JP5711452B2 - Active energy ray-curable antistatic composition - Google Patents

Description

  The present invention cures by irradiation with active energy rays and gives a cured film having high hardness, high antistatic properties and high transparency when applied to a substrate, and is particularly useful as an active energy ray curing as a hard coating agent. The present invention relates to a mold antistatic composition.

Conventionally, hard coating agents have been used for the purpose of preventing dust adhesion to the plastic surface and preventing scratches due to friction.
In particular, hard coating agents used in the display field such as cathode ray tube (CRT), liquid crystal display (LCD), plasma display (PDP), electroluminescence display (EL), touch panel, etc., as well as surface protection of the front surface of the panel, adhesion of dust due to static electricity It has been desired to have prevention and high transparency for obtaining high image quality.
Further, in other fields such as optical disks, optical fibers, and polarizers in LCDs, a hard coating agent having antistatic performance, surface protection function, and high transparency is desired.

  Generally, in the antistatic hard coating agent, there is a method of forming a coating layer containing an antistatic property imparting agent for the purpose of imparting antistatic property to the hard coating film, and as an antistatic property imparting agent therefor. , Surfactants, salts (for example, Patent Document 1), inorganic conductive fillers (for example, Patent Document 2), and ionic liquids (for example, Patent Document 3) have been proposed.

JP 2003-41194 A JP 10-235807 A JP 2007-70399 A

However, in the case of surfactants and salts, if the content in the coating layer is low, sufficient antistatic properties will not be exhibited, and if the content is high, it will easily bleed out to the surface of the coating layer, and then easily with running water, wiping, etc. There is a problem that the antistatic property is not long-lasting.
In the case of an inorganic conductive filler, if the content in the coating layer is small, the antistatic property will not be exhibited, and if the content is large, the transparency of the coating film will be impaired, it will be colored, the cost will be very high, etc. There was a problem.
Further, in the case of an ionic liquid, there is a problem that when the content is small, sufficient antistatic properties are not exhibited, and when the content is large, the hardness of the coating film is impaired.

  Then, an object of this invention is to provide the coating composition which provides the cured film which expresses the outstanding antistatic property, without impairing high hardness and high transparency.

The inventors of the present invention have reached the present invention as a result of studies to achieve the above object.
That is, the present invention relates to an ionic liquid (A) composed of an anion (a) and an onium cation group (b) represented by the following general formula (1), a polyfunctional (meth) acrylate (B), and polymerization An active energy ray-curable antistatic composition (D) comprising an initiator (C).
^Q-Y - (1)
Wherein (1), the organic group Q is a path perfluoroalkyl group, a part may be modified with polyoxyethylene groups. Y ^- is COO ^- or PO ₄ ^- represents a. ]

The active energy ray-curable antistatic resin composition of the present invention has the following effects.
(1) A cured product obtained by curing the composition exhibits high hardness.
(2) A cured product obtained by curing the composition exhibits high antistatic properties.
(3) A cured product obtained by curing the composition exhibits high transparency.

  The active energy ray-curable antistatic composition (D) of the present invention includes an ionic liquid (A), a polyfunctional (meth) acrylate (B) having a specific chemical structure excellent in surface concentration performance, and polymerization. It is obtained by mixing the initiator (C).

  Since the ionic liquid (A) having a specific chemical structure in the present invention is excellent in surface concentration performance, the ionic liquid (A) is used together with the polyfunctional (meth) acrylate (B) and the polymerization initiator (C). When applied to a material and cured, a cured film having high hardness, high antistatic properties, and high transparency can be provided.

  The ionic liquid (A) in the present invention comprises an onium cation group (b) paired with an anion portion (a) having a specific chemical structure site effective as a surface concentrating agent.

Examples of the anion portion (a) include a carboxylate anion (a1), a sulfonate anion (a2), and a phosphate anion (a3) having a specific chemical structure represented by the following general formula (1). .
^Q-Y - (1)
In Expression (1), Q is an alkyl group, a perfluoroalkyl group or a polysiloxane group, Y ^- is ^COO -, SO ₃ ^- or PO ₄ ^- is. ]

The anion portion (a) includes a hydrophobic group site Q represented in the above formula (1) in the molecule.
Specific examples of Q include an aliphatic saturated alkyl group having 6 to 18 carbon atoms (Q1), a perfluoroalkyl group (Q2) represented by the following general formula (2), and the following general formula (3). The polysiloxane group (Q3) represented is mentioned.

_{CF 3 - (CF 2) k-} (CH 2) m- (CH 2 CH 2 O) n- (2)
[In the formula (2), k represents 3 to 20, m represents 0 or 1 to 10, and n represents 0 or an integer of 1 to 5. ]

[In Formula (3), X represents the alkyl group by which the terminal was substituted by the hydroxyl group or the (meth) acrylate group. Y represents an alkyl group having 1 to 10 carbon atoms or an alkyl group containing an oxyethylene group in the chain. p, q, and r each independently represents 0 or an integer of 1 to 10. However, p + q + r is 1 or more. ]

Examples of the aliphatic saturated alkyl group having 6 to 18 carbon atoms (Q1) as the hydrophobic group site Q include a hexyl group, an octyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, and an octadecyl group.
Of these, a decyl group, a dodecyl group, and a tetradecyl group are preferable from the viewpoint of surface concentration.

  Examples of the perfluoroalkyl group (Q2) represented by the general formula (2) as the hydrophobic group site Q include a perfluoroalkyl group (Q21) and an ethylene oxide-modified perfluoroalkyl group (Q22).

Incidentally, k in the above formula (2) represents the number of repeating units (CF _2), usually 3 to 20, from the viewpoint of surface concentrating property, preferably 3 to 10, more preferably 3-5 integer It is.
m represents the number of methylene groups, and is usually 0 or 1 to 10, preferably 0 or 1 to 5, more preferably an integer of 0 or 1 to 3, from the viewpoint of surface concentration and compatibility.
n represents the number of oxyethylene groups, and is usually an integer of 0 or 1 to 5, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, from the viewpoint of compatibility.

Perfluoroalkyl group (Q21) includes perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, perfluorodecyl group, perfluorododecyl group, perfluorotetradecyl group, perfluorohexadecyl group, perfluorooctadecyl group. Group, perfluoroicosyl group, perfluorobutylethyl group, perfluorobutylhexyl group, perfluorobutyldecyl group, perfluorooctylethyl group, perfluorooctylhexyl group, perfluorooctyldecyl group, perfluorododecylethyl group, Examples include perfluorododecylhexyl group and perfluorododecyldecyl group.
Among these, a perfluorohexyl group and a perfluorododecyl group are preferable from the viewpoint of surface concentration.

As the ethylene oxide (hereinafter abbreviated as EO) modified perfluoroalkyl group (Q22), EO2 mol addition perfluorobutyl group, EO5 mol addition perfluorobutyl group, EO2 mol addition perfluorooctyl group, EO5 mol addition perfluorooctyl Group, EO2 mole addition perfluorododecyl group, EO5 mole addition perfluorododecyl group, EO2 mole addition perfluorohexadecyl group, EO5 mole addition perfluorohexadecyl group, EO2 mole addition perfluorobutylethyl group, EO5 mole addition perfluorododecyl group Butyl ethyl group, EO 2 mol addition perfluorododecyl hexyl group, and EO 5 mol addition perfluoro dodecyl hexyl group.
Among these, from the viewpoint of surface concentrating properties, preferred are an EO2 mole added perfluorooctyl group and an EO2 mole added perfluorododecyl group.

  The polysiloxane group (Q3) represented by the general formula (3) as the hydrophobic group site Q includes a linear polysiloxane group, a polysiloxane having an EO-modified alkyl group in the side chain, and a side chain. A polysiloxane having a hydroxyl group or (meth) acrylate may be mentioned.

In addition, X in said formula (3) represents the alkyl group by which the terminal was substituted by the hydroxyl group or the (meth) acrylate group.
X is usually an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group or a (meth) acrylate group, and from the viewpoint of surface concentration and compatibility, the terminal is preferably substituted with a hydroxyl group or a (meth) acrylate group It is an alkyl group substituted with a (meth) acrylate group, particularly preferably an alkyl group having 1 to 4 carbon atoms.
Y represents an alkyl group having 1 to 10 carbon atoms or an alkyl group containing an oxyethylene group in the chain. Y is usually an alkyl group having 1 to 10 carbon atoms and an alkyl group containing an oxyethylene group, and from the viewpoint of surface concentration and compatibility, the number of alkyl groups having 1 to 5 carbon atoms and the number of oxyethylene groups is preferably 1. A C1-5 alkyl group having 5 to 5 carbon atoms, more preferably a C1 to C2 alkyl group, and a C1-2 alkyl group having 1 to 2 oxyethylene groups, ease of synthesis and availability From the viewpoint of price, and particularly preferable are an alkyl group having 1 carbon atom and an alkyl group having 1 to 2 carbon atoms having 1 to 2 oxyethylene groups.
p, q, and r each independently represents 0 or an integer of 1 to 10. However, p, q, and r are not 0 simultaneously, and p + q + r is 1 or more. Preferably p + q + r is 3-20, more preferably 5-10.

  From the viewpoint of improving compatibility, it is preferable that a part or a plurality of parts of the polysiloxane group (Q3) is modified with a hydroxyl group, a polyoxyethylene group, and a (meth) acryl group, and modified with a polyoxyethylene group. It is particularly preferable.

  The polysiloxane having an EO-modified alkyl group in the side chain is preferably a polysiloxane having an EO addition mole number of 1 to 20, particularly preferably an EO addition mole number of 2 to 10, from the viewpoint of compatibility.

  Examples of the polysiloxane group (Q3) include dimethylpolysiloxane, methylethylpolysiloxane, methylhexylpolysiloxane, methyldecylsiloxane, EO2 mol addition ethylmethylpolysiloxane, EO2 mol addition hexylmethylpolysiloxane, EO2 mol addition decylmethylpolysiloxane. , EO4 mol addition butyl methyl polysiloxane, EO 4 mol addition octyl methyl polysiloxane, hydroxy containing dimethyl polysiloxane, hydroxy containing ethyl methyl polysiloxane, hydroxy containing EO 2 mol addition ethyl methyl polysiloxane, (meth) acrylate containing dimethyl polysiloxane, ( (Meth) acrylate-containing ethylmethylpolysiloxane, (meth) acrylate-containing EO 2 mol addition ethylmethylpolysiloxane, and (meth) ) Acrylate-containing EO2 mols hydroxyl-containing ethyl methyl polysiloxanes.

  Of these, dimethylpolysiloxane, EO2 mole addition ethylmethylpolysiloxane, hydroxy-containing dimethylpolysiloxane, (meth) acrylate-containing dimethylpolysiloxane, and (meth) acrylate-containing EO2 mole addition are preferable from the viewpoint of surface concentration. Hydroxy-containing ethyl methyl polysiloxane.

  The solubility parameter (SP value) of the organic group Q, which is a hydrophobic group site in the anion portion (a), is usually 3.0 to 9.0, preferably from the viewpoint of increasing surface concentration performance and obtaining excellent antistatic performance. Is 5.0 to 9.0, more preferably 7.0 to 9.0.

Here, the solubility parameter (SP value) is obtained by the following equation.
SP = (ΔH / V) ^1/2
In the formula, ΔH represents the heat of molar evaporation (cal / mol), and V represents the molar volume (cm ³ / mol). In addition, ΔH and V are the heat of molar evaporation (Δei) of the atomic group described in “POLYMERENGINEERING AND SCIENCE, FEBRUARY, 1974, Vol. 14, No. 2, ROBERT F. FEDORS. The sum (ΔH) and the sum (V) of the molar volume (Δvi) can be used.

As the anion portion (a) of the present invention, among those represented by the general formula (1), those having a hydrophobic group site Q having a solubility parameter of 3.0 to 9.0 as shown above are preferable.
Examples of the anion moiety (a) include a carboxylate anion (a1), a sulfonate anion (a2), and a phosphate anion (a3).

  Examples of the carboxylate anion (a1) include an aliphatic saturated alkylcarboxylate anion having 6 to 18 carbon atoms, a perfluoroalkylcarboxylate anion, and a polysiloxane group-containing carboxylate anion.

Of these, decylcarboxylate anion, dodecylcarboxylate anion, tetradecylcarboxylate anion, perfluorohexylcarboxylate anion, perfluorododecylcarboxylate anion, EO2 mol-added perfluorooctyl are preferable from the viewpoint of surface concentration. Carboxylic acid anion, EO2 mole addition perfluorododecyl carboxylate anion, dimethylpolysiloxane group-containing carboxylate anion, EO2 mole addition ethylmethylpolysiloxane group-containing carboxylate anion, hydroxy-containing dimethylpolysiloxane group-containing carboxylate anion, (meth) Acrylate-containing dimethylpolysiloxane group-containing carboxylate anion, and (meth) acrylate-containing EO2 mole addition hydroxy-containing ethylmethylpolysiloxane group-containing carbo It is an acid anion.
More preferred are tetradecylcarboxylate anion, perfluorododecylcarboxylate anion, and EO2 mole added perfluorododecylcarboxylate anion.

  Examples of the sulfonate anion (a2) include an aliphatic saturated alkyl sulfonate anion having 6 to 18 carbon atoms, a perfluoroalkyl sulfonate anion, and a polysiloxane group-containing sulfonate anion.

Of these, decyl sulfonate anion, dodecyl sulfonate anion, tetradecyl sulfonate anion, perfluorohexyl sulfonate anion, perfluorododecyl sulfonate anion, EO2 mol-added perfluorooctyl are preferable from the viewpoint of surface concentration. Sulfonic acid anion, EO2 mol addition perfluorododecyl sulfonate anion, dimethylpolysiloxane group-containing sulfonate anion, EO2 mol addition ethylmethylpolysiloxane group-containing sulfonate anion, hydroxy-containing dimethylpolysiloxane group-containing sulfonate anion, (meth) Acrylate-containing dimethylpolysiloxane group-containing sulfonate anion and (meth) acrylate-containing EO 2 mol addition hydroxy-containing ethylmethylpolysiloxane group-containing sulfone It is an acid anion.
More preferred are tetradecyl sulfonate anion, perfluorododecyl sulfonate anion, and EO2 mole added perfluorododecyl sulfonate anion.

  Examples of the phosphate anion (a3) include an aliphatic saturated alkyl phosphate anion having 6 to 18 carbon atoms, a perfluoroalkyl phosphate anion, and a polysiloxane group-containing phosphate anion.

  Among these, decyl phosphate anion, dodecyl phosphate anion, tetradecyl phosphate anion, perfluorohexyl phosphate anion, perfluorododecyl phosphate anion, EO2 mol-added perfluorooctyl phosphate are preferable from the viewpoint of surface concentration. Anion, EO2 mol addition perfluorododecyl phosphate anion, dimethylpolysiloxane group-containing phosphate anion, EO2 mol addition ethylmethylpolysiloxane group-containing phosphate anion, hydroxy-containing dimethylpolysiloxane group-containing phosphate anion, (meth) acrylate-containing A dimethylpolysiloxane group-containing phosphate anion, and a (meth) acrylate-containing EO 2-mole addition hydroxy-containing ethylmethylpolysiloxane group-containing phosphate anion, more preferably tetradecyl Phosphate anion, perfluoro dodecyl phosphate anion, and EO2 mole addition perfluoro dodecyl phosphate anion.

  Of the carboxylate anion (a1), sulfonate anion (a2), and phosphate anion (a3), the carboxylate anion (a1) and phosphate are preferable from the viewpoints of synthesis, availability, and price. The anion (a2), particularly preferred is the carboxylate anion (a1).

  The onium cation group (b) includes an amidinium cation (b1), a guanidinium cation (b2), and a mixture thereof.

  Examples of the amidinium cation (b1) include an imidazolinium cation (b11), an imidazolium cation (b12), a tetrahydropyrimidinium cation (b13), and a dihydropyrimidinium cation (b14).

(B11) imidazolinium cation 5 to 15 carbon atoms (hereinafter abbreviated as C), such as 1,2,3,4-tetramethylimidazolinium, 1,3,4-trimethyl-2-ethylimidazolinium, 1 , 3-dimethylimidazolinium, 1,3-dimethyl-2,4-diethylimidazolinium, 1,2-dimethyl-3,4-diethylimidazolinium, 1-methyl-2,3,4-triethylimidazole Linium, 1,2,3,4-tetraethylimidazolinium, 1,2,3-trimethylimidazolinium, 1,3-dimethyl-2-ethylimidazolinium, 1-ethyl-2,3-dimethylimidazole Linium, 1,2,3-triethylimidazolinium, 4-cyano-1,2,3-trimethylimidazolinium, 3-cyanomethyl-1,2-dimethyli Midazolinium, 2-cyanomethyl-1,3-dimethylimidazolinium, 4-acetyl-1,2,3-trimethylimidazolinium, 3-acetylmethyl-1,2-dimethylimidazolinium, 4-methylcarbooxymethyl -1,2,3-trimethylimidazolinium, 3-methylcarbooxymethyl-1,2-dimethylimidazolinium, 4-methoxy-1,2,3-trimethylimidazolinium, 3-methoxymethyl-1, 2-dimethylimidazolinium, 4-formyl-1,2,3-trimethylimidazolinium, 3-formylmethyl-1,2-dimethylimidazolinium, 3-hydroxyethyl-1,2-dimethylimidazolinium, 4-hydroxymethyl-1,2,3-trimethylimidazolinium, 2-hydroxyethyl- , 3-dimethyl imidazolinium

(B12) imidazolium cation C5-15, such as 1,3-dimethylimidazolium, 1,3-diethylimidazolium, 1-ethyl-3-methylimidazolium, 1,2,3-trimethylimidazolium, 1,2 , 3,4-tetramethylimidazolium, 1,3-dimethyl-2-ethylimidazolium, 1,2-dimethyl-3-ethyl-imidazolium, 1,2,3-triethylimidazolium, 1,2,3 , 4-tetraethylimidazolium, 1,3-dimethyl-2-phenylimidazolium, 1,3-dimethyl-2-benzylimidazolium, 1-benzyl-2,3-dimethyl-imidazolium, 4-cyano-1, 2,3-trimethylimidazolium, 3-cyanomethyl-1,2-dimethylimidazolium, 2-cyanomethyl-1 , 3-dimethyl-imidazolium, 4-acetyl-1,2,3-trimethylimidazolium, 3-acetylmethyl-1,2-dimethylimidazolium, 4-methylcarbooxymethyl-1,2,3-trimethylimidazole Lithium, 3-methylcarbooxymethyl-1,2-dimethylimidazolium, 4-methoxy-1,2,3-trimethylimidazolium, 3-methoxymethyl-1,2-dimethylimidazolium, 4-formyl-1, 2,3-trimethylimidazolium, 3-formylmethyl-1,2-dimethylimidazolium, 3-hydroxyethyl-1,2-dimethylimidazolium, 4-hydroxymethyl-1,2,3-trimethylimidazolium, 2 -Hydroxyethyl-1,3-dimethylimidazolium

(B13) Tetrahydropyrimidinium cation C6-15, such as 1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 1,2,3-trimethyl-1,4,5,6-tetrahydropyri Midinium, 1,2,3,4-tetramethyl-1,4,5,6-tetrahydropyrimidinium, 1,2,3,5-tetramethyl-1,4,5,6-tetrahydropyrimidinium 8-methyl-1,8-diazabicyclo [5,4,0] -7-undecenium, 5-methyl-1,5-diazabicyclo [4,3,0] -5-nonenium, 4-cyano-1,2 , 3-trimethyl-1,4,5,6-tetrahydropyrimidinium, 3-cyanomethyl-1,2-dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-cyanomethyl-1,3-dimethyl Til-1,4,5,6-tetrahydropyrimidinium, 4-acetyl-1,2,3-trimethyl-1,4,5,6-tetrahydropyrimidinium, 3-acetylmethyl-1,2-dimethyl -1,4,5,6-tetrahydropyrimidinium, 4-methylcarbooxymethyl-1,2,3-trimethyl-1,4,5,6-tetrahydropyrimidinium, 3-methylcarbooxymethyl-1 , 2-dimethyl-1,4,5,6-tetrahydropyrimidinium, 4-methoxy-1,2,3-trimethyl-1,4,5,6-tetrahydropyrimidinium, 3-methoxymethyl-1, 2-dimethyl-1,4,5,6-tetrahydropyrimidinium, 4-formyl-1,2,3-trimethyl-1,4,5,6-tetrahydropyrimidinium, 3-formylmethi -1,2-dimethyl-1,4,5,6-tetrahydropyrimidinium, 3-hydroxyethyl-1,2-dimethyl-1,4,5,6-tetrahydropyrimidinium, 4-hydroxymethyl-1 , 2,3-Trimethyl-1,4,5,6-tetrahydropyrimidinium, 2-hydroxyethyl-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium

(B14) Dihydropyrimidinium cation C6-20, such as 1,3-dimethyl-1,4- or -1,6-dihydropyrimidinium [these are 1,3-dimethyl-1,4 (6)- This is expressed as dihydropyrimidinium, and the same notation is used hereinafter. 1,2,3-trimethyl-1,4 (6) -dihydropyrimidinium, 1,2,3,4-tetramethyl-1,4 (6) -dihydropyrimidinium, 1,2,3 5-tetramethyl-1,4 (6) -dihydropyrimidinium, 8-methyl-1,8-diazabicyclo [5,4,0] -7,9 (10) -undecadienium, 5-methyl- 1,5-diazabicyclo [4,3,0] -5,7 (8) -nonadienium, 4-cyano-1,2,3-trimethyl-1,4 (6) -dihydropyrimidinium, 3-cyanomethyl- 1,2-dimethyl-1,4 (6) -dihydropyrimidinium, 2-cyanomethyl-1,3-dimethyl-1,4 (6) -dihydropyrimidinium, 4-acetyl-1,2,3- Trimethyl-1,4 (6) -dihydropyrimidinium, 3 Acetylmethyl-1,2-dimethyl-1,4 (6) -dihydropyrimidinium, 4-methylcarbooxymethyl-1,2,3-trimethyl-1,4 (6) -dihydropyrimidinium, 3- Methylcarbooxymethyl-1,2-dimethyl-1,4 (6) -dihydropyrimidinium, 4-methoxy-1,2,3-trimethyl-1,4 (6) -dihydropyrimidinium, 3-methoxy Methyl-1,2-dimethyl-1,4 (6) -dihydropyrimidinium, 4-formyl-1,2,3-trimethyl-1,4 (6) -dihydropyrimidinium, 3-formylmethyl-1 , 2-Dimethyl-1,4 (6) -dihydropyrimidinium, 3-hydroxyethyl-1,2-dimethyl-1,4 (6) -dihydropyrimidinium, 4-hydroxymethyl-1,2,3 Trimethyl-1,4 (6) - dihydropyrimidinium, 1,3 2-hydroxyethyl dimethyl-1,4 (6) - hydro pyrimidinium.

  Examples of the guanidinium cation (b2) include a guanidinium cation (b21) having an imidazolinium skeleton, a guanidinium cation (b22) having an imidazolium skeleton, and a guanidinium cation (b23) having a tetrahydropyrimidinium skeleton. Is mentioned.

(B21) Guanidinium cation having an imidazolinium skeleton C8-15, such as 2-dimethylamino-1,3,4-trimethylimidazolinium, 2-diethylamino-1,3,4-trimethylimidazolinium, 2 -Diethylamino-1,3-dimethyl-4-ethylimidazolinium, 2-dimethylamino-1-methyl-3,4-diethylimidazolinium, 2-diethylamino-1-methyl-3,4-diethylimidazolinium 2-diethylamino-1,3,4-tetraethylimidazolinium, 2-dimethylamino-1,3-dimethylimidazolinium, 2-diethylamino-1,3-dimethylimidazolinium, 2-dimethylamino-1- Ethyl-3-methylimidazolinium, 2-diethylamino-1,3-diethylimid Dazolinium, 1,5,6,7-tetrahydro-1,2-dimethyl-2H-imide [1,2a] imidazolinium, 1,5-dihydro-1,2-dimethyl-2H-imide [1,2a] Imidazolinium, 1,5,6,7-tetrahydro-1,2-dimethyl-2H-pyrimido [1,2a] imidazolinium, 1,5-dihydro-1,2-dimethyl-2H-pyrimido [1, 2a] imidazolinium, 2-dimethylamino-4-cyano-1,3-dimethylimidazolinium, 2-dimethylamino-3-cyanomethyl-1-methylimidazolinium, 2-dimethylamino-4-acetyl-1 , 3-dimethylimidazolinium, 2-dimethylamino-3-acetylmethyl-1-methylimidazolinium, 2-dimethylamino-4-methylcarbooxime 1,3-dimethylimidazolinium, 2-dimethylamino-3-methylcarbooxymethyl-1-methylimidazolinium, 2-dimethylamino-4-methoxy-1,3-dimethylimidazolinium, 2- Dimethylamino-3-methoxymethyl-1-methylimidazolinium, 2-dimethylamino-4-formyl-1,3-dimethylimidazolinium, 2-dimethylamino-3-formylmethyl-1-methylimidazolinium, 2-dimethylamino-3-hydroxyethyl-1-methylimidazolinium, 2-dimethylamino-4-hydroxymethyl-1,3-dimethylimidazolinium;

(B22) Guanidinium cation having an imidazolium skeleton C8-15, such as 2-dimethylamino-1,3,4-trimethylimidazolium, 2-diethylamino-1,3,4-trimethylimidazolium, 2-diethylamino- 1,3-dimethyl-4-ethylimidazolium, 2-dimethylamino-1-methyl-3,4-diethylimidazolium, 2-diethylamino-1-methyl-3,4-diethylimidazolium, 2-diethylamino-1 , 3,4-tetraethylimidazolium, 2-dimethylamino-1,3-dimethylimidazolium, 2-diethylamino-1,3-dimethylimidazolium, 2-dimethylamino-1-ethyl-3-methylimidazolium, 2 -Diethylamino-1,3-diethylimidazolium, 1,5, 6,7-tetrahydro-1,2-dimethyl-2H-imide [1,2a] imidazolium, 1,5-dihydro-1,2-dimethyl-2H-imide [1,2a] imidazolium, 6,7-tetrahydro-1,2-dimethyl-2H-pyrimido [1,2a] imidazolium, 1,5-dihydro-1,2-dimethyl-2H-pyrimido [1,2a] imidazolium, 2-dimethylamino -4-cyano-1,3-dimethylimidazolium, 2-dimethylamino-3-cyanomethyl-1-methylimidazolium, 2-dimethylamino-4-acetyl-1,3-dimethylimidazolinium, 2-dimethylamino -3-acetylmethyl-1-methylimidazolium, 2-dimethylamino-4-methylcarbooxymethyl-1,3-dimethylimidazolium 2-dimethylamino-3-methylcarbooxymethyl-1-methylimidazolium, 2-dimethylamino-4-methoxy-1,3-dimethylimidazolium, 2-dimethylamino-3-methoxymethyl-1-methylimidazolium 2-dimethylamino-4-formyl-1,3-dimethylimidazolium, 2-dimethylamino-3-formylmethyl-1-methylimidazolium, 2-dimethylamino-3-hydroxyethyl-1-methylimidazolium, 2-dimethylamino-4-hydroxymethyl-1,3-dimethylimidazolium;

(B23) Guanidinium cation having a tetrahydropyrimidinium skeleton C10-20, such as 2-dimethylamino-1,3,4-trimethyl-1,4,5,6-tetrahydropyrimidinium, 2-diethylamino-1 , 3,4-trimethyl-1,4,5,6-tetrahydropyrimidinium, 2-diethylamino-1,3-dimethyl-4-ethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethyl Amino-1-methyl-3,4-diethyl-1,4,5,6-tetrahydropyrimidinium, 2-diethylamino-1-methyl-3,4-diethyl-1,4,5,6-tetrahydropyrimidi Ni, 2-diethylamino-1,3,4-tetraethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-1,3- Dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-diethylamino-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-1-ethyl-3-methyl -1,4,5,6-tetrahydropyrimidinium, 2-diethylamino-1,3-diethyl-1,4,5,6-tetrahydropyrimidinium, 1,3,4,6,7,8-hexahydro -1,2-dimethyl-2H-imide [1,2a] pyrimidinium, 1,3,4,6-tetrahydro-1,2-dimethyl-2H-imide [1,2a] pyrimidinium, 1,3,4,6 , 7,8-Hexahydro-1,2-dimethyl-2H-pyrimido [1,2a] pyrimidinium, 1,3,4,6-tetrahydro-1,2-dimethyl-2H-pyrimido [1,2a] pyrim Dinium, 2-dimethylamino-4-cyano-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-3-cyanomethyl-1-methyl-1,4,5,6 -Tetrahydropyrimidinium, 2-dimethylamino-4-acetyl-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-3-acetylmethyl-1-methyl-1, 4,5,6-tetrahydropyrimidinium, 2-dimethylamino-4-methylcarbooxymethyl-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-3-methyl Carbooxymethyl-1-methyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-4-methoxy-1,3-dimethyl-1, , 5,6-tetrahydropyrimidinium, 2-dimethylamino-3-methoxymethyl-1-methyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-4-formyl-1,3- Dimethyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-3-formylmethyl-1-methyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-3-hydroxy Ethyl-1-methyl-1,4,5,6-tetrahydropyrimidinium, 2-dimethylamino-4-hydroxymethyl-1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium;

  Of these onium cation groups (b), the amidinium cation (b1) is preferable from the viewpoint of the antistatic performance of the cured film of the antistatic composition, and the imidazolium cation (b12) is particularly preferable. Is the 1-ethyl-3-methylimidazolium cation.

  Examples of the polyfunctional (meth) acrylate (B) as the second essential component in the present invention include polyfunctional (meth) acrylates having at least 2 to 6 (meth) acryloyl groups and mixtures thereof.

  As polyfunctional (meth) acrylate having 2 to 6 (meth) acryloyl groups, di (meth) acrylate (B1), poly (trivalent to hexavalent) (meth) acrylate (B2), polyester (meth) Acrylate (B3), urethane (meth) acrylate (B4), epoxy (meth) acrylate (B5), butadiene polymer (B6) having (meth) acryloyl groups, dimethylpolysiloxane (B7) having (meth) acryloyl groups Etc.

(B1) di (meth) acrylate (B11) polyoxyalkylene (alkylene is C2-4) [molecular weight 106 or more and number average molecular weight [hereinafter abbreviated as Mn. The measurement is based on a gel permeation chromatography (GPC) method. ] 3,000 or less] di (meth) acrylate polyethylene glycol (hereinafter abbreviated as PEG) (Mn400), polypropylene glycol (hereinafter abbreviated as PPG) (Mn200) and polytetramethylene glycol (hereinafter abbreviated as PTMG) ( Each di (meth) acrylate of Mn650);

(B12) Alkylene oxide of dihydric phenol compound (hereinafter abbreviated as AO) (2 to 30 mol) Adduct di (meth) acrylate Dihydric phenol compound [C6-18, for example, monocyclic phenol (catechol, resorcinol) , Hydroquinone, etc.), condensed polycyclic phenols (dihydroxynaphthalene, etc.), bisphenol compounds (bisphenol A, -F, -S, etc.)] AO adduct [resorcinol ethylene oxide 4 mol adduct di (meth) acrylate, dihydroxy Propylene oxide of naphthalene (hereinafter abbreviated as PO) 4 mol adduct di (meth) acrylate, bisphenol A, -F and -S, EO 2 mol, PO4 mol adducts, etc.] ) Acrylate, etc .;

(B13) Di (meth) acrylate of aliphatic dihydric alcohol (C2-30) Each of dipentyl glycol (hereinafter abbreviated as NPG) and 1,6-hexanediol (hereinafter abbreviated as 1,6-HD) (Meth) acrylate and the like;

(B14) Di (meth) acrylate of alicyclic dihydric alcohol (C6-30) Di (meth) acrylate of dimethyloltricyclodecane, di (meth) acrylate of cyclohexanedimethanol and di (meth) hydrogenated bisphenol A Acrylate etc.

(B2) Poly (trivalent to hexavalent) (meth) acrylate C3-40 polyvalent (trivalent to hexavalent or higher) alcohol and its AO adduct poly (meth) acrylate trimethylolpropane (hereinafter referred to as TMP) Abbreviated) tri (meth) acrylate, glycerin (hereinafter abbreviated as GR) tri (meth) acrylate, TMP EO 3 mol and PO 3 mol adduct tri (meth) acrylate, GR EO 3 mol and PO 3 mol adduct Each of tri (meth) acrylate, pentaerythritol (hereinafter abbreviated as PE), tri (meth) acrylate, PE tetra (meth) acrylate, PE EO4 mol adduct tetra (meth) acrylate, dipentaerythritol (hereinafter referred to as PE) , Abbreviated as DPE) penta (meth) acrylate, DPE hexa (meth) a Relate and the like;

(B3) Polyester (meth) acrylates obtained by esterification of polyvalent (divalent to tetravalent) carboxylic acids, polyvalent (divalent to octavalent or higher) alcohols and ester-forming acryloyl group-containing compounds Polyester acrylate having an ester bond and 5 or more acryloyl groups and a molecular weight of 150 or more and Mn 4,000 or less

  Examples of the polyvalent carboxylic acid constituting the polyester include aliphatic [C3-20, such as malonic acid, maleic acid (anhydride), adipic acid, sebacic acid, succinic acid, and an acid anhydride reaction product (dipentaerythritol. And cycloaliphatic [C5-30, such as cyclohexanedicarboxylic acid, tetrahydro (anhydrous) phthalic acid, methyltetrahydro (anhydride) phthalic acid] and aromatic polycarboxylic acids [C8-30] For example, isophthalic acid, terephthalic acid, phthalic acid (anhydride), trimellitic acid (anhydride), pyromellitic acid (anhydride)].

(B4) Urethane (meth) acrylate plural obtained by urethanization reaction with poly (bifunctional to trifunctional or higher) isocyanate, polyvalent (divalent to hexavalent or higher) polyol, hydroxyl group-containing (meth) acrylate Urethane bond (meth) acrylate having a molecular weight of 400 or more and Mn of 5,000 or less having a urethane bond of 2 and two or more acryloyl groups

  Corresponding polyisocyanates include C6-33 (excluding the carbon of the NCO group), such as aliphatic polyisocyanates [hexamethylene diisocyanate (HDI) etc.], aromatic (aliphatic) polyisocyanates [2,4- and / or 2 , 6-tolylene diisocyanate (TDI), 1,5-naphthalene diisocyanate (NDI), xylylene diisocyanate (XDI), etc.], cycloaliphatic polyisocyanates [isophorone diisocyanate (IPDI), 4,4′-methylenebis (cyclohexyl isocyanate) And the like].

  Examples of the polyol include a molecular weight of 62 or more and Mn of 3,000 or less, such as ethylene glycol, 1,4-butanediol (hereinafter abbreviated as EG and 1,4-BD, respectively), NPG, polyether polyol, polycaprolactone polyol, polyester polyol, Examples thereof include polycarbonate polyol and PTMG.

  Examples of the hydroxyl group-containing (meth) acrylate include C5-30, such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, PE tri (meth) acrylate, DPE penta (meth) acrylate, and the like.

(B5) Epoxy (meth) acrylate Epoxy (meth) acrylate having a molecular weight of 400 or more and Mn of 5,000 or less obtained by reacting a polyvalent (2 to 4 valent) epoxide with (meth) acrylic acid;

(B6) butadiene polymer having a (meth) acryloyl group in the main chain and / or side chain, polybutadiene poly (meth) acrylate (Mn 500 to 500,000), etc.

(B7) A siloxane polymer having a (meth) acryloyl group in the main chain and / or side chain of dimethylpolysiloxane, dimethylpolysiloxane poly (meth) acrylate (Mn 300 to 20,000)

  Of these (B1) to (B7), from the viewpoint of the hardness of the cured film of the antistatic composition, preferably (B2) to (B7), more preferably (B2), and particularly preferably DPE penta (meth). Hexa (meth) acrylate of acrylate and DPE.

  The content of the ionic liquid (A) relative to (B) in the resin composition of the present invention is usually 0.1 to 10% by weight, preferably from the viewpoint of antistatic properties, toughness of the coating film, and coating properties. Is 0.2 to 5% by weight, more preferably 0.2 to 2% by weight.

  As the polymerization initiator (C) as the third essential component in the present invention, a hydroxybenzoyl compound (2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, benzoin alkyl ether) ), Benzoylformate compound (such as methylbenzoylformate), thioxanthone compound (such as isopropylthioxanthone), benzophenone (such as benzophenone), phosphate compound (such as 1,3,5-trimethylbenzoyldiphenylphosphine oxide), benzyldimethyl Ketals and the like, and mixtures thereof.

  Of these, from the viewpoint of preventing coloring of the cured product, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone and 1,3,5-trimethylbenzoyldiphenylphosphine oxide are preferable. Particularly preferred is 1-hydroxycyclohexyl phenyl ketone.

  The amount of (C) used is preferably 0.5 to 15% by weight, more preferably 1 to 10% from the viewpoint of curability and coloring of the cured product based on the sum of (A) and (B) and (C). % By weight.

  The active energy ray-curable antistatic composition (D) of the present invention may further contain various additives (E) that are used in coatings as necessary as long as the effects of the present invention are not impaired.

  Additives (E) include inorganic fillers, organic pigments, dispersants, antifoaming agents, leveling agents, silane coupling agents, thixotropic agents (thickeners), slip agents, antioxidants and UV absorbers. Is included.

  The additive (E) capable of improving the hardness includes inorganic fillers, and from the viewpoint of transparency, silica fine particles and inorganic oxide fine particles having a diameter of 5 to 50 nm are preferable, and silica having a diameter of 10 to 30 nm is preferable. Particulates are particularly preferred.

  The amount of the inorganic filler used is usually 60% by weight or less based on the total weight of the composition of the present invention, preferably 5 to 30% by weight, particularly preferably 10 to 20% by weight from the viewpoint of the effect of addition and transparency. %.

  Examples of the additive (E) that can improve the coating property and the surface smoothness include a leveling agent, and a fluorine-based leveling agent and a silicone-based leveling agent are preferable.

  The amount of the leveling inorganic filler used is usually 2% by weight or less based on the total weight of the composition of the present invention, preferably 0.05 to 1% by weight, particularly preferably 0, from the viewpoint of addition effect and transparency. .1 to 0.5% by weight.

  In order to adjust the viscosity of the composition of the present invention to a viscosity suitable for coating, a coating diluted with a solvent as necessary can be used.

  The amount of the solvent used is usually 2,000% or less, preferably 10 to 500%, based on the total weight of the composition. Moreover, the viscosity of a coating material is the temperature (usually 5-60 degreeC) at the time of use, and is 5-5000 mPa * s normally, Preferably it is 50-1,000 mPa * s from a viewpoint of stable coating.

  The solvent is not particularly limited as long as it dissolves the resin component in the composition of the present invention.

  Among these solvents, from the viewpoint of the smoothness of the coating film and the efficiency of solvent removal, preferred are esters, ketones and alcohols having a boiling point of 50 to 100 ° C., more preferred are ethyl acetate, methyl ethyl ketone, acetone, i-propanol, Ethanol, methanol and mixtures thereof, particularly preferably ethyl acetate, methyl ethyl ketone, i-propanol and mixtures thereof.

  The composition of the present invention is diluted with a solvent, if necessary, applied to at least a part of at least one side of the substrate, and dried if necessary, and then irradiated with active energy rays such as ultraviolet rays, electron beams, and X-rays. The hard coat coating material having a cured film can be obtained by curing.

In coating, for example, a coating machine [bar coater, gravure coater, roll coater (size press roll coater, gate roll coater, etc.), air knife coater, spin coater, blade coater, etc.] can be used.
A coating film thickness is 0.5-300 micrometers normally as a film thickness after hardening drying. The upper limit is preferably 250 μm from the viewpoints of drying properties and curability, and the lower limit is preferably 1 μm from the viewpoints of wear resistance, solvent resistance, and contamination resistance.

When the composition of the present invention is used after being diluted with a solvent, it is preferably dried after coating. Examples of the drying method include hot air drying (such as a dryer).
The drying temperature is usually 10 to 200 ° C., the upper limit is preferably 150 ° C. from the viewpoint of the smoothness and appearance of the coating film, and the lower limit is preferably 30 ° C. from the viewpoint of the drying speed.

When the composition of the present invention is cured by ultraviolet irradiation, a known ultraviolet irradiation apparatus can be used.
The irradiation amount of ultraviolet rays (mJ / cm ² ) is usually 10 to 10,000, and preferably 100 to 5,000 from the viewpoint of the curability of the composition and the flexibility of the cured product.

When the composition of the present invention is cured by electron beam irradiation, a known electron beam irradiation apparatus can be used.
The irradiation amount (Mrad) of the electron beam is preferably 0.5 to 20, and preferably 1 to 15 from the viewpoint of the curability of the composition, the flexibility of the cured product, and avoiding damage to the cured film and the substrate. is there.

  Hereinafter, although an example and a comparative example explain the present invention further, the present invention is not limited to these. Hereinafter, unless otherwise specified, “%” represents “% by weight” and “parts” represents “parts by weight”.

Production Example 1
1-ethyl-3-methylimidazolium monomethyl carbonate was synthesized according to the method described in JP-A No. 2001-316372.
Perfluoroalkylcarboxylic acid [trade name “Factent A”, manufactured by Neos Co., Ltd.] (a-1) and the above 1-ethyl-3-methylimidazolium monomethyl carbonate are mixed in an equimolar amount. Ethyl-3-methylimidazolium perfluoroalkylcarboxylate salt (A-1) was obtained.

Production Example 2
Perfluoroalkyl phosphate [trade name “Megafac F-493”, manufactured by Dainippon Ink & Chemicals, Inc.] (a-2) and the above 1-ethyl-3-methylimidazolium monomethyl carbonate in equimolar amounts. By mixing, 1-ethyl-3-methylimidazolium perfluoroalkyl phosphate (A-2) was obtained.

Comparative production example 1
Mono (acryloyloxyethyl) phthalate [trade name “Aronix M-5400”, manufactured by Toagosei Co., Ltd.] (a′-1) and the above 1-ethyl-3-methylimidazolium monomethyl carbonate To obtain 1-ethyl-3-methylimidazolium mono (acryloyloxyethyl) phthalate salt (A′-1).

Example 1
1 part by weight of 1-ethyl-3-methylimidazolium perfluoroalkylcarboxylate salt (A-1) synthesized in Production Example 1, dipentaerythritol hexaacrylate [trade name “Neomer DA-600”, Sanyo Chemical Industries ( (B-1) 99 parts by weight, 1-hydroxycyclohexyl phenyl ketone [trade name “Irgacure 184”, manufactured by Ciba Specialty Chemicals Co., Ltd.] (C-1) 10 parts by weight, methanol 60 parts, methyl ethyl ketone 40 Parts were mixed at once and mixed and stirred uniformly with a disperser to obtain 210 parts (non-volatile content 50%) of the coating composition (D-1) of the present invention.
This composition was applied to a film by a method described later to prepare a coating film.

Example 2
In Example 1, instead of (A-1), 0.5 part of 1-ethyl-3-methylimidazolium perfluoroalkyl phosphate (A-2) synthesized in Production Example 2 was used, and (B-1) The same operation as in Example 1 was performed except that the number of parts was 95.5 parts, and 210 parts by weight of the coating composition (D-2) of the present invention was obtained.

Example 3
In Example 1, the same operation as in Example 1 was performed except that 0.5 part of (A-1) and 0.5 part of (A-2) were used as the ionic liquid (A) component. The coating composition (D-3) 210 parts by weight was obtained.

Comparative Example 1
In Example 1, instead of (A-1), 5 parts by weight of 1-ethyl-3-methylimidazolium mono (acryloyloxyethyl) phthalate salt (A′-1) synthesized in Comparative Production Example 1 was used. Except for using 95 parts by weight of (B-1) as the polyfunctional (meth) acrylate (B) component, the same operation as in Example 1 was performed to obtain 210 parts by weight of the coating composition (D′-1). .

Comparative Example 2
In Example 1, instead of (A-1), (A′-1) was 20 parts by weight, and the polyfunctional (meth) acrylate (B) component was (B-1) 80 parts by weight. The same operation as in Example 1 was performed to obtain 210 parts by weight of a coating composition (D′-2).

Comparative Example 3
In Example 1, instead of (A-1), 5 parts by weight of a polysiloxane / lithium compound [trade name “PC-3600”, manufactured by Maruhishi Oil Chemical Co., Ltd.] was used, and a polyfunctional (meth) acrylate ( B) The same operation as in Example 1 was carried out except that (B-1) was 95 parts by weight as component to obtain 210 parts by weight of a coating composition (D′-3).

Comparative Example 4
In Example 1, instead of (A-1), zinc antimonate [trade name “CELNAX CX-S204”, manufactured by Nissan Chemical Industries, Ltd.], 40 parts by weight, and polyfunctional (meth) acrylate (B) The same operation as in Example 1 was performed except that 60 parts of (B-1) was used as a component to obtain 210 parts by weight of a coating composition (D′-4).

<Method for creating coating film>
100 μm thick PET film [trade name “Cosmo Shine A4300” manufactured by Toyobo Co., Ltd.] Using a bar coater on one side of the base material, the film thickness after drying and curing is applied to 8 μm. did. Furthermore, it was dried at 70 ° C. for 1 minute.
Finally, ultraviolet rays were irradiated at 150 mJ / cm ² by an ultraviolet irradiation device [model number “VPS / I600”, manufactured by Fusion UV Systems Co., Ltd.], and cured to form a coating film.
The performance of this coating film was evaluated by the following method. The performance results are shown in Table 1.

<Performance evaluation method>

(1) Transmittance Based on JIS-K7105, the transmittance is measured using a total light transmittance measuring device [trade name “haze-garddual” manufactured by BYK Gardner Co., Ltd.]. Units%.

(2) Transparency (haze)
Based on JIS-K7105, a haze is measured using the total light transmittance measuring apparatus [Brand name "haze-garddual" BYK gardner Co., Ltd. product]. Units%.

(3) Pencil hardness Pencil hardness is measured according to JIS K-5400.

(4) Antistatic properties [conforms to ASTM D257 (established in 1984)]
A test piece (100 × 100 mm) cut out from the coating film was allowed to stand at 23 ° C. and a humidity of 50% RH for 24 hours, and then a digital super insulation meter [DSM-8103, manufactured by Toa Denpa Kogyo Co., Ltd., and so on. ] Under the same conditions. Unit is Ω / □

As shown in Examples 1 to 3, the antistatic resin of the present invention is excellent in all aspects of transparency, pencil hardness, and surface resistance.
On the other hand, Comparative Example 1, which does not use an ionic liquid having an anion having a low SP value of the main chain as in the present invention, is not satisfactory because the effect is not obtained in a small amount and the surface resistance value is high. Further, Comparative Example 2 in which the ratio of the ionic liquid component is too high is not satisfactory because the pencil hardness is low. Similarly, in Comparative Example 3, since the effect is not obtained with a small amount of inorganic salt, the surface resistance value is not high and satisfactory, and Comparative Example 4 in which the blending ratio of the inorganic filler is too high does not satisfy transparency.

In the antistatic composition of the present invention, since the cured film after curing is excellent in antistatic property, hardness and transparency, surface protection of the front surface of the panel in the display field such as CRT, LCD, PDP, EL and touch panel It is also useful as a cured film and a cured film having a property of preventing dust adhesion due to static electricity. The cured film obtained by curing the antistatic composition of the present invention is also useful as a protective film for a polarizing plate.

Claims (5)

An ionic liquid (A) composed of an anion (a) represented by the following general formula (1) and an onium cation group (b), a polyfunctional (meth) acrylate (B), and a polymerization initiator (C) An active energy ray-curable antistatic composition (D) characterized by containing.
^Q-Y - (1)
Wherein (1), the organic group Q is a path perfluoroalkyl group, a part may be modified with polyoxyethylene groups. Y ^- is COO ^- or PO ₄ ^- represents a. ]   The active energy ray-curable antistatic composition according to claim 1, wherein the ionic liquid (A) contains at least one imidazolium cation. The active energy ray-curable antistatic composition according to claim 1 or 2, wherein the organic group Q in the formula (1) is an organic group represented by the following general formula (2).
_{CF 3 - (CF 2) k} - (CH 2) m - (CH 2 CH 2 O) n - (2)
[In formula (2), k represents 3-20, m represents 0-10, n represents the integer of 0-5. ]   The active energy ray-curable antistatic composition according to any one of claims 1 to 3, wherein the content of the ionic liquid (A) with respect to the (meth) acrylate (B) is 0.1 to 10% by weight.   An antistatic cured product obtained by applying the curable composition according to any one of claims 1 to 4 to a substrate and irradiating with an active energy ray to be cured.