JP2002069138A - UV curable resin composition and use thereof - Google Patents

Abstract

(57) [Problem] To provide an ultraviolet curable resin composition having excellent adhesion to polyester film, metal, and glass. (A) hydrogenated polybutadiene polyol,
Urethane acrylate resin obtained by reacting polyisocyanate and hydroxyalkyl acrylate,
(B) a radiation-curable resin composition containing an aliphatic or alicyclic alkyl acrylate having 6 or more carbon atoms, preferably (C) a Michael adduct of acrylic acid, or 2
-A radiation-curable resin composition containing acryloyloxyethyl dicarboxylic acid monoester.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ultraviolet-curable resin composition having good adhesion to plastic films such as metal, glass, polyester and the like, and to its use.

[0002]

2. Description of the Related Art Conventionally, active energy ray-curable resin compositions have been widely used as adhesives for films and the like because curing is completed by irradiation of ultraviolet rays or the like for a very short time. For example, JP-A-6-184498 discloses a curable adhesive composition comprising at least one selected from the group consisting of (meth) acrylic acid and carboxyl-containing (meth) acrylate and polyurethane poly (meth) acrylate. ing. Such an adhesive composition exhibits an adhesive strength to a film by being cured by an electron beam, and is used as an adhesive for lamination.

[0003]

However, since the electron beam irradiator required in the above-mentioned publication is still expensive, the present inventors have applied a general-purpose and inexpensive ultraviolet curing instead of the electron beam curing. As a result, it was found that although the adhesive strength to a plastic material was moderate, there was a disadvantage that the adhesion to metal, glass, and untreated polyester film was weakened. In the market for electronic materials, non-ferrous metal materials, and the like, ultraviolet curable adhesives for metals, glass, and untreated polyester films are also frequently used, and thus improvements in such compositions are desired.

[0004]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies in view of such circumstances, and as a result, (A) a urethane acrylate resin obtained by reacting hydrogenated polybutadiene polyol, polyisocyanate and hydroxyalkyl acrylate, (B) an ultraviolet-curable resin composition comprising an aliphatic or alicyclic alkyl acrylate having 6 or more carbon atoms, preferably (C) a Michael adduct of acrylic acid, or a monoester of 2-acryloyloxyethyldicarboxylic acid The present inventors have found that an ultraviolet-curable resin composition containing the above compound meets the above object, and completed the present invention.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The hydrogenated polybutadiene polyol (A), which is a component of the urethane acrylate resin obtained by reacting the hydrogenated polybutadiene polyol, the polyisocyanate and the hydroxyalkyl acrylate (hereinafter, may be simply referred to as (A)) used in the present invention ( a1) is the following (1)
It has a structure represented by the formula, and has a molecular weight of 300 to 6
000, preferably 500-3000 are useful. The iodine value is 0 to 50 KOH mg / g, preferably 0 to 20 KOH mg / g, and the hydroxyl value is 15 to 400 KOH mg / g.
KOHmg / g, preferably 30 to 250 KOHmg / g
g is appropriate.

[0006]

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The polyisocyanate (a2) is not particularly restricted but includes, for example, aromatic, aliphatic, cycloaliphatic and alicyclic polyisocyanates. Diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, modified diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethyl xylylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, 1,3-bis Diisocyanates such as (isocyanatomethyl) cyclohexane or trimers thereof are preferably used. The molecular weight of the polyisocyanate compound (a2) is preferably from 150 to 700 from the viewpoint of reactivity with a hydroxyl group.

Hydroxyalkyl acrylate (a3)
Examples thereof include, but are not particularly limited to, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxyethyl acryloyl phosphate, 4-butylhydroxy (Meth) acrylate, 2- (meth) acryloyloxyethyl-2-
Hydroxypropyl phthalate, glycerin di (meth)
Acrylate, 2-hydroxy-3-acryloyloxypropyl (meth) acrylate, caprolactone modified 2
-Hydroxyethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, and the like.

In the present invention, if necessary, other polyols may be used in addition to the hydrogenated polybutadiene polyol (a1). For example, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene Glycol, dipropylene glycol, polypropylene glycol, butylene glycol, 1,4-butanediol, polybutylene glycol, 1,6-hexanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, trimethylolethane, Trimethylolpropane, polytrimethylolpropane, pentaerythritol, polypentaerythritol, sorbitol, mannitol, arabit Polyethers having at least one structure of polyhydric alcohols such as toluene, xylitol, galactitol, glycerin, polyglycerin, and polytetramethylene glycol, polyethylene oxide, polypropylene oxide, ethylene oxide / propylene oxide block or random copolymerization Polyol, polyester polyol, caprolactone-modified poly which is a condensate of the polyhydric alcohol or polyether polyol with a polybasic acid such as maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, itaconic acid, adipic acid, isophthalic acid, etc. Caprolactone-modified polyols such as tetramethylene polyol, polyolefin-based polyols,
And polybutadiene-based polyols such as hydrogenated polybutadiene polyol.

(A) used in the present invention is hydrogenated polybutadiene polyol (a1), polyisocyanate (a2)
And a urethane acrylate resin obtained by reacting a hydroxyalkyl acrylate (a3), and its production method is not particularly limited. For example, a method in which three components of a hydrogenated polybutadiene polyol (a1), a polyisocyanate (a2) and a hydroxyalkyl acrylate (a3) are mixed and reacted at a time, a reaction is performed by reacting the hydrogenated polybutadiene polyol (a1) with the polyisocyanate (a2). Then, a method of reacting the hydroxyalkyl acrylate (a3), a method of reacting the polyisocyanate (a2) with the hydroxyalkyl acrylate (a3), and a reaction of the hydrogenated polybutadiene polyol (a1) are then exemplified. Among them, a method is preferable in terms of stability of reaction control and reduction of production time.

In the above, the hydrogenated polybutadiene polyol (a1) and the polyisocyanate (a2) are represented by n: n +
After reacting at a reaction molar ratio of 1 (molar ratio) (n is an integer of 1 or more), the reaction product is further reacted with a hydroxyalkyl acrylate (a3) at a reaction molar ratio of 1: 2. Is preferred. In these reactions, it is also preferable to use a catalyst such as dibutyltin dilaurate for the purpose of accelerating the reaction.

Thus, (A) is obtained. In the present invention, the weight average molecular weight of (A) is preferably from 2,000 to 40,000, and more preferably from 10,000 to 27,000.
0. If the weight average molecular weight is less than 2,000, the cured product (such as a coating film) becomes brittle, and if it exceeds 40,000, the curability deteriorates, which is not preferable.

The above-mentioned weight-average molecular weight is a weight-average molecular weight in terms of standard polystyrene molecular weight, and is a high-performance liquid chromatography (Showa Denko;
xGPC system-11 type ”), column: Sh
Odex GPC KF-806L (exclusion limit molecular weight:
2 × 10 ^7, separation range: 100-2 × 10 ^7, the number of theoretical plates:
It is measured by using three series of 10,000 steps / strand, filler material: styrene-divinylbenzene copolymer, filler particle size: 10 μm).

Further, the glass transition temperature (measured by TMA (thermomechanical analysis) method) of (A) is -45 to 70 ° C.
Is more preferable, and more preferably -40 to 65 ° C. If the temperature is lower than -45 ° C, the curability is poor. If the temperature exceeds 70 ° C, the cured product (such as a coating film) becomes brittle, which is not preferable. (B) used in the present invention
As the aliphatic or alicyclic alkyl acrylate having 6 or more carbon atoms, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate , Stearyl (meth) acrylate, lauryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate and the like.

The amount of the above (A) and (B) is preferably 20 to 200% by weight of (B) based on (A), and more preferably 5 to 200% by weight.
0 to 150% by weight. 20% by weight of (B)
If the amount is less than the above, the adhesion will be poor, while if it exceeds 200% by weight, the curability will be poor and a practical problem will occur.

In the present invention, for the purpose of further improving the adhesion, (C) a Michael adduct of acrylic acid or 2-acryloyloxyethyldicarboxylic acid monoester (hereinafter sometimes simply referred to as (C)) may be used in combination. Examples of the Michael adduct of acrylic acid include acrylic acid dimer [formula (2)], methacrylic acid dimer, acrylic acid trimer [formula (3)], methacrylic acid trimer, acrylic acid tetramer [formula (4)], Examples thereof include methacrylic acid tetramers, and among them, acrylic acid dimers are preferable.

[0017]

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The 2-acryloyloxyethyl dicarboxylic acid monoester is a carboxylic acid having a specific substituent, for example, 2-acryloyloxyethyl succinic acid monoester [formula (5)], 2-methacryloyloxy Ethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester [(6) below)
Formula], 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl hexahydrophthalic acid monoester [formula (7) below], 2-methacryloyloxyethyl hexahydrophthalic acid monoester, and the like. 2-acryloyloxyethyl hexahydrophthalic acid monoester.

[0019]

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The compounding weight ratio of (C) / (B) is 0.01 to
0.5, particularly preferably 0.05 to 0.3. If the compounding weight ratio is less than 0.01, the adhesion to glass deteriorates, which is not preferable. If it exceeds 0.5, the hardness may not be sufficiently increased even after ultraviolet curing, or the wet heat resistance may be poor, and as a coating agent, etc. Not preferred.

In the present invention, a reactive diluent may be used in addition to the above, and a monofunctional (meth) acrylate,
Functional (meth) acrylates and trifunctional or higher (meth) acrylates may be mentioned. Examples of the monofunctional (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, phenoxyethyl (meth) acrylate, glycerin mono (meth) acrylate, glycidyl (meth) acrylate, dicyclopentenyl (meth) acrylate, n-butyl (meth) acrylate,
Benzyl (meth) acrylate, phenol ethylene oxide modified (n = 2) (meth) acrylate, nonylphenol propylene oxide modified (n = 2.5)
(Meth) acrylate, 2- (meth) acryloyloxyethyl acid phosphate, furfuryl (meth) acrylate, carbitol (meth) acrylate, benzyl (meth) acrylate, butoxyethyl (meth) acrylate, allyl (meth) acrylate, 2- (meth) acrylate Hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate , 3-chloro-
2-hydroxypropyl (meth) acrylate and the like can be mentioned.

Examples of the bifunctional (meth) acrylate include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and propylene glycol di (meth) acrylate. (Meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth)
Acrylate, ethylene oxide modified bisphenol A type di (meth) acrylate, propylene oxide modified bisphenol A type di (meth) acrylate, 1,6
-Hexanediol di (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, diglycidyl phthalate Di (meth) acrylate,
Hydroxypivalic acid-modified neopentyl glycol di (meth) acrylate;

The trifunctional or higher functional (meth) acrylate includes, for example, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, Examples thereof include dipentaerythritol hexa (meth) acrylate, tri (meth) acryloyloxyethoxytrimethylolpropane, and glycerin polyglycidyl ether poly (meth) acrylate. Among these, a monofunctional (meth) acrylate containing no hydroxyl group is preferable, and further, the acrylate having a molecular weight of about 100 to 300 is preferable.

In the present invention, it is preferable to further use a photopolymerization initiator. The photopolymerization initiator is not particularly limited as long as it generates a radical by the action of light.
Specifically, 4-phenoxydichloroacetophenone,
4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylenephenyl) -2-hydroxy-2-methylpropane-1
-One, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl Phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, benzophenone, benzoyl Benzoic acid, methyl benzoylbenzoate,
4-phenylbenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3'-dimethyl-4-methoxybenzophenone, thioxanthone, 2-chlorothioxanthone, 2-
Methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, camphorquinone,
Dibenzosuberone, 2-ethylanthraquinone, 4 ',
4 "-diethylisophthalophenone, 3,3 ', 4
4'-tetra (t-butylperoxycarbonyl) benzophenone, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, 4- (2-
(Hydroxyethoxy) phenyl- (2-hydroxy-2
-Propyl) ketone and the like, among which benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, benzoyl isopropyl ether, 4- (2-
Hydroxyethoxy) -phenyl (2-hydroxy-2
-Propyl) ketone, 2-hydroxy-2-methyl-1
-Phenylpropan-1-one is preferably used.

The amount of the photopolymerization initiator is as follows.
(A) The amount is preferably from 2 to 5 parts by weight, more preferably from 3 to 4 parts by weight, per 100 parts by weight. If the amount is less than 2 parts by weight, the curing speed in the case of ultraviolet curing is extremely slow, and if it exceeds 5 parts by weight, the curability is not improved and it is useless.

Further, triethanolamine, triisopropanolamine, 4,4 '
-Dimethylaminobenzophenone (Michler's ketone),
4,4'-diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid (n-butoxy)
Ethyl, isoamyl 4-dimethylaminobenzoate, 4-
2-ethylhexyl dimethylaminobenzoate, 2,4-
It is also possible to use diethylthioxanthone, 2,4-diisopropylthioxanthone or the like in combination.

In addition to the above (A) to (C) and the photopolymerization initiator, an antioxidant, a flame retardant, an antistatic agent, a filler,
Leveling agents, stabilizers, reinforcing agents, matting agents, grinding agents and the like can also be blended. In addition, a solvent can also be blended, and examples of such a solvent include ethyl acetate, toluene, xylene, methanol, ethanol, butanol, acetone, methyl isobutyl ketone, methyl ethyl ketone, cellosolves, and diacetone alcohol.
It is possible to add about 1 to 10% by weight based on the total amount of (A), (B) and (C).

As a method for curing the ultraviolet-curable resin composition obtained as described above, a high-pressure mercury lamp, a metal halide lamp, a xenon lamp, a chemical lamp or the like which emits light in a wavelength range of 150 to 450 nm is used.
Irradiation may be about 0 to 3000 mJ / cm ² .

The ultraviolet-curable resin composition of the present invention comprises a coating agent for various substrates such as metal, ceramic, glass, and plastic films such as polyester films;
It can be widely used for paints, putty sealing agents, etc., especially for untreated polyester film, silicate glass, alkali silicate glass, soda-lime glass,
It is useful as a coating agent for a glass substrate such as potassium lime glass, lead glass, barium glass, and borosilicate glass, aluminum, SUS, copper plate, steel plate and the like, and as a laminating adhesive.

[0030]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. In the examples, “%” and “parts” are based on weight unless otherwise specified. Urethane acrylate resins (A-1 to 3) were produced in the following manner. Urethane acrylate resin (A-1) In a four-necked flask equipped with a thermometer, a stirrer, a water-cooled condenser, and a nitrogen gas inlet, 102.2 g (0.46 mol) of isophorone diisocyanate, hydrogenated polybutadiene polyol (average molecular weight) 2343, Iodine value 21 KO
Hmg / g or less, hydroxyl value 47.9 KOHmg / g) 3
59 g (0.15 mol) and hydrogenated polybutadiene polyol (average molecular weight 1740, iodine value 21 KOHmg /
g, hydroxyl value 64.5 KOHmg / g) 266.6
g (0.15 mol) and reacted at 90 ° C., and when the remaining isocyanate groups became 1.4%, the temperature was lowered to 7%.
The temperature was lowered to 0 ° C., and 72.2 g of caprolactone-modified acrylate (“Placcel FA-IDDM” manufactured by Daicel Chemical Industries, Ltd.).
(0.3 mol), and the reaction was terminated when the remaining isocyanate groups became 0.3%. The urethane acrylate resin (A-1) [glass transition temperature -37 ° C, average molecular weight 16,000] was added. Obtained.

Urethane acrylate resin (A-2) In a four-necked flask equipped with a thermometer, a stirrer, a water-cooled condenser and a nitrogen gas inlet, 122.6 g (0.55 mol) of triphorone diisocyanate, hydrogenated polybutadiene Polyol (average molecular weight 2267, iodine value 21 KO)
Hmg / g or less, hydroxyl value 49.5 KOHmg / g) 8
33.6 g (0.36 mol) was charged and reacted at 90 ° C., and when the remaining isocyanate groups became 1.6%,
The temperature was lowered to 70 ° C., and 43.8 g (0.38 mol) of 2-hydroxyethyl acrylate was added and reacted. When the remaining isocyanate groups became 0.3%, the reaction was terminated, and the urethane acrylate resin (A- 2) [Glass transition temperature -38 ° C, average molecular weight 17000] was obtained.

Urethane acrylate resin (A-3) 9.87 g (0.06 mol) of hexamethylene diisocyanate and hydrogenated polybutadiene were placed in a four-necked flask equipped with a thermometer, a stirrer, a water-cooled condenser, and a nitrogen gas inlet. Polyol (average molecular weight 2343, iodine value 21K
OH mg / g or less, hydroxyl value 47.9 KOH mg / g)
46.37 g (0.02 mol) and hydrogenated polybutadiene polyol (average molecular weight 1740, iodine value 21 KOH
mg / g or less, hydroxyl value 64.5 KOHmg / g) 3
4.43 g (0.02 mol) was charged and reacted at 90 ° C., and when the remaining isocyanate groups became 1.8%,
The temperature was lowered to 70 ° C., and caprolactone-modified acrylate (“Placcel FA-IDDM” manufactured by Daicel Chemical Industries, Ltd.)
9.33 g (0.04 mol) was added and reacted. When the remaining isocyanate groups became 0.3%, the reaction was terminated.
A urethane acrylate resin (A-3) [glass transition temperature -38 ° C, average molecular weight 15,000] was obtained.

The following was used as (B). (B-1): Octaacrylate (B-2): Decyl acrylate (B-3): Cyclohexyl acrylate (B-4): Phenoxyethyl acrylate (B-5): Benzyl acrylate Using. (C-1) Acrylic acid dimer (C-2) 2-acryloyloxyethyl hexahydrophthalic acid monoester (C-3) 2-acryloyloxyethyl succinic acid monoester

Examples 1 to 7 and Comparative Examples 1 to 3 The above (A), (B) and (C) were mixed in the amounts shown in Table 1 and further a photopolymerization initiator (manufactured by Ciba Geigy, 4 parts of Irgacure 184 ") to obtain an ultraviolet-curable resin composition. [Table 1] (A) (B) (C) Kind Content (parts) Kind Content (parts) Kind Content (parts) Example 1 A-1 50 B-1 50 〃2 A-2 48 B- 247 C-3 10 〃 3 A- 348 B-347 C-35 ４ 4 A-150 B-250 ５ 5 A- 248 B- 147 C-155 ６ 6 A- 348 B- 247C - 35 @ 7 A-148 B-347C-25 Comparative Example 1 A-150 B-450 @ 2 A-148 B- 547 C- 35 @ 3A -1 50 B-550 The following evaluation was performed on the obtained composition.

(Adhesiveness of Polyester Film) The composition obtained on each of the following base materials was applied with a 200 μ applicator, and an untreated polyester film (thickness: 100 μ) was stuck. Then, a tabletop UV irradiation device (Iwasaki Electric Co., Ltd.) Company
80W / cm (high pressure mercury lamp) x 13cmH x 1.5m / min x Pas with "Conveyor tabletop irradiation device"
s (total 3000 mJ / cm ² ), cured by irradiating ultraviolet rays from the untreated polyester film side,
A 180 degree peel test was performed according to JIS K6854. In each case, the adhesive strength at which the polyester film broke the material was obtained. However, none of the comparative examples could be cured.

(Cross-cut adhesion test [1 mm × 1 mm]) After applying the composition obtained on each base material with a # 20 bar coater, a tabletop UV irradiation device (manufactured by Iwasaki Electric Co., Ltd .; Desktop irradiation device ") at 80 W / cm (high pressure mercury lamp) x 13 cmH x 1.5 m / min x Pass
After curing by irradiation with ultraviolet rays under the condition of (integration of 3000 mJ / cm ² ), the measurement was carried out according to JIS K5400. In each case, adhesion was 100/100. However, none of the comparative examples could be cured.

Aluminum plate (manufactured by Nippon Test Panel Co., Ltd.
Size 1.0 (thickness) x 70 x 150 mm) Copper plate (Nippon Test Panel Co., Ltd., size 1.0 (thickness) x 70 x 150 mm) SUS plate (Nippon Test Panel Co., Ltd., size 1.0)
(Thickness) x 70 x 150 mm) Silicate glass plate (Nippon Test Panel Co., Ltd., size 1.0 (thickness) x 70 x 150 mm)

[0038]

The ultraviolet-curable resin composition of the present invention comprises:
(A) a urethane acrylate resin obtained by reacting a hydrogenated polybutadiene polyol, a polyisocyanate and a hydroxyalkyl acrylate, and (B) a radiation-curable resin composition containing (B) an aliphatic or alicyclic alkyl acrylate having 6 or more carbon atoms. And preferably further comprises (C) a radiation-curable resin composition blended with Michael adduct of acrylic acid or 2-acryloyloxyethyldicarboxylic acid monoester, and is used for bonding various substrates such as polyester film, metal and glass. It is useful as an agent, a coating agent (paint), a putty sealing agent, etc., and particularly very useful as a laminating adhesive or a coating agent.

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[Procedure amendment]

[Submission date] August 30, 2000 (2008.3.
0)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0035

[Correction method] Change

[Correction contents]

(Adhesiveness of Polyester Film) The composition obtained on each of the following base materials was applied with a 200 μ applicator, and an untreated polyester film (thickness: 100 μ) was stuck. Then, a tabletop UV irradiation device (Iwasaki Electric Co., Ltd.) Company
80W / cm (high pressure mercury lamp) x 13cmH x 1.5m / min x Pas with "Conveyor tabletop irradiation device"
s (total 3000 mJ / cm ² ), cured by irradiating ultraviolet rays from the untreated polyester film side,
A test for tensile shear adhesive strength was performed according to JIS K 6850 . In each case, the adhesive strength at which the polyester film broke the material was obtained. However, none of the comparative examples could be cured.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4J011 QA02 QA03 QA15 QA23 QA24 QB24 SA06 SA07 SA22 SA26 SA32 SA36 SA42 SA63 SA64 SA83 SA84 UA01 VA01 WA02 WA06 4J027 AG05 AG09 AG23 AG24 AG27 AG32 AJ01 BA06 BA07 BA10 BA21 BA20 BA26 CB10 CC05 CD08 CD09 4J038 FA131 FA132 FA152 FA281 FA282 GA06 KA03 NA12 PA17 PC02 PC04 PC08 4J040 FA151 FA152 FA182 FA291 FA292 JB07 KA13 LA06 MA02 MA05 MA10

Claims (4)

[Claims] 1. A urethane acrylate resin obtained by reacting (A) a hydrogenated polybutadiene polyol, a polyisocyanate and a hydroxyalkyl acrylate, (B)
An ultraviolet curable resin composition comprising an aliphatic or alicyclic alkyl acrylate having 6 or more carbon atoms. 2. The composition according to claim 1, further comprising (C) Michael adduct of acrylic acid or 2-acryloyloxyethyldicarboxylic acid monoester. 3. A coating agent for metal, glass and plastic films, comprising the ultraviolet-curable resin composition according to claim 1. 4. A laminating adhesive for metal, glass and plastic films containing the ultraviolet-curable resin composition according to claim 1.