JP6874877B2 - Active energy ray-polymerizable adhesive for optics and laminate for optics - Google Patents

Description

The present invention relates to an active energy ray-polymerizable adhesive for optics and a laminate for optics.

In optical applications such as display devices such as displays, active energy ray-polymerizable adhesives have a high polymerization rate and can generally be used without a solvent, so that they have excellent workability and the energy required for polymerization is extremely low. It is widely used because it has excellent characteristics. As the active energy ray-polymerizable adhesive, a radically polymerizable active energy ray-polymerizable adhesive and a cationically polymerizable active energy ray-polymerizable adhesive are generally known.

Display devices such as displays usually have various films depending on the application, such as an antireflection film for preventing reflection from an external light source and a protective film (protective film) for preventing scratches on the surface of the display device. For example, in a liquid crystal cell member constituting a liquid crystal display (LCD), a polarizing plate and a retardation film are laminated.

Further, the flat panel display (FPD) is not only used as a display device, but may also be used as an input device by providing a touch panel function on the surface thereof. A protective film, an antireflection film, an ITO vapor-deposited resin film, and the like are also used for the touch panel.

In addition, a backlight system that illuminates the liquid crystal layer from the back surface to emit light has become widespread in the display device, and a backlight unit such as an edge light type or a direct type is provided on the lower surface side of the liquid crystal layer. The edge light type backlight unit is basically a linear lamp as a light source, a square plate-shaped light guide plate arranged along the end of the lamp, and arranged on the surface side of the light guide plate. It is provided with a light diffusing sheet to be formed and a prism sheet arranged on the surface side of the light diffusing sheet. Recently, as a light source, a light emitting diode (LED) having excellent color reproducibility and power saving has been used instead of a cold electrode tube (CCFL), so that the demand for heat resistance and dimensional stability is increasing. It's coming.

By the way, display devices have come to be used in various environments as their applications expand. For example, in-vehicle liquid crystal display devices such as car navigation systems are exposed to a harsh high-temperature atmosphere in the summer, and therefore require adhesive strength at high temperatures. Furthermore, in cold regions in winter, adhesive strength at low temperatures is required.

As an adhesive used for a display device, an adhesive containing a carboxyl group-containing vinyl polymer and a vinyl monomer (Patent Document 1) is disclosed.

Patent Document 2 discloses an active energy ray adhesive containing an alicyclic epoxy resin, a polyol having a number average molecular weight of 400 or more, and an active energy ray sensitive catalyst.

Japanese Unexamined Patent Publication No. 2015-10763 JP-A-2007-224235

However, the conventional display device using the active energy ray adhesive has insufficient adhesive force in a wide temperature range from high temperature to low temperature for in-vehicle use, and particularly has insufficient adhesive force at low temperature.

An object of the present invention to be solved is to provide an active energy ray adhesive for optics having excellent adhesive strength in a wide temperature range from high temperature to low temperature.

The present inventors have completed the present invention as a result of diligent studies in order to solve the above problems.
That is, the present invention has a (meth) acrylate monomer (A) having a heterocycle having a molecular weight of less than 500 (excluding acryloylmorpholine) and a (meth) acrylate monomer (B) having a hydroxyl group having a molecular weight of less than 500 (however, however). , (Excluding the (meth) acrylate monomer (A) having a heterocycle) and the (meth) acrylate monomer (C) having a ring other than the heterocycle having a molecular weight of less than 500 (however, having a heterocycle having a molecular weight of less than 500 (excluding) (Excluding the meta) acrylate monomer (A) and the (meth) acrylate monomer (B) having a hydroxyl group), the heterocycle is selected from the group consisting of sulfur, oxygen and nitrogen as atoms constituting the ring. The present invention relates to an optical active energy ray-polymerizable adhesive containing one or more heteroatoms.

Further, the present invention further comprises a polyurethane-based oligomer having a (meth) acryloyl group (D1), a polyester-based oligomer having a (meth) acryloyl group (D2), and an epoxy-based oligomer having a (meth) acryloyl group (D3). The above-mentioned active energy ray-polymerizable adhesive for optics containing one or more oligomers selected from the above group.
Regarding.

Further, in the present invention, the (meth) acrylate monomer (A) having a heterocycle is 5 to 70% by mass and the (meth) acrylate monomer (B) having a hydroxyl group is 20 to 80 in the active energy ray-polymerizable adhesive for optics. The above-mentioned optical active energy ray-polymerizable adhesive containing 5 to 50% by mass of a (meth) acrylate monomer (C) having a ring structure other than a heterocycle.
Regarding.

The present invention also relates to an optical laminate comprising a first base material, a resin layer which is a cured product of the above-mentioned active energy ray-polymerizable adhesive for optics, and a second base material.

INDUSTRIAL APPLICABILITY According to the present invention, it has become possible to provide an active energy ray-polymerizable adhesive for optics having excellent adhesive strength in a wide temperature range from high temperature to low temperature.

Hereinafter, embodiments of the present invention will be described.
<Active energy ray-polymerizable adhesive for optics>
The active energy ray-polymerizable adhesive for optics of the present invention (hereinafter, may be simply referred to as "adhesive") has a (meth) acrylate monomer having a heterocycle having a molecular weight of less than 500 (where, acryloyl). (Excluding morpholin), (meth) acrylate monomer (B) having a hydroxyl group having a molecular weight less than 500 (excluding (meth) acrylate monomer (A) having a heterocycle), and a ring other than a heterocyclic ring having a molecular weight less than 500. (Excluding the (meth) acrylate monomer (A) having a heterocycle having a molecular weight of less than 500 and the (meth) acrylate monomer (B) having a hydroxyl group) having the (meth) acrylate monomer (C). Is characterized by containing two or more heteroatoms selected from the group consisting of sulfur, oxygen and nitrogen as the atoms constituting the ring.

Here, the "active energy ray" is an energy ray in a broad sense that can provide the energy required for activation to cause a chemical reaction, including ultraviolet rays, visible rays, infrared rays, electron beams (EB), and radiation. means. In the active energy ray-polymerizable adhesive of the present invention, the polymerization reaction proceeds by irradiation with the above-mentioned active energy rays to form a cured product such as a resin layer.

In addition, in this specification, when it is described as "(meth) acryloyl", "(meth) acrylic acid", "(meth) acrylate", "(meth) acryloyloxy", and "(meth) allyl", Unless otherwise noted, "acryloyl and / or methacrylic acid", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", "acryloyloxy and / or methacryloyloxy", and "allyl and /", respectively. Or it shall mean "methacrylic".

<(Meta) acrylate monomer (A) having a heterocycle having a molecular weight of less than 500>
The (meth) acrylate monomer (A) having a heterocycle having a molecular weight of less than 500 (hereinafter, also referred to as compound (A)) is a group consisting of sulfur, oxygen and nitrogen as atoms (ring member atoms) constituting the ring. Refers to a compound having a heterocycle containing two or more heteroatoms selected from the above and a (meth) acryloyl group.
By including the compound (A) in the adhesive, a hydrogen bond is formed between the heteroatom of the heterocycle and a functional group such as a hydroxyl group on the surface of the base material, and the adhesive strength at room temperature and low temperature is improved. Further, the annular structure improves the cohesive force at high temperature and improves the adhesive force at high temperature.

Examples of the heterocycle containing two or more heteroatoms selected from the group consisting of sulfur, oxygen and nitrogen as ring member atoms include a heterocycle having two or more sulfur atoms such as a dithiolane ring and a dithiol ring, and a carbonate ring. A heterocycle having two or more oxygen atoms such as a dioxolane ring and a dioxane ring, an isocyanul ring, an imidazole ring, a pyrazole ring, a pyrazine ring, a pyrimidine ring, a piperazin ring and the like having two or more nitrogen atoms, an oxazole ring. , Isooxazole ring, Oxazine ring, Oxaziazole ring, Oxaziazine ring, etc. Examples include a heterocycle having a sulfur atom and a nitrogen atom.
Among these heterocycles, a heterocycle having two or more oxygen atoms as ring member atoms is preferable, and a heterocycle having two oxygen atoms as ring member atoms is preferable in that it is excellent in a wide temperature range from high temperature to low temperature. Is preferable. Further, a monocyclic heterocycle is preferable to a fused heterocycle, and an aliphatic heterocycle is preferable to an aromatic heterocycle. More specifically, a dioxolane ring and a dioxane ring are particularly preferable.

Although the reason is unknown, it is not preferable to include acryloyl morpholine in the active energy ray-polymerizable adhesive for optics because the viscosity of the adhesive decreases when it is stored for a long period of time.

The number of (meth) acryloyl groups in the compound (A) is preferably 1 to 6 in that the adhesive strength is improved in a wide temperature range from high temperature to low temperature, and particularly preferably one.

Specific examples of the compound (A) include (2-methyl-2-ethyl-1,3 dioxolane-4-yl) methyl (meth) acrylate and 5-ethyl (meth) acrylate-1,3-dioxane-5. -Ilmethyl, (meth) acrylic acid (2-oxo-1,3-dioxolan-4-yl) methyl, 1,3-dioxane-2-one-5-yl (meth) acrylate, 1- (meth) acryloyl- 4-Methylpiperazin, (meth) acrylic acid 11- [1', 3', 3'
-Trimethylspiro [3H-naphtho [2,1-b] [1,4] oxazine-3,2'(3'H)-[1H] indol] -5'-yloxy] undecyl, 2,5-bis ( (Meta) acroyloxyethylthiomethyl) -1,4-dithiane and the like, 2-methyl-2-ethyl-1,3 dioxolane-4-yl) methyl (meth) acrylate, (meth) acrylic acid 5 -Ethyl-1,3-dioxane-5-ylmethyl is preferable because it is excellent in a wide temperature range from high temperature to low temperature.

<(Meta) acrylate monomer (B) having a hydroxyl group having a molecular weight less than 500>
The (meth) acrylate (B) having a hydroxyl group having a molecular weight of less than 500 (hereinafter, also referred to as compound (B)) is not particularly limited as long as it is a (meth) acrylate having a hydroxyl group.
By including the compound (B) in the adhesive, hydrogen bonds are formed with the hydroxyl groups and the like of the base material, and the adhesive strength at room temperature and low temperature is improved.

Examples of the compound (B) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, ( 6-Hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, mono (meth) acrylic acid ester of cyclohexanedimethanol, 12-hydroxylauryl (meth) acrylate, ethyl-α- (meth) acrylate Monofunctional (meth) glycerol acrylate such as hydroxymethyl);
Fatty acid ester-based (meth) acrylic acid ester such as (meth) glycidyl lauric acid ester;

Cyclic of cyclohexanedimethanol mono (meth) acrylate, cyclohexanediethanol mono (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-a (meth) acryloylxyethyl-2-hydroxyethylphthalic acid, etc. (Meta) acrylic acid ester;
A (meth) acrylic acid ester having a hydroxyl group at the molecular end by ring-opening addition of ε-caprolactone to the (meth) acrylate having a hydroxyl group;
An aliphatic (meth) acrylic acid ester or the like of an alkylene oxide-added (meth) acrylic acid ester or the like in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is repeatedly added to the (meth) acrylate having a hydroxyl group can be mentioned. Be done.

As the compound (B), 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and (meth) acrylic are excellent in adhesive strength at low temperatures. 4-Hydroxybutyl acid is preferred, and 4-hydroxybutyl (meth) acrylate is particularly preferred.

<A (meth) acrylate monomer (C) having a ring structure other than a heterocycle having a weight average molecular weight of less than 500>
The (meth) acrylate monomer (C) having a ring structure other than the heterocycle having a molecular weight of less than 500 (hereinafter, also referred to as compound (C)) is a hydrocarbon ring (aromatic hydrocarbon ring or aliphatic) other than the heterocycle. Refers to a (meth) acrylate compound containing a hydrocarbon ring. Compound (C) is preferably a (meth) acrylate compound that does not contain a heterocycle but contains a hydrocarbon ring (aromatic hydrocarbon ring or aliphatic hydrocarbon ring). By containing the compound (C), an active energy ray-polymerizable adhesive for optics having excellent adhesive strength at high temperatures can be obtained.

Examples of the compound (C) include benzyl (meth) acrylate, phenoxy (meth) acrylate, ethylene oxide-modified phenoxy (meth) acrylate, bisphenol A di (meth) acrylate, alkylene oxide-modified bisphenol A di (meth) acrylate, and bisphenol. It has an aromatic hydrocarbon ring such as F-di (meth) acrylate, alkylene oxide-modified bisphenol F-di (meth) acrylate, 2- (meth) acryloylxyethylphthalic acid, neopentyl glycol-acrylic acid-benzoic acid ester (meth). ) Acrylate compound;
A (meth) acrylate compound having one or more aliphatic hydrocarbon rings such as di (meth) acrylate of hydrogenated bisphenol A, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, and cyclohexyl methacrylate;
3,3-Dicyclopropyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, Tricyclodecanedimethanol di (meth) acrylate, isobonyl (meth) acrylate, 3-hydroxy-1-adamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate, 2-ethyl-2-adamantyl (meth) ) Acrylic, 2-propyl-2-adamantyl (meth) acrylate, 3,5-dihydroxy-1-adamantyl (meth) acrylate, 1,3-adamantyldiol di (meth) acrylate, 1,3,5-adamantili (meth) acrylate Examples thereof include (meth) acrylate compounds having an aliphatic hydrocarbon ring of fused rings such as meta) acrylate and 3-hydroxy-1,5-adamantyldi (meth) acrylate.

As the compound (C), a (meth) acrylate compound having an aliphatic hydrocarbon ring of a condensed ring is preferable because it has excellent adhesive strength at a high temperature. Specifically, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, and isobonyl (meth) acrylate are preferable. , Tricyclodecanedimethanol di (meth) acrylate and isobonyl (meth) acrylate are particularly preferable.

The contents of the compounds (A), (B), and (C) in the active energy ray-polymerizable adhesive for optics were 5 to 70% by mass of the compound (A), 20 to 80% by mass of the compound (B), and the compound ( C) is preferably 5 to 50% by mass, more preferably 10 to 70% by mass of compound (A), 30 to 70% by mass of compound (B), and 5 to 40% by mass of compound (C). Further, the total amount of the compounds (A), (B) and (C) in the active energy ray-polymerizable adhesive for optics is preferably 70% by mass or more.

The active energy ray-polymerizable adhesive for optics of the present invention further comprises a polyurethane-based oligomer (D1) having a (meth) acryloyl group (hereinafter, also referred to as compound (D1)) and a polyester-based oligomer having a (meth) acryloyl group. It contains at least one oligomer selected from the group consisting of (D2) (hereinafter, also referred to as compound (D2)) and an epoxy-based oligomer (D3) having a (meth) acryloyl group (hereinafter, also referred to as compound (D3)). Therefore, it is preferable in that the adhesive strength at room temperature is improved.
The weight average molecular weight of the compounds (D1), (D2) and (D3) is preferably 500 to 100,000. The weight average molecular weight in the present specification is a value measured by gel permeation chromatography (GPC) using polystyrene having a known weight average molecular weight as a standard substance.

<Polyurethane-based oligomer having (meth) acryloyl group (D1)>
The polyurethane-based oligomer (D1) (compound (D1)) having a (meth) acryloyl group is a compound having a urethane bond and a (meth) acryloyl group in the molecule. For example, it can be obtained by reacting a compound having an isocyanate group at the terminal obtained by reacting a compound having one or more isocyanate groups with a compound having a hydroxyl group with a (meth) acryloyl group having a hydroxyl group.

Examples of the compound having at least one or more isocyanate groups include aromatic isocyanates such as 4,4'-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, and 1,4-phenylene bismethylene diisocyanate, and 3-isocyanate methyl-. Examples thereof include aliphatic isocyanates such as 3,5,5-trimethylcyclohexyl isocyanate and hexamethylene diisocyanate.

Specific examples of the compound (D1) include aromatic polyurethane-based oligomers such as EBECRYL210, EBECRYL220 (above, manufactured by Daicel Ornex), CN9782, CN9783 (above, manufactured by SARTOMER), purple light 3000B, purple light 3700B (above, Japan). Examples thereof include aliphatic polyurethane oligomers such as EBECRYL230, EBECRYL270, EBECRYL8402, and EBECRYL8701 (manufactured by Daicel Ornex).

<Polyester-based oligomer having (meth) acryloyl group (D2)>
The polyester oligomer (D2) having a (meth) acryloyl group (compound (D2)) is a compound having an ester bond and a (meth) acryloyl group in the molecule. For example, it has one or more carboxyl groups in the terminal of polyester obtained by polycondensing polybasic acid and polyhydric alcohol in the main chain skeleton, or in a hydroxyl group in the polyester chain and a molecule such as (meth) acrylic acid (meth). ) It can be obtained by an esterification reaction with acrylate.

Examples of the polybasic acid include aliphatic polyusic acids such as oxalic acid, malonic acid, succinic acid, adipic acid, sebatic acid, azelaic acid, suberic acid, maleic acid, fumaric acid, itaconic acid, succinic anhydride, and maleic anhydride. Examples include alicyclic systems such as basic acid, dimer acid and cyclohexanedicarboxylic acid, and aromatic systems such as isophthalic acid, terephthalic acid and biphenyldicarboxylic acid.

Examples of the polyhydric alcohol include relatively low molecular weight polyols having a number average molecular weight (Mn) of 50 to 500 and relatively high molecular weight polyols having a number average molecular weight (Mn) of 500 to 30,000.

Specific examples of the compound (D2) include aromatic polyester-based oligomers such as CN296, CN2203, CN2259, and CN2261 (manufactured by SARTOMER), and aliphatic polyesters such as CN294, CN2270, and CN2271 (manufactured by SARTOMER). System oligomers can be mentioned.

<Epoxy oligomer with (meth) acryloyl group (D3)>
The epoxy-based oligomer (D3) having a (meth) acryloyl group (compound (D3)) is a partial structure obtained by reacting an epoxy group of an epoxy compound with a compound having a carboxyl group and / or a hydroxyl group, and (meth). It is a compound having an accriloyl group.

Examples of the epoxy compound include aromatic epoxy compounds such as bisphenol type epoxy, aliphatic epoxy compounds such as diglycidyl ether having 2 to 20 carbon atoms, and alicyclic epoxy compounds.

Specific examples of the compound (D3) include aromatic epoxy oligomers such as CN104, CN110 (above, manufactured by SARTOMER), EBECRYL600, EBECRYL3701 (above, manufactured by Daicel Ornex), CN111, CN113 (above, manufactured by SARTOMER). ), EBECRYL860 (manufactured by Daicel Ornex) and other aliphatic epoxy-based oligomers.

The content of the compounds (D1), (D2) and (D3) in the active energy ray-polymerizable adhesive for optical is 1 to 30% by mass in total of the compounds (D1), (D2) and (D3). It is preferably present, and more preferably 3 to 20% by mass.

The active energy ray-polymerizable adhesive for optics of the present invention includes other (meth) acrylate compounds (E) other than the compounds (A), (B), (C), (D1), (D2) and (D3). It may also contain (hereinafter, also referred to as compound (E)) or a cationically polymerizable compound (F) (hereinafter, also referred to as compound (F)).

By containing the compound (E), the viscosity of the active energy ray-polymerizable adhesive for optics can be lowered to improve the coatability, and the durability such as wet heat resistance can be further improved.

Examples of the compound (E) include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, n-hexyl (meth) acrylate, lauryl (meth) acrylate, and (meth). (Meta) acrylic acid alkyl ester such as stearyl acrylate;
(Meta) acrylate (meth) allyl, (meth) acrylate 1-butenyl, (meth) acrylate 3,7-dimethylocta-6-ene-1-yl, 2- (2-vinyloxyethoxy) acrylate (Meta) acrylates containing ethyl and other unsaturated groups such as vinyl (meth) acrylate;

Perfluoroalkyl esters of (meth) acrylates such as perfluoromethyl (meth) acrylate, 2-perfluoroethyl ethyl (meth) acrylate, and 2-perfluorohexadecylethyl (meth) acrylate;
(Meta) acrylate (methoxycarbonyl) methyl, (meth) acrylate 2- (ethoxycarbonyloxy) hexyl, (meth) acrylate 2- (propoxycarbonyloxy) ethyl, and (meth) acrylate 2- (octyloxy) An aliphatic (meth) acrylic acid ester having one carbonyl group such as carbonyloxy) butyl;
2-Oxobutanoylethyl (meth) acrylate, 3-oxobutanoylpropyl (meth) acrylate, 2,3-di (oxobutanoyl) butyl (meth) acrylate, 2,3-di (meth) acrylate An aliphatic (meth) acrylic acid ester having two carbonyl groups such as di (oxobutanoyl) hexyl;

2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-propoxyethyl (meth) acrylate, 3-propoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, An alkoxy group-containing (meth) acrylic acid ester such as 3-butoxyethyl (meth) acrylate and 4-butoxyethyl (meth) acrylate;
An alkylene oxide-containing (meth) acrylic acid derivative such as an alkylene oxide adduct of (meth) acrylic acid;

Di (meth) acrylate ethylene glycol, di (meth) acrylate triethylene glycol, di (meth) acrylate tetraethylene glycol, di (meth) acrylate 2,2-dimethylpropyldiol, di (meth) acrylate hydroxy Pivalyl hydroxypivalate, di (meth) acrylic acid 2,5-hexanediol, di (meth) acrylic acid 1,2-octanediol, di (meth) acrylic acid 2,2-diethyl-1,3-propanediol , And bifunctional (meth) acrylic acid esters such as di (meth) acrylic acid 2,5-dimethyl-2,5-hexanediol;
Tri (meth) acrylate 1,2,3-propanetriol, tri (meth) acrylate trimethyl hexane, tri (meth) acrylate trimethyl octane, and tri (meth) acrylate 1,1,1-trishydroxy Trifunctional (meth) acrylic acid ester such as methyl ethane;

Pentaerythritol tetra (meth) acrylate, 2,2-bis (hydroxymethyl) 1,3-propanediol tetra (meth) acrylate, and di22-bis (hydroxymethyl) 1,2-bis (hydroxymethyl) hepta (meth) acrylate 1, Polyfunctional (meth) acrylic acid ester such as 3-propanediol polyalkylene oxide;
(Meta) acrylate compounds having cationically polymerizable functional groups such as glycidyl (meth) acrylate and 3,4-epoxycyclohexylmethyl (meth) acrylate;
Examples thereof include (meth) acrylate compounds having a heterocycle containing one heteroatom such as tetrahydrofurfuryl (meth) acrylate.

<Cation-polymerizable compound (F)>
Examples of the compound (F) include a compound having an epoxy group which is a 3-membered ring ether, a compound having an oxetanyl group which is a 4-membered ring ether, a vinyl ether compound, a cyclic ester compound, a cyclic formal compound, a cyclic carbonate compound and a fluorine-containing compound. Cyclic compounds and the like are preferable. Among the above compounds, none of the compounds having a ring has a (meth) acryloyl group, and is therefore different from the compounds (A), (B) and (C).
By containing the compound (F), the curing shrinkage of the adhesive is reduced, and the adhesive strength at room temperature is improved.

As the compound having an epoxy group (epoxy compound), an aromatic epoxy compound, an aliphatic epoxy compound, an alicyclic epoxy compound and the like are preferable.

Examples of the aromatic epoxy compound include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, bisphenol A propylene oxide adduct diglycidyl ether, and phenol novolac. Examples thereof include epoxy, cresol novolac epoxy, biphenyl type epoxy, resorcindiglycidyl ether, phenylglycidyl ether, phenolethylene oxide glycidyl ether, and t-butylphenyl glycidyl ether.

As the aliphatic epoxy compound, aliphatic monoalcohol, aliphatic polyalcohol, and glycidyl ether as an alkylene oxide adduct thereof are preferable. The aliphatic epoxy compounds include, for example, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, 1,4-butanjiol diglycidyl ether, neopentyl glycol diglycidyl ether, and 1,6-hexanediol diglycidyl ether. 1 or 2 for aliphatic polyhydric alcohols such as glycerin triglycidyl ether, trimethylpropane triglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, ethylene glycol, polypropylene glycol, and glycerin. Examples thereof include polyglycidyl ether, which is a polyether polyol obtained by adding more than one kind of alkylene oxide (ethylene oxide or polypropylene oxide).

Examples of the alicyclic epoxy compound include 1,2-epoxy-4-vinylcyclohexane, 1,2: 8,9 diepoxylimonene, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, and 2, -(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-meth-dioxane, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6) -Methylcyclohexylmethyl) Adipate and the like can be mentioned.

The epoxy equivalent of the epoxy compound is usually preferably about 30 to 3000 g / eq, more preferably 50 to 1500 g / eq. When the epoxy equivalent is 30 g / eq or more, the flexibility of the sheet after curing is excellent and the adhesive strength is further improved. Further, when it is 3000 g / eq or less, the curability is excellent and the adhesive strength is improved.

Examples of the compound having an oxetanyl group include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene, and di (1-ethyl-3-oxetanyl). Methyl ether, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, phenolnovolac oxetane, 3-ethyl-{(3-triethoxysilylpropoxy) Methyl} oxetane and the like.

Examples of the vinyl ether compound include n-amyl vinyl ether, i-amyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, 2-ethylhexyl vinyl ether, n-dodecyl vinyl ether, stearyl vinyl ether, oleyl vinyl ether and the like having 5 to 20 carbon atoms. Vinyl ethers of alkyl and alkenyl alcohols;
Monoalcohol vinyl ether having an aliphatic ring or aromatic ring such as cyclohexyl vinyl ether, 2-methylcyclohexylvinyl ether, cyclohexylmethylvinyl ether, benzylvinyl ether;
Glycerol monovinyl ether, 1,4-butanjiol monovinyl ether, 1,4-butanjiol divinyl ether, 1,6-hexanediol divinyl ether, neopentyl glycol divinyl ether, pentaerythritol-rudivinyl ether, pentaerythritol Tetravinyl ether, trimethyl propandivinyl ether, trimethyl propantrivinyl ether, 1,4-dihydroxycyclohexane monovinyl ether, 1,4-dihydroxycyclohexanedivinyl ether, 1,4-dihydroxymethylcyclohexanemonovinyl ether, 1,4-dihydroxy Monovinyl ethers and polyvinyl ethers of polyhydric alcohols such as methylcyclohexanedivinyl ethers;
Polyalkylene glycol monodivinyl ethers and divinyl ethers such as triethylene glycol divinyl ethers and diethylene glycol monobutyl monovinyl ethers;
Other vinyl ethers such as glycidyl vinyl ether and ethylene glycol vinyl ether methacrylate can be mentioned.

Examples of the cyclic ester compound include lactone and the like. Examples of the cyclic carbonate compound include ethylene carbonate and propylene carbonate. Examples of the cyclic formal compound include dioxolane, dioxane, trioxane and the like. Compound (F) can be used alone or in combination of two or more.

The compound (F) is preferably a compound having an epoxy group and a compound having an oxetanyl group. Among compounds having an epoxy group and compounds having an oxetanyl group, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (3,4-epoxycyclohexylmethyl) adipate, bisphenol A di. Glycidyl ether, bisphenol F diglycidyl ether, and 1,6-hexanediol diglycidyl ether are preferable because they have particularly excellent reactivity.

<Active energy ray polymerization initiator (G)>
The active energy ray-polymerizable adhesive for optics is an active energy ray polymerization initiator (G) (hereinafter referred to as “)”.
It may also contain compound (G)). Examples of the compound (G) include an active energy ray radical polymerization initiator (g1), an active energy ray cationic polymerization initiator (g2), and an active energy ray anionic polymerization initiator (g3).
As the active energy ray radical polymerization initiator (g1), a known active energy ray radical polymerization initiator can be used. Examples of commercially available products include Irgacure-184, 907, 651, 1700, 1800, 819, 369, 261 and DAROCUR-TPO (above, manufactured by BASF), DaroCure-1173 (manufactured by Merck), Ezacure-KIP150, TZT (manufactured by Nippon Shibel Hegner), Kayacure BMS, Kayacure DMBI, (above, manufactured by Nippon Kayaku Co., Ltd.) and the like can be mentioned.

As the active energy ray cationic polymerization initiator (g2), a known active energy ray cationic polymerization initiator can be used. Examples of commercially available products include sulfonium salts such as UVACURE1590 (manufactured by Daicel Cytec) and CPI-110P (manufactured by Sun Appro), IRGACURE250 (manufactured by BASF), WPI-113 (manufactured by Wako Pure Chemical Industries, Ltd.), and Rp. Examples thereof include iodonium salts such as −2074 (manufactured by Rhodia Japan).

As the active energy ray anionic polymerization initiator (g3), a known active energy ray anionic polymerization initiator can be used. Examples of commercially available products include WPBG-165, WPBG-018, WPBG-172, WPBG-140, WPBG-166, WPBG-027, WPBG-082, WPBG-167, WPBG-168, WPBG-266 (above, Wako Pure Chemical Industries, Ltd.) and the like.

The compound (G) is preferably blended in an amount of 0.1 to 10% by mass, more preferably 0.5 to 5% by mass, in 100% by mass of the active energy ray polymerizable adhesive for optics.

The active energy ray-polymerizable adhesive for optics of the present invention further comprises a photosensitizer, an amine-based catalyst, a phosphorus-based catalyst, a filler, an antistatic agent, an antioxidant, an antioxidant, and a tackifier, if necessary. , Antiblocking agent, antifoaming agent, plasticizer, silane coupling agent, titanium coupling agent and the like can be contained.

The active energy ray-polymerizable adhesive for optics of the present invention preferably contains substantially no organic solvent, and preferably does not contain any organic solvent. However, since the compound (G) is often poorly soluble in the polymerizable component, a small amount of an organic solvent may be contained in order to dissolve the compound (G). The content of the organic solvent in the adhesive is preferably 5% by mass or less.

The active energy ray-polymerizable adhesive for optics of the present invention preferably has a viscosity at 25 ° C. of 1 to 2000 mPa · s from the viewpoint of controlling the smoothness of the coating film and the dimensional stability of the cured resin product. , 10 to 1500 mPa · s, more preferably 20 to 1000 mPa · s.

When the active energy ray-polymerizable adhesive for optics is used as an adhesive layer of an optical laminate (hereinafter, may be simply referred to as "laminate"), the thickness of the adhesive layer is 0.1 to 6 μm. Is preferable, and 0.1 to 3 μm is more preferable. When the thickness of the adhesive layer is within the above range, the adhesive strength is further improved.

A known coating device can be used for coating the adhesive on the base material. For example, wire bar, appliquer, brush, sprayer, roller, gravure coater, die coater, micro gravure coater, lip coater, comma coater, Examples thereof include a filter coater, a knife coater, a river coater, and a spin coater.

The active energy ray used for curing the adhesive is preferably light containing ultraviolet rays, and in that case, the wavelength is preferably 150 to 550 nm. Examples of the light source of the active energy ray include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, an LED lamp, a xenon lamp, and a metal halide lamp. ..

The irradiation intensity of the active energy ray is preferably 10 to ^{500 mW / cm 2.} The integrated irradiation amount expressed as the product of the irradiation intensity and the irradiation time is preferably 10 to ^{5000 mJ / cm 2, preferably 30.}
~ 4000 mJ / cm ² is more preferable.

The optical laminate of the present invention comprises a resin layer, an adhesive layer, and a base material formed from an optical active energy ray-polymerizable adhesive.

The polymerization reaction of the adhesive proceeds by irradiating the active energy rays at the time of applying the adhesive, at the time of laminating, and after laminating, but after laminating the base material, irradiating the active energy rays. It is preferable to proceed with the polymerization reaction. At that time, in order to allow the polymerization reaction to proceed by irradiation with the active energy rays, it is preferable that at least one of the first base material and the second base material is made of a material that easily transmits the active energy rays. Specifically, a transparent film, a plastic lens, a transparent glass plate and the like are preferable. For example, if a transparent film or a transparent glass plate is used as the first base material, a base material that is difficult for active energy rays to pass through as the second base material, for example, wood, metal plate, plastic plate, processed paper product, etc. You may use it.

In the laminate of the present invention, it is preferable to use a film-like base material as the base material. Examples of the film-like substrate include cellophane, various plastic films, and paper. Of these, the use of various transparent plastic films is preferable. Further, the film-like base material may have a single layer or a multi-layer structure in which a plurality of base materials are laminated, as long as the film is transparent.

Hereinafter, a more specific embodiment of the optical laminate of the present invention will be described by taking a case where a transparent film is used as a base material as an example.

The laminate of the present invention is in the form of a sheet obtained by laminating a plurality of transparent films such as a transparent film / adhesive layer / transparent film or a transparent film / adhesive layer / transparent film / adhesive layer / transparent film. It is a multilayer film. Further, it is also preferable that the sheet-shaped multilayer film is adhered to another optical member such as glass or an optical sheet. The laminate can be obtained by curing the adhesive layer by irradiating the active energy ray-polymerizable adhesive for optical with active energy rays from one side or both sides of the film to polymerize and cure the film.

As the transparent film, for example, a polyolefin-based film such as a polyvinyl alcohol film, a polytriacetyl cellulose film, polypropylene, polyethylene, a polycycloolefin, and an ethylene-vinyl acetate copolymer; and a polyester-based film such as polyethylene terephthalate and polybutylene terephthalate. ; Polycarbonate-based film, polynorbornen-based film, polyarylate-based film, polyacrylic-based film, polyphenylene sulfide-based film, polystyrene-based film, polyvinyl-based film, polyamide-based film, polyimide-based film, polyoxylan-based film, and the like. ..
When a transparent film is used as the base material, the laminate of the present invention can be suitably used for optical applications.

The thickness of the transparent film can be appropriately determined, but in general, 1 to 500 μm is preferable, 1 to 300 μm is more preferable, and 5 to 200 μm is preferable from the viewpoint of film strength, workability, thin layer property and the like. More preferred. When used for optical applications, the thickness of the transparent film is preferably 5 to 150 μm.

As an example of the embodiment of the optical laminate of the present invention, as the optical element laminate, it is preferable to use an optical film mainly used for optical applications as a transparent film.

Optical films include, for example, hard coat film, antistatic coat film, antiglare coat film, polarizing film, retardation film, elliptically polarizing film, antireflection film, light diffusing film, brightness improving film, prism film (prism film). Examples thereof include a decorative film (also referred to as a light guide plate), a decorative film (including a filling sheet for a touch panel), and a light guide film (also referred to as a light guide plate).

The active energy ray-polymerizable adhesive for optics of the present invention can be used to form a laminate of a liquid crystal display device, a PDP module, a touch panel module, an organic EL module, or the like.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. In addition, "part" is "mass%", and "%" represents "mass%".

<Weight average molecular weight>
The weight average molecular weight was determined by using Showa Denko's GPC (Gel Permeation Chromatry) "Shodex GPC System-21" as a measuring device and two Showa Denko's Shodex GPC LF-604 as columns, and tetrahydrofuran (as a developing solvent). THF), a flow velocity of 0.6 ml / min, and a column temperature of 40 ° C. were measured. The weight average molecular weight was determined by a calibration line prepared using a monodisperse molecular weight polystyrene having a known weight average molecular weight as a standard substance.

[Example 1]
<Production example of active energy ray-polymerizable adhesive>
In a light-shielded glass bottle with a capacity of 300 mL, as compound (A), (2-methyl-2-ethyl-1,3-dioxolan-4-yl) methyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name MEDOL-10, molecular weight 208) ) 40 parts, compound (B) 40 parts 4-hydroxybutyl acrylate, compound (C) dicyclopentenyl acrylate (Hitachi Kasei Co., Ltd. trade name Funkryl 511AS, molecular weight 204) 18 parts, Irgacure 184 (BASF Co., Ltd. light 2 parts of a radical polymerization initiator) was added, and the mixture was sufficiently stirred and defoamed to obtain an active energy ray-polymerizable adhesive. The viscosity (initial viscosity) measured under the following conditions immediately after the production of the adhesive was 8 mPa · s.

《Viscosity over time》
The obtained active energy ray-polymerizable adhesive was stored at 40 ° C. for one month, and then the viscosity with time was measured under the following conditions. The adhesive can be used when the viscosity change rate calculated by Equation 1 is within ± 20%.
<Equation 1>
Viscosity change rate (%) = ((viscosity over time-initial viscosity) / initial viscosity) x 100

<Viscosity measurement conditions>
Using an E-type viscometer (TV-22 manufactured by Toki Sangyo Co., Ltd.), 1.2 mL of active energy ray-polymerizable adhesive was used as a measurement sample, and the conditions were 23 ° C., rotation speed 0.5 to 100 rpm, and rotation for 1 minute. The viscosity was measured with.

<Manufacturing example of laminated body>
As a transparent film, a polytriacetyl cellulose-based film containing an ultraviolet absorber manufactured by Fuji Film Co., Ltd .: trade name "Fujitac: 80 μm" (thickness 80 μm), and a polynorbornene-based film manufactured by Nippon Zeon Co., Ltd. containing no ultraviolet absorber. (Thickness 100 μm) was used. The surface of one side of the two transparent films was subjected to corona treatment at a discharge rate of ^{300 W / min / m 2.} Within 1 hour thereafter, the active energy ray-polymerizable adhesive is applied onto the corona-treated surface of the polytriacetyl cellulose-based film containing an ultraviolet absorber to a thickness of 4 μm using a wire bar coater. I painted it like this. Further, a polynorbornene-based film containing no ultraviolet absorber was layered, and the polytriacetyl cellulose-based film containing an ultraviolet absorber was fixed to the tin plate with cellophane tape on all sides so that the polytriacetyl cellulose-based film was in contact with the tin plate.

Active energy ray irradiation device (high-pressure mercury lamp manufactured by Toshiba) with a maximum illuminance of 500 mW / cm ² ,
A laminate was prepared by irradiating ultraviolet rays with an integrated light amount of 1000 mJ / cm ² from the polynorbornen-based film side manufactured by Nippon Zeon Co., Ltd., which does not contain an ultraviolet absorber.

With respect to the obtained laminate, the room temperature adhesive force, the high temperature adhesive force and the low temperature adhesive force were determined according to the following methods, and the results are shown in Table 1.

《Room temperature adhesive strength》
The adhesive strength was measured according to Japanese Industrial Standards (JIS) K6854-4 Adhesive-Peeling Adhesive Strength Test Method-Part 4: Floating Roller Method. That is, the obtained laminate was cut into a size of 25 mm × 150 mm using a cutter to prepare a sample for measurement. A double-sided adhesive tape (DF8712S manufactured by Toyokem Co., Ltd.) was attached to a polynorbornene-based film surface containing no ultraviolet absorber of the sample, and fixed on a metal plate using a laminator. The laminating body for measurement is provided with a peeling kick in advance between the transparent films, and the laminating body for measurement is placed at 23 ° C. and a relative humidity of 50% at a speed of 300 mm / min and 90 ° C. The ultraviolet absorber-containing polytriacetyl cellulose-based film was peeled off at the angle of 1 and the adhesive strength was measured. This adhesive strength was evaluated on a 4-point scale. If the evaluation is ◎, ○, △, there is no problem in practical use.
⊚: Not peelable or base material destroyed (extremely good)
◯: Peeling force is 2.0 (N / 25 mm) or more (good)
Δ: Peeling force is 1.0 (N / 25 mm) or more and less than 2.0 (N / 25 mm) (usable)
X: Peeling force is less than 1.0 (N / 25 mm) (cannot be used)

《High temperature adhesive strength》
In the above method for evaluating the room temperature adhesive force, the adhesive force was measured in the same manner as the room temperature adhesive force except that the temperature was changed from 23 ° C. to 60 ° C. This adhesive strength was evaluated on a 4-point scale. If the evaluation is ◎, ○, △, there is no problem in practical use.
⊚: Peeling force is 1.5 (N / 25 mm) or more (extremely good)
◯: Peeling force is 1.0 (N / 25 mm) or more and less than 1.5 (N / 25 mm) (good)
Δ: Peeling force is 0.5 (N / 25 mm) or more and less than 1.0 (N / 25 mm) (usable)
X: Peeling force is less than 0.5 (N / 25 mm) (cannot be used)

《Low temperature adhesive strength》
In the above method for evaluating room temperature adhesive strength, the adhesive strength was measured in the same manner as the room temperature adhesive strength except that the temperature was changed from 23 ° C. to 0 ° C. This adhesive strength was evaluated on a 4-point scale. If the evaluation is ◎, ○, △, there is no problem in practical use.
⊚: Cannot be peeled off or destroys base material (extremely good)
◯: Peeling force is 1.0 (N / 25 mm) or more (good)
Δ: Peeling force is 0.5 (N / 25 mm) or more and less than 1.0 (N / 25 mm) (usable)
X: Peeling force is less than 0.5 (N / 25 mm) (cannot be used)

[Examples 2-26, Comparative Examples 1-5]
Except for the changes to the materials and compositions shown in Tables 1 and 2, active energy ray-polymerizable adhesives and laminates were produced in the same manner as in Example 1, respectively, and the viscosity, viscosity with time, viscosity change rate, room temperature adhesive strength, and so on. The high temperature adhesive strength and the low temperature adhesive strength were evaluated. The evaluation results are shown in Tables 1 and 2.
Examples 18 and 19 in Table 1 are reference examples.

The materials used in the examples and their abbreviations are shown below.
<Compound (A)>
MEDOL-10: (2-Methyl-2-ethyl-1,3-dioxolane-4-yl) methyl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name MEDOL-10
Viscoat 200: 5-ethyl acrylate-1,3-dioxane-5-ylmethyl, manufactured by Osaka Organic Chemical Industry, trade name Viscoat # 200

<Compound (C)>
FA511AS: Dicyclopentenyl Acrylate Made by Hitachi Kasei Co., Ltd. Product name Funkrill FA511AS
IBXA: Isobornyl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name IBXA
A-DCP: Tricyclodecanedimethanol diacrylate Shin Nakamura Chemical Industry Co., Ltd. Brand name NK ester A-DCP
BPE-80N: Ethoxylated bisphenol A dimethacrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd. Brand name NK ester BPE-80N

<Compound (D1)>
UV3000B: Urethane acrylate oligomer, manufactured by Nippon Synthetic Chemical Industry Co., Ltd., trade name Shikou UV3000B
EBECRYL210: Urethane acrylate oligomer, manufactured by Daicel Ornex, trade name EBECRYL210
<Compound (D2)>
EBECRYL525: Polyester acrylate oligomer (containing 40% by mass of tripropylene glycol diacrylate), manufactured by Daicel Ornex, trade name EBECRYL525
EBECRYL884: Polyester acrylate oligomer, manufactured by Daicel Ornex, trade name EBECRYL884
<Compound (D3)>
KAYARAD R-9485: Epoxy acrylate oligomer, manufactured by Nippon Kayakusha, trade name KAYARAD R-9485
BAEM-100: Mepoxy methacrylate oligomer, manufactured by KSM, trade name BAEM-100

<Compound (E)>
THFA: Tetrahydrofurfuryl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat # 150
<Compound (F)>
2021P: 3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexylcarboxylate, manufactured by Daicel Corporation, trade name Serokiside 2021P
EX212L: 1,6-hexanediol diglycidyl ether (low chlorine grade), manufactured by Nagase Chemitex, trade name Denacol EX212L
<Compound (G)>
Irgacure 184: 1-Hydroxycyclohexyl-phenyl-ketone, manufactured by BASF, trade name Irgacure 184
CPI-100P: Active energy ray cationic polymerization initiator, manufactured by San-Apro, trade name CPI-110P

The active energy ray-polymerizable adhesive of the present invention has excellent storage stability, and the laminates using the active energy ray-polymerizable adhesive of the present invention (Examples 1 to 26) are the laminates of Comparative Examples 1 to 5. It was clarified that the adhesive strength at room temperature, the adhesive strength at high temperature, and the adhesive strength at low temperature were superior to those of the above.

Claims (4)

Mono (meth) acrylate monomer (A) having a molecular weight of less than 500 and having a heterocycle containing two or more oxygens as atoms constituting the ring (excluding acryloylmorpholine),
A (meth) acrylate monomer (B) having a molecular weight of less than 500 and having a hydroxyl group (excluding the (meth) acrylate monomer (A) having a heterocycle), and a ring having a molecular weight of less than 500 and having a non-heterocyclic ring. (Meta) acrylate monomer (C) (excluding the mono (meth) acrylate monomer (A) and the (meth) acrylate monomer (B)).
The (meth) acrylate monomer (A), (B), and (C) are contained in an amount of 48 % by mass or more in total, and the (meth) acrylate monomer (A) is contained in an amount of 3 to 75 % by mass, said (meth) acrylate. An optical active energy ray-polymerizable adhesive containing 10 to 85 % by mass of the monomer (B) and 5 to 55% by mass of the (meth) acrylate monomer (C).
(However, mono (meth) acrylate monomer (A) having a molecular weight of less than 500 and having a heterocycle containing two or more oxygens as atoms constituting the ring (however, excluding acryloylmorpholine),
A (meth) acrylate monomer (B) having a molecular weight of less than 500 and having a hydroxyl group (excluding the (meth) acrylate monomer (A) having a heterocycle), and
Includes (meth) acrylate monomer (C) having a molecular weight less than 500 and having a ring other than a heterocycle (excluding the mono (meth) acrylate monomer (A) and the (meth) acrylate monomer (B)). ,
The (meth) acrylate monomer (A), (B), and (C) are contained in an amount of 70% by mass or more in total, and the (meth) acrylate monomer (A) is contained in an amount of 5 to 70% by mass, said (meth) acrylate. (Excluding the active energy ray-polymerizable adhesive for optical use, which contains the monomer (B) in a ratio of 20 to 80% by mass and the (meth) acrylate monomer (C) in a ratio of 5 to 50% by mass).
Further, an oligomer selected from the group consisting of a polyurethane-based oligomer having a (meth) acryloyl group (D1), a polyester-based oligomer having a (meth) acryloyl group (D2), and an epoxy-based oligomer having a (meth) acryloyl group (D3). The active energy ray-polymerizable adhesive for optics according to claim 1, which comprises one or more of. The optical active energy according to claim 1 or 2, wherein the (meth) acrylate monomer (B) is at least one (meth) acrylate monomer selected from the group consisting of the following (B1) to (B3). Linear polymerizable adhesive.
The (meth) acrylate monomer (B1) is 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-Hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, ethyl-α- (hydroxymethyl) (meth) acrylate, glycidyl (meth) acrylate Lauric acid ester, cyclohexanedimethanol mono (meth) acrylate, cyclohexanediethanol mono (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and 2- (meth) acryloylxyethyl-2-hydroxyethylphthalic acid. Selected from the group consisting of.
The (meth) acrylate monomer (B2) is a (meth) acrylate ester in which a hydroxyl group is added to the molecular end by ring-opening addition of ε-caprolactone to the (meth) acrylate monomer (B1).
The (meth) acrylate monomer (B3) is an alkylene oxide-added (meth) acrylic acid ester in which an alkylene oxide is repeatedly added to the (meth) acrylate monomer (B1). An optical laminate comprising a first base material, a resin layer which is a cured product of the active energy ray-polymerizable adhesive for optics according to any one of claims 1 to 3, and a second base material. ..