JP3475492B2 - Compositions and uses thereof - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a protective coating agent,
More specifically, the present invention relates to a protective coating agent which is useful for optical media such as optical discs, which has excellent antistatic properties and surface stability over time.

[0002]

2. Description of the Related Art Conventionally, various types of coating agents for optical media, especially optical discs, have been proposed. However, the coating agents proposed so far have various antistatic properties because they impart antistatic ability. Contains an inhibitor. Examples of the antistatic agent include a surfactant and a metal filler, but there is a problem in stability over time such as bleeding out.

[0003]

An object of the present invention is to provide a composition having an excellent antistatic ability when cured. In particular, it is to provide a composition which prevents dust and the like from adhering to the surface of a disk when used as a protective coating agent for an optical disk. Another object of the present invention is to use an antistatic agent (quaternary ammonium salt having a phenylketone skeleton) having reactivity with an ultraviolet curable resin, so that the surface of the disk due to bleeding out after curing can be removed. It is an object of the present invention to provide a composition which is a protective coating agent which avoids contamination and is excellent in surface stability over time.

[0004]

The inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, the film formed on the surface of the disk has an antistatic function and is less likely to be contaminated by dust. We have completed a UV-curable protective coating agent that cures in the atmosphere with excellent temporal stability of the surface condition of the film in the environment of high temperature and high humidity, which is a durability test condition for optical media.

That is, the present invention provides a compound (A1) represented by the formula (1),

[0006]

[Chemical 2]

Quaternary ammonium salt having a phenyl ketone skeleton (B), compound (C) having at least one hydroxyl group and at least one unsaturated group in the molecule, (meth) acrylic acid ester (D), And a photoinitiator (E), an ultraviolet curable coating agent and an optical disk protective coating agent which are curable in the atmosphere, and an antistatic plasticizer containing a quaternary ammonium salt. (A2), quaternary ammonium salt having phenyl ketone skeleton (B), compound (C) having at least one hydroxyl group and at least one unsaturated group in the molecule, (meth)
The present invention relates to a composition containing an acrylic acid ester (D) and a photoinitiator (E), an ultraviolet-curable coating agent curable in the atmosphere, and a protective coating agent for an optical disk, which composition comprises the composition.

The present invention will be described in detail below.

The compound (A1) represented by the formula (1) used in the present invention is known as a reactive anionic surfactant or a nonionic surfactant, and specifically, a reactive anionic surfactant is used. As an activator, manufactured by Asahi Denka Co., Ltd., trade name "ADEKA REASOAP Series SE-10N" (X =-
SO ₃ NH ₄ ), as a nonionic surfactant, manufactured by Asahi Denka Co., Ltd. under the trade name “Adeka Rear Soap Series NE-1”
0 "(X = -H).

The addition amount of the compound (A1) in the present invention is 0.1% by weight or more and 20% by weight or less, preferably 0.5% by weight or more and 15% by weight or less in the composition. More preferably, it is 1% by weight or more and 10% by weight or less. 0.1
If the addition amount is less than wt%, it is difficult to impart sufficient antistatic ability, and if the addition amount exceeds 20 wt%, the stability over time of the film may decrease.

As the antistatic plasticizer (A2) containing a quaternary ammonium salt used in the present invention, phthalic acid diester, phosphoric acid triester, aliphatic dibasic acid ester, glycol ester, epoxy compound and the like and quaternary Compositions with ammonium salts are mentioned. The quaternary ammonium salt can be used without particular limitation. Since these antistatic plasticizers themselves have positive and negative dipoles, etc., their addition reduces the intermolecular force of the material, making it easier for them to enter between molecules and tending to develop the antistatic effect. Become. Specific examples of the antistatic plasticizer (A2) include, for example, "Adeka Sizer LV-" manufactured by Asahi Denka Co., Ltd., which has a phthalate derivative (formula (2)) and a quaternary ammonium salt. 70 ", a product of Asahi Denka Co., Ltd., which has an aliphatic dibasic acid ester derivative (formula (3)) and a quaternary ammonium salt, and a trade name" ADEKA CIZER LV-808 ".

[0012]

[Chemical 3]

[0013]

[Chemical 4]

The antistatic plasticizer (A2) is added in an amount of 0.1% by weight or more and 20% by weight or less, preferably 0.1% by weight or less.
2% by weight or more and 15% by weight or less, more preferably 0.3
It is from 10% by weight to 10% by weight. If the amount added is less than 0.1% by weight, it is difficult to impart sufficient antistatic ability, and if the amount added exceeds 20% by weight, the stability over time of the film may deteriorate.

Examples of the quaternary ammonium salt type surfactant (B) having a phenylketone skeleton which can be used in the present invention include (4-benzoylbenzyl) trimethylammonium chloride and 4-benzoyl-N, N. -Dimethyl- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethanaminium bromide, 2-hydroxy-3- (3,4-dimethyl-9-oxo-9H-thioxanthene 2-yloxy) -N , N,
N-trimethyl-1-propanaminium chloride and the like can be mentioned.

The addition amount of the surfactant (B) of the present invention is 0.1% by weight or more and 15% by weight or less, preferably 0.5% by weight or more and 10% by weight or less, more preferably 1% by weight in the composition.
It is at least 8% by weight. If the amount added is less than 0.1% by weight, it is difficult to obtain the effect of imparting antistatic ability, and if the amount added exceeds 15% by weight, the stability of the film with time may decrease.

As the compound (C) having at least one hydroxyl group and at least one unsaturated group in the molecule which can be used in the present invention, for example, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2 -Hydroxy-3-phenoxypropyl acrylate, 2-hydroxybutyl acrylate, 2-acryloyloxyethyl acid phosphate, pentaerythritol triacrylate, 3-acryloyloxyglycerin monomethacrylate, 2-acryloyloxyethyl-2-hydroxypropyl phthalate, glycerin Methacrylate acrylate, isocyanuric acid E
Examples thereof include O-modified (n = 3) diacrylate.

The amount of compound (C) added is 0.5 in the composition.
% To 50% by weight, preferably 1 to 4% by weight
It is 5% by weight or less, more preferably 2% by weight or more and 30% by weight or less. If it is less than 0.5% by weight, it is difficult to obtain a transparent and uniform composition, and if it is more than 50% by weight, the hardness and scratch resistance of the film are lowered, and the film is stable over time. There is a case where the sex is deteriorated.

The (meth) acrylic acid ester (D) in the present invention is, for example, an acrylic and / or methacrylic acid ester, and more specifically, it is monofunctional or difunctional.
Functional and trifunctional or higher functional acrylic and / or methacrylic acid esters.

Examples of the monofunctional acrylic and / or methacrylic acid ester that can be used in the present invention include tetrahydrofurfuryl acrylate and isobornyl acrylate.

The addition amount of the monofunctional acrylic and / or methacrylic acid ester is 0% by weight or more and 50% by weight or less,
Preferably, it can be used in an amount of 5% by weight or more and 45% by weight or less. When it is used in an amount of more than 50% by weight, it may be difficult to form a three-dimensional crosslinked structure of the cured film.

A typical example of the bifunctional acrylic and / or methacrylic acid ester that can be used in the present invention is polyethylene glycol (PEG) # 40.
Examples thereof include 0-diacrylate, PEG # 600 diacrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate ethylenoxide-modified bisphenol A diacrylate, and hydrogenated dicyclopentadienyl diacrylate.

The addition amount of the bifunctional acrylic and / or methacrylic acid ester is 5% by weight or more and 50% by weight or less, preferably 8% by weight or more and 45% by weight or less. 5
When the concentration is lower than 50% by weight, the adhesion to the polycarbonate substrate may not be exhibited, and when it is added in excess of 50% by weight, the protective property of the film may be deteriorated.

Typical examples of trifunctional or higher functional acrylic and / or methacrylic acid esters that can be used in the present invention include trimethylolpropane triacrylate, ethylene oxide-modified trimethylolpropane triacrylate, pentaerythritol triacrylate and penta. Examples thereof include erythritol tetraacrylate and dipentaerythritol hexaacrylate.

The amount of trifunctional or higher functional acrylic and / or methacrylic acid ester added is from 5% by weight to 80% by weight.
Hereafter, the range is preferably 20% by weight or more and 70% by weight or less. If it is less than 5% by weight, the hardness and scratch resistance required for protection may be lowered, and if it exceeds 80% by weight, the film shrinkage ratio upon curing the coating agent may be high.

As the (meth) acrylic acid ester used in the present invention, one kind may be used, or two or more kinds may be used in combination.

As the photoinitiator (E) in the present invention,
Examples thereof include acetophenone-based, benzoin ether-based, thioxanthone-based, and benzophenone-based photoinitiators. Moreover, you may add a hydrogen donor as needed.

The photoinitiator (E) that can be used in the present invention is, for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexylphenylketone, or 2
-Methyl-2-morpholino (4-thiomethylphenyl)
Propane 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, benzoin methyl ether, benzoinetyl ether, benzoyl isopropyl ether, benzoyl isobutyl ether, benzophenone, 3,3 ', 4 , 4'-tetra (t-butylperoxycarbonyl) benzophenone,
Methyl o-benzoylbenzoate, 4,4'-dichlorobenzophenone, 4-phenylbenzophenone, 4-benzoyl-4'-methylphenyl sulfide, hydroxybenzophenone, 2-isopropylthioxanthone,
Examples include 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone.

Examples of hydrogen donors usable in the present invention include triethanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate and 4-dimethylaminobenzoate. 2-ethylhexyl acid, benzoic acid (2
-Dimethylamino) ethyl, 4,4'-dimethylaminobenzophenone, 4,4'-diethylaminobenzophenone, 4-dimethylaminoacetophenone and the like can be exemplified.

The addition amount of the photoinitiator (E) in the present invention is 0.1% by weight or more and 15% by weight or less, preferably 1% by weight or more and 10% by weight or less in the composition. More preferably, it is 2% by weight or more and 8% by weight or less. If added in excess of 15% by weight, unreacted photoinitiator during curing may reduce the stability of the film over time. Also, 0.1
If the addition amount is less than wt%, the curability will be significantly reduced, and thus it is not practical.

If desired, the composition of the present invention may further contain commonly used additives.

A protective coating agent can be obtained by polymerizing the above ultraviolet curable composition using a high pressure mercury lamp. It can be inferred from the light emission spectrum pattern that an ultra-high pressure mercury lamp, a metal halide lamp, etc. can be used as an ultraviolet ray source other than the high pressure mercury lamp.

Further, for the purpose of imparting a uniform coating property and suppressing the occurrence of coating defects such as orange peel and craters, one or more leveling agents can be added to the coating agent. Silicone-based surfactants and fluorine-based surfactants are generally known as leveling agents, and they can be used within a range that does not impair the performance of a coating agent intended for them.

The integrated quantity of light when the ultraviolet irradiation in the present invention, 200 mJ / cm ² or more 1500 mJ / cm ² or less,
Preferably 300 mJ / cm ² or more and 1000 mJ / c
m ² or less. If it is less than 200 mJ / cm ² , the curability may be poor, and if it exceeds 1500 mJ / cm ² , the cured film may shrink.

[0035]

The UV-curable composition obtained by using the photoinitiator system of the present invention thus obtained is photocured under predetermined conditions to enhance the antistatic property of the substrate surface and It is a protective coating agent with excellent stability over time.

[0036]

EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.

Example 1 As the compound (A1), n = 10 and X = in the above formula (1)
Compound of SO ₃ NH ₄ (manufactured by Asahi Denka Co., Ltd., trade name “SE-
10N ") 20 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name" KAYAC ").
URE BTC ") 30 g, 2 as the compound (C)
-Hydroxyethyl acrylate 50 g, (meth) acrylic acid ester (D) trimethylolpropane triacrylate 450 g, polyethylene glycol (P
EG) # 400 diacrylate 300 g, hydrogenated dicyclopentadienyl diacrylate 100 g, 1,6-hexanediol diacrylate 100 g, photoinitiator (E)
As a leveling agent, 30 g of methyl benzoyl formate and 1 g of a silicone-based paint additive (trade name “KP-306” manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent are mixed and dissolved, and the resin composition of the present invention ( A protective coating agent for optical disc) was obtained.

After 1.5 g of this resin composition was dispensed onto the non-grooved surface of a polycarbonate magneto-optical disk substrate having a diameter of 90 mm, a thickness of 10 μm was obtained by spin coating.
m, which was exposed and cured using a 120 W / cm high pressure mercury lamp. The above process is 23 ± 1
It was performed in an environment of 50 ° C. and 50 ± 3% RH.

The exposure was performed from a height of 100 mm above the film so that the integrated irradiation amount of ultraviolet rays was 650 mJ / cm ² (λ = 365 nm).

The test evaluation of scratch resistance was carried out by visually observing the coated surface state with a steel wool # 0000 under a load of 100 g under a fluorescent lamp, and the pencil hardness was measured by J
Performed according to ISK-6911. After the disk was stored for 2000 hours in an environment of a temperature of 80 ° C. and a humidity of 85% RH, the surface of the film was observed with an optical microscope. The test results are shown in Table 1.

Example 2 As compound (A1), n = 10 and X = in the above formula (1)
Compound of SO ₃ NH ₄ (manufactured by Asahi Denka Co., Ltd., trade name “SE-
10N ") 50 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name" KAYAC ").
URE BTC ") 30 g, 2 as the compound (C)
-Hydroxyethyl acrylate 50 g, (meth) acrylic acid ester (D) as trimethylolpropane triacrylate 450 g, polyethylene glycol (PEG) # 400 diacrylate 300 g, hydrogenated dicyclopentadienyl diacrylate 100 g, 1,6-
100 g of hexanediol diacrylate, 30 g of methylbenzoyl formate as a photoinitiator (E),
And 1 g of a silicone-based paint additive (trade name "KP-306" manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent.
Were thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disks).

Using this resin composition, a coated substrate was prepared in the same manner as in Example 1, the film test was conducted in the same manner as in Example 1, and the environment preservation test was conducted to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 1.

Example 3 As the compound (A1), n = 10 and X = in the above formula (1)
Compound of SO ₃ NH ₄ (manufactured by Asahi Denka Co., Ltd., trade name “SE-
10N ") 50 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name" KAYAC ").
URE BTC ") 30 g, 2 as the compound (C)
50 g of hydroxypropyl acrylate, 450 g of trimethylolpropane triacrylate as (meth) acrylic acid ester (D), 300 g of polyethylene glycol (PEG) # 400 diacrylate, 100 g of hydrogenated dicyclopentadienyl diacrylate, 1,6-
100 g of hexanediol diacrylate, 30 g of methylbenzoyl formate as a photoinitiator (E),
And 1 g of a silicone-based paint additive (trade name "KP-306" manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent.
Were thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disks).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, the film was tested in the same manner as in Example 1, and the environment preservation test was carried out to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 1.

Example 4 As compound (A1), n = 10 and X = in the above formula (1)
Compound of H (Asahi Denka Co., Ltd., trade name "NE-10")
50 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name “KAYACURE BT
C "), 50 g of 2-hydroxyethyl acrylate as compound (C), 350 g of dipentaerythritol hexaacrylate as (meth) acrylic acid ester (D), polyethylene glycol (PEG) # 40.
0 diacrylate 400 g, 1,6-hexanediol diacrylate 100 g, tetrahydrofurfuryl acrylate 100 g, and 2-hydroxy-2-methyl-1-phenylpropan-1-one 5 as a photoinitiator (E).
0 g, and a silicone-based paint additive as a leveling agent (Shin-Etsu Chemical Co., Ltd., trade name "KP-306")
Was thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disk).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, the film was tested in the same manner as in Example 1, and the environment preservation test was carried out to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 1.

Example 5 As the compound (A1), n = 10 and X = in the above formula (1)
Compound of H (Asahi Denka Co., Ltd., trade name "NE-10")
50 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name “KAYACURE BT
C "), 50 g of 2-hydroxypropyl acrylate as the compound (C), 350 g of dipentaerythritol hexaacrylate as the (meth) acrylic acid ester (D), polyethylene glycol (PEG) # 4.
00 diacrylate 400 g, 1,6-hexanediol diacrylate 100 g, tetrahydrofurfuryl acrylate 100 g, 2-hydroxy-2-methyl-1-phenylpropan-1-one 50 g as a photoinitiator (E), and a leveling agent As a silicone-based paint additive (Shin-Etsu Chemical Co., Ltd., trade name "KP-30"
6 ") was thoroughly mixed and dissolved to obtain a resin composition (protective coating agent for optical disc) of the present invention.

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 1.

Comparative Example 1 As the compound (A1), n = 10 and X = in the above formula (1).
Compound of SO ₃ NH ₄ (manufactured by Asahi Denka Co., Ltd., trade name “SE-
10N ") 50 g, as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name" KAYAC ").
URE BTC "), 500 g of trimethylolpropane triacrylate as (meth) acrylic acid ester (D), polyethylene glycol (PEG) # 40
0 diacrylate 300 g, hydrogenated dicyclopentadienyl diacrylate 100 g, 1,6-hexanediol diacrylate 100 g, methylbenzoyl formate 30 g as a photoinitiator (E), and a silicone-based coating additive ( Shin-Etsu Chemical Co., Ltd.
1 g of the product name "KP-306" manufactured by Kanamoto Co., Ltd. was well mixed and dissolved, but the resin composition became cloudy and could not be uniformly dissolved.

Comparative Example 2 As the compound (A1), n = 10 and X = in the above formula (1).
Compound of SO ₃ NH ₄ (manufactured by Asahi Denka Co., Ltd., trade name “SE-
10N "), 50 g of 2-hydroxyethyl acrylate as the compound (C), 450 g of trimethylolpropane triacrylate as the (meth) acrylic acid ester (D), polyethylene glycol (PEG) # 4.
00 diacrylate 300 g, hydrogenated dicyclopentadienyl diacrylate 100 g, 1,6-hexanediol diacrylate 100 g, methylbenzoyl formate 30 g as a photoinitiator (E), and a silicone-based coating additive ( Shin-Etsu Chemical Co., Ltd.
The product (trade name: “KP-306”) manufactured by Kuraray Co., Ltd. was thoroughly mixed and dissolved to obtain a resin composition (protective coating agent for optical disc).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 1.

Comparative Example 3 As the quaternary ammonium salt (B), (4-benzoylbenzyl) trimethylammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name "KAYACUREBTC") 30
g, 50 g of 2-hydroxyethyl acrylate as the compound (C), 450 g of trimethylolpropane triacrylate as the (meth) acrylic acid ester (D),
Polyethylene glycol (PEG) # 400 diacrylate 300 g, hydrogenated dicyclopentadienyl diacrylate 100 g, 1,6-hexanediol diacrylate 100 g, as a photoinitiator (E), methylbenzoyl formate 30 g, and as a leveling agent Silicone paint additive (Shin-Etsu Chemical Co., Ltd., trade name "K
P-306 ") was thoroughly mixed and dissolved to obtain a resin composition (protective coating agent for optical disk).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 1.

[0054]

[Table 1]

Example 6 As an antistatic plasticizer (A2), Asahi Denka Co., Ltd., trade name "Adeka Sizer LV-70" 3 g, and as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethyl Ammonium chloride (Nippon Kayaku Co., Ltd., K
AYACUREBTC) 30 g, as the compound (C),
50 g of 2-hydroxyethyl acrylate, 350 g of trimethylolpropane triacrylate as (meth) acrylic acid ester (D), 400 g of polyethylene glycol (PEG) # 400 diacrylate, 1,6-
100 g of hexanediol diacrylate, 100 g of tetrahydrofurfuryl acrylate, 30 g of methylbenzoyl formate as a photoinitiator (E), and a silicone-based coating additive as a leveling agent (Shin-Etsu Chemical Co., Ltd., trade name "KP-306" 1) was thoroughly mixed and dissolved to obtain the resin composition of the present invention (protective coating agent for optical disks).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 2.

Example 7 As an antistatic plasticizer (A2), 3 g of Adeka Sizer LV-70, trade name, manufactured by Asahi Denka Co., Ltd., and 4-benzoyl-N, N as a quaternary ammonium salt (B) were used. -Dimethyl-N- [2- (1-oxo-2-propenyloxy)
Ethyl] benzenemethanaminium bromide (Nippon Kayaku Co., Ltd., KAYACURE ABQ) 30 g, 2-hydroxyethyl acrylate 50 as compound (C)
g, as (meth) acrylic acid ester (D), trimethylolpropane triacrylate 350 g, polyethylene glycol (PEG) # 400 diacrylate 40
0 g, 1,6-hexanediol diacrylate 100
g, tetrahydrofurfuryl acrylate 100 g, methyl benzoyl formate 3 as a photoinitiator (E)
0 g, and a silicone-based paint additive as a leveling agent (Shin-Etsu Chemical Co., Ltd., trade name "KP-306")
Was thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disk).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 2.

Example 8 As an antistatic plasticizer (A2), Asahi Denka Co., Ltd., trade name "Adeka Sizer LV-808" 3 g, and as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethyl Ammonium chloride (manufactured by Nippon Kayaku Co., Ltd.,
30 g of KAYACURE BTC), 50 g of 2-hydroxyethyl acrylate as the compound (C), 250 g of dipentaerythritol hexaacrylate as the (meth) acrylic acid ester (D), 400 g of polyethylene glycol (PEG) # 400 diacrylate,
150 g of 1,6-hexanediol diacrylate, 150 g of tetrahydrofurfuryl acrylate, 30 g of methylbenzoyl formate as a photoinitiator (E),
And 1 g of a silicone-based paint additive (trade name "KP-306" manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent.
Were thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disks).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 2.

Example 9 As an antistatic plasticizer (A2), Asahi Denka Co., Ltd., trade name "Adeka Sizer LV-808 (Asahi Denka Co., Ltd.)"
3 g, as a quaternary ammonium salt (B), 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2
-Propenyloxy) ethyl] benzenemethanaminium bromide (manufactured by Nippon Kayaku Co., Ltd., KAYACURE A)
BQ) 30 g, 2-hydroxyethyl acrylate 50 g as compound (C), dipentaerythritol hexaacrylate 250 g, polyethylene glycol (PEG) # 4 as (meth) acrylic acid ester (D).
00 diacrylate 400 g, 1,6-hexanediol diacrylate 150 g, tetrahydrofurfuryl acrylate 150 g, methyl benzoyl formate 30 g as a photoinitiator (E), and a silicone-based paint additive as a leveling agent (Shin-Etsu Chemical Co., Ltd. ), Trade name "KP-306"), was well mixed and dissolved to obtain the resin composition of the present invention (protective coating agent for optical disks).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 2.

Example 10 As an antistatic plasticizer (A2), 3 g of Adeka Sizer LV-70, trade name, manufactured by Asahi Denka Co., Ltd., and quaternary ammonium salt (B) of (4-benzoylbenzyl) trimethyl were used. Ammonium chloride (Nippon Kayaku Co., Ltd., K
AYACUREBTC) 30 g, as the compound (C),
50 g of 2-acryloyloxyethyl acid phosphate, 350 g of trimethylolpropane triacrylate as (meth) acrylic acid ester (D), 400 g of polyethylene glycol (PEG) # 400 diacrylate, 1,6-hexanediol diacrylate 1
00g, tetrahydrofurfuryl acrylate 100
g, 30 g of methylbenzoyl formate as a photoinitiator (E), and a silicone-based coating additive as a leveling agent (manufactured by Shin-Etsu Chemical Co., Ltd., trade name "KP-30"
6 ") was thoroughly mixed and dissolved to obtain a resin composition (protective coating agent for optical disc) of the present invention.

A substrate coated with this resin composition was prepared in the same manner as in Example 1, the film was tested in the same manner as in Example 1, and the environment preservation test was carried out to determine the surface condition with an optical microscope. Observed at. The results are shown in Table 2.

Comparative Example 4 As an antistatic plasticizer (A2), 3 g manufactured by Asahi Denka Co., Ltd. under the trade name "Adeka Sizer LV-70", and as a quaternary ammonium salt (B), (4-benzoylbenzyl) trimethyl was used. Ammonium chloride (manufactured by Nippon Kayaku Co., Ltd., trade name "KAYACURE BTC") 30 g, (meta)
As acrylic acid ester (D), 400 g of trimethylolpropane triacrylate, 400 g of polyethylene glycol (PEG) # 400 diacrylate, 1,6
-Hexanediol diacrylate 100 g, tetrahydrofurfuryl acrylate 100 g, photoinitiator (E)
As a leveling agent, 30 g of methylbenzoyl formate and 1 g of a silicone-based paint additive (trade name “KP-306” manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent are mixed well.
Although dissolved, the resin composition became cloudy and could not be uniformly dissolved.

Comparative Example 5 As an antistatic plasticizer (A2), Asahi Denka Co., Ltd., trade name "ADEKA CIZER LV-70" 3 g, as compound (C) 50 g of 2-hydroxyethyl acrylate, (meth) acrylic As the acid ester (D), 350 g of trimethylolpropane triacrylate, 400 g of polyethylene glycol (PEG) # 400 diacrylate,
100 g of 1,6-hexanediol diacrylate, 100 g of tetrahydrofurfuryl acrylate, 30 g of methylbenzoyl formate as a photoinitiator (E),
And 1 g of a silicone-based paint additive (trade name "KP-306" manufactured by Shin-Etsu Chemical Co., Ltd.) as a leveling agent.
Were thoroughly mixed and dissolved to obtain a resin composition of the present invention (protective coating agent for optical disks).

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to determine the surface condition by an optical microscope. Observed at. The results are shown in Table 2.

Comparative Example 6 30 g of (4-benzoylbenzyl) trimethylammonium chloride (KAYACURE BTC, manufactured by Nippon Kayaku Co., Ltd.) as the quaternary ammonium salt (B), and 2-hydroxyethyl acrylate as the compound (C) 5
0 g, as (meth) acrylic acid ester (D), trimethylolpropane triacrylate 350 g, polyethylene glycol (PEG) # 400 diacrylate 4
00 g, 1,6-hexanediol diacrylate 10
0 g, tetrahydrofurfuryl acrylate 100 g,
30 g of methylbenzoyl formate as a photoinitiator (E), and a silicone-based coating additive as a leveling agent (Shin-Etsu Chemical Co., Ltd., trade name "KP-30"
6 ") was thoroughly mixed and dissolved to obtain a resin composition (protective coating agent for optical disc) of the present invention.

A substrate coated with this resin composition was prepared in the same manner as in Example 1, and a film test was conducted in the same manner as in Example 1, and an environmental preservation test was conducted to examine the surface condition with an optical microscope. Observed at. The results are shown in Table 2.

[0070]

[Table 2]

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Claims (3)

(57) [Claims] 1. A compound (A1) represented by formula (1): Quaternary ammonium salt having phenyl ketone skeleton (B), compound (C) having at least one hydroxyl group and at least one unsaturated group in the molecule, (meth) acrylic acid ester (D) and photoinitiator ( A composition comprising E) in the following proportions: (A1): 0.1 wt% or more and 20 wt% or less, (B): 0.1 wt% or more and 15 wt% or less, (C): 0.5 wt% or more and 50 wt% or less, (D): Single Functional acrylic and / or methacrylic
Acid ester 0% to 50% by weight, bifunctional acrylic and / or methacrylic acid ester 5% to 50% by weight, trifunctional or more acrylic and / or methacrylic acid ester
Tell 5% to 80% by weight, (E): 0.1% to 15% by weight 2. An ultraviolet curable coating agent comprising the composition according to claim 1, which is curable in the atmosphere. 3. A protective coating agent for an optical disk, which is curable in the atmosphere and comprises the composition according to claim 1 .