JP2002003748A - Active energy ray curing type coating composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an extremely useful active energy ray curing type coating resin composition excellent in strength and elongation and having quick curability. SOLUTION: This active energy ray cutting type coating composition is characterized as comprising (A) a urethane acrylate resin composed of (a1) an alkylene oxide adduct of bisphenols or their hydrogenated substances, (a2) an organic diisocyanate and (a3) a hydroxy group-containing radical- polymerizable monomer and (B) radical-polymerizable monomers consisting essentially of (b1) nitrogen atom-containing radical-polymerizable monomers and including (b1) >=20 wt.% of the nitrogen atom-containing radical- polymerizable monomers in the radical-polymerizable monomers (B).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel and useful active energy ray-curable coating composition. More specifically, the present invention comprises a specific urethane acrylate resin and a nitrogen-containing radically polymerizable monomer as essential components, can provide a coating film having excellent strength and elongation, and can be rapidly cured. The present invention relates to an extremely useful coating composition having properties.

[0002]

2. Description of the Related Art Recently, due to social needs, productivity is high.
Also, there is an increasing demand for the development of paints with even higher performance.

[0003] Such high-performance paints include (1)
Active energy ray-curable resins are cited from the viewpoint of quick curing, (2) low energy cost, and (3) non-pollution by eliminating solvent.

[0004] As the energy ray-curable resin, for example, unsaturated polyester can be cited, but it is widely used in the field of woodwork paints and the like because of its good luster and solid feeling and giving a beautiful finish. However, there is a problem in that the curability is relatively poor when irradiated with active energy rays.

A urethane acrylate resin is mentioned as an energy ray-curable resin. Although there is a problem in terms of cost, it is superior in curability as compared with unsaturated polyester, and has begun to be widely used in the field of building material coating. .

[0006] In recent years, in the field of woodwork coating, imported wood of low quality and inexpensive wood has been increasing, and this imported plywood has a large internal distortion and is liable to crack under severe cold conditions. For this reason, when a general active energy ray-curable resin paint that easily causes internal distortion is applied, there is a problem that cracks are remarkably generated in a thermal cycle test.

To solve this problem, Japanese Patent Application Laid-Open No. 2000-344
No. 41, urethane acrylate resin comprising bisphenol A or bisphenol F or an alkylene oxide adduct of these hydrogenated products, an organic diisocyanate and a radical polymerizable monomer containing a hydroxyl group,
An active energy ray-curable coating composition for woodwork comprising a radical polymerizable monomer having an average concentration of a polymerizable double bond of 3 to 6 mol / Kg and a photoinitiator is disclosed. Has been improved in preventing the occurrence of cracks. However, in what is shown in the examples,
Improvements such as crack generation under cold conditions were not yet sufficient.

[0008]

The problem to be solved by the present invention is to improve the curability when irradiated with active energy rays, and to reduce cracks and the like when used in the field of woodwork paints. An active energy ray-curable coating composition is provided.

[0009]

Means for Solving the Problems Accordingly, the present inventors have conducted intensive studies with the aim of aiming at the above-mentioned problems, and as a result, the radical polymerizable monomer has a specific nitrogen atom-containing radical as an essential component. When an active energy ray-curable resin composition containing 20% by weight or more of a polymerizable monomer is used as a primer for wood, it is possible to achieve the object of preventing cracks even under more severe cold conditions. Have completed the present invention.

That is, the present invention relates to [1] an alkylene oxide adduct of a bisphenol and / or an alkylene oxide adduct of a hydrogenated bisphenol (a
1) a urethane acrylate resin (A) comprising an organic diisocyanate (a2) and a hydroxyl-containing radical polymerizable monomer (a3); and a nitrogen atom-containing radical polymerizable monomer (b1). A radical polymerizable monomer (B) as a component, and a nitrogen atom-containing radical polymerizable monomer (b) in the radical polymerizable monomer (B).
The present invention also provides an active energy ray-curable coating composition containing 20% by weight or more of (1), and [2] a radical polymerizable monomer containing a nitrogen atom in the radical polymerizable monomer (B). [1] containing 30 to 90% by weight of the monomer (b1)
The present invention also provides an active energy ray-curable coating composition as described in [3], wherein the nitrogen-containing radical polymerizable monomer (b1) is acryloylmorpholine,
N-vinylpyrrolidone, N-vinylcaprolactam, N
-The active energy ray-curable coating composition according to the above [1] or [2], which is at least one of vinylacetamide and N-vinylformamide,
Further, the present invention provides the above-mentioned [4], wherein the alkylene oxide adduct (a1) of the alkylene oxide adduct of bisphenols and / or hydrogenated bisphenols has an average addition mole number of alkylene oxide of 3 to 50 mol. An active energy ray-curable coating composition according to [1], [2] or [3] is provided.

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
The present invention uses a urethane acrylate resin as the active energy ray-curable coating composition.

The alkylene oxide adduct of bisphenols and / or the alkylene oxide adduct of hydrogenated bisphenols (a1), which is a component of the urethane acrylate resin (A) used in the present invention, comprises bisphenols and / or bisphenols Obtained by addition polymerization of an alkylene oxide to a hydrogenated product of

The bisphenols include, for example, bisphenol A, bisphenol F, bisphenol S, etc. Among them, bisphenol A and bisphenol F are preferred.

As the alkylene oxide, for example,
Ethylene oxide, propylene oxide, butylene oxide and the like can be mentioned, and they can be used alone or in combination of two or more.

Further, with respect to the alkylene oxide adduct of bisphenols and / or hydrogenated bisphenols, the average addition mole number of alkylene oxide is as follows:
Since the elongation of the urethane acrylate resin can be sufficiently obtained and the viscosity becomes appropriate, the compounding amount of the diluent is reduced and the performance of the urethane acrylate resin can be sufficiently exhibited.
モ ル 50 mol, more preferably 1-50 mol.
0 to 30 mol.

The alkylene oxide addition reaction to bisphenols and / or hydrogenated hydrogenated bisphenols is carried out, for example, at a temperature in the range of 100 to 120 ° C. in a range in which heat generation can be controlled. The alkylene oxide is sequentially added to the hydrogenated products until the desired addition amount is reached. After adding a predetermined amount of alkylene oxide,
The reaction is carried out for about an hour, and the reaction is terminated when the pressure does not decrease. These compounds are also used as BA
-4 glycol (4 mol ethylene oxide adduct of bisphenol A; Nippon Emulsifier Co., Ltd.), BA-6 glycol (6 mol ethylene oxide adduct of bisphenol A; Nippon Emulsifier Co., Ltd.), BAP-4 glycol ( 4-Molecule propylene oxide adduct of bisphenol A; Nippon Emulsifier Co., Ltd .; and BPF-4 glycol (4-moleene oxide adduct of bisphenol F; Nippon Emulsifier Co., Ltd.). Can also.

The organic diisocyanate (a) used in the present invention
As 2), for example, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate, diphenylmethane-4,4
An aromatic diisocyanate compound such as diisocyanate and 1,5-naphthalenediisocyanate; an alicyclic diisocyanate such as dicyclohexylmethane diisocyanate or isophorone diisocyanate; an aliphatic diisocyanate such as hexamethylene diisocyanate; hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane. Examples include compounds obtained by hydrogenating various aromatic ring-containing diisocyanate compounds as described above, such as 4,4-diisocyanate. These organic diisocyanates (a2) can be used alone or in combination of two or more.

Next, as the radical polymerizable monomer (a3) containing a hydroxyl group used in the present invention, various types can be used. For example, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate,
Examples include hydroxyethyl vinyl ether, hydroxybutyl vinyl ether, pentaerythritol triacrylate, isocyanuric acid ethylene oxide modified diacrylate, and ethylene oxide adducts, propylene oxide adducts, tetramethylene glycol adducts, lactone adducts, and the like. These compounds can be used alone or in combination of two or more.

In producing the urethane acrylate resin (A) used in the present invention, first, an alkylene oxide adduct of a bisphenol and / or an alkylene oxide adduct of a hydrogenated bisphenol (a1) and an organic diisocyanate (A) are used. a2) is the equivalent ratio (NCO / OH) of the isocyanate group (NCO) of the organic diisocyanate (a2) to the alkylene oxide adduct of bisphenols and / or the hydroxyl group (OH) of the hydrogenated bisphenols (a1). However, after a urethane resin is prepared by reacting in the range of 1.2 to 3.0, the hydroxyl group-containing radically polymerizable monomer (a3) may be reacted.

As the catalyst used in the above reaction, for example, various catalysts such as dibutyltin laurate, dibutyltin acetate and the like can be used, and can be produced under the conditions of a usual urethane-forming reaction. If necessary, a radical-polymerizable monomer (B) containing a solvent such as ethyl acetate, butyl acetate, methyl isobutyl ketone, toluene, or xylene or a site that does not react with isocyanate may be used. May be used as a solvent within the range described above.

The radically polymerizable monomer (B) used in the present invention is, for example, an aromatic vinyl monomer, an alkyl or cycloalkyl vinyl ether, or a mixture of the above monomer and various monohydric alcohols. Ester monomers, carboxylic acid amide group-containing vinyl monomers, polyfunctional vinyl monomers, polysiloxane bond-containing monomers, hydrolyzable silyl group-containing vinyl monomers, etc. Is mentioned.

Examples of the aromatic vinyl monomers include styrene, α-methylstyrene, p-tert-butylstyrene, chlorostyrene and vinyltoluene.

Examples of the alkyl vinyl ether or cycloalkyl vinyl ether include methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, iso-butyl vinyl ether, 2-ethylhexyl vinyl ether, cyclopentyl vinyl ether, and cyclohexyl vinyl ether. .

Examples of the polyfunctional vinyl monomers further include di (meth) acrylates of dihydric alcohols such as ethylene glycol, 1,6-hexanediol, neopentyl glycol, polyethylene glycol and polypropylene glycol; Vinyl ethers: diallyl phthalate, divinyl benzene; trimethylolpropane tri (meth) acrylate, divinyl ether; allyl (meth) acrylate, pentaerythritol tetra (meth) acrylate; tetravinyl ether, dipentaerythritol hexa (meth) acrylate; Hexavinyl ether and the like can be mentioned.

Further, the polysiloxane bond-containing monomer is
For example, as monomers with non-functional silicon atoms
If CH_Two = CHCOO (CH_Two)_Three[Si (CH_Three)
_TwoO]_nSi (CH_Three)_Three; CH_Two = C (CH_Three ) COOC
₆ H_Four [Si (CH_Three )_TwoO] nSi (CH_Three)_Three, CH_Two
= C (CH_Three) COO (CH_Two)_Three[Si (CH_Three)_TwoO] _n
Si (CH_Three)_Three, CH_Two= C (CH_Three) COO (CH_Two)_Three
[Si (CH_Three) (C₆H_Five) O]_nSi (CH_Three)_Three, CH
_Two= C (CH_Three ) COO (CH_Two )_Three [Si (C₆ H
_Five )_Two O]_n Si (CH_Three )_Three(However, n in each formula is
It shall be 0 or an integer of 1 to 130. )Such
Various monomers represented by a general formula such as
Can be

Examples of the vinyl monomer having a hydrolyzable silyl group include γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) acryloxypropyltriethoxysilane, γ- (meth) acryloxy Propylmethyldimethoxysilane, γ- (meth) acryloxypropylmethyldiethoxysilane, γ- (meth) acryloyloxypropyltriisopropenyloxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyl (tris-β-methoxyethoxy) ) Silane, vinyltriacetoxysilane, vinyltrichlorosilane and the like.

The radical polymerizable monomer (B) used in the present invention is a compound containing a nitrogen atom-containing radical polymerizable monomer (b).
It is essential that 1) is contained in an amount of 20% by weight or more, and more preferably 30 to 90% by weight or less.
When the amount of the nitrogen-containing radical polymerizable monomer (b1) is 2
If the amount is less than 0% by weight, there is a problem that sufficient cold resistance cannot be obtained, which is not preferable.

Examples of the nitrogen-containing radical polymerizable monomer (b1) which is an essential component of the present invention include amide group, amino group, imide group and the like. Unless the nitrogen atom-containing radically polymerizable monomer (b1) is used, sufficient cold heat resistance cannot be obtained, especially during woodwork painting, and cracks are caused by the cold cycle.

Nitrogen atom-containing radical polymerizable monomers (b
When (1) is exemplified, (meth) acrylamide, N, N-
Dimethyl (meth) acrylamide, N-alkoxymethyl (meth) acrylamide, N-vinylformamide,
Diacetone (meth) acrylamide, N-methylol (meth) acrylamide, (meth) acryloylmorpholine, N-vinylacetamide, N-vinylpyrrolidone, N-vinylcaprolactam, 2-dimethylaminoethyl (meth) acrylate, 2-diethylaminoethyl methacrylate , 4- (N, N-diethylamino) styrene, 4-vinylpyridine and the like. Among them, acryloylmorpholine, N-vinylpyrrolidone,
N-vinylcaprolactam, N-vinylacetamide,
N-vinylformamide is particularly preferred in terms of curability and strength of the cured coating film.

Further, a photoinitiator can be used if necessary.
Although various types of photoinitiators can be used, particularly typical ones among them include benzophenone, benzyl, Michler's ketone, thioxanthone, and a compound of a type that generates a radical by hydrogen abstraction such as anthraquinone. Generally, these compounds are used in combination with a tertiary amine such as methylamine, diethanolamine, N-methyldiethanolamine, and tributylamine. Other photoinitiators, for example,
A compound that generates radicals by intramolecular fission, such as benzoin, dialkoxyacetophenone,
Acyl oxime esters, benzyl ketals, hydroxyalkyl phenones, halogenoketones and the like can be mentioned.

The above urethane acrylate resin (A)
The mixing ratio of the photoinitiator in the active energy ray-curable resin composition comprising the polymer and the radical polymerizable monomer (B) and the photoinitiator is such that the cured film is not colored and is sufficiently cured. It is preferably 0.1 to 10 parts by weight based on 100 parts by weight of the active energy ray-curable resin composition.

The coating composition of the present invention as described above is adjusted to an appropriate coating viscosity with an organic solvent such as ethyl acetate, methyl ethyl ketone, and toluene or a diluting monomer, and is applied to an object to be coated. It can be cured by irradiation.

The active energy ray means an electromagnetic wave or a charged particle beam having an energy quantum capable of polymerizing or cross-linking a molecule. Usually, an ultraviolet ray, an electron beam or the like is used. Ultra high pressure mercury lamp, high pressure mercury lamp,
Low pressure mercury lamp, carbon arc, black light lamp,
A light source such as a metal halide lamp can be used.
As the ultraviolet wavelength, a wavelength range of usually 1900 to 3800 angstroms is mainly used.

In the case of an electron beam, an irradiation source such as a Cockloft-Walton type, a bandeograph type, a resonance transformer type, an insulation core transformer type, or various electron beam accelerators such as a linear type, a dynamitron type and a high frequency type. Can be used, and 100 to 1000 KeV, preferably 100
Irradiate with electrons with energy of ~ 300 KeV. The irradiation dose is usually preferably about 0.5 to 30 Mrad.

Further, depending on the purpose, other conventional vinyl ester resins, polyisocyanate compounds, polyepoxides, acrylic resins, alkyd resins, urea resins, melamine resins, polyvinyl acetate, vinyl acetate Copolymers, polybutadiene elastomers, saturated polyesters, saturated polyethers; cellulose derivatives such as nitrocellulose, cellulose acetate butyrate; linseed oil, tung oil, soybean oil, castor oil or epoxidized oil Natural or synthetic polymer substances such as oils and fats; active energy ray-curable resins such as unsaturated polyester resin, urethane acrylate resin and epoxy acrylate resin; calcium carbonate, talc, mica, clay, silica powder, colloidal silica, Aluminum hydroxide Various fillers such as zinc stearate, zinc white, titanium white, red iron oxide, azo pigment; pigments; addition of polymerization inhibitors such as hydroquinone, benzoquinone, toluhydrinoquinone, and paratertiary butyl catechol Can also.

The thus-obtained active energy ray-curable resin composition of the present invention is suitable for coating objects to be deformed after coating, objects to be deformed, especially woodwork products such as plywood and furniture.

[0037]

The present invention will be described in more detail with reference to the following examples. In the following, all parts and percentages are by weight unless otherwise specified. Reference Example 1 (Preparation Example 1 of urethane acrylate resin) In a 1-liter flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, 127.2 parts of ethyl acetate was added.
174 parts of tolylene diisocyanate, 1.02 parts of tert-butylhydroxytoluene, 0.15 parts of methoxyhydroquinone, and 0.05 parts of dibutyltin diacetate were added, and the temperature was raised to 70 ° C., and a 4-mol ethylene oxide adduct of bisphenol A was added. 202.25 parts were added dropwise over 1 hour. After the dropwise addition, the mixture was reacted at 70 ° C. for 3 hours.
Add 118.3 parts of hydroxyethyl acrylate,
The reaction was further carried out at 70 ° C.
The reaction was continued until the infrared absorption spectrum at 50 cm ^-1 disappeared to obtain a urethane acrylate resin. Hereinafter, this resin is referred to as (A-1).

Reference Example 2 (Formulation of urethane acrylate resin)
Production example 2) Equipped with stirrer, gas inlet tube, condenser, and thermometer
123.7 parts of butyl acetate in a 1 liter flask,
174 parts of tolylene diisocyanate, tertiary butyl
Hydroxytoluene 1.0 part, methoxyhydroquinone
0.15 parts and 0.05 parts of dibutyltin diacetate
The temperature was raised to 70 ° C, and ethylene oxide of bisphenol F
188.2 parts of side 4 mol adduct are added dropwise over 1 hour
I dropped it. After the dropwise addition, the mixture was reacted at 70 ° C. for 3 hours.
132.7 parts of xypropyl acrylate were added, and
At a temperature of 70 ° C. to give 2250
cm ^-1The reaction was continued until the infrared absorption spectrum of
Thus, a urethane acrylate resin was obtained. Hereafter this resin
(A-2).

Reference Example 3 (Preparation Example 3 of urethane acrylate resin) In a 1-liter flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, 103.6 parts of butyl acetate was added.
111 parts of isophorone diisocyanate, 0.83 parts of tert-butylhydroxytoluene, 0.12 parts of methoxyhydroquinone and 0.08 parts of dibutyltin diacetate are added, and the temperature is raised to 70 ° C., and 4 moles of ethylene oxide of hydrogenated bisphenol A is added. 247.4 parts of the product were added dropwise over 1 hour. After dropping, reacting at 70 ° C for 3 hours,
66.3 parts of 2-hydroxypropyl acrylate was added, and the mixture was further reacted at 70 ° C. until the infrared absorption spectrum at 2250 cm ⁻¹ indicating an isocyanate group disappeared to obtain a urethane acrylate resin. Hereinafter, this resin is referred to as (A-3).

Reference Example 4 (Preparation Example 4 of urethane acrylate resin) In a 1-liter flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, 121.4 parts of butyl acetate was added.
113.2 parts of isophorone diisocyanate, 0.97 part of tert-butylhydroxytoluene, 0.15 part of methoxyhydroquinone and 0.1 part of dibutyltin diacetate are added, and the temperature is raised to 70 ° C., and 17 mol of ethylene oxide of bisphenol A is added. 332.2 parts were added dropwise over 1 hour. After dropping, reacting at 70 ° C for 3 hours,
40.2 parts of hydroxyethyl acrylate was added, and the mixture was further reacted at 70 ° C.
The reaction was carried out until the infrared absorption spectrum at 0 cm ^-1 disappeared to obtain a urethane acrylate resin. Hereinafter, this resin is referred to as (A-4).

Reference Example 5 (Preparation Example 5 of Urethane Acrylate Resin) In a 1-liter flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, 114.8 parts of butyl acetate was placed.
80.0 parts of isophorone diisocyanate, 1.15 parts of tert-butylhydroxytoluene, 0.17 parts of methoxyhydroquinone and 0.11 part of dibutyltin diacetate are added, and the temperature is raised to 70 ° C., and 40 mol of ethylene oxide of bisphenol A is added. 358.2 parts were added dropwise over 1 hour. After dropping, reacting at 70 ° C for 3 hours,
21.3 parts of hydroxyethyl acrylate were added, and the mixture was further reacted at 70 ° C. to obtain 225 showing an isocyanate group.
The reaction was carried out until the infrared absorption spectrum at 0 cm ^-1 disappeared to obtain a urethane acrylate resin. Hereinafter, this resin is referred to as (A-5).

Comparative Reference Example 1 A 1-liter flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer was charged with a butyl acetate portion, an isophorone diisocyanate portion, a tertiary butyl hydroxytoluene portion, a methoxyhydroquinone portion, a dibutyltin dibutyltin portion. An acetate portion was added, the temperature was raised to 70 ° C., and 358.2 parts of polypropylene glycol (number average molecular weight 1000) was added dropwise over 1 hour. After the dropwise addition, the mixture was reacted at 70 ° C. for 3 hours, 21.3 parts of hydroxyethyl acrylate was added, and the mixture was further reacted at 70 ° C. until the infrared absorption spectrum at 2250 cm ⁻¹ indicating an isocyanate group disappeared. And a urethane acrylate resin. Hereinafter, this resin is referred to as (A'-1).

Examples 1 to 5 Coatings C1 to C5 were prepared according to the formulations shown in Table 1. Comparative Examples 1 to 3 Paints R1 to R3 were prepared according to the formulation shown in Table 2.

<Evaluation method> Examples 1 to 5 and Comparative examples 1 to 5
Using the paint prepared in No. 3, painting and evaluation were performed by the methods described below.

(1) Coating method: Bar coater (No. 30)
And coated on a Bonde 144-treated steel sheet (bending test test), oak plywood (10 cm × 10 cm × 1 cm) (cold heat test), and a glass plate (elongation at break), and a conveyer speed of 10 m / The coating surface was passed (passed) under the conditions of minutes (approximately 100 mj / cm2 per pass) until there was no tack (touch) on the coated surface. (2) Curability: The number of UV irradiation passes until touch drying under the conditions of (1) was shown. (3) Cold repetition test: Test for the number of cracks in the coating film after 4 cycles of 4 cycles of 1 cycle of 80 ° C. for 2 hours and -20 ° C. for 2 hours.
Measure the number of cracks. (The crack length is 1cm
If the number of occurrences of the above is 10 or less, it is marked as ○, and 10 to 30
(4) Bending test: The film was bent 180 ° using a bending tester, and the state of cracks in the coating film was observed.も の indicates that no crack was generated, X indicates that the cracked coating film was completely broken, and △ indicates that some cracks were generated. (5) Tensile test: Tensile tester (TOYO B)
ALDWIN TENSILON UTM4-10
0), cured film (1cm peeled from glass plate)
The elongation at break (%) of the test piece having a width at normal temperature was measured.

[0046]

[Table 1]

[0047]

[Table 2]

<Footnotes to Tables 1 and 2> ACMO: Acryloylmorpholine NVP: N-vinylpyrrolidone PE-300: Polyethylene glycol 300 diacrylate (manufactured by Toagosei) TMPTA: Trimethylolpropane triacrylate D-1173: Darocure 1173 (Photoinitiator manufactured by Ciba Geigy) P-2M: bis (2-methacryloyloxyethyl) acid phosphate

[0049]

[Table 3]

[0050]

According to the present invention, by using a specific urethane acrylate resin and a nitrogen-containing radically polymerizable monomer as subcomponents, the strength and elongation are excellent, and cracks hardly occur under cold conditions. An extremely useful active energy ray-curable coating resin composition having fast curing properties can be provided.

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Claims (4)

[Claims] 1. An alkylene oxide adduct of bisphenols and / or an alkylene oxide adduct of hydrogenated bisphenols (a1), an organic diisocyanate (a2), and a hydroxyl-containing radical polymerizable monomer (a3) And a nitrogen atom-containing radically polymerizable monomer (b)
A radical polymerizable monomer (B) having 1) as an essential component, wherein the radical polymerizable monomer (b1) contains 20% by weight of the radical polymerizable monomer (b1) in the radical polymerizable monomer (B). An active energy ray-curable coating composition comprising: 2. The radically polymerizable monomer (B) is replaced with a nitrogen atom-containing radically polymerizable monomer (b1) by 30 to 90.
The active energy ray-curable coating composition according to claim 1, wherein the coating composition contains 0.1% by weight. 3. The nitrogen-containing radical polymerizable monomer (b1) is selected from the group consisting of (meth) acryloylmorpholine, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylacetamide and N-vinylformamide. 2. The at least one monomer as claimed in claim 1,
Or the active energy ray-curable coating composition according to 2. 4. The alkylene oxide adduct of bisphenols and / or the alkylene oxide adduct of hydrogenated bisphenols (a1) has an average alkylene oxide addition mole number of 3 to 50 moles.
4. The active energy ray-curable coating composition according to 2 or 3.