[go: up one dir, main page]

WO2000009620A1 - Composition de resine photodurcissable a faible teneur en chlore - Google Patents

Composition de resine photodurcissable a faible teneur en chlore Download PDF

Info

Publication number
WO2000009620A1
WO2000009620A1 PCT/NL1999/000511 NL9900511W WO0009620A1 WO 2000009620 A1 WO2000009620 A1 WO 2000009620A1 NL 9900511 W NL9900511 W NL 9900511W WO 0009620 A1 WO0009620 A1 WO 0009620A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
manufactured
glycol
information
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/NL1999/000511
Other languages
English (en)
Inventor
Toshihiko Takahashi
Yuichi Takehana
Hideaki Takase
Takashi Ukachi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JSR Corp
Japan Fine Coatings Co Ltd
Koninklijke DSM NV
Original Assignee
JSR Corp
Japan Fine Coatings Co Ltd
DSM NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JSR Corp, Japan Fine Coatings Co Ltd, DSM NV filed Critical JSR Corp
Publication of WO2000009620A1 publication Critical patent/WO2000009620A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/147—Polyurethanes; Polyureas
    • 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
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • 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
    • G11B7/253—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 substrates
    • G11B7/2533—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 substrates comprising resins
    • G11B7/2534—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 substrates comprising resins polycarbonates [PC]

Definitions

  • the present invention relates to photocurable resin compositions having a low chlorine content.
  • the present invention relates to a photocurable resin compositions suitable for use with information disks, including in particular, disks having multiple elements comprising information (or the ability to receive and retain information) , preferably, this will include optical disks ⁇ i . e . , those wherein the information, preferably digital information, is recorded and/or retrieved using optics) for example, digital video disks or digital versatile disks, commonly referred to as a DVD's.
  • Recent progress of information technologies including computer devices, computer software, and communication technologies has allowed a high speed conveyance of mass information.
  • recording media which can record much more information at high density have been desired and the development of such recording media is ongoing.
  • An example of such high-density recording media is a DVD which has been developed as a recording media for wide use in the next generation.
  • the DVD differs from conventional CDs (compact disks) in that the DVD is manufactured by adhering two sheets of disks. Therefore, an adhesive for adhering the two sheets of disks is required and use of hot -melt, heat -curable, anaerobic curable, or similar adhesives has been attempted.
  • hot-melt adhesives have insufficient heat stability and weatherability. Because these adhesives soften at a high temperature, the decreased adhesive strength causes the adhered disks to be separated and deformed. In addition, since transparency of the adhesive is insufficient, it is difficult to use these adhesives for the DVD comprising two recording films of which one is translucent .
  • a problem with heat-curable adhesives is that heat during curing causes the substrate for forming a disk to deform and the curing time is long. On the other hand, anaerobic curable adhesives require a certain period of time for curing, thereby resulting in reduced productivity.
  • UV curable adhesives comprising a urethane acrylate as a major component have been disclosed in Japanese Patent Applications Laid-open No. 142545/1986 and No.
  • optical disks manufactured using these conventional photocurable adhesives exhibit only insufficient moisture resistance and heat resistance. Information recorded in such disks may be lost over time under high temperature and high humidity conditions .
  • the present invention provides a photocurable resin composition useful as an adhesive for fabricating information disks exhibiting superior heat resistance and moisture resistance.
  • the present inventors have undertaken extensive studies and found that a photocurable resin composition with a reduced chlorine content, when used as an adhesive for information disks, induces almost no deterioration of metallic films on substrate surfaces for optical disks and can produce information recording disks with excellent moisture resistance and heat resistance.
  • an object of the present invention is to provide a photocurable resin composition
  • a photocurable resin composition comprising (A) an urethane (meth) acrylate, (B) a (meth) acrylate compound having at least one (meth) acryloyl group in the molecule, and (C) a photo- initiator, wherein the content of chlorine in the composition is not more than 0.001 wt%.
  • Another object of the present invention is to provide a process for preparing the photocurable resin composition according to claim 1, comprising a step of washing the components (A) , (B) , and (C) either prior, during or after blending two or more of the components (A) , (B) , and (C) .
  • Still another object of the present invention is to provide an information disk comprising two elements adhered to each other using the above photocurable resin composition.
  • the urethane (meth) acrylate used as the component (A) is obtained by reacting a polyol compound, a polyisocyanate compound, and a hydroxyl group-containing (meth) acrylate .
  • polyether polyol As the polyol compound used in the present invention, a polyether polyol, polyester polyol, polycarbonate polyol, polycaprolactone polyol, aliphatic hydrocarbon containing two or more hydroxyl groups in the molecule, alicyclic hydrocarbon containing two or more hydroxyl groups in the molecule, unsaturated hydrocarbon containing two or more hydroxyl groups in the molecule, and the like can be given.
  • polyol compounds may be used either independently or in combinations of two or more.
  • the above polyether polyol includes aliphatic polyether polyols, alicyclic polyether polyols, and aromatic polyether polyols.
  • aliphatic polyether polyols examples include polyhydric alcohols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, pentaerythritol , dipentaerythritol , trimethylolpropane, and alkylene oxide addition polyols such as ethylene oxide addition triol of trimethylolpropane, propylene oxide addition triol of trimethylolpropane, ethylene oxide and propylene oxide addition triol of trimethylolpropane, ethylene oxide addition tetraol of pentaerythritol, and ethylene oxide addition hexaol of dipentaerythritol; polyether polyols produced by ring-opening polymerization of two or more ionic polymerizable cyclic compounds; and the like.
  • polyhydric alcohols such as polyethylene glycol, polypropylene glyco
  • cyclic ethers such as ethylene oxide, propylene oxide, butene-1 -oxide, isobutene oxide, 3 , 3 -bischloromethyl oxetane, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane, trioxane, tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl ether, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monoxide, isoprene monoxide, vinyloxetane, vinyltetrahydrofuran, vinylcyclohexene oxide, phenyl glycidyl ether, butyl glycidyl ether, and glycidyl benzoate.
  • cyclic ethers such as ethylene oxide, propylene oxide, butene-1 -oxide
  • Examples of specific combinations of two or more of the above ionic polymerizable cyclic compounds include combinations of tetrahydrofuran and ethylene oxide, tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyltetrahydrofuran, tetrahydrofuran and 3 -methyltetrahydrofuran, ethylene oxide and propylene oxide, butene-1 -oxide and ethylene oxide, and tetrahydrofuran, butene-1-oxide, and ethylene oxide.
  • a polyether polyol produced by ring-opening polymerization of one of the above ionic polymerizable cyclic compounds and cyclic imines such as ethyleneimine, cyclic lactic acids such as ⁇ - propyolactone and glycolic acid, or dimethylcyclopolysiloxane can also be used.
  • Examples of the alicyclic polyether polyols include alkylene oxide addition diol of hydrogenated bisphenol A, alkylene oxide addition diol of hydrogenated bisphenol F, and alkylene oxide addition diol of 1, 4-cyclohexanediol .
  • aromatic polyether polyols examples include alkylene oxide addition diol of bisphenol A, alkylene oxide addition diol of bisphenol F, alkylene oxide addition diol of hydroquinone , alkylene oxide addition diol of naphthohydroquinone , and alkylene oxide addition diol of anthrahydroquinone .
  • Polyether polyols are commercially available under the following trade names: examples of aliphatic polyether polyols include PTMG650, PTMG1000, PTMG2000 (manufactured by Mitsubishi Chemical Corp.), PPG1000, EXCENOL1020, EXCENOL2020, EXCENOL3020, EXCENOL4020 (manufactured by Asahi Glass Co., Ltd.), PEG1000, Unisafe DC1100, Unisafe DC1800, Unisafe
  • DCB1100, Unisafe DCB1800 manufactured by Nippon Oil and Fats Co., Ltd.
  • PPTG1000, PPTG2000, PPTG4000, PTG400, PTG650, PTG2000, PTG3000, PTGL1000, PTGL2000 manufactured by Hodogaya Chemical Co., Ltd.
  • Z-3001- 4, Z-3001-5 PBG2000, PBG2000B (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), TMP30, PNT4 Glycol, EDA P4 , EDA P8 (manufactured by Nippon Nyukazai Co., Ltd.) , and Quadrol (manufactured by Asahi Denka Kogyo K.K.)
  • aromatic polyether polyols include Uniol DA400, DA700, DAIOOO, and DB400 (manufactured by Nippon Oil and Fats Co . ,
  • the above-mentioned polyester polyol can be obtained by reacting a polyhydric alcohol with a polybasic acid.
  • a polyhydric alcohol examples include ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol,
  • polyester polyols examples include phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid, sebacic acid, and the like.
  • polycarbonate diols shown by the formula ( 1 ) are given :
  • R 1 represents an alkylene group having 2-20 carbon atoms, a residual group of (poly) ethylene glycol, a residual group of
  • R residual groups of 1 , 4-butanediol , 1, 5-pentanediol , neopentyl glycol, 1 , 6-hexanediol, 1,4- cyclohexanedimethanol, 1, 7-heptanediol, 1 , 8-octanediol, 1, 9-nonanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and the like.
  • polycarbonate polyols are commercially available under the trade names, for example, DN-980, DN-981, DN-982, DN-983 (manufactured by Nippon Polyurethane Industry Co., Ltd.), PC-8000 (manufactured by PPG), PNOC1000, PNOC2000, PMC100, PMC2000 (manufactured by Kuraray Co., Ltd.), PLACCEL CD-205, CD-208, CD-210, CD-220, CD-205PL, CD-208PL, CD- 210PL, CD-220PL, CD-205HL, CD-208HL, CD-210HL, CD- 220HL, CD-210T, CD-221T (manufactured by Daicel Chemical Industries, Ltd.), and the like.
  • polycaprolactone polyol examples include polycaprolactone diols obtained by the addition reaction of ⁇ -caprolactone to a diol such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1 , 2-polybutylene glycol, 1, 6-hexanediol , neopentyl glycol, 1,4- cyclohexanedimethanol , and 1, 4-butanediol .
  • ethylene glycol polyethylene glycol
  • propylene glycol polypropylene glycol
  • tetramethylene glycol polytetramethylene glycol
  • polytetramethylene glycol 1
  • 2-polybutylene glycol 1, 6-hexanediol
  • neopentyl glycol 1,4- cyclohexanedimethanol
  • 4-butanediol are commercially available under the
  • Examples of the above aliphatic hydrocarbon containing two or more hydroxyl groups in the molecule include ethylene glycol, propylene glycol, tetramethylene glycol, 1, 4-butanediol , 1, 5-pentanediol , 1, 6-hexanediol, 1 , 7-heptanediol , 1 , 8-octanediol , 1,9- nonanediol, neopentyl glycol, 2 , 2-diethyl-l, 3- propanediol, 3 -methyl-1 , 5-pentanediol , 2 -methyl-1 , 8- octanediol, hydrogenated polybutadiene with terminal hydroxyl groups, glycerol , trimethylolpropane, pentaerythritol, and sorbitol .
  • Examples of the above alicyclic hydrocarbon having two or more hydroxyl groups in the molecule include 1 , 4-cyclohexanediol , 1 , 4-cyclohexanedimethanol , 1 , 2-bis (hydroxyethyl) cyclohexane, dimethylol compounds of dicyclopentadiene, and tricyclodecanedimethanol .
  • examples of polyols other than the above-mentioned polyol compounds include ⁇ -methyl- ⁇ -valerolactone diol, castor oil-modified diol, a polydimethylsiloxane with diols at the terminals, and a polydimethylsiloxane carbitol-modified diol.
  • the number average molecular weight of these polyol compounds is preferably from 50 to 15000, and more preferably from 100 to 8000.
  • diisocyanate compounds are preferable.
  • diisocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, 1,5- naphthalene diisocyanate, m-phenylene diisocyanate, p- phenylene diisocyanate, 3 , 3 ' -dimethyl-4 , 4 ' - diphenylmethane diisocyanate, 4 , 4 ' -diphenylmethane diisocyanate, 3 , 3 ' -dimethylphenylene diisocyanate, 4 , 4 ' -biphenylene diisocyanate, 1,6-hexane diisocyanate, is
  • 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, and the like are preferable.
  • These diisocyanate compounds may be used either singly or in combinations of two or more.
  • Examples of the hydroxyl group-containing (meth) acrylate compound include 2 -hydroxyethyl (meth) acrylate , 2 - hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2 -hydroxy-3 - phenyloxypropyl (meth) acrylate, 1 , 4-butanediol mono (meth) acrylate, 2-hydroxyalkyl (meth) acryloyl phosphate, 4 -hydroxycyclohexyl (meth) acrylate, 1,6- hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolethane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and (me
  • CH 2 C—C—OCH 2 CH 2 —(OCCH 2 CH 2 CH 2 CH 2 CH 2 )n—OH (2 )
  • R ,2 represents a hydrogen atom or a methyl group and n denotes an integer from 1 to 15, and preferably from 1 to 4.
  • Compounds obtained by the addition reaction of a (meth) acrylic acid and a compound containing a glycidyl group such as alkyl glycidyl ether, allyl glycidyl ether, and glycidyl (meth) acrylate can also be given as examples of the (meth) acrylate compound.
  • 2- hydroxyethyl (meth) acrylate, 2- hydroxypropyl (meth) acrylate , 2 - hydroxybutyl (meth) acrylate, and the like are preferable .
  • urethanization catalyst such as copper naphthanate, cobalt naphthanate, zinc naphthanate, di-n-butyltin dilaurate, triethylamine, 1, 4-diazabicyclo [2.2.2] octane, and l,4-diaza-2- methylbicyclo [2.2.2] octane in an amount from 0.01 to 1 part by weight for 100 parts by weight of the total reaction components.
  • the reaction is generally carried out at a temperature of 0 to 90°C, and preferably 10 to 80°C.
  • the number average molecular weight of the urethane (meth) acrylate used in the present invention is preferably from 400 to 20000, and more preferably from 600 to 10000.
  • the urethane (meth) acrylate (A) is incorporated in the composition of the present invention in an amount preferably from 5 to 70 parts by weight for 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • the (meth) acrylate compound having at least one (meth) acryloyl group in the molecule which is used as component (B) in the resin composition of the present invention either a monofunctional compound having only one (meth) acryloyl group or a polyfucntional compound having two or more (meth) acryloyl groups, or combination of these at an appropriate proportion, can be used.
  • Examples of the monofunctional compound include 2 -hydroxyethyl (meth) acrylate, 2- hydroxypropyl (meth) acrylate , 2 - hydroxybutyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth) acrylate, t -butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl
  • (meth) acrylate ethoxydiethylene glycol (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, methoxyethylene glycol mono (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol
  • (meth) acrylate isobornyl (meth) acrylate, adamantyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 7-amino-3,7- dimethyloctyl (meth) acrylate, (meth) acryloylmorpholine, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxypropylphthalic acid,
  • R 3 represents an alkylene group or a hydroxyalkylene group having 2-6 carbon atoms
  • R 4 represents a hydrogen atom or a methyl group
  • R represents a hydrogen atom or an alkyl group having 1- 12 carbon atoms
  • p denotes an integer from 0 to 20;
  • R represents a hydrogen atom or a methyl group
  • R represents an alkylene group having 2-8 carbon atoms, and q denotes an integer from 0 to 8;
  • R represents a hydrogen atom or a methyl group
  • R represents an alkylene group having 2-8 carbon atoms
  • r denotes an integer from 0 to 8
  • R 1 and R independently represent a hydrogen atom or an alkyl group having 1-6 carbon atoms.
  • Examples of a polyfunctional compound include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1 , 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1,9- nonanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate,
  • Examples of commercially available products of these compounds include SA-1002, SA-2006, SA-2007, SA-4100, SA-5001, SA-6000, SA-7600, SA-8000, SA-9000 (manufactured by Mitsubishi Chemical Corp.), Viscoat #195, #195D, #214HP, #215, #215D, #230, #230D, #260, #295, #295D, #300, #310HP, #310HG, #312, #335HP, #335D, #360, #400, V#540, #700, GPT (manufactured by Osaka Organic Chemical Industry Co., Ltd.), KAYARAD MANDA, R- 526, NPGDA, PEG400DA, R-167, HX-220, HX-620, R-551, R- 712, R-604, R-684, GPO-303, TMPTA, THE-330, TPA-320, TPA-330, PET-30, RP-1040, T-1420, DPHA, D-310, D-330, DPCA-20,
  • (meth) acrylate compounds used as the component (B) is incorporated in the composition of the present invention preferably in an amount from 30 to 90 parts by weight for 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • any known photo-polymerization initiator may be used as component (C) in the composition of the present invention without specific limitations.
  • the photo-polymerization initiator (C) are 1-hydroxycyclohexyl phenyl ketone, 3- methylacetophenone , 2 , 2 -dimethoxy-2 -phenylacetophenone , xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone, triphenylamine, carbazole, 3- methylacetophenone, benzophenone, 4-chlorobenzophenone, 4,4' -dimethoxybenzophenone , 4,4' -diaminobenzophenone , benzoin ethyl ether, benzoin propyl ether, Michler's ketone, benzyl methyl ketal, 1- (4-isopropylphenyl) -2- hydroxy-2 -methylpropan- 1-one , 2 ,
  • photo-polymerization initiators are commercially available under the trade names, for example, IRGACURE 184, 261, 369, 500, 651, 907, CGI- 403, 819, 1700, 1800, 1850 (manufactured by Ciba Specialty Chemicals Co., Ltd.), Lucirin TPO, TPO-L, LR8893 (manufactured by BASF), Darocur 953, 1116, 1173, 1664, 2273, 2959, ZLl 3331 (manufactured by Merck), Ubecryl P36 (manufactured by UCB) , VICURE55 (manufactured by Akzo) , ESACURE KIP100F, KIP150 (manufactured by Lamberti) , and KAYACURE ITX, QTX, DETX, BMS (manufactured by Nippon Kayaku Co., Ltd.) .
  • IRGACURE 184, 369, 651, 907 Darocurable
  • photo-polymerization initiators may be used either individually or in combinations of two or more.
  • the component (C) is incorporated in the composition of the present invention in an amount usually from 0.1 to 20 parts by weight, preferably from 0.5 to 15 parts by weight, and particularly preferably from 1 to 10 parts by weight, for 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • radically polymerizable compounds other than compounds containing an acryl group may be incorporated in the composition of the present invention as a component (D) .
  • radically polymerizable compounds other than compounds containing an acryl group may be incorporated in the composition of the present invention as a component (D) .
  • such compounds are N-vinylpyrrolidone, N-vinylcaprolactam, vinyl acetate, vinyl propionate, styrene, divinylbenzene, and unsaturated polyesters.
  • the unsaturated polyesters are esters of a dicarboxylic acid containing a radically polymerizable unsaturated double bond and an alcohol.
  • Examples of a dicarboxylic acid containing a radically polymerizable unsaturated double bond include maleic acid anhydride, itaconic acid, and fumaric acid.
  • Examples of an alcohol include monohydric alcohols such as methanol , ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n- hexanol, cyclohexanol , and 2-ethylhexyl alcohol; (poly) ethylene glycols such as ethylene glycol, diethylene glycol, triethylene glycol, and the like; (poly) propylene glycols such as propylene glycol, dipropylene glycol, and tripropylene glycol; dihydric alcohols such as 1 , 6-hexanediol ; and trihydric alcohols such as glycerol and trimethylolpropane.
  • an epoxy resin polyamide, polyamideimide, polyurethane, polybutadiene, chloroprene, polyether, polyester, pentadiene derivatives, SBS (styrene/butadiene/styrene block copolymer) , hydrogenated products of SBS, SIS (styrene/isoprene/styrene block copolymer) , petroleum resin, xylene resin, ketone resin, fluorine-based oligomer, silicone-based oligomer, polysulfide-based oligomer, and the like may be incorporated in the composition of the present invention as other additives .
  • composition of the present invention may further include various additives used for paints other than the above additives, for example, antioxidants, UV absorbers, light stabilizers, aging preventives, silane coupling agents, antifoaming agents, leveling agents, antistatic agents, surfactants, preservatives, heat polymerization inhibitors, plasticizers, and wettability improvers.
  • additives used for paints other than the above additives for example, antioxidants, UV absorbers, light stabilizers, aging preventives, silane coupling agents, antifoaming agents, leveling agents, antistatic agents, surfactants, preservatives, heat polymerization inhibitors, plasticizers, and wettability improvers.
  • antioxidants include Irganox 245, 259, 565, 1010, 1035, 1076, 1081, 1098, 1222, 1330 (manufactured by Ciba Specialty Chemicals Co., Ltd.), and the like.
  • UV absorbers include benzotriazole type and triazine type UV absorbers and commercially available products such as Tinuvin P, 234, 320, 326, 327, 328, 213, 400 (manufactured by Ciba Specialty Chemicals Co., Ltd.), Sumisorb 110, 130, 140, 220, 250, 300, 320, 340, 350, 400 (manufactured by Sumitomo Chemical Industries Co., Ltd.), and the like.
  • Examples of light stabilizers include commercially available products such as Tinuvin 144, 292, 622LD (manufactured by Ciba Specialty Chemicals Co., Ltd.), Sanol LS440, LS770 (manufactured by Sankyo Co., Ltd.), and Sumisorb TM-061 (manufactured by Sumitomo Chemical Industries Co., Ltd.).
  • aging preventives examples include phenol type, allylamine type, and ketone amine type aging preventives. Examples of commercially available products of these aging preventives include Antigene W,
  • silane coupling agents examples include:
  • S520, S530, S610, S620, S710, S810 manufactured by Chisso Corp.
  • SH6020, SZ6023, SZ6030, SH6040, SH6076, SZ6083, AY43-062 manufactured by Toray-Dow Corning Silicone Co., Ltd.
  • KBM403, KBM503, KBM602, KBM603, KBM803, KBE903 manufactured by Shin-Etsu Silicone Co., Ltd.
  • antifoaming agents include organic copolymers excluding silicon and fluorine which are commercially available under the trade names, for example, Flowlen AC-202 , AC-300, AC-303, AC-326F, AC- 900, AC-1190,and AC-2000 (manufactured by Kyoeisha
  • silicon-containing antifoaming agents which are commercially available under the trade names, for example, Flowlen AC-901, AC-950, AC-1140, AO-3, AO- 40H (manufactured by Kyoeisha Yushi Co., Ltd.), FS1265, SH200, SH5500, SC5540, SC5570, F-l, and SD5590
  • fluorine-containing antifoaming agents which are commercially available under the trade names, for example, MEGAFAC F-142D, F-144D, F-178K, F-179, F-815 (manufactured by Dainippon Ink and Chemicals, Inc.); and the like.
  • leveling agents examples include Polyflow No. 7, No. 38, No. 50E, S, No. 75, No. 77, No. 90, No. 95, No. 300, No. 460, ATF, KL-245 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.
  • the amount of these additives can be appropriately determined so that the objectives of the present invention are not adversely affected.
  • the amount of chlorine is defined as relative to the total composition, and more preferably relative to total of components (A) , (B) and (C) .
  • some chlorine may be present, for instance, 0.1 ppm or more, but should not be more than 0.001 wt%, preferably not more than 0.0003 wt%, and even more preferably not more than 0.0005 wt%.
  • Distortion on the surface of a metal film for optical disk substrate can be reduced using the resin composition with a small chlorine content.
  • the moisture resistance and heat resistance of the optical disk substrate are improved.
  • Reducing the chlorine content to less than 0.001 wt% can be achieved by using the raw materials such as components (A) , (B) , and (C) , as well as other additives, having a chlorine content of less than 0.001 wt%.
  • the raw materials such as components (A) , (B) , and (C) , as well as other additives, having a chlorine content of less than 0.001 wt%.
  • some raw materials may have a chlorine content of more than
  • Preferred methods for reducing the chlorine content in the composition of the present invention to less than 0.001 wt% include (1) a method of washing the raw materials, an intermediate containing two or more raw materials, or the composition prepared by mixing all the components with purified water and (2) a method of treating one or more of these materials with an ion exchange material .
  • the method for removing chlorine by washing preferably includes thoroughly mixing with purified water the treating material, i . e .
  • purified water means water with a sufficiently low content of chlorine.
  • purified water includes distilled water, ion exchanged water, and water prepared by filtering these waters through a suitable filter.
  • an organic solvent may be added to the treating material prior to washing with water. Such an organic solvent is removed after washing.
  • a hydrophobic solvent which can abundantly dissolve the raw materials, the intermediate comprising at least two raw material components, or the composition containing all raw materials, but can only scarcely dissolve water, can be used in this washing operation.
  • Such a solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as n-hexane, cyclohexane, and n-pentane; and ethers such as diethyl ether and isopropyl ether.
  • Suitable ion exchange materials include organic ion exchange materials and inorganic ion exchange materials.
  • a treatment by means of "contact” is a typical treatment with these ion exchange materials.
  • a specific method of treatment comprises mixing the ion exchange material with the treating material, i . e . , (1) the raw materials, (2) the intermediate comprising at least two raw material components, or (3) the composition containing all raw materials.
  • the ion exchange material is usually removed by precipitation in a sedimentation tank, forcedly separated by a centrifugal separator, or removed by filtration using a suitable filter.
  • the ion exchange material need not be removed, if there is no adverse effect on the performance of the adhered disks.
  • ion exchange material used in the present invention should be mutually insoluble with and easily separated from the resin composition, and is preferably in the form of particles.
  • Suitable ion- exchange resins include organic materials, and inorganic ion exchange materials.
  • suitable inorganic materials having an ion exchange capabilities include activated carbon, zeolite, synthetic zeolite, silica gel, activated alumina, hydrotalcite, hydrocalumite, acid clay, dolomite, zirconium hydroxide, titanium hydroxide, cerium hydroxide, bismuth hydroxide, manganese hydroxide, hydroxide lead phosphate, various hydrate oxide containing Mg, Zn, Ca, Mn, Fe, Co, Ni , Cu, Al , Si, or the like as a major component, and inorganic ion exchange materials containing various metal phosphate as a major component.
  • Preferred inorganic ion-exchange materials include hydrotalcite compounds are DHT-4A, KW-1000, KW- 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.); as hydrocalumite compound, Solcat C (manufactured by Nippon Chemical Industrial Co., Ltd.); as bismuth-type ion exchange materials, IXE-500, IXE- 550, IXE-600, IXE-633, and IXE-680; as aluminum-type ion exchange materials, IXE-700 and IXE-702; as zirconium-type ion exchange material, IXE-800; as lead- based inorganic ion exchange material, IXE-1000; as calcium-type ion exchange material, IXE-1100; and as antimony-type ion exchange material, IXE-1320 (all manufactured by Toagosei Co., Ltd.) .
  • the viscosity of the composition of the present invention is preferably from 10
  • the glass transition temperature of the resulting cured product is from -50 to 200°C, preferably from -20 to 150°C, and more preferably from 0 to 100°C. If the glass transition temperature is too low, the cured products may soften when heated in summer or in a closed and sunny room, thereby resulting in decrease in adhesion strength. This may cause the adhered members to peel off or slip out. On the contrary, if the glass transition temperature is too high, adhesion may be insufficient or the coated members break when dropped or bent.
  • the glass transition temperature described here is defined as the temperature at which a loss tangent (tan ⁇ ) reaches a peak when measured by a dynamic viscoelasticity measuring device at an oscillation frequency of 10 Hz.
  • the composition of the present invention can be cured by exposure to ultraviolet radiation, visible rays, electron beams, or the like in the same manner as in the case of using conventional photocurable resin compositions.
  • the composition of the present invention can be easily cured by filling the composition between the members to be coated so that the thickness of the adhesive layer is from 10 to 100 mm and irradiating the adhesive layer at a dose of 50 to 2000 J/cm using a metal halide lamp, whereby the members can be glued to each other.
  • the cured products made from the composition of the present invention are desired to have excellent transparency.
  • the cured products with a thickness of 60 mm have a light transmittance of 90% or more at a wave length of 400 to 700 nm. If the light transmittance is less than 90%, not only is the appearance of the optical disks impaired, but also the light for reading the information recorded on the disk is reduced by the adhesive layer, thereby making it difficult to read the information. Therefore, in preparing the composition of the present invention, each component should be blended so that the light transmittance of the resulting cured product satisfy this requirement.
  • the refractive index of the photocured product made from the composition of the present invention is in the range from 1.51 to 1.70. If the refractive index is out of this range, reading of the information recorded on the disk may be difficult.
  • composition of the present invention exhibits excellent adhesion to plastics such as polycarbonate (PC) and poly (methylmethacrylate) (PMMA), metals such as gold and aluminum, and inorganic materials such as glass. Therefore, the composition of the present invention is suitable as an adhesive for various elements of an information disk in particular those employed in optical disks.
  • plastics such as polycarbonate (PC) and poly (methylmethacrylate) (PMMA)
  • metals such as gold and aluminum
  • inorganic materials such as glass. Therefore, the composition of the present invention is suitable as an adhesive for various elements of an information disk in particular those employed in optical disks.
  • the resin composition of the present invention is useful as an adhesive for information disks made by adhering two sheets of substrate, particularly for adhering a layer comprising information (or material suitable for recording information) which may consist, for example, of a light reflection layer made of a thin metal film provided on a resin substrate, to a second substrate.
  • the second substrate may similarly comprise information (or material suitable for recording information) consisting of a light reflection layer made of a thin metal film provided on a resin substrate, or another element not comprising an information storage/recording components.
  • Preferred examples of an information disk comprising multiple elements include DVD, DVD-R, DVD-ROM, and the like.
  • chlorine content relative to the total composition of the present invention exceeds 0.001 wt%, corrosion or deterioration of the thin metal film on the information recording layer will be conspicuous due to moisture invading from outside into the cured adhesive layer or into the interface of the cured adhesive and metal film.
  • composition wherein the urethane (meth) acrylate for the component (A) has a number average molecular weight from 600 to 10,000. 2. The composition, wherein the component (A) is incorporated in an amount from 5 to 70 parts by weight of 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • composition wherein the component (B) is incorporated in an amount from 30 to 90 parts by weight of 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • composition wherein the component (C) is incorporated in an amount from 1 to 10 parts by weight of 100 parts by weight of the total amount of the components (A) , (B) , and (C) .
  • composition having a chlorine content of not more than 0.0005% by weight.
  • composition having a viscosity from 100 to 2000 mPa.s at 25°C.
  • composition, of which the cured product obtained by irradiation with UV light has a glass transition temperature from 0 to 100°C.
  • composition, of which the cured product obtained by irradiation with UV light has a refractive index from 1.51 to 1.70 at 25°C.
  • urethane acrylate (A2) 200 g was dissolved in 400 g of toluene. After the addition of 1000 g of ion exchanged water, the solution was thoroughly stirred and then allowed to stand to separate the water layer from the organic layer. After the addition of 1000 g of ion exchange water to the resulting organic layer, the mixture was stirred and allowed to stand, followed by separation of the water layer. The organic layer thus obtained was subjected to a rotary evaporator to evaporate toluene and water, thus obtaining purified urethane acrylate (A2) .
  • Synthesis Example 2 175.8 g of 1,3- bis (isocyanatemethyl) cyclohexane (Takenate 600, manufactured by TAKEDA CHEMICAL INDUSTRIES Co., Ltd.), 0.3 g of 3, 5 -di-t-butyl-4 -hydrox toluene, and 505.6 g of polycarbonate diol having a hydroxyl value of 224 mg KOH/g (PLACCEL CD205, manufactured by Daicel Chemical Industries, Ltd.) were placed in a separable flask (1 liter) equipped with a stirrer and a thermometer. The mixture was stirred and cooled to 10°C in a cold water bath in dry air.
  • urethane acrylate (A3) having a number average molecular weight of 1130.
  • the urethane acrylate (A3) was washed with ion exchanged water in the same manner as in Synthesis Example 1 to obtain urethane acrylate (A4) .
  • Example 1 The components shown in Table 1 were placed in a reaction vessel equipped with a stirrer and stirred to prepare the compositions of Examples 1-5 and Comparative Examples 1-4. The amount of each component is indicated by parts by weight in Table 1. After preparation, the compositions of Example 1 and Example 3 were passed through a glass tube with a diameter of 5 cm packed with granules of a bismuth-type ion exchange material (IXE-500G, manufactured by Toagosei Co., Ltd.) to a depth of 50 cm and maintained at 50 °C, thereby removing chloride ion. This treatment for removing chloride ion is hereinafter called "column treatment". The components shown in Table 1 are as follows.
  • Component (D) (other component) DI : Sodium chloride
  • the chlorine content for the compositions (Examples 1-5 and Comparative Examples 1-4) thus prepared were measured as follows. 4 g of each composition shown in Table 1 and 80 g ion exchanged water were sealed in a Teflon container and heated in a pressure cooker for 24 hours at 120°C to hydrolyze hydrolyzable chlorine compounds into chloride ion. The chloride ion was dissolved in ion exchanged water and quantitatively analyzed by ion chromatography using DIONEX 2010i manufactured by DIONEX Co.
  • Ion Pac AS12A was used as a separation column and an aqueous solution of Na 2 C0 3 (0.0027 mol/liter) and NaHC0 3 (0.0003 mol/liter) used as an eluate at a flow rate of 1.1 ml/minute.
  • Viscosity of the compositions prepared above, refractive index and glass-transition temperature of the cured products made from the compositions, and moisture resistance and heat resistance of disks prepared by using these compositions as adhesives were evaluated according to the following method.
  • Viscosity was measured at 25°C using a
  • Brookfield type viscometer (BM-type, Rotor No. 2) manufactured by Tokyo Keiki Co., Ltd.
  • Refractive index of the composition was applied on a flat glass plate using an applicator bar and cured by irradiating with ultraviolet radiation at a dose of 1 J/cm 2 using a conveyer-type ultraviolet radiation apparatus with a metal halide lamp as a light source (manufactured by the Eye Graphics Co., Ltd.) .
  • the cured product was peeled off from the glass plate to obtain a cure film with a thickness 0.2 mm.
  • Refractive index of the cure film was measured at 25 °C using an Abbe's refractometer manufactured by ATAGO Co., Ltd.
  • a polycarbonate substrate with a thickness of 0.6 mm and another substrate prepared by sputtering an aluminum film by vapor deposition to a thickness of 200 angstrom on one side of the same polycarbonate substrate were used for the test.
  • the compositions prepared in the above Examples and Comparative Examples were dropped onto the aluminum surface of the latter substrate, i.e. the substrate with an aluminum film sputtered by vapor deposition.
  • the polycarbonate substrate was layered over the aluminum surface onto which the composition was dropped.
  • the substrates were rotated by a spin coater to cause the composition to permeate into the both substrates.
  • Light was irradiated at a dose of 300 mJ/cm through the polycarbonate substrate to cure the composition.
  • the adhered substrate thus prepared was allowed to stand for 200 hours in a thermo-hygrostat at 80°C, 95%RH, to observe the outward appearance both by the naked eyes and microscope.
  • the moisture resistance and heat resistance was rated as "0" for the composition exhibiting no uniform corrosion, pitting corrosion, intergranular corrosion, or corrosion breaking on aluminum surface. Otherwise, the moisture resistance and heat resistance was rated as "X" .
  • the viscosity of the resin compositions of Examples and Comparative Example, all comprising the components (A) , (B) , and (C) of the present invention, at 25°C was between 400 and 1500 mP-s.
  • the glass transition temperature and refractive index at 25°C of the cured products obtained from these composition by irradiation of ultraviolet radiation was respectively from 45 to 63°C and from 1.51 to 1.52, indicating that all compositions satisfy the standard required for the adhesive used for preparing information record disks.
  • the compositions of the Examples with a chlorine content of less than 0.001 wt% exhibited no corrosion, whereas the disks fabricated using the compositions of the Comparative Examples containing more than 0.001 wt% of chlorine produced corrosion, failing to pass through the corrosion test.
  • the photocurable resin composition of the present invention comprises specific components and has a chlorine content of not more than 0.001 wt%.
  • Optical disks fabricated by using the photocurable resin composition of the present invention as an adhesive exhibit superior heat resistance and moisture resistance .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Polymerisation Methods In General (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition de résine photodurcissable comprenant (A) un uréthanne (méth)acrylate préparé par la réaction d'un composé de polyol, d'un composé de polyisocyanate et d'un composé de (méth)acrylate contenant un groupe hydroxyle, (B) un composé de (méth)acrylate ayant au moins un groupe (méth)acryloyle dans la molécule et (C) un photo-initiateur, et ayant une teneur en chlore ne dépassant pas 0,001 % en poids. L'invention concerne également un procédé de préparation de la composition de résine photodurcissable ainsi qu'un disque d'enregistrement d'informations fabriqué à l'aide de la composition de résine durcissable en tant qu'adhésif.
PCT/NL1999/000511 1998-08-17 1999-08-11 Composition de resine photodurcissable a faible teneur en chlore Ceased WO2000009620A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10230469 1998-08-17
JP10230469A JP2000063446A (ja) 1998-08-17 1998-08-17 光硬化型樹脂組成物

Publications (1)

Publication Number Publication Date
WO2000009620A1 true WO2000009620A1 (fr) 2000-02-24

Family

ID=16908322

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1999/000511 Ceased WO2000009620A1 (fr) 1998-08-17 1999-08-11 Composition de resine photodurcissable a faible teneur en chlore

Country Status (2)

Country Link
JP (1) JP2000063446A (fr)
WO (1) WO2000009620A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1120447A1 (fr) * 2000-01-28 2001-08-01 Dainippon Ink And Chemicals, Inc. Composition durcissable par UV et support d' enregistrement optique
WO2002014386A1 (fr) * 2000-08-11 2002-02-21 Sony Chemicals Corp. Composition de resine photopolymerisable pour supports d'enregistrement optiques, et supports d'enregistrement optiques
EP1247828A1 (fr) * 2001-04-02 2002-10-09 Sony Chemicals Corporation Support optique
US6645595B2 (en) 1999-08-23 2003-11-11 Sony Chemicals Corp. Optical medium
WO2004029115A1 (fr) * 2002-09-30 2004-04-08 Jsr Corporation Composition de resine liquide durcissable
WO2004048490A1 (fr) * 2002-11-26 2004-06-10 Nippon Kayaku Kabushiki Kaisha Composition adhesive polymerisable par uv pour disque optique, matiere et articles traites
EP2161309A4 (fr) * 2007-06-26 2012-07-11 Fujikura Kasei Kk Composition de revêtement pour film mince métallique et film de revêtement composite brillant obtenu à partir de la composition de revêtement
EP2594616A3 (fr) * 2009-12-28 2013-07-17 Dai Nippon Printing Co., Ltd. Composition de revêtement et feuille utilisant celle-ci
AU2014262249B2 (en) * 2009-12-28 2015-09-24 Dai Nippon Printing Co., Ltd. Coating composition and sheet using same
US9567676B2 (en) 2006-03-31 2017-02-14 Fujikura Kasei Co., Ltd. Hard coating composition for metal substrate

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4582734B2 (ja) * 2000-03-23 2010-11-17 トッパン・フォームズ株式会社 紫外線硬化型感圧接着剤を用いた感圧接着性プリント用シート
JP2002201457A (ja) * 2001-01-05 2002-07-19 Sumitomo Chem Co Ltd 易剥離性硬化型接着剤
JP4013532B2 (ja) * 2001-11-26 2007-11-28 東亞合成株式会社 光学部材用活性エネルギー線硬化型組成物
JP4158409B2 (ja) * 2002-05-13 2008-10-01 ソニー株式会社 光ディスクの製造方法
WO2005014748A1 (fr) * 2003-08-12 2005-02-17 Nippon Kayaku Kabushiki Kaisha Composition adhesive et disque optique fabrique a l'aide de cette derniere
JP2005068348A (ja) * 2003-08-27 2005-03-17 Nippon Kayaku Co Ltd 光ディスク用接着剤組成物及びその硬化物を用いた物品
JP4493002B2 (ja) * 2003-12-12 2010-06-30 三菱レイヨン株式会社 光ディスク用硬化性組成物、保護コーティング材、接着剤および光ディスク
JP4888625B2 (ja) 2004-08-10 2012-02-29 ソニーケミカル＆インフォメーションデバイス株式会社 非溶剤型光硬化型保護膜用樹脂組成物
TW200838696A (en) * 2007-03-12 2008-10-01 Toagosei Co Ltd Optical film laminate and display device using the same
JP5022098B2 (ja) * 2007-05-07 2012-09-12 ソニーケミカル＆インフォメーションデバイス株式会社 光学的記録媒体
JP5343452B2 (ja) * 2008-08-26 2013-11-13 Ｄｉｃ株式会社 光ディスク用紫外線硬化型組成物および光ディスク

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61142545A (ja) * 1984-12-13 1986-06-30 Ricoh Co Ltd 情報記録媒体
JPH02116034A (ja) * 1988-10-24 1990-04-27 Mitsubishi Plastics Ind Ltd 光ディスク
JPH0689462A (ja) * 1992-09-07 1994-03-29 Three Bond Co Ltd 光ディスク
EP0835917A1 (fr) * 1996-04-25 1998-04-15 Nippon Kayaku Kabushiki Kaisha Composition adhesive a sechage aux u.v. et article correspondant
WO1998036325A1 (fr) * 1997-02-13 1998-08-20 Dsm N.V. Composition de resine photodurcissable
EP0889465A2 (fr) * 1997-07-03 1999-01-07 Sumitomo Chemical Company, Limited Composition de résine photoréticulable pour DVD

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61142545A (ja) * 1984-12-13 1986-06-30 Ricoh Co Ltd 情報記録媒体
JPH02116034A (ja) * 1988-10-24 1990-04-27 Mitsubishi Plastics Ind Ltd 光ディスク
JPH0689462A (ja) * 1992-09-07 1994-03-29 Three Bond Co Ltd 光ディスク
EP0835917A1 (fr) * 1996-04-25 1998-04-15 Nippon Kayaku Kabushiki Kaisha Composition adhesive a sechage aux u.v. et article correspondant
WO1998036325A1 (fr) * 1997-02-13 1998-08-20 Dsm N.V. Composition de resine photodurcissable
EP0889465A2 (fr) * 1997-07-03 1999-01-07 Sumitomo Chemical Company, Limited Composition de résine photoréticulable pour DVD

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 010, no. 341 (P - 517) 18 November 1986 (1986-11-18) *
PATENT ABSTRACTS OF JAPAN vol. 014, no. 337 (P - 1079) 20 July 1990 (1990-07-20) *
PATENT ABSTRACTS OF JAPAN vol. 018, no. 353 (P - 1764) 4 July 1994 (1994-07-04) *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6645595B2 (en) 1999-08-23 2003-11-11 Sony Chemicals Corp. Optical medium
US6924017B2 (en) 2000-01-28 2005-08-02 Dainippon Ink And Chemicals, Inc. Ultraviolet-curable composition and optical recording
EP1120447A1 (fr) * 2000-01-28 2001-08-01 Dainippon Ink And Chemicals, Inc. Composition durcissable par UV et support d' enregistrement optique
WO2002014386A1 (fr) * 2000-08-11 2002-02-21 Sony Chemicals Corp. Composition de resine photopolymerisable pour supports d'enregistrement optiques, et supports d'enregistrement optiques
AU2001278676B2 (en) * 2000-08-11 2007-02-15 Sony Chemicals Corp. Photopolymerizable resin composition for optical recording media and optical recording media
US6855389B2 (en) 2000-08-11 2005-02-15 Sony Chemicals Corp. Photopolymerizable resin compositions for optical recording media and optical recording media
EP1247828A1 (fr) * 2001-04-02 2002-10-09 Sony Chemicals Corporation Support optique
WO2004029115A1 (fr) * 2002-09-30 2004-04-08 Jsr Corporation Composition de resine liquide durcissable
CN1312187C (zh) * 2002-09-30 2007-04-25 捷时雅株式会社 液状固化性树脂组合物
WO2004048490A1 (fr) * 2002-11-26 2004-06-10 Nippon Kayaku Kabushiki Kaisha Composition adhesive polymerisable par uv pour disque optique, matiere et articles traites
US9567676B2 (en) 2006-03-31 2017-02-14 Fujikura Kasei Co., Ltd. Hard coating composition for metal substrate
EP2161309A4 (fr) * 2007-06-26 2012-07-11 Fujikura Kasei Kk Composition de revêtement pour film mince métallique et film de revêtement composite brillant obtenu à partir de la composition de revêtement
US8728618B2 (en) 2007-06-26 2014-05-20 Fujikura Kasei Co., Ltd. Coating composition for metal thin film and photoluminescent coating film formed from same
EP2594616A3 (fr) * 2009-12-28 2013-07-17 Dai Nippon Printing Co., Ltd. Composition de revêtement et feuille utilisant celle-ci
AU2014262249B2 (en) * 2009-12-28 2015-09-24 Dai Nippon Printing Co., Ltd. Coating composition and sheet using same
US9221983B2 (en) 2009-12-28 2015-12-29 Dai Nippon Printing Co., Ltd. Coating composition and sheet using same
CN105602441A (zh) * 2009-12-28 2016-05-25 大日本印刷株式会社 涂覆剂组合物及使用其的片材

Also Published As

Publication number Publication date
JP2000063446A (ja) 2000-02-29

Similar Documents

Publication Publication Date Title
US6337118B1 (en) Adhesive for optical disks
WO2000009620A1 (fr) Composition de resine photodurcissable a faible teneur en chlore
KR100539141B1 (ko) 광경화성 수지 조성물
EP1112330B1 (fr) Adhesif pour disques optiques
JPH11100419A (ja) 放射線硬化性樹脂組成物
KR100838132B1 (ko) 액상 경화성 수지 조성물
JPH10287718A (ja) 光硬化型樹脂組成物
US20010046644A1 (en) Process for manufacturing information recording media and the information recording media
EP1309666B1 (fr) Composition adhesive pour disques optiques
JP4982923B2 (ja) 光ディスク用接着剤組成物
JP2001049198A (ja) 光ディスク用接着剤
JP2002501556A (ja) 光硬化性樹脂組成物
US7976922B2 (en) Optical recording medium
JPWO2005019282A1 (ja) 紫外線硬化型樹脂組成物およびその硬化物
JP2008171535A (ja) 光情報記録媒体
JP2009170065A (ja) 多層光記録媒体の製造方法およびそれにより得られる多層光記録媒体
JP4212076B2 (ja) 光硬化性樹脂組成物および硬化物
JP2008024724A (ja) 紫外線硬化型樹脂組成物およびその硬化物
TW574339B (en) Adhesive composition for optical disks
JP2000219713A (ja) 光硬化性樹脂組成物
JP2008117468A (ja) 光記録媒体及びその製造方法
WO2000022022A1 (fr) Composition de resine photopolymerisable pour elements de tensionnement

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CN KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase