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TW201037002A - 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 PDF

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Publication number
TW201037002A
TW201037002A TW099109827A TW99109827A TW201037002A TW 201037002 A TW201037002 A TW 201037002A TW 099109827 A TW099109827 A TW 099109827A TW 99109827 A TW99109827 A TW 99109827A TW 201037002 A TW201037002 A TW 201037002A
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Taiwan
Prior art keywords
meth
resin composition
acrylate
optical disc
curable resin
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TW099109827A
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Chinese (zh)
Inventor
Hiroki Tsutsumi
Daisuke Kobayashi
Yuichiro Matsuo
Satoshi Ogi
Masahiro Naitou
Jun Kidoba
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Nippon Kayaku Kk
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Publication of TW201037002A publication Critical patent/TW201037002A/en

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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)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Manufacturing Optical Record Carriers (AREA)
  • Optical Record Carriers And Manufacture Thereof (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

201037002 六、發明說明： 【發明所屬之技術領域】 本發明係關於一種光碟用紫外線硬化型樹脂組成物及 其硬化物，且關於一種與反射臈層或介電質層之密合力 高、自壓模之剝離性優異之用以有效率地生產下一代高密 度光碟的樹脂組成物。 【先前技術】 近年來，對光碟之大容量化之要求顯著。作為提高光 €)碟之記錄容量之技術，可列舉記錄/播放光束之短波長化、 記錄/播放光束照射光學系統之物鏡之高ΝΑ化、記錄層之 多層化等。該等之中，藉由記錄層之多層化所實現的大容 量化，與短波長化或高ΝΑ化相較之下，可實現低成本下之 大容量化。 例如，具有2個記錄層之DVD碟片，係採用將2個記 錄層透過透明樹脂中間層加以積層之構造。具體而言，係 依序積層G.6 mm之第i透明樹脂基板、第i記錄層、第！ 半透明反射膜層、透明樹脂中間層、第2記錄層、第2反 射膜層、接著層、〇6随之第2透明樹脂基板的構造。此 時透明樹脂中間層，係於第1半透明反射膜層上塗佈形 成透明樹月旨巾間層之紫外線硬化型樹脂組成物，並將其按 壓於具有記錄/播放光束之引導用引導槽等凹凸圖案之透明 樹&壓模’再使紫外線硬化樹脂組成物硬化後將壓模剝 將凹凸轉印於紫外線硬化型樹脂組成物之表面而形成。 I光碟片中’讀取專用碟片係於基板（例如直徑1 20 3 201037002 mm、厚度1.1 mm之聚碳酸酯基板）單面轉印凹坑狀記錄圖 案，並於該基板表面形成作為第1記錄層之第！反射膜層（例 如銀合金反射膜層）。並且並且，於第1反射膜層上形成轉 印有凹i几狀記錄圖案之透明樹脂中間層，並於該中間膜上 开y成作為第2 3己錄層之第2反射膜層（例如銀合金反射膜 層）。於是成為積層透明樹脂層之結構。此外，關於銀合金 反射膜層’例如已提出有II由濺锻法於真空中成膜之方法。 記錄型碟片係呈如下構造：於基板（例如直徑120 mm、 厚度1 · 1 mm之聚碳酸酯基板）單面轉印凹坑狀記錄圖案，並 於該基板表面積層第丨反射膜層、第丨介電質層、第丨記 錄層及第2介電質層，並且並且依序積層透明樹脂中間層、 第2反射膜層、第3介電質層、第2記錄層、第4介電質 層、透明樹脂層。 於上述情況下，透明樹脂中間層，係於反射膜層或介 電質層上塗佈形成透明樹脂中間層之紫外線硬化型樹脂組 成物，並將其按壓於具有記錄/播放光束之引導用引導槽等 凹凸圖案之透明樹脂壓模上，再使紫外線硬化樹脂組成物 硬化後將壓模剝離，將凹凸轉印於紫外線硬化型樹脂組成 物之表面而形成。此處，通常，透明樹脂中間層於讀取專 用碟片中，係由接著於第2反射膜層之剝離層及接著於第i 反射膜層之接著層所構成，而於記錄型碟片中則係由接著 於第2反射膜層之剝離層及接著於第2介電質層之接著層 所構成。 通常將5亥轉印法稱為2P(Photo Polymerization)法，將 201037002 所使用之紫外線硬化型樹脂組成物稱為2p樹脂。 透明樹脂壓模，可列舉丙稀酸系樹脂、甲基丙稀酸系 樹脂、聚碳酸醋樹脂' 聚締烴系樹脂(特別是非晶質聚稀 煙）、聚醋系樹脂、聚苯乙烯樹脂、環氧樹脂等。該等之中， 就使2P樹脂硬化後之剝離性、㈣濕@、形狀敎性等方 面而言’以非晶質聚烯烴較佳，就材料成本之方面而言， 以聚碳酸酯樹脂較佳。 € 通常，DVD之0.6 mm樹腊基板、藍光碟片之丨」_ 樹脂基板係使用聚碳酸酯樹脂。於使用聚㈣㈣脂作為 透明樹脂壓模時’藉由將與21>樹脂不同之紫外線硬化型樹 脂用於樹脂基板側，可使聚碳酸酯製樹脂壓模易於自硬化 後2P樹脂層剝離。 若自透明樹脂壓模之剝離性差，則會產生透明樹脂中 間層之一部分與透明樹脂壓模一起剝離之缺陷。若轉印性 較差，則δ己錄/播放時會產生誤差。若紫外線硬化後翹曲大， 則無法於所形成之凹凸圖案上均勻地形成記錄層或反射膜 〇 層，或於DVD之情況下無法貼合第2基板，或於藍光碟片 之情況下無法均勻形成0.1 mm之透光層。又，若於高溫高 濕下凹凸圖案發生變形，則第1、2記錄層之記錄特性（例如 抖動特性）會變得不同。 專利文獻1〜4之2P樹脂係使用金屬製之壓模於玻璃 基板上形成凹凸圖案’而並無利用透明樹脂壓模形成凹凸 圖案之相關記載。又’專利文獻5〜8中雖有2P樹脂之記 載，但並無本發明之樹脂之相關記載。 5 201037002 專利文獻1 : 專利文獻2 : 專利文獻3 : 專利文獻4 : 專利文獻5 : 專利文獻6 : 專利文獻7 : 專利文獻8 : 【發明内容】 曰本特開平5-59139號公報 曰本特開平5-132534號公報 日本特開平5-140254號公報 曰本特開平5-132506號公報 曰本特開2003-331463號公報 曰本特開2004-288242號公報 曰本特開2004-288264號公報 曰本特開2005-3 325 64號公報 通常作為2P劑所使用之紫外線硬化型樹脂，必須能 夠自形成有凹凸圖案之壓模於保持該圖案之狀態下從壓模 .工易地剝離。此時’若不易自壓模剝離，則會產生樹脂附 著於壓模而不接著於反射膜層或介電質層等之問題，導致 生產效率下降。又’即使為自壓模之剝離性高之樹脂，若 在置於南溫多濕下時剝離，則會產生讀取誤差的問題。 因此’本發明蓉於上述實際情況，藉由使用多官能丙 烯，酯改質胺甲酸乙酯丙烯酸酯及(甲基)丙烯酸酯單體，而 可提供種自壓模之剝離性特別優異、且即使於高溫多濕 下亦會役合於反射膜層或介電質層之樹脂成分。 並且’本發明因能夠於使壓模剝離時選擇性地接著於 反射膜層或介電質層，故可省略2P劑之紫外線硬化型樹脂 之接著劑層。 本發明人等發現了 一種樹脂組成，其藉由使用有機異 氮@文S曰與具有經基之多官能丙烯酸酯反應所得之胺甲酸乙 201037002 醋（甲基）丙烯酸酯紫外線硬化型樹脂組成物，而可提高自壓 模之剝離性，且即使置於高溫多濕下亦緊緊地密合於反射 膜層或介電質層。藉此’開發出一種自壓模之剝離性高、 對反射膜層或記錄膜之密合性優異的紫外線效應型樹脂組 成物。 本發明係關於以下之（1)〜（7)。 (1) 一種多層光碟用紫外線硬化型樹脂組成物，其含 有：（A)使1分子中具有2個以上之異氰酸酯基之有機異氰 〇 酸酯與具有羥基之3官能以上（甲基）丙烯酸酯反應所得的6 官能以上之胺曱酸乙酯（甲基）丙烯酸酯、（B)3官能以下之 (甲基）丙烯酸酯單體、及（C)光聚合起始劑。 (2) 如上述（1)所記載之多層光碟用紫外線硬化型樹脂組 成物’其中’於使1分子中具有2個以上之異氰酸酯基之 有機異氰酸醋與具有羥基之3官能以上之（甲基）丙烯酸酯 反應所得的胺曱酸乙酯（甲基）丙烯酸酯（A)中，有機異氰酸 酯係選自由異佛_二異氰酸酯、六亞甲基二異氰酸酯、甲 〇 苯二異氰酸酯、二甲苯二異氰酸酯、二苯基曱烷-4,4'-二異 氰酸酯、二異氰酸二環戊烯酯、及下述式（1)所表示之3官 能異氰酸酯所構成之群中的1種或2種以上，[Technical Field] The present invention relates to an ultraviolet curable resin composition for a photovoltaic disc and a cured product thereof, and relates to a high adhesion force with a reflective ruthenium layer or a dielectric layer, and self-pressure A resin composition excellent in releasability of a mold for efficiently producing a next-generation high-density optical disc. [Prior Art] In recent years, the demand for the large capacity of optical discs has been remarkable. As a technique for increasing the recording capacity of the optical disk, the short wavelength of the recording/playing beam, the high-definition of the objective lens for recording/playing the beam irradiation optical system, and the multilayering of the recording layer can be cited. Among these, the large capacity realized by the multilayering of the recording layer can achieve a large capacity at a low cost as compared with the short wavelength or high enthalpy. For example, a DVD disc having two recording layers has a structure in which two recording layers are laminated through a transparent resin intermediate layer. Specifically, the i-th transparent resin substrate, the i-th recording layer, and the first layer of the G.6 mm layer are sequentially laminated! The semitransparent reflective film layer, the transparent resin intermediate layer, the second recording layer, the second reflective film layer, the adhesive layer, and the crucible 6 follow the structure of the second transparent resin substrate. In this case, the transparent resin intermediate layer is coated on the first semi-transparent reflective film layer to form an ultraviolet curable resin composition which forms a transparent intercalation layer, and is pressed against a guiding groove having a recording/playing beam. The transparent tree & stamper of the concave-convex pattern is formed by curing the ultraviolet curable resin composition and then transferring the unevenness onto the surface of the ultraviolet curable resin composition. In the I-disc, the 'reading disc is attached to the substrate (for example, a polycarbonate substrate having a diameter of 1 20 3 201037002 mm and a thickness of 1.1 mm), and a pit-like recording pattern is formed on the surface of the substrate. The record layer! A reflective film layer (e.g., a silver alloy reflective film layer). Further, a transparent resin intermediate layer to which a concave recording pattern is transferred is formed on the first reflection film layer, and a second reflection film layer as a second recording layer is opened on the intermediate film (for example) Silver alloy reflective film layer). Then, it becomes a structure in which a transparent resin layer is laminated. Further, regarding the silver alloy reflective film layer, for example, a method of forming a film by vacuum sputtering in a vacuum has been proposed. The recording type disc has the following structure: a single-sided transfer pit-shaped recording pattern on a substrate (for example, a polycarbonate substrate having a diameter of 120 mm and a thickness of 1.1 mm), and a second reflective layer on the surface area of the substrate, a second dielectric layer, a second recording layer, and a second dielectric layer, and sequentially laminating a transparent resin intermediate layer, a second reflective film layer, a third dielectric layer, a second recording layer, and a fourth dielectric layer An electric layer and a transparent resin layer. In the above case, the transparent resin intermediate layer is coated on the reflective film layer or the dielectric layer to form an ultraviolet curable resin composition which forms a transparent resin intermediate layer, and is pressed against a guiding guide having a recording/playing beam. In the transparent resin stamper of the concave-convex pattern such as a groove, the ultraviolet curable resin composition is cured, the stamper is peeled off, and the unevenness is transferred onto the surface of the ultraviolet curable resin composition. Here, in general, the transparent resin intermediate layer is formed in the read-only disc by the peeling layer following the second reflective film layer and the subsequent layer of the i-th reflective film layer, and is formed in the recording type disc. Then, it consists of a peeling layer following the second reflective film layer and an adhesive layer next to the second dielectric layer. The 5H transfer method is generally referred to as 2P (Photo Polymerization) method, and the ultraviolet curable resin composition used in 201037002 is referred to as 2p resin. Examples of the transparent resin stamper include an acrylic resin, a methyl acrylate resin, a polycarbonate resin, a polyalkylene resin (especially an amorphous polystyrene), a polyester resin, and a polystyrene resin. , epoxy resin, etc. Among these, in terms of the peeling property after curing the 2P resin, (4) wetness, shape and the like, it is preferable to use an amorphous polyolefin, and in terms of material cost, a polycarbonate resin is used. good. € Usually, the 0.6 mm wax substrate and the Blu-ray disc of the DVD are used. _ The resin substrate is made of polycarbonate resin. When the poly(tetra)(tetra) grease is used as the transparent resin stamper, the ultraviolet curable resin different from the 21> resin is used on the resin substrate side, whereby the polycarbonate resin stamper can be easily peeled off from the 2P resin layer. If the peelability from the transparent resin stamper is poor, a defect in which one portion of the intermediate layer of the transparent resin is peeled off together with the transparent resin stamper is generated. If the transferability is poor, an error occurs in the δ recording/playback. If the warpage is large after the ultraviolet curing, the recording layer or the reflective film layer cannot be uniformly formed on the formed concave-convex pattern, or the second substrate cannot be bonded in the case of a DVD, or in the case of a Blu-ray disc. A 0.1 mm light transmissive layer was uniformly formed. Further, when the uneven pattern is deformed under high temperature and high humidity, the recording characteristics (e.g., jitter characteristics) of the first and second recording layers are different. In the 2P resin of Patent Documents 1 to 4, a concave-convex pattern ‘ is formed on a glass substrate by using a metal stamper, and there is no description about forming a concave-convex pattern by a transparent resin stamper. Further, in Patent Documents 5 to 8, although there is a description of 2P resin, there is no description about the resin of the present invention. 5 201037002 Patent Document 1: Patent Document 2: Patent Document 3: Patent Document 4: Patent Document 5: Patent Document 6: Patent Document 7: Patent Document 8: [Summary of the Invention] 曰本特开平5-59139号Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. In the ultraviolet curable resin which is generally used as a 2P agent, it is necessary to be able to peel off from a stamper in a state in which the pattern is held while holding the pattern. At this time, if it is not easy to peel off from the stamper, there is a problem that the resin adheres to the stamper without being attached to the reflective film layer or the dielectric layer, resulting in a decrease in production efficiency. Further, even if the resin having high peeling property from the stamper is peeled off when it is placed under humid humidity in the south, a problem of reading error occurs. Therefore, the present invention provides a particularly excellent exfoliation property from a stamper by using a polyfunctional propylene, an ester-modified amine urethane acrylate, and a (meth) acrylate monomer. The resin component of the reflective film layer or the dielectric layer is used even under high temperature and humidity. Further, since the present invention can selectively adhere to the reflective film layer or the dielectric layer when the stamper is peeled off, the adhesive layer of the ultraviolet curable resin of the 2P agent can be omitted. The present inventors have found a resin composition which is obtained by reacting an organic isocyanine with a polyfunctional acrylate having a transbasic group, and a urethane (meth) acrylate ultraviolet curable resin composition obtained by reacting a polyfunctional acrylate having a trans group. Moreover, the peeling property of the self-pressing die can be improved, and it is tightly adhered to the reflective film layer or the dielectric layer even under high temperature and high humidity. By this, an ultraviolet effect type resin composition having high peelability from a stamper and excellent adhesion to a reflective film layer or a recording film has been developed. The present invention relates to the following (1) to (7). (1) An ultraviolet curable resin composition for a multilayer optical disc comprising: (A) an organic isocyanurate having two or more isocyanate groups in one molecule and a trifunctional or higher (meth)acrylic acid having a hydroxyl group A 6-functional or higher amine ethyl methacrylate (meth) acrylate obtained by an ester reaction, (B) a trifunctional or lower (meth) acrylate monomer, and (C) a photopolymerization initiator. (2) The ultraviolet curable resin composition for a multilayer optical disc according to the above (1), wherein the organic isocyanate having two or more isocyanate groups in one molecule and the trifunctional or higher having a hydroxyl group ( In the ethyl phthalate (meth) acrylate (A) obtained by the reaction of methyl acrylate, the organic isocyanate is selected from the group consisting of iso-diisocyanate, hexamethylene diisocyanate, formamyl diisocyanate, xylene. One or two of a group consisting of diisocyanate, diphenyldecane-4,4'-diisocyanate, dicyclopentenyl diisocyanate, and a trifunctional isocyanate represented by the following formula (1) More than one kind,

201037002 (式中，R表示 ch3201037002 (where R is ch3

ch3Ch3

(3)如上述（1)或（2)項之多層光碟用紫外線硬化型樹脂 組成物，其中，於使1分子中具有2個以上之異氰酸酯基 201037002 之有機異氰酸酯與具有羥基之3官能以上之（甲基）丙烯酸 酯反應所得的胺曱酸乙酯（曱基）丙烯酸酯（A)中，具有經基 之3官能以上之（甲基）丙烯酸酯係選自由新戊四醇三（甲基） 丙烯酸酯、二新戊四醇五（曱基）丙烯酸酯、新戊四醇之石· 己内酯加成物之三（曱基）丙烯酸酯、及二新戊四醇之£_己 内&9加成物之二或四或五（曱基）丙稀酸醋所構成之群中的1 種或2種以上。 (4) 如上述（1)項至（3)項中任一項之多層光碟用紫外線 〇 硬化型樹脂組成物，其中，3官能以下之（甲基）丙烯酸酯單 體（B)係選自由丙婦酸異莰酯、新戊二醇二丙稀酸酯、環氧 丙炫改質新戊二醇二丙稀酸酯、三環癸烧二甲醇二丙烯酸 酯、及氫三甲基乙路改質三羥甲基丙烷二丙烯酸酯所構成 之群中的1種或2種以上。 (5) 如上述（1)項至（4)項中任一項之多層光碟用紫外線 硬化型樹脂組成物，其中，相對於樹脂組成物總體，含有5 〜80重量％之（A)成分、1〇〜80重量。/。之⑺）成分及1〜15重 〇 量％之（(:）成分。 (6) —種硬化物’其係對上述（丨）項至（5)項中任一項之多 層光碟用紫外線硬化型樹脂組成物照射活性能量射線而獲 得。 (7) —種多層光碟，其具有上述（6)項之硬化物。 本發明之紫外線硬化型樹脂組成物及其硬化物，適用 作為自壓模之剝離性優異、且即使置於高溫多濕下亦密合 於反射膜層或介電質層之2P劑功用。又，可提供能省略接 9 201037002 著層而以一液體來形成中間層之紫外線硬化型樹脂。 【實施方式】 本發明係於樹脂組成物中含有（A)使1分子中具有2個 以上之異氰酸酯基之有機異氰酸酯與具有羥基之3官能以 上之（甲基）丙烯酸酯反應所得的6官能以上之胺甲酸乙醋 (曱基）丙烯酸酯、（B)3官能以下之（甲基）丙烯酸酯單體、及 (C)光聚合起始劑之光碟用紫外線硬化型樹脂組成物。 於本發明之紫外線硬化型樹脂組成物中，使用（A)使1 分子中具有2個以上之異氰酸酯基之有機異氰酸酯與羥基 改質多官能丙烯酸酯反應所得的6官能以上之胺甲酸乙酯 (甲基）丙烯酸酯。 本發明中使用之有機異氰酸酯，係分子内具有2個以 上之異氰酸酯基之化合物，只要為公知者則可無特別限定 地使用。作為其例，可列舉異佛酮：異氰㈣、六亞甲基 二異氰酸醋、甲苯二異氰酸酯、〔甲苯二異氰酸醋、二苯 基甲烧·4,4’_二異氰酸s旨或二異氰酸二環戊稀自旨等二異氰酸 酯類。 並且，於本發明中，係使用對二異氰酸酯單體進行異 氰尿酸酯改質而成之-p、+、j ^ 士 下迷式（1)所表示之3官能異氰酸酯作 為改質異氰酸S旨， 201037002(3) The ultraviolet curable resin composition for a multilayer optical disc according to the above (1) or (2), wherein the organic isocyanate having two or more isocyanate groups 201037002 in one molecule and the trifunctional group having a hydroxyl group or more In the ethyl phthalate acrylate (A) obtained by the reaction of (meth) acrylate, the (meth) acrylate having a trifunctional or higher functional group is selected from the group consisting of neopentyl alcohol (tri) ) acrylate, dipentaerythritol penta(indenyl) acrylate, neopentaerythritol stone · caprolactone adducts of tris(decyl) acrylate, and dipentaerythritol One or two or more of the group consisting of two or four or five (mercapto) lactic acid vinegars of the &9 adduct. (4) The ultraviolet ray hardening type resin composition for a multilayer optical disk according to any one of the above items, wherein the (meth) acrylate monomer (B) having a trifunctional or lower functional group is selected from the group consisting of Isodecyl acetophenate, neopentyl glycol diacrylate, epoxy propylene modified neopentyl glycol diacrylate, tricyclic terpine dimethanol diacrylate, and hydrogen trimethyl ethane One or two or more of the group consisting of modified trimethylolpropane diacrylate. (5) The ultraviolet curable resin composition for a multilayer optical disc according to any one of the above (1), wherein the resin composition contains 5 to 80% by weight of the component (A), 1〇~80 weight. /. (7)) Component and 1 to 15% by weight of the ((:) component. (6) A cured product which is ultraviolet-cured by the multilayer optical disk of any one of the above items (丨) to (5) The resin composition is obtained by irradiating an active energy ray. (7) A multilayer optical disc having the cured product of the above item (6). The ultraviolet curable resin composition of the present invention and a cured product thereof are suitable as a self-pressing mold. It has excellent peelability and is suitable for 2P agent function of the reflective film layer or the dielectric layer even under high temperature and high humidity. Further, it can provide ultraviolet rays which can eliminate the layer of 201037002 and form a middle layer with a liquid. [Embodiment] The present invention relates to a resin composition comprising (A) an organic isocyanate having two or more isocyanate groups in one molecule and a trifunctional or higher functional (meth) acrylate having a hydroxyl group. Ultraviolet-curing resin composition for optical discs of 6-functional or higher urethane (mercapto) acrylate, (B) (3-)-functional (meth) acrylate monomer, and (C) photopolymerization initiator In the ultraviolet of the present invention In the linear curable resin composition, (A) a 6-functional or higher urethane (meth)acrylic acid obtained by reacting an organic isocyanate having two or more isocyanate groups in one molecule with a hydroxy-modified polyfunctional acrylate The organic isocyanate used in the present invention is a compound having two or more isocyanate groups in the molecule, and is not particularly limited as long as it is known. Examples thereof include isophorone: isocyanide (four), and six Methylene diisocyanate, toluene diisocyanate, [toluene diisocyanate, diphenylmethane, 4,4'-diisocyanate or dicyclopentanyl diisocyanate Further, in the present invention, a trifunctional isocyanate represented by the formula (1) which is obtained by modifying an isocyanurate to a diisocyanate monomer is used as the trifunctional isocyanate represented by the formula (1). Modified isocyanate S, 201037002

NCO "•⑴ (式中，R表示NCO "•(1) (where R is

或 201037002Or 201037002

該等化合物可使用適當公知之方法合成而獲得，市售 品，例如可列舉：武田藥品工業公司製造之以“⑽化 D_170N ;住化拜耳聚胺酯SumikaBayer Urethane公司.製造 之 Sumidur N-3300、Desmodur L、Desmodur HL ; Degussa 公司製造之T-1890。 作為有機異氰酸酯，於本案中較佳為式所表示之3 官能異氰酸酯，特佳為六亞甲基二異氰酸酯異氰尿酸酯三 聚物（R=-(ch2)6-)之化合物。 又’並且’作為改質異亂酸g旨，亦可為對二異氰酸酉旨 單體進行縮二脲反應而成之下述式（2)(式中，R與上述式 之R相同）所表示之異氰酸酯。 0These compounds can be obtained by a method known in a known manner, and commercially available products can be, for example, "(10) D_170N; Sumidur N-3300, Desmodur L manufactured by Sumika Bayer Urethane Co., Ltd., manufactured by Takeda Pharmaceutical Co., Ltd. Desmodur HL; T-1890 manufactured by Degussa. As an organic isocyanate, a 3-functional isocyanate represented by the formula in the present invention, particularly preferably a hexamethylene diisocyanate isocyanurate trimer (R = - (ch2) 6-) A compound of the formula (2) which is obtained by reacting a biuret with a diisocyanate monomer as a modified heterologous acid. In the formula, R is the same as the isocyanate represented by the above formula R.

〇〇

NCO NCO 作為具有羥基之3官能以上之（甲基）丙烯酸酯，具體係 指具有羥基之3〜8官能之（甲基）丙烯酸酯，只要為公知者 則可無特別限定地使用。作為其例，可列舉新戊四醇三（甲 基）丙烯酸s旨、二新戊四醇五（曱基）丙稀酸@旨、新戍四醇之 12 201037002 ε-己内酯加成物之三（甲基）丙烯酸酯、二新戊四醇之£_己 内醋加成物之三或四或五（甲基）丙烯酸酯等。本發明中，特 佳為新戊四醇三（甲基）丙烯酸酯及二新戊四醇五（甲基）内歸 酸醋。The NCO NCO is a (meth) acrylate having a trifunctional or higher functional group having a hydroxyl group, and specifically, a (meth) acrylate having a 3 to 8 function having a hydroxyl group, and is not particularly limited as long as it is known. As an example, neopentyl alcohol tris(meth)acrylic acid, dipentaerythritol penta (indenyl) acrylic acid, and neodymidine 12 201037002 ε-caprolactone adducts are mentioned. Tris (meth) acrylate, dipentaerythritol, _ _ hexane vinegar addition of three or four or five (meth) acrylate and the like. In the present invention, pentaerythritol tri(meth)acrylate and dipentaerythritol penta(methyl)-endo-acid vinegar are particularly preferred.

反應係以如下方式進行。即，相對於具有羥基之3官 能以上之（甲基）丙烯酸酯之羥基每1當量而將有機聚異氛 酸a旨以其異氰酸酯基達到較佳為1 ·丨〜2 〇當量之方式混 合’於較佳為70〜90。(：之反應溫度下反應，藉此可獲得目 標胺甲酸乙酯（甲基）丙烯酸酯（A)。 上述（A)胺曱酸乙酯（甲基）丙烯酸酯可使用1種或將2 種以上以任意比例混合使用。胺曱酸乙酯（甲基）丙烯酸 醋於組成物中之使用量，以内比例計為5〜80重量％，較佳 為15〜75重量％，尤佳為2〇〜70重量。/。左右。 本發明所使用之（B)3官能以下之（曱基）丙烯酸酯單 體，只要為公知者則可無特別限定地使用。作為其例，可 列舉：三環癸烷（甲基）丙烯酸酯、丙烯酸苄酯、（甲基）丙烯 酸二環戊酯、（甲基）丙烯酸異莰酯、（曱基）丙烯酸金剛烷基 酉曰、（甲基）丙烯酸苄酯、（曱基）丙烯酸四氫糠酯、嗎福林（甲 基）丙烯酸酯、新戊二醇二（曱基）丙烯酸酯、環氧丙烷改質 新戊二醇二（曱基）丙烯酸酯、三環癸烷二羥甲基二（甲基）丙 烯酸酯、羥基三曱基乙醛改質三羥曱基丙烷二（曱基）丙烯酸 酉曰、羥基二曱基乙酸新戊二醇二（曱基）丙烯酸酯等。 此處，為提高剝離性，所使用之（甲基）丙烯酸酯單體較 佳為使用丙稀酸異莰酯、新戊二醇二丙烯酸酯、環氧丙烷 13 201037002 改質新戊二醇二丙烯酸酯、三環癸烷二甲醇二丙烯酸酯、 氫三甲基乙醛改質三羥甲基丙烷二丙烯酸酯。組成物中之 使用量，以内比例計為10〜80重量％，以15〜75重量0/〇為 佳，20〜70重量％更佳。 本發明之紫外線硬化型樹脂組成物所含有之光聚合 起始劑’可列舉.1 -經基環己基苯基綱（lrgacure 1 84，汽巴 精化製造）、1-[4-(2-羥基乙氧基）_苯基]_2_羥基-2-甲基-卜丙 烷-卜酮（Irgacure 2959，汽巴精化製造）、2-羥基-l-{4-[4-(2-羥基-2-曱基-丙醯基）_苄基]_苯基卜2_甲基-丙烷-^酮 (1^&〇1^6 127，汽巴精化製造）、2,2-二曱氧基-2-苯基苯乙酮 (Irgacure 651，汽巴精化製造；)、低聚[2_羥基·2_曱基 甲基乙稀基）苯基]丙酮](Esacure ONE，Lamberti製造）、2-輕基-2-甲基-1-苯基-丙烧-i_酮（Darocur 1173，汽巴精化製 ie_)、2-甲基-1-[4-(甲硫基）苯基]-2-嗎琳基丙院-1_剩 (Irgacure 907，汽巴精化製造）、2-苄基-2-二甲基胺基-1-(4- 嗎琳基苯基）-丁烧-1-酮、2 -氯嚷"镇酮、2,4-二甲基ί塞領酮、 2,4-二異丙基噻噸酮、異丙基噻噸酮、2,4,6-三甲基苯甲醯 基二苯基氧化膦（1^11(^1*丨11丁？0，8八8?製造）、雙（2,4,6-三甲 基苯曱醢基）-苯基氧化膦（Irgacure 819，汽巴精化製造）、雙 (2,6-二甲氧基苯甲醯基）_2,4,4_三甲基戊基氧化膦等。 該等光聚合起始劑可使用一種，亦可將多種以任意比 例加以混合使用，亦可與胺類等之光聚合起始助劑併用。 本發明之紫外線硬化型樹脂組成物中之（C)光聚合起始 劑之含量’係使用1〜15重量％，較佳為1〜10重量％左右。 14 201037002 本發明中可使用之胺類等之光聚合起始助劑，例如可 列舉：二乙醇胺、2_二甲基胺基苯甲酸乙酯、二甲基胺基笨 乙酮、對二甲基胺基苯甲酸乙酯、對二甲基胺基苯甲酸異 戊酯等。於併用光聚合起始助劑時，本發明之紫外線硬化 型樹脂組成物中之含量，較佳為〇 〇5〜5重量％，特佳為工 〜3重量％左右。 本發明之紫外線硬化型樹脂組成物中，視需要可添加 磷酸（甲基）丙烯酸酯。磷酸（曱基）丙烯酸酯雖可提升鋁、銀 C)或銀合金與接著劑硬化物之接著性升，但恐有腐蝕金屬膜 之虞’故限制其使用量β 並且’於本發明中’除上述成分以外，視需要可併用 石夕烧偶合劑、均染劑、消泡劑、聚合抑制劑、光穩定劑（受 阻胺系等）、抗氧化劑、防靜電劑、表面潤滑劑、填充劑等 添加劑。此種添加劑之例，例如可列舉：信越化學（股）公司 製造之 ΚΒΜ-502、ΚΒΜ-503、ΚΒΜ-5103、ΚΒΜ-802、 ΚΒΜ-803 ; BYK-Chemie 公司製造之 ΒΥΚ-333、ΒΥΚ-307、 G BYK-3500、BYk-3530、BYK-3570 ;東麗道康寧（股）公司製 造之 Z-6062、SH-6062、SH-29PA : Adeka(股）公司製造之 LA-82 等。 本發明之紫外線硬化型樹脂組成物，可將上述各成分 於常溫〜80°C下混合溶解後，視需要過濾而得。 本發明之紫外線硬化型樹脂組成物之黏度，利用B型 黏度計於25C下測定為10〜800 mPa.s，較佳為40〜5〇〇 mPa · s ° 15 201037002 DVD之情況下，透明樹脂中間層係（1)於積層有第}透 明樹脂基板、帛i記錄層、第i半透明反射膜層之基板盥 透明樹脂壓模中至少一者之上，藉由旋塗法、網版印刷法、 輥塗法等方法來塗佈本發明之樹脂組成物後，加以貼合， 並從透明樹脂壓模側照射紫外線而形成。或者亦可（2)於透 明樹脂壓模上藉由上述方法塗佈本發明之樹脂組成物後， 進行紫外線硬化，利用任意之紫外線硬化型樹脂，與積層 有第1透明樹脂基板、第丨記錄層、第丨半透明反射膜層 之基板貼合而形成。（1)之形成方法就省略生產效率之觀點 而言，因可望降低生產成本而較佳。此外，藍光碟片亦利 用與DVD相同之方法來形成透明樹脂中間層。通常 或HD-DVD之0.6 mm之第1透明樹脂基板、藍光碟片之 1.1 mm之樹脂基板係使用聚碳酸酯樹脂。於使用聚碳酸酯 製透明樹脂壓模時，亦就剝離性之方面而言較佳為（丨）之 方法。 透明樹脂壓模，例如可列舉：丙烯酸系樹脂、甲基丙 烯酸系樹脂、聚碳酸酯樹脂、聚稀烴系樹脂（特別是非晶質 聚烯烴）、聚酯系樹脂、聚苯乙烯樹脂、環氧樹脂等。該等 之中，就使2P樹脂硬化後之剝離性、低吸濕性、形狀穩定 性而言，以非晶質聚烯烴為佳，就材料成本而言，以聚碳 酸S旨樹脂為佳。本發明之2P硬化型樹脂組成物可使用任— 透明樹脂壓模。 本發明之紫外線硬化型樹脂組成物，係藉由照射活性 能量射線而形成硬化物。該活性能量射線，例如可列舉紫 16 201037002 外〜近紫外之光線。例如可列舉：低壓、高壓、超高壓水 銀燈、金屬鹵素燈、（脈衝）氙氣燈、無電極燈、紫外線發光 二極體等。上述硬化物亦包含於本發明中。 由上述硬化物所得之透明樹脂中間層上所形成的記錄 層，可使用有機色素或相變化材料之任一種。例如，有機 色素可列舉含金屬偶氮系、聚次曱基系、酞青系等，相變 化材料可列舉於Sb(銻）及Te(碲）中添加有&(銦）、Ag(銀）、 Au(金）、Bi(銘）、Se(栖）、A1(紹）、p(填）、Ge(錯）、Η(氫）、 C) Si(石夕）、c(碳）、v(釩）、w(鎮）' Ta(组）、Ζη(辞）、Ti(欽）、The reaction was carried out in the following manner. That is, the organic polyisophthalic acid is mixed with the isocyanate group in an amount of preferably 1 · 丨 〜 2 〇 equivalent per 1 equivalent of the hydroxyl group of the trifunctional or higher (meth) acrylate having a hydroxyl group. It is preferably 70 to 90. (: reacted at the reaction temperature, whereby the desired ethyl urethane (meth) acrylate (A) can be obtained. The above (A) ethyl citrate (meth) acrylate can be used alone or in combination of two. The above may be used in combination at any ratio. The amount of the amine acetoacetate (meth) acrylate in the composition is, in an internal ratio of 5 to 80% by weight, preferably 15 to 75% by weight, particularly preferably 2 Å. The (B) trifunctional or lower (fluorenyl) acrylate monomer used in the present invention is not particularly limited as long as it is known. Examples thereof include a tricyclic ring. Decane (meth) acrylate, benzyl acrylate, dicyclopentanyl (meth) acrylate, isodecyl (meth) acrylate, adamantyl fluorenyl (meth) acrylate, benzyl (meth) acrylate , (fluorenyl) tetrahydrofurfuryl acrylate, wortene (meth) acrylate, neopentyl glycol di(decyl) acrylate, propylene oxide modified neopentyl glycol di(mercapto) acrylate, Tricyclodecane dimethylol di(meth) acrylate, hydroxytrimercaptoacetaldehyde modification Tris(hydroxy)propane bis(indenyl) ruthenium acrylate, hydroxydimercaptoacetic acid neopentyl glycol bis(indenyl) acrylate, etc. Here, in order to improve the releasability, the (meth) acrylate single used is used. Preferably, isodecyl acrylate, neopentyl glycol diacrylate, propylene oxide 13 201037002 modified neopentyl glycol diacrylate, tricyclodecane dimethanol diacrylate, hydrogen trimethyl b The aldehyde is modified to trimethylolpropane diacrylate. The amount used in the composition is 10 to 80% by weight in terms of the internal ratio, preferably 15 to 75 parts by weight/twice, more preferably 20 to 70% by weight. The photopolymerization initiator contained in the ultraviolet curable resin composition can be exemplified by a 1-cyclohexylphenyl group (lrgacure 1 84, manufactured by Ciba Specialty Chemicals), 1-[4-(2-hydroxyethyl) Oxy)-phenyl]_2-hydroxy-2-methyl-propane-propanone (Irgacure 2959, manufactured by Ciba Specialty Chemicals), 2-hydroxy-l-{4-[4-(2-hydroxy-2) - mercapto-propionyl)-benzyl]_phenyl b-2-methyl-propane-ketone (1^&〇1^6 127, manufactured by Ciba Specialty Chemicals), 2,2-dioxane Alkyl-2-phenylacetophenone (Irgacure 651, Manufactured by Bajing;), oligomeric [2-hydroxy-2-indolylmethylethene)phenyl]acetone] (Esacure ONE, manufactured by Lamberti), 2-light-2-methyl-1-benzene Base-propanone-i-ketone (Darocur 1173, Ciba refined i_), 2-methyl-1-[4-(methylthio)phenyl]-2-morphinyl-propyl-1 (Irgacure 907, manufactured by Ciba Specialty Chemicals), 2-benzyl-2-dimethylamino-1-(4-morphinylphenyl)-butan-1-one, 2-chloroindole" town Ketone, 2,4-dimethylulonone, 2,4-diisopropylthioxanthone, isopropylthioxanthone, 2,4,6-trimethylbenzhydryldiphenyl oxide Phosphine (1^11(^1*丨11丁? 0,8 8 8?), bis(2,4,6-trimethylphenylhydrazino)-phenylphosphine oxide (Irgacure 819, manufactured by Ciba Specialty Chemicals), bis(2,6-dimethoxy Benzobenzyl) 2,4,4-trimethylpentylphosphine oxide, and the like. These photopolymerization initiators may be used singly or in combination of any of them in any ratio, or may be used in combination with a photopolymerization initiator such as an amine. The content (C) of the photopolymerization initiator in the ultraviolet curable resin composition of the present invention is 1 to 15% by weight, preferably about 1 to 10% by weight. 14 201037002 The photopolymerization initiation aid of an amine or the like which can be used in the present invention, for example, diethanolamine, ethyl 2-dimethylaminobenzoate, dimethylaminoethylidene, and dimethylene Ethyl benzyl benzoate, p-amyl dimethylaminobenzoate, and the like. When the photopolymerization initiation aid is used in combination, the content of the ultraviolet curable resin composition of the present invention is preferably from 5 to 5% by weight, particularly preferably from about 3% to about 3% by weight. In the ultraviolet curable resin composition of the present invention, phosphoric acid (meth) acrylate may be added as needed. Phosphate (mercapto) acrylate can enhance the adhesion of aluminum, silver C) or silver alloy to the hardener of the adhesive, but it is likely to corrode the metal film, so it limits its use amount β and 'in the present invention' In addition to the above components, if necessary, a combination of a sulphur coupling agent, a leveling agent, an antifoaming agent, a polymerization inhibitor, a light stabilizer (a hindered amine system, etc.), an antioxidant, an antistatic agent, a surface lubricant, and a filler may be used in combination. And other additives. Examples of such an additive include ΚΒΜ-502, ΚΒΜ-503, ΚΒΜ-5103, ΚΒΜ-802, ΚΒΜ-803 manufactured by Shin-Etsu Chemical Co., Ltd.; ΒΥΚ-333, ΒΥΚ- manufactured by BYK-Chemie Co., Ltd. 307, G BYK-3500, BYk-3530, BYK-3570; Z-6062, SH-6062, SH-29PA manufactured by Toray Dow Corning Co., Ltd.: LA-82 manufactured by Adeka Co., Ltd., etc. The ultraviolet curable resin composition of the present invention can be obtained by mixing and dissolving each of the above components at a temperature of from ordinary temperature to 80 ° C, followed by filtration as needed. The viscosity of the ultraviolet curable resin composition of the present invention is measured by a B-type viscometer to be 10 to 800 mPa·s at 25 C, preferably 40 to 5 μmPa · s ° 15 201037002 DVD, transparent resin The intermediate layer (1) is formed by spin coating or screen printing on at least one of a substrate/transparent resin stamper having a layer of a transparent resin substrate, a 帛i recording layer, and an ith semi-transparent reflective film layer. The resin composition of the present invention is applied by a method such as a method or a roll coating method, and then bonded, and formed by irradiating ultraviolet rays from the side of the transparent resin stamper. Alternatively, (2) applying the resin composition of the present invention to the transparent resin stamper by the above method, and then performing ultraviolet curing, using any ultraviolet curable resin, and laminating the first transparent resin substrate and recording the first transparent resin substrate. The substrate of the layer and the second semi-transparent reflective film layer is bonded to each other. (1) The formation method is preferable from the viewpoint of omitting production efficiency because it is expected to reduce the production cost. Further, the Blu-ray disc is also formed into a transparent resin intermediate layer by the same method as the DVD. A polycarbonate resin is usually used for the first transparent resin substrate of 0.6 mm for HD-DVD or the resin substrate of 1.1 mm for Blu-ray disc. In the case of using a polycarbonate transparent resin stamper, it is preferably a method of peeling. Examples of the transparent resin stamper include an acrylic resin, a methacrylic resin, a polycarbonate resin, a polyolefin resin (particularly an amorphous polyolefin), a polyester resin, a polystyrene resin, and an epoxy resin. Resin, etc. Among these, an amorphous polyolefin is preferred in terms of peelability, low moisture absorption, and shape stability after curing the 2P resin, and a polycarbonic acid S resin is preferred in terms of material cost. The 2P hardening type resin composition of the present invention can be molded using any of a transparent resin. The ultraviolet curable resin composition of the present invention forms a cured product by irradiation with an active energy ray. The active energy ray may, for example, be a light source of violet 16 201037002 to near ultraviolet light. For example, a low pressure, a high pressure, an ultrahigh pressure mercury lamp, a metal halide lamp, a (pulse) xenon lamp, an electrodeless lamp, an ultraviolet light emitting diode, and the like can be cited. The above cured product is also included in the present invention. Any one of an organic dye or a phase change material can be used as the recording layer formed on the transparent resin intermediate layer obtained from the above cured product. For example, the organic dye may be a metal-containing azo-based, poly-indenyl-based or indigo-based system, and the phase-change material may be added to Sb (锑) and Te (碲) with & (indium) and Ag (silver). ), Au (gold), Bi (Ming), Se (Ha), A1 (Sho), p (fill), Ge (wrong), Η (hydrogen), C) Si (Shi Xi), c (carbon), v (vanadium), w (town) 'Ta (group), Ζη (word), Ti (chin),

Ce(鈽）、Tb(铽）、Sn(錫）、Pb(鉛）中任一種以上者。 另外’本發明之樹脂組成物可用於貼合聚碳酸酯製基 板之構造之光碟或藍光碟片中之任一種。 塗佈方法，例如可列舉旋塗法、2p法、輥塗法、網版 印刷法等。 另外’由於下一代高密度光碟於讀取及/或寫入時係使 用400 nm左右之藍色雷射，故於臈厚9〇〜1〇〇 #讯之硬化 C) 物中405 nm之透射率以8〇%以上為佳。 實施例 以下，以實施例詳細說明本發明。 合成例1 :胺甲酸乙酯丙烯酸酯（A_1}之合成 於附有擾拌裝置、冷卻管及溫度計之圓底燒瓶中，添 加異佛_ 一異氰酸酉旨〇63重量份、新戍四醇三丙稀酸酿 93.9重$份、作為聚合抑制劑之對甲氧基苯紛〇 重量份 及一丁基錫一月桂酸酯〇〇5重量份，於室溫下混合％分 17 201037002 鐘’於80°C下反應5小時。於異氰酸酯濃度達到〇·1 %以下 時結束反應，獲得目標胺甲酸乙酯丙烯酸酯。 合成例2 :胺甲酸乙酯丙烯酸酯（A-2)之合成 於附有攪拌裝置、冷卻管及溫度計之圓底燒瓶中，添 加六亞曱基二異氰酸酯之異氰尿酸酯改質類型（武田藥品工 業公司製造之 Takenate D-170N，式（1)R = -(CH2)6-)11.6 重 里伤、—新戍四醉五丙稀酸S曰8 8 · 4重量份' 作為聚合抑制 劑之對甲氧基苯酌 〇.〇5重量份及二丁基錫二月桂酸g旨ο.” 重量份，於室溫下混合30分鐘，於8(TC下反應5小時。於 異氰酸酯濃度達到0· 1 %以下時結束反應，獲得目標胺甲酸 乙酯丙稀酸酯。 合成例3 :胺甲酸乙酯丙浠酸酯（A-3)之合成 於附有攪拌裝置 '冷卻管及溫度計之圓底燒瓶中，添 加六亞曱基二異氰酸酯14.8質量份 '二新戊四醇五丙嫦酸 8曰85.1重量份 '作為聚合抑制劑之對甲氧基苯酚〇 〇3重量 伤及—丁基錫二月桂酸酯〇 05重量份，於室溫下混合3〇分 鐘，於80 C下反應5小時。於異氰酸酯濃度達到〇」％以下 之時結束反應，獲得目標胺甲酸乙酯丙烯酸酯。 實施例及試驗例 對於貫施例1〜3及比較例1〜3之樹脂組成物，將構 成材料及使用量以及對下述項目進行評價之結果示於表 1β再者，記載中之「份」表示重量份。 18 201037002 [表η 表1 樹脂組成及評價結果 實施例1實施例2實施例3比較例1比較例2比較例3 成分(A)(份） A-1Any one of Ce (钸), Tb (铽), Sn (tin), and Pb (lead). Further, the resin composition of the present invention can be used for any one of a disc or a Blu-ray disc having a structure in which a polycarbonate substrate is bonded. Examples of the coating method include a spin coating method, a 2p method, a roll coating method, and a screen printing method. In addition, since the next-generation high-density optical disc uses a blue laser of about 400 nm for reading and/or writing, it transmits 405 nm in the hardened C〇9~1〇〇# The rate is preferably 8〇% or more. EXAMPLES Hereinafter, the present invention will be described in detail by way of examples. Synthesis Example 1: Synthesis of urethane acrylate (A_1} in a round bottom flask equipped with a scrambler, a cooling tube, and a thermometer, and adding isophora _ monoisocyanate 〇 63 parts by weight, new 戍 four Alcohol triacetic acid is brewed in a weight of 93.9 parts by weight, as a polymerization inhibitor, by weight of p-methoxybenzene and 5 parts by weight of monobutyltin monolaurate, mixed at room temperature for 17 minutes 201037002 The reaction was carried out for 5 hours at 80 ° C. The reaction was terminated when the isocyanate concentration reached 〇·1% or less to obtain the desired ethyl urethane acrylate. Synthesis Example 2: Synthesis of urethane acrylate (A-2) In a round bottom flask of a stirring device, a cooling tube and a thermometer, an isocyanurate modified type of hexamethylene diisocyanate (Takenate D-170N manufactured by Takeda Pharmaceutical Co., Ltd., formula (1) R = -(CH2) 6-)11.6 Heavy injury, - Xinyi four drunk five acrylic acid S曰8 8 · 4 parts by weight as a polymerization inhibitor of p-methoxybenzene, 〇 5 parts by weight and dibutyl tin dilaurate g ο. parts by weight, mixed at room temperature for 30 minutes, reacted at 8 (TC for 5 hours). When the acid ester concentration reached 0.1% or less, the reaction was terminated to obtain the desired ethyl urethane acrylate. Synthesis Example 3: Synthesis of ethyl urethane propionate (A-3) was stirred with a stirring device Tube and thermometer round bottom flask, adding hexamethylene diisocyanate 14.8 parts by mass of 'dipentaerythritol pentapropanoic acid 8 曰 85.1 parts by weight' as a polymerization inhibitor of p-methoxyphenol oxime 3 weight injury And butyltin dilaurate 〇05 parts by weight, mixed at room temperature for 3 minutes, and reacted at 80 C for 5 hours. When the isocyanate concentration reached below 〇%, the reaction was terminated to obtain the desired urethane acrylate. Examples and Test Examples The results of the evaluation of the constituent materials, the amount of use, and the evaluation of the following items in the resin compositions of Examples 1 to 3 and Comparative Examples 1 to 3 are shown in Table 1β. Part" represents parts by weight. 18 201037002 [Table η Table 1 Resin composition and evaluation results Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Component (A) (part) A-1

A-2 A-3 成分(B)(份） DBA RP-1040 THE-330 DPHA 成分(C)(份） Irgacure 184 其他成分(份） (剝離性試驗） 剝離強度(kgf) 剝離性判定 (耐久性試驗密合力) 密合判定 43 43 43 52 52 52 5 5 5 0.9 0.7 0.8 〇 〇 〇 〇 〇 〇 43 19 19 76 76 52 5 5 5 0.9 2.4 2.6 〇 X X X 〇 〇A-2 A-3 Ingredient (B) (parts) DBA RP-1040 THE-330 DPHA Ingredient (C) (parts) Irgacure 184 Other components (parts) (peelability test) Peel strength (kgf) Peelability judgment (durability) Test adhesion (closed force) 43 43 43 52 52 52 5 5 5 0.9 0.7 0.8 〇〇〇〇〇〇43 19 19 76 76 52 5 5 5 0.9 2.4 2.6 〇XXX 〇〇

再者，表1中以簡稱所示之各成分如下。 A-1 :合成例1中獲得之胺曱酸乙酯丙烯酸酯 A-2 :合成例2中獲得之胺曱酸乙酯丙烯酸酯 A-3 :合成例3中獲得之胺曱酸乙酯丙烯酸酯 IBA :丙烯酸異莰酯，第一工業化學公司製造 RP-1040 :新戊四醇環氧乙烷改質四丙烯酸酯，日本化 藥公司製造 THE-3 3 0:環氧乙烷改質三羥曱基丙烷三丙烯酸酯，曰 本化藥公司製造 201037002 DPHA .二新戊四醇六丙稀酸酯，日本化藥公司製造 Irgacure 184 : 1-羥基環己基苯基酮，汽巴精化公司製 造 (評價用樣品之製作） 使用所得之紫外線硬化型樹脂組成物，利用以下丨〜3 之方法製作評價用樣品碟片。 1·於形成有作為記錄層之偶氮系色素層、反射膜層、作 為介電質層之ZnS.Si〇2層的直徑120 rnm/0.6 mm厚之聚碳 酸酯製基板（第1基板）内周上，以不混入氣泡之方式載置所 製作之透明樹脂，再於該樹脂上載置壓模，以2〇〇〇卬爪旋 塗4秒鐘而進行貼合。 2.使高壓水銀燈（8〇W/cm)自透明樹脂壓模側照射4〇〇 mJ/cm2 ’使第2紫外線硬化型樹脂組成物硬化。 3·使用碟片剝離裝置（〇rigin電機（股）製造）剥離透明樹 脂壓模，製作出評價用樣品碟片。 (a) 剝離性測試 利用計測器（FGC-5B，Nidec-Shimpo(股）製）對使用碟片 剝離裝置（Origin電機（股）製造）而剝離性較差之内柙 6〇 nim時之剝離強度進行測定，藉此進行剝離性測試。= 離良好性之判斷係依照下述基準來進行。 ' 〇…剝離強度為1.5 kgf以下 X…剝離強度超過1.5 kgf (b) 耐久性（耐濕性）測試 耐濕性測試，係將上述步驟製作之剝離後之樣品碟片 20 201037002 於80°(：、85%之高溫多濕下之條件下放置96小時後，於室 溫下保存24小時，根據在置於高溫多濕下之前與於室溫下 保存後是否自記錄膜剝離來判定。 〇…密合 X…剝離 由表1可清楚發現’本發明之紫外線硬化型樹脂組成 物及其硬化物之實施例1〜3，相較於比較例1，即使於高 溫多濕之狀況下其密合力亦優異。相較於使用多官能丙烯 g^\ 酸酯單體之比較例2與比較例3，可確認為剝離性特別優異 之樹脂組成物。 [產業上之可利用性] 本發明之紫外線硬化型樹脂組成物及其硬化物，適用 作為剥離性優異、且即使置於高溫多濕下亦密合於反射膜 層或介電質層之2P劑功用。此外，並可提供能省略接著層 而以一液體來形成中間層之紫外線硬化型樹脂。 Q 參照特定之態樣對本發明進行了詳細說明，但業者應 明確，於不偏離本發明之精神及範圍之情況下可進行各種 變更及修正。 再者，本申請案係基於2009年3月31日提出申請之 曰本專利申請案（日本專利特願2〇〇9_〇8453句，並以引用之 方式援用其所有内容。另外，此處所引用之所有參照係將 所有内容併入至本文中。 【圖式簡單說明】 無 21 201037002 【主要元件符號說明】 無 22In addition, each component shown by the abbreviation in Table 1 is as follows. A-1: Amino phthalate acrylate A-2 obtained in Synthesis Example 1: Amino phthalate acrylate A-3 obtained in Synthesis Example 2: Amino phthalate acrylate obtained in Synthesis Example 3 Ester IBA: isodecyl acrylate, RP-1040 manufactured by First Industrial Chemical Co., Ltd.: neopentyl alcohol ethylene oxide modified tetraacrylate, manufactured by Nippon Kayaku Co., Ltd. THE-3 3 0: Ethylene oxide modified III Hydroxymercaptopropane triacrylate, manufactured by Sakamoto Chemical Co., Ltd. 201037002 DPHA. Dipentaerythritol hexaacrylate, manufactured by Nippon Kayaku Co., Ltd. Irgacure 184: 1-hydroxycyclohexyl phenyl ketone, Ciba Specialty Chemicals Co., Ltd. Manufacture (Production of Sample for Evaluation) Using the obtained ultraviolet curable resin composition, a sample disc for evaluation was produced by the following method. 1. A polycarbonate substrate (first substrate) having a diameter of 120 rnm/0.6 mm formed with an azo dye layer, a reflective film layer, and a ZnS.Si 2 layer as a dielectric layer. On the inner circumference, the produced transparent resin was placed so as not to be mixed with air bubbles, and the stamper was placed on the resin, and the film was spin-coated with 2 jaws for 4 seconds to bond. 2. The high-pressure mercury lamp (8 〇 W/cm) was irradiated from the transparent resin stamper side by 4 〇〇 mJ/cm 2 ' to cure the second ultraviolet curable resin composition. 3. The transparent resin stamper was peeled off using a disc peeling apparatus (manufactured by 〇rigin Motor Co., Ltd.) to prepare a sample disc for evaluation. (a) Peeling test The peel strength of the inner crucible 6〇nim which is inferior in peelability using a disc peeling device (made by Origin Motor) by a measuring device (FGC-5B, manufactured by Nidec-Shimpo Co., Ltd.) The measurement was performed, whereby the peelability test was performed. = Judgment from goodness is based on the following criteria. ' 〇...peel strength is 1.5 kgf or less X...peel strength exceeds 1.5 kgf (b) Durability (moisture resistance) Test The moisture resistance test is performed by peeling the sample disc 20 201037002 at 80° ( :, after 85% of the conditions under high temperature and high humidity for 96 hours, it was stored at room temperature for 24 hours, and it was judged based on whether it peeled off from the recording film after being stored at room temperature and before being stored at room temperature. In the case of the ultraviolet ray-curable resin composition of the present invention and the cured product thereof, the examples 1 to 3 of the present invention are clearly found in the case of high temperature and high humidity. In the second comparative example and the comparative example 3, the resin composition which is especially excellent in peeling property was confirmed compared with the comparative example 2 and the comparative example 3. [Industrial Applicability] The present invention The ultraviolet curable resin composition and the cured product thereof are suitable for use as a 2P agent which is excellent in peelability and which is adhered to the reflective film layer or the dielectric layer even under high temperature and high humidity. Layer and form a liquid with a liquid The present invention has been described in detail with reference to the specific embodiments thereof, and it should be understood that various changes and modifications may be made without departing from the spirit and scope of the invention. This is based on the patent application filed on March 31, 2009 (Japanese Patent Option 2〇〇9_〇8453, and all references are cited by reference. In addition, all references cited here will be All contents are incorporated into this article. [Simple description of the diagram] None 21 201037002 [Main component symbol description] No 22

Claims (1)

201037002 七、申請專利範圍： 1. —種多層光碟用紫外線硬化型樹脂組成物，其含有： ()使1刀子中具有2個以上之異氰酸酯基之有機異氰酸酯 與具有包基之3官能以上之（甲基）丙稀酸醋反應所得的6官 能以上之胺甲酸乙酯（甲基）丙烯酸酯、（B)3官能以下之（甲 基）丙烯酸酯單體、及（C)光聚合起始劑。 2. 如申請專利議i項之多層光碟用紫外線硬化型 ❹ 樹脂組成物，其中’於使i分子中具有2個以上之異氰酸 醋基之有機異氰酸醋與具有羥基之3官能以上之(甲基)丙 稀酸醋反應所得的6官能以上之胺甲酸乙_ (甲基）丙稀酸 醋（A)中，有機異氰酸醋係選自由異佛酮二異氰酸醋、六亞 甲基二異氰酸醋、甲苯二異氰酸醋、甲笨二異氰酸醋、 二苯基甲燒-4,二異氛酸酿、二異氰酸二環戊稀醋、及式 ⑴所表示之3官能異氣酸醋所構成之群中的i種或2種以 上，201037002 VII. Patent application scope: 1. A UV-curable resin composition for a multilayer optical disc, comprising: () an organic isocyanate having two or more isocyanate groups in one knife and a trifunctional or higher having a basis group ( a 6-functional or higher urethane (meth) acrylate obtained by reacting methyl acetoacetate, (B) a trifunctional (meth) acrylate monomer, and (C) a photopolymerization initiator . 2. For example, the ultraviolet curable styrene resin composition for a multilayer optical disc of the patent application item i, wherein 'the organic isocyanic acid having two or more isocyanate groups in the i molecule and the trifunctional or higher having a hydroxyl group In the 6-functional or higher carbamic acid ethyl methacrylate (A) obtained by the reaction of (meth)acrylic acid vinegar, the organic isocyanic acid vinegar is selected from the group consisting of isophorone diisocyanate, Hexamethylene diisocyanate, toluene diisocyanate, toluene diisocyanate, diphenylmethane-4, diiso-acidic acid, diisocyanate dicyclopentan vinegar, and i or more of the group consisting of trifunctional isogastric acid vinegar represented by formula (1), (式中，R表示 23 201037002(where R represents 23 201037002 3.如申請專利範圍第丨項或 ^ , 〜夕增先碟用紫外線 硬化型樹脂組成物，其中，於使i 田好& 于中具有2個以上之 異鼠酸酯基之有機異氰酸酯與罝右 兴有羥基之3官能以上之（曱 基）丙烯酸醋反應所得的Μ酸乙醋（曱基）丙烯酸酷⑷ 中\具有經基之3官能以上之（甲基）丙稀酸醋係選自由新戊 四醇三（甲基）丙烯酸酯、二新戊四醇五（甲基）丙烯酸酯新 24 201037002 戊四醇之ε·己内酯加成物之三（甲基）丙烯酸酯、及二新戊 四醇之e -己内酯加成物之三或四或五（甲基）丙烯酸酯所構 成之群中的1種或2種以上。 4.如申請專利範圍第1項至第3項中任一項之多層光碟 用紫外線硬化型樹脂組成物，其中3官能以下之（甲基）丙晞 酸酯單體（B)係選自由丙烯酸異莰酯、新戊二醇二丙烯酸 醋、環氧丙烷改質新戊二醇二丙烯酸酯、三環癸烷二甲醇 二丙烯酸酯、及氫三甲基乙醛改質三羥甲基丙烷二丙烯酸 ( 醋所構成之群中的1種或2種以上。 5 ·如申请專利範圍第1項至第4項中任一項之多層光碟 用紫外線硬化型樹脂組成物，其中，相對於樹脂組成物總 體，含有5〜80重量％之0)成分、1〇〜8〇重量％之（”成分 及1〜15重量❶之（c)成分。 6.-種硬化物，其係、對如中請專利範圍第1項至第$項 ▲ ^項之多層光碟用紫外線硬化型樹脂組成物照射活性 能量射線而獲得。 〇 ·種多層光碟，其含有如申請專利範圍第6項之硬化 八、圖式： 益 253. For example, the application of the scope of the patent, or the use of an ultraviolet curable resin composition, wherein the organic isocyanate having two or more iso- succinate groups in i.罝 兴 兴 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 乙 乙 乙 乙 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( Free neopentyl alcohol tri(meth) acrylate, dipentaerythritol penta (meth) acrylate new 24 201037002 pentaerythritol ε · caprolactone adduct tris (meth) acrylate, and One or two or more of the group consisting of three or four or five (meth) acrylates of the e-caprolactone adduct of dipentaerythritol. 4. The ultraviolet curable resin composition for a multilayer optical disc according to any one of claims 1 to 3, wherein the trifunctional or lower (meth)propionic acid ester monomer (B) is selected from the group consisting of acrylic acid. Isodecyl ester, neopentyl glycol diacrylate vinegar, propylene oxide modified neopentyl glycol diacrylate, tricyclodecane dimethanol diacrylate, and hydrogen trimethyl acetaldehyde modified trimethylolpropane II The ultraviolet curable resin composition for a multilayer optical disc according to any one of the items 1 to 4, wherein the composition of the resin is relative to the resin composition. The whole material contains 5 to 80% by weight of 0) component, 1〇~8〇% by weight of ("component and 1~15 weight of ((c) component. 6.------ Please obtain the multi-layer optical disc of the patent range from item 1 to item ▲ ^ to obtain the active energy ray by ultraviolet curable resin composition. 〇 Multi-layer optical disc containing the hardening as shown in the sixth paragraph of the patent application. Type: Benefit 25
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