JPH11271504A - Composition curable with activation energy beam for sheetlike optical article - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compsn. having a low viscosity, excellent in releasability from a lens matrix after curing, giving a cured body excellent in adhesion to a transparent substrate and suitable for producing a flexible tough sheetlike optical article less liable to warp by using an imido(meth)acrylate and a specified compd. SOLUTION: The compsn. comprises 20-95 wt.% imido (meth)acrylate and 80-5 wt.% compd. having two or more ethylenically unsatd. groups. The imido(meth)acrylate is preferably one or more selected from the compds. represented by formulae I-V, wherein R1 -R3 , are each H or methyl, R4 is H or Cn H2n+1 , (n) is 1-6, (l) is 2-3 and (m) is 1-3. The compd. having two or more ethylenically unsated. groups is preferably one or more selected from urethane poly(meth) acrylates, polyester poly(meth)acrylates and epoxy poly(meth)acrylates.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a Fresnel lens,
The present invention relates to an active energy ray-curable composition suitable for producing sheet-like optical articles such as lenticular lenses and prism sheets.

[0002]

2. Description of the Related Art Hitherto, sheet-like optical articles such as Fresnel lenses have generally been manufactured by injection molding or hot press molding of a thermoplastic resin. However, these production methods have a problem that heating and cooling during production require a long time, and the productivity is low. Therefore, in recent years, as a method of manufacturing a sheet-shaped optical article that solves the above-mentioned problem, an active energy between a lens-shaped base material such as a mold or a resin mold and a transparent base material such as a transparent resin substrate or a film is used. A method of pouring a radiation-curable composition and irradiating the composition with an active energy ray such as ultraviolet rays to cure the composition has been adopted. As the active energy ray-curable composition used in the production method,
Generally, a (meth) acrylate-based composition that is cured by active energy ray-initiated radical polymerization and is composed of oligomers such as urethane (meth) acrylate, epoxy (meth) acrylate, and polyester (meth) acrylate is used.

[0003]

The properties required for the active energy ray-curable composition used in the above-mentioned production method are as follows. The cured product is soft so that it has a low viscosity, and after curing, the resulting sheet-shaped optical article can be peeled off from the lens-type base material without cracking or chipping. And high strength, and excellent adhesion to a transparent substrate. In addition to these, it is also required that the surface of the sheet after peeling is not damaged, and that the sheet does not warp. Oligomers such as urethane (meth) acrylate, epoxy (meth) acrylate, and polyester (meth) acrylate used in the composition had high viscosity and were difficult to use as they were. Therefore, for the purpose of viscosity reduction,
It is necessary to incorporate a large amount of a reactive diluent such as a monofunctional acrylate into the composition.However, a composition containing a large amount of the reactive diluent has a brittle cured product and is separated from the lens-type base material. In some cases, it was cracked or peeled off due to insufficient adhesion with the transparent substrate. Particularly, in the production of sheet-shaped optical articles, a composition composed of urethane (meth) acrylate is preferably used because the cured product thereof has excellent elongation and flexibility. However, since the composition has a very high urethane (meth) acrylate viscosity, it is necessary to incorporate a large amount of a reactive diluent into the composition in order to reduce the viscosity. Because it contains a large amount of reactive diluent, the characteristics of urethane (meth) acrylate, that is, the excellent elongation and strength of the cured product are reduced, and the adhesion to the transparent substrate is also reduced. It was a mess. In addition, various compositions other than these have been studied, but none satisfying all of the above requirements has yet been obtained. We have:
Low viscosity, excellent releasability from the cured lens mold base material, excellent adhesion of the cured product to the transparent substrate, suitable for producing sheet-shaped optical articles that are flexible, tough and less warped In order to find an active-energy-ray-curable composition, the present inventors have conducted intensive studies.

[0004]

Means for Solving the Problems In view of the present situation, the present inventors have made various studies and found that imide (meth)
A composition comprising an acrylate and a compound having two or more ethylenically unsaturated groups has a low viscosity and can be easily released from a lens-type base material after curing, and the cured product has good adhesion to a transparent substrate. The present invention was found to be excellent in flexibility, excellent in toughness, and low in warpage. Hereinafter, the present invention will be described in detail. In the present specification, acrylate or / and methacrylate is represented as (meth) acrylate, acryloyl or / and methacryloyl is represented as (meth) acryloyl, and acrylic acid or / and / or methacrylic acid is represented by (meth) acrylic acid. It expresses.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION (A) Imide (meth) acrylate As the imide (meth) acrylate of the component (A) used in the present invention, various compounds can be used.
One or two selected from compounds represented by formula (5)
More than species are preferred.

[0006]

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[0007]

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[0008]

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[0009]

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[0010]

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(However, in each formula, R ₁ , R ₂ and R ₃ are a hydrogen atom or a methyl group, R ₄ is a hydrogen atom or C _n H _{2n + 1} , and n = 1 to 6. And l = 2
3, m = 1 to 3. )

The compound represented by the formula (1) is an imide (meth) acrylate having a tetrahydrophthalimide skeleton having a double bond at the 4- and 5-positions, and m = 1 to 3. In the formula (1), when m is 4 or more, the imide moiety concentration in the molecule is reduced, so that the curability of the composition is reduced, and the toughness of the cured product is reduced and the composition becomes brittle. In some cases.

The compound represented by the formula (2) is an imide (meth) acrylate having a tetrahydrophthalimide skeleton having a double bond at the 1 and 2 positions, and m = 1 to 3. In the formula (2), when m is 4 or more, the imide moiety concentration in the molecule is reduced, so that the curability of the composition is reduced, and the toughness of the cured product is reduced and the composition becomes brittle. In some cases.

The compound represented by the formula (3) is an imide (meth) acrylate having a hexahydrophthalimide skeleton, and m = 1 to 3. In the formula (3), when m is 4 or more, the imide moiety concentration in the molecule is reduced, so that the curability of the composition is reduced, or the toughness of the cured product is reduced and the composition becomes brittle. In some cases.

The compound represented by the formula (4) is an imide (meth) acrylate having a succinimide skeleton.
= 1-3. In the formula (4), when m is 4 or more, the imide moiety concentration in the molecule is reduced, so that the curability of the composition is reduced or the toughness of the cured product is reduced, resulting in brittleness. In some cases.

The compound represented by the formula (5) is an imide (meth) acrylate having a phthalimide skeleton.
= 2-3. In the formula (5), the compound of l = 1 has extremely high crystallinity, low solubility in other monomers or oligomers, and is likely to precipitate crystals, which is not preferable in handling. Further, when l is 4 or more, the imide moiety concentration in the molecule is reduced, so that the curability of the composition may be reduced, or the toughness of the cured product may be reduced and the composition may become brittle. .

Among the compounds represented by the formula (1), R ₁
To R ₄ is a hydrogen atom, m is having 1, among the compounds represented by formula (2), R ₁ ~R ₄ is a hydrogen atom, m is 1
Things, among the compounds represented by formula (3), R ₁ ~
Among the compounds represented by the formula (4), those in which R ₄ is a hydrogen atom and m is 1, those in which R _{1 to} R ₄ are a hydrogen atom and m is 1 are represented by the formula (5). R _{1 to} R
_It is more preferable that ₄ is a hydrogen atom and 1 is 2 because of excellent curability of the composition and toughness and flexibility of the cured product.

Further, among the compounds represented by the formulas (1) to (5), the compound represented by the formula (3) is particularly preferable because the toughness and flexibility of the cured product are particularly excellent.

The compounds represented by the formulas (1) to (5) can be synthesized, for example, by the methods described in the following documents and patents. -Kiyoshi Kato et al., Synthetic Organic Chemistry Association, 30 (10), 89
7, (1972)-Javier de Abajo et al., Polymer, vol33.
(5), (1992) JP-A-56-53119 JP-A-1-242569

(B) Compound having two or more ethylenically unsaturated groups In the present invention, a compound having two or more ethylenically unsaturated groups as the component (B) is blended into the composition. Thereby, toughness can be imparted to the cured product. On the other hand, in the composition consisting only of imide (meth) acrylate, the cured product becomes brittle because the imide (meth) acrylate is a monofunctional (meth) acrylate. As the component (B), various compounds can be used as long as the compound has two or more radically polymerizable ethylenically unsaturated groups, and a compound having two or more (meth) acryloyl groups is preferable. As the compound having a (meth) acryloyl group,
Examples include poly (meth) acrylate, urethane poly (meth) acrylate, polyester poly (meth) acrylate, epoxy poly (meth) acrylate, and poly (meth) acrylate of (meth) acrylic polymer. Further, di (meth) acrylate having two (meth) acryloyl groups is preferable because the obtained cured product is excellent in elongation and flexibility.

Poly (meth) acrylate Poly (meth) acrylate includes alkylene glycol di (meth) acrylates such as ethylene glycol di (meth) acrylate and propylene glycol di (meth) acrylate; tetraethylene glycol di (meth) acrylate , Polyethylene glycol di (meth)
Acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate and polytetramethylene glycol di (meth)
Polyalkylene glycol di (meth) such as acrylate
Acrylates; glycol di (meth) acrylates such as 1,6-hexanediol di (meth) acrylate and neopentyl glycol di (meth) acrylate; bisphenol A di (meth) acrylate or its halogen nucleus-substituted product and bisphenol F di (meth) acrylate ) Bisphenol-type di (meth) acrylates such as acrylate or a halogen-nucleus-substituted product thereof; dimethyloltricyclodecanedi (meth) acrylate, trimethylolpropanetri (meth) acrylate, ditrimethylolpropanetetra (meth) acrylate, pentaerythritol tri Polyol poly (meth) acrylates such as (meth) acrylate, pentaerythritol tetra (meth) acrylate and dipentaerythritol hexa (meth) acrylate; Poly (meth) acrylates of alkylene oxide adducts of; isocyanuric di- or tri (meth) acid alkylene oxide acrylate. In addition to these, the document "Latest UV curing technology"
53-56 of [Printing Information Association Co., Ltd., issued in 1991]
And the like, for example, compounds described on the page.

Urethane poly (meth) acrylate Examples of urethane poly (meth) acrylate include compounds obtained by reacting a polyol and an organic polyisocyanate with a hydroxyl group-containing (meth) acrylate.

Here, examples of the polyol include low molecular weight polyols, polyethylene glycol and polyester polyols.
Examples include ethylene glycol, propylene glycol, cyclohexane dimethanol, and 3-methyl-1,5-pentanediol. Examples of polyether polyols include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol, and polyethylene polyether glycols. Block or random polymer diols such as propoxy block polymer diols, and the like. Polyester polyols include these low molecular weight polyols and / or polyether polyols, adipic acid, succinic acid, phthalic acid,
Examples thereof include an esterification reaction product with an acid component such as a dibasic acid such as tetrahydrophthalic acid, hexahydrophthalic acid, and terephthalic acid, or an anhydride thereof.

Examples of the organic polyisocyanate include tolylene diisocyanate, 1,6-hexane diisocyanate, 4,4'-diphenylmethane diisocyanate, polymethylene polyphenyl isocyanate, 1,6-hexane diisocyanate trimer, hydrogenated tolylene diisocyanate, Hydrogenated 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, paraphenylene diisocyanate, tolylene diisocyanate dimer, 1,5-naphthalene diisocyanate, hexamethylene diisocyanate mutual adduct, 4,4'- Dicyclohexylmethane diisocyanate, trimethylolpropane tris (tolylene diisocyanate) adduct, isophorone diisocyanate, and the like.

Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxypentyl (meth) acrylate, and hydroxyhexyl (meth) acrylate. Examples include acrylate, hydroxyoctyl (meth) acrylate, pentaerythritol tri, di- or mono (meth) acrylate, and hydroxyalkyl (meth) acrylate such as trimethylolpropane di- or mono (meth) acrylate.

As examples of other urethane poly (meth) acrylates, refer to the document “UV / EB cured material”.
70-74 of [CMC Co., Ltd., issued in 1992]
And the like, for example, compounds described on the page.

Polyester poly (meth) acrylate Examples of the polyester poly (meth) acrylate include dehydration condensates of polyester polyol and (meth) acrylic acid. Here, examples of the polyester polyol include a reaction product of the polyol with a carboxylic acid or an anhydride thereof, and examples of the polyol include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, and diethylene glycol. Propylene glycol, tripropylene glycol, polypropylene glycol, butylene glycol, polybutylene glycol,
Tetramethylene glycol, hexamethylene glycol, neopentyl glycol, cyclohexanedimethanol, 3-methyl-1,5-pentanediol, 1,6
-Hexanediol, trimethylolpropane, glycerin, low molecular weight polyols such as pentaerythritol and dipentaerythritol, and alkylene oxide adducts thereof, and the like.Orthophthalic acid, isophthalic acid, terephthalic acid, etc. Acid, adipic acid, succinic acid, fumaric acid, maleic acid,
Examples include dibasic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, and trimellitic acid or anhydrides thereof. Other polyester poly (meth) acrylates include the above-mentioned “UV / EB cured materials”, 74 to
Compounds such as those described on page 76 are exemplified.

Epoxy poly (meth) acrylate Epoxy poly (meth) acrylate is a compound obtained by adding (meth) acrylic acid to an epoxy resin, and is described in the above-mentioned document “UV / EB curing material”, pp. 74-75. Compounds such as those described are mentioned. Examples of the epoxy resin include an aromatic epoxy resin and an aliphatic epoxy resin.

Specific examples of the aromatic epoxy resin include resorcinol diglycidyl ether; bisphenol A, bisphenol F, bisphenol S, bisphenolfluorene or its alkylene oxide adduct di- or polyglycidyl ether; phenol novolak epoxy resin And novolak type epoxy resins such as cresol novolak type epoxy resin; glycidyl phthalimide; and diglycidyl ester of o-phthalic acid. In addition to these, Chapter 2 of the document “Epoxy Resin-Recent Advances” (issued by Shokodo, 1990) and the book “Polymer Processing”, Sep. 9, Vol. Published in 1973], pages 4 to 6 and 9 to 16 can be mentioned.

As the aliphatic epoxy resin, specifically, ethylene glycol, propylene glycol, 1,1,
Diglycidyl ethers of alkylene glycols such as 4-butanediol and 1,6-hexanediol; diglycidyl ethers of polyalkylene glycols such as diglycidyl ethers of polyethylene glycol and polypropylene glycol; neopentyl glycol, dibromoneopentyl glycol and alkylene oxide addition thereof Diglycidyl ethers of the form: di- or triglycidyl ethers of trimethylolethane, trimethylolpropane, glycerin and its alkylene oxide adducts, and polyvalents such as di, tri or tetraglycidyl ethers of pentaerythritol and its alkylene oxide adducts Polyglycidyl ether of alcohol; di- or polyglycol of hydrogenated bisphenol A and its alkylene oxide adduct Jill ether; tetrahydrophthalic acid diglycidyl ether; hydroquinone diglycidyl ether, and the like. In addition to these, there may be mentioned the compounds described on pages 3 to 6 of the above-mentioned document "Polymer processing", separate volume epoxy resin.

As the epoxy poly (meth) acrylate, an aliphatic epoxy (meth) acrylate is preferable in that the cured product is excellent in elongation and flexibility. Other than these aromatic epoxy resins and aliphatic epoxy resins, epoxy compounds having a triazine nucleus as a skeleton, such as TEPI
C [Nissan Chemical Co., Ltd.], Denacol EX-310 [Nagase Kasei Co., Ltd.] and the like, and compounds such as those described in the aforementioned "Polymer Processing" separate volume epoxy resin, pp. 289-296. Is mentioned. In the above, as the alkylene oxide of the alkylene oxide adduct, ethylene oxide and propylene oxide are preferable.

(Poly (meth) acrylate of (meth) acrylic polymer) The poly (meth) acrylate of (meth) acrylic polymer includes (meth) acrylic polymer having a functional group and (meth) acryloyl in a side chain. Compounds into which a group has been introduced, such as the compounds described on pages 78 to 79 of the above-mentioned document "UV / EB curing material".

Among the above-mentioned components (B), urethane poly (meth) acrylate, polyester poly (meth)
Acrylates and epoxy (meth) acrylates are preferred. When the urethane poly (meth) acrylate is used, the cured product becomes flexible and tough. When the polyester poly (meth) acrylate is used, the cured product becomes excellent in flexibility, becomes flexible and tough, and when the epoxy (meth) acrylate is used. The cured product is soft and tough. Among these, urethane poly (meth) acrylate,
It is more preferable because the cured product is particularly excellent in elongation, flexibility and toughness.

◎ Other components In addition to the above essential components, a compound having one ethylenically unsaturated group, an inorganic filler, a dye, a pigment, a viscosity controlling agent , A processing agent and an inert component such as an ultraviolet ray blocking agent.

Examples of the compound having one ethylenically unsaturated group include mono (meth) acrylate and N-vinylpyrrolidone. Examples of the mono (meth) acrylate include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; phenoxyethyl (meth) acrylate, phenol ethylene oxide modified (meth) acrylate, and phenol (Meth) acrylate of alkylene oxide adduct of phenol such as propylene oxide-modified (meth) acrylate, and its halogen nucleus; nonylphenol ethylene oxide-modified (meth) acrylate, nonylphenol-propylene oxide-modified (meth) acrylate and paracumylphenol alkylene oxide (Meth) acrylates of alkylene oxide adducts of alkyl phenols such as modified (meth) acrylates, and the like Modified (meth) acrylate of alkylene oxide of phenylphenol and its halogen-substituted product; 2-hydroxy-3-phenoxypropyl (meth) acrylate and substituted product of its halogen nucleus; (meth) acrylic acid of phenylphenol glycidyl ether Epoxy mono (meth) acrylates such as adducts and their halogen nucleus substitutes and cyclohexene oxide (meth) acrylic acid adducts; 2-ethylhexyl carbitol (meth) acrylate; isobornyl (meth) acrylate; and (meth) acryloyl morpho Phosphorus and the like. Other than these, there may be mentioned compounds such as those described in the document "Latest UV Curing Technology" (published by Technical Information Association, 1991), pp. 48-52.

In the present invention, when the composition is cured by ultraviolet rays, a photo-radical polymerization initiator is added.
Various photo-radical polymerization initiators can be used. Specifically, benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether and benzoin isopropyl ether and its alkyl ether; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxyacetophenone, 1-hydroxycyclohexylphenyl ketone and 2-methyl-1- [4
Acetophenones such as-(methylthio) phenyl] -2-morpholino-propan-1-one; anthraquinones such as 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone and 2-amylanthraquinone; 2,
Thioxanthones such as 4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone and 2,4-diisopropylthioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenones such as benzophenone; and xanthone. Can be Other than these, compounds described on pages 82 to 98 of the above-mentioned document “UV / EB curing material” can be mentioned. Two or more photoradical initiators can be used in combination, and furthermore, benzoic acid-based and amine-based photopolymerization initiators can be used in combination.

The content of these photo-radical polymerization initiators is based on the total amount of the components (A) and (B).
It is preferably 0.1 to 10% by weight, more preferably 0.1 to 5% by weight. When the amount is less than 0.1% by weight, the curability becomes sufficient. On the other hand, when the amount exceeds 10% by weight, the light transmittance becomes poor and the internal curability of a thick film may be deteriorated.

[0038] The composition may optionally contain an ultraviolet absorber, a light stabilizer, an antioxidant, and the like. As the ultraviolet absorber, 2- (5-methyl-2-hydroxyphenyl) benzotriazole and 2- (3,
Benzotriazole ultraviolet absorbers such as 5-di-t-amyl-2-hydroxyphenyl) benzotriazole and the like can be mentioned. As a light stabilizer, bis (1,
2,2,6,6-pentamethyl-4-piperidinyl) sebacate and bis (1,2- (3,5-di-t-butyl-4-hydroxybenzyl) -2-n-butylmalonate
Hindered amine light stabilizers such as 2,2,6,6-pentamethyl-4-piperidyl) and 2,4-di-t-
And benzoate light stabilizers such as butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate. As the antioxidant, triethylene glycol-bis [3- (3-t-butyl-5-methyl-4-hydroxyphenyl) propionate] and 1,6-hexanediol-bis [3,5-di-t-butyl-4] -Hydroxyphenyl) propionate] and the like.

Production Method The composition of the present invention can be obtained by mixing the above essential components and, if necessary, other components according to a conventional method.

In the present invention, the proportions of the components (A) and (B) in the composition are based on the total amount of these components.
The component (A) is 20 to 95% by weight and the component (B) is 80 to 5%.
% By weight. When the proportion of the component (A) is less than 20% by weight, the curability of the composition is poor, the viscosity of the obtained composition is high, and the foam is easily bitten when the composition is poured into the lens-type base material. And it becomes difficult to defoam the foam from the composition, or the cured product becomes hard without flexibility and breaks when peeled from the lens mold base material,
The film warps. On the other hand, when the ratio of the component (A) is 9
If the content exceeds 5% by weight, the cured product becomes brittle, breaks when peeled from the lens-type base material, and has poor resistance to damage.
The mixing ratio of the components (A) and (B) may be determined within the above range in consideration of the required viscosity of the composition, the hardness of the cured product, and the like. 30
Those having a kgf / cm ² or more and an elongation of 10% or more are preferable.

◎ Sheet Optical Article The sheet optical article of the present invention comprises a cured product obtained by irradiating the composition with an active energy ray to cure the composition. Examples of the sheet-shaped optical article include a Fresnel lens, a lenticular lens, a prism sheet, and the like.
As a method for manufacturing the sheet-shaped optical article, a method conventionally used in manufacturing the article may be used. For example, a method of pouring the composition between a resin or metal mold frame and a transparent substrate, irradiating the composition with an active energy ray, curing the composition, and peeling the composition from the mold to produce the composition may be used. Examples of the transparent substrate include glass, plastic plates such as acrylic resin and polycarbonate resin, and plastic films such as polyester resin, polycarbonate resin and acrylic resin. The thickness of the lens may be appropriately selected according to the purpose of use. Examples of the active energy rays include ultraviolet rays, X-rays, and electron beams. When irradiating ultraviolet rays, various light sources can be used, and examples thereof include a low-pressure or high-pressure mercury lamp, a metal halide lamp, a xenon lamp, an electrodeless discharge lamp, and a carbon arc lamp. In the case of curing with an electron beam, various irradiation devices can be used, and examples thereof include a Cockloft-Waldsin type, a Vandegraf type or a resonance transformer type, and the electron beam preferably has an energy of 50 to 1000 ev. And more preferably 100 to 300 eV. In the present invention, it is preferable to use ultraviolet light because an inexpensive device can be used.

[0042]

The present invention will now be described more specifically with reference to examples and comparative examples. In the following, “parts” means parts by weight.

Example 1 80 parts of a compound represented by the following formula (6) were mixed with 20 parts of a bisphenol A-type ethylene oxide modified diacrylate [Aronix M-210, manufactured by Toagosei Co., Ltd.]
Further, 3 parts of 1-hydroxycyclohexyl phenyl ketone (Irgacure 184, manufactured by Ciba Specialty Chemicals Co., Ltd.) as a photopolymerization initiator was added and mixed.
An active energy ray-curable composition was prepared. The following evaluation was performed about the obtained composition. Table 2 shows the obtained results.

Viscosity measurement The viscosity was measured at 25 ° C. using an E-type viscometer. Tensile strength and elongation The obtained composition was irradiated with an ultraviolet ray irradiator equipped with a parallel mercury lamp of 60 w / cm [lamp height = 30 cm, irradiation intensity: 40 mW / cm ² , 30 mJ / cm ² (conveyor speed 10 m / (measured in min.)], and irradiate for a total of 3 minutes on the front and back to make a dumbbell No. 2 with a thickness of 1 mm.
It was measured according to IS K6301. -Releasability The obtained composition was poured into a resin Fresnel lens form having a thickness of 400 microns, laminated with a PET film from above, and then a conveyor-type ultraviolet irradiation device equipped with a 120 w / cm metal halide lamp ( Using a lamp height of 10 cm, a conveyor speed of 10 m / min, and an irradiation intensity of 780 mW / cm ² , 320 mJ / cm ² ), three passes were made (10 m / min is defined as one pass). The obtained lens was peeled off from the mold, and the mold releasability at that time was evaluated as ○ when the mold was peeled cleanly from the mold, and x when the resin remained or cracked in the mold. The obtained lens had no problem in performance as a lens.

Examples 2 to 13 Using 1 part of 1-hydroxycyclohexyl phenyl ketone (Irgacure 184) at a composition ratio shown in Table 1,
A composition was prepared in the same manner as in Example 1. The obtained composition was evaluated in the same manner as in Example 1. Table 2 shows the results. The obtained lens had no problem in performance as a lens.

[0046]

[Table 1]

The abbreviations in Table 1 mean the following compounds. A: imide acrylate represented by the following formula (6)

[0048]

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B: imide acrylate represented by the following formula (7)

[0050]

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C: imide acrylate represented by the following formula (8)

[0052]

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D: imide acrylate represented by the following formula (9)

[0054]

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E: bisphenol A type ethylene oxide modified diacrylate [Aronix M-210, manufactured by Toagosei Co., Ltd.] F: tripropylene glycol diacrylate [Aronix M-220, manufactured by Toagosei Co., Ltd.] G: Trimethylolpropane propylene oxide modified triacrylate [Toagosei Co., Ltd., Aronix M-350] H: Urethane acrylate [Nihon Gosei Kagaku Co., Ltd.
Purple light UV-7000B] I: urethane acrylate [manufactured by Nippon Synthetic Chemical Co., Ltd.
Purple light UV-7500B] ・ J: Urethane acrylate [Toagosei Co., Ltd., Aronix M-1600] ・ K: Urethane acrylate [Toagosei Co., Ltd., Aronix M-1310] ・ L: Polyester acrylate [Toagosei ( Co., Ltd.
Aronix M-6200] M: 1,6-hexanediol diglycidyl ether acrylic acid adduct [Epoxyester 1600A, manufactured by Kyoeisha Yushi Kagaku Co., Ltd.] N: Glycerin diglycidyl ether acrylic acid adduct [Kyoeisha Yushi Kagaku ( Co., Ltd., epoxy ester 80M
FA] · O: bisphenol A type diglycidyl ether acrylic acid adduct [Lipoxy SP-15, manufactured by Showa Polymer Co., Ltd.]
09] -P: 2-hydroxy-3-phenoxypropyl acrylate [manufactured by Toagosei Co., Ltd., Aronix M-570
0] Q: Isoboronyl acrylate [Light acrylate IB-XA, manufactured by Kyoeisha Yushi Kagaku KK]

[0056]

[Table 2]

Comparative Examples 1 to 4 Using 1 part of 1-hydroxycyclohexyl phenyl ketone (Irgacure 184) at a composition ratio shown in Table 3,
A composition was prepared in the same manner as in Example 1. The obtained composition was evaluated in the same manner as in Example 1. Table 3 shows the results.

[0058]

[Table 3] 1) The unit is mPa · s / 25 ° C

The abbreviations in Table 3 mean the following compounds. S: Phenol ethylene oxide modified acrylate [Toagosei Co., Ltd., Aronix M-101] T: Acryloylmorpholine [Kojin Co., Ltd., AC
MO] F: Tripropylene glycol diacrylate [Toagosei Co., Ltd., Aronix M-220] H: Urethane acrylate [Nippon Synthetic Chemical Co., Ltd.
Purple light UV-7000B] · J: urethane acrylate [Toagosei Co., Ltd., Aronix M-1600]

[0060]

The composition for an active energy ray-curable sheet-like optical article of the present invention has a low viscosity, is excellent in releasability from a cured lens mold base material, and has a cured product in close contact with a transparent substrate. The cured product is excellent in flexibility, excellent in toughness and low in warpage, and is extremely practical.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI G03F 7/027 514 G03F 7/027 514 7/038 505 7/038 505 // B29D 11/00 B29D 11/00

Claims (4)

[Claims] (A) an imide (meth) acrylate 20 or more
An active energy ray-curable composition for sheet-like optical articles, comprising 95% by weight and (B) 80 to 5% by weight of a compound having two or more ethylenically unsaturated groups. 2. The active energy for a sheet-like optical article according to claim 1, wherein the component (A) is one or more selected from compounds represented by the following formulas (1) to (5). A line-curable composition. Embedded image Embedded image Embedded image Embedded image Embedded image (However, in each formula, R ₁ , R ₂ and R ₃ are a hydrogen atom or a methyl group, and R ₄ is a hydrogen atom or C _n H _{2n + 1.}
And n = 1 to 6. Also, l = 2-3, m = 1-3
It is. ) 3. The method according to claim 1, wherein the component (B) is one or more selected from urethane poly (meth) acrylate, polyester poly (meth) acrylate and epoxy poly (meth) acrylate. An active energy ray-curable composition for a sheet-like optical article according to any of the above items. 4. A sheet-like optical article comprising a cured product obtained by irradiating the composition according to claim 1, 2 or 3 with an active energy ray to cure the composition.