TW201541188A - Resin composition hardened by active energy ray, hardened object, adhesive and laminated film - Google Patents

Abstract

This invention provides a solvent-free resin composition hardened by active energy rays that features high adhesion strength even for adhesion-resistant plastic films, a.k.a., adhesion-resistant films, such as unprocessed PET films, fluorine-based films and polycarbonate films, and maintains a high adhesion strength even in a hot and humid condition. This invention also provides an adhesive containing the resin composition and a laminated film formed by using the adhesive. A polyester resin (A), which has an acid value smaller than 20, a polyester (meth)acrylate compound (B) and a photoinitiator (C) are used as essential components to make the solvent-free resin composition hardened by active energy rays, an adhesive and a laminated film.

Description

Active energy ray-curable resin composition, cured product, adhesive, and laminated film

The present invention relates to an active energy ray-curable resin composition, an adhesive obtained by using the resin composition, and a laminated film obtained by using the same.

A laminated film in which various functional films are bonded to each other by an adhesive is an essential member in various products such as a liquid crystal display device, a personal computer, and a solar battery module. A polyethylene terephthalate (hereinafter abbreviated as "PET") film has been widely used as a substrate for the laminated film, but the PET film is one of substrates which are difficult to use with an adhesive. In the state in which the adhesion is improved by the easy-to-treat treatment such as corona treatment on the adhesive film of the PET film. Therefore, in order to improve the productivity of the laminated film and to reduce the cost, it is necessary to firmly carry out the adhesive after the PET film (hereinafter simply referred to as "untreated PET film") which is easily subjected to the subsequent treatment. Further, in recent years, as electronic devices such as car navigation systems and solar battery modules have increased opportunities for outdoor use, an adhesive agent capable of maintaining high adhesion strength even in an outdoor high-temperature and high-humidity environment has been sought.

As a coating excellent for adhesion to untreated PET film As the resin composition for the material, a homopolymer containing methyl methacrylate (Tg: 105 ° C, weight average molecular weight (Mw): 47, 500, SP value: 10.0), and a coating of pentaerythritol tetraacrylate are known. A resin composition is used (refer to Citation 1). In the case where the resin composition is superior to the conventional resin composition for a coating material, the adhesion to the untreated PET film is excellent. However, since it is an inventor who has completed the use of the coating material, it is not available. A high degree of adhesion to the extent that the films are adhered to each other.

Further, among the various functional films used for the laminated film, in addition to the untreated PET film, there are many films which are difficult to follow. For example, a fluorine-based film composed of a polyvinyl fluoride resin or a polyvinylidene fluoride resin is excellent in weather resistance, heat resistance, and stain resistance, and can be used as a member of a solar cell module or the like, but is hydrophobic. The oiliness is high, so it is difficult to use an adhesive. Further, although the polycarbonate film has a characteristic of excellent impact resistance, it is difficult to firmly adhere with a conventional adhesive. Because of such a thing, there is a need for an adhesive having high adhesion to various difficult-to-adhesive plastic films represented by untreated PET films.

Thus, a polyester (meth) acrylate compound having a polyester moiety and a (meth) acryl oxime group, a polyester resin having a acid value of 40 to 90 mg KOH/g, and a polymerization initiator were found as essential components. The active energy ray-curable resin composition exhibits high adhesion strength even in difficult-to-adhere films such as untreated PET film, fluorine-based film, and polycarbonate film, and maintains the bonding strength even under moist heat conditions ( Patent Document 2). However, when the resin composition is applied, there is It is necessary to be diluted by an organic solvent for the purpose of imparting coating properties or imparting workability. Therefore, after the application, there is a need to dry and volatilize the organic solvent, and there is room for improvement from the viewpoint of environmental load or productivity.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2006-257226

[Patent Document 2] International Publication No. 2013/058330

The problem to be solved by the present invention is to provide a plastic film which is difficult to adhere to an untreated PET film, a fluorine-based film, a polycarbonate film or the like, that is, a so-called difficult-to-attach film having high bonding strength, especially even under moist heat conditions. A solventless active energy ray-curable resin composition capable of maintaining the strength of the adhesive; an adhesive comprising the resin composition; and a laminated film obtained by using the adhesive.

As a result of intensive studies to solve the above problems, the present inventors have found that a polyester resin (A), a polyester (meth) acrylate compound (B), and a polymerization containing an acid value of 20 mgKOH/g or less The initiator (C) is an essential component and does not substantially contain a solvent-free active energy ray-curable resin composition of an organic solvent, and it is difficult to carry out an untreated PET film, a fluorine film, a polycarbonate film or the like. The film also exhibits high adhesion strength and maintains its bonding strength even under moist heat conditions, and the present invention has been completed.

That is, the present invention relates to a solvent-free active energy ray-curable resin composition characterized by comprising a polyester resin (A) having a acid value of 20 mgKOH/g or less, and a polyester (meth)acrylic acid. The ester compound (B) and the photoinitiator (C) are essential components.

The present invention is further directed to an adhesive comprising the above active energy ray-curable resin composition.

The present invention is further directed to a laminated film obtained by using the above-mentioned adhesive.

According to the present invention, it is possible to provide a solvent-free active energy which exhibits high adhesion to a difficult-to-adhere film of an untreated PET film, a fluorine-based film, a polycarbonate film or the like and maintains its adhesion even under moist heat conditions. a wire-curable resin composition; an adhesive comprising the resin composition; and a laminated film obtained by using the adhesive.

[Formation of the Invention]

The solvent-free active energy ray-curable resin composition of the present invention is characterized by containing a polyester resin (A), a polyester (meth) acrylate compound (B) having an acid value of 20 or less, and light-emitting The starting agent (C) is an essential component.

The polyester resin (A) used in the present invention has an acid value in the range of 20 mgKOH/g or less. By this range, even if it does not substantially contain an organic solvent, so-called solvent-free, the resin composition of the present invention The affinity of the article for the PET film or the fluorine-based film is improved, and the wettability at the time of coating is improved. In addition, it is preferable that the resin composition which is excellent in the adhesive strength after hardening, and the adhesive strength after the hardening of the base material is improved, and the acidity is preferably 3 to 20 mgKOH/ The range of g.

In addition, when the aromatic ring concentration of the polyester resin (A) is in the range of 4 mmol/g or more, the affinity of the resin composition of the present invention to the PET film or the fluorine-based film is improved, and the organic substance is substantially not contained. The solvent, that is, the so-called wettability at the time of application without a solvent tends to be good, and is preferable.

In addition, when the hydroxyl value of the polyester resin (A) is in the range of 40 to 90 mgKOH/g, the affinity of the resin composition of the present invention to the PET film or the fluorine-based film is improved, and substantially no organic substance is contained. The solvent, that is, the so-called wettability at the time of application without a solvent tends to be good, and is preferable.

The polyester resin (A) is obtained by reacting an aliphatic polyhydric alcohol with an aliphatic or aromatic polybasic acid as a main raw material component.

The aliphatic polyol to be used as a raw material of the polyester resin (A) is not particularly limited as long as the effects of the present invention are not impaired, and examples thereof include ethylene glycol, diethylene glycol, and propylene glycol. 3-propanediol, 1,2,2-trimethyl-1,3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,4-butanediol, 1, 3-butanediol, 3-methyl-1,3-butanediol, 1,5-pentanediol, 3-methyl 1,5-pentanediol, neopentyl glycol, 1,6-hexane Alcohol, 2,2,4-trimethyl-1,3-pentanediol, 1,4-bis(hydroxymethyl)cyclohexane, trimethylolethane, trimethylolpropane, glycerol An aliphatic polyol such as hexanetriol or pentaerythritol. The polyol can be used alone or in combination Two or more types can be used in combination. Among them, ethylene glycol, diethylene glycol, propylene glycol, 1,3-propanediol, 1, 2 are preferably used in combination with a resin composition excellent in adhesion to a plastic film substrate at the time of lamination. , 2-trimethyl-1,3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 3 -methyl-1,3-butanediol, 1,5-pentanediol, 3-methyl 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 2,2,4 - an aliphatic diol such as trimethyl-1,3-pentanediol or 1,4-bis(hydroxymethyl)cyclohexane, and trimethylolethane, trimethylolpropane, and glycerol A trifunctional or higher aliphatic polyol such as hexanetriol or neopentyl alcohol.

Examples of the polybasic acid used as a raw material of the polyester resin (A) include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, and cerium. An aliphatic dibasic acid such as an acid; an aromatic dibasic acid such as citric acid, phthalic anhydride, terephthalic acid, isophthalic acid or phthalic acid; hexahydrofurfuric acid or 1,4-cyclohexane An alicyclic dibasic acid such as a carboxylic acid; an aliphatic unsaturated dibasic acid such as tetrahydrofurfuric acid, maleic acid, maleic anhydride, fumaric acid, citraconic acid, itaconic acid or glutaconic acid; An aliphatic tribasic acid such as 1,2,5-hexanetricarboxylic acid or 1,2,4-cyclohexanetricarboxylic acid; or aroma of trimellitic acid or 2,5,7-naphthalenetricarboxylic acid Family tribasic acid and so on. These polybasic acids may be used alone or in combination of two or more. Among these, from the viewpoint of obtaining a resin composition having high coatability, the aliphatic dibasic acid is preferred, and succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid are more preferred. An aliphatic dibasic acid having a carbon number of 4 to 8 is particularly preferred as adipic acid. Further, in the case where the target is an untreated PET film, it is preferable to use tannic acid or tannic acid from the viewpoint of obtaining a resin composition excellent in adhesion to the untreated PET film and having a higher bonding strength. An aromatic dibasic acid such as an anhydride, terephthalic acid, isophthalic acid or phthalic acid is more preferably terephthalic acid. That is, the polybasic acid raw material of the polyester resin (A) is preferably a combination of the above-mentioned succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and the like having a carbon number of 4 to 8. An aliphatic dibasic acid and an aromatic dibasic acid such as citric acid, phthalic anhydride, terephthalic acid, isophthalic acid or phthalic acid.

In the method of producing the polyester resin (A), for example, the polyhydric alcohol is reacted with the polybasic acid while removing the generated water at a temperature of 150 to 250 ° C using an esterification catalyst as needed. Method etc.

The polyester resin (A) is excellent in compatibility with the polyester (meth) acrylate compound (B), and is excellent in adhesion to the plastic film substrate at the time of lamination. The weight average molecular weight (Mw) of the polyester resin (A) thus obtained is preferably in the range of 3,000 to 20,000, and more preferably in the range of 5,000 to 15,000, from the viewpoint of the resin composition having excellent fluidity.

The polyester (meth) acrylate compound (B) used in the present invention has a polyester structural moiety and a (meth) acrylonitrile group in a molecular structure, and is irradiated by an active energy ray to make a molecular structure. The (meth)acrylonitrile group is polymerized and hardened, and the plastic films are bonded to each other, and the composition of the bonding strength under moist heat conditions is increased by forming a crosslinked structure. On the other hand, as described above, the polyester resin (A) is a difficult-to-adhere film of the resin composition of the present invention against an untreated PET film or a fluorine-based film by a solvent having a specific range and having no solvent. The ingredients for improved affinity. The resin composition of the present invention is obtained by containing the polyester tree The fat (A) and the polyester (meth) acrylate compound (B) are bonded to each other with an adhesive, and are hardly adhered at a stage before the irradiation of the active energy ray to be hardened, that is, a so-called lamination step. The adhesion between the plastic film and the adhesive is improved even in the absence of a solvent. By performing the curing reaction of the polyester (meth) acrylate compound (B) in such a close contact state, the films can be adhered to each other very strongly.

The weight average molecular weight (Mw) of the polyester (meth) acrylate compound (B) used in the present invention is not particularly limited, but the weight average molecular weight (Mw) thereof is preferably in the range of 5,000 to 100,000; The coating property is more preferably in the range of 8,500 to 85,000 from the viewpoint of a resin composition exhibiting a higher bonding strength for various types of difficult-to-adhere films. Among them, the weight average molecular weight (Mw) is preferably in the range of 10,000 to 50,000 from the resin composition having excellent adhesion to the substrate in the laminating step and suitable for coating.

Further, in the present invention, the weight average molecular weight (Mw) is a value measured by gel permeation chromatography (GPC) under the following conditions.

Measuring device: HLC-8220GPC manufactured by TOSOH Co., Ltd.

Pipe column: TSK-GEL SuperHZ M-M×4 made by TSK-GUARDCOLUMN SuperHZ-L+TOSOH Co., Ltd.

Detector: RI (differential refractometer)

Data Processing: Multistation GP C-8020modelII by TOSOH Co., Ltd.

Measurement conditions: column temperature 40 ° C

Solvent tetrahydrofuran

Flow rate 0.35ml/min

Standard: monodisperse polystyrene

Sample: A tetrahydrofuran solution having a resin solid content of 0.2% by mass was filtered through a microfilter to obtain (100 μl)

The polyester (meth) acrylate compound (B) preferably has a polyester structure in which a fatty polyol is reacted with an aliphatic and/or aromatic polybasic acid as a main raw material component in a molecular structure, And a compound having a (meth) acrylonitrile group. The polyester (meth) acrylate compound (A) is exemplified by the number of moles of the isocyanate group in the polyisocyanate compound (b2) relative to the hydroxyl group of the polyester polyol (b1). The polyester polyol (b1) obtained by reacting an aliphatic polyol with an aliphatic and/or aromatic polybasic acid and the polyisocyanate compound (b2) are reacted under an excessive amount of the ear, and the reaction is allowed to proceed. The intermediate obtained by the reaction, a method of reacting with a hydroxyl group-containing (meth) acrylate (b3), and the like.

Examples of the aliphatic polyol which is a raw material of the polyester polyol (b1) include ethylene glycol, diethylene glycol, propylene glycol, 1,3-propanediol, and 1,2,2-trimethyl-1. 3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 3-methyl-1,3-butyl Glycol, 1,5-pentanediol, 3-methyl 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 2,2,4-trimethyl-1,3- An aliphatic polyol such as pentanediol, 1,4-bis(hydroxymethyl)cyclohexane, trimethylolethane, trimethylolpropane, glycerol, hexanetriol or pentaerythritol; An ether diol such as polyoxyethylene glycol or polyoxypropylene glycol; by the aforementioned aliphatic polyol and ethylene oxide Ring-opening polymerization of various cyclic ether bond-containing compounds such as propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether The obtained modified polyether polyol; a lactone-based polyester polyol obtained by a polycondensation reaction of the above-mentioned aliphatic polyol with various lactones such as ε-caprolactone. These may be used alone or in combination of two or more. Among these, a resin composition excellent in adhesion to a plastic film substrate at the time of lamination and high in adhesion strength after curing is preferable, and 1,2,2-trimethyl-1 is preferable. 3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,3-butanediol, 3-methyl-1,3-butanediol, 3-methyl 1 a branched aliphatic diol such as 5-pentanediol, neopentyl glycol or 2,2,4-trimethyl-1,3-pentanediol, particularly preferably 3-methyl 1,5- Pentylene glycol.

Examples of the polybasic acid which is a raw material of the polyester polyol (b1) include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, and sebacic acid. Aliphatic dibasic acid; aromatic dibasic acid such as citric acid, phthalic anhydride, terephthalic acid, isophthalic acid, phthalic acid; hexahydrofurfuric acid, 1,4-cyclohexane dicarboxylic acid An alicyclic dibasic acid such as an acid; an aliphatic unsaturated dibasic acid such as tetrahydrofurfuric acid, maleic acid, maleic anhydride, fumaric acid, citraconic acid, itaconic acid or glutaconic acid; , an aliphatic tribasic acid such as 2,5-hexanetricarboxylic acid or 1,2,4-cyclohexanetricarboxylic acid; or an aromatic hydrocarbon such as trimellitic acid or 2,5,7-naphthalenetricarboxylic acid Tribasic acid and so on. These may be used alone or in combination of two or more. Among these, from the viewpoint of obtaining a resin composition having high coatability, the aliphatic dibasic acid is preferred, and succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid are more preferred. An aliphatic dibasic acid having a carbon number of 4 to 8 is particularly preferred. It is adipic acid. Further, in the case where the subsequent target is an untreated PET film, it is preferable to use citric acid or phthalic anhydride from the viewpoint of obtaining a resin composition excellent in adhesion to the untreated PET film and having a higher strength. An aromatic dibasic acid such as terephthalic acid, isophthalic acid or phthalic acid is more preferably terephthalic acid. Further, from the viewpoint of exhibiting excellent coatability and adhesion strength, it is particularly preferred in the present invention to use the above aliphatic polybasic acid and aromatic polybasic acid in combination. In the case of using the above aliphatic polybasic acid and aromatic polybasic acid, the ratio is not particularly limited unless the effect of the present invention is not impaired, but it is preferably 10 to 50 mol% of aliphatic dibasic acid and aromatic polybasic Acid 50~90 mol%.

In the method of producing the polyester polyol (b1), for example, the polyhydric alcohol and the polybasic acid are removed while removing the generated water at a temperature of 150 to 250 ° C using an esterification catalyst as needed. The method of reaction, and the like.

The number average molecular weight (Mn) of the polyester polyol (b1) thus obtained is preferably 500 to be excellent in the adhesion of the substrate in the laminating step, and is suitable for the viscosity of the coated resin composition. The range of 6,000 is more preferably in the range of 750 to 4,000, and particularly preferably in the range of 900 to 3,000.

In addition, the hydroxyl group of the polyester polyol (b1) is preferably a resin composition having a small shrinkage due to curing and excellent adhesion strength after curing, and is preferably in the range of 6 to 300 mgKOH/g, more preferably The range of 20 to 200 mgKOH/g is particularly preferably in the range of 50 to 160 mgKOH/g.

The polyisocyanate compound (b2) which is a raw material of the above-mentioned polyester (meth) acrylate compound (B) is exemplified by various diisocyanates. An ester monomer or an addition type polyisocyanate compound having a urethane bonding site in a molecule, a nurate type polyisocyanate compound having an isomeric cyanate ring structure in the molecule, and the like .

Examples of the diisocyanate monosystem include butane-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethyl. An aliphatic diisocyanate such as hexamethylene diisocyanate, benzodimethyl diisocyanate or m-tetramethyl dimethyl diisocyanate; cyclohexane-1,4-diisocyanate, isophorone diisocyanate, An alicyclic diisocyanate such as diamine diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, methylcyclohexane diisocyanate; 1,5 -naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-diphenylmethyl diisocyanate, dialkyl diphenyl Methane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, etc. Aromatic diisocyanate and the like.

The addition type polyisocyanate compound having a urethane bonding site in the molecule is obtained, for example, by reacting a diisocyanate monomer with a polyol. The diisocyanate monomer to be used in the reaction may be any of the above-mentioned various diisocyanate monomers, and they may be used alone or in combination of two or more. In addition, examples of the polyol used in the reaction include various polyols exemplified as the raw material of the polyester polyol (b1), or various polyesters exemplified as the polyester polyol (b1). Alcohols and the like may be used alone or in combination of two or more.

The cyanuric acid type polyisocyanate compound having an isomeric cyanate ring structure in the molecule is obtained, for example, by reacting a diisocyanate monomer with a monool and/or a diol. The diisocyanate monomer to be used in the reaction may be any of the above-mentioned various diisocyanate monomers, and they may be used alone or in combination of two or more. Further, as the monool used in the reaction, hexanol, 2-ethylhexanol, octanol, n-nonanol, n-undecyl alcohol, n-dodecyl alcohol, n-tridecyl alcohol, and positive tenth may be mentioned. Tetraol, n-pentadecanol, n-heptadecanol, n-octadecyl alcohol, n-nonadecanol, eicosyl alcohol, 5-ethyl-2-nonanol, trimethylnonanol, 2-hexyl decyl alcohol, 3 , 9-diethyl-6-tridecyl alcohol, 2-isoheptyl isoundecyl alcohol, 2-octyldodecanol, 2-decyltetradecyl alcohol, etc.; Various diols exemplified as the raw material of the polyester polyol (a1). These monools or diols may be used alone or in combination of two or more.

Among the above various isocyanate compounds (b2), the weight average molecular weight (Mw) of the obtained polyester (meth) acrylate compound (B) can be easily adjusted to the above-mentioned appropriate range, and a diisocyanate monomer is preferable. Further, a resin composition excellent in adhesion to the plastic film substrate and adhesion strength after curing at the time of lamination is preferably isophorone diisocyanate or dicyclohexylmethane-4. 4'-diisocyanate, 4,4'-diphenylmethane diisocyanate, toluene diisocyanate.

The hydroxyl group-containing (meth) acrylate compound (b3) which is a raw material of the polyester (meth) acrylate compound (B) may, for example, be 2-hydroxyethyl (meth) acrylate or (methyl) 2-hydroxypropyl acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyl acrylamide, glycerin di(meth)acrylate, trishydroxyl Propane di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and the like. These may be used alone or in combination of two or more. Among these, a resin composition which is small in shrinkage at the time of curing and which is more excellent in adhesion strength after curing is preferably 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate or 4-hydroxybutyl acrylate. A monofunctional (meth) acrylate compound such as 2-hydroxyethyl acrylamide or the like is more preferably 2-hydroxyethyl acrylate or 2-hydroxypropyl acrylate.

The method for producing the polyester (meth) acrylate compound (A) is exemplified by the molar number (OH) of the hydroxyl group contained in the polyester polyol (b1) and the polyisocyanate compound (b2). The molar ratio (NCO) of the isocyanate group (NCO) is ratio of 1/2 to 1/2.1, and the polyester polyol (b1) and the aforementioned polyisocyanate compound are used. (b2), the reaction is carried out in the presence of a urethanization catalyst at a temperature of from 20 to 120 ° C to obtain an intermediate, and the number of moles of the isocyanate group contained in the intermediate is (NCO), the ratio of the molar number (OH) of the hydroxyl group contained in the hydroxyl group-containing (meth) acrylate compound (b3) [(OH)/(NCO)] is 1/0.95 to 1/1.05 a ratio of the range, using the intermediate and the hydroxyl group-containing (meth) acrylate compound (b3), at a temperature of 20 to 120 ° C, if necessary, in the presence of a urethane catalyst Method, etc.

For the other production method, for example, a method of reacting the polyester polyol (b1), the polyisocyanate compound (b2), and the hydroxyl group-containing (meth) acrylate compound (b3) in a batch, and reacting them, may be mentioned. Or after reacting the isocyanate compound (b2) with the hydroxyl group-containing (meth) acrylate compound (b3), the intermediate obtained in the reaction is obtained. A method of reacting with the polyester polyol (b1) or the like.

The glass transition of the polyester (meth) acrylate compound (B) thus obtained is obtained from the resin composition having improved adhesion to the plastic film substrate at the time of lamination and excellent adhesion strength after curing. The temperature (hereinafter referred to as "Tg") is preferably in the range of -70 to 100 ° C, more preferably in the range of -40 to 60 ° C.

From the viewpoint of obtaining a crosslinked structure which can form an optimum density as an adhesive, that is, a resin composition which is hard to cause volume shrinkage at the time of curing, and which has high water resistance and excellent adhesion strength under wet heat conditions, the aforementioned polyester ( The (meth)acrylonitrile group concentration of the methyl acrylate compound (B) is preferably in the range of 0.04 to 0.5 mmol/g, more preferably in the range of 0.1 to 0.3 mmol/g.

Further, the polyester (meth) acrylate compound (B) is a compound obtained by reacting the polyester polyol (b1), the polyisocyanate compound (b2), and the hydroxyl group-containing (meth) acrylate (b3). In this case, the urethane bond concentration of the polyester (meth) acrylate compound (B) is improved in adhesion to the plastic film substrate at the time of lamination, and is excellent in adhesion strength after curing. The viewpoint of the resin composition is preferably in the range of 0.6 to 5 mmol/g, more preferably in the range of 0.8 to 3 mmol/g.

The solvent-free active energy ray-curable type of the present invention is obtained from a resin composition which is improved in adhesion strength after curing due to improvement in adhesion at the time of lamination, and further excellent in adhesion strength under wet heat conditions. The resin composition preferably contains the polyester resin (A) and the polyester (meth) acrylate compound (B) such that the mass ratio [(A)/(B)] of the two is 2/98 to 80/ 20 range, better to make it 5/95~ Contained in the range of 55/45.

The polymerization initiator (C) used in the present invention may, for example, be 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4- (2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivative, 2,2'-dimethoxy-1 ,2-diphenylethan-1-one, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzylidene)phenyl Phosphonium oxide, 2-methyl-1-[4-(methylthio)phenyl]-2- Lolinyl-1-propanone, 2-benzyl-2-dimethylamino-1-(4- Polinylphenyl)-butan-1-one and the like.

Commercial products of such polymerization initiators (C) include, for example, "IRGACURE-184", "IRGACURE-149", "IRGACURE-261", "IRGACURE-369", "IRGACURE-500", "IRGACURE" -651", "IRGACURE-754", "IRGACURE-784", "IRGACURE-819", "IRGACURE-907", "IRGACURE-1116", "IRGACURE-1664", "IRGACURE-1700", "IRGACURE-1800" "IRGACURE-1850", "IRGACURE-2959", "IRGACURE-4043", "DAROCUR-1173" (made by BASF Corporation (old Ciba Specialty Chemicals)), "Lucirin TPO" (made by BASF Corporation), "KAYACURE" -DETX", "KAYACURE-MBP", "KAYACURE-DMBI", "KAYACURE-EPA", "KAYACURE-OA" (made by Nippon Kayaku Co., Ltd.), "Vicure-10", "Vicure-55" (Stauffer "Chemical"), "Trigonal P1" (made by Akzo), "Sandoray 1000" (made by Sandys), "DEEP" (made by Upjohn), "Quantacure-PDO" "Quantacure-ITX", "Quantacure-EPD" (made by Ward Blenkinsop), etc. Among these, from the viewpoint of exhibiting higher curability of the solvent-free active energy ray-curable resin composition of the present invention, 1-hydroxycyclohexyl phenyl ketone (commercial product "IRGACURE 184") is preferably used in combination. And diphenyl (2,4,6-trimethylbenzylidene) phosphine oxide (commercial product "Rulicin TPO").

The blending amount of the polymerization initiator (C) is based on the solvent-free active energy ray of the present invention from the viewpoint of maintaining the sensitivity of light and preventing precipitation of crystals or deterioration of physical properties of the coating film. The resin component of the curable resin composition is preferably from 0.05 to 20 parts by mass, more preferably from 0.1 to 10 parts by mass, per 100 parts by mass of the resin component.

The solvent-free active energy ray-curable resin composition of the present invention may further contain various photosensitizers in combination with the photopolymerization initiator. The photo sensitizer may, for example, be an amine, a urea, a sulfur-containing compound, a phosphorus-containing compound, a chlorine-containing compound or a nitrile or another nitrogen-containing compound, and these may be used alone or in combination of two or more. . The solvent-free active energy ray-curable resin composition of the present invention contains the amount of the light sensitizing agent in an amount of 100 parts by mass based on the resin component of the solventless active energy ray-curable resin composition of the present invention. It is preferably in the range of 0.01 to 10 parts by mass.

The solventless active energy ray-curable resin composition of the present invention does not substantially contain an organic solvent. However, the fact that the organic solvent-free resin composition does not contain an organic solvent means that the active energy ray-curable resin composition does not contain an organic solvent, or even if it is contained in a very small amount, it is necessary to volatilize the organic solvent before bonding, and it is sufficient to show a coating. Adhesion, adhesion Active energy ray-curable resin composition. Specifically, the concentration of the organic solvent in the active energy ray-curable resin composition of the present invention is preferably 0 ppm, but may be 1000 ppm or less, preferably 100 ppm or less, and more preferably 10 ppm or less.

The solventless active energy ray-curable resin composition of the present invention may contain various other additives. Examples of the various additives include ultraviolet absorbers, antioxidants, lanthanoid additives, fluorine-based additives, rheology control agents, degassing agents, antistatic agents, and antifogging agents. The solvent-free active energy ray-curable resin composition of the present invention contains the content of such an additive, and exhibits the effect of the additive and does not hinder the ultraviolet curing, and is solvent-free active energy ray hardening with respect to the present invention. The resin component of the resin composition is preferably in a range of 0.01 to 40 parts by mass based on 100 parts by mass of the resin component.

The solvent-free active energy ray-curable resin composition of the present invention has an object of improving adhesion to a film substrate, and the like, and other resins can be used in combination. Examples of the other resin include acrylic resins such as methyl methacrylate resin and methyl methacrylate copolymer; polystyrene, methyl methacrylate-styrene copolymer; and polyester resin. Polyurethane resin; polybutadiene resin such as polybutadiene or butadiene-acrylonitrile copolymer; bisphenol epoxy resin, phenoxy resin or novolak epoxy resin Epoxy resin, etc. The content of the solvent-free active energy ray-curable resin composition of the present invention in the case of containing such a resin is in a range in which the effects expressed by the present invention are not hindered and sufficiently exhibited, and the polyester resin (A) and the aforementioned 100 parts by mass of the polyester (meth) acrylate compound (B), preferably 1 to 50 parts by mass The scope.

Further, the solvent-free active energy ray-curable resin composition of the present invention has a purpose of adjusting the viscosity thereof and the like, and a monofunctional monomer can be used in combination. Examples of such a monofunctional monomer include a monofunctional monomer having one ethylenically unsaturated bond in one molecule, and preferably one (meth)acryl fluorenyl group in one molecule. Or a compound of a vinyl group. Specific examples thereof include vinyl monomers such as N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, and vinylpyridine; isodecyl (meth)acrylate; ) decyl acrylate, tricyclodecyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylate Benzyl methyl ester, 4-butylcyclohexyl (meth)acrylate, acrylonitrile Porphyrin, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate , (meth) propyl acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth) acrylate, (meth) acrylate Butyl ester, amyl (meth)acrylate, isoamyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, (meth)acrylic acid Octyl ester, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, Methyl)dodecyl acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl methacrylate, (meth) acrylate Hydroquinone ester, butoxyethyl (meth)acrylate, ethoxy diethylene glycol (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate Methoxyethylene glycol (methyl) propyl Acid ester, ethoxyethyl (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate, diacetone (meth) acrylamide, Isobutoxymethyl (meth) acrylamide, N,N-dimethyl(meth) acrylamide, tertiary octyl (meth) acrylamide, dimethylamine (meth)acrylate Ethyl ethyl ester, diethylaminoethyl (meth)acrylate, 7-amino-3,7-dimethyloctyl (meth)acrylate, N,N-diethyl(meth)acryl Amine, N,N-dimethylaminopropyl (meth) acrylamide, hydroxybutyl vinyl ether, lauryl vinyl ether, hexadecyl vinyl ether, 2-ethylhexyl vinyl ether And monofunctional monomers represented by the following general formulae (1) and (2).

(In the formula (1), R ¹ represents a hydrogen atom or a methyl group, and R ² represents an alkylene group having 2 to 8 carbon atoms. m represents an integer of 1 to 8)

(In the formula (2), R ¹ each independently represents a hydrogen atom or a methyl group, R ² represents an alkylene group having 2 to 8 carbon atoms, and m represents an integer of 1 to 8)

These monofunctional monomers may be used alone or in combination of two or more.

For the commercially available product of the monofunctional monomer, for example, Viscoat 150D (manufactured by Osaka Organic Chemical Industry Co., Ltd.) or ACMO (manufactured by Xingren Co., Ltd.) or the like can be mentioned.

The content of the solvent-free active energy ray-curable resin composition of the present invention in the case where these monofunctional monomers are contained may be in a range in which the effects exhibited by the present invention are not impeded and sufficiently exhibited, for example, with respect to the aforementioned polyester. The total of 100 parts by mass of the resin (A) and the polyester (meth) acrylate compound (B) is preferably in the range of 1 to 50 parts by mass.

The viscosity of the solventless active energy ray-curable resin composition of the present invention is preferably 1000 mPa. s~150,000mPa. The range of s is better at 5000mPa. s~100,000mPa. The scope of s. When the viscosity is in this range, the solvent-free active energy ray-curable resin composition can be applied to a uniform thickness even under high-speed coating conditions.

The laminated film of the present invention is characterized in that an adhesive containing the solvent-free active energy ray-curable resin composition of the present invention is applied to a film-form coated substrate of a coated object, and then a film-form coated substrate is laminated. When the binder is cured, at least one of the coating substrate or the coating substrate is a film having a poor adhesion.

Here, specific examples of the difficult-to-attach film include a polycarbonate film, a polyethylene terephthalate film, a polymethyl methacrylate film, a melamine resin film, a decylene-based resin film, and a ring. An olefin-based resin film, a polyimide film, a polyvinyl fluoride resin film, a polyvinylidene fluoride resin film, or the like. In the present invention, in particular, an untreated polyethylene terephthalate film, a polycarbonate film, a polyvinyl fluoride resin film, a polyvinylidene fluoride resin film, or the like is used. In the case of using a fluorine-based film or the like which is difficult to laminate a film to be used as a coating substrate or a coating substrate, excellent adhesion can be exhibited.

On the other hand, when one of the coated substrate or the coated substrate is used as the above-mentioned difficult-to-attach film, the other can be used as described above, and an easily adhesive film which is relatively easy to be used can be used. Here, examples of the easy-adhesive film include a film composed of polystyrene, polyester, polyolefin, polyvinyl alcohol, epoxy resin, ABS resin, AS resin, triacetyl cellulose resin, or the like. . In the present invention, it is particularly noted that when both the coated substrate and the coated substrate are used in the case of using the above-mentioned difficult-to-attach film, excellent bonding strength, particularly excellent adhesion strength even under moist heat conditions, is exhibited. The point.

When the laminated film is obtained by using the adhesive of the present invention, it is preferred to apply the adhesive of the present invention in a range of 0.5 to 100 μm in thickness, more preferably in the range of 1 to 50 μm.

Examples of the coating method for the above-mentioned adhesive for polarizing plate include bar coater coating, roll coater coating, spray coating, gravure coating, reverse gravure coating, lithography, flexographic printing, and screen printing. Any method can be used.

Hereinafter, an example of a method of obtaining a laminated film using the adhesive of the present invention will be described. First, the adhesive of the present invention is applied to the surface of the plastic film on which the substrate is coated by any of the above-described coating methods. In the case where the adhesive of the present invention contains the organic solvent, in order to volatilize the solvent after coating, it is dried at a temperature equal to or higher than the boiling point of the solvent for several minutes.

Next, the other plastic film covering the substrate is overlapped Pressed on the adhesive layer. At this time, higher bonding strength is obtained by heating at a temperature of 100 to 120 ° C for about 1 minute as needed.

Next, the laminated laminated film is irradiated with an active energy ray to harden the adhesive layer. The active energy ray system in the case where the solvent-free active energy ray-curable resin of the present invention or the adhesive containing the same is cured may, for example, be an ultraviolet ray or an electron beam. In the case where it is hardened by ultraviolet rays, an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, or a metal halide lamp is used as a light source, and the amount of light and the arrangement of the light source can be adjusted as needed; and in the case of using a high-pressure mercury lamp, it is generally preferable to use a high-pressure mercury lamp. A lamp 1 having a light amount in the range of 80 to 160 W/cm is hardened at a conveying speed of 5 to 50 m/min. On the other hand, in the case where it is hardened by an electron beam, it is generally preferable to use an electron beam acceleration device having an acceleration voltage in the range of 10 to 300 kV, and to cure it at a conveying speed of 5 to 50 m/min.

The laminated film obtained by using the adhesive of the present invention can be suitably used for, for example, a reflective film, an antireflection film, an antiglare film, a retardation film, etc., since the films are difficult to peel off from each other and maintain the bonding strength even under moist heat conditions. A member for a liquid crystal display device such as a polarizing film, a brightness enhancing film, or a diffusion film, or a back sheet of a solar cell.

[Examples]

The present invention will be more specifically described by the following examples and comparative examples, but the present invention is not limited to the examples.

Manufacturing example 1

<Manufacture of Polyester (Meth)acrylate Compound (A-1)>

In a flask equipped with a thermometer, a stirrer, and a condenser, put 531 After the mass fraction of 3-methyl-1,5-pentanediol is heated to 80 ° C to dissolve it, 482 parts by mass of terephthalic acid, 142 parts by mass of adipic acid, and 0.5 part by mass of dibutyl oxide are added. The tin was gradually heated to 250 ° C in a nitrogen atmosphere and reacted for 20 hours to obtain a polyester polyol (a-1) having a number average molecular weight (Mn) of 2,000 and a hydroxyl value of 56 mgKOH/g. 522 parts by mass of the polyester polyol (a-1) and 400 parts by mass of a tetrahydrofurfuryl alcohol acrylate polymer ("Viscoat #150D" manufactured by Osaka Organic Chemical Industry Co., Ltd.), 0.1 g of sim Zinc silicate and 0.2 g of methoquinone were heated to 80 ° C while stirring, and 74 parts by mass of 4,4'-methylenedicyclohexyl=diisocyanate was added. After the addition, the reaction was carried out for 5 hours, and then 4.6 parts by mass of hydroxyethyl acrylate was added, and the reaction was further carried out for 7 hours. The absorption of the isocyanate group was confirmed by infrared absorption mass spectrometry to obtain a solution of the polyester acrylate compound (A-1) having a weight average molecular weight (Mw) of 30,000.

Manufacturing Example 2

<Manufacture of Polyester (Meth)acrylate Compound (A-2)>

In a flask equipped with a thermometer, a stirrer, and a condenser, 531 parts by mass of 3-methyl-1,5-pentanediol was charged, and after heating to 80 ° C to dissolve it, 482 parts by mass of terephthalic acid and 142 were added. A part by mass of adipic acid and 0.5 part by mass of dibutyltin oxide were gradually heated to 250 ° C in a nitrogen atmosphere for 20 hours to obtain a polycondensation of a number average molecular weight (Mn) of 2,000 and a hydroxyl value of 56 mgKOH/g. Ester polyol (a-2). 522 parts by mass of the polyester polyol (a-2) and 400 parts by mass of a tetrahydrononyl alcohol acrylate polymer ("Viscoat #150D" manufactured by Osaka Organic Chemical Industry Co., Ltd.), 0.1 g of sim Zinc silicate, 0.2 g of methoxy hydrazine, While stirring, the temperature was raised to 80 ° C, and 84 parts by mass of 4,4'-methylenedicyclohexyl=diisocyanate was added. After the addition, the reaction was carried out for 5 hours, and then 12.7 parts by mass of hydroxyethyl acrylate was added, and the reaction was further carried out for 7 hours. The absorption of the isocyanate group was confirmed by infrared absorption mass spectrometry to obtain a solution of the polyester acrylate compound (A-2) having a weight average molecular weight (Mw) of 10,000.

Manufacturing Example 3

<Manufacture of Polyester (Meth)acrylate Compound (A-3)>

In a flask equipped with a thermometer, a stirrer, and a condenser, 532 parts by mass of "Kuraray Polyol P-2010" (a mixture of 3-methyl-1,5-pentanediol and adipic acid) was obtained, and the number average molecular weight ( Mn) 2,000, a hydroxyl value of 56 mgKOH/g), as a polyester polyol (a-3), 400 parts by mass of "Viscoat #150D", 0.1 g of zinc octylate, and 0.2 g of methoxy hydrazine, and stirred. While raising the temperature to 80 ° C, 63 parts by mass of isophorone diisocyanate was added. After the addition, the reaction was carried out for 5 hours, and then 4.7 parts by mass of hydroxyethyl acrylate was added, and the reaction was further carried out for 7 hours. The absorption of the isocyanate group was confirmed by infrared absorption mass spectrometry to obtain a solution of the acrylate compound (A-3) having a weight average molecular weight (Mw) of 30,000.

Manufacturing Example 3

<Manufacture of Polyester Resin (B-1)>

In a flask equipped with a thermometer, a stirrer, and a condenser, 224 parts by mass of ethylene glycol and 185 parts by mass of neopentyl glycol were charged, and after heating to 80 ° C to dissolve it, 311 parts by mass of terephthalic acid and 466 were added. Parts by mass of isophthalic acid and 0.1 parts by mass of tetraisopropyl titanate are slowly heated to 240 ° C under the environment of nitrogen gas. In the hour, a polyester resin (B-1) having a weight average molecular weight (Mw) of 2,900, an acid value of 7.8 mgKOH/g, a hydroxyl value of 67 mgKOH/g, and an aromatic ring concentration of 4.7 mmol/g was obtained.

Comparative manufacturing example 1

<Manufacture of Comparative Polyester Resin (B-2)>

In a flask equipped with a thermometer, a stirrer, and a condenser, 436 parts by mass of neopentyl glycol was charged, and after heating to 80 ° C to dissolve it, 180 parts by mass of sebacic acid, 296 parts by mass of isophthalic acid, and 132 were added. A part by mass of phthalic anhydride and 0.5 part by mass of dibutyltin oxide were gradually heated to 240 ° C under a nitrogen atmosphere, and when the acid value became 1.0 mg KOH / g, the temperature was lowered to 180 ° C. 96 parts by mass of trimellitic anhydride was added thereto and reacted for 1 hour to obtain a polyester resin having a weight average molecular weight (Mw) of 3,700, an acid value of 53 mgKOH/g, a hydroxyl value of 15 mgKOH/g, and an aromatic ring concentration of 3.1 mmol/g (B- 2).

Examples 1 to 5 and Comparative Example 1

<Manufacture of Sample 1 for Evaluation>

The adhesives (1) to (6) were prepared in the compositions described in Table 1. Then, as an original film, an untreated PET film (Cosmo Shine A4100, manufactured by Toyobo Co., Ltd.) having a thickness of 100 μm was used, and each adhesive was applied to 5 g/m ² , and a 100 μm thick untreated PET film was bonded in the same manner. (Cosmo Shine A4100, manufactured by Toyobo Co., Ltd.), and test pieces (1a) to (6a) were produced by irradiating 1000 mJ/cm ² with a high-pressure mercury lamp.

<Viscometry>

It was measured at 25 ° C using an E-type viscometer ("TV-20-shaped" tapered plate type manufactured by Toki Sangyo Co., Ltd.).

<Measurement of refractive index>

The refractive index of the liquid was measured at 25 ° C under a temperature condition using an Abbe refractometer ("NAR-3T" manufactured by ATAGO Co., Ltd.).

<Measurement of transparency>

The haze value of the test pieces (1a) to (6a) was measured using a haze and a haze meter (manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with JIS K7105, and evaluated according to the following criteria.

The haze value is less than 1%. . . . . . . . . . . "○"

The haze value is above 1% and less than 3%. . . "△"

The haze value is more than 3%. . . . . . . . . . . . "×"

<Measurement of strength>

Using a tensile tester ("AGS500NG" manufactured by SHIMADU Co., Ltd.), the strength (N/15 mm, T-peel) at a peeling speed of 300 mm/min was evaluated as the adhesion.

<Determination of Moisture and Heat Resistance / PCT Test>

After standing at 60 ° C and 90 RH% for 500 hours, the appearance of the sample was visually observed and the change before and after standing was evaluated according to the following criteria.

No change. . . . . "○"

Slightly whitened. . . "△"

Albino. . . . . . . "×"

<Manufacture of Sample 2 for Evaluation>

The above-mentioned adhesives (1) to (6) were applied to a polypropylene plate to have a film thickness of 50 μm after hardening, and test pieces (1b) to (6b) were produced by irradiating 1000 mJ/cm ² with a high-pressure mercury lamp under a nitrogen atmosphere. ).

<Measurement of Coating Film Tg>

The obtained test pieces (1b) to (6b) were measured at a frequency of 1 Hz and a temperature increase rate of 3 ° C/min using DMA ("RSA II" manufactured by Rheometric Scientific Co., Ltd.), and the temperature at which tan δ was maximized was defined as a coating film Tg ( °C).

<Measurement of storage elastic modulus>

The storage elastic modulus at 25 ° C was measured by the aforementioned DMA.

Among them, the terms in the table are as follows.

ACMO. . . . . Acrylate Porphyrin

V#150D. . . Osaka Organic Chemical Industry Co., Ltd. "Viscoat #150D"

2HPA. . . . . 2-hydroxypropyl acrylate

#184D. . . . . 1-hydroxy-cyclohexyl-phenyl-ketone ("IRGACURE 184D" manufactured by BASF Corporation)

TPO. . . . . 2,4,6-trimethylbenzimidyl-diphenylphosphine oxide ("DAROCUR TPO", manufactured by BASF Corporation)

Claims (16)

A solvent-free active energy ray-curable resin composition characterized by comprising a polyester resin (A) having a acid value of 20 mgKOH/g or less, a polyester (meth) acrylate compound (B), and The photoinitiator (C) is an essential component. The active energy ray-curable resin composition of claim 1, wherein the aromatic ring concentration of the polyester resin (A) is in the range of 4 mmol/g or more. The active energy ray-curable resin composition of claim 1, wherein the polyester resin (A) has a hydroxyl value in the range of 40 to 90 mgKOH/g. The active energy ray-curable resin composition according to claim 1, wherein the polyester resin (A) is obtained by reacting an aliphatic polyol, an aliphatic or an aromatic polybasic acid as a main raw material component. The active energy ray-curable resin composition of claim 1, wherein the polyester resin (A) has a weight average molecular weight (Mw) in the range of 3,000 to 20,000. The active energy ray-curable resin composition of claim 1, wherein the polyester (meth) acrylate compound (B) has an aliphatic polyol, and an aliphatic and/or aromatic polybasic acid in a molecular structure. The polyester structural portion obtained by the reaction of the main raw material component and the (meth) acrylonitrile group. The active energy ray-curable resin composition of claim 1, wherein the polyester (meth) acrylate compound (B) has a mass average molecular weight (Mw) in the range of 10,000 to 50,000. The active energy ray-curable resin composition of claim 1, wherein the polyester (meth) acrylate compound (B) is a polyester polyol (b1) having a number average molecular weight (Mn) in the range of 500 to 6,000. Polyisocyanate The compound obtained by reacting the compound (b2) and the hydroxyl group-containing (meth) acrylate compound (b3) as essential components. The active energy ray-curable resin composition of claim 1, wherein the (meth) acrylate group concentration of the polyester (meth) acrylate compound (B) is in the range of 0.04 to 0.5 mmol/g. An active energy ray-curable resin composition according to claim 1, which comprises the polyester (meth) acrylate compound (B) and the polyester resin (B) in a mass ratio [(A)/ (B)] becomes a range of 20/80 to 80/20. The active energy ray-curable resin composition of claim 1, wherein the photoinitiator (C) is in the range of 0.01 to 10 parts by mass based on 100 parts by mass of the polyester (meth) acrylate compound (B) . The active energy ray-curable resin composition of claim 1, which further contains free of the polyester resin (A), the polyester (meth) acrylate compound (B), and the photoinitiator (C). Base polymerizable monomer (D). An active energy ray-curable resin composition according to claim 6, which comprises the polyester resin (A) and the polyester (meth) acrylate compound (B), and a monomer having the radical polymerizable property (D) ), so that the mass ratio of [[(A)+(B)]/(D)]) is in the range of 90/10 to 30/70. An adhesive comprising the active energy ray-curable resin composition according to any one of claims 1 to 13. A laminate film obtained by using the adhesive of claim 14. A cured product obtained by hardening an active energy ray-curable resin composition according to any one of claims 1 to 13.