WO2006019023A1 - 光ディスク用接着剤組成物、硬化物および物品 - Google Patents
光ディスク用接着剤組成物、硬化物および物品 Download PDFInfo
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- WO2006019023A1 WO2006019023A1 PCT/JP2005/014652 JP2005014652W WO2006019023A1 WO 2006019023 A1 WO2006019023 A1 WO 2006019023A1 JP 2005014652 W JP2005014652 W JP 2005014652W WO 2006019023 A1 WO2006019023 A1 WO 2006019023A1
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- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- modified
- optical disk
- resin composition
- Prior art date
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- 230000003287 optical effect Effects 0.000 title claims abstract description 109
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 98
- 239000000758 substrate Substances 0.000 claims abstract description 57
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- 150000005846 sugar alcohols Polymers 0.000 description 3
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- NIDZWWNRMZPMLN-UHFFFAOYSA-N [1,4,4-tris(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCC(CO)(CO)CC1 NIDZWWNRMZPMLN-UHFFFAOYSA-N 0.000 description 1
- HTMMMSIQFWMMIJ-UHFFFAOYSA-N [3-[2,2-dimethyl-3-(6-prop-2-enoyloxyhexanoyloxy)propanoyl]oxy-2,2-dimethylpropyl] 6-prop-2-enoyloxyhexanoate Chemical compound C=CC(=O)OCCCCCC(=O)OCC(C)(C)COC(=O)C(C)(C)COC(=O)CCCCCOC(=O)C=C HTMMMSIQFWMMIJ-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
Definitions
- the present invention relates to an ultraviolet curable adhesive resin composition used for bonding optical disk substrates, particularly when bonding two optical disk substrates used for digital video disks (hereinafter referred to as DVDs).
- the present invention relates to an ultraviolet curable adhesive resin composition that is cured by ultraviolet to near ultraviolet light and is useful for bonding two optical disk substrates, and an optical disk bonded therewith.
- DVDs that are currently in practical use are DVD-ROM types on which information such as movies have been recorded since the manufacture of the disc, and no information is recorded at the time of manufacture, and are consumed in the dye recording layer and the inorganic recording layer.
- the DVD-ROM type information is recorded on the substrate, and in the configuration of the recording layer, the recording layer is a single-sided reading layer with a recording capacity of approximately 5 GB DVD-5, and the single-sided reading layer is recorded with two layers.
- the recording layer is a single-sided reading layer with a recording capacity of approximately 9 GB, 9 DVDs with double-sided reading and recording capacity of 10 GB, and DVDs with double-sided reading with a recording capacity of approximately 18 GB.
- DVD-9 is the current mainstream because it has a recording capacity capable of recording about 2.5 hours of movies. Since DVD-9 is a single-sided reading two-layer system, a total reflection film and a semitransparent reflection film are used. However, an aluminum alloy is used as the total reflection film, and gold is used as the semitransparent reflection film. Unlike a total reflection film, a semi-transparent reflection film has to be thinned because it must transmit a laser, but gold, which is a relatively stable material that is easy to make a thin film, has been used.
- DVD—R DVD + R
- DVD—RW DVD + RW
- DVD—RAM DVD—RAM
- the mainstream DVD-R, DV D-RAM, DVD + R, and DVD + RW are single-sided single-layer types, and are used by bonding together a polycarbonate substrate and an optical disc substrate having a recording layer and a reflective film layer.
- a material for the reflective film layer silver or silver alloy having a high reflectance is used with a certain thickness.
- the new format has a type with two layers of a semi-transparent reflection film and a total reflection film layer as in the DVD-9 system, and silver or silver alloy having high reflectivity is used as the material of the reflection film layer. Yes.
- Patent Document 1 discloses an alicyclic structure for use in the production of a bonded optical disk using a translucent reflective film of silver or a silver alloy.
- An ultraviolet curable adhesive resin composition for optical discs containing (meth) acrylate as a main component is described, and it is shown that durability is improved.
- the UV curable adhesive resin composition for optical discs mainly composed of (meth) acrylate having an alicyclic structure the semi-transparent reflection film or the total reflection film and the adhesive cured product are adhered to each other. There was a problem of weakness!
- Patent Documents 2, 3, 4, 5, 6 and 7 mainly contain urethane (meth) acrylate for use in the production of bonded optical disks using a translucent reflective film of silver or silver alloy.
- An ultraviolet curable adhesive resin composition for optical discs is described, which has been shown to improve durability.
- Patent Document 8 describes an ultraviolet curable adhesive resin composition for optical discs mainly composed of epoxy (meth) acrylate, and has been shown to suppress the generation of bubbles. Further, the adhesiveness between the translucent reflective film or the total reflective film and the cured adhesive is disclosed.
- Patent Document 1 Japanese Unexamined Patent Publication No. 2001-167478
- Patent Document 3 Japanese Unexamined Patent Publication No. 2002-114949
- Patent Document 4 Japanese Patent Laid-Open No. 2002-155245
- Patent Document 5 JP 2002-256228
- Patent Document 6 Japanese Patent Laid-Open No. 2002-265885
- Patent Document 7 JP 2002-265886 A
- Patent Document 8 JP 2004-175866 A
- the present invention uses a conventional gold translucent reflective film in a bonded optical disk obtained by bonding an optical disk substrate having a total reflection film or a semitransparent reflection film made of silver or a silver alloy.
- an adhesive resin composition that can provide high durability equivalent to that of a bonded optical disc, and that is excellent in adhesion between the reflective film and the adhesive cured product, and between the polycarbonate substrate and the adhesive cured product.
- the inventors of the present invention have a specific composition even when laminating an optical disk having a total reflection film or a semitransparent reflection film having the same strength as silver or a silver alloy. It has been found that the ultraviolet curable resin composition has excellent durability and adhesion, and the present invention has been completed.
- the present invention provides:
- (1) Contains bisphenol type epoxy (meth) acrylate (A), di (meth) acrylate (B) and photoinitiator (C), and di (meth) acrylate (B) has an adipate structure.
- Alkylene oxide-modified neopentyldalicol di (meth) attareitol toy compound (B3) is a neopentyl glycol ditalate with 2 moles of propylene oxide, ethylene oxide-modified neopentyl glycol diatariate.
- the urethane (meth) acrylate (E) further contains (1), and (6) the ultraviolet curable adhesive resin composition according to item 1 of
- Durability can be obtained, and furthermore, high adhesion strength between the metal reflection film and the cured adhesive and between the polycarbonate substrate and the cured adhesive can be obtained. Due to its high adhesion strength, the optical disk that is bonded will not peel off even if the DVD is used repeatedly.
- the resin composition for adhesion of the present invention contains a bisphenol type epoxy (meth) acrylate (A), di (meth) acrylate (B) and a photopolymerization initiator (C).
- the (meth) acrylate refers to meta acrylate or ate.
- V (di (meth) atalylate (B) is a di (meth) atalylate (B-1) having an adipate structure, and a di (meth) atalylate (B) having a force prolatatone modified structure.
- the bisphenol type epoxy (meth) acrylate (A) contained in the composition of the present invention is a reaction of bisphenol type epoxy resin and (meth) acrylic acid under conditions such as those described below.
- (Epoxy (meth) acrylate) obtained by the following.
- the bisphenol type epoxy resin include bisphenol A type epoxy resin (for example, EPA-37 manufactured by Nippon Kayaku, Epicoat 802, 1001, 1004, etc. manufactured by Japan Epoxy Resin Co., Ltd.) or bisphenol F type epoxy. Resin (for example, Epoxy Coat 400 1P, 4002P, 4003P, etc.
- the bisphenol type epoxy (meth) acrylate (A) contained in the composition of the present invention contains, for example, (meth) acrylic acid with respect to 1 mol of the epoxy group of the bisphenol type epoxy resin. It can also be obtained by reacting at a ratio of 9 to 1.5 equivalents, more preferably 0.995-1. In this reaction, the reaction temperature is preferably 80 to 120 ° C., and the reaction time is about 10 to 35 hours. In order to accelerate the reaction, it is preferable to use a catalyst such as triphenylphosphine, triethanolamine, tetraethylammonium chloride and the like. Further, during the reaction, a polymerization inhibitor (for example, paramethoxyphenol, methylnodroquinone, etc.) can be used to prevent polymerization.
- a polymerization inhibitor for example, paramethoxyphenol, methylnodroquinone, etc.
- the bisphenol type epoxy (meth) atrelate (A) can be used singly or in combination of two or more at any ratio.
- the content of the bisphenol type epoxy (meth) acrylate (A) in the ultraviolet curable resin composition is usually 1 to 70% by weight, preferably 5 to 50% by weight.
- the molecular weight of bisphenol type epoxy (meth) acrylate (A) is preferably 500 to 10,000!
- Di (meth) attairele HB-1) having an adipate structure contained in the adhesive resin composition of the present invention has a cured film that is soft and strong due to the effect of a flexible adipate site.
- the metal reflective film such as silver, silver alloy, or aluminum and the cured adhesive, and the adhesion between the polycarbonate substrate and the cured adhesive are improved.
- the di (meth) acrylate (B-1) having an adipate structure is obtained by a dehydration condensation reaction between a diol having an adipate structure and (meth) acrylic acid.
- a diol having an adipate structure for example, bis (atalyloxyneopentildaricol) adipate or a modified product thereof (for example, force prolatatatone modified bis (ataryloxynepentyldaricol) adipate, polyether modified bis (ataryloxynepentyldaricol)) Adipate, etc.), and bis (ataryloxynepentyldaricol) adipate is preferable.
- the di (meth) attalylate (B-2) having a force prolatatone modified structure contained in the resin composition for bonding of the present invention has silver, silver alloy or aluminum due to the effect of the force prolatatone modified structure. It has a function of improving the adhesion between the metal reflective film such as a film and the cured adhesive, and between the polycarbonate substrate and the cured adhesive.
- the di (meth) acrylate (B-2) having a force prolatatone modified structure is obtained by a dehydration condensation reaction between a diol having a force prolatatone modified structure and (meth) acrylic acid.
- force prolatatone-modified hydroxybivalic acid neopentyldaricol ditalylate for example, KAYARAD HX-220, KAYARAD HX-660 manufactured by Nippon Kayaku Co., Ltd.
- ⁇ of hydrogenated bisphenol A -Di (meth) attalylate of products with force prolatataton
- ⁇ - force of cyclohexane-1,4-dimethanol and di (meth) acrylate of products with force prolatataton.
- Alkylene oxide modified neopentyldaricoldi (meth) attareito toy compound (B-3) and alkylene oxide modified 1,6-hexane Diol Di (meth) attareito toy compound (B-4) has the function of improving adhesion to metal reflective films such as silver, silver alloys and aluminum due to the flexibility effect of alkylene oxide. is there.
- alkylene oxide-modified neopentyl glycol di (meth) acrylate compound (B-3) include ethylene oxide-modified neopentyldaricol di (meth) acrylate, propylene oxide-modified neopentyldaricol. Di (meta) attalate, etc. Can be mentioned.
- the amount of adhesion of alkylene oxide is preferably 1 to 6 mol, more preferably 2 to 4 mol.
- Specific examples of 4) include ethylene oxide-modified 1,6 hexanediol di (meth) acrylate, propylene oxide-modified 1,6 hexanediol di (meth) acrylate.
- the amount of alkylene oxide added in these modifications is preferably 1 to 6 mol, more preferably 2 to 4 mol.
- these components (B) can be used alone or in admixture of two or more in any proportion.
- the content of the component (B) in the ultraviolet curable resin composition is usually 5 to 90% by weight, preferably 10 to 85% by weight.
- the adhesive resin composition of the present invention includes a (meth) acrylate monomer other than the component (B).
- component ( ⁇ ′) can be added.
- component ( ⁇ ′) that can be used are monofunctional monomers such as tricyclodecane (meth) acrylate, dicyclopentagenoxychetyl (meth) acrylate, dicyclopental (meta ) Atalylate, isobornyl (meth) atrelate, adamantyl (meth) atarylate, phenoxychetyl (meth) atalylate, phenoxypolyethylene glycol (meth) attalylate, benzyl (meth) attalylate, tetrahydrofurfuryl (meth) atalyte , Morpholine (meth) acrylate, ferulglycidyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, stearyl (meth) acrylate , Isooctyl
- the component ( ⁇ ') is a polyfunctional (meth) acrylate monomer having two or more (meth) acrylate groups in the molecule, for example, cyclohexane-1,4-dimethanol di ( Meta) Atalylate, Cyclohexane-1,3 Dimethanol di (meth) atarylate, Tricyclodecane dimethylol di (meth) atarylate (for example, KAYARAD R—684, Tricyclo, manufactured by Nippon Gyaku Co., Ltd.) Decanedimethylol diatalylate, etc.), hydroxypivalaldehyde-modified trimethylolpropane di (meth) acrylate, hydrogenated bisphenol ⁇ polyethoxy di (meth) acrylate, hydrogenated bisphenol A polypropoxydi (meth) attaly Rate, hydrogenated Bisphenol F polyethoxydi (meth) acrylate, cyclohexanone 1,4-dimethanol polyethoxy
- these (meth) acrylate monomers ( ⁇ ') can be used singly or in combination of two or more in any proportion.
- the content of the (meth) acrylate monomer ( ⁇ ′) in the ultraviolet curable resin composition of the present invention is usually 0 to 85% by weight, preferably 10 to 60% by weight.
- Examples of the photopolymerization initiator (C) contained in the adhesive resin composition of the present invention include (i): 1-hydroxycyclohexyl phenol ketone, 2,2-dimethoxy-2-phenol. 1- [4- (2-hydroxyethoxy) monophenyl] 2-hydroxy-1-2-methyl 1-propane-1-one or 2-methyl- [4 (methylthio) phenol 2) Morpholino 1 propanone, 2 Benjirou 2 Dimethylamino 1 (4 morpholinophenol) Butane 1 ON, etc.
- the content of these photopolymerization initiators (C) in the adhesive resin composition of the present invention is usually 0.5 to 20% by weight, preferably 1 to 10% by weight.
- the amount is usually 0.005 to 5% by weight, preferably 0.01 to 3% by weight.
- amines and the like that can serve as photopolymerization initiation assistants can be used in combination with the above photopolymerization initiator.
- examples of amines that can be used include benzoic acid 2-dimethylaminoethyl ester, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, and p-dimethylaminobenzoic acid isoamyl ester.
- the content in the adhesive resin composition of the present invention is usually 0.005 to 5% by weight, preferably 0.01 to 3% by weight. .
- Phosphoric acid (meth) acrylate (D) can be added to the adhesive resin composition of the present invention, if necessary. Phosphoric acid (meth) acrylate (D) improves the adhesion between aluminum, silver or a silver alloy and the cured adhesive, but may corrode the metal film and its usage is limited.
- the phosphoric acid (meth) acrylate (D) that can be contained in the adhesive resin composition of the present invention is a monoester or a diester as long as it is a (meth) acrylate having a phosphate ester skeleton.
- a monoester or a diester as long as it is a (meth) acrylate having a phosphate ester skeleton.
- examples thereof include ethylene oxide-modified phenoxylated phosphate (meth) acrylate, ethylene oxide-modified butoxylated phosphate (meth) acrylate, ethylene oxide modified octyloxylated phosphate (meta) ) Acrylate, ethylene oxide-modified di (meth) acrylate, ethylene oxide-modified tri (meth) acrylate, etc.
- PM-2 ethylene oxide manufactured by Nippon Gyaku Co., Ltd. (Xoxide modified dimetatalyl phosphate).
- ethylene oxide-modified dimetatalyl phosphate is preferably used.
- Phosphoric acid (meth) acrylate (D) may be used alone or in combination of two or more in any proportion. Phosphoric acid (meth) acrylate (D) When contained in the composition, the content is usually 0.005 to 5% by weight, preferably 0.05 to 3% by weight.
- the adhesive resin composition of the present invention can include urethane (meth) acrylate (E) if necessary.
- Urethane (meth) acrylate (E) was bonded using an adhesive containing urethane (meth) acrylate (E) by further improving the adhesion and improving the flexibility of the adhesive hardened film. There is a function of reducing warpage of the bonded optical disk.
- the urethane (meth) acrylate (E) used as necessary in the present invention can be obtained by reacting a polyhydric alcohol, an organic polyisocyanate, and a hydroxy (meth) ate tale toy compound.
- examples of the polyhydric alcohol include neopentyl glycol, 3-methylolene 1,5-pentanediol, ethylene glycolol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, Aliphatic polyols such as methylolpropane, pentaerythritol, tricyclodecane dimethylol, bis (hydroxymethyl) cyclohexane, these aliphatic polyols and polybasic acids (for example, succinic acid, phthalic acid, hexahydrophthalic anhydride) Polyester polyols obtained by reaction with acid, terephthalic acid, adipic acid, azelaic acid, tetrahydrophthalic anhydride, etc.), prolacton alcohol, polycarbonate polyol obtained by reaction of aliphatic polyol with ⁇ -prolacton (E.g.,
- Polycarbonate diol obtained by the reaction of hexanediol and diphenyl carbonate
- polyether polyol eg, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide modified bisphenol ⁇ etc.
- the organic polyisocyanate includes, for example, isophorone diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, xylene diisocyanate, diphenylenomethane 4, 4'-dioxide. And isocyanato or dicyclopenta-noreoisocyanate.
- examples of the hydroxy (meth) attareito toy compound include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylol cyclohexyl mono (Meth) Atarylate, Hydroxycaprolataton (Meth) Talirate and the like can be mentioned.
- Urethane (meth) acrylate (E) can be obtained, for example, by reacting as follows. That is, an organic polyisocyanate is mixed with polyhydric alcohol so that the isocyanate group is preferably 1.1 to 2.0 equivalents per equivalent of hydroxyl group, and the reaction temperature is preferably 70 to 90 ° C. To produce a urethane oligomer. Next, a hydroxy (meth) attareito toy compound is mixed so that the hydroxyl group is preferably 1 to 1.5 equivalent per equivalent of isocyanate group of the obtained urethane oligomer, preferably at 70 to 90 ° C. When reacted, the desired urethane (meth) acrylate (E) is obtained. The molecular weight of urethane (meth) acrylate (E) is ⁇ .
- one or more urethane (meth) acrylates ( ⁇ ) can be mixed and used in an arbitrary ratio.
- polyether urethane acrylate is preferred.
- urethane (meth) acrylate ( ⁇ ) is contained in the ultraviolet curable resin composition, the content thereof is usually 1 to 50% by weight, preferably 5 to 40% by weight.
- the molecular weight is a weight average molecular weight
- the measuring method is based on a light scattering method
- An antioxidant which may further contain an acid proof agent (F) in the adhesive resin composition of the present invention.
- (F) examples include hindered phenol compounds, amine compounds, compounds and
- Mention may be made of koji or linny compounds.
- hindered phenol compound as the antioxidant (F) include 2, 6 tert-butyl-4-methylphenol, 2, 2'-methylene bis (4-methyl-6-tert-butylphenol), 2,2'-methylene monobis (4 ethyl 6-tert-butylphenol), 4,4'-thiobis (3-methyl-6-tert butylphenol), 4,4'-butylidenebis (3-methyl-6-tert) Butylphenol), triethylene glycol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenol) propionate], 1,6-mono-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenol) ) Pionate], 2, 2 thiodiethylenebis [3- (3,5 ditert-butynole 4-hydroxyl) propionate], octadecyl 3- (3,5-di-tertbutyl-4 -Hydroxyphenol) prop
- amine compound as the antioxidant (F) include octyl diphenylamine (eg, 4,4'-dioctyldiphenylamine), 4, 4'- Examples include dicumyl diphenylamine, 6 ethoxy 2,2,4-trimethylolene 1,2 dihydroquinoline, 2,2,4 trimethylol 1,2-dihydroquinoline polymer, and the like.
- Specific examples of the iow compound as the antioxidant (F) include 2 mercaptobenzimidazole, 2,4 bis (octylthiomethyl) o-cresol, 2,4 bis (n-octylthio)- 6- (4-Hydroxy-3,5 di-tert-butyla-lino) 1, 3, 5 Triazine, Adekastab AO-412S (Asahi Denki Kogyo Co., Ltd.) and the like can be mentioned.
- Specific examples of the phosphorus compound as the antioxidant (F) include tris (nonylated phenyl) phosphate, ADK STAB PER-4C (Asahi Denka Kogyo Co., Ltd.), ADK STAB 260 (Asahi Denka) Kogyo Co., Ltd.), ADK STAB 522A (Asahi Denso Kogyo Co., Ltd.), and the like.
- antioxidants (F) particularly preferred are hindered phenol compounds. These antioxidants can be used alone or in combination of two or more.
- the content thereof is usually 0.005 to 10% by weight, preferably 0.01 to 5% by weight.
- the adhesive resin composition of the present invention may include a polyester-based, polycarbonate-based, polyacrylic-based, polyurethane-based, or polybule-based resin as a polymer.
- organic solvents silane coupling agents, polymerization inhibitors, leveling agents, antistatic agents, surface lubricants, fluorescent brighteners, light stabilizers (for example, hindered amine compounds), fillers, etc. Additives may be added.
- the adhesive resin composition of the present invention can be obtained by mixing and dissolving the aforementioned components at room temperature to 80 ° C, and if necessary, impurities may be removed by an operation such as filtration.
- the ultraviolet ray curable resin composition of the present invention has a viscosity at 25 ° C in the range of 100 to 5000 mPa's in consideration of applicability. It is preferable to appropriately adjust the compounding ratio of the components so as to be in the range.
- the adhesive resin composition of the present invention is a bonded optical disk adhesive, particularly an optical disk substrate in which one or both of the bonded optical disk substrates have a total reflection film or a semitransparent reflection film of silver or a silver alloy.
- the composition is optically discriminated by any method such as spin coating, 2P method, roll coating method, screen printing method, etc., so that the adhesive layer has a film thickness of ⁇ 100 m.
- the adhesive layer is cured and bonded by irradiating from one or both sides with ultraviolet to near-ultraviolet rays (wavelength around 250 to 400 nm).
- the irradiation dose is about 50 to: LOOOmjZcm 2 is particularly preferred, and is preferably about 100 to 700 mjZ cm 2 .
- any light source may be used as long as it is a lamp that irradiates ultraviolet to near ultraviolet rays.
- a low-pressure, high-pressure or ultrahigh-pressure mercury lamp, a metal nitride lamp, a (pulse) xenon lamp, or an electrodeless lamp can be used.
- the optical disk substrate a known one, that is, a material using gold as a translucent reflective film, a material using silicon, a silicon compound, silver and a silver alloy, or the like can be used.
- the composition of the present invention is suitable for an optical disk using silver or a silver alloy as a total reflection film or a semitransparent reflection film.
- a bonded optical disk which is an optical disk substrate having an alloy total reflection film or a semitransparent reflection film is also included.
- the optical disc is DVD-ROM (DVD-5, DV D-10, DVD-9, DVD-14, DVD-18), DVD-R ⁇ DVD + R ⁇ DVD-RW, DVD + RW, DVD-RAM, DVD — R single-sided double-layer, DVD + R single-sided double-layer, DV D—RW single-sided double-layer, DVD + R single-sided double-layer DVD, etc.
- the silver alloy translucent reflective film substrate and the aluminum alloy total reflective film substrate were bonded by the following 1-4, and the DVD-9 type of the present invention A bonded optical disk was produced. Further, using the resin composition for bonding of the present invention, a silver reflective film substrate and a polycarbonate (hereinafter referred to as PC) substrate were bonded by the following procedures 5 to 8 to produce a DVD + R type bonded optical disk.
- PC polycarbonate
- the silver alloy translucent reflective film substrate was prepared by using 0.6mm thick PC substrate and silver alloy TTP-55A made by Target Technology Co., Ltd., and vapor deposition (hereinafter referred to as sputtering) to an average lOnm film thickness. .
- the aluminum alloy total reflection film substrate was produced by sputtering a 0.6 mm thick PC substrate using an aluminum alloy made by Unaxis Co., Ltd. to an average film thickness of 45 nm.
- the DVD disc has a silver alloy translucent reflection film on the upper side and an aluminum alloy total reflection film on the lower side. 5.
- the silver reflective film substrate has pits for DVD + R formed.
- a 0.6 mm thick PC substrate was prepared by spin coating the azo dye recording layer and dried at 80 ° C for 15 minutes. Sputters were made using silver from Unaxis Co., Ltd. to an average film thickness of lOOnm.
- the adhesive resin composition of the present invention was cured by irradiating 8 shots at 1800 V from the upper side to bond the disk substrate.
- the direction of the DVD disc is the upper PC board and the lower silver reflective film board.
- Example 1 the resin composition for bonding of the present invention was prepared with the composition shown in Table 1, and subsequently, a bonded optical disk was prepared in the same manner as in Example 1.
- Example 1 the resin composition for bonding of the present invention was prepared with the composition shown in Table 1, and subsequently, a bonded optical disk was prepared in the same manner as in Example 1.
- an ultraviolet curable resin composition that does not contain a di (meth) acrylate compound (B-1) having an adipate structure and contains a (meth) acrylate compound having an alicyclic structure was fabricated in substantially the same manner as in Example 1, and then a bonded optical disk was fabricated in the same manner as in Example 1.
- Viscosity (mPa.s 25 ° C) 560 570 540 540 The components shown in abbreviations in Table 1 are as follows. The numbers represent parts. EPA-37: Bisphenol A diglycidyl ether diatalylate, Nippon Kayaku Co., Ltd.
- R-526 Bis (Atalyloxyneopentyldaricol) adipate, Nippon Gyaku Co., Ltd.
- Irgacure 907 2-Benzyl-2-dimethylamino 1- (4 morpholinophenol) -butane 1-one , Chinoku 'Specialty Chemicals Co., Ltd.
- Irgacure 184 1-Hydroxycyclohexyl phenyl ketone, manufactured by Ciba 'Specialty' Chemicals Co., Ltd.
- FA—512A dicyclopentagenoxychetyl talylate, manufactured by Hitachi Chemical Co., Ltd.
- PM-2 ethylene oxide-modified dimetathalyl phosphate, manufactured by Nippon Gyaku Co., Ltd.
- R-684 Tricyclodecane dimethylol diatalylate, manufactured by Nippon Gyaku Co., Ltd.
- Example 5 the viscosity of the adhesive resin composition of the present invention was 530 mPa ⁇ s (measured with a B-type viscometer manufactured by Toki Sangyo Co., Ltd.) at 25 ° C. Subsequently, a bonded optical disk was produced in the same manner as in Example 1.
- Example 5 the viscosity of the adhesive resin composition of the present invention was 530 mPa ⁇ s (measured with a B-type viscometer manufactured by Toki Sangyo Co., Ltd.) at 25 ° C. Subsequently, a bonded optical disk was produced in the same manner as in Example 1.
- Example 5 the viscosity of the adhesive resin composition of the present invention was 530 mPa ⁇ s (measured with a B-type viscometer manufactured by Toki Sangyo Co., Ltd.) at 25 ° C. Subsequently, a bonded optical disk was produced in the same manner as in Example 1.
- Example 5 the visco
- Example 4 In the same manner as in Example 4, a resin composition for bonding according to the present invention was produced with the composition shown in Table 2, and subsequently, a bonded optical disk was produced in the same manner as in Example 1.
- Example 4 In the same manner as in Example 4, a resin composition for bonding according to the present invention was produced with the composition shown in Table 2, and subsequently, a bonded optical disk was produced in the same manner as in Example 1.
- an ultraviolet-curing compound containing a (meth) atalylate compound having a cycloaliphatic structure without a di (meth) atalytoi compound (B-2) having a force prolatatone modified structure As shown in the composition of Table 2, an ultraviolet-curing compound containing a (meth) atalylate compound having a cycloaliphatic structure without a di (meth) atalytoi compound (B-2) having a force prolatatone modified structure.
- a compounded rosin composition was produced in substantially the same manner as in Example 4, and subsequently bonded in the same manner as in Example 1 to produce an optical disk.
- HX-220 Power Prolatatone Modified Hydroxybivalate Neopentyl Glycol Ditalate, Nippon Kayaku Co., Ltd.
- Irgacure 907 2-Benzyl-2-dimethylamino 1- (4 morpholinophenol) -butane 1-one, Chinoku's made by Specialty Chemicals
- Irgacure 184 1-Hydroxycyclohexyl phenyl ketone, manufactured by Ciba 'Specialty' Chemicals Co., Ltd.
- FA—512A dicyclopentagenoxychetyl talylate, manufactured by Hitachi Chemical Co., Ltd.
- PM-2 ethylene oxide-modified dimetathalyl phosphate, manufactured by Nippon Gyaku Co., Ltd.
- R-684 Tricyclodecane dimethylol diatalylate, manufactured by Nippon Gyaku Co., Ltd.
- the viscosity of the ultraviolet curable resin composition of the present invention was 500 mPa 's (measured with a B-type viscometer) at 25 ° C.
- a bonded optical disk was prepared by bonding the ultraviolet curable resin composition by the following methods 1 to 4.
- the silver reflective film substrate was coated with an azo dye on a 0.6 mm thick PC substrate transferred with a DVD + R stamper, and pure silver was sputtered to form a recording layer.
- a pair of 0.6 mm PC boards was prepared by molding.
- An adhesive was supplied in a circular shape of 2.5 g on the inner circumference of a 0.6 mm PC substrate.
- a DVD substrate with a silver reflective film sputtered is placed on a PC substrate supplied with an adhesive so that the sputter surface is down, and spin coated at a speed of 2000 rpm for 4 seconds. Lamination was done so that the distance was 5 to 65 m.
- the optical disk laminating apparatus used was a global experimental apparatus.
- PC surface side force Xenon flash lamp was used and cured and adhered by irradiating 8 shots at 60J.
- Example 7 In the same manner as in Example 7, a resin composition for bonding according to the present invention was prepared with the composition shown in Table 3. Subsequently, in the same manner as in Example 7, a bonded optical disk was prepared.
- Example 7 the adhesive resin composition of the present invention was prepared with the composition shown in Table 3, and then In the same manner as in Example 7, a bonded optical disk was produced.
- NPGDA2PO Propylene oxide modified neopentyl glycol ditalylate, manufactured by Daiichi Kogyo Seiyaku
- R-684 Tricyclodecane dimethylol diatalylate, manufactured by Nippon Kayaku Co., Ltd.
- R-128H Phenyldaricidyl acrylate, manufactured by Nippon Kayaku Co., Ltd.
- Irgacure 184 1-Hydroxycyclohexyl phenyl ketone, photopolymerization initiator manufactured by Ciba 'Specialty Chemical Co., Ltd.
- Irgacure 907 2-methyl- [4- (methylthio) phenol] -2 morpholino 1 propanone, photopolymerization initiator manufactured by Ciba Specialty Chemicals
- the viscosity of the ultraviolet curable resin composition of the present invention was 500 mPa ⁇ s (measured with a B-type viscometer) at 25 ° C. Subsequently, a bonded optical disk was produced in the same manner as in Example 7.
- Example 9 a resin composition for bonding according to the present invention was produced with the composition shown in Table 4, and subsequently, a bonded optical disk was produced in the same manner as in Example 7.
- Example 9 an adhesive resin composition having the composition shown in Table 4 was prepared. Subsequently, in the same manner as in Example 7, a bonded optical disk was prepared.
- R—684 Tricyclodecane dimethylol diatalylate, manufactured by Nippon Kayaku Co., Ltd.
- R—128H phenyldaricidyl acrylate, manufactured by Nippon Kayaku Co., Ltd.
- Irgacure 184 1-Hydroxycyclohexyl phenyl ketone, Ciba 'Specialte Photopolymerization initiator manufactured by i-Chemical
- Irgacure 907 2-methyl- [4 (methylthio) phenol] 2 morpholino 1 propanone, photopolymerization initiator manufactured by Ciba Specialty Chemicals
- Example 1 to Example 6 or Comparative Example 1 to Comparative Example 2 were evaluated by the following methods.
- the bonded optical disk of the present invention and the bonded optical disk of the comparative example were left in an environment of 80 ° C. and 85% RH (relative humidity) for 500 hours and 700 hours.
- the state of the reflective film was observed visually.
- the observation results are shown in Table 5 and Table 6 by the following notation.
- the evaluation after 500 hours shows no change in the state of the total reflection film and the semitransparent reflection film, but the evaluation after 700 hours shows no change in the total reflection film and the semitransparent reflection film. Many discoloration or pinholes.
- the bonded optical disk of the present invention and the bonded optical disk of the comparative example were left in an environment of 80 ° C. and 85% RH for 700 hours.
- DVD data signal measuring device AECO DVD-2000 was used to measure and evaluate the electrical signal (system jitter, PI error) of the bonded optical disc after the durability test.
- System jitter and PI error are one of the electrical signals of optical discs, and the higher these values, the worse the data on the bonded optical disc.
- the bonded optical disk of the present invention and the bonded optical disk of the comparative example were left in an environment of 80 ° C. and 85% RH for 480 hours.
- DVD data signal measuring device DVD made by AUDIO DEV.
- Tilt jitter, PISum8 is one of the electrical signals of the optical disk. The higher the value, the more the data on the bonded optical disk deteriorates.
- the adhesive strength between the reflective film of the bonded optical disk of the present invention and the bonded optical disk of the comparative example and the optical disk substrate was evaluated. The evaluation is based on observing the state of the reflective film after peeling off the bonded optical disk with a finger and making a small cut with a cutter at the bonding interface of the bonded optical disk. ⁇ 'Excellent adhesion, and more than half of the translucent reflective film or total reflective film was peeled off from the polycarbonate substrate during peeling.
- the adhesive strength between the reflective film of the bonded optical disk of the present invention and the bonded optical disk of the comparative example and the optical disk substrate was evaluated.
- the evaluation is based on observing the state of the reflective film after peeling off the bonded optical disk with a finger and making a small cut with a cutter at the bonding interface of the resulting bonded optical disk with a cutter.
- ⁇ ⁇ 'Excellent adhesion, and more than half of the total reflection film peels off from the interface with the dye layer when peeling.
- ⁇ ⁇ 'Adhesiveness was insufficient, and only a part of the total reflection film peeled off the interfacial force with the dye layer during peeling.
- Example 7 to Example 10 or Comparative Example 3 to Comparative Example 4 were evaluated by the following methods.
- the obtained bonded optical disk was left in an environment of 80 ° C. and 85% RH for 480 hours.
- the state of the reflective film was observed visually.
- the observation results were written as follows and shown in Table 9 and Table 10.
- the resulting bonded optical disk was recorded and recorded at full speed at 8x speed using a Plextor DVD writer PX-708A.
- the durability test was conducted in an environment of 80 ° C and 85% RH for 480 hours.
- DVDCATS SA300 a DVD data signal measuring device manufactured by AudioDev, the electrical signal of the bonded optical disk after the durability test was evaluated.
- Tilt jitter PISum8 is one of the electrical signals on the optical disc. The higher the value, the more the data on the bonded optical disc deteriorates.
- the adhesion strength between the surface of the polycarbonate and the total reflection film of the obtained bonded optical disk and the adhesive was evaluated. Make a small incision of about 5 mm in depth with a cutter at the bonding interface of the resulting bonded optical disk. The cutting force was peeled off with a finger, and the state of the reflective film after peeling was observed.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05770517A EP1780251A1 (en) | 2004-08-19 | 2005-08-10 | Adhesive composition for optical disk, cured product and article |
US11/660,013 US20080152857A1 (en) | 2004-08-19 | 2005-08-10 | Adhesive Compositon for Optical Disk, Cured Product and Article |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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JP2004-239972 | 2004-08-19 | ||
JP2004239958 | 2004-08-19 | ||
JP2004-239958 | 2004-08-19 | ||
JP2004239972 | 2004-08-19 | ||
JP2004-264391 | 2004-09-10 | ||
JP2004264401 | 2004-09-10 | ||
JP2004-264401 | 2004-09-10 | ||
JP2004264391 | 2004-09-10 |
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WO2006019023A1 true WO2006019023A1 (ja) | 2006-02-23 |
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PCT/JP2005/014652 WO2006019023A1 (ja) | 2004-08-19 | 2005-08-10 | 光ディスク用接着剤組成物、硬化物および物品 |
Country Status (4)
Country | Link |
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US (1) | US20080152857A1 (ja) |
EP (1) | EP1780251A1 (ja) |
TW (1) | TW200621927A (ja) |
WO (1) | WO2006019023A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2040259A1 (en) * | 2006-07-10 | 2009-03-25 | Nippon Kayaku Kabushiki Kaisha | Ultraviolet-curable resin composition and use thereof |
Families Citing this family (6)
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WO2007142229A1 (ja) * | 2006-06-07 | 2007-12-13 | Nippon Kayaku Kabushiki Kaisha | 光ディスク及びそのための紫外線硬化型樹脂組成物 |
TWI418603B (zh) * | 2007-03-16 | 2013-12-11 | Mitsubishi Gas Chemical Co | 光穿透型電磁波屏蔽積層體及其製造方法、光穿透型電波吸收體,以及接著劑組成物 |
WO2014077589A1 (ko) * | 2012-11-13 | 2014-05-22 | 주식회사 케이오씨솔루션 | 에폭시 아크릴계의 고굴절 광학재료용 중합성 조성물 및 에폭시 아크릴계 고굴절 광학재료의 제조방법 |
KR20160022815A (ko) | 2013-06-24 | 2016-03-02 | 다이니폰 인사츠 가부시키가이샤 | 수지 조성물 |
CN103952086B (zh) * | 2014-04-29 | 2015-06-10 | 烟台德邦科技有限公司 | 一种紫外光固化胶及其制备方法 |
CN104610898A (zh) * | 2014-12-31 | 2015-05-13 | 东莞金杯印刷有限公司 | 一种uv覆膜胶水、应用uv覆膜胶水的覆膜机及其处理方法 |
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JP2002030260A (ja) * | 2000-07-14 | 2002-01-31 | Toagosei Co Ltd | 紫外線硬化型接着剤組成物及び感熱孔版印刷原紙 |
JP2004011386A (ja) * | 2002-06-11 | 2004-01-15 | Sekisui Chem Co Ltd | 建築内装材の接着方法及びアクリル系感圧接着シート |
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US7052756B2 (en) * | 2001-05-17 | 2006-05-30 | Nippon Kayaku Kabushiki Kaisha | Adhesive for optical disk and optical disk |
-
2005
- 2005-08-10 EP EP05770517A patent/EP1780251A1/en not_active Withdrawn
- 2005-08-10 US US11/660,013 patent/US20080152857A1/en not_active Abandoned
- 2005-08-10 WO PCT/JP2005/014652 patent/WO2006019023A1/ja not_active Application Discontinuation
- 2005-08-17 TW TW094128075A patent/TW200621927A/zh unknown
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JPH0433915A (ja) * | 1990-05-29 | 1992-02-05 | Ajinomoto Co Inc | 一液型エポキシ樹脂組成物 |
JPH0931416A (ja) * | 1995-04-28 | 1997-02-04 | Nippon Kayaku Co Ltd | 紫外線硬化型接着剤組成物、硬化物、物品及び接着方法 |
JP2002030260A (ja) * | 2000-07-14 | 2002-01-31 | Toagosei Co Ltd | 紫外線硬化型接着剤組成物及び感熱孔版印刷原紙 |
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EP2040259A1 (en) * | 2006-07-10 | 2009-03-25 | Nippon Kayaku Kabushiki Kaisha | Ultraviolet-curable resin composition and use thereof |
EP2040259A4 (en) * | 2006-07-10 | 2010-09-22 | Nippon Kayaku Kk | UV-CURABLE RESIN COMPOSITION AND ITS USE |
US8192821B2 (en) | 2006-07-10 | 2012-06-05 | Nippon Kayaku Kabushiki Kaisha | Ultraviolet-curable resin composition and use thereof |
TWI480290B (zh) * | 2006-07-10 | 2015-04-11 | Nippon Kayaku Kk | 紫外線硬化型樹脂組成物及其用途 |
Also Published As
Publication number | Publication date |
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TW200621927A (en) | 2006-07-01 |
US20080152857A1 (en) | 2008-06-26 |
EP1780251A1 (en) | 2007-05-02 |
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