CN102741927A - UV-curable resin composition for use in optical disc, cured product, and article - Google Patents
UV-curable resin composition for use in optical disc, cured product, and article Download PDFInfo
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- CN102741927A CN102741927A CN2010800627728A CN201080062772A CN102741927A CN 102741927 A CN102741927 A CN 102741927A CN 2010800627728 A CN2010800627728 A CN 2010800627728A CN 201080062772 A CN201080062772 A CN 201080062772A CN 102741927 A CN102741927 A CN 102741927A
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- acrylic ester
- resin composition
- ultraviolet
- curing resin
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—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
- G11B7/257—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 having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B7/2572—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 having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials
- G11B7/2575—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 having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials resins
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
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- Optical Record Carriers And Manufacture Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Manufacturing Optical Record Carriers (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Disclosed is a UV-curable resin which can impart excellent recording signal characteristics and durability to optical discs having an organic dye recording layer. The disclosed UV-curable resin is suitable for use as an agent for forming a light-transmitting layer on optical discs having an organic dye recording layer, and comprises (1) (A) a (meth) acrylate having a C7-18 alkylene group, and (B) a photo-polymerisation initiator.
Description
Technical field
The present invention relates to the ultraviolet-curing resin composition useful to CD with organic pigment recording layer.
Background technology
At present, as the optical disc recording medium of practicability, exist: the polycarbonate substrate laminated at thickness 1.2mm has recording layer, reflection horizon, comprises CD-R, the CD-RW of the protective seam of ultraviolet curing resin; With ultraviolet curing resin the polycarbonate substrate of thickness 0.6mm and the polycarbonate substrate of the thickness 0.6mm with recording layer and reflection horizon are pasted and DVD-R, DVD+R, DVD-RW, DVD+RW, the DVD-RAM of formation.
In addition, in recent years, selling the Blu-ray Disc (BD-R) of about 5 times recording capacity of the DVD with single-layer type.Blu-ray Disc is meant; Have on the transparent of thickness 1.1mm or plastic opaque system substrate and form reflection horizon, recording layer and contact bed; Follow euphotic structure, and see through the CD that photic zone carries out recording/reproducing at the about 0.1mm of contact bed laminated thickness.Use organic pigment or mineral compound in the recording layer, contact bed uses the inorganics of light transmission, and photic zone uses the solidfied material layer of ultraviolet curing resin.
For Blu-ray Disc,, and utilize the volume change of organic pigment and record is carried out in the distortion that causes to the recording layer irradiating laser with the recording layer that comprises organic pigment.Volume change for accessory pigments; (for example obtain good tracer signal characteristic; Jittering characteristic), having proposed at the elastic modulus that is formed on the contact bed under 25 ℃ is that the technology (patent documentation 1) of the curable resin below the 40MPa, the elastic modulus that is formed under 25 ℃ are the technology (patent documentation 2) of the curable resin of 34 ~ 96MPa.
In addition, as the evaluation index of the reliability of aforesaid optical disc recording medium, carry out 100 hours environmental test of environment held at 80 ℃/relative humidity 80%RH of temperature.For the degradation that makes the tracer signal before and after this environmental test is in the scope of regulation, proposed to be below the 100MPa and the ratio of 5 ℃ elastic modulus and 55 ℃ elastic modulus is the technology (patent documentation 3) of the curable resin below 10 being formed on elastic modulus under 5 ℃ and 55 ℃ on the contact bed.
But, in patent documentation 1 ~ 3, be not disclosed in the concrete example of the curable resin that forms on the interface.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2008-123631 communique
Patent documentation 2: TOHKEMY 2008-269703 communique
Patent documentation 3: TOHKEMY 2009-026379 communique
Summary of the invention
The object of the present invention is to provide in CD, can give the good tracer signal characteristic and the ultraviolet-curing resin composition of permanance with organic pigment recording layer.
The inventor has carried out research extensively and profoundly in order to solve aforementioned problems; The result finds; Through containing the ultraviolet-curing resin composition of (methyl) acrylic ester with ad hoc structure; Can give have the organic pigment recording layer CD with good tracer signal characteristic and permanance, and accomplished the present invention.
That is, the present invention relates to following (1) ~ (7).
(1) a kind of CD with organic pigment recording layer is used ultraviolet-curing resin composition, and it contains (methyl) acrylic ester and (B) Photoepolymerizationinitiater initiater that (A) has the alkylidene of carbon number 7 ~ 18.
(2) use ultraviolet-curing resin composition like above-mentioned (1) described CD; Wherein, (methyl) acrylic ester (A) of alkylidene with carbon number 7 ~ 18 is for being selected from by (methyl) Isooctyl acrylate monomer, (methyl) lauryl acrylate, (methyl) isodecyl acrylate, (methyl) stearyl acrylate ester, (methyl) acrylic acid cetyl, the different myristin of (methyl) acrylic acid, (methyl) acrylic acid tridecane ester, 2-ethyl-2-butyl propylene glycol two (methyl) acrylic ester, 1; 9-nonanediol two (methyl) acrylic ester and 1, more than one in the group that 10-decanediol two (methyl) acrylic ester is formed.
(3) use ultraviolet-curing resin composition like above-mentioned (1) or (2) described CD, wherein, contain (C) (A) in addition (methyl) acrylic ester.
(4) use ultraviolet-curing resin composition like each described CD in above-mentioned (1) to (3), wherein,, contain (methyl) acrylic ester that 10 ~ 95 weight % (A) have the alkylidene of carbon number 7 ~ 18 with respect to composition in its entirety.
(5) use ultraviolet-curing resin composition like each described CD in above-mentioned (1) to (4); Wherein, (A) in addition (methyl) acrylic ester (C) be polyester polyol or polyether glycol and polyisocyanates and hydroxyl (methyl) acrylic ester reactant and/or, the bisphenol A-type diacrylate of oxirane modification.
(6) a kind of solidfied material is through obtaining with ultraviolet-curing resin composition irradiation active energy beam each described CD in above-mentioned (1) to (5).
(7) a kind of CD use ultraviolet-curing resin composition through each described CD in coating above-mentioned (1) to (5) on optical disc substrate, and shines active energy beam and obtain.
The invention effect
When in the photic zone of CD, using the ultraviolet-curing resin composition of (methyl) acrylic ester that contains alkylidene of the present invention with carbon number 7 ~ 18 with organic pigment recording layer, the high CD of reliability when can be provided in record and in the long-time use under hot and humid.
Embodiment
CD with organic pigment recording layer of the present invention contains (methyl) acrylic ester and the Photoepolymerizationinitiater initiater of the alkylidene with carbon number 7 ~ 18 with ultraviolet-curing resin composition (following also abbreviate as " ultraviolet-curing resin composition ").In addition, among the present invention, (methyl) acrylic ester is meant methacrylate or acrylic ester, the not special restriction of its kind.
(methyl) acrylic ester (A) of the alkylidene that contains in the ultraviolet-curing resin composition of the present invention with carbon number 7 ~ 18; In the scope of carbon number 7 ~ 18, can be not limited to straight or branched and use structurally, carbon number is ungood less than 7 o'clock tracer signal characteristics and permanance; On the other hand; Carbon number surpasses 18 o'clock fluid separation applications, is difficult to be coated with equably, does not expect from manufacture view.(methyl) acrylic ester (A) as alkylidene with carbon number 7 ~ 18; Preferably: (methyl) lauryl acrylate (for example; Block レ Application マ one LA that Japan Oil Co makes), (methyl) Isooctyl acrylate monomer (for example; The ラ イ ト ア Network リ レ one ト IO-A that Kyoeisha Chemical Co., Ltd. makes), (methyl) isodecyl acrylate (for example; The SR-395 that サ one ト マ one Co., Ltd. makes), (methyl) stearyl acrylate ester (for example; The ラ イ ト ア Network リ レ one ト IS-A that Kyoeisha Chemical Co., Ltd. makes), (methyl) acrylic acid cetyl (for example; Block レ Application マ one CA that Japan Oil Co makes), the different myristin of (methyl) acrylic acid (for example; The ラ イ ト ア Network リ レ one ト IM-A that Kyoeisha Chemical Co., Ltd. makes), (methyl) acrylic acid tridecane ester (for example, the SR-489 of サ one ト マ one Co., Ltd. manufacturing), 2-ethyl-2-butyl-propylene glycol two (methyl) acrylic ester (for example, the ニ ユ one Off ロ Application デ イ ア C9A of Di-ichi Kogyo Seiyaku Co., Ltd.'s manufacturing), 1; 9-nonanediol two (methyl) acrylic ester (for example; The Off ア Application Network リ Le FA-129AS that Hitachi Chemical Co., Ltd. makes) and 1,10-decanediol two (methyl) acrylic ester (for example, Xin Zhong village KCC make NK エ ス テ Le A-DOD-N).Wherein, (methyl) acrylic ester that preferably has the alkylidene of carbon number 7 ~ 14.
(A) content of composition in ultraviolet-curing resin composition is generally 10 ~ 95 weight %, preferred 20 ~ 80 weight %.When being lower than 10 weight %, volume change that can not accessory pigments is as jitter value (%) variation of the index of tracer signal characteristic.
The Photoepolymerizationinitiater initiater that contains in the ultraviolet-curing resin composition of the present invention (B), not special restriction, for example can enumerate: (Irgacure 184 for the 1-hydroxycyclohexylphenylketone; Ciba is made), 2-hydroxy-2-methyl-[4-(1-methyl ethylene) phenyl] propyl alcohol oligomer (ONE-Rifined), [4-(2-hydroxyl-oxethyl) phenyl]-the 2-hydroxy-2-methyl-(Irgacure 2959 for 1-propane-1-ketone for 1-; The Ciba manufacturing), 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propiono) benzyl] phenyl }-(Irgacure 127 for 2-methyl-propane-1-ketone; Ciba is made), 2, the 2-dimethoxy-(Irgacure 651 for 2-phenyl acetophenone; The Ciba manufacturing), (Darocur 1173 for 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone; The Ciba manufacturing), the 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-(Irgacure 907 for 2-morpholino propane-1-ketone; Ciba is made), 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone, 2-clopenthixal ketone, 2,4-dimethyl thioxanthones, 2,4-diisopropyl thioxanthones, isopropyl thioxanthone, 2; 4,6-trimethylbenzoyl diphenyl phosphine oxide, two (2,4; The 6-trimethylbenzoyl) phenyl phosphine oxide, two (2; 6-dimethoxy benzoyl)-2,4,4-tri-methyl-amyl phosphine oxide etc.
In the ultraviolet-curing resin composition of the present invention, these (B) compositions can use a kind of or use two or more with the arbitrary proportion mixing.(B) content of composition in ultraviolet-curing resin composition is generally 0.5 ~ 20 weight %, preferred 1 ~ 10 weight %.
In addition, also can be with using with above-mentioned Photoepolymerizationinitiater initiater combination as the amine etc. that photopolymerization causes auxiliary agent.As amine that can use etc., can enumerate benzoic acid-2-dimethylaminoethyl, dimethylamino acetophenone, (dimethylamino)-ethyl benzoate or p-(dimethylamino)-benzoic acid isopentyl ester etc.When using photopolymerization such as this amine to cause auxiliary agent, the content in ultraviolet-curing resin composition of the present invention is generally 0.005 ~ 5 weight %, preferred 0.01 ~ 3 weight %.
In the ultraviolet-curing resin composition of the present invention, except mentioned component, can also contain (A) (methyl) acrylic ester (C) in addition.
(A) that contains in the ultraviolet-curing resin composition of the present invention (methyl) acrylic ester (C) in addition for example can be enumerated: (methyl) acrylic ester with (methyl) acryloyl group more than.In addition; Among the present invention; (methyl) acrylic ester is meant methacrylate or acrylic ester; The not special restriction of its kind as (A) (methyl) acrylic ester (C) in addition, can be used (C-1) epoxy (methyl) acrylic ester, (C-2) carbamate (methyl) acrylic ester, (C-3) (methyl) acrylate monomer etc.Especially; In the present invention; Preferably with (C-1) epoxy (methyl) acrylic ester and/or (C-2) carbamate (methyl) acrylic ester use separately separately with (C-3) (methyl) acrylate monomer or combination is used, more preferably will (C-2) carbamate (methyl) acrylic ester and (C-3) (methyl) acrylate monomer combination use.
Operable among the present invention (C-1) epoxy (methyl) acrylic ester has the hardness that improves curable, improves solidfied material, the function that improves curing rate.In addition; Among the present invention; As epoxy (methyl) acrylic ester; So long as epoxy (methyl) acrylic ester that glycidol ether type epoxy compound obtains with the reaction of (methyl) acrylic acid; Then can use any one; As the glycidol ether type epoxy compound that is used for obtaining preferred epoxy (methyl) acrylic ester that uses of the present invention, can enumerate the diglycidyl ether, ethylene glycol diglycidylether, propylene glycol diglycidylether, neopentylglycol diglycidyl ether, butanediol diglycidyl ether, hexanediol diglycidyl ether, cyclohexanedimethanodiglycidyl diglycidyl ether, polypropylene glycol diglycidyl ether etc. of diglycidyl ether, A Hydrogenated Bisphenol A F or its alkylene oxide addition product of diglycidyl ether, hydrogenated bisphenol A or its alkylene oxide addition product of diglycidyl ether, Bisphenol F or its alkylene oxide addition product of bisphenol-A or its alkylene oxide addition product.
Epoxy (methyl) acrylic ester can obtain through these glycidol ether type epoxy compounds and (methyl) acrylic acid are reacted under following condition.
With respect to epoxy radicals 1 equivalent of glycidol ether type epoxy compound, make (methyl) acrylic acid with 0.9 ~ 1.5 mole, more preferably 0.95 ~ 1.1 mole ratio reacts.Preferred 80 ~ 120 ℃ of temperature of reaction, the reaction time is about 10 ~ about 35 hours.In order to promote reaction, preferably use for example triphenylphosphine, 2,4, catalyzer such as 6-three (dimethylamino methyl) phenol (TAP), triethanolamine, etamon chloride.In addition, in the reaction in order to prevent that polymerization from for example also can use p methoxy phenol, methyl hydroquinone etc. as polymerization inhibitor.
Among the present invention, as (C-1) epoxy (methyl) acrylic ester, bisphenol type epoxy (methyl) acrylic ester that more preferably obtains by the epoxy compound of bisphenol A-type.Among the present invention, as the molecular weight of (C-1) epoxy (methyl) acrylic ester, preferred 500 ~ 10000.
Operable among the present invention (C-2) carbamate (methyl) acrylic ester has the function of mechanical property (warpage, strain etc.) that improve to use the CD that ultraviolet-curing resin composition of the present invention pastes.Carbamate (methyl) acrylic ester can react through polyvalent alcohol, polyisocyanates and hydroxyl (methyl) acrylate compounds and obtain.
As polyvalent alcohol; For example can enumerate: neopentyl glycol, 3-methyl isophthalic acid; 5-pentanediol, (gathering) monoethylene glycol, (gathering) propylene glycol, 1; 4-butylene glycol, 1,6-hexanediol, trimethylolpropane, pentaerythrite, tristane dimethanol, two [methylol] cyclohexane etc., these polyvalent alcohols and polyprotonic acid (for example, succinic acid, phthalic acid, hexahydrophthalic anhydride, terephthalic acid (TPA), hexane diacid, azelaic acid, tetrabydrophthalic anhydride etc.) reaction and the polyester polyol, the polyvalent alcohol that obtain are pure with the caprolactone that the 6-caprolactone reaction obtains, polycarbonate polyol (for example; 1; The PCDL that 6-hexanediol and diphenyl carbonate reaction obtain etc.) or polyether glycol (for example, polyglycol, polypropylene glycol, gather 1, the bisphenol-A of 4-butylene glycol, oxirane modification etc.) etc.Wherein, preferred polyester polyvalent alcohol or polyether glycol.
As polyisocyanates; For example can enumerate: IPDI, hexamethylene diisocyanate, toluene diisocyanate, XDI, diphenyl methane-4,4 '-diisocyanate or tetrahydrochysene dicyclopentadiene isocyanates (ジ シ Network ロ ペ Application タ ニ Le イ ソ シ ア ネ one ト) etc.
As hydroxyl (methyl) acrylate compounds, for example can enumerate: (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid hydroxy butyl ester, hydroxymethyl-cyclohexane list (methyl) acrylic ester or hydroxyl caprolactone (methyl) acrylic ester etc.Wherein, preferred (methyl) hydroxy-ethyl acrylate, preferred especially (methyl) 2-Hydroxy ethyl acrylate.
Previous reaction is for example carried out in the following manner.That is, in polyvalent alcohol, the mode that is preferably 1.1 ~ 2.0 equivalents with the NCO with respect to its hydroxyl 1 equivalent organic multiple isocyanate is mixed organic multiple isocyanate, preferably under 70 ~ 90 ℃ of temperature of reaction, reacts the synthesis of carbamates oligomer.Then; NCO 1 equivalent with respect to oligourethane; The mode that is preferably 1 ~ 1.5 equivalent with the hydroxyl of hydroxyl (methyl) acrylic ester is mixed hydroxyl (methyl) acrylate compounds; And react, thereby can obtain target carbamate (methyl) acrylic ester at 70 ~ 90 ℃.In addition, also can obtain UX-0937: polyether-type urethane acrylate (Nippon Kayaku K. K's manufacturing) etc. from market.(C-2) molecular weight of carbamate (methyl) acrylic ester is preferably about 400 ~ about 10000.
Can be used as (methyl) acrylate monomer (C-3) that (A) (methyl) acrylic ester (C) in addition uses; Not special restriction; For example; (methyl) acrylate monomer as having (methyl) acryloyl group can be enumerated: (methyl) acrylic acid phenoxy ethyl, (methyl) acrylic acid phenoxy group macrogol ester, (methyl) benzyl acrylate, (methyl) tetrahydrofurfuryl acrylate, (methyl) acrylic acid morpholine ester, (methyl) acrylic acid phenyl glycidyl ester, (methyl) acrylic acid-2-hydroxy propyl ester, (methyl) acrylic acid ethoxy binaryglycol ester, (methyl) acrylic acid methoxyl two tripropylene glycol esters, (methyl) acrylic acid tristane ester, (methyl) IBOA, (methyl) acrylic acid dicyclopentadiene 2-ethoxyethyl acetate, acrylic acid dihydro dicyclopentadiene ester (ジ シ Network ロ ペ Application テ ニ Le ア Network リ レ one ト) are (for example; The FANCRYL FA-511A that Hitachi Chemical Co., Ltd. makes), acrylic acid dihydro dicyclopentadiene 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le ア Network リ レ one ト) (for example; The FANCRYL FA-512A that Hitachi Chemical Co., Ltd. makes), metering system acid dihydride dicyclopentadiene 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le メ タ Network リ レ one ト) (for example; The FANCRYL FA-512M that Hitachi Chemical Co., Ltd. makes), acrylic acid tetrahydrochysene dicyclopentadiene ester (ジ シ Network ロ ペ Application タ ニ Le ア Network リ レ one ト) (for example; The FANCRYL FA-513A that Hitachi Chemical Co., Ltd. makes), methacrylic acid tetrahydrochysene dicyclopentadiene ester (ジ シ Network ロ ペ Application タ ニ Le メ タ Network リ レ one ト) (for example; The FANCRYL FA-513M that Hitachi Chemical Co., Ltd. makes), acrylic acid-the 1-adamantane esters (for example; The Adamantate AA that Idemitsu Kosen Co., Ltd. makes), acrylic acid-the 2-methyl-the 2-adamantane esters (for example; The Adamantate MA that Idemitsu Kosen Co., Ltd. makes), acrylic acid-2-ethyl-the 2-adamantane esters (for example; The Adamantate EA that Idemitsu Kosen Co., Ltd. makes), phosphoric acid (methyl) acrylic ester of the octyloxyization of phosphoric acid (methyl) acrylic ester of the butoxyization of phosphoric acid (methyl) acrylic ester of the phenoxy groupization of methacrylic acid-1-adamantane esters (for example, Idemitsu Kosen Co., Ltd. make Adamantate AM), oxirane modification, oxirane modification and oxirane modification etc.(methyl) acrylate monomer with (methyl) acryloyl group has the function of the mechanical property (suppressing warpage, strain etc.) of the CD that raising forms as photic zone with ultraviolet-curing resin composition of the present invention.
For (methyl) acrylate monomer (C-3) that can be used as (A) (methyl) acrylic ester (C) use in addition; As (methyl) acrylate monomer with two (methyl) acryloyl groups; Can enumerate cyclohexane-1; 4-dimethanol two (methyl) acrylic ester, cyclohexane-1; 3-dimethanol two (methyl) acrylic ester, tristane dimethanol two (methyl) acrylic ester are (for example; The KAYARAD R-684 that Nippon Kayaku K. K makes; Tristane dimethanol diacrylates etc.), dioxane glycol two (methyl) acrylic ester (for example; The KAYARAD R-604 that Nippon Kayaku K. K makes; Dioxane glycol diacrylate etc.), neopentyl glycol two (methyl) acrylic ester, tetrahydrochysene dicyclopentadiene two (methyl) acrylic ester (ジ シ Network ロ ペ Application タ ニ Le ジ (メ タ) Network リ レ one ト), 1; 1 of 6-hexanediol two (methyl) acrylic ester, alkylene oxide modification, bisphenol A-type two (methyl) acrylic ester of neopentyl glycol two (methyl) acrylic ester of 6-hexanediol two (methyl) acrylic ester, neopentyl glycol two (methyl) acrylic ester, alkylene oxide modification, 3-hydroxypivalic acid DOPCP two (methyl) acrylic ester, polyglycol two (methyl) acrylic ester, polypropylene glycol two (methyl) acrylic ester, oxirane modification and di(2-ethylhexyl)phosphate (methyl) acrylic ester of oxirane modification etc.Among the present invention, especially preferably use bisphenol A-type two (methyl) acrylic ester of oxirane modification.
For (methyl) acrylate monomer (C-3) that can be used as (A) (methyl) acrylic ester (C) use in addition; As (methyl) acrylate monomer, can enumerate: isocyanuric acid three [(methyl) acrylyl oxy-ethyl] ester of trimethylolpropane tris (methyl) acrylic ester, trihydroxy methyl octane three (methyl) acrylic ester, the many ethoxys three of trimethylolpropane (methyl) acrylic ester, the many propoxyl group three of trimethylolpropane (methyl) acrylic ester, the many propoxyl group three of the many ethoxys of trimethylolpropane (methyl) acrylic ester, isocyanuric acid three [(methyl) acrylyl oxy-ethyl] ester, caprolactone modification, pentaerythrite three (methyl) acrylic ester, trimethylolpropane tris (methyl) acrylic ester of oxirane modification, trimethylolpropane tris (methyl) acrylic acid of epoxy pronane modification etc. with three (methyl) acryloyl groups.
For (methyl) acrylate monomer (C-3) that can be used as (A) (methyl) acrylic ester (C) use in addition; As (methyl) acrylate monomer, can enumerate: the many ethoxys four of pentaerythrite (methyl) acrylic ester, the many propoxyl group four of pentaerythrite (methyl) acrylic ester, pentaerythrite four (methyl) acrylic ester, two (trimethylolpropane) four (methyl) acrylic ester, dipentaerythritol four (methyl) acrylic ester etc. with four (methyl) acryloyl groups.
For (methyl) acrylate monomer (C-3) that can be used as (A) (methyl) acrylic ester (C) use in addition; As (methyl) acrylate monomer, can enumerate: dipentaerythritol five (methyl) acrylic ester of dipentaerythritol five (methyl) acrylic ester, caprolactone modification etc. with five (methyl) acryloyl groups.
For (methyl) acrylate monomer (C-3) that can be used as (A) (methyl) acrylic ester (C) use in addition; As (methyl) acrylate monomer, can enumerate: dipentaerythritol six (methyl) acrylic ester of dipentaerythritol six (methyl) acrylic ester, caprolactone modification etc. with six (methyl) acryloyl groups.In addition, operable among the present invention (methyl) acrylate monomer also can be for having multifunctional (methyl) acrylate monomer of (methyl) acryloyl group more than seven.
In the ultraviolet-curing resin composition of the present invention, these (C) compositions can use a kind of or be two or more with mixed use arbitrarily.(C) content of composition in ultraviolet-curing resin composition is generally 30 ~ 80 weight %, preferred 40 ~ 70 weight %.In addition; With (C-1) and/or when (C-2) and (C-3) combination is used as (C) composition; Usually (C-1) and/or (C-2) be about 5 ~ about 70 weight portions with respect to ultraviolet-curing resin composition 100 weight portions separately; Preferred about 10 ~ about 60 weight portions, (C-3) composition uses with respect to the mode of the scope of satisfied 20 ~ 80 weight portions of ultraviolet-curing resin composition 100 weight portions, preferred 25 ~ 75 weight portions with (C-3) composition and (A) the total amount of composition.
In the ultraviolet-curing resin composition of the present invention; Can add adjuvants such as rust preventive, anti-oxidant, organic solvent, silane coupling agent, polymerization inhibitor, levelling agent (レ ベ リ Application グ drug), antistatic agent, surface lubricant, fluorescer, light stabilizer (for example, hindered amine compound etc.), filling agent as required.Hindered amine compound is not so long as known hindered amine compound then can especially restrictedly use, and concrete example for example can be enumerated: 1,2,2; 6,6-pentamethyl-4-piperidines alcohol, 2,2,6; 6-tetramethyl-4-piperidines alcohol, (methyl) acrylic acid 1,2,2; 6, (ア デ カ Co., Ltd. makes 6-pentamethyl-4-piperidines ester, LA-82) etc.
Ultraviolet-curing resin composition of the present invention can be removed snotter through operations such as filtrations as required through a ℃ following mixed dissolution obtains in normal temperature ~ 80 with aforesaid each composition.Ultraviolet-curing resin composition of the present invention is considered coating, preferably is in the proportioning that the mode of 30 ~ 2000mPas scope is suitably regulated composition with 25 ℃ viscosity.
Ultraviolet-curing resin composition of the present invention can be suitably uses with the smears as the photic zone of the laser light incident side of Blu-ray Disc etc.Particularly, with any means, for example spin-coating method, 2P method, rolling method, silk screen print method etc. are that the mode of 1 ~ 100 μ m is applied to composition on the optical disc substrate with the thickness of resin of coating.After the coating, be cured from light one-sided or two sides irradiation ultraviolet ~ near ultraviolet (the about 200 ~ about 400nm of wavelength).Exposure is preferably about 50 ~ about 1500mJ/cm
2, preferred especially about 100 ~ about 1000mJ/cm
2In the curing that ultraviolet ~ near ultraviolet irradiate light is carried out, so long as the lamp of irradiation ultraviolet ~ near ultraviolet light is not then considered its light source.For example, can enumerate low pressure, high pressure or ultrahigh pressure mercury lamp, metal halide lamp, (pulse) xenon lamp or electrodeless lamp etc.
In addition, ultraviolet-curing resin composition of the present invention also can be applied to the situation that photic zone comprises multilayer.For example, by first resin bed that is forming on recording layer or the contact bed with seeing from first resin bed under the situation that second resin bed that forms with recording layer or the opposite face of contact bed side constitutes, can suitably be used for said first resin bed at photic zone.
At this moment, the thickness of said first resin bed is generally 1 μ m ~ 50 μ m, preferred 5 μ m ~ 40 μ m, more preferably 10 μ m ~ 30 μ m.
In addition, the thickness of said second resin bed is generally 50 μ m ~ 100 μ m, preferred 60 μ m ~ 95 μ m, more preferably 70 μ m ~ 90 μ m.
Photic zone is by under the two-layer situation about constituting; As euphotic formation method; Particularly; With any means, for example spin-coating method, 2P method, rolling method, silk screen print method etc. are that the mode of 1 μ m ~ 50 μ m is applied to composition on the optical disc substrate with the thickness as the resin of first resin bed coating.After the coating, be cured from light one-sided or two sides irradiation ultraviolet ~ near ultraviolet (the about 200 ~ about 400nm of wavelength).Exposure is preferably about 50 ~ about 1500mJ/cm
2, preferred especially about 100 ~ about 1000mJ/cm
2After the curing, with any means, for example spin-coating method, 2P method, rolling method, silk screen print method etc. are that the mode of 50 μ m ~ 100 μ m is applied to composition on the optical disc substrate with the thickness as the resin of second resin bed coating.After the coating, be cured from light one-sided or two sides irradiation ultraviolet ~ near ultraviolet (the about 200 ~ about 400nm of wavelength).Exposure is preferably about 50 ~ about 1500mJ/cm
2, preferred especially about 100 ~ about 1000mJ/cm
2In addition, in the curing that ultraviolet ~ near ultraviolet irradiate light is carried out, so long as the lamp of irradiation ultraviolet ~ near ultraviolet light is not then considered its light source.For example, can enumerate low pressure, high pressure or ultrahigh pressure mercury lamp, metal halide lamp, (pulse) xenon lamp or electrodeless lamp etc.
Embodiment
Below, through embodiment the present invention is described more specifically, but in any case the present invention is not limited to these embodiment.
In embodiment 1 ~ 4, comparative example 1 ~ 2, preparation has the ultraviolet-curing resin composition of forming shown in the table 1.
Table 1: resin combination and evaluation result
In addition, each composition of representing with abbreviation in the table 1 is described below.
LA: lauryl acrylate, the acrylic ester of the alkylidene that Japan Oil Co makes with carbon number 12
ISA: the different stearyl ester of acrylic acid, the acrylic ester that Kyoeisha Chemical Co., Ltd. makes with carbon number 18
NDDA:1,9-nonanediol diacrylate, the diacrylate of the alkylidene that Hitachi Chemical Co., Ltd. makes with carbon number 9
HDDA:1,6-hexanediyl ester, the diacrylate of the alkylidene that Nippon Kayaku K. K makes with carbon number 6
VA: acrylic acid Shan Yu ester, the acrylic ester of the alkylidene that Japan Oil Co makes with carbon number 22
UA-1: gather 1, the urethane acrylate that 4-butylene glycol (molecular weight 850), IPDI and three kinds of compositions of 2-Hydroxy ethyl acrylate obtain with mol ratio 1:2:2 reaction
BPE-10: the bisphenol A-type diacrylate of 10 moles of modifications of oxirane, Di-ichi Kogyo Seiyaku Co., Ltd. makes
FA-512A: acrylic acid dihydro dicyclopentadiene 2-ethoxyethyl acetate, Hitachi Chemical Co., Ltd. makes
Irgacure 184:1-hydroxycyclohexylphenylketone, Ciba Co., Ltd. makes
LA-82: methacrylic acid 1,2,2,6,6-pentamethyl-4-piperidines ester, rising sun electrification Co., Ltd. makes
The PMP:4-mercapto-phenol
Use resulting ultraviolet-curing resin composition of the present invention to make and have the Blu-ray Disc of organic pigment recording layer, and carry out evaluating characteristics.
Making (embodiment 1 ~ 3, comparative example 1 ~ 2) with Blu-ray Disc of organic pigment recording layer
On the polycarbonate substrate of the diameter 12cm of guiding groove, thickness 1.1mm with track pitch 0.32 μ m with the thickness sputtering silver alloy of 100nm, form the reflection horizon.Then, azopigment is dissolved in the pigment solution that forms in TFP (tetrafluoropropanol) solvent, thereby formed the organic pigment recording layer in 30 minutes 80 ℃ of dryings through the spin-coating method coating.Again with the thickness sputter ZnS-SiO of about 15nm
2(mol ratio 80:20) forms contact bed, thereby makes the Blu-ray Disc substrate.
2. the mode that the Blu-ray Disc substrate is made progress with contact bed is carried and is placed on the universal stage, is that the mode of 11.5mm is carried out circular cap rock and handled to cover internal diameter, then ultraviolet-curing resin composition 2.0g of the present invention is supplied on the cap rock of central part.
3. according to the viscosity of ultraviolet-curing resin composition of the present invention,, be that the mode of 25 μ m is coated with each coating film thickness with the velocity range spin coating of 1000rpm to 1500rpm 4 seconds to 7 seconds.Carry out twice xenon flash lamp irradiation when spin coating will finish, being cured to the surface does not have mobile degree.
4. use high-pressure sodium lamp, from upside with 400mJ/cm
2Shone 3 seconds, and made ultraviolet-curing resin composition full solidification of the present invention.
5. the mode that makes progress with the ultraviolet-curing resin composition of the present invention after solidifying is carried and is put on the universal stage; To cover internal diameter is that the mode of 11.5mm is carried out circular cap rock and handled, and then BRD-864 (Blu-ray Disc that Nippon Kayaku K. K makes is used resin with photic zone) 3.0g is supplied on the cap rock of central part.
6. with the velocity range spin coating of 1500rpm 4 seconds to 7 seconds, be that the mode of 75 μ m is coated with coating film thickness.Carry out twice xenon flash lamp irradiation when spin coating will finish, being cured to the surface does not have mobile degree.
7. use high-pressure sodium lamp, from upside with 400mJ/cm
2Shone 3 seconds, and made the BRD-864 full solidification, make Blu-ray Disc of the present invention.
Making (embodiment 4) with Blu-ray Disc of organic pigment recording layer
On the polycarbonate substrate of the diameter 12cm of guiding groove, thickness 1.1mm with track pitch 0.32 μ m with the thickness sputtering silver alloy of 100nm, form the reflection horizon.Then, azopigment is dissolved in the pigment solution that forms in TFP (tetrafluoropropanol) solvent, thereby formed the organic pigment recording layer in 30 minutes 80 ℃ of dryings through the spin-coating method coating.Again with the thickness sputter ZnS-SiO of about 15nm
2(mol ratio 80:20) forms contact bed, thereby makes the Blu-ray Disc substrate.
2. the mode that the Blu-ray Disc substrate is made progress with contact bed is carried and is placed on the universal stage, is that the mode of 11.5mm is carried out circular cap rock and handled to cover internal diameter, then ultraviolet-curing resin composition 2.0g of the present invention is supplied on the cap rock of central part.
3. according to the viscosity of ultraviolet-curing resin composition of the present invention,, be that the mode of 100 μ m is coated with coating film thickness with the velocity range spin coating of 800rpm to 1300rpm 4 seconds to 7 seconds.Carry out twice xenon flash lamp irradiation when spin coating will finish, being cured to the surface does not have mobile degree.
4. use high-pressure sodium lamp, from upside with 400mJ/cm
2Shone 3 seconds, and made ultraviolet-curing resin composition full solidification of the present invention, make Blu-ray Disc of the present invention.
Tracer signal characteristic before and after the endurancing of Blu-ray Disc
With the Blu-ray Disc of Blu-ray Disc of the present invention and comparative example 1 80 ℃, the environment held of 85%RH 250 hours.Use the Blu-ray Disc signal measuring device ODU-1000 of パ Le ス テ Star Network manufactured, measure the tracer signal characteristic (jitter value) of the Blu-ray Disc of endurancing front and back, and estimate with following benchmark.Jitter value is one of electric signal of CD, and their numerical value is high more, representes that then the signal data of Blu-ray Disc is poor more, is 10% to be difficult to carry out data write when above.
The evaluation of jitter value
Zero ... Jitter value is lower than 10.0%
* ... Jitter value is more than 10.0%
Ocular estimate when ultraviolet-curing resin composition is preserved
Behind the ultraviolet-curing resin composition of preparation the present invention and comparative example, after room temperature (25 ℃, 45%RH) is preserved 24 hours down, the outward appearance of observing liquid.Produce under the situation of fluid separation applications during preservation, be difficult to be coated with ultraviolet-curing resin composition equably and be difficult to solidify, therefore not preferred.
The ocular estimate of liquid
Zero ... Ultraviolet-curing resin composition does not separate
* ... Ultraviolet-curing resin composition separates
Can find out from the result of table 1; The resin combination of the present invention of embodiment 1 ~ 4 that contains (methyl) acrylic ester of the alkylidene with carbon number 7 ~ 18 obtains good tracer signal characteristic before and after endurancing when having good coating.On the other hand, the comparative example 1 that does not contain (methyl) acrylic ester of the alkylidene with carbon number 7 ~ 18 does not obtain good tracer signal characteristic before and after the endurancing.In addition, after the comparative example 2 that does not likewise contain (methyl) acrylic ester of the alkylidene with carbon number 7 ~ 18 is at room temperature preserved 24 hours, owing to the separation of liquid produces bad order.
With reference to specific mode the present invention is specified, still, it will be apparent for a person skilled in the art that under the situation that does not break away from the spirit and scope of the present invention and can carry out various changes and correction.
In addition, the application is based on the Japanese patent application (Japan special hope 2010-017575) of application on January 29th, 2010, and the integral body of this application is quoted by reference.In addition, incorporate this instructions on whole reference in its entirety of quoting.
Claims (7)
1. the CD with organic pigment recording layer is used ultraviolet-curing resin composition, and it contains (methyl) acrylic ester and (B) Photoepolymerizationinitiater initiater that (A) has the alkylidene of carbon number 7 ~ 18.
2. CD as claimed in claim 1 is used ultraviolet-curing resin composition; Wherein, (methyl) acrylic ester (A) of alkylidene with carbon number 7 ~ 18 is for being selected from by (methyl) Isooctyl acrylate monomer, (methyl) lauryl acrylate, (methyl) isodecyl acrylate, (methyl) stearyl acrylate ester, (methyl) acrylic acid cetyl, the different myristin of (methyl) acrylic acid, (methyl) acrylic acid tridecane ester, 2-ethyl-2-butyl propylene glycol two (methyl) acrylic ester, 1; 9-nonanediol two (methyl) acrylic ester and 1, more than one in the group that 10-decanediol two (methyl) acrylic ester is formed.
3. according to claim 1 or claim 2 CD is used ultraviolet-curing resin composition, wherein, contains (C) (A) in addition (methyl) acrylic ester.
4. use ultraviolet-curing resin composition like each described CD in the claim 1 to 3, wherein,, contain (methyl) acrylic ester that 10 ~ 95 weight % (A) have the alkylidene of carbon number 7 ~ 18 with respect to composition in its entirety.
5. use ultraviolet-curing resin composition like each described CD in the claim 1 to 4; Wherein, (A) in addition (methyl) acrylic ester (C) be polyester polyol or polyether glycol and polyisocyanates and hydroxyl (methyl) acrylic ester reactant and/or, the bisphenol A-type diacrylate of oxirane modification.
6. a solidfied material obtains through each described CD in the claim 1 to 5 is shone active energy beam with ultraviolet-curing resin composition.
7. CD use ultraviolet-curing resin composition through each described CD in the coating claim 1 to 5 on optical disc substrate, and shines active energy beam and obtain.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-017575 | 2010-01-29 | ||
| JP2010017575 | 2010-01-29 | ||
| PCT/JP2010/058505 WO2011061953A1 (en) | 2010-01-29 | 2010-05-20 | Uv-curable resin composition for use in optical disc, cured product, and article |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102741927A true CN102741927A (en) | 2012-10-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800627728A Pending CN102741927A (en) | 2010-01-29 | 2010-05-20 | UV-curable resin composition for use in optical disc, cured product, and article |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP4824840B2 (en) |
| CN (1) | CN102741927A (en) |
| SG (1) | SG182792A1 (en) |
| TW (1) | TW201125918A (en) |
| WO (1) | WO2011061953A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516864A (en) * | 2011-12-07 | 2012-06-27 | 华南理工大学 | Composite aqueous UV coating |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001143323A (en) * | 1999-11-18 | 2001-05-25 | Nippon Zeon Co Ltd | Laminate |
| JP2008192217A (en) * | 2007-02-02 | 2008-08-21 | Mitsubishi Rayon Co Ltd | Curing composition for optical information medium and optical information medium |
| JP2009158026A (en) * | 2007-12-27 | 2009-07-16 | Dic Corp | Uv-curable composition for optical disk and optical disk |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007080448A (en) * | 2005-09-16 | 2007-03-29 | Mitsubishi Rayon Co Ltd | Optical information medium |
| JP2008088382A (en) * | 2006-10-05 | 2008-04-17 | Mitsubishi Rayon Co Ltd | Curable composition, its cured product and optical information medium |
| CN101641741A (en) * | 2007-03-26 | 2010-02-03 | Dic株式会社 | Ultraviolet-curable composition for optical disk and optical disk |
| JP5016368B2 (en) * | 2007-05-09 | 2012-09-05 | 株式会社ブリヂストン | Photocurable transfer sheet, method for producing optical information recording medium using the same, and optical information recording medium |
| JP2009185222A (en) * | 2008-02-08 | 2009-08-20 | Mitsubishi Chemicals Corp | Radiation-curable composition for optical recording medium, its cured product, and optical recording medium using the same |
| JP2010009634A (en) * | 2008-06-24 | 2010-01-14 | Mitsubishi Rayon Co Ltd | Material for light transmission layer, curable composition, and optical information medium |
| JP2010009743A (en) * | 2009-10-13 | 2010-01-14 | Dic Corp | Ultraviolet-curable composition for optical disk and optical disk |
-
2010
- 2010-05-20 SG SG2012056289A patent/SG182792A1/en unknown
- 2010-05-20 CN CN2010800627728A patent/CN102741927A/en active Pending
- 2010-05-20 WO PCT/JP2010/058505 patent/WO2011061953A1/en active Application Filing
- 2010-05-20 JP JP2011505712A patent/JP4824840B2/en not_active Expired - Fee Related
- 2010-05-21 TW TW099116219A patent/TW201125918A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001143323A (en) * | 1999-11-18 | 2001-05-25 | Nippon Zeon Co Ltd | Laminate |
| JP2008192217A (en) * | 2007-02-02 | 2008-08-21 | Mitsubishi Rayon Co Ltd | Curing composition for optical information medium and optical information medium |
| JP2009158026A (en) * | 2007-12-27 | 2009-07-16 | Dic Corp | Uv-curable composition for optical disk and optical disk |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4824840B2 (en) | 2011-11-30 |
| TW201125918A (en) | 2011-08-01 |
| SG182792A1 (en) | 2012-09-27 |
| WO2011061953A1 (en) | 2011-05-26 |
| JPWO2011061953A1 (en) | 2013-04-04 |
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