TWI663471B - Active energy ray-curable resin composition, cured product, adhesive, and laminated film - Google Patents

Abstract

The present invention provides a hard-to-bond plastic film, such as an untreated PET film, a fluorine-based film, and a polycarbonate film. The so-called hard-to-bond film also has high bonding strength, and can maintain its bonding strength even under hot and humid conditions. A solventless active energy ray-curable resin composition; an adhesive containing the resin composition; and a laminated film obtained by using the adhesive. A solvent-free active energy ray-curable resin containing a polyester resin (A), a polyester (meth) acrylate compound (B), and a photoinitiator (C) as an essential component in a range of an acid value of 20 or less Composition, adhesive and 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 using the resin composition, and a laminated film obtained by using the adhesive.

Laminated films in which various functional films are bonded to each other with an adhesive are necessary components in various products such as liquid crystal display devices, personal computers, and solar cell modules. Conventionally, polyethylene terephthalate (hereinafter referred to as "PET") film has been widely used as a base material of the laminated film. However, PET film is one of the substrates that are difficult to be adhered by an adhesive. Generally, It is a state in which the adhesion is improved by applying easy adhesion treatment such as corona treatment to the adhesion surface of the PET film. Therefore, in order to improve the productivity of the laminated film and reduce the cost, there is a need for an adhesive that can perform strong adhesion even without applying a PET film (hereinafter simply referred to as "untreated PET film") that is easily adhered. Moreover, in recent years, as electronic devices such as car navigation systems and solar cell modules have increased opportunities for outdoor use, an adhesive agent that can maintain high adhesion strength even in outdoor high-temperature and high-humidity environments has been sought.

As a coating with excellent adhesion to untreated PET film As a resin composition for a material, a homopolymer containing methyl methacrylate (Tg: 105 ° C, weight average molecular weight (Mw): 47,500, SP value: 10.0), and a coating with neopentyltetraacrylate is known. A resin composition is used (refer to Citation 1). This resin composition is superior to conventional resin compositions for coatings in that it has excellent adhesion to untreated PET films. However, it is an inventor who has completed assuming the use of coatings. The degree of high adhesion of the adhesive to which the films are bonded to each other.

In addition, among various functional films for laminated films, in addition to untreated PET films, there are many difficult-to-adhere films. For example, a fluorine-based film made of a polyvinyl fluoride resin or a polyvinylidene fluoride resin is excellent in weather resistance, heat resistance, and pollution resistance, and can be used as a member of a solar cell module. Since it is oily, it is difficult to adhere with an adhesive. Moreover, although a polycarbonate film has a characteristic of being excellent in impact resistance, it is difficult to adhere | attach strongly with the conventional adhesive agent. Because of this, a highly adhesive adhesive is required for these various non-adhesive plastic films typified by untreated PET films.

Therefore, it was found that a polyester (meth) acrylate compound having a polyester structure portion and a (meth) acryl group, a polyester resin having an acid value in the range of 40 to 90 mgKOH / g, and a polymerization initiator were found as essential components. Active energy ray-curable resin composition, even for difficult-to-adhere films such as untreated PET films, fluorine-based films, and polycarbonate films, it exhibits high adhesion strength, and maintains its adhesion strength even under hot and humid conditions ( Patent Document 2). However, when applying this resin composition, It is necessary to dilute with an organic solvent for the purpose of imparting applicability or operability. Therefore, after coating, it is necessary to dry and volatilize the organic solvent, and there is room for improvement from the viewpoint of environmental impact or productivity.

[Prior technical literature] [Patent Literature]

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

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

The problem to be solved by the present invention is to provide a hard-to-bond plastic film, such as an untreated PET film, a fluorine-based film, and a polycarbonate film, that is, a so-called hard-to-bond film having a high bonding strength, especially even in hot and humid conditions. A solvent-free active energy ray-curable resin composition capable of maintaining its adhesive strength; an adhesive containing the resin composition; and a laminated film obtained by using the adhesive.

As a result of intensive research to solve the above-mentioned problems, the present inventors have found that a polyester resin (A), a polyester (meth) acrylate compound (B) containing an acid value in a range of 20 mgKOH / g or less, and polymerization are found. The solvent-free active energy ray-curable resin composition containing the initiator (C) as an essential component and substantially containing no organic solvent is difficult to adhere to untreated PET films, fluorine-based films, and polycarbonate films. The film also exhibited high adhesion strength, and maintained its adhesion strength even under humid and hot conditions, and completed the present invention.

That is, the present invention relates to a solventless active energy ray-curable resin composition, which is characterized in that it contains a polyester resin (A) and polyester (meth) acrylic acid having an acid value in a range of 20 mgKOH / g or less. The ester compound (B) and the photoinitiator (C) are essential components.

The present invention further relates to an adhesive containing the aforementioned active energy ray-curable resin composition.

The present invention further relates to a laminated film obtained by using the aforementioned adhesive.

According to the present invention, it is possible to provide a solvent-free active energy that exhibits high adhesion to difficult-to-adhere films such as untreated PET film, fluorine-based film, and polycarbonate film, and maintains its adhesion even under hot and humid conditions A wire-curable resin composition; an adhesive containing the resin composition; and a laminated film obtained by using the adhesive.

[Form of Implementing Invention]

The solvent-free active energy ray-curable resin composition of the present invention is characterized in that it contains a polyester resin (A) having an acid value in the range of 20 or less, a polyester (meth) acrylate compound (B), and Kogyo The initiator (C) is used as an essential component.

The polyester resin (A) used in the present invention has an acid value in a range of 20 mgKOH / g or less. With this range, even if the organic solvent is not substantially contained, that is, the so-called solvent-free, the resin composition of the present invention The affinity of the material for the PET film or the fluorine-based film is improved, and the wettability during coating becomes good. Among them, a resin composition having an improved adhesive strength after hardening by improving the adhesiveness of the substrate at the time of lamination, and further having excellent adhesive strength under moist heat conditions can be obtained. The acid value 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 resin composition of the present invention has an improved affinity for a PET film or a fluorine-based film, and substantially does not contain organic compounds. A solvent, that is, so-called solventless coating tends to have good wettability, and is preferred.

In addition, when the hydroxyl value of the polyester resin (A) is in the range of 40 to 90 mgKOH / g, since the affinity of the resin composition of the present invention to a PET film or a fluorine-based film is improved, it does not substantially contain organic compounds. A solvent, that is, so-called solventless coating tends to have good wettability, and is preferred.

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

The aliphatic polyhydric alcohol 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, but examples thereof include ethylene glycol, diethylene glycol, propylene glycol, and 1, 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-hexanedidiol Alcohol, 2,2,4-trimethyl-1,3-pentanediol, 1,4-bis (hydroxymethyl) cyclohexane, trimethylolethane, trimethylolpropane, glycerol , Hexatriol, Neopentyl Alcohol, etc. The polyol can be used alone, or Two or more types can be used together. Among these, from the viewpoint of obtaining a resin composition having excellent adhesion to the plastic film substrate at the time of lamination, it is preferred to use a combination of ethylene glycol, diethylene glycol, propylene glycol, 1,3-propanediol, 1,2 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-hexanediol, 2,2,4 -Aliphatic diols such as trimethyl-1,3-pentanediol, 1,4-bis (hydroxymethyl) cyclohexane, and trimethylolethane, trimethylolpropane, glycerol Trifunctional or higher aliphatic polyhydric alcohols such as hexatriol and neopentyl tetraol.

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, azelaic acid, and sebacic acid. Aliphatic dibasic acids such as acids; aromatic dibasic acids such as phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid, phthalic acid; hexahydrophthalic acid, 1,4-cyclohexane di Alicyclic dibasic acids such as carboxylic acids; aliphatic unsaturated dibasic acids such as tetrahydrophthalic acid, maleic acid, maleic anhydride, fumaric acid, citraconic acid, itaconic acid, and pentenedioic acid; Aliphatic tribasic acids such as 1,2,5-hexanetricarboxylic acid and 1,2,4-cyclohexanetricarboxylic acid; aromatics such as trimellitic acid and 2,5,7-naphthalenetricarboxylic acid Family of tribasic acids. The polybasic acid may be used singly or in combination of two or more kinds. Among these, from the viewpoint of obtaining a highly coating resin composition, the aforementioned aliphatic dibasic acid is preferred, and succinic acid, glutaric acid, adipic acid, pimelic acid, and suberic acid are more preferred. In the case of an aliphatic dibasic acid having 4 to 8 carbon atoms, adipic acid is particularly preferred. When the object to be bonded is an untreated PET film, from the standpoint of obtaining a resin composition having excellent adhesion to the untreated PET film and higher bonding strength, phthalic acid and phthalic acid are preferably used. Aromatic dibasic acids such as anhydride, terephthalic acid, isophthalic acid, and phthalic acid are preferably terephthalic acid. That is, the polybasic acid raw material system of the polyester resin (A) is preferably in a range of 4 to 8 in which the carbon number of the succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and the like is used in combination. Aliphatic dibasic acids, and aromatic dibasic acids such as phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid, and phthalic acid.

Examples of the method for producing the polyester resin (A) include, for example, the use of an esterification catalyst at a temperature of 150 to 250 ° C. as needed, and the polyhydric alcohol and the polybasic acid are reacted while removing generated water. Methods etc.

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

The polyester (meth) acrylate compound (B) used in the present invention has a polyester structure site and a (meth) acrylfluorenyl group in the molecular structure, and the molecular structure is irradiated with active energy rays. (Meth) acrylfluorene group is a component that generates a polymerization reaction and hardens, and makes plastic films adhere to each other, and improves the bonding strength under moist heat conditions by forming a crosslinked structure. On the other hand, as described above, the polyester resin (A) has a specific range of acid value and makes the resin composition of the present case difficult to adhere to untreated PET films, fluorine-based films, and the like without solvents. Ingredients with improved affinity. The resin composition of the present invention contains the polyester tree The resin (A) and the polyester (meth) acrylate compound (B) are adhered to each other with an adhesive, and then the active energy ray is irradiated to harden the film, which is a difficult-to-adhere property in the so-called lamination step. The adhesiveness between the plastic film and the adhesive is improved even in the absence of a solvent. By carrying out the curing reaction of the polyester (meth) acrylate compound (B) in such an adhered state, the films can be adhered to each other very strongly.

The weight average molecular weight (Mw) of the aforementioned polyester (meth) acrylate compound (B) used in the present invention is not particularly limited, but its weight average molecular weight (Mw) is preferably in the range of 5,000 to 100,000; It is more preferably in the range of 8,500 to 85,000 from the viewpoint of coating properties of various resin compositions that exhibit higher adhesion strength to various difficult-to-adhere films. Among them, from the resin composition having excellent adhesion to the substrate in the lamination step and suitable viscosity for coating, the weight average molecular weight (Mw) is more preferably in the range of 10,000 to 50,000.

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.

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

Detector: RI (differential refractometer)

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

Measurement conditions: column temperature 40 ℃

Solvent tetrahydrofuran

Flow rate 0.35ml / min

Standard: Monodisperse Polystyrene

Sample: A solution obtained by filtering a tetrahydrofuran solution having a mass of 0.2% by mass in terms of the solid content of the resin through a microfilter (100 μl)

The polyester (meth) acrylate compound (B) preferably has a polyester structure in a molecular structure obtained by reacting an aliphatic polyol with an aliphatic and / or aromatic polybasic acid as a main raw material component. And compounds having a (meth) acrylfluorenyl group. Examples of such a polyester (meth) acrylate compound (A) include, for example, the number of moles of the isocyanate group in the polyisocyanate compound (b2) with respect to the number of hydroxyl groups in the polyester polyol (b1). The polyester polyol (b1) obtained by reacting an aliphatic polyhydric alcohol with an aliphatic and / or aromatic polybasic acid is reacted with the polyisocyanate compound (b2) under the condition that the number of ears is excessive, and the reaction is allowed to proceed. A method of reacting the intermediate obtained in the above with a hydroxyl group-containing (meth) acrylate (b3) and the like.

Examples of the aliphatic polyhydric alcohols that serve as a raw material for 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-butanediol Diol, 1,5-pentanediol, 3-methyl 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 2,2,4-trimethyl-1,3- Aliphatic polyols such as pentanediol, 1,4-bis (hydroxymethyl) cyclohexane, trimethylolethane, trimethylolpropane, glycerol, hexanetriol, neopentyl tetraol; Ether diols such as polyoxyethylene glycol, polyoxypropylene glycol, etc .; through the aforementioned aliphatic polyol and ethylene oxide Ring-opening polymerization of various compounds containing cyclic ether bonds, such as propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, etc. The obtained modified polyether polyol; a lactone-based polyester polyol obtained by a polycondensation reaction between the aforementioned aliphatic polyol and various lactones such as ε-caprolactone. These can be used individually or in combination of 2 or more types. Among these, a resin composition having excellent adhesiveness with a plastic film substrate during lamination and high adhesive strength after curing can be obtained, and preferably 1, 2, 2-trimethyl-1, 3-propanediol, 2,2-dimethyl-3-isopropyl-1,3-propanediol, 1,3-butanediol, 3-methyl-1,3-butanediol, 3-methyl-1 5,5-pentanediol, neopentyl glycol, 2,2,4-trimethyl-1,3-pentanediol and other branched aliphatic diols, particularly preferably 3-methyl 1,5- Pentanediol.

Examples of the polybasic acid to be the raw material of the polyester polyol (b1) include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid. And other aliphatic dibasic acids; phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid, phthalic acid and other aromatic dibasic acids; hexahydrophthalic acid, 1,4-cyclohexane dicarboxylic acid Alicyclic dibasic acids such as acids; aliphatic unsaturated dibasic acids such as tetrahydrophthalic acid, maleic acid, maleic anhydride, fumaric acid, citraconic acid, itaconic acid, and pentenedioic acid; 1 Aliphatic tribasic acids such as 2,2,5-hexanetricarboxylic acid, 1, 2,4-cyclohexanetricarboxylic acid; aromatics such as trimellitic acid, 2,5,7-naphthalenetricarboxylic acid Tribasic acid and so on. These can be used individually or in combination of 2 or more types. Among these, from the viewpoint of obtaining a highly coating resin composition, the aforementioned aliphatic dibasic acid is preferable, and succinic acid, glutaric acid, adipic acid, pimelic acid, and suberic acid are more preferable. Such as aliphatic dibasic acids having 4 to 8 carbon atoms, particularly preferred For adipic acid. In the case where the untreated PET film is to be adhered, a phthalic acid, a phthalic anhydride, or a phthalic anhydride is preferably used from the viewpoint of obtaining a resin composition having excellent adhesion to the untreated PET film and having a higher adhesive strength. As the aromatic dibasic acid such as terephthalic acid, isophthalic acid, and phthalic acid, terephthalic acid is more preferably used. Furthermore, from the viewpoint of exhibiting excellent coating properties and adhesion strength, the present invention is particularly preferably used in combination with the aforementioned aliphatic polybasic acid and aromatic polybasic acid. In the case where the foregoing aliphatic polybasic acid and aromatic polybasic acid are used in combination, the proportion of the aliphatic polybasic acid and the aromatic polybasic acid is not particularly limited if the effects of the present invention are not impaired, but it is preferably 10-50 mol% of the aliphatic dibasic acid and the aromatic polybasic Acid 50 ~ 90 mol%.

Examples of the method for producing the polyester polyol (b1) include, for example, the use of an esterification catalyst at a temperature of 150 to 250 ° C as needed, and the polyol and the polyacid are reacted while removing generated water. Method of reaction, etc.

The number-average molecular weight (Mn) of the polyester polyol (b1) obtained in this manner is preferably 500 to 500 ~ of a resin composition having excellent adhesion to the substrate in the lamination step and a viscosity suitable for coating. A range of 6,000, more preferably a range of 750 to 4,000, and a particularly good range of 900 to 3,000.

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

Examples of the polyisocyanate compound (b2) used as a raw material of the polyester (meth) acrylate compound (B) include various diisocyanates. Ester monomers, or adduct-type polyisocyanate compounds having urethane bonding sites in the molecule, nurate-type polyisocyanate compounds having an isotricyanate ring structure in the molecule, etc. .

Examples of the diisocyanate single system include butane-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethyl ether. Aliphatic diisocyanates such as hexamethylene diisocyanate, xylylene diisocyanate, m-tetramethylxylylene diisocyanate; cyclohexane-1,4-diisocyanate, isophorone diisocyanate, ion Alicyclic diisocyanates such as urethane 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, dialkyldiphenyl Methane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, toluene diisocyanate, etc. Aromatic diisocyanates and the like.

The adduct-type polyisocyanate compound having a urethane bonding site in the molecule is obtained by, for example, reacting a diisocyanate monomer with a polyol. Examples of the diisocyanate monomer used in this reaction include the aforementioned various diisocyanate monomers, and each of them may be used alone, or two or more of them may be used in combination. The polyol used in this reaction includes various polyols exemplified as the raw material of the polyester polyol (b1), and various polyester polyols exemplified as the polyester polyol (b1). Alcohol and the like may be used alone or in combination of two or more kinds.

The cyanurate-type polyisocyanate compound having an isotricyanate ring structure in the molecule is obtained by, for example, reacting a diisocyanate monomer with a monoalcohol and / or a diol. Examples of the diisocyanate monomer used in this reaction include the aforementioned various diisocyanate monomers, and each of them may be used alone, or two or more of them may be used in combination. Examples of the monoalcohol used in this reaction include hexanol, 2-ethylhexanol, octanol, n-decanol, n-undecanol, n-dodecanol, n-tridecanol, n-decyl Tetraol, n-pentadecyl alcohol, n-heptadecanyl alcohol, n-octadecanol, n-nonadecanol, eicosanol, 5-ethyl-2-nonanol, trimethylnonanol, 2-hexyldecanol, 3 , 9-diethyl-6-tridecanol, 2-isoheptyl isoundecyl alcohol, 2-octyldodecanol, 2-decyltetradecanol, etc .; as for the diol, it can be exemplified as the aforementioned Various diols exemplified as the raw material of the polyester polyol (a1). These monoalcohols or diols may be used singly or in combination of two or more kinds.

Among the various isocyanate compounds (b2), the weight average molecular weight (Mw) of the obtained polyester (meth) acrylate compound (B) can be easily adjusted to the appropriate range described above, and a diisocyanate monomer is preferred. Furthermore, from the viewpoint of obtaining a resin composition excellent in both adhesion to a plastic film substrate at the time of lamination and adhesive strength after curing, isophorone diisocyanate and dicyclohexylmethane-4 are preferred, 4'-diisocyanate, 4,4'-diphenylmethane diisocyanate, toluene diisocyanate.

Examples of the hydroxyl-containing (meth) acrylate compound (b3) that is a raw material of the polyester (meth) acrylate compound (B) include, for example, 2-hydroxyethyl (meth) acrylate, (meth) 2-hydroxypropyl acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxyethyl acrylamide, glycerin di (meth) acrylate, trimethylol Propane di (meth) acrylate, neopentaerythritol tri (meth) acrylate, dinepentaerythritol penta (meth) acrylate, and the like. These can be used individually or in combination of 2 or more types. Among these, a resin composition having small shrinkage upon curing and more excellent adhesive strength after curing can be obtained, and 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 4-hydroxybutyl acrylate are preferred. Monofunctional (meth) acrylate compounds such as 2-hydroxyethylpropenamide and 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate are more preferred.

Examples of the method for producing the polyester (meth) acrylate compound (A) include a molar number (OH) of a hydroxyl group contained in the polyester polyol (b1), and a polyisocyanate compound (b2). The ratio [(OH) / (NCO)] of the number of moles (NCO) of the isocyanate group contained is a ratio in the range of 1/2 to 1 / 2.1. The polyester polyol (b1) and the polyisocyanate compound are used. (b2) Under a temperature condition of 20 to 120 ° C, an intermediate is obtained by performing a reaction in the presence of a urethane catalyst as needed, so that the Molar number of the isocyanate group contained in the intermediate is obtained. (NCO), the ratio [(OH) / (NCO)] to the molar number (OH) of the hydroxyl group contained in the hydroxyl group-containing (meth) acrylate compound (b3) is 1 / 0.95 to 1 / 1.05 In the range ratio, the intermediate is reacted with the hydroxyl-containing (meth) acrylate compound (b3) at a temperature of 20 to 120 ° C in the presence of a urethane catalyst as required. Method, etc.

Other production methods include, for example, a method in which the polyester polyol (b1), the polyisocyanate compound (b2), and the hydroxyl group-containing (meth) acrylate compound (b3) are charged in batches and reacted. Or after reacting the said isocyanate compound (b2) with the said hydroxyl-containing (meth) acrylate compound (b3), the intermediate obtained by this reaction is made A method of reacting with the polyester polyol (b1) and the like.

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

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

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 the case of the urethane bond concentration of the polyester (meth) acrylate compound (B), the adhesiveness with the plastic film substrate during lamination is improved, and the adhesive strength after curing is excellent From the viewpoint of the resin composition, the range of 0.6 to 5 mmol / g is preferable, and the range of 0.8 to 3 mmol / g is more preferable.

From the viewpoint of obtaining a resin composition that has improved adhesive strength after curing due to improved substrate adhesion during lamination, and further has excellent adhesive strength under wet heat conditions, the solventless active energy ray hardening type of the present invention The resin composition preferably contains the polyester resin (A) and the polyester (meth) acrylate compound (B) so that the mass ratio [(A) / (B)] of the two is 2/98 to 80 / The range of 20 is more preferably 5/95 ~ 55/45 range.

Examples of the polymerization initiator (C) used in the present invention include 1-hydroxycyclohexylphenyl 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 derivatives, 2,2'-dimethoxy-1 2,2-diphenylethyl-1-one, 2,4,6-trimethylbenzylidene diphenylphosphine oxide, bis (2,4,6-trimethylbenzylidene) phenyl Phosphine oxide, 2-methyl-1- [4- (methylthio) phenyl] -2- Phenyl-1-acetone, 2-benzyl-2-dimethylamino-1- (4- Phenylphenyl) -but-1-one and the like.

Examples of commercially available strains of these polymerization initiators (C) include: "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 "(manufactured by BASF (formerly Ciba Specialty Chemicals))," Lucirin TPO "(manufactured by BASF)," KAYACURE " -DETX "," KAYACURE-MBP "," KAYACURE-DMBI "," KAYACURE-EPA "," KAYACURE-OA "(manufactured by Nippon Kayaku Co., Ltd.)," Vicure-10 "," Vicure-55 "(Stauffer Chemical company), `` Trigonal P1 '' (manufactured by Akzo), `` Sandoray 1000 '' (manufactured by Sandys), `` DEEP '' (manufactured by Upjohn), `` Quantacure-PDO "," Quantacure-ITX "," Quantacure-EPD "(made by Ward Blenkinsop), etc. Among these, from the viewpoint of exhibiting higher hardenability to the solventless active energy ray-curable resin composition of the present invention, it is preferable to use 1-hydroxycyclohexylphenyl ketone in combination (commercial product "IRGACURE 184"). With diphenyl (2,4,6-trimethylbenzyl) phosphine oxide (commercial product "Rulicin TPO").

The blending amount of the polymerization initiator (C) is better than the solventless active energy ray of the present invention from the viewpoint that the sensitivity of light is well maintained without causing precipitation of crystals or deterioration of coating film properties. The resin component of the curable resin composition is 100 parts by mass, preferably in a range of 0.05 to 20 parts by mass, and more preferably in a range of 0.1 to 10 parts by mass.

The solvent-free active energy ray-curable resin composition of the present invention may contain various photosensitizers in combination with the aforementioned photopolymerization initiator. Examples of the light sensitizers include amines, ureas, sulfur compounds, phosphorus compounds, chlorine compounds, nitriles, and other nitrogen compounds. These can be used alone or in combination of two or more kinds. . In the case where the solvent-free active energy ray-curable resin composition of the present invention contains such a photosensitizer, the content is 100 parts by mass relative to the resin component of the solvent-free 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 solvent-free active energy ray-curable resin composition of the present invention does not substantially contain an organic solvent. However, the so-called "substantially no organic solvent system" means that the active energy ray-curable resin composition does not contain an organic solvent, or even a very small amount, and it is necessary to volatilize the organic solvent before lamination and to show sufficient coating. Coverability, adhesion An 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 contained in a trace amount in a proportion of 1,000 ppm or less, preferably 100 ppm or less, and further 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, silicon-based additives, fluorine-based additives, rheology control agents, deaerators, antistatic agents, and anti-fog agents. The content of the case where the solvent-free active energy ray-curable resin composition of the present invention contains such additives is in a range where the effects of the additives are fully exerted without hindering the ultraviolet curing, compared with the solvent-free active energy ray hardening of the present invention. The resin component of the type resin composition is 100 parts by mass, preferably in a range of 0.01 to 40 parts by mass.

The solvent-free active energy ray-curable resin composition of the present invention may be used in combination with other resins for the purpose of improving adhesion to a film substrate and the like. Examples of other resins include acrylic resins such as methyl methacrylate resin and methyl methacrylate copolymer; polystyrene, methyl methacrylate-styrene copolymer; and polyester resins. ; Polyurethane resin; polybutadiene resin such as polybutadiene or butadiene-acrylonitrile copolymer; bisphenol epoxy resin, phenoxy resin or novolac epoxy resin, etc. Epoxy. The content of the case where the solvent-free active energy ray-curable resin composition of the present invention contains these resins is in a range in which the effects exhibited by the present invention are not impeded and fully exerted, and is relative to the polyester resin (A) and the aforementioned polyester resin (A). 100 parts by mass of the polyester (meth) acrylate compound (B) in total, preferably 1 to 50 parts by mass Range.

The solvent-free active energy ray-curable resin composition of the present invention may be used in combination with a monofunctional monomer for the purpose of adjusting its viscosity and the like. Examples of such monofunctional monomers include monofunctional monomers having one ethylenically unsaturated bond in one molecule, and preferred examples thereof include one (meth) acrylfluorenyl group in one molecule. Or vinyl compounds. Specific examples include vinyl monomers such as N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, and vinylpyridine; isoamyl (meth) acrylate, (methyl) ) Acrylic acid acrylate, tricyclodecyl (meth) acrylate, dicyclopentyl (meth) acrylate, dicyclopentenyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid Benzyl methyl ester, 4-butylcyclohexyl (meth) acrylate, allyl Porphyrin, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate Tertiary, (propyl) (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth) acrylate, (meth) acrylic tertiary Butyl ester, amyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isopropyl (meth) acrylate Octyl ester, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, ( Dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, tetramethyl (meth) acrylate Hydrofurfuryl ester, butoxyethyl (meth) acrylate, ethoxy diethylene glycol (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate Methoxyethylene glycol (methyl) propylene 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, diethylaminoethyl (meth) acrylate, 7-amino-3,7-dimethyloctyl (meth) acrylate, N, N-diethyl (meth) acrylic acid Amine, N, N-dimethylaminopropyl (meth) acrylamide, hydroxybutyl vinyl ether, lauryl vinyl ether, cetyl 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, R ² represents an alkylene group having 2 to 8 carbon atoms, and m represents an integer of 1 to 8)

(In 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 kinds.

Examples of commercially available monofunctional monomers include Viscoat 150D (manufactured by Osaka Organic Chemical Industry Co., Ltd.) and ACMO (manufactured by Keihin Corporation).

The content in the case where the solvent-free active energy ray-curable resin composition of the present invention contains such monofunctional monomers is only within a range in which the effects exhibited by the present invention are not impeded and fully exhibited, for example, relative 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 more preferably 5000 mPa. s ~ 100,000mPa. The range of s. If the viscosity is within this range, the solventless active energy ray-curable resin composition can be applied evenly under a high-speed coating condition.

The laminated film of the present invention is characterized in that an adhesive containing the above-mentioned solvent-free active energy ray-curable resin composition of the present invention is applied to a film-shaped coating substrate of an object to be coated, and then a laminated film-shaped coating substrate is applied. It is obtained by hardening the said adhesive material, and the at least one of the said coating base material or a coating base material uses a hard-to-adhesive film.

Here, specific examples of the difficult-to-adhere film include a polycarbonate film, a polyethylene terephthalate film, a polymethyl methacrylate film, a melamine resin film, a norbornene-based resin film, and a ring. Olefin-based resin films, polyimide resin films, polyvinyl fluoride resin films, polyvinylidene fluoride resin films, and the like. Among these, the present invention particularly relates to an untreated polyethylene terephthalate film, a polycarbonate film, a polyvinyl fluoride resin film, a polyvinylidene fluoride resin film, etc. In the case of a thin film such as a fluorine-based film, which has hitherto been difficult to form a thin film, when it is used as a coating substrate or a coating substrate, it exhibits excellent adhesion.

On the other hand, when the above-mentioned difficult-to-adhere film is used by one of the coating substrate or the coating substrate, the other is an easily-adhesive film that can be easily adhered as described above. Here, examples of the easily-adhesive film include films made of polystyrene, polyester, polyolefin, polyvinyl alcohol, epoxy resin, ABS resin, AS resin, and triethyl cellulose resin. . In the present invention, it is worth pointing out that the use of the above-mentioned difficult-to-adhere film on both the coated substrate and the coated substrate exhibits excellent adhesion strength, and particularly exhibits excellent adhesion strength even under hot and humid conditions. Point.

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

Examples of the method for applying the adhesive for polarizing plates 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 the method of obtaining a laminated film using the adhesive agent of this invention is demonstrated. First, the adhesive of the present invention is applied to the surface of a plastic film on which a substrate is coated by any of the aforementioned coating methods. When the adhesive of the present invention contains the aforementioned organic solvent, in order to volatilize the solvent after coating, it is dried at a temperature higher than the boiling point of the solvent for several minutes.

Next, overlay the other plastic film covering the substrate Press on the adhesive layer. At this time, a higher adhesive strength can be obtained by heating at a temperature of 100 to 120 ° C. for about one minute as needed.

Next, the laminated laminated film is irradiated with active energy rays to harden the adhesive layer. Examples of the active energy ray system at the time of curing the solventless active energy ray-curable resin or the adhesive containing the solvent of the present invention include, for example, ultraviolet rays and electron beams. In the case of hardening by ultraviolet rays, as a light source, an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, and a metal halide lamp can be used. The amount of light and the configuration of the light source can be adjusted as required. When a high-pressure mercury lamp is used, it is usually better than A lamp 1 having a light amount in a range of 80 to 160 W / cm is hardened at a conveying speed in a range of 5 to 50 m / min. On the other hand, when the electron beam is used to harden it, it is generally preferred to use an electron beam acceleration device having an acceleration voltage in the range of 10 to 300 kV to harden it at a conveying speed in the range of 5 to 50 m / min.

The laminated film obtained by using the adhesive of the present invention is difficult to peel from each other, and can maintain its adhesive strength even under wet heat conditions. Therefore, it can be suitably used in, for example, reflective films, anti-reflective films, anti-glare films, retardation films, Components for liquid crystal display devices, such as polarizing films, brightness enhancing films, and diffusion films;

[Example]

Examples and comparative examples are given below to explain the present invention more specifically, but the present invention is not limited to these examples.

Manufacturing example 1

<Production of polyester (meth) acrylate compound (A-1)>

In a flask equipped with a thermometer, a stirrer and a condenser, put 531 Parts of 3-methyl-1,5-pentanediol were heated to dissolve at 80 ° C, and then 482 parts by mass of terephthalic acid, 142 parts by mass of adipic acid, and 0.5 parts by mass of dibutyl oxide were added. Tin was gradually heated to 250 ° C. under a nitrogen gas 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 acrylic polymer ester ("Viscoat # 150D" manufactured by Osaka Organic Chemical Industry Co., Ltd.) and 0.1 g of octane Zinc enoate and 0.2 g of methoquinone were heated to 80 ° C. while stirring, and 74 parts by mass of 4,4′-methylene dicyclohexyl diisocyanate was added. After the addition, a reaction was performed for 5 hours, and then 4.6 parts by mass of hydroxyethyl acrylate was added, and the reaction was further performed for 7 hours. It was confirmed by infrared absorption mass spectrometry that the absorption of isocyanate groups disappeared, and a solution of a polyester acrylate compound (A-1) having a weight average molecular weight (Mw) of 30,000 was obtained.

Manufacturing example 2

<Production of polyester (meth) acrylate compound (A-2)>

A flask equipped with a thermometer, a stirrer and a condenser was charged with 531 parts by mass of 3-methyl-1,5-pentanediol and heated to 80 ° C to dissolve it. Then, 482 parts by mass of terephthalic acid and 142 parts were added. Parts of adipic acid and 0.5 parts by mass of dibutyltin oxide were slowly heated to 250 ° C. under a nitrogen gas atmosphere and reacted for 20 hours to obtain a polymer having 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 tetrahydrofurfuryl alcohol acrylic polymer ester ("Viscoat # 150D" manufactured by Osaka Organic Chemical Industry Co., Ltd.) and 0.1 g of octane Zinc enoate, 0.2 g of methoxyquinone, The temperature was raised to 80 ° C while stirring, and 84 parts by mass of 4,4'-methylenedicyclohexyl diisocyanate was added. After the addition, a reaction was performed for 5 hours, and then 12.7 parts by mass of hydroxyethyl acrylate was added, and the reaction was further performed for 7 hours. It was confirmed by infrared absorption mass spectrometry that the absorption of the isocyanate group disappeared, and a solution of the polyester acrylate compound (A-2) having a weight average molecular weight (Mw) of 10,000 was obtained.

Manufacturing example 3

<Production of polyester (meth) acrylate compound (A-3)>

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

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 added, and the mixture was heated to 80 ° C to dissolve, and 311 parts by mass of terephthalic acid and 466 parts were added. Mass parts of isophthalic acid and 0.1 parts by mass of tetraisopropyl titanate are slowly heated to 240 ° C. under a nitrogen atmosphere to react 5 Hours, 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

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

A flask equipped with a thermometer, a stirrer and a condenser was charged with 436 parts by mass of neopentyl glycol, and heated to 80 ° C to dissolve it, and then 180 parts by mass of sebacic acid, 296 parts by mass of isophthalic acid, and 132 parts were added. Mass parts of phthalic anhydride and 0.5 parts by mass of dibutyltin oxide were gradually heated to 240 ° C under the environment of nitrogen gas, and then cooled to 180 ° C when the acid value became 1.0 mgKOH / g. 96 parts by mass of trimellitic anhydride was added thereto and reacted for 1 hour to obtain a polyester resin (B-, 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. 2).

Examples 1 to 5, Comparative Example 1

<Manufacture of Evaluation Sample 1>

Adhesives (1) to (6) were prepared with the compositions described in Table 1. Next, an untreated PET film ("Cosmo Shine A4100" manufactured by Toyobo Co., Ltd.) was used as the original sheet, and each of the adhesives was applied to 5 g / m ² , and a 100-μm-thick untreated PET film was similarly bonded. ("Cosmo Shine A4100" manufactured by Toyobo Corporation), and irradiated with 1000mJ / cm ² with a high-pressure mercury lamp to produce test pieces (1a) to (6a).

<Viscosity measurement>

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

<Measurement of refractive index>

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

<Measurement of transparency>

The haze values of the test pieces (1a) to (6a) were measured using a turbidity and haze meter (manufactured by Nippon Denshoku Industries) 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%. ． ． 「△」

Haze value is above 3%. ． ． ． ． ． ． ． ． ． ． ． 「×」

<Measurement of adhesion strength>

Using a tensile tester ("AGS500NG" manufactured by Shimadu Corporation), the strength (N / 15mm, T-peel) at a peeling speed of 300 mm / min was evaluated as the adhesive force.

<Damp heat resistance measurement / PCT test>

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

No change. ． ． ． ． "○"

Slightly albino. ． ． 「△」

Albino. ． ． ． ． ． ． 「×」

<Manufacture of Evaluation Sample 2>

The aforementioned adhesives (1) to (6) were applied to a polypropylene plate so that the film thickness after curing was 50 μm, and test pieces (1b) to (6b) made by irradiating 1000mJ / cm ² with a high-pressure mercury lamp under a nitrogen atmosphere were manufactured. ).

<Measurement of Coating Film Tg>

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

<Measurement of storage elastic modulus>

The aforementioned DMA was used to measure the storage elastic modulus at 25 ° C.

The terms used in the table are as follows.

ACMO. ． ． ． ． Allyl Porphyrin

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

2HPA. ． ． ． ． 2-hydroxypropyl acrylate

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

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

Claims (16)

A solvent-free active energy ray-curable resin composition characterized in that it contains a polyester resin (A) having an acid value in a range 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 according to claim 1, wherein the aromatic ring concentration of the polyester resin (A) is in a range of 4 mmol / g or more. The active energy ray-curable resin composition according to claim 1, wherein the polyester resin (A) has a hydroxyl value in a 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 polyacid as a main raw material component. The active energy ray-curable resin composition according to claim 1, wherein the weight average molecular weight (Mw) of the polyester resin (A) is in the range of 3,000 to 20,000. The active energy ray-curable resin composition according to claim 1, wherein the polyester (meth) acrylate compound (B) has an aliphatic polyhydric alcohol and an aliphatic and / or aromatic polybasic acid in its molecular structure. Polyester structural site and (meth) acrylfluorenyl group obtained by reacting as main raw material components. The active energy ray-curable resin composition according to claim 1, wherein the mass average molecular weight (Mw) of the polyester (meth) acrylate compound (B) is in a range of 10,000 to 50,000. The active energy ray-curable resin composition according to claim 1, wherein the polyester (meth) acrylate compound (B) is a polyester polyol (b1) having a number average molecular weight (Mn) in a range of 500 to 6,000. , A compound obtained by reacting polyisocyanate compound (b2) and a hydroxyl group-containing (meth) acrylate compound (b3) as essential components. The active energy ray-curable resin composition according to claim 1, wherein the (meth) acrylfluorenyl group concentration of the polyester (meth) acrylate compound (B) is in a range of 0.04 to 0.5 mmol / g. For example, the active energy ray-curable resin composition of claim 1, which contains the polyester resin (A) and the polyester (meth) acrylate compound (B) such that the mass ratio of the two is [(A) / (B)] The range is 20/80 to 80/20. For example, the active energy ray-curable resin composition of claim 1, wherein the photoinitiator (C) is 0.01 to 10 parts by mass relative to 100 parts by mass of the polyester (meth) acrylate compound (B). range. The active energy ray-curable resin composition according to claim 1, further comprising the polyester resin (A), the polyester (meth) acrylate compound (B), and the photoinitiator (C). Radical polymerizable monomer (D). The active energy ray-curable resin composition according to claim 12, comprising the polyester resin (A) and the polyester (meth) acrylate compound (B), and a monomer (D) having the radical polymerizability ) So that the mass ratio [[(A) + (B)] / (D)] of the two 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 laminated film obtained by using an adhesive as claimed in claim 14. A cured product obtained by curing the active energy ray-curable resin composition according to any one of claims 1 to 13.