TW201247758A - Antistatic agent used for active-energy-ray curable resin, and active-energy-ray curable resin containing the same - Google Patents

Abstract

The present invention provides an antistatic agent used for the composition of active-energy-ray curable resin, which is able to even lower the surface resistance value than the composition of active-energy-ray curable resin containing the antistatic property from prior art. The antistatic agent used in the composition of active-energy-ray curable resin is characterized by being represented by the below-mentioned general formula (1) and/or (2) (wherein R represents alkyl group of carbon number 8 to 13, and 0 ≤ n ≤ 6).

Description

[Technical Field] The present invention relates to an antistatic agent for an active energy ray-curable resin and an active energy ray-curable resin containing the antistatic agent. [Prior Art] An energy ray-curable resin composition is used for coating and subsequent use of various substrates. The energy-line-hardening resin composition of the sample is easy to be electrostatically charged, and dust or dust adheres to the grain, and depending on the application, antistatic property is required. Thus, in order to improve the antistatic property of the energy ray-curable resin composition Sexual food b and & various proposals. There is disclosed, for example, a coated composition (Patent Document 1) and an ultraviolet curable resin composition (Patent Document 2), the coated composition containing a monomer containing a phosphate ester and a propylene oxide in a molecule. The base and/or mercapto acetonitrile resin composition contains a monomer having a quaternary ammonium salt group and a (fluorenyl) acrylonitrile group. However, although it has been confirmed that these compositions have an effect of lowering a certain surface resistance value, an antistatic agent for an energy ray-curable resin composition is required to have more excellent antistatic properties. [PRIOR ART DOCUMENT] (Patent Document) Patent Document 1. Japanese Patent Laid-Open Publication No. JP-A-63-56-64-A-Patent Publication No. JP-A-2010-285480 The present invention has been made in view of the above circumstances, and an object of the invention is to provide an antistatic agent for an active energy ray-curable resin composition and an active energy ray-curable resin composition containing the antistatic agent, which is capable of A more conventional active energy ray-curable resin composition having antistatic properties further lowers the surface resistance value. [Technical means for solving the problem] The present inventors have repeatedly made efforts to carry out research, and as a result, have focused on the fact that it was found that when a specific phosphate compound is used, the phosphate compound is locally present on the surface of the resin composition to exhibit excellent results. The surface resistance value, and the completion of the present invention, is a fact that is directed to a conventional active energy ray-curable resin composition having antistatic properties, and a phosphate ester group and a quaternary ammonium salt group dispersion due to antistatic properties of the tribute When the resin composition is initially dried, the surface resistance value is increased, that is, the antistatic property is lowered. In other words, the first gist of the present invention is an antistatic agent for a resin composition characterized by '«=*1 line hardenability: the following general formula (1) and/or (7) 0

R0(CH2CH20)rrP-0H

OH ...(2) 201247758

R0(CH2CH20) R0(CH2CH20)n (wherein R represents an alkyl group having 8 to 13 carbon atoms, 0$η$6). According to a second aspect of the present invention, an active energy ray-curable resin composition is characterized by comprising an antistatic agent for the active energy ray-curable resin composition. Further, the surface resistance of the active energy ray-curable resin composition of the present invention is preferably 1 〇 12 Ω or less. [Embodiment] [Best Mode for Carrying Out the Invention] Next, an embodiment of the present invention will be described. The antistatic agent (hereinafter referred to as "antistatic agent") for the active energy ray-curable resin composition of the present invention is a compound represented by the following general formula (1) and/or (2).

OH 0

RO(CH2CH2〇)jf Ρ-OH

I

OH R0(CH2CH20), R0(CH2CH20)n (2) 201247758 (wherein R represents an alkyl group having 8 to 13 carbon atoms, 〇$nS6). In the formula (1) and/or (2), r is an alkyl group having 8 to 13 carbon atoms. These substituents are not particularly limited and can represent a linear alkyl group such as an octyl group, a decyl group, a decyl group, a dodecyl group, an undecyl group or a dodecyl group; or a tridecyl hexyl group or a group Heptylheptyl, dinonylheptyl, trihanylheptyl, tetramethylheptyl, 6-heptyl, methyloctyl, methyldecyl, methylmercapto, methyldodecyl, a branched alkyl group such as methyl undecyl or decyltridecyl. In the general formulae (1) and/or (2), n is not less than 〇 and not more than 6. When n exceeds 6, the following problem occurs. The antistatic performance may be insufficient, that is, the surface resistance may become 1 〇 13 Ω or more. The compounding ratio of the compounds of the formulae (1) and (2) is not particularly limited, and the molar ratio thereof is preferably 60: 40 to 40: 60. The antistatic agent of the present invention may be used singly or in combination of two or more. A commercially available alkyl (ether) phosphate type surfactant can be used as the antistatic agent of the present invention. For example, "Phosphanol (registered trademark) series" manufactured by Toho Chemical Co., Ltd., "ADEKA C0L (registered trademark) PS/CS/TS series manufactured by ADEKA Co., Ltd." and "PLYSURF (registered trademark) manufactured by Daiichi Kogyo Co., Ltd. ) series" and so on. The compounding amount of the antistatic agent of the present invention is not particularly limited, and is preferably from 3 to 15 parts by weight, more preferably from 5 to 1 part by weight, per 100 parts by weight of the active energy ray-curable resin. If it is less than 3 parts by weight, sufficient electrical conductivity cannot be obtained, and if it exceeds 15 parts by weight, the problem of bleeding may occur. The active energy wire-curable resin of the present invention is not particularly limited, and the active energy ray-curable tree of 201247758 can be used for the target fat of the present invention. Preferred examples of the active energy ray-curable resin include an active energy ray-curable resin containing an acrylic polymer, and the acrylic polymer has a compound as a main component: a carbon number &quot Alkyd acrylic and / or methyl acrylate vinegar - (four) two or more. Further, an example of a one-liquid type or a two-liquid type of urethane, or an acrylic resin or an epoxy resin which can be polymerized by thermal polymerization or radiation polymerization. The acrylic polymer of the present invention is not particularly limited, and is obtained by polymerizing a conventional monomer which is conventionally known by thermal polymerization or radiation polymerization. Representative examples of the above monomers include, for example, (fluorenyl) propylene oxime 2-ethylhexyl vinegar, styrene decyl decyl acrylate, acryl hydrazinomorph, (indenyl) arsenazo quinone 0, (A) Acetyl acetoacetate, (meth)propane phenoxypropacetin (meth)acrylic acid polyethoxyphenyl ester, (meth)acrylic acid polyethoxybenzoquinone (A) Phenyl phenyl benzoate, o-phenylphenol (meth) acrylate, o-phenylphenoxy ethoxy(meth)acrylate, polyethoxyphenyl phenoxy phenoxy (meth) acrylate Ethoxylate, isophorone (meth)acrylate, mono(meth)acryloxyethyl phthalate, ethylene glycol bis(mercapto)acrylate, propylene glycol di(meth)acrylate, Polyethylene glycol bis(indenyl)acrylic acid vinegar, polypropylene glycol bis(indenyl) acrylate, polytetradecyl bis(meth)acrylic acid vinegar, 丨'4 butanediol bis(indenyl) acrylate, 1 , 6-hexanediol di(meth) acrylate, hydrazine, 9-nonanediol bis(indenyl) acrylate, EO (ethylene oxide, following Same as) modified bisphenol bis(indenyl) acrylate, PO (propylene oxide, the same as 201247758) modified bisphenol di(meth) acrylate, trishydroxypropyl propane tris(fluorenyl) acrylate , EO modified trishydroxypropyl propane tri (meth) acrylate, P0 modified trimethylol propyl tris(decyl) acrylate, pentaerythritol tris(fluorenyl) acrylate, ((meth) propylene oxime Oxyethyl)isocyanurate, pentaerythritol tetrakis(meth)acrylate, EO-modified pentaerythritol tetra(meth)acrylate, PO-modified pentaerythritol tetra(meth)acrylate, bis(trishydroxyl) Mercaptopropane) tetra(meth)acrylate, EO modified bis(trimethylolpropane)tetrakis(meth)acrylic acid, PO modified bis(trimethylolpropane)tetrakis(meth)acrylate, Dipentaerythritol hexa (meth) acrylate, EO modified dipentaerythritol hexa (meth) acrylate, PO modified dipentaerythritol hexa(indenyl) acrylate, dipentaerythritol penta (meth) acrylate, and the like. These may be used alone or in combination. Further, the amine ester resin which can be polymerized by thermal polymerization or radiation polymerization is specifically, for example, an amine ester (mercapto) acrylate. The amine ester (meth) acrylate is obtained by reacting the following compounds: (A) a polyhydric alcohol, (B) a polyisocyanate, and (c) a (meth)acrylic acid vinegar having a hydroxyl group in the molecule. The (A) polyol is not particularly limited, and specifically, a polyfluorene polyol, a polycarbonate polyol, a polyfluorene polyol, an aliphatic hydrocarbon polyol, or an alicyclic hydrocarbon polyol can be used. Further, the (B) polyisocyanate is not particularly limited, and specific examples thereof include aliphatic polyisocyanuric acid, alicyclic polyiso(iv) vinegar, musk _ vinegar, and aromatic aliphatic polyisocyanate. The aliphatic polyisocyanate is exemplified by tetramethylene diisocyanate, decamethyl diisocyanate 'hexamethylene isocyanate, 2,2'4-trimethylhexamethylene diisocyanate , Μ,心; 201247758 hexamethylene dimethyl sulphate-"cyanate ester, bis- phthalic acid di-n-butyl t-1,5-diisocyanine, 3 mm methyl pentane isocyanate can be steamed" Pentane·1,5-diisocyanate. Cycloaliphatic polyacids, 44 such as: different sulphuric acid, sulphuric acid, xylene diisocyanate, ketone; Cyanic acid vinegar, α-cyclohexanyl diisocyclohexane, etc.: Swallow % hexyl diisocyanate, bis (isocyanatomethyl) 2, 2, two polyisocyanate, for example : A stupid diisocyanate vinegar, vinegar, diisocyanate vinegar, 2,4, diphenyl ketone diisocyanate nitrite bismuth bismuth diiso-acid _), 4,4'-diphenyl Methyl diisoiso-acid acid, vr; iso-poly, xylene diisocyanate, stupid two, such as hetero-poly, etc.. Aromatic aliphatic polyiso-acid vinegar can be π soil-based methane diisocyanate, tetradecane Diphenyl phenylacetate 7 isocyanate vinegar 'α,α,α,α_tetradecyl xylene Nitric acid, etc., for example, such dimers, trimers, and trimmers such as tweezers/isodecyl esters of organic polyisocyanates can be used, or they can be used alone, or Further, two or more kinds are used. The (meth)acrylic acid vinegar having a transbasic group in the ν() knife is not particularly limited. Specifically, for example, acrylic acid 2, base ethyl s|, methyl methacrylate Yin diyl B曰, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, olefin I 4 butyl vinegar, caprolactone modified acrylic acid, ethyl acetonate, polyethanol monopropyl acrylate, polypropylene glycol Acrylic vinegar, polybutylene glycol monopropylene, S-day, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, etc. Also, bisphenol A type epoxy resin, bisphenol 1 type epoxy tree can be used. Epoxy acryl vinegar obtained by (meth)acrylic acidification of an epoxy group, such as a ruthenium epoxy resin, etc. These can be used alone or in combination of plural 201247758

2 Amine vinegar (10)) Acrylic acid 8 of the invention can be combined by a conventional method:: enough to be synthesized in the following manner, for example: - a predetermined amount of (4) component and (B) component are fed in a predetermined amount, and at 7 〇 8 (ΓΓ祛甘、也/ “Μ p 8GC makes it react until it becomes predetermined = green read s, then suppresses: there is a lower-order feed (C) component' and heats at 70~ In addition, it is also possible to add a tin-based catalyst such as dibutyltin laurate to promote the reaction. Examples of the radiation include ultraviolet rays, thunder rays, alpha rays, and general rays m. X-ray, electron beam, etc. In addition, when a UV-ray is used as a radiation, a photopolymerization initiator is added. The photopolymerization initiator can be used as long as it is irradiated by the type of the radiation-reactive component. The ultraviolet light of a suitable wavelength of the polymerization reaction can generate a radical or a cation. The photoradical polymerization initiator can be, for example, benzoin, benzoin methyl ether, benzoin ethyl ether, methyl o-benzoylbenzoate. Benzoin ethyl ether, benzoin Benzoin such as propyl ether, α-methylbenzoin, benzoyl-methyl ketal, tri-o-acetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl, etc. Acetophenones; 2-hydroxy-2-mercaptopropiophenone, 2-hydroxy-4, isopropylidene-2-mercaptopropiophenone, etc.; benzophenone, decylbenzhydryl, Dimethyl ketones such as dibenzophenone and p-nonylaminodibenzophenone; 2-chlorothioxanthone, 2-ethylthioxanthone, 2-isopropyl Thioxanthone such as ketene; bis(2,4,6-trimercaptobenzoyl)-phenylphosphonium oxide 2,4,6-tridecyl albino diphenylphosphine oxide , 2,4,6-triple 201247758 sulfhydryl-ethoxyl-phenylphosphine oxide and other mercaptophosphine oxides; stupid brewing 'dibenzosuberone' (dibenzosuberone); α-醯The cation-polymerization initiator may, for example, be an aromatic diazonium salt, an aromatic sulfonium salt, a rust salt such as an aromatic strontium salt, an iron-propylene di-alkaline complex, or a ferrocene compound. Organic metal complexes such as aryl sterol-aluminum complex; nitrophenyl decyl ester; sulfonic acid derivative; Phosphate ester; sulfonic acid derivative; phosphate ester; phenolsulfonate; diazonaphthoquinone; hydrazine-hydroxy quinone sulfonate, etc. Photopolymerization initiation relative to 1 part by weight of active energy ray-hardening resin The agent is usually blended in an amount of 0.1 to 1 part by weight, preferably 2 to 7 parts by weight. Further, a photopolymerization initiation aid such as an amine can be further used in combination. 2-dimethylaminoethyl benzoate, di-decylaminoacetophenone, ethyl p-dimethylaminobenzoate, p-dimethylamino benzalmate isoamyl ester, etc. The above photopolymerization initiation The active energy ray-curable resin composition of the present invention can be obtained by disposing a predetermined amount of an antistatic agent in a raw material of the active energy ray-curable resin and causing it to be used in combination. Perform polymerization. In the active energy ray-curable resin composition of the present invention, in addition to the above-mentioned polymerization initiator and polymerization initiator, it is also possible to add '·diluting solvent, lubricant, leveling agent, filler, as needed. Wait. The surface resistance of the active energy ray-curable resin composition of the present invention is preferably ΙΟ12 Ω or less, more preferably 1 Å. When Q or less exceeds 1〇12 Ω, the problem arises that dust adheres due to charging. 201247758 [Embodiment] However, in the present invention and comparative examples, the following examples will be given to more specifically explain that the present invention is not limited thereto. The embodiment is defined. Further, in the examples, unless otherwise specified, the parts and % are based on the weight. 1. Synthesis of active energy ray-curable resin [Synthesis Example 1] An acrylate of bisphenol A type epoxy propyl ether (epoxy equivalent = 45 Å) was fed into a flask, 3445 g (3.3 mol), hydroquinone </ br> ^ Sex energy line hardening resin. [Synthesis Example 2] An acrylate of bisphenol oxime type epoxy propyl ether (epoxy equivalent = 45 Å) was fed into a flask, and 3445 g (3.3 mol) of 'hydroquinone monodecyl ether 181 g, phenoxy acrylate was fed. 2422 g of ethyl ester, 188 g (1 m〇i) of diphenylene diisocyanate, and active energy ray-hardening type was obtained by reacting at 70 to 8 (TC conditions until the residual isocyanate concentration became 0.1%). Resin 2. Adjustment of active energy ray-curable resin composition In the synthesis example 1 or 2 obtained above, the antistatic agents shown in Table 1 below were prepared in the proportions (parts by weight) shown in Table 2, respectively. And an α-hydroxyalkyl phenyl ketone (product name: Irgacure 1 84 'BASF Corporation) 3% by weight as a photopolymerization initiator, 50% by weight of ethyl acetate as a diluent, and mixed to obtain an activity Energy line hardening resin composition. 12 201247758 [Table 1] Zhuo vinegar (general π)) and Moer jman type / neutralization of acid type - · ~ a · acid type --- acid type

Antistatic agent octyl 13 antistatic agent 8 4 12 base 12 acid type 1 - 11 % 6 styrenated phenyl antistatic agent 9 antistatic agent ίο | ίο | thirteen yard based antistatic agent 11 19.8~[Τ Dialkyl antistatic agent 12 ethyl sulphate lauryl dimethyl hydride antistatic agent 13 ethyl sulphate octyl sulfhydryl antistatic agent 14 phosphoric acid mono propylene methoxyethyl ester 13 12 acid type Type acid type--^1. Acid type 13 201247758 [Table 2] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Synthesis Example 1 100 Synthesis Example 2 100 100 100 100 100 100 100 Antistatic agent 1 5 Antistatic agent 2 5 Antistatic agent 3 5 5 Antistatic agent 4 5 Antistatic agent 5 5 Antistatic agent 6 5 Antistatic agent 7 5 Antistatic agent 8 Antistatic agent 9 Antistatic Agent 10 Antistatic agent 11 Antistatic agent 12 Antistatic agent 13 Antistatic agent 14 Surface resistance (Ω) 4.2E+12 6.5E+15 2.5E+9 5.2E + 9 1.9E+9 1.2E+8 2.6E+ 8 8.1E+8 Embodiment 9 Embodiment 10 Embodiment 11 Example 12 Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Synthesis Example 1 100 100 100 Synthesis Example 2 100 100 100 100 100 Antistatic agent 1 Antistatic agent 2 Antistatic agent 3 5 7 10 Antistatic agent 4 Antistatic agent 5 Antistatic Agent 6 Antistatic agent 7 Antistatic agent 8 5 Antistatic agent 9 5 Antistatic agent 10 5 Antistatic agent Π 5 Antistatic agent 12 Antistatic agent 13 Antistatic agent 14 Surface resistance (Ω) 5.5E+9 4.2E+ 12 1.7E+11 3.5E4-10 2·1Ε 十16 1.3Ε+16 2.0Ε+14 3.2Ε+16 14 201247758 Comparative Example 5 Comparative Example 6 Comparative Example 7 Synthesis Example 1 100 100 100 Synthesis Example 2 Antistatic Agent 1 Antistatic agent 2 Antistatic agent 3 Antistatic agent 4 Antistatic agent 5 Antistatic agent 6 Antistatic agent 7 Antistatic agent 8 Antistatic agent 9 Antistatic agent 10 Antistatic agent 11 Antistatic agent 12 5 Antistatic agent 13 5 Antistatic agent 14 5 Surface resistance (Ω) 2.4Ε+16 2.4E-M6 2Ε+17 3. Evaluation of active energy ray-curable resin composition &lt;Production of evaluation sample&gt; The active energy ray-curable resin composition obtained above was spin-coated (500 rpm, 5 sec = 1500 rpm, 15 sec) on a PET film (LUMIRROR manufactured by Toray) (corona treated surface) at 80 ° C After drying for 10 minutes, ultraviolet rays of 200 mJ/cm 2 were irradiated by a high pressure mercury lamp to prepare an evaluation sample. &lt;Surface resistance measurement condition&gt; The measurement was carried out under the conditions of a temperature of 20 ° C and a humidity of 65% using R8340 ULTRA HIGH RESISTANCE METER manufactured by ADVANTEST Co., Ltd. The evaluation results are shown in Table 1 above. As is clear from the results shown in Table 2, when R and η in the general formula (1) exceeded the pre-15 201247758 ( (Comparative Examples 2 to 3), and when the structure was different from the general formula (1) (Comparative Example) 5~7) 'The surface resistance of the antistatic agent will exceed ΙΟ12 Ω. The antistatic agent of the present invention and the active energy ray-curable resin composition using the antistatic agent can be suitably used for a hard coat film for an optical film, an optical film, and an antistatic protective film. The present invention has been described in detail above with reference to the specific embodiments of the present invention, and various modifications and changes can be made without departing from the spirit and scope of the invention. And easy to know. The present application is based on a Japanese patent application filed on Apr. 7, 2011 (Japanese Patent Application No. 2011-085008), the disclosure of which is incorporated herein by reference. [Simple description of the diagram] Benefits [Main component symbol description] None 16

Claims (1)

201247758 VII. Patent application scope: 1. An antistatic agent for an active energy ray-curable resin composition, which is characterized by the following general formula (1) and/or (2): RO(CH2CH20)n-P-OH OH R0(CH2CH20) R0(CH2CH20)n (2) (wherein R represents an alkyl group having a carbon number of 8 to 13, 0SnS6) 2. An active energy ray-curable resin composition comprising the active energy ray-curable resin composition of claim 1 Antistatic agent for use. 3. The active energy ray-curable resin composition according to claim 2, wherein the surface resistance is ΙΟ12 Ω or less. 17 201247758 IV. Designation of representative drawings: (1) The representative representative of the case is: No (2) The symbol of the symbol of the representative figure is simple: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 201247758 Dijon) 1 1 〇ς 〇4 9 Patent 8.11 Amendment I, invention patent description 1 (This specification format, order 'Do not change any 1 part of the note, please do not fill in: please ask the case number Fill in) ※Application number: 101106049 ※Working PC classification: ※Application date: February 23, 2012. Name of the invention: Antistatic agent for active energy ray-curable resin and active energy ray hardening containing the antistatic agent Abstract: The present invention provides an antistatic agent for an active energy ray-curable resin which can reduce the surface resistance value more than the conventional active energy ray-curable resin having antistatic properties. The antistatic agent for a line curable resin is characterized by the following general formula (1) and/or (2): RO(CH2CH2〇)tp 〒-OH (1) OH R0 (CH2CH20) R0(CH2CH20)n OH (wherein R represents a carbon number of 8 to 13 and 0$η$6). III. Summary of the Invention of the Invention: (2) 201247758 VI. Description of the Invention: [Technical Field] The present invention relates to an antistatic agent for an active energy ray-curable resin, and an active energy ray hardenability containing the antistatic agent Resin. [Prior Art] An energy ray-curable resin is used for coating and entanglement of various substrates. Such an energy ray-curable resin is likely to be attached with dust or dust due to the fact that it is easy to carry static electricity. Depending on the application, antistatic properties are required. Thus, various proposals have been made to improve the antistatic performance of the energy ray-curable resin. There is disclosed, for example, a coating composition (Patent Document 1) and an ultraviolet curable resin (Patent Document 2), the coating composition containing a monomer containing a phosphate ester and an acryloxy group in a molecule and / 甲基 or methacryloxyloxy group, the ultraviolet curable resin contains a monomer having a quaternary ammonium salt group and a (meth) acrylonitrile group. However, although it is possible to clarify that these compositions have a function of lowering a certain surface resistance value, an antistatic agent for an energy ray-curable resin is required, which has more excellent antistatic properties. [Prior Art Document] (Patent Document) Patent Document 1 Japanese Patent Laid-Open Publication No. SHO-63-64-54 Patent Publication No. 2 Japanese Patent Publication No. 2281〇_28548〇 No. 201247758 [Summary of the Invention] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an antistatic agent for an active energy first-line curable resin and an active energy ray-curable resin containing the antistatic agent. The agent can lower the surface resistance value more than the conventional active energy ray-curable resin having antistatic properties. [Means for Solving the Problems] The present inventors have repeatedly made efforts to conduct research. The results have focused on the fact that when a specific phosphate compound is used, the phosphate compound is locally present on the surface of the resin to exhibit excellent surface resistance. The value of the present invention is completed as follows: the conventional active energy ray-curable resin having antistatic properties is dispersed in the resin by the use of the antistatic property and the quaternary salt base. The increase in surface resistance value, that is, the antistatic property is lowered. b In other words, the first gist of the present invention is an antistatic agent for an active energy ray-curable resin characterized by the following general formula (1) and/or TFT* 0 RO(CH2CH20)fr-p-〇H OH 4 ... (2) 201247758 R0(CH2CH20) R0(CH2CH20)n (wherein R represents a carbon group of 8 to 13 and 〇$η$6). According to a second aspect of the invention, there is provided an active energy ray-curable resin comprising the antistatic agent for an active energy ray-curable resin. Further, the surface electric resistance of the active energy ray-curable resin of the present invention is preferably 1012 Ω or less. [Embodiment] [Best Mode for Carrying Out the Invention] Next, an embodiment of the present invention will be described. The antistatic agent for an active energy ray-curable resin of the present invention (hereinafter referred to as "antistatic agent") is a compound represented by the following general formula (1) and/or (2). Q (1) RO(CH2CH2〇)fj—P—OH I OH (2 R0(CH 2 CH 20 ), knife R 0 (CH 2 CH 20 ) n / X 〇 H (wherein R represents an alkyl group having 8 to 13 carbon atoms, 〇 In the formula (1) and/or (2), R is an alkyl group having 8 to 13 carbon atoms. These substituents are not particularly limited, and can represent an octyl group, an anthracenyl group, or a fluorenyl group. a linear alkyl group such as dodecyl, eleven alkyl or tridecyl; or trimethylhexyl, methylheptyl, dimethylheptyl, trimethylheptyl or tetramethylglycol a branched alkyl group such as an ethyl group, an ethylheptyl group, a decyloctyl group, an indenyl fluorenyl group, a fluorenyl fluorenyl group, a decyl dodecyl group, a methyl undecyl group or a methyltridecyl group. In the formula (1) and/or (2), n is not less than 〇 and not more than 6. When n exceeds 6, the following problem occurs: the antistatic property is insufficient, that is, the surface resistance is 1013 Ω or more. The compounding ratio of the compounds of the formulae (1) and (2) is not particularly limited, and the molar amount thereof is preferably 60: 40 to 40: 60. The antistatic agent of the present invention may be used alone or in combination of two kinds. Used above. 抗 Antistatic agent of the present invention A commercially available alkyl (ether) phosphate vinegar type surfactant is used. For example, "Ph〇sphan〇1 (registered trademark) series" manufactured by Toho Chemical Co., Ltd., and "ADEKA COL (registered trademark) PS by Adeka Co., Ltd. /CS/TS series", "PLYSURF (registered trademark) series" manufactured by Daiichi Kogyo Co., Ltd., etc. The amount of the antistatic agent of the present invention is not particularly limited, and the weight of the active energy ray-curable resin is 1 〇〇. The portion is preferably 3 to 15 parts by weight, more preferably 5 to 10 parts by weight. If it is less than 3 parts by weight, it is not obtained: if the conductive property of the portion exceeds 15 parts by weight, the problem of bleeding may occur. The active energy ray-curable resin of the invention is not particularly limited, and an active energy ray-curable resin which has hitherto been used for the intended use of the present invention can be used. Preferred examples of the resin are active energy ray-curable resins of acrylic polymers, alkyl groups having 1 to 14 carbon atoms, or two or more compounds. Further, the main component of the acrylic acid and/or the methyl acrylate may be, for example, a one-liquid type or a two-liquid type of urethane resin (or an urethane resin; or a thermal polymerization or a radiation polymerization) Acrylic resin, epoxy resin, etc. to be polymerized. The acrylic polymer of the present invention is not particularly limited, and is obtained by polymerizing a conventional monomer which is conventionally known by thermal polymerization or radiation polymerization. Representative examples of the above monomers include, for example, (meth)acrylic acid 2-ethylhexyl acrylate, styrene, methyl methacrylate, acryloylmorpholine, tetrahydrofurfuryl (meth) acrylate, (methyl) ) phenoxyethyl acrylate, phenoxypropyl (meth) acrylate, polyethoxy phenyl (meth) acrylate, phenyl phenyl hydrazine (mercapto) acrylate, o-phenyl phenol (methyl) Acrylate, o-phenylphenoxyethoxyacetic acid (meth)acrylate, polyethoxyphenylphenoxyethoxy(meth)acrylate, isophorone (meth)acrylate, phthalic acid Mono(indenyl) propylene methoxy acetate, ethylene glycol di(mercapto) acrylate, propylene glycol di(meth) acrylate, polyglycol bis(indenyl) acrylate, polypropylene glycol di(methyl) ) acrylate, polytetramethylene glycol bis(indenyl) acrylate, 1,4 butanediol di(meth) acrylate, 1,6-hexanediol di(meth) acrylate, l,9-nonanediol di(meth) acrylate, EO (ethylene oxide, all of the same) modified bisphenol di(methyl) propyl Acid vinegar, PO (propylene oxide, the same as below) modified bisphenol di(meth)acrylic acid vinegar, trishydroxypropyl propane tri (meth) acrylate, EO modified trihydroxy decyl propyl sulphur Acrylate, PO modified trimethylolpropane tris(indenyl)propene 7 201247758 enoate, pentaerythritol tri(meth)acrylate, ((meth)acryloxyethyl)isocyanuric acid Ester, pentaerythritol tetra(meth) acrylate, E 〇 modified pentaerythritol tetra (meth) acrylate, p 〇 modified pentaerythritol tetra (meth) acrylate vine, bis (trimethylolpropane) tetra (methyl) Acrylate, E 〇 modified bis (trimethyl methacrylate) tetra (methyl) acrylate, p 〇 modified bis (trihydroxy thiopropyl propyl) tetra (meth) acrylate, dipentaerythritol (Meth) acrylate, E 〇 modified dipentaerythritol hexa (meth) acrylate, PO modified dipentaerythritol hexa(methyl decyl) acrylate, dipentaerythritol penta (meth) acrylate, and the like. These can be used alone or in combination. Further, the amine vinegar resin which can be polymerized by thermal polymerization or radiation polymerization is specifically, for example, an amine ester (meth) acrylate. The amine ester (mercapto) acrylate is obtained by reacting the following compound (A) a poly 70 alcohol, (B) a polyisocyanate ', and (c) a (meth)acrylic acid having a hydroxyl group in the molecule. The (A) polyol is not particularly limited, and specifically, a polyester polyol, a polycarbonate polyol, a polyether polyol, an aliphatic hydrocarbon polyol, or an alicyclic hydrocarbon polyol can be used. The (B) polyisocyanate is not particularly limited, and specific examples thereof include aliphatic polyisocyanate, alicyclic polyisocyanate, aromatic polyisocyanate, and aromatic aliphatic polyisocyanate. The aliphatic polyisocyanate may, for example, be tetramethylene diisocyanate, decamuthylene diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2, 4,4_Trimethylhexamethylene diisocyanate lysine diisocyanate, 2-methylpentane 1,5-diisocyanate, 3-methylpentane q,5-diisocyanate alicyclic 8 201247758 The isocyanate may, for example, be isophorone diisocyanate, hydrogenated xylene diisocyanate S曰, 4,4′-dicyclohexyldecane diisocyanate, “4-cyclohexane diisocyanate methyl extension ring” Hexyl diisocyanate, hydrazine, 3 bis(isocyanatomethyl) hexyl hexane, etc. The aromatic polyisocyanate may, for example, be toluene diisocyanate, styrene-based diisocyanate, 2,4,-diphenyl fluorene Sodium diisocyanate, 4'4'-diphenyldecane diisocyanate 4,4,-diphenyldecyl diisocyanate S曰, naphthalene diisocyanate, xylene diisocyanate, 1,3-benzene ❹ Ο Ο Ο 曰 1,4- 1,4- 1,4- 1,4- 1,4- 1,4- 1,4- 1,4- 1,4- 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 Alkane diisocyanate, tetraalkyl diphenyl ketone diisocyanate, α,α,α,α-tetramethylxylene diiso oleic acid vinegar, etc. Further, for example, such organic polyisocyanate A dimer, a trimer, a modified body such as a phalloid-urea isocyanate, etc. can also be used singly or in combination of two or more. - (C) a (hydroxy) acrylate having a hydroxyl group in the above molecule In particular, it can be specifically exemplified by: 2-hydroxyethyl acrylate, methacrylic acid, acetyl acrylate, 2' propyl acrylate, methacrylic acid 2- propyl acrylate, 4-hydroxy butyl acrylate Ester, caprolactone modified 2-hydroxyethyl acrylate, polyethylene acrylate acrylic acid, polypropylene glycol monoacrylic acid brewing, polybutylene glycol monoacrylic acid brewing, pentaerythritol triacrylate vinegar, dipentaerythritol acryl vinegar and the like. And 'can also be used: double A-type epoxy resin, double? An epoxy acrylate which is obtained by subjecting an epoxy group to (meth)acrylic acid sulfonate, such as an epoxy resin or a (iv) epoxide type. These can be used alone or in combination with a plurality of 0 amine vinegars of the present invention (φ Iγ &amp; (methyl)propionate can be obtained by a conventional method 9 201247758. This is enough for the following test; , formula &amp;, for example: - a predetermined amount of (A) into (B) components, and reacted at 80 c until it becomes a predetermined, '-t acid Se $ &amp; The polymerization inhibitor such as methyl mystery has a sub-feeder (C) component, and is heated at 7G to Saki until the free isocyanate g is used to eliminate &amp; μ, ndt. At this time, it can also be promoted. In the reaction, a tin-based catalyst such as dibutyltin dilaurate is added. Ο The radiation may be, for example, ultraviolet rays, thunder rays, alpha rays, beta gamma rays, X-rays, electron beams, etc. Further, when ultraviolet rays are used as a line The photopolymerization initiator is added to the photopolymerization initiator, and the photopolymerization initiator is capable of generating radicals by irradiating ultraviolet rays of an appropriate wavelength capable of initiating the polymerization reaction by the type of the radiation reaction component. Cationic. Photoradical polymerization initiator Examples are: benzoin, benzoin thiol ether, benzoin ethyl sulphate, o-branched benzoic acid ketone _ benzoin ethyl ether, benzoin isopropyl ether, α-methyl benzoin and other benzoin; benzoquinone Methyl condensed _, dichloro acetophenone, 2,2 diethoxy acetophenone, hydroxycyclohexyl phenyl ketone and the like acetophenone; 2 - hydroxy 2 - nonyl phenyl acetonide, hydrazine hydroxy group 4 , phenylpropanone such as isopropyl-2-mercaptopropiophenone; benzophenone, decyl dibenzophenone, p-chlorobenzophenone, p-didecylaminobenzophenone, etc. Ketones; 2-chlorothioxanthone, 2-ethyl sinone, 2-isopropyl thioxanthone, etc.; bis(2,4,6-trimethylbenzene) Mercapto) phenylphosphine oxide, 2,4,6-trimethyl benzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyl-ethoxy-phenyl a mercaptophosphine oxide such as a phosphine oxide; a benzil, a dibenzosuberone; an α-fluorenyl 201247758 oxime ester, etc. The photocationic polymerization initiator may, for example, be an aromatic Heavy gas, salt, aromatic strontium salt, aromatic strontium salt, etc.镔 salt; iron _ propylene dilute complex ' 二 鈇曰 鈇曰 彡 彡 石 石 醇 醇 醇 醇 醇 醇 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 ; ; 确 确 确 确 确 确 确 确 确 确 确 确 确 确 确 确Rheutic acid brewing; heavy atmosphere Cai parent; quinone imine acid salt, etc. Relative to the active energy ray-curable resin 1 〇〇 by weight, photopolymerization ❹ 始 剂 剂 通 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 In the range of the formulation, it is preferred to use U to 7 parts by weight. It is also possible to further carry out photopolymerization initiation aids such as amines, etc. The photopolymerization initiation aid may, for example, be phthalic acid 2-dimethylamino group. Ethyl vinegar, dimethylaminophenyl benzene, ethyl p-dimethylaminobenzoate, p-dimethylamino; isoamyl formate. Two or more kinds of the above-mentioned photopolymerization initiation aids can also be used in combination. The active energy ray-curable resin of the present invention can be obtained by disposing a predetermined amount of an antistatic agent in the raw material of the active energy ray-curable (IV) and polymerizing it. In addition to the above-mentioned polymerization initiator and polymerization initiation assistant, the active energy ray-curable resin of the present invention can be added as needed: a diluent solvent, a lubricant, a leveling agent, a filler, and the like. The surface resistance of the active energy ray-curable resin of the present invention is preferably ΙΟ 12 Ω or less, more preferably 101. Below Ω. When the surface resistance value exceeds 1〇1: Ω, there is a problem that dust adheres due to charging. [Embodiment] 11 201247758, but in the present invention and comparative examples, the present invention will be more specifically described below by way of examples. Further, in the examples, unless otherwise specified, the parts and % are based on the weight. 1. Synthesis of active energy ray-curable resin [Synthesis Example 1] The flask was fed with propylene glycol 3445 g (3.3 mol) of bisphenol A type epoxy propyl ether (epoxy equivalent = 45 Å), 181 g of hydroquinone monodecyl ether, and 188 g of xylene diisocyanate (l mol). The reaction was carried out under the conditions of 70 to 8 Torr until the residual isocyanate concentration became 0.1%, and an active energy ray-curable resin was obtained. [Synthesis Example 2] An acrylate of bisphenol A type epoxy propyl ether (epoxy equivalent = 45 Å) was introduced into a flask, and 3445 g (3.3 mol) of acrylate, 181 g of hydroquinone monomethyl ether, and phenoxy acrylate were fed. 2422 g of ethyl ester and 188 g (1 m〇1) of xylene diisocyanate were reacted at 70 to 80 ° C until the residual isocyanate concentration became 0.1% to obtain an active energy ray-curable resin. 2. Adjustment of active energy ray-curable resin In the synthesis example 1 or 2 obtained above, the antistatic agents shown in the following Table i were prepared in the proportions (parts by weight) shown in Table 2, respectively, and formulated as Photo-polymerization initiator α-hydroxyalkyl phenyl ketone (product name: Irgacure 184, manufactured by BASF Corporation) 3 wt%, ethyl acetate 5 wt% as a diluent, and mixed 'to obtain active energy ray hardenability Resin. 12 201247758 [Table i] 比例 Monoester (ratio of formula (1)) and diester (formula (2)), 50: 19.8 agent 12 ethyl sulphate dodecyl ruthenium sulphate - ammonium sulphate and octyl sulphate hydride 14 1 phosphorus si _ single propyl g rni ^ z Tm. hair - electricity 9 electric agent 1 〇 13 201247758 [Table 2] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Synthesis Example 1 100 Synthesis Example 2 100 100 100 100 100 100 100 Antistatic agent 1 5 Antistatic agent 2 5 Antistatic Agent 3 5 5 Antistatic 剤4 | 5 Antistatic agent 5 5 Antistatic agent 6 5 Antistatic agent 7 5 Antistatic agent 8 Antistatic agent 9 Antistatic agent 10 Antistatic agent 11 Antistatic agent 12 Antistatic agent 13 Electrostatic agent 14 Surface resistance (Ω) 4.2E+12 6.5E+15 2.5E + 9 5.2E + 9 1.9E + 9 1.2E + 8 2.6E + 8 8.1E4-8 Example 9 Example 10 Example 11 Implementation Example 12 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Synthesis Example 1 100 100 100 Synthesis Example 2 100 100 100 100 100 Antistatic agent 1 Antistatic agent 2 Antistatic agent 3 5 7 10 Antistatic agent 4 Antistatic agent 5 antistatic agent 6 antistatic agent 7 antistatic agent 8 5 antistatic agent 9 5 antistatic agent 10 5 antistatic agent 11 5 antistatic Agent 12 Antistatic agent 13 Antistatic agent 14 Surface resistance (Ω) | 5.5E+9 4.2E+12 1.7E+11 3.5E+10 2.1E+16 1.3E+16 2.0E+14 3.2E+16 14 201247758 |Comparative Example 5 Comparative Example 6 Comparative Example 7 Synthesis Example 1 100 100 100 Synthesis Example 2 Antistatic Agent 1 Antistatic Agent 2 Antistatic Agent 3 I Antistatic Agent 4 Antistatic Agent 5 Antistatic Agent 6 Antistatic Agent 7 | Antistatic agent 8 | Antistatic agent 9 Antistatic agent 10 Antistatic agent 11 Antistatic agent 12 5 Antistatic agent 13 5 Antistatic agent 14 | 5 Surface resistance (Ω) | 2.4Ε+16 2.4Ε+16 2Ε+17 θ 3 . Evaluation of active energy ray-curable resin &lt;Production of evaluation sample&gt; The active energy ray-curable resin obtained above was spin-coated (500 rpm, 5 sec = H500 rpm, 15 sec) on a PET film (Toray) On the LUMIRROR) (corona treated surface), after drying at 80 ° C for 10 minutes, ultraviolet rays of 200 mJ/cm 2 were irradiated by a high pressure mercury lamp to prepare an evaluation sample. &lt;Surface resistance measurement condition&gt; The measurement was carried out under the conditions of a temperature of 20 ° C and a humidity of 65% using R8340 ULTRA HIGH RESISTANCE METER manufactured by ADVANTEST Co., Ltd. The evaluation results are shown in Table 1 above. As is clear from the results shown in Table 2, when R and η in the general formula (1) are outside the pre-201224,477,58 * 疋范园 (Comparative Examples 2 to 3), when the structure is different from the general formula (1) (comparison In Examples 5 to 7), the surface resistance of the antistatic agent exceeds ι 〇ΐ 2 Ω. The antistatic agent of the present invention and the active energy ray curable resin obtained by using the antistatic agent can be suitably used for a hard coat film for an optical film, an optical film, and an antistatic protective film. The present invention has been described in detail above with reference to the specific embodiments of the present invention, and various modifications and changes can be made without departing from the spirit and scope of the invention. It is obvious and easy to know. The present application is based on a Japanese patent application filed on Apr. 7, 2011 (Japanese Patent Application No. 2011-085008), the disclosure of which is incorporated herein by reference. W [Simple description of the diagram] No flaws [Description of main components] No 16 201247758 Dimensional) 1 1 〇ς 〇 4 9 Patent 8.11 Amendment I, invention patent description 1 (This specification format, order 'Do not Please do not fill in the number of any change 1 mark: Please fill in the number of the case number. ※Application number: 101106049 ※Working PC classification: ※Application date: February 23, 2012. Name of the invention: Active energy line hardening An antistatic agent for a resin and an active energy ray-curable resin containing the antistatic agent. Abstract: The present invention provides an antistatic agent for an active energy ray-curable resin, which can be more resistant to conventional use. The electrostatic energy ray-curable resin further reduces the surface resistance value. The antistatic agent for the active energy ray-curable resin is characterized by the following general formula (1) and/or (2): RO (CH2CH2 〇) Tp 〒 OH (1) OH R0 (CH2CH20) R0(CH2CH20)n OH (wherein R represents a carbon number of 8 to 13 and 0$η$6). III. Abstract of English invention: (2) 201247758 • VII. Patent application scope: It is characterized by (1) (2): Contains request 1 · An antistatic agent for active energy ray-curable resin, with the following general formula (1) And/or (2) to indicate: 〇ROfC^C^O^P^OH OH O r〇(ch2ch2〇)v 〇R0(CH2CH20)n/ X〇H (wherein R represents a carbon number of 8~13 Alkyl, 0$n$6). An active energy ray-curable resin, which is characterized by the active energy ray-curable resin according to claim 2, wherein the surface resistance is ΙΟ12 Ω or less. 201247758 IV. Designated representative map: (1) The representative representative of the case is: None (2) The symbol of the representative figure is a simple description: None 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: