CN102741929B - Blu-ray Disc, Blu-ray Disc ultraviolet-curing resin composition and solidfied material - Google Patents
Blu-ray Disc, Blu-ray Disc ultraviolet-curing resin composition and solidfied material Download PDFInfo
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- CN102741929B CN102741929B CN201180007767.1A CN201180007767A CN102741929B CN 102741929 B CN102741929 B CN 102741929B CN 201180007767 A CN201180007767 A CN 201180007767A CN 102741929 B CN102741929 B CN 102741929B
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- Prior art keywords
- methyl
- acrylate
- composition
- weight
- ultraviolet
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- 239000011342 resin composition Substances 0.000 title claims abstract description 81
- 239000000463 material Substances 0.000 title claims abstract description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 233
- 238000012986 modification Methods 0.000 claims abstract description 45
- 230000004048 modification Effects 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 239000012860 organic pigment Substances 0.000 claims abstract description 30
- 238000007711 solidification Methods 0.000 claims abstract description 27
- 230000008023 solidification Effects 0.000 claims abstract description 27
- 150000004767 nitrides Chemical class 0.000 claims abstract description 22
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims description 188
- -1 alkyl (methyl) acrylate Chemical compound 0.000 claims description 113
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 51
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 40
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 claims description 38
- 229920001451 polypropylene glycol Polymers 0.000 claims description 36
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 35
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 32
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 31
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- 125000004386 diacrylate group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 15
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 9
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- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 5
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- IRHICGGRMJVIOW-UHFFFAOYSA-N 2-(2,4,6-trioxo-1,3,5-triazinan-1-yl)ethyl prop-2-enoate Chemical class C=CC(=O)OCCN1C(=O)NC(=O)NC1=O IRHICGGRMJVIOW-UHFFFAOYSA-N 0.000 claims description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 4
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- 238000012360 testing method Methods 0.000 abstract description 6
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
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- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 6
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-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
- 238000004090 dissolution Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-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
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QPCCFOGFUGARRV-UHFFFAOYSA-N nonane-1,1,1-triol Chemical compound CCCCCCCCC(O)(O)O QPCCFOGFUGARRV-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 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
- 238000002834 transmittance Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- G11B7/254—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 protective topcoat layers
- G11B7/2542—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 protective topcoat layers consisting essentially of organic resins
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacturing Optical Record Carriers (AREA)
Abstract
The present invention relates to Blu-ray Disc and this Blu-ray Disc ultraviolet-curing resin composition and solidfied material thereof, the feature of described Blu-ray Disc is, contact bed on organic pigment recording layer has the solidification nitride layer of ultraviolet-curing resin composition, described ultraviolet-curing resin composition contains phenol (methyl) acrylate and (B) Photoepolymerizationinitiater initiater of oxirane (2 to the 10 moles) modification that (A) following general formula (1) (n is 2 to 10) represents, also containing (methyl) acrylate monomer (C) beyond above-mentioned (A) in preferred mode.There is the above-mentioned Blu-ray Disc of this solidification nitride layer, all there is excellent tracer signal characteristic (low jitter value) before and after long duration test.
Description
Technical field
The present invention relates to the ultraviolet-curing resin composition that the CD to having organic pigment recording layer, particularly Blu-ray Disc are useful.
Background technology
At present, as practical optical disc recording medium, exist: in the polycarbonate substrate of thickness 1.2mm, be laminated with recording layer, reflection horizon, comprise CD-R, 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, DVD-RAM of formation.
In addition, in recent years, the Blu-ray Disc (BD-R) of the recording capacity of about 5 times of the DVD with single-layer type is being sold.Blu-ray Disc refers to, have and form reflection horizon, recording layer and contact bed (also referred to as dielectric layer) on the transparent or opaque plastics substrate of thickness 1.1mm, then on contact bed, stacked thickness is about the structure of the photic zone (overlayer) of 0.1mm, and carries out the CD of recording/reproducing through photic zone.Recording layer uses organic pigment or mineral compound, and contact bed uses the mineral compound of light transmission.In addition, as photic zone, use the solidification nitride layer of ultraviolet curing resin.
For having the Blu-ray Disc of the recording layer comprising organic pigment, to recording layer irradiating laser, and record is carried out in the distortion utilizing the volume change of organic pigment and cause.In order to the volume change of accessory pigments, obtain excellent tracer signal characteristic (such as, jittering characteristic), propose a kind of optical information recording medium, it is characterized in that, light transmission overlayer is formed with curable resin, and the elastic modulus of the interface zone relative with recording layer is below 40MPa (patent documentation 1) at 25 DEG C, and a kind of optical information recording medium, its elastic modulus having on organic pigment recording layer at 25 DEG C is the resin solidification nitride layer (patent documentation 2) of 34 ~ 96MPa.But can reach such elastic modulus for the solidification nitride layer of the resin combination of which kind of composition, these documents then do not disclose completely.
In addition, as the evaluation index of the reliability of aforesaid optical disc recording medium, carry out the environmental test of placing 100 hours under the environment of temperature 80 DEG C/relative humidity 80%RH.Be in the scope of regulation to make the degradation of the tracer signal before and after this environmental test, propose a kind of elastic modulus be formed on the recording layer at 5 DEG C and 55 DEG C and be below 100MPa, and the elastic modulus of 5 DEG C and the ratio of the elastic modulus of 55 DEG C are the technology (patent documentation 3) of the solidification nitride layer of the curable resin of less than 10, described curable resin contains flexible amino formic ether acrylate as principal ingredient, and containing monofunctional acrylate as thinning agent, or containing urethane acrylate as principal ingredient, and containing monofunctional acrylate and polyfunctional acrylic ester as thinning agent.But, as mentioned above, it is urethane acrylate that the document only discloses principal ingredient, and thinning agent is independent monofunctional acrylate or the technical scheme combinationally using monofunctional acrylate and polyfunctional acrylic ester, does not disclose concrete one-tenth and is grouped into.
In addition, disclose a kind of Photocurable resin composition of the tackifier as stickup CD in patent documentation 4, described composition contains the phenol acrylate (Embodiment B 5) of thiophenol compound and oxirane 2 mole simultaneously.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2008-123631 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2008-269703 publication
Patent documentation 3: Japanese Unexamined Patent Publication 2009-026379 publication
Patent documentation 4:WO2009/144926A1 publication
Summary of the invention
The object of the present invention is to provide the CD, particularly Blu-ray Disc and its ultraviolet-curing resin composition used that possess the organic pigment recording layer with excellent tracer signal characteristic and permanance.
The present inventor has carried out research extensively and profoundly for solving described problem, found that, there is the CD of organic pigment recording layer, particularly in Blu-ray Disc, although the Blu-ray Disc with the resin solidification nitride layer of phenol (methyl) acrylate comprising (methyl) acrylate or oxirane 1 mole does not obtain good result, but be surprised to find that, the Blu-ray Disc with the cured layer of the ultraviolet-curing resin composition of phenol (methyl) acrylate of oxirane 2 to 10 mole comprising aftermentioned formula (1) demonstrates excellent tracer signal characteristic and permanance, and complete the present invention.
That is, the present invention relates to following (1) to (18).
1. a Blu-ray Disc, wherein, the contact bed on organic pigment recording layer is laminated with the solidification nitride layer of ultraviolet-curing resin composition, described ultraviolet-curing resin composition contains:
(A) there is (methyl) acrylate of the structure that following general formula (1) represents,
In formula, n represents the integer of 2 to 10; With
(B) Photoepolymerizationinitiater initiater.
2. the Blu-ray Disc as described in above-mentioned 1, is characterized in that, also containing (methyl) acrylate (C) beyond described (methyl) acrylate (A).
3. the Blu-ray Disc as described in above-mentioned 1 or 2, wherein, relative to composition in its entirety, the content of described (methyl) acrylate (A) is 10 to 95 % by weight.
4. the Blu-ray Disc as described in above-mentioned 2 or 3, wherein, described (methyl) acrylate (C) for (i) following or (ii) in any one or both:
(i) the reaction product (c-2a) of polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate (c-3a).
5. a manufacture method for CD, it comprises following operation:
On contact bed stacked on the organic pigment recording layer of optical disc substrate, coated UV line curable resin composition, forms coating layer, and then irradiate the operation that active energy beam makes it solidify, described ultraviolet-curing resin composition contains:
(A) (methyl) acrylate of representing of following general formula (1),
In formula, n represents the integer of 2 to 10; With
(B) Photoepolymerizationinitiater initiater.
6. there is a ultraviolet-curing resin composition for the Blu-ray Disc of organic pigment recording layer, it is characterized in that, contain:
(A) (methyl) acrylate of representing of following general formula (1),
In formula, n represents the integer of 2 to 10; With
(B) Photoepolymerizationinitiater initiater.
7. the ultraviolet-curing resin composition as described in above-mentioned 6, is characterized in that, also containing (methyl) acrylate (C) beyond described (methyl) acrylate (A).
8. the ultraviolet-curing resin composition as described in above-mentioned 6 or 7, wherein, relative to composition in its entirety, the content of described (methyl) acrylate (A) is 10 to 95 % by weight.
9. the ultraviolet-curing resin composition as described in above-mentioned 7 or 8, wherein, described (methyl) acrylate (C) for (i) following or (ii) in any one or both:
(i) the reaction product (c-2a) of polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate (c-3a).
10. as the ultraviolet-curing resin composition according to any one of above-mentioned 7 ~ 9, wherein, as (methyl) acrylate (C) beyond described (methyl) acrylate (A), not containing carbamate (methyl) acrylate, or when containing carbamate (methyl) acrylate, relative to this (A) composition and the total amount of being somebody's turn to do (C) composition, its content is lower than 30 % by weight.
11. ultraviolet-curing resin compositions as described in above-mentioned 9 or 10, wherein, (c-3a) composition to be the number of repeat unit of polyethylene oxide be 5 to 15 polyethylene oxide modified bisphenol A-type diacrylate.
12. as the ultraviolet-curing resin composition according to any one of above-mentioned 7 to 11, and wherein, relative to the total amount of (A) composition with (C) composition, (A) component content is greater than 25 % by weight and is less than 90 % by weight.
13. as the ultraviolet-curing resin composition according to any one of above-mentioned 7 to 12, wherein, relative to the total amount of ultraviolet-curing resin composition, (A) component content is 10 to 95%, (B) component content is 1 to 10%, the content of other adjuvant (adjuvant described later) beyond (A) to (C) composition is 0 to 15%, and all the other are (C) composition; Further, relative to the total amount of (A) composition and (C) composition, (i) (A) component content is greater than 25% and is less than 90%, or the content of carbamate (methyl) acrylate (C-2) (ii) in (C) composition is zero or lower than 30%; And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
14. as ultraviolet-curing resin composition according to any one of above-mentioned 7 to 13, wherein, as (methyl) acrylate (C) beyond (A) composition, containing (i) following or (ii) in any one or both:
(i) the reaction product (c-2a) of polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate (c-3a);
(c-3a) repeat number of the ethylene oxide,1,2-epoxyethane in composition is 5 to 15;
Relative to the total amount of (A) composition with (C) composition, the content of (c-2a) composition is lower than 30 % by weight, and (c-2a) composition is 10 to 85 % by weight with the total content of (c-3a) composition, and (A) component content is less than more than 15 % by weight 90 % by weight;
Relative to the total amount of ultraviolet-curing resin composition, (A) total amount of composition, (c-2a) composition and (c-3a) composition is 70 to 99 % by weight, the content of (C) composition beyond described (c-2a) composition and (c-3a) composition is 0 to 29 % by weight, and the content of (B) Photoepolymerizationinitiater initiater is 1 to 10 % by weight;
And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
15. ultraviolet-curing resin compositions as described in above-mentioned 7, wherein, as described (methyl) acrylate (C), comprise at least one be selected from group that (methyl) acrylate monomer (c-3c) of being organized by urethane acrylate (C-2), 5 to 15 moles of polyethylene oxide modified bisphenol A-type diacrylates (c-3a of 5 to 15 mole), (methyl) acrylate monomer (c-3b) that following (I) organizes and following (II) forms;
And, relative to the total amount of ultraviolet-curing resin composition, being selected from the content of at least one in described group with the total content of (A) component content is 70 to 99 % by weight, and (B) composition is 1 to 10 % by weight, and (methyl) other than the above acrylate (C) is 0 to 10 % by weight;
(I) group:
(i) C5 to C18 alkyl (methyl) acrylate or C7 to C18 alkylene glycol two (methyl) acrylate,
(ii) there is (methyl) acrylate of poly-BDO structure or (methyl) acrylate of epoxy pronane modification,
(iii) (methyl) acrylate of caprolactone modification;
(II) group:
(methyl) acrylic acid dihydro dicyclopentadiene base 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le (メ タ) ア Network リ レ mono-ト), 1,6-hexanediol two (methyl) acrylate, dipropylene glycol two (methyl) acrylate or tripropylene glycol two (methyl) acrylate.
16. ultraviolet-curing resin compositions as described in above-mentioned 15, wherein, (methyl) acrylate monomer (c-3b) that described (I) organizes is for being selected from least one in the group that is made up of following (methyl) acrylate:
(i) (methyl) Isooctyl acrylate monomer, (methyl) isoamyl acrylate, (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) acrylate, 1,9-nonanediol two (methyl) acrylate and 1,10-decanediol two (methyl) acrylate;
(ii) poly-(ethylene glycol-1, 4-butylene glycol) diacrylate, poly-(propylene glycol-1, 4-butylene glycol) diacrylate, poly-1, 4-butanediol diacrylate, poly-(ethylene glycol-1, 4-butylene glycol) dimethylacrylate, poly-(propylene glycol-1, 4-butylene glycol) dimethylacrylate, poly-1, 4-butanediol dimethylacrylate, polypropylene glycol (methyl) acrylate, polypropylene glycol two (methyl) acrylate, nonyl phenyl (methyl) acrylate of polypropylene oxide, neopentyl glycol two (methyl) acrylate of polypropylene oxide, 1 of polypropylene oxide, 6-hexanediol two (methyl) acrylate, bisphenol A-type two (methyl) acrylate of polypropylene oxide and methoxyl tripropylene glycol (methyl) acrylate,
(iii) dipentaerythritol six (methyl) acrylate of (methyl) hydroxy butyl acrylate of (methyl) Hydroxyethyl Acrylate of caprolactone modification, caprolactone modification, 3-hydroxypivalic acid DOPCP two (methyl) acrylate of caprolactone modification, three (acrylyl oxy-ethyl) isocyanuric acid esters of caprolactone modification and caprolactone modification.
17. as the ultraviolet-curing resin composition according to any one of above-mentioned 6 to 16, and wherein, the molecular weight of polyester polyol or polyether glycol is the scope of 200 to 3000.
18. as the ultraviolet-curing resin composition according to any one of above-mentioned 6 to 17, and wherein, the elastic modulus of solidfied material when being solidified by ultraviolet-curing resin composition at 25 DEG C is 0.1 to 100MPa.
The solidfied material of the ultraviolet-curing resin composition according to any one of 19. above-mentioned 10 to 18.
The purposes of the ultraviolet-curing resin composition according to any one of 20. above-mentioned 10 to 18, for the formation of resin solidification nitride layer stacked on the contact bed in Blu-ray Disc on organic pigment recording layer.
21. 1 kinds of Blu-ray Discs, wherein, the contact bed on organic pigment recording layer are laminated with the solidification nitride layer of the ultraviolet-curing resin composition described in any one in above-mentioned 10 to 18.
Invention effect
Directly be layered in the Blu-ray Disc of the present invention of the solidification nitride layer contact bed on organic pigment recording layer (also referred to as dielectric layer) with ultraviolet-curing resin composition of the present invention, jitter value before and after long duration test is all low, even if use for a long time under hot and humid condition, the reliability of record and regeneration is also high, and manufacture is also easy.In addition, the solidfied material of ultraviolet-curing resin composition of the present invention, the transmittance of the light under about 400nm blue light is also high, and, owing to having suitable elastic modulus, therefore in the Blu-ray Disc with organic pigment recording layer, both can use as the photic zone be directly layered on contact bed stacked on this recording layer (overlayer), also can use as the resin solidification nitride layer be layered between contact bed and photic zone.
Embodiment
Ultraviolet-curing resin composition of the present invention (hereinafter also referred to resin combination of the present invention), (methyl) acrylate (A) represented containing formula (1) and Photoepolymerizationinitiater initiater (B).
As (methyl) acrylate (A) (hereinafter also referred to as (A) composition) that the general formula (1) contained by composition of the present invention represents, as long as n is the scope of 2 to 10, then can use arbitrarily.Specifically, can enumerate: phenol (methyl) acrylate of oxirane 2 to 10 mole.
They can use commercially available product.Such as, Newfrontier can be obtained from market
rTMpHE-2: Shi Zhong n=2(Di-ichi Kogyo Seiyaku Co., Ltd. manufacture), Newfrontier
rTMpHE-6: Shi Zhong n=6(Di-ichi Kogyo Seiyaku Co., Ltd. manufactures).
In addition, in this instructions, subscript RTM represents registered trademark.
Relative to the total amount of said composition, the content of (A) composition in ultraviolet-curing resin composition is generally 10 to 95 % by weight, and preferably 15 to 90 % by weight, more preferably 20 to 80 % by weight (below unless otherwise noted, then % represents % by weight).
Such as, when the contact bed of Blu-ray Disc with organic pigment recording layer arranges the solidification nitride layer of resin combination of the present invention, the content being somebody's turn to do (A) composition can be above-mentioned scope, but with regard to the mode that content is more, such as relative to the total amount of said composition, be greater than 25 % by weight and be less than 90 % by weight mode be also one of optimal way.
In addition, relative to the total amount of said composition, should the content of (A) composition be the mode of mode, preferably about 20 to about 80% of about 15 to about 80%, in addition according to circumstances for being greater than 25% and the mode etc. of less than 80% is also all one of optimal ways.
When content is very few, cannot the volume change of accessory pigments, thus the jitter value (%) of index as tracer signal characteristic is deteriorated.
As the Photoepolymerizationinitiater initiater (B) contained by composition of the present invention, be not particularly limited, can enumerate such as: 1-hydroxycyclohexylphenylketone (Irgacure
rTM184; Ciba manufactures), 2-hydroxy-2-methyl-[4-(1-methyl ethylene) phenyl] propyl alcohol oligomer (ONE-Rifined), 1-[4-(2-hydroxyl-oxethyl)-phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone (Irgacure
rTM2959; Ciba manufactures), 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl propiono) benzyl] phenyl-2-methylpropane-1-ketone (Irgacure
rTM127; Ciba manufacture), 2,2-dimethoxy-2-phenyl acetophenone (Irgacure
rTM651; Ciba manufacture), 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone (Darocur
rTM1173; Ciba manufactures), 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino propane-1-ketone (Irgacure
rTM907; Ciba manufacture), 2-benzyl-2-dimethylamino-1-(4-morphlinophenyl)-butane-1-ketone, CTX, 2; 4-dimethyl thioxanthone, 2; 4-diisopropylthioxanthone, isopropyl thioxanthone, 2; 4,6-trimethyl benzoyl diphenyl base phosphine oxide, two (2,4; 6-trimethylbenzoyl)-phenyl phosphine oxide, two (2; 6-Dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide etc.
In ultraviolet-curing resin composition of the present invention, these (B) compositions can use one or used in combination two or more with arbitrary proportion.Relative to the total amount of this resin combination, the content of (B) composition in ultraviolet-curing resin composition, is generally 0.5 to 20 % by weight, and preferably 1 to 10 % by weight.
In addition, also can as required the amine etc. that can cause auxiliary agent as photopolymerization be combinationally used with above-mentioned Photoepolymerizationinitiater initiater.As the amine etc. that can use, can enumerate: benzoic acid-2-dimethylaminoethyl, dimethylamino acetophenone, (dimethylamino)-ethyl benzoate or IADB etc.The photopolymerization such as this amine cause auxiliary agent and can not use, but, when using the photopolymerization such as this amine to cause auxiliary agent as required, relative to the total amount in resin combination of the present invention, content in this resin combination is generally 0.005 ~ 5 % by weight, and preferably 0.01 ~ 3 % by weight.
As (methyl) acrylate (C) (hereinafter also referred to as (C) composition) beyond (A) contained by composition of the present invention, (methyl) acrylate that there is more than, there is to six (methyl) acryloyl group usually can be enumerated.In addition, (methyl) acrylate in the present invention is methacrylate or acrylate.Its kind is not particularly limited.Can use such as: (C-1) epoxy (methyl) acrylate (hereinafter also referred to (C-1) composition) and/or (C-2) carbamate (methyl) acrylate (hereinafter also referred to (C-2) composition), and (methyl) acrylate compounds (hereinafter referred to as (methyl) acrylate monomer (C-3)) etc. beyond above (A) composition, (C-1) composition and (C-2) composition.
Above-mentioned epoxy (methyl) acrylate (C-1), has and improves curability or improve the hardness of solidfied material or the function of curing rate.This epoxy (methyl) acrylate (C-1), can obtain by making diglycidyl ether type epoxy compound and (methyl) acrylic acid react.
As the preferred diglycidyl ether type epoxy compound in order to obtain epoxy (methyl) acrylate (C-1), the diglycidyl ether of the glycol of record can be listed below.
As the glycol for obtaining above-mentioned diglycidyl ether, can enumerate: bisphenol-A or its alkylene oxide addition product, Bisphenol F or its alkylene oxide addition product, hydrogenated bisphenol A or its alkylene oxide addition product, A Hydrogenated Bisphenol A F or its alkylene oxide addition product, ethylene glycol, propylene glycol, neopentyl glycol, butylene glycol, hexanediol, cyclohexanedimethanol, polypropylene glycol etc.
Epoxy (methyl) acrylate, by making these diglycidyl ether type epoxy compounds and (methyl) acrylic acid react, makes the epoxy radicals of (methyl) acrylic acid carboxyl and epoxy compound carry out open loop addition and obtain.
Relative to epoxy radicals 1 equivalent of diglycidyl ether type epoxy compound, make (methyl) acrylic acid with 0.9 to 1.5 mole, preferably the ratio reaction of 0.95 to 1.1 mole.Temperature of reaction preferably 80 to 120 DEG C, the reaction time is about 10 to about 35 hours.For promoting reaction, preferably use the catalyzer such as such as triphenylphosphine, 2,4,6-tri-(dimethylamino methyl) phenol (TAP), triethanolamine, etamon chloride.In addition, in order to prevent polymerization in reaction, such as p methoxy phenol, methyl hydroquinone etc. can be used as polymerization inhibitor.
In the present invention, as epoxy (methyl) acrylate, the bisphenol type epoxy more preferably obtained by the epoxy compound of bisphenol A-type (methyl) acrylate.In the present invention, the molecular weight of epoxy (methyl) acrylate (C-1) preferably 500 to 10000.
Described carbamate (methyl) acrylate (C-2), can obtain by making polyvalent alcohol, polyisocyanates and hydroxyl (methyl) acrylate compounds react.More specifically, can react by making polyvalent alcohol and polyisocyanates and obtain oligourethane, and make this oligourethane and hydroxyl (methyl) acrylate compounds react and obtain.
This carbamate (methyl) acrylate (C-2), there is the viscosity regulating resin combination of the present invention, the elastic modulus regulating solidfied material, and improve the function of mechanical property (reducing warpage, distortion etc.) when being used as photic zone by the cured layer of this resin combination.
The polyvalent alcohol used in synthesis as carbamate (methyl) acrylate (C-2), can enumerate following polyvalent alcohol.
(i) aliphatic polyol, the aliphatic polyol of preferred carbon number 2 to 10, as: neopentyl glycol, 3-methyl isophthalic acid, 5-pentanediol, ethylene glycol, propylene glycol, 1,4 butylene glycols, 1,6-hexanediol, trimethylolpropane, pentaerythrite, Tricyclodecane Dimethanol, two-[methylol]-cyclohexane etc.
(ii) the polyester polyol obtained by a kind of the reaction with polyprotonic acid in the described aliphatic polyol (i) recorded.
In addition, as above-mentioned polyprotonic acid, can enumerate such as: succinic acid, phthalic acid, hexahydrophthalic anhydride, terephthalic acid (TPA), hexane diacid, azelaic acid, tetrabydrophthalic anhydride etc.
(iii) by caprolactone alcohol that polyvalent alcohol and 6-caprolactone react and obtain.
(iv) polycarbonate polyol.The PCDL etc. such as obtained by 1,6-hexanediol and diphenyl carbonate reaction.
(v) polyether glycol.The bisphenol-A etc. of the poly-C2-C4 alkylene glycols such as such as polyglycol, polypropylene glycol or poly-BDO, alkylene oxide modification.
In above-mentioned, polyvalent alcohol preferred, polyethers polyvalent alcohol or polyester polyol.Their mean molecular weight preferably about 200 to about 8000, more preferably from about 200 to about 3000, further preferably about 300 to about 1800.
The organic multiple isocyanate used in synthesis as carbamate (methyl) acrylate (C-2), can enumerate such as: isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, Xylene Diisocyanate, diphenyl methane-4,4'-diisocyanate or tetrahydrochysene dicyclopentadiene group diisocyanate (ジ シ Network ロ ペ Application タ ニ Le ジ イ ソ シ ア ネ mono-ト) etc.In these materials, preferred isophorone diisocyanate.
As hydroxyl (methyl) acrylate compounds used in the synthesis of carbamate (methyl) acrylate (C-2), such as hydroxyl C2 to C8 aliphatic hydrocarbon (methyl) acrylate can be enumerated, as: (methyl) Hydroxyethyl Acrylate, (methyl) hydroxypropyl acrylate, (methyl) hydroxy butyl acrylate, list (methyl) acrylic acid dihydroxymethyl cyclohexyl, hydroxyl caprolactone (methyl) acrylate etc.
The synthetic reaction of described carbamate (methyl) acrylate (C-2), such as, can as described belowly carry out.
That is, in polyvalent alcohol, mix organic multiple isocyanate in the mode being preferably 1.1 ~ 2.0 equivalents relative to the isocyanate group of its hydroxyl 1 equivalent organic multiple isocyanate, preferably react at temperature of reaction 70 ~ 90 DEG C, synthesis of carbamates oligomer.Then, relative to isocyanate group 1 equivalent of oligourethane, the mode being preferably 1 ~ 1.5 equivalent with the hydroxyl of hydroxyl (methyl) acrylate mixes hydroxyl (methyl) acrylate compounds, and react at 70 ~ 90 DEG C, thus desired carbamate (methyl) acrylate can be obtained.
As preferred carbamate (methyl) acrylate (C-2), can enumerate and use polyester polyol or polyether glycol as polyvalent alcohol, and use carbamate (methyl) acrylate that (methyl) acrylic acid 2-hydroxy methacrylate obtains as hydroxyl (methyl) acrylate, carbamate (methyl) acrylate (c-2a) such as obtained by polyester polyol or polyether glycol, polyisocyanates and acrylic acid 2-hydroxy methacrylate three.
In addition, use molecular weight about 200 to about 3000(preferred molecular weight 300 to 1800) polyester polyol or polyether glycol and carbamate (methyl) acrylate that obtains also is one of preferred carbamate (methyl) acrylate.
In addition, according to circumstances, by poly-C3 to the C5 alkylene glycol of poly-C2 to C6 alkylene glycol, more preferably molecular weight about 300 to about 1800 of about 300 to about 1800, your Buddhist ketone diisocyanate different and hydroxyl C2 to C4(methyl) reaction of acrylate and carbamate (methyl) acrylate that obtains also is one of preferred carbamate (methyl) acrylate.
In addition, also UX-0937 can be obtained from the market: polyethers urethane acrylate (Nippon Kayaku K. K's manufacture) etc.
As the molecular weight of carbamate (methyl) acrylate (C-2), preferably about 400 to about 10000.
(methyl) acrylate monomer (C-3) that can use as (methyl) acrylate (C) beyond (A) composition, (C-1) composition and (C-2) composition is not particularly limited, and can enumerate following simple function or multifunctional (preferably 2 to 6 officials' energy) (methyl) acrylate.
Such as, as simple function (methyl) acrylate (there is (methyl) acrylate of (methyl) acryloyl group) in (C-3) composition, following compound can be illustrated particularly.
(i) the preferred C7 to C18 of C5 to C18() alkyl (methyl) acrylate, as: (methyl) Isooctyl acrylate monomer, (methyl) isoamyl acrylate, (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 etc.;
(ii) there is the acrylate compounds of C7 to C10 aliphatics ring, as tristane (methyl) acrylate, (methyl) isobornyl acrylate, acrylic acid dihydro dicyclopentadiene ester (ジ シ Network ロ ペ Application テ ニ Le ア Network リ レ mono-ト) (such as, the FANCRYL of Hitachi Chemical Co., Ltd.'s manufacture
rTMfA-511A), acrylic acid dihydro dicyclopentadiene base 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le ア Network リ レ mono-ト) (such as, Hitachi Chemical Co., Ltd. manufacture FANCRYLFA-512A), (methyl) acrylic acid dicyclopentadiene 2-ethoxyethyl acetate (such as, metering system acid dihydride dicyclopentadiene base 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le メ タ Network リ レ mono-ト), the FANCRYL that Hitachi Chemical Co., Ltd. manufactures
rTMfA-512M), acrylic acid tetrahydrochysene dicyclopentadiene ester (such as, the FANCRYL of Hitachi Chemical Co., Ltd.'s manufacture
rTMfA-513A), methacrylic acid tetrahydrochysene dicyclopentadiene ester (ジ シ Network ロ ペ Application タ ニ Le メ タ Network リ レ mono-ト) (such as, the FANCRYL of Hitachi Chemical Co., Ltd.'s manufacture
rTMfA-513M), acrylic acid 1-diamantane ester (such as, Idemitsu Kosen Co., Ltd. manufacture AdamantateAA), acrylic acid 2-methyl-2 diamantane ester (such as, Idemitsu Kosen Co., Ltd. manufacture AdamantateMA), acrylic acid 2-ethyl-2 diamantane ester (such as, the AdamantateEA that Idemitsu Kosen Co., Ltd. manufactures), methacrylic acid 1-diamantane ester (such as, Idemitsu Kosen Co., Ltd. manufacture AdamantateAM) etc.;
(iii) (methyl) acrylate of polypropylene oxide, as: polypropylene glycol (methyl) acrylate, nonyl phenyl (methyl) acrylate of polypropylene oxide, methoxyl tripropylene glycol (methyl) acrylate etc., or ethylene-oxide-modified (methyl) acrylate, as ethoxydiglycol (methyl) acrylate, phosphoric acid (methyl) acrylate of ethylene-oxide-modified phenoxylation, ethylene-oxide-modified butoxylated phosphoric acid (methyl) acrylate and phosphoric acid (methyl) acrylate etc. of ethylene-oxide-modified octyloxy,
That is, (methyl) acrylate compounds of C2 or C3 alkylene oxide modification;
(iv) (methyl) dihydroxypropyl C1 to C5 Arrcostab of caprolactone modification, as (methyl) Hydroxyethyl Acrylate of caprolactone modification, (methyl) hydroxy butyl acrylate etc. of caprolactone modification;
(v) in addition, as monofunctional acrylate other than the above, can enumerate such as: (methyl) benzyl acrylate, (methyl) tetrahydrofurfuryl acrylate, (methyl) acrylic acid morpholine ester, (methyl) phenylethyl ethylene oxidic ester, (methyl) acrylic acid 2-hydroxy propyl ester etc.
There is (methyl) acrylate monomer of (methyl) acryloyl group, there is the function improving the mechanical property (suppressing warpage, distortion etc.) ultraviolet-curing resin composition of the present invention being formed as euphotic CD (Blu-ray Disc).
Such as, be laminated with in the Blu-ray Disc of solidification nitride layer of ultraviolet-curing resin composition of the present invention in the Blu-ray Disc with organic pigment recording layer, on this contact bed formed on this organic pigment recording layer with the direct way of contact, play above-mentioned functions.
In above-mentioned, in order to regulate the elastic modulus of the solidfied material of resin combination of the present invention in preferred scope, the preferred C7 to C18 of C5 to C18(can be used) alkyl (methyl) acrylate.By comprising this composition, jitter value can be reduced further.The preferred C7 to C18 of C5 to C18() most preferably lauryl acrylate in alkyl (methyl) acrylate.
As multifunctional (methyl) acrylate monomer in above-mentioned (methyl) acrylate monomer (C-3), following (methyl) acrylate monomer with six two to six (methyl) acryloyl groups can be enumerated.
(i) as (methyl) acrylate monomer with two (methyl) acryloyl groups of (C-3) composition;
Can enumerate: cyclohexane-1, 4-dimethanol two (methyl) acrylate, cyclohexane-1, 3-dimethanol two (methyl) acrylate, tristane dihydroxymethyl two (methyl) acrylate (such as, Nippon Kayaku K. K manufactures, KAYARADR-684, tristane dihydroxymethyl diacrylate etc.), dioxane support glycol two (methyl) acrylate (such as, Nippon Kayaku K. K manufactures, KAYARADR-604, dioxane support omega-diol diacrylate etc.), neopentyl glycol two (methyl) acrylate, tetrahydrochysene dicyclopentadiene base two (methyl) acrylate (ジ シ Network ロ ペ Application タ ニ Le ジ (メ タ) Network リ レ mono-ト), 1, 6-hexanediol two (methyl) acrylate, ethylene-oxide-modified 1, 6-hexanediol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate that (gathering) is ethylene-oxide-modified, 3-hydroxypivalic acid DOPCP two (methyl) acrylate, polyglycol two (methyl) acrylate, polypropylene glycol two (methyl) acrylate, ethylene-oxide-modified bisphenol A-type two (methyl) acrylate (preferably polyethylene oxide modified bisphenol A-type two (methyl) acrylate, more preferably bisphenol A-type two (methyl) acrylate of oxirane 5 to 15 mole) and (gathering) ethylene-oxide-modified di(2-ethylhexyl)phosphate (methyl) acrylate etc.
In above-mentioned, preferably polyethylene oxide modified bisphenol A-type two (methyl) acrylate (c-3a), according to circumstances bisphenol A-type two (methyl) acrylate of more preferably oxirane 5 to 15 mole.
In addition, also preferably there is two (methyl) acrylate of the glycol of the alkylidene of carbon number 7 to 18, as: 2-ethyl-2-butyl propylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate and 1,10-decanediol two (methyl) acrylate etc.Elastic modulus in order to the solidfied material by resin combination is adjusted to preferred scope, can use these materials.
(ii) as (methyl) acrylate monomer with 3 (methyl) acryloyl groups of (C-3) composition;
Can enumerate: trimethylolpropane tris (methyl) acrylate, trihydroxy methyl octane three (methyl) acrylate, trimethylolpropane many ethoxys three (methyl) acrylate, trimethylolpropane many propoxyl group three (methyl) acrylate, the many ethoxys of trimethylolpropane many propoxyl group three (methyl) acrylate, three [(methyl) acryloyl group oxygen ethyl] isocyanuric acid ester, three [(methyl) acryloyl group oxygen ethyl] isocyanuric acid ester of caprolactone modification, pentaerythrite three (methyl) acrylate, ethylene-oxide-modified trimethylolpropane tris (methyl) acrylate, trimethylolpropane tris (methyl) acrylate etc. of epoxy pronane modification.
(iii) as (methyl) acrylate monomer with four (methyl) acryloyl groups of (C-3) composition;
Can enumerate: the many ethoxys of pentaerythrite four (methyl) acrylate, pentaerythrite many propoxyl group four (methyl) acrylate, pentaerythrite four (methyl) acrylate, two (trimethylolpropane) four (methyl) acrylate, dipentaerythritol four (methyl) acrylate etc.
(iv) as (methyl) acrylate monomer with five (methyl) acryloyl groups of (C-3) composition;
Can enumerate: dipentaerythritol five (methyl) acrylate etc. of dipentaerythritol five (methyl) acrylate, caprolactone modification.
(v) as (methyl) acrylate monomer with six (methyl) acryloyl groups of (C-3) composition;
Can enumerate: dipentaerythritol six (methyl) acrylate etc. of dipentaerythritol six (methyl) acrylate, caprolactone modification.
In addition, (methyl) acrylate monomer operable in the present invention also can for having multifunctional (methyl) acrylate monomer of more than seven (methyl) acryloyl groups.
In (C-3) composition ((methyl) acrylate monomer) more than enumerated, (methyl) acrylate monomer (c-3b) recorded in following (I) group, when using together with described (A) composition, when the reliability of the record regenerating making obtained Blu-ray Disc improves, it is one of preferred (methyl) acrylate monomer.
(I) group:
(i) C5 to C18 alkyl (methyl) acrylate, as (methyl) Isooctyl acrylate monomer, (methyl) isoamyl acrylate, (methyl) lauryl acrylate, (methyl) isodecyl acrylate, (methyl) stearyl acrylate ester, (methyl) acrylic acid cetyl, the different myristin of (methyl) acrylic acid or (methyl) acrylic acid tridecane ester etc.; Or C7 to C18 alkylene glycol (methyl) acrylate, as: 2-ethyl-2-butyl propylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate and 1,10-decanediol two (methyl) acrylate etc.;
(ii) have poly-1, (methyl) acrylate of 4-butylene glycol structure, as: poly-(ethylene glycol-1,4-butylene glycol) diacrylate, poly-(propylene glycol-1,4-butylene glycol) diacrylate, poly-BDO diacrylate, poly-(ethylene glycol-BDO) dimethylacrylate, poly-(propylene glycol-1,4-butylene glycol) dimethylacrylate, poly-BDO dimethylacrylate etc.; And (methyl) acrylate of epoxy pronane modification, as: 1,6-hexanediol two (methyl) acrylate of nonyl phenyl (methyl) acrylate of polypropylene glycol (methyl) acrylate, polypropylene glycol two (methyl) acrylate, polypropylene oxide, neopentyl glycol two (methyl) acrylate of polypropylene oxide, polypropylene oxide, bisphenol A-type two (methyl) acrylate of polypropylene oxide and methoxyl tripropylene glycol (methyl) acrylate etc.;
(iii) (methyl) acrylate of caprolactone modification, as: dipentaerythritol six (methyl) acrylate etc. of (methyl) Hydroxyethyl Acrylate of caprolactone modification, (methyl) hydroxy butyl acrylate of caprolactone modification, 3-hydroxypivalic acid DOPCP two (methyl) acrylate of caprolactone modification, three (acrylyl oxy-ethyl) isocyanuric acid esters of caprolactone modification and caprolactone modification;
Above-mentioned (methyl) acrylate monomer (c-3b), by using in resin combination of the present invention as required, contribute to the reliability of the solidification nitride layer improving resin combination of the present invention thus, the recording characteristic of the Blu-ray Disc obtained is excellent.
The elastic modulus of solidification nitride layer at 25 DEG C of resin combination of the present invention is adjusted to 0.1 to 100MPa, when being preferably adjusted to the scope of 0.1 to 50MPa, the recording characteristic that the contact bed being layered in organic pigment recording layer has the Blu-ray Disc of this solidification nitride layer is excellent.
In above-mentioned, (methyl) acrylate of epoxy pronane modification is one of the preferred substance as (methyl) acrylate monomer (c-3b), according to circumstances, can give more excellent tracer signal characteristic and permanance to Blu-ray Disc of the present invention.
The repeat number (modification molal quantity) preferred about 2 to about 15 of trimethylene oxygen unit in (methyl) acrylate of this epoxy pronane modification.When the number of (methyl) acryloyl group in molecule is many, the modification molal quantity of preferred epoxypropane is many.When such as, there is in molecule (methyl) acryloyl group, the repeat number (modification molal quantity) of trimethylene oxygen unit preferably more than 2, more preferably from about 2 to about 20, further preferably about 5 to about 15.When there is two (methyl) acryloyl groups, the repeat number of trimethylene oxygen unit preferably more than 7, more preferably from about 7 to about 15, further preferably about 10 to about 15.
As (methyl) acrylate of preferred epoxy pronane modification, can enumerate such as: nonyl phenyl (methyl) acrylate of polypropylene glycol (methyl) acrylate, epoxy pronane modification, methoxyl tripropylene glycol (methyl) acrylate or polypropylene glycol two (methyl) acrylate etc.
As polypropylene glycol (methyl) acrylate, can enumerate such as: the BLEMMER that Japan Oil Co manufactures
rTMthe repeat number 3 of AP-150(trimethylene oxygen unit), the repeat number 6 of AP-400(trimethylene oxygen unit), the repeat number 9 of AP-550(trimethylene oxygen unit) etc.In addition, as polypropylene glycol two (methyl) acrylate, can enumerate such as: the FANCRYL that Hitachi Chemical Co., Ltd. manufactures
rTMthe repeat number 7 of FA-P240A(propylene glycol units), the repeat number 12 of FA-P270A(propylene glycol units); As nonyl phenyl (methyl) acrylate of polypropylene oxide, can enumerate such as: the repeat number 2.5 of M-177(propylene glycol units that Toagosei Co., Ltd manufactures), the Newfrontier that manufactures of Di-ichi Kogyo Seiyaku Co., Ltd.
rTMthe repeat number 5 of NP-5P(propylene glycol units); In addition, as methoxyl tripropylene glycol (methyl) acrylate, can enumerate such as: the repeat number 3 of the NKEsterAM-30PG(propylene glycol units that KCC of Xin Zhong village manufactures) etc.The repeat number of the propylene glycol units such as above-mentioned FA-P270A many (such as repeat number 7 to 15, preferably 10 to 15, most preferably 12), due to excellent recording characteristic can be obtained, therefore preferably.
In addition, in described (C-3) composition ((methyl) acrylate monomer), (methyl) acrylate monomer (c-3c) that following (II) organizes, owing to can improve the hardness of solidfied material when using together with described (A) composition, therefore preferably as (methyl) acrylate monomer (C-3) being used for such object.
(II) (methyl) acrylate monomer (c-3c) organized:
(methyl) acrylic acid dihydro dicyclopentadiene base 2-ethoxyethyl acetate (ジ シ Network ロ ペ Application テ ニ Le オ キ シ エ チ Le (メ タ) ア Network リ レ mono-ト), 1,6-hexanediol two (methyl) acrylate, dipropylene glycol two (methyl) acrylate or tripropylene glycol two (methyl) acrylate etc.
By using above-mentioned (methyl) acrylate monomer (c-3c) as required, the change that according to circumstances can obtain the elastic modulus of the solidfied material that temperature variation causes is less, and has the solidfied material of suitable hardness.
In ultraviolet-curing resin composition of the present invention, these (C) compositions can use one or can be used in combination two or more with arbitrary proportion.
In the present invention, as the more preferably combination of these (C) compositions, for being selected from least one in the group that is made up of the bisphenol-A of carbamate (methyl) acrylate (C-2) (preferred, polyethers carbamate (methyl) acrylate), oxirane 5 to 15 mole, C5 to C18 alkyl (methyl) acrylate and propylene glycol diacrylate, the more preferably combination of at least two kinds.
Usually, in ultraviolet-curing resin composition of the present invention, relative to the total amount of this resin combination, the content of (C) composition is generally 4 to 89 % by weight, and preferably 9 to 84 % by weight, more preferably 19 to 79 % by weight.
In addition, according to circumstances, relative to the total amount of this resin combination, the content of (C) composition can be 30 to 80 % by weight, preferably 40 to 70 % by weight.
In addition, use in (C-1) composition or (C-2) composition any one or will both when combinationally using as (C) composition with (C-3) composition, the content ratio of any one or both usually in (C-1) or (C-2) composition, by the total amount of (C) composition as 100 weight portion time, be respectively about 5 to about 50 weight portions, the preferably ratio of about 10 to about 30 weight portions, all the other are (C-3) composition.By the total amount of (C) composition as 100 weight portion time, (C-3) composition with the ratio of about 20 to about 80 weight portions use, preferably use with the ratio of about 25 to about 75 weight portions.
In the present invention, using the mode that any one in (C-2) composition (carbamate (methyl) acrylate) or (C-3) composition ((methyl) acrylate monomer) or both combinationally use together with (A) composition as (C) composition, it is one of preferred mode.
In addition, in above-mentioned preferred mode, be used as (c-2a) composition that described preferred carbamate (methyl) acrylate is enumerated as carbamate (methyl) acrylate (C-2), and, using preferably ethylene-oxide-modified bisphenol A-type two (methyl) acrylate (c-3a) as the mode of (C-3) composition, is one of preferred mode.
In the present invention, excellent and there is the solidification nitride layer of sufficient hardness in order to obtain recording characteristic, usually preferably containing outside (A) composition and (B) composition, the mode also containing (C) composition.
In above-mentioned, relative to the total amount of resin combination, the ratio of the total of (A) composition and (C) composition is generally more than 70 % by weight, and preferably more than 80 % by weight, more preferably more than 90 % by weight.
In above-mentioned, as preferred mode, can enumerate: relative to the total amount of resin combination, the total of (A) composition, (C-2) composition, (c-3a) composition, (c-3b) composition and (c-3c) composition is generally more than 70 % by weight, the preferably mode of more than 80 % by weight.Now, as ethylene-oxide-modified bisphenol A-type two (methyl) acrylate in (c-3a) composition, the number of repeat unit 5 to 15 of preferred ethylene oxide,1,2-epoxyethane, particularly preferably 10.
In addition, in above-mentioned, as preferred mode, can enumerate: relative to the total amount of (A) composition and (C) composition, (A) component content be greater than 25 % by weight and be less than 90 % by weight mode.
In addition, as one of another preferred mode, can enumerate: relative to the total amount of (A) composition and (C) composition, (C-2) (urethane acrylate) component content think 0 or comprise for the content being less than 30 % by weight mode (more preferably think 0 or be less than 28 % by weight the mode that comprises of content).
In addition, several optimal way (resin combination) comprising the resin combination of the present invention of above-mentioned (A) composition, (B) composition and (C) composition is below recorded.If be not particularly illustrated, " % " expression " % by weight ".
1. a mode, wherein, relative to the total amount of resin combination of the present invention, (A) component content is 10 to 95%, (B) component content is 1 to 10%, and the content of other adjuvant (adjuvant described later) beyond (A) to (C) composition is 0 to 15%, and all the other are (C) composition;
Further, relative to the total amount of (A) composition and (C) composition, (i) (A) component content is greater than 25% and is less than 90%, or the content of urethane acrylate (C-2) (ii) in (C) composition is zero or lower than 30%;
And which does not comprise inorganic or organic filler.
2. as mode described in above-mentioned 1, wherein, as (methyl) acrylate (C), containing (i) following or (ii) in any one or both:
(i) carbamate (methyl) acrylate (c-2a) that obtains of the reaction of polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate;
(ii) polyethylene oxide modified bisphenol A-type diacrylate (c-3a).
3., as the mode described in above-mentioned 2, wherein, the repeat number of the ethylene oxide,1,2-epoxyethane in (c-3a) composition is 5 to 15.
4., as mode described in above-mentioned 2 or 3, wherein, relative to the total amount of (A) composition and (C) composition, the content of (c-2a) is zero or lower than 30 % by weight, (c-2a) is 10 to 85 % by weight with the total content of (c-3a) composition.
5. as mode described any one of above-mentioned 2 to 4, wherein, the content of (A) composition is more than 15 % by weight and less than 90 % by weight; Relative to the total amount of ultraviolet-curing resin composition, the total amount of (A) composition, (c-2a) composition and (c-3a) composition is 70 to 99 % by weight, and (C) component content beyond above-mentioned (c-2a) and (c-3a) composition is 0 to 29 % by weight.
6. mode described any one of above-mentioned 2 to 5, wherein, as the adjuvant beyond (A) to (C) composition, containing hindered amine compound.
7. a mode, wherein, the elastic modulus of solidification nitride layer at 25 DEG C of the ultraviolet-curing resin composition of mode described any one of above-mentioned 2 to 5 is 0.1 to 100MPa.
In CD ultraviolet-curing resin composition of the present invention, as required, also can add rust preventive, antioxidant, organic solvent, silane coupling agent, polymerization inhibitor, levelling agent, antistatic agent, surface lubricant, fluorescer, light stabilizer (such as hindered amine compound), filling agent, for improving the adjuvants such as the adjuvant (such as thiophenols) of permanance.
As hindered amine compound, as long as hindered amine compound, be then not particularly limited, as its concrete example, can exemplify such as: 1,2,2,6,6-pentamethyl-4-piperidine alcohols, 2,2,6,6-tetramethyl-4-piperidine alcohols, (methyl) acrylic acid 1,2,2,6,6-pentamethyl-4-piperidine ester (ア デ カ (Co., Ltd.) makes, LA-82) etc.
Relative to the total amount of resin combination of the present invention, these adjuvants add with the scope of 0 to 15% usually with total amount.
In resin combination of the present invention, comprising hindered amine compound as the mode of light stabilizer is one of optimal way.The content of the hindered amine compound in resin combination of the present invention, relative to the total amount of resin combination, is about 0 to about 5%, preferably about 0.05 to about 2%.
Resin combination of the present invention, due to uses such as the photic zones as Blu-ray Disc, does not therefore comprise the organic or inorganic filling agent hindering light transmission usually.
CD ultraviolet-curing resin composition of the present invention, can each composition described in mixed dissolution at normal temperature to 80 DEG C and obtaining, and also as required snotter can be carried out the operations such as filtration and remove.From the viewpoint of coating, gluing resin combination of the present invention, preferably the mixing ratio of suitable modifying ingredients, makes the viscosity at its 25 DEG C be the scope of 30 to 2000mPas.
CD ultraviolet-curing resin composition of the present invention, can suitably use as the photic zone smears of the laser incidence side of Blu-ray Disc etc.That is, in the Blu-ray Disc with organic pigment recording layer, the upper coating of contact bed (dielectric layer) for being formed on organic pigment recording layer can being suitable as, forming the resin combination use of cured layer.
Specifically, with any means, composition is applied in optical disc substrate by the mode that such as spin-coating method, 2P method, rolling method, silk screen print method etc. are 1 ~ 100 μm with the thickness of the resin of coating.After coating, the light irradiating ultraviolet ~ near ultraviolet (wavelength about 200 ~ about 400nm) from one-sided or two sides is cured.Exposure is preferably about 50 ~ about 1500mJ/cm
2, particularly preferably about 100 ~ about 1000mJ/cm
2.The light source that ultraviolet ~ near ultraviolet light irradiates, as long as irradiate ultraviolet ~ near ultraviolet light, does not then consider its light source.Such as, low pressure, high pressure or ultrahigh pressure mercury lamp, metal halide lamp, (pulse) xenon lamp or electrodeless lamp etc. can be enumerated.
In addition; when photic zone (or protective seam) is made up of the first resin bed formed on recording layer or contact bed and the second resin bed of being formed in face contrary with recording layer or contact bed side viewed from the first resin bed, ultraviolet-curing resin composition of the present invention also can suitably for described first resin bed.Particularly be organic pigment recording layer at recording layer and have thereon in the Blu-ray Disc of contact bed, being suitable as the first resin-cured layer formed on this contact bed.
Now, the thickness of described first resin bed is generally 1 μm ~ 50 μm, preferably 5 μm ~ 40 μm, more preferably 10 μm ~ 30 μm.
In addition, the thickness of described second resin bed is generally 50 μm ~ 100 μm, preferably 60 μm ~ 95 μm, more preferably 70 μm ~ 90 μm.
Protective seam by two-layer form when; as the formation method of protective seam; specifically; with any means, composition is applied in optical disc substrate by the mode that such as spin-coating method, 2P method, rolling method, silk screen print method etc. are 1 μm ~ 30 μm using the thickness of the resin as the first resin bed coating.After coating, the light irradiating ultraviolet ~ near ultraviolet (wavelength about 200 ~ about 400nm) from one-sided or two sides is cured.Exposure is preferably about 50 ~ about 1500mJ/cm
2, particularly preferably about 100 ~ about 1000mJ/cm
2.After solidification, with any means, composition is applied in optical disc substrate by the mode that such as spin-coating method, 2P method, rolling method, silk screen print method etc. are 70 μm ~ 100 μm using the thickness of the resin as the second resin bed coating.After coating, the light irradiating ultraviolet ~ near ultraviolet (wavelength about 200 ~ about 400nm) from one-sided or two sides is cured.Exposure is preferably about 50 ~ about 1500mJ/cm
2, particularly preferably about 100 ~ about 1000mJ/cm
2.In addition, irradiated in the solidification carried out by ultraviolet ~ near ultraviolet light, as long as irradiate the lamp of ultraviolet ~ near ultraviolet light, then do not consider its light source.Such as, low pressure, high pressure or ultrahigh pressure mercury lamp, metal halide lamp, (pulse) xenon lamp or electrodeless lamp etc. can be enumerated.
The solidfied material of resin combination of the present invention, the elastic modulus preferably at 25 DEG C is 0.1 to 100MPa, more preferably 0.1 to 50MPa.
With the CD of the present invention that said method obtains, at least having the plastic support substrates such as carbonic ester containing guiding groove, the reflection horizon that this guiding groove is formed, organic pigment (the being generally azopigment) recording layer that this reflection horizon is formed, the contact bed (dielectric layer) that this recording layer is formed, the CD of the solidification nitride layer (photic zone) of resin combination of the present invention that formed on this contact bed.
In CD of the present invention, on the cured layer of resin combination of the present invention, the cured layer of other resin combination can also be had.Now, photic zone is by the cured layer of resin combination of the present invention and the solidification nitride layer of other resin combination is two-layer is formed.
In CD of the present invention, on the contact bed that the recording layer containing organic pigment (being generally azopigment) is formed, need the cured layer directly forming resin combination of the present invention, effect of the present invention can be realized thus.
As known to those skilled in the art, the layer of contact bed for being formed by inorganicss such as the compounds containing metallic atoms such as zinc.
(embodiment)
Below, further illustrate the present invention by embodiment, but in any case the present invention is not limited to these embodiments.
Embodiment 1 to 4 and comparative example 1
By the composition shown in table 1 with ratio (weight portion) Homogeneous phase mixing shown in table 1, thus, the ultraviolet-curing resin composition of embodiment 1 to 4 and comparative example 1 is prepared.
Use the ultraviolet-curing resin composition of the present invention that obtains, with the method for following (i) (embodiment 1 to 3) and (ii) (embodiment 4), making has the Blu-ray Disc of Pigment Record layer.
In addition, the evaluating characteristics of Blu-ray Disc carries out with method described later, and its result is recorded in table 1.
(i) the making with the Blu-ray Disc of Pigment Record layer of embodiment 1 to 3
1. in the polycarbonate substrate with the diameter 12cm of guiding groove of track pitch 0.32 μm, thickness 1.1mm with the thickness sputtering silver alloy of 100nm, form reflection horizon.Then, by spin-coating method coating, azopigment is dissolved in TFP(tetrafluoropropanol) pigment solution that formed in solvent, form organic Pigment Record layer 80 DEG C of dryings 30 minutes.Again thereon with the sputter thickness ZnS-SiO of about 15nm
2(mol ratio 80:20), forms contact bed, thus makes Blu-ray Disc substrate.
2. Blu-ray Disc substrate is placed on universal stage in contact bed mode upwards, carries out circular cap rock process to cover the mode that internal diameter is 11.5mm, 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, with the velocity range spin coating 4 seconds to 7 seconds of 1000rpm to 1500rpm, be coated with in the mode that each coating film thickness is 25 μm.Spin coating will at the end of carry out twice xenon flash lamp irradiation, be cured to surface without the degree of mobility.
4. use high-pressure sodium lamp, from upside with 400mJ/cm
2irradiate 3 seconds, ultraviolet-curing resin composition of the present invention is solidified completely.
5. be placed on universal stage in the ultraviolet-curing resin composition of the present invention mode upwards after solidification, circular cap rock process is carried out, then by Blu-ray Disc photic zone resin that BRD-864(Nippon Kayaku K. K manufactures to cover mode that internal diameter is 11.5mm) 3.0g is supplied on the cap rock of central part.
6., with the velocity range spin coating 4 seconds to 7 seconds of 1500rpm, be coated with in the mode that coating film thickness is 75 μm.Spin coating will at the end of carry out twice xenon flash lamp irradiation, be cured to surface without the degree of mobility.
7. use high-pressure sodium lamp, from upside with 400mJ/cm
2irradiate 3 seconds, BRD-864 is solidified completely, makes Blu-ray Disc of the present invention.
(ii) the Blu-ray Disc of embodiment 4
There is the making of the Blu-ray Disc of organic pigment recording layer
1. in the polycarbonate substrate with the diameter 12cm of guiding groove of track pitch 0.32 μm, thickness 1.1mm with the thickness sputtering silver alloy of 100nm, form reflection horizon.Then, by spin-coating method coating, azopigment is dissolved in TFP(tetrafluoropropanol) pigment solution that formed in solvent, form organic Pigment Record layer 80 DEG C of dryings 30 minutes.Again with the sputter thickness ZnS-SiO of about 15nm
2(mol ratio 80:20), forms contact bed, thus makes Blu-ray Disc substrate.
2. Blu-ray Disc substrate is placed on universal stage in contact bed mode upwards, carries out circular cap rock process to cover the mode that internal diameter is 11.5mm, 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, with the velocity range spin coating 4 seconds to 7 seconds of 800rpm to 1300rpm, be coated with in the mode that coating film thickness is 100 μm.Spin coating will at the end of carry out twice xenon flash lamp irradiation, be cured to surface without the degree of mobility.
4. use high-pressure sodium lamp, from upside with 400mJ/cm
2irradiate 3 seconds, ultraviolet-curing resin composition of the present invention is solidified completely, makes Blu-ray Disc of the present invention.
(iii) the tracer signal characteristic before and after the endurancing of Blu-ray Disc
By the CD of above-mentioned obtained CD of the present invention and comparative example 1 80 DEG C, place 250 hours under 85%RH environment.Use the Blu-ray Disc signal measuring device ODU-1000 that パ Le ス テ ツク company manufactures, record (long 0.08 μm of 1T) mode continuously with linear velocity 4.92m/s, regenerating power 0.30mW, T and carry out record, and measure the tracer signal characteristic (jitter value) of the Blu-ray Disc before and after endurancing with this determinator, and evaluate with following benchmark.Evaluation result and above-mentioned composition are together represented in following table 1.
Jitter value is one of electric signal of CD, and their numerical value is higher, then represent that the signal data of Blu-ray Disc is poorer, is difficult to the read-write carrying out data when being more than 10%.
The evaluation of jitter value
Zero ... jitter value is lower than 10.0%
× ... jitter value is more than 10.0%
Table 1 resin combination and evaluation result
In addition, each composition represented with abbreviation in table 1 is as described below.
PHE-2: the phenol acrylate of oxirane 2 mole, n=2 in formula, Di-ichi Kogyo Seiyaku Co., Ltd. manufactures
PHE-6: the phenol acrylate of oxirane 6 mole, n=6 in formula, Di-ichi Kogyo Seiyaku Co., Ltd. manufactures
PHE: acrylate, n=1 in formula, Di-ichi Kogyo Seiyaku Co., Ltd. manufactures
UA-1: the urethane acrylate that three compositions of poly-BDO (molecular weight 850), different that Buddhist ketone diisocyanate, acrylic acid 2-hydroxy methacrylate carry out reacting with mol ratio 1:2:2 and obtain.
BPE-10: the bisphenol a diacrylate of oxirane 10 mole, Di-ichi Kogyo Seiyaku Co., Ltd. manufactures
Irgacure
rTM184:1-hydroxycyclohexylphenylketone, Ciba Co., Ltd. manufactures
LA-82: light stabilizer (hindered amine: methacrylic acid 1,2,2,6,6-pentamethyl-4-piperidine ester, rising sun electrification Co., Ltd. manufactures)
PMP:4-mercapto-phenol
(iv) the mensuration of the elastic modulus of resin-cured layer of the present invention
Elastic modulus take JISK7244-5 as benchmark, measures with Measurement of Dynamic Viscoelasticity method.That is, resin combination of the present invention is 1mm with the thickness after solidification mode forms film, uses and merges lamp D bulb (FusionlampDbulb), with 1J/cm
2accumulated light solidification after, make the test film of long 5cm, wide 1cm, thick 1mm size, with SIINanoTechnology company manufacture determination of viscoelasticity device DMS6100 test.Measure and carry out in a flexural mode, measure in the scope of-50 DEG C to 200 DEG C in the condition of amplitude loading 10mN, cycle 1Hz, programming rate 2 DEG C/min.
Embodiment 5 to 7
By the composition shown in table 2 with ratio (weight portion) Homogeneous phase mixing shown in table 2, thus, the ultraviolet-curing resin composition of embodiment 5 to 7 is prepared.
Use the ultraviolet-curing resin composition of the present invention that obtains, with the described method that (i) (embodiment 1 to 3) is identical, make the Blu-ray Disc with Pigment Record layer.
In addition, the evaluating characteristics of Blu-ray Disc is to carry out with described identical method, and its result is recorded in table 2.
Table 2 resin combination and evaluation result
In addition, in the abbreviation in table 2, the abbreviation identical with table 1 is as shown in table 1, and each composition is in addition as follows.
UX-0937: polyethers urethane acrylate (Nippon Kayaku K. K's manufacture)
FA-P270A: (Hitachi Chemical Co., Ltd. makes polypropylene glycol two (methyl) acrylate, trade name FANCRYL
rTMthe repeat number 12 of FA-P270A(propylene glycol units))
The transmissivity of the 405nm light of cured film:
The resin combination obtained with above-described embodiment makes the cured film of 100 μm, uses a point luminometer (U-3310, high-tech Co., Ltd. of Hitachi system), measures the value of the absorbance of this film under 405nm, thus obtain the transmissivity of light.As a result, the transmissivity of the cured film obtained by the composition of embodiment 1 to 7 is more than 85%.
From the result of table 1 and table 2, containing the resin combination of the present invention of embodiment 1 to 7 of (methyl) acrylate with the structure that formula (1) represents, all there is before and after endurancing good tracer signal characteristic.On the other hand, not containing the comparative example 1 of (methyl) acrylate with the structure that general formula (1) represents, good tracer signal characteristic can not be obtained before and after endurancing.
Claims (24)
1. a Blu-ray Disc, wherein, contact bed on organic pigment recording layer is laminated with accessory pigments to recording layer irradiating laser and in the Blu-ray Disc that records of the distortion utilizing the volume change of organic pigment and cause volume change, the solidification nitride layer of ultraviolet-curing resin composition, described ultraviolet-curing resin composition contains:
There is (methyl) acrylate A of the structure that following general formula (1) represents,
In formula, n represents the integer of 2 to 10; With
Photoepolymerizationinitiater initiater B;
Wherein, overall relative to described ultraviolet-curing resin composition, the content of described (methyl) acrylate A is 10 to 95 % by weight.
2. Blu-ray Disc as claimed in claim 1, wherein, the elastic modulus of solidfied material when being solidified by ultraviolet-curing resin composition at 25 DEG C is 0.1 to 100MPa.
3. Blu-ray Disc as claimed in claim 1, it is characterized in that, also containing (methyl) acrylate C beyond described (methyl) acrylate A, described (methyl) acrylate C is selected from epoxy (methyl) acrylate C-1, carbamate (methyl) acrylate C-2, and A composition, (methyl) acrylate compounds beyond C-1 composition and C-2 composition, described " A composition, (methyl) acrylate compounds beyond C-1 composition and C-2 composition " be selected from A composition, simple function beyond C-1 composition and C-2 composition or multifunctional (methyl) acrylate.
4. Blu-ray Disc as claimed in claim 3, wherein, described (methyl) acrylate C is any one or both in following (i) or (ii):
The reaction product c-2a of (i) polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate c-3a.
5. Blu-ray Disc as claimed in claim 3, wherein, as (methyl) acrylate C beyond described (methyl) acrylate A, not containing carbamate (methyl) acrylate C-2, or when containing carbamate (methyl) acrylate C-2, relative to the total amount of described A composition and described C composition, its content is lower than 30 % by weight.
6. Blu-ray Disc as claimed in claim 4, wherein, c-3a composition to be the number of repeat unit of polyethylene oxide be 5 to 15 polyethylene oxide modified bisphenol A-type diacrylate.
7. Blu-ray Disc as claimed in claim 3, wherein, relative to the total amount of A composition and C composition, A component content is greater than 25 % by weight and is less than 90 % by weight.
8. Blu-ray Disc as claimed in claim 3, wherein,
Relative to the total amount of ultraviolet-curing resin composition, B component content is the content of other adjuvant beyond 1 to 10 % by weight, A to C composition is 0 to 15 % by weight, and all the other are C composition;
And, relative to the total amount of A composition and C composition, i () A component content is greater than 25 % by weight and is less than 90 % by weight, or the content of carbamate (methyl) acrylate C-2 in (ii) C composition is zero or lower than 30 % by weight;
And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
9. Blu-ray Disc as claimed in claim 3, wherein,
As (methyl) acrylate C beyond A composition, containing any one in following (i) or (ii) or both:
The reaction product c-2a of (i) polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate c-3a;
The repeat number of the ethylene oxide,1,2-epoxyethane in c-3a composition is 5 to 15;
Relative to the total amount of A composition and C composition, the content of c-2a composition is that 10 to 85 % by weight, A component contents are more than 15 % by weight and less than 90 % by weight lower than the total content of 30 % by weight, c-2a compositions and c-3a composition;
Relative to the total amount of ultraviolet-curing resin composition, the total amount of A composition, c-2a composition and c-3a composition is 70 to 99 % by weight, the content of the C composition beyond described c-2a composition and c-3a composition is 0 to 29 % by weight, and the content of Photoepolymerizationinitiater initiater B is 1 to 10 % by weight;
And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
10. Blu-ray Disc as claimed in claim 3, wherein,
As described (methyl) acrylate C, comprise at least one be selected from group that (methyl) acrylate monomer c-3c of being organized by carbamate (methyl) acrylate C-2,5 to 15 moles of polyethylene oxide modified bisphenol A-type diacrylate i.e. c-3a of 5 to 15 mole, (methyl) acrylate monomer c-3b that following (I) organizes and following (II) forms;
And, relative to the total amount of ultraviolet-curing resin composition, the total content of the content and A component content that are selected from least one in described group is 70 to 99 % by weight, and B component is 1 to 10 % by weight, and (methyl) other than the above acrylate C is 0 to 10 % by weight;
(I) group:
(i) C5 to C18 alkyl (methyl) acrylate or C7 to C18 alkylene glycol two (methyl) acrylate,
(ii) there is (methyl) acrylate of poly-BDO structure or (methyl) acrylate of epoxy pronane modification,
(iii) (methyl) acrylate of caprolactone modification;
(II) group:
(methyl) acrylic acid dihydro dicyclopentadiene base 2-ethoxyethyl acetate, 1,6-hexanediol two (methyl) acrylate, dipropylene glycol two (methyl) acrylate or tripropylene glycol two (methyl) acrylate.
11. Blu-ray Discs as claimed in claim 10, wherein,
(methyl) acrylate monomer c-3b that described (I) organizes is for being selected from least one in the group that is made up of following (methyl) acrylate:
(i) (methyl) Isooctyl acrylate monomer, (methyl) isoamyl acrylate, (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) acrylate, 1,9-nonanediol two (methyl) acrylate and 1,10-decanediol two (methyl) acrylate;
(ii) neopentyl glycol two (methyl) acrylate of nonyl phenyl (methyl) acrylate of polypropylene glycol (methyl) acrylate, polypropylene glycol two (methyl) acrylate, polypropylene oxide, polypropylene oxide, 1,6-hexanediol two (methyl) acrylate of polypropylene oxide, bisphenol A-type two (methyl) acrylate of polypropylene oxide and methoxyl tripropylene glycol (methyl) acrylate;
(iii) dipentaerythritol six (methyl) acrylate of (methyl) hydroxy butyl acrylate of (methyl) Hydroxyethyl Acrylate of caprolactone modification, caprolactone modification, 3-hydroxypivalic acid DOPCP two (methyl) acrylate of caprolactone modification, three (acrylyl oxy-ethyl) isocyanuric acid esters of caprolactone modification and caprolactone modification.
12. Blu-ray Discs as claimed in claim 4, wherein, the molecular weight of polyester polyol or polyether glycol is the scope of 200 to 3000.
13. 1 kinds of ultraviolet-curing resin compositions for the application in the volume change of accessory pigments to recording layer irradiating laser and in the Blu-ray Disc that records of the distortion utilizing the volume change of organic pigment and cause, described ultraviolet-curing resin composition contains:
(methyl) acrylate A that following general formula (1) represents,
In formula, n represents the integer of 2 to 10; With
Photoepolymerizationinitiater initiater B;
Wherein, overall relative to described ultraviolet-curing resin composition, the content of described (methyl) acrylate A is 10 to 95 % by weight.
14. apply as claimed in claim 13, and wherein, the elastic modulus of solidfied material when being solidified by ultraviolet-curing resin composition at 25 DEG C is 0.1 to 100MPa.
15. apply as claimed in claim 13, it is characterized in that, described ultraviolet-curing resin composition is also containing (methyl) acrylate C beyond described (methyl) acrylate A, described (methyl) acrylate C is selected from epoxy (methyl) acrylate C-1, carbamate (methyl) acrylate C-2, and A composition, (methyl) acrylate compounds beyond C-1 composition and C-2 composition, described " A composition, (methyl) acrylate compounds beyond C-1 composition and C-2 composition " be selected from A composition, simple function beyond C-1 composition and C-2 composition or multifunctional (methyl) acrylate.
16. apply as claimed in claim 15, and wherein, described (methyl) acrylate C is any one or both in following (i) or (ii):
The reaction product c-2a of (i) polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate c-3a.
17. apply as claimed in claim 15, wherein, as (methyl) acrylate C beyond described (methyl) acrylate A, not containing carbamate (methyl) acrylate C-2, or when containing carbamate (methyl) acrylate C-2, relative to the total amount of described A composition and described C composition, its content is lower than 30 % by weight.
18. apply as claimed in claim 16, wherein, c-3a composition to be the number of repeat unit of polyethylene oxide be 5 to 15 polyethylene oxide modified bisphenol A-type diacrylate.
19. apply as claimed in claim 15, and wherein, relative to the total amount of A composition and C composition, A component content is greater than 25 % by weight and is less than 90 % by weight.
20. apply as claimed in claim 15, wherein,
Relative to the total amount of ultraviolet-curing resin composition, B component content is the content of other adjuvant beyond 1 to 10 % by weight, A to C composition is 0 to 15 % by weight, and all the other are C composition;
And, relative to the total amount of A composition and C composition, i () A component content is greater than 25 % by weight and is less than 90 % by weight, or the content of carbamate (methyl) acrylate C-2 in (ii) C composition is zero or lower than 30 % by weight;
And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
21. apply as claimed in claim 15, wherein,
As (methyl) acrylate C beyond A composition, containing any one in following (i) or (ii) or both:
The reaction product c-2a of (i) polyester polyol or polyether glycol and polyisocyanates and acrylic acid 2-hydroxy methacrylate,
(ii) polyethylene oxide modified bisphenol A-type diacrylate c-3a;
The repeat number of the ethylene oxide,1,2-epoxyethane in c-3a composition is 5 to 15;
Relative to the total amount of A composition and C composition, the content of c-2a composition is that 10 to 85 % by weight, A component contents are more than 15 % by weight and less than 90 % by weight lower than the total content of 30 % by weight, c-2a compositions and c-3a composition;
Relative to the total amount of ultraviolet-curing resin composition, the total amount of A composition, c-2a composition and c-3a composition is 70 to 99 % by weight, the content of the C composition beyond described c-2a composition and c-3a composition is 0 to 29 % by weight, and the content of Photoepolymerizationinitiater initiater B is 1 to 10 % by weight;
And this ultraviolet-curing resin composition does not comprise organic or inorganic filler.
22. apply as claimed in claim 15, wherein,
As described (methyl) acrylate C, comprise at least one be selected from group that (methyl) acrylate monomer c-3c of being organized by carbamate (methyl) acrylate C-2,5 to 15 moles of polyethylene oxide modified bisphenol A-type diacrylate i.e. c-3a of 5 to 15 mole, (methyl) acrylate monomer c-3b that following (I) organizes and following (II) forms;
And, relative to the total amount of ultraviolet-curing resin composition, the total content of the content and A component content that are selected from least one in described group is 70 to 99 % by weight, and B component is 1 to 10 % by weight, and (methyl) other than the above acrylate C is 0 to 10 % by weight;
(I) group:
(i) C5 to C18 alkyl (methyl) acrylate or C7 to C18 alkylene glycol two (methyl) acrylate,
(ii) there is (methyl) acrylate of poly-BDO structure or (methyl) acrylate of epoxy pronane modification,
(iii) (methyl) acrylate of caprolactone modification;
(II) group:
(methyl) acrylic acid dihydro dicyclopentadiene base 2-ethoxyethyl acetate, 1,6-hexanediol two (methyl) acrylate, dipropylene glycol two (methyl) acrylate or tripropylene glycol two (methyl) acrylate.
23. apply as claimed in claim 22, wherein,
(methyl) acrylate monomer c-3b that described (I) organizes is for being selected from least one in the group that is made up of following (methyl) acrylate:
(i) (methyl) Isooctyl acrylate monomer, (methyl) isoamyl acrylate, (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) acrylate, 1,9-nonanediol two (methyl) acrylate and 1,10-decanediol two (methyl) acrylate;
(ii) neopentyl glycol two (methyl) acrylate of nonyl phenyl (methyl) acrylate of polypropylene glycol (methyl) acrylate, polypropylene glycol two (methyl) acrylate, polypropylene oxide, polypropylene oxide, 1,6-hexanediol two (methyl) acrylate of polypropylene oxide, bisphenol A-type two (methyl) acrylate of polypropylene oxide and methoxyl tripropylene glycol (methyl) acrylate;
(iii) dipentaerythritol six (methyl) acrylate of (methyl) hydroxy butyl acrylate of (methyl) Hydroxyethyl Acrylate of caprolactone modification, caprolactone modification, 3-hydroxypivalic acid DOPCP two (methyl) acrylate of caprolactone modification, three (acrylyl oxy-ethyl) isocyanuric acid esters of caprolactone modification and caprolactone modification.
24. apply as claimed in claim 16, and wherein, the molecular weight of polyester polyol or polyether glycol is the scope of 200 to 3000.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-017577 | 2010-01-29 | ||
| JP2010017577 | 2010-01-29 | ||
| PCT/JP2011/000401 WO2011093063A1 (en) | 2010-01-29 | 2011-01-26 | Blu-ray disc, uv-curable resin composition therefor, and cured resin |
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| Publication Number | Publication Date |
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| CN102741929A CN102741929A (en) | 2012-10-17 |
| CN102741929B true CN102741929B (en) | 2016-02-17 |
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| JP (1) | JP4977807B2 (en) |
| CN (1) | CN102741929B (en) |
| SG (1) | SG181738A1 (en) |
| TW (1) | TWI495696B (en) |
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| JP2013242941A (en) * | 2012-05-22 | 2013-12-05 | Nippon Kayaku Co Ltd | Ultraviolet-curable resin composition |
| CN103709831B (en) * | 2014-01-09 | 2015-07-01 | 东周化学工业（昆山）有限公司 | Ultraviolet-curable jet printing ink |
| EP3601442A1 (en) * | 2017-03-28 | 2020-02-05 | Arkema France | Compositions useful for forming soft touch coatings |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1844229A (en) * | 2006-05-16 | 2006-10-11 | 广东工业大学 | UV curable aqueous resin composition |
| CN101490759A (en) * | 2006-07-10 | 2009-07-22 | 日本化药株式会社 | Ultraviolet-curable resin composition and use thereof |
| WO2009144926A1 (en) * | 2008-05-30 | 2009-12-03 | 日本化薬株式会社 | Ultraviolet-curing resin composition for optical disk, cured material and optical disk |
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| JP4783327B2 (en) * | 2007-04-19 | 2011-09-28 | 太陽誘電株式会社 | Optical information recording medium |
| EP2302003A4 (en) * | 2008-05-30 | 2011-11-02 | Mitsubishi Kagaku Media Co Ltd | Azo metal chelate dye and optical recording medium |
| JP2010009271A (en) * | 2008-06-26 | 2010-01-14 | Oki Semiconductor Co Ltd | Image processor |
| JP2010009721A (en) * | 2008-06-30 | 2010-01-14 | Toshiba Corp | Write once information recording medium |
-
2011
- 2011-01-26 CN CN201180007767.1A patent/CN102741929B/en not_active Expired - Fee Related
- 2011-01-26 JP JP2011551758A patent/JP4977807B2/en not_active Expired - Fee Related
- 2011-01-26 WO PCT/JP2011/000401 patent/WO2011093063A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1844229A (en) * | 2006-05-16 | 2006-10-11 | 广东工业大学 | UV curable aqueous resin composition |
| CN101490759A (en) * | 2006-07-10 | 2009-07-22 | 日本化药株式会社 | Ultraviolet-curable resin composition and use thereof |
| WO2009144926A1 (en) * | 2008-05-30 | 2009-12-03 | 日本化薬株式会社 | Ultraviolet-curing resin composition for optical disk, cured material and optical disk |
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| TWI495696B (en) | 2015-08-11 |
| SG181738A1 (en) | 2012-07-30 |
| TW201139575A (en) | 2011-11-16 |
| WO2011093063A1 (en) | 2011-08-04 |
| JP4977807B2 (en) | 2012-07-18 |
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| CN102741929A (en) | 2012-10-17 |
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