WO1992000588A1 - Disque optique - Google Patents

Disque optique Download PDF

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Publication number
WO1992000588A1
WO1992000588A1 PCT/JP1991/000886 JP9100886W WO9200588A1 WO 1992000588 A1 WO1992000588 A1 WO 1992000588A1 JP 9100886 W JP9100886 W JP 9100886W WO 9200588 A1 WO9200588 A1 WO 9200588A1
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WO
WIPO (PCT)
Prior art keywords
weight
curable resin
resin composition
acrylate
optical disc
Prior art date
Application number
PCT/JP1991/000886
Other languages
English (en)
Japanese (ja)
Inventor
Tsuneo Hagiwara
Utami Yonemura
Eiichi Hashimoto
Original Assignee
Teijin Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2172656A external-priority patent/JPH0467329A/ja
Priority claimed from JP2172657A external-priority patent/JPH0467330A/ja
Priority claimed from JP2172658A external-priority patent/JPH0467331A/ja
Priority claimed from JP2172655A external-priority patent/JPH0467328A/ja
Priority claimed from JP3033371A external-priority patent/JPH04247338A/ja
Priority claimed from JP3033368A external-priority patent/JPH04247336A/ja
Priority claimed from JP3033369A external-priority patent/JPH04247337A/ja
Application filed by Teijin Limited filed Critical Teijin Limited
Publication of WO1992000588A1 publication Critical patent/WO1992000588A1/fr

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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/254—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

Definitions

  • the present invention relates to an optical disc that records and reproduces information using light such as a laser beam.
  • Optical discs are attracting attention as high-density, large-capacity information recording media, and various types of optical discs are being researched and developed. Among them, erasable and rewritable magneto-optical discs have a wide range of applications and great expectations for the future. Various materials and systems have already been announced and their practical use has begun.
  • optical discs need to be subjected to antistatic treatment to prevent dust and the like from adhering.
  • an antistatic agent is applied to the surface of the substrate, or the antistatic agent is kneaded into the substrate.
  • the former treatment has a problem in durability, and the latter treatment has problems in moldability and light transmittance.
  • the substrate of an optical disc is generally made of polycarbonate resin or the like, the surface hardness of the substrate is moderate. No. Therefore, it has been proposed to form a hard coat layer using a UV curable resin or the like as a surface hardening treatment to avoid surface damage.
  • a UV curable resin or the like as a surface hardening treatment to avoid surface damage.
  • the resin is charged due to friction with the air while the disk is rotating, and there are many dirt and dust on the read surface due to the adhesion of dust. There is a problem that reduces reliability.
  • the formation of the hard coat layer is performed in a clean room because the optical disc is extremely unlikely to adhere or mix foreign matter such as dust in terms of reliability. Under these constraints, the use of solvents and high temperatures is not preferred.
  • the present inventors have developed a low-viscosity curable resin composition which can be applied as a thin film even in a solvent-free manner from the above-mentioned objects, particularly from the viewpoint of coatability.
  • a curable composition containing a specific mono (meth) acrylate monomer has excellent surface hardness and low surface electric resistance, and has reached the present invention.
  • the present invention provides the following specific items of the first invention.
  • the present invention is based on a hard coat layer of an acrylic ester and comprises three inventions including two inventions of a hard coat layer of a composition derived therefrom.
  • the first invention provides an optical disc having a hard coat layer formed on at least a light irradiation surface (read surface), wherein the hard coat layer has the following formula (e):
  • R 1 and R 2 represent a hydrogen atom or a methyl group, and n represents an integer of 1 to 23. ]
  • a second invention provides an optical disc having the same configuration as the first invention, wherein the hard coat layer has the following formula ( ⁇ ):
  • R 1 and R 2 represent a hydrogen atom or a methyl group
  • R 3 represents an alkyl group having 1 to 9 carbon atoms, a phenyl group, a phenyl group substituted with an alkyl group having 1 to 9 carbon atoms, A phenyl group substituted with an alkoxy group of
  • the third invention also provides an optical disc having the same configuration as the first invention, wherein the hard coat layer has the following formula ( ⁇ ) ft 1 R 2
  • R 1 and R 2 represent a hydrogen atom or a methyl group
  • n represents an integer of 1 to 23
  • m represents an integer of 1 or 2.
  • An antistatic composition obtained by curing a curable resin composition containing 0.1 to 60% by weight of a mono (meth) acrylate monodiphosphate compound of polyethylene glycol or polypropylene glycol represented by the following formula: Is a paint film An optical disc characterized by the above-mentioned.
  • the optical disc of the present invention includes a pit-type optical disc known as a compact disc ⁇ CD> composed of a recording medium having pits formed on a substrate made of glass, resin, or the like, and a thermal recording layer formed on the substrate. From a recording medium on which a bubble is formed by irradiating a laser beam, etc., and a bubble-tired optical disk that detects a level change based on a change in reflected light, or a recording medium on which a magneto-optical recording layer is formed on a substrate And other magneto-optical disks.
  • a pit-type optical disc known as a compact disc ⁇ CD> composed of a recording medium having pits formed on a substrate made of glass, resin, or the like, and a thermal recording layer formed on the substrate. From a recording medium on which a bubble is formed by irradiating a laser beam, etc., and a bubble-tired optical disk that detects a level change based on a change in reflected light, or
  • an organic resin substrate such as polycarbonate, polymethyl methacrylate, or amorphous polyolefin is used.
  • the recording surface of an optical disk is a surface on which a recording layer is formed on a substrate.
  • the surface opposite to the recording surface, that is, the light irradiation surface (read surface) is, for example, a flat surface without a groove formed on a magneto-optical disk.
  • a mono (meth) acrylic acid ester of polyethylene glycol or polypropylene dalicol of the formula (E) [In the present invention, the (meth) acrylic acid ester is an acrylic acid ester and Represents a methacrylic acid ester] as long as it has a necessary antistatic property.
  • the content when the antistatic property is imparted only with a mono (meth) acrylate of polyethylene glycol or polypropylene glycol of the formula (I) without containing an anionic surfactant or the like described below is 5 to 7 0% by weight is preferred, and more preferably 20 to 4% by weight, and if less than 5% by weight, the antistatic effect is insufficient, while if more than 70% by weight, the composition is coated and cured. The surface hardness of the resulting optical disc is insufficient, which is not preferable.
  • R 1 and R 2 in the formula (e) are a hydrogen atom or a methyl group, taking into account their UV curability, compatibility with the resin used in combination, and the surface electrical resistance and surface hardness of the cured product. Is chosen. n is an integer of 1 to 23, preferably 4 to 6. A (meth) acrylate in this range has the highest compatibility and gives a coating film having a low surface electric resistance.
  • the content of the ether derivative of the mono (meth) acrylate of polyethylene glycol or polypropylene glycol represented by the formula (H) in the curable resin composition is 5 to 70. % By weight, preferably from 10 to 60% by weight, particularly preferably from 15 to 50% by weight.
  • the compound is less than 5% by weight, the antistatic effect is insufficient, and on the other hand, it exceeds 70% by weight.
  • the surface hardness of the optical disk coated with the curable resin composition is insufficient, which is not preferable.
  • n is an integer of 5 to 23. Among them, n is preferably from 20 to 20. If n, which represents an alkylene glycol unit, is less than 5, the dalicol residue has low hydrophilicity and does not exhibit sufficient static elimination properties. On the other hand, if n exceeds 23, the solubility decreases, which is not preferable.
  • R 1 and R 2 represent a hydrogen atom or a methyl group
  • R 3 represents an alkyl group having 1 to 9 carbon atoms, a phenyl group, and a carbon number.
  • a phenyl group substituted with an alkyl group having 1 to 9 carbon atoms and a phenyl group substituted with an alkoxy group having 1 to 9 carbon atoms.
  • Examples of the alkyl group having 1 to 9 carbon atoms in R 3 include a methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl group and the like, which may be branched. Of these, a methyl, ethyl, propyl, or butyl group having 1 to 4 carbon atoms is preferred. Further, a phenyl group substituted with an alkyl group having 1 to 9 carbon atoms includes: Examples include diphenyl, butylphenyl, methylphenyl and the like.
  • Examples of the ether derivative of the mono (meth) acrylate ester of polyethylene daricol or polypropylene glycol represented by the formula (E) include:
  • CH 2 C-C0 (0CH 2 CH 2 ) a 0C 2 H 5
  • CH 2 CHC0 (0CH 2 CH 2 ) a 0C 2 H 5 CH 3
  • n 5 to 23
  • Pli represents a p-phenylene group.
  • CH 2 C-CO (OCH 2 CH 2 ) 8 OPI1C9 H19, but not limited thereto.
  • the content of the mono (meth) acrylate compound of the polyethylene (glycol) or polypropylene glycol represented by the formula (M) in the curable resin composition is 0.1 to 0.1%.
  • the amount is preferably 6% by weight, more preferably 0.2 to 50% by weight, and particularly preferably 0.5 to 50% by weight. ⁇ If the content exceeds 10% by weight, the surface hardness of the coated optical disk is insufficient, which is not preferable.
  • R 1, ⁇ . 2 is also hydrogen atom a methyl group
  • n represents an integer of 1 to 23
  • m is an integer of 1 or 2.
  • n is preferably 1 to 15 and particularly preferably 1 to 1.
  • a mono- or diphosphate compound of a ter compound for example,
  • CH 2 CH-C0 (0CH 2 CH) a 0P (0H) 2 CH 3
  • n represents an integer of from 0.1 to 23].
  • the phosphoric ester compound is an ethylene glycol mono (meth) acrylic acid ester phosphoric acid monoester compound of the formula ( ⁇ /), which is a 1: 1 adduct of an organic amine compound. Contained in curable resin composition By doing so, the antistatic performance and, consequently, the surface hardness can be improved.
  • the content of the adduct in the curable resin composition is from 0.1 to '20% by weight, preferably from 0.2 to 15% by weight, particularly preferably from 0.5 to 10% by weight. If the amount of the adduct is less than 0.1% by weight, the antistatic effect is insufficient, while if it exceeds 20% by weight, it becomes difficult to be compatible with the curable resin, which is not preferable from the viewpoint of coatability.
  • CH 2 C- C00CH 2 CH 2 OP (OH) 2 /
  • CH 2 C- COOCH2 CH 2 OP (OH) 2 /
  • CH 2 C- C00CH 2 CH 2 N (C 2 H 5 ) 2
  • CH 2 C- COOCH2 CH 2 0P (0H) 2 / H 2 N CH 2 CH 2 OH CH 3
  • CH 2 C- COOCH2 CH 2 0P ⁇ 0H ⁇ 2 Z (C 2 H 5 ) 3 N And the like.
  • polymerizable monomers polymerizable oligomers
  • polymerizable copolymers are used.
  • Multifunctional oligoester acrylate polyfunctional polyacrylate, acrylate modified phosphazene compound, polyfunctional acrylate of isocyanuric acid, etc.
  • Use may be made of vinyl polymerizable compounds, acrylic polymerizable compounds, etc. These polymerizable compounds may be used alone or as a mixture.
  • the curable resin composition of the present invention is used by adding a radical polymerization initiator such as a photopolymerization initiator and a thermal polymerization initiator, if necessary.
  • a radical polymerization initiator such as a photopolymerization initiator and a thermal polymerization initiator
  • the antistatic performance and A curable resin composition having the following composition is preferred from the viewpoint of both surface hardness and surface hardness, and further from the viewpoint of film forming properties.
  • the (meth) acrylic acid ester of the formula (I) has n of 4 to 6, and the other components of the curable resin composition include dipentaerythritol hexaacrylate or its allolactone. It is a curable resin composition comprising a modified product, if necessary, a polymerizable diluent other than these, and a polymerization initiator.
  • Dipentaerythritol hexacrylate or its modified allolactone is suitable in that it has relatively low clay and high curability, and among these, the modified allolactone is more preferable.
  • the modified force allolactone is represented by the following formula.
  • CA30, DPCA60, and DPCA120 are dipentaerythritols modified with 2, 3, 6, and 12 molecules of force prolactone, respectively, on average, and have low skin irritation and low odor.
  • the curing speed is extremely fast, and the cured product is Since it shows flexibility despite its high hardness, it gives cured products with excellent weather resistance. Furthermore, since the viscosity is low, the coatability is good when the composition is formed.
  • the content of this component in the curable resin composition is 40 to 80% by weight, preferably 50 to 80% by weight. Above this, the surface electric resistance of the coating film is undesirably high. In addition, if it is lower than that, it is not preferable because the surface hardness of the coating film cannot be increased.
  • the polymerizable diluent is used as needed for the purpose of lowering the viscosity at the time of applying the curable resin composition. Therefore, low-viscosity (meth) acrylates having 1 to 3 functionality are used.
  • Component (a) the (meth) acrylate and component (b) the dipentaerythr Retile (meta) Depends on the type and composition of acrylate
  • a (meth) acrylate having a viscosity of 10 vise or less, preferably 5 poise or less, at 25 C measured by a 13-type viscometer is used.
  • hexamethylene glycol diacrylate, tetrahydrofurfuryl acrylate, hexamethylene glycol dimethacrylate, tetrahydrofurfuryl methacrylate, and trimethylethyl-1-fluoropropria Preferably used are acrylate, neopentyl glycol hydroxypivalate, glyceryl dimethacrylate, neopentyl glycol dimethacrylate, neopentyl glycol dimethacrylate, and pentaerythritol tetraacrylate.
  • hexamethylene glycol diacrylate and tetrahydrofuryl acrylate are particularly suitably used for improving the adhesion of the cured product to the polycarbonate substrate and adjusting the viscosity of the composition.
  • the amount of the polymerizable diluent used as the component (c) is 0 to 40% by weight, preferably 0 to 30% by weight of the curable resin composition including the case where it is not used. Above that, the surface hardness increases depending on the type, but the surface electric resistance does not decrease and the adhesion to the substrate is deteriorated. Thus, the polymerization initiator is not preferable.
  • Acrylic The acid ester, the dipentaerythritol (meta) acrylate of the component (b), and the polymerizable diluent of the component (C) are preferably 0.1 to 10 phr (weight.part per hundred resin) based on the total weight. Is 0.5 to 7 phr, more preferably 2 to 5 phr.
  • photopolymerization initiator examples include benzophenone-based initiators such as benzophenone and Michler's ketone; diketone-based initiators such as benzyl and phenylmethoxydiketone; acetphenone-based initiators such as acetophenone; benzoinethyl ether and benzyldimethine.
  • Benzoin-based initiators such as / reketane / re, thioxanthone-based initiators such as 2,4-getylthioxanthone, and quinone-based initiators such as 2-methylanthraquinone and camphorquinone are preferably used.
  • an accelerator such as an amine accelerator can be used in combination.
  • azobisdisbutyronitrile ⁇ AIBN> benzoylperoxide (BPO), cumene hydroperoxide, dicumyl peroxyloxide, dibutyl butylperoxide Oxide, peryl yl beloxide and the like.
  • anionic surfactant saturated and non-saturated Saturated fatty acid metal salts, saturated or unsaturated aliphatic sulfonates, aromatic sulfonates that may have substituents, sulfonates containing ethylene glycol units, and sulfur containing various substituents —Salt sodium salt.
  • anionic surfactants saturated and non-saturated Saturated fatty acid metal salts, saturated or unsaturated aliphatic sulfonates, aromatic sulfonates that may have substituents, sulfonates containing ethylene glycol units, and sulfur containing various substituents —Salt sodium salt.
  • fatty acid tests such as sodium alkyl ether sulfonate, alkyl sulfate sodium salt, sodium alkyl ether sulfate, potassium oleate and potassium coconut fatty acid, among which sulfonic acid salt compounds and sulfate ester salt compounds are preferred. Good.
  • the content of the anionic surfactant is determined by the formula of the component (a).
  • (I) 0.01 to 200% by weight, more preferably 0.1 to 200% by weight, based on the amount of the (meth) acrylic acid ester in (I).
  • (meth) acrylate of the component (a), dipentaerythritol of the component (b) and the component (c) )) Is 0.0 ° to 1 to 10% by weight based on the total weight of the polymerizable diluent.
  • the content of the component (a) in the curable resin composition is determined when the component (e) is not used.
  • the preferred range is from 3 to 40% by weight, and the component (a) is less than 3% by weight.
  • the curable resin composition of the present invention described above can coat the surface of the optical disc by a known spin coating method, dip coating method, coating with a doctor knife, or a method with a bar coater.
  • the spin coating method is practically most preferable because the film thickness is easily controlled.
  • covering the side surface of the optical disk also improves the antistatic effect.
  • the viscosity of the curable resin composition is measured at 25 C using a B-type viscometer. Is less than 20 boys, preferably less than 10 boys, more preferably less than 5 boys. Above that, it is not preferable because the coating film cannot be controlled smoothly.
  • the thickness of the cured coating film of the present invention is 1 to 30 m, preferably 5 to 25 m. If it is lower than this, sufficient performance is not exhibited in terms of hardness, and if it is higher than this, not only is it difficult to control the film thickness, but also the internal curability decreases, which is not preferable.
  • the optical disk coated with the composition is cured by known methods and conditions using an active lamp such as an ultraviolet lamp such as a low-pressure mercury lamp, a medium-pressure mercury lamp, and a high-pressure mercury lamp, a halogen lamp, an electron beam, or a heat treatment. .
  • an active lamp such as an ultraviolet lamp such as a low-pressure mercury lamp, a medium-pressure mercury lamp, and a high-pressure mercury lamp, a halogen lamp, an electron beam, or a heat treatment.
  • actinic rays such as an ultraviolet lamp, a halogen lamp, and an electron beam from the viewpoint of operability and productivity.
  • the antistatic property in the present invention may be any as long as foreign substances such as dust and dust do not adhere to the surface. This is displayed in detail on the surface resistivity, 1 0 1 5 ⁇ ⁇ ⁇ less than the optical disc, preferably it is said that less than 1 0 1 4 ⁇ ⁇ ]. It is said that the surface hardness must be small enough not to cause scratches due to normal handling, specifically cleaning the surface with a cloth, or catching with a nail. 'Specifically, this can be represented by the pencil hardness specified in JIS standard, and is generally HB or more, preferably F or more. In the present invention, these are used as criteria. As described above, the present invention can provide an optical disc having an antistatic ability with a high degree of durability and a sufficient surface hardness. BEST MODE FOR CARRYING OUT THE INVENTION
  • the surface resistance () is J I S K
  • the pencil hardness was measured using a Mitsubishi Pencil-made unit. Parentheses after the compound indicate the names of commercial products actually used and the manufacturer's name.
  • a curable resin composition (NSC-710, manufactured by Nippon Seika Co., Ltd.) and the following various objects (meta) are placed on the flat surface of a polycarbonate substrate with a thickness of 1.2 mm and a diameter of 13 OM.
  • Acrylic ester, its phosphoric ester, or a mixture of a 1: 1 adduct of it and an organic amine compound with each of the copolymerized monomers is applied by spin coating to a thickness of about 1 O ⁇ tm.
  • ultraviolet rays were irradiated from a height of 20 cm for 1 minute using a high-pressure mercury lamp of about 27 cm in length and 2 Kw to cure the coating film.
  • CH 2 C- C00CH 2 CH 2 0P (0H) 2 /
  • CH 2 C- C00CH 2 CH 2 N (CH 3) 2
  • CH 2 C- C00CH 2 CH 2 0P (0H) 2 /
  • CH 2 C- COOCH2 CH 2 0P (0H) 2 / H 2 NCH 2 CH 2 OH
  • Comparative Example 1 was a case where the copolymerized monomer was not added, and Comparative Example 2 was a solution in which a kneading-type antistatic agent sorbitan laurate (Newcol 20, manufactured by Nippon Emulsion Co., Ltd.) was dissolved in alcohol on a polycarbonate substrate. And apply, dry It is a thing.
  • a kneading-type antistatic agent sorbitan laurate Newcol 20, manufactured by Nippon Emulsion Co., Ltd.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • Hexafunctional urethane acrylate oligomer (U1226, manufactured by Shin-Nakamura Chemical Co., Ltd.) 40% by weight, Hexafunctional acrylate oligomer (KAY AR AD DPCA60, manufactured by Nippon Kayaku Co., Ltd.) 20% by weight, and tetraethylene glycol mono Methacrylate (Blemmer PE 200, manufactured by Nippon Oil & Fats Co., Ltd.) 40% by weight, photoinitiator ⁇ -hydroxyisobutylphenone (Darocur 1 173, manufactured by Merck) 3 Phr of curable resin composition of thickness 1
  • a flat surface of a polycarbonate substrate having a diameter of 2 mm and a diameter of 13 ⁇ M was applied to a thickness of about 1 ⁇ m by a spin coating method, and was photocured in the same manner as in Examples 1-21.
  • the surface hardness of the cured surface of the substrate was HB, and the surface resistance was 2.1 ⁇ 10 13 ⁇ . ⁇ .
  • Hexaacrylate of phosphazene (U-1000, Made by Idemitsu Petrochemical Co., Ltd.> 40% by weight, tetraaropyrene glycol monomethacrylate ⁇ Blemmer PP—
  • a curable resin composition consisting of 330%, manufactured by Nippon Oil & Fat Co., Ltd., 60% by weight, and a photoinitiator, Irgaki Yua 907 (manufactured by Ciba Geigy Co., Ltd.), 5 phr, was applied to a polycarbonate substrate in the same manner as in Example 22,
  • the cured coating film had a surface hardness of HB and a surface resistance of 3.6 X 10 ⁇ / ⁇ .
  • Hexaacrylate of phosphazene (U-100, manufactured by Idemitsu Petrochemical Co., Ltd.) 30% by weight, tetraethylene glycol monomethacrylate (Blemma 1-200, manufactured by NOF Corporation) 70% by weight, Photoinitiator Irgacure
  • a curable resin composition consisting of 5 phr was applied to a polycarbonate substrate in the same manner as in Example 22 and light-cured.
  • the surface hardness of the cured coating film was HB and the surface resistance was 5.3 X 10 ⁇ ⁇ .
  • Hexaacrylate of phosphazene (U-100, manufactured by Idemitsu Petrochemical Co., Ltd.) 80% by weight, tetraethylene glycol monometaacrylate (Blenmer 200, manufactured by NOF Corporation) 2% by weight, AIBN A curable resin composition of 5 phr was coated on a polycarbonate substrate according to Example 22. And heat cured at 80. The surface hardness of the cured coating film was F and the surface resistance was 6.3 X 10 14 ⁇ ,
  • Phosphazene to the Kisaakurireto (U- 1 000, manufactured by Idemitsu Petrochemical Co., Ltd.> 80 wt%, main butoxy tetraethylate les glycol monomethacrylate ⁇ methacrylonitrile rate 20 wt%, implementing a curable resin composition comprising AIBN 5 P hr Example 2
  • the composition was applied on a polycarbonate substrate and thermally cured in the same manner as in 5.
  • the cured film had a surface hardness of F and a surface resistance of 7.3 ⁇ 10 14 ⁇ / ⁇ .
  • Hexafunctional urethane acrylate oligomer (U1226A manufactured by Shin-Nakamura Chemical Co., Ltd.) 4% by weight, hexafunctional acrylate oligomer (KAY ARAD DPCA 60, manufactured by Nippon Kayaku Co., Ltd.) 20% by weight, and tetraethyleneglycol A curable resin composition consisting of 40% by weight of luminomethacrylate (Light Ester DM, manufactured by Kyoeisha Oil & Fats Co., Ltd.) and 3 phr of photoinitiator Darocure 1173 (manufactured by Merck) was applied to a polycarbonate substrate in the same manner as in Example 22.
  • the coated and photocured disk had a surface hardness of F and a surface resistance of 11 ⁇ 10 12 ⁇ 1.
  • Hexaacrylate of phosphazene (U-1 000, manufactured by Idemitsu Petrochemical Co., Ltd.) 55% by weight of monoethylene glycol phosphate methacrylate (light ester DM, manufactured by Kyoeisha Oil Co., Ltd.) 45% by weight, photoinitiator Irgacure 9 ⁇ 7 (manufactured by Ciba-Geigy Corporation)
  • a curable resin composition consisting of 5 plir was applied to a polycarbonate substrate and light-cured in the same manner as in Example 22.
  • the surface hardness of the cured coating was HB and the surface resistance was 3 8X 10 10 ⁇ .
  • Hexaacrylate of phosphazene (U-1000, manufactured by Idemitsu Petrochemical Co., Ltd.) 95% by weight of monoethylene glycol methacrylate phosphate (light ester DM, manufactured by Kyoeisha Oil & Fat Co., Ltd.) 5% by weight, radical initiator AI BN
  • a curable resin composition consisting of 5 phr was applied to a polycarbonate substrate and thermally cured in the same manner as in Example 25.
  • the surface hardness of the cured coating film was HB and the surface resistance was 5.2 ⁇ 10 14. ⁇ ].
  • Hexafunctional urethane acrylate oligomer (U1226, manufactured by Shin-Nakamura Chemical Co., Ltd.) 40% by weight, hexafunctional acrylate oligomer (KAYARAD DPCA 60, manufactured by Nippon Kayaku Co., Ltd.) 40% by weight, and tetraethylene glycol Lumonomethacrylate (Phosmer M, manufactured by Kyoeisha Yushi Co., Ltd.) 20% by weight, photoinitiator Darocure 1 173 (manufactured by Merck)
  • a curable resin composition consisting of 3 phr was applied to a polycarbonate substrate in the same manner as in Example 22.
  • the surface hardness of the obtained disk was HB, and the surface resistance was 1.1 ⁇ 10 ⁇ , / ⁇ .
  • Hexaacrylate of phosphazene (U-1000, manufactured by Idemitsu Petrochemical Co., Ltd.) 99% by weight of monoester of ethylene glycol monomethacrylate and triethylamine 1: 1 adduct 1% by weight, photoinitiator Irgacure
  • a curable resin composition consisting of 5 phr was applied to a polycarbonate substrate in the same manner as in Example 22 and light-cured.
  • the surface hardness of the cured coating film was 3H, and the surface resistance was 8.5 ⁇ 10 14 ⁇ square.
  • Hexaacrylate of phosphazene (U-1000, manufactured by Idemitsu Petrochemical Co., Ltd.) 99.5% by weight of phosphoric acid monoester of ethylene glycol monomethacrylate and triethylamine 1: 1 adduct 0.5% by weight and AIBN 5
  • a curable resin composition composed of Phr was applied on a polycarbonate substrate in the same manner as in Example 25, and was thermally cured. Hardening The surface hardness of the coating film was 3H, and the surface resistance was 9.5 ⁇ 10 14 ⁇ ⁇ .
  • tetraethylene diol monoacrylate represented by the formula: 20% by weight of DPCA 60 and 20% by weight of DPCA 30 as dihexaerythritol hexyl acrylate.
  • the viscosity of this composition was 25 using a B-type viscometer.
  • the value of C was 1.3 voise.
  • This composition was applied to a flat surface of a polycarbonate substrate having a thickness of 1.2 mm and a diameter of 130 mm by a spin coating method so as to have a thickness of 8 m. Subsequently, using a high-pressure mercury lamp of about 27 cm in length and 2 KW, ultraviolet light was irradiated for 1 minute from a height of 20 cm to cure the coating film.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface pencil hardness is H
  • the surface resistivity was 1.
  • the substrate with the cured coating film was subjected to a weather resistance test in a humidifier at 80 or 85% humidity. After 2000 hours, no change was observed in the cured coating before and after the test.
  • hexaethylene dalicol monoacrylate represented by the following formula: 30% by weight of DPCA 120 and 20% by weight of DPCA 20 as dialloerythone-modified dipentaerythritol hexaacrylate, and 20% by weight of dipentaerythritol hexaacrylate.
  • a curable resin composition containing 10% by weight of xamethylene glycol diacrylate and a photoinitiator Irgacure 907 (manufactured by Ciba Geigy Co., Ltd.) for 5i> hr was prepared, and the viscosity of the composition was B-type. As measured at 25 C with a viscometer, the result was' 1.1 vois.
  • This composition was applied to a polycarbonate substrate in the same manner as in Example 33 so as to have a thickness of 1 Om, and was light-cured.
  • Example 33 so as to have a thickness of 1 Om, and was light-cured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the hardened surface is H and the surface resistance is 6.5 X
  • a curable resin composition containing 3 p r of a photopolymerization initiator Irgacure 907 (manufactured by Ciba-Geigy Co., Ltd.) in a composition consisting of 10% by weight of lugia acrylate was prepared, and the viscosity of the composition was measured at 25 ° C using a B-type viscometer. This composition was applied to a polycarbonate substrate in the same manner as in Example 34, and was cured by light.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was F, and the surface resistance was 1. IX 10 13 ⁇ 1.
  • a photopolymerization initiator was added to a composition comprising 30% by weight of tetraethylene dalicol monoacrylate represented by the following formula, 35% by weight of DPCA 60 and 35% by weight of DPCA 30 as a hexaolactone-modified dipentaerythritol hexaacrylate.
  • a curable resin composition containing 3g of Irgacure 907 (manufactured by Ciba Geigy) was prepared. Of this composition The viscosity was measured at 25 using a B-type viscometer and found to be 2.1 vois. This composition was applied to a polycarbonate substrate in the same manner as in Example 34, and photocured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the obtained cured surface was F, and the surface resistance was 4.3 ⁇ 10 13 ⁇ 1.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the hardened surface is F and the surface resistance is 5.8 X
  • a curable resin composition containing 3 Phr of a photopolymerization initiator Darocure 1 173 (manufactured by Merck) in a composition consisting of 10% by weight of mono-diacrylate was prepared. It was 0.98 boise at a measurement of 5 ° C. This composition was applied to a polycarbonate substrate in the same manner as in Example 34 and photocured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was F, and the surface resistance was 4. IX 10 13 ⁇ 1.
  • hexene ethylene diol monoacrylate represented by the following formula: 30% by weight of DPCA 60 and 2% by weight of DPCA 30 as a hexaolacrylate modified dipentaerythritol hexaacrylate; 20% per liter pantoliac acrylate, tetrahydrofurfurfuryl
  • a curable resin composition containing 3 phr of a photopolymerization initiator Irgacure 907 manufactured by Ciba-Geigy Corporation
  • the viscosity of this composition was 1.1 Boys as measured at 25 C by a B-type viscometer. This composition was applied to a polycarbonate substrate in the same manner as in Example 34, and photocured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was H, and the surface resistance was 6.5 ⁇ 10 ′′ b.
  • hexaethylene glycol monoacrylate represented by the following formula: 30% by weight of DPCA 60 and 35% by weight of DPCA 20 as a dialloerythone-modified dipentaerythritol hexaacrylate, neopentylglycol-l-diacrylate 1 ⁇ % by weight
  • a curable resin composition containing 4 Phr of a photopolymerization initiator Irgacure 907 manufactured by Ciba-Geigy Co., Ltd.
  • the viscosity of this composition was measured at 25 ° C using a B-type viscometer.
  • the composition was 2.3 poises ..
  • the composition was applied to a polycarbonate substrate and light-cured in the same manner as in Example 34.
  • the surface hardness of the cured surface was F, and the surface resistance was 6.9 ⁇ 10 13 ⁇ .
  • tetraethylene dimethyl monomethacrylate represented by the following formula: 50% by weight of DPCA120 as a dialloerythone-modified dipentaerythritol-hexahexyl acrylate, and 10% by weight of neopentyldaricol diacrylate hydroxypivalate
  • a curable resin composition containing 5 phr of a photopolymerization initiator Irgacure 907 (manufactured by Ciba-Geigy Corporation) in a composition consisting of 10% by weight of glycerol and 10% by weight of glycerol / dimethacrylate was prepared. The viscosity was measured by a B-type viscometer at 25. The measured viscosity at C was 2.6 V. This composition was applied to a polycarbonate substrate in the same manner as in Example 34, and photocured.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the hardened surface is F and the surface resistance is 9.8 X
  • a composition comprising 30% by weight, 60% by weight of DPCA 60 as a dialloerythrone-modified dipentaerythryl hexacrylate, and 10% by weight of pentaerythritol tetraacrylate is added to a photopolymerization initiator Irgacure 907 (manufactured by Ciba Geigy Corporation)
  • Irgacure 907 manufactured by Ciba Geigy Corporation
  • a curable resin composition containing 3 pl of was prepared. The viscosity of this composition was 3.3 Boyes as measured by a B-type viscometer in 2 steps. This composition was applied to a polycarbonate substrate in the same manner as in Example 34 and photocured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was H, and the surface resistance was 2.8 ⁇ 10 13 ⁇ 1.
  • tetrapropylene glycol monoacrylate represented by the following formula: 60% by weight of DPCA 60 as a hexaacrylate of dipentaerythritol modified with force allolactone
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the hardened surface is F and the surface resistance is 5.8 X
  • a curable resin composition containing 3 phr of a photopolymerization initiator il Gacure 9 ⁇ 7 (manufactured by Ciba Geigy Co., Ltd.) in a composition consisting of 20% by weight was prepared using a B-type viscometer. 25. The measured value of C was 3.3 V.
  • This composition was placed on the flat surface of a polycarbonate substrate having a thickness of 1.2 mm and a diameter of 130 mm in the same manner as in Example 33. m to a thickness of 20 m, and then apply UV light from a height of 20 cm for 1 minute using a high-pressure mercury lamp of about 27 cm in length and 2 KW to illuminate the coating film. Cured.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate disk were measured. As a result, the surface pencil hardness was H, and the surface resistance was 6.5 ⁇ 10 15 ⁇ 3.
  • Curing resin composition (NSC-7106, manufactured by Nippon Seika) 96% by weight on the flat surface of a polycarbonate substrate with a diameter of 130mm and a diameter of 130mm, the following compound (MA150, Nippon Emulsifier)
  • MA150 Nippon Emulsifier
  • a mixture of 4% by weight of a composition containing 0.1 phr of sodium dodecyl benzene sulfonate was applied by spin coating to a thickness of 10 m in the same manner as in Example 34.
  • Ultraviolet rays were irradiated for 1 minute from a height of 20 cm using a high-pressure mercury lamp of about 27 cm and 2 Kw, and the coating was photocured.
  • a curable resin composition (NSC-7106, manufactured by Nippon Seika) was 96% by weight, and the compound described in Example 44 (MA 1 50, 4% by weight of Japan Emulsifier Co., Ltd.
  • the product was applied by spin coating to a thickness of 10 m in the same manner as in Example 44, and then UV rays were applied from a height of 20 cm using a high-pressure mercury lamp of about 27 cm in length and 2 Kw.
  • the coating was light cured for 1 minute.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the pencil hardness was H, but the surface resistance was 1.2 ⁇ 10 15 ⁇ ⁇ 1.
  • Hexafunctional urethane acrylate oligomer (U1226 ⁇ , manufactured by Shin-Nakamura Chemical Co., Ltd.) 50% by weight, trimethylol aropan triacrylate 40% by weight, and tetraethylene glycol monomethacrylate 10% by weight
  • a curable resin composition containing 1 phr of sodium todecylbenzenesulfonate and 3 phr of a photoinitiator Darocure 1173 (manufactured by Merck) was applied to the polycarbonate substrate in the same manner as in Example 34.
  • the cured surface of the substrate had a surface hardness of F and a surface resistance of 3.6 ⁇ 10 13 ⁇ .
  • Hexafunctional urethane acrylate oligomer (U1226 ⁇ , manufactured by Shin-Nakamura Chemical Co., Ltd.) 50% by weight, trimethylol aropantriacrylate 40% by weight, and tetrae 1 phr weight of Tylendalcol monomethacrylate, 3 phr of Darocur 1 173 (manufactured by Merck) photoinitiator
  • the curable resin composition was applied to a polycarbonate substrate in the same manner as in Example 45. Coated and light cured. Surface hardness of the cured surface of the substrate is F, surface resistance 1. 0 5 ⁇ 1 0 15 ⁇ 1 der ivy.
  • Hexaacrylate of phosphazene (U-1 000, manufactured by Idemitsu Petrochemical Co., Ltd.) 70% by weight, tetrapropylene d'alicole monomethacrylate 30% by weight, Avanel
  • the curable resin composition comprising PhK and 3 phr of photoinitiator Irgacure 907 (manufactured by Ciba-Geigy Co., Ltd.) was prepared in the same manner as in Example 34. It was applied to a bottle substrate and light cured. The surface hardness of the cured coating film was H and the surface resistance was 3.5 ⁇ 10 12 ⁇ .
  • Tetraethylene dalicol monoacrylate represented by
  • a curable resin composition containing 0.5% by weight of sodium dodecylbenzenesulfonate and 3pr of a photopolymerization initiator Irgacure 907 (manufactured by Ciba-Geigy Corporation) was prepared in a composition consisting of 10% by weight.
  • the B-type viscosity was measured to be 1.9 vois by measurement at 25.
  • the composition was spin-coated to a thickness of 10 mm, as in Example 34, to a thickness of 10 jum. Apply it to the flat surface of a polycarbonate substrate with a diameter of 13 OM, and then irradiate ultraviolet rays for 1 minute from a height of 2 Ocm using a high-pressure mercury lamp of about 27 cm in length and 2 KW to harden the coating. It was. The surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface pencil hardness at H, the surface resistance 2. were 6 X 1 ⁇ 13 ⁇ 1.
  • the substrate having the cured product coating film was subjected to a weather resistance test for 2000 hours in a wet heat tester at 8 CTC and 85% humidity, but no change was observed in the cured coating film before and after the test.
  • tetraethylene dalicol monoacrylate represented by the following formula: 30% by weight of DPCA60 and 30% by weight of DPCA30 as a dialloerythone-modified dipentaerythrylhexaacrylate, 20% by weight of dipentaerythryl-hexaacrylate, 20% by weight of hexamethylene glycol recall di ⁇ chestnut rate 1 0 wt% composition comprising and a photopolymerization initiator Irugakyua 907 (Ciba-Geigy Ltd. one company) and 3-curable resin composition comprising P r was prepared.
  • This composition was applied to a polycarbonate substrate as in Example 48 and photocured.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • a curable resin composition was prepared which contained 10% by weight of xamethylene dimethyl alcohol, 1 phr of sodium dodecylbenzenesulfonate and 5 Phr of a photopolymerization initiator irgacure 907 (manufactured by Ciba-Geigy Corporation). The viscosity of this composition was 1.7 voise as measured by a B-type viscometer at 25.
  • This composition was applied to the flat surface of a polycarbonate substrate by spin coating so as to have a thickness of 10> am in the same manner as in Example 34, and then a high-pressure mercury lamp of about 27 cm in length and 2 KW was used. Ultraviolet rays were irradiated from a height of 20 cm for 1 minute to photo-cur the coating film. The surface resistance and pencil hardness of the cured surface of the polycarbonate substrate after curing were measured.
  • the surface hardness of the cured surface was H, and the surface resistance was 1.5 ⁇ 10 13 ⁇ / 0.
  • a curable resin composition containing 5 phr of a photopolymerization initiator Irgacure 907 (manufactured by Ciba Geigy Corporation) in a composition comprising 10% by weight of acrylate was prepared.
  • the composition was 1.7 voices as measured at 25 ° C. This composition was applied to a polycarbonate substrate in the same manner as in Example 49 and photocured.
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was H, and the surface resistance was 1.5 ⁇ 10 15 ⁇ 3.
  • pentaethyleneglycol monoacrylate represented by the following formula: 45% by weight of DPCA 60 as a di-proerythritol-modified hexacrylate, and 20% by weight of DPCA 30 as trihexyrolitol triacrylate
  • DPCA 60 a di-proerythritol-modified hexacrylate
  • DPCA 30 a trihexyrolitol triacrylate
  • a composition comprising 20% by weight of hexamethylene darico-diacrylate and 10% by weight of Sodium kill ether sulfonate (Avanel S70; manufactured by NOF Corporation) l phr, photopolymerization initiator irgacure
  • a curable resin composition containing 3 piir of 907 (manufactured by Ciba-Geigy Co., Ltd.) was prepared, and the viscosity of the composition was 2.1 Boys as measured at 25 C using a B-type viscometer.
  • the surface resistance and pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the surface hardness of the cured surface was H, and the surface resistance was 3. IX 10 13 ⁇ ].
  • the surface resistance and the pencil hardness of the cured surface of the cured polycarbonate substrate were measured.
  • the present invention provides a hard coat layer for an optical disk such as a well-known compact disk (CD) and a magneto-optical disk that has been put into practical use, and has an antistatic performance with excellent durability and a required surface hardness. It has a hard coat layer that can be formed even without solvent. It is required to have a high degree of reliability, especially for the auxiliary storage device of computers where it is essential to prevent the adhesion of foreign substances such as dust and dust. It is suitable for an optical disk such as a magneto-optical disk.

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  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

L'invention se rapporte à un disque optique qui se caractérise par une résistance de surface faible et par une excellente résistance à l'abrasion et dans lequel au moins la surface devant être irradiée de lumière est recouverte d'une couche d'enduction dure comprenant un revêtement antistatique formé par vulcanisation d'une composition à base de résine vulcanisable contenant au moins l'un des mono(méth)acrylates de polyéthylène-glycol et de polypropylène-glycol représenté par la formule (I), où R1 et R2 représentent chacun un hydrogène ou un méthyle et n représente un nombre entier compris entre 1 et 23.
PCT/JP1991/000886 1990-07-02 1991-07-01 Disque optique WO1992000588A1 (fr)

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
JP2172656A JPH0467329A (ja) 1990-07-02 1990-07-02 光デイスク
JP2/172655 1990-07-02
JP2/172656 1990-07-02
JP2/172657 1990-07-02
JP2172657A JPH0467330A (ja) 1990-07-02 1990-07-02 光デイスク
JP2172658A JPH0467331A (ja) 1990-07-02 1990-07-02 光デイスク
JP2172655A JPH0467328A (ja) 1990-07-02 1990-07-02 光デイスク
JP2/172658 1990-07-02
JP3033371A JPH04247338A (ja) 1991-02-04 1991-02-04 光ディスク
JP3/33368 1991-02-04
JP3033368A JPH04247336A (ja) 1991-02-04 1991-02-04 光ディスク
JP3033369A JPH04247337A (ja) 1991-02-04 1991-02-04 光ディスク
JP3/33371 1991-02-04
JP3/33369 1991-02-04

Publications (1)

Publication Number Publication Date
WO1992000588A1 true WO1992000588A1 (fr) 1992-01-09

Family

ID=27564347

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1991/000886 WO1992000588A1 (fr) 1990-07-02 1991-07-01 Disque optique

Country Status (1)

Country Link
WO (1) WO1992000588A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205105B2 (en) 1999-12-08 2007-04-17 Epoch Biosciences, Inc. Real-time linear detection probes: sensitive 5′-minor groove binder-containing probes for PCR analysis
US7348146B2 (en) 2003-10-02 2008-03-25 Epoch Biosciences, Inc. Single nucleotide polymorphism analysis of highly polymorphic target sequences
US7759126B2 (en) 2003-10-28 2010-07-20 Elitech Holding B.V. Real-time linear detection probes: sensitive 5′-minor groove binder-containing probes for amplification (or PCR) analysis
CN102741928A (zh) * 2010-01-29 2012-10-17 日本化药株式会社 具有有机色素记录层的光盘、用于该光盘的紫外线固化型树脂组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5622364A (en) * 1979-08-01 1981-03-02 Matsushita Electric Ind Co Ltd Coating composition
JPS59168946A (ja) * 1983-03-16 1984-09-22 Matsushita Electric Ind Co Ltd 光デイスク
JPS6254770A (ja) * 1985-07-31 1987-03-10 イ−・アイ・デユポン・ドウ・ヌム−ル・アンド・カンパニ− 光コ−テイング組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5622364A (en) * 1979-08-01 1981-03-02 Matsushita Electric Ind Co Ltd Coating composition
JPS59168946A (ja) * 1983-03-16 1984-09-22 Matsushita Electric Ind Co Ltd 光デイスク
JPS6254770A (ja) * 1985-07-31 1987-03-10 イ−・アイ・デユポン・ドウ・ヌム−ル・アンド・カンパニ− 光コ−テイング組成物

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205105B2 (en) 1999-12-08 2007-04-17 Epoch Biosciences, Inc. Real-time linear detection probes: sensitive 5′-minor groove binder-containing probes for PCR analysis
US7485442B2 (en) 1999-12-08 2009-02-03 Epoch Biosciences, Inc. Real-time linear detection probes: sensitive 5'-minor groove binder-containing probes for PCR analysis
US7348146B2 (en) 2003-10-02 2008-03-25 Epoch Biosciences, Inc. Single nucleotide polymorphism analysis of highly polymorphic target sequences
US7718374B2 (en) 2003-10-02 2010-05-18 Elitech Holding B.V. Single nucleotide polymorphism analysis of highly polymorphic target sequences
US7759126B2 (en) 2003-10-28 2010-07-20 Elitech Holding B.V. Real-time linear detection probes: sensitive 5′-minor groove binder-containing probes for amplification (or PCR) analysis
CN102741928A (zh) * 2010-01-29 2012-10-17 日本化药株式会社 具有有机色素记录层的光盘、用于该光盘的紫外线固化型树脂组合物

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