TW202336044A - Active energy ray curable composition and film wherein the active energy ray curable composition contains a compound (A) having a (meth)acrylyl group and a compound (B) having a triazine structure or a triazole structure - Google Patents

Abstract

The present invention provides an active energy ray curable composition capable of forming a hard coat layer and a film of cured coating film using the composition. The hard coat layer can impart hardness to the film surface and is excellent in hot water adhesion and light adhesion. The present invention relates to a film characterized by having an active energy ray curable composition/cured coating film formed by curing an active energy ray curable composition. The active energy ray curable composition contains a compound (A) having a (meth)acrylyl group and a compound (B) having a triazine structure or a triazole structure.

Description

Active energy ray curable composition and film

The present invention relates to an active energy ray curable composition and a film.

As display devices for various electronic devices such as personal computers, televisions, mobile phones, and electronic dictionaries, liquid crystal displays (LCD), organic electroluminescent (EL) displays (Organic Light Emitting Display, OLED), Plasma Display Panel (PDP) and other flat panel displays (Flat Panel Display, FPD), etc. In addition, electrodes containing conductive electrode materials such as indium tin oxide (ITO) are provided on display elements or touch panels (touch sensors) inside the display.

Various resin films are used to prevent damage to the surface of these displays, protective films for electrodes inside displays or touch panels, decorative films (sheets) for interior and exterior decoration of automobiles, low-reflection films for windows, and heat-ray cutting films, etc. use. However, since the hardness or light resistance of the resin film surface may be low, in order to compensate for these problems, a hard coating agent containing an ultraviolet (UV) curable composition or the like is generally applied to the film surface and hardened. , set the hard coating layer on the membrane surface. The hard coat layer is also required to have high adhesion to the resin film (base material). Especially in the protective film of the electrode inside the display or touch panel, in order to prevent moisture or salt from intruding into the electrode or protective film, the adhesion becomes poor. Got to be important.

Therefore, from the viewpoint of being usable in a variety of applications, a hard coat layer is required that has both hardness, light resistance, and substrate adhesion.

As a composition with high adhesiveness, a composition containing 2 mass % or more of an active energy ray-curable component having a tertiary amine group and a cured coating film thereof are known. (For example, refer to Patent Document 1) Furthermore, Patent Document 2 discloses a cured coating film of a composition containing a polymerizable monomer having an isocyanurate skeleton and a polymerizable monomer having an oxyethylene group as a substance exhibiting high hot water resistance adhesion. .

However, in the invention described in Patent Document 1, the penetration of water between the base material and the cured coating film was not tested, and in the invention described in Patent Document 2, the light resistance test was not performed. Therefore, it is difficult to realize a composition that fully satisfies hardness, light resistance, and substrate adhesion.

[Prior art documents] [Patent Document] [Patent Document 1] Japanese Patent Application Laid-Open No. 2020-197737 [Patent Document 2] Japanese Patent Publication No. 2019-235206

[Problem to be solved by the invention]

The problem to be solved by the present invention is to provide an active energy ray-curable composition capable of forming a hard coat layer excellent in film surface hardness, hot water resistance adhesion and light resistance, and a cured coating film using the composition. [Means to solve the problem]

The present invention provides an active energy ray curable composition, which contains a compound (A) having a (meth)acrylyl group and a compound (B) having a triazine structure or a triazole structure. Furthermore, the present invention provides a film having a cured coating film of the active energy ray curable composition.

That is, the present invention provides the following inventions. [1] An active energy ray curable composition containing a compound (A) having a (meth)acrylyl group and a compound (B) having a triazine structure or a triazole structure. [2] The active energy ray curable composition according to [1], wherein the compound (A) has four or more (meth)acrylyl groups in the molecule and a double bond equivalent of 80 g/mol ~160 g/mol range. [3] The active energy ray-curable composition according to [1] or [2], wherein the compound (A) has no urethane bond in the molecule and has a (meth)acrylyl group Either or both of the compound (A-1) and the compound (A-2) having a urethane bond and a (meth)acrylyl group in the molecule. [4] The active energy ray curable composition according to [3], wherein the compound (A-1) contains a compound (A-1-1) containing a hydroxyl group in the molecule and a compound not containing a hydroxyl group in the molecule Either or both of (A-1-2). [5] The active energy ray curable composition according to [3] or [4], wherein the compound (A) contains the compound (A-1) and the compound (A-2), The compounding ratio [(A-1)/(A-2)] of the compound (A-2) relative to the compound (A-1) is in the range of 1/10 to 40/1. [6] The active energy ray-curable composition according to any one of [1] to [5], wherein the compound (B) is a compound represented by the following formula (I). [Chemical 1] (I) (In formula (I), R ₁ represents a group represented by any one of the following formulas (a) to formula (e), and R ₂ represents any of the following formulas (f) to formula (h). A represented group, multiple R ₂ in the same molecule may be the same or different) [Chemical 2] (In formula (a), * represents the bonding bond) [Chemical 3] (In formula (b), * represents the bonding bond) [Chemical 4] (In formula (c), * represents a bond, and R ₃ represents an alkyl group having 1 to 10 carbon atoms) [Chemical 5] (In formula (d), * represents the bonding bond) [Chemical 6] (In formula (e), * represents the bonding bond) [Chemical 7] (In formula (f), * represents a bond, and R ₄ is any one of a hydrogen atom, a methyl group, and a phenyl group. Multiple R _4s in the same molecule may be the same or different) [Chemical 8] (In formula (g), * represents the bonding bond) [Chemical 9] (In the formula (h), * represents a bond, and R ₅ represents an alkyl group having 1 to 8 carbon atoms) [7] The active energy ray curable composition according to any one of [1] to [6] , wherein the content of the compound (B) is 0.5 to 6 parts by mass relative to 100 parts by mass of the resin solid content. [8] The active energy ray-curable composition according to any one of [1] to [7], further containing an acrylic resin (C). [9] The active energy ray-curable composition according to [8], wherein the acrylic resin (C) has a weight average molecular weight in the range of 5,000 to 30,000 and a double bond equivalent in the range of 200 to 450. [10] The active energy ray-curable composition according to [8] or [9], wherein the acrylic resin (C) has a structure represented by the following formula (II) or formula (III). [Chemical 10] (II) [Chemical 11] [Chemical 12] [Chemical 13] (In formula (II) and formula (III), R ₆ represents a hydrogen atom or a methyl group, and the repeat number n is an arbitrary natural number; in formula (II), R ₇ represents an alkyl group with 1 to 8 carbon atoms, and the formula Any one of the groups represented by (i); in the formula (III), R ₈ represents any one of the alkyl group having 1 to 8 carbon atoms and the group represented by the formula (j), and the repeat number m is Any of 2 to 4; multiple R ₆ , R ₇ , R ₈ , and m in the same molecule may be the same or different. In formula (i) and formula (j), * represents a bond, and R ₉ and R ₁₀ represents a hydrogen group or a methyl group) [11] The active energy ray curable composition according to any one of [8] to [10], wherein the content of the acrylic resin (C) is The solid content is 5 to 60 parts by mass per 100 parts by mass. [12] The active energy ray curable composition according to any one of [1] to [11], further containing inorganic particles (D). [13] The active energy ray-curable composition according to [12], wherein the particle diameter of the inorganic particles (D) is 200 nm or less, and the content of the inorganic particles (D) is 100 nm relative to the resin solid content. Parts by mass are 5 parts by mass to 65 parts by mass. [14] The active energy ray-curable composition according to [12] or [13], wherein the inorganic particles (D) are inorganic oxides modified with a surface modifier having a reactive group. [15] A film characterized by having a cured coating film obtained by curing the composition according to any one of [1] to [14]. [16] The film according to [15], wherein the wetting tension of the hardened coating film surface is in the range of 35 mN/m to 60 mN/m. [Effects of the invention]

The active energy ray curable composition of the present invention can be coated on the surface of a resin film and hardened to form a hard coat layer. The hard coat layer can impart high hardness to the film surface and has excellent light adhesion resistance and hot water resistance. Tightness.

Therefore, the active energy ray curable composition of the present invention is widely used in liquid crystal displays (LCDs), organic EL displays (OLEDs), and plasma displays that are display devices for various electronic devices such as personal computers, televisions, mobile phones, and electronic dictionaries. Anti-damage film on the surface of flat panel displays (FPD) such as (PDP), protective films for display elements inside these displays or touch panels or electrodes of touch panels (touch sensors), decorative films (sheets) for interior and exterior decoration of automobiles, Among various applications such as low-reflection films for windows and heat-ray cutting films, it is particularly suitable as a hard coating agent for protective films of electrodes inside touch panels.

In this specification, the compound represented by formula (I) is called "compound (I)", and the same applies to compounds represented by other formulas. In addition, "acrylate" and "methacrylate" are collectively referred to as "(meth)acrylate", and "(meth)acrylyl" and "acrylyl" are collectively referred to as "(meth)acrylyl" base". The compound (A) having a (meth)acrylyl group is called "component (A)", and the same applies to the other compound (B) to compound (D) components.

＜Active energy ray curable composition＞ The active energy ray curable composition of the present invention has components (A) and (B) as essential components, and optionally contains components (C) to (D), or other compounds. As an evaluation method of the present invention, the hardness of the coating film after curing the composition was tested. Furthermore, the adhesion to the base material after the coating film was immersed in boiling water or irradiated with ultraviolet rays was tested. In the case of a coating film that easily absorbs moisture, the volume increases and the adhesion to the base material decreases. Therefore, when the test result is excellent, it is considered to be excellent in hot water resistance adhesion and light resistance.

[(A) Ingredient] The component (A) is a compound having one or more (meth)acrylyl groups in the molecule, and a mixture thereof. Furthermore, (A) component contains the compound (A-1) which does not have a urethane bond in a molecule|numerator and has a (meth)acrylyl group, and a compound (A-1) which has a urethane bond and (meth)acryl group in a molecule|numerator. Either or both of the acyl-based compounds (A-2).

[Compound (A-1)] Compound (A-1) contains any one or both of a compound (A-1-1) containing a hydroxyl group in the molecule and a compound (A-1-2) containing no hydroxyl group in the molecule. Since the hydroxyl-containing compound (A-1-1) has a hydroxyl group, it can increase the reactivity of the (meth)acrylyl group through intermolecular interaction, thereby improving the hardness of the cured coating film and the adhesion to the substrate. In addition, the hydroxyl-free compound (A-1-2) allows the viscosity of the composition and the concentration of each compound to be appropriately adjusted.

Specific examples of the compound (A-1-1) containing a hydroxyl group in the molecule include di-trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and dipentaerythritol tri(meth)acrylate. ) acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol (meth)acrylate, tripentaerythritol hepta(meth)acrylate, etc. One type of these may be used, or two or more types may be used.

Specific examples of the compound (A-1-2) that does not contain a hydroxyl group include 1,4-butanediol di(meth)acrylate and 3-methyl-1,5-pentanediol di(meth)acrylate. (Meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 2-methyl-1,8-octanediol di(meth)acrylate ) acrylate, 2-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate and other di(meth)acrylates Acrylate; di(meth)acrylate, trimethylolpropane tri(methyl) glycol obtained by adding 2 mol of ethylene oxide or propylene oxide to 1 mol of bisphenol A Acrylate, di-trimethylolpropane tetra(meth)acrylate, glyceryl tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate Meth)acrylate, polypentaerythritol poly(meth)acrylate, (poly)ethylene glycol dipentaerythritol hexa(meth)acrylate, (poly)ethylene glycol di(meth)acrylate, (poly)ethylene glycol Glycol (meth)acrylate, (poly)propylene glycol dipentaerythritol hexa(meth)acrylate, (poly)propylene glycol di(meth)acrylate, (poly)propylene glycol (meth)acrylate, ethoxylation Dipentaerythritol poly(meth)acrylate, di(meth)acrylate obtained by adding 4 moles or more of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol, epoxy Acrylates with alkylene oxide structures such as ethane-modified trimethylolpropane tri(meth)acrylate, epoxypropane-modified trimethylolpropane tri(meth)acrylate, etc.; amine-modified polyether tetrahydrofuran Acrylates with an amine skeleton such as acrylates; polyfunctional (meth)acrylates such as acrylates with a thiol group such as ethylene dithiol-modified poly(meth)acrylates. One type of these may be used, or two or more types may be used.

[Compound (A-2)] The synthesis method of compound (A-2) is not particularly limited as long as it is a compound having at least a urethane bond and a (meth)acrylyl group in the molecule. Examples thereof include combining a compound having an isocyanate group and a hydroxyl group and a (meth)acrylyl group. A compound obtained by dehydration condensation reaction of a (meth)acrylyl compound. In addition, since the compound (A-2) has a urethane bond, the reactivity of the (meth)acryl group is increased through intermolecular interaction, and the hardness and hot water resistance adhesion of the cured coating film are improved.

Examples of the compound having an isocyanate group that can be used as a raw material of the compound (A-2) include aromatic isocyanates such as diphenylmethane diisocyanate and toluene diisocyanate; 1,6-hexamethylene diisocyanate, 1,4 -Butane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine acid diisocyanate, lysine acid triisocyanate, etc. Aliphatic isocyanates; isophorone diisocyanate, 4,4'-methyl bis(cyclohexyl isocyanate), 1,3-bis(methyl isocyanate)cyclohexane, norbornane diisocyanate, hydrogenated diisocyanate Alicyclic isocyanate compounds such as toluene diisocyanate, 2-methyl-1,3-diisocyanatecyclohexane, 2-methyl-1,5-diisocyanatecyclohexane, etc. Alternatively, dimers or trimers of these isocyanate compounds (isocyanurate, biuret, allophanate, etc.) may also be used. One type of these may be used, or two or more types may be used.

Examples of the compound having a hydroxyl group and a (meth)acrylyl group that can be used as a raw material of the compound (A-2) include pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and (meth)acrylate. ) 2-hydroxyethyl acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate ester, caprolactone-modified hydroxy mono(meth)acrylate (for example, trade name "Placcel (registered trademark) FA-2D" manufactured by DAICEL, etc.), Polycarbonate-modified hydroxyl mono(meth)acrylate (for example, trade name "HEMAC" (registered trademark) manufactured by DAICEL, etc.), modified with polyethylene glycol or polypropylene glycol hydroxyl mono(meth)acrylate (for example, trade names "Blemmer (registered trademark) AE-200", "Blemmer (registered trademark) AP-400" manufactured by NOF Corporation "etc. One type of these may be used, or two or more types may be used.

Among the above, the component (A) is more preferably a compound having four or more (meth)acrylyl groups in the molecule. Specifically, as the compound (A-1-1), dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, tripentaerythritol hepta(meth)acrylate, etc. are more preferred. As the compound (A-1-2), pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc. are more preferred. As the compound (A-2), a dimer of 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 1,6-hexamethylene diisocyanate and pentaerythritol tri(methyl) is more preferred. Acrylates, reactants of dipentaerythritol penta(meth)acrylate, etc. By using four or more (meth)acrylyl compounds as component (A) in the molecule in this way, the crosslinking density when the composition is cured is increased, and the hardness is increased. Furthermore, the hardened coating film becomes less likely to absorb moisture, and the hot water resistance adhesion is also improved.

In addition, the compound used as component (A) is preferably a compound with a double bond equivalent in the range of 20 g/mol to 300 g/mol, more preferably a compound in the range of 50 g/mol to 250 g/mol, and is particularly preferred. Compounds in the range of 80 g/mol to 160 g/mol. The double bond equivalent in this specification refers to the amount obtained by dividing the mass of the compound by the mass of the double bond in the compound. By using a compound with a double bond equivalent within these ranges, the crosslinking density becomes optimal and hardness, hot water resistance adhesion, and light resistance can be improved in a balanced manner.

When the component (A) contains both the compound (A-1) and the compound (A-2), the compounding ratio of the compound (A-2) to the compound (A-1) [(A -1)/(A-2)] is preferably in the range of 1/100 to 100/1, more preferably in the range of 1/40 to 60/1, and particularly preferably in the range of 1/10 to 40/1. By setting it as these ranges, the light-resistant adhesiveness improves.

When compound (A-1) contains both a compound (A-1-1) containing a hydroxyl group in its molecule and a compound (A-1-2) not containing a hydroxyl group in its molecule, the compound (A-1) -2) The compounding ratio [(A-1-1)/(A-1-2)] relative to the compound (A-1-1) is preferably in the range of 20/80 to 95/5, more preferably The range is 30/70~90/10, and the best range is 50/50~80/20. By setting it within these ranges, the hydrophilicity of compound (A-1) can be adjusted to an optimal range, and the hot water resistance adhesion can be improved.

[(B)Component] (B) The component is a compound having a triazine structure or a triazole structure in the molecule. Component (B) can weaken the water absorption of the hardened coating film of the composition and improve the hot water resistance adhesion. Furthermore, since it can absorb ultraviolet rays, it can also improve light-resistant adhesion.

Specific examples include 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazole- 2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylbis[6-(2H-benzotriazol-2-yl)-4 -(1,1,3,3-tetramethylbutyl)phenol], 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol) Benzotriazoles such as azol-2-yl)-6-tert-butyl-4-methylphenol, 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole; or the following Triazine represented by formula (I), etc.

[Chemical 1] (I)

In formula (I), R ₁ represents a group represented by any one of the following formulas (a) to formula (e), and R ₂ represents a group represented by any one of the following formulas (f) to formula (h). group, multiple R _2's in the same molecule may be the same or different.

[Chemicalization 2]

[Chemical 3]

[Chemical 4]

In formula (c), R ₃ is an alkyl group having 1 to 10 carbon atoms.

[Chemistry 5]

[Chemical 6]

[Chemical 7]

R ₄ is any one of a hydrogen atom, a methyl group and a phenyl group, and a plurality of R ₄ in the same molecule may be the same or different.

[Chemical 8]

[Chemical 9]

R ₅ is an alkyl group having 1 to 8 carbon atoms.

In the formulas (a) to (h), * represents a bonding bond.

Among the components (B), 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzene is more preferred from the viewpoint of weakening the water absorption of the cured coating film and maintaining adhesion to the substrate. Triazole or compound (I), particularly preferably a compound in which R ₁ in compound (I) is (b), R ₂ is (f), and R ₄ in (f) is a hydrogen atom.

(B) One type of component may be used, or two or more types may be used.

The content of compound (B) is preferably in the range of 0.1 to 20 parts by mass, more preferably in the range of 0.3 to 8 parts by mass, and particularly preferably 0.5, based on 100 parts by mass of the total resin solid content in the composition. The range is from parts by mass to 6.0 parts by mass. By setting it within these ranges, the composition can be cured without any problem, the water absorption of the cured coating film can also be reduced, and the light resistance can also be improved. Therefore, hot water resistance adhesion and light resistance are improved.

The composition of the present invention may further contain component (C) if necessary.

[(C)Component] (C) Component is acrylic resin, which is a polymer of acrylate or methacrylate. When the composition of the present invention contains the component (C), the cured coating film is easily deformed appropriately. Therefore, even if the volume of the base material increases, the shape of the cured coating film changes according to the base material, and the adhesion to the base material improves.

The weight average molecular weight of the acrylic resin used as component (C) is preferably in the range of 1,000 to 50,000, more preferably in the range of 2,000 to 40,000, particularly preferably in the range of 5,000 to 30,000. By setting it within these ranges, hot water resistance adhesion and light resistance are improved.

Furthermore, the double bond equivalent of the acrylic resin that can be used as component (C) is preferably in the range of 100 g/mol to 700 g/mol, more preferably in the range of 150 g/mol to 600 g/mol, and particularly preferably 200 g/mol～450 g/mol range. By setting it within these ranges, hot water resistance adhesion and light resistance are improved.

As component (C), specifically, it is preferable to use a compound having a structure represented by the following formula (II) or the following formula (III).

[Chemical 10] (II) [Chemical 11]

In formula (II) and formula (III), R ₆ represents a hydrogen atom or a methyl group, and the repeating number n is an arbitrary natural number. In formula (II), R ₇ represents either an alkyl group having 1 to 8 carbon atoms or a group represented by formula (i). In formula (III), R ₈ represents either an alkyl group having 1 to 8 carbon atoms or a group represented by formula (j), and the repeating number m is any one of 2 to 4. A plurality of R ₆ , R ₇ , R ₈ and m in the same molecule may be the same or different.

[Chemical 12]

[Chemical 13]

In formula (i) or formula (j), * represents a bond, and R ₉ and R ₁₀ represent a hydrogen group or a methyl group.

The content of the acrylic resin (C) is preferably in the range of 1 to 90 parts by mass, more preferably in the range of 3 to 80 parts by mass based on 100 parts by mass of the total resin solid content in the composition, and particularly preferably The range is 5 parts by mass to 60 parts by mass. By setting it within these ranges, it is possible to moderately change the shape while maintaining the high cross-linking density of the cured coating film. Therefore, the water absorption of the coating film can be reduced, and the coating film can follow the shape change of the base material, thereby improving the hot water-resistant adhesion.

The composition of the present invention may further contain component (D) if necessary.

[(D)Component] (D) The component is inorganic particles. When the composition contains inorganic particles (D), volume shrinkage when the composition hardens is suppressed. Therefore, stress deformation is less likely to occur between the base material and the hardened coating film, and hot water-resistant adhesion and light-resistant adhesion are improved. In addition, by exposing the inorganic particles to the surface of the coating film, the wetting tension on the surface of the coating film also increases.

As the inorganic particles (D), specifically, silica, aluminum oxide, magnesium oxide, titanium dioxide, zirconium oxide, etc. can be used; as the inorganic particles excellent in thermal conductivity, boron nitride, aluminum nitride, aluminum oxide, oxide, etc. can be used. Titanium, magnesium oxide, zinc oxide, etc.; as inorganic particles with excellent conductivity, those using a single metal or an alloy (such as iron, copper, magnesium, aluminum, gold, silver, platinum, zinc, manganese, stainless steel, etc.) can be used Metal fillers and/or metal-coated fillers; as inorganic particles with excellent barrier properties, minerals such as mica, clay, kaolin, talc, zeolite, wollastonite, and montmorillonite, or potassium titanate, magnesium sulfate, and seafoam can be used Sepiolite, vermiculite, aluminum borate, calcium carbonate, titanium oxide, barium sulfate, zinc oxide, magnesium hydroxide; as inorganic particles with high refractive index, barium titanate, zirconium oxide, titanium oxide, etc. can be used; as a display Inorganic particles that produce photocatalytic properties can use titanium, cerium, zinc, copper, aluminum, tin, indium, phosphorus, carbon, sulfur, ruthenium, nickel, iron, cobalt, silver, molybdenum, strontium, chromium, barium, lead, etc. Catalyst metals, complexes of these metals, their oxides, etc.; as inorganic particles excellent in wear resistance, metals such as alumina, zirconium oxide, magnesium oxide, and their complexes and oxides, etc. can be used; as As inorganic particles with excellent conductivity, metals such as silver and copper, tin oxide, indium oxide, etc. can be used; as inorganic particles with excellent ultraviolet shielding, titanium oxide, zinc oxide, etc. can be used. These inorganic fine particles may be appropriately selected according to the intended use, and may be used alone or in combination.

For example, when silica is used as the component (D), it is not particularly limited, and known silica fine particles such as powdered silica or colloidal silica can be used. Examples of commercially available powdery silica fine particles include: "Aerosil (registered trademark)" series (50, 200, etc.) manufactured by Nippon Aerosil Co., Ltd. under the trade name The trade name "Sildex" series manufactured by AGC Corporation (H31, H32, H51, H52, H121, H122, etc.), the trade name "E220A" or "E220" manufactured by Tosoh Silicon Dioxide Corporation , brand name "SYLYSIA (registered trademark) 470" manufactured by Fuji Silysia Chemical Co., Ltd., brand name "SG Flake" manufactured by Nippon Sheet Glass Co., Ltd., etc. Examples of commercially available colloidal silica include "Methanol Silica Sol", "IPA-ST", "MEK-ST", "PGM-ST", and "NBA" under the trade names manufactured by Nissan Chemical Industries, Ltd. -ST", "XBA-ST", "DMAC-ST", "ST-UP", "ST-OUP", "ST-20", "ST-40", "ST-C", "ST-N ”, “ST-O”, “ST-50”, “ST-OL”, etc.

Silica Reactive silica can also be used. Examples of reactive silica include reactive compound-modified silica. As the reactive compound, from the viewpoint of reducing the water absorption of the cured coating film, for example, a reactive silane coupling agent having a hydrophobic group, a compound having a (meth)acrylyl group, a compound having a maleyl group is preferable. A compound having an amine group and a compound having a glycidyl group. Among them, from the viewpoint of compatibility with component (A) or other components, diamine modified with a compound having a (meth)acrylyl group is particularly preferred. Silicon oxide. Examples of commercially available powdery silica modified with a compound having a (meth)acrylyl group include "Aerosil (registered) manufactured by Japan Aerosil Corporation" Trademark) RM50", "Aerosil (registered trademark) R711", etc. Examples of commercially available colloidal silica modified with a compound having a (meth)acrylyl group include Nissan Chemical Industries, Ltd. Manufactured under the trade names "MIBK-SD", "MIBK-SD-L", "MIBK-AC-2140Z", "MEK-AC-2140Z", etc. Examples of reactive silica include silica modified with a glycidyl group such as 3-glycidoxypropyltrimethoxysilane and then subjected to an addition reaction of acrylic acid, or silica having a Silica obtained by modifying a substance obtained by urethanizing 3-isocyanatopropyltriethoxysilane with a hydroxyl and (meth)acrylyl compound.

The method for producing silica that can be used in the present invention is not particularly limited. For example, silica produced by a wet method can be used. In addition, a sedimentation method and a gel method are known as wet methods, but silica produced by either method can be used. Furthermore, both the sedimentation method and the gel method can adjust the reaction conditions (pH, raw material concentration, reaction temperature, etc.) between sodium silicate, which is the raw material of silica particles, and mineral acid (mineral acid) such as sulfuric acid. The primary average particle size and secondary average particle size of silicon oxide are adjusted.

Preferably, a substance obtained by pulverizing a substance obtained by secondary agglomeration of silica particles having a primary average particle diameter (the particle diameter after pulverization is referred to as a secondary average particle diameter) is preferred as the silica particles. The crushing device can use ball mill, bead mill, rod mill, SAG mill, high-pressure crushing roller, longitudinal axis impact (VSI) mill, colloid mill, conical mill, disc mill, wheel mill Machine, hammer mill, mortar, jet mill, etc.

In addition, when pulverizing the silica particles, a moist dispersing agent or a silane coupling agent can be added to modify the surface of the silica particles with organic groups while pulverizing. As the wetting dispersant or silane coupling agent, for example, DISPERBYK-103, DISPERBYK-106, DISPERBYK-161, DISPERBYK DISPERBYK-2152, DISPERBYK P104, 3-(meth)acrylylpropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 2- (3,4-Epoxycyclohexyl)ethyltrimethoxysilane, etc.

The inorganic particles (D) preferably have a secondary average particle diameter in the range of 10 nm to 300 nm, more preferably in the range of 20 nm to 250 nm, and particularly preferably in the range of 50 nm to 200 nm. By setting it within these ranges, the transparency of the cured coating film can be maintained.

The compounding amount of the inorganic particles (D) is preferably in the range of 0 to 90 parts by mass, more preferably in the range of 3 to 80 parts by mass based on 100 parts by mass of the total resin solid content in the composition, and is particularly preferred. It is in the range of 5 parts by mass to 65 parts by mass. By setting it within these ranges, it is possible to reduce the water absorbency of the cured coating film while suppressing shrinkage when the composition is cured. That is, since it is difficult to form a space between the base material and the cured coating film, hot water-resistant adhesion and light-resistant adhesion are improved, and the wetting tension of the coating film surface can also be increased.

In addition, the active energy ray curable composition of the present invention may also contain a photopolymerization initiator.

[Photopolymerization initiator] Examples of the photopolymerization initiator include: 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxy Ethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-di Phenylethane-1-one, diphenyl (2,4,6-trimethoxybenzoyl)phosphine oxide, 2,4,6-trimethylbenzyldiphenylphosphine oxide, bis (2,4,6-Trimethylbenzyl)phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinylpropan-1-one, 2- Benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, etc.

The photopolymerization initiator may be used alone, or two or more types may be used in combination.

The content of the photopolymerization initiator is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and particularly preferably 0.01 to 20 parts by mass relative to 100 parts by mass of the solid content of the active energy ray curable composition. 1 to 5 parts by mass. When the content of the photopolymerization initiator is 0.1 parts by mass or more, the curing reaction proceeds appropriately and a cured coating film with high hardness can be obtained, which is preferable. On the other hand, when the content of the photopolymerization initiator is 10 parts by mass or less, yellowing is less likely to occur and a cured coating film with high transparency can be obtained, which is preferable.

In addition, the active energy ray curable composition of the present invention may also contain a solvent. By including a solvent, the viscosity of the composition can be adjusted.

[solvent] Examples of the solvent include alcohol solvents such as methanol, ethanol, 1-propanol, tert-butanol, and diacetone alcohol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and propylene glycol. Alcohol ether solvents such as monomethyl ether, propylene glycol monoethyl ether, carbitol, and cellosolve; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.; methyl acetate, ethyl acetate, Ester solvents such as butyl acetate; aromatic solvents such as toluene, xylene, dibutylhydroxytoluene, etc.

The solvent may be used alone, or two or more types may be used in combination.

The content of the solvent is preferably 0 to 300 parts by mass, and more preferably 0 to 100 parts by mass relative to 100 parts by mass of the solid content of the active energy ray curable composition. When the content of the solvent is 300 parts by mass or less, it is easier to control the film thickness, which is preferable. In addition, when the content of the solvent is 10 parts by mass or more, it is preferable because various coating methods such as spray coating and flow coating can be used.

Furthermore, the active energy ray curable composition of the present invention may contain other additives as necessary.

[Other ingredients] Typical examples of other components include reactive compounds, various resins, fillers, ultraviolet absorbers, and leveling agents. However, it is assumed that these do not belong to components (A) to (D). In addition, it may also contain inorganic pigments, organic pigments, extender pigments, clay minerals, waxes, catalysts, surfactants, stabilizers, flow regulators, coupling agents, dyes, rheology control agents, antioxidants, and plasticizers. wait.

As the reactive compound and resin, a compound having a double bond such as a (meth)acrylate compound or a vinyl group other than the component (A) and (C) may be blended.

To adjust the viscosity, liquid organic polymers can also be used. The so-called liquid organic polymers are liquid organic polymers that do not directly participate in the hardening reaction. Examples include: modified polymers containing carboxyl groups (Flowlen) G-900, NC-500: Kyoei Chemical Industrial Co., Ltd.), acrylic polymer (Flowlen WK-20: manufactured by Gyoei Chemical Industry Co., Ltd.), amine salt of special modified phosphate ester (HIPLAAD (registered trademark) ED-251 : Manufactured by Kusumoto Chemical Co., Ltd.), modified acrylic block copolymer (DISPERBYK (registered trademark) 2000: manufactured by BYK-Chemie Co., Ltd.), etc.

As various resins, thermosetting resin or thermoplastic resin can be used. A thermosetting resin is a resin that is substantially insoluble and can be changed to infusibility when cured by means such as heating, radiation, or a catalyst. Specific examples thereof include phenolic resin, urea resin, melamine resin, benzoguanamine resin, alkyd resin, unsaturated polyester resin, vinyl ester resin, diallyl terephthalate resin, and epoxy resin. Resin, silicone resin, urethane resin, furan resin, ketone resin, xylene resin, thermosetting polyimide resin, benzoxazine resin, active ester resin, aniline resin, cyanate ester resin, Styrene-Maleic Anhydride (SMA) resin, etc. These thermosetting resins may be used alone or in combination of two or more types.

Thermoplastic resin refers to a resin that can be melted and molded by heating. Specific examples thereof include polyethylene resin, polypropylene resin, polystyrene resin, rubber-modified polystyrene resin, acrylonitrile-butadiene-styrene (ABS) resin, acrylonitrile- Styrene (Acrylonitrile Styrene, AS) resin, polymethyl methacrylate resin, acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyethylene terephthalate resin, ethylene vinyl alcohol resin, acetic acid Cellulose resin, ionomer resin, polyacrylonitrile resin, polyamide resin, polyacetal resin, polybutylene terephthalate resin, polylactic acid resin, polyphenylene ether resin, modified polyphenylene ether resin, Polycarbonate resin, polystyrene resin, polyphenylene sulfide resin, polyether imide resin, polyether imide resin, polyacrylate resin, thermoplastic polyimide resin, polyamide imine resin, polyether ether Ketone resin, polyketone resin, liquid crystal polyester resin, fluororesin, syndiotactic polystyrene resin, cyclic polyolefin resin, etc. These thermoplastic resins may be used alone or in combination of two or more types.

As the filler, substances other than the component (D) may be used, and for example, inorganic fibers or organic fibers may be used.

Examples of the inorganic fibers include, in addition to inorganic fibers such as carbon fibers, glass fibers, boron fibers, alumina fibers, and silicon carbide fibers, carbon fibers, activated carbon fibers, graphite fibers, tungsten carbide fibers, ceramic fibers, and natural fibers. , basalt and other mineral fibers, boron nitride fibers, boron carbide fibers and metal fibers, etc. Examples of the metal fibers include aluminum fibers, copper fibers, brass fibers, stainless steel fibers, and steel fibers.

Examples of organic fibers include polybenzodiazole, polyarylamine, poly p-phenylene benzo-oxazole (PBO), polyphenylene sulfide, polyester, acrylic, Synthetic fibers of resin materials such as polyamide, polyolefin, polyvinyl alcohol, and polyarylate, or natural fibers such as cellulose, pulp, cotton, wool, silk, etc., proteins, polypeptides, regenerated fibers such as alginic acid, etc.

Examples of ultraviolet absorbers include benzophenone-based, cyclic iminoester-based, cyanoacrylate-based, and polymer-type ultraviolet absorbers.

For the purpose of improving light resistance, a light stabilizer may be used in combination with the composition of the present invention. Examples of light stabilizers include hindered amine light stabilizers (Hindered Amine Light Stabilizer, HALS) and the like.

Various surface modifiers may be added to the composition of the present invention for the purpose of improving leveling properties during coating, or for improving the sliding properties of the cured film to improve scratch resistance. As the surface modifier, various additives that modify surface physical properties and are commercially available as surface conditioners, leveling agents, smoothness-imparting agents, antifouling agents, etc. can be used. Among these, silicone-based surface modifiers and fluorine-based surface modifiers are preferred. Specifically, silicone-based polymers and oligomers having silicone chains and polyalkylene oxide chains, silicone-based polymers and oligomers having silicone chains and polyester chains, silicone-based polymers and oligomers having perfluorinated Fluorine-based polymers and oligomers with alkyl and polyalkylene oxide chains, fluorine-based polymers and oligomers with perfluoroalkyl ether chains and polyalkylene oxide chains, etc. Just use more than one of these. For the purpose of improving the durability of sliding properties, a substance containing a (meth)acrylyl group in the molecule can be used. Specific surface modifiers include: EBECRYL (registered trademark) 350 (manufactured by Daicel-Ornex), BYK-333 (BYK -Chemie Japan), BYK-377 (manufactured by BYK-Chemie Japan), BYK-378 (manufactured by BYK-Chemie Japan), BYK-UV3500 (BYK-Chemie Japan) BYK-Chemie Japan), BYK-UV3505 (BYK-Chemie Japan), BYK-UV3576 (BYK-Chemie Japan), Mag Megaface (registered trademark) RS-75 (manufactured by DIC Corporation), Megaface (registered trademark) RS-76-E (manufactured by DIC Corporation), Megaface Megaface (registered trademark) RS-72-K (manufactured by DIC Corporation), Megaface (registered trademark) RS-76-NS (manufactured by DIC Corporation), Megaface (registered trademark) RS-90 (manufactured by DIC Corporation), Megaface (registered trademark) RS-91 (manufactured by DIC Corporation), Megaface Megaface (registered trademark) RS-55 (manufactured by DIC Corporation), Optool (registered trademark) DAC-HP (manufactured by Daikin Corporation), ZX-058-A (T&K TOKA manufacturing), ZX-201 (T&K TOKA manufacturing), ZX-202 (T&K TOKA manufacturing), ZX-212 (T&K TOKA manufacturing), ZX-214-A (T&K TOKA manufacturing), X-22-164AS (Shin-Etsu Chemical Industrial Co., Ltd.), X-22-164A (Manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Shin-Etsu Chemical Industry Co., Ltd.), X-22-174DX (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), etc.

The active energy ray-curable composition of the present invention can be preferably used as a cured coating film that imparts hardness and light resistance to the base material and has adhesiveness by applying it to at least one side of various materials and then irradiating active energy rays. High hardened coating film. The hardened coating film containing the composition of the present invention can form a hard coat layer that imparts hardness and light resistance to the film surface and has excellent hot water resistance and adhesion. Therefore, it can be used in harsh high-temperature and high-humidity environments or outdoors. Hard coatings of materials that have been used for a long time exhibit particularly excellent results when used.

＜Hard coating film, membrane＞ (structure, material) The film of the present invention includes a coating film containing a cured product of the active energy ray curable composition of the present invention, and a base material. The base material is not particularly limited and can be appropriately selected according to the application. Examples include plastic, glass, wood, metal, metal oxide, paper, silicon, modified silicon, etc. It can also be a base obtained by joining different raw materials. material. The shape of the substrate is not particularly limited and may be any shape depending on the purpose, such as a flat plate, a sheet, or a three-dimensional shape having curvature on the entire surface or part of the base. In addition, the hardness, thickness, etc. of the base material are not limited.

The plastic base material is not particularly limited as long as it contains a resin. For example, the above-mentioned thermosetting resin or thermoplastic resin may be used. The mechanical material may be a single resin or a base material in which a plurality of resins are mixed, or may have a single layer or a laminated structure of two or more layers. In addition, these plastic substrates can be fiber reinforced (Fiber Reinforced Polymer (FRP)).

In addition, within the scope that does not hinder the effects of the present invention, the base material may also contain known antistatic agents, antifogging agents, anticaking agents, ultraviolet absorbers, antioxidants, pigments, organic fillers, inorganic fillers, optical fillers, etc. Stabilizers, crystal nucleating agents, lubricants and other known additives.

The film of the present invention may further have a second base material on the base material and the cured coating film. The material of the second base material is not particularly limited, and examples thereof include glass, wood, metal, metal oxide, plastic, paper, silicon, modified silicon, etc. It may also be a base material obtained by joining different raw materials. The shape of the base material is not particularly limited and may be any shape depending on the purpose, such as a flat plate, a sheet, or a three-dimensional shape having curvature on the entire surface or part of the base. In addition, the hardness, thickness, etc. of the base material are not limited.

The cured coating film of the present invention has high adhesion to both plastics and inorganic substances, and therefore can be preferably used as an interlayer material of dissimilar materials. Preferred are the case where the base material is plastic and the second base material is an inorganic layer, and the case where the base material is plastic and the second base material is an adhesive material or a curable resin coating film. Examples of the inorganic layer include quartz, sapphire, glass, optical films, ceramic materials, inorganic oxides, evaporated films (Chemical Vapor Deposition, CVD), and Physical Vapor Deposition (PVD). , sputtering), magnetic film, reflective film, Ni, Cu, Cr, Fe, stainless steel and other metals, paper, Spin On Glass (SOG), Spin On Carbon (SOC), polyester- Plastic layers such as polycarbonate and polyimide, thin film transistor (TFT) array substrates, PDP electrode plates, conductive substrates such as ITO or metal, insulating substrates, silicon, silicon nitride, polycrystalline silicon , silicon oxide, amorphous silicon and other silicon-based substrates.

The wetting tension of the surface of the cured coating film of the present invention is preferably in the range of 35 mN/m to 60 mN/m, and the range of 40 mN/m to 55 mN/m is effective for adhesion to the second base material. Better words. In addition, the wetting tension is a value measured based on Japanese Industrial Standards (JIS) test method K6768:1999.

(manufacturing method) The film of the present invention is obtained by coating the composition of the present invention on the surface of a base material and then hardening the composition. Coating of the base material can be performed by directly applying the composition to the base material or directly molding the composition onto the base material and hardening the composition. When direct coating is performed, the coating method is not particularly limited, and examples thereof include spray coating, spin coating, dipping, roller coating, blade coating, doctor roll, doctor blade, and curtain coating. , slit coating method, screen printing method, inkjet method, etc. When direct molding is performed, examples include in-mold molding, insert molding, vacuum molding, extrusion lamination molding, and stamping molding. In addition, the film of the present invention can also be obtained by laminating a cured product of the composition on a base material. When laminating a cured product of the composition, a semi-cured cured product may be laminated on the base material and then completely cured, or a fully cured cured product may be laminated on the base material.

Since the composition of the present invention contains a compound having a polymerizable unsaturated group, it can be hardened by irradiating active energy rays. Examples of active energy rays include ultraviolet rays, electron beams, alpha rays, beta rays, and gamma rays plasma radiation. Among these, ultraviolet (UV) is preferred in terms of curability and convenience. Here, when ultraviolet rays are used as active energy rays, examples of devices that irradiate the ultraviolet rays include: low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, electrodeless lamps (melting lamps), chemical lamp, black light lamp, mercury-xenon lamp, short arc lamp, helium-cadmium laser, argon laser, sunlight, light-emitting diode (light-emitting diode, LED) lamp, etc. By using these to irradiate ultraviolet rays with a wavelength of about 180 nm to 400 nm to a coated or formed composition, a cured coating film or a cured product can be obtained. The amount of ultraviolet irradiation can be appropriately selected depending on the type and amount of the photopolymerization initiator used.

(use) The hardened coating film of the composition of the present application has high hardness and excellent hot water resistance and light resistance. Therefore, it can protect the object from external impact, moisture and light while maintaining high adhesion, and can be relatively It is ideal for use as an anti-damage film on the surface of flat panel displays (FPD) such as liquid crystal displays (LCDs), organic EL displays (OLED), and plasma displays (PDP), as well as display elements or touch panels (touch sensors) inside the displays. ) and other applications including protective films for electrodes containing conductive electrode materials. In addition, it can be preferably used in various applications such as decorative films (sheets) for interior and exterior decoration of automobiles, low-reflective films for windows, and heat-ray cutting films.

[Example] Hereinafter, the present invention will be described in more detail using Examples and Comparative Examples, but the present invention is not limited to the following forms. In addition, in this example, unless otherwise stated, "parts" and "%" are based on mass.

(Synthesis Example 1: Synthesis of urethane acrylate compound (1)) In a 1-liter flask including a stirrer, a gas introduction tube, a condenser, and a thermometer, "Covestro Co., Ltd." Desmodur H" (168.2 parts by mass), 2,6-di-tert-butyl-4-methylphenol (1.05 parts by mass), methoxyhydroquinone (0.11 parts by mass), Dibutyltin acetate (0.11 parts by mass) was heated to 70°C, and pentaerythritol triacrylate (trade name "Aronix M-306" manufactured by Toagosei Co., Ltd., containing approximately 30% by mass) was added in batches over 1 hour. Pentaerythritol tetraacrylate) (356.9 parts by mass). After the addition, the reaction was carried out at 80°C until the infrared absorption spectrum at 2250 cm ^-1 indicating the isocyanate group disappeared, thereby obtaining a urethane acrylate compound (1) (containing approximately 20.4% of pentaerythritol tetraacrylate).

(Synthesis Example 2: Synthesis of urethane acrylate compound (2)) In a 1-liter flask including a stirrer, a gas introduction tube, a condenser, and a thermometer, "Covestro Co., Ltd."IPDI" (222.3 parts by mass), 2,6-di-tert-butyl-4-methylphenol (1.16 parts by mass), methoxyhydroquinone (0.12 parts by mass), dibutyltin diacetate (0.12 parts by mass) ; parts by mass). After the addition, the reaction was carried out at 80°C until the infrared absorption spectrum at 2250 cm ^-1 indicating the isocyanate group disappeared, thereby obtaining a urethane acrylate compound (2) (containing approximately 18.5% of pentaerythritol tetraacrylate).

(Synthesis Example 3: Synthesis of urethane acrylate compound (3)) In a 1-liter flask including a stirrer, a gas introduction tube, a condenser, and a thermometer, "Covestro Co., Ltd."IPDI" (222.3 parts by mass), 2,6-di-tert-butyl-4-methylphenol (1.49 parts by mass), methoxyhydroquinone (0.15 parts by mass), dibutyltin diacetate (0.15 parts by mass) ), raise the temperature to 70°C, and add "MIRAMER M500" (524 parts by mass) manufactured by MIWON in batches over 1 hour. After the addition, the reaction was carried out at 80°C until the infrared absorption spectrum of 2250 cm ^-1 indicating the isocyanate group disappeared, thereby obtaining a urethane acrylate compound (3).

(Synthesis Example 4: Synthesis of urethane acrylate compound (4)) In a 1-liter flask including a stirrer, a gas introduction pipe, a condenser, and a thermometer, "Bath" manufactured by BASF Corporation was added. Basnonat HB100" (186.67 parts by mass), 2,6-di-tert-butyl-4-methylphenol (1.09 parts by mass), methoxyhydroquinone (0.11 parts by mass), diacetic acid Dibutyltin (0.11 parts by mass) was heated to 70°C, and pentaerythritol triacrylate (trade name "Aronix M-306" manufactured by Toagosei Co., Ltd., containing approximately 30% by mass of pentaerythritol) was added in batches over 1 hour. Tetraacrylate) (356.87 parts by mass). After the addition, the reaction was carried out at 80°C until the infrared absorption spectrum of 2250 cm ^-1 indicating the isocyanate group disappeared, thereby obtaining a urethane acrylate compound (4) (containing approximately 19.7% of pentaerythritol tetraacrylate).

(Synthesis Example 5: Synthesis of Acrylic Resin (1)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 229 parts by mass of glycidyl methacrylate, 153 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 46 parts by mass and 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) 24 parts by mass The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 118 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-1). The property values of the acrylic acrylate resin (ACAC-1) are as follows. Weight average molecular weight (Mw): 10,000, double bond equivalent: 305.34.

(Synthesis Example 6: Synthesis of Acrylic Resin (2)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 283 parts by mass of glycidyl methacrylate, 73 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 43 parts by mass and 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) 21.5 parts by mass The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 144 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-2). The property values of the acrylic acrylate resin (ACAC-2) are as follows. Weight average molecular weight (Mw): 10,000, double bond equivalent: 250.21.

(Synthesis Example 7: Synthesis of Acrylic Resin (3)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 165 parts by mass of glycidyl methacrylate, 251 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 43 parts by mass and 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) 21.5 parts by mass The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 84 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-3). The property values of the acrylic acrylate resin (ACAC-3) are as follows. Weight average molecular weight (Mw): 10,000, double bond equivalent: 428.93.

(Synthesis Example 8: Synthesis of Acrylic Resin (4)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 283 parts by mass of glycidyl methacrylate, 73 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 30 parts by mass and 15 parts by mass of 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 144 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-4). The property values of the acrylic acrylate resin (ACAC-4) are as follows. Weight average molecular weight (Mw): 30,000, double bond equivalent: 250.28.

(Synthesis Example 9: Synthesis of Acrylic Resin (5)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 165 parts by mass of glycidyl methacrylate, 251 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 30 parts by mass and 15 parts by mass of 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 84 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-5). The property values of the acrylic acrylate resin (ACAC-5) are as follows. Weight average molecular weight (Mw): 30,000, double bond equivalent: 428.93.

(Synthesis Example 10: Synthesis of Acrylic Resin (6)) In a high-pressure sealed reaction device including a stirring device, a cooling tube, a dropping funnel and a nitrogen introduction tube, 254 parts by mass of methyl isobutyl ketone was put in, and the temperature was raised to 150°C while stirring, and then continued for three hours. From the dropping funnel, 153 parts by mass of glycidyl methacrylate, 229 parts by mass of methyl methacrylate, and tert-butyl peroxy-2-ethylhexanoate ("Pabzil" manufactured by Nippon Oils and Fats Co., Ltd. (Perbutyl)O") 56 parts by mass and 28 parts by mass of 1,1'-bis-(tert-butylperoxy)cyclohexane ("Perhexa C" manufactured by Nippon Oils and Fats Co., Ltd.) The included mixture is then maintained at 150°C for two hours. Next, after the temperature was lowered to 90°C, 0.1 parts by mass of methoquinone and 118 parts by mass of acrylic acid were added, and then 3 parts by mass of triphenylphosphine were added. Then, the temperature was further raised to 110°C, and the acid value was confirmed to be 3 mgKOH/g or less, thereby obtaining acrylic acid. Acrylic resin (ACAC-6). The property values of the acrylic acrylate resin (ACAC-6) are as follows. Weight average molecular weight (Mw): 5,000, double bond equivalent: 305.34.

(Example 1) As a solid component, 100 parts by mass of dipentaerythritol pentaacrylate ("MIRAMER M400" manufactured by MIWON Corporation containing 50% of dipentaerythritol hexaacrylate), 2-(2-hydroxy -5-tert-butylphenyl)-2H-benzotriazole ("Tinuvin PS" manufactured by BASF Japan) 0.5 parts by mass, Omnirad 184 (IGM) Production) 5 parts by mass, a mixed solvent of propylene glycol monomethyl ether/methyl ethyl ketone = 50/50 wt% was uniformly mixed so that the solid content became 40 wt%, thereby preparing an active energy ray curable composition (1) .

(Example 2 to Example 51, Comparative Example 1 to Comparative Example 2) Active energy ray curable compositions of each example were obtained in the same manner as in Example 1 except that the solid content compositions shown in Tables 2 to 6 were changed.

[Preparation of Evaluation Samples] The active energy ray curable composition of each example was applied to a polyethylene terephthalate (PET) base material (product manufactured by Toray Corporation) so that the film thickness became 1.25 μm. Named "Lumirror UH-13" thickness: 50 μm), dried at 60°C for 1 minute, irradiated with ultraviolet rays using a high-pressure mercury lamp under the conditions of 120 mW/cm ² and 250 mJ/cm ² , and The obtained laminate of the PET base material and the cured coating film was used as a test piece.

[Measurement of pencil hardness] On the surface of the hardened coating film of the evaluation sample obtained above, the pencil hardness was measured under the load condition of 500 g in accordance with JIS K5600-5-4 (1999). Each hardness was measured five times, and the hardness measured four or more times without damage was defined as the surface hardness of the laminated film. In addition, the hardness of pencils in descending order of hardness is 2H, H, F, HB, B, and HB or above is considered acceptable.

[Measurement of wetting tension] On the hardened coating surface of the evaluation sample obtained above, the wetting tension was measured in an environment of 23° C. and 50 RH% humidity using a mixture for wetting tension testing (manufactured by Wako Pure Chemical Industries, Ltd.). Measurement is performed in accordance with JIS test method K6768:1999, and the range of 35 mN/m or more and 60 mN/m or less is considered acceptable.

[Boiling water resistance test] ·Tightness Warm water was adjusted at 100°C in a constant-temperature water tank (T-104NA manufactured by THOMAS Scientific), and the evaluation sample obtained above was immersed for a certain period of time, taken out, and left to stand at room temperature for 24 hours. , and then cut 100 squares in a checkerboard near the center of the evaluation sample after the test, attach transparent tape to the cut part, and quickly peel it off to confirm whether peeling occurs. The immersion time when peeling occurs is described in Tables 1 to 6, and a time exceeding 2.5 minutes or more was considered acceptable.

[Light resistance test] · Adhesion: The evaluation sample obtained above was irradiated with ultraviolet rays for a certain period of time using a high-pressure mercury lamp under conditions of 300 mW/cm ² and 250 mJ/cm ² , and then left to stand at room temperature for 24 hours. , cut a 100-square checkerboard near the center of the evaluation sample after the test, attach transparent tape to the cut part, and quickly peel it off to confirm whether peeling occurs. The irradiation dose when peeling occurs is described in Tables 1 to 6, and an irradiation dose exceeding 250 mJ/cm ² or more was considered acceptable. In addition, the irradiation dose was calculated as 250 mJ/cm ² × ultraviolet irradiation time.

The active energy ray curable compositions (1) to active energy ray curable compositions (51) obtained in Examples 1 to 51, and the active energy ray curable compositions obtained in Comparative Examples 1 to 2 The compositions and evaluation results of the substance (C1) to the active energy ray curable composition (C2) are shown in Tables 1 to 6.

[Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 (A) Ingredients Compound (A-1) M400 100.0 M403 100.0 M404 100.0 M405 100.0 DPHA 100.0 PETA 100.0 18.5 TEM PTA 100.0 EO modified TEMPTA 100.0 Compound (A-2) Urethane Acrylate (2) 81.5 (B) Ingredients Tinuvin PS 0.5 0.5 0.5 5.0 0.5 0.5 0.5 0.5 0.5 starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness F F F F HB F HB F HB Wetting tension [mN/m] 38 35 35 35 35 35 35 35 35 Hot water resistance [min] 10.0 7.5 10.0 10.0 7.5 7.5 5.0 10.0 5.0 Light adhesion resistance [mJ/cm ² ] 750 750 750 750 750 750 500 750 500

[Table 2] Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 Example 17 Example 18 (A) Ingredients Compound (A-1) M400 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 (B) Ingredients Tinuvin 405 0.5 LA-46 0.5 1.0 1.5 2.0 4.0 Tinuvin 479 0.5 Tinuvin 460 0.5 Tinuvin 152 0.5 starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness F F F F F F F F F Wetting tension [mN/m] 38 38 38 38 38 38 38 38 38 Hot water resistance [min] 15.0 15.0 15.0 15.0 15.0 20.0 25.0 30.0 30.0 Light adhesion resistance [mJ/cm ² ] 1500 1500 1500 1500 750 2000 2500 3000 3500

[table 3] Example 19 Example 20 Example 21 Example 22 Example 23 Example 24 Example 25 Example 26 Example 27 (A) Ingredients Compound (A-1) M400 100.0 100.0 100.0 100.0 95.0 90.0 80.0 60.0 50.0 (B) Ingredients Tinuvin PS Tinuvin 405 1.0 LA-46 5.0 6.0 3.0 3.0 3.0 3.0 3.0 Tinuvin 479 Tinuvin 460 Tinuvin 152 2.0 1.0 (C) Ingredients acrylic resin(1) 5.0 10.0 20.0 40.0 50.0 (D) Ingredients Methacrylate-modified nanosilica starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness F F F F F F F F F Wetting tension [mN/m] 38 38 38 38 38 38 38 38 38 Hot water resistance [min] 25.0 20.0 30.0 30.0 35.0 40.0 45.0 45.0 40.0 Light adhesion resistance [mJ/cm ² ] 3500 3500 1000 2000 3500 3500 3500 3500 3000

[Table 4] Example 28 Example 29 Example 30 Example 31 Example 32 Example 33 Example 34 Example 35 Example 36 (A) Ingredients Compound (A-1) M400 40.0 80.0 80.0 80.0 80.0 80.0 77.5 75.0 54.9 PETA 0.5 1.0 5.1 Compound (A-2) Urethane Acrylate (1) 2.0 4.0 20.0 (B) Ingredients LA-46 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 (C) Ingredients acrylic resin (1) 60.0 20.0 20.0 20.0 acrylic resin(2) 20.0 acrylic resin (3) 20.0 acrylic resin (4) 20.0 acrylic resin (5) 20.0 Acrylic resin (6) 20.0 starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness F F F F F F F F F Wetting tension [mN/m] 38 38 38 38 38 38 38 38 38 Hot water resistance [min] 35.0 45.0 45.0 45.0 45.0 45.0 45.0 45.0 45.0 Light adhesion resistance [mJ/cm ² ] 3000 3500 3500 3500 3500 3500 4000 4500 4500

[table 5] Example 37 Example 38 Example 39 Example 40 Example 41 Example 42 Example 43 Example 44 Example 45 (A) Ingredients Compound (A-1) M400 20.0 55.0 34.9 55.5 60.0 55.1 50.0 41.6 36.1 PETA 8.2 1.0 5.1 4.5 0.0 4.9 4.1 3.4 2.9 Compound (A-2) Urethane Acrylate (1) 31.8 4.0 20.0 Urethane Acrylate (2) 20.0 18.0 15.0 13.0 Urethane Acrylate (3) 20.0 Urethane Acrylate (4) 20.0 (B) Ingredients LA-46 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 (C) Ingredients acrylic resin (1) 40.0 40.0 40.0 20.0 20.0 20.0 18.0 15.0 13.0 (D) Ingredients Methacrylate-modified nanosilica 10.0 25.0 35.0 starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness F F F F F F F H H Wetting tension [mN/m] 38 38 38 38 38 38 40 40 42 Hot water resistance [min] 45.0 45.0 45.0 45.0 45.0 45.0 50.0 55.0 60.0 Light adhesion resistance [mJ/cm ² ] 4000 4500 4500 4750 4250 4000 5000 5500 6000

[Table 6] Example 46 Example 47 Example 48 Example 49 Example 50 Example 51 Comparative example 1 Comparative example 2 (A) Ingredients Compound (A-1) M400 33.3 30.5 27.8 25.0 33.3 19.4 100.0 PETA 2.7 2.5 2.3 2.0 1.8 1.6 A9300 50.0 EO modified TEMPTA 50.0 Compound (A-2) Urethane Acrylate (2) 12.0 11.0 10.0 9.0 8.0 7.0 (B) Ingredients LA-46 3.0 3.0 3.0 3.0 3.0 3.0 (C) Ingredients acrylic resin (1) 12.0 11.0 10.0 9.0 8.0 7.0 (D) Ingredients Methacrylate-modified nanosilica 40.0 45.0 50.0 55.0 60.0 65.0 starter Rantecure 1104 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Evaluation pencil hardness H H H H H H F HB Wetting tension [mN/m] 42 ≥44 ≥44 ≥44 ≥44 ≥44 38 35 Hot water resistance [min] 60.0 60.0 60.0 60.0 60.0 50.0 2.5 2.5 Light adhesion resistance [mJ/cm ² ] 6000 6000 6000 6000 6000 5000 250.0 250.0

The abbreviations shown in Tables 1 to 6 represent the following compounds. ·M400: A mixture of 50% dipentaerythritol pentaacrylate and 50% dipentaerythritol hexaacrylate, trade name "Miramer M400", manufactured by MIWON Corporation ·M403: Dipentaerythritol pentaacrylate 40 %, a mixture of 60% dipentaerythritol hexaacrylate, trade name "Miramer M403", manufactured by MIWON Corporation·M404: 60% dipentaerythritol pentaacrylate and 40% dipentaerythritol hexaacrylate The mixture, trade name "Miramer M404", manufactured by MIWON Company. M405: a mixture of 80% dipentaerythritol pentaacrylate and 20% dipentaerythritol hexaacrylate, trade name "Miramer" Miramer M405", manufactured by MIWON Company. DPHA: dipentaerythritol hexaacrylate, trade name "Miramer M600", manufactured by MIWON Company, double bond equivalent 96.4 g/ mol ·PETA: Pentaerythritol tetraacrylate, double bond equivalent 88.1 g/mol ·TEMPTA: Trimethylolpropane triacrylate, trade name "Miramer M300", manufactured by MIWON Company, double bond Bond equivalent 98.7 g/mol · EO modified TEMPTA: Trimethylolpropane EO modified triacrylate, trade name "Miramer M3190", manufactured by MIWON Company, double bond equivalent 392.1 g /mol · A9300: Tris-(2-propenyloxyethyl) isocyanurate, trade name "NK ester A9300", manufactured by Shin-Nakamura Chemical Co., Ltd. · Urethane acrylate (1): Synthesis example The reaction product of hexamethylene diisocyanate and pentaerythritol triacrylate obtained in 1 (the mass fraction of the amount after removing pentaerythritol tetraacrylate is recorded in the table), double bond equivalent 127.5 g/mol ·carbamic acid Ester acrylate (2): the reaction product of isophorone diisocyanate and pentaerythritol triacrylate obtained in Synthesis Example 2 (the mass fraction of the amount after removing pentaerythritol tetraacrylate is recorded in the table), double bond equivalent 136.5 g/mol · Urethane acrylate (3): The reaction product of isophorone diisocyanate and dipentaerythritol pentaacrylate obtained in Synthesis Example 3, double bond equivalent 127.1 g/mol · Carbamic acid Ester acrylate (4): The reaction product of biuret-type hexamethylene diisocyanate and pentaerythritol triacrylate obtained in Synthesis Example 4 (the mass fraction of the amount after removing pentaerythritol tetraacrylate is shown in the table) , double bond equivalent 152.6 g/mol ·Tinuvin PS: 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole, trade name "Tinuvin PS ”, Tinuvin 405 manufactured by BASF Japan: R ₁ in formula (I) is (a), R ₂ is all the base represented by (f), and R in (f) ₄ is a structure of all methyl groups, the trade name is "Tinuvin 405", manufactured by BASF Japan Co., Ltd. LA-46: R ₁ in formula (I) is (b), and R ₂ is all The group represented by (f) and R ₄ in (f) have a structure in which all hydrogen atoms are used. The trade name is "Adekastab LA-46", manufactured by ADEKA Co., Ltd.·Dinubin (Tinuvin) 479: R ₁ in formula (I) is (c), R ₂ is all the group represented by (f), and the internal bond with respect to R ₄ in (f) is R ₄ in the para position. It has a structure of phenyl group and other hydrogen atoms. The trade name is "Tinuvin 479", manufactured by BASF Japan. Tinuvin 460: R ₁ in formula (I) It is a structure in which (d) and _R2 are all groups represented by (g). The trade name is "Tinuvin 460", manufactured by BASF Japan. Tinuvin 152: Formula ( In I), R ₁ is a structure represented by (e) and R ₂ are all groups represented by (h). The trade name is "Tinuvin 152", manufactured by BASF Japan Co., Ltd. Acrylic resin (1 ): The acrylic resin obtained in Synthesis Example 5, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has a structure represented by (i), the double bond equivalent is 305.3 g/mol·acrylic resin (2 ): The acrylic resin obtained in Synthesis Example 6, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has the structure represented by (i), the double bond equivalent is 250.2 g/mol·acrylic resin (3 ): The acrylic resin obtained in Synthesis Example 7, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has the structure represented by (i), the double bond equivalent is 428.9 g/mol·Acrylic resin (4 ): The acrylic resin obtained in Synthesis Example 8, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has the structure represented by (i), the double bond equivalent is 250.2 g/mol·acrylic resin (5 ): The acrylic resin obtained in Synthesis Example 9, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has a structure represented by (i), the double bond equivalent is 428.9 g/mol·Acrylic resin (6 ): The acrylic resin obtained in Synthesis Example 10, R ₆ in the formula (II) is a methyl group, R ₇ is a methyl group or has the structure represented by (i), the double bond equivalent is 305.3 g/mol·methacrylamide Modified nanosilica: Trade name "Aerosil R7200" manufactured by Evonik

The cured coating film of the active energy ray-curable composition of the present invention shows high hardness and wetting tension, and is confirmed to be excellent in hot water-resistant adhesion and light-resistant adhesion. On the other hand, it was confirmed that the hardness, hot water resistance adhesiveness, and light resistance adhesiveness of Comparative Example 1 and Comparative Example 2 which did not contain (B) component were reduced.

without

without.

Claims (16)

An active energy ray curable composition contains a compound (A) having a (meth)acrylyl group and a compound (B) having a triazine structure or a triazole structure. The active energy ray curable composition according to claim 1, wherein the compound (A) has four or more (meth)acrylyl groups in the molecule, and the double bond equivalent is 80 g/mol to 160 g. /mol range. The active energy ray curable composition according to claim 1, wherein the compound (A) contains a compound (A-1) that does not have a urethane bond in the molecule and has a (meth)acrylyl group. , and any one or both of the compounds (A-2) having a urethane bond and a (meth)acrylyl group in the molecule. The active energy ray curable composition according to claim 3, wherein the compound (A-1) contains a compound (A-1-1) containing a hydroxyl group in the molecule and a compound (A- Any or both of 1-2). The active energy ray curable composition according to claim 3, wherein the compound (A) contains the compound (A-1) and the compound (A-2), The compounding ratio [(A-1)/(A-2)] of the compound (A-2) relative to the compound (A-1) is in the range of 1/10 to 40/1. The active energy ray curable composition according to claim 1, wherein the compound (B) is a compound represented by the following formula (I); (I) In the formula (I), R ₁ represents a group represented by any one of the following formulas (a) to (e), and R ₂ represents any one of the following formulas (f) to (h). For the group represented, multiple R ₂ in the same molecule may be the same or different, In formula (a), * is the bonding bond, In formula (b), * is the bonding bond, In formula (c), * represents a bond, R ₃ represents an alkyl group having 1 to 10 carbon atoms, In formula (d), * is the bonding key, In formula (e), * is the bonding bond, In formula (f), * represents a bond, and R ₄ is any one of a hydrogen atom, a methyl group, and a phenyl group. Multiple R _4's in the same molecule may be the same or different, In formula (g), * is the bonding bond, In the formula (h), * represents a bond, and R ₅ represents an alkyl group having 1 to 8 carbon atoms. The active energy ray curable composition according to claim 1, wherein the content of the compound (B) is 0.5 to 6 parts by mass relative to 100 parts by mass of the resin solid content. The active energy ray curable composition according to claim 1, further containing an acrylic resin (C). The active energy ray curable composition according to claim 8, wherein the weight average molecular weight of the acrylic resin (C) is in the range of 5,000 to 30,000, and the double bond equivalent is in the range of 200 to 450. The active energy ray curable composition according to claim 8, wherein the acrylic resin (C) has a structure represented by the following formula (II) or formula (III); (II) In formula (II) and formula (III), R ₆ represents a hydrogen atom or a methyl group, and the repeat number n is an arbitrary natural number; in formula (II), R ₇ represents an alkyl group with 1 to 8 carbon atoms, and the formula ( Any one of the groups represented by i); in formula (III), R ₈ represents any one of the alkyl group having 1 to 8 carbon atoms and the group represented by formula (j), and the repeat number m is 2 Any of ~4; multiple R ₆ , R ₇ , R ₈ and m in the same molecule may be the same or different. In formula (i) and formula (j), * is a bond, R ₉ and R ₁₀ represents a hydrogen group or a methyl group. The active energy ray curable composition according to claim 8, wherein the content of the acrylic resin (C) is 5 to 60 parts by mass relative to 100 parts by mass of the resin solid content. The active energy ray curable composition according to claim 1, further containing inorganic particles (D). The active energy ray curable composition according to claim 12, wherein the particle diameter of the inorganic particles (D) is 200 nm or less, The content of the inorganic particles (D) is 5 to 65 parts by mass relative to 100 parts by mass of the resin solid content. The active energy ray curable composition according to claim 12, wherein the inorganic particles (D) are inorganic oxides modified with a surface modifier having a reactive group. A film characterized by having a cured coating film obtained by curing the composition according to any one of claims 1 to 14. The film according to claim 15, wherein the wetting tension on the surface of the hardened coating film is in the range of 35 mN/m to 60 mN/m.