JP2007169407A - Antistatic coating composition and film obtained by curing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an antistatic coating composition having high compatibility with a hard coat base and an antistatic film which excels in antistatic properties, transparency, and mar resistance, is hard, and has excellent adhesion to a plastic base material. <P>SOLUTION: The antistatic coating composition comprises 100 pts.wt. hard coat base containing at least one of a monomer containing a plurality of ethylene groups and a prepolymer containing a plurality of ethylene groups and 0.5-50 pts.wt. polymer compound having a repeating unit of a polar structure of one of an ion pair and betaine and a fluorocarbon group. The antistatic film is obtained by curing this composition. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a composition that imparts antistatic properties by applying a coating to a plastic substrate, and a film obtained by curing the composition.

  Plastic base materials are widely used as raw materials for parts of home appliances, automobile parts, optical members, organic glass sheets, and the like. Plastic substrates are easily scratched and easily charged. Therefore, as disclosed in Patent Documents 1 and 2, it is coated with a coating layer containing metal fine particles of an antistatic agent or a conductive filler.

  However, if the coating layer contains a large amount of a cationic, anionic or nonionic surfactant, an alkali metal salt, an alkaline earth metal salt, an ammonium salt, etc. as an antistatic agent, it will cause bleeding. In other words, the antistatic property under high humidity is lowered, and the scratch resistance is lowered. Further, when the coating layer contains a conductive filler, the antistatic property is excellent, but the transparency is impaired.

Japanese Patent Laid-Open No. 10-244618 JP 2000-281736 A

  The present invention is an antistatic coating composition having high compatibility with a hard coat base, and an antistatic coating composition that is excellent in antistatic properties, transparency, scratch resistance, is hard, and has excellent adhesion to a plastic substrate. The object is to provide a coating.

  The antistatic coating composition according to claim 1, which has been made to achieve the above object, comprises a hard material containing at least one of an ethylene group-containing monomer and an ethylene group-containing prepolymer. 100 parts by weight of a coat base, 0.5 to 50 parts by weight of a polymer compound containing a repeating unit having a polar structure of any one of an ion pair and betaine and a fluorocarbon group are included.

  The antistatic coating composition according to claim 2 is the antistatic coating composition according to claim 1, wherein the polar structure has a quaternary ammonium halide group, an ammonium phosphate ester group, an ammonium sulfate ester in the polymer compound. At least one selected from a group, a halogenated quaternary phosphonium group, a basic sulfonic acid group and a basic carboxylic acid group; a sulfonic acid ion group or a carboxylic acid ion group and a quaternary ammonium group or a quaternary phosphonium group It is the said betaine which has these.

  An antistatic coating composition according to claim 3 is the antistatic coating composition according to claim 2, wherein the polymer compound contains any of a halogenated alkyl group, a halogenated aryl group, and a halogenated aralkyl group. A tertiary amine or a tertiary phosphine is reacted with a copolymer of the unsaturated macromonomer having a repeating unit and the unsaturated monomer containing the fluorocarbon group or the unsaturated macromonomer containing the fluorocarbon group. It is characterized by forming the ion pair of a halogenated quaternary ammonium group or the halogenated quaternary phosphonium group.

  The antistatic coating composition according to claim 4 is the antistatic coating composition according to claim 3, and has a repeating unit containing any one of the halogenated alkyl group, the halogenated aryl group, and the halogenated aralkyl group. The unsaturated macromonomer is a macromonomer derived from chloromethylstyrene.

  The antistatic coating composition according to claim 5 is the composition according to claim 3, wherein the copolymer is a (meth) acrylic acid monoester monomer, an unsaturated carboxylic acid monomer, a (meth) acrylamide monomer, It is copolymerized with at least one other unsaturated monomer selected from styrene monomers, vinyl ether monomers, and vinyl ester monomers.

  The antistatic coating composition according to claim 6 is the antistatic coating composition according to claim 1 and is characterized by containing a photopolymerization initiator or a thermal polymerization initiator.

  The antistatic film according to claim 7 is obtained by curing the antistatic coating composition according to any one of claims 1 to 6.

  The method for forming an antistatic coating according to claim 8 is obtained by applying the antistatic coating composition according to any one of claims 1 to 6 to a plastic substrate and irradiating the active energy ray thereon. The ethylene group-containing monomer and / or the ethylene group-containing prepolymer is crosslinked and cured.

  The antistatic coating composition of the present invention has good compatibility between a polymer compound exhibiting antistatic properties and a hard coat base containing a plurality of ethylene group-containing monomers and a plurality of ethylene group-containing prepolymers. In addition, since this polymer compound has high surface modification properties, a coating composition that exhibits excellent antistatic properties can be prepared by simply adding a small amount thereof. This composition is easy to apply to plastic substrates. When this composition is cured, a film having a low surface resistance, excellent antistatic properties, transparency, scratch resistance, durability, and high pencil hardness can be easily obtained.

  Examples of the present invention will be described in detail below, but the scope of the present invention is not limited to these examples.

  A preferred example of an antistatic coating composition is prepared as follows.

  After obtaining a block polymer of halogenated alkylstyrene having 2-mercaptoethanol introduced at the terminal, an alkyl halide having an unsaturated group introduced at the terminal by adding 2- (meth) acryloyloxyethyl isocyanate to the hydroxyl group A group-containing unsaturated macromonomer is synthesized.

  For this unsaturated macromonomer containing an alkyl halide group into which an unsaturated group is introduced at the end, a chain transfer agent having a carboxylic acid in the molecule such as 2-mercaptopropionic acid is used instead of 2-mercaptoethanol. Thus, after obtaining a block polymer of halogenated alkylstyrene, it can also be obtained by adding a vinyl compound having a glycidyl group in its molecule, such as glycidyl methacrylate, to the carboxylic acid group.

  The halogenated alkyl group-containing unsaturated macromonomer, the fluorocarbon group-containing unsaturated monomer, and the (meth) acrylic acid monoester monomer are copolymerized at a weight ratio of 5 to 90: 5 to 90: 0 to 80. A polymer compound in which a tertiary amine or tertiary phosphine is reacted with a halogenated alkyl group in the copolymer to form a repeating unit of a halogenated quaternary ammonium group or a halogenated quaternary phosphonium group is synthesized. .

  In the synthesis of the halogenated alkyl group-containing unsaturated macromonomer used when synthesizing the polymer compound in which the halogenated quaternary ammonium group or the halogenated quaternary phosphonium group repeating unit is formed, Instead, for example, a vinyl compound having a tertiary amine in the molecule such as dimethylaminoethyl methacrylate is used, and carbon and halogen in the molecule such as benzyl chloride are used instead of the tertiary amine or tertiary phosphine used later. It can also be obtained by using an alkyl halide, an aryl halide, or an aralkyl halide having a bond. In addition, by using phosphate esters or sulfate esters such as trimethyl phosphate, dimethyl sulfate or methyl p-toluenesulfonate instead of benzyl chloride, halogen-free ion pairs can be used as polar structural repeating units. A polymer compound having a fluorocarbon group can be obtained.

  When this polymer compound, an ethylene group-containing monomer and / or an ethylene group-containing prepolymer as a hard coat base, and a polymerization initiator are kneaded, an antistatic coating composition is obtained.

  In the antistatic coating composition, with respect to 100 parts by weight of the hard coat base containing the ethylene group-containing monomer and / or the ethylene group-containing prepolymer, the polymer compound is 0.5 to 10 parts by weight, and the polymerization initiator is When it is contained in an amount of 1 to 10 parts by weight, it is more preferable because it exhibits extremely excellent antistatic properties and hardness.

  The fluorocarbon group in the polymer compound is easily compatible with oxygen in the air. Therefore, the film obtained by curing this composition is easy to orient the polymer containing fluorocarbon groups on the surface. As a result, the surface resistance value of the coating can be kept low even if the polymer compound in the composition is small. This becomes more remarkable when a fluorocarbon group-containing unsaturated macromonomer in which an unsaturated group is introduced at the terminal by block polymerization of the fluorocarbon group-containing unsaturated monomer is used.

  Specifically, the raw material of the antistatic coating composition is as follows.

  Examples of the halogenated alkyl, aryl halide, or halogenated aralkyl-containing unsaturated compound include chloromethylstyrene. The tertiary amine and tertiary phosphine are not particularly limited, but amines having a methyl group or an ethyl group are particularly preferable.

  The fluorocarbon group-containing unsaturated monomer may be a fluorocarbon group-containing (meth) acrylate, such as 2,2,2-trifluoro (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H octafluoropentyl (meth) acrylate, perfluorooctylethyl (meth) acrylate, perfluoroisopropylethyl (meth) acrylate, p-perfluorooctyloxybenzyl (meth) acrylate and the like can be mentioned. Among them, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trifluoroethyl acrylate, perfluorooctylethyl methacrylate, perfluorooctylethyl acrylate and the like having a perfluoroalkyl group at the terminal are preferable. In particular, it is not limited to these. These fluorocarbon group-containing unsaturated monomers can be used alone or in combination of two or more.

  (Meth) acrylic acid monoester monomer which is one of the other unsaturated monomers constituting the copolymer is methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, Cyclohexyl (meth) acrylate, cyclopentyl (meth) acrylate, benzyl (meth) acrylate, ethylhexyl (meth) acrylate, hydroxyethyl (meth) acrylate, glycidyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate , (Meth) acrylates such as isobornyl (meth) acrylate, monofunctional polyoxyalkylene (meth) acrylate, monofunctional polyester (meth) acrylate, monofunctional polycaprolactone (meth) acrylate Relate including but not limited to this. In addition, copolymerizable unsaturated monomers other than (meth) acrylic acid monoester monomers include unsaturated carboxylic acid monomers such as (meth) acrylic acid, crotonic acid, maleic acid, and itaconic acid; t-butyl-n -(Meth) acrylic acid amide monomers such as butoxymethylacrylamide; styrene monomers such as styrene and α-methylstyrene; vinyl ether monomers such as lauryl vinyl ether; vinyl ester monomers such as vinyl butyrate However, it is not particularly limited to this. These unsaturated monomers can be used alone or in combination of two or more.

  The polymer compound is an ion pair-containing unsaturated monomer exemplified by trialkylammoniomethylstyrene chloride or trialkylphosphoniomethylstyrene chloride, or (3-propyl sulfonic acid-1) in the same weight ratio as described above. Polarities derived from betaine structure-containing unsaturated monomers exemplified by 2-vinylpyridinium betaine and N, N-dimethyl-N- (2-methacryloyloxyethyl) -N- (3-sulfopropyl) ammonium betaine An unsaturated macromonomer having a repeating unit of structure, a fluorocarbon group-containing unsaturated monomer or a fluorocarbon group-containing unsaturated macromonomer, and a (meth) acrylic acid monoester may be copolymerized. The macromonomer is prepared in the same manner as described above.

  Ethylene glycol di (meth) acrylate, hexylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerin di (meth) acrylate, glycerin Examples include monomethacrylate monoacrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.

  Ethylene group-containing prepolymer is obtained by condensing trimethylolpropane ethylene oxide adduct tri (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polyhydric alcohol and polybasic acid. Compound (meth) acrylate, hexamethylene diisocyanate, isophorone diisocyanate, toluene diisocyanate and polyisocyanates such as burettes and uretrates, glycerol monomethacrylate monoacrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta Examples thereof include a reaction product with (meth) acrylate having a hydroxyl group in the molecule such as (meth) acrylate.

  The polymerization initiator is a photopolymerization initiator, such as 1-hydroxycyclohexyl phenyl ketone, 1-phenyl-2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-2-phenylacetophenone, benzophenone, 2-methyl [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy- 2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 4- (2-acryloyloxyethoxy) phenyl- (2-hydroxy-2-propyl) Ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide; thermal polymerization initiator For example, benzoyl peroxide, lauroyl peroxide, stearoyl peroxide, 1,1-bis (t-butylperoxy) 2-methylcyclohexane, 2,2-bis (4,4-di-butylperoxycyclohexyl) propane, , 1-bis (t-butylperoxy) cyclododecane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxymaleic acid, t-butylperoxy-3,5,5-trimethylhexanoate, t- Butyl peroxylaurate, 2,5-dimethyl-2,5-di (m-toluoyl peroxy) hexane, t-butyl peroxyisopropyl monocarbonate, t-butyl peroxy 2-ethylhexyl monocarbonate, t-hexyl Peroxybenzoate, 2,5-di- Til-2,5-di (benzoylperoxy) hexane, t-butylperoxyacetate, 2,2-bis (t-butylperoxy) butane, t-butylperoxybenzoate, n-butyl-4,4- Bis (t-butylperoxy) valerate, di-t-butylperoxyisophthalate, α, α′-bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, t-butylcumyl peroxide, di- Organic peroxide initiators such as t-butyl peroxide, t-butyltrimethylsilyl peroxide, t-butyl hydroperoxide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1-[(1 -Cyano-1-methylethyl) azo] formamide, 1,1'-azobis (cyclohexane- -Carbonitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2, 2'-azobis (2-methylpropionamidine) dihydrochloride, 2,2'-azobis (2-methyl-N-phenylpropionamidine) dihydrochloride, 2,2'-azobis [N- (4-chlorophenyl) -2 -Methylpropionamidine] dihydride chloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane], 2,2'-azobis [2-methyl-N- [1,1-bis ( Hydroxymethyl) ethyl] propionamide], 2,2′-azobis (2,4,4-trimethylpentane), 2,2′-azobis (2-methylpropane) Dimethyl-2,2-azobis (2-methylpropionate), 4,4′-azobis (4-cyanopentanoic acid), 2,2′-azobis [2- (hydroxymethyl) propionitrile], etc. Examples thereof include azo initiators.

  The antistatic coating composition may contain additives such as silicon-based resins, silica particles, metal particles, metal oxide particles, organic salts, inorganic salts, and diluents depending on the performance required for the film. Good.

  Diluents include monoalkyl ethers of alkylene glycols such as propylene glycol monomethyl ether; alkyl alcohols such as isopropyl alcohol; alkyl carboxylic acid esters of alkylene glycol monoalkyl alcohols such as butyl glycol acetate; ketones such as methyl ethyl ketone; Examples include acid esters such as ethyl acetate; aliphatic hydrocarbons such as hexane; alicyclic hydrocarbons such as cyclohexane; aromatic hydrocarbons such as toluene; and halogenated solvents such as methyl chloride.

  The antistatic coating composition is applied to a molded substrate made of a plastic substrate such as an acrylic resin, a urethane resin, a polycarbonate resin, an epoxy resin, or a polyethylene terephthalate resin. When it is irradiated with an active energy ray such as ultraviolet ray, radiation, infrared ray, X-ray, electron beam, visible light or heat, it is cured and an antistatic coating is formed.

  Examples of the antistatic coating composition of the present invention and an antistatic coating obtained by curing the composition are shown below.

  First, a macromonomer as a raw material was synthesized.

(Synthesis Example 1) Synthesis of Macromonomer of Chloromethylstyrene 100 parts by weight of chloromethylstyrene (CMS), 5 parts by weight of 2-mercaptoethanol, 100 parts by weight of methyl ethyl ketone, and dimethyl 2,2′-azobis in a four-necked flask 5 parts by weight of (2-methylpropionate) was added and reacted at 75-80 ° C. for 13 hours under a nitrogen atmosphere. Thereafter, 9.93 parts by weight of 2-methacryloyloxyethyl isocyanate, 0.04 parts by weight of methoquinone and 0.01 parts by weight of dibutyltin dilaurate were added and reacted at 75-80 ° C. for 6 hours. In the infrared absorption spectrum, it was confirmed that the peak of the isocyanate group at 2250 cm ⁻¹ disappeared, and a chloromethylstyrene macromonomer (CMS macromonomer) was obtained.

(Synthesis example 2) Synthesis | combination of the macromonomer of trifluoroethyl methacrylate Light ester M-3F (Kyoeisha Chemical Co., Ltd. brand name) which is 2,2,2- trifluoroethyl methacrylate in a four necked flask; M- (3F monomer) 100 parts by weight, 2-mercaptoethanol 5 parts by weight, methyl ethyl ketone 100 parts by weight, and dimethyl 2,2′-azobis (2-methylpropionate) 5 parts by weight. The reaction was carried out at 0 ° C. for 7 hours. Thereafter, 9.93 parts by weight of 2-methacryloyloxyethyl isocyanate, 0.04 parts by weight of methoquinone and 0.01 parts by weight of dibutyltin dilaurate were added and reacted at 75-80 ° C. for 6 hours. In the infrared absorption spectrum, it was confirmed that the peak of the isocyanate group at 2250 cm ⁻¹ disappeared, and a macromonomer (M-3F macromonomer) of trifluoroethyl methacrylate was obtained.

  Next, a polymer compound was synthesized.

(Synthesis Example 3) Synthesis of Polymer Compound A In a four-necked flask, 100 parts by weight of the chloromethylstyrene macromonomer obtained in Synthesis Example 1 in terms of resin content and 84 parts by weight of methyl ethyl ketone containing it. The mixture, 20 parts by weight of light ester M-3F, 80 parts by weight of methyl methacrylate and 10 parts by weight of dimethyl 2,2′-azobis (2-methylpropionate) were added, and the mixture was heated at 75-80 ° C. under nitrogen atmosphere. Reacted for hours. To the reaction mixture, 55.3 parts by weight of triethylamine and 55.6 parts by weight of ethanol were added and reacted at 60 ° C. for 6 hours. The amine value was measured by a titration method, and it was confirmed that all the tertiary amines were quaternized, and a polymer compound A (CMSmacro / MMA / M-3F; 50/40/10) was obtained.

(Synthesis Example 4) Synthesis of Polymer Compound B 20 parts by weight in terms of the resin content of the trifluoroethyl methacrylate macromonomer obtained in Synthesis Example 2 instead of the light ester M-3F used in Synthesis Example 3 Polymer compound B (CMSmacro / MMA / M-3Fmacro; 50/40/10) was obtained in the same manner as in Synthesis Example 3 except that a mixture of benzene and 17 parts by weight of methyl ethyl ketone containing it was used.

(Synthesis Example 5) Synthesis of Polymer Compound C Obtained in Synthesis Example 2 instead of 80 parts by weight of methyl methacrylate used in Synthesis Example 3 and 20 parts by weight of light ester M-3F Polymer compound C (CMSmacro / MMA) was prepared in the same manner as in Synthesis Example 3 except that a mixture of 80 parts by weight in terms of the resin content of the macromonomer of trifluoroethyl methacrylate and 67 parts by weight of methyl ethyl ketone containing the same was used. / M-3Fmacro; 50/10/40).

(Synthesis Example 6) Synthesis of Polymer Compound a In a four-necked flask, 100 parts by weight of the chloromethylstyrene macromonomer obtained in Synthesis Example 1 in terms of resin and 84 parts by weight of methyl ethyl ketone containing the same. The mixture, 100 parts by weight of methyl methacrylate, and 10 parts by weight of dimethyl 2,2′-azobis (2-methylpropionate) were added, and the mixture was reacted at 75-80 ° C. for 9 hours in a nitrogen atmosphere. To the reaction mixture, 55.3 parts by weight of triethylamine and 55.6 parts by weight of ethanol were added and reacted at 60 ° C. for 6 hours. The amine value was measured by a titration method, and it was confirmed that all the tertiary amines were quaternized, and a polymer compound a (CMSmacro / MMA /; 50/50) was obtained.

  Examples 1 to 9 show examples of antistatic coating compositions to which the present invention is applied and trial manufactures of antistatic coatings obtained by curing the compositions. Comparative Examples 1 and 2 show trial examples of coating compositions to which the present invention is not applied and a film obtained by curing the coating composition.

(Examples 1-9 and Comparative Examples 1-2)
Polymer compounds obtained in Synthesis Examples 3 to 5, dipentaerythritol hexaacrylate (trade name: Light Acrylate DPE-6A, manufactured by Kyoeisha Chemical Co., Ltd.) and pentaerythritol triacrylate isophorone diisocyanate urethane prepolymer (as a hard coat base) Kyoeisha Chemical Co., Ltd. product name: urethane acrylate UA-306I), solvent as methyl ethyl ketone and ethanol, and photopolymerization initiator as 1-hydroxycyclohexyl phenyl ketone (product name: Irgacure 184, manufactured by Ciba Specialty Chemicals) ) As shown in Table 2 and kneaded uniformly to prepare a composition. The obtained composition was applied to a transparent polymethylmethacrylate substrate with a thickness of about 10 μm with a bar coater (No. 14) to form a coating film, and dried at 90 ° C. for 5 minutes. It was placed on a conveyor with a speed of 5 m / min and irradiated with ultraviolet light with an 80 W / cm high-pressure mercury lamp 10 cm away from it to cure the coating film to obtain a test piece having a film thickness of 3 μm.

  The physical properties of the obtained test pieces were evaluated by performing appearance observation, haze measurement test, surface resistance value measurement test, pencil hardness measurement test, scratch resistance evaluation test, and adhesion evaluation test as follows.

(Appearance observation)
The film of the test piece was visually observed. The evaluation was made in two steps, with ○ being transparent and smooth, and × being non-smooth.

(Haze measurement test)
The haze of the coating film of the test piece was measured using a haze meter Ultra Scan XE (manufactured by HUNTER ASSOCIATES LABORATORY: trade name). Evaluation was made in two stages, with a haze of less than 0.5 being ◯ and a haze of 0.5 or more being x.

(Surface resistance measurement test)
About the surface resistance value of the film of the test piece under relative humidity 60% at 20 degreeC, it measured using resistivity meter DSM-8103 and SME-8311 (all are the Toa DKK company brand name).

(Pencil hardness measurement test)
According to JIS K 5400, the pencil hardness of the coating film of the test piece was measured using a pencil scratch tester. A load of 1 kg was applied from above while maintaining pencils of various hardnesses at an angle of 45 °, the coating on the test piece was scratched 1 cm, and the presence or absence of scratches was visually observed. Repeated 5 times, the highest hardness among the pencil hardnesses that were not damaged in 5 times was defined as the hardness of the coating.

(Abrasion resistance evaluation test)
The coating of the test piece was rubbed 10 times with a No. 0000 steel wool applied with a load of 200 g / cm ² , and the presence or absence of scratches was visually observed. Evaluation was made on a four-point scale, with ◎ having almost no scratches, ◯ with slightly scratches, △ with countless scratches, and X with scratches as whitening occurred.

(Adhesion evaluation test)
On the coating surface of the test piece, 11 cuts of 1 mm in length and width were cut with a cutter knife to form 100 grid-like squares. Cellophane tape was affixed from above, and the number of cells remaining without being peeled off was counted.

  These results are summarized in Table 2.

As is clear from Table 2, the coating films of Examples 1 to 9 have a surface resistance value as low as about 10 ⁸ to 10 ¹⁰ Ω / cm ² , excellent antistatic properties, good transparency, scratch resistance, and adhesion. And showed high hardness. In particular, as the blending amount of the polymer compound was increased as in Examples 3 to 5 and 6 to 9, the surface resistance value was decreased, and further excellent antistatic properties were exhibited. On the other hand, the coating films of Comparative Examples 1 and 2 were inferior in antistatic properties.

  The antistatic coating composition of the present invention is used to form an antistatic coating on liquid crystal screens, home appliances, and their production lines that should avoid charging and dust adsorption.

Claims (8)

  A polymer containing 100 parts by weight of a hard coat base containing at least one of an ethylene group-containing monomer and an ethylene group-containing prepolymer, a repeating unit having a polar structure of any one of an ion pair and betaine, and a fluorocarbon group An antistatic coating composition comprising 0.5 to 50 parts by weight of a compound.   In the polymer compound, the polar structure is selected from a halogenated quaternary ammonium group, a phosphoric ester ammonium group, a sulfate ester ammonium group, a halogenated quaternary phosphonium group, a basic sulfonic acid group, and a basic carboxylic acid group. 2. The antistatic coating composition according to claim 1, wherein the betaine has at least one of the ion pairs; a sulfonate ion group or a carboxylate ion group and a quaternary ammonium group or a quaternary phosphonium group. .   The polymer compound is an unsaturated macromonomer having a repeating unit containing any one of a halogenated alkyl group, a halogenated aryl group, and a halogenated aralkyl group, and the unsaturated monomer or the fluorocarbon containing the fluorocarbon group. A copolymer with an unsaturated macromonomer containing a group is reacted with a tertiary amine or tertiary phosphine to form the ion pair of the halogenated quaternary ammonium group or the halogenated quaternary phosphonium group. The antistatic coating composition according to claim 2, wherein the antistatic coating composition is.   The unsaturated macromonomer having a repeating unit containing any one of the halogenated alkyl group, the halogenated aryl group, and the halogenated aralkyl group is a macromonomer derived from chloromethylstyrene. Item 4. The antistatic coating composition according to Item 3.   The copolymer is at least one other unsaturated monomer selected from a (meth) acrylic acid monoester monomer, an unsaturated carboxylic acid monomer, a (meth) acrylamide monomer, a styrene monomer, a vinyl ether monomer, and a vinyl ester monomer; 4. The antistatic coating composition according to claim 3, which is copolymerized.   The antistatic coating composition according to claim 1, which contains a photopolymerization initiator or a thermal polymerization initiator.   An antistatic coating film obtained by curing the antistatic coating composition according to claim 1.   The antistatic coating composition according to any one of claims 1 to 6 is applied to a plastic substrate and irradiated with an active energy ray, whereby the ethylene group-containing monomer and / or the ethylene group-containing monomer is contained. A method of forming an antistatic coating, characterized in that a prepolymer is crosslinked and cured.