JP2005048095A - Active-energy-ray-hardenable resin composition for adhesion of information recording medium - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an active-energy-ray-hardenable resin composition for adhesion of information recording media which ensures reliability of a disk for a long period and causes no change of the appearance of an adhesive-hardened layer even in cases involving use of gold, silver or silicon nitride in the information recording layer. <P>SOLUTION: The composition is for adhesion of information recording media consisting of (a) two boards having an information recording layer or (b) one board having an information recording layer and a resin layer, stuck together. The composition consists of a resin composition comprising (1) an epoxy (meth)acrylate obtained by reacting (A) a hydroxy-containing (meth)acrylate with (B) an acid anhydride containing one acid anhydride group to form an ester and reacting the ester with (C) a difunctional or higher epoxy resin, (2) a (meth)acryloyl-containing compound other than (1) and (3) an photopolymerization initiator. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an information recording medium comprising a resin composition comprising an epoxy (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylate, an acid anhydride and an epoxy resin, an acryloyl group-containing compound and a photopolymerization initiator. Regarding the active energy ray-curable resin composition for adhesion, the resin composition is used when two substrates are bonded together or when a cured product layer is formed on the back surface of one substrate having an information recording layer, The adhesiveness is good, and the cured product of the adhesive is excellent in durability.

Among information recording media, in particular, digital versatile (or digital video) discs (DVDs) are made by a method of bonding two substrates, of which at least one substrate has an information recording layer. Yes.
Further, there are cases where two substrates having an information recording layer are used without forming a substrate having an information recording layer and a cured product having a film thickness of 50 to 120 μm.
In recent years, the use of an active energy ray-curable resin composition as an adhesive for DVD has been studied (for example, JP-A-9-31416, JP-A-10-245467, etc.). Conventionally, aluminum has been used for the information recording layer, and an active energy ray-curable adhesive corresponding to the aluminum has been studied, and has sufficient adhesive force to the polycarbonate substrate and the aluminum layer. As the recording capacity increases, the type of evaporated metal shifts to gold, silver, and silicon nitride. With conventional UV curable adhesives, the adhesion to gold, silver, and silicon nitride decreases, and long-term reliability There is a problem that the performance decreases.

JP-A-9-31416 JP-A-10-245467 Japanese Patent Application No. 2002-19183

  The object of the present invention is to secure the reliability of the disc over a long period of time even when gold, silver or silicon nitride is used for the information recording layer, and to adhere the information recording medium so that the appearance of the cured adhesive layer does not change. An active energy ray-curable resin composition for use is provided.

  As a result of intensive studies to solve the above problems, the present inventor was obtained by reacting a hydroxyl group-containing (meth) acrylate, an acid anhydride, and an epoxy resin previously proposed in Japanese Patent Application No. 2002-19183. The present inventors have found that the above problems can be solved by using a resin composition comprising an epoxy (meth) acrylate, an acryloyl group-containing compound and a photopolymerization initiator, and have reached the present invention.

That is, the first of the present invention is an active energy ray-curable resin composition for adhering an information recording medium, which is obtained by bonding two substrates having an information recording layer, and includes (1) a hydroxy group-containing (meth) acrylate. An epoxy (meth) acrylate obtained by reacting (A) with an acid anhydride (B) containing one acid anhydride group to form an ester and then reacting with a bifunctional or higher epoxy resin (C), (2) (meth) acryloyl group-containing compound [excluding (1)], (3) an active energy ray-curable adhesive for information recording media, comprising a resin composition containing a photopolymerization initiator A resin composition is provided.
A second aspect of the present invention is an active energy ray-curable resin composition for adhering an information recording medium comprising a single substrate having an information recording layer and a resin layer, wherein (1) a hydroxy group-containing (meth) acrylate (A ) And an acid anhydride (B) containing one acid anhydride group to form an ester, and then an epoxy (meth) acrylate obtained by reacting with a bifunctional or higher epoxy resin (C), (2 (2) An active energy ray-curable resin composition for adhesion to an information recording medium, comprising a (meth) acryloyl group-containing compound [except for (1)] and (3) a photopolymerization initiator.
In the third aspect of the present invention, the hydroxyl group-containing (meth) acrylate (A) is hydroxyalkyl (2 to 6 carbon atoms) (meth) acrylate, polyalkylene (2 to 6 carbon atoms) glycol mono (meth) acrylate, glycerol Mono or di (meth) acrylate, glycerol methacrylate acrylate, 2- (meth) acryloylethyl-2-hydroxyethyl phthalate, pentaerythritol tri (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, of these (meth) acrylates The active energy for adhering to an information recording medium according to the invention 1 or 2, which is at least one selected from a lactone (carbon number 4 to 8) modified product, an alkylene (carbon number 2 to 6) oxide modified product, or a mixture thereof. Wire-curing type It provides fat compositions.
According to a fourth aspect of the present invention, there is provided the active energy ray-curable resin composition for bonding an information recording medium according to the first or second aspect, wherein the acid anhydride is phthalic anhydride.
A fifth aspect of the present invention is the information recording according to any one of the first to fourth aspects, wherein the bifunctional or higher functional epoxy resin is at least one selected from a bisphenol type epoxy resin, a novolac type epoxy resin, and an alicyclic epoxy resin. An active energy ray-curable resin composition for medium adhesion is provided.
A sixth aspect of the present invention is the active energy ray-curable resin composition for adhering to an information recording medium according to the first aspect, wherein the (meth) acryloyl group-containing compound is neopentyl glycol diacrylate and / or dimethylol dicyclopentane diacrylate. Offer things.
A seventh aspect of the present invention provides the active energy ray-curable resin composition for adhering an information recording medium according to any one of the first to sixth aspects, wherein the information recording medium is a digital versatile disk (DVD).
An eighth aspect of the present invention is the active energy ray curing for bonding an information recording medium according to any one of the first to seventh aspects, wherein the light transmittance at a wavelength of 750 nm or less is 90% or more in a cured product having a film thickness of 50 to 120 μm. A mold resin composition is provided.

  The active energy ray-curable resin composition for adhering information recording media of the present invention is excellent in adhesiveness even when gold, silver or silicon nitride is used for the information recording layer, and the cured product of the obtained adhesive resin composition is bonded. Excellent in durability, durability and light transmittance.

Hereinafter, the present invention will be described in detail.
Examples of the hydroxy group-containing (meth) acrylate (A) used in the present invention include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxy Hydroxyalkyl (2 to 12 carbon atoms) (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono, which may have a substituent on the alkyl group such as butyl (meth) acrylate and phenoxyhydroxypropyl (meth) acrylate Polyalkylenes (2 to 6 carbon atoms) glycol mono (meth) acrylate, glycerol mono (meth) acrylate, glycerol methacrylate acrylate, 2- (meth) acryloylethyl-2-hydride such as (meth) acrylate Xylethyl phthalate, pentaerythritol tri (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate or lactone (4 to 8 carbon atoms) modified product of the above compound, alkylene such as ethylene oxide or propylene oxide (2 to 6 carbon atoms) Examples include oxide-modified products. Among these, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and polypropylene glycol mono (meth) acrylate are preferable.
Examples of lactone-modified products include those obtained by adding 0.3 to 10 moles of lactone such as ε-caprolactone and γ-butyrolactone to the hydroxyl group of hydroxyalkyl (2 to 6 carbon atoms) (meth) acrylate group. It is done. Commercially available products include Daicel Chemical Industries' Plaxel FA or Plaxel FM [2-hydroxyethyl acrylate or methacrylate added with 0.3 to 10 mol of ε-caprolactone] series. It is particularly preferable to use it when flexibility is required.
Examples of the modified alkyl oxide include those obtained by adding 0.5 to 20 moles of ethylene oxide, propylene oxide or the like to the hydroxyl group of hydroxyalkyl (2 to 6 carbon atoms) (meth) acrylate group. As commercial products, there are Bremer PE, AE, PP, AP, PEP and AEP series manufactured by Nippon Oil & Fats Co., Ltd.

The acid anhydride (B) contains one acid anhydride group. For example, phthalic anhydride, maleic anhydride, succinic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, tetrahydro Examples thereof include succinic anhydride, tetrahydrophthalic anhydride, dodecenyl succinic anhydride, dodecenyl phthalic anhydride, octenyl succinic anhydride, octenyl phthalic anhydride and the like. Of these, phthalic anhydride, maleic anhydride, and succinic anhydride are preferred.
The epoxy resin (C) is a bifunctional or higher functional epoxy resin, for example, bisphenol type epoxy resin such as bisphenol A type epoxy resin, bisphenol S type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac. Type epoxy resin and other novolak type epoxy resins, 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxy-cyclohexylmethyl-3,4-epoxy Examples include alicyclic epoxy resins such as cyclohexanecarboxylate.

As a method for producing an epoxy (meth) acrylate that is a main resin raw material of the active energy ray-curable resin composition for bonding an information recording medium of the present invention, a hydroxyl group and an acid anhydride group of the hydroxy group-containing acrylate (A) are used. There is no particular limitation as long as it is a method in which an acid anhydride of one acid anhydride (B) is reacted to form an ester and then reacted with an epoxy group in the epoxy resin (C).
The reaction ratio of the hydroxyl group-containing (meth) acrylate (A), acid anhydride (B), and epoxy resin (C) is such that (A) is 0.1 to 3 mol, preferably 0, per 1 mol of (C). .2 to 2.5 mol, and (B) is 0.1 to 3 mol, preferably 0.2 to 2.5 mol. When (A) and (B) are less than 0.1 mol, the obtained epoxy (meth) acrylate cannot exhibit sufficient curability. Here, the molar ratio of (A) to (B) is 0.95: 1 to 1: 0.95, preferably 1: 1.
The epoxy (meth) acrylate of component (1) in the active energy ray-curable resin composition for adhering information recording media of the present invention obtained by reacting at such a ratio usually has a (meth) acryloyl group mainly at the terminal. Although it is a di (meth) acrylate having an epoxy group, it is possible to obtain a poly (meth) acrylate having an epoxy group by using a tri- or higher functional epoxy compound as the component (C) as a raw material.

In order to prevent the polymerization of the (meth) acryloyl group of the hydroxyl group-containing (meth) acrylate (A), the above reaction is carried out by hydroquinone, hydroquinone monomethyl ether, phenothiazine pt-butylcatechol, 2,5-di-t- Butyl hydroquinone, mono-t-butyl hydroquinone, p-benzoquinone, naphthoquinone, 2,5-diphenyl-p-benzoquinone, di-t-butyl-p-cresol, 2,5-di-t-butyl-4-methylphenol It is preferable to carry out in the presence of a polymerization inhibitor.
The amount of these polymerization inhibitors is 1 to 10,000 ppm (hereinafter, based on weight), preferably 100 to 5000 ppm, and more preferably 200 to 1000 ppm with respect to the epoxy (meth) acrylate to be produced. If the amount of the polymerization inhibitor is less than 1 ppm relative to the epoxy (meth) acrylate, a sufficient polymerization inhibition effect may not be obtained, and if it exceeds 10,000 ppm, the physical properties of the product may be adversely affected.
For the same reason, this reaction is preferably performed in a molecular oxygen-containing gas atmosphere. The oxygen concentration is appropriately selected in consideration of safety.

In this reaction [reaction between (A) and (B) and then reaction with (C)], this reaction is preferably carried out using a catalyst in order to obtain a sufficient reaction rate. Examples of the catalyst include organic phosphine compounds such as triphenylphosphine, tertiary amines such as triethylamine and benzyldimethylamine, quaternary ammonium salts such as trimethylammonium chloride, triethylbenzylammonium chloride and trimethylammonium bromide, and 2-methylimidazole. , Imidazole compounds such as 2-ethyl-4-methylimidazole, organometallic salts such as chromium octenoate, cobalt octenoate, and chromium naphthenate. The addition amount of the catalyst is 0.01 to 5.0% with respect to the epoxy (meth) acrylate. Preferably it is 0.05 to 2.0%.
If it is less than 0.01%, a sufficient reaction rate may not be obtained. If it is added more than 5.0%, the physical properties of the product may be adversely affected.

  The reaction temperature is preferably 60 to 130 ° C. for both the reaction of (A) and (B) and then the reaction of (C). More preferably, it is 80-120 degreeC.

The (meth) acryloyl group-containing compound of component (2) in the active energy ray-curable resin composition for bonding an information recording medium of the present invention is not particularly limited, and a compound containing a known (meth) acryloyl group may be used. Can be used. Examples of the (meth) acryloyl group-containing compound include various (meth) acrylates such as phenoxyethyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, and cyclohexyl (meth) acrylate, and 2-hydroxyethyl acrylate. Monofunctional monomers such as (meth) acrylates having a hydroxyl group such as 2-hydroxyethyl acrylate and caprolactone, dicyclopentenyloxyethyl acrylate, acryloylmorpholine, 1,6-hexanediol di (meth) acrylate, tripropylene Glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate , Tri (meth) acrylate of 3 mol propylene oxide adduct of trimethylolpropane, tri (meth) acrylate of 6 mol propylene oxide adduct of trimethylolpropane, glycerin propoxytri (meth) acrylate, dipentaerythritol hexa (meth) ) And polyfunctional monomers such as hexa (meth) acrylate of a modified caprolactone of dipentaerythritol. Representative oligomers include urethane (meth) acrylate, epoxy (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, acrylic group-containing acrylic polymerizable oligomer, unsaturated polyester, and the like. .
The amount of the component (2) (meth) acryloyl group-containing compound is 1-1000 parts by weight, preferably 1-500 parts by weight, more preferably 100 parts by weight of the component (1) epoxy (meth) acrylate. Is 1 to 100 parts by weight. If the amount is less than 1 part by weight, there is no point in adding it as a solvent.

  As the photopolymerization initiator of component (3) in the active energy ray-curable resin composition for adhering information recording media of the present invention, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane- 1-one, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropane-1- ON, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1, benzoin, benzoin methyl ether Benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, Zoin phenyl ether, benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3'-dimethyl- 4-methoxybenzophenone, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone Son, 2,4-diisopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, methylphenylglyoxylate, benzyl, camphorquinone and the like. The blending amount of the photopolymerization initiator is 1 to 10% by weight, preferably 1 to 5% by weight, and more preferably about 3% by weight with respect to the whole composition. If it is less than 1% by weight, the curing rate is slow, and conversely if used in an amount exceeding 10% by weight, the curing rate is not improved, and the physical properties of the cured product are impaired.

The active energy ray-curable resin composition for bonding an information recording medium of the present invention is adjusted so as to be liquid at room temperature to 40 ° C. In this adjustment, it is preferable not to use a solvent, and even if it is used, it is preferable to keep it as small as possible. When the resin composition is applied with a spin coater, the viscosity is preferably adjusted to 20 to 2500 mPa · s, and when the film is relatively thick, the viscosity is 100 to 2500 mPa · s. It is good to adjust to.
In addition to spine coating, it can also be used by coating methods such as screen printing.

  In the active energy ray-curable resin composition for adhesion of information recording medium of the present invention, if necessary, as other additives, thermal polymerization inhibitors, hindered phenols, hindered amines, phosphine and other antioxidants, plasticizers Silane coupling agents such as epoxy silane, mercapto silane, (meth) acryl silane, etc. can be blended for the purpose of improving various properties.

The active energy ray used for curing the active energy ray-curable resin composition for bonding an information recording medium of the present invention includes ultraviolet rays and electron beams, and ultraviolet rays are preferably used. A high pressure mercury lamp, an ultrahigh pressure mercury lamp, a carbon arc lamp, a xenon lamp, a metal halide lamp, or the like is used as a light source when performing ultraviolet irradiation. The irradiation time varies depending on the type of the light source, the distance between the light source and the coating surface, and other conditions, but is several tens of seconds at most, and usually several seconds. After the ultraviolet irradiation, heating can be performed as necessary to complete the curing. In the case of electron beam irradiation, it is preferable to use an electron beam having an energy in the range of 50 to 1,000 KeV and set the irradiation amount to 2 to 5 Mrad. Usually, an irradiation source having a lamp output of about 80 to 300 W / cm is used. The thickness of the cured adhesive is usually about 50 to 300 μm.
As an ultraviolet irradiation method for curing the active energy ray-curable resin composition for bonding an information recording medium of the present invention, in addition to a generally used continuous irradiation method, once in a short time of the order of μsec to msec. Irradiation may be performed at once, or may be performed by a flash irradiation method in which irradiation of the order of μsec to msec is repeated several times.
The cured layer of the active energy ray-curable resin composition for bonding an information recording medium of the present invention is particularly excellent in adhesion to vapor deposited metal and reliability of an information recording medium such as a DVD over a long period of time.
As an information recording medium to which the active energy ray-curable resin composition for bonding an information recording medium of the present invention can be applied, there is a Blu-ray system in addition to a DVD, but in particular, gold, silver, silicon nitride, etc. as a metal on a substrate. It is preferably applied to a DVD used by vapor deposition.

(Example)
EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.
The disk was manufactured and the adhesion and long-term reliability tests were performed as follows.
Fabrication method 1: substrate (a) in which aluminum is laminated on a polycarbonate disc by sputtering, substrate (b) in which gold is similarly laminated, substrate (c) in which silver is laminated, substrate (d) in which silicon nitride is laminated The active energy curable resin composition prepared on the substrate (a) was applied with a spin coater so as to have a film thickness of 10 microns, and (a) to (d) were bonded to each other, and a metal halide lamp was used. And then cured by irradiating with an irradiation amount of 500 mJ / cm ² , disk 1 (a and a combined), disk 2 (a and b combined), disk 3 (a and c bonded) Disc 4) (a product obtained by bonding a and d).
Moreover, the active energy ray-curable resin composition prepared on each of the substrates (b) to (d) was applied with a screen machine so as to have a film thickness of 100 microns, and a dose of 500 mJ / cm ² was applied using a metal halide lamp. Irradiated and cured to obtain disks 5-7.

Test Method 1: Adhesion Test With respect to the disks 1 to 4, the end surfaces of the obtained disks were slightly cut, the two substrates were peeled off by hand, and the peeled state was observed. About the disks 5-7, the cellophane peeling test was done to the obtained coating film, and the mode that it peeled was observed.
Test Method 2: Durability Test The obtained disk was put in a high temperature and high humidity test (temperature 80 ° C., humidity 85%, 2000 hours), and the cured layer of the active energy ray-curable resin composition and the black of the laminated metal layer were tested. Changes and turbidity were visually observed.
Test Method 3: Transmittance Test A test piece was prepared by laminating a resin having a film thickness of 50 μm with two white slide glasses and using a metal halide lamp to irradiate with an irradiation dose of 500 mJ / cm ² . The obtained test piece was measured for light transmittance (%) at a wavelength of 200 to 900 nm with an ultraviolet-visible light spectrometer, and values at 380, 405, and 650 nm were shown as representative values. The blank was white slide glass only.
○: The transmittance is 90% or more, Δ: the transmittance is 70 to 89%, and x: the transmittance is less than 70%.

Abbreviations and the like of those used as raw materials for the active energy ray-curable resin composition are shown below.
PLACCEL FA1: manufactured by Daicel Chemical Industries, 2-hydroxyethyl acrylate modified with 1 mol of ε-caprolactone PLACCEL FA2D: manufactured by Daicel Chemical Industries, 2-hydroxyethyl acrylate modified with 2 mol of ε-caprolactone PLACCEL FA3: manufactured by Daicel Chemical Industries, Ltd. 2-hydroxyethyl acrylate modified with 3 mol of ε-caprolactone Epicoat 828EL: manufactured by Japan Epoxy Resin, bisphenol A diglycidyl ether (epoxy equivalents 184 to 194)
AP400: manufactured by NOF, polypropylene glycol monoacrylate (OH value: about 134 KOHmg / g)
AP800: Polypropylene glycol monoacrylate (OH value: about 67 KOHmg / g), manufactured by NOF

(Example 1)
(1) 30 parts by weight of an epoxy acrylate composed of ε-caprolactone-modified 2-hydroxyethyl acrylate (Placcel FA1 manufactured by Daicel Chemical Industries, Ltd.) (2 mol), phthalic anhydride (2 mol) and Epicoat 828EL (1 mol); 2) ε-caprolactone-modified 2-hydroxyethyl acrylate (Placcel FA2D manufactured by Daicel Chemical Industries, Ltd.) 20 parts by weight, (3) Neopentyl glycol diacrylate 30 parts by weight, (4) dimethylol dicyclopentane diacrylate 20 parts by weight (5) 3 parts by weight of 1-hydroxycyclohexyl phenyl ketone was mixed to prepare an active energy ray-curable resin composition.
Using this composition, a disc having a substrate attached thereto by Production Method 1 was produced. In each disk, when the bonded disks were peeled off manually by Test Method 1, all the disks 1 to 4 were peeled off from the interface between the polycarbonate substrate and the laminated metal, and the active energy ray-curable resin composition. The cured product and the laminated metal were bonded very firmly. As a result of performing a cellophane peel test on the disks 5 to 7, the cells were bonded very firmly.
In addition, as a result of performing a durability test on each manufactured disk by the test method 2, no change was observed in the appearance of all the disks 1 to 7, and the transmittance was good and the transmittance was 90% or more. there were.

(Example 2)
(1) 30 parts by weight of an epoxy acrylate comprising ε-caprolactone-modified 2-hydroxyethyl acrylate (Placcel FA3 manufactured by Daicel Chemical Industries, Ltd.) (2 mol), phthalic anhydride (2 mol) and Epicoat 828EL (1 mol), 2) ε-caprolactone-modified 2-hydroxyethyl acrylate (Placcel FA2D) 20 parts by weight, (3) neopentyl glycol diacrylate 30 parts by weight, (4) dimethylol dicyclopentane diacrylate 20 parts by weight, (5) 1- The active energy ray-curable resin composition obtained by mixing 3 parts by weight of hydroxycyclohexyl phenyl ketone was tested in the same manner as in Example 1. As a result, the adhesive properties of all of the disks 1 to 4 were polycarbonate. Peel from the interface between the substrate and each laminated metal, The metal is laminated with the cured product of the sexual energy ray-curable resin composition was very strongly bonded. As a result of performing a cellophane peel test on the disks 5 to 7, the cells were bonded very firmly.
Further, the durability was good for all the disks 1 to 7, and the transmittance was also good at 90% or more.

(Example 3)
(1) 30 parts by weight of epoxy acrylate composed of 2-hydroxypropyl acrylate (2 mol), phthalic anhydride (2 mol) and Epicoat 828EL (1 mol), (2) ε-caprolactone-modified 2-hydroxyethyl acrylate (Daicel Chemical) 20 parts by weight of Plaxel FA2D manufactured by Kogyo Co., Ltd., (3) 30 parts by weight of neopentyl glycol diacrylate, (4) 20 parts by weight of dimethylol dicyclopentane diacrylate, (5) 3 parts by weight of 1-hydroxycyclohexyl phenyl ketone The resulting active energy ray-curable resin composition was mixed and tested in the same manner as in Example 1. As a result, the adhesive properties of all the disks 1 to 4 were measured with the polycarbonate substrate and the respective laminated metals. Cured product of active energy ray-curable resin composition And the laminated metal were very firmly bonded. As a result of performing a cellophane peel test on the disks 5 to 7, the cells were bonded very firmly. Further, the durability was good for all the disks 1 to 7, and the transmittance was also good at 90% or more.

(Example 4)
(1) 30 parts by weight of an epoxy acrylate comprising propylene glycol monoacrylate (AP400) (2 mol), phthalic anhydride (2 mol) and Epicoat 828EL (1 mol), (2) ε-caprolactone-modified 2-hydroxyethyl acrylate ( PLACCEL FA2D) 20 parts by weight, (3) neopentyl glycol diacrylate 30 parts by weight, (4) dimethylol dicyclopentane diacrylate 20 parts by weight, (5) 1-hydroxycyclohexyl phenyl ketone 3 parts by weight, The obtained active energy ray-curable resin composition was tested in the same manner as in Example 1. As a result, the adhesive property was peeled off from the interface between the polycarbonate substrate and each laminated metal in all the disks 1 to 4. And laminated with a cured product of an active energy ray-curable resin composition The metal was very firmly bonded. As a result of performing a cellophane peel test on the disks 5 to 7, the cells were bonded very firmly. Further, the durability was good for all the disks 1 to 7, and the transmittance was also good at 90% or more.

(Example 5)
(1) 30 parts by weight of an epoxy acrylate composed of propylene glycol monoacrylate (AP800) (2 mol), phthalic anhydride (2 mol) and Epicoat 828EL (1 mol), (2) ε-caprolactone-modified 2-hydroxyethyl acrylate ( PLACCEL FA2D) 20 parts by weight, (3) neopentyl glycol diacrylate 30 parts by weight, (4) dimethylol dicyclopentane diacrylate 20 parts by weight, (5) 1-hydroxycyclohexyl phenyl ketone 3 parts by weight, The obtained active energy ray-curable resin composition was tested in the same manner as in Example 1. As a result, the adhesive property was peeled off from the interface between the polycarbonate substrate and each laminated metal in all the disks 1 to 4. And laminated with a cured product of an active energy ray-curable resin composition The metal was very firmly bonded. As a result of performing a cellophane peel test on the disks 5 to 7, the cells were bonded very firmly. Further, the durability was good for all the disks 1 to 7, and the transmittance was also good at 90% or more.

(Comparative Example 1)
(1) 30 parts by weight of an epoxy acrylate composed of acrylic acid (2 moles) and Epicoat 828EL (1 mole), (2) 20 parts by weight of ε-caprolactone-modified 2-hydroxyethyl acrylate (Placcel FA2D), (3) neopentyl glycol 30 parts by weight of diacrylate, (4) 20 parts by weight of dimethylol dicyclopentane diacrylate, (5) 3 parts by weight of 1-hydroxycyclohexyl phenyl ketone The above active energy obtained by mixing (1) to (5) above As a result of testing the linear curable resin composition in the same manner as in Example 1, the adhesive was peeled off from the interface between the polycarbonate substrate and each laminated metal in the disk 1, and the active energy ray curable resin composition The cured product and the laminated metal were bonded very firmly. However, in the disks 2 to 7, it peels off at the interface between the laminated metal other than aluminum and the cured product of the active energy ray curable resin composition, and the laminated metal and the cured product of the active energy ray curable resin composition Adhesiveness was insufficient. Durability was good for all the disks 1-7, but the transmittance at 308,405 nm was insufficient.

(Comparative Example 2)
(1) Polytetramethylene glycol (molecular weight 1000) (1 mol), isophorone diisocyanate (2 mol), urethane acrylate consisting of 2-hydroxyethyl acrylate (2 mol), 30 parts by weight, (2) ε-caprolactone modified 2-hydroxy 20 parts by weight of ethyl acrylate (Placcel FA2D), (3) 30 parts by weight of neopentyl glycol diacrylate, (4) 20 parts by weight of dimethylol dicyclopentane diacrylate, (5) 3 parts by weight of 1-hydroxycyclohexyl phenyl ketone As a result of testing the obtained active energy ray-curable resin composition in the same manner as in Example 1, the adhesiveness of the disc 1 was peeled off from the interface between the polycarbonate substrate and each laminated metal. , Product and cured product of active energy ray curable resin composition The layered metal was very firmly bonded. However, in the disks 2 to 7, it peels off at the interface between the laminated metal other than aluminum and the cured product of the active energy ray curable resin composition, and the laminated metal and the cured product of the active energy ray curable resin composition Adhesiveness was insufficient. In terms of durability, the metal laminated on all the disks 1 to 7 turned black, and the transmittance at 308 and 405 nm was insufficient.
Table 1 summarizes the evaluation results.

  From the above results, the cured product using epoxy acrylate having a skeleton derived from an acid anhydride in the molecule, such as the active energy ray-curable resin composition for bonding an information recording medium of the present invention, has adhesiveness and durability. The cured product of the adhesive in the comparative example that does not have a skeleton derived from an acid anhydride in the molecule, while having excellent properties and light transmittance in the cured layer is adhesive and / or durable, and further cured It is clear that the light transmission in the layer is poor.

Claims (8)

  An active energy ray-curable resin composition for adhering an information recording medium obtained by bonding two substrates having an information recording layer, wherein (1) a hydroxy group-containing (meth) acrylate (A) and an acid anhydride group 1 An epoxy (meth) acrylate obtained by reacting an acid anhydride (B) containing a single group to form an ester and then reacting with a bifunctional or higher epoxy resin (C), containing (2) (meth) acryloyl group An active energy ray-curable resin composition for adhesion to an information recording medium, comprising a compound [excluding (1)] and (3) a resin composition containing a photopolymerization initiator.   An active energy ray-curable resin composition for adhering an information recording medium comprising a single substrate having an information recording layer and a resin layer, wherein (1) a hydroxy group-containing (meth) acrylate (A) and an acid anhydride group 1 An epoxy (meth) acrylate obtained by reacting an acid anhydride (B) containing a single group to form an ester and then reacting with a bifunctional or higher epoxy resin (C), containing (2) (meth) acryloyl group An active energy ray-curable resin composition for adhesion to an information recording medium, comprising a compound [excluding (1)], and (3) a photopolymerization initiator.   Hydroxyl group-containing (meth) acrylate (A) is hydroxyalkyl (2 to 6 carbon atoms) (meth) acrylate, polyalkylene (2 to 6 carbon atoms) glycol mono (meth) acrylate, glycerol mono or di (meth) acrylate Glycerol methacrylate acrylate, 2- (meth) acryloylethyl-2-hydroxyethyl phthalate, pentaerythritol tri (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, lactones of these (meth) acrylates (4 to 8 carbon atoms) 3. The active energy ray-curable resin composition for adhering to an information recording medium according to claim 1, which is at least one selected from a modified product, an alkylene (2 to 6 carbon atoms) oxide modified product, or a mixture thereof.   The active energy ray-curable resin composition for bonding an information recording medium according to claim 1 or 2, wherein the acid anhydride is phthalic anhydride.   The active energy ray curing for information recording medium adhesion according to any one of claims 1 to 4, wherein the bifunctional or higher functional epoxy resin is at least one selected from a bisphenol type epoxy resin, a novolac type epoxy resin, and an alicyclic epoxy resin. Mold resin composition.   The active energy ray-curable resin composition for adhesion to an information recording medium according to claim 1, wherein the (meth) acryloyl group-containing compound is neopentyl glycol diacrylate and / or dimethylol dicyclopentane diacrylate.   The active energy ray-curable resin composition for adhering to an information recording medium according to any one of claims 1 to 6, wherein the information recording medium is a digital versatile disk (DVD).   8. The active energy ray-curable resin composition for adhering to an information recording medium according to claim 1, wherein the cured product having a thickness of 50 to 120 μm has a light transmittance of 90% or more at a wavelength of 750 nm or less.