applies below) modified bisphenol di (meth) acrylate, PO (propylene oxide, the same applies below) modified bisphenol di (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, neopenti Glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate.

  Examples of the compound containing a compound containing three or more (meth) acryloyl groups in the molecule include trimethylolpropane tri (meth) acrylate, EO-modified trimethylolpropane tri (meth) acrylate, PO-modified trimethylolpropane tri ( (Meth) acrylate, pentaerythritol tri (meth) acrylate, ((meth) acryloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, EO-modified pentaerythritol tetra (meth) acrylate, PO-modified pentaerythritol tetra (meth) acrylate , Ditrimethylolpropane tetra (meth) acrylate, EO-modified ditrimethylolpropane tetra (meth) acrylate, PO-modified ditrimethylolpropane tetra (meth) acrylate, Pentaerythritol hexa (meth) acrylate, EO modified dipentaerythritol hexa (meth) acrylate, PO modified dipentaerythritol hexa (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, etc. Is mentioned.

  Although the number of (meth) acryloyl groups should just be 1 or more in 1 molecule, 2-6 pieces are preferred and 3-6 pieces are more preferred. When the number of (meth) acryloyl groups is within the above range, a cured product having high hardness can be obtained.

  The coating agent of this invention adds the polymerization initiator by an active energy ray as needed. The polymerization initiator by active energy rays here includes both a photopolymerization initiator and a polymerization initiator by active energy rays such as ultraviolet rays.

  Examples of the photopolymerization initiator include aromatic ketones such as benzophenone, aromatic compounds such as anthracene and α-chloromethylnaphthalene, and sulfur compounds such as diphenyl sulfide and thiocarbamate.

Examples of the polymerization initiator by active energy rays such as ultraviolet rays include, for example, acetophenone, acetophenone benzyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, xanthone, fluorenone, Benzaldehyde, fluorene, anthraquinone, triphenylamine, carbazole, 3-methylacetophenone, 4-chlorobenzophenone, 4,4′-dimethoxybenzophenone, 4,4′-diaminobenzophenone, benzoinpropyl ether, benzoin ethyl ether, benzyldimethyl ketal, 1- (4-Isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, thioxa , Diethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis- (2 , 6-Dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, oligo (2-hydroxy-2
-Methyl-1- (4- (1-methylvinyl) phenyl) propanone) and the like.

  As a commercial item of the polymerization initiator by the active energy ray, for example, trade name: Irgacure 184,369,651,500,819,907,784,2959,1000,1300,1700,1800 manufactured by Ciba Specialty Chemicals , 1850, Darocur 1116, 1173, manufactured by BASF, Inc. Product name: Lucillin TPO, manufactured by UCB, Inc. Product name: Ubekrill P36, manufactured by Fratteri Lamberti, Inc. Product names: Ezacure KIP150, KIP100F, KT37, KT55, KTO46, TZT, KIP75LT, Nippon Kayaku Co., Ltd. trade name: Kayacure DETX and the like.

  If necessary, a radical polymerization initiator can be used in combination with the active energy ray initiator. Examples of the radical polymerization initiator include benzoyl peroxide, methylcyclohexanone peroxide, cumene hydroperoxide, diisopropylbenzene peroxide, di-t-butyl peroxide, t-butyl peroxybenzoate, diisopropyl peroxycarbonate, t- Organic peroxides such as butyl peroxyisopropyl monocarbonate and azo compounds such as 2,2′-azobisisobutyronitrile (AIBN) can be used.

  Although content of these polymerization initiators changes with kinds etc., they are 1 mass part or more and 8 mass parts or less with respect to 100 mass parts of coating agents of this invention. If the content is less than 1 part by mass, the sensitivity of the active energy ray becomes insufficient, and if it exceeds 8 parts by mass, the active energy ray does not reach the deep part of the coating film sufficiently and the curability of the deep part of the coating film tends to decrease. .

  Various additives usually contained in the coating agent and the like can be added to the coating agent of the present invention as necessary. Examples of the additive include a light stabilizer, an ultraviolet absorber, a catalyst, a leveling agent, an antifoaming agent, a polymerization accelerator, an antioxidant, a flame retardant, an infrared absorber, an antistatic agent, and a slip agent.

  Although the coating agent of this invention is apply | coated to a transparent base material layer, a base material is not specifically limited, From the well-known transparent plastic film of 10 micrometers-5 mm in thickness with a total light transmittance of 90% or more. It can be appropriately selected and used. Examples of such transparent base material layers include saturated polyester resins, polycarbonate resins, polyacrylate resins, polyolefin resins, polystyrene resins, polyvinyl chloride resins, polyvinyl acetate resins, and polyimide resins. What processed resin, such as resin, in the shape of a film or a sheet can be used. More specifically, polyester film, polyethylene film, polypropylene film, cellophane, diacetyl cellulose film, triacetyl cellulose film, acetyl cellulose butyrate film, polyvinyl chloride film, polyvinylidene chloride film, polyvinyl alcohol film, ethylene vinyl alcohol film , Polystyrene film, polycarbonate film, polymethylpentene film, polysulfone film, polyetheretherketone film, polyethersulfone film, polyetherimide film, polyimide film, fluorine resin film, nylon film, acrylic film, etc. .

  The coating method is not particularly limited, and is a known spray coating, roll coating, die coating, air knife coating, blade coating, spin coating, reverse coating, gravure coating, wire bar coating method or gravure printing, screen printing, offset printing. It can be formed by a printing method such as inkjet printing. The thickness of the hard coat layer is preferably 1 μm to 10 μm. The refractive index of the hard coat layer is preferably in the range of 1.50 to 1.80. After semi-curing the coating agent, a low refractive index resin layer is formed on this surface. Examples of the low refractive index resin include silicone resins and fluorine resins. After applying the low refractive index tree, using an ultraviolet irradiator, with an irradiation intensity of 500 mW / cm2 to 3000 mW / cm2, performing an ultraviolet treatment with a work amount of 50 to 400 mJ / cm2, and completely curing the coating agent, The low refractive index resin layer can be adhered to the hard coat layer.

  The present invention will be described more specifically based on examples, but the present invention is not limited to this. Those skilled in the art can make various changes, modifications, and alterations without departing from the scope of the present invention. The coating agents and cured products obtained in the following examples were evaluated as follows.

(Coating agent and cured product evaluation method)
[Dispersion stability]
The appearance of the adjusted and cured product was visually observed, and the stability was evaluated according to the following criteria.
○: Fluidity is good and transparent ×: Fluidity is lowered or cloudiness is generated

(Evaluation method of film)
[Surface resistance value]
Using a surface resistance measuring device (trade name: R8340A) manufactured by Advantest Co., Ltd., the surface resistance value of the obtained film (cured product) was measured and evaluated in an atmosphere of 20 ° C. and 65% RH.

[Haze]
Using a haze computer (model: HGM-2DP) manufactured by Suga Test Instruments Co., Ltd., the haze of the obtained coating (cured product) was measured and evaluated in accordance with JIS K7136.

[Refractive index]
Using a refractive index measuring device (product name: prism coupler) manufactured by Metricon Corporation, the refractive index at a wavelength of 589 nm of the obtained coating film (cured product) was measured and evaluated.

[Appearance of cured product]
The appearance of the film obtained by curing the coating agent was visually observed, and the transparency was evaluated according to the following criteria.
A: 12-point alphabet characters can be clearly distinguished.
○: A slight turbidity is generated in the cured film, but an alphabet character of 12 points can be discriminated.
X: The cured film has turbidity, and 12-point alphabet characters cannot be identified.

[Dispersant production example]
Into a toluene solvent, 640 g (1 mol) of ethylene oxide 10 mol adduct and 152 g (1.3 mol) of sodium monochloroacetate are uniformly added to a reactor, and branched C11-14 alkyl alcohol (product name: EXXAL13, manufactured by ExxonMobil). It stirred so that it might become. Thereafter, 52 g of sodium hydroxide was added at a reaction system temperature of 60 ° C. Subsequently, the temperature of the reaction system was raised to 80 ° C. and aged for 3 hours. After aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise with the reaction system at 50 ° C. to obtain a white suspension.

Subsequently, this white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure to obtain a dispersant (A). In this dispersant (A), the hydrophobic group R ₀ in the following general formula (1) is a branched C11-14 alkyl group, the oxyalkylene group AO is ethylene oxide, and the average number of added moles of oxyalkylene chain is n = 10. Yes, the linking group X has a structure of —CH ₂ —.

（実施例１）
無機化合物微粒子として、日産化学工業株式会社製の酸化スズゾル（商品名：セルナックスCX-S501M，50重量％、のメタノール（ゾル用溶媒）を含有する分散体）および市販のジルコニア分散体（堺化学社製の商品名ＳＺＲ−Ｍ、一次粒子径３ｎｍ、３０重量％のジルコニアを含有するメタノール分散体）を用い、重合性化合物として、ジペンタエリスリトールヘキサアクリレート（日本化薬株式会社製の商品名：KAYARAD DPHA）を用い、分散剤としてω−カルボキシ−ポリカプロラクトンモノアクリレート（東亞合成株式会社製の商品名：アロニックスＭ−５３００）を用い、溶媒として、メチルイソブチルケトン（MIBK）プロピレングリコールモノメチルエーテル（PGME）（株式会社クラレ製の商品名アーコソルブPM）を用いた。

Example 1
As inorganic compound fine particles, a tin oxide sol (trade name: Celnax CX-S501M, a dispersion containing 50% by weight of methanol (solvent for the sol)) manufactured by Nissan Chemical Industries, Ltd. and a commercially available zirconia dispersion (Sakai Chemical) Dipentaerythritol hexaacrylate (trade name, manufactured by Nippon Kayaku Co., Ltd.) is used as a polymerizable compound using a product name SZR-M manufactured by the company, a methanol dispersion containing zirconia having a primary particle size of 3 nm and a primary particle size of 3 nm. KAYARAD DPHA), ω-carboxy-polycaprolactone monoacrylate (trade name: Aronix M-5300, manufactured by Toagosei Co., Ltd.) as the dispersant, and methyl isobutyl ketone (MIBK) propylene glycol monomethyl ether (PGME) as the solvent ) (Trade name Arcosolve PM manufactured by Kuraray Co., Ltd.) was used.

  140 parts by mass of the tin oxide sol, 100 parts by mass of the zirconium oxide sol, 33 parts by mass of the dipentaerythritol hexaacrylate, 10 parts by mass of the ω-carboxy-polycaprolactone monoacrylate, and the MIBK 200 parts by mass and 100 parts by mass of the above PGME were blended and mixed, and the solvent for sol (methanol) was removed under reduced pressure using a rotary evaporator to prepare the coating agent for film formation of Example 1.

After adding 3 parts by mass of a photopolymerization initiator (trade name (registered trademark): Irgacure 184 manufactured by BASF Japan Ltd.) to 400 parts by mass of the obtained coating agent, a polyethylene terephthalate (PET) film It apply | coated using the 22-micrometer bar-coater on the surface of (Toray Industries, Inc. brand name: Lumirror # 100 T60). Thereafter, the solvent was volatilized under the conditions of 100 ° C. × 1 minute, and the coating agent was cured by irradiating with a light of 300 mJ / cm ² (oxygen concentration 0.3% or less) with a high-pressure mercury lamp. Thereby, the coating film (film thickness 4 μm) of Example 1 was formed in the present invention. The obtained film was evaluated.

(Example 2)
A coating agent and a film were prepared in the same manner as in Example 1 except that the tin oxide sol was 100 parts by mass and the zirconium oxide sol was 167 parts by mass.

(Example 3)
A coating agent and a film were produced in the same manner as in Example 1 except that dipentaerythritol hexaacrylate was changed to 7.6 parts by mass.

Example 4
A coating agent and a coating film were prepared in the same manner as in Example 1 except that 56 parts by mass of dipentaerythritol hexaacrylate was used.

(Example 5)
A coating agent and a film were produced in the same manner as in Example 1 except that ω-carboxy-polycaprolactone monoacrylate was changed to the dispersant (A) produced in the above-mentioned dispersant production example.

(Comparative Example 1)
A coating agent and a film were prepared in the same manner as in Example 1 except that the zirconium oxide sol was not used as the inorganic compound fine particles, and only the tin oxide sol was changed to 200 parts by mass.

(Comparative Example 2)
A coating agent and a film were prepared in the same manner as in Example 1 except that tin oxide sol was not used as the inorganic compound fine particles, and only zirconium oxide sol was changed to 333 parts by mass.

(Comparative Example 3)
A coating agent and a film were prepared in the same manner as in Example 1 except that 43 parts by mass of dipentaerythritol hexaacrylate and ω-carboxy-polycaprolactone monoacrylate were not used.

(Comparative Example 4)
A coating agent and a film were prepared in the same manner as in Example 1 except that the solvent was not used and the sol solvent was not removed under reduced pressure.

  In Comparative Example 3, the coating stability was not evaluated because the dispersion stability was poor. Moreover, in the comparative example 4, since the external appearance of the coating film was unsatisfactory, evaluation of haze, refractive index, and surface resistance value was not performed.

以上の結果から、本発明に係るコーティング組成物及びその硬化物（実施例１〜５）は、いずれも、優れた外観、光学特性、及び帯電防止性を有することが分かる。

From the above results, it can be seen that the coating composition according to the present invention and the cured product thereof (Examples 1 to 5) all have excellent appearance, optical properties, and antistatic properties.

  However, when only the tin oxide sol was used as the inorganic compound fine particles (Comparative Example 1) and when only the zirconium oxide was used (Comparative Example 2), the surface resistance value was high. (Comparative Example 1) When the ω-carboxy-polycaprolactone monoacrylate, which is a dispersant, was not used, the dispersion stability of the coating composition was poor (Comparative Example 3). In addition, when the methanol of the low boiling point solvent contained in the inorganic compound fine particle sol was not distilled off and methyl isobutyl ketone and propylene glycol monomethyl ether as the high boiling point solvent were not added, the appearance of the cured product was poor. .

  It should be noted that the present invention is not limited to the description of the above-described embodiment, and various modifications are possible within the scope shown in the scope of the claims, and are disclosed in different embodiments and a plurality of modifications. Embodiments obtained by appropriately combining the technical means are also included in the technical scope of the present invention.

  The coating composition and cured product of the present invention are suitable for fields requiring an antireflection function, such as an antireflection film for flat panel displays such as LCD and PDP, plastic optical components, touch panels, mobile phones, and film liquid crystal elements.

Claims (3)

Containing tin oxide, zirconia, a solvent having a boiling point of 100 ° C. or higher and 300 ° C. or lower, a dispersant, and a compound having one or more (meth) acryloyl groups in the molecule ;
The dispersant is 2-methacryloyloxyethyl succinic acid, 2-methacryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl acid phosphate, 2-acryloyloxyethyl succinic acid, 2-acryloyloxyethyl hexahydrophthalic acid, 2-acryloyloxyethylphthalic acid, 2-acryloyloxy-1-methylethylphthalic acid, 2-acryloyloxyethyl acid phosphate, ω-carboxy-polycaprolactone monoacrylate, acrylic acid dimer, propoxylated allyl methacrylate, acid modification A film-forming coating agent comprising at least one component selected from the group consisting of an acrylate oligomer and a compound represented by the following formula (1) .

However, in Formula (1), R ₀ is an alkyl group having 11 to 14 carbon atoms, AO is an oxyethylene group, the average added mole number n is 10, and the linking group X is CH ₂ .   The total content of tin oxide and zirconia is 100 parts by mass, the content of tin oxide is 40 parts by mass or more and less than 100 parts by mass, the content of zirconia is more than 0 parts by mass and 60 parts by mass or less, and tin oxide and zirconia 2. The film-forming coating agent according to claim 1, wherein the total content is 60 parts by mass or more and 90 parts by mass or less with respect to 100 parts by mass of the film-forming coating agent.   A cured product obtained by curing the film-forming coating agent according to claim 1.