WO2010137501A1 - Composition de résine durcissable par rayonnement énergétique pour feuille de lentille optique et produit durci correspondant - Google Patents

Composition de résine durcissable par rayonnement énergétique pour feuille de lentille optique et produit durci correspondant Download PDF

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WO2010137501A1
WO2010137501A1 PCT/JP2010/058421 JP2010058421W WO2010137501A1 WO 2010137501 A1 WO2010137501 A1 WO 2010137501A1 JP 2010058421 W JP2010058421 W JP 2010058421W WO 2010137501 A1 WO2010137501 A1 WO 2010137501A1
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meth
group
acrylate
resin composition
compound
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PCT/JP2010/058421
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English (en)
Japanese (ja)
Inventor
典子 清柳
聡 小木
淳子 市川
敬夫 小柳
貴文 水口
弘 桜井
律子 設楽
伸彦 内藤
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日本化薬株式会社
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Priority to JP2011515992A priority Critical patent/JPWO2010137501A1/ja
Publication of WO2010137501A1 publication Critical patent/WO2010137501A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Definitions

  • the present invention relates to an energy ray curable resin composition for an optical lens sheet and a cured product thereof. More specifically, the present invention relates to a resin composition and a cured product particularly suitable for lenses such as a Fresnel lens, a lenticular lens, a prism lens, and a microlens.
  • the above-described lens has been molded by a method such as a press method or a cast method (casting method).
  • the former pressing method was poor in productivity because it was manufactured by heating, pressurizing and cooling cycles.
  • 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 manufacturing cost increases because a large number of molds are required.
  • Patent Documents 1 and 2 various proposals have been made for using an ultraviolet curable resin composition.
  • a method for producing an optical lens sheet used for a transmission screen or the like by using these ultraviolet curable resin compositions has been somewhat successful.
  • these conventional cured resin compositions have the drawback of poor adhesion to the substrate and releasability from the mold. If the adhesion is poor, the types of substrates that can be used are limited, making it difficult to obtain the intended optical properties. If the releasability is poor, the resin remains in the mold at the time of mold release, and the mold cannot be used.
  • a resin composition that gives a cured product with good adhesion is likely to have poor mold releasability because of good adhesion to the mold.
  • a resin composition with good mold releasability tends to have poor adhesion. is there. Therefore, it is desired to provide a resin composition that can satisfy both the performance of adhesion to the substrate and the releasability from the mold.
  • the composition for lenses used in these optical lens sheets and the like has been demanded to have a high refractive index in accordance with recent high-definition images and thinning of final products.
  • a low-viscosity one tends to be required.
  • the fine structure is not easily crushed when the lens sheet is wound up.
  • a high glass transition temperature (Tg) is required.
  • Patent Document 3 proposes a resin composition having both adhesiveness and releasability, but it cannot be said that the viscosity for processing into a finer shape is sufficient.
  • Reference 4 discloses that ⁇ -N-carbazolylethyl acrylate is used as a monomer for obtaining a photoconductive resin, but the performance of ⁇ -N-carbazolylethyl acrylate before polymerization is disclosed. And its optical features are not specified.
  • Patent Document 5 proposes a transparent resin composition containing a compound having a carbazolyl group, but the compound is an antioxidant and is not a monomer for an energy ray curable resin, but a cured product. It prevents coloring.
  • Patent Document 6 discusses a curable composition containing a compound having a carbazolyl group, but the compound is a polymer having a carbazolyl group as a structural unit, not a monomer.
  • the object of the present invention is a low-viscosity resin composition suitable for the production of lens sheets such as Fresnel lenses, lenticular lenses, prism lenses, and micro lenses, and is excellent in releasability, mold reproducibility, adhesion, and light resistance. It provides a cured product having a high refractive index.
  • an ultraviolet curable resin composition having a specific composition and a cured product thereof can solve the above problems, and have completed the present invention.
  • the present invention provides (1) an energy ray curable resin composition for an optical lens sheet comprising a compound (A) having a carbazolyl group and a photopolymerization initiator (B), (2) Compound (C) in which compound (A) having a carbazolyl group is represented by formula (2)
  • the resin composition of the present invention has a low viscosity, and its cured product is excellent in releasability, mold reproducibility, and adhesion to a substrate, and has a high refractive index and good light resistance. Therefore, it is particularly suitable for optical lens sheets such as Fresnel lenses, lenticular lenses, prism lenses, and micro lenses.
  • the resin composition of the present invention contains a compound (A) having a carbazolyl group and a photopolymerization initiator (B).
  • the compound (A) having a carbazolyl group used in the resin composition of the present invention will be described.
  • the compound (A) having a carbazolyl group is not limited as long as it has a carbazolyl group, and examples thereof include compounds represented by the following general formula (1).
  • R 1 to R 9 are the same or different and are a hydrogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkylthio group, amino group, alkylamino group, aryl group, aryloxy group, arylthio group, aryl amino group, a diarylamino group, an alkylaryl group, a heterocyclic group, a polymerizable group, among .R 2 ⁇ R 9 at least one is a polymerizable group of R 1 ⁇ R 9, two adjacent Two substituents may be bonded to each other to form a ring structure, and R 2 to R 9 may further have a substituent.
  • the alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 8 carbon atoms. Specific examples include methyl, ethyl, t-butyl, cyclohexyl and the like.
  • the alkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, still more preferably 2 to 8 carbon atoms. Specific examples include vinyl, 1-propenyl, 1-buten-2-yl, cyclohexen-1-yl and the like.
  • the alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, and still more preferably 2 to 8 carbon atoms. Specific examples include ethynyl, 1-propynyl and the like.
  • the alkoxy group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, still more preferably 2 to 8 carbon atoms.
  • Specific examples include methoxy group, ethoxy group, butoxy group, octyloxy group, 2-ethylhexyloxy group and the like.
  • the alkylthio group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, and still more preferably 2 to 8 carbon atoms.
  • Specific examples include a methylthio group, an ethylthio group, a butylthio group, and an octylthio group.
  • the alkylamino group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, and still more preferably 2 to 8 carbon atoms.
  • Specific examples include a methylamino group, an ethylamino group, a butylamino group, a phenoxypropylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a piperidino group, and a morpholino group.
  • the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, and still more preferably 6 to 12 carbon atoms.
  • Specific examples include phenyl, biphenyl, tolyl, xylyl, naphthyl, pyrenyl and the like.
  • the aryloxy group preferably has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, still more preferably 6 to 8 carbon atoms.
  • Specific examples include a phenoxy group and a tolyloxy group.
  • the arylthio group preferably has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, and still more preferably 6 to 8 carbon atoms.
  • Specific examples include a phenylthio group.
  • the arylamino group preferably has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, and still more preferably 6 to 8 carbon atoms.
  • an anilino group, a toluidino group, etc. can be mentioned, for example.
  • the diarylamino group preferably has 12 to 30 carbon atoms, more preferably 12 to 20 carbon atoms, and still more preferably 12 to 15 carbon atoms. Specific examples include a diphenylamino group.
  • the alkylarylamino group preferably has 7 to 30 carbon atoms, more preferably 7 to 15 carbon atoms, and still more preferably 7 to 8 carbon atoms.
  • Specific examples include an N-methylanilino group and an N-ethylanilino group.
  • the heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms, and still more preferably 4 to 8 carbon atoms.
  • Specific examples include a pyrrole group, a furan group, and a carbazolyl group. These heterocyclic groups may have the above substituents represented by R 1 to R 9 .
  • a cyclic structure such as a cyclic hydrocarbon, an aromatic ring, a hetero ring, a hetero aromatic ring, etc. Also good.
  • Particularly preferred ring structures are aromatic hydrocarbon rings or heteroaromatic rings having a ring skeleton selected from thiophene, furan, pyrrole, selenophene and carbazole.
  • examples of the polymerizable group include a high strain hydrocarbon group such as a cyclopropane group and a cyclobutane group, a cyclic ether group such as an epoxy group and an oxetane group, an acrylic group, a methacryl group, a vinyl group, A vinyl ether group, a vinyl ester group, etc. are mentioned.
  • the polymerizable group is preferably an acryl group, a methacryl group, a vinyl group, an epoxy group, or an oxetane group, and particularly preferably an acryl group or a methacryl group.
  • the polymerizable group may be directly substituted on the ring structure or may be substituted via a divalent linking group.
  • Examples of the divalent linking group include an ether group and an alkylene group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as a methylene group (— CH 2- ), ethylene group (-CH 2 CH 2- ), trimethylene group (-CH 2 CH 2 CH 2- ), etc.), arylene group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include a phenylene group (—C 6 H 4 —), a naphthylene group (—C 10 H 6 —), and the like, and an oxyalkylene group ( Preferably it has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms.
  • an alkylene group preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon
  • oxymethylene group (—OCH 2 —), oxyethylene group (—OCH 2 CH 2 —) ,Such . Cited
  • oxyarylene group (preferably 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example oxy-phenylene group (-OC 6 H 4 -), An oxynaphthylene group (—OC 10 H 6 —) and the like), an oxycarbonyl group (—COO—), an iminocarbonyl group (—CONH—), a ureylene group (—NHCONH—) and the like.
  • These divalent linking groups may be further substituted with the above substituents.
  • the divalent linking group has a structure in which the same kind of divalent linking group (for example, ethylene oxide group) is repeatedly bonded. Or you may have a structure which couple
  • the compound represented by the general formula (1) can be synthesized by a known method.
  • a carbazole derivative can be obtained by synthesis or the like by an efficient cyclization reaction.
  • the raw material carbazole derivative is commercially available as an aryl hydrazine having a substituent corresponding to R 1, and is available from, for example, Aldrich or NJR Aromatics GmdH.
  • the obtained carbazole derivative is reacted with, for example, alkylene oxide or alkylene carbonate, and subjected to dehydration condensation reaction in the presence of (meth) acrylic acid and an acid catalyst, or reacted with epichlorohydrin, and then (meth) acrylic acid.
  • the compound represented by the general formula (1) can be obtained by reacting, but is not limited thereto.
  • a compound in which the heterocyclic group is a carbazolyl group can be synthesized by a known method described in WO 2005/014398 and J. Org. Chem. 2009, 74, p.4490-4498, and is also commercially available. .
  • the compound (A) having a carbazolyl group used in the resin composition of the present invention at least one of the substituents is a polymerizable group, and at least one of the substituents is a polymerizable group and is substituted.
  • at least one of the groups is a carbazolyl group which may have a substituent.
  • R 10 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms
  • R 11 is the same or different hydrocarbon group having 1 to 4 carbon atoms
  • n is an average number of repetitions
  • n 0 to 4 (which may have a substituent on the carbazolyl group)
  • the compound (C2) represented by the formula (wherein R 10 and R 11 and n are the same as those in the general formula (2)) is more preferable.
  • the compound (C) represented by the general formula (2) can be obtained by reacting carbazole with alkylene oxide or alkylene carbonate, followed by dehydration condensation reaction in the presence of (meth) acrylic acid and an acid catalyst. .
  • carbazole and alkylene oxide 1 to 8 mol of alkylene oxide is reacted with 1 mol of carbazole.
  • carbazole and alkylene carbonate 1 to 3 mol of alkylene carbonate is reacted with 1 mol of carbazole.
  • Alkylene oxide or alkylene carbonate may be used alone or in combination of two or more. When used alone, R 11 is all the same, and when used in a mixture of two or more, R 11 can be arbitrarily different.
  • the compound (C2) represented by the general formula (3) is obtained by reacting 3,3′-bi [9H-carbazole] with alkylene oxide or alkylene carbonate, and subsequently in the presence of (meth) acrylic acid and an acid catalyst. It can be obtained by dehydrating condensation reaction. In the reaction of carbazole with alkylene oxide, 2 to 16 moles of alkylene oxide are reacted with 1 mole of 3,3′-bi [9H-carbazole]. In the reaction of 3,3′-bi [9H-carbazole] with alkylene carbonate, 2 to 6 mol of alkylene carbonate is reacted with 1 mol of 3,3′-bi [9H-carbazole]. Alkylene oxide or alkylene carbonate may be used alone or in combination of two or more. When used alone, R 11 is all the same, and when used in a mixture of two or more, R 11 can be arbitrarily different.
  • alkylene oxide examples include alkylene oxides (1 to 4 carbon atoms) such as ethylene oxide, propylene oxide, and butylene oxide.
  • alkylene carbonate examples include alkylene carbonates (having 1 to 4 carbon atoms) such as ethylene carbonate (ethylene carbonate), propylene carbonate (propylene carbonate), butylene carbonate (butylene carbonate).
  • the reaction of carbazole or 3,3′-bi [9H-carbazole] with alkylene oxide or alkylene carbonate is carried out under an alkali catalyst such as sodium hydroxide or potassium hydroxide for a reaction time of 1 to 48 hours and a reaction temperature of 90 ° C. to 200 ° C. Performed between ° C.
  • an alkali catalyst such as sodium hydroxide or potassium hydroxide
  • 0.01 to 5% by mass of an alkali catalyst is used with respect to 100% by mass of the reaction mixture.
  • (meth) acrylic acid is carbazole or 3,3′-bi [ 9H-carbazole] is used in an amount of 0.1 to 20 moles per mole.
  • a reaction solvent in the dehydration condensation reaction an azeotropic solvent capable of distilling off water generated in the reaction can be used.
  • the azeotropic solvent here has a boiling point of 60 to 130 ° C.
  • non-reactive organic solvents such as benzene, toluene, n-hexane, n-heptane, and cyclohexane. It is desirable to use one kind or a mixture of two or more kinds.
  • the amount used is arbitrary, but is preferably 10 to 70% by mass with respect to the reaction mixture.
  • the reaction time in the dehydration condensation reaction may be 1 to 24 hours, and the reaction temperature may be in the range of 60 to 150 ° C., but it is preferably performed at 75 to 120 ° C. from the viewpoint of shortening the reaction time and preventing polymerization.
  • a commercially available (meth) acrylic acid used as a raw material is usually already added with a polymerization inhibitor such as p-methoxyphenol, but a polymerization inhibitor may be added again during the reaction.
  • a polymerization inhibitor such as p-methoxyphenol
  • examples of such polymerization inhibitors include hydroquinone, p-methoxyphenol, 2,4-dimethyl-6-t-butylphenol, 3-hydroxythiophenol, p-benzoquinone, 2,5-dihydroxy-p-benzoquinone, Examples include phenothiazine.
  • the amount used is 0.01 to 1% by mass with respect to the reaction mixture.
  • the acid catalyst used in the dehydration condensation reaction can be arbitrarily selected from known ones such as sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and the amount used is 1 mol of (meth) acrylic acid.
  • the content is 0.01 to 10 mol%, preferably 1 to 5 mol%.
  • the compound (C) that can be used in the resin composition of the present invention is a compound obtained by reacting 1 to 2 moles of alkylene oxide with 1 mole of carbazole in consideration of the refractive index and compatibility with other components.
  • a compound obtained by reacting (meth) acrylic acid with a compound obtained by reacting 1 to 2 moles of alkylene carbonate with 1 mole of carbazole is preferable.
  • the alkylene oxide may be any alkylene oxide having a methylene group of 1 to 4, but ethylene oxide or propylene oxide is preferred.
  • the alkylene carbonate may be any alkylene carbonate having a methylene group of 1 to 4, but ethylene carbonate (ethylene carbonate) or propylene carbonate (propylene carbonate) is preferred.
  • the compound (C2) that can be used in the resin composition of the present invention is 2 to 2 mol per mol of 3,3′-bi [9H-carbazole] in consideration of the refractive index and compatibility with other components.
  • (Meth) acrylic acid is reacted with a compound obtained by reacting 4 mol of alkylene oxide or a compound obtained by reacting 2 to 4 mol of alkylene carbonate with 1 mol of 3,3′-bi [9H-carbazole].
  • the compound obtained is preferred.
  • the alkylene oxide may be any alkylene oxide having a methylene group of 1 to 4, but ethylene oxide or propylene oxide is preferred.
  • the alkylene carbonate may be any alkylene carbonate having a methylene group of 1 to 4, but ethylene carbonate (ethylene carbonate) or propylene carbonate (propylene carbonate) is preferred.
  • Examples of the photopolymerization initiator (B) contained in the resin composition of the present invention include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether; acetophenone, 2,2-diethoxy- 2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2 Acetophenones such as methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, oligo [2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone] 2-D Anthraquinones such as luanthraquinone, 2-tert-butylanthra
  • the photopolymerization initiator (B) may be used singly or as a mixture of a plurality of types, but 2,4,6-trimethylbenzoyldiphenylphosphine oxide At least one phosphine oxide such as bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide or diphenyl- (2,4,6-trimethylbenzoyl) -phosphine oxide is preferably used.
  • the monoacrylate monomer (D) having a phenyl ether group that can be used in the present invention will be described.
  • Examples of the monoacrylate monomer (D) having a phenyl ether group include phenoxyethyl (meth) acrylate, phenyl (poly) ethoxy (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, and tribromophenyloxyethyl (meth).
  • Acrylate phenylthioethyl (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, phenylphenol (poly) ethoxy (meth) acrylate, phenylphenol epoxy (meth) acrylate, and the like.
  • Phenylphenol (poly) ethoxy (meth) acrylate and phenylphenol epoxy (meth) acrylate are preferred, among which o-phenylphenol (poly) ethoxy (meth) acrylate, - phenylphenol (poly) ethoxy (meth) acrylate, o- phenylphenol epoxy (meth) acrylate, p- phenylphenol epoxy (meth) acrylate.
  • the monoacrylate monomer (D) may be used alone or in combination of two or more.
  • the phenylphenol (poly) ethoxy (meth) acrylate is preferably a compound having an average number of repeating ethoxy structure moieties of 1 to 3, and a reaction product of phenylphenol and ethylene oxide, which is a raw material, and (meth) It can be obtained by reacting acrylic acid.
  • Phenylphenol can be obtained by using commercially available o-phenylphenol which is ortho form and p-phenylphenol which is para form (for example, O-PP and P-PP, both Can be obtained).
  • a reaction product of phenylphenol and ethylene oxide can be obtained by a known method, and a commercially available product can also be used.
  • the reaction product of phenylphenol and ethylene oxide is preferably a solvent (for example, toluene, cyclohexane, n- Phenylphenol polyethoxy (meth) acrylate is obtained by reacting with (meth) acrylic acid in the presence of hexane, n-heptane, etc., preferably at 70 to 150 ° C.
  • a solvent for example, toluene, cyclohexane, n- Phenylphenol polyethoxy (meth) acrylate is obtained by reacting with (meth) acrylic acid in the presence of hexane, n-heptane, etc., preferably at 70 to 150 ° C.
  • the proportion of (meth) acrylic acid used is 1 to 5 mol, preferably 1.05 to 2 mol, per mol of the reaction product of phenylphenol and ethylene oxide.
  • the esterification catalyst is 0.1 to 15 mol%, preferably 1 to 6 mol%, based on (meth) acrylic acid to be used.
  • the phenylphenol epoxy (meth) acrylate is obtained by reacting the above phenylphenol with an epihalohydrin in the presence of an alkali metal hydroxide, and reacting an epoxy resin as a reaction product with acrylic acid.
  • epihalohydrin epichlorohydrin, ⁇ -methylepichlorohydrin, ⁇ -methylepichlorohydrin, epibromohydrin and the like can be used, and among them, epichlorohydrin which is easily available industrially is preferable.
  • the amount of epihalohydrin used is usually 2 to 20 mol, preferably 3 to 15 mol, per 1 mol of phenylphenol.
  • alkali metal hydroxide examples include sodium hydroxide and potassium hydroxide, and a solid substance or an aqueous solution thereof may be used.
  • aqueous solution When using an aqueous solution, the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system, and water and epihalohydrin are distilled off continuously under reduced pressure or normal pressure, followed by liquid separation to remove the water. Alternatively, the epihalohydrin may be continuously returned to the reaction system.
  • the amount of alkali metal hydroxide used is usually 0.1 to 10.0 moles, preferably 0.3 to 5.0 moles, more preferably 0.8 to 3.0 moles per mole of the above phenylphenol. Is a mole.
  • a quaternary ammonium salt such as tetramethylammonium chloride, tetramethylammonium bromide, trimethylbenzylammonium chloride as a catalyst.
  • the amount used is usually 0.1 to 20 g, preferably 0.2 to 15 g, per 1 mol of the phenylphenol.
  • reaction it is preferable for the reaction to proceed by adding an aprotic polar solvent such as aliphatic alcohols such as methanol, ethanol and isopropyl alcohol, dimethylsulfone, dimethylsulfoxide, tetrahydrofuran and dioxane.
  • an aprotic polar solvent such as aliphatic alcohols such as methanol, ethanol and isopropyl alcohol, dimethylsulfone, dimethylsulfoxide, tetrahydrofuran and dioxane.
  • the amount used is usually 1 to 50% by mass, preferably 2 to 30% by mass, based on the amount of epihalohydrin used.
  • an aprotic polar solvent is used, it is usually 3 to 100% by mass, preferably 5 to 80% by mass, based on the amount of epihalohydrin used.
  • the reaction temperature is usually 30 to 100 ° C, preferably 35 to 90 ° C.
  • the reaction time is usually 0.2 to 10 hours, preferably 0.5 to 8 hours.
  • an alkali metal hydroxide, epihalohydrin and the like are removed under heating and reduced pressure after washing the reaction solution of phenylphenol and epihalohydrin with or without washing with water.
  • the obtained epoxy resin is dissolved in a solvent such as toluene or methyl isobutyl ketone, and an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is dissolved.
  • the reaction can be carried out by adding an aqueous solution to ensure ring closure.
  • the amount of alkali metal hydroxide used is usually 0.01 to 0.5 mol, preferably 0.05 to 0.3 mol, relative to 1 mol of phenylphenol used.
  • the reaction temperature is usually 50 to 120 ° C., and the reaction time is usually 0.5 to 2 hours.
  • the produced salt is removed by filtration, washing with water, etc., and the solvent is distilled off under heating and reduced pressure to obtain the desired epoxy resin.
  • An epoxy resin that can be used without special purification is obtained by a method represented by such a formulation.
  • Phenylphenol epoxy (meth) acrylate is obtained by reacting the aforementioned epoxy resin with (meth) acrylic acid.
  • (Meth) acrylic acid is preferably reacted in an amount of 0.8 to 1.1 equivalents, more preferably 0.9 to 1.05 equivalents, based on an epoxy equivalent of 1 of the epoxy resin.
  • the reaction can be carried out without a solvent, but if necessary, a solvent having no alcoholic hydroxyl group, for example, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aromatic carbonization such as benzene, toluene, xylene and tetramethylbenzene Hydrogens, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether and other glycol ethers, ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl Cellosolve acetate, butyl cellosolve acetate, carbitol acetate, propylene glycol monomethyl ether monoacetate, Esters such as dialkyl talates, dialkyl succinates, dialkyl
  • acryloylmorpholine terminal acrylic acid ester of 2-phenylphenol ethylene oxide adduct
  • Polyethylene glycol di (meth) acrylate tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane polyethoxytri (meth) acrylate, glycerin polypropoxytri (meth) Di (meth) acrylate (e.g. Nippon Kayaku Co., Ltd.
  • the reaction can be performed in a reaction product of pentaerythritol and ⁇ -caprolactone, such as poly (meth) acrylate or dipentaerythritol poly (meth) acrylate.
  • a reaction product of pentaerythritol and ⁇ -caprolactone such as poly (meth) acrylate or dipentaerythritol poly (meth) acrylate.
  • a catalyst for promoting the reaction.
  • the amount of the catalyst used is 0.1 to 10% by mass with respect to the reaction product.
  • the reaction temperature at that time is 60 to 150 ° C., and the reaction time is preferably 5 to 60 hours.
  • the catalyst used include triethylamine, benzyldimethylamine, triethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, triphenylphosphine, triphenylstibine, methyltriphenylstibine, chromium octoate, zirconium octoate and the like. Can be mentioned.
  • a thermal polymerization inhibitor may be used, and examples of the thermal polymerization inhibitor include hydroquinone monomethyl ether, 2-methylhydroquinone, hydroquinone, 2,6-di-tert-butyl-p-cresol, and diphenylpicryl. Examples include hydrazine and diphenylamine.
  • a thermal polymerization inhibitor is used, it is preferably used in an amount of about 0.1 to 10% by mass with respect to the reaction product. The reaction is terminated at an appropriate time when the acid value of the sample is 5 mg ⁇ KOH / g or less, preferably 3 mg ⁇ KOH / g or less.
  • the (meth) acrylate compound (E) other than the component (A) and the component (D) may be used alone or in combination of two or more. Good.
  • the (meth) acrylate compound (E) include (meth) acrylate monomers and (meth) acrylate oligomers.
  • Examples of the (meth) acrylate monomer include a monofunctional (meth) acrylate monomer, a bifunctional (meth) acrylate monomer, a trifunctional or higher polyfunctional (meth) acrylate monomer, and the like.
  • Examples of the monofunctional (meth) acrylate monomer include acryloylmorpholine, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexane-1,4-dimethanol mono (meth) acrylate, and tetrahydrofurfuryl.
  • bifunctional (meth) acrylate monomers include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, and tricyclodecanedi.
  • Examples of the trifunctional or higher polyfunctional (meth) acrylate monomer include tris (acryloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, Examples include pentaerythritol hexa (meth) acrylate, tripentaerythritol penta (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane polyethoxytri (meth) acrylate, and ditrimethylolpropane tetra (meth) acrylate. it can.
  • Examples of (meth) acrylate oligomers include urethane (meth) acrylate, epoxy (meth) acrylate, and polyester (meth) acrylate.
  • urethane (meth) acrylate examples include diol compounds (for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4-butanediol, neopentyl glycol, 1,6- Hexanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentane Diol, 2-butyl-2-ethyl-1,3-propanediol, cyclohexane-1,4-dimethanol, polyethylene glycol, polypropylene glycol, bisphenol A polyethoxydiol, bisphenol A polypropoxydiol Etc.) or polyesters that are the reaction product of these diol compounds
  • Epoxy (meth) acrylates include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, terminal glycidyl ether of bisphenol A propylene oxide adduct, and fluorene epoxy resin and (meth) Examples include a reaction product with acrylic acid.
  • polyester (meth) acrylate examples include a reaction product of polyester diol which is a reaction product of the above diol compound and the above dibasic acid or anhydride thereof, and (meth) acrylic acid.
  • the (meth) acrylate compound (E) that can be used in the resin composition of the present invention is preferably a compound having a bisphenol A skeleton in consideration of the refractive index, such as bisphenol A polyethoxydi (meth) acrylate and bisphenol A poly.
  • (Meth) acrylate monomers such as propoxy di (meth) acrylate, urethane (meth) acrylate oligomers having a bisphenol A skeleton (diol compounds such as bisphenol A polyethoxydiol and bisphenol A polypropoxydiol, or these diol compounds and dibasic compounds
  • a bisphenol A skeleton diol compounds such as bisphenol A polyethoxydiol and bisphenol A polypropoxydiol, or these diol compounds and dibasic compounds
  • a bisphenol A skeleton Poxy (meth) acrylate oligomer bisphenol A type epoxy resin, epoxy resin such as terminal glycidyl ether of bisphenol A propylene oxide adduct and a reaction product of (
  • monofunctional or bifunctional (meth) acrylate monomers are suitable as the (meth) acrylate compound (E), and among them, acryloylmorpholine, tetrahydrofurfuryl (meth).
  • the (meth) acrylate compound (E) includes tris (acryloxyethyl) isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, Trifunctional or higher functional (meth) acrylate monomers such as dipentaerythritol penta (meth) acrylate and trimethylolpropane tri (meth) acrylate are preferred.
  • each component of the resin composition of the present invention is determined in consideration of the desired refractive index, glass transition temperature, viscosity, adhesion, etc., but component (A) + component (D) + component (E) Is 100 parts by mass, the content of component (A) is 2 to 100 parts by mass, preferably 5 to 100 parts by mass.
  • the content of component (D) is 0 to 85 parts by mass, preferably 0 to 75 parts by mass.
  • the content of component (E) is 0 to 60 parts by mass, preferably 0 to 50 parts by mass.
  • Component (B) is usually used in an amount of 0.1 to 10 parts by weight, preferably 0.3 to 7 parts by weight, based on 100 parts by weight of the total amount of component (A) + component (D) + component (E). It is.
  • the energy ray curable resin composition of the present invention includes a mold release agent, an antifoaming agent, a leveling agent, a light stabilizer, an antioxidant, and a polymerization prohibition in order to improve convenience during handling.
  • An agent, an antistatic agent, an ultraviolet absorber and the like can be used in combination depending on the situation.
  • polymers such as acrylic polymer, polyester elastomer, urethane polymer and nitrile rubber, inorganic or organic light diffusing filler, and the like can be added as necessary.
  • the resin composition of the present invention can be obtained by adding a solvent as necessary, in the present invention, it is preferable not to add a solvent.
  • the resin composition of the present invention can be prepared by mixing and dissolving each component according to a conventional method.
  • each component can be charged into a round bottom flask equipped with a stirrer and a thermometer and stirred at 40 to 80 ° C. for 0.5 to 6 hours.
  • the viscosity of the resin composition of the present invention is 4,000 mPa ⁇ s at 25 ° C. measured using an E-type viscometer (TV-200: manufactured by Toki Sangyo Co., Ltd.) as a viscosity suitable for producing optical lens sheets. Compositions that are s or less are preferred.
  • a cured product obtained by curing the resin composition of the present invention by irradiating energy rays such as ultraviolet rays according to a conventional method is also included in the present invention.
  • the cured product is obtained by applying the resin composition of the present invention on a stamper having a shape of, for example, a Fresnel lens, a lenticular lens, or a prism lens to form a layer of the resin composition, and a hard transparent substrate on the layer.
  • a back sheet (for example, a substrate or film made of polymethacrylic resin, polycarbonate resin, polystyrene resin, polyester resin, or a blend of these polymers) is adhered, and then ultraviolet light is emitted from the hard transparent substrate side by a high-pressure mercury lamp or the like. After the resin composition is cured by irradiation, the cured product can be peeled off from the stamper. Moreover, it can also carry out by a continuous process as these applications.
  • the refractive index can be measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
  • the resin composition of the present invention is useful as an optical lens sheet as described above.
  • Applications other than those for optical lens sheets include various coating agents and adhesives.
  • Synthesis example 1 Synthesis of Compound (A) In an autoclave, 167.2 g (1.0 mol) of carbazole, 114.5 g of toluene and 0.5 g of potassium hydroxide were charged, and after nitrogen substitution, 48.5 g (1.1 mol) ) was added dropwise within a range of 120 ° C. to 140 ° C. and a reaction pressure of 0.2 MPa or less, and reacted for 6 hours. After the reaction, unreacted ethylene oxide and toluene were distilled off under reduced pressure to obtain 211.3 g of N- (2-hydroxyethyl) carbazole.
  • Synthesis example 2 Synthesis of Compound (E) Synthesis was performed according to Synthesis Example 2 and Example 2 of International Publication 2008/136262.
  • a flask equipped with a thermometer, a cooler, and a stirrer was charged with 181 g of p-phenylphenol (P-PP Sanko Co., Ltd.), 394 g of epichlorohydrin, and 80 g of methanol while being purged with nitrogen gas.
  • the mixture was further heated to 70 ° C., 44 g of flaky sodium hydroxide was added in portions over 90 minutes, and then reacted at 70 ° C. for 60 minutes.
  • Etc. were distilled off to obtain 227 g of the desired epoxy resin (e-1).
  • the obtained epoxy resin (e-1) had an epoxy equivalent of 242 g / eq. It was white crystalline at room temperature.
  • 145.2 g (0.6 eq.) Of the obtained epoxy resin (e-1) was used as a thermal polymerization inhibitor in a 1 L flask equipped with a stirrer and a reflux tube, and 2,6-di-tert- 0.57 g of butyl-p-cresol, 43.3 g (0.6 eq.) Of acrylic acid and 0.57 g of triphenylphosphine as a reaction catalyst were charged and reacted at 98 ° C. for 30 hours.
  • the first reaction was completed at 2 mg ⁇ KOH / g. After the completion of the first reaction, the reaction temperature was 40 ° C., 232.0 g of o-phenylphenol monoethoxy acrylate was added as a reaction diluent, and the mixture was stirred and mixed. Next, 0.070 g of dibutyltin dilaurate was added as a urethane reaction catalyst, 43.6 g (0.5 eq.) Of 2,4-tolylene diisocyanate was added, the reaction temperature was raised to 60 ° C., and the reaction was allowed to proceed for 24 hours. %). At this time, NCO (%) was 0.00%, and the reaction was terminated. The product was 460 g, and an o-phenylphenol monoethoxy acrylate mixture containing 50% by mass of the urethane acrylate as the compound (E) was obtained.
  • Synthesis example 3 Synthesis of Compound (E) 139.3 parts of 2,4-tolylene diisocyanate, 0.05 parts of di-n-butyltin dilaurate and 0.16 parts of methoquinone were placed in a drying container and heated to 40 ° C. , Stirred. To this was added 185.6 parts of 2-hydroxyethyl acrylate dropwise over 1 hour while confirming the exotherm, and reacted at 80 ° C. for 1-2 hours. The isocyanate value after the reaction was 0.1 or less, indicating that the reaction was almost quantitatively completed, and urethane acrylate as compound (E) was obtained.
  • Synthesis example 4 Synthesis of Compound (E) Synthesis was performed according to Synthesis Example 1 of JP-A-2008-94987. After attaching a stirrer, thermometer, condenser water separator, etc. to a 2 L 4-neck flask, 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene (trade names: BPEF, JEF Chemical Co., Ltd.) )), 401.0 g, acrylic acid 161.0 g, toluene 600 ml, p-toluenesulfonic acid 45.6 g, hydroquinone 4.6 g, heated with stirring and dehydrated for esterification reaction. went.
  • the reaction time was 5 hours, the reaction temperature was 103 to 120 ° C., and the amount of distilled water by dehydration reaction was 38 g.
  • the reaction solution was diluted with 1500 ml of toluene, neutralized by adding 200 g of a 20% by weight aqueous sodium hydroxide solution, washed with 500 g of a 15% by weight aqueous sodium chloride solution, and further toluene was distilled off.
  • 458.2g of bifunctional acrylate which is a compound (E) was obtained.
  • the resin composition and the cured product of the present invention were obtained with the composition as shown in the following examples (numerical values indicate parts by mass).
  • the evaluation method and evaluation criteria for the resin composition and the cured film were as follows.
  • Viscosity Viscosity was measured at 25 ° C. using an E-type viscometer (TV-200: manufactured by Toki Sangyo Co., Ltd.).
  • Releasability Expresses the degree of difficulty when releasing a cured resin from a mold.
  • ⁇ ⁇ Mold reproducibility The surface shape of the cured ultraviolet curable resin layer and the surface shape of the mold were observed. ⁇ ⁇ Reproducibility is good ⁇ ⁇ Reproducibility is poor
  • a test piece was prepared by applying a resin composition on a substrate to a film thickness of about 50 ⁇ m and then irradiating it with a high-pressure mercury lamp (80 W / cm, ozone-less) at 1000 mJ / cm 2.
  • the adhesion was evaluated according to JIS K5600-5-6. In the evaluation results, 0 to 2 were marked with ⁇ , and 3 to 5 were marked with ⁇ .
  • Refractive index (25 ° C.) The refractive index (25 ° C.) of the cured ultraviolet curable resin layer was measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
  • DMS-6000 viscoelasticity measurement system
  • a test piece was prepared by applying a resin composition on a substrate to a film thickness of about 80 ⁇ m and then irradiating it with a high-pressure mercury lamp (80 W / cm, ozone-less) at 600 mJ / cm 2 . .
  • a light resistance test was conducted for 4 hours under conditions of 60 ° C. and 60% RH using EYE SUPER UV TESTER SUV-W11 (manufactured by Iwasaki Electric Co., Ltd.), and the state of the film was visually evaluated.
  • ⁇ ⁇ State of great appearance change such as coloring and cracking of resin layer
  • Example 1 20 parts of the compound obtained in Synthesis Example 1 as component (A), 31 parts of o-phenylphenol monoethoxyacrylate as component (D), and 3 parts of Irgacure 184 (1-hydroxycyclohexyl phenyl ketone) as component (B) Parts, 0.1 parts of diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, 20 parts of KAYARAD R-551 (Nippon Kayaku: bisphenol A polyethoxydiacrylate) as component (E), KAYARAD 4 parts of R-115 (Nippon Kayaku: bisphenol A epoxy acrylate), 18 parts of tris (2-acryloyloxyethyl) isocyanurate, 7 parts of acryloylmorpholine, heated to 60 ° C., and mixed.
  • component (A) 20 parts of the compound obtained in Synthesis Example 1 as component (A), 31 parts of o-phenylphenol monoethoxyacrylate as component (D), and 3
  • a resin composition was obtained.
  • the viscosity of this resin composition was 690 mPa ⁇ s.
  • the refractive index (25 ° C.) of the 200 ⁇ m-thick UV curable resin layer obtained by curing this resin composition by irradiation with 600 mJ / cm 2 with a high-pressure mercury lamp (80 w / cm, ozone-less) is 1.589.
  • the glass transition temperature (Tg) was 82 ° C.
  • this resin composition was applied onto a prism lens mold so that the film thickness was 50 ⁇ m, and an easy-adhesion PET film (Toyobo Cosmo Shine A4300, 100 ⁇ m thickness) was adhered thereon as a base material,
  • the prism lens sheet of the present invention was obtained from above by being cured by irradiating with an ultraviolet ray of 600 mJ / cm 2 with a high-pressure mercury lamp and then curing. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ .
  • Example 2 In Example 1, 52 parts of o-phenylphenol monoethoxyacrylate as component (D), 3 parts of 2-hydroxy-2-methyl-1-phenylpropan-1-one as component (B), and as component (E) 10 parts of the compound obtained in Synthesis Example 3, 13 parts of acryloylmorpholine, 5 parts of tetrahydrofurfuryl acrylate, heated to 60 ° C. and mixed to obtain a resin composition of the present invention. The viscosity of this resin composition was 150 mPa ⁇ s.
  • the resin layer obtained in the same manner as in Example 1 had a refractive index (25 ° C.) of 1.599 and a glass transition temperature (Tg) of 59 ° C.
  • Tg glass transition temperature
  • a prism lens sheet of the present invention was obtained in the same manner as in Example 1. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ , light resistance: ⁇ .
  • Example 3 In Example 1, 65 parts of the compound obtained in Synthesis Example 1 as component (A), 3 parts of Irgacure 184 as component (B), and 0 of diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide .1 part, 25 parts phenoxyethyl acrylate as component (D), 10 parts KAYARAD DPHA (manufactured by Nippon Kayaku: dipentaerythritol hexaacrylate) as component (E), heated to 60 ° C. and mixed, An inventive resin composition was obtained. The viscosity of this resin composition was 340 mPa ⁇ s.
  • the resin layer obtained in the same manner as in Example 1 had a refractive index (25 ° C.) of 1.622 and a glass transition temperature (Tg) of 69 ° C.
  • Tg glass transition temperature
  • a prism lens sheet of the present invention was obtained in the same manner as in Example 1. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ .
  • Example 4 In Example 1, 10 parts of the compound obtained in Synthesis Example 1 as component (A), 59 parts of o-phenylphenol monoethoxy acrylate, 8 parts of phenoxyethyl acrylate as component (D), and Irga as component (B) 5 parts of Cure 184, 0.1 part of diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, 3 parts of KAYARAD DPHA as component (E), 30 parts of the mixture obtained in Synthesis Example 2 5 parts of the compound obtained in Example 3 and 3 parts of 1,4-butanediol diacrylate were heated to 60 ° C. and mixed to obtain a resin composition of the present invention.
  • the viscosity of this resin composition was 510 mPa ⁇ s.
  • the resin layer obtained in the same manner as in Example 1 had a refractive index (25 ° C.) of 1.604 and a glass transition temperature (Tg) of 52 ° C.
  • Tg glass transition temperature
  • a prism lens sheet of the present invention was obtained in the same manner as in Example 1. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ .
  • Example 5 In Example 1, 55 parts of the compound obtained in Synthesis Example 1 as component (A), 7 parts of o-phenylphenol monoethoxyacrylate as component (D), 25 parts of phenoxyethyl acrylate, and Irga as component (B) 3 parts of Cure 184, 0.1 part of diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, 10 parts of KAYARAD DPHA as component (E), 60 parts of the compound obtained in Synthesis Example 4
  • the resin composition of the present invention was obtained by heating to °C and mixing. The viscosity of this resin composition was 465 mPa ⁇ s.
  • the resin layer obtained in the same manner as in Example 1 had a refractive index (25 ° C.) of 1.618 and a glass transition temperature (Tg) of 71 ° C.
  • Tg glass transition temperature
  • a prism lens sheet of the present invention was obtained in the same manner as in Example 1. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ .
  • Comparative Example 1 According to Example 1 of Patent Document 1 (Japanese Patent Laid-Open No. 63-167301), 70 parts of Aronics M-315 (tris (2-acryloyloxyethyl) isocyanurate), 30 parts of tetrahydrofurfuryl acrylate, 1 as a photopolymerization initiator 3 parts of-(4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one were heated to 60 ° C. and mixed to obtain a comparative resin composition. The viscosity of this resin composition was 134 mPa ⁇ s. The refractive index (25 ° C.) of the resin layer obtained in the same manner as in Example 1 was 1.520. From this result, the composition of Comparative Example 1 has a lower refractive index than the composition of the present invention, and is not suitable for the production of the lenses of the present invention.
  • Aronics M-315 tris (2-acryloyloxyethyl) isocyanur
  • the viscosity of this resin composition was 4420 mPa ⁇ s. Further, the refractive index (25 ° C.) of the resin layer obtained in the same manner as in Example 1 was 1.574. From this result, the composition of Comparative Example 2 has a higher viscosity than the composition of the present invention, and is unsuitable for fine processing and continuous processing of roll-shaped sheets and films.
  • Comparative Example 3 Without component (A), 51 parts o-phenylphenol monoethoxyacrylate as component (D), 3 parts Irgacure 184 as component (B), diphenyl- (2,4,6-trimethylbenzoyl) phosphine 0.1 parts of oxide, 20 parts of KAYARAD R-551 as component (E), 4 parts of KAYARAD R-115, 18 parts of tris (2-acryloyloxyethyl) isocyanurate, 7 parts of acryloylmorpholine, 60 ° C. The mixture was heated and mixed to obtain a comparative resin composition. The viscosity of this resin composition was 409 mPa ⁇ s.
  • the resin layer obtained in the same manner as in Example 1 had a refractive index (25 ° C.) of 1.581 and a glass transition temperature (Tg) of 71 ° C.
  • a comparative prism lens sheet was obtained in the same manner as in Example 1 using the obtained resin composition. From this result, the composition of Comparative Example 3 has a lower refractive index than the composition of the present invention, and is not suitable for the production of the lenses of the present invention. Evaluation results: releasability: ⁇ , mold reproducibility: ⁇ , adhesion: ⁇ , light resistance: ⁇ .
  • the resin composition of the present invention has a low viscosity, and the cured product of the present invention has a high refractive index, as well as releasability and mold reproduction. And excellent adhesion to the substrate. For this reason, it is suitable for an optical lens sheet having a fine structure, for example, a Fresnel lens, a lenticular lens, a prism lens, a microlens and the like. In particular, since it has a high refractive index, it is suitable for high-luminance products, and it is suitable for manufacturing that requires fine processing and processes that require continuous processing.
  • the ultraviolet curable resin composition of the present invention and the cured product thereof are particularly suitable mainly for optical lens sheets such as Fresnel lenses, lenticular lenses, prism lenses, and micro lenses.

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Abstract

L'invention a trait à une composition de résine qui possède une excellente aptitude au démoulage, une excellente reproductibilité de forme de moule, une excellente adhérence à une base et une excellente résistance à la lumière, et qui présente également un indice de réfraction élevé, un point de transition vitreuse élevé et une faible viscosité. L'invention concerne en particulier une composition de résine durcissable par rayonnement énergétique pour une feuille de lentille optique, qui contient (A) un composé comportant un groupe carbazolyle et (B) un initiateur de photopolymérisation.
PCT/JP2010/058421 2009-05-25 2010-05-19 Composition de résine durcissable par rayonnement énergétique pour feuille de lentille optique et produit durci correspondant WO2010137501A1 (fr)

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