WO2006057413A1 - Composition de résine photodurcissable et élément optique - Google Patents

Composition de résine photodurcissable et élément optique Download PDF

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Publication number
WO2006057413A1
WO2006057413A1 PCT/JP2005/021915 JP2005021915W WO2006057413A1 WO 2006057413 A1 WO2006057413 A1 WO 2006057413A1 JP 2005021915 W JP2005021915 W JP 2005021915W WO 2006057413 A1 WO2006057413 A1 WO 2006057413A1
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Prior art keywords
meth
acrylate
resin composition
curable resin
ultraviolet curable
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PCT/JP2005/021915
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English (en)
Japanese (ja)
Inventor
Satoshi Futami
Hiroshi Miyao
Takayoshi Tanabe
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Jsr Corporation
Japan Fine Coatings Co. Ltd.
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Publication of WO2006057413A1 publication Critical patent/WO2006057413A1/fr

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    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/142—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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

Definitions

  • the present invention relates to a photocurable resin composition, and more specifically, a prism lens sheet used for a backlight of a liquid crystal display device, a Fresnel lens sheet used for a screen of a projection television, and a lenticular lens.
  • the present invention relates to a photocurable resin composition useful for forming a lens portion of a lens sheet such as a sheet, or an optical member such as a backlight using such a sheet, and an optical member made of the cured product.
  • lenses such as Fresnel lenses and lenticular lenses have been manufactured by techniques such as a press method and a cast method, but both methods require a long time to manufacture the lenses and have poor productivity.
  • ultraviolet curable resins In order to solve such problems, in recent years, studies have been made on the production of lenses using ultraviolet curable resins. Specifically, an ultraviolet curable resin composition is poured between a lens-shaped mold and a transparent resin substrate, and the lens is irradiated in a short time by irradiating ultraviolet rays from the substrate side to cure the composition. Can be manufactured.
  • Patent Document 1 discloses that (A) diol (a) obtained by reacting bisphenol A and alkylene oxide is reacted with aromatic organic polyisocyanate (b), and then hydroxyl group-containing.
  • Urethane (meth) acrylate which is a reaction product obtained by reacting (meth) acrylate (c), (B) an ethylenically unsaturated group-containing compound other than (A) component, and (C) a photopolymerization initiator
  • An ultraviolet curable resin composition for a transmission type screen is described.
  • Patent Document 1 Japanese Patent Laid-Open No. 5-255464
  • An object of the present invention is to provide a resin for a Fresnel lens and a rear processing TV Fresnel lens with improved blue loss on a rear process TV screen. Disclosure of the invention
  • urethane (meta) composed of a diol having a specific structure by a certain process.
  • Various plastic substrates with a high refractive index can be obtained by producing a cured product using an ultraviolet curable resin composition in which atallate, other ethylenically unsaturated group-containing compound, and a photopolymerization initiator are combined. It was found that a transmissive screen such as a Fresnel lens or a lenticular lens can be obtained.
  • the present invention provides the following ultraviolet curable resin composition and a rear project using the same.
  • R 1 represents a hydrogen atom, a methyl group, or Echiru group, Yogu even if Mashimashi these mixed to R 1 in one molecule, however, R 1 of at least 50 mol% of all R 1 Is other than a hydrogen atom, R 2 represents a hydrogen atom or a methyl group, and m and n each represent a number from 1 to 20. G;
  • a rear projection TV Fresnel lens comprising a cured product of the ultraviolet curable resin composition according to any one of [1] to [4] above.
  • the required characteristics required for a lens such as adhesion to various plastic substrates, mold force peelability, coatability (viscosity), and resilience are sufficiently satisfied.
  • a cured product can be provided.
  • the cured product obtained by curing the ultraviolet curable resin composition of the present invention can improve blue loss particularly in a thin rear-projection TV, and can improve image quality.
  • the component (A) used in the ultraviolet curable resin composition of the present invention comprises: (a) a hydroxyl group-containing (meth) acrylate and (b) an organic polyisocyanate, and then (c) It is urethane (meth) acrylate which is a reaction product obtained by reacting the diol represented by the formula (1).
  • Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2 hydroxy-3 phenyl.
  • R 8 represents a hydrogen atom or a methyl group
  • V represents a number of:! To 15
  • a compound obtained by an addition reaction between a glycidyl group-containing compound such as alkyl glycidyl ether, allyl glycidyl ether, glycidyl (meth) acrylate, and (meth) attalinoleic acid can also be used.
  • a glycidyl group-containing compound such as alkyl glycidyl ether, allyl glycidyl ether, glycidyl (meth) acrylate, and (meth) attalinoleic acid
  • These hydroxyl group-containing (meth) acrylates may be used alone or in combination of two or more.
  • Examples of the organic polyisocyanate include 2, 4_tolylene diisocyanate, 2, 6-tolylene diisocyanate, 1,3_xylylene diisocyanate, and 1,4_xylylene diisocyanate.
  • 2, 4_ birds It is preferable to use range isocyanate, 2, 6_tolylene diisocyanate, 1,3_xylylene diisocyanate, 1,4_xylylene diisocyanate.
  • R 1 is a hydrogen atom, a methyl group, or an ethyl group, and these may be mixed in R 1 in one molecule, but 50 mol% or more of the total R 1 R 1 is other than a hydrogen atom.
  • the ratio in which R 1 is other than a hydrogen atom is preferably at least 60 mol%, more preferably at least 80 mol%, particularly preferably at least 90 mol%, and most preferably all R 1 are methyl groups. Preferred.
  • R 1 is a hydrogen atom
  • R 2 represents a hydrogen atom or a methyl group, and a methyl group is particularly preferable.
  • m and n are each a number from 1 to 20, and the average power of m + n is preferably 4 to 30, especially 6 to 25. When the average value of m + n is 2 or less, the adhesion to the substrate is lowered. Conversely, when it exceeds 40, it is difficult to obtain the refractive index required for the lens.
  • examples of commercially available products include Uniunore DB-360, DB-400, DB-800, DB-900 (above, Nippon Oil & Fats Co., Ltd.).
  • the urethane (meth) acrylate (A) is produced by first reacting a hydroxyl group-containing (meth) acrylate and an organic polyisocyanate and then reacting the diol in the next step.
  • the viscosity becomes high and difficult to handle. Since it may become, it is not preferable.
  • the diol, the organic polyisocyanate, and the hydroxyl group-containing (meth) acrylate are used in proportion to the isocyanate group contained in the organic polyisocyanate compound with respect to 1 equivalent of the hydroxyl group contained in the diol. 1 .:! ⁇ 2 equivalents, It is preferable that the hydroxyl group of the hydroxyl group-containing (meth) acrylate is 0.:! ⁇ 1 equivalents.
  • urethane (meth) acrylate usually, copper naphthenate, cobalt naphthenate, zinc naphthenate, di-dilaurate, n_butyltin, triethylenamine, triethylenediamine _ 2 _
  • a urethanization catalyst such as methyltriethyleneamine is used in an amount of 0.0 :! to 1% by mass based on the total amount of the reaction raw materials.
  • the reaction temperature is usually 10 to 90 ° C, preferably 30 to 80 ° C.
  • the preferred number average molecular weight of the urethane (meth) acrylate of component (A) is 500 to 20,000, and preferably 1,000 to 15,000. If the number average molecular weight of the component (A) urethane (meth) acrylate is less than 500, the adhesion of the cured product obtained by curing the resin composition to the substrate is lowered, and conversely the number average When the molecular weight exceeds 20,000, the viscosity of the resin composition becomes high and it is difficult to handle.
  • the urethane (meth) acrylate of component (A) is preferably added in an amount of 5 to 70% by mass, particularly preferably 10 to 60% by mass, in the total resin composition.
  • the lower limit of the blending amount is preferably in the above range from the viewpoint of imparting appropriate mechanical properties such as toughness to the cured product and imparting adhesion to the substrate.
  • the upper limit of the blending amount is preferably in the above range from the viewpoint of preventing the viscosity of the composition from increasing and deteriorating workability and coating property.
  • the component (B) used in the ultraviolet curable resin composition of the present invention is an ethylenically unsaturated group-containing compound other than the component (A), and a compound containing a (meth) atalyloyl group or a bur group.
  • unsaturated monomer a monofunctional monomer and a polyfunctional monomer can be used. Examples of monofunctional monomers include N-Buylpyrrolidone, N-Buyl Prolactam, vinyl imidazole, and Bulpyridine.
  • Monomers isobornyl (meth) acrylate, bornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentyl (meth) acrylate, cyclohexyl (Meth) Atalylate, Benzyl (Meth) Atalylate, 4-Butylcyclohexyl (Meth) Atalylate, Atariloy Noremonorephorine, 2-Hydroxyethyl (meth) atarylate, 2-Hydroxypropyl (meth) atalylate, 2- Hydroxybutyl (meth) Atarire DOO, methyl (meth) Atari rate, Echinore (meth) Atari rate, propyl (meth) Atari rate, isopropyl (meth) Atari rate, butyl ( 'Relate, aminore (meth) acrylate, isobutyl (me
  • R 9 represents a hydrogen atom or a methyl group
  • R 1Q represents an alkylene group having 2 to 8 carbon atoms
  • Di (meth) talylate of diol which is an adduct of polyethylene oxide or propylene oxide of bis (r) hexa (meth) acrylate, bisphenol A, Di of diol, which is an adduct of ethylene oxide or propylene oxide of bisphenol A (Meth) acrylate, bisphenol A diglycidyl ether and polyfunctional monomers such as epoxy (meth) acrylate and triethylene glycol divinyl ether obtained by carotenating (meth) acrylate.
  • the cured product has an Abbe number of 40 or more and a refractive index ( n 25 ) at 589 nm of 1.55 or more.
  • a monomer having a tricyclodecane group is essential in order to obtain a composition satisfying all of the restorability, and that the content is 10 parts by weight or more.
  • the Abbe number of the cured product obtained by curing the composition of the present invention is 40 or more, and the refractive index (n 25 ) at 589 nm is 1.55 or more.
  • the refractive index (n 25 ) at 589 nm is 1.55 or more.
  • the Abbe number per minute is preferably 40 or more, more preferably 50 or more, and particularly preferably 60 or more.
  • the component (B) having an Abbe number force of less than S40 may be used in a range that does not lower the Abbe number of the cured product to less than 40.
  • the refractive index of each component (B) is preferably 1.54 or more, more preferably 1.55 or more, and particularly preferably 1.56 or more. However, multiple When the component (B) is used in combination, the component (B) having a refractive index of less than 1.54 may be used in a range that does not lower the Abbe number of the cured product to less than 40.
  • preferable monofunctional monomers include N-bule force prolatatum (Abbe number 47.1, refractive index 1.54), attalyleuno monomonophorin (Abbe number 44.4). And the refractive index 1.55).
  • preferred polyfunctional monomers include trimethylol propanetriatalylate (Abbe number 45.7, refractive index 1.51), dipentaerythritol hexaatalylate (Abbe number 51.3, refractive index 1.50), tris ( Atari mouth kichetil) isocyanurate (Abbe number 53.0, refractive index 1.53), nonanediol ditalylate (Abbe number 57.7, refractive index 1 ⁇ 50), tricyclodecane-3,8-di
  • Examples of commercially available monofunctional monomers include New Frontier PHE (Daiichi Kogyo Seiyaku).
  • ALONIX M110, M120, M150, M156 (above, manufactured by Toagosei Co., Ltd.), LA, IBXA, 2—MTA, HPA, Pisco Ichigo # 150, # 155, # 158, # 190, # 2000, # 2100, # 2150 (Osaka Organic Chemical Industry Co., Ltd.), Light Atylate BO— A, EC— A, DMP— A, THF— A, HOP— A, HOA— MPE, HOA— MPL (above, manufactured by Kyoeisha Igaku Co., Ltd.), KAYARAD TCI 1 OS (produced by Nippon Kayaku Co., Ltd.), FA—511A, 512A, 513A (above, manufactured by Hitachi Chemical Co., Ltd.), VP (BASF Co., Ltd.), ACMO, DMAA, DM APAA (manufactured by Kojin Co., Ltd.) and the like.
  • polyfunctional monomers include, for example, New Frontier LA-9A (Daiichi Kogyo Seiyaku Co., Ltd.), Neopol V779 (Nippon Cupica), Upimar UV SA1002, SA 2007 (above, Mitsubishi Chemical) (Made by Co., Ltd.), Biscote # 195, # 230, # 215, # 260, # 335HP, # 295, # 300, # 360, # 700, GPT, 3PA (above, made by Osaka Organic Chemicals Co., Ltd.) ), Light acrylate 4EG—A, 9EG—A, NP—A, DCP—A, BP—4EA, B P_4PA, TMP_A, PE_3A, PE_4A, DPE—6A (above, manufactured by Kyoeisha Chemical Co., Ltd.), KAYARAD PET-30, TMPTA, R-604, DPHA, DPCA-20, -30, -60, -120, H
  • R 3 represents a hydrogen atom or a methyl group
  • R 4 represents — ( ⁇ CH 2 CH 3) p—, ⁇ (OCH
  • each R 5 is independently hydrogen
  • R 6 is a hydrogen atom, a halogen atom excluding fluorine, or Ph_C (CH 2) —, Ph— (where Ph represents a phenyl group), carbon number 1 ⁇ 20
  • phenoxychetyl (meth) acrylate phenoxy_2_methylethyl (meth) acrylate, phenoxyethoxyethyl (meth) acrylate, 3-phenoxy-2-hydroxypropyl (meth) acrylate, 2 —Fueurphenoxychetyl (meth) atarylate, 4_Fueurphenoxychetyl (meth) atalylate, 3-(2 _Fuylphenyl) _ 2 _Hydroxypropyl (meth) atalylate, ethylene oxide (Meth) atarylate of p_tamylphenol, 2-bromophenoxychetyl (meth) ate, 2,4-dibromophenoxytetyl (meth) ate, 2, 4, 6-tribromophenol Phenoxy modified with multiple moles of chill (meth) acrylate and ethylene oxide and propylene oxide ( Data) Atari rate, and the like.
  • phenoxychetyl (meth) acrylate particularly preferred are phenoxychetyl (meth) acrylate, phenoxy ethoxy ethyl (meth) acrylate, phenoxy phthalate modified with 4 moles of ethylene oxide, and (meth) acrylate of p-tammyl phenol reacted with ethylene oxide.
  • Component (B) is preferably blended in the total composition in an amount of 10 to 70 mass%, particularly preferably 20 to 60 mass%.
  • the lower limit of the amount is preferably in the above range from the viewpoint of the viscosity of the composition and the refractive index of the cured product.
  • the upper limit of the blending amount is preferably within the above range in terms of maintaining sufficient mechanical properties and coating strength.
  • the ultraviolet curable resin composition of the present invention is cured by ultraviolet rays.
  • the photocuring reaction requires a photopolymerization initiator as component (C), and if necessary, a photosensitizer is further added. Any photopolymerization initiator may be used as long as it can be decomposed by light irradiation to generate radicals to initiate polymerization.
  • photopolymerization initiators include, for example, Irgacurel 84, 369, 651, 500, 819, 9 07, 784, 2959, CGI-1700, -1750, -1850, CG24-61, Darocur 1116, 1173 ( Ciba 'Specialty' Chemicals Co., Ltd.), Lucirin TP ⁇ , LR8893 LR8970 (manufactured by BASF Corp.), ubecryl P36 (manufactured by UCB Corp.) and the like.
  • the optimal amount of photopolymerization initiator for curing the ultraviolet curable resin composition of the present invention is 0.01 to 10 mass%, particularly 0.5 to 7 in the total composition. Mass% is preferred.
  • the upper limit of the compounding amount is preferable from the viewpoint of the curing characteristics of the composition, the mechanical and optical properties of the cured product, the handling amount, etc.
  • the lower limit of the compounding amount is from this point of preventing the decrease in the curing rate. An enclosure is preferred.
  • photosensitizers include triethylamine, jetylamine, N-methylethanolamine, ethanolamine, 4-dimethylaminobenzoic acid, 4-dimethylaminobenzoic acid methyl, 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid.
  • Isoamyl and the like can be mentioned, and as commercially available products, for example, Ubekryl P102, 103, 104, 105 (above, manufactured by UCB) and the like can be mentioned.
  • thermal polymerization initiator When the ultraviolet curable resin composition of the present invention is cured, a thermal polymerization initiator may be used in combination as necessary.
  • Preferred examples of the thermal polymerization initiator include peroxides and azo compounds. Specific examples include benzoyl peroxide, t-butyl peroxybenzoate, and azobisisobutyronitrile.
  • the ultraviolet curable resin composition of the present invention includes other oligomers that are curable within a range that does not impair the characteristics of the ultraviolet curable resin composition of the present invention, if necessary. Or a polymer can be mix
  • curable oligomers or polymers include polyurethane (meth) acrylates other than component (A), polyester (meth) acrylates, epoxy (meth) acrylates, polyamide (meth) acrylates, (meth) acrylates.
  • examples thereof include a siloxane polymer having a royloxy group, and a reactive polymer obtained by reacting a copolymer of glycidyl methacrylate and other polymerizable monomers with (meth) acrylic acid.
  • additives as necessary include, for example, antioxidants, ultraviolet absorbers, light stabilizers, silane coupling agents, coating surface improvers, thermal polymerization inhibitors, leveling agents.
  • Agents, surfactants, colorants, storage stabilizers, plasticizers, lubricants, mold release agents, solvents, fillers, anti-aging agents, wettability improvers and the like can be blended as necessary.
  • UV absorption for example, Tinuvin P, 234, 320, 326, 327, 328, 329, 213 (above, manufactured by Chino Spessianorety Chemikanoles Co., Ltd.), Seesorbl02, 103, 110, 501, 202, 712, 704 (above, manufactured by Siploi Co., Ltd.), etc.
  • Tinuvin 292, 144, 622LD (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), Sanol LS770 (Sankyo Co., Ltd.), Sumisorb TM_061 (Sumitomo Chemical Co., Ltd.)
  • the silane coupling agent for example, ⁇ -aminopropyltriethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -metaallyloxypropyltrimethoxysilane, commercially available products such as SH6062, 6030 (above, Toray Dowco Ning's (made by Silicone Co., Ltd.), KBE903, 603, 403 (made by Shin-Etsu Chemical Co., Ltd.), etc.
  • the coating surface improver include silicone additives such as dimethylsiloxane polyether.
  • Examples of commercially available products include DC-57, DC-190 (above, manufactured by Dowco), SH-28PA, SH-29PA, SH-30PA, SH-190 (above, Toray Dowco. Silicone Co., Ltd.), KF351, KF352, KF353, KF354 (above, Shin-Etsu Chemical Co., Ltd.), L—700, L—7002, L—7500, FK—024—90 (above, Nippon Tunica ( Etc.).
  • the ultraviolet curable resin composition of the present invention can be produced by mixing the above-mentioned components by a conventional method.
  • the viscosity of the ultraviolet curable resin composition of the present invention thus prepared is usually 200 to 50,000 mPa's / 25. C, preferably 1,500 to 10,000 mPa-s / 25 ° C. If the viscosity is too high, unevenness and undulation will occur in the production of the lens, and it will be difficult to obtain the target lens thickness, and the lens performance will not be fully demonstrated. On the other hand, if it is too low, it may not be possible to form a uniform lens with a constant thickness that makes it difficult to control the lens thickness.
  • a cured product obtained by curing the ultraviolet curable resin composition of the present invention has good restorability.
  • the recoverability of the cured product refers to, for example, a characteristic in which a trace of compression remaining on the lens surface disappears after a certain load is applied to the lens surface of the lens substrate peeled from the lens mold. Due to the good resilience, the contact marks caused by the load applied when the lenses are stacked and transported quickly disappear. If this contact mark remains, the image quality when set on TV is low. Invite the bottom, but the problem does not occur.
  • the cured product obtained by curing the ultraviolet curable resin composition of the present invention has an Abbe number of 40 or more and a refractive index at 589 nm of 1.55 or more.
  • a large Abbe number means that the dispersibility of the refractive index is small, that is, the refractive index difference between the blue light and the red light with a small variation in the refractive index over the entire visible region. Means.
  • the Abbe number is more preferably 42 or more, and 45 or more.
  • the refractive index difference between 436 nm (red light) and 589 nm (blue light) is preferably 0.015 or less, more preferably 0.010 or less.
  • the refractive index at 589 nm is high, light on the red side (short-wavelength light) is refracted more than conventional organic resins, so no blue loss occurs on the TV screen. For example, rear projection TV It is possible to design a thinner thickness. In addition, even if the angle of the Fresnel lens is not made acute, blue spots do not occur, so that it is easy to manufacture the Fresnel lens.
  • the refractive index is less than 1.55, when a transmission screen is formed using the ultraviolet curable resin composition of the present invention, sufficient front luminance may not be secured.
  • the ultraviolet curable resin composition of the present invention is useful as a material for producing optical parts by having the above-mentioned advantageous characteristics.
  • the ultraviolet curable resin composition of the present invention is a Fresnel lens material useful for designing a rear projection TV with a thinner thickness.
  • the present invention optimizes the physical properties required for a rear projection TV Fresnel lens application of an ultraviolet curable resin composition.
  • the rear projection TV Fresnel lens of the present invention has a refractive index dispersion. Since the blue light has a low refractive index and the refractive index is high, no blue dropout occurs, so that the image quality is improved and a rear-projection TV with higher visibility can be configured.
  • a reaction vessel equipped with a stirrer, 4-tolylene iso Xia sulphonate 35.47 wt%, Jirauri Rusanji n-butyltin 0.08 wt 0/0, 2, 6-di t-butyl-p Tarezoru 0.02 weight % was charged. While stirring, 23.65% by weight of 2-hydroxyethyl acrylate was added dropwise so that the temperature was kept below 30 ° C. After completion of the dropwise addition, the mixture was reacted at 30 ° C for 1 hour.
  • each component having the composition shown in Table 1 was charged into a reaction vessel to obtain each liquid curable resin composition.
  • Refractive index (n measurement: applicator bar so that the film thickness is 200 x m on the glass plate.
  • the resin composition was applied using 1. and irradiated with ultraviolet rays of Oj / cm 2 under nitrogen to prepare a test piece.
  • the refractive index at 25 ° C was measured using an Abbe refractometer manufactured by Atago Co., Ltd.
  • the refractive index (n 25 ) of component (A) and component (B) is determined as 1.
  • the refractive power of D-line (589 nm), F-line (486 nm), and C-line (656 nm) was calculated using a multi-wavelength Abbe refractometer manufactured by Atago Co., Ltd.
  • the Abbe number of component (A) and component (B) is determined as “X” when less than 40, “ ⁇ ” when exceeding 40 and less than 50, and “ ⁇ ” when exceeding 50 and less than 60. ",” Exceeding 60 was rated as “ ⁇ ”.
  • the sample was kept at 25 ° C and measured according to JIS K-7117 using a B-type viscometer.
  • Phenoxetyl Atylate New Frontier PHE p-cumino phenoxyethylene glycol acrylate (D-cumyl phenol acrylate modified with 1 mol of ethylene oxide), manufactured by Daiichi Kogyo Seiyaku Co., Ltd .: Made by Toagosei Co., Ltd., Alonics Ml 10 Vininole Power Prolatatum: Made by BASF
  • Atariloyl morpholine manufactured by Kojin Co., Ltd., ACMO
  • Tetrabromobisphenol A epoxy acrylate Showa Polymer Co., Ltd., VR77 EO-modified bisphenol A diathalate: Osaka Organic Chemical Industry Co., Ltd., Biscoat 700 Tricyclodecane-3,8-diyldimethyldiatalate: Mitsubishi Chemical Co., Ltd., Upima UV SA1002
  • Nonanediol ditalylate Daiichi Kogyo Seiyaku Co., Ltd., New Frontier LA-9A Tetrabromobisphenol A Epoxy Atallate: Nippon Pica Co., Ltd. Neoponole V779
  • Tris (2-ataryllooxychetyl) isocyanurate Toagosei Co., Ltd., ALONIX M315
  • Trimethylolpropane tritalylate Osaka Organic Chemical Industry Co., Ltd., Biscoat 295 Dipentaerythritol Hexaatalylate: Nippon Kayaku Co., Ltd., DPHA
  • the ultraviolet curable resin composition of the present invention has a high refractive index (n 25 ) and excellent adhesion to a substrate.
  • optical members such as lens sheets.
  • the cured product obtained by curing the ultraviolet curable resin composition of the present invention has a high Abbe number and a high refractive index at 589 nm. Therefore, the dispersibility of the refractive index depending on the wavelength is small, and particularly a thin rear projection.
  • Conventional organic resin when used as a Fresnel lens for TV The blue color which is a problem with the lens made of is not generated, and good image quality is provided.

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  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition de résine durcissable par ultraviolets qui comprend un (méth)acrylate d’uréthane (A) obtenu par réaction d’un (méth)arylate hydroxylé (a) et d’un polyisocyanate organique (b) et ensuite par une autre réaction avec un diol (c) représenté par la formule (1) ci-dessous ; un composant (B) contenant un groupe non saturé éthyléniquement autre que le composant (A) ; et un initiateur de photopolymérisation (C). La composition de résine durcissable par ultraviolets est caractérisée en ce qu’un produit durci de celle-ci a un nombre d’Abbe d’au moins 40 et un indice de réfraction (nD25) à 589 nm d’au moins 1,55.
PCT/JP2005/021915 2004-11-29 2005-11-29 Composition de résine photodurcissable et élément optique WO2006057413A1 (fr)

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JP2007034072A (ja) * 2005-07-28 2007-02-08 Dainippon Printing Co Ltd フレネルレンズシート、透過型スクリーン、背面投射型表示装置
JPWO2008013217A1 (ja) * 2006-07-27 2009-12-17 日本化薬株式会社 樹脂組成物、レンズ用樹脂組成物及びその硬化物
CN102667935B (zh) * 2009-11-03 2016-01-20 拜尔材料科学股份公司 具有不同书写共聚单体的光聚合物制剂
JP5442527B2 (ja) * 2010-04-30 2014-03-12 株式会社オプトプラス メタクリレート系共重合体からなる色消し組合せレンズ
JP5985100B1 (ja) * 2015-05-21 2016-09-06 デクセリアルズ株式会社 透明積層体

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JP2001294631A (ja) * 2000-04-10 2001-10-23 Mitsubishi Rayon Co Ltd アクリル系凝集体、光拡散剤、光拡散性樹脂組成物、成形品
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JPH0532735A (ja) * 1991-07-31 1993-02-09 Mitsubishi Rayon Co Ltd プラスチツクレンズ用組成物およびプラスチツクレンズの製造方法
JP2003137938A (ja) * 2001-11-07 2003-05-14 Daiso Co Ltd 光学的特性に優れた硬化性組成物
JP2003277451A (ja) * 2002-03-27 2003-10-02 Jsr Corp 光硬化性樹脂組成物及び光学部材

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