WO2006051895A1 - Composition de resine durcissable aux ultraviolets et son produit de durcissement - Google Patents

Composition de resine durcissable aux ultraviolets et son produit de durcissement Download PDF

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Publication number
WO2006051895A1
WO2006051895A1 PCT/JP2005/020702 JP2005020702W WO2006051895A1 WO 2006051895 A1 WO2006051895 A1 WO 2006051895A1 JP 2005020702 W JP2005020702 W JP 2005020702W WO 2006051895 A1 WO2006051895 A1 WO 2006051895A1
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WO
WIPO (PCT)
Prior art keywords
curable resin
resin composition
ultraviolet curable
meth
cured product
Prior art date
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PCT/JP2005/020702
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English (en)
Japanese (ja)
Inventor
Kiyohisa Tokuda
Go Mizutani
Hideaki Kametani
Kazuhiko Ishii
Masahiro Naitoh
Original Assignee
Nippon Kayaku Kabushiki Kaisha
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Publication of WO2006051895A1 publication Critical patent/WO2006051895A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • 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
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers

Definitions

  • Ultraviolet curable resin composition and cured product thereof
  • the present invention relates to an ultraviolet curable resin composition and a cured product thereof, and more particularly, an ultraviolet curable resin composition and a cured product that are excellent in transparency and durability with low water absorption rate and curing shrinkage rate. And a next generation high density optical disc having the cured product layer.
  • CD compact disc
  • MO magnetic-optical disc
  • CD—R write-once compact disc
  • CD—RW Rewritable compact disc
  • a method of forming the cover layer a method of laminating a transparent film having a thickness of 100 m and a method of forming a layer having a thickness of 100 / zm on the recording film using an ultraviolet curable resin are used.
  • the 2P method and the spin coater method are proposed as methods for forming the UV-curable resin layer. It has been proposed.
  • an ultraviolet curable resin for forming a cover layer on a recording film for example, 2P agents such as the compositions described in Patent Document 2 and Patent Document 3 have been proposed.
  • protective coating agents such as the compositions described in Patent Document 4, Patent Document 5, and Patent Document 6 have been proposed.
  • Patent Document 1 Japanese Patent Laid-Open No. 11-273147
  • Patent Document 2 JP-A-5-059139
  • Patent Document 3 Japanese Patent Laid-Open No. 5-132534
  • Patent Document 4 Japanese Patent Laid-Open No. 3-131605
  • Patent Document 5 Japanese Patent Laid-Open No. 3-172358
  • Patent Document 6 Japanese Patent Laid-Open No. 2003-268263
  • the present invention relates to
  • component (A) comprising a di (meth) acrylic ester of pentacyclopentadecane dimethanol, a photopolymerization initiator (B), and an ethylenically unsaturated compound (C) other than component (A), UV curable resin composition having a viscosity of 100 to 5000 mPa's at 25 ° C measured with a B-type viscometer,
  • R represents a hydrogen atom or a methyl group.
  • the ultraviolet curable resin composition according to (1) which is a mixture of
  • the present invention is a UV curable resin composition and a cured product thereof, useful as a protective coating agent for high-density optical discs, having excellent durability with low transparency, excellent water absorption, and low warpage.
  • it can also be applied to materials related to optical applications such as optical finos and optical switching elements.
  • the ultraviolet curable resin composition of the present invention comprises pentacyclopentadecane dimethanol dimer.
  • Containing component (A) consisting of (meth) acrylic acid ester, photopolymerization initiator (B), and ethylenically unsaturated compound (C) other than component (A), measured at 25 ° C with a B-type viscometer UV curable resin composition having a viscosity at 100 to 5000 mPa's.
  • the component (A) contained in the ultraviolet curable resin composition of the present invention contributes to the low water absorption performance and low shrinkage performance of the cured product.
  • pentacyclopentadeca It can be obtained by a method of dehydration condensation of dimethylethanol and (meth) acrylic acid in the presence of an acid catalyst.
  • the raw material pentacyclopentadecane dimethanol can be obtained, for example, by hydrogenating formaldehyde of tricyclopentagen and dialdehyde obtained (for example, JP 2001-10999).
  • tricyclopentagen has a left-right symmetric structure and a left-right asymmetric structure, and usually exists as a mixture thereof.
  • the component (A) contained in the ultraviolet curable resin composition of the present invention also has a symmetrical structure in which the pentacyclopentadecane dimethanol moiety is represented by the following general formula (1) and the following general formula: There is a left-right asymmetric structure shown in (2), which usually exists as a mixture.
  • R represents a hydrogen atom or a methyl group.
  • the content of the component (A) in the ultraviolet curable resin composition of the present invention is preferably 5 to 98 parts by weight, particularly preferably 10 to 100 parts by weight based on the total amount of the resin composition. 96 parts by weight.
  • the photopolymerization initiator (B) contained in the ultraviolet curable resin composition of the present invention includes 1-hydroxycyclohexyl phenyl ketone (Irgacure 184; manufactured by Chinoku Specialty Chemicals), 2,2 Dimethoxy-2-phenylacetophenone (Irgacure 651; manufactured by Tinoku Specialty Chemicals), 2-hydroxy-1-2-methyl-1-phenyl-propane-1-one (Darocur 1173; Chinok 1special) Chemicals), 2-Methyl 1— [4- (Methylthio) phenol] 2 Morpholinopropane 1-one (Irgacure 907; Ciba Specialty Chemicals), 2-Benzyl-2-dimethylamino 1- (4 Morpholi Nophenyl) Butane 1-on, 2 Black mouth thixanthone, 2, 4 Dimethylthioxanthone, 2, 4 Diisopropinoretioxanthone, Isopropinor
  • the content of the photopolymerization initiator (B) in the ultraviolet curable resin composition of the present invention is preferably 0.5 to 20 parts by weight based on 100 parts by weight of the total amount of the resin composition. Particularly preferred is 1 to 10 parts by weight.
  • Examples of photopolymerization initiation assistants such as amines that can be used in the present invention include diethanolamine, 2-dimethylaminoethylbenzoate, dimethylaminoacetophenone, and p-dimethyl. Examples include luaminobenzoic acid ethyl ester, P-dimethylaminobenzoic acid isoamyl ester, and the like.
  • the content in the ultraviolet curable oil composition of the present invention is 0.05 to 5 parts by weight with 100 parts by weight of the total amount of the resin composition. Particularly preferred is 0.1 to 3 parts by weight.
  • Examples of the ethylenically unsaturated compound (C) other than the component (A) that can be used in the ultraviolet curable resin composition of the present invention include an acrylate monomer, an acrylate oligomer, and the like. May be used arbitrarily.
  • the acrylate monomer as the ethylenically unsaturated compound (C) includes a monofunctional monomer having one (meth) acrylate group in the molecule and two or more (meth) acrylate groups in the molecule.
  • the polyfunctional monomer can be classified.
  • Examples of monofunctional monomers having one (meth) acrylate group in the molecule include tricyclodecane (meth) acrylate, dicyclopentagenoxychetyl (meth) acrylate, dicyclopental ( (Meth) Atarylate, Isovolyl (Meth) Atarylate, Adamantyl (Meth) Atarylate, Ferrochechetyl (Meth) Atarylate, Benzyl (Meth) Atrelate, Tetrahydrofurfuryl (Meth) Atarylate, Morpholine (Meth) Examples include attalylate, ferricglycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, ethyl carbitol (meth) acrylate.
  • examples of the (meth) acrylate monomer (C) having two or more (meth) acrylate groups in the molecule include neopentyl dalycol di (meth) acrylate, tricyclodecane dimethylol di ( (Meth) Atalylate, hydroxypivalaldehyde-modified trimethylolpropane di (meth) atalylate, neopentyl glycol di (meth) acrylate, hydroxybivalate, polyethylene glycol di (meth) attalylate, dicyclopenta-ldi (meth) atari 1, 6-Hexanediol di (meth) acrylate, polypropylene glycol di (meth) acrylate, ethylene oxide modified bisphenol A di (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) Atalylate, ethylene oxide Sex Pentaerisu Ritorutetora (meth) A
  • acrylate monomers may be used alone or in any combination of two or more. May be used together.
  • the content in the ultraviolet curable resin composition of the present invention is preferably 1 to 90 parts by weight, particularly preferably 5 to 100 parts by weight based on the total amount of the resin composition. 85 parts by weight.
  • the ultraviolet curable resin composition of the present invention has a viscosity at 25 ° C of 10 measured by a B-type viscometer.
  • Examples of the acrylate oligomer as the ethylenically unsaturated compound (C) include urethane (meth) acrylate having a molecular weight of 400 to 10,000 and epoxy acrylate having a molecular weight of 500 to 10,000.
  • Urethane (meth) atalylate having a molecular weight of 400 to 10,000 is obtained by a reaction of the following polyhydric alcohol, an organic polyisocyanate, and a hydroxy (meth) atalytoi compound.
  • polyhydric alcohol examples include neopentyl glycol, 3-methyl-1,5-pentanediol, ethylene glycol, propylene glycol, 1,4 butanediol, 1,6 hexanediol, trimethylolpropane, pentaerythritol.
  • Tricyclodecane dimethylol Tricyclodecane dimethylol, bis (hydroxymethyl) cyclohexane and the like
  • the polyhydric alcohols and polybasic acids for example, succinic acid, phthalic acid, hexahydrophthalic anhydride, terephthalic acid, adipic acid, azelaic acid, tetrahydro Polyester polyol obtained by reaction with phthalic anhydride, etc., and force prolataton alcohol obtained by reaction of the polyhydric alcohol with ⁇ -force prolataton, and polycarbonate polyol (eg, 1, 6 to one) Xanthandiol and diphe And polycarbonate polyols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and ethylene oxide-modified bisphenol ⁇ obtained by reaction with carbonate).
  • polycarbonate polyol eg, 1, 6 to one
  • organic polyisobutylene Xia sulfonates such as isophorone di-iso-Xia sulfonate, to Kisamechiren Jiisoshianeto, tolylene iso Xia sulfonates, xylylene iso Xia sulfonates, Jifuenirumeta Hmm 4, 4 'over-di iso Xia sulfonate, dicyclopenta - Ruisoshianeto etc. Is mentioned.
  • hydroxy (meth) attareito toy compound examples include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylol cyclohexyl mono (meta) ) Atarylate, hydroxycaprolataton (meth) attareido And so on.
  • the content of the ultraviolet ray curable resin composition of the present invention is 1 to 100 parts by weight based on the total amount of the resin composition. 90 parts by weight is preferred, with 3 to 85 parts by weight being particularly preferred.
  • the molecular weight 500 to be used in the ultraviolet curable resin composition of the present invention is not particularly limited, but it is preferable to use a bisphenol type epoxy acrylate, for example, oil Epoxy Coat Epoxy Coat 802, 1001, 1004, etc., and Epoxy Coat obtained by the reaction of Bisphenol F type epoxy resin, Epicoat 4001, P2, 4003P, etc. with (meth) acrylic acid Atallate is mentioned. Moreover, you may use the alicyclic epoxy acrylate which hydrogenated the above.
  • the content in the ultraviolet ray curable resin composition of the present invention is preferably 1 to 90 parts by weight based on 100 parts by weight of the total amount of the resin composition. Particularly preferred is 3 to 85 parts by weight.
  • the ultraviolet curable resin composition of the present invention may contain a polyester-based, polycarbonate-based, polyacrylic-based, polyurethane-based, or polybull-based resin as a high-molecular polymer as necessary. it can. Furthermore, additives such as organic solvents, silane coupling agents, polymerization inhibitors, leveling agents, light stabilizers, antioxidants, antistatic agents, surface lubricants, fillers and the like can be used in combination.
  • the ultraviolet curable resin composition of the present invention can be obtained by mixing and dissolving the above-mentioned components at 20 to 80 ° C by stirring and mixing, and may be filtered after obtaining the composition.
  • the cured product of the ultraviolet curable resin composition of the present invention can be obtained by irradiating the ultraviolet curable resin composition of the present invention with light such as ultraviolet rays and visible light by the following method.
  • Light irradiation curing of the ultraviolet curable resin composition of the present invention may be performed using any light source as long as it is a lamp that irradiates light in the ultraviolet region to the near ultraviolet region.
  • Examples include low-pressure, high-pressure or ultra-high pressure mercury lamps, metal nitride lamps, (pulse) xenon lamps, and electrodeless lamps.
  • the ultraviolet curable resin composition of the present invention has a curing shrinkage rate of 6% or less when cured, and a water absorption rate (measurement temperature 25 ° C) of the cured product is 2.0% or less. Is preferred.
  • the protective coating agent for optical disks using the ultraviolet curable resin composition of the present invention may be applied by any coating method as long as the film thickness can be 50-100 ⁇ m. Examples of the method include spin coating, 2P, roll coating, and screen printing.
  • the transmittance around 400 to 500 nm is 70 in a cured product with a film thickness of 50 to 150 m. % Or more is preferable.
  • the optical disk according to the present invention having a cured product layer of the above-described ultraviolet curable resin composition, and the ultraviolet curable adhesive on the side on which recording light and Z or reproduction light are incident.
  • cured material layer of the fat composition is formed is mentioned as a suitable thing.
  • Example 1 Example 2 Example 3 Comparative Example 1 Example Ingredient (A) (Part)
  • UX-6101 Polyester urethane acrylate (molecular weight; 2700 ⁇ 500), Nippon Kayaku Made by company.
  • R-604 Hydroxypivalaldehyde-modified trimethylolpropane di (meth) acrylate, manufactured by Enomoto Kayaku Co., Ltd.
  • PEG—400DA Polyethylene glycol ditalylate, manufactured by Nippon Kayaku Co., Ltd.
  • LA Lauryl acrylate, manufactured by NOF Corporation.
  • Irgacure 184 1-Hydroxycyclohexylphenyl ketone, photopolymerization initiator manufactured by Tinoku 'Specialty' Chemicals.
  • BP—100 Benzophenone, manufactured by Nippon Kayaku Co., Ltd.
  • the viscosity was measured with a B-type viscometer.
  • the curing shrinkage is a value calculated from the following formula (1) from the liquid specific gravity before curing at 25 ° C and the film specific gravity at 25 ° C obtained by curing.
  • Curing shrinkage (Membrane specific gravity Liquid specific gravity) Z Membrane specific gravity X 100 (1)
  • the water absorption is a value obtained by a method according to JIS K-7209 7.2.1.
  • the transmittance is measured by applying a resin to a polycarbonate substrate by spin coating to a thickness of 100 ⁇ 10 ⁇ m, and after UV curing, measure the transmittance at 405 nm using the polycarbonate substrate as a reference. It went by.
  • a DVD substrate on which aluminum was sputtered was used for warpage evaluation.
  • Each of the compositions shown in Table 1 was applied onto an aluminum sputtered DVD substrate by a spin coater to form a coating film having an average film thickness of 100 m.
  • the obtained test piece was allowed to stand for 24 hours and then placed on a glass plate, and the warpage was evaluated according to the following criteria.
  • the test piece used for the evaluation of the warp was used and left for 500 hours in an environment of 80 ° C. and 85% RH.
  • the state of the reflective film was visually observed, and the durability was evaluated according to the following criteria.
  • the ultraviolet curable resin composition and the cured product thereof according to the present invention are excellent in transparency, low water absorption, and have high durability with little warpage, and the cured product thereof. It can be used as a protective coating agent for high-density optical discs, and is extremely useful when applied to optical discs that perform reading and Z or writing using a blue laser. It is.
  • the ultraviolet curable resin composition and the cured product thereof according to the present invention include a protective coating agent for optical discs and a force that provides the cured product, and other materials related to optical applications such as optical finos and optical switching elements. It can also be applied to.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

Le problème à résoudre dans le cadre de cette invention consiste à prévoir une composition de résine durcissable aux ultraviolets, ou son produit de durcissement, qui présente une excellente transparence et une faible absorption d'eau, et dont le gauchissement est réduit et la durabilité élevée. La composition de résine durcissable aux ultraviolets de l'invention ou son produit de durcissement peuvent être utilisés sous forme d'agent de revêtement protecteur, ou son produit de durcissement, pour un disque optique de densité élevée, en particulier un disque optique capable de lire et/ou d'écrire à l'aide d'un laser bleu. La solution proposée consiste à prévoir une composition de résine durcissable aux ultraviolets d'une viscosité de 100 à 5 000 mPa mesurée à 25 °C par l'utilisation d'un viscosimètre du type B, ladite composition comprenant un composant consistant en un ester di(méth)acrylique du pentacyclopentadécanediméthanol (A), un initiateur de photopolymérisation (B) et un composé à insaturation éthylénique (C) différent du composant (A).
PCT/JP2005/020702 2004-11-15 2005-11-11 Composition de resine durcissable aux ultraviolets et son produit de durcissement WO2006051895A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-330498 2004-11-15
JP2004330498A JP2008024724A (ja) 2004-11-15 2004-11-15 紫外線硬化型樹脂組成物およびその硬化物

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WO2006051895A1 true WO2006051895A1 (fr) 2006-05-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109575758A (zh) * 2018-10-31 2019-04-05 澳达树熊涂料(惠州)有限公司 一种紫外光固化全净味镭射涂装哑光面漆制备方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5846709B2 (ja) * 2008-03-31 2016-01-20 太陽ホールディングス株式会社 活性エネルギー線硬化性樹脂組成物、およびその硬化物と透明成型品
CN102203862B (zh) * 2008-11-05 2013-10-23 日本化药株式会社 光盘用紫外线固化型树脂组合物及其固化产物
JP5931057B2 (ja) 2011-05-16 2016-06-08 三井化学株式会社 歯科材料、歯科材料組成物、歯科修復材料および硬化物
WO2012157568A1 (fr) 2011-05-16 2012-11-22 三井化学株式会社 Nouveau composé, composition le contenant, et produit durci
JP6048029B2 (ja) * 2012-09-21 2016-12-21 三菱瓦斯化学株式会社 高硬度樹脂組成物
JP6677047B2 (ja) * 2016-03-30 2020-04-08 三菱ケミカル株式会社 脂環式多官能（メタ）アクリレート化合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0312837A (ja) * 1989-06-09 1991-01-21 Mitsubishi Petrochem Co Ltd 光学材料の製造法
JP2003268263A (ja) * 2002-03-15 2003-09-25 Toagosei Co Ltd 硬化性ハードコート形成剤
JP2005075968A (ja) * 2003-09-02 2005-03-24 Mitsubishi Gas Chem Co Inc 透明樹脂材料の製造方法
JP2005154543A (ja) * 2003-11-25 2005-06-16 Mitsubishi Gas Chem Co Inc 透明樹脂材料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0312837A (ja) * 1989-06-09 1991-01-21 Mitsubishi Petrochem Co Ltd 光学材料の製造法
JP2003268263A (ja) * 2002-03-15 2003-09-25 Toagosei Co Ltd 硬化性ハードコート形成剤
JP2005075968A (ja) * 2003-09-02 2005-03-24 Mitsubishi Gas Chem Co Inc 透明樹脂材料の製造方法
JP2005154543A (ja) * 2003-11-25 2005-06-16 Mitsubishi Gas Chem Co Inc 透明樹脂材料

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109575758A (zh) * 2018-10-31 2019-04-05 澳达树熊涂料(惠州)有限公司 一种紫外光固化全净味镭射涂装哑光面漆制备方法

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JP2008024724A (ja) 2008-02-07

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