CN102379007A - Uv-curable resin composition for use in multi-layer optical disc - Google Patents
Uv-curable resin composition for use in multi-layer optical disc Download PDFInfo
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- CN102379007A CN102379007A CN2010800148704A CN201080014870A CN102379007A CN 102379007 A CN102379007 A CN 102379007A CN 2010800148704 A CN2010800148704 A CN 2010800148704A CN 201080014870 A CN201080014870 A CN 201080014870A CN 102379007 A CN102379007 A CN 102379007A
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- 0 **N(C(N(*N=C=O)C(N1*N=C=O)=O)=O)C1=O Chemical compound **N(C(N(*N=C=O)C(N1*N=C=O)=O)=O)C1=O 0.000 description 3
Classifications
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- 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
- G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
- G11B7/263—Preparing and using a stamper, e.g. pressing or injection molding substrates
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
-
- 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
-
- 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
-
- 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
- G11B7/256—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 layers improving adhesion between layers
-
- 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
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- 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
- G11B7/2403—Layers; Shape, structure or physical properties thereof
- G11B7/24035—Recording layers
- G11B7/24038—Multiple laminated recording layers
-
- 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
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Manufacturing Optical Record Carriers (AREA)
- Paints Or Removers (AREA)
Abstract
Disclosed is a base for use in an optical disc which has excellent mass productivity for substrate formation by a 2P method, particularly favorable release properties from a stamper, and high adhesion strength to a reflective film layer or a dielectric layer even under high-temperature and high-humidity conditions. Specifically disclosed is a UV-curable resin composition for use in a multi-layer optical disc, with which such a base for use in an optical disc can be formed. The UV-curable resin composition for use in a multi-layer optical disc contains (A) a hexa- or higher-functional urethane (meth)acrylate obtained by reacting an organic isocyanate having two or more isocyanate groups per molecule with a tri- or higher-functional (meth)acrylate having a hydroxy group, (B) a tri- or lower-functional (meth)acrylate monomer, and (C) a photopolymerization initiator.
Description
Technical field
The present invention relates to CD with ultraviolet-curing resin composition and solidfied material thereof, and relate to the closing force that is used for producing efficiently with reflective coating or dielectric layer high, from the resin combination of the good high density compact disc of future generation of the fissility of pressing mold.
Background technology
In recent years, remarkable to the requirement of the high capacity of CD.As the technology of the recording capacity that improves CD, can enumerate: high NA (numerical aperture) change of the object lens of the short wavelengthization of recording/reproducing light beam, recording/reproducing light beam irradiates optical system, the multiple stratification of recording layer etc.Wherein, utilize the high capacity of the multiple stratification realization of recording layer to compare with high NAization with the short wavelengthization, can be with the implemented with low cost high capacity.
For example, the DVD disk that has two recording layers adopts two recording layers across the transparent resin middle layer and range upon range of structure.Particularly, be the structure of second transparent resin substrate of first transparent resin substrate that stacks gradually 0.6mm, first recording layer, the first semitransparent reflector rete, transparent resin middle layer, second recording layer, second reflective coating, adhesive layer, 0.6mm.In this case; The transparent resin middle layer forms as follows: coating forms the ultraviolet-curing resin composition in transparent resin middle layer on the first semitransparent reflector rete; And be pressed in the transparent resin pressing mold of guiding with recording/reproducing light beam with relief patterns such as guiding grooves; After being solidified, the ultraviolet curable resin composition peels off pressing mold, thereby with the concavo-convex surface that is transferred to ultraviolet-curing resin composition.
With regard to the read-only type disk in the blu-ray disc; Be that recording figure forming with the pit shape is transferred on the surface as the polycarbonate substrate of the for example diameter 120mm of substrate, thick 1.1mm, and on the surface of this substrate, form first reflective coating, for example silver alloy reflective layer as first recording layer.And then, on first reflective coating, form the transparent resin middle layer that transfer printing has pit shape recording figure forming, and on this intermediate coat, form second reflective coating, for example silver alloy reflective layer as second recording layer.So, formed the structure of range upon range of transparent resin layer.In addition, proposed to form in a vacuum the method for silver alloy reflective layer through for example sputtering method.
With regard to the recordable type disk; Has following structure: the recording figure forming of pit shape is transferred on the surface as the polycarbonate substrate of the for example diameter 120mm of substrate, thick 1.1mm; And, stack gradually transparent resin middle layer, second reflective coating, the 3rd dielectric layer, second recording layer, the 4th dielectric layer, transparent resin layer again in surperficial laminated first reflective coating, first dielectric layer, first recording layer, second dielectric layer of this substrate.
Under above-mentioned situation; The transparent resin middle layer forms as follows: coating forms the ultraviolet-curing resin composition in transparent resin middle layer on reflective coating or dielectric layer; And by being pressed on the transparent resin pressing mold of guiding with recording/reproducing light beam with relief patterns such as guiding grooves; Peel off pressing mold after the ultraviolet curable resin composition is solidified, thereby make the concavo-convex surface that is transferred to ultraviolet-curing resin composition.At this; The transparent resin middle layer; In read-only type disk usually by constituting with the gluing peel ply of second reflective coating with the gluing adhesive layer of first reflective coating, in record type disk usually by constituting with the gluing peel ply of second reflective coating with the gluing adhesive layer of second dielectric layer.
Usually, this transfer printing is called 2P (Photo Polymerization, photopolymerization) method, employed ultraviolet-curing resin composition is called the 2P resin.
The transparent resin pressing mold can be enumerated: acrylic resin, metering system resinoid, polycarbonate resin, polyolefin resin (particularly amorphous polyolefin), polyester resin, polystyrene resin, epoxy resin etc.Wherein, the preferred amorphous polyolefin of viewpoint such as the fissility behind the 2P resin solidification, agent of low hygroscopicity, shape stability is from the viewpoint optimization polycarbonate resin of material cost.
Usually, the resin substrate of the 1.1mm of the resin substrate of the 0.6mm of DVD, blu-ray disc uses polycarbonate resin.When using polycarbonate resin,, can improve 2P resin bed and the fissility of polycarbonate system resin moulding-die after the curing through using the ultraviolet curing resin different with the 2P resin in the resin substrate side as the transparent resin pressing mold.
If the fissility on the self-induced transparency resin moulding-die is poor, thereby then the part in transparent resin middle layer can be peeled off the generation defective with the transparent resin pressing mold.If transfer printing property is poor, then can make a mistake during recording/reproducing.If warpage is big after the ultraviolet curing, then can't on established relief pattern, be formed uniformly recording layer or reflective coating, under the situation of DVD, can't make second baseplate-laminating, under the situation of blu-ray disc, can't be formed uniformly the light-transmitting layer of 0.1mm.In addition, if relief pattern deforms under hot and humid condition, then the recording characteristic of first, second recording layer (for example, jittering characteristic) can't keep identical.
The 2P resin of patent documentation 1～4 forms relief pattern through using metal pressing mold on glass substrate, form not record for the relief pattern that utilizes the transparent resin pressing mold.In addition, though the record of 2P resin is arranged in the patent documentation 5～8, for not record of resin of the present invention.
The prior art document
Patent documentation
Patent documentation 1: japanese kokai publication hei 5-59139 communique
Patent documentation 2: japanese kokai publication hei 5-132534 communique
Patent documentation 3: japanese kokai publication hei 5-140254 communique
Patent documentation 4: japanese kokai publication hei 5-132506 communique
Patent documentation 5: TOHKEMY 2003-331463 communique
Patent documentation 6: TOHKEMY 2004-288242 communique
Patent documentation 7: TOHKEMY 2004-288264 communique
Patent documentation 8: TOHKEMY 2005-332564 communique
Summary of the invention
Usually, the ultraviolet curing resin as the 2P agent needs and can under the state that keeps relief pattern, easily peel off from the pressing mold that is formed with this relief pattern.At this moment, if be difficult to peel off from pressing mold, then resin can be attached on the pressing mold, thereby produces not and problems such as reflective coating or dielectric layer be gluing, causes production efficiency to reduce.In addition,, peel off under hot and humid, also can produce the problem that read error occurs if place even from the high resin of the fissility of pressing mold.
Therefore; The present invention is in view of this actual conditions; Through using polyfunctional acrylic ester modified amido formic ether acrylic ester and (methyl) acrylate monomer, provide good especially and also can form down with the resin of reflective coating or dielectric layer driving fit hot and humid from the fissility of pressing mold.
And,, therefore can omit the adhesive layer of 2P agent ultraviolet curing resin because the present invention can be optionally gluing with reflective coating or dielectric layer when peeling off pressing mold.
The inventor makes organic isocyanate and carbamate (methyl) the acrylic ester ultraviolet-curing resin composition that the polyfunctional acrylic ester reaction with hydroxyl obtains through use, has found that fissility from pressing mold improves and places hot and humidly also can form with the resin of reflective coating or dielectric layer driving fit securely down.Thus, developed fissility height, the ultraviolet-curing resin composition good to the adaptation of reflective coating or recording film from pressing mold.
The present invention relates to following (1)～(7).
(1) a kind of multiplayer optical disk is used ultraviolet-curing resin composition, and it contains: above carbamate (methyl) acrylic ester of six senses that the organic isocyanate that has two above NCOs in the molecule is obtained with above (methyl) acrylate reactions of the trifunctional with hydroxyl, (methyl) acrylate monomer below (B) trifunctional and (C) Photoepolymerizationinitiater initiater.
(2) use ultraviolet-curing resin composition like above-mentioned (1) described multiplayer optical disk; Wherein, In carbamate (methyl) acrylic ester (A) that the organic isocyanate that in making a molecule, has two above NCOs obtains with (methyl) acrylate reactions more than the trifunctional with hydroxyl; Organic isocyanate is for being selected from by IPDI; 1; Hexamethylene-diisocyanate; Toluene diisocyanate; XDI; Diphenyl methane-4; 4 '-diisocyanate; Tetrahydro-dicyclopentadiene group diisocyanate (ジ シ Network ロ ペ Application タ ニ Le ジ イ ソ シ ア ネ one ト); And in the group formed of the trifunctional isocyanates of following formula (1) expression one or more
In the formula, R representes
(3) use ultraviolet-curing resin composition like above-mentioned (1) or (2) described multiplayer optical disk; Wherein, In carbamate (methyl) acrylic ester (A) that the organic isocyanate that in making a molecule, has two above NCOs obtains with (methyl) acrylate reactions more than the trifunctional with hydroxyl, has above (methyl) acrylic ester of the trifunctional of hydroxyl for being selected from the group of forming by three, four or five (methyl) acrylic ester of the 6-caprolactone addition product of three (methyl) acrylic ester of the 6-caprolactone addition product of pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, pentaerythrite and dipentaerythritol one or more.
(4) use ultraviolet-curing resin composition like each described multiplayer optical disk in above-mentioned (1)～(3); Wherein, (methyl) acrylate monomer (B) below the trifunctional is for being selected from the group of being made up of IBOA, neopentylglycol diacrylate, epoxy pronane modification neopentylglycol diacrylate, tristane dimethanol diacrylate and hydroxy pivalin aldehyde (ヒ De ロ ピ バ Le ア Le デ ヒ De) modification trimethylolpropane diacrylate one or more.
(5) use ultraviolet-curing resin composition like each described multiplayer optical disk in above-mentioned (1)～(4), wherein,, contain (A) composition 5～80 weight %, (B) composition 10～80 weight %, (C) composition 1～15 weight % with respect to the resin combination total amount.
(6) a kind of solidfied material is through obtaining with ultraviolet-curing resin composition irradiation active energy beam each described multiplayer optical disk in above-mentioned (1)～(5).
(7) a kind of multiplayer optical disk has above-mentioned (6) described solidfied material.
The invention effect
Ultraviolet-curing resin composition of the present invention and solidfied material thereof, can be used as from the fissility of pressing mold good and place under the hot and humid condition also can with the 2P agent of reflective coating or dielectric layer driving fit.In addition, can provide and to form the middle layer by a kind of solution and omit the ultraviolet curing resin of adhesive layer.
Embodiment
The present invention is that a kind of CD is used ultraviolet-curing resin composition; In resin combination, contain: above carbamate (methyl) acrylic ester of six senses that the organic isocyanate that has two above NCOs in the molecule is obtained with above (methyl) acrylate reactions of the trifunctional with hydroxyl, (methyl) acrylate monomer below (B) trifunctional and (C) Photoepolymerizationinitiater initiater.
In the ultraviolet-curing resin composition of the present invention, carbamate (methyl) acrylic ester more than six senses that the organic isocyanate that uses (A) to make to have two above NCOs in the molecule obtains with the reaction of hydroxyl modification polyfunctional acrylic ester.
The organic isocyanate that uses among the present invention is the compound that has two above NCOs in the molecule, so long as known material then can especially restrictedly not use.For example can enumerate: IPDI, hexamethylene diisocyanate, toluene diisocyanate, XDI, diphenyl methane-4, diisocyanates such as 4 '-diisocyanate or tetrahydro-dicyclopentadiene group diisocyanate.
In addition, among the present invention, as modified isocyanate, can use with diisocyanate monomer carry out isocyanurate-modifiedly obtaining, the trifunctional isocyanates of following formula (1) expression.
(in the formula, R representes
These compounds can for example can be enumerated as commercially available article through being synthesized into suitable known method: military field pharmaceutical industries corporate system タ ケ ネ one ト D-170N; Firmly change バ イ エ Le ウ レ タ Application corporate system ス ミ ジ ユ one Le N-3300, デ ス モ ジ ユ one Le L, デ ス モ ジ ユ one Le HL; デ グ Star サ corporate system T-1890.
As organic isocyanate, the trifunctional isocyanates of preferred formula among the application (1) expression, preferred especially hexamethylene diisocyanate isocyanurate trimer (R=-(CH
2)
6-) compound.
In addition, as modified isocyanate, also can make diisocyanate monomer carry out the isocyanates that biuret reaction obtains, following formula (2) is represented.
(in the formula, R is identical with the R of above-mentioned formula (1))
As (methyl) acrylic ester more than the trifunctional with hydroxyl, particularly be meant (methyl) acrylic ester of three～eight senses with hydroxyl, so long as known material then can especially restrictedly not use.As an example, can enumerate: three, four or five (methyl) acrylic ester of three (methyl) acrylic ester of the 6-caprolactone addition product of pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, pentaerythrite, the 6-caprolactone addition product of dipentaerythritol etc.Preferred especially pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester among the present invention.
Reaction is carried out as follows.Promptly; Per 1 equivalent of hydroxyl with respect to (methyl) acrylic ester more than the trifunctional with hydroxyl; Be preferably the mixed organic multiple isocyanate of 1.1～2.0 equivalents with the NCO of organic multiple isocyanate; And preferably make temperature of reaction be 70～90 ℃ and react, can access target carbamate (methyl) acrylic ester (A) thus.
Above-mentioned (A) carbamate (methyl) acrylic ester can use a kind of or use two or more with the arbitrary proportion mixing.As the use amount of (A) carbamate (methyl) acrylic ester in composition, in inherent ratio (in cut), be 5～80 weight %, be preferably 15～75 weight %, be preferably about 20 weight %～about 70 weight % especially.
As (methyl) acrylate monomer below (B) trifunctional that uses among the present invention, so long as known material then can especially restrictedly not use.As an example, can enumerate: tristane (methyl) acrylic ester, benzyl acrylate, (methyl) acrylic acid two cyclopentane esters, (methyl) IBOA, (methyl) acrylic acid diamantane ester, (methyl) benzyl acrylate, (methyl) tetrahydrofurfuryl acrylate, morpholine (methyl) acrylic ester, neopentyl glycol two (methyl) acrylic ester, epoxy pronane modification neopentyl glycol two (methyl) acrylic ester, tristane dihydroxymethyl two (methyl) acrylic ester, hydroxy pivalin aldehyde modification trimethylolpropane two (methyl) acrylic ester, 3-hydroxypivalic acid neopentyl glycol two (methyl) acrylic ester etc.
Wherein, In order to improve fissility, (methyl) acrylate monomer preferably uses IBOA, neopentylglycol diacrylate, epoxy pronane modification neopentylglycol diacrylate, tristane dimethanol diacrylate, hydroxy pivalin aldehyde modification trimethylolpropane diacrylate.As the use amount in composition, with inherent proportional meter, be 10～80 weight %, be preferably 15～75 weight %, more preferably 20～70 weight %.
As (C) Photoepolymerizationinitiater initiater that contains in the ultraviolet-curing resin composition of the present invention, can enumerate: 1-hydroxycyclohexylphenylketone (イ Le ガ キ ユ ア 1; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), 1-[4-(2-hydroxyl-oxethyl)-phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone (イ Le ガ キ ユ ア 1; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl propiono) benzyl] phenyl }-2-methylpropane-1-ketone (イ Le ガ キ ユ ア 1; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), 2,2-dimethoxy-2-phenyl acetophenone (イ Le ガ キ ユ ア 651; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), oligomeric [2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] acetone] (エ サ キ ユ ア ONE; ラ Application バ Le テ イ system), 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone (ダ ロ キ ユ ア 1173; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholinyl propane-1-ketone (イ Le ガ キ ユ ア 1; チ バ ス ペ シ ヤ リ テ イ one ケ ミ カ Le ズ system), 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl) butane-1-ketone, 2-clopenthixal ketone, 2; 4-dimethyl thioxanthones, 2; 4-diisopropyl thioxanthones, isopropyl thioxanthone, 2; 4,6-trimethylbenzoyl diphenyl phosphine oxide (Le シ リ Application TPO; The BASF system), two (2,4, the 6-trimethylbenzoyl) phenylphosphine oxide (イ Le ガ キ ユ ア 1; チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ system), two (2,6-dimethoxy benzoyl)-2,4,4-tri-methyl-amyl phosphine oxide etc.
These Photoepolymerizationinitiater initiaters can use a kind of separately, also can arbitrary proportion mix to use multiplely, also can cause auxiliary agent with photopolymerization such as amine and use.
As the content of (C) Photoepolymerizationinitiater initiater in the ultraviolet-curing resin composition of the present invention, use 1～15 weight %, be preferably about 1 weight %～about 10 weight %.
As Photoepolymerizationinitiater initiaters such as spendable amines among the present invention, can enumerate for example diethanolamine, 2-dimethyl aminoethyl benzoic ether, dimethylamino benzoylformaldoxime, ESCAROL 507 ethyl ester, ESCAROL 507 isopentyl ester etc.And when using Photoepolymerizationinitiater initiater, its content in ultraviolet-curing resin composition of the present invention is preferably 0.05～5 weight %, is preferably about 0.1 weight %～about 3 weight % especially.
In the ultraviolet-curing resin composition of the present invention, can add phosphoric acid (methyl) acrylic ester as required.Phosphoric acid (methyl) acrylic ester improves the tackiness of aluminium, silver or silver alloy and adhesive solidification thing, but also may the corroding metal film, so its consumption is restricted.
In addition, in the present invention, except that mentioned component, can also be as required also with adjuvants such as silane coupling agent, levelling agent, foam-breaking agent, polymerization inhibitor, light stabilizer (hindered amines etc.), anti-oxidant, antistatic agent, surface lubricant, filling agents.As the example of above-mentioned additive, for example can enumerate: the system KBM-502 of KCC of SHIN-ETSU HANTOTAI, KBM-503, KBM-5103, KBM-802, KBM-803; PVC Star Network ケ ミ one corporate system BYK-333, BYK-307, BYK-3500, BYK-3530, BYK-3570; The system Z-6062 of east レ ダ ウ コ one ニ Application グ Co., Ltd., SH-6062, SH-29PA; The ア デ カ of Co., Ltd. corporate system LA-82 etc.
Ultraviolet-curing resin composition of the present invention can through in normal temperature～80 ℃ down with above-mentioned each composition mixed dissolution, filter as required then and obtain.
The viscosity of ultraviolet-curing resin composition of the present invention is determined as 10～800mPas with Brookfield viscometer under 25 ℃, be preferably 40～500mPas.
Under the situation of DVD; The transparent resin middle layer can the method through following (1) form: at least one of range upon range of substrate that first transparent resin substrate, first recording layer, the first semitransparent reflector rete arranged and transparent resin pressing mold; Be coated with resin combination of the present invention through methods such as spin-coating method, silk screen print method, rolling methods; Both are fitted, and form from transparent resin pressing mold one side irradiation ultraviolet radiation.In addition; Also can the method through following (2) form: through above-mentioned coating process behind coating resin combination of the present invention on the transparent resin pressing mold; Carry out ultraviolet curing, and use arbitrarily ultraviolet curing resin and range upon range ofly the baseplate-laminating of first transparent resin substrate, first recording layer, the first semitransparent reflector rete is arranged and form.(1) formation method can be saved production efficiency, is expected to reduce production costs, and is therefore preferred.In addition, blu-ray disc also can be through forming the transparent resin middle layer with the same method of DVD.Usually, the resin substrate of the 1.1mm of first transparent resin substrate of the 0.6mm of DVD, HD-DVD, blu-ray disc uses polycarbonate resin.Under the situation of the polycarbonate system of use transparent resin pressing mold, consider from the fissility aspect, also the method for preferred (1).
As the transparent resin pressing mold, for example can enumerate: acrylic resin, methacrylic resin, polycarbonate resin, polyolefin resin (particularly amorphous polyolefin), polyester resin, polystyrene resin, epoxy resin etc.Wherein, aspects such as the fissility behind the 2P resin solidification, agent of low hygroscopicity, shape stability consider that preferred amorphous polyolefin is considered the optimization polycarbonate resin from the material cost aspect.2P curable resin composition of the present invention can use any one transparent resin pressing mold.
Ultraviolet-curing resin composition of the present invention, the irradiation through active energy beam forms solidfied material.This active energy beam can be enumerated for example ultraviolet～near ultraviolet light.For example can enumerate: low pressure mercury lamp, high-pressure sodium lamp, ultrahigh pressure mercury lamp, metal halid lamp, (pulse) xenon lamp, electrodeless lamp, ultraviolet LED etc.Above-mentioned solidfied material also is contained among the present invention.
The recording layer that on the transparent resin middle layer that is formed by above-mentioned solidfied material, forms can use in organic pigment, the phase-change material any one.For example; Organic pigment can be enumerated containing metal azo class, polymethine class, phthalocyanines, and phase-change material can be set forth in and be added with the material that is selected from any one the above material among In, Ag, Au, Bi, Se, Al, P, Ge, H, Si, C, V, W, Ta, Zn, Ti, Ce, Tb, Sn, the Pb among Sb and the Te.
In addition, resin combination of the present invention can be used for being fitted with CD, blu-ray disc any of the structure of polycarbonate system substrate.
As coating process, for example can enumerate: spin-coating method, 2P method, rolling method, silk screen print method etc.
In addition, because the blue laser that reads and/or write the about 400nm of use of high density compact disc of future generation, therefore, for the solidfied material of thickness 90～100 μ m, the transmissivity of preferred 405nm is more than 80%.
Embodiment
Below, utilize embodiment that the present invention is elaborated.
Synthetic example 1: urethane acrylate (A-1) synthetic
In the round-bottomed flask that has stirring apparatus, condenser pipe and thermometer, drop into IPDI 0.63 weight portion and pentaerythritol triacrylate 93.9 weight portions, as p methoxy phenol 0.03 weight portion and dibutyl tin laurate 0.05 weight portion of polymerization inhibitor; At room temperature mixed 30 minutes, and reacted 5 hours down at 80 ℃.Reach 0.1% cessation reaction when following in isocyanate concentration, obtain the target urethane acrylate.
Synthetic example 2: urethane acrylate (A-2) synthetic
In the round-bottomed flask that has stirring apparatus, condenser pipe and thermometer, drop into isocyanate-modified type (the military field pharmaceutical industries corporate system タ ケ ネ one ト D-170N of hexamethylene diisocyanate; Formula (1) R=-(CH
2)
6-) 11.6 weight portions and dipentaerythritol five acrylic ester 88.4 weight portions, as p methoxy phenol 0.05 weight portion and dibutyl tin laurate 0.05 weight portion of polymerization inhibitor, at room temperature mixed 30 minutes, and 80 ℃ of reactions 5 hours down.Reach 0.1% cessation reaction when following in isocyanate concentration, obtain the target urethane acrylate.
Synthetic example 3: urethane acrylate (A-3) synthetic
In the round-bottomed flask that has stirring apparatus, condenser pipe and thermometer, drop into 1; Hexamethylene-diisocyanate 14.8 weight portions and dipentaerythritol five acrylic ester 85.1 weight portions, as p methoxy phenol 0.03 weight portion and dibutyl tin laurate 0.05 weight portion of polymerization inhibitor; At room temperature mixed 30 minutes, and reacted 5 hours down at 80 ℃.Reach 0.1% cessation reaction when following in isocyanate concentration, obtain the target urethane acrylate.
Embodiment and Test Example
The constituent material of the resin combination of embodiment 1～3 and comparative example 1～3 and the evaluation result of use amount and following project are shown in table 1.In addition, " part " expression weight portion in the record content.
[table 1]
Table 1. resin is formed and evaluation result
In addition, as follows in the table 1 with each composition that is called for short expression.
A-1: the urethane acrylate that synthetic example 1 obtains
A-2: the urethane acrylate that synthetic example 2 obtains
A-3: the urethane acrylate that synthetic example 3 obtains
IBA: IBOA, the first industrial chemistry corporate system
RP-1040: pentaerythrite oxirane modification tetraacrylate, Japanese chemical drug corporate system
THE-330: oxirane modification trimethylolpropane triacrylate, Japanese chemical drug corporate system
DPHA: dipentaerythritol acrylate, Japanese chemical drug corporate system
イ Le ガ キ ユ ア one 184:1-hydroxycyclohexylphenylketone, チ バ ス ペ シ ヤ Le テ イ one ケ ミ カ Le corporate system
(estimating making) with sample
Use the ultraviolet-curing resin composition of gained, the method through following 1～3 is made to estimate and is used the sample disk.
Be formed with azo class uvea as recording layer, reflective coating, as the ZnSSiO of dielectric layer
2On the interior week of the diameter 120mm of layer, the polycarbonate system substrate (first substrate) of thick 0.6mm, place the transparent resin made from the mode that does not get into bubble, and on this resin, place pressing mold, carry out spin coating in 4 seconds and make its applying with 2000rpm then.
2. use high-pressure sodium lamp (80W/cm) from transparent resin pressing mold one side with 400mJ/cm
2Shine, second ultraviolet-curing resin composition is solidified.
3. use disk stripping off device (オ リ ジ Application Electric Co., Ltd system), peel off the transparent resin pressing mold, process to estimate and use the sample disk.
(a) fissility test
Use disk stripping off device (オ リ ジ Application Electric Co., Ltd system), the peel strength at the relatively poor internal diameter 60mm place of fissility is measured through measuring instrument (FGC-5B, Nidec シ Application ボ Co., Ltd. system).Peeling off the judgement of formedness carries out according to following benchmark.
Zero ... Below the peel strength 1.5kgf
* ... Peel strength surpasses 1.5kgf
(b) permanance (moisture-proof) test
As anti-moisture test; Will through abovementioned steps make peel off after the sample disk 80 ℃, 85% hot and humid condition held 96 hours; Afterwards; At room temperature preserved 24 hours, according to place hot and humid down before with at room temperature preserve after whether peel off and judge from recording film.
Zero ... Driving fit
* ... Peel off
Can know by table 1, as the embodiment 1～3 of ultraviolet-curing resin composition of the present invention and solidfied material thereof, compare, even closing force is also good under hot and humid situation with comparative example 1.Can confirm in addition, compare with the comparative example 2, the comparative example 3 that use polyfunctional acrylate monomer, be the good especially resin combination of fissility.
Industrial applicability
Ultraviolet-curing resin composition of the present invention and solidfied material thereof, though can be used as fissility good and place under the hot and humid condition also can with the 2P agent of reflective coating or dielectric layer driving fit.In addition, can provide and to form the middle layer by a kind of solution and omit the ultraviolet curing resin of adhesive layer.
The present invention is specified with reference to specific mode, but it will be apparent for a person skilled in the art that under the prerequisite that does not break away from spirit of the present invention and scope and can carry out various changes and correction.
In addition, the Japanese patent application that the application proposed based on March 31st, 2009 (Japan special hope 2009-084534) is quoted its full content by reference.In addition, all introduce among the present invention as a whole in these whole references of quoting.
Claims (7)
1. a multiplayer optical disk is used ultraviolet-curing resin composition, and it contains: above carbamate (methyl) acrylic ester of six senses that the organic isocyanate that has two above NCOs in the molecule is obtained with above (methyl) acrylate reactions of the trifunctional with hydroxyl, (methyl) acrylate monomer below (B) trifunctional and (C) Photoepolymerizationinitiater initiater.
2. multiplayer optical disk as claimed in claim 1 is used ultraviolet-curing resin composition; Wherein, In carbamate (methyl) acrylic ester (A) more than six senses that the organic isocyanate that in making a molecule, has two above NCOs obtains with (methyl) acrylate reactions more than the trifunctional with hydroxyl; Organic isocyanate is for being selected from by IPDI; 1; Hexamethylene-diisocyanate; Toluene diisocyanate; XDI; Diphenyl methane-4; 4 '-diisocyanate; The tetrahydro-dicyclopentadiene group diisocyanate; And in the group formed of the trifunctional isocyanates of formula (1) expression one or more
In the formula, R representes
3. according to claim 1 or claim 2 multiplayer optical disk is used ultraviolet-curing resin composition; Wherein, In carbamate (methyl) acrylic ester (A) that the organic isocyanate that in making a molecule, has two above NCOs obtains with (methyl) acrylate reactions more than the trifunctional with hydroxyl, has above (methyl) acrylic ester of the trifunctional of hydroxyl for being selected from the group of forming by three, four or five (methyl) acrylic ester of the 6-caprolactone addition product of three (methyl) acrylic ester of the 6-caprolactone addition product of pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, pentaerythrite and dipentaerythritol one or more.
4. use ultraviolet-curing resin composition like each described multiplayer optical disk in the claim 1～3; Wherein, (methyl) acrylate monomer (B) below the trifunctional is for being selected from the group of being made up of IBOA, neopentylglycol diacrylate, epoxy pronane modification neopentylglycol diacrylate, tristane dimethanol diacrylate and hydroxy pivalin aldehyde modification trimethylolpropane diacrylate one or more.
5. use ultraviolet-curing resin composition like each described multiplayer optical disk in the claim 1～4, wherein,, contain (A) composition 5～80 weight %, (B) composition 10～80 weight %, (C) composition 1～15 weight % with respect to the resin combination total amount.
6. a solidfied material obtains through each described multiplayer optical disk in the claim 1～5 is shone active energy beam with ultraviolet-curing resin composition.
7. a multiplayer optical disk has the described solidfied material of claim 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009084534A JP2010238299A (en) | 2009-03-31 | 2009-03-31 | Ultraviolet curable resin composition for multilayered optical disk |
| JP2009-084534 | 2009-03-31 | ||
| PCT/JP2010/055760 WO2010113976A1 (en) | 2009-03-31 | 2010-03-30 | Uv-curable resin composition for use in multi-layer optical disc |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102379007A true CN102379007A (en) | 2012-03-14 |
Family
ID=42828265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800148704A Pending CN102379007A (en) | 2009-03-31 | 2010-03-30 | Uv-curable resin composition for use in multi-layer optical disc |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2010238299A (en) |
| CN (1) | CN102379007A (en) |
| SG (1) | SG174979A1 (en) |
| TW (1) | TW201037002A (en) |
| WO (1) | WO2010113976A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1324389A (en) * | 1998-08-20 | 2001-11-28 | Dsm有限公司 | Adhesive for optical disks |
| JP2003096146A (en) * | 2001-07-18 | 2003-04-03 | Mitsubishi Rayon Co Ltd | Active energy ray curable composition, and optical disk |
| JP4193916B2 (en) * | 2007-03-23 | 2008-12-10 | Ｄｉｃ株式会社 | Ultraviolet curable composition for optical disc intermediate layer and optical disc |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0559139A (en) * | 1991-09-04 | 1993-03-09 | Dainippon Ink & Chem Inc | Uv ray-curable resin composition |
-
2009
- 2009-03-31 JP JP2009084534A patent/JP2010238299A/en active Pending
-
2010
- 2010-03-30 SG SG2011071008A patent/SG174979A1/en unknown
- 2010-03-30 WO PCT/JP2010/055760 patent/WO2010113976A1/en active Application Filing
- 2010-03-30 CN CN2010800148704A patent/CN102379007A/en active Pending
- 2010-03-31 TW TW099109827A patent/TW201037002A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1324389A (en) * | 1998-08-20 | 2001-11-28 | Dsm有限公司 | Adhesive for optical disks |
| JP2003096146A (en) * | 2001-07-18 | 2003-04-03 | Mitsubishi Rayon Co Ltd | Active energy ray curable composition, and optical disk |
| JP4193916B2 (en) * | 2007-03-23 | 2008-12-10 | Ｄｉｃ株式会社 | Ultraviolet curable composition for optical disc intermediate layer and optical disc |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010113976A1 (en) | 2010-10-07 |
| SG174979A1 (en) | 2011-11-28 |
| JP2010238299A (en) | 2010-10-21 |
| TW201037002A (en) | 2010-10-16 |
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Application publication date: 20120314 |