JP2005272773A - Active energy beam-curable composition for optical material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an active energy beam-curable composition for optical materials excellent in workability, and giving a cured product with high refractive index and excellent in adhesivity with a resin substrate, especially of a (meth)acrylic resin. <P>SOLUTION: This active energy-curable composition for optical materials comprises (A) a urethane(meth)acrylate and/or an epoxy(meth)acrylate and (B) a (meth)acrylate expressed by formula (1) or formula (2), where R1 and R2 each represents a hydrogen atom or a methyl group. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  TECHNICAL FIELD The present invention relates to an active energy ray-curable composition for optical materials, and belongs to the technical field of active energy ray-curable compositions and optical materials such as adhesives when assembling lens sheets and optical materials. is there.

Conventionally, lens sheets such as Fresnel lenses and lenticular lenses have been manufactured by molding by a method such as a press method or a cast method.
However, the former pressing method has a problem of poor productivity because it is manufactured by a cycle of heating, pressurizing and cooling. Further, the latter casting method has a problem that it takes a long manufacturing time because a monomer is poured into a mold for polymerization, and a large number of molds are required, resulting in an increase in manufacturing cost.

  On the other hand, since the active energy ray-curable composition has fast curability and is excellent in productivity, in order to solve the above problems, various active energy ray-curable compositions for producing lens sheets are available. Proposals have been made (for example, Patent Documents 1 to 6).

However, conventional active energy ray-curable compositions are insufficient in terms of refractive index and transparency, and in order to further improve this point, mono (meta) having a bisphenol di (meth) acrylate and an aromatic ring. ) Compositions using acrylate in combination have been studied (for example, Patent Documents 7 and 8).
In recent years, in the production of optical materials, the cured product is required to have a high refractive index even for an adhesive composition used when bonding high refractive materials. (Patent Documents 9 and 10)

JP-A-61-177215 (Claims) JP 61-248707 A (Claims) JP 61-248708 A (Claims) JP 63-163330 A (Claims) JP 63-167301 A (Claims) JP 63-199302 A (Claims) JP-A-9-87336 (Claims) Japanese Patent No. 3398448 (Claims) Japanese Examined Patent Publication No. 6-70209 (Claims) Japanese Patent Laid-Open No. 7-3237 (Claims)

However, the above-described active energy ray-curable composition is insufficient for applications that require a higher refractive index, such as those required for thinning projection televisions and the like.
In addition, in the technology for producing a lens by pouring an active energy ray-curable composition between a lens mold and a transparent substrate and curing the composition, sufficient adhesion cannot be obtained between the lens portion and the transparent substrate. There are many. In particular, when a methacrylic resin, which is excellent in transparency and weather resistance as a transparent substrate and is frequently used as this kind of material, has insufficient adhesion to the cured product of the active energy ray-curable composition. There were many.
In addition, the above-described conventional adhesive composition for optical materials may cause the cured product to be colored (Patent Document 9), or the viscosity of the composition may increase, making it difficult to handle. (Patent Document 10).
The present inventor is eager to find a composition for an active energy ray-curable optical material that is excellent in workability, has a high refractive index, and has excellent adhesion to a resin substrate, particularly (meth) acrylic resin. It was examined.

As a result of intensive studies to solve the above problems, the present inventor is effective to use a composition in which urethane (meth) acrylate and / or epoxy (meth) acrylate and a specific aromatic (meth) acrylate are used in combination. As a result, the present invention has been completed.
Hereinafter, the present invention will be described in detail.
In the present specification, acrylate or methacrylate is represented as (meth) acrylate.

The present invention relates to urethane (meth) acrylate and / or epoxy (meth) acrylate (A) [hereinafter referred to as component (A)], and (meth) acrylate represented by the following formula (1) and / or formula (2). The present invention relates to an active energy ray-curable optical material composition containing (B) [hereinafter referred to as component (B)].
Hereinafter, each component will be described.

1. (A) Component In the present invention, urethane (meth) acrylate (hereinafter referred to as (A-1) component) and / or epoxy (meth) acrylate (hereinafter referred to as (A-2) component) is used as component (A).
As the component (A-1), various urethane (meth) acrylates can be used. For example, an organic diisocyanate [hereinafter referred to as component (a)], a diol compound (hereinafter referred to as component (b)) and one in one molecule. And the like obtained by reacting (meth) acrylate having a hydroxyl group (hereinafter referred to as component (c)).

As the component (a), various organic diisocyanate compounds can be used. Specific examples include tolylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and the like. Can be mentioned.
Among these, from the viewpoint of refractive index, aromatic organic diisocyanates such as tolylene diisocyanate and sixylene diisocyanate are preferable, and isophorone diisocyanate is more preferable from the viewpoint that the member is hardly yellowed after long-term use.

  As the component (b), various compounds can be used as long as they are compounds having two hydroxyl groups. Typical examples thereof include ethylene glycol, propylene glycol, 3-methyl-1,5-pentanediol, , 3-butylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, cyclohexane dimethylol, tricyclodecane dimethylol, 2-butyl-2-ethyl-propanediol, bisphenol A polyethoxy glycol Diols such as bisphenol A polypropoxyglycol and polytetramethylene glycol; reaction of diol with dibasic acid or its anhydride (eg succinic anhydride, adipic acid, azelaic acid, isophthalic acid, terephthalic acid, phthalic anhydride, etc.) Polyes Rujioru; reaction product of the diol and ε- caprolactone; polycaprolactone diol is the reaction product of a polyester diol and ε- caprolactone; and polycarbonate diol (C4), and the like.

As the component (c), various compounds can be used as long as they are (meth) acrylates having a hydroxyl group. Specific examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4- Hydroxybutyl (meth) acrylate, polyethylene glycol mono (meth) acrylate (degree of polymerization: n = 2 to 10 as an average value), polypropylene glycol mono (meth) acrylate (degree of polymerization: n = 2 to 10 as an average value) and penta Examples include erythritol tri (meth) acrylate.
Among these, hydroxy (2 to 4 carbon atoms) alkyl acrylates such as 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate are preferable.

(A-1) The manufacturing method of a component should just follow a conventional method, for example, the said (a) component and (b) component can be urethanated, and then (c) component can be made to react with this reaction material. That's fine.
The proportion of component (a) and component (b) used is preferably 1.1 to 2.0 equivalents of the isocyanate group of component (a), more preferably 1.5 to 1 equivalent of hydroxyl group of component (b). -2.0 equivalents.
The reaction temperature for this urethanization reaction is usually from room temperature to 100 ° C, preferably from 40 to 85 ° C.
In the reaction of the compound having a terminal isocyanate group obtained by this urethanation reaction (hereinafter referred to as urethanization reaction product) and the component (c), the component (c) is added to 1 equivalent of the isocyanate group of the urethanization reaction product. It is preferable to react 0.9 to 1.5 equivalents of the hydroxyl group, and particularly preferably 1.0 to 1.2 equivalents. In this reaction, a polymerization inhibitor such as hydroquinone, hydroquinone monomethyl ether, p-methoxyphenol, p-benzoquinone or the like is usually added to the reaction mixture in order to prevent gelation due to radical polymerization during the reaction. Is preferred. The reaction temperature for the acrylated reaction is usually from room temperature to 100 ° C, preferably from 50 to 85 ° C.
Although the reaction between these isocyanate groups and hydroxyl groups proceeds without a catalyst, it is preferable to use a conventional catalyst such as triethylamine and dibutyltin dilaurate.

  Specific examples of the component (A-2) include, for example, epoxy resins (for example, bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol / novolak type epoxy resins, cresol / novolak type epoxy resins) and (meth). An epoxy (meth) acrylate which is a reaction product of acrylic acid can be used. Preferable examples include bisphenol A type epoxy acrylate.

2. (B) component In this invention, the compound represented by following formula (1) and / or Formula (2) is used as (B) component.

In [Equation (1) and (2), R ₁ and R ₂ are both a hydrogen atom or a methyl group. ]

Specific examples of the (meth) acrylate represented by the formula (1) include o-phenylphenyl acrylate in which R ₁ is a hydrogen atom, and o-phenylphenyl methacrylate in which R ₁ is a methyl group.
Specific examples of the (meth) acrylate represented by the formula (2) include p-cumylphenyl acrylate in which R ₂ is a hydrogen atom, and p-cumylphenyl methacrylate in which R ₂ is a methyl group. Can do.

  In addition, the (meth) acrylate which has one phenyl group different from the (B) component of this invention, and the compound which has an alkylene oxide group do not become what the hardened | cured material of a composition has a high refractive index.

3. Other components In the present invention, in order to improve the adhesion of the composition of the present invention to the resin substrate, to reduce the viscosity of the composition, or to improve the adhesive strength, the unsaturated components other than the component (B) A bond-containing compound [hereinafter referred to as (C)] may be used.
Specific examples of the component (C) include, for example, phenoxyethyl (meth) acrylate, phenyloxyethyloxyethyl (meth) acrylate, phenyl poly (degree of polymerization: n = 2 to 4 as an average value) ethoxy acrylate, o-phenylphenyl Oxyethyl (meth) acrylate, o-phenylphenyloxyethyloxyethyl (meth) acrylate, o-phenylphenyl poly (degree of polymerization: n = 2 to 4 as an average value) ethoxy acrylate, tribromophenyloxyethyl (meth) acrylate , Tribromobenzyl (meth) acrylate, bisphenol A poly (degree of polymerization: n = 2 to 15 as an average value) ethoxydi (meth) acrylate, 1,6-hexanediol diacrylate, polyethylene glycol di (meth) acrylate, nonane Oruji (meth) acrylate, N- vinyl caprolactam, acryloyl morpholine and trimethylolpropane polyethoxy tri (meth) acrylate.

  Among these, preferred are, for example, phenoxyethyl acrylate, phenyl poly (degree of polymerization: n = 2 to 4 as an average value) ethoxy acrylate, o-phenylphenyloxyethyl acrylate, o-phenylphenyl poly (degree of polymerization: average value) N = 2 to 4) ethoxy acrylate, tribromophenyloxyethyl acrylate, bisphenol A poly (degree of polymerization: n = 4 to 10 as an average value) ethoxydiacrylate and the like acrylate monomers having a high refractive index, and the like. .

The composition of the present invention is cured by irradiation with active energy rays, and examples of the active energy rays in this case include electron beams, visible rays, and ultraviolet rays. Among these, visible light or ultraviolet light is preferable because it does not require a special device and is simple.
When a visible light or ultraviolet curable composition is used, a photopolymerization initiator is added to the composition. In addition, when setting it as an electron beam curable composition, it is not necessary to mix | blend a photoinitiator.
Specific examples of the photopolymerization initiator [hereinafter referred to as component (D)] include benzoin such as benzoin, benzoin methyl ether and benzoin propyl ether; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy- 2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one and N, N-dimethylamino Acetophenones such as acetophenone; anthraquinones such as 2-methylanthraquinone, 1-chloroanthraquinone and 2-amylanthraquinone; 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone and 2,4-di Thioxanthones such as sopropylthioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, methylbenzophenone, 4,4′-dichlorobenzophenone, 4,4′-bisdiethylaminobenzophenone, Michler's ketone, and 4-benzoyl-4′-methyl Benzophenones such as diphenyl sulfide; and 2,4,6-trimethylbenzoyl diphenylphosphine oxide.
(D) A component may be used independently or may use 2 or more types together.

  (D) A photosensitizer can be used together with a component as needed. Examples of the photosensitizer include N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, triethylamine, and triethanolamine.

The composition of the present invention can be heated after irradiation with active energy rays by blending the composition with a thermal polymerization initiator for the purpose of further curing.
Various compounds can be used as the thermal polymerization initiator, and organic peroxides and azo initiators are preferred.
Specific examples of the organic peroxide include 1,1-bis (t-butylperoxy) 2-methylcyclohexane, 1,1-bis (t-hexylperoxy) -3,3,5-trimethylcyclohexane, , 1-bis (t-hexylperoxy) cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, , 2-bis (4,4-di-butylperoxycyclohexyl) propane, 1,1-bis (t-butylperoxy) cyclododecane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxymaleic acid, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, 2,5-dimethyl- , 5-di (m-toluoylperoxy) hexane, t-butylperoxyisopropyl monocarbonate, t-butylperoxy 2-ethylhexyl monocarbonate, t-hexylperoxybenzoate, 2,5-dimethyl-2,5 -Di (benzoylperoxy) hexane, t-butylperoxyacetate, 2,2-bis (t-butylperoxy) butane, t-butylperoxybenzoate, n-butyl-4,4-bis (t-butyl) Peroxy) valerate, di-t-butylperoxyisophthalate, α, α′-bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-di (t- Butylperoxy) hexane, t-butylcumyl peroxide, di-t-butylperoxide P-menthane hydroperoxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexyne-3, diisopropylbenzene hydroperoxide, t-butyltrimethylsilyl peroxide, 1,1,3 Examples include 3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroperoxide, and t-butyl hydroperoxide.

Specific examples of the azo compound include 1,1′-azobis (cyclohexane-1-carbonitrile), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile. Azodi-t-octane and azodi-t-butane.
These may be used alone or in combination of two or more. Moreover, an organic peroxide can also be made into a redox reaction by combining with a reducing agent.

  In addition to the above components, the composition of the present invention may further contain a light stabilizer (for example, a hindered amine compound), a plasticizer, a mold release agent, an antifoaming agent, a leveling agent, an antioxidant, and a polymerization inhibitor, as desired. An agent, an antistatic agent, a non-reactive polymer (for example, polyester elastomer, polyurethane elastomer, poly (meth) acrylate polymer, etc.), and the like can be blended.

4). Active energy ray-curable optical material composition The present invention essentially comprises the component (A) and the component (B).
As a ratio of (A) component and (B) component, (A) component is 10-70 mass parts and (B) component is 30-90 mass parts on the basis of the total amount of (A) and (B) component. More preferably, (A) component is 20-60 mass parts and (B) component is 40-80 mass parts.
If the component (A) is less than 10 parts by mass, sufficient adhesion performance may not be obtained. On the other hand, if it exceeds 70 parts by mass, the refractive index of the cured product may be insufficient. In some cases, the viscosity becomes too high and workability may be reduced.
(C) As a ratio in the case of using a component, 5-60 mass parts is preferable with respect to the total amount of (A) and (B) component, More preferably, it is 10-50 mass parts.
(D) As a ratio in the case of using a component, 0.1-15 mass with respect to 100 mass parts for the total amount of (A) and (B) component or the total amount of (A)-(C) component. Part is preferable, and more preferably 0.5 to 10 parts by mass.

  The composition of the present invention can be produced by stirring and mixing the above-mentioned components (A) and (B) and other components as necessary according to a conventional method.

As a method of using the composition of the present invention, the composition may be cured by irradiating the composition with active energy rays.
Examples of the active energy ray include an electron beam, visible light, and ultraviolet light. Among these, visible light or ultraviolet light is preferable because it does not require a special device and is simple. Examples of the ultraviolet irradiation device include a high-pressure mercury lamp.
What is necessary is just to set suitably the irradiation amount of an active energy ray, irradiation time, etc. according to the composition to be used and a use.

  The composition of the present invention preferably has a cured product having a refractive index at 25 ° C. of 1.55 or more, preferably 1.58 or more.

Since the cured product of the composition of the present invention has a high refractive index and transparency, it can be used for various optical materials such as lens sheets such as Fresnel lenses, lenticular lenses and prism sheets, and plastic lenses.
More specifically, examples of the lens sheet include uses such as a video projector, a projection television, and a liquid crystal display.

The example which manufactures a lens sheet using the composition of this invention is demonstrated.
When producing a relatively thin lens sheet, the composition of the present invention is applied to a mold called a stamper having the shape of the target lens, and a layer of the composition is provided. A transparent substrate is bonded on top.
Next, active energy rays are irradiated from the transparent substrate side to cure the composition, and then peel from the mold.

On the other hand, when producing a lens sheet having a relatively thick film thickness, the composition of the present invention is poured between a mold having a target lens shape and a transparent substrate.
Next, active energy rays are irradiated from the transparent substrate side to cure the composition, and thereafter, the mold is removed from the mold.

As the transparent substrate, a resin substrate is preferable. As a specific example, a sheet-like substrate such as a polycarbonate resin, a polystyrene resin, a polyester resin, a (meth) acrylic resin, or a mixed resin thereof can be used. Among these, (meth) acrylic resins are preferable.
The material of the mold is not particularly limited, and examples thereof include metals such as brass and nickel, and resins such as epoxy resins. It is preferable that the mold is made of metal in view of the long life of the mold.

Especially the composition of this invention can be preferably used as an adhesive agent of an optical material.
As a usage method in this case, there is a method of applying the composition to one of the substrates to be bonded, laminating with the other substrate, and irradiating with active energy rays.
As a base material at this time, for example, a polycarbonate resin, a polystyrene resin, a polyester resin, a (meth) acrylic resin, or a mixed resin thereof are bonded together, or the resin base material and a lens sheet are bonded together. . Among these, it can be preferably used for adhesion of (meth) acrylic resin.

  The composition of the present invention is low in viscosity and easy to handle, and its cured product has a high refractive index, which is suitable for the production of optical materials such as lens sheets. Furthermore, since the composition of this invention is excellent in adhesiveness, such as adhesiveness with various plastic base materials, and adhesive strength, it can be used conveniently as an adhesive agent for bonding of these optical materials.

The composition of the present invention essentially comprises the components (A) and (B).
As a composition, what further contains (C) component is preferable, and what further contains (D) component is preferable.
As a hardened | cured material of a composition, what has a refractive index in 25 degreeC of 1.55 or more is preferable.
As an application of the composition, an adhesive for optical materials is preferable.

  Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. In the following description, “part” means “part by mass” unless otherwise specified.

O Synthesis example 1. [Production of component (A)]
After charging 533 parts of isophorone diisocyanate (hereinafter referred to as IPDI) into a 3 L flask previously blown with an oxygen / nitrogen mixed gas and bubbling the oxygen / nitrogen mixed gas at room temperature for an additional hour, dibutyltin dilaurate (hereinafter referred to as DBTL). 2 parts) and 0.6 part of di-t-butylhydroxytoluene were charged, and the temperature of the bath was started at 60 ° C. Then, using a dropping funnel, polytetramethylene glycol [weight average molecular weight 1,000; Hodogaya Chemical 1234 parts of PTG-1000 manufactured by Ltd. was dropped into the flask over 1 hour.
Next, 278 parts of 2-hydroxyethyl acrylate (hereinafter referred to as HEA) was dropped into the flask over 1 hour. After completion of the dropwise addition, the bath temperature was raised to 80 ° C., and the reaction was further continued for 3 hours. The reaction was terminated because no peaks based on isocyanate were detected. The obtained urethane acrylate is referred to as (A-1-1).
(A-1-1) had a refractive index (25 ° C.) of 1.383 and a viscosity (25 ° C.) of 123,500 mPa · s.

O Synthesis example 2 [Production of component (A)]
In Synthesis Example 1, 377 parts of IPDI, 1 part of DBTL, and 0.3 part of di-t-butylhydroxytoluene were used, and instead of PTG-1000, 444 parts of Plaxel 205 (caprolactone diol manufactured by Daicel Chemical Industries, Ltd .; average molecular weight 530) A urethanization reaction was performed in the same manner as in Synthesis Example 1 except that it was used.
Next, 198 parts of HEA was used, and after raising the bath temperature to 80 ° C., the reaction was performed in the same manner as in Synthesis Example 1 except that the reaction was further continued for 2 hours.
The obtained urethane acrylate is referred to as (A-1-2).
(A-1-2) had a refractive index (25 ° C.) of 1.494 and a viscosity (25 ° C.) of 64,500 mPa · s.

O Synthesis example 3. [Production of component (A)]
In Synthesis Example 1, a 2 L flask was used, IPDI 70 parts, DBTL 0.8 parts, di-t-butylhydroxytoluene 0.3 parts were used, and instead of PTG-1000, Hiplex HX-2050 [Toho Rika Co., Ltd. The reaction was carried out in the same manner as in Synthesis Example 1 except that 500 parts of a diol consisting of repetition of 1,6-hexanediol and o-phthalic acid produced; average molecular weight of 2,000] was used.
Next, the reaction was carried out in the same manner as in Synthesis Example 1 except that a mixture of 250 parts of phenoxyethyl acrylate and 18 parts of HEA was used as a diluent, the bath temperature was raised to 80 ° C., and the reaction was further continued for 2 hours. It was.
The obtained urethane acrylate is referred to as (A-1-3).
(A-1-3) had a refractive index (25 ° C.) of 1.490 and a viscosity (25 ° C.) of 143,300 mPa · s.

○ Examples 1 to 10 and Comparative Examples 1 and 2
Each component shown in Table 1 is stirred and mixed according to a conventional method, and a solid photopolymerization initiator is heated and dissolved over 15 minutes in a drier previously maintained at 80 ° C. to prepare an ultraviolet curable composition. did.
The following evaluation was performed about the obtained composition.

(1) Viscosity In order to evaluate workability, the viscosity of the obtained composition was measured. The viscosity was measured at 25 ° C. using a RE80 type viscometer (E type) manufactured by Toki Sangyo Co., Ltd.

(2) Refractive Index The obtained composition was applied to a PMMA plate having a length of 15 cm, a width of 7 cm, and a thickness of 1 mm at a film thickness of 50 μm at room temperature using a bar coater. This was cured by two-pass ultraviolet irradiation with a high-pressure mercury lamp having a conveyor speed of 10 m / min, a lamp height of 10 cm, and an output of 80 W / cm.
Refractive index and adhesion were evaluated.
The refractive index (25 ° C.) of the obtained cured product was measured with an Abbe refractometer DR-M2 manufactured by Atago Co., Ltd.

(3) Adhesiveness About the hardened | cured material obtained by the method similar to evaluation of refractive index, the adhesiveness with the resin base material was evaluated by the cross-cut peel test. In Table 2, O, Δ, and X have the following meanings.
○: The number of remaining squares is 90-100
Δ: Number of remaining squares is 60-80
X: The number of remaining squares is 0 to 59

(4) Adhesiveness The obtained composition was applied to a PMMA plate having a length of 15 cm, a width of 7 cm, and a thickness of 1 mm at room temperature using a PET film having a thickness of 50 μm as a spacer. A resin layer having a thickness of 50 μm was obtained by laminating the film. This was cured by two-pass ultraviolet irradiation from the PMMA plate side with a high-pressure mercury lamp having a conveyor speed of 10 m / min, a lamp height of 10 cm, and an output of 80 W / cm.
The obtained cured product was cut off from the easy-adhesive PET film side with a width of 25 mm, the sample was attached to a tensile tester, and evaluation was performed by 180-degree peeling at a pulling speed of 300 mm / min.

In addition, the symbol in Table 1 shows the following meanings.
A-1-1: Urethane acrylate produced in Synthesis Example 1 A-1-2: Urethane acrylate produced in Synthesis Example 2 A-1-3: Urethane acrylate produced in Synthesis Example 3 SP-1509: Epoxy acrylate of bisphenol A, SP-1509 manufactured by Showa Polymer Co., Ltd.
P-CPA: p-cumylphenyl acrylate o-PPA: o-phenylphenyl acrylate M-110: p-cumylphenol ethylene oxide 1 mol-modified monoacrylate, Aronix M-110 manufactured by Toagosei Co., Ltd.
POA: phenoxyethyl acrylate ACMO: acryloylmorpholine M-210: bisphenol A ethylene oxide 4 mol modified diacrylate, Aronix M-210 manufactured by Toagosei Co., Ltd.
Irg184: 1-hydroxycyclohexyl phenyl ketone, Ciba Specialty Chemicals Irgacure 184

As is clear from the evaluation results in Table 2, the composition of the present invention had low viscosity and good workability. Moreover, since the cured product has a refractive index of 1.55 or more, it can be suitably used for an optical material such as a lens sheet. In addition, since it has good adhesion and adhesive strength, it can be suitably used for bonding optical materials.
On the other hand, the composition containing no component (B) is excellent in workability, adhesion and adhesive strength, but cannot obtain a cured product having a high refractive index (Comparative Example 1) or relatively good adhesion. Even if it has, only the thing inferior to workability | operativity, refractive index, and adhesive force was obtained (comparative example 2). The composition containing no component (A) has good workability and refractive index, but did not have sufficient adhesion and adhesive strength (Comparative Example 3).

The composition of the present invention can be used for the production of lens sheets such as Fresnel lenses and lenticular lenses used in video projectors, projection televisions, liquid crystal displays and the like, and is suitably used as an adhesive used in bonding these optical materials. Can be used.

Claims (5)

Activity comprising urethane (meth) acrylate and / or epoxy (meth) acrylate (A) and (meth) acrylate (B) represented by the following formula (1) and / or formula (2) Composition for energy beam curable optical material.

In [Equation (1) and (2), R ₁ and R ₂ are both a hydrogen atom or a methyl group. ] The active energy ray-curable optical material composition according to claim 1, further comprising an unsaturated group-containing compound (C) other than the component (B). The composition for an active energy ray-curable optical material according to claim 1 or 2, further comprising a photopolymerization initiator (D). The active energy ray-curable optical material composition according to any one of claims 1 to 3, wherein the cured product has a refractive index at 25 ° C of 1.55 or more. The adhesive for optical materials which consists of a composition in any one of Claims 1-4.