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WO2011052119A1 - Composition de résine durcissable par ultraviolets, produit durci et disque optique - Google Patents

Composition de résine durcissable par ultraviolets, produit durci et disque optique Download PDF

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Publication number
WO2011052119A1
WO2011052119A1 PCT/JP2010/005026 JP2010005026W WO2011052119A1 WO 2011052119 A1 WO2011052119 A1 WO 2011052119A1 JP 2010005026 W JP2010005026 W JP 2010005026W WO 2011052119 A1 WO2011052119 A1 WO 2011052119A1
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WIPO (PCT)
Prior art keywords
meth
acrylate
resin composition
curable resin
ultraviolet curable
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2010/005026
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English (en)
Japanese (ja)
Inventor
大祐 小林
裕貴 堤
正弘 内藤
潤 木戸場
雄一朗 松尾
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Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
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Filing date
Publication date
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Publication of WO2011052119A1 publication Critical patent/WO2011052119A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/254—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers
    • G11B7/2542—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers consisting essentially of organic resins
    • 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
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate

Definitions

  • the present invention relates to a novel ultraviolet curable resin composition, a cured product thereof, and an optical disc having the cured product layer (preferably an optical disc having a reflective film made of silver or a silver alloy).
  • DVDs currently in practical use are DVD-ROMs in which information such as movies have been recorded since the manufacture of the disc, and information is not recorded at the time of manufacture. It can be broadly classified into a recordable DVD for recording information.
  • the recording layer has a single-sided reading layer with a recording capacity of about 5 kigabytes DVD-5, a single-sided reading layer with a recording capacity of about 9-gigabytes DVD-9, and a double-sided reading layer with two layers.
  • DVD-9 is the mainstream because it has a recording capacity that can record about two and a half hours of movies.
  • DVD-9 is manufactured by bonding together a 0.6 mm polycarbonate substrate having a total reflection film made of an aluminum alloy and a 0.6 mm polycarbonate substrate having a translucent reflection film.
  • the translucent reflective film it is the mainstream to use silver or a silver alloy which is inexpensive and has a high reflectance.
  • a recordable DVD has many formats such as DVD-R, DVD + R, DVD-RW, DVD + RW, and DVD-RAM.
  • DVD-R, DVD-RW, DVD + R and DVD + RW are single-sided single-layer types.
  • This type is manufactured by bonding together a 0.6 mm polycarbonate substrate and a 0.6 mm polycarbonate substrate provided with a recording layer and a reflective film layer made of an organic dye or an inorganic compound.
  • a material for the reflective film layer silver or a silver alloy that is inexpensive and has a high reflectance is used.
  • BD Blu-ray Discs
  • HD DVDs having a recording capacity about five times that of single-layer DVDs
  • a Blu-ray disc has a structure in which a recording layer is formed on a transparent or opaque plastic substrate and a light transmission layer of about 0.1 mm is laminated on the recording layer, and recording / reproduction is performed through the light transmission layer. It is.
  • Blu-ray discs also use silver or a silver alloy as a reflective film, as with DVDs.
  • Patent Document 1 proposes an ultraviolet curable CD-R protective coat resin characterized by containing an alkylene thiol compound and Patent Document 2 containing an alkyl thioether compound.
  • the protective coating layer for CD-R is as thin as about 10 ⁇ m and is less affected by stress after curing. Therefore, even if the resin system has a high crosslinking density and good heat resistance, the warpage of the substrate is within the standard range. It is easy to fit in.
  • a thick adhesive layer such as a DVD or a light-transmitting layer such as a Blu-ray disc can increase the heat resistance of the resin itself because the substrate is warped when a resin having a high heat resistance and a high crosslinking density is used. Have difficulty.
  • the alkylene thiol compound and the alkyl thioether compound based on the conventional protective coating resin have sufficient characteristics to prevent alteration of the silver or silver alloy reflective film of the light-transmitting layer of an adhesive layer such as a DVD or a Blu-ray disc. It is in a situation that has not been done.
  • the present invention can improve the durability (particularly wet heat durability) of an optical disk, particularly an optical disk having a reflective film made of silver or a silver alloy, and is useful as an ultraviolet curable resin composition (ultraviolet light).
  • the purpose is to develop a curable resin composition or a photocurable resin composition).
  • the present inventors have found that when a polysulfide compound, for example, a polysulfide compound represented by the following general formula (1) is added to an ultraviolet curable resin composition, the resin
  • the optical disk having a reflective film made of silver or a silver alloy having a cured product layer of the composition has higher wet heat durability than the same optical disc having a cured product layer of the same ultraviolet curable resin composition to which the polysulfide compound is not added.
  • the optical disc regardless of the type of photopolymerizable compound (resin) used in the ultraviolet curable resin composition and the properties (crosslinking density and heat resistance) of the resin composition, the optical disc, particularly silver or silver In an optical disc having a reflective film made of an alloy, the durability of the optical disc can be improved.
  • An ultraviolet curable resin composition comprising (A) a polysulfide compound, (B) a photopolymerizable compound, and (C) a photopolymerization initiator.
  • the polysulfide compound is represented by the following general formula (1) (In the formula, n represents an integer of 2 to 6.
  • R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • X represents each independently. Represents an oxygen atom or a sulfur atom).
  • the ultraviolet curable resin composition according to the above (1).
  • the polysulfide compound (A) represented by the general formula (1) is represented by the formula (2) Formula (3) Or formula (4) The ultraviolet curable resin composition as described in said (2) represented by these. (4) The ultraviolet curable resin composition according to the above (2) or (3), wherein the polysulfide compound (A) represented by the general formula (1) is contained in an amount of 0.001 to 1% by weight based on the entire composition. object.
  • (Meth) acrylate monomer (B-2) is dicyclopentenyloxyethyl (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (Meth) acrylate, phenoxyethyl (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, ethylene oxide modified phenoxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and ethylene oxide modified bisphenol A di
  • the ultraviolet curable resin composition according to the above (6) which is at least one selected from the group consisting of (meth) acrylates.
  • Photopolymerization initiator (C) is 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2,4,6-trimethyl Benzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2-hydroxy-2-methyl- [4- (1-methylvinyl) phenyl] propanol oligomer, 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl-propan-1-one and 1- [4- (2-hydroxyethoxy) -phenyl-]- The above (1), which is at least one selected from the
  • (10) Use of the ultraviolet curable resin composition according to any one of (1) to (9) for forming a cured resin layer of an optical disk.
  • (11) The use according to (10) above, wherein the cured resin layer of the optical disc is an adhesive layer or a light transmission layer.
  • (12) Use for an optical disc having a reflective film made of silver or a silver alloy of the ultraviolet curable resin composition according to any one of (1) to (9) above.
  • (12) Use for an optical disc having a reflective film made of silver or a silver alloy of the ultraviolet curable resin composition according to any one of (1) to (9) above.
  • (13) A cured product obtained by irradiating the ultraviolet curable resin composition according to any one of (1) to (9) with active energy rays.
  • the novel ultraviolet curable resin composition containing the polysulfide compound (A) of the present invention is suitable for a resin cured product layer of an optical disk.
  • it is represented by the general formula (1) of the present invention for a cured resin layer of an optical disk using silver or a silver alloy as a reflection film (particularly for an adhesive layer such as a DVD or a light transmission layer such as a Blu-ray disk).
  • the ultraviolet curable resin composition containing the polysulfide compound (A) is used, durability is imparted to the optical disc even when the cured product of the resin composition is not of high crosslink density, An optical disk with high reliability can be provided for long-time use.
  • the ultraviolet curable resin composition of the present invention contains a polysulfide compound, a photopolymerizable compound, and a photopolymerization initiator.
  • the respective contents of the resin composition are 0.001 to 1% by weight of the polysulfide compound (A), 0.5 to 20% by weight of the photopolymerization initiator (C), and the photopolymerizable compound (B). It is the balance, and can contain an optional additive in the range of about 0 to 50% by weight, preferably about 0 to 20% by weight, if necessary.
  • the total of the polysulfide compound (A) and the photopolymerization initiator (C) is preferably 2 to 20% by weight with respect to the total amount of the resin composition, and the remaining 80 to 98% by weight is the photopolymerizable compound (B ) Is more preferable.
  • % means% by weight
  • part means part by weight.
  • the polysulfide compound (A) contained in the composition of the present invention is preferably a compound represented by the general formula (1).
  • the following compounds are preferred.
  • R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X is both an oxygen atom, and n is 2 to 4 Polysulfide compound.
  • the compound represented by the general formula (1) can be produced, for example, by the method described in JP-T-2002-524442 or a method analogous thereto.
  • the compound represented by the formula (2) is prepared by cooling a morpholine-petroleum ether solution to ⁇ 78 ° C., then adding disulfur dichloride, and at ⁇ 78 ° C. for 15 minutes, and then at room temperature for 30 minutes. It can be produced by stirring.
  • the compound represented by General formula (1) may use a commercially available compound.
  • the compound represented by Formula (2) can be obtained as Balnock RTM R (made by Ouchi Shinsei Chemical Co., Ltd.) or Actor RTM R (Kawaguchi Chemical Industry Co., Ltd.).
  • the content of the component (A) in the ultraviolet curable resin composition is usually 0.001 to 1% by weight, preferably 0.005 to 0.5% by weight, more preferably 0.01 to 0.3% by weight. is there. If the content is less than 0.001% by weight, the effect on durability performance is poor. If the content is more than 1% by weight, the reflective film made of silver or a silver alloy tends to be deteriorated under a high temperature and high humidity test.
  • a (meth) acrylate compound is preferable.
  • the (meth) acrylate compound include compounds having one or more (preferably 1 to 6) (meth) acryloyl groups, and the kind thereof is not particularly limited.
  • Preferable (meth) acrylate compounds include (B-1) epoxy (meth) acrylate and / or urethane (meth) acrylate.
  • a (B-2) (meth) acrylate monomer can also be used.
  • the component (B) preferably contains at least the component (B-1). More preferred is the combined use of the component (B-1) and the component (B-2).
  • the term “(meth) acrylate” means “methacrylate or acrylate”.
  • the epoxy (meth) acrylate and / or urethane (meth) acrylate as the component (B-1) is not a problem as long as at least one of them is contained in the resin composition of the present invention.
  • the resin composition of the present invention containing at least epoxy (meth) acrylate is more preferable.
  • the aspect containing both an epoxy (meth) acrylate and urethane (meth) acrylate is also one of the preferable aspects of this invention.
  • the epoxy (meth) acrylate (B-1) improves the curability and the hardness and curing speed of the cured product.
  • the epoxy (meth) acrylate in the present invention can be obtained by reacting a glycidyl ether type epoxy compound with (meth) acrylic acid.
  • the epoxy (meth) acrylate obtained by reaction with the following glycidyl ether type epoxy compound and (meth) acrylic acid can be mentioned.
  • the glycidyl ether type epoxy compound include bisphenols, alkylene oxide adducts thereof (preferably C2 to C5 alkylene oxide adducts), diglycidyl ethers of hydrogenated bisphenols, C2 to C10 aliphatic glycols or poly C2 ⁇ C4 alkylene glycol glycidyl ether.
  • the bisphenols are preferably bis (4-hydroxyphenyl) C1-C3 alkanes (which may have halogeno substitution on the alkanes), more preferably bisphenol A, bisphenol F, more preferably bisphenol A. is there.
  • Specific examples of the glycidyl ether type epoxy compound include, for example, diglycidyl ether of bisphenol A or its alkylene oxide adduct (also referred to as alkylene oxide-modified bisphenol A), diglycidyl ether of hydrogenated bisphenol A or its alkylene oxide adduct.
  • Bisphenol A epoxy compounds such as bisphenol F or diglycidyl ethers of alkylene oxide adducts thereof, bisphenol Fs such as hydrogenated bisphenol F or diglycidyl ethers of alkylene oxide adducts thereof
  • Epoxy compounds also called bisphenol F type epoxy compounds
  • ethylene glycol diglycidyl ether, propylene glycol diglycidyl C2-C8 aliphatic glycol diglycidyl ether such as ether, neopentyl glycol diglycidyl ether, butanediol diglycidyl ether, hexanediol diglycidyl ether, cyclohexane dimethanol diglycidyl ether
  • poly (C2 -C4 alkylene glycol) diglycidyl ether such as bisphenol F or diglycidyl ethers of alkylene oxide adducts thereof, bisphenol Fs such as hydrogenated bisphenol F or diglycidyl ether
  • the epoxy (meth) acrylate can be obtained by a reaction between the glycidyl ether type epoxy compound and (meth) acrylic acid.
  • the reaction will be described more specifically as follows.
  • (Meth) acrylic acid is reacted at a ratio of 0.9 to 1.5 mol, more preferably 0.95 to 1.1 mol, per 1 equivalent of epoxy group of the glycidyl ether type epoxy compound.
  • the reaction temperature is preferably 80 to 120 ° C., and the reaction time is about 10 to 35 hours.
  • a catalyst such as triphenylphosphine, TAP, triethanolamine, or tetraethylammonium chloride.
  • a polymerization inhibitor for example, paramethoxyphenol, methylhydroquinone, etc.
  • a polymerization inhibitor for example, paramethoxyphenol, methylhydroquinone, etc.
  • preferred epoxy (meth) acrylates are as described above, and more preferably, by reaction of bisphenols, their alkylene oxide adducts or diglycidyl ethers of hydrogenated bisphenols with (meth) acrylic acid.
  • the di (meth) acrylates of bisphenol diglycidyl ether bisphenol A epoxy di (meth) acrylate obtained from the epoxy compound of bisphenol A is more preferable, and more preferably di (meth) acrylate of bisphenol A diglycidyl ether. ) Acrylate.
  • the alkylene oxide adduct is preferably a C2-C5 alkylene oxide adduct, more preferably a C2 or C3 alkylene oxide adduct.
  • the molecular weight of the epoxy (meth) acrylate (B-1) is usually about 400 to 10,000, preferably about 500 to 10,000. In some cases, it is preferably about 400 to 5000, more preferably about 400 to 3000.
  • the urethane (meth) acrylate (B-1) that can be used in the present invention is a mechanical property (warp, distortion, etc.) of an optical disc (DVD or Blu-ray disc, etc.) having a resin cured layer using the ultraviolet curable resin composition of the present invention.
  • the urethane (meth) acrylate used in the present invention is obtained by reacting a polyhydric alcohol, an organic polyisocyanate, and a hydroxy (meth) acrylate compound.
  • polyhydric alcohol examples include aliphatic polyhydric alcohols (eg neopentyl glycol, 3-methyl-1,5-pentanediol, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, Trimethylolpropane, pentaerythritol, tricyclodecanedimethylol, bis- [hydroxymethyl] -cyclohexane, etc., these aliphatic polyhydric alcohols and polybasic acids (eg succinic acid, phthalic acid, hexahydrophthalic anhydride, terephthalic acid) Polyester polyol obtained by reaction with adipic acid, azelaic acid, tetrahydrophthalic anhydride, etc., caprolactone alcohol obtained by reaction of polyhydric alcohol with ⁇ -caprolactone, polycarbonate polyol (for example, 1,6 -Polycarbonate diol obtained by
  • polyether polyols are preferred, poly C2 to C6 alkylene glycols are more preferred, and polypropylene glycol or polytetramethylene glycol are more preferred.
  • the molecular weight is about 100 to 10,000, preferably about 300 to 3,500, and more preferably about 300 to 2500.
  • a diisocyanate compound can be exemplified.
  • the diisocyanate compound for example, C6-C13 hydrocarbon diisocyanate optionally substituted with an oxo group is preferable.
  • diisocyanate examples include isophorone diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, xylene diisocyanate, or diphenylmethane-4,4′-diisocyanate, and more preferred is isophorone diisocyanate or tolylene diisocyanate. . Isophorone diisocyanate is more preferred.
  • preferred hydroxy (meth) acrylate compounds include hydroxy-substituted C2-C10 aliphatic (meth) acrylates or hydroxycaprolactone (meth) acrylates. Of these, hydroxy-substituted C2-C10 aliphatic (meth) acrylates are more preferred.
  • Examples of hydroxy-substituted C2 to C10 aliphatic (meth) acrylates include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylol cyclohexyl mono (meth) acrylate, and the like. (Meth) acrylate is more preferable.
  • the reaction is performed as follows, for example. That is, first, the polyhydric alcohol and the organic polyisocyanate are preferably reacted at a ratio of 1.1 to 2.0 equivalents of the isocyanate group equivalent of the organic polyisocyanate to 1 equivalent of the hydroxyl group of the polyhydric alcohol. Synthesize urethane oligomers.
  • the reaction temperature is preferably 70 to 90 ° C.
  • the obtained urethane oligomer and hydroxy (meth) acrylate compound are preferably used in such a ratio that the hydroxyl equivalent of the hydroxy (meth) acrylate compound is 1 to 1.5 equivalent per equivalent of isocyanate group of the urethane oligomer.
  • the desired urethane (meth) acrylate can be obtained by reacting.
  • the reaction temperature at this time is preferably 70 to 90 ° C.
  • Preferred urethane (meth) acrylates include polyether polyols (more preferably poly C2-C6 alkylene glycols), diisocyanate compounds (eg C6-C13 hydrocarbon diisocyanates optionally substituted with oxo groups) and hydroxy (meth) acrylates.
  • the urethane (meth) acrylate is also commercially available as UX-6101 (polyether urethane acrylate: manufactured by Nippon Kayaku Co., Ltd.).
  • the molecular weight of the urethane (meth) acrylate (B-1) is usually about 400 to 10,000, preferably about 500 to 10,000, more preferably about 500 to 4000, and further preferably 500 to 3000.
  • the component (B-1) described above preferably contains at least one of epoxy (meth) acrylate and urethane (meth) acrylate, more preferably at least epoxy (meta). ) Acrylate.
  • the combined use of epoxy (meth) acrylate and urethane (meth) acrylate is also preferred.
  • the (meth) acrylate monomer of the component (B-2) in the present invention is a mono (meth) acrylate compound or a poly (meth) acrylate compound as long as it is a (meth) acrylate monomer other than the component (B-1). Any of these is not particularly limited. Usually, a (meth) acrylate monomer having a (meth) acryloyl group in the range of 1 to 6 is used. Moreover, depending on the case, it can be used even if it has 7 or more (meth) acryloyl groups.
  • the component (B-2) is usually preferably used in combination with the component (B-1).
  • (meth) acrylate monomer that can be used as the component (B-2)
  • phosphoric acid (meth) acrylate described later is also included. Since phosphoric acid (meth) acrylate achieves an action different from that of other (meth) acrylate monomers, it will be dealt with in another item described later.
  • preferable (meth) acrylate monomers having one (meth) acryloyl group used as component (B-2) include the compounds exemplified below. .
  • FANCRYL RTM FA-511A dicyclopentenyl oxyethyl acrylate (e.g., Hitachi Chemical Co., Ltd. FANCRYL RTM FA-512A), dicyclopentenyloxy methacrylate
  • FANCYR RTM FA-512M manufactured by Hitachi Chemical Co., Ltd.
  • dicyclopentanyl acrylate for example, FANCRRY RTM FA-513A manufactured by Hitachi Chemical Co., Ltd.
  • dicyclopentanyl methacrylate for example, manufactured by Hitachi Chemical Co., Ltd.
  • FANCYL RTM FA-513M 1-adamantyl acrylate
  • Adamantate AA manufactured by Idemitsu Kosan Co., Ltd.
  • 2-methyl-2-adamantyl acrylate for example, Adamantate MA manufactured by Idemitsu Kosan Co., Ltd., 2-ethyl-2-adamantyl acrylate (for example, Adamantate EA manufactured by Idemitsu
  • dicyclopentenyloxyethyl (meth) acrylate (FA-512A or 512M), phenoxyethyl (meth) acrylate and ethylene oxide-modified phenoxyethyl (meth) acrylate (such as PHE-2), phenoxypolyethylene glycol (meth) ) Acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate is more preferred.
  • the (meth) acrylate monomer having one (meth) acryloyl group described above suppresses mechanical properties (warp or distortion) of an optical disc having a cured layer (resin cured layer) of the ultraviolet curable resin composition of the present invention. ).
  • (meth) acrylate monomer having two (meth) acryloyl groups used as the component (B-2) also referred to as a di (meth) acrylate compound
  • a C5-C15 glycol dialkyl which may contain an aliphatic ring may be used.
  • examples of the di (meth) acrylate compound include di (meth) acrylates of C2-C3 alkylene oxide-modified C5-C10 aliphatic glycol.
  • the aliphatic ring in the above-mentioned C5-C15 glycol which may contain an aliphatic ring may be a dioxane ring containing an oxygen atom, and a preferred ring is preferably a 6- to 10-membered ring, and the ring comprises one. Or a ring in which a plurality of rings are bonded, such as a tricyclodecane ring.
  • Preferable rings include a cyclohexane ring, a dioxane ring, a tricyclodecane ring, and the like.
  • the number of moles of C2 to C3 alkylene oxide added to the C2 to C3 alkylene oxide modified bisphenol A di (meth) acrylate is preferably about 2 to 20 moles, more preferably about 4 to 10 moles.
  • (meth) acrylate monomer having two (meth) acryloyl groups include the compounds exemplified below. Cyclohexane-1,4-dimethanol di (meth) acrylate, cyclohexane-1,3-dimethanol di (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate (for example, KAYARAD RTM R-684 manufactured by Nippon Kayaku Co., Ltd .: Tricyclodecane dimethylol diacrylate, etc.), dioxane glycol di (meth) acrylate (for example, KAYARAD RTM R-604: dioxane glycol diacrylate, manufactured by Nippon Kayaku Co., Ltd.), neopentyl glycol di (meth) acrylate, dicyclo Pentanyl di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, alkylene oxide modified 1,
  • alkylene oxide modification is preferably C2 to C4 alkylene oxide modification.
  • terms such as “alkylene oxide modification” or “ethylene oxide modification” mean those obtained by adding alkylene oxide or ethylene oxide to glycol or the like.
  • dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, ethylene oxide modified bisphenol A di (meth) acrylate, neopentyl glycol diacrylate Etc. are preferred.
  • the resin composition of the present invention preferably contains the above di (meth) acrylate.
  • Examples of the (meth) acrylate monomer having three (meth) acryloyl groups that can be used as the component (B-2) include the compounds exemplified below.
  • Examples of the (meth) acrylate monomer having four (meth) acryloyl groups that can be used as the component (B-2) include pentaerythritol polyethoxytetra (meth) acrylate, pentaerythritol polypropoxytetra (meth) acrylate, pentaerythritol tetra ( Examples include (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, and the like, and pentaerythritol polyethoxytetra (meth) acrylate is more preferable.
  • Examples of the (meth) acrylate monomer having five (meth) acryloyl groups that can be used as the component (B-2) include dipentaerythritol penta (meth) acrylate and caprolactone-modified dipentaerythritol penta (meth) acrylate. it can.
  • Examples of the (meth) acrylate monomer having 6 (meth) acryloyl groups that can be used as the component (B-2) include dipentaerythritol hexa (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate. Dipentaerythritol hexa (meth) acrylate is more preferable.
  • the (meth) acrylate monomer that can be used in the present invention may be a polyfunctional monomer having 7 or more (meth) acryloyl groups.
  • any of the above (meth) acrylate monomers can be used.
  • preferred compounds as component (B-2) are as follows.
  • poly C2 to C4 alkylene glycol diacrylate poly is preferably 2 to 5.
  • dipropylene glycol diacrylate is preferable.
  • tripropylene glycol diacrylate, etc. C5-C6 alkylene glycol diacrylate (preferably neopentyl glycol diacrylate, 1,6 hexanediol diacrylate, etc.), dicyclopentenyloxyethyl (meth) acrylate (following FA-512A) Etc.), ethylene oxide-modified phenoxyethyl (meth) acrylate (such as PHE-2 described later), ethylene oxide 2 to 20 mole modified (preferably 3 to 15 mole modified) bisphenol A diacrylate (described later BPE4A, P-10, etc.), etc. can be mentioned.
  • C5-C6 alkylene glycol diacrylate preferably neopentyl glycol diacrylate, 1,6 hexanediol diacrylate, etc.
  • dicyclopentenyloxyethyl (meth) acrylate followeding FA-512A) Etc.
  • component (B-2) suitable for the light transmission layer of BD dicyclopentenyloxyethyl (meth) acrylate (such as FA-512A described later), ethylene oxide-modified phenoxyethyl (meth) acrylate (described later PHE) -2), ethylene oxide 2 to 20 mol modified (preferably 3 to 15 mol modified) bisphenol A diacrylate (BPE4A, BP-10 etc.
  • neopentyl glycol diacrylate, etc. tricyclodecane dimethylol Diacrylate (R-684 described later), neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol polyethoxytetraacrylate, dipentaerythritol hexaacrylate, etc. It can gel.
  • One preferred embodiment of the present invention is an embodiment containing a di (meth) acrylate compound as component (B-2). That is, in the resin composition of the present invention, an embodiment including a di (meth) acrylate compound as the component (B-1) and the component (B-2) as the component (B) is one of the preferred embodiments. is there. An embodiment in which the above-described preferred di (meth) acrylate compound is used as the di (meth) acrylate compound is one of the more preferred embodiments.
  • the content of the di (meth) acrylate compound with respect to the total amount of the component (B-2) is not particularly limited, but is preferably 30 to 100% by weight, more preferably 40 to 100% by weight, Preferably, it is 50 to 100% by weight.
  • the component (B-2) other than the di (meth) acrylate compound include (meth) acrylate compounds other than the di (meth) acrylate compounds described above, and the content thereof is preferably about 0 to 70% by weight. Is about 0 to 60% by weight, more preferably about 0 to 50% by weight.
  • an embodiment in which the component (B-2) other than the di (meth) acrylate compound is a mono (meth) acrylate compound is also preferred.
  • the mono (meth) acrylate compound is more preferable than the preferable or more preferable mono (meth) acrylate compound described above.
  • the mono (meth) acrylate compound or di (meth) acrylate compound that is preferable as the component (B-2) is preferably the mono (meth) acrylate mentioned above in the section of the (meth) acrylate monomer having one (meth) acryloyl group. Mention may be made of the di (meth) acrylate compounds mentioned as preferred in the section of (meth) acrylate compounds or (meth) acrylate monomers having two (meth) acryloyl groups.
  • the mono (meth) acrylate compound include dicyclopentenyloxyethyl (meth) acrylate (such as FA-512A), phenoxyethyl (meth) acrylate, and ethylene oxide-modified phenoxyethyl (meth).
  • the acrylate compound include dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and ethylene oxide modified (preferably 2-20 moles degeneration, more preferably at least one di (meth) acrylate compound selected from 3-15 mol modified) bisphenol A di (meth) acrylate, and the group consisting of neopentyl glycol diacrylate.
  • preferred (meth) acrylate compounds other than the mono (meth) acrylate compound or di (meth) acrylate compound are tricyclodecane dimethylol diacrylate (R-684), trimethylolpropane. Examples include triacrylate, pentaerythritol triacrylate, pentaerythritol polyethoxytetraacrylate, and dipentaerythritol hexaacrylate.
  • the above-mentioned mono (meth) acrylate compounds and di (meth) acrylate compounds can be mentioned, and as the more preferable (meth) acrylate monomer, dicyclo Pentenyloxyethyl (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, phenoxyethyl (meth) acrylate, ethylene oxide modified phenoxyethyl (Meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, and ethylene oxide modified bisphenol A di (meth) Mention may be made of acrylate.
  • these (B) components can be used 1 type or in mixture of 2 or more types by arbitrary ratios.
  • the content of the component (B) in the ultraviolet curable resin composition is usually 80 to 98% by weight, preferably 85 to 98% by weight.
  • the remaining 2 to 20% by weight, preferably 2 to 15% is the component (A) (polysulfide compound) and the component (C) (photopolymerization initiator).
  • (B-1) and (B-2) are used in combination as component (B)
  • (B-1) is usually 20 to 80 parts by weight, preferably 25 parts per 100 parts by weight of component (B).
  • the amount of (B-2) is about 20 to 80 parts by weight, preferably about 25 to 75 parts by weight, based on 100 parts by weight of component (B).
  • phosphoric acid (meth) acrylate can be added as component (B-2), if necessary.
  • Phosphoric acid (meth) acrylate improves the adhesion between aluminum, silver or a silver alloy and the cured adhesive.
  • the metal film may be corroded, and its use amount is limited.
  • it is preferably about 0 to 5% by weight, more preferably about 0 to 3% by weight, based on the total amount of the resin composition of the present invention.
  • the phosphoric acid (meth) acrylate that can be contained in the ultraviolet curable resin composition of the present invention is a monoester (also referred to as mono (meth) acrylate), a diester (if it is a (meth) acrylate having a phosphate ester skeleton. Di (meth) acrylate) or triester (also referred to as tri (meth) acrylate) may be used. Usually, ethylene oxide-modified phosphoric acid (meth) acrylate compounds are preferred.
  • Examples of the ethylene oxide-modified phosphoric acid (meth) acrylate compound include ethylene oxide-modified phenoxylated phosphoric acid (meth) acrylate, ethylene oxide-modified butoxylated phosphoric acid (meth) acrylate, ethylene oxide-modified octyloxylated phosphoric acid (meth) acrylate, and ethylene oxide.
  • Examples include modified phosphoric acid di (meth) acrylate and ethylene oxide-modified phosphoric acid tri (meth) acrylate. These are available from the market as, for example, PM-2 (ethylene oxide modified phosphoric dimethacrylate) manufactured by Nippon Kayaku Co., Ltd.
  • ethylene oxide-modified phosphate dimethacrylate is more preferable.
  • Phosphoric acid (meth) acrylate may be used alone or in combination of two or more.
  • the content thereof is usually 0.005 to 5% by weight, preferably 0.005 to 3% by weight, and more preferably in some cases. Is 0.005 to 1% by weight, more preferably 0.005 to 0.5% by weight.
  • the photopolymerization initiator (C) contained in the composition of the present invention is not particularly limited.
  • 1-hydroxycyclohexyl phenyl ketone (Irgacure RTM 184; manufactured by Ciba Specialty Chemicals)
  • 2-hydroxy- 2-methyl- [4- (1-methylvinyl) phenyl] propanol oligomer (Esacure ONE-Refined; manufactured by Nippon Sebel Hegner)
  • 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2 -Methyl-1-propan-1-one (Irgacure RTM 2959; manufactured by Ciba Specialty Chemicals)
  • 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl]- Phenyl ⁇ -2-methyl-propan-1-one (Irgacure RTM 127; Ciba Specialty Chemicals), 2,2-dimethoxy-2
  • these components (C) can be used alone or in combination of two or more at any ratio.
  • the content of the component (C) in the ultraviolet curable resin composition is usually 0.5 to 20% by weight, preferably 1 to 10% by weight.
  • amines that can serve as photopolymerization initiation assistants can be used in combination with the above photopolymerization initiator.
  • examples of amines that can be used include benzoic acid 2-dimethylaminoethyl ester, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, and p-dimethylaminobenzoic acid isoamyl ester.
  • the photopolymerization initiation assistant such as amines is an optional additive, and the content in the resin composition of the present invention is about 0 to 5% by weight. When the photopolymerization initiation assistant is used, the content in the resin composition of the present invention is usually 0.005 to 5% by weight, preferably 0.01 to 3% by weight.
  • an antioxidant In the ultraviolet curable resin composition for optical discs of the present invention, an antioxidant, an organic solvent, a silane coupling agent, a polymerization inhibitor, a leveling agent, an antistatic agent, a surface lubricant, a fluorescent whitening agent, if necessary
  • You may add arbitrary additives, such as a light stabilizer (for example, hindered amine compound etc.) and a filler.
  • the content of the optional additive is in the range of about 0 to 50% by weight based on the total amount of the resin composition of the present invention.
  • a filler may be included, but usually it is not included. Therefore, the content of any additive is 0 with respect to the total amount of the resin composition of the present invention.
  • the total amount of the three components (A), (C) and optional additives is about 2 to 20% by weight with respect to the total amount of the resin composition of the present invention.
  • an embodiment containing a light stabilizer can be mentioned.
  • the light stabilizer a hindered amine compound is preferable.
  • the content of the light stabilizer is about 0.1 to 3% by weight, more preferably about 0.1 to 1% by weight, based on the total amount of the resin composition of the present invention.
  • hindered amine compounds include 1,2,2,6,6-pentamethyl-4-piperidyl alcohol, 2,2,6,6-tetramethyl-4-piperidyl alcohol, 1,2,2,6,6. -Pentamethyl-4-piperidyl (meth) acrylate (LA-82), 2,2,6,6-tetramethyl-4-piperidyl (meth) acrylate, manufactured by Ciba Specialty Chemicals, CHIMASSORB 119FL, CHIMASSORB 2020FDL, CHIMASSORB 944FDL, TINUVIN 622LD, TINUVIN 123S, TINUVIN 144, TINUVIN 765, TINUVIN 770DF, TINUVIN 111FDL, TINUVIN 783FDL, TINUVIN 791FB, TINUVIN XT850FF, TINUVIN XT855FF, etc.
  • any hindered amine compound having a light stabilizing effect can be used.
  • One preferable example is 4-piperidyl alcohol having 4 to 6 methyl substitutions exemplified above or a (meth) acrylic acid ester thereof, and a hindered amine compound having a (meth) acryloyl group is more preferable.
  • the photopolymerizable compound contains (B-1) at least one of epoxy (meth) acrylate or urethane (meth) acrylate, and further contains (B-2) (meth) acrylate monomer, and the total amount of component (B)
  • the (meth) acrylate monomer contains a di (meth) acrylate compound, and the di (meth) acrylate compound may contain an aliphatic ring. 4.
  • the UV curable type according to 2 or 3 above which is di (meth) acrylate of C4 alkylene glycol (preferably di (meth) acrylate of di-tetra C2 to C4 alkylene glycol) or ethylene oxide-modified bisphenol A di (meth) acrylate. Resin composition. 5.
  • the di (meth) acrylate compound is contained in an amount of 30 to 100% by weight based on the total amount of the component (B-2), and other than the di (meth) acrylate compound ( 5.
  • the ultraviolet curable resin composition according to any one of 2 to 4 above, containing 0 to 70% by weight of a meth) acrylate compound.
  • Component (meth) acrylate monomer includes both (meth) acrylate monomer other than phosphoric acid (meth) acrylate and phosphoric acid (meth) acrylate, and the content of phosphoric acid (meth) acrylate is resin 7.
  • Di (meth) acrylate compound is dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, ethylene oxide modified bisphenol A di (meth) acrylate or neopentyl 8.
  • the ultraviolet curable resin composition according to any one of 4 to 7 above, which is glycol di (meth) acrylate. 9.
  • An optional additive other than the component (A), the component (B), and the component (C) is included in an amount of 0.005 to 5% by weight based on the total amount of the resin composition, the component (A), (C) 10.
  • 11. 11 The ultraviolet curable resin composition according to 10 above, wherein the optional additive is a light stabilizer, and the light stabilizer is a hindered amine.
  • the resin composition of the present invention can be obtained by mixing and dissolving the aforementioned components at room temperature to 80 ° C. If necessary, impurities may be removed by an operation such as filtration. In the resin composition of the present invention, it is preferable to appropriately adjust the blending ratio of components so that the viscosity at 25 ° C. is in the range of 100 to 5000 mPa ⁇ s, preferably 200 to 3000 mPa ⁇ s, in view of applicability.
  • the resin composition of the present invention can be used as various resin coat layers (adhesive layer, transparent resin layer, protective coat layer) and the like.
  • it is useful as a resin coating layer for an optical disk, and can be used as, for example, a protective coating layer, an adhesive layer, and a light transmission layer.
  • it can be suitably used as an adhesive for bonded optical discs such as DVDs or a coating agent for light transmitting layers on the laser incident side of Blu-ray discs or the like.
  • the resin composition of the present invention is used as various resin coat layers, the resin composition of the present invention is formed on the substrate on which the resin coat layer is to be provided by a conventional method so as to have a desired thickness.
  • the cured resin coat layer can be formed by applying and, if necessary, laminating a substrate or the like laminated thereon, and then irradiating the resin coat layer with ultraviolet rays to cure the resin coat layer.
  • the resin composition of the present invention is applied to the optical disk substrate by an arbitrary method such as spin coating, 2P, roll coating, or screen printing so that the thickness of the applied resin becomes 1 to 150 ⁇ m. Apply to.
  • two optical disk substrates are overlapped via an adhesive layer, and then the adhesive layer is cured by irradiating ultraviolet light to near ultraviolet light (wavelength 200 to 400 nm) from one or both sides. Glue.
  • a light transmission layer After the composition is applied, it is cured by irradiating ultraviolet rays to near ultraviolet rays (wavelength of 200 to 400 nm) from one side or both sides. Irradiation dose is preferably from about 50 ⁇ 1500mJ / cm 2, more preferably 100 ⁇ 1000mJ / cm 2 approximately.
  • a lamp capable of irradiating ultraviolet rays to near ultraviolet rays is usually used.
  • a low-pressure, high-pressure or ultrahigh-pressure mercury lamp, metal halide lamp, (pulse) xenon lamp, or electrodeless lamp can be used.
  • the optical disk substrate a known substrate, that is, a substrate using silicon, a silicon compound, silver or a silver alloy as a translucent reflective film can be used.
  • the composition of the present invention is suitable for an optical disk using silver or a silver alloy as a total reflection film or a semitransparent reflection film.
  • An optical disc having a cured product layer of the resin composition of the present invention includes an optical disc in which two or more optical disc substrates are bonded by the cured product layer of the resin composition of the present invention, particularly at least one of a plurality of optical disc substrates.
  • a laminated optical disk which is an optical disk substrate having a total reflection film or a semitransparent reflection film of silver or silver alloy, and an optical disk substrate having a total reflection film or a semitransparent reflection film of silver or silver alloy (normally 1.1 mm in thickness)
  • the optical disc for example, a Blu-ray disc having a cured product layer of the resin composition of the present invention is included as a light transmission layer.
  • the ultraviolet curable resin composition according to any one of (2) to (9) of the means for solving the problems is used.
  • ⁇ 11 An optical disk having a cured product layer of the ultraviolet curable resin composition according to any one of the above.
  • optical disk examples include DVD-ROM (DVD-5, DVD-10, DVD-9, DVD-14, DVD-18), DVD-R, DVD + R, DVD-RW, DVD + RW, DVD-RAM, DVD- R single-sided double layer method, DVD + R single-sided double layer method, DVD-RW single-sided double layer method, DVD + R single-sided double layer method, HD DVD-ROM, HD DVD-R, BD-ROM, BD-R, BD-RE, etc. be able to.
  • Examples D1 to D5 Comparative Examples D1 to D2 The ultraviolet curable resin compositions of each Example and each Comparative Example were prepared by mixing the components shown in Table 1 until they became uniform so that the compositions shown in Table 1 below were obtained.
  • Examples B1 to B7 Comparative examples B1 and B2 The ultraviolet curable resin compositions of each Example and each Comparative Example were prepared by mixing the components shown in Table 2 until they became uniform so as to have the compositions shown in Table 2 below.
  • each component shown with the abbreviation in Table 1 and Table 2 is as follows.
  • Compound of formula (2) Balnock R (manufactured by Ouchi Shinsei Chemical Co., Ltd.)
  • EPA Bisphenol A diglycidyl ether diacrylate
  • UA-1 Three components of polytetramethylene glycol (molecular weight 850), isophorone diisocyanate, and 2-hydroxyethyl acrylate in a molar ratio of 1: 2: 2.
  • BPE4A Ethylene oxide 4 mol modified bisphenol A diacrylate, Daiichi Kogyo Seiyaku Co., Ltd.
  • BPE-10 Ethylene oxide 10 mol modified bisphenol A diacrylate, Daiichi Kogyo Seiyaku Co., Ltd.
  • DPGDA Dipropylene glycol diacrylate
  • TPGDA Tri Propylene glycol diacrylate
  • HDDA 1,6-hexanediol diacrylate
  • FA-512A dicyclopentenyloxyethyl acrylate, Hitachi Chemical Co., Ltd.
  • PHE-2 ethylene oxide 2-mol modified phenoxyethyl acrylate
  • PM -2 Ethylene oxide modified dimethacrylate phosphate, Irgacure 184D manufactured by Nippon Kayaku Co., Ltd .: 1-hydroxycyclohexyl phenyl ketone, Ciba Specialty ONE-Refined by Micals Co., Ltd .: Esacure ONE-Refined (2-hydroxy-2-methyl- [4- (1-methylvinyl) phenyl] propanol oligomer), LA-82 by Nippon Sebel Hegner: 1,2, 2,6,6-pentamethyl-4-piperidyl methacrylate, L-7002 manufactured by Asahi Denka Co., Ltd .: silicone (leveling agent), KBM-803 manufactured by Toray Dow Corning Co., Ltd .: 3-mercaptopropyltrimethoxysilane (silane cup) Ring agent), manufactured by Shin-Etsu Chemical Co.,
  • Test Example 1 (Table 1) The ultraviolet curable resin compositions obtained in Examples D1 to D5 and Comparative Examples D1 to D2 were evaluated by the following methods.
  • a 0.6 mm thick PC substrate is placed on a silver reflective film substrate (sputtered surface is up) and spin coated at a speed of 3000 rpm for 4 seconds, and the ultraviolet curable type of the present invention between the PC substrate and the silver reflective film
  • the resin composition was laminated so that the film thickness was 35 to 55 ⁇ m.
  • the apparatus used was Global Machinery. 4).
  • the ultraviolet curable resin composition of the present invention was cured by irradiating 8 shots at 80 J from the upper side, and the disk substrate was adhered.
  • the direction of the DVD disk is the upper PC substrate and the lower silver reflective film substrate. 5.
  • a signal of about 4.7 gigabytes was recorded on the DVD + R substrate manufactured by the above 1 to 4 at a writing speed of 8 times speed by a drive manufactured by Pioneer (model: DVR-110).
  • Test Example 2 (Table 2) The ultraviolet curable resin compositions obtained in Examples B1 to B6 or Comparative Examples B1 and B2 were evaluated by the following methods.
  • the silver reflecting film substrate is a 1.1 mm thick PC substrate on which pits for BD-ROM are formed, using a silver alloy GB-100 manufactured by Kobe Steel, Ltd., and sputtered to an average film thickness of 30 nm.
  • a disk substrate with a reflective film was produced.
  • the viscosity of the ultraviolet curable resin composition of the present invention spin coating was performed at a speed range of 1000 rpm to 1500 rpm for 4 seconds to 7 seconds, and each coating film thickness was applied to 95 ⁇ m to 105 ⁇ m.
  • the xenon flash lamp was irradiated with two shots, and cured so that the fluidity of the surface disappeared. 4).
  • the UV curable resin composition of the present invention was completely cured by irradiating 8 shots at 80 J from the upper side to obtain a BD-ROM having a light transmission layer.
  • the disk of the present invention can be hard-coated on the resin surface, but in this evaluation, the durability of the light-transmitting layer itself was evaluated. It was.
  • Evaluation standard of RSER ⁇ RSER value less than 2.0E-04 (represents 2.0 ⁇ 10 ⁇ 4 ).
  • X RSER value of 2.0E-04 (represents 2.0 ⁇ 10 ⁇ 4 ) or more.
  • the RSER value “2.0E-04” represents “2.0 ⁇ 10 ⁇ 4 ”, and the same description in Table 2 also has the same meaning.
  • the initial value 5.1E-05 in Example B1 represents “5.1 ⁇ 10 ⁇ 5 ”, and the other descriptions are the same.
  • the optical disk using the resin composition of the present invention has a reflective film made of silver or a silver alloy, the optical disk is excellent in durability, such as an optical disk using silver or a silver alloy as a reflective film, particularly a DVD or the like. It is useful as a resin composition for a light transmission layer such as an adhesive layer or a Blu-ray disc.

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Abstract

La nouvelle composition de résine durcissable par ultraviolets selon l'invention contient (A) un composé de polysulfure, de préférence, un composé de polysulfure représenté par la formule générale (1) (dans la formule, n représente un nombre entier de 2 à 6 ; R1, R2, R3 et R4 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle ayant de 1 à 10 atomes de carbone ; et les X représentent chacun un atome d'oxygène ou un atome de soufre), (B) un composé photopolymérisable et (C) un initiateur de photopolymérisation. Cette composition de résine peut être utilisée comme couche de revêtement en résine pour disque optique (par exemple, couche adhésive d'un DVD lié ou couche transmettant la lumière d'un disque Blu-ray). En particulier, par l'action du composé de polysulfure, la composition de résine ci-décrite est capable d'améliorer la durabilité d'un disque optique qui est pourvu d'un film réfléchissant à base d'argent ou d'un alliage d'argent.
PCT/JP2010/005026 2009-10-29 2010-08-10 Composition de résine durcissable par ultraviolets, produit durci et disque optique Ceased WO2011052119A1 (fr)

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WO2025075971A1 (fr) * 2023-10-05 2025-04-10 Dow Global Technologies Llc Composition hybride de polyuréthane-acrylique pour produits ignifuges

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WO2012157200A1 (fr) * 2011-05-13 2012-11-22 日本化薬株式会社 Composition de résine à séchage ultraviolet
JP7514177B2 (ja) * 2019-12-20 2024-07-10 住友化学株式会社 重合性液晶組成物、偏光膜、偏光フィルムおよび偏光板

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